JP2001329264A - Liquid crystal composition containing benzylidynyltolan compound and liquid crystal element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a liquid crystal composition having a high refractive index anisotropy (Δn) and a liquid crystal element prepared by using the same. SOLUTION: The liquid crystal composition contains a compound represented by formula (1) and at least one compound selected from among compounds represented by formulas (2)-(4) (wherein A1 to A12 are each a fluorinated alkyl or alkoxy or the like; R1 and R2 are each H, F or the like; A13 to A24 are each H, F or the like; m is 0 or 1; R11 is a fluorinated 1-12C alkyl or the like; R21 is R11, F or the like; ring A to ring D are each 1,4-phenylene, 1,4- cyclohexylene or the like; R5 and R6 are each H, F or the like; Z1 to Z3 are each -COO-, -OCO- or the like; b to d are each 0 or 1 provided b+c+d>=1; B1 to B12 are each an alkyl, an alkoxy or the like; and R7 and R8 are each H, F or the like).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a liquid crystal composition and a liquid crystal device using the same. More specifically, a liquid crystal composition having a high refractive index anisotropy (Δn) and a light shutter, an STN (super twisted nematic) type liquid crystal device, and a PDLC (polymer dispersed liquid crystal) type liquid crystal device using the same are used. And a liquid crystal element such as a display element.

[0002]

2. Description of the Related Art In recent years, with the progress of the information society, various display elements have been increasingly important as one of man-machine interfaces. In such a situation, flat displays, especially liquid crystal displays (LCDs) have rapidly become popular because they have features such as thinness, light weight, low voltage driving, and low power consumption. Among liquid crystal elements represented by a liquid crystal display, a matrix type liquid crystal element having a large amount of information has two driving methods called an active matrix method and a simple matrix method. In the active matrix system, a thin film transistor or diode such as polysilicon or amorphous silicon is mounted as a nonlinear element for each pixel. However, the active matrix method has problems in terms of large area, low price, and high density due to complicated manufacturing processes and low yield, and the simple matrix method is more expensive and more productive. Influential. Currently, TN (twisted nematic) type and STN type liquid crystal elements are mainly used as simple matrix type liquid crystal elements that are currently in practical use. TN type
Widely applied as display elements such as watches and calculators, but in this method, the rise of electro-optical characteristics is gradual, and the contrast decreases significantly as the duty ratio increases, so it is difficult in principle to display a large screen. . S
The TN type is a method developed to compensate for the drawbacks of the TN type liquid crystal element, and has a steep electro-optical characteristic, so that a large screen can be obtained. At present, it is used for displays such as notebook personal computers. However, although the STN-type liquid crystal element has better characteristics than the TN-type liquid crystal element, there are still problems to be solved in order to further increase the area, reduce the cost, and increase the density. I have. For example, when compared with a TFT liquid crystal element, which is a typical liquid crystal element of the active matrix system, the STN liquid crystal element is still insufficient in view angle characteristics and response speed. In particular, high-speed response is indispensable in order to further increase the area, increase the density, display moving images, and the like. In order to make the STN-type liquid crystal element respond fast,
Reducing the cell thickness is one of the most effective methods. ST
The N-type uses the birefringence effect in the display method, and in order to use this method, it is necessary to suppress changes in the color tone and optical characteristics of the panel, that is, to set the retardation to a certain optimum value. . The retardation R is given by R = (Δ
nxd), it is necessary to increase the refractive index anisotropy Δn in order to reduce the cell thickness d. However, a liquid crystal composition having a large Δn generally has a large viscosity and is not suitable for high-speed response, and a liquid crystal composition having a large Δn and a low viscosity is desired. Response parameter η /
It is known that Δn2 has a good correlation with the response time. The smaller the response parameter, the shorter the response time. Therefore, a liquid crystal having a small response parameter is desired. Further, a compound having a large Δn generally has poor phase solubility with other liquid crystals, and it is difficult to secure a nematic phase particularly widely in a low temperature region. For example, a composition containing a liquid crystal compound exhibiting a high Δn and having improved compatibility with other liquid crystals (Japanese Patent Application Laid-Open No. 9-216841) has low temperature stability, but the composition itself has a particularly large Δn. Not something.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a liquid crystal composition having a high refractive index anisotropy (Δn) and a liquid crystal element using the same, which can be used for an optical shutter or a display element. is there. Another object of the present invention is to provide a liquid crystal composition having a nematic phase in a wide temperature range including room temperature, in addition to a high refractive index anisotropy, or a response parameter.
An object of the present invention is to provide a liquid crystal composition having a small (η / Δn 2) and excellent responsiveness, and a liquid crystal element using the same.

[0004]

That is, according to the present invention,
A benzylidinyl tolane compound represented by the formula (1):
A compound represented by the formula (2), a compound represented by the formula (3) and one or more selected from the group consisting of compounds represented by the formula (4). A liquid crystal composition is provided.

[0005]

Embedded image (In the formula (1), A ^{1 to} A ¹² each independently represent a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms which may be substituted by a fluorine atom. And R ¹ and R ² are each independently a hydrogen atom, a fluorine atom, a cyano group, —SF ₅ ,
—NCS, 4-R ³ — (cycloalkyl) group, 4-R ³ —
(Cycloalkenyl group) or a group represented by R ⁴ — (O) q ¹ (provided that R ³ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom) And R ⁴ represents an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom.
¹ represents 0 or 1). )

[0006]

Embedded image (In the formula (2), A ^{13 to} A ²⁴ each independently represent a hydrogen atom,
It represents a fluorine atom or an alkyl group having 1 to 10 carbon atoms. m
Is 0 or 1. R ¹¹ is a hydrogen atom or a carbon atom having 1 to 1 carbon atoms which may be substituted by a linear or branched fluorine atom.
2 represents an alkyl group. R ²¹ is R ¹¹ , a fluorine atom, a cyano group, a 4-R ^31- (cycloalkyl) group, a 4-R ^31-
(Cycloalkenyl group) or an R ^41- (O) q ² group (provided that R ³¹ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom) R ⁴¹ represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom. Q ² represents 0 or 1.) )

[0007]

Embedded image (In the formula (3), ring A, ring B, ring C and ring D are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexelene, 4,1-cyclohexelene 2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene, 6,3-cyclohexelene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, Represents 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl (provided that ring A, ring B, ring C and ring D
The above hydrogen atom may be replaced by a fluorine atom).
R ⁵ and R ⁶ are each independently a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group,
Trifluoromethoxy group, cyano group, alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, 1 carbon atom
An alkoxy group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, an alkynyloxy group having 3 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms or an alkoxyalkenyl group having 3 to 16 carbon atoms. The methylene group contained in these groups may contain an oxygen atom, a sulfur atom or a silicon atom, and may be either linear or branched. Z ¹ , Z ² and Z ³ are each independently -COO-,
—OCO—, —OCH ₂ —, —CH ₂ O—, having 1 to 5 carbon atoms
An alkylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. b, c and d are each independently 0 or 1, and b + c +
d ≧ 1. )

[0008]

Embedded image (In the formula (4), B ^{1 to} B ¹² each independently represent a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and at least one is an alkyl group or an alkoxy group. .R ⁷ and R ⁸ are each independently a hydrogen atom, a fluorine atom, a cyano group, 4-R ⁹ - (cycloalkyl) group, 4-R ⁹ - (cycloalkenyl group) or R ¹⁰ -
(O) represents a group (provided that R ⁹ is a hydrogen atom or a carbon atom having 1 to 5 carbon atoms which may be substituted with a linear or branched fluorine atom)
And 12 represents an alkyl group having 12 carbon atoms, and R ¹⁰ represents an alkyl group having 1 to 12 carbon atoms which may be substituted with a linear or branched fluorine atom. a represents 0 or 1). )

Further, according to the present invention, there is provided a liquid crystal element characterized in that any one of the above liquid crystal compositions is sandwiched between a pair of electrode substrates.

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in more detail. The liquid crystal composition of the present invention comprises a benzylidinyl tolane compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4). A liquid crystal composition containing a benzylidinyl tolane-based compound, comprising one or more selected from the group consisting of the compounds represented by the formula (I).

In the compound represented by the formula (1), A ¹ to
A ¹² independently represents a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms which may be substituted with a fluorine atom, and at least one alkyl group substituted with a fluorine atom Or an alkoxy group. When any of A ^{1 to} A ¹² is a fluorine atom, the number is preferably two or one. R ¹ and R ² are each independently a hydrogen atom, a fluorine atom, a cyano _{group, -SF 5, -NCS, 4-} R 3 - ( cycloalkyl) group, 4-R ³ - (cycloalkenyl group) or R ⁴
-(O) q ¹ (where R ³ represents a hydrogen atom or a carbon atom which may be substituted by a linear or branched fluorine atom)
And R ⁴ represents an alkyl group having 1 to 12 carbon atoms which may be substituted with a linear or branched fluorine atom. q ¹ is 0 or 1.

In the formula (1), R ¹ and R ² are, for example, a hydrogen atom; a fluorine atom; a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group Groups, decyl, undecyl, dodecyl and other alkyl groups and fluoroalkyl groups substituted with a fluorine atom (eg, trifluoromethyl group); methoxy, ethoxy, propoxy, butoxy, pentyloxy A hexyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, an alkoxy group such as a dodecyloxy group and a fluoroalkoxy group substituted with a fluorine atom (for example, 1 to 3 fluorine atoms Substituted methoxy group, ethoxy group substituted with 1 to 5 fluorine atoms); 2-methylpropyl Branched alkyl groups such as a group, a 2-methylbutyl group, a 3-methylbutyl group, and a 3-methylpentyl group; and a fluorobranched alkyl group in which these are substituted with a fluorine atom; a 2-methylpropyloxy group;
-Methylbutyloxy group, 3-methylbutyloxy group,
A branched alkyloxy group such as a 3-methylpentyloxy group and a fluorobranched alkyloxy group substituted with a fluorine atom; a 4-methylcyclohexyl group, a 4-ethylcyclohexyl group, a 4-propylcyclohexyl group;
4-butylcyclohexyl, 4-pentylcyclohexyl, 4-hexylcyclohexyl, 4-heptylcyclohexyl, 4-octylcyclohexyl, 4
-Nonylcyclohexyl group, 4-alkyl-cycloalkyl group such as 4-decylcyclohexyl group and the like, and 4-fluoroalkyl-cycloalkyl group substituted by fluorine atom; 4-propylcyclohexenyl group, 4-pentylcyclohexenyl group And the like, and 4-fluoroalkyl-cycloalkenyl groups in which these are substituted by fluorine atoms; cyano groups and the like.

The compound represented by the formula (1) is preferably, for example, a compound represented by the following structural formula. However, it is preferable that R ¹ and R ² in the structural formula are independently selected and combined from the above specific examples, but are not limited thereto.

[0014]

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[0015]

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[0016]

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[0017]

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[0018]

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[0019]

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The compound represented by the formula (1) can be synthesized using ordinary organic synthetic means. For example,
It can be obtained by combining the reactions described in “Organic synthesis pioneered by transition metals” (by Jiro Tsuji, Doujin Kagaku). Specifically, for example, a compound represented by the formula (12) and a compound represented by the formula (13)
By reacting with a compound represented by the following formula in the presence of copper iodide, a palladium catalyst and a base such as triethylamine.

Embedded image (In the formulas (12) and (13), A ^{1 to} A ¹² and R ¹ and R ² are the same as those in the above formula (1).)

The compound represented by the formula (12) is, for example, a compound represented by the formula
After coupling the compound represented by (14) and the compound represented by the formula (15), butyl-2-ol is reacted in the presence of copper iodide, a palladium catalyst and a base such as triethylamine, Further, it can be produced by reacting in the presence of a base such as potassium hydroxide.

Embedded image (In the formulas (14) and (15), A ¹ , A ^{3 to} A ⁵ , A ^{9 to} A ¹² and R ¹ are the same as those in the above formula (1).)

The compound represented by the formula (1) is, for example,
For example, a compound represented by the following formula (16)
Reacting with methanesulfonic acid to form a compound represented by formula (16)
The terminal OH group of the compound is -OSO_TwoCF_ThreeAnd this and equation (1)
7) a compound represented by the following formula: copper iodide, palladium catalyst
Reaction in the presence of a base such as
And can be manufactured. However, in equations (16) and (17)
A¹~ A¹², R¹And R ^TwoIs the same as in equation (1)
Show meaning.

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[0023] In the compound represented by formula (2), A ¹³ ~
A ²⁴ independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 10 carbon atoms. m is 0 or 1.
R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom. R ²¹ is R ¹¹ , a fluorine atom, a cyano group, 4-R ³¹ −
(Cycloalkyl) group, 4-R ³¹ - (cycloalkenyl group)
Or R ⁴¹ - (O) indicating the q ² group (wherein, R ³¹ represents a hydrogen atom or a straight-chain or branched fluorine atoms which may have been a good 1 to 12 carbon atoms substituted with an alkyl group, R ⁴¹ Is a carbon number 1 to 1 which may be substituted by a linear or branched fluorine atom.
Represents 12 alkyl groups. q ² is 0 or 1.

In the formula (2), R ¹¹ is, for example,
A hydrogen atom; an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group; And a fluoroalkyl group (eg, a trifluoromethyl group). In the formula (2), as R ²¹ , for example, specific examples of the above R ¹¹ , an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group,
Alkenyl groups such as dodecenyl groups and the like, and fluoroalkenyl groups substituted with fluorine atoms; alkynyl groups such as propynyl group, butynyl group, pentynyl group, hexynyl group, heptynyl group, octynyl group, noninyl group, decynyl group and dodecynyl group; A fluoroalkynyl group in which these are substituted with a fluorine atom; a methoxy group, an ethoxy group,
Propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, alkoxy groups such as dodecyloxy group and the like, and a fluoroalkoxy group substituted with a fluorine atom (for example, Methoxy group substituted by 1 to 3 fluorine atoms, ethoxy group substituted by 1 to 5 fluorine atoms); 2-methylpropyl group, 2-methylbutyl group, 3-methylbutyl group, 3-methylpentyl A branched alkyl group such as a group and a fluorobranched alkyl group substituted with a fluorine atom; 2-methylpropyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 3-methylpentyloxy group, etc. A branched alkyloxy group and a fluorobranched alkyloxy group substituted with a fluorine atom 4-methylcyclohexyl group, 4
-Ethylcyclohexyl group, 4-propylcyclohexyl group, 4-butylcyclohexyl group, 4-pentylcyclohexyl group, 4-hexylcyclohexyl group, 4-heptylcyclohexyl group, 4-octylcyclohexyl group, 4-nonylcyclohexyl group, 4-decyl 4-alkyl-cycloalkyl groups such as cyclohexyl group and the like, and 4-fluoroalkyl-cycloalkyl groups substituted with a fluorine atom; 4-propylcyclohexenyl group;
4-alkyl-cycloalkenyl groups such as -pentylcyclohexenyl group and 4
-Fluoroalkyl-cycloalkenyl group; cyano group and the like.

Specific examples of the compound represented by the formula (2) include a compound represented by the following structural formula. However, R ¹¹ and R ²¹ are preferably, but not limited to, the groups listed above.

[0026]

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[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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[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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[0039]

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[0040]

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[0041]

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In the compound represented by the above formula (3) used in the liquid crystal composition of the present invention, ring A, ring B, ring C and ring D
Is independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexelene, 4,1-
Cyclohexelene, 2,5-cyclohexelene, 5,2
-Cyclohexelene, 3,6-cyclohexelene, 6,
3-cyclohexelene, 2,5-pyrimidindiyl,
5,2-pyrimidinediyl, 2,5-pyridinediyl,
It represents 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl. However, a hydrogen atom on ring A, ring B, ring C and ring D may be substituted with a fluorine atom. R ⁵ and R ⁶ are each independently a hydrogen atom,
Fluorine atom, fluoromethyl group, difluoromethyl group,
Trifluoromethyl group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, cyano group, alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, carbon number 2-12
An alkenyloxy group, an alkynyloxy group having 3 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms or an alkoxyalkenyl group having 3 to 16 carbon atoms. The methylene group contained in these groups may contain an oxygen atom, a sulfur atom or a silicon atom, and may be either linear or branched. Z ¹ , Z ² and Z ³ are each independently —COO—, —OCO—, —OCH ₂ —, —CH ₂ O—,
It represents an alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. b, c and d are each independently 0 or 1,
And b + c + d ≧ 1.

R ⁵ and R ⁶ include, for example, a hydrogen atom;
A fluorine atom; a fluoromethyl group; a difluoromethyl group;
Trifluoromethyl group; fluoromethoxy group; difluoromethoxy group; trifluoromethoxy group; cyano group; methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group,
Alkyl groups such as decyl, undecyl and dodecyl;
Alkenyl groups such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl; methoxy, ethoxy, propoxy, butoxy, pentyl Oxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, alkoxy group such as dodecyloxy group; vinyloxy group, propenyloxy group, butenyloxy group, pentenyloxy group,
An alkenyloxy group such as a hexenyloxy group, a heptenyloxy group, an octenyloxy group, a nonenyloxy group, and a decenyloxy group; Alkynyloxy groups such as undecynyloxy group and dodecynyloxy group; methoxymethyl group, ethoxymethyl group, propoxymethyl group, butoxymethyl group, pentyloxymethyl group, hexyloxymethyl group, heptyloxymethyl group, octyloxymethyl group, nonyl Oxymethyl group, decyloxymethyl group,
Methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, pentyloxyethyl group, hexyloxyethyl group, heptyloxyethyl group, octyloxyethyl group, nonyloxyethyl group, decyloxyethyl group, methoxypropyl group, Ethoxypropyl group, propoxypropyl group, butoxypropyl group, pentyloxypropyl group, hexyloxypropyl group, heptyloxypropyl group, octyloxypropyl group,
Nonyloxypropyl, decyloxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl, octyloxybutyl, nonyloxybutyl , Decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, octyloxypentyl,
Examples include an alkoxyalkyl group such as a nonyloxypentyl group and a decyloxypentyl group.

As the compound represented by the formula (3),
Compounds represented by (5) to (11) can be preferably mentioned.

[0045]

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[0046]

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In formulas (5) to (8), R ⁵ , R ⁶ , ring A, ring B, Z ¹ and b have the same meaning as in formula (3). j is 0, 1 or 2; h is 0 or 1;
i is 0, 1 or 2. In the equation (9), E ^{1 to} E ¹²
Each independently represents a hydrogen atom, a fluorine atom or a chlorine atom. In the formula (10), X ^{9 to} X ¹² each independently represent CH or CF. J ⁴ is a hydrogen atom, a fluorine atom,
A cyano group or an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which may be substituted with a fluorine atom;
An alkenyloxy group, an alkynyloxy group having 3 to 12 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms. J ⁵ is a hydrogen atom, a fluorine atom, a cyano group or J ⁶
— (O) m ² (where m ² is 0 or 1, and J ⁶ is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 16 carbon atoms, which may be substituted with a fluorine atom. Or 3 carbon atoms
-16 represents an alkynyl group. E ¹ and E ² each independently represent a group represented by the following structural formula (provided that X ¹³ to
X ¹⁶ each independently represents CH or CF).

[0048]

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W ¹ is —C ₂ H ₄ —, —CH ₂ O— or —O
CH ₂ — is shown. f ¹ and f ² are each independently 0 or 1
, But do not become 1 at the same time. When f ¹ is 1,
At least one of E ^{1 and} E ² is a group represented by the following structural formula.

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G ^{5 to} G ⁸ each independently represent a hydrogen atom or a fluorine atom. In the formula (11), R ⁷ represents an alkyl group having 1 to 10 carbon atoms, and the hydrogen atom on the benzene ring in the formula (11) may be substituted by a fluorine atom. n, p and q
³ is 1 or 2 respectively. X ¹⁷ is a trans-form of -C
H = CH- or an ethynyl group (however, when n is 1, X ¹⁷ may be -CH ₂ -CH _2- ).

The compound represented by the formula (3) includes, for example, compounds having the following structural formulas. These examples include those of the compounds represented by the above formulas (5) to (11). However, in the structural formulas at the time, W represents a hydrogen atom or a fluorine atom, and x represents an integer of 0 to 3. Ring H represents 1,4-cyclohexylene. Ring G is
1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexene, 4,1-cyclohexene, 2,5-cyclohexene, 5,2-cyclohexene which may be substituted with a fluorine atom , 3,6-cyclohexelene, 6,3-cyclohexelene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, 5,2-pyridinediyl, 2,5-dioxanediyl or Shows 5,2-dioxanediyl. More preferably, ring G is 1,4-cyclohexylene,
4-cyclohexelene, 4,1-cyclohexelene,
2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene or 6,3-cyclohexelene is shown.

[0052]

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[0055]

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[0056]

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[0059]

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[0060]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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[0073]

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[0074]

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[0075]

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Further, as the compound represented by the formula (3),
The following can also be mentioned. 1- (1,2-difluoro-1- (E) -pentenyl) -4
-(2- (4-propylphenyl) ethynyl) benzene, 1
-(1,2-difluoro-1- (E) -heptenyl- (2-
(4-propylphenyl) ethynyl) benzene, 1- (1,
2-difluoro-1- (E) -butenyl) -4- (2- (4
-Propylphenyl) ethynyl) benzene, 1- (1,2
-Difluoro-1- (E) -hexenyl) -4- (2- (4
-Methylphenyl) ethynyl) benzene, 1- (1,2-
Difluoro-1- (E) -hexenyl) -4- (2- (4-
Ethylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -hexenyl) -4- (2- (4-butylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1 -(E) -hexenyl) -4- (2- (4-pentylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -hexenyl) -4- (2- (4-hexyl) (Phenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -hexenyl) -4- (2- (4-heptylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -Hexenyl) -4- (2- (4-methoxyphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -hexenyl) -4- (2- (4-ethoxyphenyl) ) Ethynyl) benzene, 1- (1,2-difluoro-1- (E) -hexenyl) -3-fluoro-4
(2- (4-pentylphenyl) ethynyl) benzene, 1-
(1,2-difluoro-1- (E) -hexenyl) -2-fluoro-4- (2- (4-pentylphenyl) ethynyl) benzene,

1- (1-Fluoro-1- (E) -pentenyl) -4- (2- (4-propynylphenyl) ethynyl) benzene, 1- (2-fluoro-1- (E) -pentenyl)-
4- (2- (4-propynylphenyl) ethynyl) benzene, 1- (1-fluoro-1- (E) -butenyl) -4-
(2- (4-propynylphenyl) ethynyl) benzene, 1
-(2-Fluoro-1- (E) -hexenyl) -4- (2-
(4-methylphenyl) ethynyl) benzene, 1- (1-fluoro-1- (E) -hexenyl) -4- (2- (4-ethylphenyl) ethynyl) benzene, 1- (2-fluoro-
1- (E) -hexenyl) -4- (2- (4-butylphenyl) ethynyl) benzene, 1- (1-fluoro-1- (E)
-Hexenyl) -4- (2- (4-pentylphenyl) ethynyl) benzene, 1- (2-fluoro-1- (E) -hexenyl) -4- (2- (4-hexylphenyl) ethynyl) benzene, 1- (1-fluoro-1- (E) -hexenyl)-
4- (2- (4-heptylphenyl) ethynyl) benzene,
1- (2-fluoro-1- (E) -hexenyl) -4- (2
-(4-methoxyphenyl) ethynyl) benzene, 1- (1
-Fluoro-1- (E) -hexenyl) -4- (2- (4-
(Ethoxyphenyl) ethynyl) benzene, 1- (2-fluoro-1- (E) -hexenyl) -3-fluoro-4- (2
-(4-pentylphenyl) ethynyl) benzene, 1- (1
-Fluoro-1- (E) -hexenyl) -2-fluoro-
4- (2- (4-pentylphenyl) tinyl) benzene, 4
-(1,2-difluoro-1- (E) -hexenyl) -1-
(2- (4-pentylcyclohexylphenyl) ethynyl)
Benzene, 4- (1,2-difluoro-1- (E) -hexenyl) -3-fluoro-1- (2- (4-propylcyclohexylphenyl) ethynyl) benzene, 4- (1-fluoro-1- ( E) -Hexenyl) -1- (2- (4-propylcyclohexylphenyl) ethynyl) benzene,

4- (2- (4- (1,2-difluoro-1)
-(E) -pentenyl) phenyl) ethyl) benzonitrile, 4- (2- (4- (1,2-difluoro-1- (E)-
Heptenyl) phenyl) ethyl) benzonitrile, 4- (2
-(4- (1-Fluoro-1- (E) -pentenyl) phenyl) ethyl) benzonitrile, 4- (2- (4- (2-fluoro-1- (E) -pentenyl) phenyl) ethyl) benzo Nitrile, 4- (2- (4- (1,2-difluoro-1-
(E) -pentenyl) phenyl) ethyl) -3-fluorobenzonitrile, 4- (2- (4- (1,2-difluoro-
1- (E) -hexenyl) phenyl) ethyl) -3-fluorobenzonitrile, 4- (2- (4- (1,2-difluoro-1- (E) -pentenyl) phenyl) ethyl) -3-fluoro Benzonitrile, 4- (2- (4- (1-fluoro-1- (E) -pentenyl) phenyl) ethyl) -3-fluorobenzonitrile, 4- (2- (4- (2-fluoro-
1- (E) -pentenyl) phenyl) ethyl) -3-fluorobenzonitrile,

1- (1,2-difluoro-1- (E) -heptenyl) -4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1,2-difluoro-
1- (E) -hexenyl) -4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1,2-
Difluoro-1- (E) -pentenyl) -4- (2- (4-
Trifluoromethoxyphenyl) ethynyl) benzene, 1
-(1,2-difluoro-1- (E) -heptenyl) -3
-Fluoro-4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1,2-difluoro-
1- (E) -Hexenyl) -3-fluoro-4- (2- (4
-Trifluoromethoxyphenyl) ethynyl) benzene,
1- (1,2-difluoro-1- (E) -pentenyl) -3
-Fluoro-4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1-fluoro-1-
(E) -heptenyl) -4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (2-fluoro-1- (E) -hexenyl) -4- (2- (4-trifluoro Methoxyphenyl) ethynyl) benzene, 1- (1-fluoro-1- (E) -pentenyl) -4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene,

1- (2-fluoro-1- (E) -heptenyl) -3-fluoro-4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1-fluoro-1- ( E) -Hexenyl) -3-fluoro-4- (2-
(4-trifluoromethoxyphenyl) ethynyl) benzene, 1- (2-fluoro-1- (E) -pentenyl) -3-
Fluoro-4- (2- (4-trifluoromethoxyphenyl) ethynyl) benzene, 4- (1,2-difluoro-1
-(E) -hexenyl) -1- (4-trans-propylcyclohexyl) benzene, 4- (1-fluoro-1- (E)-
Hexenyl) -1- (4-trans-propylcyclohexyl) benzene, 4- (1,2-difluoro-1- (E) -pentenyl) -1- (4-trans-propylcyclohexyl)
benzene,

4- (1,2-difluoro-1- (E) -hexenyl) -1- (4- (4-trans-propylcyclohexyl) cyclohexyl) benzene, 4- (1,2-difluoro-1- ( E) -pentenyl) -1- (4- (4-trans-
Propylcyclohexyl) cyclohexyl) benzene, 4
-(1,2-difluoro-1- (E) -hexenyl) -2-
Fluoro-1- (4- (4-trans-propylcyclohexyl) cyclohexyl) benzene, 4- (1,2-difluoro-1- (E) -hexenyl) -3-fluoro-1- (4
-(4-trans-propylcyclohexyl) cyclohexyl) benzene, 4- (1-fluoro-1- (E) -hexenyl) -1- (4- (4-trans-propylcyclohexyl)
Cyclohexyl) benzene, 4- (2-fluoro-1-
(E) -pentenyl) -1- (4- (4-trans-propylcyclohexyl) cyclohexyl) benzene, 2-fluoro-4- (1-fluoro-1- (E) -hexenyl) -1-
(4- (4-trans-propylcyclohexyl) cyclohexyl) benzene, 3-fluoro-4- (2-fluoro-1
-(E) -hexenyl) -1- (4- (4-trans-propylcyclohexyl) cyclohexyl) benzene, 4- (1,
2-difluoro-1- (E) -hexenyl) -4′-propylbiphenyl, 4- (1,2-difluoro-1- (E)-
Propenyl) -4′-propylbiphenyl, 4- (1,2
-Difluoro-1- (E) -heptenyl) -4'-propylbiphenyl, 4- (1,2-difluoro-1- (E) -hexenyl) -4'-methylbiphenyl, 4- (1,2-difluoro -1- (E) -heptenyl) -4′-ethylbiphenyl, 4- (1,2-difluoro-1- (E) -heptenyl) -4′-pentylbiphenyl, 4- (1,2-difluoro-1 -(E) -nonenyl) -4'-decylbiphenyl,
4- (1,2-difluoro-1- (E) -nonenyl) -4 ′
-Nonylbiphenyl, 4- (1,2-difluoro-1-
(E) -hexenyl) -4′-fluorobiphenyl, 4-
(1,2-difluoro-1- (E) -hexenyl) -4′-
Cyanobiphenyl, 4- (1,2-difluoro-1-
(E) -hexenyl) -3′-fluoro-4′-cyanobiphenyl,

2-fluoro-4- (1,2-difluoro-1- (E) -hexenyl) -4′-propylbiphenyl,
2'-fluoro-4- (1,2-difluoro-1- (E)-
(Hexenyl) -4'-propylbiphenyl, 3-fluoro-4- (1,2-difluoro-1- (E) -hexenyl)-
4'-propylbiphenyl, 2,3-difluoro-4-
(1,2-difluoro-1- (E) -hexenyl) -4′-
Propylbiphenyl, 2,3-difluoro-4- (1,
2-difluoro-1- (E) -nonenyl) -4′-decylbiphenyl, 4- (1-fluoro-1- (E) -hexenyl)
-4'-propylbiphenyl, 4- (2-fluoro-1-
(E) -propenyl) -4′-propylbiphenyl, 4-
(1-Fluoro-1- (E) -heptenyl) -4′-propylbiphenyl, 4- (2-fluoro-1- (E) -hexenyl) -4′-methylbiphenyl, 4- (1-fluoro-
1- (E) -heptenyl) -4′-ethylbiphenyl, 4-
(2-Fluoro-1- (E) -heptenyl) -4′-pentylbiphenyl, 4- (1-fluoro-1- (E) -nonenyl) -4′-decylbiphenyl, 4- (2-fluoro-1
-(E) -nonenyl) -4'-nonylbiphenyl, 4- (1
-Fluoro-1- (E) -hexenyl) -4′-fluorobiphenyl, 4- (2-fluoro-1- (E) -hexenyl)
-4'-cyanobiphenyl, 4- (1-fluoro-1-
(E) -hexenyl) -3′-fluoro-4′-cyanobiphenyl,

2-fluoro-4- (2-fluoro-1-
(E) -hexenyl) -4′-propylbiphenyl, 2′-
Fluoro-4- (1-fluoro-1- (E) -hexenyl)
-4'-propylbiphenyl, 3-fluoro-4- (2-
Fluoro-1- (E) -hexenyl) -4′-propylbiphenyl, 2,3-difluoro-4- (1-fluoro-1
-(E) -hexenyl) -4'-propylbiphenyl, 2,
3-difluoro-4- (1-fluoro-1- (E) -nonenyl) -4′-decylbiphenyl, 4- (1,2-difluoro-1- (E) -hexenyl) -4 ″ -propyl- p-
Terphenyl, 4- (1,2-difluoro-1- (E)-
(Hexenyl) -4 ''-cyano-p-terphenyl, 4-
(1,2-difluoro-1- (E) -hexenyl) -4 ''-
Cyano-3 ''-fluoro-p-terphenyl, 4- (1
-Fluoro-1- (E) -hexenyl) -4 ''-propyl-p-terphenyl, 4- (2-fluoro-1- (E)-
(Hexenyl) -4 ''-cyano-p-terphenyl,

2- (4- (1- (1,2-difluoro-1)
-(E) -hexenyl)) phenyl) -5-propylpyrimidine, 2- (4- (1- (1,2-difluoro-1- (E)
-Pentenyl)) phenyl) -5-propylpyrimidine,
2- (4- (1- (1,2-difluoro-1- (E) -nonenyl)) phenyl) -5-decylpyrimidine, 2- (4-
(1- (1,2-difluoro-1- (E) -nonenyl))-
2,3-difluorophenyl) -5-decylpyrimidine, 2- (4- (1- (1,2-difluoro-1- (E)-
Nonenyl))-3-fluorophenyl) -5-decylpyrimidine, 2- (4- (1- (1-fluoro-1- (E) -hexenyl)) phenyl) -5-propylpyrimidine, 2-
(4- (1- (2-fluoro-1- (E) -pentenyl)) phenyl) -5-propylpyrimidine, 2- (4- (1- (1
-Fluoro-1- (E) -nonenyl)) phenyl) -5-decylpyrimidine, 2- (4- (1- (2-fluoro-1-
(E) -nonenyl))-2,3-difluorophenyl) -5
-Decylpyrimidine, 2- (4- (1- (1-fluoro-
1- (E) -nonenyl))-3-fluorophenyl) -5
Decyl pyrimidine,

1- (4-methylphenyl-methyl) -4-
(1,2-difluoro-1- (E) -pentenyl) benzene, 1- (4-ethylphenyl-methyl) -4- (1,2
-Difluoro-1- (E) -pentenyl) benzene, 1-
(4-propylphenyl-methyl) -4- (1-fluoro-1- (E) pentenyl) benzene, 1- (4-propylphenyl-methyl) -4- (1,2-difluoro-1- (E)
-Hexenyl) benzene, 1- (4-propylphenyl-
Methyl) -4- (2-fluoro-1- (E) -heptenyl)
Benzene, 1- (4-trifluoromethylphenyl-methyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (3,4,5-trifluorophenyl-methyl)- 4- (1-fluoro-1- (E) -pentenyl) benzene, 1- (2- (4-methylphenyl) ethyl)
-4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-ethylphenyl) ethyl) -4-
(2-fluoro-1- (E) -pentenyl) benzene, 1-
(2- (4-propylphenyl) ethyl) -4- (1,2-
Difluoro-1- (E) -pentenyl) benzene, 1- (2
-(4-butylphenyl) ethyl) -4- (1-fluoro-
1- (E) -pentenyl) benzene,

1- (2- (4-pentylphenyl) ethyl)
-4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-hexylphenyl) ethyl) -4
-(2-fluoro-1- (E) -pentenyl) benzene, 1
-(2- (4-heptylphenyl) ethyl) -4- (1,2
-Difluoro-1- (E) -pentenyl) benzene, 1-
(2- (4-octylphenyl) ethyl) -4- (1-fluoro-1- (E) -pentenyl) benzene, 1- (2- (4
-Nonylphenyl) ethyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-decylphenyl) ethyl) -4- (2-fluoro-1- ( E)
-Pentenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4- (1,2-difluoro-1- (E)-
Propenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4- (1-fluoro-1- (E) -butenyl)
Benzene, 1- (2- (4-propylphenyl) ethyl)-
4- (1,2-difluoro-1- (E) -hexenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4-
(2-fluoro-1- (E) -heptenyl) benzene, 1-
(2- (4-propylphenyl) ethyl) -4- (1,2-
Difluoro-1- (E) -octenyl) benzene, 1- (2
-(4-decylphenyl) ethyl) -4- (1-fluoro-
1- (E) -nonenyl) benzene, 1- (2- (4-decylphenyl) ethyl) -4- (1,2-difluoro-1-
(E) -nonenyl) benzene,

1- (4-propylcyclohexyl) -4-
(2- (4- (2-fluoro-1- (E) -propenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2- (4- (1,2-difluoro- 1-
(E) -butenyl) -phenyl) ethyl) benzene, 1- (4
-Propylcyclohexyl) -4- (2- (4- (1-fluoro-1- (E) -pentenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2-
(4- (1,2-difluoro-1- (E) -hexenyl)-
Phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2- (4- (2-fluoro-1- (E)-
Heptenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2- (4- (1,2-difluoro-1- (E) -octenyl) -phenyl) ethyl) benzene, (4-propylcyclohexyl) -4- (2
-(4- (1-fluoro-1- (E) -nonenyl) -phenyl) ethyl) benzene, 1- (4-butylcyclohexyl)
-4- (2- (4- (1,2-difluoro-1- (E) -pentenyl) -phenyl) ethyl) benzene, 1- (4-pentylcyclohexyl) -4- (2- (4- (2 -Fluoro-
1- (E) -pentenyl) -phenyl) ethyl) benzene,
1- (4-propyl-1-cyclohexenyl) -4- (2
-(4- (1,2-difluoro-1- (E) -pentenyl)
-Phenyl) ethyl) benzene, 1- (4-propyl-1
-Cyclohexenyl) -4- (2- (4- (1-fluoro-
1- (E) -heptenyl) -phenyl) ethyl) benzene,

1- (2- (4-trifluoromethylphenyl) ethyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-cyanophenyl) ethyl ) -4- (2-Fluoro-1- (E) -pentenyl) benzene, 1- (2- (4-fluorophenyl) ethyl) -4-
(1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (3,4-difluorophenyl) ethyl) -4
-(1-fluoro-1- (E) -pentenyl) benzene, 1
-(2- (3,4-difluorophenyl) ethyl) -4-
(1,2-difluoro-1- (E) -heptenyl) benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (2-fluoro-1- (E) -propenyl ) Benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1,2-difluoro-1- (E) -butenyl) benzene, 1- (2- (3,4 , 5-trifluorophenyl) ethyl) -4- (1-fluoro-1- (E) -pentenyl) benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1 , 2-Difluoro-1- (E)
-Hexenyl) benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (2-fluoro-1-
(E) -heptenyl) benzene, 1- (2- (3,4,5-
(Trifluorophenyl) ethyl) -4- (1,2-difluoro-1- (E) -octenyl) benzene, 1- (2- (3,
4,5-trifluorophenyl) ethyl) -4- (1-fluoro-1- (E) -nonenyl) benzene,

1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1,2-difluoro-1-
(E) -propenyl) benzene, 1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (2-fluoro-1- (E) -butenyl) benzene, 1- (2 − (4-
Propyl-3,5-difluorophenyl) ethyl) -4-
(1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1-fluoro-1- (E) -Hexenyl) benzene, 1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1,2-difluoro-1
-(E) -heptenyl) benzene, 1- (2- (4-methyl-3,5-difluorophenyl) ethyl) -4- (2-fluoro-1- (E) -pentenyl) benzene, 1- ( 2- (4
-Ethyl-3,5-difluorophenyl) ethyl) -4-
(1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4-butyl-3,5-difluorophenyl) ethyl) -4- (1-fluoro-1- (E) -Pentenyl) benzene, 1- (2- (4-pentyl-3,5-difluorophenyl) ethyl) -4- (1,2-difluoro-1
-(E) -pentenyl) benzene,

2-Fluoro-1- (2- (4-propylphenyl) ethyl) -4- (2-fluoro-1- (E) -pentenyl) benzene, 2-fluoro-1- (2- (4- Propylphenyl) ethyl) -4- (1,2-difluoro-1-
(E) -hexenyl) benzene, 2-fluoro-1- (2-
(4-propylphenyl) ethyl) -4- (1-fluoro-
1- (E) -heptenyl) benzene, 3-fluoro-1- (2
-(4-propylphenyl) ethyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 3-fluoro-1- (2- (4-propylphenyl) ethyl) -4- ( 2
-Fluoro-1- (E) -hexenyl) benzene, 2-fluoro-1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1,2-difluoro-1- (E) -Pentenyl) benzene, 2,6-difluoro-1- (2- (3,4,
5-trifluorophenyl) ethyl) -4- (1-fluoro-1- (E) -pentenyl) benzene, 2-fluoro-1-
(2- (3,4-difluorophenyl) ethyl) -4- (1,
2-difluoro-1- (E) -pentenyl) benzene,

2,6-difluoro-1- (2- (3,4-
Difluorophenyl) ethyl) -4- (2-fluoro-1-
(E) -pentenyl) benzene, 2,6-difluoro-1
-(2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 2,6-difluoro-1- (2- (4-trifluoromethyl-3,5-difluorophenyl) ethyl)-
4- (1-fluoro-1- (E) -pentenyl) benzene,
2,6-difluoro-1- (2- (4-trifluoromethoxy-3,5-difluorophenyl) ethyl) -4- (1,2
-Difluoro-1- (E) -pentenyl) benzene, 1-
(2- (4-cyano-3-fluorophenyl) ethyl) -4-
(2-fluoro-1- (E) -pentenyl) benzene, 1-
(2- (4-cyano-3-fluorophenyl) ethyl) -4-
(1,2-difluoro-1- (E) -heptenyl) benzene, 1- (2- (4-cyano-3-fluorophenyl) ethyl) -2-fluoro-4- (1-fluoro-1- (E ) -Pentenyl) benzene, 1- (2- (4-cyano-3-fluorophenyl) ethyl) -2,6-difluoro-4- (1,2-
Difluoro-1- (E) -pentenyl) benzene, 1- (2
-(4-cyano-3,5-difluorophenyl) ethyl)-
4- (2-fluoro-1- (E) -pentenyl) benzene,
1- (2- (4-cyano-3,5-difluorophenyl) ethyl) -2-fluoro-4- (1,2-difluoro-1-
(E) -pentenyl) benzene, 1- (2- (4-cyano-
3,5-difluorophenyl) ethyl) -2,6-difluoro-4- (1-fluoro-1- (E) -pentenyl) benzene,

1- (4,4-difluorocyclohexyl)-
4- (2- (4- (1,2-difluoro-1- (E) -pentenyl) phenyl) ethyl) benzene, 1- (4-fluorocyclohexyl) -4- (2- (4- (2-fluoro -1- (E)-
Pentenyl) phenyl) ethyl) benzene, 1- (2- (4 ′
-Propyl-dicyclohexyl) ethyl) -4- (1,2
-Difluoro-1- (E) -pentenyl) benzene, 1- (2
-(4 ', 4-dipropyl-dicyclohexyl) ethyl)-
4- (1-fluoro-1- (E) -pentenyl) benzene, 1
-(2- (4'-fluoro-dicyclohexyl) ethyl) -4
-(1,2-difluoro-1- (E) -pentenyl) benzene, 1- (2- (4 ', 4-difluoro-dicyclohexyl)
Ethyl) -4- (2-fluoro-1- (E) -pentenyl) benzene,

1- (3- (4-propylphenyl) propyl) -4- (1,2-difluoro-1- (E) -pentenyl) benzene, 1- (3- (3,4-difluorophenyl) (Propyl) -4- (1-fluoro-1- (E) -pentenyl)
Benzene, 1- (3- (3,4,5-trifluorophenyl) propyl) -4- (1,2-difluoro-1- (E)-
Pentenyl) benzene, 1- (4- (4-propylphenyl) butyl) -4- (2-fluoro-1- (E) -pentenyl) benzene, 1- (4- (3,4-difluorophenyl) butyl ) -4- (1,2-Difluoro-1- (E) -pentenyl) benzene, 1- (4- (3,4,5-trifluorophenyl) butyl) -4- (1-fluoro-1- ( E) -Pentenyl) benzene, 1- (4- (3,5-difluoro-4-propylphenyl) butyl) -4- (1,2-difluoro-
1- (E) -pentenyl) benzene,

4- (4-methylbenzyloxy) -1-
(2-fluoro-1- (E) -pentenyl) benzene, 4-
(4-Ethylbenzyloxy) -1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-propylbenzyloxy) -1- (1-fluoro-1- (E)- (Pentenyl) benzene, 4- (4-butylbenzyloxy)
-1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-pentylbenzyloxy) -1- (2
-Fluoro-1- (E) -pentenyl) benzene, 4- (4
-Hexylbenzyloxy) -1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-heptylbenzyloxy) -1- (1-fluoro-1- (E) -pentenyl) Benzene, 4- (4-octylbenzyloxy)
-1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-propylbenzyloxy) -1- (2
-Fluoro-1- (E) -heptenyl) benzene, 4- (4
-Nonylbenzyloxy) -1- (1,2-difluoro-
1- (E) -heptenyl) benzene, 4- (4-hexylbenzyloxy) -1- (1-fluoro-1- (E) -nonenyl) benzene, 4- (4-heptylbenzyloxy) -1
-(1,2-difluoro-1- (E) -nonenyl) benzene, 4- (4-octylbenzyloxy) -1- (2-fluoro-1- (E) -nonenyl) benzene, 4- (4- Nonylbenzyloxy) -1- (1,2-difluoro-1-
(E) -nonenyl) benzene, 4- (4-decylbenzyloxy) -1- (1-fluoro-1- (E) -nonenyl) benzene, 4- (4-undecylbenzyloxy) -1-
(1,2-difluoro-1- (E) -nonenyl) benzene,
4- (4-trifluorobenzyloxy) -1- (2-fluoro-1- (E) -pentenyl) benzene, 4- (4-trifluorobenzyloxy) -1- (1,2-difluoro-1
-(E) -heptenyl) benzene, 4- (4-cyanobenzyloxy) -1- (1-fluoro-1- (E) -pentenyl) benzene,

1- (4- (E) -pentenylbenzyloxy) -4-methylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-ethylbenzene, 1- (4- (E)
-Pentenylbenzyloxy) -4-propylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-
Butylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-pentylbenzene, 1- (4- (E) -hexenylbenzyloxy) -4-propylbenzene, 1-
(4- (E) -heptenylbenzyloxy) -4-propylbenzene, 1- (4- (E) -pentenylbenzyloxy)
-4-trifluoromethylbenzene, 1- (4- (E) -pentenylbenzyloxy) -3,4,5-trifluorobenzene, 1- (4- (E) -pentenylbenzyloxy)-
4-cyanobenzene,

4- (4-methylphenoxy) -1- (1,
2-difluoro-1- (E) -pentenyl) benzene, 4
-(4-ethylphenoxy) -1- (2-fluoro-1-
(E) -pentenyl) benzene, 4- (4-propylphenoxy) -1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-butylphenoxy) -1- (1-
Fluoro-1- (E) -pentenyl) benzene, 4- (4-
Pentylphenoxy) -1- (1,2-difluoro-1-
(E) -pentenyl) benzene, 4- (4-hexylphenoxy) -1- (2-fluoro-1- (E) -pentenyl) benzene, 4- (4-propylphenoxy) -1- (1,2
-Difluoro-1- (E) -propenyl) benzene, 4-
(4-propylphenoxy) -1- (1-fluoro-1-
(E) -butenyl) benzene, 4- (4-propylphenoxy) -1- (1,2-difluoro-1- (E) -pentenyl) benzene, 4- (4-propylphenoxy) -1- (2
-Fluoro-1- (E) -hexenyl) benzene, 4- (4
-Propylphenoxy) -1- (1,2-difluoro-1
-(E) -heptenyl) benzene, 4- (4-propylphenoxy) -1- (1-fluoro-1- (E) -octenyl)
Benzene, 4- (4-trifluoromethylphenoxy) -1
-(1,2-difluoro-1- (E) -pentenyl) benzene,

(4- (2-Fluoro-1- (E) -propenyl)) phenyl- (4-propyl) benzoate, (4-
(1,2-difluoro-1- (E) -butenyl)) phenyl- (4-propyl) benzoate, (4- (1-fluoro-
1- (E) -pentenyl)) phenyl- (4-propyl) benzoate, (4- (1,2-difluoro-1- (E) -hexenyl)) phenyl- (4-propyl) benzoate, (4
-(2-fluoro-1- (E) -heptenyl)) phenyl-
(4-propyl) benzoate, (4- (1,2-difluoro-1- (E) -octenyl)) phenyl- (4-propyl)
Benzoate, (4- (1-fluoro-1- (E) -pentenyl)) phenyl- (4-methyll) benzoate, (4-
(1,2-difluoro-1- (E) -pentenyl)) phenyl- (4-ethyl) benzoate, (4- (2-fluoro-
1- (E) -pentenyl)) phenyl- (4-propyl) benzoate, (4- (1,2-difluoro-1- (E) -pentenyl)) phenyl- (4-butyl) benzoate, (4-
(1-Fluoro-1- (E) -pentenyl)) phenyl- (4
-Pentyl) benzoate,

(4- (1,2-difluoro-1- (E) -propenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (2-fluoro-1- (E)) -Butenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1,2-difluoro-1-
(E) -pentenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1-fluoro-1-
(E) -Hexenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1,2-difluoro-1- (E) -heptenyl)) phenyl- (4- (4-propyl Cyclohexyl)) benzoate, (4- (2-fluoro-1- (E) -octenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1,2-difluoro-1- (E) -heptenyl)) phenyl- (4- (4-
Methylcyclohexyl)) benzoate, (4- (1-fluoro-1- (E) -pentenyl)) phenyl- (4- (4-ethylcyclohexyl)) benzoate, (4- (1,2-difluoro-1) -(E) -pentenyl)) phenyl- (4- (4
-Butylcyclohexyl)) benzoate, (4- (2-fluoro-1- (E) -pentenyl)) phenyl- (4- (4-
(Pentylcyclohexyl)) benzoate, (4- (1,2
-Difluoro-1- (E) -pentenyl)) phenyl- (4
-(4-propylcyclohexyl)) benzoate, (4-
(1-Fluoro-1- (E) -pentenyl)) phenyl- (4
-(4-pentylcyclohexyl)) benzoate, (4-
(1,2-difluoro-1- (E) -propenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (2
-Fluoro-1- (E) -butenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (1,2-difluoro-1- (E) -pentenyl)) phenyl- (4- Cyano-3-fluoro) benzoate, (4- (1-fluoro-
1- (E) -hexenyl)) phenyl- (4-cyano-3-
(Fluoro) benzoate, (4- (1,2-difluoro-1)
-(E) -heptenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (2-fluoro-1- (E)-
Octenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (1,2-difluoro-1- (E) -propenyl)) phenyl- (3,4-difluoro) benzoate,
(4- (1-Fluoro-1- (E) -pentenyl)) phenyl- (3,4-difluoro) benzoate, (4- (1,2-difluoro-1- (E) -heptenyl)) phenyl- (3,4
-Difluoro) benzoate, (4- (2-fluoro-1-
(E) -propenyl)) phenyl- (3,4,5-trifluoro) benzoate, (4- (1,2-difluoro-1-
(E) -pentenyl)) phenyl- (3,4,5-trifluoro) benzoate, (4- (1-fluoro-1- (E) -heptenyl)) phenyl- (3,4,5-trifluoro) benzo Art,

4-methylphenyl- (4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, 4-ethylphenyl- (4- (2-fluoro-1- (E) -pentenyl) ) Benzoate, 4-propylphenyl- (4-
(1,2-difluoro-1- (E) -pentenyl)) benzoate, 4-butylphenyl- (4- (1-fluoro-1
-(E) -pentenyl)) benzoate, 4-pentylphenyl- (4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, 4-hexylphenyl- (4- (2-
Fluoro-1- (E) -pentenyl)) benzoate, 4-
Heptylphenyl- (4- (1,2-difluoro-1-
(E) -pentenyl)) benzoate, 4-octylphenyl- (4- (1-fluoro-1- (E) -nonenyl)) benzoate, 4-nonylphenyl- (4- (1,2-difluoro-1- (E) -nonenyl)) benzoate, 4-decylphenyl- (4- (2-fluoro-1- (E) -nonenyl)) benzoate, 4-undecylphenyl- (4- (1,2-
Difluoro-1- (E) -nonenyl)) benzoate, 4-
Octylphenyl- (4- (1-fluoro-1- (E) -nonenyl)) benzoate, 4-nonyloxyphenyl-
(4- (1,2-difluoro-1- (E) -nonenyl)) benzoate, 4-decyloxyphenyl- (4- (2-fluoro-1- (E) -nonenyl)) benzoate,

4- (4-methylcyclohexyl) phenyl- (4- (1,2-difluoro-1- (E) -pentenyl))
Benzoate, 4- (4-ethylcyclohexyl) phenyl- (4- (1-fluoro-1- (E) -pentenyl)) benzoate, 4- (4-propylcyclohexyl) phenyl- (4- (1,2-difluoro -1- (E) -pentenyl))
Benzoate, 4- (4-butylcyclohexyl) phenyl- (4- (2-fluoro-1- (E) -pentenyl)) benzoate, 4- (4-pentylcyclohexyl) phenyl- (4- (1,2-difluoro -1- (E) -pentenyl))
Benzoate, 4- (4-hexylcyclohexyl) phenyl- (4- (1-fluoro-1- (E) -pentenyl)) benzoate, 4- (4-propylcyclohexyl) phenyl- (4- (1,2-difluoro -1- (E) -propenyl)) benzoate, 4- (4-propylcyclohexyl)
Phenyl- (4- (2-fluoro-1- (E) -butenyl))
Benzoate, 4- (4-propylcyclohexyl) phenyl- (4- (1,2-difluoro-1- (E) -hexenyl)) benzoate, 4- (4-propylcyclohexyl)
Phenyl- (4- (1-fluoro-1- (E) -heptenyl)) benzoate, 4- (4-propylcyclohexyl)
Phenyl- (4- (1,2-difluoro-1- (E) -octenyl)) benzoate, 4- (4-propylcyclohexyl) phenyl- (4- (2-fluoro-1- (E) -pentenyl)) Benzoate, 4- (4-cyano-3-fluoro)
Phenyl- (4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, 4- (4-cyano-3-fluoro)
Phenyl- (4- (1-fluoro-1- (E) -heptenyl)) benzoate, 4- (3,4-difluoro) phenyl-
(4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, 4- (3,4-difluoro) phenyl- (4-
(2-Fluoro-1- (E) -heptenyl)) benzoate, 4- (3,4,5-trifluoro) phenyl- (4-
(1,2-Difluoro-1- (E) -pentenyl)) benzoate, 4- (3,4,5-trifluoro) phenyl- (4
-(1-fluoro-1- (E) -heptenyl)) benzoate,

1- (4-methylphenyl-methyl) -4-
(1- (E) -pentenyl) benzene, 1- (4-ethylphenyl-methyl) -4- (1- (E) -pentenyl) benzene, 1- (4-propylphenyl-methyl) -4- (1 −
(E) -pentenyl) benzene, 1- (4-propylphenyl-methyl) -4- (1- (E) -hexenyl) benzene,
1- (4-propylphenyl-methyl) -4- (1- (E)
-Heptenyl) benzene, 1- (4-trifluoromethylphenyl-methyl) -4- (1- (E) -pentenyl) benzene, 1- (3,4,5-trifluorophenylmethyl) -4
-(1- (E) -pentenyl) benzene,

1- (2- (4-methylphenyl) ethyl)-
4- (1- (E) -pentenyl) benzene, 1- (2- (4-
Ethylphenyl) ethyl) -4- (1- (E) -pentenyl)
Benzene, 1- (2- (4-propylphenyl) ethyl)-
4- (1- (E) -pentenyl) benzene, 1- (2- (4-
(Butylphenyl) ethyl) -4- (1- (E) -pentenyl)
Benzene, 1- (2- (4-pentylphenyl) ethyl)-
4- (1- (E) -pentenyl) benzene, 1- (2- (4-
(Hexylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2- (4-heptylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2 −
(4-octylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2- (4-nonylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, − (2-
(4-decylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4- (1- (E) -propenyl) benzene, − (2-
(4-propylphenyl) ethyl) -4- (1- (E) -butenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4- (1- (E) -hexenyl) benzene, − (2-
(4-propylphenyl) ethyl) -4- (1- (E) -heptenyl) benzene, 1- (2- (4-propylphenyl) ethyl) -4- (1- (E) -octenyl) benzene, − (2
-(4-decylphenyl) ethyl) -4- (1- (E) -nonenyl) benzene, 1- (2- (4-decyloxyphenyl)
Ethyl) -4- (1- (E) -nonenyl) benzene,

1- (4-propylcyclohexyl) -4-
(2- (4- (1- (E) -propenyl) -phenyl) ethyl)
Benzene, 1- (4-propylcyclohexyl) -4-
(2- (4- (1- (E) -butenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2
-(4- (1- (E) -pentenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2
-(4- (1- (E) -hexenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2
-(4- (1- (E) -heptenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2
-(4- (1- (E) -octenyl) -phenyl) ethyl) benzene, 1- (4-propylcyclohexyl) -4- (2
-(4- (1- (E) -nonenyl) -phenyl) ethyl) benzene, 1- (4-butylcyclohexyl) -4- (2- (4
-(1- (E) -pentenyl) -phenyl) ethyl) benzene, 1- (4-pentylcyclohexyl) -4- (2- (4
-(1- (E) -pentenyl) -phenyl) ethyl) benzene, 1- (4-propyl-1-cyclohexenyl) -4-
(2- (4- (1- (E) -pentenyl) -phenyl) ethyl)
Benzene, 1- (4-propyl-1-cyclohexenyl)
-4- (2- (4- (1- (E) -heptenyl) -phenyl)
Ethyl) benzene,

1- (2- (4-trifluoromethylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
-(2- (4-cyanophenyl) ethyl) -4- (1- (E)
-Pentenyl) benzene, 1- (2- (4-fluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
-(2- (3,4-difluorophenyl) ethyl) -4- (1
-(E) -pentenyl) benzene, 1- (2- (3,4-difluorophenyl) ethyl) -4- (1- (E) -heptenyl)
Benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1- (E) -propenyl) benzene,
-(2- (3,4,5-trifluorophenyl) ethyl) -4
-(1- (E) -butenyl) benzene, 1- (2- (3,4,
5-trifluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1- (E)- Hexenyl) benzene, 1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1- (E) -heptenyl) benzene, 1- (2
-(3,4,5-trifluorophenyl) ethyl) -4- (1
-(E) -octenyl) benzene, 1- (2- (3,4,5
-Trifluorophenyl) ethyl) -4- (1- (E) -nonenyl) benzene, 1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1- (E) -Propenyl)
Benzene, 1- (2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1- (E) -butenyl) benzene, 1- (2- (4-propyl-3,5- Difluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1
-(2- (4-propyl-3,5-difluorophenyl) ethyl) -4- (1- (E) -hexenyl) benzene, 1- (2
-(4-propyl-3,5-difluorophenyl) ethyl)
-4- (1- (E) -heptenyl) benzene, 1- (2- (4
-Methyl-3,5-difluorophenyl) ethyl) -4-
(1- (E) -pentenyl) benzene, 1- (2- (4-ethyl-3,5-difluorophenyl) ethyl) -4- (1-
(E) -pentenyl) benzene, 1- (2- (4-butyl-
3,5-difluorophenyl) ethyl) -4- (1- (E)-
Pentenyl) benzene, 1- (2- (4-pentyl-3,
5-difluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene,

2-fluoro-1- (2- (4-propylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
2-fluoro-1- (2- (4-propylphenyl) ethyl)
-4- (1- (E) -hexenyl) benzene, 2-fluoro-
1- (2- (4-propylphenyl) ethyl) -4- (1-
(E) -heptenyl) benzene, 3-fluoro-1- (2-
(4-propylphenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 3-fluoro-1- (2- (4-propylphenyl) ethyl) -4- (1- (E) -hexenyl ) Benzene, 2-fluoro-1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 2,6-difluoro-1- (2- (3,4,5-trifluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 2-fluoro-1- (2- (3,4-difluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
2,6-difluoro-1- (2- (3,4-difluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
2,6-difluoro-1- (2- (4-propyl-3,5-
Difluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 2,6-difluoro-1- (2- (4-trifluoromethyl-3,5-difluorophenyl) ethyl) -4
-(1- (E) -pentenyl) benzene, 2,6-difluoro-1- (2- (4-trifluoromethoxy-3,5-difluorophenyl) ethyl) -4- (1- (E)- (Pentenyl) benzene,

1- (2- (4-cyano-3-fluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene,
-(2- (4-cyano-3-fluorophenyl) ethyl) -4
-(1- (E) -heptenyl) benzene, 1- (2- (4-cyano-3-fluorophenyl) ethyl) -2-fluoro-4-
(1- (E) -pentenyl) benzene, 1- (2- (4-cyano-3-fluorophenyl) ethyl) -2,6-difluoro-
4- (1- (E) -pentenyl) benzene, 1- (2- (4-
Cyano-3,5-difluorophenyl) ethyl) -4- (1
-(E) -pentenyl) benzene, 1- (2- (4-cyano-3,5-difluorophenyl) ethyl) -2-fluoro-4
-(1- (E) -pentenyl) benzene, 1- (2- (4-cyano-3,5-difluorophenyl) ethyl) -2,6-difluoro-4- (1- (E) -pentenyl) Benzene, 1-
(4,4-difluorocyclohexyl) -4- (2- (4-
(1- (E) -pentenyl) phenyl) ethyl) -benzene,
1- (4-fluorocyclohexyl) -4- (2- (4- (1
-(E) -pentenyl) phenyl) ethyl) -benzene, 1
-(2- (4'-propyl-dicyclohexyl) ethyl)-
4- (1- (E) -pentenyl) -benzene, 1- (2-
(4 ', 4'-dipropyl-dicyclohexyl) ethyl)-
4- (1- (E) -pentenyl) -benzene, 1- (2-
(4'-Fluoro-dicyclohexyl) ethyl) -4- (1-
(E) -pentenyl) -benzene, 1- (2- (4 ′, 4′-
(Fluoro-dicyclohexyl) ethyl) -4- (1- (E)-
Pentenyl) -benzene, 1- (3- (4-propylphenyl) propyl) -4- (1- (E) -pentenyl) benzene, 1- (3- (3,4-difluorophenyl) propyl)-
4- (1- (E) -pentenyl) benzene, 1- (3- (3,
4,5-trifluorophenyl) propyl) -4- (1-
(E) -pentenyl) benzene, 1- (4- (4-propylphenyl) butyl) -4- (1- (E) -pentenyl) benzene, 1- (4- (3,4-difluorophenyl) butyl ) -4
-(1- (E) -pentenyl) benzene, 1- (4- (3,
4,5-trifluorophenyl) butyl) -4- (1- (E)
-Pentenyl) benzene, 1- (4- (3,5-difluoro-4-propylphenyl) butyl) -4- (1- (E) -pentenyl) benzene,

4- (4-methylbenzyloxy) -1-
(1- (E) -pentenyl) benzene, 4- (4-ethylbenzyloxy) -1- (1- (E) -pentenyl) benzene, 4- (4-propylbenzyloxy) -1- (1-
(E) -pentenyl) benzene, 4- (4-butylbenzyloxy) -1- (1- (E) -pentenyl) benzene,
(4-pentylbenzyloxy) -1- (1- (E) -pentenyl) benzene, 4- (4-hexylbenzyloxy)
-1- (1- (E) -pentenyl) benzene, 4- (4-heptylbenzyloxy) -1- (1- (E) -pentenyl)
Benzene, 4- (4-octylbenzyloxy) -1-
(1- (E) -pentenyl) benzene, 4- (4-propylbenzyloxy) -1- (1- (E) -heptenyl) benzene, 4- (4-nonylbenzyloxy) -1- (1- ( E)
-Heptenyl) benzene, 4- (4-hexylbenzyloxy) -1- (1- (E) -nonenyl) benzene, 4- (4-
Heptylbenzyloxy) -1- (1- (E) -nonenyl)
Benzene, 4- (4-octylbenzyloxy) -1-
(1- (E) -nonenyl) benzene, 4- (4-nonylbenzyloxy) -1- (1- (E) -nonenyl) benzene,
-(4-decylbenzyloxy) -1- (1- (E) -nonenyl) benzene, 4- (4-undecylbenzyloxy)
-1- (1- (E) -nonenyl) benzene, 4- (4-trifluoromethylbenzyloxy) -1- (1- (E) -pentenyl) benzene, 4- (4-trifluoromethylbenzyloxy) -1- (1- (E) -heptenyl) benzene, 4- (4
-Cyanobenzyloxy) -1- (1- (E) -pentenyl) benzene,

1- (4- (E) -pentenylbenzyloxy) -4-methylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-ethylbenzene, 1- (4- (E)
-Pentenylbenzyloxy) -4-propylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-
Butylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-pentylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-propylbenzene, 1-
(4- (E) -hexenylbenzyloxy) -4-propylbenzene, 1- (4- (E) -heptenylbenzyloxy)
4-propylbenzene, 1- (4- (E) -pentenylbenzyloxy) -4-trifluoromethylbenzene, 1
-(4- (E) -pentenylbenzyloxy) -3,4,5
-Trifluorobenzene, 1- (4- (E) -pentenylbenzyloxy) -4-cyanobenzene,

4- (4-methylphenoxy) -1- (1-
(E) -pentenyl) benzene, 4- (4-ethylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4-
Propylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4-butylphenoxy) -1- (1- (E)
-Pentenyl) benzene, 4- (4-pentylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4-
Hexylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4-propylphenoxy) -1- (1-
(E) -propenyl) benzene, 4- (4-propylphenoxy) -1- (1- (E) -butenyl) benzene, 4- (4-
Propylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4-propylphenoxy) -1- (1-
(E) -hexenyl) benzene, 4- (4-propylphenoxy) -1- (1- (E) -heptenyl) benzene, 4- (4
-Propylphenoxy) -1- (1- (E) -octenyl)
Benzene, 4- (4-trifluoromethylphenoxy) -1
-(1- (E) -pentenyl) benzene,

(4- (1- (E) -propenyl)) phenyl-
(4-propyl) benzoate, (4- (1- (E) -butenyl)) phenyl- (4-propyl) benzoate, (4- (1
-(E) -pentenyl)) phenyl- (4-propyl) benzoate, (4- (1- (E) -hexenyl)) phenyl- (4
-Propyl) benzoate, (4- (1- (E) -heptenyl)) phenyl- (4-propyl) benzoate, (4- (1
-(E) -octenyl)) phenyl- (4-propyl) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4
-Methyl) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4-ethyl) benzoate, (4- (1-
(E) -pentenyl)) phenyl- (4-propyl) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4-
(Butyl) benzoate, (4- (1- (E) -pentenyl))
Phenyl- (4-pentyl) benzoate, (4- (1-
(E) -propenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1- (E) -butenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4 -(1- (E) -pentenyl)) phenyl-
(4- (4-propylcyclohexyl)) benzoate,
(4- (1- (E) -hexenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1- (E)
-Heptenyl)) phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1- (E) -octenyl))
Phenyl- (4- (4-propylcyclohexyl)) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4
-(4-methylcyclohexyl)) benzoate, (4-
(1- (E) -pentenyl)) phenyl- (4- (4-ethylcyclohexyl)) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4- (4-butylcyclohexyl))
Benzoate, (4- (1- (E) -pentenyl)) phenyl- (4- (4-pentylcyclohexyl)) benzoate,
(4- (1- (E) -pentenyl)) phenyl- (4- (4-propylcyclohexenyl)) benzoate, (4- (1-
(E) -pentenyl)) phenyl- (4- (4-pentylcyclohexenyl)) benzoate, (4- (1- (E) -propenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4 -(1- (E) -butenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (1- (E) -pentenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (1- (E) -hexenyl)) phenyl- (4-
Cyano-3-fluoro) benzoate, (4- (1- (E)-
Heptenyl)) phenyl- (4-cyano-3-fluoro) benzoate, (4- (1- (E) -octenyl)) phenyl-
(4-cyano-3-fluoro) benzoate, (4- (1-
(E) -propenyl)) phenyl- (3,4-difluoro) benzoate, (4- (1- (E) -pentenyl)) phenyl-
(3,4-difluoro) benzoate, (4- (1- (E) -heptenyl)) phenyl- (3,4-difluoro) benzoate, (4- (1- (E) -propenyl)) phenyl- (3 ,
4,5-trifluoro) benzoate, (4- (1- (E)-
(Pentenyl)) phenyl- (3,4,5-trifluoro) benzoate, (4- (1- (E) -heptenyl)) phenyl-
(3,4,5-trifluoro) benzoate,

4-methylphenyl- (4- (1- (E) -pentenyl)) benzoate, 4-ethylphenyl- (4-
(1- (E) -pentenyl)) benzoate, 4-propylphenyl- (4- (1- (E) -pentenyl)) benzoate, 4-butylphenyl- (4- (1- (E) -pentenyl)) Benzoate, 4-pentylphenyl- (4- (1-
(E) -pentenyl)) benzoate, 4-hexylphenyl- (4- (1- (E) -pentenyl)) benzoate, 4-
Heptylphenyl- (4- (1- (E) -pentenyl)) benzoate, 4-octylphenyl- (4- (1- (E) -nonenyl)) benzoate, 4-nonylphenyl- (4- (1
-(E) -nonenyl)) benzoate, 4-decylphenyl- (4- (1- (E) -nonenyl)) benzoate, 4-undecylphenyl- (4- (1- (E) -nonenyl)) benzoate , 4-octyloxyphenyl- (4- (1- (E)-
Nonenyl)) benzoate, 4-nonyloxyphenyl-
(4- (1- (E) -nonenyl)) benzoate, 4-decyloxyphenyl- (4- (1- (E) -nonenyl)) benzoate,

4- (4-methylcyclohexyl) phenyl- (4- (1- (E) -pentenyl)) benzoate, 4-
(4-ethylcyclohexyl) phenyl- (4- (1- (E)
-Pentenyl)) benzoate, 4- (4-propylcyclohexyl) phenyl- (4- (1- (E) -pentenyl))
Benzoate, 4- (4-butylcyclohexyl) phenyl- (4- (1- (E) -pentenyl)) benzoate, 4-
(4-pentylcyclohexyl) phenyl- (4- (1-
(E) -pentenyl)) benzoate, 4- (4-hexylcyclohexyl) phenyl- (4- (1- (E) -pentenyl)) benzoate, 4- (4-propylcyclohexyl)
Phenyl- (4- (1- (E) -propenyl)) 4- (4-propylcyclohexyl) phenyl- (4- (1- (E) -butenyl)) 4- (4-propylcyclohexyl) phenyl-
(4- (1- (E) -hexynyl)) 4- (4-propylcyclohexyl) phenyl- (4- (1- (E) -heptenyl))
4- (4-propylcyclohexyl) phenyl- (4- (1
-(E) -octenyl)) 4- (4-propylcyclohexenyl) phenyl- (4- (1- (E) -pentenyl)) 4- (4
-Cyano-3-fluoro) phenyl- (4- (1- (E) -pentenyl)) benzoate, 4- (4-cyano-3-fluoro) phenyl- (4- (1- (E) -heptenyl)) Benzoate, 4- (3,4-difluoro) phenyl- (4- (1-
(E) -pentenyl)) benzoate, 4- (3,4-difluoro) phenyl- (4- (1- (E) -heptenyl)) benzoate, 4- (3,4,5-trifluoro) phenyl- (4
-(1- (E) -pentenyl)) benzoate, 4- (3,
4,5-trifluoro) phenyl- (4- (1- (E) -heptenyl)) benzoate and the like.

In the compound represented by the formula (3), in particular, 1,4-phenylene, 1,4-cyclohexylene, wherein ring D in the formula (3) may be substituted by a fluorine atom,
Compounds which are 1,4-cyclohexelene, 4,1-cyclohexelene, 2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene or 6,3-cyclohexelene are preferably exemplified. These expressions
The compound represented by (3) is described in, for example, JP-A-7-3306.
It can be produced according to the method described in JP-A-36-36 and JP-A-8-99917.

In the compound represented by the formula (4), B ¹ to
B ¹² independently represents a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and at least one is an alkyl group or an alkoxy group. R ⁷ and R ⁸ are each independently a hydrogen atom, a fluorine atom, a cyano group, 4-R ⁹ - (cycloalkyl) group, 4-R ⁹
— (Cycloalkenyl group) or R ¹⁰ — (O) a group (provided that R ⁹ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom) R ¹⁰ represents an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom, and A is 0
Or 1 is shown.

In the formula (4), R ⁷ and R ⁸ are, for example, a hydrogen atom; a fluorine atom; a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group Alkyl group such as a group, decyl group, undecyl group, dodecyl group and the like, and a fluoroalkyl group substituted with a fluorine atom (for example, trifluoromethyl group); methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group A hexyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, an alkoxy group such as a dodecyloxy group, and a fluoroalkoxy group in which these are substituted with a fluorine atom (for example, 1 to 3 fluorine atoms. A substituted methoxy group, an ethoxy group substituted with 1 to 5 fluorine atoms); a methoxymethyl group, Ethoxymethyl group, propoxymethyl group, butoxymethyl group, pentyloxymethyl group, hexyloxymethyl group, heptyloxymethyl group, octyloxymethyl group, nonyloxymethyl group, decyloxymethyl group, methoxyethyl group, ethoxyethyl group, Propoxyethyl group, butoxyethyl group,
Pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl, nonyloxyethyl, decyloxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl ,
Hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl , Octyloxybutyl group, methoxypentyl group, ethoxypentyl group, propoxypentyl group, butoxypentyl group, pentyloxypentyl group, hexyloxypentyl group, alkoxyalkyl groups such as heptyloxypentyl group and these were substituted with fluorine atoms Fluoroalkoxyalkyl group; 2-methylpropyl group, 2-
Branched alkyl groups such as methylbutyl group, 3-methylbutyl group, and 3-methylpentyl group; and fluorobranched alkyl groups in which these are substituted with fluorine atoms; 2-methylpropyloxy group, 2-methylbutyloxy group, Branched alkyloxy groups such as methylbutyloxy group and 3-methylpentyloxy group and fluorobranched alkyloxy groups substituted with a fluorine atom; 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-propylcyclohexyl Group, 4-butylcyclohexyl group, 4-pentylcyclohexyl group, 4-hexylcyclohexyl group,
4-alkyl-cycloalkyl groups such as 4-heptylcyclohexyl group, 4-octylcyclohexyl group, 4-nonylcyclohexyl group, 4-decylcyclohexyl group and the like, and 4-fluoroalkyl-cycloalkyl groups in which these are substituted by fluorine atoms; 4-alkyl-cycloalkenyl groups such as 4-propylcyclohexenyl group and 4-pentylcyclohexenyl group; 4-fluoroalkyl-cycloalkenyl groups in which these are substituted by fluorine atoms; and cyano groups.

The phenylene acetylene compound represented by the formula (4) is preferably a compound represented by the following structural formula. However, R ⁷ and R ⁸ in the structural formula are preferably independently selected from the above specific examples and combined, but are not limited thereto.

[0117]

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[0118]

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[0119]

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[0120]

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[0121]

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[0122]

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[0123]

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[0124]

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[0125]

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[0126]

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In the liquid crystal composition of the present invention, the above formula (1)
And one or two selected from the group consisting of a compound represented by the above formula (2), a compound represented by the above formula (3) and a compound represented by the above formula (4) With respect to the composition ratio (the ratio of each component when the total composition is taken as 100 mol%), the compound represented by the formula (1) is 5 to 5 kinds or more.
90 mol%, the total ratio of the compound represented by the formula (2), the compound represented by the formula (3) and the compound represented by the formula (4) is 10
~ 95 mol% is preferred.

The liquid crystal composition of the present invention may further contain one or more chiral compounds as a twisting agent. The chiral compound is not particularly limited,
Preferably, the following compounds can be exemplified.
(However, * in the examples represents an asymmetric carbon).

[0129]

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In the liquid crystal composition of the present invention, the blending ratio of the chiral compound can be appropriately selected depending on the blending composition and the like, and is not particularly limited.

The liquid crystal display device of the present invention is not particularly limited as long as the above liquid crystal composition is sandwiched between a pair of electrode substrates, and may have the same configuration as a known liquid crystal display device. The type and form of the electrode are not particularly limited, and a known electrode or the like can be used. Further, the production of the liquid crystal display element of the present invention can be performed in the same manner as the production of a normal liquid crystal display element, and other elements can be appropriately added.

[0132]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. The physical properties of the liquid crystal compositions in the examples were measured by the following methods. 1) The refractive index anisotropy (Δn) is obtained by injecting and orienting a sample into a wedge-shaped cell having an apex angle of about 1.6 °, and entering He-
It was determined by measuring the refraction angle of the Ne laser. 2) the maximum temperature (TNI) of the N (nematic) phase of the liquid crystal composition,
The minimum temperature (mp) was measured using a polarizing microscope. The structural formula of each compound used in the examples is shown below.

[0133]

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Example 1 33.4% by mass of a compound (1-1) corresponding to the formula (1) was added to the compound of the formula (1-1).
23.1% by mass of a compound (2-1) corresponding to (2),
Liquid crystal composition 1 was prepared by mixing 34.6% by mass of compound (4-1) and 8.9% by mass of compound (4-2) corresponding to (4). When the liquid crystallinity of the liquid crystal phase of the liquid crystal composition 1 was measured, it showed a nematic phase in an extremely wide range of 36 to 172 ° C. Further, when the Δn of the liquid crystal composition 1 was measured by a wedge method, it showed an extremely high value of 0.39 (40 ° C.). I understood.

Example 2 26.7% by mass of the compound (1-1) corresponding to the formula (1) was added to the compound of the formula
18.5% by mass of a compound (2-1) corresponding to (2),
10.0% by mass of compound (3-1) and 10.0% by mass of compound (3-2) corresponding to (3) and a compound corresponding to formula (4)
The liquid crystal composition 2 was prepared by mixing 27.7% by mass of (4-1) and 7.1% by mass of the compound (4-2). Liquid crystal composition 2
When the liquid crystallinity of the liquid crystal phase was measured, the nematic phase was exhibited in an extremely wide range of 18 to 143 ° C. Further, when the Δn of the liquid crystal composition 2 was measured, it showed a very high value of 0.34, and the liquid crystal composition 2 was a composition having a high Δn and showing a liquid crystal phase in an extremely wide temperature range including room temperature. all right.

Comparative Example 1 A liquid crystal composition 2R was prepared from the liquid crystal composition 2 prepared in Example 2 without using the compound (1-1) corresponding to the formula (1), and the physical properties were measured in the same manner. As a result, the temperature range of the nematic phase was 41 to 138 ° C., which was narrower than that of the liquid crystal composition 2. In particular, the liquid crystal phase was not shown at room temperature because the minimum temperature increased. Δn was 0.29 (42 ° C.), which was lower than that of the liquid crystal composition 2. Therefore, it can be seen that the combination of the liquid crystal compositions of the present invention is useful in widening the temperature range of the liquid crystal phase and obtaining a large Δn.

Example 3 19.2% by mass of the compound (1-1) corresponding to the formula (1) was
15.9% by mass of compound (2-1) corresponding to (2), compound
(2-2) 10.5 mass%, compound (2-3) 7.5 mass%, and compound (4-1) 24.3 mass% corresponding to formula (4).
And 6.2% by mass of the compound (4-2) were mixed to prepare a liquid crystal composition 3. When the liquid crystallinity of the liquid crystal phase of the liquid crystal composition 3 was measured, the liquid crystal composition showed a nematic phase in an extremely wide range including 15 to 189 ° C. and room temperature. Further, when the Δn of the liquid crystal composition 3 was measured by a wedge method, the liquid crystal composition 3 showed an extremely high value of 0.41 (20 ° C.). It was found to be the composition shown.

[0138]

The liquid crystal composition of the present invention comprises a compound represented by the formula (1) and a compound represented by the formula (2) and / or the formula (3) and / or the formula (4).
Since it contains a compound represented by the formula (1), the refractive index anisotropy is large, stable, and easily mixed with other liquid crystals. It is particularly useful as a material constituting a typical liquid crystal element.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09K 19/30 C09K 19/30 19/34 19/34 G02F 1/13 500 G02F 1/13 500 (72) Inventor Kazunori Iwakura 2-1-1 Tsukahara, Takatsuki-shi, Osaka, Japan Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Masayoshi Minami 2-1-1, Tsukahara, Takatsuki-shi, Osaka Sumitomo Kagaku Kogyo Co., Ltd. Reference) 4H027 BA01 BB04 BB11 BD01 BD02 BD07 BD08 BD24 BE04 BE05 CF01 CF03 CF04 CM04 CN04 CU01 CU04

Claims (5)

[Claims] 1. A benzylidinyl tolane compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3) and a compound represented by the formula (4) A liquid crystal composition comprising one or more selected from the group consisting of: Embedded image (In the formula (1), A ^{1 to} A ¹² each independently represent a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms which may be substituted by a fluorine atom. And R ¹ and R ² are each independently a hydrogen atom, a fluorine atom, a cyano group, —SF ₅ ,
—NCS, 4-R ³ — (cycloalkyl) group, 4-R ³ —
(Cycloalkenyl group) or a group represented by R ⁴ — (O) q ¹ (provided that R ³ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom) And R ⁴ represents an alkyl group having 1 to 12 carbon atoms which may be substituted by a linear or branched fluorine atom.
¹ represents 0 or 1). ) (In the formula (2), A ^{13 to} A ²⁴ each independently represent a hydrogen atom,
It represents a fluorine atom or an alkyl group having 1 to 10 carbon atoms. m
Is 0 or 1. R ¹¹ is a hydrogen atom or a carbon atom having 1 to 1 carbon atoms which may be substituted by a linear or branched fluorine atom.
2 represents an alkyl group. R ²¹ is R ¹¹ , a fluorine atom, a cyano group, a 4-R ^31- (cycloalkyl) group, a 4-R ^31-
(Cycloalkenyl group) or an R ^41- (O) q ² group (provided that R ³¹ represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may be substituted with a linear or branched fluorine atom) shown, R ⁴¹ is a straight-chain or branched alkyl group having 1 to 12 carbon atoms which may be substituted with a fluorine atom .q ²
Represents 0 or 1). ) (In the formula (3), ring A, ring B, ring C and ring D are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexelene, 4,1-cyclohexelene 2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene, 6,3-cyclohexelene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, Represents 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl (provided that ring A, ring B, ring C and ring D
The above hydrogen atom may be replaced by a fluorine atom).
R ⁵ and R ⁶ are each independently a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group,
Trifluoromethoxy group, cyano group, alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, 1 carbon atom
An alkoxy group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, an alkynyloxy group having 3 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms or an alkoxyalkenyl group having 3 to 16 carbon atoms. The methylene group contained in these groups may contain an oxygen atom, a sulfur atom or a silicon atom, and may be either linear or branched. Z ¹ , Z ² and Z ³ are each independently -COO-,
—OCO—, —OCH ₂ —, —CH ₂ O—, having 1 to 5 carbon atoms
An alkylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. b, c and d are each independently 0 or 1, and b + c +
d ≧ 1. ) (In the formula (4), B ^{1 to} B ¹² each independently represent a hydrogen atom, a fluorine atom, or an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and at least one is an alkyl group or an alkoxy group. .R ⁷ and R ⁸ are each independently a hydrogen atom, a fluorine atom, a cyano group, 4-R ⁹ - (cycloalkyl) group, 4-R ⁹ - (cycloalkenyl group) or R ¹⁰ -
(O) represents a group (provided that R ⁹ is a hydrogen atom or a carbon atom having 1 to 5 carbon atoms which may be substituted with a linear or branched fluorine atom)
And 12 represents an alkyl group having 12 carbon atoms, and R ¹⁰ represents an alkyl group having 1 to 12 carbon atoms which may be substituted with a linear or branched fluorine atom. a represents 0 or 1). ) 2. The compound represented by the formula (3), wherein ring D may be substituted with a fluorine atom, 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexelene, The liquid crystal according to claim 1, wherein the liquid crystal is any one of 4,1-cyclohexelene, 2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene, and 6,3-cyclohexelene. Composition. 3. The compound represented by the formula (3) is a compound represented by the formula (5):
3. The liquid crystal composition according to claim 1, comprising at least one compound represented by (11). Embedded image Embedded image (In the formulas (5) to (8), R ⁵ , R ⁶ , ring A, ring B, Z ¹
And b have the same meaning as in formula (3). j is 0,
1 or 2, h is 0 or 1, and i is 0, 1 or 2. In the formula (9), E ^{1 to} E ¹² each independently represent a hydrogen atom, a fluorine atom or a chlorine atom. Also, the formula
In (10), X ^{9 to} X ¹² are each independently CH or CF
Is shown. J ⁴ is a hydrogen atom, a fluorine atom, a cyano group, or an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms,
It represents 12 alkoxy groups, an alkenyloxy group having 2 to 12 carbon atoms, an alkynyloxy group having 3 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms. J ⁵ represents a hydrogen atom, a fluorine atom, a cyano group, or J ⁶ - shows the (O) m ²
(However, m ² is 0 or 1, and J ⁶ is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 16 carbon atoms or an alkynyl having 3 to 16 carbon atoms, which may be substituted with a fluorine atom. E ¹ and E ² each independently represent a group represented by the following structural formula (provided that X ^{13 to} X ¹⁶ each independently represent CH or CF). W ¹ _{is, -C 2 H 4 -, -} CH 2 O- or -OCH ₂ - shows a. f ¹ and f ² each independently represent 0 or 1, but do not become 1 at the same time. When f ¹ is 1, at least one of E ^{1 and} E ² is a group represented by the following structural formula. Embedded image G ⁵ ~G ⁸ independently represents a hydrogen atom or a fluorine atom. In the formula (11), R ⁷ represents an alkyl group having 1 to 10 carbon atoms, and the hydrogen atom on the benzene ring in the formula (11) may be substituted by a fluorine atom. n, p and q ³ are 1 or 2, respectively. X ¹⁷ represents a trans form of —CH ＝ CH— or an ethynyl group (provided that when n is 1, X ¹⁷ is —C
H ₂ —CH ₂ —). ) 4. A composition ratio of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3) and a compound represented by the formula (4): 100 whole composition
(A ratio of each component as mol%) is 5 to 90 mol% of the compound represented by the formula (1), a compound represented by the formula (2),
The liquid crystal composition according to any one of claims 1 to 3, wherein a total ratio of the compound represented by the formula (3) and the compound represented by the formula (4) is 10 to 95 mol%. . 5. A liquid crystal device comprising the liquid crystal composition according to claim 1 sandwiched between a pair of electrode substrates.