JP2000219882A - Liquid crystal composition including phenylacetylene bearing alkyl groups in its skeleton and liquid crystal element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal composition that has high refractive index anisotropy and retain the nematic phase over a wide range of temperature by admixing a specific compound to a phenylacetylene compound. SOLUTION: The objective liquid crystal composition comprises (A) a phenylacetylene of formula I (A1-A12 are each H, F, a 1-10C alkyl; R1 and R2 are each H, F, cyano or the like), a compound of (B) formula II (ring A-D is 1,4-phenylene, 1,4-cyclohexylene, 3,6-cyclohexylene, 2,5-pyridinediyl or the like; R5 and R6 are each H, F, fluoromethyl or the like; Z1-Z3 is COO, OCO, OCH2; b-d are each 0 or 1 where b+c+d>=1) and/or (C) a compound of formula III (J1 is H, F, cyano or the like; J2 is a 1-12C alkyl or the like; A is a group of formula IV; k, m, n are each 0 or 1; X1-X8 are each CH, CF; G1-G4 are each H, F; Z4 is C≡C or the like). In a preferred embodiment, the amount of the component A is 5-50 mol.%, the component B is 0-95 mol.% and the component C is 0-95 mol.%, respectively.

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 an optical shutter, STN (super twisted nematic) type liquid crystal device, PDLC (polymer-dispersion type liquid crystal) type liquid crystal device using the same. 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 widespread 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 non-linear element for each pixel. However, the active matrix method has problems in terms of large area, low cost, and high density due to complicated manufacturing processes and low yield, and the simple matrix method is more expensive and more productive. Influential. As a simple matrix type liquid crystal element currently in practical use, a TN (twisted nematic) type or STN type liquid crystal element is mainly used. TN
The type is widely applied as a display element such as a watch or a calculator.However, in this method, the rise of the electro-optical characteristics is gradual, and the contrast is remarkably reduced as the duty ratio increases. Have difficulty. The STN 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, or display moving images. In order to make the STN-type liquid crystal element respond fast, one of the effective methods is to reduce the cell thickness. The STN type uses a birefringence effect as a 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. . Retardation R
Is represented by R = (Δn × d). Therefore, in order to reduce the cell thickness d, it is necessary to increase the refractive index anisotropy Δn. 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. It is known that the response parameter η / Δn ² 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. is not.

[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 liquid crystal having a small response parameter (η / Δn ² ) and excellent response. An object of the present invention is to provide a composition and a liquid crystal device using the liquid crystal composition.

[0004]

That is, according to the present invention,
It is characterized by containing at least one kind of the phenylacetylene compound represented by the formula (1) and at least one kind of the compound represented by the formula (2) and / or the compound represented by the formula (3). A liquid crystal composition is provided.

[0005]

Embedded image (Wherein, A ^{1 to} A ¹² each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group. R ¹ and R ² are each independently hydrogen atom, a fluorine atom, a cyano group, 4-R ³ - (cycloalkyl) group, 4-R ³ - (cycloalkenyl group) or R
⁴ - (O) indicating the q group (wherein, R ³ is a hydrogen atom may be substituted with a straight-chain or branched fluorine atoms, C 1 -C
An alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms, wherein R ⁴ may be substituted with a linear or branched fluorine atom, An alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms. q represents 0 or 1). )

[0006]

Embedded image (In the formula (2), 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, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-
Represents 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 each independently represent a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a cyano group,
Alkyl group of 12 to 12, alkenyl group of 2 to 12 carbon atoms,
An alkoxy group having 1 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 Show. The methylene group contained in these groups may be substituted with an oxygen atom, a sulfur atom or a silicon atom, and may be either linear or branched (provided that R ⁵ and / or R ⁶ are -CX =
CX-R (R represents an alkyl group, an alkoxy group or an alkynyl group having 1 to 10 carbon atoms which may be substituted by a fluorine atom, and X represents a hydrogen atom or a fluorine atom) is excluded. ). Z ¹ , Z ² and Z ³ are each independently -C
OO -, - OCO -, - OCH 2 -, - CH 2 O-, an alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, show an alkynylene group or a single bond having 2 to 5 carbon atoms, b, c and d are each independently 0 or 1,
And b + c + d ≧ 1 is satisfied. )

[0007]

Embedded image (In the formula (3), J ¹ represents a hydrogen atom, a fluorine atom, a cyano group or J ³ (O) m ¹ (provided that J ³ may be substituted with a fluorine atom, Alkyl group, having 2 to 2 carbon atoms
Indicates 12 alkenyl group or alkynyl group having 2 to 12 carbon atoms, m ¹ is 0 or 1). J ² represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms. A is

Embedded image Represents k, m and n represent 0 or 1. m and n cannot be 0 or 1 at the same time. X ^{1 to} X ⁸ are
Each independently represents CH or CF. G ^{1 to} G ⁴ each independently represent a hydrogen atom or a fluorine atom. Z ⁴ is −C≡
It represents C- or -C≡CC≡C- (however, when n = 0, Z ⁴ is -C≡C-). According to the present invention, there is provided the liquid crystal composition, further comprising at least one kind of a compound represented by the formula (4) and / or a compound represented by the formula (5).

[0008]

Embedded image (In the formula (4), 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, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, which may be substituted with a fluorine atom,
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, - (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, or 3 to 16 carbon atoms, which may be substituted with a fluorine atom.)
Represents an alkynyl group). E ¹ and E ² are each independently

Embedded image (However, X ^{13 to} X ¹⁶ each independently represent CH or CF). W ¹ is —C ₂ H ₄ —, —CH ₂ O— or —
Shows OCH ₂ —. 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

Embedded image It is. G ⁵ ~G ⁸ independently represents a hydrogen atom or a fluorine atom. )

[0009]

Embedded image (In the formula (5), R ⁷ represents an alkyl group having 1 to 10 carbon atoms,
The hydrogen atom on the benzene ring in the formula (5) may be substituted with a fluorine atom. n, p and q are each 1 or 2, and X ¹⁷ represents a trans form of —CH ＝ CH— or an ethynyl group (however, when n is 1, X ¹⁷ is —CH ₂ —CH ₂
-). According to the present invention, there is further 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]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail. The liquid crystal composition of the present invention comprises at least one kind of the compound represented by the formula (1) and at least one of the compound represented by the formula (2) and / or the compound represented by the formula (3). Including seeds. In the compound represented by the formula (1), A ^{1 to} A
¹² independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group. Preferably, A ⁴ of A ^{1 to} A ¹² ,
It is desirable that at least one selected from the group consisting of A ⁵ , A ⁹ and A ¹⁰ is an alkyl group. Also, A ³ ~
When A ¹² is all hydrogen atoms, A ¹ and A ² are preferably compounds which do not simultaneously form a methyl group, and when A ^{1 to} A ⁶ and A ^{8 to} A ¹¹ are all hydrogen atoms, A ^{7 to} A ¹² are simultaneously Compounds that do not become methyl groups are preferred. R ¹ and R ² each independently represent a fluorine atom, a cyano group, a 4-R ^3- (cycloalkyl) group, a 4-R ^3- (cycloalkenyl group) or R ⁴
-(O) represents a q group. However, R ³ may be substituted by a hydrogen atom, a linear or branched fluorine atom, and has 1 carbon atom.
An alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms, wherein R ⁴ may be substituted with a linear or branched fluorine atom, An alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms. q represents 0 or 1.

In the formula (1), specific examples of R ¹ and R ² include, 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 Groups, nonyl groups, decyl groups, undecyl groups, alkyl groups such as dodecyl groups and the like, and fluorine-substituted fluoroalkyl groups (for example, trifluoromethyl groups); ethenyl groups, propenyl groups, butenyl groups, pentenyl groups, hexenyl groups, Heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group,
Alkenyl groups such as dodecenyl group and the like, and fluorine-substituted fluoroalkenyl groups thereof; A fluorine-substituted fluoroalkynyl group; a methoxy group, an ethoxy group, a propoxy group,
Alkoxy groups such as butoxy group, pentyloxy group, hexyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, and fluorine-substituted fluoroalkoxy groups
(For example, a methoxy group substituted with 1 to 3 fluorine atoms, an ethoxy group substituted with 1 to 5 fluorine atoms);
Alkenyloxy groups such as a vinyloxy group, a propenyloxy group, a butenyloxy group, a pentenyloxy group, a hexenyloxy group, a heptenyloxy group, an octenyloxy group, a nonenyloxy group, and a decenyloxy group, and a fluorine-substituted fluoroalkenyloxy group thereof; Alkynyloxy groups such as a group, butynyloxy group, pentynyloxy group, hexynyloxy group, heptynyloxy group, octynyloxy group, noninyloxy group, decynyloxy group, undecynyloxy group, dodecynyloxy group and the like, and a fluorine-substituted fluoroalkynyloxy group; methoxy Methyl group, ethoxymethyl group, propoxymethyl group, butoxymethyl group, pentyloxymethyl group, hexyloxymethyl group, heptyloxymethyl group, Octyloxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl , Nonyloxyethyl group, decyloxyethyl group,
Methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, methoxybutyl, ethoxybutyl, propoxy Butyl group, butoxybutyl group, pentyloxybutyl group, hexyloxybutyl group, heptyloxybutyl group, octyloxybutyl group, methoxypentyl group,
An alkoxyalkyl group such as an ethoxypentyl group, a propoxypentyl group, a butoxypentyl group, a pentyloxypentyl group, a hexyloxypentyl group and a heptyloxypentyl group, and a fluorine-substituted fluoroalkoxyalkyl group thereof; 2-methylpropyl group, 2 A branched alkyl group such as -methylbutyl group, 3-methylbutyl group, or 3-methylpentyl group and a fluorine-substituted fluorobranched alkyl group thereof; a 2-methylpropyloxy group;
Branched alkyloxy groups such as a 2-methylbutyloxy group, a 3-methylbutyloxy group, and a 3-methylpentyloxy group, and fluorine-substituted fluorobranched alkyloxy groups; 4-methylcyclohexyl group and 4-ethyl Cyclohexyl group, 4-propylcyclohexyl group, 4
-Butylcyclohexyl group, 4-pentylcyclohexyl group, 4-hexylcyclohexyl group, 4-heptylcyclohexyl group, 4-octylcyclohexyl group, 4-
4-alkyl-cycloalkyl groups such as nonylcyclohexyl group and 4-decylcyclohexyl group and their fluorine-substituted 4-fluoroalkyl-cycloalkyl groups; 4-alkylcycloalkyl groups such as 4-propylcyclohexenyl group and 4-pentylcyclohexenyl group; -Alkyl-cycloalkenyl groups and their fluorine-substituted 4-fluoroalkyl-cycloalkenyl groups; cyano groups and the like.

Specific examples of the phenylene acetylene compound represented by the formula (1) are preferably compounds represented by the following structural formulas. However, R ¹ and R in the structural formula
Preferably, ² is independently selected from the above specific examples and combined, but is not limited thereto.

[0013]

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[0014]

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[0015]

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[0016]

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The phenylacetylene compound represented by the formula (1) can be synthesized by 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, it is produced by reacting a compound represented by the formula (11) with a compound represented by the formula (12) in the presence of a base such as copper iodide, a palladium catalyst and triethylamine. Can be.

[0018]

Embedded image (In the formulas (11) and (12), 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 (11) is, for example, a compound represented by the formula
After coupling the compound represented by (13) with the compound represented by the formula (14), butyl-2-ol is reacted in the presence of a base such as copper iodide, a palladium catalyst and triethylamine, Further, it can be produced by reacting in the presence of a base such as potassium hydroxide.

[0020]

Embedded image (In the formulas (13) and (14), 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 (15)
Reacting with methanesulfonic acid to form a compound represented by formula (15)
The terminal OH group of the compound is -OSO_TwoCF_ThreeAnd this and equation (1)
6) 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 formulas (15) and (16)
A¹~ A¹², R¹And R ^TwoIs the same as in equation (1)
Show meaning.

[0022]

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In the compound represented by the above formula (2) 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, ring A,
A hydrogen atom on ring B, ring C and ring D may be substituted by a fluorine atom.

In the equation (2), R^FiveAnd R⁶Is a hydrogen atom,
Fluorine atom, fluoromethyl group, difluoromethyl group,
Trifluoromethyl group, fluoromethoxy group, difluoro
Romethoxy group, trifluoromethoxy group, cyano group, charcoal
Alkyl group having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms
Group, an alkoxy group having 1 to 12 carbon atoms, 2 to 12 carbon atoms
An alkenyloxy group having 3 to 12 carbon atoms
A xy group, an alkoxyalkyl group having 2 to 16 carbon atoms,
And an alkoxyalkenyl group having 3 to 16 carbon atoms.
The methylene group contained in these groups is an oxygen atom, a sulfur
Atom, may be substituted by a silicon atom, and may be linear or branched.
Either is acceptable (however, R^FiveAnd / or R ⁶Is -CX =
CX-R or -C≡CR (R is substituted with a fluorine atom
Optionally having 1 to 10 carbon atoms, an alkyl group or alkoxy
X represents a hydrogen atom or a fluorine atom;
Atom). ). R^FiveAnd R⁶As a specific example of
A hydrogen atom; a fluorine atom; a fluoromethyl group;
Fluoromethyl group; trifluoromethyl group;
Xy group; difluoromethoxy group; trifluoromethoxy
Group; cyano group; methyl group, ethyl group, propyl group, butyral
Group, pentyl group, hexyl group, heptyl group, octyl
Group, nonyl group, decyl group, undecyl group, dodecyl group, etc.
Alkyl group; ethenyl group, propenyl group, butenyl
Group, pentenyl group, hexenyl group, heptenyl group, octyl group
Thenyl, nonenyl, decenyl, undecenyl,
Alkenyl groups such as dodecenyl groups; methoxy groups, ethoxy
Group, propoxy group, butoxy group, pentyloxy group,
Xyloxy group, heptyloxy group, octyloxy
Group, nonyloxy group, decyloxy group, undecyloxy
Alkoxy groups such as thio group and dodecyloxy group; vinyloxy
Group, propenyloxy group, butenyloxy group, pente
Nyloxy group, hexenyloxy group, heptenyloxy
Group, octenyloxy group, nonenyloxy group, decenyl
An alkenyloxy group such as an oxy group; propynyloxy
Group, butynyloxy group, pentynyloxy group, hexynyl
Loxy, heptynyloxy, octynyloxy
Group, noninyloxy group, decynyloxy group, undecinyl
Alkynyloxy such as ruoxy group and dodecynyloxy group
Group: methoxymethyl group, ethoxymethyl group, propoxy group
Methyl group, butoxymethyl group, pentyloxymethyl
Group, hexyloxymethyl group, heptyloxymethyl
Group, octyloxymethyl group, nonyloxymethyl group,
Decyloxymethyl, methoxyethyl, ethoxy
Tyl group, propoxyethyl group, butoxyethyl group, pen
Tyloxyethyl group, hexyloxyethyl group, hepti
Ruoxyethyl group, octyloxyethyl group, nonylo
Xyethyl group, decyloxyethyl group, methoxypropyl
Group, ethoxypropyl group, propoxypropyl group,
Toxypropyl group, pentyloxypropyl group, hex
Ruoxypropyl group, heptyloxypropyl group, octane
Tyloxypropyl group, nonyloxypropyl group,
Luoxypropyl group, methoxybutyl group, ethoxybuty
, Propoxybutyl, butoxybutyl, pliers
Ruoxybutyl group, hexyloxybutyl group, heptyl
Oxybutyl group, octyloxybutyl group, nonyloxy
Cybutyl group, decyloxybutyl group, methoxypentyl
Group, ethoxypentyl group, propoxypentyl group, buto
Xypentyl group, pentyloxypentyl group, hexyl
Oxypentyl group, heptyloxypentyl group, octyl
Ruoxypentyl group, nonyloxypentyl group, decyl
And alkoxyalkyl groups such as an oxypentyl group.
It is.

In the formula (2), Z ¹ , Z ² and Z ³ are each independently —COO—, —OCO—, —OCH ₂ —,
—CH ₂ O—, an alkylene group having 1 to 5 carbon atoms, 2 carbon atoms
Or an alkenylene group of 2 to 5, an alkynylene group of 2 to 5 carbon atoms or a single bond. In equation (2), b, c and d
Is independently 0 or 1 and b + c + d ≧
Meet 1.

The compound represented by the formula (2) includes
Preferred are the compounds represented by (6) to (10). However, in the formulas (6) to (10), R ⁵ , R ⁶ ,
Ring A, ring B, Z ¹ and b have the same meaning as in formula (2). j is 0, 1 or 2, h is 0 or 1, and i is 0, 1 or 2. In equation (10), B ¹
To B ¹² each independently represent a hydrogen atom, a fluorine atom or a chlorine atom.

[0027]

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Specific examples of the compound represented by the formula (2) include compounds having the following structural formulas. These examples include those of the compounds represented by the above formulas (6) to (10). However, in the structural formula 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 may be fluorine-substituted, 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexene, 4,1-cyclohexene, 2,5-cyclohexene, 5,2- Cyclohexelene, 3,6-cyclohexelene, 6,3-cyclohexelene, 2,5-
Pyrimidinediyl, 5,2-pyrimidinediyl, 2,5
-Pyridinediyl, 5,2-pyridinediyl, 2,5-
Shows dioxanediyl or 5,2-dioxanediyl. More preferably, ring G is 1,4-cyclohexylene, 1,4-cyclohexelene, 4,1-cyclohexelene, 2,5-cyclohexelene, 5,2-cyclohexelene, 3,6-cyclohexelene or Shows 6,3-cyclohexelene.

[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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[0042]

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In the compound represented by the formula (2), in particular, 1,4-phenylene, 1,4-cyclohexylene, in which the ring D in the formula (2) 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.

In the above formula (3), J ¹ represents a hydrogen atom, a fluorine atom, a cyano group or J ³ (O) m ¹ . However, J ³
May be substituted with fluorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or 2 to 2 carbon atoms.
12 represents an alkynyl group, and m ¹ represents 0 or 1. J ¹
Specific examples of the above J ³ (O) m ¹ include a methyl group,
Ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group,
Undecyl, dodecyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, propynyl, butynyl, pentynyl, hexynyl , Heptynyl group, octynyl group, noninyl group, decynyl group, dodecynyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group , Dodecyloxy, vinyloxy, propenyloxy, butenyloxy, pentenyloxy, hexenyloxy, heptenyloxy, octenyloxy, nonenyloxy, decenyloxy, propionyloxy, butini Oxy group, pentynyl group, hexynyloxy group, Hepuchiniruokishi group, Okuchiniruokishi group, Noniniruokishi group, Dodeshiniruokishi group, a trifluoromethyl group, a trifluoromethoxy group,
Examples include a difluoromethyl group, a trifluoroethyl group, a tetrafluoroethyl group, and a pentafluoroethyl group.

In the above formula (3), J ² is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or an alkoxyalkyl group having 2 to 16 carbon atoms. Specific examples of J ² include 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. An ethenyl group,
Alkenyl groups such as propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl; methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, Pentyloxymethyl group, hexyloxymethyl group, heptyloxymethyl group, octyloxymethyl group, nonyloxymethyl group,
Decyloxymethyl group, methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, pentyloxyethyl group, hexyloxyethyl group, heptyloxyethyl group, octyloxyethyl group, nonyloxyethyl group, decyloxyethyl group , Methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, decyloxypropyl, methoxybutyl , Ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl, octyloxybutyl, nonyloxybutyl, Oxybutyl group, a methoxy pentyl group, an ethoxy pentyl group, propoxy pentyl group, Butokishipenchiru group, pentyloxy pentyl group, hexyloxy pentyl group, heptyloxy pentyl group, such as alkoxyalkyl groups such as octyloxy pentyl group.

Examples of the compound represented by the formula (3) include 1- (1- (E) -pentenyl) -4- (2- (4'-propylphenyl) ethynyl) benzene and 1- (2-difluoro -1- (E) -butenyl) -4- (2- (4′-propylphenyl) ethynyl) benzene, 1- (1- (E) -hexenyl) -4- (2- (4′-methylphenyl) Ethynyl) benzene, 1- (1- (E) -hexenyl) -4- (2- (4′-
(Ethylphenyl) ethynyl) benzene, 1- (1- (E)-
Hexenyl) -4- (2- (4'-butylphenyl) ethynyl) benzene, 1- (1- (E) -hexenyl) -4- (2-
(4′-pentylphenyl) ethynyl) benzene, 1- (1
-(E) -hexenyl) -4- (2- (4'-hexylphenyl) ethynyl) benzene, 1- (1- (E) -hexenyl)-
4- (2- (4′-heptylphenyl) ethynyl) benzene, 1- (1- (E) -hexenyl) -4- (2- (4′-methoxyphenyl) ethynyl) benzene, 1- (1- ( E)-
(Hexenyl) -4- (2- (4'-ethoxyphenyl) ethynyl) benzene, 1- (1- (E) -hexenyl) -3-fluoro-4- (2- (4'-pentylphenyl) ethynyl)
Benzene, 1- (1- (E) -hexenyl) -2-fluoro-4- (2- (4′-pentylphenyl) ethynyl) benzene, 1- (1- (E) -heptenyl) -4- (2 -(4'-trifluoromethoxyphenyl) ethynyl) benzene, 1-
(1- (E) -Hexenyl) -4- (2- (4′-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1-
(E) -pentenyl) -4- (2- (4′-trifluoromethoxyphenyl) ethynyl) benzene, 1- (1- (E) -heptenyl) -3-fluoro-4- (2- (4′- (Trifluoromethoxyphenyl) ethynyl) benzene, 1- (1-
(E) -Hexenyl) -3-fluoro-4- (2- (4′-trifluoromethoxyphenyl) ethynyl) benzene, 1-
(1- (E) -pentenyl) -3-fluoro-4- (2-
(4'-trifluoromethoxyphenyl) ethynyl) benzene

1- (1,2-difluoro-1- (E) -pentenyl) -4- (2- (4'-propylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E ) -Heptenyl) -4- (2- (4′-propylphenyl) ethynyl) benzene, 1- (1,2-difluoro-1- (E) -butenyl) -4- (2- (4′-propylphenyl) ) Ethinyl)
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'-hexylphenyl) 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) ethynyl) 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

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′- (Trifluoromethoxyphenyl) 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 and the like.

The compounds represented by the formula (3) are described in, for example, JP-A-7-330636 and JP-A-8-99917.
It can be manufactured according to the method described in Japanese Patent Publication No.

In the liquid crystal composition of the present invention, the above formula (1)
The composition ratio of each of the compound represented by the formula (2) and the compound represented by the formula (3) (ratio of each component when the whole composition is 100%) is formula
It is preferable that the compound represented by the formula (1) is 5 to 50 mol%, the compound represented by the formula (2) is 0 to 95 mol%, and the compound represented by the formula (3) is 0 to 95 mol%. However, equations (2) and (3)
When none of the compounds represented by
It is preferred that the compound represented by formula (2) is at least 10 mol% and the compound represented by formula (3) is at least 5 mol%.

The liquid crystal composition of the present invention comprises a phenylacetylene compound represented by the above formula (1), a compound represented by the formula (2) and / or a compound represented by the formula (3). Further, a compound represented by the above formula (4) and / or a compound represented by the formula (5) may be contained.

In the formula (4), J ⁴ represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, An alkoxy group having 1 to 12 carbon atoms, 2 carbon atoms
An alkenyloxy group having 1 to 12 carbon atoms, an alkynyloxy group having 3 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms. Specific examples of J ^4, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, an alkyl group or those such as dodecyl A fluorine-substituted alkyl group; an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group,
An alkenyl group such as an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group or a fluorine-substituted alkenyl group thereof; a propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group,
Alkynyl groups such as noninyl group, decynyl group, dodecynyl group and the like and fluorine-substituted alkynyl groups; methoxy group,
An ethoxy group, a propoxy group, a butoxy group, a 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 or a fluorine-substituted alkoxy group thereof; a vinyloxy group, An alkenyloxy group such as a propenyloxy group, a butenyloxy group, a pentenyloxy group, a hexenyloxy group, a heptenyloxy group, an octenyloxy group, a nonenyloxy group, and a decenyloxy group, or a fluorine-substituted alkenyloxy group thereof; a propionyloxy group, a butynyloxy group, Nyloxy group, hexynyloxy group, heptynyloxy group, octynyloxy group, noninyloxy group, decynyloxy group,
An alkynyloxy group such as a dodecynyloxy group or a fluorine-substituted alkynyloxy group thereof; a hydrogen atom; a fluorine atom; a trifluoromethyl group;
And a cyano group.

In the formula (4), J ⁵ represents a hydrogen atom, a fluorine atom, a cyano group or J ^6- (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 group having 3 to 16 carbon atoms, which may be substituted with a fluorine atom. Is shown. As the above J ^6- (O) m ² , a methyl group, an ethyl group,
Propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, alkyl group such as dodecyl group or a fluorine-substituted alkyl group thereof; ethenyl group, propenyl group, butenyl group,
Alkenyl groups such as pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group and the like and fluorine-substituted alkenyl groups; methoxymethyl group, ethoxymethyl group, propoxymethyl group, pentyloxymethyl Group, hexyloxymethyl group, heptyloxymethyl group, octyloxymethyl group, nonyloxymethyl group, decyloxymethyl group, methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, pentyloxyethyl group, hexyloxy Ethyl group, heptyloxyethyl group, octyloxyethyl group, nonyloxyethyl group,
Decyloxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, decyloxypropyl , Methoxybutyl group, ethoxybutyl group, propoxybutyl group, butoxybutyl group, pentyloxybutyl group, hexyloxybutyl group, heptyloxybutyl group, octyloxybutyl group, nonyloxybutyl group,
Decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, octyloxypentyl, nonyloxypentyl, decyloxypentyl And the like, or a fluorine-substituted alkoxyalkyl group thereof.

In the formula (4), X ⁹ , X ¹⁰ , X ¹¹ and X
Specific examples of the aromatic ring having a ring structure containing ¹² include 1,
4-phenylene, 1,4- (2-fluoro) phenylene,
1,4- (3-fluoro) phenylene, 1,4- (2,5
-Difluoro) phenylene, 1,4- (3,6-difluoro) phenylene, 1,4- (2,6-difluoro) phenylene, 1,4- (3,5-difluoro) phenylene, 2,
5-pyrimidinediyl, 5,2-pyrimidinediyl,
Examples thereof include 2,5-pyridinediyl and 5,2-pyridinediyl.

In the formula (4), E ¹ and E ² are each independently:

[0058]

Embedded image (However, X ^{13 to} X ¹⁶ each independently represent CH or CF). W ¹ is —C ₂ H ₄ —, —CH ₂ O— or —
Shows OCH ₂ —. 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

[0059]

Embedded image It is. G ⁵ ~G ⁸ independently represents a hydrogen atom or a fluorine atom.

As the compound represented by the formula (4), for example, 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) benzonitrile, 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-fluorobenzonitrile, 4 '-(2- (4- (1-fluoro-1
-(E) -pentenyl) phenyl) ethyl) -3-fluorobenzonitrile, 4 '-(2- (4- (2-fluoro-1-
(E) -pentenyl) phenyl) ethyl) -3-fluorobenzonitrile, 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′-
Methyl biphenyl, 4- (1,2-difluoro-1-
(E) -heptenyl) -4′-ethylbiphenyl, 4-
(1,2-difluoro-1- (E) -heptenyl) -4′-
Pentyl biphenyl, 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-decylpyrimidine

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, 1- (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'-di (Fluorophenyl)
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 '-(1- (E) -pentenyl) benzyloxy) -4-methylbenzene, 1- (4'-(1- (E)
-Pentenyl) benzyloxy) -4-ethylbenzene,
1- (4 '-(1- (E) -pentenyl) benzyloxy)-
4-propylbenzene, 1- (4 ′-(1- (E) -pentenyl) benzyloxy) -4-butylbenzene, 1- (4 ′
-(1- (E) -pentenyl) benzyloxy) -4-pentylbenzene, 1- (4 '-(1- (E) -hexenyl) benzyloxy) -4-propylbenzene, 1- (4'-( 1-
(E) -heptenyl) benzyloxy) -4-propylbenzene, 1- (4 ′-(1- (E) -pentenyl) benzyloxy) -4-trifluoromethylbenzene, 1- (4 ′-(1-
(E) -pentenyl) benzyloxy) -3,4,5-trifluorobenzene, 1- (4 ′-(1- (E) -pentenyl) benzyloxy) -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-methyl) 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 ''-propylcyclohexyl)) 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) benzoate

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′-cyano-3′-fluoro) phenyl- (4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, (4′-cyano-3′-fluoro) phenyl- (4- (1-fluoro-1- (E) -heptenyl)) benzoate, (3 ′, 4′-difluoro) phenyl- (4- (1,
2-difluoro-1- (E) -pentenyl)) benzoate, (3 ′, 4′-difluoro) phenyl- (4- (2-fluoro-1- (E) -heptenyl)) benzoate, (3 ′,
4 ′, 5′-trifluoro) phenyl- (4- (1,2-difluoro-1- (E) -pentenyl)) benzoate, (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,
-(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, 1- (2- (4′-decylphenyl) ) Ethyl) -4
-(1- (E) -pentenyl) benzene, 1- (2- (4'-
Propylphenyl) ethyl) -4- (1- (E) -propenyl) benzene, 1- (2- (4′-propylphenyl) ethyl) -4- (1- (E) -butenyl) benzene, 1- ( 2-
(4′-propylphenyl) ethyl) -4- (1- (E) -hexenyl) benzene, 1- (2- (4′-propylphenyl) ethyl) -4- (1- (E) -heptenyl) benzene , 1
-(2- (4-propylphenyl) ethyl) -4- (1-
(E) -octenyl) benzene, 1- (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, -(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,
1- (2- (4′-cyanophenyl) ethyl) -4- (1-
(E) -pentenyl) benzene, 1- (2- (4′-fluorophenyl) ethyl) -4- (1- (E) -pentenyl) benzene, 1- (2- (3 ′, 4′-difluoro) (Phenyl) 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, 1- (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,
-(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,
1- (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'-heptylbenzyloxy) -1- (1- (E) -nonenyl) benzene, 4- (4'-octylbenzyloxy)
-1- (1- (E) -nonenyl) benzene, 4- (4′-nonylbenzyloxy) -1- (1- (E) -nonenyl) benzene, 4- (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 '-(1- (E) -pentenyl) benzyloxy) -4-methylbenzene, 1- (4'-(1- (E)
-Pentenyl) benzyloxy) -4-ethylbenzene,
1- (4 '-(1- (E) -pentenyl) benzyloxy)-
4-propylbenzene, 1- (4 ′-(1- (E) -pentenyl) benzyloxy) -4-butylbenzene, 1- (4 ′
-(1- (E) -pentenyl) benzyloxy) -4-pentylbenzene, 1- (4 '-(1- (E) -pentenyl) benzyloxy) -4-propylbenzene, 1- (4'-( 1-
(E) -Hexenyl) benzyloxy) -4-propylbenzene, 1- (4 ′-(1- (E) -heptenyl) benzyloxy) -4-propylbenzene, 1- (4 ′-(1- (E ) -Pentenyl) benzyloxy) -4-trifluoromethylbenzene, 1- (4 ′-(1- (E) -pentenyl) benzyloxy) -3,4,5-trifluorobenzene, 1- (4′- (1
-(E) -pentenyl) benzyloxy) -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'-hexylphenoxy) -1- (1- (E) -pentenyl) benzene, 4- (4'-propylphenoxy) -1-
(1- (E) -propenyl) benzene, 4- (4′-propylphenoxy) -1- (1- (E) -butenyl) benzene,
-(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)) benzoate, 4 ′-(4 ″ -propylcyclohexyl) phenyl- (4- (1- (E) -butenyl)) benzoate, 4 ′-(4 ″ -propylcyclohexyl) phenyl- (4- ( 1- (E) -hexynyl)) benzoate,
4 '-(4''-propylcyclohexyl) phenyl- (4-
(1- (E) -heptenyl)) benzoate, 4 ′-(4 ″-
Propylcyclohexyl) phenyl- (4- (1- (E)-
Octenyl)) benzoate, 4 '-(4''-propylcyclohexenyl) phenyl- (4- (1- (E) -pentenyl)) benzoate, (4'-cyano-3'-fluoro) phenyl- (4- (1- (E) -pentenyl)) benzoate, (4 ′
-Cyano-3'-fluoro) phenyl- (4- (1- (E) -heptenyl)) benzoate, (3 ', 4'-difluoro) phenyl- (4- (1- (E) -pentenyl)) benzoate ,
(3 ′, 4′-difluoro) phenyl- (4- (1- (E) -heptenyl)) benzoate, (3 ′, 4 ′, 5′-trifluoro)
Phenyl- (4- (1- (E) -pentenyl)) benzoate, (3 ′, 4 ′, 5′-trifluoro) phenyl- (4- (1
-(E) -heptenyl)) benzoate and the like.

The compound represented by the formula (4) can be produced, for example, by the method described in JP-A-9-235553.

Specific examples of the compound represented by the formula (5) include, for example, 1- (4-fluorocyclohexyl) -4-
Propenylbenzene, 1- (1-trans-butenyl) -4
-(4-fluorocyclohexyl) benzene, 1- (1-t
rans-pentenyl) -4- (4-fluorocyclohexyl) benzene, 1- (1-trans-hexenyl) -4- (4
-Fluorocyclohexyl) benzene, 1- (1-trans
-Heptenyl) -4- (4-fluorocyclohexyl) benzene, 1- (1-trans-octenyl) -4- (4-fluorocyclohexyl) benzene, 1- (1-trans-nonenyl) -4- (4-fluoro (Cyclohexyl) benzene,
1- (1-trans-decenyl) -4- (4-fluorocyclohexyl) benzene, 1- (1-trans-undecenyl)-
4- (4-fluorocyclohexyl) benzene, 1- (1
-Trans-dodecenyl) -4- (4-fluorocyclohexyl) benzene, 1- (4,4-difluorocyclohexyl) -4-propenyl-benzene, 1- (1-trans-butenyl) -4- (4,4- Difluorocyclohexyl) benzene, 1- (1-trans-pentenyl) -4- (4,4-
Difluorocyclohexyl) benzene, 1- (1-trans
-Hexenyl) -4- (4,4-difluorocyclohexyl) benzene, 1- (1-trans-heptenyl) -4-
(4,4-difluorocyclohexyl) benzene, 1-
(1-trans-octenyl) -4- (4,4-difluorocyclohexyl) benzene, 1- (1-trans-nonenyl)-
4- (4,4-difluorocyclohexyl) benzene, 1
-(1-trans-decenyl) -4- (4,4-difluorocyclohexyl) benzene, 1- (1-trans-undecenyl) -4- (4,4-difluorocyclohexyl) benzene, 1- (1-trans- Dodecenyl) -4- (4,4-difluorocyclohexyl) benzene, 4 '-(4-fluorocyclohexyl) -4-propenyl-biphenyl, 4-
(1-trans-butenyl) -4 ′-(4-fluorocyclohexyl) biphenyl, 4- (1-trans-pentenyl)-
4 '-(4-fluorocyclohexyl) biphenyl, 4-
(1-trans-hexenyl) -4 ′-(4-fluorocyclohexyl) biphenyl, 4- (1-trans-heptenyl)-
4 '-(4-fluorocyclohexyl) biphenyl, 4-
(1-trans-octenyl) -4 ′-(4-fluorocyclohexyl) biphenyl, 4- (1-trans-nonenyl)-
4 '-(4-fluorocyclohexyl) biphenyl, 4-
(1-trans-decenyl) -4 ′-(4-fluorocyclohexyl) biphenyl, 4- (1-trans-undecenyl)-
4 '-(4-fluorocyclohexyl) biphenyl, 4-
(1-trans-dodecenyl) -4 ′-(4-fluorocyclohexyl) biphenyl,

4 '-(4,4-difluorocyclohexyl) -4-propenyl-biphenyl, 4- (1-trans-
(Butenyl) -4 ′-(4,4-difluorocyclohexyl)
Biphenyl, 4- (1-trans-pentenyl) -4′-
(4,4-difluorocyclohexyl) biphenyl, 4-
(1-trans-hexenyl) -4 ′-(4,4-difluorocyclohexyl) biphenyl, 4- (1-trans-heptenyl) -4 ′-(4,4-difluorocyclohexyl) biphenyl, 4- (1-trans -Octenyl) -4 '-(4,4
-Difluorocyclohexyl) biphenyl, 4- (1-tr
ans-nonenyl) -4 ′-(4,4-difluorocyclohexyl) biphenyl, 4- (1-trans-decenyl) -4′-
(4,4-difluorocyclohexyl) biphenyl, 4-
(1-trans-undecenyl) -4 ′-(4,4-difluorocyclohexyl) biphenyl, 4- (1-trans-dodecenyl) -4 ′-(4,4-difluorocyclohexyl) biphenyl, 4-propenyl-4 ′ -(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-
trans-butenyl) -4 ′-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans
-Pentenyl) -4 '-(4-fluorocyclohexyl)-
2,3-difluorobiphenyl, 4- (1-trans-hexenyl) -4 ′-(4-fluorocyclohexyl) -2,3
-Difluorobiphenyl, 4- (1-trans-heptenyl) -4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans-octenyl)-
4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans-nonenyl) -4'-
(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans-decenyl) -4 ′-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans-undecenyl) -4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans-dodecenyl) -4'-(4-fluorocyclohexyl) -2,3-difluorobiphenyl,
4-propenyl-4 '-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tran
s-butenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans
-Pentenyl) -4 '-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tran
s-hexenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tran
s-heptenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tran
s-octenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tran
s-nonenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans
-Decenyl) -4 '-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-trans
-Undecenyl) -4 '-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl, 4- (1-tr
ans-dodecenyl) -4 ′-(4,4-difluorocyclohexyl) -2,3-difluorobiphenyl and the like.

Further, as the compound represented by the formula (5), a compound in which “2,3-difluoro” is replaced with “2-fluoro” among the compounds exemplified above; Compound replaced by "3-fluoro";
Compound in which “propenyl” is replaced by “propynyl”; compound in which “1-trans-butenyl” is replaced by “1-butynyl”; “1-trans-pentenyl” is “1”
-Pentynyl "-substituted compound;" 1-trans-
Compound in which “hexenyl” is replaced by “1-hexynyl”; “1-trans-heptenyl” is “1-heptynyl”
A compound wherein “1-trans-octenyl” is replaced by “1-octynyl”; “1-tran
A compound in which "s-nonenyl" is replaced by "1-nonylyl"; a compound in which "1-trans-decenyl" is replaced by "1-decinyl"; a compound in which "1-trans-undecenyl" is replaced by "1-undecinyl""1-tr
Compounds in which “ans-dodecenyl” is replaced by “1-dodecynyl” are exemplified.

Further, as the compound represented by the formula (5),
1- (4-fluorocyclohexyl) propylbenzene,
1-butyl-4- (4-fluorocyclohexyl) benzene, 1-pentyl-4- (4-fluorocyclohexyl)
Benzene, 1-hexyl-4- (4-fluorocyclohexyl) benzene, 1-heptyl-4- (4-fluorocyclohexyl) benzene, 1-octyl-4- (4-fluorocyclohexyl) benzene, 1-nonyl-4- (4-
(Fluorocyclohexyl) benzene, 1-decyl-4-
(4-fluorocyclohexyl) benzene, 1-undecyl-4- (4-fluorocyclohexyl) benzene, 1-
Dodecyl-4- (4-fluorocyclohexyl) benzene, 4 '-(4-fluorocyclohexyl) -4-propylbiphenyl, 4-butyl-4'-(4-fluorocyclohexyl) biphenyl, 4-pentyl-4 '-( 4-fluorocyclohexyl) biphenyl, 4-hexyl-4'-
(4-fluorocyclohexyl) biphenyl, 4-heptyl-4 ′ (4-fluorocyclohexyl) biphenyl, 4
-Octyl-4 '(4-fluorocyclohexyl) biphenyl, 4-nonyl-4'-(4-fluorocyclohexyl) biphenyl, 4-decyl-4 '-(4-fluorocyclohexyl) biphenyl, 4-undecyl-4'- (4-
(Fluorocyclohexyl) biphenyl, 4-dodecyl-
4 '-(4-fluorocyclohexyl) biphenyl, 4-
Propyl-4 ′-(4-fluorocyclohexyl) -2,
3-difluorobiphenyl, 4-butyl-4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-pentyl-4'-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-hexyl −
4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-heptyl-4'-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-
Octyl-4 '-(4-fluorocyclohexyl) -2,
3-difluorobiphenyl, 4-nonyl-4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-decyl-4'-(4-fluorocyclohexyl)
-2,3-difluorobiphenyl, 4-undecyl-
4 '-(4-fluorocyclohexyl) -2,3-difluorobiphenyl, 4-dodecyl-4'-(4-fluorocyclohexyl) -2,3-difluorobiphenyl and the like can be mentioned. A compound in which “2,3-difluoro” in the above exemplified compounds is replaced by “2-fluoro”;
Compounds in which "2,3-difluoro" is replaced by "3-fluoro" are also included.

The compound represented by the formula (5) can be produced, for example, by the method described in JP-A-10-72583.

In the liquid crystal composition of the present invention, the above formula (1)
And a compound represented by the above formula (2) and / or the above formula (3)
And a compound represented by the above formula (4) and / or the above formula (5)
Composition ratio with the compound represented by (100% of the entire composition
Can be appropriately selected so as to achieve the desired purpose. Preferably,
5 to 50 mol% of the compound represented by the formula (1), 5 to 94 mol% of the compound represented by the formula (2) and / or the formula (3),
The compound represented by formula (4) and / or formula (5) is in the range of 1 to 25 mol%.

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 (provided that * represents an asymmetric carbon).

[0101]

Embedded image

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 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.

[0104]

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. (a) The refractive index anisotropy (Δn) was measured with an Abbe refractometer. The measurement wavelength at this time is 589 nm, and the measurement temperature is 2
0 ° C. (b) Maximum temperature (TN) of the N (nematic) phase of the liquid crystal composition
I) and the minimum temperature (mp) were measured using a polarizing microscope. (c) The viscosity was measured by an automatic falling ball viscometer (AMV-200, manufactured by AntonPARR). Measurement temperature is 2
Performed at 0 ° C.

Example 1 A liquid crystal composition 1 was prepared by mixing 10.0% by weight of the compound (1-1) corresponding to the formula (1) with the composition A shown in Table 1.

[0106]

Embedded image

[0107]

[Table 1]

Subsequently, Δn and the response parameter (η / Δn2) of the composition A and the composition 1 were measured. Table 2 shows the results. η / Δn ² is known to be proportional to the response time, and is a parameter representing the response of the liquid crystal material.
The smaller η / Δn ^{2, the} faster the liquid crystal material. [Next-generation liquid crystal display technology, Tatsuo Uchida, edited by the Industrial Research Committee]
136 (1994)]. The Δn of the composition 1 was 0.125, which was larger than that of the composition A. In addition, it can be seen that the response parameter is reduced, and the response is improved by adding the compound (1-1).

[0109]

[Table 2]

Example 2 A liquid crystal composition 2 was prepared by mixing the compound A used in Example 1 with the compound (1-2) corresponding to the formula (1) at the ratio shown in Table 3. Table 4 shows the Δn and response parameters of Composition 2 and Composition A. As is clear from Table 4, the composition 2 of the present invention has a larger Δn and a smaller response parameter than the composition A, and is excellent as a liquid crystal composition.

[0111]

[Table 3]

[0112]

[Table 4]

Example 3 Compounds (3-1), (3-2) corresponding to the formula (3)
(3-3) and (3-4) were mixed with the compound (2-5) corresponding to the formula (2) at the ratio shown in Table 5, and the composition B was mixed.
I got

[0114]

[Table 5]

A liquid crystal composition 3 was obtained by mixing the compound B with the compound (1-3) corresponding to the formula (1) at a ratio shown in Table 6. Next, Table 7 shows the measurement results of Δn of the liquid crystal composition 3 and the composition B. As is clear from Table 7, the liquid crystal composition 3 of the present invention has a large Δn and is superior to the composition B. In addition, the nematic phase temperature range of the liquid crystal composition 3 was -20 to 133 ° C., and was extremely wide and excellent in both a low temperature part and a high temperature part.

[0116]

[Table 6]

[0117]

[Table 7]

Example 4 The compound (1-2) corresponding to the formula (1) was mixed with the composition B prepared in Example 3 at a ratio shown in Table 8 to obtain a liquid crystal composition 4. Subsequently, Δn of the liquid crystal composition 4 and the composition B
Was measured. Table 9 shows the results. As is clear from Table 9, the liquid crystal composition 4 of the present invention has a large Δn and is superior to the composition B. The lower limit temperature of the nematic phase of the liquid crystal composition 4 was -50 ° C or lower, and the upper limit temperature was 139 ° C.

[0119]

[Table 8]

[0120]

[Table 9]

Example 5 The compound (1-3) corresponding to the formula (1) and the composition B prepared in Example 3 were mixed at a ratio shown in Table 10 to obtain a liquid crystal composition 5. Subsequently, Δ of liquid crystal composition 5 and composition B
n was measured. Table 11 shows the results. As is clear from Table 11, the liquid crystal composition 5 of the present invention has a Δ
It can be seen that n is large and excellent. In addition, the liquid crystal composition 5
The lower limit temperature of the nematic phase was −50 ° C. or lower, and the upper limit temperature was 138 ° C., and both the low temperature portion and the high temperature portion were extremely wide and excellent.

[0122]

[Table 10]

[0123]

[Table 11]

Example 6 A liquid crystal composition 6 was obtained by mixing the compound (1-4) corresponding to the formula (1) and the composition B prepared in Example 3 at the ratio shown in Table 12. Subsequently, Δn of the liquid crystal composition 6 and the composition B were measured. Table 13 shows the results. As is clear from Table 13, the liquid crystal composition 6 of the present invention has a large Δn and is superior to the composition B.

[0125]

[Table 12]

[0126]

[Table 13]

Example 7 A liquid crystal composition 7 was obtained by mixing the compound (1-5) corresponding to the formula (1) and the composition B prepared in Example 3 at the ratio shown in Table 14. Subsequently, Δn of the liquid crystal composition 7 and the composition B were measured. Table 15 shows the results. As is clear from Table 15, the liquid crystal composition 7 of the present invention has a large Δn and is superior to the composition B. The lower limit temperature of the nematic phase of the liquid crystal composition 7 was -50 ° C or lower, and the upper limit temperature was 138 ° C.

[0128]

[Table 14]

[0129]

[Table 15]

Example 8 The compound (4-1) corresponding to the formula (4) and the composition A prepared in Example 1 were mixed at a ratio shown in Table 16 to obtain a composition C.

[0131]

[Table 16]

Next, the liquid crystal composition 8 was obtained by mixing the compound C with the compound (1-1) corresponding to the formula (1) at a ratio shown in Table 17. Subsequently, Δn of the liquid crystal composition 8 and the composition C were measured. The results are shown in Table 18. As is clear from Table 18, the liquid crystal composition 8 of the present invention has a large Δn and is superior to the composition C.

[0133]

[Table 17]

[0134]

[Table 18]

Example 9 A compound corresponding to the formula (2) was added to the composition A described in Example 1.
(2-6) was mixed at the ratio shown in Table 19 to obtain Liquid Crystal Composition D.

[0136]

[Table 19]

Next, the compound (1-2) corresponding to the formula (1) was mixed with the composition D at a ratio shown in Table 20 to obtain a liquid crystal composition 9. Subsequently, Δn of the liquid crystal composition 9 and the composition D at 30 ° C. were measured. The results are shown in Table 21.
As is clear from Table 21, the liquid crystal composition 9 of the present invention has a large Δn and is superior to the composition D.

[0138]

[Table 20]

[0139]

[Table 21]

[0140]

The liquid crystal composition of the present invention contains a compound represented by the formula (1) and a compound represented by the formula (2) and / or the formula (3). Large, stable, easy to mix with other liquid crystals, such as STN (super twisted nematic)
It is particularly useful as a material constituting a liquid crystal element represented by a liquid crystal element of a liquid crystal type or a PDLC (polymer dispersed liquid crystal) type liquid crystal element.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Chizu Sekine 6 Kitahara, Tsukuba, Ibaraki Pref. Within Sumitomo Chemical Co., Ltd. (72) Inventor Koichi Fujisawa 6 Kitahara, Tsukuba, Ibaraki Pref. Sumitomo Chemical Co., Ltd. F-term (reference) 4H027 BA01 BB04 BB11 BD02 BD07 BD08 BE05 CB04 CB05 CE01 CE03 CE04 CE05 CL01 CM04 CP05 CU01 CU03 CU04 CU05 DP01 DP03 DP04 DP05

Claims (7)

[Claims] 1. A composition comprising at least one phenylacetylene compound represented by the formula (1) and at least one compound represented by the formula (2) and / or a compound represented by the formula (3): A liquid crystal composition comprising: Embedded image (Wherein, A ^{1 to} A ¹² each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group. R ¹ and R ² are each independently hydrogen atom, a fluorine atom, a cyano group, 4-R ³ - (cycloalkyl) group, 4-R ³ - (cycloalkenyl) group or a R
⁴ - (O) indicating the q group (wherein, R ³ is a hydrogen atom may be substituted with a straight-chain or branched fluorine atoms, C 1 -C
An alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms, wherein R ⁴ may be substituted with a linear or branched fluorine atom, An alkenyl group having 2 to 12 carbon atoms or an alkynyl group having 2 to 12 carbon atoms. q represents 0 or 1). ) (In the formula (2), 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, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-
Represents 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 each independently represent a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a cyano group,
Alkyl group of 12 to 12, alkenyl group of 2 to 12 carbon atoms,
An alkoxy group having 1 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 Show. The methylene group contained in these groups may be substituted with an oxygen atom, a sulfur atom or a silicon atom, and may be either linear or branched (provided that R ⁵ and / or R ⁶ are -CX =
CX-R and -C≡CR (R represents an alkyl group, an alkoxy group or an alkynyl group having 1 to 10 carbon atoms which may be substituted by a fluorine atom, and X represents a hydrogen atom or a fluorine atom) Except in the case of. ). Z ¹ , Z ² and Z ³ are each independently —COO—, —OCO—, —OCH ₂ —,
—CH ₂ O—, an alkylene group having 1 to 5 carbon atoms, 2 carbon atoms
Represents an alkenylene group of 5 to 5, an alkynylene group of 2 to 5 carbon atoms or a single bond, b, c and d are each independently 0 or 1, and satisfy b + c + d ≧ 1. ) (In the formula (3), J ¹ represents a hydrogen atom, a fluorine atom, a cyano group or J ³ (O) m ¹ (provided that J ³ may be substituted with a fluorine atom, Alkyl group, having 2 to 2 carbon atoms
Indicates 12 alkenyl group or alkynyl group having 2 to 12 carbon atoms, m ¹ is 0 or 1). J ² represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms. A is Represents k, m and n represent 0 or 1. m and n cannot be 0 or 1 at the same time. X ^{1 to} X ⁸ are
Each independently represents CH or CF. G ^{1 to} G ⁴ each independently represent a hydrogen atom or a fluorine atom. Z ⁴ is −C≡
It represents C- or -C≡CC≡C- (however, when n = 0, Z ⁴ is -C≡C-). ) 2. The ring D in the compound represented by the above formula (2)
May be substituted with a fluorine atom, 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexene, 4,1-cyclohexene, 2,5-cyclohexene, 5,2- The liquid crystal composition according to claim 1, wherein the liquid crystal composition is any one of cyclohexelene, 3,6-cyclohexelene, and 6,3-cyclohexelene. 3. A compound represented by the formula (4) and / or a compound represented by the formula:
The liquid crystal composition according to claim 1, further comprising at least one of the compounds represented by (5). Embedded image (In the formula (4), 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, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, which may be substituted with a fluorine atom,
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, - (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, or 3 to 16 carbon atoms, which may be substituted with a fluorine atom.)
Represents an alkynyl group). E ¹ and E ² are each independently: (However, X ^{13 to} X ¹⁶ each independently represent CH or CF). W ¹ is —C ₂ H ₄ —, —CH ₂ O— or —
Shows OCH ₂ —. 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 It is. G ⁵ ~G ⁸ independently represents a hydrogen atom or a fluorine atom. ) (In the formula (5), R ⁷ represents an alkyl group having 1 to 10 carbon atoms,
The hydrogen atom on the benzene ring in the formula (5) may be substituted with a fluorine atom. n, p and q are each 1 or 2, and X ¹⁷ represents a trans form of —CH ＝ CH— or an ethynyl group (however, when n is 1, X ¹⁷ is —CH ₂ —CH ₂
-). ) 4. The compound represented by the formula (2) is a compound represented by the formula (6)
The liquid crystal composition according to any one of claims 1 to 3, which is at least one of the compounds represented by (10) to (10). Embedded image (In the formulas (6) to (10), R ⁵ , R ⁶ , ring A, ring B,
Z ¹ and b have the same meaning as in formula (2). j is 0, 1 or 2; h is 0 or 1;
Or 2. In the formula (10), B ^{1 to} B ¹² each independently represent a hydrogen atom, a fluorine atom or a chlorine atom. 5. The respective composition ratios of the compound represented by the formula (1), the compound represented by the formula (2) and the compound represented by the formula (3) (when the whole composition is 100%) The ratio of each component) is 5 to 50 mol% of the compound represented by the formula (1),
The compound represented by the formula (2) is 0 to 95 mol% and the compound represented by the formula (3) is 0 to 95 mol% (however, any of the compounds represented by the formulas (2) and (3)) Is not 0 mol%, the compound represented by the formula (2) is 10 mol% or more,
The compound represented by (3) is at least 5 mol%. The liquid crystal composition according to claim 1, 2 or 4, wherein 6. A compound represented by the formula (1), a compound represented by the formula (2) and / or the formula (3), and a compound represented by the formula (4) and / or
The composition ratio with the compound represented by (5) (10%
The proportion of each component as 0%) is 5 to 50 mol% of the compound represented by the formula (1), and 5 to 94 mol% of the compound represented by the formula (2) and / or (3). %, Formula (4) and / or formula
The liquid crystal composition according to claim 3, wherein the compound represented by (5) is 1 to 25 mol%. 7. A liquid crystal device comprising the liquid crystal composition according to claim 1 sandwiched between a pair of electrode substrates.