WO2017145611A1 - Composition de cristaux liquides et élément d'affichage à cristaux liquides - Google Patents

Composition de cristaux liquides et élément d'affichage à cristaux liquides Download PDF

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WO2017145611A1
WO2017145611A1 PCT/JP2017/002357 JP2017002357W WO2017145611A1 WO 2017145611 A1 WO2017145611 A1 WO 2017145611A1 JP 2017002357 W JP2017002357 W JP 2017002357W WO 2017145611 A1 WO2017145611 A1 WO 2017145611A1
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Prior art keywords
hydrogen
diyl
liquid crystal
replaced
fluorine
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Japanese (ja)
Inventor
将之 齋藤
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JNC Corp
JNC Petrochemical Corp
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JNC Corp
JNC Petrochemical Corp
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Priority to JP2018501063A priority Critical patent/JPWO2017145611A1/ja
Priority to CN201780004337.1A priority patent/CN108473874A/zh
Priority to KR1020187010248A priority patent/KR20180113188A/ko
Publication of WO2017145611A1 publication Critical patent/WO2017145611A1/fr
Anticipated expiration legal-status Critical
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
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    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
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    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate

Definitions

  • the present invention relates to a liquid crystal composition having a negative dielectric anisotropy, a liquid crystal display element containing the composition, and the like.
  • a liquid crystal composition containing a polar compound having a polymerizable group (or a polymer thereof) and a polymerizable compound (or a polymer thereof), and capable of achieving vertical alignment of liquid crystal molecules by the action of these compounds, and
  • the present invention relates to a liquid crystal display element.
  • the classification based on the operation mode of the liquid crystal molecules is as follows: PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS. (In-plane switching), VA (vertical alignment), FFS (fringe field switching), FPA (field-induced photo-reactive alignment) mode.
  • the classification based on the element drive system is PM (passive matrix) and AM (active matrix). PM is classified into static, multiplex, etc., and AM is classified into TFT (thin film insulator), MIM (metal film insulator), and the like. TFTs are classified into amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to the manufacturing process.
  • the classification based on the light source includes a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both natural light and backlight.
  • the liquid crystal display element contains a liquid crystal composition having a nematic phase.
  • This composition has suitable properties. By improving the characteristics of the composition, an AM device having good characteristics can be obtained. The relationship between the two characteristics is summarized in Table 1 below. The characteristics of the composition will be further described based on a commercially available AM device.
  • the temperature range of the nematic phase is related to the temperature range in which the device can be used.
  • a preferred upper limit temperature of the nematic phase is about 70 ° C. or more, and a preferred lower limit temperature of the nematic phase is about ⁇ 10 ° C. or less.
  • the viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. A shorter response time is desirable even at 1 millisecond. Therefore, a small viscosity in the composition is preferred. A small viscosity at low temperatures is even more preferred.
  • the optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, a large optical anisotropy or a small optical anisotropy, ie an appropriate optical anisotropy is required.
  • the product ( ⁇ n ⁇ d) of the optical anisotropy ( ⁇ n) of the composition and the cell gap (d) of the device is designed to maximize the contrast ratio.
  • the appropriate value for the product depends on the type of operating mode. This value is in the range of about 0.30 ⁇ m to about 0.40 ⁇ m for the VA mode element and in the range of about 0.20 ⁇ m to about 0.30 ⁇ m for the IPS mode or FFS mode element.
  • a composition having a large optical anisotropy is preferable for a device having a small cell gap.
  • a large dielectric anisotropy in the composition contributes to a low threshold voltage, a small power consumption and a large contrast ratio in the device. Therefore, a large dielectric anisotropy is preferable.
  • a large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage is preferable.
  • a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after being used for a long time is preferable.
  • the stability of the composition against ultraviolet rays and heat is related to the lifetime of the device. When this stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM device used in a liquid crystal projector, a liquid crystal television, and the like.
  • a composition to which a small amount of a polymerizable compound is added is injected into the device.
  • the composition is irradiated with ultraviolet rays while applying a voltage between the substrates of the device.
  • the polymerizable compound polymerizes to form a polymer network in the composition.
  • the response time of the device is shortened, and image burn-in is improved.
  • Such an effect of the polymer can be expected for a device having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
  • a liquid crystal composition containing a polymer and a polar compound having no polymerizable group is used.
  • a composition to which a small amount of a polymerizable compound and a small amount of a polar compound are added is injected into the device.
  • polar compounds are adsorbed and arranged on the substrate surface.
  • the liquid crystal molecules are aligned according to this arrangement.
  • the composition is irradiated with ultraviolet rays while applying a voltage between the substrates of the device.
  • the polymerizable compound is polymerized to stabilize the alignment of the liquid crystal molecules.
  • the orientation of liquid crystal molecules can be controlled by the polymer and the polar compound, the response time of the device is shortened, and image burn-in is improved. Furthermore, in the element having no alignment film, the step of forming the alignment film is unnecessary. Since there is no alignment film, the electrical resistance of the device does not decrease due to the interaction between the alignment film and the composition. Such an effect by the combination of the polymer and the polar compound can be expected for a device having a mode such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
  • a mode such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
  • a composition having a positive dielectric anisotropy is used for an AM device having a TN mode.
  • a composition having a negative dielectric anisotropy is used in an AM device having a VA mode.
  • a composition having a positive or negative dielectric anisotropy is used in an AM device having an IPS mode or an FFS mode.
  • a composition having positive or negative dielectric anisotropy is used in a polymer-supported orientation type AM device.
  • Examples of liquid crystal compositions having negative dielectric anisotropy are disclosed in the following Patent Documents 1 to 6.
  • a polar compound having a polymerizable group (or a polymer thereof) and a polymerizable compound (or a polymer thereof) are combined with a liquid crystal compound, and the composition is used for a liquid crystal display element having no alignment film. .
  • One object of the present invention is a liquid crystal composition containing a polar compound having a polymerizable group (or a polymer thereof) and a polymerizable compound (or a polymer thereof), wherein the polar compound and the polymerizable compound are High compatibility with liquid crystal compounds.
  • Another object is a liquid crystal composition capable of achieving vertical alignment of liquid crystal molecules by the action of a polymer formed from the polar compound and the polymerizable compound.
  • nematic phase low minimum temperature of nematic phase, small viscosity, appropriate optical anisotropy, negatively large dielectric anisotropy, large specific resistance, high stability against ultraviolet rays, high heat resistance
  • a liquid crystal composition satisfying at least one characteristic in characteristics such as high stability.
  • Another object is a liquid crystal composition having an appropriate balance between at least two properties.
  • Another object is a liquid crystal display device containing such a composition.
  • Another object is an AM device having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
  • the present invention contains a polar compound having at least one polymerizable group as a first additive, and a polymerizable compound having at least three polymerizable groups as a second additive, and has a negative dielectric anisotropy.
  • the present invention relates to a liquid crystal composition having the same and a liquid crystal display device containing the composition.
  • One advantage of the present invention is a liquid crystal composition containing a polar compound having a polymerizable group (or this polymer) and a polymerizable compound (or this polymer), wherein the polar compound and the polymerizable compound are: High compatibility with liquid crystal compounds.
  • Another advantage is a liquid crystal composition in which vertical alignment of liquid crystal molecules can be achieved by the action of a polymer formed from the polar compound and the polymerizable compound.
  • Another advantage is the high maximum temperature of the nematic phase, the low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, negative large dielectric anisotropy, large specific resistance, high stability against ultraviolet light, high heat resistance It is a liquid crystal composition satisfying at least one characteristic in characteristics such as high stability. Another advantage is a liquid crystal composition having an appropriate balance between at least two properties. Another advantage is a liquid crystal display device containing such a composition. Another advantage is an AM device having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
  • liquid crystal composition and “liquid crystal display element” may be abbreviated as “composition” and “element”, respectively.
  • “Liquid crystal display element” is a general term for liquid crystal display panels and liquid crystal display modules.
  • “Liquid crystal compound” is a compound having a liquid crystal phase such as a nematic phase and a smectic phase, and a liquid crystal phase, but has a composition for the purpose of adjusting characteristics such as temperature range, viscosity, and dielectric anisotropy of the nematic phase. It is a general term for compounds mixed with products.
  • This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod-like.
  • the “polymerizable compound” is a compound added for the purpose of forming a polymer in the composition.
  • a liquid crystalline compound having alkenyl is not polymerizable in that sense.
  • the liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. Additives such as optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds are added to this liquid crystal composition as necessary.
  • the Liquid crystal compounds and additives are mixed in such a procedure.
  • the ratio (content) of the liquid crystal compound is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition not containing the additive even when the additive is added.
  • the ratio (addition amount) of the additive is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition not containing the additive. Weight parts per million (ppm) may be used.
  • the ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.
  • the upper limit temperature of the nematic phase may be abbreviated as “the upper limit temperature”.
  • “Lower limit temperature of nematic phase” may be abbreviated as “lower limit temperature”.
  • High specific resistance means that the composition has a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature after long-term use. It means having.
  • “High voltage holding ratio” means that the device has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and a large voltage not only at room temperature but also at a temperature close to the upper limit temperature after long-term use.
  • compositions or devices characteristics may be examined before and after a aging test (including an accelerated deterioration test).
  • the expression “increasing dielectric anisotropy” means that when the composition has a positive dielectric anisotropy, the value increases positively, and the composition having a negative dielectric anisotropy When it is a thing, it means that the value increases negatively.
  • the compound represented by the formula (1) may be abbreviated as “compound (1)”. At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as “compound (1)”. “Compound (1)” means one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. The same applies to compounds represented by other formulas.
  • 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 the number of 'A' is 2 Even when there are more than two, their positions can be selected without restriction. This rule also applies to the expression “at least one 'A' is replaced by 'B'".
  • This rule applies not only to replacement with —O— but also to replacement with a divalent group such as —CH ⁇ CH— or —COO—.
  • alkyl at least one —CH 2 — may be replaced by a cycloalkylene having 3 to 8 carbon atoms. The carbon number of the alkyl increases with this replacement. In such a case, the maximum carbon number is 30.
  • This rule applies not only to monovalent groups such as alkyl, but also to divalent groups such as alkylene.
  • the symbol of the terminal group R 1 is used for a plurality of compounds.
  • two groups represented by two arbitrary R 1 may be the same or different.
  • R 1 of the compound (1-1) is ethyl and R 1 of the compound (1-2) is ethyl.
  • R 1 of compound (1-1) is ethyl and R 1 of compound (1-2) is propyl.
  • This rule applies to other symbols.
  • Formula (1) when a is 2, two rings A exist. In this compound, the two rings represented by the two rings A may be the same or different. This rule also applies to any two rings A when a is greater than 2. This rule applies to other symbols.
  • This rule also applies to the case of two -Sp 11 -P 5 in the compound (5-7).
  • Symbols such as A, B, C, and D surrounded by hexagons correspond to rings such as ring A, ring B, ring C, and ring D, respectively, and represent rings such as six-membered rings and condensed rings.
  • the diagonal line across this hexagon represents that any hydrogen on the ring may be replaced with a group such as —Sp 1 —P 1 .
  • a subscript such as 'k' indicates the number of groups replaced. When the subscript 'k' is 0, there is no such replacement. When the subscript 'k' is 2 or more, there are a plurality of -Sp 1 -P 1 on the ring J.
  • the plurality of groups represented by —Sp 1 —P 1 may be the same or different.
  • 2-Fluoro-1,4-phenylene means the following two divalent groups.
  • fluorine may be leftward (L) or rightward (R).
  • This rule also applies to asymmetric divalent groups generated by removing two hydrogens from the ring, such as tetrahydropyran-2,5-diyl.
  • This rule also applies to divalent linking groups such as carbonyloxy (—COO— or —OCO—).
  • the alkyl of the liquid crystal compound is linear or branched and does not include cyclic alkyl. Linear alkyl is preferred over branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl. As the configuration of 1,4-cyclohexylene, trans is preferable to cis for increasing the maximum temperature.
  • the present invention includes the following items.
  • Item 1 A liquid crystal composition containing a polar compound having at least one polymerizable group as a first additive and a polymerizable compound having at least three polymerizable groups as a second additive, and having negative dielectric anisotropy .
  • Item 2. The liquid crystal composition according to item 1, comprising at least one compound selected from the group of compounds represented by formula (1) as a first component.
  • R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen is replaced by fluorine or chlorine
  • ring A and ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran- 2,5-diyl, 1,4-phenylene, at least one hydrogen replaced with fluorine or chlorine, 1,4-phenylene, naphthalene-2,6-diyl, at least one hydrogen replaced with fluorine or chlorine Naphthalene-2,6-diyl, chroman-2,6-diyl, or at least one hydrogen is replaced by fluor
  • Item 3. The liquid crystal composition according to item 1 or 2, containing at least one compound selected from the group of compounds represented by formulas (1-1) to (1-22) as a first component.
  • R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, It is alkenyl having 2 to 12 carbons in which one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons.
  • Item 4. The liquid crystal composition according to any one of items 1 to 3, wherein the proportion of the first component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.
  • Item 5. The liquid crystal composition according to any one of items 1 to 4, comprising at least one compound selected from the group of compounds represented by formula (2) as the second component.
  • R 3 and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen is replaced by fluorine or chlorine Or alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine;
  • Ring D and Ring E are each independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene;
  • Z 3 represents a single bond, —CH 2 CH 2 —, —CH 2 O— , —OCH 2 —, —COO—, or —OCO—;
  • c is 1, 2, or 3.
  • Item 6. The liquid crystal composition according to any one of items 1 to 5, comprising at least one compound selected from the group of compounds represented by formulas (2-1) to (2-13) as a second component: object.
  • R 3 and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, It is alkyl having 1 to 12 carbons in which one hydrogen is replaced with fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced with fluorine or chlorine.
  • Item 7. The liquid crystal composition according to item 5 or 6, wherein the ratio of the second component is in the range of 10% by weight to 70% by weight based on the weight of the liquid crystal composition.
  • Item 8 The liquid crystal composition according to any one of items 1 to 7, wherein the first additive is a polar compound having a hetero atom selected from nitrogen, oxygen, sulfur, and phosphorus.
  • Item 9. The liquid crystal composition according to any one of items 1 to 8, comprising at least one compound selected from the group of polar compounds represented by formula (3) and formula (4) as a first additive.
  • R 7 is hydrogen, fluorine, chlorine, or alkyl having 1 to 25 carbon atoms, and in this alkyl, at least one —CH 2 — is —NR 0 —, —O—, — May be replaced by S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, or cycloalkylene having 3 to 8 carbon atoms, and at least one tertiary Carbon (> CH—) may be replaced with nitrogen (> N—), in which at least one hydrogen may be replaced with fluorine or chlorine, where R 0 is hydrogen or R 8 represents at least one of an oxygen atom having an OH structure, a sulfur atom having an SH structure, and a nitrogen atom having a primary, secondary, or tertiary amine
  • Polar group having; ring J, ring K and ring L are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1 , 4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6 -Diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diy
  • Z 7 and Z 8 are independently a single bond or alkylene having 1 to 10 carbon atoms, in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, or —OCO—, and at least one —CH 2 CH 2 — may be —CH ⁇ CH—, —C ( CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, or —C (CH 3 ) ⁇ C (CH 3 ) —, in which at least one hydrogen is fluorine Or may be replaced by chlorine; P 1 , P 2 , and P 3 are polymerizable groups; Sp 1 , Sp 2 , and Sp 3 are independently a single bond or alkylene having 1 to 10 carbon atoms so And in this alkylene, at least one —CH 2 — may be replaced by —O—, —COO—, —OCO—, or
  • Item 10 The liquid crystal composition according to item 9, wherein in the formula (3) according to item 9, R 8 is a group selected from the group of polar groups represented by formulas (A1) to (A4).
  • Sp 6 , Sp 8 , and Sp 9 are each independently a single bond or alkylene having 1 to 12 carbons, in which at least one —CH 2 — is —O—, —S—, —NH—, —N (R 0 ) —, —CO—, —CO—O—, —O—CO, —O—CO—O—, —S—CO—, — CO—S—, —N (R 0 ) —CO—O—, —O—CO—N (R 0 ) —, —N (R 0 ) —CO—N (R 0 ) —, —CH ⁇ CH— , Or —C ⁇ C—, in which at least one hydrogen may be replaced with fluorine
  • Sp 7 is>CH-,> CR 0 -,> N-, or> C ⁇ , where R 0 Is hydrogen or alkyl having 1 to 12 carbons;
  • X 17 is —OH, —OR 0 , —COOH, —NH 2 , —NHR 0 , —N (R 0 ) 2 , —SH, —SR 0 , Where R 0 is hydrogen or alkyl of 1 to 12 carbons;
  • X 18 is —O—, —CO—, —NH—, —NR 0 —, —S—, or a single bond Wherein R 0 is hydrogen or alkyl having 1 to 12 carbons;
  • Z 10 is a single bond or alkylene having 1 to 15 carbons, in which at least one —CH 2 — is —C ⁇ C—, —CH ⁇ CH—, —COO—, —OCO—, —CO—, or —O— may be substituted, in which at least one
  • P 1 , P 2 and P 3 are independently selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5).
  • Item 10 The liquid crystal composition according to item 9, which is a group.
  • M 1 , M 2, and M 3 are independently hydrogen, fluorine, alkyl of 1 to 5 carbon atoms or at least one hydrogen is fluorine or chlorine, 1-5 alkyl substituted with
  • Item 12. The liquid crystal according to any one of items 1 to 11, wherein the first additive is at least one compound selected from the group of polar compounds represented by formulas (3-1) to (3-15): Composition.
  • R 7 is hydrogen, fluorine, chlorine, or alkyl having 1 to 25 carbons, and in this alkyl, at least one —CH 2 — is — NR 0 —, —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, or cycloalkylene having 3 to 8 carbon atoms may be substituted.
  • At least one tertiary carbon may be replaced with nitrogen (> N—), and in these groups at least one hydrogen may be replaced with fluorine or chlorine
  • R 0 is hydrogen or alkyl having 1 to 12 carbons
  • at least one hydrogen may be replaced by fluorine or chlorine
  • Sp 10 is a single bond or alkylene having 1 to 10 carbons, in which at least one —CH 2 — is —O —, —COO—, —OCO—, or —OCOO— may be substituted, and at least one —CH 2 CH 2 — may be replaced with —CH ⁇ CH— or —C ⁇ C—
  • Item 13 The liquid crystal according to any one of items 1 to 12, wherein the first additive is at least one compound selected from the group of polar compounds represented by formulas (4-1) to (4-9): Composition.
  • R 9 is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, One hydrogen is alkyl having 1 to 12 carbon atoms replaced by fluorine or chlorine, or at least one hydrogen is alkenyl having 2 to 12 carbon atoms replaced by fluorine or chlorine;
  • Sp 4 and Sp 5 are each independently a single bond or alkylene having 1 to 7 carbon
  • Item 14 The liquid crystal composition according to any one of items 1 to 13, wherein the ratio of the first additive is in the range of 0.05% by weight to 10% by weight based on the weight of the liquid crystal composition.
  • Item 15. The liquid crystal composition according to any one of items 1 to 14, containing at least one compound selected from the group of polymerizable compounds represented by formula (5) as the second additive.
  • ring T and ring V are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine- 2-yl or pyridin-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen.
  • ring U may be 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1, 2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1, -Diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5- Diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5- Diyl, 1,3-dioxane-2,5-
  • P 4 , P 5 and P 6 are independently selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Item 16.
  • M 1 , M 2, and M 3 are independently hydrogen, fluorine, alkyl of 1 to 5 carbon atoms or at least one hydrogen is fluorine or chlorine, 1-5 alkyl substituted with
  • Item 17. The item according to any one of Items 1 to 16, comprising at least one compound selected from the group of polymerizable compounds represented by Formula (5-1) to Formula (5-7) as the second additive.
  • P 4 , P 5 , and P 6 are each independently a polymerizable group represented by formula (P-1) to formula (P-3).
  • Sp 10 , Sp 11 , and Sp 12 are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH 2 — is —O—, —COO—, — OCO—, or —OCOO— may be replaced, and at least one —CH 2 CH 2 — may be replaced with —CH ⁇ CH— or —C ⁇ C—, and in these groups, at least One hydrogen may be replaced with fluorine or chlorine.
  • Item 18 The liquid crystal composition according to any one of items 15 to 17, wherein the ratio of the second additive is in the range of 0.03% by weight to 10% by weight based on the weight of the liquid crystal composition.
  • Item 19 A liquid crystal display device comprising the liquid crystal composition according to any one of items 1 to 18.
  • Item 20 The liquid crystal display element according to item 19, wherein the operation mode of the liquid crystal display element is an IPS mode, a VA mode, an FFS mode, or an FPA mode, and the driving method of the liquid crystal display element is an active matrix method.
  • Item 21 A liquid crystal display element of a polymer-supported alignment type comprising the liquid crystal composition according to any one of items 1 to 18, wherein the first additive and the second additive in the liquid crystal composition are polymerized.
  • Item 22 Item 19. A liquid crystal display element having no alignment film, comprising the liquid crystal composition according to any one of items 1 to 18, wherein the first additive and the second additive in the liquid crystal composition are polymerized.
  • Item 23 Use of the liquid crystal composition according to any one of items 1 to 18 in a liquid crystal display device.
  • Item 24 Use of the liquid crystal composition according to any one of items 1 to 18 in a polymer supported alignment type liquid crystal display element.
  • Item 25 Use of the liquid crystal composition according to any one of items 1 to 18 in a liquid crystal display device having no alignment film.
  • the present invention includes the following items.
  • the present invention includes the following items.
  • the compounds (5) to (7) described in JP-A-2006-199941 are liquid crystal compounds having positive dielectric anisotropy, but at least selected from the group of these compounds A composition as described above containing one compound.
  • the above composition comprising at least two of the above polar compounds.
  • the above composition further comprising a polar compound different from the above polar compound.
  • One, two, or at least three of additives such as optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds A composition as described above containing one. This additive may be the same as or different from the first additive and the second additive.
  • FIG. 1 An AM device containing the above composition.
  • H A device containing the above composition and having a TN, ECB, OCB, IPS, FFS, VA, or FPA mode.
  • I A transmissive element containing the above composition.
  • J The above composition is used as a composition having a nematic phase.
  • K Use as an optically active composition by adding an optically active compound to the above composition.
  • composition of the present invention will be described in the following order. First, the composition of the composition will be described. Second, the main characteristics of the component compounds and the main effects of the compounds on the composition will be explained. Third, the combination of components in the composition, the preferred ratio of the components, and the basis thereof will be described. Fourth, a preferred form of the component compound will be described. Fifth, preferred component compounds are shown. Sixth, additives that may be added to the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Finally, the use of the composition will be described.
  • composition of the composition will be explained.
  • the composition of the present invention is classified into Composition A and Composition B.
  • the composition A may further contain other liquid crystal compounds, additives and the like in addition to the liquid crystal compound selected from the compound (1) and the compound (2).
  • the “other liquid crystal compound” is a liquid crystal compound different from the compound (1) and the compound (2).
  • Such compounds are mixed into the composition for the purpose of further adjusting the properties.
  • Additives include optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like.
  • Composition B consists essentially of a liquid crystalline compound selected from compound (1) and compound (2). “Substantially” means that the composition may contain an additive but no other liquid crystal compound. Composition B has fewer components than composition A. From the viewpoint of reducing the cost, the composition B is preferable to the composition A. The composition A is preferable to the composition B from the viewpoint that the characteristics can be further adjusted by mixing other liquid crystal compounds.
  • the main characteristics of the component compounds and the main effects of the compounds on the characteristics of the composition will be explained.
  • the main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention.
  • L means large or high
  • M means moderate
  • S means small or low.
  • L, M, and S are classifications based on a qualitative comparison among the component compounds, and the symbol 0 means that the value is zero or close to zero.
  • the main effects of the component compound on the properties of the composition are as follows.
  • Compound (1) increases the dielectric anisotropy.
  • Compound (2) increases the maximum temperature or decreases the viscosity.
  • the compound (3) and the compound (4) are adsorbed on the substrate surface by the action of the polar group and control the alignment of the liquid crystal molecules. In order to obtain the desired effect, it is essential that these compounds have high compatibility with liquid crystal compounds.
  • These compounds have a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and their molecular structure is rod-like, which is optimal for this purpose.
  • the compound (5) is added to the composition for the purpose of further adapting to the polymer-supported orientation type device.
  • Compound (3), compound (4), and compound (5) give a polymer by polymerization. This polymer stabilizes the alignment of the liquid crystal molecules, thereby reducing the response time of the device and improving image burn-in.
  • a preferred combination of components in the composition is compound (1) + compound (2).
  • Vertical alignment of liquid crystal molecules is achieved by combining such a composition with a polar compound (or a polymer thereof) and a polymerizable compound (or a polymer thereof). If the “other liquid crystalline compound” is in a small amount, the same effect can be achieved even if it is added to such a composition.
  • a desirable ratio of compound (1) is approximately 10% by weight or more for increasing the dielectric anisotropy, and approximately 90% by weight or less for decreasing the viscosity.
  • a more desirable ratio is in the range of approximately 15% by weight to approximately 80% by weight.
  • a particularly preferred ratio is in the range of approximately 20% by weight to approximately 70% by weight.
  • a desirable ratio of the compound (2) is approximately 10% by weight or more for increasing the maximum temperature or decreasing the viscosity, and approximately 70% by weight or less for increasing the dielectric anisotropy.
  • a more desirable ratio is in the range of approximately 10% by weight to approximately 65% by weight.
  • a particularly preferred ratio is in the range of approximately 15% by weight to approximately 60% by weight.
  • Compound (3) and Compound (4) are added to the composition for the purpose of controlling the alignment of liquid crystal molecules.
  • a desirable ratio of compound (3) or compound (4) is approximately 0.05% by weight or more for aligning liquid crystal molecules, and approximately 10% by weight or less for preventing display defects of the device.
  • a more desirable ratio is in the range of approximately 0.1% by weight to approximately 7% by weight.
  • a particularly desirable ratio is in the range of approximately 0.5% by weight to approximately 5% by weight.
  • Compound (5) is added to the composition for the purpose of adapting to a polymer-supported orientation type device.
  • a desirable ratio of compound (5) is approximately 0.03% by weight or more for improving the long-term reliability of the element, and approximately 10% by weight or less for preventing display defects of the element.
  • a more desirable ratio is in the range of approximately 0.1% by weight to approximately 2% by weight.
  • a particularly preferred ratio is in the range of approximately 0.2% by weight to approximately 1.0% by weight.
  • R 1 and R 2 independently represent alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen. C 2-12 alkenyl substituted with fluorine or chlorine, or C 2-12 alkenyloxy. Desirable R 1 or R 2 is alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat, and alkoxy having 1 to 12 carbons for increasing the dielectric anisotropy.
  • R 3 and R 4 are independently an alkyl having 1 to 12 carbons, an alkoxy having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, an alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine 12 alkyls or alkenyls having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine.
  • Desirable R 3 or R 4 is alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat, and alkenyl having 2 to 12 carbons for decreasing the minimum temperature or decreasing the viscosity. .
  • Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. More desirable alkyl is ethyl, propyl, butyl, pentyl, or heptyl for decreasing the viscosity.
  • Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.
  • Preferred alkenyl is 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, or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl for decreasing the viscosity.
  • the preferred configuration of —CH ⁇ CH— in these alkenyls depends on the position of the double bond.
  • Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity.
  • Cis is preferred for alkenyl such as 2-butenyl, 2-pentenyl, and 2-hexenyl.
  • Preferred alkenyloxy is vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, or 4-pentenyloxy. More preferable alkenyloxy is allyloxy or 3-butenyloxy for decreasing the viscosity.
  • alkyl in which at least one hydrogen is replaced by fluorine or chlorine are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl. Or 8-fluorooctyl. Further preferred examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl or 5-fluoropentyl for increasing the dielectric anisotropy.
  • alkenyl in which at least one hydrogen is replaced by fluorine or chlorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro -4-pentenyl, or 6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinyl or 4,4-difluoro-3-butenyl for decreasing the viscosity.
  • Ring A and Ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, at least one hydrogen is replaced by fluorine or chlorine 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-2,6-diyl, chroman-2,6-diyl, in which at least one hydrogen is replaced by fluorine or chlorine, or at least one hydrogen Chroman-2,6-diyl replaced with fluorine or chlorine.
  • Preferred ring A or ring C is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2, 3-difluoro-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl, or 7,8-difluorochroman-2,6-diyl. More preferred ring A or ring C is 1,4-cyclohexylene or 1,4-phenylene.
  • preferred ring A or ring C is 1,4-cyclohexylene for decreasing the viscosity, tetrahydropyran-2,5-diyl for increasing the dielectric anisotropy, and optically anisotropic 1,4-phenylene for increasing the properties.
  • Tetrahydropyran-2,5-diyl is Or And preferably It is.
  • Ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4, 5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl.
  • Preferred ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, or 7,8-difluorochroman-2,6-diyl. More preferred ring B is 2,3-difluoro-1,4-phenylene or 2-chloro-3-fluoro-1,4-phenylene.
  • Particularly preferred ring B is 2,3-difluoro-1,4-phenylene.
  • preferred ring B is 2,3-difluoro-1,4-phenylene for decreasing the viscosity, and 2-chloro-3-fluoro-1,4-phenylene for decreasing the optical anisotropy.
  • it is 7,8-difluorochroman-2,6-diyl.
  • Ring D and ring E are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene.
  • Preferred ring D or ring E is 1,4-cyclohexylene for decreasing the viscosity or increasing the maximum temperature, and 1,4-phenylene for decreasing the minimum temperature.
  • Z 1 and Z 2 are each independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—.
  • Desirable Z 1 or Z 2 is a single bond for decreasing the viscosity, —CH 2 CH 2 — for decreasing the minimum temperature, and —CH 2 O— or —OCH for increasing the dielectric anisotropy.
  • Z 3 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—.
  • Desirable Z 3 is a single bond for decreasing the viscosity, —CH 2 CH 2 — for decreasing the minimum temperature, and —COO— or —OCO— for increasing the maximum temperature.
  • A is 1, 2, or 3, b is 0 or 1, and the sum of a and b is 3 or less.
  • Preferred a is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.
  • Preferred b is 0 for decreasing the viscosity, and 1 for decreasing the minimum temperature.
  • c is 1, 2 or 3.
  • Preferred c is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.
  • R 8 is a polar group.
  • R 10 is a polar group.
  • the compound (3) or the compound (4) is preferably stable with respect to ultraviolet rays and heat. When compound (3) or compound (4) is added to the composition, it is preferable that this compound does not lower the voltage holding ratio of the device.
  • the compound (3) or the compound (4) preferably has low volatility.
  • a preferred molar mass is 130 g / mol or more.
  • a more preferred molar mass is in the range of 150 g / mol to 500 g / mol.
  • Preferred compound (3) or compound (4) has a polymerizable group such as acryloyloxy (—OCO—CH ⁇ CH 2 ) or methacryloyloxy (—OCO— (CH 3 ) C ⁇ CH 2 ).
  • the polar group has a non-covalent interaction with the surface of the glass substrate or metal oxide film.
  • Preferred polar groups have a heteroatom selected from the group of nitrogen, oxygen, sulfur, and phosphorus. Preferred polar groups have at least one, or at least two of these heteroatoms.
  • Further preferred polar groups include hydrogen from compounds selected from the group of alcohols, primary, secondary, and tertiary amines, ketones, carboxylic acids, thiols, esters, ethers, thioethers, and combinations thereof. It is a monovalent group derived by removing. The structure of these groups may be linear, branched, cyclic, or a combination thereof.
  • Particularly preferred polar groups have at least one oxygen atom of the OH structure or at least one nitrogen atom of a primary, secondary or tertiary amine structure.
  • the most preferred polar group is a hydroxy group (carbon-OH).
  • Examples of polar groups R 8 is a group represented by the formula (A1) in formula (A4).
  • Sp 6 , Sp 8 , and Sp 9 are each independently a single bond or alkylene having 1 to 12 carbons, in which at least one —CH 2 — is —O—, —S—, —NH—, —N (R 0 ) —, —CO—, —CO—O—, —O—CO, —O—CO—O—, —S—CO—, — CO—S—, —N (R 0 ) —CO—O—, —O—CO—N (R 0 ) —, —N (R 0 ) —CO—N (R 0 ) —, —CH ⁇ CH— , Or —C ⁇ C—, in which at least one hydrogen may be replaced with fluorine or chlorine, where R 0 is hydrogen or alkyl of 1 to 12 carbons.
  • Sp 7 is>CH—,> CR 0 —,> N—, or> C ⁇ , where R 0 is hydrogen or alkyl having 1 to 12 carbons. That is, Sp 7 in formula (A2) is>CH-,> CR 0- , or> N-, and Sp 7 in formula (A3) means> C ⁇ .
  • Preferred Sp 6 , Sp 8 or Sp 9 is a single bond, — (CH 2 ) p1 —, — (CH 2 ) p1 —O—, — (CH 2 CH 2 O) q1 —CH 2 CH 2 —, — (CH 2 ) p1 —O—CO—, — (CH 2 ) p1 —O—CO—O—, —CH 2 CH 2 —S—CH 2 CH 2 —, or —CH 2 CH 2 —NHCH 2 CH 2 Where p1 is an integer from 1 to 12 and q1 is an integer from 1 to 3.
  • Sp 6 , Sp 8 , or Sp 9 is ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene -N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene, and butenylene.
  • X 17 represents —OH, —OR 0 , —COOH, —NH 2 , —NHR 0 , —N (R 0 ) 2 , —SH, —SR 0 , Where R 0 is hydrogen or alkyl of 1 to 12 carbons.
  • X 18 represents —O—, —CO—, —NH—, —NR 0 —, —S—, or a single bond, where R 0 represents hydrogen or a carbon number of 1 to 12 Of alkyl.
  • Z 10 is a single bond or alkylene having 1 to 15 carbon atoms, and in this alkylene, at least one —CH 2 — is —C ⁇ C—, —CH ⁇ CH—, —COO—, —OCO—, -CO-, or -O- may be substituted, and in these groups, at least one hydrogen may be substituted with fluorine or chlorine.
  • Ring P is aryl having 6 to 25 carbons, in which 1 to 3 hydrogens are —OH, — (CH 2 ) q —OH, fluorine, chlorine, alkyl having 1 to 5 carbons, or At least one hydrogen may be replaced with 1 to 5 carbon alkyl replaced with fluorine or chlorine, where q is 1, 2, 3, or 4. n is 0, 1, 2, or 3, and m is 1, 2, 3, 4, or 5.
  • Aryl is a monovalent group derived by removing one hydrogen from an aromatic hydrocarbon and does not contain heteroatoms.
  • Aryl may be monocyclic or polycyclic. That is, an aryl has at least one ring that may be fused (eg, naphthyl) and the two rings may be covalently linked (eg, biphenyl).
  • Aryl may have a combination of fused and linked rings.
  • Aryl may be substituted. Examples of the substituent are —OH, — (CH 2 ) q —OH, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Where q is 1, 2, 3, or 4.
  • Preferred aryls are benzene, biphenyl, terphenyl, [1,1 ′: 3 ′, 1 ′′] terphenyl, naphthalene, anthracene, binaphthyl, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene.
  • R 8 is a polar group having at least one of an oxygen atom having an OH structure, a sulfur atom having an SH structure, and a nitrogen atom having a primary, secondary, or tertiary amine structure. is there.
  • Preferred R 8 is —OH, — (CH 2 ) n —OH, —O— (CH 2 ) n —OH, — [O— (CH 2 ) n1 —] n2 —OH, —COOH, — (CH 2 ) N —COOH, —O— (CH 2 ) n —COOH, or — [O— (CH 2 ) n1 —] n2 —COOH.
  • n, n1, and n2 are each independently an integer of 1 to 12, preferably 1, 2, 3, or 4.
  • Preferred R 8 is —NH 2 , —NH— (CH 2 ) n 3 H, — (CH 2 ) n —NH 2 , — (CH 2 ) n —NH— (CH 2 ) n 3 H, —NH— (CH 2 ) n —NH 2 , —NH— (CH 2 ) n —NH— (CH 2 ) n3 H, — (CH 2 ) n1 —NH— (CH 2 ) n2 —NH 2 , — (CH 2 ) n1 — NH— (CH 2 ) n2 —NH— (CH 2 ) n3 H, —O— (CH 2 ) n —NH 2 , — (CH 2 ) n1 —O— (CH 2 ) n —NH 2 , — (CH 2 ) n1 —O— (CH 2 ) n —NH 2 , — (CH 2 ) n1 —NH
  • R 8 is particularly preferably —OH or —NH 2 .
  • —OH is preferable to —O—, —CO—, or —COO— because it has a high anchoring force.
  • Groups having a plurality of heteroatoms are particularly preferred. The compound having such a polar group is effective even at a low concentration.
  • R 7 is hydrogen, fluorine, chlorine, or alkyl having 1 to 25 carbon atoms, and in this alkyl, at least one —CH 2 — is —NR 0 —, —O—, — May be replaced by S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, or cycloalkylene having 3 to 8 carbon atoms, and at least one tertiary Carbon (> CH—) may be replaced with nitrogen (> N—), in which at least one hydrogen may be replaced with fluorine or chlorine, where R 0 is hydrogen or Alkyl having 1 to 12 carbons. Preferred R 7 is alkyl having 1 to 25 carbons.
  • P 1 , P 2 , and P 3 are independently a polymerizable group.
  • Preferred P 1 , P 2 , or P 3 is a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). More desirable P 1 , P 2 , or P 3 is a group represented by the formula (P-1), the formula (P-2), or the formula (P-3). Particularly preferred P 1 , P 2 , or P 3 is a group represented by formula (P-1) or formula (P-2). Most preferred P 1 , P 2 or P 3 is a group represented by the formula (P-1).
  • a preferred group represented by the formula (P-1) is —OCO—CH ⁇ CH 2 or —OCO—C (CH 3 ) ⁇ CH 2 .
  • the wavy lines in the formulas (P-1) to (P-5) indicate the binding sites.
  • M 1 , M 2, and M 3 are independently hydrogen, fluorine, alkyl of 1 to 5 carbon atoms or at least one hydrogen is fluorine or chlorine, 1-5 alkyl substituted with Preferred M 1 , M 2 or M 3 is hydrogen or methyl for increasing the reactivity. More preferred M 1 is hydrogen or methyl, and more preferred M 2 or M 3 is hydrogen.
  • Sp 1 , Sp 2 , and Sp 3 are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH 2 — is —O—, —COO—, —OCO—, or —OCOO— and at least one —CH 2 CH 2 — may be replaced with —CH ⁇ CH— or —C ⁇ C— In this group, at least one hydrogen may be replaced by fluorine or chlorine.
  • Further preferred Sp 1 , Sp 2 or Sp 3 is a single bond. However, when ring J and ring L are phenyl, Sp 1 and Sp 3 are single bonds.
  • ring J, ring K, and ring L are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene.
  • At least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or At least one hydrogen may be replaced by alkyl having 1 carbon atoms which is replaced by fluorine or chlorine 12.
  • Z 7 and Z 8 are each independently a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH 2 — is —O—, —CO—, —COO—, or —OCO— may be substituted, and at least one —CH 2 CH 2 — may be —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, Or —C (CH 3 ) ⁇ C (CH 3 ) —, in which at least one hydrogen may be replaced with fluorine or chlorine.
  • Preferred Z 7 or Z 8 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—. Further preferred Z 7 or Z 8 is a single bond.
  • g and h are independently 0, 1, 2, 3, or 4, and the sum of g and h is 0, 1, 2, 3, or 4.
  • Preferred g or h is 0, 1, or 2.
  • k and p are independently 0, 1, 2, 3, or 4.
  • Preferred k or p is 1 or 2.
  • o is 1, 2, 3, or 4.
  • Preferred o is 1 or 2.
  • Sp 10 is a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH 2 — is —O—, — COO—, —OCO—, or —OCOO— may be substituted, and at least one —CH 2 CH 2 — may be replaced with —CH ⁇ CH— or —C ⁇ C—
  • at least one hydrogen may be replaced by fluorine or chlorine.
  • L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, methyl, or ethyl.
  • R 11 and R 12 are independently hydrogen or methyl.
  • R 10 is a group represented by —OH, —OR 0 , —NH 2 , —NHR 0 or —N (R 0 ) 2 , where R 0 is hydrogen or carbon number 1 to 12 alkyls.
  • R 2 is particularly preferably —OH or —NH 2 .
  • —OH is preferable to —O—, —CO—, or —COO— because it has a high anchoring force.
  • Groups having a plurality of heteroatoms (nitrogen, oxygen) are particularly preferred. The compound having such a polar group is effective even at a low concentration.
  • R 9 is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or at least one hydrogen is replaced by fluorine or chlorine Alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.
  • Preferred R 9 is alkyl having 1 to 12 carbons.
  • ring M and ring N are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3.
  • Z 9 is a single bond, —CH 2 CH 2 —, —CH ⁇ CH—, —C ⁇ C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —. , —CH 2 O—, —OCH 2 —, or —CF ⁇ CF—.
  • Preferred Z 9 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—.
  • Further preferred Z 9 is a single bond.
  • Sp 4 and Sp 5 are each independently a single bond or alkylene having 1 to 7 carbons, and in this alkylene, at least one —CH 2 — is —O—, —COO—, Or at least one —CH 2 CH 2 — may be replaced with —CH ⁇ CH—, in which at least one hydrogen is replaced with fluorine; Also good.
  • Preferred Sp 4 or Sp 5 is a single bond.
  • j is 0, 1, 2, 3, or 4.
  • Preferred j is 0, 1, or 2.
  • L 5 , L 6 , L 7 , L 8 , L 9 , L 10 , L 11 , L 12 , L 13 , L 14 , L 15 , and L 16 is independently hydrogen, fluorine, methyl, or ethyl.
  • Preferred L 5 to L 16 are hydrogen or fluorine.
  • P 4 , P 5 , and P 6 are independently a polymerizable group.
  • Preferred P 4 , P 5 , or P 6 is a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). More desirable P 4 , P 5 or P 6 is a group represented by the formula (P-1), the formula (P-2) or the formula (P-3). Particularly preferred P 4 , P 5 or P 6 is a group represented by the formula (P-1) or the formula (P-2). Most preferred P 4 , P 5 or P 6 is a group represented by the formula (P-1).
  • a preferred group represented by the formula (P-1) is —OCO—CH ⁇ CH 2 or —OCO—C (CH 3 ) ⁇ CH 2 .
  • the wavy lines in the formulas (P-1) to (P-5) indicate the binding sites.
  • M 1 , M 2, and M 3 are independently hydrogen, fluorine, alkyl of 1 to 5 carbon atoms or at least one hydrogen is fluorine or chlorine, 1-5 alkyl substituted with Preferred M 1 , M 2 or M 3 is hydrogen or methyl for increasing the reactivity. More preferred M 1 is hydrogen or methyl, and more preferred M 2 or M 3 is hydrogen.
  • Sp 10 , Sp 11 , and Sp 12 are each independently a single bond or alkylene having 1 to 10 carbon atoms.
  • this alkylene at least one —CH 2 — may be replaced by —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH 2 CH 2 — may be —CH ⁇ CH— or —C ⁇ C— may be substituted, and in these groups at least one hydrogen may be substituted with fluorine or chlorine.
  • ring T and ring V are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine- 2-yl or pyridin-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen. It may be replaced by alkyl having 1 to 12 carbon atoms replaced by fluorine or chlorine.
  • Preferred ring T or ring V is phenyl.
  • Ring U is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene -1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2 , 7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, At least one hydrogen is fluorine, chlorine,
  • Desirable compounds (1) are the compounds (1-1) to (1-22) described in item 3.
  • at least one of the first components is compound (1-1), compound (1-3), compound (1-4), compound (1-6), compound (1-8), or compound (1-10) is preferred.
  • At least two of the first components are compound (1-1) and compound (1-6), compound (1-1) and compound (1-10), compound (1-3) and compound (1-6), A compound (1-3) and a compound (1-10), a compound (1-4) and a compound (1-6), or a combination of a compound (1-4) and a compound (1-8) is preferable.
  • Desirable compound (2) is the compound (2-1) to the compound (2-13) according to item 6.
  • at least one of the second components is the compound (2-1), the compound (2-3), the compound (2-5), the compound (2-6), the compound (2-8), or the compound (2-9) is preferred.
  • At least two of the second components are compound (2-1) and compound (2-3), compound (2-1) and compound (2-5), or compound (2-1) and compound (2-6). A combination is preferred.
  • Desirable compound (3) is the compound (3-1) to the compound (3-15) according to item 12.
  • at least one of the first additives is compound (3-6), compound (3-8), compound (3-10), compound (3-11), compound (3-13), or The compound (3-15) is preferred. It is preferable that at least two of the first additives are the compound (3-1) and the compound (3-11), or the combination of the compound (3-3) and the compound (3-8).
  • Desirable compound (4) is the compound (4-1) to the compound (4-9) according to item 13.
  • at least one of the first additives is compound (4-1), compound (4-2), compound (4-3), compound (4-5), or compound (4-6).
  • Desirable compound (5) is the compound (5-1) to the compound (5-7) according to item 17.
  • additives that may be added to the composition will be described.
  • Such additives are optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like.
  • An optically active compound is added to the composition for the purpose of inducing a helical structure of liquid crystal molecules to give a twist angle. Examples of such a compound are the compound (6-1) to the compound (6-5).
  • a desirable ratio of the optically active compound is approximately 5% by weight or less. A more desirable ratio is in the range of approximately 0.01% by weight to approximately 2% by weight.
  • an antioxidant is composed. Added to the product.
  • a preferred example of the antioxidant is a compound (7) wherein n is an integer of 1 to 9.
  • the ultraviolet absorber examples include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Also preferred are light stabilizers such as sterically hindered amines.
  • a desirable ratio of these absorbers and stabilizers is approximately 50 ppm or more for achieving the effect thereof, and approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.
  • a dichroic dye such as an azo dye or an anthraquinone dye is added to the composition in order to adapt it to a GH (guest host) mode element.
  • a preferred ratio of the dye is in the range of approximately 0.01% by weight to approximately 10% by weight.
  • an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is added to the composition.
  • a desirable ratio of the antifoaming agent is approximately 1 ppm or more for obtaining the effect thereof, and approximately 1000 ppm or less for preventing a display defect.
  • a more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.
  • a polymerizable compound is used to adapt to a polymer support alignment (PSA) type device.
  • PSA polymer support alignment
  • Compound (3), compound (4), and compound (5) are suitable for this purpose.
  • a polymerizable compound different from the compound (3), the compound (4) and the compound (5) may be added to the composition together with the compound (3), the compound (4) and the compound (5).
  • Preferred examples of such a polymerizable compound are compounds such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), vinyl ketone and the like. Further preferred examples are acrylate or methacrylate.
  • a desirable ratio of compound (3), compound (4), and compound (5) is approximately 10% by weight or more based on the total weight of the polymerizable compound.
  • a more desirable ratio is about 50% by weight or more.
  • a particularly desirable ratio is approximately 80% by weight or more.
  • a particularly desirable ratio is also 100% by weight.
  • Polymerizable compound is polymerized by ultraviolet irradiation.
  • the polymerization may be performed in the presence of a suitable initiator such as a photopolymerization initiator.
  • a suitable initiator such as a photopolymerization initiator.
  • Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature.
  • Irgacure 651 registered trademark; BASF
  • Irgacure 184 registered trademark; BASF
  • Darocur 1173 registered trademark; BASF
  • a desirable ratio of the photopolymerization initiator is in the range of approximately 0.1% by weight to approximately 5% by weight based on the total weight of the polymerizable compound.
  • a more desirable ratio is in the range of approximately 1% by weight to approximately 3% by weight.
  • a polymerization inhibitor 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.
  • the polymerization inhibitor include hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol, phenothiazine and the like.
  • the polar compound is an organic compound having polarity.
  • a compound having an ionic bond is not included.
  • Atoms such as oxygen, sulfur, and nitrogen are more electronegative and tend to have partial negative charges.
  • Carbon and hydrogen tend to be neutral or have a partial positive charge.
  • Polarity arises from the fact that partial charges are not evenly distributed among different types of atoms in a compound.
  • the polar compound has at least one of partial structures such as —OH, —COOH, —SH, —NH 2 ,>NH,> N—.
  • compositions have a minimum temperature of about ⁇ 10 ° C. or lower, a maximum temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20.
  • a composition having an optical anisotropy in the range of about 0.08 to about 0.25 may be prepared by controlling the ratio of the component compounds or by mixing other liquid crystal compounds.
  • a composition having optical anisotropy in the range of about 0.10 to about 0.30 may be prepared by trial and error.
  • a device containing this composition has a large voltage holding ratio.
  • This composition is suitable for an AM device.
  • This composition is particularly suitable for a transmissive AM device.
  • This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.
  • This composition can be used for an AM device. Further, it can be used for PM elements.
  • This composition can be used for an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, FFS, VA, and FPA.
  • Use for an AM device having a mode such as TN, OCB, IPS, or FFS is particularly preferable.
  • the alignment of liquid crystal molecules may be parallel to or perpendicular to the glass substrate.
  • These elements may be reflective, transmissive, or transflective. Use in a transmissive element is preferred. It can also be used for an amorphous silicon-TFT device or a polycrystalline silicon-TFT device.
  • NCAP non-curvilinear-aligned-phase
  • PD polymer-dispersed
  • An example of a method for producing a conventional polymer-supported orientation type device is as follows. An element having two substrates called an array substrate and a color filter substrate is assembled. This substrate has an alignment film. At least one of the substrates has an electrode layer. A liquid crystal compound is prepared by mixing a liquid crystal compound. A polymerizable compound is added to the composition. You may add an additive further as needed. This composition is injected into the device. The device is irradiated with light with a voltage applied. Ultraviolet light is preferred. The polymerizable compound is polymerized by light irradiation. By this polymerization, a composition containing a polymer is generated. The polymer-supported orientation type element is manufactured by such a procedure.
  • an alignment film is not required on the substrate of the device.
  • a device without an alignment film is manufactured from a substrate without an alignment film according to the procedure described in the previous paragraph.
  • the compound (3) or the compound (4) is arranged on the substrate because the polar group interacts with the substrate surface.
  • the liquid crystal molecules are aligned according to this arrangement.
  • the alignment of liquid crystal molecules is further promoted.
  • the polymerizable group is polymerized by ultraviolet rays, so that a polymer maintaining this orientation is formed.
  • the effect of this polymer additionally stabilizes the orientation of the liquid crystal molecules and shortens the response time of the device. Since image sticking is a malfunction of the liquid crystal molecules, the effect of this polymer also improves the image sticking.
  • the present invention will be described in more detail with reference to examples. The invention is not limited by these examples.
  • the present invention includes a mixture of composition M1 and composition M2.
  • the invention also includes a mixture of at least two of the example compositions.
  • the synthesized compound was identified by a method such as NMR analysis. The characteristics of the compound, composition and device were measured by the following methods.
  • NMR analysis DRX-500 manufactured by Bruker BioSpin Corporation was used for 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 times of integration.
  • Tetramethylsilane was used as an internal standard.
  • CFCl 3 was used as an internal standard and the number of integrations was 24.
  • s is a singlet
  • d is a doublet
  • t is a triplet
  • q is a quartet
  • quint is a quintet
  • sex is a sextet
  • m is a multiplet
  • br is broad.
  • a sample was prepared in an acetone solution (0.1% by weight), and 1 ⁇ L thereof was injected into the sample vaporization chamber.
  • the recorder is a C-R5A Chromatopac manufactured by Shimadzu Corporation, or an equivalent product.
  • the obtained gas chromatogram showed the peak retention time and peak area corresponding to the component compounds.
  • capillary column As a solvent for diluting the sample, chloroform, hexane or the like may be used.
  • the following capillary column may be used.
  • HP-1 from Agilent Technologies Inc. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), Rtx-1 from Restek Corporation (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), BP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m) manufactured by SGE International Pty.
  • a capillary column CBP1-M50-025 length 50 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m
  • Shimadzu Corporation may be used.
  • Measurement sample When measuring the characteristics of the composition and the device, the composition was used as it was as a sample.
  • a sample for measurement was prepared by mixing this compound (15% by weight) with mother liquid crystals (85% by weight). The characteristic value of the compound was calculated from the value obtained by the measurement by extrapolation.
  • (Extrapolated value) ⁇ (Measured value of sample) ⁇ 0.85 ⁇ (Measured value of mother liquid crystal) ⁇ / 0.15.
  • the ratio of the compound and the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight in this order. changed.
  • the maximum temperature, optical anisotropy, viscosity, and dielectric anisotropy values for the compound were determined.
  • the following mother liquid crystals were used.
  • the ratio of the component compounds is shown by weight%.
  • nematic phase (NI; ° C.): A sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature was measured when a part of the sample changed from a nematic phase to an isotropic liquid.
  • the upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.
  • T C Minimum temperature of nematic phase
  • a sample having a nematic phase is placed in a glass bottle and placed in a freezer at 0 ° C., ⁇ 10 ° C., ⁇ 20 ° C., ⁇ 30 ° C. and ⁇ 40 ° C. for 10 days. After storage, the liquid crystal phase was observed. For example, when the sample remained in a nematic phase at ⁇ 20 ° C. and changed to a crystalline or smectic phase at ⁇ 30 ° C., the TC was described as ⁇ 20 ° C.
  • the lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.
  • Viscosity Bulk viscosity; ⁇ ; measured at 20 ° C .; mPa ⁇ s: An E-type viscometer manufactured by Tokyo Keiki Co., Ltd. was used for the measurement.
  • Viscosity (rotational viscosity; ⁇ 1; measured at 25 ° C .; mPa ⁇ s): The measurement was performed according to the method described in M. ⁇ Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). I followed. A sample was injected into a VA device having a distance (cell gap) between two glass substrates of 20 ⁇ m. This element was applied stepwise in increments of 1 volt within a range of 39 to 50 volts. After no application for 0.2 seconds, the application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds).
  • the dielectric constants ( ⁇ and ⁇ ) were measured as follows. 1) Measurement of dielectric constant ( ⁇ ): An ethanol (20 mL) solution of octadecyltriethoxysilane (0.16 mL) was applied to a well-cleaned glass substrate. The glass substrate was rotated with a spinner and then heated at 150 ° C. for 1 hour. A sample was put in a VA element in which the distance between two glass substrates (cell gap) was 4 ⁇ m, and the element was sealed with an adhesive that was cured with ultraviolet rays.
  • Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant ( ⁇ ) in the major axis direction of the liquid crystal molecules was measured.
  • 2) Measurement of dielectric constant ( ⁇ ) A polyimide solution was applied to a well-cleaned glass substrate. After baking this glass substrate, the obtained alignment film was rubbed. A sample was injected into a TN device in which the distance between two glass substrates (cell gap) was 9 ⁇ m and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant ( ⁇ ) in the minor axis direction of the liquid crystal molecules was measured.
  • Threshold voltage (Vth; measured at 25 ° C .; V): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement.
  • the light source was a halogen lamp.
  • a sample is placed in a normally black mode VA element in which the distance between two glass substrates (cell gap) is 4 ⁇ m and the rubbing direction is anti-parallel, and an adhesive that cures the element with ultraviolet rays is used. And sealed.
  • the voltage (60 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 20V by 0.02V.
  • the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured.
  • a voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum and the transmittance was 0% when the light amount was the minimum.
  • the threshold voltage was expressed as a voltage when the transmittance reached 10%.
  • VHR-2 Voltage holding ratio (VHR-2; measured at 80 ° C .;%): The voltage holding ratio was measured in the same procedure as above except that it was measured at 80 ° C. instead of 25 ° C. The obtained value was expressed as VHR-2.
  • VHR-3 Voltage holding ratio
  • the TN device used for the measurement had a polyimide alignment film, and the cell gap was 5 ⁇ m.
  • a sample was injected into this element and irradiated with light for 20 minutes.
  • the light source was an ultra high pressure mercury lamp USH-500D (manufactured by USHIO), and the distance between the element and the light source was 20 cm.
  • a decaying voltage was measured for 16.7 milliseconds.
  • a composition having a large VHR-3 has a large stability to ultraviolet light.
  • VHR-3 is preferably 90% or more, and more preferably 95% or more.
  • VHR-4 Voltage holding ratio
  • the TN device injected with the sample was heated in a constant temperature bath at 80 ° C. for 500 hours, and then the voltage holding ratio was measured to determine the stability against heat. Evaluated. In the measurement of VHR-4, a voltage decaying for 16.7 milliseconds was measured. A composition having a large VHR-4 has a large stability to heat.
  • an ultraviolet curing multimetal lamp M04-L41 manufactured by Eye Graphics Co., Ltd. was used for irradiation with ultraviolet rays.
  • a rectangular wave 120 Hz was applied to this element.
  • the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. It was considered that the transmittance was 100% when the light amount was the maximum, and the transmittance was 0% when the light amount was the minimum.
  • the maximum voltage of the rectangular wave was set so that the transmittance was 90%.
  • the minimum voltage of the rectangular wave was set to 2.5 V at which the transmittance was 0%.
  • the response time was expressed as the time required to change the transmittance from 10% to 90% (rise time; millisecond).
  • Elastic constant (K11: spray elastic constant, K33: bend elastic constant; measured at 25 ° C .; pN):
  • an EC-1 type elastic constant measuring instrument manufactured by Toyo Corporation was used. Using. A sample was injected into a vertical alignment element in which the distance between two glass substrates (cell gap) was 20 ⁇ m. A 20 to 0 volt charge was applied to the device, and the capacitance and applied voltage were measured. Fitting the measured values of capacitance (C) and applied voltage (V) using “Liquid Crystal Device Handbook” (Nikkan Kogyo Shimbun), formulas (2.98) and (2.101) on page 75 The value of the elastic constant was obtained from the formula (2.100).
  • Pretilt angle (degrees): A spectroscopic ellipsometer M-2000U (manufactured by J. A. Woollam Co., Inc.) was used to measure the pretilt angle.
  • Synthesis example 1 Compound (3-1) was synthesized by the following method.
  • Step 1 Compound (T-1) (4.98 g), Compound (T-2) (5.00 g), Potassium carbonate (6.88 g), Tetrakis (triphenylphosphine) palladium (0.289 g), and isopropyl Alcohol (IPA; 100 ml) was placed in the reactor and heated to reflux at 80 ° C. for 2 hours. The reaction mixture was poured into water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to obtain compound (T-3) (6.38 g; 99%).
  • IPA isopropyl Alcohol
  • Step 1 Compound (T-11) (25.0 g), acrylic acid (7.14 g), 4-dimethylaminopyridine (DMAP; 1.21 g), and dichloromethane (300 ml) were placed in a reactor and brought to 0 ° C. Cooled down. A solution of 1,3-dicyclohexylcarbodiimide (DCC; 24.5 g) in dichloromethane (125 ml) was slowly added dropwise thereto and stirred for 12 hours while returning to room temperature. The insoluble material was filtered off, the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and dried over anhydrous magnesium sulfate.
  • DCC 1,3-dicyclohexylcarbodiimide
  • compositions examples are shown below.
  • the component compounds were represented by symbols based on the definitions in Table 3 below.
  • Table 3 the configuration regarding 1,4-cyclohexylene is trans.
  • the number in parentheses after the symbolized compound represents the chemical formula to which the compound belongs.
  • the symbol ( ⁇ ) means other liquid crystal compounds.
  • the ratio (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the weight of the liquid crystal composition containing no additive.
  • Example 1 of device A composition containing a polar compound was injected into an element having no raw material alignment film. After irradiating with ultraviolet rays, the vertical alignment of liquid crystal molecules in this device was examined. First, the raw materials will be explained. The raw materials were appropriately selected from Composition M1 to Composition M18, Polar compounds (PC-1) to (PC-22), and Polymerizable compounds (RM-1) to (RM-7). The composition is as follows.
  • the first additive is a polar compound (PC-1) to (PC-22).
  • the second additive is a polymerizable compound (RM-1) to (RM-7).
  • Example 1 of vertical alignment of liquid crystal molecules To the composition M1, the polar compound (PC-1) was added in a proportion of 5% by weight, and the polymerizable compound (RM-1) was further added in a proportion of 0.5% by weight. This mixture was injected into a device having an alignment film having a gap (cell gap) of 4.0 ⁇ m between two glass substrates on a hot stage at 100 ° C. The element is irradiated with ultraviolet rays (28J) using an ultra-high pressure mercury lamp USH-250-BY (manufactured by USHIO) to polymerize the polar compound (PC-1) and the polymerizable compound (RM-1). It was.
  • This element was set on a polarizing microscope in which a polarizer and an analyzer were arranged orthogonally, and the element was irradiated with light from below to observe the presence or absence of light leakage.
  • the vertical alignment was judged as “good”. This is because it is presumed that the liquid crystal molecules are sufficiently aligned.
  • light passing through the element was observed, it was indicated as “defective”.
  • Examples 2 to 22 and Comparative Example 1 A device having no alignment film was manufactured using a mixture of the composition, the polar compound, and the polymerizable compound. The presence or absence of light leakage was observed in the same manner as in Example 1. The results are summarized in Table 4. In Comparative Example 1, no polar compound having a polymerizable group was added for comparison.
  • the liquid crystal composition of the present invention can be used for a liquid crystal projector, a liquid crystal television and the like.

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Abstract

L'invention concerne une composition de cristaux liquides dans laquelle l'alignement vertical des molécules de cristaux liquides peut être obtenu par l'action d'un polymère ; et un élément d'affichage à cristaux liquides qui comprend la composition. La composition de cristaux liquides, qui est une composition nématique de cristaux liquides comprenant un composé polaire portant au moins un groupe polymérisable en tant que premier additif et un composé polymérisable portant au moins trois groupes polymérisables en tant que second additif et ayant une anisotropie diélectrique négative, peut comprendre un composé cristallin liquide spécifique présentant une anisotropie diélectrique largement négative en tant que premier composant et un composé cristallin liquide spécifique ayant une limite supérieure de température élevée ou une faible viscosité en tant que deuxième composant. L'invention concerne également un élément d'affichage à cristaux liquides comprenant cette composition.
PCT/JP2017/002357 2016-02-25 2017-01-24 Composition de cristaux liquides et élément d'affichage à cristaux liquides Ceased WO2017145611A1 (fr)

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JPWO2017195585A1 (ja) * 2016-05-10 2018-05-24 Dic株式会社 液晶表示素子
WO2018221236A1 (fr) * 2017-06-01 2018-12-06 Dic株式会社 Monomère polymérisable, composition de cristaux liquides utilisant un monomère polymérisable et dispositif d'affichage à cristaux liquides
WO2019003935A1 (fr) * 2017-06-29 2019-01-03 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
JP6525227B1 (ja) * 2017-11-21 2019-06-05 Dic株式会社 液晶組成物及び液晶表示素子
WO2019124094A1 (fr) * 2017-12-21 2019-06-27 Dic株式会社 Composition de cristaux liquides
WO2019124345A1 (fr) * 2017-12-22 2019-06-27 Dic株式会社 Composition polymérisable à cristaux liquides, élément d'affichage à cristaux liquides et composé polymérisable
WO2019124093A1 (fr) * 2017-12-21 2019-06-27 Dic株式会社 Composition de cristaux liquides
WO2020116380A1 (fr) * 2018-12-07 2020-06-11 Jnc株式会社 Composé, composition de cristaux liquides et élément d'affichage à cristaux liquides
CN111373019A (zh) * 2017-12-22 2020-07-03 Dic株式会社 液晶组合物及液晶显示元件
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