TWI856246B - Compound, liquid crystal composition and liquid crystal display element - Google Patents

Abstract

A compound represented by formula (1). In formula (1), ^R1 and ^R2 are alkyl groups having 1 to 15 carbon atoms, etc.; ^Ra is hydrogen, etc.; Ring ^A1 and Ring ^A2 are 1,4-cyclohexylene, 1,4-phenylene, etc.; Ring ^N1 and Ring ^N2 are 1,2-cyclopropylene, 1,3-cyclopentylene, etc.; ^Z1 , ^Z2 , ^Z3 , and ^Z4 are single bonds, etc.; ^L1 , ^L2 , ^L3 , ^L4 , ^L5 , and ^L6 are fluorine, etc.; l and o are 0 or 1, and m and n are 0, 1, or 2.

Description

Compound, liquid crystal composition and liquid crystal display element

The present invention relates to a liquid crystal compound having a carbazole ring, a liquid crystal composition and a liquid crystal display device. More specifically, the present invention relates to a liquid crystal compound having a carbazole ring and having negative dielectric anisotropy, a liquid crystal composition containing the same and a liquid crystal display device containing the composition.

In liquid crystal display devices, the operation mode of liquid crystal molecules is classified into phase change (PC), twisted nematic (TN), super twisted nematic (STN), electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (VA), fringe field switching (FFS), field-induced photo-reactive alignment (FPA), etc. Based on the driving method of the device, it is classified into passive matrix (PM) and active matrix (AM). PM is classified into static, multiplex, etc., and AM is classified into thin film transistor (TFT), metal insulator metal (MIM), etc.

A liquid crystal composition is sealed in the element. The physical properties of the composition are related to the characteristics of the element. Examples of the physical properties in the composition are stability to heat or light, temperature range of nematic phase, viscosity, optical anisotropy, dielectric anisotropy, specific resistance, elastic constant, etc. The composition is prepared by mixing many liquid crystal compounds. The physical properties required for the compound are: high stability to environments such as water, air, heat, and light, a wide temperature range of the liquid crystal phase, small viscosity, appropriate optical anisotropy, large dielectric anisotropy, appropriate elastic constant, good compatibility with other liquid crystal compounds, etc. Preferably, it is a compound with a high upper temperature limit of the nematic phase. Preferably, it is a compound with a low lower temperature limit in a liquid crystal phase such as a nematic phase or a smectic phase. A compound with a small viscosity contributes to a short response time of the device. The appropriate value of optical anisotropy depends on the type of operation mode of the device. When the device is driven at a low voltage, a compound with a positive or negative and large dielectric anisotropy is preferred. When preparing a composition, a compound with good compatibility with other liquid crystal compounds is preferred. The device is sometimes used at a temperature below the freezing point, so a compound with good compatibility at low temperatures is preferred.

A large number of liquid crystal compounds have been synthesized so far. New liquid crystal compounds are still being developed. The reason is that for new compounds, good physical properties that do not exist in previous compounds are expected. The reason is that new compounds sometimes also give a proper balance to at least two physical properties in the composition. There are few reports related to the following compounds with divalent groups. Furthermore, in the following divalent groups, X is hydrogen or a substituent.

[Chemistry 1]

For example, in Patent Document 1, Table 4 on page 41 discloses compounds numbered 53, 54, and 56, and Table 8 on page 45 discloses compounds numbered 125 and 127.

[Chemistry 2]

In Patent Document 2, page 10 discloses the II-a compound of Example 3, and page 14 discloses the III-a compound of Example 7.

[Chemistry 3] [Prior art literature] [Patent literature]

[Patent Document 1] International Publication No. 2007/018168 [Patent Document 2] International Publication No. 2017/084231

[The problem that the invention wants to solve]

The first topic is to provide a liquid crystal compound that satisfies at least one of the following physical properties: high stability to heat or light, high clearing point (or high upper temperature limit of nematic phase), low lower temperature limit of liquid crystal phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, appropriate elastic constant, good compatibility with other liquid crystal compounds. Compared with similar compounds, a compound having negative and large dielectric anisotropy is provided. The second topic is to provide a liquid crystal composition containing the compound and fully satisfying at least one of the physical properties such as high stability to heat or light, high upper temperature limit of the nematic phase, low lower temperature limit of the nematic phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, large specific resistivity, and appropriate elastic constant. The topic is to provide a liquid crystal composition with an appropriate balance with respect to at least two physical properties. The third topic is to provide a liquid crystal display element containing the composition and having a wide temperature range in which the element can be used, a short response time, a large voltage retention rate, a low critical voltage, a large contrast ratio, a small flicker rate, and a long life. [Means for solving the problem]

The present invention relates to a compound represented by formula (1), a liquid crystal composition containing the compound, and a liquid crystal display device containing the liquid crystal composition.

[Chemistry 4]

In formula (1), ^R1 is hydrogen or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R1 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^R2 is hydrogen, fluorine, chlorine, -C≡N, -C≡CC≡N, or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R2 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently cycloalkylene groups having 3 to 5 carbon atoms. In Ring ^A1 and Ring ^A2 , at least one _-CH2- may be substituted by -O-, and at least one -( _CH2 ) _2- may be substituted by -CH=CH-; Ring ^N1 and Ring N2 are independently cycloalkylene groups having 3 to 5 carbon atoms. ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ^{ring N1} and ring ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) ^2- may _be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L1 , ^L2 , ^L3 , ^L4 , ^L5 , and ^L6 are independently hydrogen, fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; when ^L5 and ^L6 are both hydrogen, at least one of ^L1 , ^L2 , ^L3 , and ^L4 is fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; when ^L1 , ^L2 , ^L3 , and ^L4 are all hydrogen, at least one of ^L5 and ^L6 is fluorine, chlorine, _-CF3 , -CHF2, _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or _-C≡N ; l and o are independently 0 or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4; when l is 0, R ¹ will not become hydrogen, and when o is 0, R ² will not become hydrogen. [Effect of the Invention]

The first advantage is to provide a liquid crystal compound that fully satisfies at least one of the following physical properties: high stability to heat or light, high clearing point (or high upper temperature limit of nematic phase), low lower temperature limit of liquid crystal phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, appropriate elastic constant, good compatibility with other liquid crystal compounds, etc. Compared with similar compounds, a compound having negative and large dielectric anisotropy is provided. The second advantage is to provide a liquid crystal composition containing the compound and fully satisfying at least one of the physical properties such as high stability to heat or light, high upper temperature limit of the nematic phase, low lower temperature limit of the nematic phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, large specific resistance, and appropriate elastic constant. The advantage is to provide a liquid crystal composition with a proper balance with respect to at least two physical properties. The third advantage is to provide a liquid crystal display element containing the composition and having a wide temperature range in which the element can be used, a short response time, a large voltage holding ratio, a low critical voltage, a large contrast ratio, a small flicker rate, and a long life.

The terms used in this specification are as follows. The terms "liquid crystal compound", "liquid crystal composition", and "liquid crystal display element" are sometimes abbreviated as "compound", "composition", and "element", respectively. "Liquid crystal compound" is a general term for compounds having liquid crystal phases such as nematic phase and smectic phase, and compounds that do not have a liquid crystal phase but are added for the purpose of adjusting the physical properties of the composition such as the upper limit temperature, lower limit temperature, viscosity, and dielectric anisotropy. The compound has a six-membered ring such as 1,4-cyclohexyl or 1,4-phenylene, and its molecular structure is rod-like. "Liquid crystal display element" is a general term for liquid crystal display panels and liquid crystal display modules. "Polymerizable compound" is a compound added for the purpose of generating a polymer in a composition. Liquid crystal compounds having alkenyl groups are not polymerizable in their meaning.

Liquid crystal compositions are prepared by mixing a variety of liquid crystal compounds. Additives are added to the composition for the purpose of further adjusting the physical properties. Polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, thermal stabilizers, pigments, and additives such as defoamers are added as needed. Liquid crystal compounds or additives are mixed in this order. Even when additives are added, the proportion (content) of the liquid crystal compound is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition without the additive. The proportion (addition amount) of the additive is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition without the additive. That is, the proportion of the liquid crystal compound or additive is calculated based on the total weight of the liquid crystal compound. Sometimes parts per million (ppm) by weight is also used. The proportions of the polymerization initiator and the polymerization inhibitor are exceptionally expressed based on the weight of the polymerizable compound.

The "transparent point" is the transition temperature of the liquid crystal phase-isotropic phase in the liquid crystal compound. The "lower limit temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (smectic phase, nematic phase, etc.) in the liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature of the nematic phase-isotropic phase in a mixture of the liquid crystal compound and the mother liquid crystal or in a liquid crystal composition, and is sometimes referred to as the "upper limit temperature". Sometimes the "lower limit temperature of the nematic phase" is referred to as the "lower limit temperature". The expression "increasing dielectric anisotropy" refers to a positive increase in its value when the dielectric anisotropy is a composition, and a negative increase in its value when the dielectric anisotropy is a composition. "High voltage retention rate" means that the component has a high voltage retention rate not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and has a high voltage retention rate not only at room temperature but also at a temperature close to the upper limit temperature after long-term use. In compositions or components, characteristics are sometimes studied before and after time-dependent change tests (including accelerated degradation tests).

The compound represented by formula (1) is sometimes referred to as compound (1). At least one compound selected from the group of compounds represented by formula (1) is sometimes referred to as compound (1). "Compound (1)" refers to one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. These rules also apply to compounds represented by other formulas. In formulas (1) to (15), symbols such as A ¹ , B ¹ , and C ¹ surrounded by hexagons correspond to rings such as ring A ¹ , ring B ¹ , and ring C ¹ , respectively. The hexagon represents a six-membered ring such as cyclohexane or benzene. The hexagon sometimes represents a condensed ring such as naphthalene, or a cross-linked ring such as diamond.

In the chemical formula of the component compound, the symbol of the terminal group R ¹¹ is used for a plurality of compounds. In these compounds, the two groups represented by any two R ¹¹ may be the same or different. For example, there is a case where R ¹¹ of compound (2) is an ethyl group, and R ¹¹ of compound (3) is an ethyl group. There is also a case where R ¹¹ of compound (2) is an ethyl group, and R ¹¹ of compound (3) is a propyl group. This rule also applies to symbols such as R ¹² , R ¹³ , and Z ^11. In compound (15), when i is 2, there are two rings E ¹ . In this compound, the two groups represented by the two rings E ¹ may be the same or different. When i is greater than 2, this also applies to any two rings E ¹ . This rule also applies to other symbols.

The expression "at least one 'A'" means that the number of 'A' is arbitrary. The expression "at least one 'A' may be replaced by 'B'" means that when the number of 'A' is one, the position of 'A' is arbitrary, and when the number of 'A' is two or more, the positions may also be selected without restriction. This rule also applies to the expression "at least one 'A' is replaced by 'B'". The expression "at least one 'A' may be replaced by 'B', 'C', or 'D'" means including: any case where 'A' is replaced by 'B', any case where 'A' is replaced by 'C', and any case where 'A' is replaced by 'D', and further the case where multiple 'A' are replaced by at least two of 'B', 'C', and/or 'D'. For example, "an alkyl group in which at least one -CH ₂ - may be substituted with -O- or -CH=CH-" includes: alkyl, alkoxy, alkoxyalkyl, alkenyl, alkoxyalkenyl, alkenyloxyalkyl. Furthermore, the situation where two consecutive -CH ₂ - are substituted with -O- to become -OO- is not favorable. The situation where the -CH ₂ - of the methyl part (-CH ₂ -H) of an alkyl group is substituted with -O- to become -OH is also not favorable.

Sometimes, the expression "R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one -CH ₂ - in the alkyl group and the alkenyl group may be substituted by -O-, and at least one hydrogen in these groups may be substituted by fluorine" is used. In this expression, "these groups" can be interpreted as the language. In this expression, "these groups" refers to alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, etc. That is, "these groups" means all the groups described before the term "these groups". This common sense explanation also applies to the term "these monovalent groups" or "these divalent groups". For example, "these monovalent groups" means all the groups described before the term "these monovalent groups".

Halogen refers to fluorine, chlorine, bromine, and iodine. Preferred halogens are fluorine and chlorine. Further preferred halogens are fluorine. The alkyl group of the liquid crystal compound is linear or branched and does not contain a cyclic alkyl group. A linear alkyl group is generally preferred over a branched alkyl group. The same is true for terminal groups such as alkoxy and alkenyl. In order to increase the upper temperature limit, the stereo configuration associated with 1,4-cyclohexyl is trans preferred over cis. 2-Fluoro-1,4-phenylene refers to the following two divalent groups. In the chemical formula, fluorine can be to the left (L) or to the right (R). This rule also applies to asymmetric divalent groups such as tetrahydropyran-2,5-diyl generated by removing two hydrogen atoms from the ring.

[Chemistry 5]

The present invention includes the following items, etc.

Item 1. A compound represented by formula (1),

[Chemistry 6]

In formula (1), ^R1 is hydrogen or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R1 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^R2 is hydrogen, fluorine, chlorine, -C≡N, -C≡CC≡N, or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R2 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^Ra is hydrogen, a straight chain alkyl group having 1 to 6 carbon atoms, or a branched chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently cycloalkylene groups having 3 to 5 carbon atoms. In Ring ^A1 and Ring ^A2 , at least one _-CH2- may be substituted by -O-, and at least one -( _CH2 ) _2- may be substituted by -CH=CH-; Ring ^N1 and Ring N2 are independently cycloalkylene groups having 3 to 5 carbon atoms. ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ^{ring N1} and ring ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) ^2- may _be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L1 , ^L2 , ^L3 , ^L4 , ^L5 , and ^L6 are independently hydrogen, fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; when ^L5 and ^L6 are both hydrogen, at least one of ^L1 , ^L2 , ^L3 , and ^L4 is fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; when ^L1 , ^L2 , ^L3 , and ^L4 are all hydrogen, at least one of ^L5 and ^L6 is fluorine, chlorine, _-CF3 , -CHF2, _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or _-C≡N ; l and o are independently 0 or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4; when l is 0, ^R1 will not be hydrogen, and when o is 0, ^R2 will not be hydrogen.

Item 2. The compound according to Item 1, which is represented by Formula (1-1) to Formula (1-13),

[Chemistry 7]

In formula (1-1) to formula (1-13), R ¹ is hydrogen, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; R ² is hydrogen, fluorine, chlorine, -CF ₃ , -OCF ₃ , -C≡N, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring A ¹ and Ring A ² are independently cycloalkylene groups having 3 to 5 carbon atoms, and in Ring A ¹ and Ring A ² , at least one -CH ₂ - may be substituted by -O-, at least one -(CH ₂ ) ₂ - may be substituted by -CH=CH-; Ring N ¹ and Ring N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ring ^N1 and ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, -CF3 _{, -CHF2} , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and ^Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L1 , ^L2 , ^L3 , and ^L4 are independently hydrogen, fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2 F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; in formula (1-1), formula (1-3), formula (1-5), formula (1-7), formula (1-9), formula (1-11), and formula (1-13), R ¹ will not be hydrogen; in formula (1-1) to formula (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1-13), R ² will not be hydrogen.

Item 3. The compound as described in Item 2, wherein in the formula (1-1) to (1-13), ^R1 and ^R2 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently 1,2-cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; Ring ^N1 and Ring N2 are independently cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, or benzo[b]thiophene-2,6-diyl, and at least one hydrogen in the ring ^N1 and the ring ^N2 may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , -OCF Z ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² , Z ³ , and Z ⁴ are independently a single bond, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N, and at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; In formula (1-1), formula (1-3), formula (1-5), formula (1-7), formula (1-9), formula (1-11), and formula (1-13), R ¹ will not be hydrogen, and in formula (1-1) to formula (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1-13), R ² will not be hydrogen.

Item 4. The compound according to Item 1, which is represented by Formula (1-14) to Formula (1-26),

[Chemistry 8]

In formula (1-14) to formula (1-26), ^R1 is hydrogen, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; ^R2 is hydrogen, fluorine, chlorine, _-CF3 , _-OCF3 , -C≡N, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently cycloalkyl groups having 3 to 5 carbon atoms, and in Ring ^A1 and Ring ^A2 , at least one -CH ₂ - may be substituted by -O-, and at least one -(CH ₂ ) ₂ - may be substituted by -CH=CH-; Ring N ¹ and Ring N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine ... pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ring ^N1 and ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, -CF3 _{, -CHF2} , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and ^Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L5 and ^L6 are independently hydrogen, fluorine, chlorine, -CF3, _-CHF2 , _-CH2F , _{-OCF3, -OCHF2 ,} or -OCH2F. ₂ , -OCH ₂ F, or -C≡N, at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; in formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26), R ¹ will not be hydrogen, and in formula (1-14) to formula (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1-26), R ² will not be hydrogen.

Item 5. The compound as described in Item 4, wherein in the formula (1-14) to the formula (1-26), ^R1 and ^R2 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently 1,2-cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; Ring ^N1 and Ring N2 are independently cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, or benzo[b]thiophene-2,6-diyl, and at least one hydrogen in the ring ^N1 and the ring ^N2 may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , -OCF Z ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² , Z ³ , and Z ⁴ are independently a single bond, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N, and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; In formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26), R ¹ will not be hydrogen, and in formula (1-14) to formula (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1-26), R ² will not be hydrogen.

Item 6. The compound according to any one of Items 1 to 3, which is represented by Formula (1-1-1), Formula (1-3-1) to Formula (1-3-6), Formula (1-5-1) to Formula (1-5-4), or Formula (1-9-1) to Formula (1-9-3),

[Chemistry 9]

In formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), and formula (1-9-1) to formula (1-9-3), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; ^Z2 and ^Z3 are independently a single bond, -O-, -COO-, _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , -OCF2-, -( _CH2 ) _2- , -CH=CH-, -C≡C-, -( _CH2 ) _4- , -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 7. The compound according to Item 6, wherein in Formula (1-1-1), Formula (1-3-1) to Formula (1-3-6), Formula (1-5-1) to Formula (1-5-4), Formula (1-9-1) to Formula (1-9-3), ^R1 and ^R2 are independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms; ^Ra is hydrogen, a linear alkyl group having 1 to 6 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms; ^Z2 and ^Z3 are independently a single bond, -COO-, -OCO-, _-CH2O- , _-OCH2- , _-CF2O- , _-OCF2- , -( _CH2 ) _2- , -CH=CH-, -( _CH2 ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ or -OCF ₃ , at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ or -OCF ₃ , and at least two of L ¹ , L ² , L ³ , and L ⁴ are hydrogen; X ¹ and X ² are independently hydrogen, fluorine or chlorine.

Item 8. The compound according to any one of Item 1, Item 4, and Item 5, which is represented by Formula (1-14-1), Formula (1-16-1) to Formula (1-16-6), Formula (1-18-1) to Formula (1-18-4), or Formula (1-22-1) to Formula (1-22-3),

[Chemistry 10]

In formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), and formula (1-22-1) to formula (1-22-3), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; ^Z2 and ^Z3 are independently a single bond, -O-, -COO-, -OCO-, _-CH2O- , _-OCH2- , _-CF2O- , _-OCF2- , -( _CH2 ) ₂ -, -CH=CH-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF 2 -, _{-OCF 2 (} CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 9. The compound as described in Item 8, wherein in the formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), and formula (1-22-1) to formula (1-22-3), ^R1 and ^R2 are independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to ₆ carbon atoms; ^Z2 and ^Z3 are independently a single bond, -COO-, -OCO-, _-CH2O- , -OCH2-, _-CF2O- , _-OCF2- , -( _CH2 ) _2- , -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F, and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 10. The compound according to any one of Items 1 to 3, Item 6, and Item 7, which is represented by Formula (1-1-1), or Formula (1-3-1) to Formula (1-3-6),

[Chemistry 11]

In formula (1-1-1), and formula (1-3-1) to formula (1-3-6), ^R1 and ^R2 are independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 or 4 carbon atoms; ^Z2 is a single bond, -COO-, _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , -OCF2-, -( _CH2 ) _2- , -CH=CH-, -( _{CH2 ) 4-} , -( _CH2 )3O-, -O( _{CH2 )} 3-, -CH=CH-( _CH2 ) _2- , -( _CH2 ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , or -OCF ₃ , at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , or -OCF ₃ , and at least two of L ¹ , L ² , L ³ , and L ⁴ are hydrogen; X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 11. The compound according to any one of Item 1, Item 4, Item 5, Item 8, and Item 9, which is represented by Formula (1-14-1) or Formula (1-16-1) to Formula (1-16-6),

[Chemistry 12]

In formula (1-14-1), and formula (1-16-1) to formula (1-16-6), ^R1 and ^R2 are independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to ₄ carbon atoms, or a branched-chain alkyl group having _{3 or 4 carbon atoms; Z2 is a single bond, -COO-, -OCO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, -(CH2)2-} ^, _{-CH = CH- ,} - _{( CH2} ) _4- , -( _CH2 )3O-, _-O (CH2) _3- , -CH=CH-( _CH2 ) _2- , -( _CH2 ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , or -OCF ₃ , and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , or -OCF ₃ ; X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 12. The compound according to any one of Items 1 to 3, Item 6, Item 7, and Item 10, which is represented by Formula (1-1-1), Formula (1-3-1-1) to Formula (1-3-1-7), Formula (1-3-2-1), Formula (1-3-2-2), Formula (1-3-3-1), Formula (1-3-3-2), Formula (1-3-4-1), Formula (1-3-4-2), Formula (1-3-5-1), Formula (1-3-5-2), or Formula (1-3-6-1) to Formula (1-3-6-4),

[Chemistry 13]

In the formula (1-1-1), formula (1-3-1-1) to formula (1-3-1-7), formula (1-3-2-1), formula (1-3-2-2), formula (1-3-3-1), formula (1-3-3-2), formula (1-3-4-1), formula (1-3-4-2), formula (1-3-5-1), formula (1-3-5-2), and formula (1-3-6-1) to formula (1-3-6-4), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight chain alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms; L1, L2, L3, and ^L4 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having ² to 9 carbon atoms, alkenyl having 2 to ¹⁰ carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ⁴ is independently hydrogen, fluorine, -CF ₃ or -OCF ₃ , at least two of L ¹ , L ² , L ³ and L ⁴ are fluorine, -CF ₃ or -OCF ₃ , at least one of L ¹ , L ² , L ³ and L ⁴ is hydrogen; X ¹ and X ² are independently hydrogen or fluorine.

Item 13. The compound as described in any one of Item 1, Item 4, Item 5, Item 8, Item 9, and Item 11, which is represented by Formula (1-14-1), Formula (1-16-1-1) to Formula (1-16-1-7), Formula (1-16-2-1), Formula (1-16-2-2), Formula (1-16-3-1), Formula (1-16-3-2), Formula (1-16-4-1), Formula (1-16-4-2), Formula (1-16-5-1), Formula (1-16-5-2), or Formula (1-16-6-1) to Formula (1-16-6-4),

[Chemistry 14]

In formula (1-14-1-1), formula (1-16-1-1) to formula (1-16-1-7), formula (1-16-2-1), formula (1-16-2-2), formula (1-16-3-1), formula (1-16-3-2), formula (1-16-4-1), formula (1-16-4-2), formula (1-16-5-1), formula (1-16-5-2), and formula (1-16-6-1) to formula (1-16-6-4), ^R1 and ^{R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; Ra is hydrogen, a straight chain alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms; L5 and L2} are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight chain alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms; ^L5 and L2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^L6 is independently hydrogen, fluorine, _-CF3 , or _-OCF3 ; at least one of ^L5 and ^L6 is fluorine, _-CF3 , or _-OCF3 ; ^X1 and ^X2 are independently hydrogen or fluorine.

Item 14. The compound according to any one of Items 1 to 3, Item 6, Item 7, Item 10, and Item 12, which is represented by Formula (1-1-1-1) to Formula (1-1-1-7),

[Chemistry 15]

In formula (1-1-1-1) to formula (1-1-1-7), ^R1 and ^R2 are independently an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched-chain alkyl group having 3 or 4 carbon atoms.

Item 15. The compound according to any one of Item 1, Item 4, Item 5, Item 8, Item 9, Item 11, and Item 13, which is represented by Formula (1-14-1-1) or Formula (1-14-1-2),

[Chemistry 16]

In formula (1-14-1-1) or formula (1-14-1-2), ^R1 and ^R2 are independently alkyl having 1 to 7 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkoxyalkyl having 2 to 6 carbon atoms, alkenyl having 2 to 7 carbon atoms, or alkenyloxy having 2 to 7 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl having 1 to 4 carbon atoms, or a branched-chain alkyl having 3 or 4 carbon atoms.

Item 16. A liquid crystal composition comprising at least one of the compounds described in any one of Items 1 to 15.

Item 17. The liquid crystal composition according to Item 16, comprising at least one compound selected from the group consisting of compounds represented by formula (2) to formula (4),

[Chemistry 17]

In formula (2) to formula (4), R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, at least one -CH ₂ - in R ¹¹ and R ¹² may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z ¹¹ , Z ¹² , and Z ¹³ are independently a single bond, -COO-, -(CH ₂ ) ₂ -, -CH=CH-, or -C≡C-.

Item 18. The liquid crystal composition according to Item 16 or Item 17, further comprising at least one compound selected from the group consisting of compounds represented by formula (5) to formula (13),

[Chemistry 18]

In formula (5) to formula (13), ^R13 and ^R14 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, at least one _-CH2- in said ^R13 and ^R14 may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; ^R15 is hydrogen, fluorine, alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, at least one _-CH2- in said ^R15 may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; Ring ^C1 , Ring ^C2 , Ring ^C3 , and Ring C wherein ^{Z14 , Z15} , Z16, and ^Z17 are independently a single bond, -COO-, -CH2O-, -OCF2-, -(CH2)2-, or -OCF2-(CH2)2-; ^L11 and ^L12 are independently 1,4-cyclohexylene, 1,4- ^cyclohexenyl , 1,4- _phenylene ⁱⁿ which at least ^one hydrogen atom _may be substituted by fluorine, tetrahydropyran- _2,5 - _{diyl ,} or _{decahydronaphthalene} - _2,6 -diyl; ¹² is independently fluorine or chlorine; S ¹¹ is hydrogen or methyl; X is -CHF- or -CF ₂ -; j, k, m, n, p, q, r, and s are independently 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3.

Item 19. The liquid crystal composition according to any one of Items 16 to 18, further comprising at least one compound selected from the group consisting of compounds represented by formula (21) to formula (23),

[Chemistry 19]

In formula (21) to formula (23), R ¹⁶ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one -CH ₂ - in R ¹⁶ may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; X ¹¹ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ ; Ring D ¹ , Ring D ² , and Ring D ³ are independently 1,4-cyclohexylene, 1,4-phenylene atom in which at least one hydrogen atom may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁸ , Z ¹⁹ , and Z ²⁰ are independently a single bond, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, or -(CH ₂ ) ₄ -; L ¹³ and L ¹⁴ are independently hydrogen or fluorine.

Item 20. The liquid crystal composition according to any one of Items 16 to 19, further comprising at least one compound selected from the group of compounds represented by formula (24),

[Chemistry 20]

In formula (24), R ¹⁷ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to ¹⁰ carbon atoms, in which at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring E ¹ is 1,4-cyclohexylene, 1,4-phenylene atom in which at least one hydrogen atom may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ²¹ is a single bond, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, or -C≡C-; L ¹⁵ and L ¹⁶ are independently hydrogen or fluorine; i is 1, 2, 3, or 4.

Item 21. A liquid crystal display element comprising a liquid crystal composition as described in any one of items 16 to 20.

The present invention also includes the following items: (a) The composition further contains at least one optically active compound and/or polymerizable compound. (b) The composition further contains at least one antioxidant and/or ultraviolet absorber.

The present invention also includes the following items. (c) The composition further contains one, two, or at least three additives selected from the group consisting of polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, thermal stabilizers, pigments, and defoaming agents. (d) The composition has an upper limit temperature of a nematic phase of 70°C or higher, an optical anisotropy at a wavelength of 589 nm (measured at 25°C) of 0.08 or higher, and a dielectric anisotropy at a frequency of 1 kHz (measured at 25°C) of -2 or lower.

The present invention also includes the following items. (e) A device containing the composition and having a PC, TN, STN, ECB, OCB, IPS, VA, FFS, FPA, or polymer sustained alignment (PSA) mode. (f) An AM device containing the composition. (g) A transmissive device containing the composition. (h) Use of the composition as a composition having a nematic phase. (i) Use of the composition as an optically active composition by adding an optically active compound to the composition.

The state of compound (1), the synthesis of compound (1), a liquid crystal composition, and a liquid crystal display device are described in order.

1. State of Compound (1) Compound (1) is characterized by having a divalent group represented by the following formula. In the following formula, X is hydrogen or a substituent.

[Chemistry 21]

The compound is extremely stable physically and chemically under conditions of common use of the device, and has good compatibility with other liquid crystal compounds. The composition containing the compound is stable under conditions of common use of the device. The composition has a negative and large dielectric anisotropy. The compound has the general physical properties required for the components of the composition, appropriate optical anisotropy, and appropriate dielectric anisotropy.

Preferred examples of the terminal groups ^R1 and ^R2 , the side groups ^Ra , the rings ^A1 and ^A2 , the rings ^N1 and ^N2 , the bonding groups ^Z1 , Z2, ^Z3 and ^Z4 , the side groups ^L1 , ^L2 , ^L3 , ^L4 , ^L5 and ^L6 in the compound (1) are as follows. This example is also applicable to the lower formula of the compound (1). In the compound (1 ⁾ , the physical properties can be arbitrarily adjusted by appropriately combining these groups. Since there is no great difference in the physical properties of the compounds, compound (1) may contain isotopes such as ² H (deuterium) and ¹³ C in greater amounts than the natural abundance. The symbols of compound (1) are defined as described in item 1.

[Chemistry 22]

In formula (1), ^R1 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In said ^R1 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine. ^R2 is hydrogen, fluorine, chlorine, -C≡N, -C≡CC≡N, or an alkyl group having 1 to 15 carbon atoms. In said ^R2 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine.

In formula (1), when l is 0, ^R1 will not become hydrogen, and when o is 0, ^R2 will not become hydrogen.

Preferred R ¹ or R ² is alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, alkylthioalkoxy, acyl, acylalkyl, acyloxy, acyloxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkenyl, alkenyloxy, alkenyloxyalkyl, alkoxyalkenyl, alkynyl, and alkynyloxy. In said R 1 or R ^{2, at least one hydrogen can be substituted by fluorine or chlorine. In this example, at least two hydrogens are substituted by both fluorine and chlorine. Further, at least one hydrogen is substituted by only fluorine. In said R 1 or R 2 , a straight chain is preferred over a branched chain. Even if R 1 or R 2 is} a branched chain, it is preferred to be optically active. More preferably, R ¹ or R ² is an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, a monofluoroalkyl group, a polyfluoroalkyl group, a monofluoroalkoxy group, or a polyfluoroalkoxy group. In addition to the above groups, R ² may also be fluorine, chlorine, -C≡N, or -C≡CC≡N.

The preferred stereo configuration of -CH=CH- in the alkenyl group depends on the position of the double bond. In alkenyl groups such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, and 3-hexenyl, the trans configuration is preferred. In alkenyl groups such as 2-butenyl, 2-pentenyl, and 2-hexenyl, the cis configuration is preferred.

Specific examples of ^R1 or ^R2 are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl, butoxymethyl, butoxyethyl, pentyloxymethyl, pentyloxyethyl, vinyl, 1-propenyl, 2-propenyl, 4-hexenyl, 5-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, 2-hexenyloxy, and 1-propynyl.

Specific examples of R ¹ or R ² are 2-fluoroethyl, 3-fluoropropyl, 2,2,2-trifluoroethyl, 2-fluorovinyl, 2,2-difluorovinyl, 2-fluoro-2-vinyl, 3-fluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 4-fluoro-1-propenyl, and 4,4-difluoro-3-butenyl.

Specific examples of R ² include fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -CF 2 CF ₃ , -CF ₂ CHF ₂ , -CF ₂ CH ₂ F, -CF ₂ CF ₂ CF ₃ , _{-CF 2 CHFCF 3} , -CHFCF ₂ CF ₃ , -OCF ₃ , -OCHF ₂ , -OCH ₂ F, -OCF ₂ CF ₃ , -OCF ₂ CHF ₂ , -OCF ₂ CH ₂ F, -OCF ₂ CF ₂ CF ₃ , -OCF ₂ CHFCF ₃ , and -OCHFCF ₂ CF ₃ .

Further preferred R ¹ or R ² is ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxymethyl, ethoxymethyl, ethoxyethyl, propoxymethyl, propoxyethyl, butoxymethyl, pentyloxymethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 2-propenyloxy, 2-butenyloxy, and 2-pentenyloxy. Further preferred ^R2 is _-OCF3 , _-OCHF2 , _-OCH2F , -OCF2CF3 _{, -OCF2CHF2, -OCF2CH2F, -OCF2CF2CF3, -OCF2CHFCF3, -OCHFCF2CF3, fluorine, chlorine, and -C≡N. The most preferred R1 or R2 is ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy , propoxy , butoxy , pentyloxy , methoxymethyl} ^{, ethoxymethyl} _{, propoxymethyl ,} butoxymethyl, _vinyl , 1-propenyl, 3-butenyl, and 3-pentenyl. Furthermore, the most preferable R ² is -OCF ₃ , -OCHF ₂ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₂ CHF ₂ , -OCF ₂ CHFCF ₃ , fluorine, and -C≡N.

^Ra is hydrogen, a linear alkyl group having 1 to 6 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms.

Preferred ^Ra is methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, sec-butyl, pentane-2-yl, hexane-2-yl, pentane-3-yl, hexane-3-yl, t-butyl, t-pentyl, 3-methylpentane-3-yl, and 3-ethylpentane-3-yl. Further preferred ^Ra is methyl, ethyl, propyl, butyl, isopropyl, sec-butyl, and t-butyl. Particularly preferred ^Ra is methyl, ethyl, propyl, and isopropyl. The best ^Ra is methyl and ethyl.

In formula (1), Ring ^A1 and Ring ^A2 are independently cycloalkylene groups having 3 to 5 carbon atoms. In Ring ^A1 and Ring ^A2 , at least one _-CH2- may be substituted by -O-, and at least one -( _CH2 ) _2- may be substituted by -CH=CH-.

Preferred examples of Ring ^A1 or Ring ^A2 are divalent groups represented by the following formulas (25-1) to (25-27). Further preferred examples are divalent groups represented by formulas (25-1) to (25-17). Particularly preferred examples are divalent groups represented by formulas (25-1) to (25-3) and (25-13) to (25-17). The best examples are divalent groups represented by formulas (25-1) to (25-3).

[Chemistry 23]

In formula (1), ring ^N1 and ring ^N2 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl; at least one hydrogen in ring ^N1 and ring ^N2 may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F .

Preferred examples of "at least one hydrogen in ring ^N1 and ring ^N2 may be substituted by fluorine, _chlorine , -C≡N, -CF3, _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F " are divalent groups represented by the following formulas (26-1) to (26-71). Further preferred examples are divalent groups represented by formulas (26-1) to (26-4), (26-6), (26-10) to (26-15), and (26-54) to (26-59).

[Chemistry 24]

[Chemistry 25]

[Chemistry 26]

More preferably, Ring ^N1 or Ring ^N2 is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2,3,5-trifluoro-1,4-phenylene, pyridine-2,5-diyl, 3-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl, oxazine-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and naphthalene-2,6-diyl. The stereo configuration of 1,4-cyclohexylene and 1,3-dioxane-2,5-diyl is that the trans form is more favorable than the cis form.

Particularly preferred ring ^N1 or ring ^N2 is 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyridine-2,5-diyl, and pyrimidine-2,5-diyl. The most preferred ring ^N1 or ring ^N2 is 1,4-cyclohexylene and 1,4-phenylene, 2-fluoro-1,4-phenylene, and 2,3-difluoro-1,4-phenylene.

In formula (1), Z ¹ , Z ² , Z ³ , and Z ⁴ are independently a single bond or an alkylene group having 1 to 6 carbon atoms. Among Z ¹ , Z ² , Z ³ , and Z ⁴ , at least one -CH ₂ - may be substituted by -O-, -S-, -CO-, or -SiH ₂ -, at least one -(CH ₂ ) ₂ - may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine.

Specific examples of Z ¹ , Z ² , Z ³ , or Z ⁴ are a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, -CH ₂ CO-, -COCH ₂ -, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, and -OCH ₂ -CH=CH-. The stereo configuration related to the double bond of the bonding groups such as -CH=CH-, -CF=CF-, -CH=CH-CH ₂ O-, and -OCH ₂ -CH=CH- is that the trans form is preferred to the cis form.

Preferred Z ¹ , Z ² , Z ³ , or Z ⁴ is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, and -OCH ₂ -CH=CH-. More preferably, Z ¹ , Z ² or Z ³ is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -(CH ₂ ) ₂ -, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, and -(CH ₂ ) ₂ -CH=CH-. Most preferably, Z ¹ , Z ² , Z ³ or Z ⁴ is a single bond, -CH ₂ O- or -OCH ₂ -.

In formula (1), L ¹ , L ² , L ³ , L ⁴ , L ⁵ , and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N.

In formula (1), when ^L5 and ^L6 are both hydrogen, at least one of ^L1 , ^L2 , ^L3 , and ^L4 is fluorine, chlorine, _{-CF3, -CHF2 , -CH2F} , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N, and at least one of ^L1 , ^L2 , ^L3 , and ^L4 may be hydrogen. More preferably, ^L1 , ^L2 , ^L3 , and ^L4 are fluorine or _-CF3 . Particularly preferably ^{, L1} , ^L2 , ^L3 , and ^L4 are fluorine.

In formula (1), when L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N, and at least one of L ⁵ and L ⁶ may be hydrogen. More preferably, L ⁵ and L ⁶ are fluorine or -CF ₃ . Particularly preferably, L ⁵ and L ⁶ are fluorine.

In formula (1), l and o are independently 0 or 1, m and n are independently 0, 1 or 2, and the sum of l, m, n, and o is an integer from 0 to 4. Compound (1) has one to five rings. These rings include condensed rings or cross-linked six-membered rings in addition to the usual six-membered rings. When compound (1) has one or two rings, it has good compatibility with other liquid crystal compounds and low viscosity. When compound (1) has three or four rings, the upper limit temperature is high. When compound (1) has four rings, the temperature range of the liquid crystal phase is wide.

By appropriately selecting the terminal groups, rings and bonding groups of the compound (1), physical properties such as optical anisotropy and dielectric anisotropy can be arbitrarily adjusted. The effects of the types of the terminal groups ^R1 and ^R2 , the rings ^A1 and ^A2 , the bonding groups ^Z1 , ^Z2 , ^Z3 and ^Z4 on the physical properties of the compound (1) are described below.

In compound (1), when R ¹ or R ² is a linear chain, the temperature range of the liquid crystal phase is wide and the viscosity is low. When R ¹ or R ² is a branched chain, the compatibility with other liquid crystal compounds is good. The compound in which R ¹ or R ² is an optically active group is useful as a chiral dopant. By adding the compound to the composition, the reverse twisted domain generated in the element can be prevented. The compound in which R ¹ or R ² is not an optically active group is useful as a component of the composition. When R ¹ or R ² is an alkenyl group, the preferred stereo configuration depends on the position of the double bond. The alkenyl compound having a preferred stereo configuration has a high upper limit temperature or a wide temperature range of the liquid crystal phase. A detailed description is given in "Mol. Cryst. Liq. Cryst." (1985, 131, 109) and "Mol. Cryst. Liq. Cryst." (1985, 131, 327).

When ring ^A1 or ring ^A2 is 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or oxazine-3,6-diyl, in which at least one hydrogen atom may be substituted by fluorine or chlorine, the optical anisotropy is large. When the ring is 1,4-cyclohexylene, 1,4-cyclohexenyl, or 1,3-dioxane-2,5-diyl, the optical anisotropy is small.

When at least two rings are 1,4-cyclohexylene, the upper limit temperature is high, the optical anisotropy is small, and the viscosity is low. When at least one ring is 1,4-phenylene, the optical anisotropy is relatively large, and the orientational order parameter is large. When at least two rings are 1,4-phenylene, the optical anisotropy is large, the temperature range of the liquid crystal phase is wide, and the upper limit temperature is high.

When the bonding group Z ¹ , the bonding group Z ² , the bonding group Z ³ , or the bonding group Z ⁴ is a single bond, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CF-, or -(CH ₂ ) ₄ -, the viscosity is small. When the bonding group is a single bond, -OCF ₂ -, -CF ₂ O-, -(CH ₂ ) ₂ -, or -CH=CH-, the viscosity is even lower. When the bonding group is -CH=CH-, the temperature range of the liquid crystal phase is wide, and the elastic constant ratio K ₃₃ /K ₁₁ (K ₃₃ : bending elastic constant, K ₁₁ : splay elastic constant) is larger. When the bonding group is -C≡C-, the optical anisotropy is large.

When the compound (1) has one or two rings, the viscosity is low. When the compound (1) has four or five rings, the upper limit temperature is high. As described above, by appropriately selecting the types of terminal groups, rings, and bonding groups, and the number of rings, a compound having desired physical properties can be obtained. Therefore, the compound (1) is useful as a component of a composition used in a device having a mode such as PC, TN, STN, ECB, OCB, IPS, or VA.

In formula (1), when ^L5 and ^L6 are both hydrogen, and ^L1 , ^L2 , ^L3 , or ^L4 is fluorine, chlorine, _-CF3 , or -CHF2, the compound is preferred. _When L5 and L6 are both hydrogen, and L1, ^L2 , L3, or L4 is fluorine or chlorine, the compound is further preferred. When ^L5 and ^L6 are both hydrogen, and ^L1 , L2, ^L3 , or ^L4 is fluorine, the compound is most preferred. When ^L5 and ^L6 are both hydrogen, and ^L1 , ^L2 , ^L3 , or ^L4 is fluorine, the compound is most preferred.

In formula (1), when ^L1 , ^L2 , ^L3 , and ^L4 are all hydrogen, and ^L5 or ^L6 is fluorine, chlorine, _-CF3 , or -CHF2, the compound is preferred. When L1, ^L2 , ^L3 , and ^L4 are _all hydrogen, and L5 or L6 is fluorine or chlorine, the compound is further preferred. When ^L1 , L2, L3, and L4 are all hydrogen, and ^L5 or ^L6 is fluorine, the compound is most preferred. When ^L1 , ^L2 , ^L3 , and ^L4 are all hydrogen, and ^L5 or ^L6 is fluorine, the compound is most preferred.

Preferred examples of the compound (1) are the compounds (1-1) to (1-26) described in items 2 and 4. Further preferred examples are the compounds represented by the following formulae in items 6 and 8. The compound (1) is suitable for devices having VA, IPS, PSA, and other modes.

2. Synthesis of compound (1) The synthesis method of compound (1) is described. Compound (1) can be synthesized by appropriately combining methods of organic synthetic chemistry. Methods for introducing desired terminal groups, rings, and bonding groups into starting materials are described in books such as "Organic Syntheses" (John Wiley & Sons, Inc.), "Organic Reactions" (John Wiley & Sons, Inc.), "Comprehensive Organic Synthesis" (Pergamon Press), and "New Experimental Chemistry Lectures" (Maruzen).

2-1. Formation of bonding group Z The first process is shown for the method of forming bonding groups ^Z1 to ^Z4 . Next, the reactions described in the processes (1) to (11) are described. In the processes, ^MSG1 (or ^MSG2 ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by the multiple ^MSG1 (or ^MSG2 ) used in the processes may be the same or different. Compounds (1A) to (1J) are equivalent to compound (1).

[Chemistry 27]

[Chemistry 28]

(1) Formation of a single bond In the presence of carbonate and a catalyst such as tetrakis(triphenylphosphine)palladium, an arylboronic acid (31) synthesized by a known method is reacted with a halide (32) to synthesize compound (1A). Compound (1A) can also be synthesized by reacting n-butyl lithium with a halide (33) synthesized by a known method, then reacting zinc chloride, and reacting the halide (32) in the presence of a catalyst such as dichlorobis(triphenylphosphine)palladium.

(2) Formation of -COO- N-butyl lithium is reacted with a halide (33), and then carbon dioxide is reacted to obtain a carboxylic acid (34). Compound (1B) is synthesized by dehydrating a compound (35) synthesized by a known method and a carboxylic acid (34) in the presence of 1,3-dicyclohexyl carbodiimide (DDC) and 4-dimethyl amino pyridine (DMAP).

(3) Formation of -CF ₂ O- Compound (1B) is treated with a sulfiding agent such as Lawesson's reagent to obtain a thionoester (36). Compound (1C) is synthesized by fluorinating the thionoester (36) with hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS). See M. Kuroboshi et al., "Chem. Lett." (1992, 827). Compound (1C) can also be synthesized by fluorinating the thionoester (36) with (diethyl amino)sulfur trifluoride (DAST). See WH Bunnelle et al., "Journal of Organic Chemistry (J. Org. Chem.)" (1990, 55, 768.). The bonding group can also be generated by the method described in Peer. Kirsch et al., "Angew. Chem. Int. Ed. (2001, 40, 1480.)".

(4) Formation of -CH=CH- The halide (32) is treated with n-butyl lithium and then reacted with N,N-dimethyl formamide (DMF) to obtain aldehyde (38). Phosphonium salt (37) synthesized by a known method is treated with a base such as potassium tert-butoxide to produce phosphorus ylide. The phosphorus ylide is reacted with aldehyde (38) to synthesize compound (1D). Since a cis isomer is generated by the reaction conditions, the cis isomer can be isomerized to a trans isomer by a known method as needed.

(5) Formation of -(CH ₂ ) ₂ - Compound (1E) is synthesized by hydrogenating compound (1D) in the presence of a palladium-carbon catalyst.

(6) Formation of -(CH ₂ ) ₄ - Phosphonium salt (39) is used instead of phosphonium salt (37) to obtain a compound having -(CH ₂ ) ₂ -CH=CH- according to the method of method (4). This compound is subjected to catalytic hydrogenation to synthesize compound (1F).

(7) Formation of -CH ₂ CH=CHCH ₂ - Phosphonium salt (40) is used instead of phosphonium salt (37), and aldehyde (41) is used instead of aldehyde (38) to synthesize compound (1G) according to the method of method (4). A trans isomer is generated depending on the reaction conditions, and the trans isomer can be isomerized to a cis isomer by a known method as needed.

(8) Formation of -C≡C- The halide (33) is reacted with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper halide, and then deprotected under alkaline conditions to obtain compound (32). Compound (1H) is synthesized by reacting compound (42) with the halide (32) in the presence of a catalyst of dichloropalladium and copper halide.

(9) Formation of -CF=CF- The halide (33) is treated with n-butyl lithium and then reacted with tetrafluoroethylene to obtain compound (43). The halide (32) is treated with n-butyl lithium and then reacted with compound (43) to synthesize compound (1I).

(10) Formation of -OCH ₂ - Aldehyde (38) is reduced using a reducing agent such as sodium borohydride to obtain compound (44). Compound (44) is brominated using hydrobromic acid to obtain bromide (45). In the presence of a base such as potassium carbonate, bromide (45) is reacted with compound (46) to synthesize compound (1J).

(11) The formation of -(CF ₂ ) ₂ - is carried out according to the method described in "Journal of the American Chemical Society (J. Am. Chem. Soc.)" (2001, 123, 5414). In the presence of a hydrogen fluoride catalyst, a diketone (-COCO-) is fluorinated with sulfur tetrafluoride to obtain a compound having -(CF ₂ ) ₂ -.

2-2. Production of Ring ^A1 to Ring ^A3 and Ring ^N1 Next, the production methods of Ring ^A1 to Ring ^A3 and Ring ^N1 are described. For rings such as 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, pyridine-2,5-diyl, and pyrimidine-2,5-diyl, starting materials are commercially available or production methods are well known. Therefore, Compound (64), Compound (67), and Compound (71) shown below are described.

[Chemistry 29]

Decahydronaphthalene-2,6-dione (64) is a starting material of a compound having a decahydronaphthalene-2,6-diyl group. The compound (64) can be obtained by catalytically hydroreducing the diol (63) in the presence of ruthenium oxide according to the method described in Japanese Patent Publication No. 2000-239564, and then oxidizing it with chromium oxide. The compound is converted into the compound (1) by a conventional method.

[Chemistry 30]

The structural unit of 2,3-(bistrifluoromethyl)phenylene was synthesized by the method described in "Org. Lett." (2000, 2 (21), 3345). Aniline (66) was synthesized by subjecting furan (65) to a Diels-Alder type reaction with 1,1,1,4,4,4-hexafluoro-2-butyne at high temperature. The compound was subjected to a Sandmeyer type reaction according to the method described in "Org. Synth. Coll." (Vol. 2, 1943, 355) to obtain the iodide (67). The compound was converted to compound (1) by a conventional method.

[Chemistry 31]

The structural unit of 2-difluoromethyl-3-fluorophenylene is synthesized by the following method. The hydroxyl group of compound (68) is protected by an appropriate protecting group to obtain compound (69). P represents a protecting group. Compound (69) is reacted with tert-butyl lithium and then with N,N-dimethylformamide (DMF) to obtain aldehyde (70). The compound can also be fluorinated with diethylaminosulfur trifluoride (DAST) and then deprotected to obtain phenol (71). The compound is converted into compound (1) by a conventional method.

2-3. Formation of 3,6-dihydro-2H-pyran ring The method for forming the ring is described using compounds (1a) and (1b) having a divalent group represented by formula (pr-1). A compound having a divalent group represented by formula (pr-2) can also be synthesized by this method. The synthesis process of compound (1a) is as follows.

[Chemistry 32]

Compound (s-1) is synthesized according to the method described in Japanese Patent Publication No. 2011-136924. Compound (s-1) is reduced with a reducing agent such as sodium borohydride to obtain compound (s-2). This compound is halogenated with triphenylphosphine and carbon tetrahalide, and treated with a dehalogenating agent such as diazabicyclo undecene (DBU) to obtain the target compound (1a).

[Chemistry 33]

The synthesis process of compound (1b) is as described above. Compound (s-3) is reacted with aldehyde (17) in the presence of a Lewis acid such as boron trifluoride diethyl ether complex, followed by hydrogenation to obtain compound (s-4). The compound is reduced with a reducing agent such as aluminum lithium hydride to obtain compound (s-5). The compound is halogenated with triphenylphosphine and carbon tetrahalide, and treated with a dehalogenating agent such as diazabicycloundecene (DBU) to obtain compound (1b).

2-4. Formation of carbazole ring The synthesis process of compounds (1c) to (1f) is as follows.

[Chemistry 34]

Compound (s-6), compound (s-7), Pd(amphos)Cl2, and tert-butoxysodium are reacted to obtain compound (s-8). P refers to a protecting group. The compound is deprotected to obtain compound (s-9). The compound is reacted with palladium acetate in acetic acid to obtain (1c). The compound is alkylated to obtain compound (1d). In these compounds, L ¹ , L ² , L ³ and L ⁴ have the same definitions as those described in item 1. ^{RA 1} or RA ² has the same definition as MSG ¹ and R ¹ or R ² described in item 1.

[Chemistry 35]

Compound (s-10), compound (s-11), Pd(amphos)Cl2, and tert-butoxysodium are reacted to obtain compound (s-12). P refers to a protecting group. The compound is deprotected to obtain compound (s-13). The compound is reacted with palladium acetate in acetic acid to obtain (1e). The compound is alkylated to obtain compound (1f). In these compounds, L ⁵ and L ⁶ have the same definitions as those described in item 1. RA ¹ or RA ² has the same definition as MSG ¹ and R ¹ or R ² described in item 1.

3. Liquid crystal composition 3-1. Component compounds The liquid crystal composition of the present invention is described. The composition contains at least one compound (1) as component (a). The composition may also contain two or more compounds (1). The composition may contain only compound (1). In order to exhibit good physical properties, it is preferred that the composition contains at least one compound (1) in a range of 1 wt% to 99 wt%. In a composition having a negative dielectric anisotropy, the preferred content of compound (1) is in a range of 5 wt% to 60 wt%. In a composition having a positive dielectric anisotropy, the preferred content of compound (1) is 30 wt% or less.

[Table 1] Table 1. Component compounds of the composition Element Ingredients Dielectric anisotropy Ingredient (a) Compound (1) Negative and large Ingredient (b) Compound (2) to Compound (4) Small Ingredient (c) Compound (5) to Compound (13) Negative and large Ingredient (d) Compound (21) to Compound (23) Positive and big Ingredient (e) Compound (24) Positive and big

The composition contains compound (1) as component (a). The composition preferably further contains a liquid crystal compound selected from components (b) to (e) shown in Table 1. When preparing the composition, it is preferred to select components (b) to (e) in consideration of the positive and negative sign and size of dielectric anisotropy. The composition may contain a liquid crystal compound different from compounds (1) to (13) and compounds (21) to (24). The composition may also contain no such liquid crystal compound.

Component (b) is a compound having two terminal groups being alkyl groups or the like. Preferred examples of component (b) include compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). In these compounds, R ¹¹ and R ¹² are independently alkyl groups having 1 to 10 carbon atoms or alkenyl groups having 2 to 10 carbon atoms, and in R ¹¹ and R ¹² , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by fluorine.

[Chemistry 36]

Component (b) has a small dielectric anisotropy. Component (b) is close to neutral. Compound (2) has the effect of reducing viscosity or adjusting optical anisotropy. Compound (3) and Compound (4) have the effect of expanding the temperature range of the nematic phase by increasing the upper limit temperature or adjusting optical anisotropy.

As the content of component (b) increases, the viscosity of the composition decreases, but the dielectric anisotropy decreases. Therefore, as long as the required value of the critical voltage of the device is met, it is better to have a higher content. In the case of preparing a composition for IPS, VA, etc. mode, the content of component (b) is preferably 30% by weight or more, and more preferably 40% by weight or more based on the weight of the liquid crystal composition.

Component (c) is compound (5) to compound (13). These compounds have a phenylene group substituted with two halogens at the side, like 2,3-difluoro-1,4-phenylene. Preferred examples of component (c) include compounds (5-1) to compound (5-9), compounds (6-1) to compound (6-19), compounds (7-1) and compound (7-2), compounds (8-1) to compound (8-3), compounds (9-1) to compound (9-3), compounds (10-1) to compound (10-11), compounds (11-1) to compound (11-3), compounds (12-1) to compound (12-3), and compound (13-1). In these compounds, R ¹³ and R ¹⁴ are independently alkyl groups having 1 to 10 carbon atoms or alkenyl groups having 2 to 10 carbon atoms, at least one -CH ₂ - in R ¹³ and R ¹⁴ may be replaced by -O-, and at least one hydrogen group may be replaced by fluorine, and R ¹⁵ is hydrogen, fluorine, alkyl groups having 1 to 10 carbon atoms or alkenyl groups having 2 to 10 carbon atoms, at least one -CH ₂ - in R ¹⁵ may be replaced by -O-, and at least one hydrogen group in R ¹⁵ may be replaced by fluorine.

[Chemistry 37]

[Chemistry 38]

The dielectric anisotropy of component (c) is negative and large. Component (c) can be used to prepare compositions for modes such as IPS, VA, and PSA. As the content of component (c) increases, the dielectric anisotropy of the composition becomes more negative, but the viscosity increases. Therefore, as long as the required value of the critical voltage of the element is met, it is better to have a small content. Considering that the dielectric anisotropy is about -5, in order to perform sufficient voltage drive, it is better to have a content of 40% by weight or more.

Compound (5) in component (c) is a bicyclic compound and thus has the effect of reducing viscosity, adjusting optical anisotropy, or increasing dielectric anisotropy. Compound (6) and compound (7) are tricyclic compounds and compound (8) is a tetracyclic compound and thus has the effect of increasing the maximum temperature, increasing optical anisotropy, or increasing dielectric anisotropy. Compounds (9) to (13) have the effect of increasing dielectric anisotropy.

In the case of preparing a composition for IPS, VA, PSA and other modes, the content of component (c) is preferably 40% by weight or more, and more preferably in the range of 50% by weight to 95% by weight, based on the weight of the liquid crystal composition. In the case of adding component (c) to a composition having positive dielectric anisotropy, the content of component (c) is preferably 30% by weight or less. By adding component (c), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

Component (d) is a compound having a halogen or fluorine-containing group at the right end. Preferred examples of component (d) include compounds (21-1) to (21-16), compounds (22-1) to (22-116), and compounds (23-1) to (23-59). In these compounds, R ¹⁶ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁶ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by fluorine. ^{X 11} is fluorine, chlorine, -OCF ₃ , -OCHF ₂ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ .

[Chemistry 39]

[Chemistry 40]

[Chemistry 41]

[Chemistry 42]

[Chemistry 43]

[Chemistry 44]

[Chemistry 45]

Since component (d) has positive dielectric anisotropy and is very stable to heat or light, it can be used to prepare compositions for modes such as IPS, FFS, and OCB. Based on the weight of the liquid crystal composition, the content of component (d) is preferably in the range of 1 wt % to 99 wt %, preferably in the range of 10 wt % to 97 wt %, and further preferably in the range of 40 wt % to 95 wt %. When component (d) is added to a composition having negative dielectric anisotropy, the content of component (d) is preferably less than 30 wt %. By adding component (d), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

Component (e) is a compound (24) wherein the right terminal group is -C≡N or -C≡CC≡N. Preferred examples of component (e) include compounds (24-1) to (24-64). In these compounds, R ¹⁷ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in R ¹⁷ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by fluorine. X ¹² is -C≡N or -C≡CC≡N.

[Chemistry 46]

[Chemistry 47]

Since the dielectric anisotropy of component (e) is positive and large, it can be used to prepare a composition for a TN mode or the like. By adding the component (e), the dielectric anisotropy of the composition can be increased. Component (e) has the effect of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component (e) is also useful for adjusting the voltage-transmittance curve of the device.

In the case of preparing a composition for a TN mode, the content of component (e) is preferably in the range of 1 wt % to 99 wt %, preferably in the range of 10 wt % to 97 wt %, and further preferably in the range of 40 wt % to 95 wt % based on the weight of the liquid crystal composition. In the case of adding component (e) to a composition having a negative dielectric anisotropy, the content of component (e) is preferably 30 wt % or less. By adding component (e), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

By combining a compound appropriately selected from the above components (b) to (e) with the compound (1), a liquid crystal composition can be prepared that satisfies at least one of the following physical properties: high stability to heat or light, high upper temperature limit, low lower temperature limit, low viscosity, appropriate optical anisotropy (i.e., large optical anisotropy or small optical anisotropy), positive or negative and large dielectric anisotropy, large specific resistance, appropriate elastic constant (i.e., large elastic constant or small elastic constant). A device including such a composition has a wide temperature range in which the device can be used, a short response time, a large voltage holding ratio, a low critical voltage, a large contrast ratio, a small flicker rate, and a long life.

If the device is used for a long time, flicker may occur on the display screen. The flicker rate (%) can be expressed by (|brightness when a positive voltage is applied - brightness when a negative voltage is applied|/average brightness) × 100. Even if the device is used for a long time, a device with a flicker rate in the range of 0% to 1% is unlikely to produce flicker on the display screen. It is inferred that the flicker is related to image afterimages and is produced by the potential difference between positive frames and negative frames when driven by alternating current. A composition containing compound (1) is also useful for reducing the occurrence of flicker.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, the component compounds are mixed and dissolved in each other by heating. Additives may also be added to the composition according to the application. Examples of additives are polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, defoaming agents, etc. Such additives are well known to those skilled in the art and are described in the literature.

In a liquid crystal display element having a PSA (polymer sustained alignment) mode, the composition contains a polymer. A polymerizable compound is added for the purpose of generating a polymer in the composition. UV rays are irradiated while a voltage is applied between electrodes to polymerize the polymerizable compound, thereby generating a polymer in the composition. This method can achieve an appropriate pre-tilt, thereby producing an element with a shortened response time and improved image afterimages.

Preferred examples of polymerizable compounds are acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (cyclohexyl propane, cyclohexyl butane), and vinyl ketones. Further preferred examples are compounds having at least one acryloxy group and compounds having at least one methacryloxy group. Further preferred examples also include compounds having both acryloxy and methacryloxy groups.

Further preferred examples are compounds (M-1) to (M-18). In these compounds, R ²⁵ to R ³¹ are independently hydrogen or methyl; R ³² , R ³³ , and R ³⁴ are independently hydrogen or an alkyl group having 1 to 5 carbon atoms, and at least one of R ³² , R ³³ , and R ³⁴ is an alkyl group having 1 to 5 carbon atoms; v, w, and x are independently 0 or 1; u and y are independently integers of 1 to 10. ^{L 21} to L ²⁶ are independently hydrogen or fluorine; L ²⁷ and L ²⁸ are independently hydrogen, fluorine, or methyl.

[Chemistry 48]

The polymerizable compound can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction conditions, the amount of residual polymerizable compound can be reduced. Examples of photoradical polymerization initiators are TPO, 1173, and 4265 in the Darocur series of BASF, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850, and 2959 in the Irgacure series.

Examples of additional photoradical polymerization initiators include: 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxyphenylvinyl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzophenazine, a benzophenone/michler's ketone mixture, a hexaarylbiimidazole/benzimidazole mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, benzyldimethyl ketal, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropane-1-one, a 2,4-diethyloxanthrone/methyl para-dimethylaminobenzoate mixture, and a benzophenone/methyltriethanolamine mixture.

After adding a photo-radical polymerization initiator to the liquid crystal composition, ultraviolet light is irradiated under an applied electric field to perform polymerization. However, unreacted polymerization initiator or decomposition products of the polymerization initiator may cause poor display such as image residue in the element. In order to prevent this, photopolymerization can also be performed without adding a polymerization initiator. The preferred wavelength of the irradiated light is in the range of 150 nm to 500 nm. A further preferred wavelength is in the range of 250 nm to 450 nm, and the most preferred wavelength is in the range of 300 nm to 400 nm.

When storing the polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of the polymerization inhibitor are hydroquinone, hydroquinone derivatives such as methyl hydroquinone, 4-tert-butyl o-catechol, 4-methoxyphenol, phenothiazine, etc.

The optically active compound has the following effect: by inducing a helical structure in the liquid crystal molecules to impart a desired twist angle and prevent reverse twisting. The helical pitch can be adjusted by adding the optically active compound. For the purpose of adjusting the temperature dependence of the helical pitch, two or more optically active compounds can be added. As preferred examples of the optically active compound, the following compounds (Op-1) to (Op-18) can be listed. In compound (Op-18), ring J is 1,4-cyclohexyl or 1,4-phenylene, and R ²⁸ is an alkyl group having 1 to 10 carbon atoms. The * symbol represents an asymmetric carbon.

[Chemistry 49]

Antioxidants are effective for maintaining a high voltage holding ratio. Preferred examples of antioxidants include the following compounds (AO-1) and (AO-2); Irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114, and Irganox 1098 (trade names; BASF). Ultraviolet light absorbers are effective for preventing a decrease in the upper limit temperature. Preferred examples of ultraviolet absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives, and the like. Specific examples include: the following compound (AO-3) and compound (AO-4); Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin 328, and Tinuvin 99-2 (trade names; BASF); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

Amine-like light stabilizers having stereo hindrance are preferred for maintaining a large voltage holding ratio. Preferred examples of light stabilizers include the following compounds (AO-5), (AO-6), (AO-7), (AO-8), and (AO-9); Tinuvin 144, (Tinuvin 765), (Tinuvin 770DF), and (Tinuvin 780 (trade names; BASF); and LA-52, (LA-57), (LA-77Y), and (LA-77G) (trade names; ADEKA). Thermal stabilizers are also effective for maintaining a large voltage holding ratio. A preferred example is Irgafos 168 (trade name; BASF). In order to be suitable for guest host (GH) mode components, dichroic dyes such as azo dyes and anthraquinone dyes are added to the composition. Defoamers are effective for preventing foaming. Preferred examples of defoamers are dimethyl silicone oil, methylphenyl silicone oil, etc.

[Chemistry 50]

In compound (AO-1), R ⁴⁰ is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, -COOR ⁴¹ , or -(CH ₂ ) ₂ -COOR ⁴¹ , wherein R ⁴¹ is an alkyl group having 1 to 20 carbon atoms. In compounds (AO-2) and (AO-5), R ⁴² is an alkyl group having 1 to 20 carbon atoms. In compound (AO-5), R ⁴³ is hydrogen, methyl or O ^• (oxygen free radical); ring G ¹ is 1,4-cyclohexyl or 1,4-phenyl; in compound (AO-7) and compound (AO-8), ring G ² is 1,4-cyclohexyl, 1,4-phenyl, or 1,4-phenyl in which at least one hydrogen is substituted by fluorine; in compound (AO-5), compound (AO-7), and compound (AO-8), z is 1, 2, or 3.

4. Liquid crystal display elements The liquid crystal composition can be used for liquid crystal display elements with operating modes such as PC, TN, STN, OCB, PSA, etc., and driven by active matrix. The composition can also be used for liquid crystal display elements with operating modes such as PC, TN, STN, OCB, VA, IPS, etc., and driven by passive matrix. These elements can be applied to any type of reflective, transmissive, and semi-transmissive.

The composition is also suitable for nematic curvilinear aligned phase (NCAP) elements, where the composition is microencapsulated. The composition can also be used in polymer dispersed liquid crystal display elements (PDLCD) or polymer network liquid crystal display elements (PNLCD). A large amount of polymerizable compounds are added to these compositions. On the other hand, when the proportion of the polymerizable compound is less than 10% by weight based on the weight of the liquid crystal composition, a PSA mode liquid crystal display element is prepared. The preferred ratio is in the range of 0.1% by weight to 2% by weight. A further preferred ratio is in the range of 0.2% by weight to 1.0% by weight. PSA mode elements can be driven by active matrix mode and passive matrix mode driving methods. This type of element can also be applied to any type of reflective, transmissive, or semi-transmissive type. [Example]

1. Examples of Compound (1) The present invention is described in more detail by using examples. The examples are typical examples, and the present invention is not limited to the examples. Compound (1) is synthesized by the following sequence. The synthesized compound is identified by methods such as nuclear magnetic resonance (NMR) analysis. The physical properties of the compound or composition, and the characteristics of the device are measured by the following methods.

NMR analysis: DRX-500 manufactured by Bruker BioSpin was used for the measurement. In the ¹ H-NMR measurement, the sample was dissolved in a deuterated solvent such as CDCl ₃ , and the measurement was performed at room temperature, 500 MHz, and 16 cumulative times. Tetramethylsilane was used as an internal standard. In the ¹⁹ F-NMR measurement, CFCl ₃ was used as an internal standard, and the measurement was performed at 24 cumulative times. In the description of nuclear magnetic resonance spectra, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sext means sextet, m means multiplet, and br means broad.

Gas chromatography analysis: A GC-2010 gas chromatograph manufactured by Shimadzu Corporation was used for the measurement. A capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. was used as the column. Helium (1 mL/min) was used as the carrier gas. The temperature of the sample vaporization chamber was set to 300°C, and the temperature of the detector (Flame Ionization Detector (FID)) was set to 300°C. The sample was dissolved in acetone to prepare a 1 wt% solution, and 1 μL of the obtained solution was injected into the sample vaporization chamber. The recorder used was a gas chromatography solution system (GC Solution system) manufactured by Shimadzu Corporation.

Gas chromatography mass analysis: A QP-2010Ultra gas chromatography mass analyzer manufactured by Shimadzu Corporation was used for the measurement. A capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. was used as the column. Helium (1 mL/min) was used as the carrier gas. The temperature of the sample vaporization chamber was set to 300°C, the temperature of the ion source was set to 200°C, the ionization voltage was set to 70 eV, and the luminescence current was set to 150 μA. The sample was dissolved in acetone to prepare a 1 wt% solution, and 1 μL of the obtained solution was injected into the sample vaporization chamber. The recorder used is a GCMS Solution system manufactured by Shimadzu Corporation.

High Performance Liquid Chromatography (HPLC) analysis: Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used for the measurement. The column used was YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle size 5 μm) manufactured by YMC. The eluent was a mixture of acetonitrile and water. As the detector, an ultraviolet (UV) detector, a refractive index (RI) detector, a corona (CORONA) detector, etc. were suitably used. When a UV detector was used, the detection wavelength was set to 254 nm. The sample was dissolved in acetonitrile to prepare a 0.1% by weight solution, and 1 μL of the solution was introduced into the sample chamber. As a recorder, C-R7Aplus manufactured by Shimadzu Corporation was used.

UV-visible spectrometry: PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used for the measurement. The detection wavelength was set to 190 nm to 700 nm. The sample was dissolved in acetonitrile to prepare a 0.01 mmol/L solution, and then placed in a quartz cell (optical path length 1 cm) for measurement.

Sample: When measuring phase structure and transition temperature (clearing point, melting point, polymerization starting temperature, etc.), the compound itself is used as the sample. When measuring the upper limit temperature of the nematic phase, viscosity, optical anisotropy, dielectric anisotropy and other physical properties, a mixture of the compound and mother liquid crystal is used as the sample.

When using a sample obtained by mixing a compound with a mother liquid crystal, the measurement is performed as follows. Prepare a sample by mixing 15% by weight of the compound with 85% by weight of the mother liquid crystal. Based on the measured value of the sample, calculate the extrapolated value according to the following equation and record the value. ＜Extrapolated value＞=（100×＜Measured value of sample＞－＜Weight % of mother liquid crystal＞×＜Measured value of mother liquid crystal＞）/＜Weight % of compound＞

When crystals (or smectic phases) precipitate at 25° C. at this ratio, the ratio of the compound to the mother liquid crystal is changed in the order of 10% by weight: 90% by weight, 5% by weight: 95% by weight, and 1% by weight: 99% by weight, and the physical properties of the sample are measured at a ratio at which crystals (or smectic phases) no longer precipitate at 25° C. In addition, unless otherwise specified, the ratio of the compound to the mother liquid crystal is 15% by weight: 85% by weight.

When the dielectric anisotropy of the compound is zero or positive, the following mother liquid crystal (A) is used. The ratio of each component is expressed in weight %.

[Chemistry 51]

When the dielectric anisotropy of the compound is zero or negative, the following mother liquid crystal (B) is used. The ratio of each component is expressed in weight %.

[Chemistry 52]

Mother liquid crystal (C): A mother liquid crystal (C) containing the following fluorine-based compounds as components was also used. The ratio of the components of the mother liquid crystal (C) is expressed in weight %.

[Chemistry 53]

The ratio of the compound to the mother liquid crystal (C) was set to 20 wt %:80 wt %. When crystals (or smectic phase) were precipitated at 25°C at this ratio, the ratio of the compound to the mother liquid crystal (C) was changed in the order of 15 wt %:85 wt %, 10 wt %:90 wt %, 5 wt %:95 wt %, and 1 wt %:99 wt %, and the physical properties of the sample were measured at a ratio at which crystals (or smectic phase) were no longer precipitated at 25°C. In addition, unless otherwise specified, the ratio of the compound to the mother liquid crystal (C) was 20 wt %:80 wt %.

Measurement method: Physical properties were measured using the following methods. Most of these methods are described in the JEITA standard (JEITA ED-2521B) reviewed and established by the Japan Electronics and Information Technology Industries Association (JEITA). Modified methods are also used. Thin-film transistors (TFTs) are not mounted in the TN devices used for measurement.

(1) Phase structure: The sample was placed on a heating plate (Mettler FP-52 heating stage) of a melting point measuring device equipped with a polarizing microscope. The sample was heated at a rate of 3°C/min while the phase state and its changes were observed under a polarizing microscope to determine the type of phase.

(2) Transition temperature (°C): The measurement is performed using a scanning calorimeter Diamond DSC system manufactured by Perkin Elmer or a high-sensitivity differential scanning calorimeter X-DSC7000 manufactured by SII NanoTechnology. The sample is heated and cooled at a rate of 3°C/min, and the starting point of the endothermic peak or exothermic peak accompanying the phase change of the sample is extrapolated to determine the transition temperature. The melting point and polymerization starting temperature of the compound are also measured using this device. The temperature at which a compound changes from a solid to a liquid crystal phase such as a lamellar phase or nematic phase is sometimes referred to as the "lower limit temperature of the liquid crystal phase." The temperature at which a compound changes from a liquid crystal phase to a liquid is sometimes referred to as the "clearing point."

Crystals are represented by C. When crystals can be divided into two types, they are represented by C ₁ or C ₂ . Smectic phase is represented by S, and nematic phase is represented by N. When phases such as smectic A phase, smectic B phase, smectic C phase, and smectic F phase are distinguished, they are represented by _SA , _SB , _SC , and _SF , respectively. Liquid (isotropic) is represented by I. The transition temperature is expressed as "C 50.0 N 100.0 I", for example. It means that the temperature of transition from crystal to nematic phase is 50.0°C, and the temperature of transition from nematic phase to liquid is 100.0°C.

(3) Compatibility of compounds: Prepare a sample in which the mother liquid crystal and the compound are mixed in a ratio of 20 wt%, 15 wt%, 10 wt%, 5 wt%, 3 wt%, or 1 wt%. Place the sample in a glass bottle and store it in a freezer at -10°C or -20°C for a certain period of time. Observe whether the nematic phase of the sample is maintained or whether crystals (or lamellar phase) are precipitated. Use the condition under which the nematic phase is maintained as a measure of compatibility. Sometimes, the ratio of the compound or the temperature of the freezer is changed as needed.

(4) Upper limit temperature of nematic phase ( _TNI or NI; °C): Place the sample on a heating plate of a melting point measuring device including a polarizing microscope and heat it at a rate of 1 °C/min. The temperature at which a part of the sample changes from the nematic phase to the isotropic liquid is measured. When the sample is a mixture of compound (1) and mother liquid crystal, it is represented by _TNI . When the sample is a mixture of compound (1) and a compound selected from compound (2) to compound (15), it is represented by NI. The upper limit temperature of the nematic phase is sometimes referred to as the "upper limit temperature".

(5) Lower limit temperature of nematic phase (T _C ; °C): A sample having a nematic phase was placed in a glass bottle and stored in a freezer at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days, and the liquid crystal phase was observed. For example, if the sample remains in the nematic phase at -20°C and changes to a crystalline or lamellar phase at -30°C, T _C is recorded as <-20°C. The lower limit temperature of the nematic phase is sometimes referred to as the "lower limit temperature".

(6) Viscosity (volume viscosity; η; measured at 20°C; mPa·s): The measurement was performed using an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd.

(7) Optical anisotropy (refractive index anisotropy; measured at 25°C; Δn): The measurement is performed using light of a wavelength of 589 nm with an Abbe refractometer with a polarizing plate mounted on the eyepiece. After rubbing the surface of the main prism in one direction, the sample is dropped onto the main prism. When the direction of polarization is parallel to the direction of rubbing, the refractive index (n∥) is measured. When the direction of polarization is perpendicular to the direction of rubbing, the refractive index (n⊥) is measured. The value of optical anisotropy (Δn) is calculated according to the equation Δn=n∥-n⊥.

(8) Specific resistance (ρ; measured at 25°C; Ωcm): 1.0 mL of the sample is injected into a container including electrodes. A DC voltage (10 V) is applied to the container, and the DC current is measured after 10 seconds. The specific resistance is calculated according to the following equation. (Specific resistance) = {(voltage) × (capacitance of the container)} / {(DC current) × (dielectric constant of vacuum)}.

(9) Voltage retention ratio (VHR-1; measured at 25°C; %): The TN device used for the measurement has a polyimide alignment film and the distance between the two glass substrates (cell gap) is 5 μm. The device is sealed using an adhesive that is cured by ultraviolet light after the sample is placed. A pulse voltage (5 V, 60 microseconds) is applied to the device for charging. The decaying voltage is measured over a period of 16.7 milliseconds using a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis per unit cycle is calculated. Area B is the area when there is no decay. The voltage retention ratio is expressed as a percentage of area A relative to area B.

(10) Voltage holding ratio (VHR-2; measured at 80°C; %): The voltage holding ratio was measured by the same method as above, except that the measurement was performed at 80°C instead of 25°C. The obtained result is indicated by the symbol VHR-2.

(11) Flicker rate (measured at 25°C; %): The measurement was performed using a multimedia display tester 3298F manufactured by Yokogawa Electric Co., Ltd. The light source was a light emitting diode (LED). The sample was placed in a normally black mode FFS element with a distance (cell gap) of 3.5 μm between two glass substrates and anti-parallel rubbing directions. The element was sealed using an adhesive that cures with ultraviolet light. A voltage was applied to the element, and the voltage at which the amount of light passing through the element was the maximum was measured. While applying the voltage to the element, the sensor unit was brought close to the element and the flicker rate displayed was read.

The methods for measuring physical properties may differ between samples with positive dielectric anisotropy and samples with negative dielectric anisotropy. The methods for measuring when the dielectric anisotropy is positive are described in Measurements (12a) to (16a). The methods for measuring when the dielectric anisotropy is negative are described in Measurements (12b) to (16b).

(12a) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s; sample with positive dielectric anisotropy): Measured according to the method described in M. Imai et al., "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)). The sample was placed in a TN device with a twist angle of 0 degrees and a distance between two glass substrates (cell gap) of 5 μm. Voltage was applied to the device in steps of 0.5 V from 16 V to 19.5 V. After no voltage was applied for 0.2 seconds, the voltage was repeatedly applied with only one rectangular wave (rectangular pulse; 0.2 seconds) and no voltage applied (2 seconds). The peak current and peak time of the transient current generated by the application were measured. The rotational viscosity value was obtained based on these measured values and equation (8) on page 40 of the paper by M. Imai et al. The value of the dielectric anisotropy required for the calculation was obtained by using the element for which the rotational viscosity was measured and using the method described below.

(12b) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s; sample with negative dielectric anisotropy): Measured according to the method described in M. Imai et al., "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)). The sample was placed in a VA device with a distance (cell gap) of 20 μm between two glass substrates. Voltage was applied to the device in steps of 1 V from 39 V to 50 V. After no voltage was applied for 0.2 seconds, voltage was applied repeatedly with only one rectangular wave (rectangular pulse; 0.2 seconds) and no voltage applied (2 seconds). The peak current and peak time of the transient current generated by the application were measured. The rotational viscosity was obtained based on these measured values and equation (8) on page 40 of the paper by M. Imai et al. The dielectric anisotropy required for the calculation was measured by the following dielectric anisotropy term.

(13a) Dielectric anisotropy (Δε; measured at 25°C; sample with positive dielectric anisotropy): The sample was placed in a TN device with a distance (cell gap) of 9 μm between two glass substrates and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε∥) of the liquid crystal molecules in the long axis direction was measured. A sine wave (0.5 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε⊥) of the liquid crystal molecules in the short axis direction was measured. The value of dielectric anisotropy was calculated based on the equation Δε=ε∥-ε⊥.

(13b) Dielectric anisotropy (Δε; measured at 25°C; samples with negative dielectric anisotropy): The dielectric anisotropy value was calculated based on the equation Δε=ε∥-ε⊥. The dielectric constants (ε∥ and ε⊥) were measured as follows. 1) Measurement of dielectric constant (ε∥): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a thoroughly cleaned glass substrate. The glass substrate was rotated using a rotator and then heated at 150°C for 1 hour. The sample was placed in a VA device with a gap (cell gap) of 4 μm between two glass substrates, and the device was sealed using an adhesive cured by ultraviolet light. A sine wave (0.5 V, 1 kHz) was applied to the element, and the dielectric constant (ε∥) of the liquid crystal molecules in the long axis direction was measured after 2 seconds. 2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. The glass substrate was calcined, and the obtained alignment film was rubbed. The sample was placed in a TN element with a distance (unit gap) of 9 μm between two glass substrates and a twist angle of 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to the element, and the dielectric constant (ε⊥) of the liquid crystal molecules in the short axis direction was measured after 2 seconds.

(14a) Elastic constant (K; measured at 25°C; pN; sample with positive dielectric anisotropy): The measurement was performed using an HP4284A LCR meter manufactured by Yokogawa-Hewlett-Packard Co., Ltd. The sample was placed in a horizontally aligned element with a spacing (cell gap) of 20 μm between two glass substrates. A charge of 0 V to 20 V was applied to the element, and the electrostatic capacitance (C) and the applied voltage (V) were measured. These measured values were fitted using equations (2.98) and (2.101) in the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun, p. 75), and the values of K ₁₁ and K ₃₃ were obtained based on equation (2.99). Next, the values of K ₁₁ and K ₃₃ just obtained are used in equation (3.18) on page 171 to calculate K ₂₂ . The elastic constant K is represented by the average value of K ₁₁ , K ₂₂ , and K ₃₃ thus obtained.

(14b) Elastic constants (K ₁₁ and K ₃₃ ; measured at 25°C; pN; samples with negative dielectric anisotropy): The measurements were made using an EC-1 elastic constant tester manufactured by TOYO Technica Co., Ltd. The sample was placed in a vertically aligned device with a distance (cell gap) of 20 μm between two glass substrates. A charge ranging from 20 V to 0 V was applied to the device, and the electrostatic capacitance (C) and applied voltage (V) were measured. These values were fitted using equations (2.98) and (2.101) in the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun, p. 75), and the elastic constant values were obtained from equation (2.100).

(15a) Threshold voltage (Vth; measured at 25°C; V; sample with positive dielectric anisotropy): The measurement was performed using an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The sample was placed in a TN element in a normally white mode with a distance (cell gap) between two glass substrates of 0.45/Δn (μm) and a twist angle of 80 degrees. The voltage applied to the element (32 Hz, rectangular wave) was increased stepwise from 0 V to 10 V in units of 0.02 V. At this time, light was irradiated to the element from a vertical direction, and the amount of light passing through the element was measured. A voltage-transmittance curve was prepared in which the transmittance was 100% when the light amount reached a maximum, and the transmittance was 0% when the light amount reached a minimum. The critical voltage is expressed by the voltage at which the transmittance reaches 90%.

(15b) Threshold voltage (Vth; measured at 25°C; V; sample with negative dielectric anisotropy): The measurement was performed using an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The sample was placed in a normally black mode VA element with a distance (cell gap) of 4 μm between two glass substrates and anti-parallel rubbing directions, and the element was sealed using an adhesive that cures with ultraviolet light. The voltage applied to the element (60 Hz, rectangular wave) was increased stepwise from 0 V to 20 V in units of 0.02 V. At this time, light was irradiated to the element from a vertical direction, and the amount of light passing through the element was measured. A voltage-transmittance curve is created in which the transmittance is 100% when the light intensity reaches the maximum and the transmittance is 0% when the light intensity reaches the minimum. The critical voltage is represented by the voltage when the transmittance reaches 10%.

(16a) Response time (τ; measured at 25°C; ms; sample with positive dielectric anisotropy): The measurement was performed using an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a TN element in a normally white mode with a distance (cell gap) of 5.0 μm between two glass substrates and a twist angle of 80 degrees. A rectangular wave (60 Hz, 5 V, 0.5 sec) was applied to the element. At this time, light was irradiated to the element from a vertical direction, and the amount of light passing through the element was measured. When the light amount reached a maximum, the transmittance was regarded as 100%, and when the light amount reached a minimum, the transmittance was regarded as 0%. Rise time (τr: rise time; milliseconds) is the time required for the transmittance to change from 90% to 10%. Fall time (τf: fall time; milliseconds) is the time required for the transmittance to change from 10% to 90%. The response time is expressed as the sum of the rise time and fall time calculated in the above manner.

(16b) Response time (τ; measured at 25°C; ms; for samples with negative dielectric anisotropy): The measurement was performed using an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a normally black mode Patterned Vertical Alignment (PVA) device with a spacing (cell gap) of 3.2 μm between two glass substrates and anti-parallel rubbing directions. The device was sealed using an adhesive that was cured by ultraviolet light. A voltage slightly exceeding the critical voltage is applied to the element for 1 minute, and then a voltage of 5.6 V is applied while irradiating the element with ultraviolet light of 23.5 mW/ ^cm2 for 8 minutes. A rectangular wave (60 Hz, 10 V, 0.5 seconds) is applied to the element. At this time, light is irradiated to the element from a vertical direction, and the amount of light passing through the element is measured. When the light amount reaches the maximum, the transmittance is considered to be 100%, and when the light amount is the minimum, the transmittance is considered to be 0%. The response time is expressed by the time required for the transmittance to change from 90% to 10% (fall time; milliseconds).

[Synthesis Example 1] Synthesis of compound (a-71)

[Chemistry 54]

Step 1: Synthesis of compound (t-2) The commercially available compound (t-1) (10.0 g, 68.2 mmol), iodoethane (12.8 g, 81.9 mmol), and potassium carbonate (18.9 g, 136 mmol) were dissolved in N,N-dimethylformamide (100 mL) and stirred at 70°C to 80°C for 2 hours. After the reaction was completed, it was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with water and a saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=4:1) to obtain compound (t-2) (9.83 g, 56.3 mmol) as a colorless liquid.

Step 2: Synthesis of compound (t-4) Compound (t-3) (10.0 g, 63.7 mmol), 1-iodobutane (14.1 g, 76.4 mmol), and potassium carbonate (17.6 g, 127 mmol) were dissolved in DMF (100 mL) and stirred at 70°C to 80°C for 2 hours. After the reaction was completed, it was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with water and a saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=1:1) to obtain compound (t-4) (13.2 g, 61.9 mmol) as a yellow liquid.

Step 3: Synthesis of compound (t-5) Compound (t-4) (13.2 g, 61.9 mmol) was dissolved in 2-propanol (140 mL), and 5% palladium-carbon (0.660 g) was added for hydrogenation. The catalyst was filtered and separated, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (toluene) to obtain compound (t-5) (4.50 g, 24.6 mmol) as a brown solid.

Step 4: Synthesis of compound (t-6) Compound (t-2) (4.29 g, 24.6 mmol), compound (t-5) (4.50 g, 24.6 mmol), sodium tert-butoxide (3.54 g, 36.8 mmol) and Pd(amphos)C12 (0.174 g) were dissolved in xylene (50 mL) and stirred at 110°C for 3 hours. After the reaction was completed, it was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with water and saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=4:1) to obtain compound (t-6) (4.67 g, 14.5 mmol) as a peach-colored liquid.

Step 5: Synthesis of compound (a-71) Compound (t-6) (4.67 g, 14.5 mmol) was dissolved in acetic acid (80 mL), and sodium acetate (3.91 g, 17.4 mmol) was added, and the mixture was heated to reflux for 50 minutes. After the reaction was completed, the mixture was cooled to room temperature, filtered using magnesium silicate (Florisil)/diatomaceous earth, poured into water, and extracted with toluene three times. The combined organic layer was washed with water and saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=1:1) to obtain compound (a-71) (1.61 g, 5.04 mmol) as a colorless solid.

¹ H-NMR (CDCl ₃ ; δppm): 8.13 (brs, J=8.13Hz, 1H), 7.58 (d, J=8.6Hz, 2H), 6.89 (ddd, J=7.9, 7.8, 1.1Hz, 2H) , 4.21 (q, J=7.0Hz, 2H), 4.14 (t, J=6.6Hz, 2H), 1.84 (quin, J=6.7Hz, 2H), 1.54 (sext, J=7.5Hz, 2H), 1.48 (t, J=7.1Hz, 3H), 1.00 (t, J=7.4Hz, 3H).

Phase transition temperature: C 92.4 I. Upper limit temperature (NI) = -45.7℃; dielectric anisotropy (Δε) = -1.48; optical anisotropy (Δn) = 0.147; viscosity (η) = 127.4 mPa·s.

[Synthesis Example 2] Synthesis of compound (a-74)

[Chemistry 55]

Compound (a-71) (0.710 g, 2.22 mmol) was dissolved in N,N-dimethylformamide (10 mL), cooled in an ice bath, and sodium hydroxide (0.196 g, 4.49 mmol) was added in small amounts each time, and stirred for 30 minutes. Methyl iodide (0.821 g, 2.59 mmol) was added dropwise, and stirred for 1 hour while cooling in an ice bath. After the reaction was completed, it was poured into water and extracted with toluene three times. The combined organic layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=1:1) to obtain compound (a-74) (0.52 g, 1.56 mmol) as a colorless solid.

¹ H-NMR (CDCl ₃ ; δppm): 7.56 (d, J=8.5Hz, 2H), 6.86 (dd, J=7.8, 7.8, 1.4Hz, 1H), 4.21 (s, 3H), 4.20 (q, J=7.0Hz, 2H), 4.12 (t, J=6.6Hz, 2H), 1.84 (quin, J=6.6Hz, 2H), 1.55 (sext, J=7.4Hz, 2H), 1.48 (t, J= 7.0Hz, 3H), 1.00 (t, J=7.4Hz, 3H).

Phase transition temperature: C 71.0 I. Upper limit temperature (NI) = 37.0℃; dielectric anisotropy (Δε) = -3.14; optical anisotropy (Δn) = 0.194; viscosity (η) = 54.1 mPa·s.

[Synthesis Example 3] Synthesis of compound (a-5)

[Chemistry 56]

Step 1: Synthesis of compound (t-8) Dissolve the commercially available compound (t-7) (12.5 g, 64.1 mmol) and potassium carbonate (11.6 g, 83.4 mmol) in N,N-dimethylformamide (125 mL) and heat to 60°C. Add a solution of iodoethane (11.2 g, 70.6 mmol) in N,N-dimethylformamide (20 mL) dropwise and stir at 60°C for 6 hours and 30 minutes. After the reaction is completed, cool to room temperature, pour into water, and extract with toluene three times. Wash the combined organic layer with 1N-NaOH aqueous solution and water, dry with anhydrous magnesium sulfate, and concentrate under reduced pressure. The residue was purified by short-path silica gel chromatography (heptane) to obtain compound (t-8) (12.5 g, 56.9 mmol) as a colorless liquid.

Step 2: Synthesis of compound (t-9) The commercially available compound (t-7) (12.5 g, 65.5 mmol), 1-bromobutane (9.86 g, 72.0 mmol), and potassium carbonate (11.8 g, 85.1 mmol) were dissolved in N,N-dimethylformamide (125 mL) and stirred at 80°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with 2N-NaOH aqueous solution and water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by short-path silica gel chromatography (heptane) to obtain compound (t-9) (14.2 g, 57.5 mmol) as a light brown liquid.

Step 3: Synthesis of compound (t-10) Compound (t-9) (14.0 g, 56.7 mmol), benzylamine (7.29 g, 68.0 mmol), and sodium tert-butoxide (8.17 g, 85.0 mmol) were dissolved in toluene (196 mL), degassed under reduced pressure, and palladium (0) bis(dibenzylideneacetone) (0.652 g) and 2-(di-tert-butylphosphino)biphenyl (0.676 g, 2.27 mmol) were added, and heated and stirred at 60°C. When the heat subsided, the temperature was gradually raised to reflux temperature and heated to reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate = 9:1) to obtain compound (t-10) (15.0 g, 54.9 mmol) as a brown liquid.

Step 4: Synthesis of compound (t-11) Compound (t-10) (11.0 g, 40.2 mmol), compound (t-8) (8.82 g, 40.2 mmol), sodium tert-butoxide (5.80 g, 60.4 mmol) and Pd(amphos)C12 (0.0285 g) were dissolved in toluene (330 mL) and heated under reflux for 3 hours. After the reaction was completed, it was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with water and saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=1:1) to obtain compound (t-11) (11.6 g, 28.2 mmol) as a colorless liquid.

Step 5: Synthesis of compound (t-12) Compound (t-11) (11.6 g, 28.2 mmol) was dissolved in toluene (30 mL) and 2-propanol (60 mL), and potassium hydroxide (0.580 g) was added for hydrogenation. The catalyst was filtered and separated, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: ethyl acetate = 4:1) to obtain compound (t-12) (7.70 g, 24.0 mmol) as a brown liquid.

Step 6: Synthesis of compound (a-5) Compound (t-12) (6.70 g, 20.9 mmol) was dissolved in acetic acid (110 mL), and sodium acetate (5.61 g, 25.0 mmol) was added, and the mixture was heated to reflux for 50 minutes. After the reaction was completed, the mixture was cooled to room temperature, filtered through magnesium silicate/diatomaceous earth, poured into water, and extracted three times with toluene. The combined organic layers were washed with water and saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1:1) to obtain compound (a-5) (1.34 g, 4.20 mmol) as a colorless solid.

¹ H-NMR (CDCl ₃ ; δppm): 7.80 (brs, 1H), 7.56 (dd, J=11.0, 2.1Hz, 2H), 6.94 (d, J=6.9Hz, 1H), 4.15 (q, J= 7.0Hz, 2H), 4.08 (t, J=6.6Hz, 2H), 1.86 (quin, J=6.6, 2H), 1.54 (sext, J=7.5Hz, 2H), 1.50 (t, J=7.0Hz, 3H), 1.00 (t, J=7.4Hz, 3H).

Phase transition temperature: C 217.3 I. Upper limit temperature (NI) = 71.0℃; dielectric anisotropy (Δε) = -22.5; optical anisotropy (Δn) = 0.220; viscosity (η) = 202.9 mPa·s.

[Synthesis Example 4] Synthesis of compound (a-11)

[Chemistry 57]

Compound (a-5) (0.26 g, 0.81 mmol) was dissolved in N,N-dimethylformamide (5.0 mL), cooled in an ice bath, and sodium hydroxide (0.0718 g, 1.64 mmol) was added in small amounts each time, and stirred for 30 minutes. Methyl iodide (0.301 g, 2.11 mmol) was added dropwise, and stirred for 3 hours while cooling in an ice bath. After the reaction was completed, it was poured into water and extracted with toluene three times. The combined organic layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=1:1) to obtain compound (a-11) (0.20 g, 0.600 mmol) as a colorless solid.

¹ H-NMR (CDCl ₃ ; δppm): 7.58 (dd, J=11.0, 2.3Hz, 2H), 6.86 (d, J=6.8Hz, 1H), 4.21 (q, J=7.0Hz, 2H), 4.13 (t, J=6.6Hz, 2H), 3.75 (s, 3H), 1.88 (quin, J=6.6Hz, 2H), 1.56 (sext, J=7.5Hz, 2H), 1.52 (t, J=7.0Hz , 3H), 1.01 (t, J=7.4Hz, 3H).

Phase transition temperature: C 142.5 I.; 3% was not dissolved, so the physical properties could not be determined.

[Synthesis Example 5] Synthesis of compound (a-36)

[Chemistry 58]

Step 1: Synthesis of compound (t-14) Commercially available compound (t-13) (25.0 g, 120 mmol), iodoethane (20.5 g, 132 mmol), and potassium carbonate (21.5 g, 156 mmol) were dissolved in N,N-dimethylformamide (250 mL) and stirred at 80°C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with 2N-NaOH aqueous solution and water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by short-path silica gel chromatography (toluene) to obtain compound (t-14) (25.8 g, 109 mmol) as a brown liquid.

Step 2: Synthesis of compound (t-16) Compound (t-15) (18.0 g, 72.8 mmol), benzylamine (9.37 g, 87.4 mmol), and tert-butoxysodium (10.5 g, 109 mmol) were dissolved in toluene (252 mL), degassed under reduced pressure, and palladium (0) bis(dibenzylideneacetone) (0.838 g) and 2-(di-tert-butylphosphino)biphenyl (0.870 g, 2.91 mmol) were added, and heated and stirred at 60°C. When the heat subsided, the temperature was gradually raised to reflux temperature and heated to reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate = 9:1) to obtain compound (t-16) (15.6 g, 57.1 mmol) as a brown liquid.

Step 3: Synthesis of compound (t-17) Compound (t-14) (13.0 g, 54.9 mmol), compound (t-16) (15.0 g, 54.9 mmol), and sodium tert-butoxide (7.91 g, 82.3 mmol) were dissolved in toluene (450 mL), degassed under reduced pressure, and Pd(amphos)C12 (0.0389 g) was added. The mixture was stirred under heating at 60°C. When the heating subsided, the temperature was gradually raised to reflux temperature and heated under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane:toluene=2:1) to obtain compound (t-17) (15.0 g, 34.9 mmol) as a brown liquid.

Step 4: Synthesis of compound (t-18) Compound (t-17) (15.0 g, 34.9 mmol) was dissolved in toluene (37.5 mL) and 2-propanol (75 mL), and potassium hydroxide (0.75 g) was added to carry out hydrogenation. After the catalyst was filtered and separated, it was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to obtain compound (t-18) (13.1 g, 38.6 mmol) as a light brown liquid.

Step 5: Synthesis of compound (a-36) Compound (t-18) (12.0 g, 35.4 mmol) and potassium carbonate (0.489 g, 3.54 mmol) were dissolved in trimethylacetic acid (120 mL), and potassium acetate (0.794 g) was added, and the mixture was heated under reflux for 16 hours under air. After the reaction was completed, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were neutralized with sodium carbonate, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: ethyl acetate = 3:1) to obtain compound (a-36) (1.50 g, 4.45 mmol) as a colorless solid.

¹ H-NMR (CDCl ₃ ; δppm): 7.83 (brs, 1H), 7.74 (d, J=10.5Hz, 1H), 6.94 (d, J=6.5Hz, 1H), 6.72 (d, J=5.5Hz , 1H), 4.16 (q, J=7.0Hz, 2H), 4.08 (t, J=6.5Hz, 2H), 1.86 (quin, J=7.1, 2H), 1.55 (sext, J=7.5Hz, 2H) , 1.50 (t, J=7.0Hz, 3H), 1.00 (t, J=7.5Hz, 3H).

Phase transition temperature: C 187.5 I. Upper limit temperature (NI) = 84.3℃; dielectric anisotropy (Δε) = -21.5; optical anisotropy (Δn) = 0.187; viscosity (η) = 149.4 mPa·s.

[Comparison experiment] The dielectric anisotropy of compound (a-5) and comparison compound (Ref-1) were compared as follows. Comparison compound (Ref-1) is compound (1-2-5) described in paragraph [0143] of International Publication No. 2015/129412. The synthesis was carried out according to the method of paragraphs [0143] to [0154] of International Publication No. 2015/129412. The dielectric anisotropy (Δε) of compound (a-5) obtained in the synthesis of compound (3) was compared with that of comparison compound (Ref-1). It was found that the dielectric anisotropy of compound (a-5) was negative and very large. Therefore, it was concluded that compound (1) was superior to similar compounds.

[Table 2] Table 2. Comparison of dielectric anisotropy Compound Dielectric anisotropy (Δε) Synthesis Example 3 Compound (a-5) -22.5 Comparison with compound 1 Comparison compound (Ref-1) -10.4

The compounds shown below can be synthesized by referring to the methods described in the synthesis examples or the section "2. Synthesis of compound (1)".

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[Chemistry 98]

[Chemistry 99]

[Chemical 100]

[Chemistry 101]

[Chemistry 102]

[Chemistry 103]

[Chemistry 104]

[Chemistry 105]

[Chemistry 106]

The following compounds were synthesized by referring to the methods described in the synthesis examples or the section "2. Synthesis of compound (1)".

[Chemistry 107]

¹ H-NMR (CDCl ₃ ; δppm): 7.79 (brs, 1H), 7.62 (d, J=10.9Hz, 1H), 7.50 (d, J=10.3Hz, 1H), 7.15 (d, J=6.3Hz , 1H), 6.94 (d, J=6.9Hz, 1H), 4.17 (q, J=6.9Hz, 2H), 2.76 (t, J=7.5Hz, 2H), 1.67 (quin, J=7.5Hz, 2H ), 1.51 (t, J=6.9Hz, 3H), 1.40-1.32 (m, 4H), 0.90 (t, J=7.5Hz, 3H).

The physical properties of compound (a-4) are as follows: Transition temperature: C 173.7 I. Upper limit temperature (T _NI ) = 47.3°C; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = -15.18; viscosity (η) = 258.2 mPa·s.

[Chemistry 108]

¹ H-NMR (CDCl ₃ ; δppm): 7.64 (d, J=11.5Hz, 1H), 7.53 (d, J=9.7Hz, 1H), 7.10 (d, J=6.3Hz, 1H), 6.87 (d , J=6.9Hz, 1H), 4.22 (q, J=6.9Hz, 2H), 3.77 (s, 3H), 2.80 (t, J=7.5Hz, 2H), 1.70 (quin, J=7.5Hz, 2H ), 1.53 (t, J=6.9Hz, 3H), 1.41-1.35 (m, 4H), 0.91 (t, J=7.5Hz, 3H).

The physical properties of compound (a-9) are as follows: Transition temperature: C 73.4 I. Upper limit temperature (T _NI ) = -44.7°C; optical anisotropy (Δn) = 0.127; dielectric anisotropy (Δε) = -7.72; viscosity (η) = 145.7 mPa·s.

[Chemistry 109]

¹ H-NMR (CDCl ₃ ; δppm): 7.79 (brs, 1H), 7.57 (d, J=4.0Hz, 1H), 7.55 (d, J=3.5Hz, 1H), 6.95 (d, J=6.3Hz , 1H), 6.94 (d, J=6.3Hz, 1H), 4.17 (q, J=6.9Hz, 2H), 3.88 (d, J=6.3Hz, 2H), 1.98-1.94 (m, 2H), 1.87 -1.80 (m, 3H), 1.51 (t, J=6.9Hz, 3H), 1.37-1.16 (m, 5H), 1.09 (dq, J=2.9, 12.6Hz, 2H), 0.96 (dq, J=2.9, 12.6Hz, 2H), 0.89 (t, J=7.5Hz, 3H).

The physical properties of compound (b-7) are as follows: Transition temperature: C 233.1 I. Upper limit temperature (T _NI ) = 114.3°C; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = -10.5; viscosity (η) = 99.4 mPa·s.

[Chemistry 110]

¹ H-NMR (CDCl ₃ ; δppm): 7.59 (d, J=3.5Hz, 1H), 7.57 (d, J=4.0Hz, 1H), 6.87 (d, J=6.9Hz, 1H), 6.85 (d , J=6.9Hz, 1H), 4.21 (q, J=6.9Hz, 2H), 3.91 (d, J=6.3Hz, 2H), 3.75 (s, 3H), 2.00-1.96 (m, 2H), 1.91 -1.81 (m, 3H), 1.52 (t, J=6.9Hz, 3H), 1.37-1.17 (m, 5H), 1.11 (dq, J=3.5, 12.6Hz, 2H), 0.97 (dq, J=3.5, 12.6Hz, 2H), 0.89 (t, J=7.5Hz, 3H).

The physical properties of compound (b-19) are as follows: Transition temperature: C 170.9 I. Upper limit temperature (T _NI ) = 84.3°C; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = -11.5; viscosity (η) = 145.4 mPa·s.

2. Examples of compositions The present invention is described in more detail by way of examples. The examples are typical examples, and therefore the present invention is not limited to the examples. For example, in addition to the compositions of the use examples, the present invention also includes a mixture of the composition of use example 1 and the composition of use example 2. The present invention also includes a mixture prepared by mixing at least two of the compositions of the use examples. The compounds in the use examples are represented by symbols based on the definitions in Table 3 below. In Table 3, the stereo configuration associated with 1,4-cyclohexylene is trans. The numbers in parentheses after the symbols in the use examples indicate the chemical formula to which the compounds belong. The symbol (-) refers to a liquid crystal compound different from compound (1) to compound (15). The ratio (percentage) of the liquid crystal compound is the weight percentage (weight %) based on the weight of the liquid crystal composition without additives. Finally, the physical property values of the composition are summarized. Physical properties were determined according to previously reported methods and the values are reported directly (without extrapolation).

[Table 3]

[Example 1] 2O-Ca(3F,6F)-O4                                         （a-5）          3% 1-BB-3                                             （2-8）          7% 1-BB-5                                             （2-8）          8% 2-BTB-1                                           （2-10）        3% 3-HHB-1                                               （3-1）          8% 3-HHB-O1                                               （3-1）          5% 3-HHB-3                                           （3-1）          14% 3-HHB-F                                           （22-1）        4% 2-HHB(F)-F                                      （22-2）        7% 3-HHB(F)-F                                      （22-2）        7% 5-HHB(F)-F                                      （22-2）        7% 3-HHB(F,F)-F                                   （22-3）        2% 3-HHEB-F                                        （22-10）      4% 5-HHEB-F                                        （22-10）      4% 2-HB-C                                           (24-1) 5% 3-HB-C 12% NI=95.7℃; η=22.1 mPa·s; Δn=0.112; Δε=3.8.

[Use Example 2] 4O-Ca(1F,8F)-O2                                                                                   12% 7-HB-1 3% 5-HB- O2                                                                                                                          7% 5-HBB(F)B-3                                                         6% 3-HB-CL                                                                                            5% 3-HHB(F,F)-F                                                                       30% 5-HBB(F,F)-F                                                                                  ) 24% NI=73.6℃; eta=32.5 mPa·s; Δn=0.125; Δε=5.2.

[Example 3] 2O-Ca(3F,6F,9Me)-O4                           （a-11）        3% 1V2-HH-1                                         （2-1）          3% 1V2-HH-3                                         （2-1）          4% 7-HB(F,F)-F                                         （21-4）        3% 2-HHB(F)-F                                            （22-2）        10% 3-HHB(F)-F                                            （22-2）        10% 7% 2-HBB-F                                                                                                                                                                                                                                     4% 5-HBB-F （22-22） 3% 2-HBB(F)-F （22- 23) 9% 3-HBB(F)-F （22-23） 9% 5-HBB(F)-F （2 2-23) 16% 3-HBB(F,F)-F                                                    5% 5-HBB (F, F)-F

[Use Example 4] 4O-Ca(1F,8F,9Me)-O2 (a-74) 10% 2-HH-3 (2-1) 4% 3-HH-4 12% 1O1- HBBH-5                                   （4-1）          3% 5-HB-CL                                          （21-2）        16% 3-HHB-F                                          （22-1）        4% 3-HHB-CL                                        （22-1）       3% 4-HHB-CL                                                                                5% 4-HHB (F)-F -F                                                     9% 7-HHB(F)-F                                                                                                                                                                                                                             (22-2) (F)-F                                                       4% 3-HHBB(F,F)                                                                        23-6) 2% 4-HHBB(F,F)-F                                                                                 % 3-HH2BB(F,F)-F                                                            ) 3% 4-HH2BB(F,F)-F （23-15） 3% NI=106.7℃; η=21.6 mPa·s; Δn=0.101; Δε=2.7.

[Use Example 5] 2O-Ca(3F,4F,6F)-O4                                                                    10% 1O1-HBBH-4 4% 1O1- HBBH-5                                                                                                                                                                                                            H2HB(F,F)-F                                                         8% 4-H2HB(F, F)-F （22-15） 8% 5-H2HB(F,F)-F （22-15） 8% 3-HBB(F,F)-F (22-24) 11% 5-HBB(F,F)- f -F                                                                     3% 3-HH2BB(F,F) -F (23-15) 3% 5-HHEBB-F (23-17) 2% NI=103.0℃; η=34.3 mPa·s; Δn=0.123; Δε=7.8.

[Example 6] 2O-Ca(3F,4F,6F)-4                                 （a-232）      3% 5-HBBH-3                                          （4-1）          3% 3-HB(F)BH-3                                      （4-2）          3% 5-HB-F                                               （21-2）        9% 6-HB-F                                               （21-2）        9% 7-HB-F                                               （21-2）        7% 2-HHB-OCF3                                          （22-1）      7% 3-HHB-OCF3 (22-1) 7% 4-HHB-OCF3 (22-1) 7% 5-HHB-OCF3 (22-1) 5% 3-HHB(F,F)-OCF2H (22-3) 4% 3-HHB(F ,F)-OCF3 (22-3) 5% 3-HH2B-OCF3 (22-4) 4% 5-HH2B-OCF3 (22-4) 4% 3-HH2B(F)-F                                                             3-HBB(F)        10% 5-HBB (F)-F

[Use Example 7] 2O-Ca(3F,6F)-5                                                                                5% 3-HH-4 4% 5-B( F)BB-2                                                                                                                          11% 3-HHB (F,F)-F F (22-12) 7% 4-HHEB(F,F)-F                                                 3% 5-                              3-HBB(F,F)-F (22-24 ） 20% 5-HBB(F,F)-F （22-24） 15% 2-HBEB(F,F)-F （22-3 9) 3% 3-HBEB(F,F)-F （22- 39) 5% 5-HBEB(F,F)-F (22-39) 3% 3-HHBB(F,F)-F (23-6) 6%

[Example 8] 2O-Ca(3F,4F)-4                                            （a-233）      3% V2-HHB-1                                              （3-1）          5% 3-HB-CL                                             （21-2）        6% 5-HB-CL                                             （21-2）        4% 3-HHB-OCF3                                        （22-1）        5% 5-HHB(F)-F                                            （22-2）        5% V-HHB(F)-F                                            （22-2）      5% 3-H2HB-OCF3 (22-13) 5% 5-H2HB(F,F)-F (22-15) 5% 5-H4HB-OCF3 (22-21) 12% 5-H4HB(F,F)-F H4HB(F,F)-CF3 (22-21) 8% 5-H4HB(F,F)-CF3 (22-21) 10% 2-H2BB(F)-F                                           （22-26） 5% 3-H2BB(F)-F （22-26） 10% 3-HBEB(F,F)-F (22-39) 5%

[Use Example 9] 2O-Ca(6F)-5 (a-234) 3% 3-HH-4 (2-1)                                                                                                    ( 2-5) 15% 3-HHB-1 3-1 8% 3-HHB-O1 (3-1) 5% 5-HB-CL (21-2) 14% 7-HB(F,F)-F                                                                                      7% 3-HHB(F)-F 7% 5 -HHB(F)-F                                                                                                                6% 3-H2HB(F,F)-F                               (22-15)                                                                                                                                                                  H2HB(F,F)-F (22-15) 5%

[Use Example 10] 5-HCa(3F,6F)-3                                                                                                   ) 9% 3-HH-5 10% 3-HHB- 4 3% 7-HB(F)-F                                                             7% 2-HHB(F,F)-F                                                                                    4% 3-HHB(F,F)-F                                                                                     8% 5-HHEB-F                                                                                 8% 3-HHEB(F,F )-F                                                                     10% 4-HHEB(F,F)-F                                                                                                                       ’ f F)-F (22-109) 6% 5-GHB(F,F)-F                                     7% NI=82.6℃; η=21.7 mPa·s; Δn=0.068; Δε=5.9.

[使用例11] 3-H1OCa(3F,6F)-3                           （b-227）      3% 3-HH-VFF                                        （2-1）          5% 5-HH-VFF                                       （2-1）          25% 2-BTB- 1                                                                                                            4% VFF-HHB-1                                                                                           11% 3-H2BTB-2                                                                                                            4% 3-H2BTB-4 （3-17） 4% 3-HB-C （24- 1) 18% 1V2-BEB(F,F)-C (24-15) 6%

[Use Example 12] 2O-Ca(3F,6F)-O4 (a-5) 4% 3-HH-V (2-1) 35% 3-HH-V1 5% 5-HH- V                                                                                4% V-HHB-1                                                                                                                                            5% 3-HHEH-5                                                                                                      3% 3-BB(F,F)XB(F,F)-F 6% 3 -BB(2F,3F)XB(F,F)-F (22-114) 3% 3-HHBB(F,F)-F (23-6) 3% 3-HBBXB( F,F)-F                                23-32) 3% 5-HB (F)B (F,F) 23-47) 3% 4-BB(F)B(F,F)XB(F,F)-F （23-47） 5% 5-BB(F)B(F,F)XB(F,F )-F (23-47) 3% NI=81.0℃; η=18.0 mPa·s; Δn=0.102; Δε=3.5.

[Use Example 13] 4O-Ca(1F,8F)-O2                                                                                       31% 3-HH-V1 7% V-HH- V1                                                                                            4% V-HHB-1                                                                                                             4% 3-HHEH-5                                                                                             3% 3-BB(F,F)XB(F,F)-F 3% 3 -HHXB(F,F)-CF3                            （22-100）    3% 3-GB(F,F)XB(F,F)-F                         （22-113）    2% 3-GB(F)B(F,F )-F               (22-116)  2% 3-HHBB(F,F)-F                  (23-6) 3% 3-BB(F)B(F,F)XB(F,F)-F （23-47） 3% 4-BB(F)B(F,F)XB(F, F)-F                 (23-47)   5% 5-BB(F)B(F,F)XB(F,F)-F                                                 3% 3-GB(F)B(F,F) XB(F,F)-F (23-57) 3% NI=72.3℃; η=19.9 mPa·s; Δn=0.106; Δε=3.7.

[Use Example 14] 2O-Ca(3F,6F,9Me)-O4 (a-11) 5% 3-HH-V (2-1) 30% 3-HH-V1 5% 3- HHB-1                                                                                   5% 3-HBB-2                                                                                                                           5% 3-HHEH-3                                                                                                              3% 1V2-BB-F 3-BB(F,F)XB(F, F)-F                           (22-97)     4% 3-GB(F,F) (23-6) 3 % 3-HBB(F,F)XB(F,F)-F （23-38） 3% 3-BB(F)B(F,F)XB(F)-F （23-46） 3% 4-BB(F)B(F,F)XB(F,F) -F                   (23-47) 3% 5-BB(F)B(F,F)XB(F,F)-F                                                             3% 3-GB(F)B(F,F)XB( F,F)-F (23-57) 5% 4-GB(F)B(F,F)XB(F,F)-F (23-57) 3% 5-GB(F)B(F, F)XB(F,F)-F (23-57) 2%

[Use Example 15] 4O-Ca(1F,8F,9Me)-O2 (a-74) 9% 3-HH-V (2-1) 25% 3-HH-V1 4% 3- HHB-1                                                                                                                                4% V2-BB(F)B-1                                                                                                            3% 3-HHEBH-3                                                                                        4% 3-BB(F)B(F,F)-F 3-BB (F,F)XB(F,F)-F (22-97) 5% 3-HHBB(F,F)-F (23-6) 3% 5-HB(F)B( F,F)XB (F,F)-F (23-41) 4% 4-BB (F)B (F, F) 23-47) 3% 2-dhBB(F,F)XB(F,F)-F （23-50） 2% 3-dhBB(F,F)XB(F,F)-F （23-50） 3% 3-GBB(F)B(F,F)-F                                       3% 4-GBB(F)B(F,F)-F                                                           . 3% 3-BB(F,F)

[Use Example 16] 2O-Ca(3F,4F,6F)-O4 (a-36) 2% 3-HH-V (2-1) 33% 3-HH-V1 5% 3- HHB-1                                                                                   5% V2-BB(F)B-1                                                                                                      3% 1V2-BB-F                                                                                                       3% 3-BB(F,F)XB(F,F)- f (22-113) 3% 3- GB(F)B(F)-F (22-115) 3% 3-HHBB(F,F)-F                                （23-6）        3% 5-HB(F)B(F,F)XB(F,F)-F                  （23-41）      3% 3-GB( F)B (F,F) F, F) 3% 3-GB(F)B(F)B(F)-F                            (23-59) 3% NI=81.9℃; η=19.0 mPa·s; Δn=0.096; Δε=5.4.

[Use Example 17] 2O-Ca(3F,4F,6F)-4                                                                                           5% 3-HB-O1 15% 3- HHB-1                                                                                                                        12% 5-HB(2F,3F)-O2                 (5-1) 12% 2-HHB(2F, 3F)-1 （6-1） 8% 3-HHB(2F,3F)-1 （6-1） 12% 3-HHB(2F,3F)-O2 (6-1) 13% 5-HHB(2F,3F)- O2 (6-1) 13%

[Use Example 18] 2O-Ca(3F,6F)-5                                                                                        ) 3% 3-HH-4 15% 3-HH- 5                                                                                                        12% 3-HHB-1 3-1 3-HHB-3 3-HHB-3 3-1) 4% 3-HHB-O1                                                                         15% 5-H2B(2F,3F)-O2 13% 2- HBB(2F,3F)-O2 （6-7） 3% 3-HBB(2F,3F)-O2 （6-7） 9% 5-HB B(2F,3F)-O2               (6-7)                                                                                                                  -HHB(2F,3Cl)-O2                                                              5%

[Use Example 19] 2O-Ca(3F,4F)-4                                                                                            16% 2-HH-5 5% 3-HH- 4                                                                                                    2% 1-BB-3                                                                              3-1) 5% 3-HHB-O1                                                                                         2% 3-BB(2F,3F)-O2 5-3 9% 5-BB (2F,3F)-O2 (5-3) 6% 2-HH1OB(2F,3F)-O2 (6-5) 13% 3-HH1 OB(2F,3F)-O2 (6-5) 17%

[Use Example 20] 2O-Ca(6F)-5 (a-234) 3% 2-HH-3 (2-1 )                                                                                                              ( 2-5) 8% 5-HBB(F)B-2 （4-5） 7% 5-HBB(F)B-3 (4-5) 10% 3-HB(2F,3F)-O2 (5 -1) 17% 5-HB(2F,3F)-O2                                         16% 3-HHB(2F,3Cl)-O2                            3% 4-HHB(2F,3Cl)-O2                 (6-12 ) 3% 5-HHB(2F,3Cl)-O2 （6-12） 2% 3-HH1OCro(7F,8F)-5 （10-6） 5%

[Use Example 21] 5-HCa(3F,6F)-3                                                                                        29% 1-BB-3 10% 3-HHB- 1                                                                                                  6% 3-BB(2F,3F)-O2                (5-3) 13% 2-HH1OB(2F,3F)- O2                                                                                                17% 3-HH1OB(2F,3F)-O2 (6-5) 14%

[Use Example 22] 3-H1OCa(3F,6F)-3                                         （b-227）      2% 2-HH-3                                                （2-1）          6% 3-HH-V1                                             （2-1）          9% 1V2-HH-1                                            （2-1）          7% 1V2-HH-3                                            （2-1）          6% 4-HH-V                                                   （2-1）          3% 3-HHB-1                                                             （3-1）        3% 3-HHB-3                                                                                            8% 5-BB(2F,3F)-O2 （5-3） 4% 3-H1OB(2F,3F)-O2 （5-5） 7% 3-HDhB(2F,3F)-O2 （6-3） 7% 2-HH1OB(2F,3F)-O2 （6-5） 8% 3-HH1OB(2F,3F)-O2 （6-5） 17% 2-BB(2F,3F)B-3 （7-1） 11%

[Use Example 23] 2O-Ca(3F,6F)-O4 (a-5) 3% 3-HH-4 (2-1) 5% 3-HH-VFF 4% 3-HB- O1                                                                                              4% 3-HHB-1                                                                                                    9% V-HB(2F,3F)-O2                                                                                      12% 3-HHB(2F,3F)-1 (6-1 ) 12% 3-HHB(2F,3F)-O2 （6-1） 13% 5-HHB(2F,3F)-O2 （6-1 ) 13% NI=88.1℃; η=37.4 mPa·s; Δn =0.096; Δε=-3.5.

[Use Example 24] 4O-Ca(1F,8F)-O2 (a-71) 5% 2-HH-3 (2-1) 16% 7-HB-1 8% 5-HB- O2                                                               7% 5-                                                % 5-HBB(F)B-3                                                               10% 3-HB(2F,3F)-O2 (5-1) 13% 5-HB(2F,3F)-O2                                     11% 2-H1OB(2F, 3F)-O2                        2% 3-H1OB(2F,3F)-O2               (5-5 ) 2% 2O-B(2F,3F)B(F)-O2 （5-9） 2% 4O-B(2F,3F)B(F)-O2 （5-9）        2% V-HHB(2F ,3F)-O2                                                                5% V2-HHB(2F,3F)-O2 (6-1) 4% 5-HHB(2F,3Cl)-O2 (6-12) 2% 3-HH1 OCro(7F,8F)-5 (10-6 ) 2% NI=74.1℃; η=24.6 mPa·s; Δn=0.108; Δε=-2.4.

[Use Example 25] 2O-Ca(3F,6F,9Me)-O4 (a-11) 3% 2-HH-5 (2-1) 3% 3-HH-4 15% 3- HH-5                                                                                                  12% 3-HHB-1 3-1 3-HHB-3 3-HHB-3 3-1) 4% 3-HHB-O1                                                                                 3% 2-BB(2F,3F)-O2 9% 5- H2B(2F,3F)-O2 (5-4) 9% 3-HH2B(2F,3F)-O2 (6-4) 3% HBB(2F,3F)-O2               (6-7)                                                                                                                                                  -HBB(2F,3F)-O2 （6-7） 9% V-HBB(2F,3F)-O2 （6-7） 3% 3-HHB(2F,3Cl)-O2 （6-1 2) 5% 2O-B(2F,3F)B (F)H-3 (6-19) 3%

[Use Example 26] 4O-Ca(1F,8F,9Me)-O2 (a-74) 12% 2-HH-3 (2-1) 6% 3-HH-V1 10% 1V2- HH-1                                                                                          7% V-HHB-1                                                                                                3% 3-HHB-1                                                                                        1) 2% 5-BB(2F,3F)-O2          (5-3) 4% V2-BB(2F,3F )-O2 (5-3) 4% 3-H1OB(2F,3F)-O2 (5-5) 7% 3-HDhB(2F,3F) -O2 (6-3) 7% 3-HH1OB(2F, 3F)-O2 （6-5） 13% 3-dhBB(2F,3F)-O2 （6-9） 3% 3-HchB(2F,3F)-O2 （6 -18) 3% 2-BB(2F,3F)B -3                   (7-1) 5% NI=84.1℃; η=20.7 mPa·s; Δn=0.114; Δε=-3.7.

[Use Example 27] 2O-Ca(3F,4F,6F)-O4 (a-36) 2% 2-HH-3 (2-1) 21% 3-HH-4 9% 3- HB-O2                                                                          5% 3-HHB-1 3-1 3-HHB-O1 3-HHB-O1 -1) 3% V-HBB-2                                                                                                                   3% 3-BB(2F,3F)-O2 5-3 9% 5-BB (2F,3F)-O2 (5-3) 6% 2-HH1OB(2F,3F)-O2 (6-5) 13% 3-HH1OB( 2F,3F)-O2 (6-5) 13% 3- HB(2F,3F)B-2 (7-2) 4% V-HH2BB(2F,3F)-O2 (8-3) 4% NI=76.8℃; η=17.2 mPa·s; Δn=0.100; Δε=-3.2.

[Use Example 28] 2O-Ca(3F,4F,6F)-4 (a-232) 4% 3-HH-V (2-1) 28% 1-BB-3 7% 3- HHB-1                                                                                                                    6% 3-BB(2F,3F)-O2              (5-3) 12% 2-HH1OB(2F,3F )-O2 （6-5）             15% 3-HH1OB(2F,3F)-O2                                      （6-5）         14% 3-H2BBB(2F,3F)-O2                                    （8-1）          3% 5-HFLF4-3                                                              （13-1 ） 3% [Industrial availability]

The liquid crystal compound of the present invention has good physical properties. The liquid crystal composition containing the compound can be widely used in liquid crystal display elements such as personal computers and televisions.

without

without

Claims (21)

A compound represented by formula (1):

In formula (1), ^R1 is hydrogen or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R1 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^R2 is hydrogen, -C≡N, -C≡CC≡N, or an alkyl group having 1 to 15 carbon atoms, at least one _-CH2- in said ^R2 may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^Ra is hydrogen, a linear alkyl group having 1 to 6 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms; Ring A Ring ^A1 and Ring ^A2 are independently cycloalkylene groups having 3 to 5 carbon atoms. In the rings ^A1 and ^A2 , at least one _-CH2- may be substituted by -O-, and at least one -( _CH2 ) _2- may be substituted by -CH=CH-. Ring ^N1 and Ring N2 are independently cycloalkylene groups having 3 to 5 carbon atoms. ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ^{ring N1} and ring ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) ^2- may _be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L1 , ^L2 , ^L3 , ^L4 , ^L5 , and ^L6 are independently hydrogen, fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; when ^L5 and ^L6 are both hydrogen, at least one of ^L1 , ^L2 , ^L3 , and ^L4 is fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , -OCF3, -OCHF2, _-OCH2F , or -C≡N; when ^L1 , ^L2 , ^L3 , and ^L4 are both hydrogen, at least one of ^L5 and ^L6 is fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , _-OCH2F , or _{-C≡N .} F, or -C≡N; l and o are independently 0, or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4; when l is 0, ^R1 will not become hydrogen, and when o is 0, ^R2 will not become hydrogen. The compound as described in claim 1, which is represented by formula (1-1) to formula (1-13),

In formula (1-1) to formula (1-13), R ¹ is hydrogen, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; R ² is hydrogen, -CF ₃ , -OCF ₃ , -C≡N, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring A ¹ and Ring A ² are independently cycloalkylene groups having 3 to 5 carbon atoms, and in Ring A ¹ and Ring A ² , at least one -CH ₂ - may be substituted by -O-, at least one -(CH ₂ ) ₂ - may be substituted by -CH=CH-; Ring N ¹ and Ring N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ring ^N1 and ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, -CF3 _{, -CHF2} , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and ^Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted by -O-, -S-, or -CO-, at least one -( _CH2 ) _2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L1 , ^L2 , ^L3 , and ^L4 are independently hydrogen, fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2 F, _-OCF3 , _-OCHF2 , _-OCH2F , or -C≡N; at least one of ^L1 , ^L2 , ^L3 , and ^L4 is fluorine, chlorine, _-CF3 , _-CHF2 , _-CH2F , -OCF3, _-OCHF2 , _-OCH2F , or -C≡N; in formula (1-1), formula ( _1-3 ), formula (1-5), formula (1-7), formula (1-9), formula (1-11), and formula (1-13), ^R1 will not be hydrogen; in formula (1-1) to formula (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1-13), ^R2 will not be hydrogen. The compound as described in claim 2, wherein in the formula (1-1) to (1-13), ^R1 and ^R2 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently 1,2-cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; Ring ^N1 and Ring N2 are independently cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, or benzo[b]thiophene-2,6-diyl, and at least one hydrogen in the ring ^N1 and the ring ^N2 may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , -OCF Z ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² , Z ³ , and Z ⁴ are independently a single bond, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N, and at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; in formula (1-1), formula (1-3), formula (1-5), formula (1-7), formula (1-9), formula (1-11), and formula (1-13), R ¹ will not become hydrogen, and in formula (1-1) to formula (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1-13), R ² will not become hydrogen. The compound as described in claim 1, which is represented by formula (1-14) to formula (1-26),

In formula (1-14) to formula (1-26), R ¹ is hydrogen, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; R ² is hydrogen, -CF ₃ , -OCF ₃ , -C≡N, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkoxyalkyl group having 2 to 14 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkenyloxy group having 2 to 14 carbon atoms; ^Ra is hydrogen, a linear alkyl group having 1 to 6 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms; Ring A ¹ and Ring A ² are independently cycloalkylene groups having 3 to 5 carbon atoms, and in the Ring A ¹ and Ring A ² , at least one -CH ₂ - may be substituted by -O-, at least one -(CH ₂ ) ₂ - may be substituted by -CH=CH-; Ring N ¹ and Ring N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, benzo[b]thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-oxanthracene-2,6-diyl, or 9H-fluorene-2,7-diyl, wherein the ring N In the ^{ring N1} and ring ^N2 , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F ; ^Z1 , ^Z2 , ^Z3 , and Z4 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the ^Z1 , ^Z2 , ^Z3 , and ^Z4 , at least one _-CH2- may be substituted _by -O-, -S-, or -CO-, at least one -( _CH2 ) ^2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; ^L5 and ^L6 are independently hydrogen, fluorine, chlorine, -CF3, _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or -OCH2F. ₂ , -OCH ₂ F, or -C≡N, at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; in formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26), R ¹ will not be hydrogen, and in formula (1-14) to formula (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1-26), R ² will not be hydrogen. The compound as described in claim 4, wherein in the formula (1-14) to the formula (1-26), ^R1 and ^R2 are independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, or a branched-chain alkyl group having 3 to 6 carbon atoms; Ring ^A1 and Ring ^A2 are independently 1,2-cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; Ring ^N1 and Ring N2 are independently cyclopropyl, 1,3-cyclobutyl, or 1,3-cyclopentyl; ² is independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo[b]thiophene-2,5-diyl, or benzo[b]thiophene-2,6-diyl, and at least one hydrogen in the ring ^N1 and the ring ^N2 may be substituted by fluorine, chlorine, -C≡N, _-CF3 , _-CHF2 , _-CH2F , -OCF Z ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² , Z ³ , and Z ⁴ are independently a single bond, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N, and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C≡N; in formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26), R ¹ will not become hydrogen, and in formula (1-14) to formula (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1-26), R ² will not become hydrogen. The compound as described in any one of claims 1 to 3, which is represented by formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), or formula (1-9-1) to formula (1-9-3),

In formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), and formula (1-9-1) to formula (1-9-3), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; ^Z2 and ^Z3 are independently a single bond, -O-, -COO-, _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , -OCF2-, -( _CH2 ) _2- , -CH=CH-, -C≡C-, -( _CH2 ) _4- , -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF ₂ -, -OCF ₂ (CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; and X ¹ and X ² are independently hydrogen, fluorine, or chlorine. The compound of claim 6, wherein in the formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), formula (1-9-1) to formula (1-9-3), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 10 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to _{6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; Z2 and Z3 are independently a single bond, -COO-, -OCO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, -(CH2)2-} ^{, -CH} _{= CH- , - ( CH2} ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ or -OCF ₃ , at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ or -OCF ₃ , at least two of L ¹ , L ² , L ³ , and L ⁴ are hydrogen; X ¹ and X ² are independently hydrogen, fluorine or chlorine. The compound as described in any one of claim 1, claim 4, and claim 5, which is represented by formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), or formula (1-22-1) to formula (1-22-3),

In formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), and formula (1-22-1) to formula (1-22-3), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; ^Z2 and ^Z3 are independently a single bond, -O-, -COO-, -OCO-, _-CH2O- , _-OCH2- , _-CF2O- , _-OCF2- , -( _CH2 ) ₂ -, -CH=CH-, -C≡C-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₂ COO-, -(CH ₂ ) ₂ OCO-, -OCO(CH ₂ ) ₂ -, -COO(CH ₂ ) ₂ -, -(CH ₂ ) ₂ CF ₂ O-, -(CH ₂ ) ₂ OCF 2 -, _{-OCF 2 (} CH ₂ ) ₂ -, -CF ₂ O(CH ₂ ) ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; and X ¹ and X ² are independently hydrogen, fluorine, or chlorine. The compound of claim 8, wherein in the formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), and formula (1-22-1) to formula (1-22-3), R ¹ and R ² are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched alkyl having 3 to 6 carbon atoms; Z ² and Z ³ are independently a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F, and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; X ¹ and X ² are independently hydrogen, fluorine, or chlorine. The compound as described in any one of claims 1 to 3, which is represented by formula (1-1-1) or formula (1-3-1) to formula (1-3-6),

In formula (1-1-1), and formula (1-3-1) to formula (1-3-6), ^R1 and ^R2 are independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 or 4 carbon atoms; ^Z2 is a single bond, -COO-, _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , -OCF2-, -( _CH2 ) _2- , -CH=CH-, -( _{CH2 ) 4-} , -( _CH2 )3O-, -O( _{CH2 )} 3-, -CH=CH-( _CH2 ) _2- , -( _CH2 ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , or -OCF ₃ , at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , or -OCF ₃ , at least two of L ¹ , L ² , L ³ , and L ⁴ are hydrogen; X ¹ and X ² are independently hydrogen, fluorine, or chlorine. The compound as described in any one of claim 1, claim 4 and claim 5, which is represented by formula (1-14-1) or formula (1-16-1) to formula (1-16-6),

In formula (1-14-1), and formula (1-16-1) to formula (1-16-6), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl having 1 to 4 carbon atoms, or a branched-chain alkyl having 3 or 4 carbon atoms; ^Z2 is a single bond, _-COO- , -OCO-, _-CH2O- , _-OCH2- , _-CF2O- , -OCF2-, -( _CH2 ) _2- , -CH=CH-, -( _{CH2 )4-} , -(CH2)3O-, _-O ( _CH2 ) _3- , -CH= _CH- ( _CH2 ) _2- , -( _CH2 ) ₂ -CH=CH-, -CH=CH-CH ₂ O-, or -OCH ₂ -CH=CH-; L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , or -OCF ₃ , and at least one of L ⁵ and L ⁶ is fluorine, chlorine, -CF ₃ , or -OCF ₃ ; X ¹ and X ² are independently hydrogen, fluorine, or chlorine. The compound as described in any one of claims 1 to 3, which is represented by formula (1-1-1), formula (1-3-1-1) to formula (1-3-1-7), formula (1-3-2-1), formula (1-3-2-2), formula (1-3-3-1), formula (1-3-3-2), formula (1-3-4-1), formula (1-3-4-2), formula (1-3-5-1), formula (1-3-5-2), or formula (1-3-6-1) to formula (1-3-6-4),

In the formula (1-1-1), (1-3-1-1) to (1-3-1-7), (1-3-2-1), (1-3-2-2), (1-3-3-1), (1-3-3-2), (1-3-4-1), (1-3-4-2), (1-3-5-1), (1-3-5-2), and (1-3-6-1) to (1-3-6-4), R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched alkyl having 3 or 4 carbon atoms; L1 ^{, L2} , L3, and L4 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched alkyl having 3 or 4 carbon atoms; ^L1 , ^L2 , ^L3 , and L4 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ⁴ is independently hydrogen, fluorine, -CF ₃ or -OCF ₃ , at least two of L ¹ , L ² , L ³ and L ⁴ are fluorine, -CF ₃ or -OCF ₃ , at least one of L ¹ , L ² , L ³ and L ⁴ is hydrogen; X ¹ and X ² are independently hydrogen or fluorine. The compound as described in any one of claim 1, claim 4 and claim 5, which is represented by formula (1-14-1), formula (1-16-1-1) to formula (1-16-1-7), formula (1-16-2-1), formula (1-16-2-2), formula (1-16-3-1), formula (1-16-3-2), formula (1-16-4-1), formula (1-16-4-2), formula (1-16-5-1), formula (1-16-5-2), or formula (1-16-6-1) to formula (1-16-6-4),

In formula (1-14-1-1), formula (1-16-1-1) to formula (1-16-1-7), formula (1-16-2-1), formula (1-16-2-2), formula (1-16-3-1), formula (1-16-3-2), formula (1-16-4-1), formula (1-16-4-2), formula (1-16-5-1), formula (1-16-5-2), and formula (1-16-6-1) to formula (1-16-6-4), ^R1 and ^R2 are independently alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkenyl having 2 to 10 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms; ^Ra is hydrogen, a straight chain alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms; L ^L5 and ^L6 are independently hydrogen, fluorine, _-CF3 , or _-OCF3 ; at least one of ^L5 and ^L6 is fluorine, _-CF3 , or _-OCF3 ; ^X1 and ^X2 are independently hydrogen or fluorine. The compound as described in any one of claims 1 to 3, which is represented by formula (1-1-1-1) to formula (1-1-1-7),

In formula (1-1-1-1) to formula (1-1-1-7), ^R1 and ^R2 are independently an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched-chain alkyl group having 3 or 4 carbon atoms. The compound as described in any one of claim 1, claim 4 and claim 5, which is represented by formula (1-14-1-1) or formula (1-14-1-2),

In formula (1-14-1-1) or formula (1-14-1-2), ^R1 and ^R2 are independently an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms; ^Ra is hydrogen, a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched-chain alkyl group having 3 or 4 carbon atoms. A liquid crystal composition comprising at least one of the compounds described in any one of claims 1 to 15. The liquid crystal composition according to claim 16 contains at least one compound selected from the group consisting of compounds represented by formula (2) to formula (4),

In formula (2) to formula (4), R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms; at least one -CH ₂ - in R ¹¹ and R ¹² may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; and Z ¹¹ , Z ¹² , and Z ¹³ are independently a single bond, -COO-, -(CH ₂ ) ₂ -, -CH=CH-, or -C≡C-. The liquid crystal composition as described in claim 16 or claim 17 further contains at least one compound selected from the group of compounds represented by formula (5) to formula (13),

In formula (5) to formula (13), ^R13 and ^R14 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, at least one _-CH2- in ^R13 and ^R14 may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; ^R15 is hydrogen, fluorine, alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, at least one _-CH2- in ^R15 may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; Ring ^C1 , Ring ^C2 , Ring ^C3 , and Ring C ^{wherein L11} and L17 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene in which at least one hydrogen atom may be substituted by fluorine, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; ^C5 and ^C6 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; ^Z14 , ^Z15 , ^Z16 , and ^Z17 are independently a single bond, -COO-, _-CH2O- , _-OCF2- , -( _CH2 ) _2- , or _-OCF2- ( _CH2 ) _2- ; ^L11 and L17 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; ¹² is independently fluorine or chlorine; S ¹¹ is hydrogen or methyl; X is -CHF- or -CF ₂ -; j, k, m, n, p, q, r, and s are independently 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3. The liquid crystal composition according to claim 16 or claim 17 further comprises at least one compound selected from the group consisting of compounds represented by formula (21) to formula (23),

In formula (21) to formula (23), R ¹⁶ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms; in said R ¹⁶ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; X ¹¹ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ ; ring D ¹ , ring D ² , and ring D ³ are independently 1,4-cyclohexylene, 1,4-phenylene atom in which at least one hydrogen atom may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁸ , Z ¹⁹ , and Z ²⁰ are independently a single bond, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, or -(CH ₂ ) ₄ -; L ¹³ and L ¹⁴ are independently hydrogen or fluorine. The liquid crystal composition according to claim 16 or claim 17, further comprising at least one compound selected from the group of compounds represented by formula (24),

In formula (24), R ¹⁷ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one -CH ₂ - in R ¹⁷ may be substituted by -O-, and at least one hydrogen atom may be substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring E ¹ is 1,4-cyclohexylene, 1,4-phenylene atom in which at least one hydrogen atom may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ²¹ is a single bond, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, or -C≡C-; L ¹⁵ and L ¹⁶ is independently hydrogen or fluorine; i is 1, 2, 3, or 4. A liquid crystal display element comprising a liquid crystal composition as described in any one of claim 16 to claim 20.