JPH0940958A - Liquid crystal composition and liquid crystal element containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal composition having a high dielectric anisotropy (Δε), an N phase in a wide range of temperatures including room temperature and having an excellent response by mixing specified compounds with each other. SOLUTION: This liquid crystal composition is obtained by mixing at least one compound selected from among compounds of formula I [wherein R is a 1-12C alkyl, a 2-16C alkenyl or a 2-16C alkoxyalkyl; X1 to X4 and Y1 to Y4 are each CH, CF or N; A is H, a 4-R1 -(cycloalkyl), a 4-R1 -(cycloalkenyl) or an R1 -(O)p group; R1 is a 1-12C alkyl, a 2-12C alkenyl or an alkynyl or an alkoxyalkyl; (p) is 0 or 1; (z) is C≡C or a single bond], formula II (wherein B is F, trifluoromethyl, trifluoromethoxy or cyano) and formula III (wherein C is a 1-12C alkyl, a 2-12C alkenyl, a 2-16C alkoxyalkyl, A or B) with at least one compound (e.g. a compound of formula VI) represented by general formula V.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel nematic liquid crystal composition and a liquid crystal device using the same. More specifically, it is represented by a liquid crystal composition having a high refractive index anisotropy (Δn), an optical shutter using the same, an STN (super twist nematic) type liquid crystal element, and a PDLC (polymer dispersion type liquid crystal) type liquid crystal element. Display element.

[0002]

2. Description of the Related Art With the progress of information society in recent years, various display elements have become more and more important as one of man-machine interfaces. Under these circumstances, flat displays, especially liquid crystal displays (LCDs)
Are rapidly spreading because of their features such as thinness, light weight, low voltage drive, 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 price, and high density due to complicated manufacturing process and poor yield. Considering price and productivity, the simple matrix method is preferable. It is influential.

[0004] As a liquid crystal element of a simple matrix type which is currently in practical use, a TN (twisted nematic) type, S
A device using a TN (super twisted nematic) type liquid crystal element is mainly used. The TN type is widely used as a display element for watches and calculators. However, in this method, the rise of electro-optical characteristics is gradual, and the contrast significantly decreases as the duty ratio increases. Is difficult.

The STN type is a method developed to compensate for the drawbacks of such a TN type liquid crystal element, and has a steep electro-optical characteristic, so that a large screen can be realized.
At present, it is used for displays such as laptop personal computers.

However, although the STN type liquid crystal element has excellent characteristics as compared with the TN type liquid crystal element as described above, it is still necessary to further increase the area, cost and density. It leaves a problem to be solved.

For example, the STN type liquid crystal element is still insufficient in view angle characteristics and response speed when compared with the TFT type liquid crystal element which is a typical active matrix type liquid crystal element. In particular, high-speed response is indispensable in order to further increase the area, increase the density, or display a moving image.

In order to make the STN type liquid crystal device have a high speed response, reducing the cell thickness is one of the most effective methods.
The STN type utilizes the birefringence effect in the display method, and in order to use this method, it is necessary to suppress changes in the color tone and optical characteristics of the panel, that is, to set the retardation to a certain optimum value. . Retardation R is (equation-
Since it is expressed by 1), it is necessary to increase the refractive index anisotropy Δn in order to reduce the cell thickness d. R = Δn × d (formula-1)

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. Further, the temperature dependence of Δn is also one of the problems to be solved. In order to suppress the change in Δn in the operating temperature range, it is generally considered effective to raise the transition temperature of the liquid crystal composition.

Further, from the viewpoint of low power consumption, it is effective to lower the threshold voltage, but for this purpose, it is usually necessary to increase the dielectric anisotropy Δε. ing.

[0011]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a liquid crystal composition having a high refractive index anisotropy (Δn) and a liquid crystal device which can be used as an optical shutter or a display device using the same. To do. In addition to the high refractive index anisotropy (Δn), the present invention also has a high dielectric anisotropy (Δε).
, A liquid crystal composition having an N phase in a wide temperature range including room temperature, a liquid crystal composition having a low viscosity and a small response parameter (η / Δn ² ) and excellent responsiveness, and those liquid crystal compositions It is intended to provide a liquid crystal device using the.

[0012]

Based on the above, the inventors of the present invention have conducted diligent studies, and as a result, found a liquid crystal composition having a high refractive index anisotropy (Δn), and completed the present invention. Came to. The present invention relates to a liquid crystal composition described in items [1] and [2] below.

[1] The following general formula (1)

Embedded image (In the formula, R is an alkyl group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms.
A 16 alkenyl group or a C2-C16 alkoxyalkyl group is shown. X ₁ , X ₂ , X ₃ , X ₄ , Y ₁ , Y
₂ , Y ₃ , and Y ₄ each independently represent CH, CF, or N. A is a hydrogen atom, 4-R _1- (cycloalkyl) group, 4-R _1- (cycloalkenyl) group or R ₁
Represents a-(O) p group, R ₁ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms. , P is 0 or 1. Z represents -C≡C- or a single bond. ) Or a compound represented by the following general formula (2)

[0014]

Embedded image (In the formula, B represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group. R, X ₁ ,
X ₂ , X ₃ , X ₄ , Y ₁ , Y ₂ , Y ₃ , Y ₄ and Z have the same meanings as described above. ) Or a compound represented by the following general formula (3)

[0015]

Embedded image (In the formula, C is an alkyl group having 1 to 12 carbon atoms and 2 to 2 carbon atoms.
12 alkenyl groups, C 2-16 alkoxyalkyl groups, 4-R _1- (cycloalkyl) groups, 4-R _1-
A (cycloalkenyl) group, an R _1- (O) p group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group is shown. R, X ₁ , X ₂ , X ₃ , X ₄ , Y
₁ , Y ₂ , Y ₃ , Y ₄ , R ₁ and p have the same meanings as described above. ) At least 1 selected from the compounds represented by
Compound and the following general formula (4)

[0016]

Embedded image (In the formula, ring C, ring D, ring E and ring F are each independently 1,4-phenylene and 1,4-cyclohexylene, 1,4-cyclohexene, 4, which may be substituted with a fluorine atom. 1-cyclohexylene, 2,5-cyclohexylene, 5,2-cyclohexene, 3,6-cyclohexylene, 6,3-cyclohexene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5 -Pyridinediyl, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown.
R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms.
R ₃ is 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, an alkyl group having 1 to 12 carbon atoms, or 2 carbon atoms.
To alkenyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 16 carbon atoms or alkoxyalkyl groups having 2 to 16 carbon atoms.
Z ₁ , Z ₂ , and Z ₃ are each independently -COO-,
_{-OCO -, - OCH 2 -,} - CH 2 O-, 1~ carbon atoms
5 represents an alkylene group having 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. J and K each independently represent methylene or -O-.
a, b, c, d, and e are each independently 0 or 1
And satisfies b + c + d ≧ 1. However,
When R ₂ is an alkoxy group, a is 0, and when R ₃ is an alkoxy group, e is 0. When R ₂ and R ₃ are not an alkoxy group, b is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, or 5 , 2
-In the case of pyridinediyl, b is 0, c is 1, and ring D is 1,4-phenylene, 2,5-pyrimidinediyl, 5,
In the case of 2-pyrimidinediyl, 2,5-pyridinediyl, or 5,2-pyridinediyl, and b is 0, c
Is 0, d is 1, and ring E is 1,4-phenylene, 2,5
-Pyrimidinediyl, 5,2-pyrimidinediyl, 2,
In the case of 5-pyridinediyl or 5,2-pyridinediyl, a is 1, and F is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5- In the case of pyridinediyl or 5,2-pyridinediyl, e is 1. Further, those included in the general formulas (1), (2) and (3) are excluded. )
A liquid crystal composition comprising at least one compound selected from the compounds represented by:

[2] The following general formula (5)

[Chemical 21] (In the formula, R is an alkyl group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms.
12 represents an alkenyl group or an alkoxyalkyl group having 2 to 16 carbon atoms. X ₁ , X ₂ , X ₃ , X ₄ , Y ₁ , Y
₂ , Y ₃ , and Y ₄ each independently represent CH, CF, or N. A is a hydrogen atom, 4-R _1- (cycloalkyl) group, 4-R _1- (cycloalkenyl) group or R ₁
Represents a — (O) p group, R ₁ represents 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, and p is 0 or 1. ) Or a compound represented by the following general formula (6)

[0018]

Embedded image (In the formula, B represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group. R, X ₁ ,
X ₂ , X ₃ , X ₄ , Y ₁ , Y ₂ , Y ₃ and Y ₄ have the same meanings as described above. ) Or a compound represented by the following general formula (7)

Embedded image (In the formula, C is a hydrogen atom, 4-R _1- (cycloalkyl)
Group, 4-R _1- (cycloalkenyl) group, R _1- (O)
p group, fluorine atom, trifluoromethyl group, trifluoromethoxy group or cyano group. R ₁ and p have the same meanings as described above. R is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or 2-1 to 2 carbon atoms.
6 represents an alkoxyalkyl group. X and Y each independently represent a hydrogen atom or a fluorine atom. r and s are 0
To 3 are integers. And at least one compound selected from compounds represented by the following general formula (8)

[0019]

Embedded image (In the formula, R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms. L, ring M, and ring N are each independently 1,4-phenylene, 1,4-cyclohexylene,
2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown. 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, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. W ₁ represents a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a cyano group, and W ₂ and W ₃ are independently hydrogen. An atom or a fluorine atom is shown, and f is independently 0 or 1. ) Or a compound represented by the following general formula (9)

[0020]

Embedded image (In the formula, each R ₂ is independently a hydrogen atom or a carbon number of 1 to 1.
A 12-alkyl group, a C2-C12 alkenyl group, a C1-C16 alkoxy group, or a C2-C16 alkoxyalkyl group is shown. Ring L, Ring M, Ring N and Ring P are each independently 1,4-phenylene and 1,4-
Cyclohexylene, 2,5-pyrimidinediyl, 5,2
-Denotes pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl. Z ₁ , Z ₂ and Z
₃ are independently -COO-, -OCO-, -OCH
₂ -, - CH ₂ O-, an alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group or a single bond having 2 to 5 carbon atoms. f independently represents 0 or 1. And at least one compound selected from the compounds represented by the formula (1). Further, the present invention provides a liquid crystal device comprising at least one liquid crystal composition selected from the liquid crystal compositions according to the above items [1] and [2], which is sandwiched between a pair of electrode substrates. It is related. Hereinafter, the present invention will be described in detail.

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION As a preferred embodiment of the present invention, the liquid crystal composition of each item described below can be mentioned. [3] At least one compound selected from the compounds represented by the above general formulas (1) and (2), at least one compound selected from the compounds represented by the above general formula (3), and the above The liquid crystal composition according to item [1], which contains at least one compound selected from the compounds represented by formula (4). [4] at least one compound selected from the compounds represented by the general formula (1) and the general formula (2) and at least one compound selected from the compounds represented by the general formula (4) The liquid crystal composition according to the item [1], which contains.

[5] At least one compound selected from the compounds represented by the above general formulas (5) and (6), and at least one compound selected from the compounds represented by the above general formula (7) And at least one compound selected from the compounds represented by the above general formulas (8) and (9), the liquid crystal composition according to the above item [2]. [6] At least one compound selected from the compounds represented by the general formula (5) and the general formula (6) and at least selected from the compounds represented by the general formula (8) and the general formula (9) The liquid crystal composition according to item [2], which contains one compound.

[7] At least one compound selected from the compounds represented by the above general formulas (1) and (2) and at least one compound selected from the compounds represented by the above general formula (4) [1] containing the compound of
The liquid crystal composition according to the above. However, in the above general formula (4),
1,4-phenylene in which at least one ring of ring C, ring D, ring E, and ring F is substituted with a fluorine atom,
1,4-cyclohexylene, 4,1-cyclohexylene, 2,5-cyclohexene, 5,2-cyclohexene, 3,6-cyclohexene, 6,3-cyclohexene, 2,5-pyrimidinediyl, 5 , 2-pyrimidinediyl, 2,5-pyridindiyl, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl at least one compound is contained.

[8] At least one compound selected from the compounds represented by the above general formulas (1) and (2), and in the above general formula (4), ring F may be fluorine-substituted. Good 1,4-cyclohexylene, 2,5
-The liquid crystal composition according to the above item [1], containing at least one compound selected from compounds that are dioxanediyl or 5,2-dioxanediyl.

[0025]

[9] At least one compound selected from the compounds represented by the above general formulas (1) and (2), and the following general formula (10)

[Chemical formula 26] (In the formula, ring C, ring D, ring E, R ₂ , R ₃ , Z ₁ , Z ₂ ,
Z ₃ , J, a, b, c and d have the same meanings as described in the general formula (4). [4] The liquid crystal composition according to the above item [1], which comprises at least one compound selected from the compounds represented by [10] At least one compound selected from the compounds represented by the general formulas (1) and (2), and the ring F in the general formula (4) may be substituted with a fluorine atom. The above item containing at least one compound selected from compounds that are 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridindiyl or 5,2-pyridinediyl. The liquid crystal composition according to [1].

[11] At least one compound selected from the compounds represented by the above general formulas (1) and (2), and the following general formula (11)

Embedded image (In the formula, R ₂ , J, ring C and ring D have the same meanings as described in the above general formula (4). A or g is independently 0 or 1, and f is 0, 1 or However, when R ₂ is an alkoxy group, a is 0. When R ₂ is not an alkoxy group, g is
Is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl or 5,2-pyridinediyl, a is 1, and Those included in the general formulas (1) and (2) are excluded. ) At least 1 selected from the compounds represented by
The liquid crystal composition according to the above item [1], which comprises one kind of compound.

[12] At least one compound selected from the compounds represented by the above general formulas (1) and (2) and the following general formula (12)

Embedded image (In the formula, R ₂ , J, ring C, rings D, a, g and f have the same meanings as described in the general formula (11), and R ₃ and K have the same meanings as those described in the general formula (4). E is R
0 when ₃ is an alkoxy group, 1 otherwise.
Represents However, those included in the general formulas (1) and (2) are excluded. [4] The liquid crystal composition according to the above item [1], which comprises at least one compound selected from the compounds represented by

[13] At least one compound selected from the compounds represented by the above general formulas (1) and (2), and the following general formula (13)

[Chemical 29] (In the formula, R ₂ , J, ring C, ring D, a, g and f have the same meanings as described in the general formula (11). However, when R ₂ is an alkoxy group, a is Further, when R ₂ is not an alkoxy group, g is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridindiyl or 5 , 2-pyridinediyl, a is 1, and those included in the general formulas (1) and (2) are excluded) and the following general formula (14).

Embedded image (Wherein R ₂ , J, C, a, g, R ₃ , K, e and f
Has the same meaning as described in the general formula (11).
h represents 0 or 1. However, those included in the general formulas (1) and (2) are excluded. [4] The liquid crystal composition according to the above item [1], which comprises at least one compound selected from the compounds represented by

[14] At least one compound selected from the compounds represented by the general formulas (1) and (2), and in the general formula (4), the ring F is substituted with a fluorine atom. Optionally 1,4-cyclohexene, 4,1-cyclohexene, 2,5-cyclohexene, 5,2-cyclohexene, 3,6-cyclohexene, or 6,3-cyclohexene The liquid crystal composition according to item [1], which contains at least one compound selected from compounds.

[15] The above general formulas (5) and (6)
And at least one selected from the compounds represented by the general formula (7), and the following general formula (15)

[Chemical 31] (In the formula, R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms; L and ring M are each independently 1,4-
Phenylene, 1,4-cyclohexylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown, and W ₁ is a hydrogen atom, a fluorine atom or fluoromethyl. Base,
Difluoromethyl group, trifluoromethyl group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group or cyano group, W ₂ and W ₃ each independently represent a hydrogen atom or a fluorine atom, and f is 0 or 1 Show. ) Or a compound represented by the following general formula (16)

Embedded image (In the formula, R ₂ is independently a hydrogen atom or a carbon number of 1 to 1.
2 represents an alkyl group having 2 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms or an alkoxyalkyl group having 2 to 16 carbon atoms, and ring L, ring M and ring N are each independently 1,4- It shows phenylene, 1,4-cyclohexylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl, and f shows 0 or 1. The liquid crystal composition according to the above item [2], which comprises at least one compound selected from the compounds represented by the formula (1):

[16] At least one compound selected from the compounds represented by the above general formulas (5) and (6), and at least one compound selected from the compounds represented by the above general formula (7) And the liquid crystal composition according to item [2], containing at least one compound selected from compounds represented by the general formulas (15) and (16). [17] At least one compound selected from the compounds represented by the general formula (5) and the general formula (6) and at least selected from the compounds represented by the general formula (15) and the general formula (16). The liquid crystal composition according to the above item [2], which comprises one compound.

[18] R is a fluorine atom-substituted alkyl group, alkenyl group or alkoxyalkyl group, or R ₁ , R ₂ or R ₃ is a fluorine atom-substituted alkyl group, alkenyl group, alkynyl group or The liquid crystal composition according to item [1], which is an alkoxyalkyl group. [19] An alkyl group, an alkenyl group, or an alkoxyalkyl group in which R is substituted with a fluorine atom, or R ₁
Alternatively, the liquid crystal composition according to item [2], wherein R ₂ is a fluorine atom-substituted alkyl group, alkenyl group, alkynyl group or alkoxyalkyl group. As a preferred embodiment of the present invention, the above item [3]
The invention of a liquid crystal element is characterized in that at least one liquid crystal composition selected from the liquid crystal compositions according to item [19] is sandwiched between a pair of electrode substrates.

The compounds used in the liquid crystal composition of the present invention will be described in detail below. Specific examples of the compounds represented by the general formulas (1) and (5) are shown below. In the general formulas (1) and (5), A is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethenyl optionally substituted with a fluorine atom. , Propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, propynyl, butynyl, pentynyl, hexynyl,
Heptinyl, octynyl, noninyl, decynyl, dodecinyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, vinyloxy, propenyloxy, butenyloxy, pentenyloxy , Hexynyloxy, heptenyloxy, octenyloxy, nonenyloxy, decenyloxy, propynyloxy, butynyloxy, pentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, noninyloxy, decynyloxy, undecinyloxy, dodecynyl, methoxymethyl, ethoxymethyl, propoxymethyl, propoxymethyl Pentyloxymethyl, hexyloxymethyl, hept Ruoxymethyl, octyloxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl, nonyloxyethyl, decyloxyethyl, Methoxypropyl, ethoxypropyl, propoxypropyl,
Butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, decyloxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl. , Octyloxybutyl, nonyloxybutyl, decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, heptyloxypentyl, octyloxypentyl, nonyloxypentyl, decyl Oxypentyl, 4
-Methylcyclohexyl, 4-ethylcyclohexyl,
4-propylcyclohexyl, 4-butylcyclohexyl, 4-pentylcyclohexyl, 4-hexylcyclohexyl, 4-heptylcyclohexyl, 4-octylcyclohexyl, 4-nonylcyclohexyl, 4-decylcyclohexyl, 4-propylcyclohexenyl, hydrogen atom and the like No.

As R, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, which may be substituted with a fluorine atom,
Undecyl, dodecyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl,
Methoxymethyl, ethoxymethyl, propoxymethyl,
Butoxymethyl, pentyloxymethyl, hexyloxymethyl, heptyloxymethyl, octyloxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, pentyloxyethyl, hexyloxyethyl, heptyloxyethyl , Octyloxyethyl, nonyloxyethyl, decyloxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl, decyloxypropyl, methoxy Butyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, hep Ruoxybutyl, octyloxybutyl, nonyloxybutyl, decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, heptyloxypentyl, octyloxypentyl, nonyloxypentyl, Decyloxypentyl and the like can be mentioned.

Specific examples of the aromatic ring having a ring structure containing X ₁ , X ₂ , X ₃ and X ₄ and the aromatic ring having a ring structure containing Y ₁ , Y ₂ , Y ₃ and Y ₄ include: Independently, 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, 2,5-pyridinediyl, 5,2-pyridinediyl and the like. Further, specific examples of Z include a single bond and —C≡C—.

In the general formulas (2) and (6), specific examples of B include a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group and a cyano group, and R, Z, X ₁ and Specific examples of the aromatic ring having a ring structure containing X ₂ , X ₃ and X ₄ and the aromatic ring having a ring structure containing Y ₁ , Y ₂ , Y ₃ and Y ₄ include R in the general formula (1). , Z, X ₁ , X ₂ , X ₃ , X ₄ and the aromatic ring having a ring structure containing Y ₁ , Y ₂ , Y ₃ , and Y ₄ are the same as the specific examples.

In the general formula (3), the specific examples of C are the same as A in the general formula (1) or B in the general formula (2), and R, X ₁ , X ₂ , X ₃ , X. specific examples of the aromatic ring consisting of ring structures containing an aromatic ring and _{Y 1, Y 2, Y 3} , Y 4 consisting of ring structures containing _4, the general formula (1)
Specific examples of the aromatic ring having a ring structure containing R, X ₁ , X ₂ , X ₃ and X ₄ and the aromatic ring having a ring structure containing Y ₁ , Y ₂ , Y ₃ and Y ₄ in In the general formula (7), specific examples of C and R are the same as those in the general formula (3), and X and Y represent a hydrogen atom or a fluorine atom. r and s are integers of 0-3. Specific examples of the compound represented by the general formula (4) include the compounds shown below. In addition, general formulas (8) to (1
Specific examples of the compound represented by 6) are also included in these compounds.

[0038]

[Chemical 33]

[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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[0054]

[Chemical 49]

[0055]

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[0056]

[Chemical 51]

[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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[0065]

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[0066]

[Chemical formula 61]

[0067]

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[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

[Chemical 76]

[0082]

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Specific examples of R _{2 in} the above examples are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, which may be substituted with hydrogen atom or fluorine atom. Dodecyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, methoxy, ethoxy,
Propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy,
Decyloxy, undecyloxy, dodecyloxy, vinyloxy, propenyloxy, butenyloxy, pentenyloxy, hexynyloxy, heptenyloxy,
Octenyloxy, nonenyloxy, decenyloxy,
Propynyloxy, butynyloxy, pentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, nonynyloxy, decynyloxy, undecynyloxy, dodecynyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl, hexyloxymethyl, heptyloxymethyl, octyl Oxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl, nonyloxyethyl, decyloxyethyl, methoxypropyl, Ethoxypropyl, propoxypropyl, butoxypropyl, pentyloxypropyl, hex Oxy propyl, heptyloxy propyl, octyloxy propyl, nonyl propyl,

Decyloxypropyl, methoxybutyl,
Ethoxybutyl, propoxybutyl, butoxybutyl,
Pentyloxybutyl, hexyloxybutyl, heptyloxybutyl, octyloxybutyl, nonyloxybutyl, decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, heptyloxy Pentyl, octyloxypentyl, nonyloxypentyl,
Decyloxypentyl and the like can be mentioned.

In the above examples, specific examples of R ₃ include hydrogen atom, fluorine atom, methyl group, methoxy group, fluoromethyl group, difluoromethyl group, trifluoromethyl group,
Fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, cyano group, optionally substituted with a fluorine atom, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethenyl, Propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, ethoxy,
Propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy,
Decyloxy, undecyloxy, dodecyloxy, vinyloxy, propenyloxy, butenyloxy, pentenyloxy, hexynyloxy, heptenyloxy,
Octenyloxy, nonenyloxy, decenyloxy,
Propynyloxy, butynyloxy, pentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, nonynyloxy, decynyloxy, undecynyloxy, dodecynyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl, hexyloxymethyl, heptyloxymethyl, octyl Oxymethyl, nonyloxymethyl, decyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, pentyloxyethyl, hexyloxyethyl, heptyloxyethyl, octyloxyethyl, nonyloxyethyl, decyloxyethyl, methoxypropyl, Ethoxypropyl, propoxypropyl,

Butoxypropyl, pentyloxypropyl, hexyloxypropyl, heptyloxypropyl, octyloxypropyl, nonyloxypropyl,
Decyloxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, pentyloxybutyl, hexyloxybutyl, heptyloxybutyl, octyloxybutyl, nonyloxybutyl, decyloxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxy. Examples thereof include pentyl, pentyloxypentyl, hexyloxypentyl, heptyloxypentyl, heptyloxypentyl, octyloxypentyl, nonyloxypentyl, decyloxypentyl and the like. Further, W represents a hydrogen atom or a fluorine atom, and x is an integer of 0 to 3.

[0087]

Embedded image Represents 1,4-cyclohexylene,

[0088]

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Is optionally substituted with a fluorine atom,
_1, 4-Feniren'n, _1, 4-cyclohexylene,
1,4-cyclohexylene, 4,1-cyclohexylene, 2,5-cyclohexene, 5,2-cyclohexene, 3,6-cyclohexene, 6,3-cyclohexene, 2,5-pyrimidinediyl, 5 , 2-pyrimidinediyl, 2,5-pyridinediyl, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl. More preferably, in the above formula, ring G may be substituted with a fluorine atom, 1
_, 4-phenylene, 1,4-cyclohexylene, 1,
4-cyclohexelene, 4,1-cyclohexelene,
It is 2,5-cyclohexylene, 5,2-cyclohexene, 3,6-cyclohexene or 6,3-cyclohexene. General formulas (8), (9),
In (15) and (16), W ₁ represents a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a cyano group, and W ₂ and W ₃ each independently represent a hydrogen atom or a fluorine atom. 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, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond is shown. Further, 1 ring L, ring M, ring N and ring P are each _{independently} 4-Feniren'n, _1, 4-cyclohexylene, 4,1-cyclohexylene selenium, 2,5-pyrimidinediyl, 5,2- pyrimidine Indicates diyl, 2,5-dioxanediyl or 5,2-dioxanediyl. More preferably _1, 4-Feniren'n, 1 _are those 4-cyclohexylene or 4,1-cyclohexylene selenium.

The composition may contain one or more chiral compounds as a twisting agent.
The chiral compound is not particularly limited, but the following compounds are preferable.

[0091]

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[0092]

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[0093]

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 composition used in the present invention were measured by the methods described below. -Refractive index anisotropy ((DELTA) n) was calculated | required by measuring retardation using the Senarmont method. The measurement wavelength at this time was 589 nm. The dielectric anisotropy (Δε), which is the difference between the dielectric constants of the liquid crystal molecules in the major axis direction and the minor axis direction, was determined as follows by measuring the capacitance of the liquid crystal composition. That is, the liquid crystal composition is sandwiched between homogeneous alignment cells with transparent electrodes, and the capacitance when a voltage is applied to the cells is measured.
At this time, the dielectric constant in the direction of the major axis of the liquid crystal molecule is calculated by using Equation-2, by obtaining the capacitance when the applied voltage is infinite, from the extrapolated value of the plot of the inverse of the capacitance and the applied voltage. did. On the other hand, the dielectric constant in the minor axis direction of the molecule was similarly obtained from the electrostatic capacity below the threshold voltage, and the dielectric anisotropy (Δε) was obtained by taking the difference between the two dielectric constants. ε * ε0 = C * d / s (Equation-2) (ε0: Dielectric constant of vacuum, C: Capacitance, d: Cell thickness,
s; electrode area) -upper limit temperature (TN) of the N (nematic) phase of the liquid crystal composition
I) was obtained by measuring the clearing point at the time of temperature increase using a polarization microscope. -The viscosity of the liquid crystal composition is measured by an automatic falling ball viscometer
It was measured by PAAR, AMV-200).

Example 1 General formula (4) or (8) or (11) or (1
Compounds (4-1) to (4-4) represented by 5) were mixed in the ratios shown in Table 1 to prepare a composition A.

[0096]

[Table 1] The composition B was prepared by mixing the composition A with the compound (1-1) represented by the general formula (1) or (5) at a ratio shown in Table 2.

[0097]

[Table 2]

Table 3 shows the refractive index anisotropy Δn of the composition A and the composition B at this time.

[Table 3] As is clear from Table 3, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 2 Composition C was prepared by mixing the composition A described in Example 1 with the compound (1-2) represented by the general formula (1) or (5) at the ratio shown in Table 4. .

[0100]

[Table 4] The refractive index anisotropies Δn and N of the compositions A and C at this time
Table 5 shows the maximum temperature (TNI) of the phases.

[0101]

[Table 5] As is clear from Table 5, the composition of the present invention has a large refractive index anisotropy (Δn). In addition to this, the composition has a higher maximum temperature (TNI) of the N phase.

Example 3 Composition D was prepared by mixing the composition A described in Example 1 with the compound (2-1) represented by the general formula (2) or (6) at the ratio shown in Table 6. .

[0103]

[Table 6] Table 7 shows the refractive index anisotropy Δn of the compositions A and D at this time.

[0104]

[Table 7] As is clear from Table 7, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 4 Composition E was prepared by mixing the composition A described in Example 1 with the compound (2-2) represented by the general formula (2) or (6) at the ratio shown in Table 8. .

[0106]

[Table 8] Table 9 shows the refractive index anisotropy Δn and the dielectric anisotropy (Δε) of the compositions A and E at this time.

[0107]

[Table 9] As is clear from Table 9, the composition of the present invention has a large refractive index anisotropy (Δn). In addition to this, the present composition has a high dielectric anisotropy (Δε).

Example 5 Composition F was prepared by mixing the composition A described in Example 1 with the compound (2-3) represented by the general formula (2) or (6) at the ratio shown in Table 10. .

[0109]

[Table 10] Table 11 shows the refractive index anisotropy Δn of the compositions A and F at this time.

[0110]

[Table 11] As is clear from Table 11, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 6 Composition G was prepared by mixing the composition A described in Example 1 with the compound (2-4) represented by the general formula (2) or (6) in the ratio shown in Table 12. .

[0112]

[Table 12] Table 13 shows the refractive index anisotropy Δn of the compositions A and G at this time.

[0113]

[Table 13] As is clear from Table 13, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 7 Composition H was prepared by mixing the composition A described in Example 1 with the compound (2-5) represented by the general formula (2) or (6) at the ratio shown in Table 14. .

[0115]

[Table 14] Table 15 shows the refractive index anisotropy Δn of the compositions A and H at this time.

[0116]

[Table 15] As is clear from Table 15, the composition of the present invention has a large refractive index anisotropy (Δn). In addition to this, the present composition has a high dielectric anisotropy (Δε).

Example 8 General formula (4) or (8) or (11) or (1
Compound (4-1) represented by 5) and compound (4-6) represented by general formula (4) or (9) or (10) or (12) or (16) and compound (4-7) ) Was mixed in the ratio shown in Table 16 to prepare Composition J.

[0118]

[Table 16] The composition K was prepared by mixing the composition J with the compound (2-2) represented by the general formula (2) or (6) in the ratio shown in Table 17.

[0119]

[Table 17] Table 18 shows the refractive index anisotropy Δn of the composition J and the composition K at this time.

[0120]

[Table 18] As is apparent from Table 18, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 9 General formula (4) or (8) or (11) or (1
Composition L was prepared by mixing the compounds (4-1), (4-8) and (4-9) represented by 5) at the ratio shown in Table 19.

[0122]

[Table 19] This composition L was mixed with (2-2) represented by the general formula (2) or (6) at a ratio shown in Table 20 to prepare a composition M.

[0123]

[Table 20] Table 21 shows the refractive index anisotropy Δn of the composition L and the composition M at this time.

[0124]

[Table 21] As is clear from Table 21, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 10 General formula (4) or (8) or (11) or (1
Composition N was prepared by mixing the compounds (4-8) and (4-9) represented by 5) at the ratios shown in Table 22.

[0126]

[Table 22] The ratio of the compound (1-1) represented by the general formula (1) or (5) and the compound (2-1) represented by the general formula (2) or (6) to the composition N shown in Table 23. To prepare composition O (Table 23).

[0127]

[Table 23] Table 24 shows the refractive index anisotropy Δn of the composition N and the composition M at this time.

[0128]

[Table 24] As is clear from Table 24, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 11 General formula (4) or (9) or (10) or (1
The compound (4-6) and the compound (4-7) represented by 2) or (16) are mixed in the ratios shown in Table 25 to obtain the composition P.
Was adjusted.

[0130]

[Table 25] In this composition P, the compounds (1-3), (1-4) and (1-5) represented by the general formula (1) or (5) are shown in Table 26.
The composition Q was adjusted by mixing in the ratio shown in.

[0131]

[Table 26] Table 27 shows the refractive index anisotropy Δn of the composition P and the composition Q at this time.

[0132]

[Table 27] As is clear from Table 27, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 12 The compound (1-3), (1-4), (1-5) represented by the general formula (1) or (5) and the general formula (2) or (6) were added to the composition P. ) Compounds (2-5) and (2
-6) was mixed and added at a ratio shown in Table 28 to prepare a composition R.

[0134]

[Table 28] Table 29 shows the refractive index anisotropy Δn of the compositions P and R at this time.

[0135]

[Table 29] As is clear from Table 29, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 13 The composition P described in Example 11 and the compound (4-5) represented by the general formula (4) or (8) or (11) or (15) at the ratios shown in Table 30 were used. Composition S was prepared by mixing.

[0137]

[Table 30] The composition T was prepared by mixing the composition S with the compound (1-5) represented by the general formula (1) or (5) in the ratio shown in Table 31.

[0138]

[Table 31] Table 32 shows the refractive index anisotropy Δn of the compositions S and T at this time.

[0139]

[Table 32] As is clear from Table 32, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 14 The composition S was prepared by adding the compound (1-5) represented by the general formula (1) or (5) and the compound (2-5) represented by the general formula (2) or (6). Composition U mixed in the proportions shown in Table 33
Was adjusted.

[0141]

[Table 33] Table 34 shows the refractive index anisotropy Δn of the composition S and the composition U at this time.

[0142]

[Table 34] As is clear from Table 34, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 15 The ratio of the composition P described in Example 11 to the compound (4-5) represented by the general formula (4) or (8) or (11) or (15) is shown in Table 35. And mixed to prepare a composition V.

[0144]

[Table 35] The composition V is represented by the compounds (1-3), (1-4), (1-5) represented by the general formula (1) or (5) and the general formula (2) or (6). Compound (2-5), (2
-6) was mixed in the ratio shown in Table 36 to prepare the composition W.

[0145]

[Table 36] Table 37 shows the refractive index anisotropy Δn of the composition V and the composition W at this time.

[0146]

[Table 37] As is clear from Table 37, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 16 The ratio of the composition P described in Example 11 to the compound (4-5) represented by the general formula (4) or (8) or (11) or (15) is shown in Table 38. And mixed to prepare a composition X.

[0148]

[Table 38] The composition X is represented by the compounds (1-3), (1-4), (1-5) represented by the general formula (1) or (5) and the general formula (2) or (6). Compound (2-5), (2
-6) was mixed in the ratio shown in Table 39 to prepare the composition Y.

[0149]

[Table 39] Table 40 shows the refractive index anisotropy Δn of the composition X and the composition Y at this time.

[0150]

[Table 40] As is clear from Table 40, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 17 The composition A described in Example 1 was mixed with the compound (3-1) represented by the general formula (3) at a ratio shown in Table 41 to obtain a composition Z.
Was adjusted.

[0152]

[Table 41] Refractive index anisotropy Δn and N of the composition A and the composition Z at this time
The upper temperature limits (TNI) for the phases are shown in Table 42.

[0153]

[Table 42] As is clear from Table 42, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 18 The composition AA was prepared by mixing the composition P described in Example 11 with the compound (1-6) represented by the general formula (1) in the ratio shown in Table 43.

[0155]

[Table 43] Table 44 shows the refractive index anisotropy Δn of the composition P and the composition AA at this time.

[0156]

[Table 44] As is clear from Table 44, the composition of the present invention has a large refractive index anisotropy (Δn).

Example 19 Compound (4-1) represented by formula (4) or (10)
0) and (4-11) were mixed in the ratios shown in Table 45 to prepare composition AB.

[0158]

[Table 45] The composition AB was mixed with the compound (2-2) represented by the general formula (2) or (6) at a ratio shown in Table 46 to obtain a composition A.
C was adjusted (Table 46).

[0159]

[Table 46] Refractive index anisotropy Δ of composition AB and composition AC at this time
Table 47 shows n, the dielectric anisotropy Δε and the upper limit temperature (TNI) of the N phase.

[0160]

[Table 47] As is clear from Table 47, the refractive index anisotropy (Δn) is large in the composition of the present invention. In addition to this, the composition has a high dielectric anisotropy (Δε) and a high upper limit temperature (TNI) of the N phase.

Example 20 The composition P described in Example 11 was mixed with the compound (4-12) represented by the general formula (4) or (8) or (13) at a ratio shown in Table 48 to form a composition. The product AD was adjusted.

[0162]

[Table 48] This composition AD was mixed with the compound (1-7) represented by the general formula (1) or (5) at a ratio shown in Table 49 to obtain a composition A.
Adjusted E.

[0163]

[Table 49] Refractive index anisotropy Δn of composition AD and composition AE at this time
Is shown in Table 50.

[0164]

[Table 50] As is clear from Table 50, the refractive index anisotropy (Δn) is large in the composition of the present invention.

Example 21 The compound represented by the general formula (1) or (5) (1-
5), the compound (4-6) and the compound (4-7) represented by the general formula (4) or (9) or (10) or (12) or (16), and the general formula (4) or ( The compound (4-5) represented by 8), (11) or (15) is mixed in a ratio shown in Table 51 to obtain a composition AF.
Was prepared.

[0166]

[Table 51] The refractive index anisotropy of the composition AF and the composition A (Δ
n), the viscosity η and the response parameter (η / Δn ² ) are shown in Table 52.

[0167]

[Table 52] Table 52. Refractive index anisotropy Δn, viscosity η, response parameter (η / Δn ² ) As is clear from Table 52, the liquid crystal composition of the present invention has a high refractive index anisotropy (Δn), a low viscosity, and a small response parameter (η / Δn ² ).

Since the liquid crystal composition of the present invention has a high refractive index anisotropy (Δn), by using it, an optical shutter, an STN (super twisted nematic) type liquid crystal element or a PDLC (polymer dispersion type liquid crystal) type liquid crystal element is used. A liquid crystal element that can be used as a display element typified by a liquid crystal element can be provided. Further, since some liquid crystal compositions of the present invention have extremely high specific resistance values, they are also useful for liquid crystal elements using active driving such as TFTs.

[0169]

The liquid crystal composition of the present invention has a high refractive index anisotropy (Δn). In addition to the high refractive index anisotropy, the liquid crystal composition of the present invention also has a high dielectric anisotropy (Δε),
A liquid crystal composition having a wide range of N phases including room temperature, or a liquid crystal composition having excellent response because it exhibits a low viscosity and a small response parameter (η / Δn ² ) in addition to high refractive index anisotropy. Things are included. Further, the liquid crystal composition of the present invention is expected to have a steep threshold characteristic due to the structure of the liquid crystal compound constituting the liquid crystal composition, and is very useful for improving the image quality and the yield of STN liquid crystal elements. is there.

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─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical display location G02F 1/13 500 G02F 1/13 500 (72) Inventor Koichi Fujisawa 6 Kitahara, Tsukuba, Ibaraki Sumitomo Chemical Industrial Stock Company (72) Inventor Yukari Fujimoto 2-10-1, Tsukahara, Takatsuki City, Osaka Prefecture Sumitomo Chemical Co., Ltd. (72) Inventor Tsutomu Matsumoto 2-10-1, Tsukahara City, Takatsuki City, Osaka Prefecture Sumitomo Kagaku Industrial Co., Ltd. (72) Inventor Masayoshi Minai 2-10-1, Tsukahara, Takatsuki City, Osaka Sumitomo Chemical Co., Ltd.

Claims (20)

[Claims] 1. The following general formula (1): (In the formula, R is an alkyl group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms.
A 16 alkenyl group or a C2-C16 alkoxyalkyl group is shown. X ₁ , X ₂ , X ₃ , X ₄ , Y ₁ , Y
₂ , Y ₃ , and Y ₄ each independently represent CH, CF, or N. A is a hydrogen atom, 4-R _1- (cycloalkyl) group, 4-R _1- (cycloalkenyl) group or R ₁
Represents a-(O) p group, R ₁ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms. , P is 0 or 1. Z represents -C≡C- or a single bond. ) Or a compound represented by the following general formula (2): (In the formula, B represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group. R, X ₁ ,
X ₂ , X ₃ , X ₄ , Y ₁ , Y ₂ , Y ₃ , Y ₄ and Z have the same meanings as described above. ) Or a compound represented by the following general formula (3): (In the formula, C is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms,
An alkenyl group having 2 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms, a 4-R _1- (cycloalkyl) group,
4-R _1- (cycloalkenyl) group, R _1- (O) p
Represents a group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group. R, X ₁ , X ₂ , X ₃
, X ₄ , Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₁ and p have the same meanings as described above. And at least one compound selected from compounds represented by the following general formula (4): (In the formula, ring C, ring D, ring E and ring F are each independently 1,4-phenylene and 1,4-cyclohexylene, 1,4-cyclohexene, 4, which may be substituted with a fluorine atom. 1-cyclohexylene, 2,5-cyclohexylene, 5,2-cyclohexene, 3,6-cyclohexylene, 6,3-cyclohexene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5 -Pyridinediyl, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown.
R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms.
R ₃ is 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, an alkyl group having 1 to 12 carbon atoms, or 2 carbon atoms.
To alkenyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 16 carbon atoms or alkoxyalkyl groups having 2 to 16 carbon atoms.
Z ₁ , Z ₂ , and Z ₃ are each independently -COO-,
_{-OCO -, - OCH 2 -,} - CH 2 O-, 1~ carbon atoms
5 represents an alkylene group having 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. J and K each independently represent methylene or -O-.
a, b, c, d, and e are each independently 0 or 1
And satisfies b + c + d ≧ 1. However,
When R ₂ is an alkoxy group, a is 0, and when R ₃ is an alkoxy group, e is 0. When R ₂ and R ₃ are not an alkoxy group, b is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl, or 5 , 2
-In the case of pyridinediyl, b is 0, c is 1, and ring D is 1,4-phenylene, 2,5-pyrimidinediyl, 5,
In the case of 2-pyrimidinediyl, 2,5-pyridinediyl, or 5,2-pyridinediyl, and b is 0, c
Is 0, d is 1, and ring E is 1,4-phenylene, 2,5
-Pyrimidinediyl, 5,2-pyrimidinediyl, 2,
In the case of 5-pyridinediyl or 5,2-pyridinediyl, a is 1, and F is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5- In the case of pyridinediyl or 5,2-pyridinediyl, e is 1. Further, those included in the general formulas (1), (2) and (3) are excluded. )
A liquid crystal composition comprising at least one compound selected from the compounds represented by: 2. At least one compound selected from the compounds represented by the above general formulas (1) and (2), and at least one compound selected from the compounds represented by the above general formula (3). And a liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by the above general formula (4). 3. At least one compound selected from the compounds represented by the general formulas (1) and (2) and at least one compound selected from the compounds represented by the general formula (4). The liquid crystal composition according to claim 1, wherein the liquid crystal composition further comprises: 4. The following general formula (5): (In the formula, R is an alkyl group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms.
12 represents an alkenyl group or an alkoxyalkyl group having 2 to 16 carbon atoms. X ₁ , X ₂ , X ₃ , X ₄ , Y ₁ , Y
₂ , Y ₃ , and Y ₄ each independently represent CH, CF, or N. A is a hydrogen atom, 4-R _1- (cycloalkyl) group, 4-R _1- (cycloalkenyl) group or R ₁
Represents a — (O) p group, R ₁ represents 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, and p is 0 or 1. ) Or a compound represented by the following general formula (6): (In the formula, B represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a cyano group. R, X ₁ ,
X ₂ , X ₃ , X ₄ , Y ₁ , Y ₂ , Y ₃ and Y ₄ have the same meanings as described above. ) Or a compound represented by the following general formula (7): (In the formula, C is a hydrogen atom, 4-R _1- (cycloalkyl)
Group, 4-R _1- (cycloalkenyl) group, R _1- (O)
p group, fluorine atom, trifluoromethyl group, trifluoromethoxy group or cyano group. R ₁ and p have the same meanings as described above. R is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms or 2-1 to 2 carbon atoms.
6 represents an alkoxyalkyl group. X and Y each independently represent a hydrogen atom or a fluorine atom. r and s are 0
To 3 are integers. And at least one compound selected from compounds represented by the following general formula (8): (In the formula, R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms. L, ring M, and ring N are each independently 1,4-phenylene, 1,4-cyclohexylene,
2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown. 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, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond. W ₁ represents a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a cyano group, and W ₂ and W ₃ are independently hydrogen. An atom or a fluorine atom is shown, and f is independently 0 or 1. ) Or a compound represented by the following general formula (9): (In the formula, each R ₂ is independently a hydrogen atom or a carbon number of 1 to 1.
A 12-alkyl group, a C2-C12 alkenyl group, a C1-C16 alkoxy group, or a C2-C16 alkoxyalkyl group is shown. Ring L, Ring M, Ring N and Ring P are each independently 1,4-phenylene and 1,4-
Cyclohexylene, 2,5-pyrimidinediyl, 5,2
-Denotes pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl. Z ₁ , Z ₂ and Z
₃ are independently -COO-, -OCO-, -OCH
₂ -, - CH ₂ O-, an alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group or a single bond having 2 to 5 carbon atoms. f independently represents 0 or 1. And at least one compound selected from the compounds represented by the formula (1). 5. At least one compound selected from the compounds represented by the general formula (5) and the general formula (6), at least one compound selected from the compounds represented by the general formula (7), and The liquid crystal composition according to claim 4, containing at least one compound selected from the compounds represented by the general formulas (8) and (9). 6. A compound selected from at least one compound selected from the compounds represented by the general formulas (5) and (6) and a compound represented by the general formulas (8) and (9). 5. The liquid crystal composition according to claim 4, further comprising: 7. At least one compound selected from the compounds represented by the above general formulas (1) and (2),
The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by the general formula (4). However, in the general formula (4), 1,4-phenylene or 1,4-cyclohexene in which at least one ring of ring C, ring D, ring E and ring F is substituted with a fluorine atom. , 4,1-cyclohexylene, 2,5-cyclohexene, 5,2-cyclohexene, 3,6-cyclohexene, 6,3-cyclohexene, 2,5-
Pyrimidinediyl, 5,2-pyrimidinediyl, 2,5
-Pyridinediyl, 5,2-pyridinediyl, 2,5-
At least one compound that is dioxanediyl or 5,2-dioxanediyl is included. 8. At least one compound selected from the compounds represented by the above general formulas (1) and (2),
In the above general formula (4), the ring F is at least one kind selected from compounds which are optionally substituted by a fluorine atom and are 1,4-cyclohexylene, 2,5-dioxanediyl or 5,2-dioxanediyl. The liquid crystal composition according to claim 1, containing a compound. 9. At least one compound selected from the compounds represented by the above general formulas (1) and (2),
The following general formula (10): (In the formula, ring C, ring D, ring E, R ₂ , R ₃ , Z ₁ , Z ₂ ,
Z ₃ , J, a, b, c and d have the same meanings as described in the general formula (4). The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by the formula (1). 10. At least one compound selected from the compounds represented by the above general formulas (1) and (2), and in the above general formula (4), the ring F is substituted with a fluorine atom. And at least one compound selected from compounds which are 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridindiyl or 5,2-pyridinediyl. The liquid crystal composition according to claim 1. 11. At least one compound selected from the compounds represented by the above general formulas (1) and (2) and the following general formula (11): (In the formula, R ₂ , J, ring C and ring D have the same meanings as described in the above general formula (4). A or g is independently 0 or 1, and f is 0, 1 or However, when R ₂ is an alkoxy group, a is 0. When R ₂ is not an alkoxy group, g is
Is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridinediyl or 5,2-pyridinediyl, a is 1, and Those included in the general formulas (1) and (2) are excluded. ) At least 1 selected from the compounds represented by
The liquid crystal composition according to claim 1, further comprising a compound of one kind. 12. At least one compound selected from the compounds represented by the above general formulas (1) and (2) and the following general formula (12): (In the formula, R ₂ , J, ring C, rings D, a, g and f have the same meanings as described in the general formula (11), and R ₃ and K have the same meanings as those described in the general formula (4). E is R
0 when ₃ is an alkoxy group, 1 otherwise.
Represents However, those included in the general formulas (1) and (2) are excluded. The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by the formula (1). 13. At least one compound selected from the compounds represented by the above general formulas (1) and (2) and the following general formula (13): (In the formula, R ₂ , J, ring C, ring D, a, g and f have the same meanings as described in the general formula (11). However, when R ₂ is an alkoxy group, a is Further, when R ₂ is not an alkoxy group, g is 1 and ring C is 1,4-phenylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-pyridindiyl or 5 , 2-pyridinediyl, a is 1, and those included in the general formulas (1) and (2) are excluded) and the following general formula (14): (In the formula, R ₂ , J, rings C, a, g, R ₃ , K, e and f have the same meanings as described in the general formula (11). H represents 0 or 1. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the compounds represented by formulas (1) and (2). 14. At least one compound selected from compounds represented by the above general formulas (1) and (2), and in the above general formula (4), ring F is substituted with a fluorine atom. 1,4-cyclohexene, 4,
1-cyclohexylene, 2,5-cyclohexene,
The liquid crystal composition according to claim 1, which contains at least one compound selected from compounds showing any one of 5,2-cyclohexene, 3,6-cyclohexene, and 6,3-cyclohexene. 15. At least one compound selected from the compounds represented by the above general formulas (5), (6) and (7), and the following general formula (15): (In the formula, R ₂ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms; L and ring M are each independently 1,4-
Phenylene, 1,4-cyclohexylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl is shown, and W ₁ is a hydrogen atom, a fluorine atom or fluoromethyl. Base,
Difluoromethyl group, trifluoromethyl group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group or cyano group, W ₂ and W ₃ each independently represent a hydrogen atom or a fluorine atom, and f is 0 or 1 Show. ) Or a compound represented by the following general formula (16): (In the formula, R ₂ is independently a hydrogen atom or a carbon number of 1 to 1.
2 represents an alkyl group having 2 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 16 carbon atoms or an alkoxyalkyl group having 2 to 16 carbon atoms, and ring L, ring M and ring N are each independently 1,4- It shows phenylene, 1,4-cyclohexylene, 2,5-pyrimidinediyl, 5,2-pyrimidinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl, and f shows 0 or 1. The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by the formula (1). 16. At least one compound selected from the compounds represented by the above general formulas (5) and (6),
5. At least one compound selected from the compounds represented by the general formula (7) and at least one compound selected from compounds represented by the general formulas (15) and (16). The liquid crystal composition described. 17. A compound selected from the compounds represented by the general formulas (5) and (6) and the compounds represented by the general formulas (15) and (16). The liquid crystal composition according to claim 4, further comprising: 18. An alkyl group, an alkenyl group or an alkoxyalkyl group in which R is substituted with a fluorine atom, or an alkyl group, an alkenyl group or an alkynyl group in which R ₁ , R ₂ or R ₃ is substituted with a fluorine atom. Alternatively, the liquid crystal composition according to claim 1, which is an alkoxyalkyl group. 19. An alkyl group, an alkenyl group, or an alkoxyalkyl group, wherein R is a fluorine atom,
The liquid crystal composition according to claim 4, wherein R ₁ or R ₂ is a fluorine atom-substituted alkyl group, alkenyl group, alkynyl group or alkoxyalkyl group. 20. A liquid crystal device comprising at least one liquid crystal composition selected from the liquid crystal compositions according to claim 1 sandwiched between a pair of electrode substrates.