JPH0987626A - Liquid crystal composition and liquid crystal display element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal composition containing a mixture of specific carboxylic acids with a compound containing a specific terminal group, especially high in clearing point, having a low viscosity, excellent in rapid responding property and useful for an active matrix-type liquid crystal display element. SOLUTION: This liquid crystal composition contains (A) a compound of formula I (R<0> is a 1-10C alkyl, a 2-10C alkenyl, etc.) or a compound of the formula: R<1> -A<0> -COOH [R<1> is R<0> ; A<0> is a 1,4-phenylene (substituted by one F)], (B) a compound of formula II (R<2> is R<0> ; Z<0> is C2 H4 - or a single bond), a compound of formula III (R<3> is R<0> ; Z<1> is Z<0> ; A<1> is A<0> ) or a compound of the formula R<4> -A<2> -Z<2> -A<3> -COOH [R<4> is R<0> ; Z<2> is Z<0> ; A<2> is A<0> ; A<3> is A<0> or a trans-1,4- cyclohexylene (one F is substituted)] and (C) a compound having a terminal group of formula IV (X is F, Cl, CF3 , etc.; Q<1> , Q<2> are each H or F), in a ratio of e.g. 2-50wt.% component A, 2-30wt.% component B and 40-95wt.% component C based on the total weight of the composition.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a nematic liquid crystal composition containing at least one kind of chiral additive and a liquid crystal composition provided in a closed cell formed of two substrates having transparent electrodes. The present invention relates to a liquid crystal display element used. More specifically, Active Matrix (AM-L
The present invention relates to a liquid crystal composition suitable for the CD system and a liquid crystal display device using the liquid crystal composition.

[0002]

2. Description of the Related Art As a display system of a liquid crystal display device (LCD), a twist nematic (TN) system, a super twist nematic (STN) system, an active matrix (AM-LCD) system and the like have been proposed and put into practical use one after another. . Among them, active matrix LCDs (AM-LCDs) such as thin film transistors (TFTs) have been attracting attention as a favorite of flat displays due to progress in colorization and high definition. As the liquid crystal material for the display device, a compound having characteristics suitable for the purpose of use must be appropriately selected, but no compound alone satisfying the above conditions has been found. Alternatively, a non-crystalline compound is further mixed to prepare a liquid crystal composition having necessary characteristics, and the liquid crystal composition is used as a material for an LCD. The characteristics of the liquid crystal composition used for the AM-LCD type liquid crystal display device are (1) to exhibit a nematic liquid crystal phase in a wide temperature range including room temperature. Especially the nematic-isotropic phase transition temperature (clearing point)
Is high. (2) In order to minimize the response time (τ),
Low viscosity (η). (3) Appropriate refractive index anisotropy (Δ
n). (4) Be chemically stable. (5) The voltage holding ratio (VHR) is high in order to maintain high contrast. And the like. In order to increase the nematic range of the liquid crystal composition, it is essential to introduce a liquid crystal compound having a high NI point and good compatibility with other liquid crystals. Generally NI
To raise the point, a compound having a large number of rings may be used, but in this case, the viscosity of the liquid crystal composition also increases at the same time.
On the other hand, there has been a strong demand in recent years for the LCD to support moving images, but in order to support moving images, the response speed when driving the LCD must be low, and the response speed is the liquid crystal composition. Therefore, it is urgently required to develop a liquid crystal composition having a low viscosity, because the liquid crystal composition is proportional to the viscosity. Also, AM-
In LCDs, there is a demand for a so-called highly reliable liquid crystal composition having a high voltage holding ratio (VHR) or a large specific resistance value in order to maintain a high contrast. By the way, carboxyl group (-COOH) at the end
The compound having is dimerization
n) and develops liquid crystallinity (DD
emus, Flussige Kristale i
n Tabellen, 57 (1974)). As an application of such a compound having a carboxyl group, JP-A-54-151951 discloses a liquid crystal composition using an alkylcyclohexylcarboxylic acid. However, although the use of alkylcyclohexylcarboxylic acid can reduce the viscosity of the liquid crystal composition, it has a drawback that the clearing point and the refractive index anisotropy (Δn) become small. In addition, JP-A-6-5725
No. 2 discloses a liquid crystal composition using alkylbenzoic acid or alkoxybenzoic acid. These benzoic acids have the drawback that the viscosity of the liquid crystal composition can be reduced and Δn can be increased, but the clearing point cannot be increased. In addition, since the liquid crystal compositions disclosed therein use a liquid crystal compound having a CN group, it is said that the voltage holding ratio is particularly low among the strongly required characteristics of the liquid crystal composition for AM-LCD. It has drawbacks.

[0003]

SUMMARY OF THE INVENTION The object of the present invention is to have a high clearing point and a high clearing point in order to respond to high speed responsiveness while satisfying various characteristics required for the AM-LCD display system. Another object is to provide a liquid crystal composition having a relatively low viscosity. The present inventors have found that a liquid crystal composition satisfying these characteristics can be prepared by combining various fluorine-based liquid crystal compounds having no CN group and compounds having a carboxyl group.

[0004]

The first invention of the present invention is as follows:
As the first component, the general formula (Ia) and / or (I
-Containing at least one compound selected from b),
As a second component, at least one compound selected from the general formulas (Ic) to (Ie) is contained, and as a third component, at least a compound having a terminal group structure of the general formula (II) is contained. The present invention relates to a liquid crystal composition containing one or more kinds.

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[Chemical 21]

Embedded image (In formula, R < ⁰ > -R < ⁴ > shows a C1-C10 alkyl group or a C2-C10 alkenyl group each independently.
In any case, any one of the groups or two or more non-adjacent methylene groups (—CH ₂ —) is an oxygen atom (—O).
-) May be substituted. Z ⁰ , Z ¹ and Z ²
-C ₂ H each independently is ₄ - or a single bond, A ³
Represents a 1,4-phenylene group or trans-1,4-cyclohexylene group in which one H on the side position may be substituted with F, and A ^{0 to} A ² each independently represent one H on the side position. Is F
Represents a 1,4-phenylene group which may be substituted with. )

Embedded image (In the formula, X is F, Cl, CF ₃ , OCF ₃ , CF ₂ H,
OCF ₂ H, OCF ₂ CF ₂ H, OCF ₂ Cl or O
CF ₂ CFHCF ₃ and Q ¹ and Q ² each independently represent H or F. ) By using a combination of a monocyclic (Ia) and / or (Ib) compound having a carboxyl group and a bicyclic (Ic) to (Ie) compound, Basically, adjustment, clearing point adjustment, and Δn adjustment are possible. These compounds are used as a raw material or an intermediate in the synthesis of liquid crystal compounds, and have another advantage that an inexpensive liquid crystal composition can be produced by using them. A second aspect of the present invention provides a compound of general formula (II)
-A), (II-b), (II-c) and (II-d)

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[Chemical formula 26]

Embedded image (In the formula, R ⁵ represents an alkyl group having 1 to 10 carbon atoms, X 5
Is F, Cl, CF ₃ , OCF ₃ , CF ₂ H, OCF ₂
H, OCF ₂ CF ₂ H, OCF ₂ Cl or OCF ₂ C
FHCF ₃ , Q ¹ and Q ² each independently represent H or F, L ¹ and L ² each independently represent H or F, and Z ³ and Z ⁴ each independently —CH _2. CH
₂ -or a single bond is shown. ) A liquid crystal composition according to the first invention, which is a compound represented by In a third aspect of the present invention, the first component is 2 to 50% by weight and the second component is 2 to 30% by weight based on the total weight of the liquid crystal composition.
The liquid crystal composition according to the first or second invention is characterized in that the weight percentage and the third component are 40 to 95 wt%. A fourth aspect of the present invention provides, as the fourth component, the compounds represented by the general formulas (III), (IV) and (V)

Embedded image (In the formula, R ⁶ and R ⁷ each independently have 1 to 10 carbon atoms.
However, any one or two or more non-adjacent methylene groups (—CH ₂ —) in the group may be substituted with an oxygen atom. B and C are each independently a trans-1,4-cyclohexylene group or 1,
Shows the 4-phenylene group, Z ⁵ is -CH ₂ CH ₂ - shows a or a single bond. )

[Chemical 29] (In the formula, R ⁸ and R ⁹ each independently have 1 to 10 carbon atoms.
Is an alkyl group. In any case, any 1 in the group
Two or more methylene groups that are not adjacent to each other (-CH ₂
-) May be replaced by an oxygen atom (-O-).
D is a trans-1,4-cyclohexylene group or 1,
A 4-phenylene group is shown, and E is a trans-1,4-cyclohexylene group or a 1,4-phenylene group in which one H at the side position may be substituted with F. Z ⁶ is -CH ₂ C
H ₂ - or a single bond, Z ⁷ is -CH ₂ CH ₂ -,
-CH = CH-, -C≡C- or a single bond is shown. )

Embedded image (In the formula, R ¹⁰ is an alkyl group having 1 to ¹⁰ carbon atoms, and any one of the groups or two or more methylene groups (—CH ₂ —) not adjacent to each other are substituted with an oxygen atom (—O—). R ¹¹ represents an alkyl group having 1 to 10 carbon atoms,
Q ³ represents H or F. And a liquid crystal composition according to the first, second or third invention, further comprising one or more compounds selected from the group consisting of: A fifth invention of the present invention relates to the liquid crystal composition according to the fourth invention, wherein the fourth component is 0.1 to 40% by weight based on the total weight of the liquid crystal composition. A sixth invention of the present invention is represented by the general formula (VI-a),
(VI-b), (VI-c) and (VI-d)

[Chemical 31]

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[Chemical 33]

Embedded image (In the formula, R ¹² represents an alkyl group having 1 to 10 carbon atoms, and Y 12
Is F, Cl, CF ₃ , OCF ₃ , CF ₂ H, OCF ₂
H, OCF ₂ Cl or OCF ₂ CFHCF ₃
Q ⁴ and Q ⁵ each independently represent H or F. The invention further relates to the liquid crystal composition according to any one of the second to fifth inventions, which further comprises one or more compounds selected from the group consisting of: A seventh invention of the present invention relates to a liquid crystal display device using the liquid crystal composition according to any one of the first to sixth inventions.

The liquid crystal compounds constituting the liquid crystal composition of the present invention will be described below. As the compound represented by formula (Ia) and / or (Ib) which is the first component of the present invention, the following compounds can be preferably exemplified.

[0006]

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(R represents an alkyl group or an alkenyl group.)

Among these compounds, the compounds of the general formula (Ia-) are used because of their low viscosity and good compatibility at low temperature.
The compounds 1) to (Ib-3) are particularly preferably used in the present invention. General formula (Ia) and / or (I-
The compound of b) exhibits the characteristics of a bicyclic liquid crystal compound having a dielectric anisotropy Δε of about | Δε | <5 by dimerization. Therefore, it exhibits an excellent effect particularly in reducing the viscosity of the liquid crystal composition.

The second component of the present invention, the general formula (I-
As the compounds represented by c) to (Ie), the following compounds can be preferably mentioned.

[0010]

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[0011]

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[0012]

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[0013]

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(R represents an alkyl group or an alkenyl group.)

Among these compounds, the compounds of the general formula (I-c-) are used because of their low viscosity and good compatibility at low temperature.
1) to (I-c-3), (I-d-1) to (I-d-)
3), (I-e-1) to (I-e-3), (I-e-1)
Compounds such as 9) to (Ie-21) are particularly preferably used in the present invention. The compounds of the general formulas (Ic) to (Ie) have a dielectric anisotropy Δε of |
The characteristic of a 4-ring liquid crystal compound with Δε | <5 is exhibited.
Therefore, it is particularly effective in increasing the clearing point of the liquid crystal composition.

The first component of the present invention is the general formula (Ia)
And / or (Ib) and the general formula (I
By using the compounds (c) to (Ie) in combination, viscosity adjustment, clearing point adjustment, and Δn adjustment are basically possible.

The compounds of the general formulas (II-a) to (II-d) of the present invention are preferably the following compounds.

[0018]

[Chemical 40]

[0019]

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[0020]

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[0021]

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[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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[0029]

[Chemical 51]

[0030]

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[0031]

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[0032]

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(R represents an alkyl group.)

Among these compounds, the compounds of formula (II-a) are represented by formulas (II-a-1), (II-a-2),
(II-a-3), (II-a-4), (II-a-7),
(II-a-10), (II-a-13), (II-a-1)
6), (II-a-19), (II-a-22), (II-a
-23), (II-a-24), (II-a-28), (II
The compound represented by formula (-a-31), (II-a-34), (II-a-37) or (II-a-40) is particularly preferably used in the present invention. Further, as the compound of the formula (II-b), the compounds of the formulas (II-b-1), (II-b-2) and (II-b-
3), (II-b-4), (II-b-7), (II-b-1)
0), (II-b-13), (II-b-14), (II-b
-15), (II-b-19), (II-b-22), (II
-B-23), (II-b-24), (II-b-28),
(II-b-31), (II-b-34), (II-b-3)
5), (II-b-36), (II-b-40), (II-b
-43), (II-b-44), (II-b-45), (II
-B-46), (II-b-47), (II-b-49),
(II-b-52), (II-b-55), (II-b-5)
6), (II-b-57), (II-b-59) and (II
The compound represented by formula (-b-61) is particularly preferably used in the present invention. Further, as the compound of the formula (II-c), the compounds of the formula (II-c-1), (II-c-2), (II-c-3),
(II-c-5), (II-c-6), (II-c-9),
(II-c-12), (II-c-15), (II-c-1)
6), (II-c-17), (II-c-18), (II-c
-21), (II-c-22), (II-c-24), (II
-C-25), (II-c-26), (II-c-28),
(II-c-30), (II-c-33), (II-c-3)
5), (II-c-38), (II-c-39), (II-c
-40), (II-c-44), (II-c-47), (II
-C-48), (II-c-49) and (II-c-5)
The compound represented by 0) is particularly preferably used in the present invention. Further, as the compound of the formula (II-d), a compound of the formula (II-d
-2), (II-d-3), (II-d-5) or (II-
The compound represented by d-6) is particularly preferably used in the present invention.

The general formulas (II-a) to (II
The compound represented by -d) is a compound having a positive dielectric anisotropy, is very excellent in thermal stability and chemical stability, and has a particularly high voltage holding ratio or a high specific resistance value. It is an indispensable compound when preparing a liquid crystal composition for AM-LCD, which is required to have a large property. Of these, the bicyclic compounds are mainly used for the purpose of voltage adjustment and / or viscosity adjustment. Tricyclic compounds are mainly used for clearing point and nematic range adjustment and / or voltage adjustment,
It is used for the purpose of adjusting Δn and adjusting viscosity. The tetracyclic compound is mainly used for the purpose of adjusting the clearing point and the nematic range.

The fourth component of the present invention is the general formula (III),
Preferred examples of the compounds represented by (IV) and (V) include the following compounds.

[0037]

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[0038]

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(R and R'each independently represent an alkyl group.)

Among these compounds, the compounds of the general formula (III) are represented by the formulas (III-1), (III-2), (III-4),
(III-5) and (III-6) are particularly preferably used in the present invention. Further, as the compound of the general formula (IV),
-1), (IV-2), (IV-3), (IV-9), (IV-
The compounds 10) and (IV-11) are particularly preferably used in the present invention. Further, as the compound of the general formula (V), the compounds of the formulas (V-1), (V-2) and (V-3) are particularly preferably used. The compound of the general formula (III) is a bicyclic compound having negative or weak dielectric anisotropy, and is mainly used for the purpose of decreasing viscosity and / or adjusting Δn. The compound of the general formula (IV) is a tricyclic compound having a negative or weak dielectric anisotropy, and is mainly used for the purpose of increasing the clearing point and widening the nematic range and / or for adjusting Δn. Further, the compound of the general formula (V) has a negative or weak positive dielectric anisotropy of 4
It is a ring compound and is mainly used for the purpose of expanding the nematic range.

As the compounds represented by the general formulas (VI) and (VII) which are the additional components (fifth component) of the present invention, the following compounds can be preferably mentioned.

[0042]

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[0043]

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(R represents an alkyl group.)

Among these compounds, the compounds of the general formula (IV) are represented by the formulas (IV-a-1), (IV-b-1) and (IV
-B-3), (IV-c-1) and (IV-c-3) are particularly preferably used in the present invention. The compound of the general formula (IV) has a positive dielectric anisotropy and a large value, and is used for the purpose of reducing the threshold voltage.

The amount of the first component used in the present invention is
The amount is preferably 2 to 50% by weight based on the total weight of the liquid crystal composition. If it is less than 2% by weight, the effect of the subject Δn and clearing point is difficult to obtain, and if it exceeds 50% by weight, the threshold voltage of the liquid crystal composition becomes large, which is not preferable. It is more preferably 3 to 40% by weight. The amount of the second component used is preferably 2 to 30% by weight based on the total weight of the liquid crystal composition. Two
If it is less than wt%, the effect of the subject Δn and the clearing point is difficult to obtain, and if it exceeds 30 wt%, the threshold voltage of the liquid crystal composition becomes large, which is not preferable. More preferably 3 to 2
0% by weight is preferred. The amount of the third component used is 40 to 95.
% By weight is preferred. If it is less than 40% by weight, the threshold voltage becomes large, and if it exceeds 95% by weight, it is difficult to obtain the effect of the subject Δn and the clearing point, which is not preferable. More preferably, it is 50 to 90% by weight. The amount of the fourth component used is preferably 0.1 to 40% by weight. If it exceeds 40% by weight, the threshold voltage becomes large, which is not preferable. It is more preferably 0.1 to 30% by weight. The amount of the fifth component used is preferably 0.1 to 40% by weight. If it exceeds 40% by weight, the threshold voltage becomes large, which is not preferable. It is more preferably 0.1 to 30% by weight.

The liquid crystal composition of the present invention has a threshold voltage, a nematic range, and Δn in addition to the compounds represented by the above general formulas (I) to (V) depending on the purpose of the liquid crystal display device used. For the purpose of adjusting the dielectric anisotropy, viscosity, etc., other compounds can be contained in appropriate amounts within the range not impairing the object of the present invention.

The liquid crystal composition used in accordance with the present invention is prepared in a manner which is conventional per se. Generally, a method of dissolving various components at a high temperature is used. Further, the liquid crystal material of the present invention is improved and optimized according to the intended use by appropriate additives. Such additives are well known to those skilled in the art and are described in detail in the literature and the like. Normally, the spiral structure of the liquid crystal is induced to adjust the required twist angle, and the reverse twist
chiral dopants (chiral d) to prevent
ant) and the like are added.

Further, the liquid crystal composition used in accordance with the present invention contains a dichroic dye such as a merocyanine-based, styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, and tetrazine-based liquid It can also be used as a liquid crystal composition for the host (GH) mode.
Alternatively, a polymer dispersed liquid crystal display device (PDLCD) typified by NCAP manufactured by encapsulating nematic liquid crystal or a polymer network liquid crystal display device (PNLCD) manufactured by forming a three-dimensional network polymer in the liquid crystal.
As a liquid crystal composition. In addition, it can be used as a liquid crystal composition for a birefringence control (ECB) mode or a dynamic scattering (DS) mode.

[0050]

EXAMPLES The present invention is described in detail below with reference to examples, but the present invention is not limited to these examples. Further, the composition ratios of Comparative Examples and Examples are all shown by weight%. The threshold voltage is the voltage at which the transmittance in the electro-optical response corresponds to 10% of the saturation value. The voltage holding ratio was determined by the area method.

Comparative Example 1 The following liquid crystal composition disclosed in Mixing Example 2 of JP-A-54-151951 was prepared.

[0052]

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The clearing point of this liquid crystal composition is T _NI = 67.6.
(° C), the viscosity at 20 ° C is η ₂₀ = 55.7 (mPa
.S), the refractive index anisotropy at 25 ° C. is Δn = 0.16.
The dielectric anisotropy at 9, 20 ° C. is Δε = 9.2, 20
The threshold voltage at C was Vth = 1.56 (V). Moreover, the voltage holding ratio of this liquid crystal composition was measured. As a result, the voltage holding ratio at 25 ° C. was 83.3%, and the voltage holding ratio at 60 ° C. was 56.2%.

Comparative Example 2 The following liquid crystal composition disclosed in Example 2 of JP-A-6-57252 was prepared.

[0055]

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The clearing point of this liquid crystal composition is T _NI = 76.5.
(° C), the viscosity at 20 ° C is η ₂₀ = 22.3 (mPa
.S), the refractive index anisotropy at 25 ° C. is Δn = 0.13.
The dielectric anisotropy at 2, 20 ° C. is Δε = 9.3, 20
The threshold voltage at C was Vth = 1.65 (V). Voltage holding ratio at 25 ℃ is 85.4%, 60 ℃
The voltage holding ratio was 53.8%.

Embodiment 1

[0058]

[Chemical formula 61]

A liquid crystal composition consisting of was prepared. The clearing point of this liquid crystal composition is T _NI = 104.0 (° C.), the viscosity at 20 ° C. is η ₂₀ = 21.2 (mPa · s), and the refractive index anisotropy at 25 ° C. is Δn = 0.091. The dielectric anisotropy at 20 ° C. was Δε = 4.3, and the threshold voltage at 20 ° C. was Vth = 2.32 (V). The voltage holding ratio at 25 ° C was 97.8%, and the voltage holding ratio at 60 ° C was 96.1%. As compared with the liquid crystal composition of Comparative Example 1, the clearing point and the voltage holding ratio were high, and the viscosity was low.

Example 2

[0061]

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[0062]

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A liquid crystal composition consisting of was prepared. The clearing point of this liquid crystal composition is T _NI = 95.0 (° C.), the viscosity at 20 ° C. is η ₂₀ = 30.4 (mPa · s), and the refractive index anisotropy at 25 ° C. is Δn = 0.104. The dielectric anisotropy at 20 ° C. was Δε = 8.0, and the threshold voltage at 20 ° C. was Vth = 1.78 (V). The voltage holding ratio at 25 ° C was 98.4%, and the voltage holding ratio at 60 ° C was 96.4%. The clearing point and the voltage holding ratio were higher than those of the liquid crystal composition of Comparative Example 2.

Example 3

[0065]

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[0066]

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A liquid crystal composition consisting of was prepared. The clearing point of this liquid crystal composition is T _NI = 100.0 (° C.), the viscosity at 20 ° C. is η ₂₀ = 24.8 (mPa · s), and the refractive index anisotropy at 25 ° C. is Δn = 0.097. The dielectric anisotropy at 20 ° C. was Δε = 6.0, and the threshold voltage at 20 ° C. was Vth = 2.02 (V). The voltage holding ratio at 25 ° C was 98.2%, and the voltage holding ratio at 60 ° C was 96.5%.

Embodiment 4

[0069]

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The clearing point of this liquid crystal composition is T_NI= 106.
The viscosity at 6 (℃) and 20 ℃ is η ₂₀= 29.1 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 94 and 20 ° C. is Δε = 4.1, 2
The threshold voltage at 0 ° C. is Vth = 2.45 (V)
there were. The voltage holding ratio at 25 ° C was 98.5%.
Was.

Example 5

[0072]

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The clearing point of this liquid crystal composition is T_NI= 133.
Viscosity at 5 (° C) and 20 ° C is η ₂₀= 32.3 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 97 and 20 ° C. is Δε = 4.4, 2
The threshold voltage at 0 ° C. is Vth = 2.55 (V)
there were. The voltage holding ratio at 25 ° C was 98.6%.
Was.

Embodiment 6

[0075]

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The clearing point of this liquid crystal composition is T_NI= 154.
The viscosity at 4 (° C) and 20 ° C is η ₂₀= 35.4 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 97 and 20 ° C. is Δε = 4.4, 2
The threshold voltage at 0 ° C. is Vth = 2.77 (V)
there were. The voltage holding ratio at 25 ° C was 98.4%.
Was.

Embodiment 7

[0078]

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[0079]

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The clearing point of this liquid crystal composition is T _NI = 100.
The viscosity at 6 (° C) and 20 ° C is η ₂₀ = 30.8 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 78 and 20 ° C. is Δε = 2.8, 2
The threshold voltage at 0 ° C. was Vth = 3.11 (V). The voltage holding ratio at 25 ° C was 98.6%.

Example 8

[0082]

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[0083]

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The clearing point of this liquid crystal composition is T _NI = 102.
The viscosity at 9 (° C) and 20 ° C is η ₂₀ = 37.1 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
Dielectric anisotropy at 92 and 20 ° C. is Δε = 7.9, 2
The threshold voltage at 0 ° C. was Vth = 1.72 (V). The voltage holding ratio at 25 ° C was 98.4%.

Example 9

[0086]

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[0087]

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The clearing point of this liquid crystal composition is T _NI = 95.2.
(° C.), viscosity at 20 ° C. is η ₂₀ = 26.4 (mPa
・ S), the refractive index anisotropy at 25 ° C. is Δn = 0.08.
Dielectric anisotropy at 2, 20 ° C. is Δε = 7.8, 20
The threshold voltage at C was Vth = 2.11 (V). The voltage holding ratio at 25 ° C was 98.4%.

Example 10

[0090]

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[0091]

[Chemical 76]

The clearing point of this liquid crystal composition is T _NI = 102.
The viscosity at 7 (° C) and 20 ° C is η ₂₀ = 42.8 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 96 and 20 ° C. is Δε = 5.2, 2
The threshold voltage at 0 ° C. was Vth = 2.31 (V). The voltage holding ratio at 25 ° C was 98.6%.

Example 11

[0094]

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[0095]

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The clearing point of this liquid crystal composition is T _NI = 103.
The viscosity at 2 (° C) and 20 ° C is η ₂₀ = 43.7 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 01 and 20 ° C. is Δε = 6.6, 2
The threshold voltage at 0 ° C. was Vth = 2.11 (V). The voltage holding ratio at 25 ° C was 98.6%.

Example 12

[0098]

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[0099]

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The clearing point of this liquid crystal composition is T _NI = 115.
The viscosity at 6 (° C) and 20 ° C is η ₂₀ = 47.8 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 18 and 20 ° C. is Δε = 8.3, 2
The threshold voltage at 0 ° C. was Vth = 2.06 (V). The voltage holding ratio at 25 ° C was 98.5%.

Embodiment 13

[0102]

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[0103]

[Chemical formula 82]

The clearing point of this liquid crystal composition is T _NI = 103.
The viscosity at 5 (° C) and 20 ° C is η ₂₀ = 33.0 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.0
The dielectric anisotropy at 89 and 20 ° C. is Δε = 7.8, 2
The threshold voltage at 0 ° C. was Vth = 1.91 (V). The voltage holding ratio at 25 ° C was 98.2%.

Example 14

[0106]

[Chemical 83]

[0107]

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The clearing point of this liquid crystal composition is T _NI = 104.
The viscosity at 5 (° C) and 20 ° C is η ₂₀ = 34.7 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 15 and 20 ° C. is Δε = 7.4, 2
The threshold voltage at 0 ° C. was Vth = 2.02 (V). The voltage holding ratio at 25 ° C was 98.4%.

Example 15

[0110]

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[0111]

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The clearing point of this liquid crystal composition is T _NI = 100.
The viscosity at 2 (° C) and 20 ° C is η ₂₀ = 33.9 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 08 and 20 ° C. is Δε = 8.0, 2
The threshold voltage at 0 ° C. was Vth = 1.90 (V). The voltage holding ratio at 25 ° C was 98.5%.

Example 16

[0114]

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[0115]

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The clearing point of this liquid crystal composition is T _NI = 123.
The viscosity at 9 (° C) and 20 ° C is η ₂₀ = 31.5 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 01 and 20 ° C. is Δε = 3.6, 2
The threshold voltage at 0 ° C. was Vth = 2.95 (V). The voltage holding ratio at 25 ° C was 98.4%.

Example 17

[0118]

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[0119]

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The clearing point of this liquid crystal composition is T _NI = 123.
The viscosity at 9 (° C) and 20 ° C is η ₂₀ = 31.5 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 01 and 20 ° C. is Δε = 3.6, 2
The threshold voltage at 0 ° C. was Vth = 2.95 (V). The voltage holding ratio at 25 ° C was 98.3%.

Example 18

[0122]

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[0123]

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The clearing point of this liquid crystal composition is T _NI = 91.2.
(° C), viscosity at 20 ° C is η ₂₀ = 21.5 (mPa
.S), the refractive index anisotropy at 25 ° C. is Δn = 0.10
The dielectric anisotropy at 3, 20 ° C. is Δε = 4.7, 20
The threshold voltage at C was Vth = 2.21 (V). The voltage holding ratio at 25 ° C was 98.4%.

Example 19

[0126]

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[0127]

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The clearing point of this liquid crystal composition is T _NI = 121.
The viscosity at 8 (° C) and 20 ° C is η ₂₀ = 34.3 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 19 and 20 ° C. is Δε = 6.5, 2
The threshold voltage at 0 ° C. was Vth = 2.95 (V). The voltage holding ratio at 25 ° C was 98.3%.

Example 20

[0130]

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[0131]

[Chemical 96]

The clearing point of this liquid crystal composition is T _NI = 119.
The viscosity at 6 (° C) and 20 ° C is η ₂₀ = 31.8 (mP
a · s), the refractive index anisotropy at 25 ° C. is Δn = 0.1
The dielectric anisotropy at 05 and 20 ° C. is Δε = 6.3, 2
The threshold voltage at 0 ° C. was Vth = 2.14 (V). The voltage holding ratio at 25 ° C was 94.1%.

[0133]

As shown in the embodiments, according to the present invention, while satisfying various characteristics required for the AM-LCD display system, the clear point is particularly high in order to cope with high-speed response. It is possible to provide a liquid crystal composition having a relatively low viscosity for a high ratio.

Claims (7)

[Claims] 1. As a first component, at least one compound selected from the general formula (Ia) and / or (Ib) is contained, and as a second component, the general formula (Ic) to
A liquid crystal containing at least one compound selected from (Ie) and at least one compound having a terminal group structure of the general formula (II) as a third component. Composition. Embedded image Embedded image Embedded image Embedded image Embedded image (In formula, R < ⁰ > -R < ⁴ > shows a C1-C10 alkyl group or a C2-C10 alkenyl group each independently.
In any case, any one of the groups or two or more non-adjacent methylene groups (—CH ₂ —) is an oxygen atom (—O).
-) May be substituted. Z ⁰ , Z ¹ and Z ²
-C ₂ H each independently is ₄ - or a single bond, A ³
Represents a 1,4-phenylene group or trans-1,4-cyclohexylene group in which one H on the side position may be substituted with F, and A ^{0 to} A ² each independently represent one H on the side position. Is F
Represents a 1,4-phenylene group which may be substituted with. ) (In the formula, X is F, Cl, CF ₃ , OCF ₃ , CF ₂ H,
OCF ₂ H, OCF ₂ CF ₂ H, OCF ₂ Cl or O
CF ₂ CFHCF ₃ and Q ¹ and Q ² each independently represent H or F. ) 2. The compound of general formula (II) is a compound of general formula (II-
a), (II-b), (II-c) and (II-d) embedded image Embedded image Embedded image Embedded image (In the formula, R ⁵ represents an alkyl group having 1 to 10 carbon atoms, X 5
Is F, Cl, CF ₃ , OCF ₃ , CF ₂ H, OCF ₂
H, OCF ₂ CF ₂ H, OCF ₂ Cl or OCF ₂ C
FHCF ₃ , Q ¹ and Q ² each independently represent H or F, L ¹ and L ² each independently represent H or F, and Z ³ and Z ⁴ each independently —CH _2. CH
₂ -or a single bond is shown. The liquid crystal composition according to claim 1, which is a compound represented by the formula (1). 3. The liquid crystal composition, wherein the first component is 2 to 50% by weight, the second component is 2 to 30% by weight, and the third component is 40 to 95% by weight, based on the total weight of the liquid crystal composition. Claim 1
Alternatively, the liquid crystal composition according to item 2. 4. A compound represented by the general formula (III) or (IV) as the fourth component
And (V) (In the formula, R ⁶ and R ⁷ each independently have 1 to 10 carbon atoms.
However, any one or two or more non-adjacent methylene groups (—CH ₂ —) in the group may be substituted with an oxygen atom. B and C are each independently a trans-1,4-cyclohexylene group or 1,
Shows the 4-phenylene group, Z ⁵ is -CH ₂ CH ₂ - shows a or a single bond. ) (In the formula, R ⁸ and R ⁹ each independently have 1 to 10 carbon atoms.
Is an alkyl group. In any case, any 1 in the group
Two or more methylene groups that are not adjacent to each other (-CH ₂
-) May be replaced by an oxygen atom (-O-).
D is a trans-1,4-cyclohexylene group or 1,
A 4-phenylene group is shown, and E is a trans-1,4-cyclohexylene group or a 1,4-phenylene group in which one H at the side position may be substituted with F. Z ⁶ is -CH ₂ C
H ₂ - or a single bond, Z ⁷ is -CH ₂ CH ₂ -,
-CH = CH-, -C≡C- or a single bond is shown. ) [Chemical 13] (In the formula, R ¹⁰ is an alkyl group having 1 to ¹⁰ carbon atoms, and any one of the groups or two or more methylene groups (—CH ₂ —) not adjacent to each other are substituted with an oxygen atom (—O—). R ¹¹ represents an alkyl group having 1 to 10 carbon atoms,
Q ³ represents H or F. 4. The liquid crystal composition according to claim 1, 2 or 3, further containing one or more compounds selected from the group consisting of: 5. The fourth component is 0.1 to 40% by weight based on the total weight of the liquid crystal composition.
3. The liquid crystal composition according to item 1. 6. General formulas (VI-a), (VI-b), (VI-
c) and (VI-d) [Chemical 15] Embedded image Embedded image (In the formula, R ¹² represents an alkyl group having 1 to 10 carbon atoms, and Y 12
Is F, Cl, CF ₃ , OCF ₃ , CF ₂ H, OCF ₂
H, OCF ₂ Cl or OCF ₂ CFHCF ₃
Q ⁴ and Q ⁵ each independently represent H or F. 6. The liquid crystal composition according to claim 2, further containing one or more compounds selected from the group consisting of: 7. A liquid crystal display device using the liquid crystal composition according to claim 1.