JPH1095761A - Propionitrile derivative, liquid crystal composition and liquid crystal display element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the novel subject compound which manifests specific liquid crystal characteristics by combination of kinds of rings and connection groups and has excellent properties as a liquid crystal composition, for example, the low viscosity and wide liquid crystal temperature range and is useful in clocks and electronic calculators. SOLUTION: This novel compound is represented by formula I (n1 and n2 are each 0 or 1; A1, A2 and A3 are each 1,4-phenylene; Z1, Z2 and Z3 are each a single bond, ethylene, ethenylene; R is a 1-1OC saturated hydrocarbon group; X1 and X2 are each F, Cl or H), typically 3-fluoro-4-cyanoethynyl-1-(trans-4- propylcyclohexyl)benzene. The compound of formula I is prepared, for example, in the case that Z1, Z2 and Z3 are esters, by reaction of a halogenated ethynylene represented by formula II with 1 equivalent amount to a largely excessive amount, based on the substrate, of a metal cyanide as a cyanidation reagent in an aprotic polar solvent. The reaction temperature is preferably near the boiling point of the solvent form the view point of the reaction rate and 1-200mol% of an acid is added as an additive in order to increase the yield of the objective compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal compound comprising a novel propiolonitrile derivative, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device using the liquid crystal composition.

[0002]

2. Description of the Related Art Display devices utilizing characteristics such as optical anisotropy and dielectric anisotropy of liquid crystal materials are widely used in watches, calculators and the like. The liquid crystal phase includes a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, and practically, the nematic phase is the most common. As a display method in this case, there are a TN (twisted nematic) type, a DS (dynamic scattering) type, a GH (guest / host) type, a DAP (alignment phase deformation) type, and the like. Many liquid crystal compounds used for these have been developed so far, but there is no example in which a single compound is sealed in a display element and put to practical use. As a liquid crystal material for display devices, it shows a liquid crystal phase over a wide temperature range around room temperature, and is stable against moisture, light, heat, air, electric fields, and electromagnetic radiation in the environment in which it is used. It is necessary to have physical properties sufficient to drive the display element.

The physical properties such as optical anisotropy, dielectric anisotropy and electric conductivity required for a liquid crystal material depend on the display system and the shape of the element. In particular, the liquid crystal material used in the STN mode used in high-quality liquid crystal displays in recent years is:
In order to obtain a good display having a high steepness and a fast response speed, the liquid crystal composition is set to have a large elastic constant ratio (k ₃ / k ₁ ) and a large dielectric anisotropy value and a low viscosity. Must-have.

However, at the same time, a single compound satisfying these conditions has not yet been known, and the liquid crystal material currently used in displays is a composition composed of a mixture of liquid crystal compounds having the respective characteristics. . Mixing a simple compound with various characteristics causes frequency dependency,
The temperature dependency increases, and it is difficult to obtain a uniform display under each use environment. Therefore, in order to obtain a display by the STN method having good characteristics with the frequency dependence and temperature dependence as small as possible, it is necessary to have a large elastic constant ratio, a large dielectric anisotropy value, and a set constant. An important key is a compound that has an optical anisotropy value close to that, has a wide liquid crystal temperature range, has high compatibility with other liquid crystals, is stable, and has low viscosity so as not to impair the response speed. Has become.

A liquid crystal compound having a large elastic constant ratio and a large dielectric anisotropy and having a relatively low viscosity is represented by the following formula:
Alkenyl compounds as shown in (A) (JP-A-59-176221)
However, this compound has a relatively narrow nematic liquid crystal temperature range, and when used as a component of a liquid crystal composition, it must be used in combination with a compound having a high clearing point to compensate for this. There is. However, since compounds having a high clearing point generally show high viscosity, the addition of the alkenyl compound results in an increase in the viscosity of the entire composition. On the other hand, a cinnamnitrile derivative represented by the following formula (B) (wherein R represents an alkyl group having 1 to 8 carbon atoms)
55-9012) is also known as a liquid crystal compound,
In particular, the stability to light is poor. The following formula (C) (where R
Represents an alkyl or alkoxy group having 1 to 9 carbon atoms) and a propiolonitrile derivative (JP-A-58-1105).
No. 27) has a wide liquid crystal range and a relatively large dielectric anisotropy value and elastic constant ratio, but is not sufficient.

[0006]

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[0007]

The present invention has excellent properties as components of a liquid crystal composition, that is, has a wide liquid crystal temperature range, a large dielectric anisotropy value, and excellent compatibility with other liquid crystal compounds. It is an object of the present invention to provide a novel liquid crystal compound capable of maintaining a property such as low viscosity of a composition and giving a large elastic constant ratio. Another object of the present invention is to provide a liquid crystal composition containing the liquid crystal compound and a liquid crystal display device composed of the composition.

[0008]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, have determined the types of rings of the propiolonitrile derivative of the formula (C), combinations of the linking groups thereof, and rings. The present inventors have found that a group of compounds having different substituents and substitution positions have specific liquid crystal characteristics, and have completed the present invention.

The present invention is represented by the following general formula (1), wherein n1 and n2 are each independently 0 or 1; A1, A2 and A3 are each independently 1,4-phenylene, Or 1,4-phenylene substituted with two F, trans-1,4-cyclohexylene, 1,3-dioxane-
2,5-diyl or 1,3-pyrimidine-2,5-diyl; Z1, Z2 and Z3 each independently represent a single bond, an ethylene group, an ethenylene group, an ethinylene group, a carbonyloxy group, an oxycarbonyl group, a methyleneoxy group; R, an oxymethylene group, a 1,4-butylene group or a 1,4-butenylene group; R is a saturated or unsaturated aliphatic hydrocarbon group having up to 10 carbon atoms, and a carbon having at least one ether bond in a chain. A saturated or unsaturated aliphatic hydrocarbon group having a number of up to 10,
Or a saturated or unsaturated fluorine-substituted aliphatic hydrocarbon group containing at least one F and having up to 10 carbon atoms; X1 and X2 each independently represent F, Cl or H, provided that n1 =
n2 = 0, Z1 is a single bond, ethylene group, carbonyloxy group or oxycarbonyl group, and R is an alkyl group or an alkoxy group, and n1 = 1, n2 = 0 or 1, Z1 and Z2 are a single bond or ethylene. When the group, Z3 is an ethylene group, and R is an alkyl group or an alkoxy group, at least one of X1 and X2 is a propionitrile derivative in which F or Cl is used.

[0010]

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Another aspect of the present invention is a liquid crystal composition comprising at least two components containing at least one propionitrile derivative represented by the above general formula (1). One component has the general formula (1)
At least one of the propiolonitrile derivatives represented by
A liquid crystal composition wherein the seed and the second component are at least one selected from the group of compounds represented by the following general formula (2) and / or at least one selected from the group of compounds represented by the general formula (3) And a liquid crystal display device using these liquid crystal compositions.

[0012]

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In the general formula (2), a is 1 or 2, b is 0 or 1, and A4 is trans-1,4-cyclohexylene, or unsubstituted or substituted with one or two Fs. 1,4-phenylene; Z4 and Z5 are each independently an ethylene group, an ethenylene group or a single bond; R1 is an alkyl group having 1 to 10 carbon atoms; X5 is -F, -CF _3, -OC
F _3, -OCF ₂ H or -Cl; (F) is F or H.

R2-(-A5-Z6-) _c -(-A6-Z7-) _d -(-A7-Z8-) _e -A8-(-COO-) _f -R3 (3) General formula (3) Wherein c, d, e and f are each independently 0 or 1; A5, A6 and A7 are each independently trans-1,4-cyclohexylene, unsubstituted or 1 or 2 F Substituted 1,4-phenylene,
A8 is trans-1,4-cyclohexylene, or unsubstituted or one or two F 1, 3-dioxane-2,5-diyl or 1,3-pyrimidine-2,5-diyl;
1,6-phenylene substituted with: Z6, Z7 and Z8 are
Each independently an ethylene group, an ethenylene group, an ethinylene group, a 1-butene-3-inylene group, a carbonyloxy group or a single bond; R2 is up to 10 carbon atoms which may have one or more ether bonds in the chain. aliphatic hydrocarbon group, saturated or unsaturated; R3 is -CN, -F, -OCF _3, -OCF
₂ H, -CF _3, a -CF ₂ H, aliphatic saturated or unsaturated hydrocarbon group of 1 or more ether bonds to carbon atoms 10 have in -CFH ₂ or chain.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION The propionitrile derivative of the present invention is represented by the general formula (1), wherein n1, n2, A1, A2,
A3, Z1, Z2, Z3, R, X1 and X2 have the same meaning as described above.

[0016]

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R in the general formula (1) is a linear or branched saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, and 1 in the chain.
Or a linear or branched C2-C2 unsaturated group containing two unsaturated groups, for example, an ethenylene group or an ethynylene group.
10 unsaturated aliphatic hydrocarbon groups, a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms containing one or more ether bonds (-O-) in the chain, or one or more It is a saturated or unsaturated fluorine-substituted aliphatic hydrocarbon group having 1 to 10 carbon atoms containing F.

The saturated aliphatic hydrocarbon group is a so-called alkyl group, for example, ethyl group, methyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, pentyl group, 2-methylbutyl group. , Hexyl group, 2-methylpentyl group, 3-methylpentyl group, heptyl group, 2
-Methylhexyl group, octyl, 2-ethylhexyl,
Examples include a 3-methylheptyl group, a nonyl group, and a decyl group. The unsaturated aliphatic hydrocarbon group is an alkenyl group, an alkynyl group, an alkadienyl group and the like, for example, a vinyl group, an allyl group, a 1-butenyl group, a 3-butenyl group,
3-methyl-1-butenyl group, 1-pentenyl group, 3-
Examples include a pentenyl group, a 4-methyl-3-pentenyl group, a 3-nonenyl group, an ethynyl group, a propynyl group, a 1-butynyl group, a butadienyl group, and a 1,5-hexadienyl group.

The saturated aliphatic hydrocarbon group having an ether bond in the chain is, for example, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group having one or more ether bonds in the alkyl chain, such as a methoxy group and an ethoxy group. , Isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, methoxymethyl, methoxyethyl, ethoxymethyl, propoxy Examples include a methyl group, a propoxypropyl group, an ethoxymethoxy group, and a propoxyethoxy group. The unsaturated aliphatic hydrocarbon group having an ether bond in the chain is the alkenyl chain, an alkenyloxy group having one or more ether bonds in the alkynyl chain, an alkynyloxy group, an alkenyloxyalkyl group, and the like. , 2-butenyloxy group, pentenyloxy group, propynyloxy group, allyloxymethyl group and the like.

Further, the saturated or unsaturated fluorine-substituted aliphatic hydrocarbon group may have a fluorine atom in the chain of the saturated or unsaturated aliphatic hydrocarbon group or the saturated or unsaturated aliphatic hydrocarbon group having an ether bond. A fluoroalkyl group, a fluoroalkenyl group, a fluoroalkoxy group, a fluoroalkoxyalkyl group, a fluoroalkenyloxy group, and the like, for example, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a difluoroethyl group, a trifluoroethyl group. Ethyl group,
Perfluoroethyl group, 2,2-difluorovinyl group,
4-fluoro-3-butenyl group, 4,4-difluoro-
Examples thereof include a 3-butenyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a trifluoromethoxymethyl group, and a 3-fluoro-1-propenyloxy group.

The propiolonitrile derivative represented by the general formula (1) is a compound represented by the following general formula wherein n1 and n2 are both 0:
A bicyclic compound represented by (1a), a tricyclic compound represented by the following general formula (1b) wherein n1 is 1 and n2 is 0, and a tricyclic compound represented by the following general formula (1c) wherein both n1 and n2 are 1 They can be roughly classified into four-ring compounds. In the general formulas (1a), (1b) and (1c), A
1, A2, A3, Z1, Z2, Z3, R, X1 and X2 have the same meanings as described above.

[0022]

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The bicyclic compound represented by the general formula (1a) has a liquid crystal temperature range around room temperature among propionitrile derivatives, has a low viscosity, and when it is used as a component of a liquid crystal composition, a crystal precipitates. It is an excellent material that is difficult to do.
Further, a liquid crystal display using a two-ring compound can perform display at a faster response speed than using another compound having a larger number of rings. More specific examples of the bicyclic compound are shown in formulas (1a-1) to (1a-28). In the formula, R represents the same meaning as described above, and Alkyl represents an alkyl group having 1 to 10 carbon atoms;
lkenyl represents an alkenyl group having 2 to 10 carbon atoms, and (F) represents F or H.

[0024]

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[0025]

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The tricyclic compound represented by the general formula (1b) has a high clearing point, has good compatibility with other liquid crystal compounds, and has good steepness of the liquid crystal composition. It has a large elastic constant ratio required for. More specific examples of the tricyclic compound are shown in formulas (1b-1) to (1b-81). Where R, Alkyl, Alke
nyl and (F) have the same meaning as described above.

[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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Each of the four-ring compounds represented by the general formula (1c) has a very high clearing point, a large elastic constant ratio, and a relatively large optical anisotropy value. It is extremely important as a component. More specific examples of the four-ring compound are shown in formulas (1c-1) to (1c-33). Where A1, A2, A
3, Alkyl, Alkenyl, R and (F) have the same meaning as described above.

[0033]

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[0034]

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[0035]

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Further, among the molecular constituents in the general formula (1), the combination with the selection of the rings A1, A2 and A3, the combination with the selection of the linking groups Z1, Z2 and Z3, the terminal group R and the propionitrile group Can be selected as the substituents X1 and X2 of the phenyl ring to be bonded to adjust the physical property value of the propiolonitrile derivative to a desired value, so that it can be suitably used as a component of a liquid crystal composition having good characteristics. Can be.

In the general formula (1), the above-mentioned formulas 1a-1 to 5 and 15 wherein the terminal group R is an alkyl group or an alkenyl group.
-19, 1b-1-5, 16-20 and 31-34, and 1c-1-1
Each of the compounds represented by 3 has a high clearing point, a large elastic constant ratio, a large dielectric anisotropy, and a large optical anisotropy value, and is excellent as a component of a liquid crystal material. Especially 1a-3 ~
Compounds 5 and 17-19, 1b-3-5, 18-20, 33 and 34, and 1c-3, 4, 7, 8, 11 and 12 have large elastic constants and low viscosities, and are STN It is useful as a display material.

In the general formula (1), the linking groups Z1, Z2 and
Formula 1a-7, 11, 1 or 2 as described above, which contains an ethylene group, a 1,4-butylene group or a 1,4-butenylene group in any of Z3.
2, 21, 25 and 26, 1b-6, 10, 11, 21, 25, 26, 36, 4
0, 41, 47, 53, 54, 56, 60, 61, 65, 71, 72, 74, 78
The compounds 79 and 79, and 1c-15, 19, 20, 26, 32 and 33 are all useful because they have high compatibility and a wide nematic liquid crystal phase which is preferable when applied to liquid crystal display.

In the general formula (1), the compounds of the above formulas 1a-6, 8, 15 to 19, 2 which are compounds having a highly conjugated partial structure
0, 22 and 26, 1b-5, 7, 16-20, 22, 26, 30, 31-4
The compounds represented by 3, 45, 46, 48, 55, 57, 64, 66 and 73 to 81, and 1c-5 to 12, 14, 16, 25, and 27 have a wide liquid crystal temperature range and a particularly large optical anisotropy. It is useful as a liquid crystal material for a display having a small cell thickness. In particular 1a-20 and 22, and 1b-20, 22, 35, 37,
55, 73 and 75 have an unparalleled value of optical anisotropy, and are useful as constituents of materials used for polymer dispersed liquid crystal display devices.

In the general formula (1), any of the linking groups Z1, Z2 and Z3 contains an oxycarbonyl group or a carbonyloxy group, or any of the rings A1, A2 and A3 is 1,3.
Formulas 1a-13, 14, 27 and 28, 1b-12, 13, 14, 15, 27, 28, as defined above, which are -dioxane-2,5-diyl or 1,3-pyrimidin-2,5-diyl 29, 30, 42, 4
3, 44, 45, 51, 52, 58, 59, 62, 63, 69, 70, 76, 7
The ester derivatives, pyrimidine derivatives, and dioxane derivatives represented by 7, 80 and 81, and 1c-12 to 13, 21, 22, 23, and 24 have particularly large values of dielectric anisotropy, and are used for low-voltage driven displays. Excellent as a liquid crystal material. Furthermore, the above-mentioned formula 1a-1 containing a cyclohexane ring in its skeleton.
-14, 1b-1 to 30 and 46 to 72, and 1c-1 to 13 have a wide liquid crystal temperature range and have excellent compatibility with other liquid crystals.

The propiolonitrile derivative represented by the general formula (1) can substitute one or both of the carbons adjacent to the propionitrile group of the phenyl ring to which the propiolonitrile group is bonded with F. Since such a fluorine-containing compound has a large dielectric anisotropy value, it is useful as a component of a liquid crystal composition for STN for the purpose of setting a low driving voltage. A compound in which the phenyl ring is not substituted with a fluorine atom can give the liquid crystal composition a higher clearing point than a fluorine-containing compound.

The propiolonitrile derivative represented by the general formula (1) of the present invention can be synthesized by any of the following methods A to C. A-1. When none of Z1, Z2 and Z3 in the general formula (1) is an ester bond (carbonyloxy group or oxycarbonyl group); Z1, Z2 and Z3 in the general formula (1) are each independently a single bond, Ethylene, ethenylene, ethinylene, methyleneoxy, oxymethylene, 1,4-butylene or 1,4-butenylene; n1, n2,
R, A1, A2, A3, X1 and X2 are propionitrile derivatives representing the same meaning as described above, are represented by the following general formula (4),
Wherein X3 is Cl, Br or I, and n1, n2, R, A1, A
2, A3, Z1, Z2, Z3, X1 and X2 can be obtained by cyanating a halogenated ethynylene having the same meaning as above with a cyanating agent.

[0043]

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This reaction is usually carried out in an aprotic polar solvent,
As the cyanating agent, metal cyanide, preferably, sodium cyanide, copper cyanide, potassium cyanide, or the like is used. The amount of metal cyanide used is 1 per substrate.
Although it is in the range of an equivalent to a large excess, a range of 1 to 3 equivalents is preferable in consideration of the post-treatment. As the aprotic polar solvent, tetrahydrofuran, dimethylformamide, acetonitrile, acetone, dioxane, N-methylpyrrolidone, and the like are preferable, and tetrahydrofuran, dimethylformamide, and N-methylpyrrolidone are particularly preferable since a good yield can be obtained. The reaction temperature of this reaction is selected from the range of the boiling point of the solvent selected from room temperature, but is preferably near the boiling point of the solvent in that the reaction proceeds promptly. In addition, an additive can be added for the purpose of promptly proceeding the reaction and increasing the yield. As the additive, salts such as lithium bromide, lithium chloride, sodium bromide, and sodium iodide are preferable, and the amount of the additive is selected from the range of 1 to 200 mol% of the reaction substrate.

The general formula (4), which is a raw material in this reaction,
The halogenated ethynylene represented by the method described in DE 4027458, or the following reaction formula (where Z1, Z2, Z3,
n1, n2, R, A1, A2, A3, X1 and X2 have the same meanings as described above), and are easily synthesized from the aldehyde compound represented by the general formula (5) in the reaction formula. be able to.

[0046]

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A-2. When any of Z1, Z2 and Z3 in the general formula (1) is an ester bond (a carbonyloxy group or an oxycarbonyl group); represented by the general formula (1), and Z1, Z2 and Z3 in the formula
Is a carbonyloxy group or an oxycarbonyl group, and the others are each independently a single bond, an ethylene group, an ethenylene group, an ethinylene group, a methyleneoxy group,
Propiononitrile derivatives that are an oxymethylene group, a 1,4-butylene group or a 1,4-butenylene group include a carboxylic acid compound represented by the following general formula (6) and an alcohol compound represented by the following general formula (7). Or an alcohol compound represented by the following general formula (8) and a general formula
A carboxylic acid compound represented by (9) (in the general formulas (6) to (9), n′1, n ″ 1, n′2 and n ″ 2 are 0 or 1, and
n′1 + n ″ 1 = 1, n′2 + n ″ 2 = 1, and R, A1, A2,
A3, X1 and X2 have the same meanings as described above). This esterification reaction is carried out in a solvent most inert to the reaction itself, such as toluene or xylene, in the presence of an acid catalyst while performing azeotropic dehydration, or in the presence of a base in an aprotic polar solvent. A method using a dehydrating condensing agent such as DCC can be employed below, and a method suitable for the substrate is employed.

[0048]

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As another method, a carboxylic acid compound represented by the general formula (6) or a carboxylic acid compound represented by the general formula (9) is reacted with a halogenated compound such as thionyl halide in a solvent inert to the reaction. Using the following general formula (10) or (11)
(In the general formulas (10) and (11), X4 is Cl, Br or I
And n′1, n ″ 1, n′2, n ″ 2, R, A1, A2, A3, Z
1, Z2, Z3, X1 and X2 represent the same meaning as described above), and then each of the general formulas
It can also be synthesized by esterification with an alcohol compound represented by (7) or the general formula (8). In this case, dehydrohalogenation treatment is carried out in a solvent inert to the reaction in the absence of a catalyst or in the presence of a base to obtain one kind of a desired propiolonitrile derivative represented by the general formula (1).

[0050]

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The raw material used in this reaction is represented by the above general formula
The alcohol compounds represented by (7) and (9) can be easily obtained by applying the method of C described later or by a method known per se. On the other hand, the general formulas (6) and (8)
The carboxylic acid compounds represented by the following formulas are described, for example, in
It can be obtained by the method described in JP-A No. 01275, JP-A-4-503523 or JP-A-59-122440.

B. In the case where an unsaturated bond other than a propionitrile group is not contained in the molecule in the general formula (1);
(1) wherein Z1, Z2 and Z3 in the formula each independently represent a single bond, an ethylene group, a carbonyloxy group, an oxycarbonyl group, a methyleneoxy group, an oxymethylene group or a 1,4-butylene group, and A propionitrile derivative in which R is a saturated aliphatic hydrocarbon group, an oxygen-containing saturated aliphatic hydrocarbon group or a fluorine-substituted saturated aliphatic hydrocarbon group is a cinnamnitrile derivative represented by the following general formula (12), To obtain a dibromo compound represented by the following general formula (13), followed by dehydrobromination treatment using a base (in general formulas (12) and (13), n1, n2, A1, A2, A3, X1 and X2 represent the same meaning as described above). In the bromination reaction of the cinnamnitrile derivative represented by the general formula (12) to the dibromo compound represented by the general formula (13), for example, a solvent inert to a reaction such as chloroform, carbon tetrachloride, dichloroethylene, and dichloromethane is used. During,
At room temperature, one equivalent or more of bromine is added to the cinnamnitrile derivative to cause a reaction. Dibromo compound represented by the general formula (13), tetrahydrofuran, dioxane, toluene, in a solvent inert to the reaction itself such as benzene, diazabicycloundecene, potassium butoxide, base such as sodium hydride dibromo compound By adding 1 equivalent or more to the compound to give a propiolonitrile derivative compound represented by the general formula (1). The cinnamnitrile derivative represented by the general formula (12) is represented by the following formula (1)
As shown in 4), the aldehyde compound represented by the general formula (5) is obtained by reacting diethyl cyanomethylphosphonate and sodium hydride in an aprotic polar solvent.

[0053]

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C. When there is no thermally unstable partial structure in the molecule; cyanomethylene triphenylphosphorane, such as benzene, toluene, monochlorobenzene, nitrobenzene, etc., is added to the acid halide represented by the following general formula (15). The reaction is performed in a solvent inert to the reaction, and the phosphorane derivative represented by the following general formula (16) (in general formulas (15) and (16), n1, n2, A1, A2, A3, Z1, Z2 , Z3,
R, X1 and X2 represent the same meaning as defined in the above general formula (1)), and then these are reduced under reduced pressure, for example, from 200 to 300
By heating to ° C. and thermally decomposing, a propiolonitrile derivative represented by the general formula (1) can be obtained. The acid halide represented by the general formula (15), which is a raw material for this reaction, is obtained by oxidizing the aldehyde derivative represented by the general formula (5) to obtain a carboxylic acid derivative by using a halogenating agent such as thionyl halide. And can be obtained by reacting

[0055]

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Tables 1 to 24 show specific examples of the propiolonitrile derivative of the present invention.

[0057]

[Table 1]

[0058]

[Table 2]

[0059]

[Table 3]

[0060]

[Table 4]

[0061]

[Table 5]

[0062]

[Table 6]

[0063]

[Table 7]

[0064]

[Table 8]

[0065]

[Table 9]

[0066]

[Table 10]

[0067]

[Table 11]

[0068]

[Table 12]

[0069]

[Table 13]

[0070]

[Table 14]

[0071]

[Table 15]

[0072]

[Table 16]

[0073]

[Table 17]

[0074]

[Table 18]

[0075]

[Table 19]

[0076]

[Table 20]

[0077]

[Table 21]

[0078]

[Table 22]

[0079]

[Table 23]

[0080]

[Table 24]

The liquid crystal composition of the present invention has the general formula described in detail above.
It is a composition comprising at least two components containing at least one of the propiolonitrile derivatives represented by (1). The second component may be another kind of a propiolonitrile derivative, but is preferably a composition comprising at least one liquid crystal compound other than the propiolonitrile derivative.
In these compositions, it is preferable to contain the propiolonitrile derivative in a ratio of 0.1 to 99.9% by weight in order to exhibit excellent characteristics.

More specifically, the liquid crystal composition of the present invention comprises:
As a first component, it contains at least one kind of a propiolonitrile derivative represented by the general formula (1), and as a second component, at least one kind selected from the group of compounds represented by the general formula (2) and And / or a composition containing at least one selected from the group of compounds represented by the general formula (3).

The compound represented by the general formula (2) is more specifically represented by the following general formulas (2a), (2b) and (2c) (where a, Z
4, Z5, R1, X5 and (F) have the same meaning as described above).

[0084]

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As preferred specific examples of the compounds contained in the general formulas (2a), (2b) and (2c), (2a-1) to (2a-
15), (2b-1) to (2b-48) and (2c-1) to (2c-55). In these formulas, R1 has the same meaning as described above.

[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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The compounds represented by these general formulas (2a) to (2c) have a positive dielectric anisotropy value, and are very excellent in thermal stability and chemical stability.

The compound represented by the general formula (3) can be more specifically represented by the following general formulas (3a), (3b), (3c), (3d) and (3e).

[0097]

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In the general formula (3a), c and e are 0
Or 1, ring A8 is 1,4-phenylene or trans-1,4-unsubstituted or substituted with F at the 3- and / or 5-position with the carbon atom to which the terminal group -CN is bonded at the 4-position
Cyclohexylene, ring A6 is trans-1,4-cyclohexylene, 1,4-phenylene or 1,3-dioxane-2,5-diyl, ring A7 is trans-1,4-cyclohexylene, 1,4-phenylene Or 1,3-pyrimidine-
2,5-diyl, the linking groups Z7 and Z8 each represent an ethylene group, a carbonyloxy group or a single bond, and the terminal group R2 is a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms and an unsaturated aliphatic group having 2 to 10 carbon atoms. And represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms and having one or more ether bonds in a chain. More specific compounds represented by the general formula (3a) are shown in (3a-1) to (3a-24). In these formulas, R2 has the same meaning as described above.

[0099]

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[0100]

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In the general formula (3b), d represents 0 or 1, R2 represents an alkyl group having 1 to 10 carbon atoms, and (F) represents F or H. More specific compounds are shown in (3b-1) to (3b-3). In these formulas, R2 has the same meaning as described above.

[0102]

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In the general formula (3c), c, d and e
Is 0 or 1, provided that c + d + e is at least 1, and rings A6 and A7 are each independently trans-1,4
-Cyclohexylene or 1,4-phenylene, linking group Z
6 and Z7 are each independently a carbonyl group or a single bond, linking group Z8 is a carbonyl group or an ethynylene group, terminal group R2 is an alkyl group having 1 to 10 carbon atoms, terminal groups R3 is -F, -OCF _3, -OCHF _2, -CF ₃ or -CFH _2,
(F) represents F or H. However terminal group R3 is -OCF _3, -O
In the case of CHF ₂ , —CF ₃ or —CFH ₂ , at least one of (F) is F. A more specific compound represented by the general formula (3c)
The results are shown in (3c-1) to (3c-28). In these formulas, R2 has the same meaning as described above.

[0104]

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[0105]

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In the general formula (3d), f is 0 or 1, and ring A5 is trans-1,4-cyclohexylene, 1,3
-Pyrimidine-2,5-diyl or 1,4-phenylene, ring A8 is trans-1,4-cyclohexylene or 1,4-phenylene, linking group Z6 is an ethynylene group,
Carbonyloxy group, ethylene group, 1,2-ethynylene-3,4-ethenylene group or single bond, terminal groups R2 and R
3 independently represent a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms or 1 to 10 carbon atoms having at least one ether bond in a chain.
Represents a saturated or unsaturated aliphatic hydrocarbon group. General formula
More specific compounds represented by (3d) (3d-1) ~ (3d-8)
Shown in In these formulas, R2 has the same meaning as described above.

[0107]

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In the general formula (3e), e is 0 or 1, and ring A5 is trans-1,4-cyclohexylene, 1,4.
-Phenylene or 1,3-pyrimidine-2,5-diyl, ring A6 is trans-1,4-cyclohexylene, unsubstituted or 1,4-phenylene substituted with one or more F, or 1,3-pyrimidine 2,5-diyl, ring A8 is trans-1,4-cyclohexylene or 1,4-phenylene, linking groups Z6 and Z8 are each independently a carbonyloxy group, ethylene or a single bond, bridge Z7 is ethenylene Group, ethynylene group, carbonyloxy group or single bond, terminal groups R2 and R3 each independently have 1 to
A saturated aliphatic hydrocarbon group having 10 carbon atoms, an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms, or a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms having at least one ether bond in a chain; Represent. More specific compounds represented by the general formula (3e) are shown in (3e-1) to (3e-13). Where R
2 has the same meaning as above.

[0109]

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The compounds represented by the above general formulas (3a) to (3c) have a positive dielectric anisotropy value and a large value, and are used as a composition component particularly for the purpose of reducing the threshold voltage. You. It is also used for the purpose of adjusting the viscosity, adjusting the refractive index anisotropy value, expanding the temperature range of the liquid crystal phase, and further improving the steepness.

The compounds represented by the general formulas (3d) and (3e) are compounds having a negative or slightly positive dielectric anisotropy value. In particular, the compound represented by the general formula (3d) is mainly used for the purpose of lowering the viscosity and / or adjusting the refractive index anisotropy, and the compound represented by the general formula (3e) increases the clearing point. And the like, and / or for the purpose of adjusting the refractive index anisotropy value. Especially ST
It is an indispensable compound when preparing a liquid crystal composition for an N display system and a normal TN display system.

The liquid crystal composition of the present invention comprises at least one of 0.1 to 99.9% by weight selected from the propiolonitrile derivatives represented by the above general formula (1), based on the total composition; 1 to 99% by weight, preferably 10 to 97% by weight, at least one selected from compounds represented by (2),
More preferably, it contains 40 to 95% by weight.

In the case of another liquid crystal composition of the present invention, for example, a liquid crystal composition for a normal TN display mode or STN display mode, propiolonitrile represented by the above general formula (1) on the basis of the total composition. At least one selected from derivatives;
1 to 99.9% by weight, at least one selected from compounds represented by the general formula (3) 1 to 99% by weight, preferably 10 to 97% by weight, more preferably 40 to 95% by weight.
It contains. In this composition, a part of the compound represented by the general formula (3) may be replaced with the compound represented by the general formula (2).

The liquid crystal composition of the present invention may further contain a known compound for the purpose of adjusting the threshold voltage, the liquid crystal phase temperature range, the refractive index anisotropy value, the dielectric anisotropy value, the viscosity and the like. It can also be contained as a third component.

By using the liquid crystal composition of the present invention for a TFT liquid crystal display device, the sharpness and the viewing angle are improved. Since the compound represented by the general formula (1) is a low-viscosity compound, the response speed of a liquid crystal display device using the compound is greatly improved.

The liquid crystal composition of the present invention is prepared by a conventional method. Generally, a method is used in which various components are dissolved at a high temperature. However, after dissolving and mixing in an organic solvent in which the liquid crystal dissolves, the solvent may be distilled off under reduced pressure.

When the liquid crystal composition of the present invention is used as a liquid crystal material for a liquid crystal display device, it is improved and optimized by appropriate additives depending on the intended use.
Such additives are well known to those skilled in the art and are described in detail in the literature and the like. In general, the following formula (C) is used as a chiral dopant for inducing a helical structure of a liquid crystal, adjusting a required twist angle, and preventing reverse twist (reverse twist).
Optically active compounds as shown in -1) to (C-8) are added.

[0118]

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Further, a dichroic dye such as a merocyanine-based, styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye is added to obtain a guest-host (GH) mode liquid crystal composition. Can be used. Alternatively, NCAP made by encapsulating nematic liquid crystal or polymer network liquid crystal display device (PNLC made by forming a three-dimensional network polymer in liquid crystal)
Polymer dispersed liquid crystal display device (PDLCD) represented by D)
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.

[0120]

The present invention will be described in more detail with reference to the following examples. A. Example 1 Synthesis of Propioronitrile Derivative Example 1 3-Fluoro-4-cyanoethynyl-1-
Synthesis of (trans-4-propylcyclohexyl) benzene (Compound No. 2) 15 mmol of 3-fluoro-4-ethynyl-1- (trans-4-propylcyclohexyl) benzene was dissolved in 5 ml of tetrahydrofuran and cooled to −78 ° C. 30 mmol of n-butyllithium was added dropwise. After completion of the dropwise addition, the reaction solution was further stirred for 2 hours, and a solution of 20 mmol of iodine in 3 ml of tetrahydrofuran was added dropwise. After the completion of the dropwise addition, the reaction solution was heated to room temperature and poured into an aqueous solution of sodium thiosulfate. This was extracted with heptane, and the obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained yellow oil was isolated and purified using silica gel column chromatography to obtain colorless crystals. As a result of various instrumental analyses, 3-fluoro-4-iodoethynyl-1-
It was confirmed to be (trans-4-propylcyclohexyl) benzene.

10 mmol of the obtained 3-fluoro-4-iodoethynyl-1- (trans-4-propylcyclohexyl) benzene is dissolved in 3 ml of tetrahydrofuran, 11 mmol of copper cyanide and 3 mmol of lithium bromide are added, and the mixture is heated under reflux. Stir for 5 hours. 10 ml of a 6N hydrochloric acid saturated solution of ferric chloride was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. After completion of the stirring, the reaction solution was extracted with toluene, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained brown oil was isolated and purified by silica gel column chromatography to obtain a colorless oil. This was recrystallized from ethanol to obtain colorless crystals. As a result of various instrumental analysis, it was confirmed that this was the title compound. By the same method as described above, among the compounds shown in Tables 1 to 24, compound numbers 1 to 5, 11 to 15, 21 to 29, and 41
~ 45, 51-55, 61-65, 71-75, 81-
85, 91 to 95, 101 to 105, 111 to 114,
121-125, 131-135 and 221-240
Can be synthesized.

Example 2 Synthesis of 3-fluoro-4-cyanoethynyl-1- (4-propylphenyl) carbonyloxybenzene (Compound No. 153) 100 mmol of 3-fluoro-4-cyanophenol was dissolved in 200 ml of dimethylformamide. While stirring the solution under ice-cooling, 110 mmol of dimethylbutylsilyl chloride and 110 mmol of imidazole were added, the temperature was gradually raised to room temperature, and the solution was further stirred for 3 hours. The solution was poured into water and extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a colorless oil. This was distilled under reduced pressure to obtain 100 mmol of 2-fluoro-4-dimethylbutylsilyloxybenzonitrile.

The obtained 2-fluoro-4-dimethylbutylsilyloxybenzonitrile (72 mmol) was dissolved in toluene 10
The solution was dissolved in 0 ml, and while cooling to -70 ° C, 100 ml of a toluene solution of diisobutylaluminum hydride (1M) was added dropwise. After completion of the dropwise addition, the reaction solution was stirred at the same temperature for 1 hour, then poured into an ammonium chloride solution, and extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 26 mmol of 2-fluoro-4-dimethylbutylsilyloxybenzaldehyde as a yellow oil. This was used for the next reaction without purification. The obtained 2-fluoro-4-dimethylbutylsilyloxybenzaldehyde (26 mmol) was dissolved in methylene chloride (50 ml), a methylene chloride solution of triphenylphosphine (110 mmol) and carbon tetrabromide (52 mmol) was added dropwise under ice-cooling. Stirred for hours. Remove insolubles from the reaction solution,
Concentration under reduced pressure gave a yellow oil. This was purified using silica gel column chromatography to obtain 26 mmol of 2-fluoro-4-dimethylbutylsilyloxyphenyl-2,2-dibromoethylene as a colorless oil.

1- (2-fluoro-4-dimethylbutylsilyloxyphenyl) -2,2-dibromoethylene 26
mmol was dissolved in 50 ml of tetrahydrofuran, and 134 ml of n-butyllithium (1.6M) was added dropwise while stirring at -70 ° C. After the completion of the dropwise addition, the reaction solution was stirred for 3 hours, and then a solution of 30 mmol of iodine in 10 ml of tetrahydrofuran was added dropwise.
The temperature was gradually raised to room temperature. After completion of the stirring, the solution was poured into a sodium thiosulfate solution and extracted with heptane. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a brown solid. This was purified by silica gel column chromatography to give 1- (2-fluoro-4-dimethylbutylsilyloxyphenyl) -2-iodoethyne 25m
mol was obtained as a yellow solid. After dissolving 25 mmol of 1- (2-fluoro-4-dimethylbutylsilyloxyphenyl) -2-iodoethine in 50 ml of tetrahydrofuran,
Copper cyanide and lithium bromide were added and reacted under reflux for 3 hours. After the completion of the reaction, the solution was poured into a hydrochloric acid solution of iron chloride and extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-fluoro-4-hydroxyphenylpropionitrile.
0 mmol was obtained as a colorless solid.

20 mmol of 2-fluoro-4-hydroxyphenylpropionitrile and 21 mmol of 4-propylbenzoic acid chloride were dissolved in 50 ml of methylene chloride, 25 mmol of pyridine was added dropwise with stirring under ice cooling, and the mixture was further stirred for 3 hours. After water was added to the reaction solution, it was extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was purified by silica gel column chromatography, and recrystallized from ethanol to obtain 8 mmol of the title compound. Compounds of compound numbers 141 to 220 among the compounds shown in Tables 1 to 24 can be synthesized by the same method as described above.

Example 3 4- [2- [trans-4-
Synthesis of (3-butenyl) cyclohexyl] ethyl] phenylpropionitrile (Compound No. 32) 4- [2- [trans-4- (3-butenyl) cyclohexyl] ethyl] benzonitrile (42 mmol) was dissolved in toluene 10
The mixture was dissolved in 0 ml, and 45 ml of a toluene solution of isobutylaluminum hydride (1M) was added dropwise while stirring under ice cooling.
After the reaction solution was further stirred at room temperature for 2 hours, it was poured into an aqueous ammonium chloride solution and extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4- [2- [trans-4- (3
-Butenyl) cyclohexyl] ethyl] benzaldehyde (35 mmol) was obtained. This was used for the next reaction without purification. Carbon tetrabromide 10mm in methylene chloride 100ml
ol and 138 mmol of triphenylphosphine were dissolved in a solution of 35 mmol of 4- [2- [trans-4- (3-butenyl) cyclohexyl] ethyl] benzaldehyde in methylene chloride. After completion of the dropwise addition, the reaction solution was stirred at room temperature for 3 hours to remove undissolved substances from the reaction system and concentrated. The obtained brown oil was purified by silica gel column chromatography, and 2 ', 2'-dibromo-4- [2-
30 mmol of [trans-4- (3-butenyl) cyclohexyl] ethyl] styrene were obtained as colorless crystals.

30 mmol of 2 ', 2'-dibromo-4- [2- [trans-4- (3-butenyl) cyclohexyl] ethyl] styrene was dissolved in 100 ml of tetrahydrofuran, and a hexane solution of n-butyllithium (1.6M) was obtained. 37.
5 ml was added dropwise under ice cooling. After completion of the dropwise addition, a solution of iodine in tetrahydrofuran was added dropwise to the reaction solution, the temperature was gradually raised to room temperature, and the mixture was stirred for 3 hours. After the completion of the reaction, the solution was poured into a sodium thiosulfate solution and extracted with heptane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was purified by silica gel column chromatography to give 2- [4- [2- [trans-
18 mmol of 4- (3-butenyl) cyclohexyl] ethyl] phenyl] iodoethyne were obtained as colorless crystals. 2-
13.7 mmol of [4- [2- [trans-4- (3-butenyl) cyclohexyl] ethyl] phenyl] iodoethine
Was dissolved in tetrahydrofuran, 1 mmol of lithium bromide and 22 mmol of copper cyanide were added, and the mixture was reacted for 5 hours under reflux with heating. After completion of the reaction, the solution was poured into a 6N hydrochloric acid solution of ferric chloride and extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was isolated and purified by silica gel column chromatography, and recrystallized from ethanol to obtain 4.1 mmol of the title compound. In the same manner as above, Tables 1-2
Among the compounds described in 4, compound numbers 6 to 10, 16 to
20, 31-39, 46-49, 56-59, 66-6
9, 76-79, 86-90, 96-100, 106-
110, 116 to 119, 126, 127, 129, 1
Compounds 30, 30, 136, 137, 139 and 140 can be synthesized.

Example 4 3-Fluoro-4- [2- (4
Synthesis of -propylphenyl) ethynyl] phenylpropionitrile (Compound No. 30) 33 mmol of 3-fluoro-4-bromoiodobenzene, 0.6 mmol of copper iodide and 1.1 mmol of dichlorobistriphenylphosphine palladium were added to 100 ml of diethylamine.
And 33 mmol of 4-propylphenylacetylene was added dropwise with stirring under an argon stream. After dropping,
The mixture was further stirred at room temperature for 2 hours and poured into water. This was extracted with heptane, washed with water, and concentrated under reduced pressure to obtain a brown oil. This was isolated and purified by silica gel column chromatography to obtain 33 mmol of 2-fluoro-4- [2- (4-propylphenyl) ethynyl] bromobenzene as a pale yellow oil. 2-fluoro-4- [2- (4-
Propylphenyl) ethynyl] bromobenzene 33 mmo
l, 1.2 mmol of copper iodide and 1.2 mmol of dichlorobistriphenylphosphine palladium in diethylamine 10
It was dissolved in 0 ml and stirred under a stream of argon. 20 ml of a diethylamine solution containing 50 mmol of trimethylsilylacetylene was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 5 hours. After completion of the stirring, water was added to the reaction solution, and extracted with heptane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was isolated and purified using silica gel column chromatography to obtain 7 g of 1- [2-fluoro-4- [2- (4-propylphenyl) ethynyl] phenyl] -2-trimethylsilylacetylene as a colorless solid.

22 mmol of 1- [2-fluoro-4- [2- (4-propylphenyl) ethynyl] phenyl] -2-trimethylsilylacetylene and potassium hydroxide 10
g in 100 ml of ethanol and 10 ml of water.
Stirred for 6 hours while stirring at ° C. After completion of the stirring, the reaction solution was poured into dilute hydrochloric acid and extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was isolated and purified using silica gel column chromatography, and 2-fluoro-4-
5.7 g of [2- (4-propylphenyl) ethynyl] phenylacetylene was obtained as a colorless solid. 2-fluoro-
22 mmol of 4- [2- (4-propylphenyl) ethynyl] phenylacetylene is dissolved in 50 ml of tetrahydrofuran, and n-butyllithium (1.6
M) 30 ml were added dropwise. After the dropwise addition, the reaction solution was stirred for 2 hours, and a solution of 28 mmol of iodine in 50 ml of tetrahydrofuran was added.
Was added dropwise, and the mixture was heated to room temperature, then poured into a sodium thiosulfate solution, and extracted with heptane. After washing the organic layer with water,
Dry over anhydrous magnesium sulfate and concentrate under reduced pressure to give a brown oil. This was isolated and purified by silica gel column chromatography to give 1- [2-fluoro-4- [2-
(4-propylphenyl) ethynyl] phenyl] -2-iodoacetylene (22 mmol) was obtained as yellow crystals. 1-
22 mmol of [2-fluoro-4- [2- (4-propylphenyl) ethynyl] phenyl] -2-iodoacetylene,
2 g of lithium bromide and 56 mmol of copper cyanide were dissolved in 100 ml of tetrahydrofuran, and the mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, the reaction solution was poured into a 6N hydrochloric acid solution of ferric chloride and extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a brown oil. This was isolated and purified using silica gel column chromatography, and recrystallized from ethanol to obtain 0.6 g of the title compound as colorless crystals. Among the compounds described in Tables 1 to 24, Compound Nos. 30, 40, 50, 60, 70, 80, 115 and 12 were prepared in the same manner as described above.
Compounds 0, 128 and 138 can be synthesized.

B. Liquid crystal composition Nematic phase transition temperature (T _NI ) of a liquid crystal composition containing the propiolonitrile derivative of the present invention, viscosity at 20 ° C.
An example in which (η ₂₀ ), refractive index anisotropy (Δn) at 25 ° C., dielectric anisotropy (Δε) at 25 ° C. and threshold voltage (V _th ) were measured is shown below.

In the examples, the chemical structures of the compounds are represented by the following abbreviations. When the terminal group is an alkyl group, only the number of carbon atoms is indicated. Hx: trans-1,4-cyclohexylene Be: 1,4-phenylene Be (F) and Be (F, F): 3- and 3-5-substituted 1,4-substituted 1,4
-Phenylene Py: 1,3-pyrimidine-2,5-diyl Do: 1,3-dioxane-2,5-diyl Tr: ethynylene group

[0132] Example 5 3-Hx-Be (F ) -Tr-CN ( Compound No.2) 17.0% 3-Hx- Be-CN 15.0% 3-Hx-Be-OC 2 H 5 5.0% 3-Hx -Hx-4 11.0% 3-Hx-Hx-5 5.0% 5-Hx-Hx-2 4.0% 3-Hx-Hx-Be-1 10.0% 3-Hx-Hx-Be-3 16.0% 3-Hx- Be (F) -Tr-Be-2 5.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3- Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0% T _NI = 104.8 [° C] η = 14.0 [mPa · s] Δn = 0.137 Δε = 7.8 V _th = 2.23 [V]

Example 6 3-Hx-Be (F) -Tr-CN (Compound No. 2) 15.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 3.0% 3 -Hx-Be-CN 14.0% 3 -Hx-Be-OC 2 H 5 7.0% 3-Hx-Hx-4 11.0% 3-Hx-Hx-5 5.0% 5-Hx-Hx-2 4.0% 3-Hx -Hx-Be-1 10.0% 3-Hx-Hx-Be-3 16.0% 3-Hx-Be (F) -Tr-Be-2 3.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be- 2 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-3 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-4 4.0% T NI = 100.2 [℃] eta = 14.7 [ mPa · s] Δn = 0.132 Δε = 8.8 V _th = 2.13 [V]

Example 7 CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No. 7) 10.0% 3-Hx-Be (F) -Tr-CN (Compound No. 2) 9.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-CN 10.0% CH ₃ CH = CHC ₂ H ₄ -Hx-Be-CN 13.0% 3-Hx-Hx-4 11.0% 3-Hx-Hx-5 10.0% 3- Hx-Hx-Be-1 10.0% 3-Hx-Be (F) -Tr-Be-2 7.0% 3-Hx-Be (F) -Tr-Be-3 7.0% 3-Hx-Be (F)- Tr-Be-4 7.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 6.0% T _NI = 11.7 [° C] η = 15.6 [mPa · s] Δn = 0.164 Δε = 8.1 V _th = 2.20 [V]

Example 8 CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 8.0% 3-Hx-Be-CN 20.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-CN 9.0% 3-Hx-Hx-4 9.0% 2-Be-Tr-Be-1 10.0% 2-Be-Tr-Be-3 8.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-OCH ₃ 5.0% 3-Hx-Hx-Be-F 4.0% 3-Hx-Hx-Be-3 7.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 _{4.0% 3-Hx-C 2} H 4 -Be-Tr-Be-3 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-4 4.0% T NI = 81.3 [℃] eta = 13.1 [mPa・ S] Δn = 0.155 Δε = 7.1 V _th = 1.96 [V]

Example 9 3-Be-COO-Be (F) -Tr-CN (Compound No.153) 12.0% 3-Hx-Be-COO-Be (F) -Tr-CN (Compound No.162) 8.0% C ₃ H ₇ OCH ₂ -Be-COO-Be (F) -CN 12.0% 2-Hx-Be-CN 12.0% 3-Hx-Be-CN 19.0% 3-Hx-Be-OC ₂ H ₅ 7.0 3-Hx-Hx-Be-1 7.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 3.0 % 3-Hx-C 2 H 4 -Be-Tr-Be-4 3.0% 2-Hx-Hx-Be-CN 4.0% 3-Hx-Hx-Be-CN 5.0% T _NI = 91.4 [° C] η = 33.7 [mPa · s] Δn = 0.163 Δε = 20.9 V _th = 1.13 [V]

Example 10 3-Be-Tr-Be (F) -Tr-CN (Compound No. 30) 10.0% 3-Hx-Be-CN 20.0% 1-Be-Tr-Be-3 8.0% 2- Be-Tr-Be-1 10.0% 2-Be-Tr-Be-OCH ₃ 1.6% 3-Be-Tr-Be-OCH ₃ 1.6% 4-Be-Tr-Be-OCH ₃ 1.6% 4-Be-Tr -Be-OC ₂ H ₅ 1.6% 5-Be-Tr-Be-OCH ₃ 1.6% 3-Hx-Hx-Be-1 11.0% 3-Hx-Hx-Be-3 9.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0% 3-Hx -Be (F) -Tr-Be-2 6.0% 3-Hx-Be (F) -Tr-Be-3 6.0% T _NI = 98.1 [° C] η = 16.3 [mPa · s] Δn = 0.220 Δε = 7.3 V _th = 2.07 [V]

Example 11 3-Hx-Be (F) -Tr-CN (Compound No. 2) 10.0% 2-Hx-Be (F) -CN 10.0% 3-Hx-Be (F) -CN 10.0% _{3-Hx-Be-OC 2} H 5 10.0% 3-Hx-Hx-4 10.0% 2-Be-Tr-Be-OCH 3 10.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx- Be-3 16.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be- 3 4.0% 3-Hx-Hx-Be-CN 4.0% T _NI = 88.7 [° C] η = 16.1 [mPa · s] Δn = 0.136 Δε = 7.7 V _th = 1.86 [V]

Example 12 CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 8.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F , F) -CN 4.0% C ₃ H ₇ OCH ₂ -Be-COO-Be (F) -CN 8.0% 2-Hx-Be (F) -CN 8.0% 5-Py-Be-F 3.0% 3-Py -Be (F) -F 3.0% 3 -Hx - Be-OC 2 H 5 10.0% 3-Hx-Hx-4 10.0% 2-Be-Tr-Be-OCH 3 10.0% 3-Hx-Hx-Be -1 10.0% 3-Hx-Hx -Be-3 14.0% 3-Hx-Hx-Be-OCH 3 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% T _NI = 69.2 [° C] η = 17.6 [mPa · s] Δn = 0.133 Δε = 10.3 V _th = 1.40 [V]

Example 13 CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 10.0% 3-Hx-Be-CN 20.0% 3-Hx-Be (F ) -CN 5.0% 2-Hx-Hx-Be (F) -CN 7.0% 3-Hx-Hx-Be (F) -CN 7.0% 3-Hx-Hx-4 10.0% 3-Hx-Be-OC _{2 H 5 11.0% 3-Hx-} Hx-Be-1 7.0% 3-Hx-Hx-Be-OCH 3 4.0% 3-Hx-Hx-Be-3 4.0% 3-Hx-C 2 H 4 -Be-Tr -Be-2 3.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 3.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 3.0% CH ₃ OCH ₂ -Hx-Be -Be-Hx-3 6.0% T _NI = 101.0 [° C] η = 20.3 [mPa · s] Δn = 0.134 Δε = 9.1 V _th = 1.91 [V]

Example 14 3-Be-Tr-Be (F) -Tr-CN (Compound No. 30) 13.0% 3-Hx-Be-CN 15.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-CN 9.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 2.0% 3-Hx-Hx-COO-CH ₃ 2.0% 3-Hx-Hx-4 9.0% 2-Be- Tr-Be-1 10.0% 2-Be-Tr-Be-3 6.0% 3-Hx-Hx-Be-1 5.0% 3-Hx-Hx-Be-OCH ₃ 5.0% 3-Hx-Be-Be-F 5.0% 3-Hx-Hx-Be-3 15.0% 3-Hx-COO-Be-COO-Be-2 2.0% 3-Hx-COO-Be-COO-Be-F 2.0% T _NI = 84.2 [° C] η = 16.6 [mPa · s] Δn = 0.170 Δε = 8.7 V _th = 1.69 [V]

Example 15 3-Be-COO-Be (F) -Tr-CN (Compound No.153) 11.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No.7) 11.0 % 3-Hx-Be-OC 2 H 5 3.0% 2-Be-Tr-Be-OCH 3 6.8% 3-Be-Tr-Be-OCH 3 6.8% 4-Be-Tr-Be-OCH 3 6.8% 4 _{-Be-Tr-Be-OC 2} H 5 6.8% 5-Be-Tr-Be-OCH 3 6.8% 3-Hx-Hx-Be-OCH 3 3.0% 3-Hx-C 2 H 4 -Be-Tr- Be-2 2.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 3.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 3.0% 3-Hx-Be (F)- Tr-Be-2 6.0% 3-Hx-Be (F) -Tr-Be-3 6.0% 3-Hx-Be (F) -Tr-Be-4 6.0% 2-Py-Be-Hx-3 4.0% 3-Py-Be-Hx-3 4.0% 3-Py-Be-Be-2 4.0% T _NI = 108.8 [° C] η = 27.4 [mPa · s] Δn = 0.246 Δε = 9.6 V _th = 1.93 [V]

Example 16 CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No. 7) 9.0% 3-Hx-Be-COO-Be (F) -Tr-CN (Compound No. 162) _{) 10.0% CH 3 CH = CHC} 2 H 4 -Hx-Be-CN 9.0% 3-Hx-Be-CN 14.0% CH 3 OCH 2 -Hx-Be-CN 8.0% C 2 H 5 OCH 2 -Hx-Be -CN 4.0% 3-Hx-Hx-4 10.0% CH ₃ OCH ₂ -Hx-Hx-5 8.0% 2-Be-Tr-Be-OCH ₃ 11.0% 3-Hx-Hx-Be-1 8.0% 3- Hx-Hx-Be-3 9.0% T _NI = 84.0 [° C] η = 16.8 [mPa · s] Δn = 0.143 Δε = 12.0 V _th = 1.64 [V]

Example 17 3-Be-COO-Be (F) -Tr-CN (Compound No. 153) 12.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 6.0 % C ₃ H ₇ OCH ₂ -Be-COO-Be (F) -CN 6.0% 2-Hx-Be-CN 12.0% 3-Hx-Be-CN 16.0% 2-Hx-Hx-Be-CN 4.0% 3 -Hx-Hx-Be-CN 5.0 % 4-Hx-Hx-Be-CN 4.0% 5-Hx-Hx-Be-CN 4.0% 3-Hx-Be-OC 2 H 5 10.0% 3-Hx-Hx- Be-1 7.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be- 3 3.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 3.0% T _NI = 90.4 [° C] η = 28.5 [mPa · s] Δn = 0.155 Δε = 19.0 V _th = 1.20 [V]

Example 18 3-Be-COO-Be (F) -Tr-CN (Compound No. 153) 10.0% C ₃ H ₇ OCH ₂ -Be-COO-Be (F) -CN 8.0% C ₅ H ₁₁ OCH ₂ -Be-COO-Be (F) -CN 4.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 10.0% C ₂ H ₅ OCH ₂ -Hx-Be- COO-Be (F) -CN 2.0% 3-Hx-Be (F) -COO-Be (F) -CN 2.0% 2-Hx-Be-COO-Be (F, F) -CN 2.0% 3-Hx -Hx-COO-Be-F 5.0 % 5-Hx-Hx-COO-Be-F 4.0% 3-Hx-Be-COO-Be-F 6.0% 3-Hx-Be-OC 2 H 5 10.0% 3- Hx-Hx-4 10.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-3 10.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-Be (F)- CH = CH-Be-2 5.0% T _NI = 99.0 [° C] η = 36.8 [mPa · s] Δn = 0.135 Δε = 23.6 V _th = 1.10 [V]

Example 19 CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No. 7) 10.0% 3-Hx-Be (F) -Tr-CN (Compound No. 2) 7.0% 2 -Hx-Be (F) -CN 10.0% 3-Hx-Be (F) -CN 10.0% 5-Hx-Be (F) -CN 9.0% 2-Be-COO-Be-CN 10.0% 3-Be- COO-Be-CN 4.0% 2-Hx-Hx-Be (F) -CN 9.0% 3-Hx-Hx-Be (F) -CN 12.0% 3-Py-Be-Be-F 8.0% 2-Hx- Hx-Be-CN 3.0% 3-Hx-Hx-Be-CN 3.0% 3-Hx-Be-COO-Be-Be-CN 3.0% 5-Hx-Hx-COO-Be-Be-CN 2.0% T _NI = 91.5 [° C] η = 52.8 [mPa · s] Δn = 0.164 Δε = 19.3 V _th = 1.00 [V]

Example 20 3-Hx-Be (F) -Tr-CN (Compound No. 2) 13.0% CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 10.0% 2-Be-Be-CN 8.0% 4-Be-Be-CN 6.0% 3-Hx-Hx-Be-F 5.0% 2-Hx-Hx-Be-CN 4.0% 3-Hx-Hx- Be-CN 6.0% 5-Py-Be-F 6.0% 3-Py-Be-Be-F 6.0% 2-Be-Tr-Be-OCH ₃ 2.0% 2-Hx-Hx-Be-1 6.0% 3- Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-3 15.0% 3-Hx-Hx-Be-OCH ₃ 5.0% T _NI = 105.6 [° C] η = 21.6 [mPa · s] Δn = 0.169 Δε = 11.3 V _th = 1.66 [V]

Example 21 3-Hx-Be-COO-Be (F) -Tr-CN (Compound No. 162) 11.0% 3-Hx-Be-OC ₂ H ₅ 14.0% 3-Hx-Be-OC ₄ H ₉ 13.0% 3-Py-Be-4 3.1% 4-Py-Be-4 3.1% 6-Py-Be-4 3.2% 3-Py-Be-5 3.2% 4-Py-Be-5 3.2% 6 -Py-Be-5 3.2% 6 -Py-Be-OC 5 H 11 4.0% 6-Py-Be-OC 6 H 13 4.0% 6-Py-Be-OC 7 H 15 4.0% 6-Py-Be- OC ₈ H ₁₇ 4.0% 2-Hx-Hx-Be-1 4.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-3 10.0% 3-Hx-Hx-Be-OCH ₃ 5.0 % T _NI = 78.8 [° C] η = 35.3 [mPa · s] Δn = 0.130 Δε = 5.4 V _th = 2.47 [V]

Example 22 3-Be-COO-Be (F) -Tr-CN (Compound No. 153) 10.0% 3-Do-Be-CN 10.0% 4-Do-Be-CN 12.0% 5-Do- Be-CN 8.0% 5-Py-Be (F) -F 10.0% 2-Py-Be-2 1.4% 3-Py-Be-2 1.3% 4-Py-Be-2 1.3% 3-Hx-COO- Be-OC ₄ H ₉ 5.0% 4-Hx-COO-Be-OC ₂ H ₅ 3.7% 3-Hx-COO-Be-OC ₂ H ₅ 3.1% 1O-Be-COO-Be-2 2.5% 5-Hx -COO-Be-1 3.7% 4-Hx-COO-Be-4 5.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-Hx-Be-3 13.0% 2-Py-Be-Hx- 3 6.0% T _NI = 63.5 [° C] η = 30.2 [mPa · s] Δn = 0.123 Δε = 15.6 V _th = 1.25 [V]

Example 23 3-Be-COO-Be (F) -Tr-CN (Compound No. 153) 6.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No. 7) 4.0 % 3-Be-COO-Be (F) -CN 8.0% 5-Py-Be-CN 8.0% CH ₂ = CH-Hx-Be-CN 4.0% CH ₃ CH = CH-Hx-Be-CN 4.0% 5 -Hx-Hx-CH = CH ₂ 10.0% 3-Hx-Hx-C ₂ H ₄ CH = CH ₂ 7.0% 3-Hx-Hx-C ₂ H ₄ CH = CHCH ₃ 7.0% CH ₂ = CH-Hx- Hx-Be-1 8.0% CH ₂ = CHC ₂ H ₄ -Hx-Hx-Be-1 15.0% 3-Hx-Hx-COO-Be (F) -F 5.0% 3-Hx-Be-Tr-Be- 1 5.0% 3-Hx-Be-Tr-Be-2 5.0% 3-Hx-Be-Tr-Be-3 4.0% T _NI = 101.0 [° C] η = 15.8 [mPa · s] Δn = 0.143 Δε = 11.1 V _th = 1.86 [V]

Example 24 CH ₂ = CHC ₂ H ₄ -Hx-Be-Tr-CN (Compound No. 7) 5.0% 7-Hx-Be (F, F) -F 4.0% 3-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 12.0% 4-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 10.0% 5-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 10.0% 3-Hx -Hx-Be (F, F) -F 10.0% 3-Hx-Hx-C 2 H 4 -Be (F, F) -F 11.0% 5-Hx-Hx-C ₂ H ₄ -Be (F, F) -F 10.0% 3-Hx-Be-Be (F, F) -F 12.0% 5-Hx-Be-Be (F, F) -F 12.0% 3-Hx- Hx-Be-Be (F, F) -F 2.0% 5-Hx-Hx-C 2 H 4 -Be-Be (F, F) -F 2.0% T NI = 78.9 [℃] eta = 26.9 [mPa · s] Δn = 0.097 Δε = 9.2 V _th = 1.53 [V]

Example 25 CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 15.0% 7-Hx-Be (F, F) -F 5.0% 3- Hx-C ₂ H ₄ -Hx-Be (F, F) -F 9.0% 4-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 8.0% 5-Hx-C ₂ H ₄ -Hx -Be (F, F) -F 8.0% 3-Hx-Hx-C ₂ H ₄ -Be (F, F) -F 10.0% 3-Hx-Be-Be (F, F) -F 9.0% 5- Hx-Be-Be (F, F) -F 9.0% 3-Hx-Hx-Be (F, F) -F 6.0% 4-Hx-Hx-Be (F, F) -F 5.0% 3-Hx- Be-COO-Be (F, F) -F 3.0% 5-Hx-Be-COO-Be (F, F) -F 3.0% 3-Hx-Hx-COO-Be (F, F) -F 10.0% T _NI = 68.2 [° C] η = 25.4 [mPa · s] Δn = 0.105 Δε = 13.7 V _th = 1.17 [V]

Example 26 3-Hx-Be (F) -Tr-CN (Compound No. 2) 7.0% 3-Hx-Be-COO-Be (F) -Tr-CN (Compound No. 162) 6.0% 5-Hx-C ₂ H ₄ -Be (F) -F 4.0% 7-Hx-Be (F) -F 7.0% 2-Hx-Hx-Be (F) -F 9.0% 3-Hx-Hx-Be (F) -F 9.0% 5-Hx-Hx-Be (F) -F 9.0% 2-Hx-C ₂ H ₄ -Hx-Be (F) -F 4.0% 3-Hx-C ₂ H ₄ -Hx -Be (F) -F 2.0% 5-Hx-C ₂ H ₄ -Hx-Be (F) -F 4.0% 3-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 6.0% 4 -Hx-C ₂ H ₄ -Hx-Be (F, F) -F 5.0% 5-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 5.0% 3-Hx-Hx-Be (F , F) -F 8.0% 3- Hx-Hx-C 2 H 4 -Be (F, F) -F 8.0% 5-Hx-Hx-C 2 H 4 -Be (F, F) -F 7.0% T _NI = 82.4 [° C] η = 25.0 [mPa · s] Δn = 0.093 Δε = 7.6 V _th = 1.60 [V]

Example 27 3-Be-Tr-Be (F) -Tr-CN (Compound No. 30) 10.0% 3-Hx-Be-Cl 7.0% 4-Hx-C ₂ H ₄ -Be-Be ( F) -F 3.0% 2-Hx-Be-Be (F) -F 6.0% 3-Hx-Be-Be (F) -F 6.0% 5-Hx-Be-Be (F) -F 12.0% 2- Hx-Hx-Be-Cl 5.0% 4-Hx-Hx-Be-Cl 10.0% 5-Hx-Hx-Be-Cl 4.0% 3-Hx-Be-Be (F, F) -F 17.0% 5-Hx -Be-Be (F, F) -F 12.0% 5-Hx-C ₂ H ₄ -Be-Be (F, F) -F 5.0% 3-Hx-Hx-Be-1 3.0% T _NI = 93.7 [ ° C] η = 24.9 [mPa · s] Δn = 0.160 Δε = 7.8 V _th = 1.60 [V]

Example 28 3-Be-COO-Be (F) -Tr-CN (Compound No. 153) 5.0% 5-Hx-COO-Be-F 2.0% 7-Hx-COO-Be-F 2.0% 2-Hx-Hx-Be (F) -F 10.0% 3-Hx-Hx-Be (F) -F 10.0% 5-Hx-Hx-Be (F) -F 10.0% 2-Hx-Be-Be ( F) -F 7.0% 3-Hx-Be-Be (F) -F 7.0% 5-Hx-Be-Be (F) -F 14.0% 2-Hx-Be-Be-F 4.0% 3-Hx-Be -Be-F 4.0% 5-Hx-Be-Be-F 3.0% 3-Hx-Be-Be (F, F) -F 5.0% 5-Hx-Be-Be (F, F) -F 10.0% 3 _{-Hx-Be-OC 2 H 5} 7.0% T NI = 87.4 [℃] eta = 25.7 [mPa · s] _{Δn = 0.121 Δε = 7.8 V th} = 1.72 [V]

Example 29 CH ₂ = CHC ₂ H ₄ -Hx-Be (F, F) -Tr-CN (Compound No. 8) 7.0% 5-Hx-Be-F 12.0% 6-Hx-Be-F 9.0% 2-Hx-Hx-Be-OCF ₃ 7.0% 3-Hx-Hx-Be-OCF ₃ 11.0% 4-Hx-Hx-Be-OCF ₃ 7.0% 5-Hx-Hx-Be-OCF ₃ 10.0% 3-Hx-Be-Be ( F) -F 13.0% 5-Hx-Be-Be (F) -F 10.0% 3-Hx-Hx-C 2 H 4 -Be-OCF 3 4.0% 5-Hx-Hx -C ₂ H ₄ -Be-OCF ₃ 4.0% 3-Hx-Be (F) -Be-Hx-3 2.0% 5-Hx-Be (F) -Be-Hx-3 2.0% 5-Hx-Be ( F) -Be-Hx-5 2.0% T _NI = 99.4 [° C] η = 16.1 [mPa · s] Δn = 0.109 Δε = 6.1 V _th = 1.94 [V]

Example 30 3-Hx-Be (F) -Tr-CN (Compound No. 2) 6.0% 5-Hx-Be-F 5.0% 7-Hx-Be-F 6.0% 2-Hx-Hx- Be-OCF ₃ 8.0% 3-Hx-Hx-Be-OCF ₃ 9.0% 5-Hx-Hx-Be-OCF ₃ 11.0% 3-Hx-Hx-Be-OCF ₂ H 5.0% 5-Hx-Hx-Be -OCF ₂ H 4.0% 3-Hx-Hx-Be (F, F) -OCF ₂ H 7.0% 5-Hx-Hx-Be (F, F) -OCF ₂ H 13.0% 3-Hx-Hx-C ₂ H ₄ -Be (F) -F 11.0% 5-Hx-Hx-C ₂ H ₄ -Be (F) -F 5.0% 3-Hx-Hx-COO-Be (F) -F 5.0% 5-Hx- Hx-COO-Be (F) -F 5.0% T _NI = 101.0 [° C] η = 21.1 [mPa · s] Δn = 0.093 Δε = 7.0 V _th = 2.11 [V]

Example 31 3-Be-COO-Be (F) -Tr-CN (Compound No.153) 10.0% 3-Hx-Be-COO-Be (F) -Tr-CN (Compound No.162) 5.0% 3-Hx-Be (F) -CN 5.0% CH ₂ = CH-Hx-Be-CN 10.0% CH ₃ CH = CH-Hx-Be-CN 10.0% 2-Be-Tr-Be-OCH ₃ 10.0 % 3-Hx-Be-OC ₂ H ₅ 10.0% CH ₂ = CHC ₂ H ₄ -Hx-Hx-3 5.0% CH ₂ = CH-Hx-Hx-4 5.0% CH ₂ = CH-Hx-Hx-Be -1 10.0% CH ₃ CH = CHC ₂ H ₄ -Hx-Be-Be-2 10.0% 3-Hx-Hx-Be-1 10.0% T _NI = 83.1 [° C] η = 19.0 [mPa · s] Δn = 0.151 Δε = 10.3 V _th = 1.40 [V]

Example 32 CH ₃ CH = CH-Hx-Hx-Be-Tr-CN (Compound No. 87) 10.0% CH ₂ = CHC ₂ H ₄ -Hx-Be-CN 11.0% CH ₃ CH = CHC ₂ H ₄ -Hx-Be-CN 10.0% CH ₃ OCH ₂ -Hx-Be-CN 10.0% 2-Hx-Be-CN 5.0% 3-Hx-Be-CN 5.0% 3-Hx-Hx-4 11.0% 2 _{-Be-Tr-Be-OCH 3} 4.2% 3-Be-Tr-Be-OCH 3 4.2% 4-Be-Tr-Be-OCH 3 4.2% 4-Be-Tr-Be-OC 2 H 5 4.2% 5 -Be-Tr-Be-OCH ₃ 4.2% 3-Hx-Hx-Be-CN 5.0% 5-Hx-Hx-Be-CN 5.0% 3-Hx-Hx-Be-1 4.0% 3-Hx-Hx- Be-F 3.0%

Example 33 5-Be-COO-Be (F, F) -Tr-CN (Compound No. 155) 12.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F)- CN 6.0% C ₃ H ₇ OCH ₂ -Be-COO-Be (F) -CN 6.0% 2-Hx-Be-CN 12.0% 3-Hx-Be-CN 19.0% 2-Hx-Hx-Be-CN 4.0 % 3-Hx-Hx-Be -CN 5.0% 4-Hx-Hx-Be-CN 4.0% 5-Hx-Hx-Be-CN 4.0% 3-Hx-Be-OC 2 H 5 7.0% 3-Hx- Hx-Be-1 7.0% 3-Hx-Hx-Be-OCH ₃ 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr- Be-3 3.0% 3-Hx -C 2 H 4 -Be-Tr-Be-4 3.0%

Example 34 CH ₃ O-Be-COO-Be (F) -Tr-CN (Compound No. 151) 4.0% 5-Hx-CH = CH-Hx-Be-Tr-CN (Compound No. 63) ) 3.0% CH ₂ = CH-Hx-CH = CH-Hx-Be-Tr-CN (Compound No.66) 3.0% 3-Hx-Be-CN 20.0% 1-Be-Tr-Be-3 5.0% 2 -Be-Tr-Be-1 10.0 % 3-Hx-Hx-4 11.0% 3-Hx-Hx-Be-1 11.0% 3-Hx-Hx-Be-3 9.0% 3-Hx-C 2 H 4 - Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0% 3-Hx-Be (F) -Tr-Be-2 6.0% 3-Hx-Be (F) -Tr-Be-3 6.0%

Example 35 3-Be-COO-Be (F, F) -Tr-CN (Compound No. 154) 6.0% 5-Be-COO-Be (F, F) -Tr-CN (Compound No. 154) 155) 4.0% 3-Hx- Be (F, F) -Tr-CN ( compound No. 3) 5.0% 3-Hx -Be-CN 17.0% 3-Hx-Be-OC 2 H 5 4.0% 3-Hx -Hx-4 11.0% 3-Hx-Hx-5 5.0% 2-Hx-Hx-Be-1 2.0% 3-Hx-Hx-Be-1 10.0% 3-Hx-Hx-Be-3 15.0% 3- Hx-Be (F) -Tr-Be-2 5.0% 3-Hx-Be (F) -Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3- Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0%

Example 36 CH ₂ = CH-Hx-Be-Tr-CN 15.0% 3-Hx-Be-CN 20.0% 5-Hx-Be-CN 31.0% 7-Hx-Be-CN 21.0% 7-Hx -Be-Be-CN 13.0% T _NI = 75.0 [° C] η = 23.6 [mPa · s] Δn = 0.155 Δε = 13.1 Vth = 1.58 [V]

Example 37 3-Hx-Be (F, F) -Tr-CN 15.0% 3-Hx-Be-CN 20.0% 5-Hx-Be-CN 31.0% 7-Hx-Be-CN 21.0% 7 -Hx-Be-Be-CN 13.0% T _NI = 66.0 [° C] η = 26.4 [mPa · s] Δn = 0.145 Δε = 15.2 V _th = 1.44 [V]

Example 38 CH ₂ = CH-Hx-Be-Tr-CN 5.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 5.0% 3-Hx-Be-CN 20.0% 1-Be-Tr-Be-3 5.0% 2-Be-Tr-Be-1 10.0% 3-Hx-Hx-4 11.0% 3-Hx-Hx-Be-1 11.0% 3-Hx-Hx- Be-3 9.0% 3-Hx -C 2 H 4 -Be-Tr-Be-2 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-3 4.0% 3-Hx-C 2 H 4 - Be-Tr-Be-4 4.0% 3-Hx-Be (F) -Tr-Be-2 6.0% 3-Hx-Be (F) -Tr-Be-3 6.0% T _NI = 94.8 [℃] η = 14.0 [mPa · s] Δn = 0.166 Δε = 7.2 V _th = 2.13 [V]

In 100 parts of the above composition, a chiral dopant C-
The pitch when 0.8 part of No. 4 was added was 11.2 μm.

Example 39 CH ₂ = CH-Hx-Be-Tr-CN 7.0% 5-Py-Be-F 4.0% 3-Py-Be (F) -F 4.0% 2-Be-Be-CN 5.0% 4-Be-Be-CN 4.0 % 2-Py-Be-2 2.0% 3-Py-Be-2 2.0% 4-Py-Be-2 2.0% 6-Py-Be-OC 5 H 11 3.0% 6- _{Py-Be-OC 6 H 13} 3.0% 6-Py-Be-OC 7 H 15 3.0% 6-Py-Be-OC 8 H 17 3.0% 3-Py-Be-Be-F 6.0% 4-Py-Be -Be-F 6.0% 5-Py -Be-Be-F 6.0% 3-Hx-Hx-Be-1 6.0% 3-Hx-Hx-Be-3 6.0% 2-Hx-C 2 H 4 -Be- Tr-Be-2 4.0% 2-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 2-Hx-C ₂ H ₄ -Be-Tr-Be-4 5.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 5.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 5.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 5.0% T _NI = 97.7 [° C] η = 33.1 [mPa · s] Δn = 0.206 Δε = 6.6 V _th = 2.24 [V]

Example 40 CH ₂ = CH-Hx-Be-Tr-CN 7.0% C ₂ H ₅ OCH ₂ -Be-COO-Be (F) -CN 5.0% C ₃ H ₇ OCH ₂ -Be-COO- Be (F) -CN 12.0% C ₅ H ₁₁ OCH ₂ -Be-COO-Be (F) -CN 4.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 14.0% _{3-Hx-Be-OC 2} H 5 10.0% 3-Hx-Hx-4 3.0% 3-Hx-Hx-Be-F 3.0% 3-Hx-Hx-Be-1 3.0% 3-Hx-Hx-Be -OCH ₃ 4.0% 3-Hx-Be-COO-Be-F 4.0% 3-Hx-Hx-COO-Be-F 7.0% 5-Hx-Hx-COO-Be-F 7.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0% 3- Hx-Be (F) -Tr-Be-2 5.0% T _NI = 88.9 [° C] η = 38.9 [mPa · s] Δn = 0.150 Δε = 28.1 V _th = 1.01 [V]

[0169] Example _{41 CH 2 = CH-Hx-} Be-Tr-CN 7.0% 2-Hx-Be-CN 5.0% 3-Hx-Be-CN 12.0% 3-Hx-Be-OC 2 H 5 12.0% 2-Be-Tr-Be-1 3.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-F 4.0% 3-Hx-Hx-Be-OCH ₃ 5.0% 3-Hx-Hx -Be-3 10.0% 3-Hx-Hx-COO-Be-F 4.0% 5-Hx-Hx-COO-Be-F 4.0% 2-Hx-Hx-Be (F) -F 7.0% 3-Hx- Hx-Be (F) -F 7.0% 5-Hx-Hx-Be (F) -F 7.0% 3-Hx-Hx-Be (F, F) -F 5.0% T _NI = 100.9 [° C] η = 18.1 [MPa · s] Δn = 0.110 Δε = 6.0 V _th = 2.15 [V]

Example 42 CH ₂ = CH-Hx-Be-Tr-CN 5.0% 3-Hx-Be (F, F) -Tr-CN 5.0% 3-Be-COO-Be (F) -CN 8.0% 3-Hx-Be-CN 8.0 % CH 2 = CH-Hx-Be-CN 8.0% CH 3 CH = CH-Hx-Be-CN 3.0% 3-Hx-Be-OC 2 H 5 3.0% 3-Hx- Hx-C ₂ H ₄ CH = CH ₂ 14.0% 3-Hx-Hx-C ₂ H ₄ CH = CHCH ₃ 7.0% CH ₂ = CHC ₂ H ₄ -Hx-Hx-Be-1 10.0% 3-Hx-Hx -Be-1 5.0% 3-Hx-Hx-COO-Be-F 7.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 6.0% 3-Hx-C ₂ H ₄ -Be-Tr- Be-3 6.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 5.0% T _NI = 96.2 [° C] η = 14.9 [mPa · s] Δn = 0.141 Δε = 10.7 V _th = 1.98 [V ]

Example 43 3-Hx-Be (F, F) -Tr-CN 5.0% C ₂ H ₅ OCH ₂ -Be-COO-Be (F) -CN 5.0% C ₃ H ₇ OCH ₂ -Be- COO-Be (F) -CN 5.0% C ₄ H ₉ OCH ₂ -Be-COO-Be (F) -CN 5.0% C ₅ H ₁₁ OCH ₂ -Be-COO-Be (F) -CN 5.0% 2- Hx-Hx-Be (F) -C 15.0% 3-Hx-Hx-Be (F) -C 15.0% 3-Hx-Be (F) -Tr-Be-2 4.0% 3-Hx-Be (F) -Tr-Be-3 4.0% 3 -Hx-Be (F) -Tr-Be-4 4.0% 3-Hx-Hx-Be-1 8.0% 3-Hx-Hx-Be-OCH 3 4.0% T NI = 79.8 [° C] η = 82.9 [mPa · s] Δn = 0.166 Δε = 32.0 V _th = 0.84 [V]

Example 44 3-Hx-Be (F, F) -Tr-CN 7.0% C ₂ H ₅ OCH ₂ -Be-COO-Be (F) -CN 5.0% C ₃ H ₇ OCH ₂ -Be- COO-Be (F) -CN 12.0% C ₅ H ₁₁ OCH ₂ -Be-COO-Be (F) -CN 4.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 10.0% 3-Hx-Hx- COOCH 3 10.0% 3-Hx-Be-OC 2 H 5 16.0% 7-Hx-COO-Be-F 2.0% 3-Hx-Hx-COO-Be-F 2.0% 5- Hx-Hx-COO-Be-F 2.0% 3-Hx-Be-COO-Be-F 4.0% C ₂ H ₅ OCH ₂ -Hx-Be-COO-Be (F) -CN 2.0% 3-Hx-Be (F) -COO-Be (F) -CN 2.0% 3-Hx-Be-COO-Be (F, F) -CN 2.0% 3-Hx-Hx-Be-F 4.0% 3-Hx-Hx-Be -OCH ₃ 4.0% 3-Hx-Hx-Be-3 8.0% 3-Hx-COO-Be-COO-Be-F 2.0% 3-Hx-COO-Be-COO-Be-1 2.0% T _NI = 70.1 [° C] η = 36.0 [mPa · s] Δn = 0.121 Δε = 25.9 V _th = 0.95 [V]

Example 45 CH ₂ = CH-Hx-Be-Tr-CN 6.0% 2-Hx-Hx-Be (F) -F 2.0% 3-Hx-Hx-Be (F) -F 2.0% 5- Hx-Hx-Be (F) -F 2.0% 2-Hx-Be-Be (F) -F 6.0% 3-Hx-Be-Be (F) -F 6.0% 5-Hx-Be-Be (F) -F 4.0% 2-Hx-C ₂ H ₄ -Be-Be (F) -F 9.0% 3-Hx-C ₂ H ₄ -Be-Be (F) -F 9.0% 3-Hx-Be-Be ( F, F) -F 25.0% 5-Hx-Be-Be (F, F) -F 19.0% CH ₃ OCH ₂ -Hx-Be-Be-Hx-4 5.0% CH ₃ OCH ₂ -Hx-Be-Be -Hx-4 5.0% T _NI = 97.3 [° C] η = 34.1 [mPa · s] Δn = 0.141 Δε = 8.1 V _th = 1.85 [V]

Example 46 CH ₂ = CH-Hx-Be-Tr-CN 6.0% 3-Hx-Be (F, F) -Tr-CN 6.0% 3-Hx-C ₂ H ₄ -Hx-Be (F , F) -F 7.0% 5-Hx-C ₂ H ₄ -Hx-Be (F, F) -F 8.0% 3-Hx-Hx-Be (F, F) -F 10.0% 4-Hx-Hx- Be (F, F) -F 5.0% 3-Hx-Hx-C ₂ H ₄ -Be (F, F) -F 3.0% 5-Hx-Hx-C ₂ H ₄ -Be (F, F) -F 3.0% 3-Hx-Be-Be (F, F) -F 15.0% 5-Hx-Be-Be (F, F) -F 15.0% 3-Hx-Be-COO-Be (F, F) -F 2.0% 4-Hx-Be-COO-Be (F, F) -F 2.0% 5-Hx-Be-COO-Be (F, F) -F 2.0% 3-Hx-Hx-COO-Be (F, F) -F 10.0% 4-Hx-Hx-COO-Be (F, F) -F 3.0% 5-Hx-Hx-COO-Be (F, F) -F 3.0% T _NI = 79.0 [℃] η = 29.5 [mPa · s] Δn = 0.110 Δε = 13.7 V _th = 1.57 [V]

Example 47 CH ₂ = CH-Hx-Be-Tr-CN 10.0% 3-Hx-Be (F) -Tr-CN 5.0% 3-Hx-Be (F, F) -Tr-CN 2.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 6.0% 3-Hx-Be-OC ₂ H ₅ 4.0% 3-Hx-Hx-CH = CF ₂ 18.0% 5-Hx -Hx-CH = CF ₂ 20.0% CF ₂ = CH-Hx-Hx-Be-1 8.0% CF ₂ = CHC ₂ H ₄ -Hx-Hx-Be-1 10.0% 3-Hx-C ₂ H ₄ -Be -Tr-Be-2 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-3 4.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-4 4.0% 3-Hx-Be ( F) -Tr-Be-2 5.0% T _NI = 100.4 [° C] η = 11.2 [mPa · s] Δn = 0.136 Δε = 7.9 V _th = 2.14 [V]

Example 48 CH ₂ = CH-Hx-Be-Tr-CN 2.0% 3-Hx-Be (F) -Tr-CN 11.0% 3-Hx-Be (F, F) -Tr-CN 2.0% CH ₃ CH = CHC ₂ H ₄ -Be-COO-Be (F, F) -CN 6.0% CH ₂ = CHC ₂ H ₄ -Hx-Hx-CH = CF ₂ 35.0% 5-Hx-Hx-CH = CF ₂ 3.0% CF ₂ = CH-Hx-Hx-Be-1 8.0% CF ₂ = CHC ₂ H ₄ -Hx-Hx-Be-1 18.0% 3-Hx-C ₂ H ₄ -Be-Tr-Be-2 _{4.0% 3-Hx-C 2} H 4 -Be-Tr-Be-3 4.0% 3-Hx-C 2 H 4 -Be-Tr-Be-4 4.0% 3-Hx-Be (F) -Tr-Be -2 3.0% T _NI = 100.7 [° C] η = 10.7 [mPa · s] Δn = 0.132 Δε = 8.1 V _th = 2.09 [V]

C. Characteristic comparison test Example 49 About the following composition 1 and composition 2 having different first components,
A sex comparison test was performed. Each compound uses the same abbreviation as described above.
Displayed.Composition Composition 1 Composition 2  3-Hx-Be-Tr-CN 15wt%-3-Hx-Be (F) -Tr-CN (Compound No.2)-15wt% 3-Hx-Be-CN 20wt% 20wt% 5-Hx- Be-CN 31wt% 31wt% 7-Hx-Be-CN 21wt% 21wt% 5-Hx-Be-Be-CN 13wt% 13wt%

The measurement results are shown below. Property item composition 1 composition 2 T _NI [° C] 76.8 72.7 η [mPa · s] 26.5 23.0 Δn [-] 0.150 0.150 Δε [-] 12.0 13.5 Vth [V] 1.63 1.43

[0179]

According to the present invention, excellent properties as a liquid crystal component, that is, properties such as a wide liquid crystal temperature range, good compatibility with other liquid crystals, low viscosity, and large dielectric anisotropy are maintained. The present invention can provide a novel liquid crystal compound capable of giving a large elastic constant ratio, a liquid crystal composition containing the same, and a liquid crystal display device composed of the composition.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C09K 19/12 C09K 19/12 19/14 19/14 19/18 19/18 19/20 19/20 19/30 19/30 19/34 19/34 19/42 19/42 19/44 19/44 19/46 19/46 G02F 1/13 500 G02F 1/13 500 (72) Inventor Norio Tamura 1963 Yawata Kaigan-dori, Ichihara City, Chiba Prefecture -4 (72) Inventor Norihisa Hachiya 2-5-5 Aobadai, Ichihara City, Chiba Prefecture (72) Inventor Etsuo Nakagawa 8890 Goi, Ichihara City, Chiba Prefecture

Claims (32)

[Claims] 1. A compound of the general formula (1) Wherein n 1 and n 2 are each independently 0 or 1; A 1, A 2 and A 3 are each independently 1,4-phenylene, 1,1 or 2 substituted with 1 or 2 fluorine atoms, 4-phenylene, trans-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,3-
Represents pyrimidine-2,5-diyl; Z1, Z2 and Z3
Is independently a single bond, an ethylene group, an ethenylene group, an ethynylene group, a carbonyloxy group, an oxycarbonyl group, a methyleneoxy group, an oxymethylene group,
Represents a -butylene group or a 1,4-butenylene group;
Is a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, 2 carbon atoms
An unsaturated hydrocarbon group having 1 to 10 carbon atoms, a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms having one or more ether bonds (-O-) in the chain, or one or more fluorine atoms in the chain Represents a saturated or unsaturated fluorine-substituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, and X1 and X2 each independently represent F, Cl or H, provided that n1 = n2 = 0,
When Z1 is a single bond, an ethylene group, a carbonyloxy group or an oxycarbonyl group, and R is an alkyl group or an alkoxy group; When an ethylene group and R is an alkyl group or an alkoxy group, X1, X2
Is at least one of F and Cl). 2. The propionitrile derivative according to claim 1, wherein n1 = n2 = 0 in the general formula (1). 3. The propionitrile derivative according to claim 1, wherein n1 = 1 and n2 = 0 in the general formula (1). 4. The propionitrile derivative according to claim 1, wherein n1 = n2 = 1 in the general formula (1). 5. The propionitrile derivative according to claim 1, wherein in the general formula (1), R is an alkenyl group having 2 to 10 carbon atoms. 6. The propionitrile derivative according to claim 1, wherein in the general formula (1), R is an alkenyl group having 2 to 10 carbon atoms, and both X1 and X2 are H. 7. The propionitrile derivative according to claim 1, wherein in the general formula (1), n1 = n2 = 0 and R is an alkenyl group having 2 to 10 carbon atoms. 8. In the general formula (1), n1 = 1 and n2 = 0,
The propiolonitrile derivative according to claim 1, wherein R is an alkenyl group having 2 to 10 carbon atoms. 9. The propiolonitrile derivative according to claim 1, wherein in the general formula (1), n1 = n2 = 0, Z1 is a single bond, and R is an alkenyl group having 2 to 10 carbon atoms. 10. The propionitrile derivative according to claim 1, wherein in formula (1), n1 = 1 and n2 = 0, Z1 is a single bond, and R is an alkenyl group having 2 to 10 carbon atoms. 11. The propionitrile according to claim 1, wherein in formula (1), one or both of X1 and X2 are F and / or Cl, and R is an alkyl group having 1 to 10 carbon atoms. Derivatives. 12. In the general formula (1), one of Z1, Z2 and Z3 is an ethylene group, a 1,4-butylene group, an oxymethylene group or a methyleneoxy group, and the other is a single bond or an ethylene group. The propiolonitrile derivative according to claim 1, which is: 13. In the general formula (1), n1 = n2 = 0 and Z1
Is a propiolonitrile derivative according to claim 1, wherein is a ethylene group, a 1,4-butylene group, an oxymethylene group or a methyleneoxy group. 14. In the general formula (1), n1 = 1 and n2 = 0, and one of Z1 and Z2 is an ethylene group, 1,4-
2. A butylene group, an oxymethylene group or a methyleneoxy group, and the other is a single bond or an ethylene group.
The propiolonitrile derivative according to the above. 15. In the general formula (1), n1 = n2 = 1 and Z
1, one of Z2 and Z3 is an ethenylene group,
2. The propiolonitrile derivative according to claim 1, wherein the derivative is a 4-butenylene group or an ethynylene group, and the other is a single bond or an ethylene group. 16. In the general formula (1), n1 = n2 = 0 and Z1
Is a ethenylene group, a 1,4-butenylene group or an ethynylene group. 17. In the general formula (1), n1 = 1 and n2 = 0, and one of Z1 and Z2 is an ethenylene group, 1,4.
The propiolonitrile derivative according to claim 1, wherein the derivative is a butenylene group or an ethynylene group, and the other is a single bond or an ethylene group. 18. In the general formula (1), n1 = n2 = 1 and Z
2. The propionitrile derivative according to claim 1, wherein one of 1, Z2 and Z3 is a carbonyloxy group or an oxycarbonyl group, and the other is a single bond or an ethylene group. 19. In the general formula (1), n1 = n2 = 1 and Z
1, one of Z2 and Z3 is a carbonyloxy group or an oxycarbonyl group, the other is a single bond or an ethylene group, and one or both of X1 and X2 are F
The propiolonitrile derivative according to claim 1, which is: 20. In the general formula (1), n1 = n2 = 0 and Z1
Is a carbonyloxy group or an oxycarbonyl group. 21. In the general formula (1), n1 = n2 = 0 and Z1
Is a carbonyloxy group or an oxycarbonyl group, and one or both of X1 and X2 is F. The propiolonitrile derivative according to claim 1, wherein 22. In the general formula (1), n1 = 1 and n2 = 0, and one of Z1 and Z2 is a carbonyloxy group or an oxycarbonyl group, and the other is a single bond or an ethylene group. The propiolonitrile derivative according to the above. 23. In the general formula (1), n1 = 1 and n2 = 0, one of Z1 and Z2 is a carbonyloxy group or an oxycarbonyl group, the other is a single bond or an ethylene group, and X1 and The propiolonitrile derivative according to claim 1, wherein one or both of X2 is F. 24. In the general formula (1), n1 = n2 = 0 and A1
Is trans-1,4-cyclohexylene.
The propiolonitrile derivative according to the above. 25. In the general formula (1), n1 = n2 = 0 and A1
Is a fluorine-substituted 1,4-phenylene. 26. The propionitrile derivative according to claim 1, wherein in formula (1), n1 = 1 and n2 = 0, and A1 and / or A2 are trans-1,4-cyclohexylene. 27. The propionitrile derivative according to claim 1, wherein in formula (1), n1 = 1 and n2 = 0, and A1 and / or A2 is 1,4-phenylene. 28. A liquid crystal composition comprising at least two components containing at least one selected from the propionitrile derivatives represented by the general formula (1) according to claim 1. 29. The general formula (1) according to claim 1, wherein the first component is
Wherein at least one selected from propionitrile derivatives represented by the following formulas and the second component are represented by the general formula (2): Wherein a is 1 or 2, b is 0 or 1, and A4 is trans-1,4-cyclohexylene, or unsubstituted or 1,4-phenylene substituted with 1 or 2 F; Z4 and Z5 are each independently an ethylene group, an ethenylene group or a single bond; R1 is an alkyl group having 1 to 10 carbon atoms; X5 is _{-F, -CF 3, -OCF 3,} -OCF 2 H or -Cl;
(F) represents F or H), a liquid crystal composition comprising at least one selected from the group consisting of compounds represented by the following formula: 30. The general formula (1) according to claim 1, wherein the first component is
At least one kind selected from the propiolonitrile derivative represented by the following formula, and the second component are represented by the general formula (3): R2-(-A5-Z6-) _c -(-A6-Z7-) _d -(-A7- Z8-) _e- A8-(-COO-) _f- R3 (3) (wherein c, d, e and f are each independently 0 or 1, and A5, A6 and A7 are each independently Trans-1,4-cyclohexylene, 1,4-phenylene unsubstituted or substituted by one or two F, 1,3-
Dioxane-2,5-diyl or 1,3-pyrimidine-
2,5-diyl, A8 is trans-1,4-cyclohexylene, or 1,4-phenylene unsubstituted or substituted by one or two F; Z6, Z7 and Z8 each independently represent ethylene. Group, ethenylene group, ethinylene group, 1
-Butene-3-inylene group, carbonyloxy group or single bond; R2 is a saturated or unsaturated aliphatic hydrocarbon group having up to 10 carbon atoms which may have one or more ether bonds in a chain, and R3 is _{-CN, -F, -OCF 3, -OCF} 2 H, -CF 3, -
CF ₂ H, -CFH ₂ or a saturated or unsaturated aliphatic hydrocarbon group having up to 10 carbon atoms which may have one or more ether bonds in the chain). A liquid crystal composition comprising at least one of the following: 31. The general formula (1) according to claim 1, wherein the first component is
And at least one selected from propiolonitrile derivatives represented by the following formulas, and the compound represented by the general formula (2) according to claim 29 and the compound represented by the general formula (3) according to claim 30: A liquid crystal composition comprising at least one selected from the group consisting of: 32. A liquid crystal display device comprising the liquid crystal composition according to claim 28.