JPH10236989A - Liquid crystal compound having negative anisotropic value of dielectric constant, liquid crystal composition containing the same and liquid crystal display element using the composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a low-viscosity liquid crystal compound suitable for a liquid crystal display element, excellent in negative anisotropic value of dielectric constant, anisotropy of refractive index, chemical/physical stability and voltage retention, containing a trifluoromethylcyclohexenediyl group in a skeleton structure. SOLUTION: This liquid crystal compound containing a 2- trifluoromethylcylohexene-1,4-diyl group in a skeleton structure is shown by the formula [R<1> and Y<1> are each a 1-20C alkyl, H, a halogen, cyano, etc.; X<1> to X<4> are each a single bond, (CH2 )2 , CH=CH, C<=, COO, etc.; rings A<1> to A<5> are each 2-trifluoromethylcyclohexene-1,4-diyl, trans-cyclohexene-1,4-diyl, 1,4-phenylene, etc.; a<1> to a<5> are each 0 or 1; a<1> +a<2> +a<3> +a<4> +a<5> >=1].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention mainly relates to a liquid crystal display device, for example, a vertical alignment system, IPS = in-plane switching, TFT = thin film transistor, TN = twisted nematic, or STN = super twisted nematic, etc., and especially vertical alignment. TECHNICAL FIELD The present invention relates to a novel liquid crystal compound capable of exhibiting various physical properties suitable for a liquid crystal composition for a system and an IPS, a liquid crystal composition having suitable physical properties using the same, and a liquid crystal display device using the liquid crystal composition. In the present application, the term “liquid crystalline compound” is used as a general term for a compound that exhibits a liquid crystal phase and a compound that does not exhibit a liquid crystal phase but is useful as a component of a liquid crystal composition.

[0002]

BACKGROUND ART Conventionally, various liquid crystal display systems have been proposed. As an example of them, the following display method is mentioned (Latest technology of liquid crystal, edited by the Industrial Research Council (1983)). As a method of using a liquid crystal composition having a positive dielectric anisotropy value, T
N, STN, or TN based AM = active matrix (TFT or MIM = metal, insulating film, metal, etc.) or a method using a liquid crystal composition having a negative dielectric anisotropy value , ECB = field controlled birefringence effect (HAN
= Hybrid molecular arrangement or DAP = vertical molecular arrangement, etc.), DS = dynamic scattering, GH = guest host or PC
= There is a method such as phase transition. Of these systems, the mainstream of those currently in practical use is a system using a liquid crystal composition having a positive dielectric anisotropy value. Compared to this, practical use of the method using a liquid crystal composition having a negative dielectric anisotropy value has been delayed. In connection with this, the development of liquid crystal compositions having a negative dielectric anisotropy value and the compounds used for the same were also compared with the development of liquid crystal compositions having a positive dielectric anisotropy value and the compounds used for the same. Then, it is not enough.

Under these circumstances, recently, attempts to improve the narrow viewing angle, which is one of the drawbacks of the liquid crystal display, have been actively made. One of the methods is
IPS (R. Kiefer et al, JAPAN DISPLAY'92,547
(1992), M. Oh-e et al, ASIADISPLAY '95, 577 (1995), JP-T5-505247, JP-A-7-128647.
No.). One of the features of the IPS is that, in the conventional liquid crystal panel, electrodes are provided on upper and lower substrates, respectively, whereas in the liquid crystal panel of this system, interdigital electrodes are provided only on one substrate. It is. Another feature of this method is that the liquid crystal composition can be used regardless of the positive or negative value of the dielectric anisotropy value. As another example of an attempt to improve the narrow viewing angle, there is a method in which the vertical angle of liquid crystal molecules is used to improve the viewing angle (Japanese Patent Laid-Open No. 2-176625). One of the features of this method is that a liquid crystal composition having a negative dielectric anisotropy is used. From such a background, liquid crystal compounds and liquid crystal compositions having a negative dielectric anisotropy value have been strongly demanded.

In all display systems, the liquid crystal composition used has not only an appropriate dielectric anisotropy value but also other characteristics such as a refractive index anisotropy value (△ n) and an elastic constant ratio K. _It is necessary to adjust various physical property values such as ₃₃ / K ₁₁ (K ₃₃ : bend elastic constant, K ₁₁ : splay elastic constant) to an optimum value, and that the liquid crystal phase is in an appropriate temperature range In addition, low viscosity is required even at a low temperature. None of the conventionally known liquid crystalline compounds satisfy all of these conditions alone. Therefore, in order to obtain a composition that can be usually used as a liquid crystal phase, it is prepared by mixing a compound having several to twenty and several kinds of liquid crystal phases and, if necessary, a compound having no more than several kinds of liquid crystal phases. . Therefore, each liquid crystal compound is
Characteristics such as good compatibility with other liquid crystal compounds and good compatibility in a low temperature range are also required due to demand for use in a low temperature environment.

However, as described above, the conventional display system mainly uses a liquid crystal composition containing a liquid crystal compound having a positive dielectric anisotropy value. However, the development of the compound or composition was not sufficient. For this reason, the method of diversification in this way and the corresponding various characteristics have been insufficient. For example, even if the dielectric anisotropy value is negative, the absolute value is small, the driving voltage cannot be reduced due to the large elastic constant, the compatibility is poor, and the compound cannot be used in large quantities. It is difficult to freely set the value of the refractive index anisotropy, there is a problem that the viscosity is large, and the chemical and physical stability is poor.

As an example of the liquid crystal compound known before the present invention, a liquid crystal compound having a 2-fluorocyclohexene-1,4-diyl skeleton (JP-A-6-21997)
9) and 1-trifluoromethylcyclohexene-4-
Liquid crystalline compound having an il skeleton (German Patent 4,415,
No. 881A1). However, each of these compounds has a positive dielectric anisotropy value, and necessary for using these compounds in a liquid crystal composition, for example, an appropriate refractive index anisotropy value and a small elastic constant. Physical properties such as good compatibility, low viscosity, and high chemical and physical stability are not always satisfactory, and further improvement has been demanded. Here, no attempt has been made to induce a compound having a cyclohexene-1,4-diyl skeleton into a compound having a negative dielectric anisotropy value.
In particular, there has been no idea of introducing a trifluoromethyl group at the 2-position of a compound having a cyclohexene-1,4-diyl skeleton. Thus, the compounds of the present invention are not readily conceivable from the prior art.

[0007]

An object of the present invention is to provide a vertical alignment system, IPS, ECB (HAN or DAP, etc.) as described in JP-A-2-176625,
Not only can it be used for various display methods using compounds or compositions having a negative dielectric anisotropy value such as S, GH or PC, but also TN, STN, or TN-based AM (TF
T or MIM), which solves the above-mentioned problem that can be used for adjusting various characteristics of a liquid crystal composition for various display systems using a compound or a composition having a positive dielectric anisotropy value. It is an object of the present invention to provide a novel liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal display device prepared using the liquid crystal composition.

[0008]

Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above-mentioned problems, and as a result, the compounds according to claims 1 to 2 have not only a large absolute value but a negative dielectric anisotropy value. ,
A liquid crystal composition having a suitable refractive index anisotropy value, a small elastic constant, good compatibility, low viscosity, high chemical and physical stability, and a compound according to claim 1 or 2. When used in a product, the liquid crystal composition has a small elastic constant, can appropriately set the dielectric anisotropy value and the refractive index anisotropy value, has a low viscosity, and has excellent chemical and physical stability. In particular, they have found that a liquid crystal composition having a large absolute value and a negative dielectric anisotropy value can be obtained, and that a liquid crystal display device can be obtained using the composition, thereby completing the present invention.

That is, the present invention provides the following [1] to [1]
2). [1] A liquid crystalline compound having a 2-trifluoromethylcyclohexene-1,4-diyl group in a skeleton structure. [2] General formula (1)

[0010]

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(Wherein R ¹ and Y ¹ each independently represent an alkyl group having 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a cyano group, a cyanate group, an isocyano group or an isothiocyanate group; One or more non-adjacent methylene groups in the alkyl group may be an oxygen atom, a sulfur atom, a nitrogen atom,
C- One or more hydrogen atoms may be substituted with a silylene group which may be substituted with an alkyl group having 1 to 10 carbon atoms, or a vinylene group;
One or more hydrogen atoms may be substituted with a fluorine atom or a chlorine atom, and these alkyl groups may be optically active, and X ¹ , X ² , X ³ and X ⁴ each independently represent a single atom. _{bond, - (CH 2) 2 -} , - CH = CH -, - C≡C -, -
COO -, - OCO -, - CH 2 O -, - OCH 2 -, -
_{(CH 2) 4 -, -} (CH 2) 3 O -, - O (CH 2) 3 -,
_{-CH = CHCH 2 CH 2 -,} - CH 2 CH = CHCH
_{2 -, - CH 2 CH 2} CH = CH -, - CH = CHCH =
_{CH -, - CF 2 O -} , - OCF 2 -, - CH = CHCH
_{2 O -, - OCH 2 CH} = CH -, - CF = CF -, - C
_{H 2 CF 2 -, - CF} 2 CH 2 -, - (CF 2) 2 -, - (C
_{F 2) 4 -, - (} CH 2) 2 COO -, - OCO (CH 2) 2
-, -CH = CHCOO-, -OCOCH = CH-,-
CH ＝ CHC≡C— or —C≡CCH ＝ CH—, wherein ring A ¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are each independently 2-trifluoromethylcyclohexene-1 , 4-
Diyl, bicyclo [1.1.1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,4-diyl, or 1,4-
Represents phenylene, the carbon atoms constituting these rings may be substituted with a nitrogen atom, an oxygen atom or a sulfur atom, and the hydrogen atoms on these rings may be substituted with a halogen atom or a cyano group Has at least one of ring A ¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵
Trifluoromethylcyclohexene-1,4-diyl, and a ¹ , a ² , a ³ , a ⁴ and a ⁵ each independently represent 0 or 1, but a ¹ + a ² + a ³ + a ⁴ + a ⁵ ≧ 1 and
Further, each atom constituting the compound may be substituted with its isotope. The liquid crystalline compound according to item [1], which is represented by the formula (1).

[3] A liquid crystal composition comprising at least two components, comprising at least one liquid crystal compound according to any one of [1] to [2]. [4] As a first component, at least one compound according to any one of the items [1] to [2] is contained, and as a second component, the compounds represented by the general formulas (2), (3) and (4) A liquid crystal composition comprising at least one compound selected from the group consisting of:

[0013]

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(Wherein R ² represents an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group may be substituted with an oxygen atom or —CH ＝ CH—). In addition, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ² is a fluorine atom, a chlorine atom, —OCF ₃ , —OCF ₂ H, —C
_{F 3, -CF 2 H, -CFH} 2, -OCF 2 CF 2 H or -
Represents OCF ₂ CFHCF _3, L ¹ and L ² represents a hydrogen atom or a fluorine atom each independently, Z ¹ and Z ² are each independently _{- (CH 2) 2 -,} - (CH 2) 4 - , -COO-,-
CF ₂ O—, —OCF ₂ —, —CH ＝ CH— or a single bond, and ring Q ¹ is trans-cyclohexane-1,4-diyl, 1,3-dioxane-2,5-diyl, or a hydrogen atom Represents 1,4-phenylene which may be substituted by a fluorine atom, and ring Q ² is trans-cyclohexane-
1,4-diyl or 1,4-phenylene in which a hydrogen atom may be substituted with a fluorine atom, and each atom constituting these compounds may be substituted with its isotope. )

[5] As the first component, [1] to [1]
[2] contains at least one kind of the compound described in any one of the above items, and contains, as a second component, at least one kind of a compound selected from the compound group consisting of the general formulas (5) and (6). A liquid crystal composition characterized by the following.

[0016]

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(Wherein R ³ and R ⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
May be substituted with CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ³ represents a cyano group or -C 環 C-CN; Q ³ is trans-cyclohexane-1,4-diyl,
Represents 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl, and ring Q ⁴ is trans-cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, Or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, and ring Q ⁵ is trans-cyclohexane-1,4-diyl or 1,4
Represents phenylene, and Z ³ represents — (CH ₂ ) ₂ —, —COO
Or represents a single bond, L ³ , L ⁴ and L ⁵ each independently represent a hydrogen atom or a fluorine atom, b, c and d each independently represent 0 or 1, and these compounds The constituent atoms may be substituted by their isotopes. )

[6] As the first component, [1] to [1]
[2] It contains at least one kind of the compound according to any one of the items [2], and as the second component, the above-mentioned general formulas (2) and (3).
And at least one compound selected from the compound group consisting of (4) and at least one compound selected from the compound group consisting of general formulas (7), (8) and (9) as a third component. A liquid crystal composition characterized by containing various types.

[0019]

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(Wherein R ⁵ and R ⁶ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and ring Q ⁶ , ring Q ⁷ and ring Q ⁸ are each independently , Trans-cyclohexane-1,4-diyl, pyrimidine-
Represents 2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, and Z ⁴ and Z ⁵ each independently represent -C≡C-, -COO-,-( CH ₂ ) ₂
Represents-, -CH = CH- or a single bond, and atoms constituting these compounds may be substituted with an isotope thereof. )

[7] As the first component, [1] to [1]
Item (2) contains at least one kind of the compound according to any one of the above items, and as the second component, the compound represented by the above general formula (10) or (1)
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds (1) and (12).

[0022]

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(Wherein, R ⁷ and R ⁸ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and ring Q ⁹ and ring Q ¹⁰ are each independently trans-
Represents cyclohexane-1,4-diyl or 1,4-phenylene, it represents an L ⁶ and L ⁷ each independently represent a hydrogen atom or a fluorine atom not represent simultaneously hydrogen atoms, Z ⁶
And Z ⁷ are each independently — (CH ₂ ) ₂ —, —COO—
Or a single bond, and the atoms constituting these compounds may be substituted with isotopes thereof. )

[8] As the first component, [1] to
[2] It contains at least one kind of the compound according to any one of the items [2], and as the second component, the general formulas (7) and (8).
And at least one compound selected from the compound group consisting of (9) and at least a compound selected from the compound group consisting of the general formulas (10), (11) and (12) as the third component. A liquid crystal composition comprising one type.

[9] As a first component, at least one compound according to any one of the items [1] to [2] is contained, and as a second component, the compound comprises the general formulas (5) and (6). A compound selected from the compound group consisting of the general formulas (7), (8) and (9) as a third component. Characteristic liquid crystal composition.

[10] As the first component, [1] to
[2] It contains at least one kind of the compound according to any one of the items [2], and as the second component, the above-mentioned general formulas (2) and (3).
And at least one compound selected from the compound group consisting of (4) and as a third component at least one compound selected from the compound group consisting of the general formulas (5) and (6). A liquid crystal composition comprising, as a fourth component, at least one compound selected from the compound group consisting of the general formulas (7), (8) and (9). [11] A liquid crystal composition, which further comprises one or more optically active compounds in addition to the liquid crystal composition according to any one of [3] to [10]. [12] A liquid crystal display device formed using the liquid crystal composition according to any one of the items [3] to [11].

The inventions of the items [7] and [8] relate to an N-type (negative Δε) liquid crystal composition. The N-type liquid crystal composition can be driven by various display methods such as a vertical alignment method described in JP-A-2-176625 and IPS. In addition, [4], [5],
[6],

The inventions of the items [9] and [10] relate to a P-type (Δε is positive) liquid crystal composition.
An N-type compound can also be used as a component of the liquid crystal composition. This not only allows the dielectric anisotropy value to be freely set according to the intended use of the liquid crystal composition, but also
Other characteristics, such as control of the refractive index anisotropy value and elastic constant of the liquid crystal composition, are also possible.

Preferred embodiments of the compound of the present invention represented by the general formula (1) are shown below. R ¹ and Y ¹ are each independently an alkyl group having 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a cyano group, a cyanate group, an isocyano group or an isothiocyanate group, and are not adjacent to each other in the alkyl group. One or more methylene groups are an oxygen atom, a sulfur atom, a nitrogen atom, -C≡C-, and one or more hydrogen atoms have 1 to 10 carbon atoms.
May be substituted with a silylene group which may be substituted with an alkyl group, or a vinylene group, and one or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or a chlorine atom. Also, these alkyl groups may be optically active.

As the alkyl group represented by R ¹ and Y ¹ in the general formula (1), specifically, a saturated alkyl group consisting only of carbon atoms and hydrogen atoms, a haloalkyl group,
Alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxyalkyl, haloalkoxyalkyl, alkoxyalkoxy Group, haloalkoxyalkoxy group, alkanoyl group,
Examples include a haloalkanoyl group, an alkanoyloxy group, a haloalkanoyloxy group, an alkoxycarbonyl group, and a haloalkoxycarbonyl group.

More specifically, examples of R ¹ and Y ¹ include the following groups or atoms. -CH _3, -C ₂ H
_{5, -C 3 H 7, -C} 4 H 9, -C 5 H 11, -C 6 H 13, -C 7
_{H 15, -C 8 H 17,} -C 9 H 19, -C 10 H 21, -CF
_{H 2, -CF 2 H, -CF} 3, -CH 2 CH 2 F, -CH 2 C
_{HF 2, -CH 2 CF 3,} -CF 2 CH 3, -CF 2 CF
_{2 H, -CFHCF 3, -CF 2} CF 3, - (CH 2) 2 CH
₂ F,-(CH ₂ ) ₂ CHF ₂ ,-(CH ₂ ) ₂ CF ₃ , -C
_{H 2 CF 2 CH 3, -CH} 2 CF 2 CF 3, -CF 2 C 2 H 5,
_{-C 3 F 7, -CF 2 CFHCF} 3, - (CH 2) 3 CH
_{2 F, - (CH 2)} 4 CH 2 F, - (CH 2) 5 CH 2 F, -
_{CF 2 C 3 H 7, -CH} 2 CF 2 C 2 H 5, - (CH 2) 2 CF 2
_{CH 3, -CF 2 C 4 H} 9, -CH 2 CF 2 CH 3, - (C
_{H 2) 2 CF 2 C 2} H 5, - (CH 2) 3 CF 2 CH 3,

-OCH ₃ , -OC ₂ H ₅ , -OC ₃ H ₇ ,-
_{OC 4 H 9, -OC 5 H} 11, -OC 6 H 1 3, -OC 7 H 15,
_{-OC 8 H 17, -OC 9 H} 19, -OC 10 H 21, -OCFH
_{2, -OCF 2 H, -OCF 3} , -OCH 2 CH 2 F, -O
_{CH 2 CHF 2, -OCH 2 CF} 3, -OCF 2 CH 3, -O
_{CF 2 CF 2 H, -OCFHCF 3} , -OCF 2 CF 3, -
O (CH ₂ ) ₂ CH ₂ F, —O (CH ₂ ) ₂ CHF ₂ , —O
(CH ₂ ) ₂ CF ₃ , —OCH ₂ CF ₂ CH ₃ , —OCH ₂ C
_{F 2 CF 3, -OCF 2 C} 2 H 5, -OC 3 F 7, -OCF 2 C
FHCF ₃ , —O (CH ₂ ) ₃ CH ₂ F, —O (CH ₂ ) ₄ C
_{H 2 F, -O (CH 2} ) 5 CH 2 F, -OCF 2 C 3 H 7, -
OCH ₂ CF ₂ C ₂ H ₅ , —O (CH ₂ ) ₂ CF ₂ CH ₃ , —O
_{CF 2 C 4 H 9, -OCH} 2 CF 2 CH 3, -O (CH 2) 2 C
_{F 2 C 2 H 5, -O} (CH 2) 3 CF 2 CH 3,

-CH = CH ₂ , -CH = CHCH ₃ , -C
_{H = CHC 2 H 5, -CH} = CHC 3 H 7, -CH = CHC
_{4 H 9, -CH 2 CH =} CHCH 3, -CH 2 CH = CHC 2
_{H 5, -CH 2 CH = CHC} 3 H 7, -CH 2 CH = CHC 4
_{H 9, - (CH 2)} 2 CH = CHCH 3, - (CH 2) 2 CH
_{= CHC 2 H 5, - (} CH 2) 2 CH = CHC 3 H 7, - (C
_{H 2) 2 CH = CHC 4} H 9, -CH 2 CH = CH 2, - (C
_{H 2) 2 CH = CH 2} , - (CH 2) 3 CH = CH 2, - (C
_{H 2) 4 CH = CH 2} , - (CH 2) 5 CH = CH 2, -CH
ＣＨCHCH ＝ CH ₂ , —CH ＝ CHCH ₂ CH ＝ CH ₂ ,
_{-CH = CH (CH 2) 2} CH = CH 2, -CH = CH
_{(CH 2) 3 CH = CH} 2, -CH 2 CH = CH (CH 2) 2
_{CH = CH 2, - (CH} 2) 2 CH = CH (CH 2) 2 CH
= CH ₂ ,

-CF = CF ₂ , -CH = CF ₂ , -CH =
_{CHF, -CH 2 CF = CF 2} , -CH 2 CH = CFH,
_{- (CH 2) 2 CH =} CF 2, - (CH 2) 2 CH = CH
_{F, - (CH 2) 3} CH = CF 2, - (CH 2) 3 CH = C
_{HF, - (CH 2) 4} CH = CF 2, - (CH 2) 4 CH =
_{CHF, - (CH 2) 5} CH = CF 2, - (CH 2) 5 CH
_{= CHF, -CH = CHCH 2 CH} 2 F, -CH = CHC
_{H 2 CH 2 Cl, -CH =} CHCH 2 CHF 2, -CH = C
_{HCH 2 CF 3, -CH = CH} (CH 2) 2 CH 2 F, -C
_{H = CH (CH 2) 2} CHF 2, -CH = CH (CH 2) 2
_{CF 3, -CH = CH (CH} 2) 3 CH 2 F, -CH = CH
(CH ₂ ) ₃ CHF ₂ , —CH ＝ CH (CH ₂ ) ₃ CF ₃ ,
_{CH = CH (CH 2) 4} CH 2 F, -CH = CH (CH 2)
₄ CHF ₂ , —CH ＝ CH (CH ₂ ) ₄ CF ₃ , —CH ₂ CH
_{= CH (CH 2) 2 CH} 2 F, -CH 2 CH = CHCH 2 C
_{H 2 F, - (CH 2} ) 2 CH = CH (CH 2) 2 CH 2 F, -
_{(CH 2) 2 CH = CHCH} 2 CH 2 F, -CH = CHCH
_{2 CH = CF 2, -CH =} CH (CH 2) 2 CH = CF 2,
_{-CH = CH (CH 2) 2} CF = CF 2, -CH = CH
(CH ₂ ) ₃ CHFCH ₃ ,

--OCH ₂ CH = CHCH ₃ , --OCH ₂ C
_{H = CHC 2 H 5, -OCH} 2 CH = CHC 3 H 7, -OC
_{H 2 CH = CHC 4 H 9} , -O (CH 2) 2 CH = CHC
_{H 3, -O (CH 2)} 2 CH = CHC 2 H 5, -O (CH 2)
₂ CH = CHC ₃ H ₇ , —O (CH ₂ ) ₂ CH = CHC
_{4 H 9, -OCH 2 CH =} CH 2, -O (CH 2) 2 CH = C
_{H 2, -O (CH 2)} 3 CH = CH 2, -O (CH 2) 4 CH
ＣＨCH ₂ , —O (CH ₂ ) ₅ CH ＝ CH ₂ , —OCH ₂ CH
ＣＨCH (CH ₂ ) ₂ CH 2CH ₂ , —O (CH ₂ ) ₂ CH =
CH (CH ₂ ) ₂ CH = CH ₂ ,

-OCH ₂ CF = CF ₂ , -OCH ₂ CH =
_{CF 2, -OCH 2 CF = CHF} , -O (CH 2) 2 CH =
_{CF 2, -O (CH 2)} 2 CH = CHF, -O (CH 2) 3
CH = CF ₂ , —O (CH ₂ ) ₃ CH = CHF, —O (C
_{H 2) 4 CH = CF 2} , -O (CH 2) 4 CH = CHF, -
_{O (CH 2) 5 CH =} CF 2, -O (CH 2) 5 CH = CH
_{F, -OCH 2 CH = CHCH 2} CH 2 F, -O (CH 2)
_{2 CH = CH (CH 2)} 2 CH 2 F, -O (CH 2) 2 CH =
CHCH ₂ CH ₂ F,

-C≡CH, -C≡CCH ₃ , -C≡CC _{2
H 5, -C≡CC 3 H 7,} -C≡CC 4 H 9, -CH 2 C≡C
_{H, -CH 2 C≡CCH 3, -CH} 2 C≡CC 2 H 5, -C
_{H 2 C≡CC 3 H 7, -CH} 2 C≡CC 4 H 9, - (CH 2) 2
C≡CH, — (CH ₂ ) ₂ C≡CCH ₃ , — (CH ₂ ) ₂ C
_{≡CC 2 H 5, - (CH} 2) 2 C≡CC 3 H 7, - (CH 2) 2
C≡CC ₄ H ₉ , — (CH ₂ ) ₃ C≡CH, — (CH ₂ ) ₃ C
{CCH ₃ ,-(CH ₂ ) ₃ C} CC ₂ H ₅ ,-(CH ₂ ) _{3
C≡CC 3 H 7, - (CH} 2) 3 C≡CC 4 H 9, -C≡CC
_{F 3, -C≡CC 2 F 5,} -C≡CC 3 F 7, -CH 2 C≡C
CF ₃ , — (CH ₂ ) ₂ C≡CCF ₃ ,

[0036] -OCH ₂ C≡CH, -OCH ₂ C≡CCH
₃ , —OCH ₂ C≡CC ₂ H ₅ , —OCH ₂ C≡CC ₃ H ₇ ,
—OCH ₂ C≡CC ₄ H ₉ , —O (CH ₂ ) ₂ C≡CH,
O (CH ₂ ) ₂ C≡CCH ₃ , —O (CH ₂ ) ₂ C≡CC ₂ H
_{5, -O (CH 2) 2} C≡CC 3 H 7, -O (CH 2) 2 C≡
CC ₄ H ₉ , —O (CH ₂ ) ₃ C≡CH, —O (CH ₂ ) ₃ C
{CCH ₃ , —O (CH ₂ ) ₃ C} CC ₂ H ₅ , —O (C
_{H 2) 3 C≡CC 3 H 7} , -O (CH 2) 3 C≡CC 4 H 9,

--OCH ₂ C≡CCF ₃ , --O (CH ₂ ) ₂ C
≡CCF ₃ , —CH ₂ OCH ₃ , —CH ₂ OC ₂ H ₅ , —CH
_{2 OC 3 H 7, -CH 2} OC 4 H 9, -CH 2 OC 5 H 11, -
_{(CH 2) 2 OCH 3,} - (CH 2) 2 OC 2 H 5, - (C
_{H 2) 2 OC 3 H 7} , - (CH 2) 2 OC 4 H 9, - (CH 2) 2
_{OC 5 H 11, - (CH} 2) 3 OCH 3, - (CH 2) 3 OC 2
_{H 5, - (CH 2)} 3 OC 3 H 7, - (CH 2) 3 OC 4 H 9,
— (CH ₂ ) ₃ OC ₅ H ₁₁ , — (CH ₂ ) ₄ OCH ₃ ,

--CF ₂ OCH ₃ , --CF ₂ OC ₂ H ₅ , --C
_{F 2 OC 3 H 7, -CF} 2 OC 4 H 9, -CF 2 OC 5 H 11, -
_{CH 2 OCF 3, -CH 2 OC} 2 F 5, -OCH 2 OCH 3,
_{-OCH 2 OC 2 H 5, -OCH} 2 OC 3 H 7, -OCH 2 O
_{C 4 H 9, -OCH 2 OC} 5 H 11, -O (CH 2) 2 OC
_{H 3, -O (CH 2)} 2 OC 2 H 5, -O (CH 2) 2 OC 3 H
_{7, -O (CH 2) 2} OC 4 H 9, -O (CH 2) 2 OC
_{5 H 11, -O (CH 2} ) 3 OCH 3, -O (CH 2) 3 OC 2
_{H 5, -O (CH 2)} 3 OC 3 H 7, -O (CH 2) 3 OC 4 H
_{9, -O (CH 2) 3} OC 5 H 11, -O (CH 2) 4 OC
H ₃ ,

--OCH ₂ OCF ₃ , --OCH ₂ OC ₂ F ₅ ,
_{-COCF 3, -COCHF 2, -COC 2} F 5, -COC
_{3 F 7, -COCH 2 CF 3} , -OCOCH 3, -OCOC 2
_{H 5, -OCOC 3 H 7,} -OCOC 5 H 11, -OCOC 7
H ₁₅ , —OCOCF ₃ , —OCOCHF ₂ , —OCOC _{2
F 5, -OCOC 3 F 7,} -OCOCH 2 CF 3, -COO
_{CH 3, -COOC 2 H 5,} -COOC 3 H 7, -COOC 4
_{H 9, -COOC 5 H 11,} -COOCH (CH 3) C
_{6 H 13, -COOCH 2 F,} -COOCH 2 CF 3, -CO
_{O (CH 2) 2 CF 3} , -COO (CH 2) 3 CF 3, -CO
O (CH ₂ ) ₄ CH ₂ F,

Hydrogen atom, halogen atom, cyano group, cyanate group, isocyano group and isothiocyanate group.

Chemical formula of the compound represented by the general formula (1)
When particular attention is paid to physical stability, R ¹ and Y ¹ are a saturated alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkoxyalkyl group, a haloalkoxyalkyl group consisting only of a carbon atom and a hydrogen atom, An alkoxyalkoxy group, a haloalkoxyalkoxy group, an alkanoyl group, a haloalkanoyl group, an alkanoyloxy group, a haloalkanoyloxy group, an alkoxycarbonyl group, a haloalkoxycarbonyl group, a hydrogen atom, a halogen atom, a cyano group, a cyanic acid group or an isocyano group Preferably, there is.

When it is desired to increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), R ¹ and Y ¹ are the same as those of a saturated alkyl composed of only carbon atoms and hydrogen atoms. Group, alkoxy group, alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkoxyalkyl group, alkoxyalkoxy group, alkanoyl group, alkanoyloxy group, alkoxycarbonyl group,
Alternatively, a substituent having a small polarity such as a hydrogen atom is preferable.

X ^{1 of} the compound represented by the general formula (1),
X ² , X ³ and X ⁴ are a single bond, — (CH ₂ ) ₂ —, —CH
= CH-, -C≡C-, -COO-, -OCO-, -C
_{H 2 O -, - OCH 2} -, - (CH 2) 4 -, - (CH 2) 3
_{O -, - O (CH 2} ) 3 -, - CH = CHCH 2 CH 2 -,
_{-CH 2 CH = CHCH 2 -,} - CH 2 CH 2 CH = CH
-, - CH = CHCH = CH -, - CF 2 O -, - OC
F ₂ —, —CH ＝ CHCH ₂ O—, —OCH ₂ CH ＝ CH
-, - CF = CF -, - CH 2 CF 2 -, - CF 2 CH
_{2 -, - (CF 2)} 2 -, - (CF 2) 4 -, - (CH 2) 2
_{COO -, - OCO (CH 2} ) 2 -, - CH = CHCOO
—, —OCOCH ＝ CH—, —CH ＝ CHC≡C—, or —C≡CCH ＝ CH—.

The chemical reaction of the compound represented by the general formula (1)
When paying particular attention to physical stability, X ¹ , X ² , X ³ and X ⁴ are each a single bond, — (CH ₂ ) ₂ —, —COO—, or —OC.
_{O -, - CH 2 O -} , - OCH 2 -, - (CH 2) 4 -, -
_{(CH 2) 3 O -,} - O (CH 2) 3 -, - CF 2 O -, -
_{OCF 2 -, - CH 2 CF} 2 -, - CF 2 CH 2 -, - (C
_{F 2) 2 -, - (} CF 2) 4 -, - (CH 2) 2 COO-, or -OCO (CH _{2) 2} - are preferred.

The ring A ^{1 of the} compound represented by the general formula (1)
At least one of ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ is 2-
Trifluoromethylcyclohexene-1,4-diyl, but other preferred rings include bicyclo [1.
1.1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-
1,4-diyl or 1,4-phenylene,
The carbon atoms constituting these rings may be substituted by nitrogen atoms, oxygen atoms or sulfur atoms, and the hydrogen atoms on the rings may be substituted by halogen atoms or cyano groups.

Specifically, 1-cyano-trans-cyclohexane-1,4-diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohex-1-ene-1, 4-diyl, 2,3-
Difluorobenzene-1,4-diyl and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. Further, a hydrogen atom on the ring is a fluorine atom,
The ring which may be substituted with a chlorine atom or a cyano group also includes the following rings. Bicyclo [1.1.
1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,
4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3, 6-diyl, tetrahydropyran-2,
5-diyl, 1,3-dithiane-2,5-diyl, 1,
3-oxathiane-2,5-diyl, and bicyclo [2.2.2] octane-1,4-diyl).

Chemical formula of the compound represented by the general formula (1)
When particular attention is paid to physical stability, ring A ¹ , ring A ² , ring A
^3, the preferred ring to the ring A ⁴ and ring A ⁵ are, is a 2-trifluoromethyl-cyclohexene-1,4-diyl, in other rings, ring A ^1, ring A ^2, ring A ^3, ring A ⁴ and include the rings illustrated below as a preferred ring in the ring a ^5. 1-cyano-trans-cyclohexane-1,4-diyl, 2,
2-difluoro-trans-cyclohexane-1,4-
Diyl, 2-fluorocyclohex-1-ene-1,4
-Diyl, 2,3-difluorobenzene-1,4-diyl, and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. Bicyclo [1.1.1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl as a ring in which a hydrogen atom on the ring may be substituted by a fluorine atom, a chlorine atom or a cyano group; , Cyclohex-1-ene-1,4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyridazine-3 , 6-Diyl, tetrahydropyran-2,5
-Diyl, 1,3-dithiane-2,5-diyl, and 1,3-oxathiane-2,5-diyl.

When it is desired to further increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), the ring A ¹ ,
A preferred ring for ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ is 2-trifluoromethylcyclohexene-1,4-diyl, but other rings include ring A ¹ , ring A ² , Preferred rings for the ring A ³ , the ring A ⁴ and the ring A ⁵ include the following rings. 1-cyano-trans-cyclohexane-1,4-
Diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohex-1-
Ene-1,4-diyl, 2,3-difluorobenzene-
1,4-diyl and 2,2-dichlorobicyclo [1.
1.1] Pentane-1,3-diyl. Trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,4-diyl, pyridazine-3, trans-cyclohexane-1,4-diyl as a ring in which a hydrogen atom on the ring may be substituted with a fluorine atom, a chlorine atom or a cyano group. 6-diyl and tetrahydropyran-
2,5-diyl.

The compound of the present invention according to claim 1 or 2 has a negative value of a dielectric anisotropy having a large absolute value. Therefore, by mainly using the compound of the present invention,
A liquid crystal composition having a negative dielectric anisotropy value can be adjusted. This liquid crystal composition is disclosed, inter alia, in JP-A-2-17662.
No. 5, the vertical alignment method described in
It is useful for producing a device using a liquid crystal composition having a negative dielectric anisotropy value such as S. In addition, by mixing and using the compound of the present invention with another liquid crystal compound or composition, an appropriate setting of the dielectric anisotropy value can be performed. Can be spread. The compound of the present invention according to claim 1 or 2 has a small elastic constant and the temperature dependence of the constant is small. Therefore, a novel liquid crystal composition having a low driving voltage can be prepared by using the compound of the present invention.

The compound of the present invention described in claim 1 or 2 has good compatibility with other liquid crystal compounds. For this reason, when the compound of the present invention is compounded in a liquid crystal composition, problems such as precipitation of the compound hardly occur. In addition, the compound of the present invention can be incorporated in a large amount into a liquid crystal composition,
As a result, the excellent properties of the compound of the present invention can be strongly reflected in the liquid crystal composition.

The compound of the present invention described in claim 1 or 2 can obtain a desired magnitude of refractive index anisotropy value by appropriately designing its structure. That is, when a particularly high refractive index anisotropy value is required, a ring having many sites having a resonance structure such as an aromatic ring may be selected. When a low refractive index anisotropy value is required, a ring having many sites having no resonance structure, such as a trans-cyclohexane-1,4-diyl ring, may be selected. More specifically,
The compound of the present invention represented by the general formula (1) includes R ¹ , Y ¹ ,
X ¹ , X ² , X ³ , X ⁴ , ring A ¹ , ring A ² , ring A ³ , ring A ⁴ , ring A ⁵ , a ¹ , a ² , a ³ , a ⁴ and a ⁵ are appropriately selected. By doing so, a desired value of the refractive index anisotropy value can be obtained.
More specifically, the refractive index anisotropy value can be adjusted by appropriately selecting the ring A ¹ , the ring A ² , the ring A ³ , the ring A ⁴ and the ring A ⁵ . That is, when a particularly high refractive index anisotropy value is required, a ring having many sites having a resonance structure such as an aromatic ring may be selected. When a low refractive index anisotropy value is required, a ring having many sites having no resonance structure, such as a trans-cyclohexane-1,4-diyl ring, may be selected. By freely selecting the refractive index anisotropy value, the degree of freedom in designing the liquid crystal panel is increased.

Each of the compounds of the present invention according to claim 1 or 2 has a low viscosity, and does not significantly increase the viscosity of the whole liquid crystal composition even when used in a large amount in the liquid crystal composition. . Further, the temperature dependence of the viscosity, particularly at low temperatures, is extremely small. By using the liquid crystal compound having the excellent viscosity, a liquid crystal composition having a high-speed response can be adjusted. Each of the compounds of the present invention described in claim 1 or 2 is chemically and physically stable, and a liquid crystal composition using the compound has a high specific resistance and a high voltage holding ratio.
It has high stability against external factors such as ultraviolet rays and heating, and has sufficient chemical and physical stability as a component of a practical liquid crystal composition.

The phase transition temperature of the compound of the present invention according to claim 1 or 2 can be adjusted by appropriately selecting the number of rings. That is, a compound having four or more rings is required when a particularly high clearing point is required, a three-ring compound is required when a moderate clearing point is required, and a two-ring compound is required when a particularly low clearing point is required. You just have to select More specifically, the compound of the present invention represented by the general formula (1) can adjust its phase transition temperature by appropriately selecting a ¹ , a ² , a ³ , a ⁴ and a ^5. Can be. That is, when a particularly high transparent point is required, a ¹ + a ² + a ³ + a ⁴ +
When a compound having four or more rings satisfying a ⁵ ≧ 4 needs a moderate clearing point, a ¹ + a ² + a ³ + a ⁴ + a ⁵ = 3 is satisfied.
When the ring compound is required, especially when a low clearing point is required, a ¹
It is sufficient to select a bicyclic compound in which + a ² + a ³ + a ⁴ + a ⁵ = 2.

As described above, the compound of the present invention described in claim 1 or 2 has various physical properties suitable as an electro-optical display material. By using the compound of the present invention, a novel liquid crystal composition having good characteristics can be prepared. In addition, a liquid crystal compound having desired characteristics, a liquid crystal composition and a liquid crystal display device using the same can be obtained by appropriately designing the structure according to the application. For example, although the compound of the present invention is characterized by exhibiting a large negative dielectric anisotropy value, it can be used not only for a liquid crystal composition having a negative dielectric anisotropy value but also for a positive liquid crystal composition. It can be added to a composition having a dielectric anisotropy value to adjust the dielectric anisotropy value and other properties. More specifically, the compound of the present invention or a liquid crystal composition using the same may be prepared in various display systems using a compound or a composition having a negative dielectric anisotropy value (for example, described in JP-A-2-176625). Vertical alignment method, IPS, ECB (HAN or DAP etc.), DS, GH or PC etc., especially vertical alignment method as described in JP-A-2-176625 or IPS. it can. However, not only can they be used in those methods, but also various display methods (for example, TN,
STN or TN based AM (TFT or MI
M) etc.) (for example, dielectric anisotropy value, elastic constant, refractive index anisotropy value, viscosity,
It can also be used to improve or adjust physical stability).

Hereinafter, the liquid crystal composition of the present invention will be described. The liquid crystal composition according to the present invention comprises at least one compound according to any one of claims 1 to 2 in the range of 0.1 to 99.9.
It is preferable that the content is contained in a ratio of% by weight in order to exhibit excellent characteristics. More specifically, the liquid crystal composition provided by the present invention comprises, in addition to a first component containing at least one compound according to any one of claims 1 to 2, a general formula ( It is completed by mixing the compounds selected from the compound group represented by 2) to (12) at an appropriate ratio. The compounds represented by the general formulas (2) to (4) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ² and Y ² represent the same meaning as described above.)

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The compounds represented by the general formulas (2) to (4) are compounds having a positive dielectric anisotropy value, have excellent thermal stability and chemical stability, and particularly have a high voltage holding property. High rate,
Alternatively, when a liquid crystal composition for TFT requiring high reliability such as a large specific resistance value is prepared, it is a preferable compound. When adjusting the liquid crystal composition for TFT,
The compound represented by the general formulas (2) to (4) can be used in an amount of 0.1 to 99.9% by weight based on the total weight of the liquid crystal composition, but preferably 10 to 97% by weight. %, More preferably 40 to 95% by weight. Further, the compounds represented by the general formulas (7) to (9) may be further contained for the purpose of adjusting the viscosity. When preparing a liquid crystal composition for STN or TN, the compounds represented by general formulas (2) to (4) can also be used. In that case, the use amount of 50% by weight or less is preferable.

The compounds represented by formulas (5) and (6) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ³ , Y ³ and R ⁴
Represents the same meaning as described above. )

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The compounds represented by the general formulas (5) and (6) have a positive and large dielectric anisotropy value, and are used particularly for the purpose of reducing the threshold voltage of the liquid crystal composition. Also,
It is also used for the purpose of expanding the nematic range such as adjusting the refractive index anisotropy value and increasing the clearing point. Further, it is also used for the purpose of improving the steepness of the VT curve of the liquid crystal composition for STN or TN.

The compounds represented by the general formulas (5) and (6) are preferable compounds particularly when preparing liquid crystal compositions for STN and TN. When the amount of the compounds represented by the general formulas (5) and (6) is increased, the threshold voltage of the liquid crystal composition decreases and the viscosity increases. Therefore,
As long as the viscosity of the liquid crystal composition satisfies the required characteristics, it is advantageous to use a large amount of the liquid crystal composition because low-voltage driving can be performed. The amount of the compounds represented by the general formulas (5) and (6) is 0.1 to 9 when adjusting the liquid crystal composition for STN or TN.
Although it can be used in the range of 9.9% by weight,
It is 97% by weight, more preferably 40 to 95% by weight.

The compounds represented by formulas (7) to (9) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ⁵ and R ⁶ represent the same meaning as described above.)

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The compounds represented by the general formulas (7) to (9) are compounds having a small absolute value of dielectric anisotropy and being almost neutral. The compound represented by the general formula (7) is mainly used for the purpose of adjusting the viscosity or adjusting the refractive index anisotropy value. Further, the compounds represented by the general formulas (8) and (9) are used for the purpose of expanding the nematic range such as increasing the clearing point or adjusting the refractive index anisotropy value. General formula (7)-
When the amount of the compound represented by (9) is increased, the threshold voltage of the liquid crystal composition increases, and the viscosity decreases.
Therefore, as long as the required value of the threshold voltage of the liquid crystal composition is satisfied, it can be used in a large amount. General formula (7)
When preparing a liquid crystal composition for TFT, the amount of the compound represented by (9) is preferably 40% by weight, more preferably 35% by weight or less. In addition, when adjusting the liquid crystal composition for STN or TN, preferably 7
0% by weight or less, more preferably 60% by weight or less.

The compounds represented by formulas (10) to (12) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ⁷ and R ⁸ represent the same meaning as described above.)

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The compounds represented by the general formulas (10) to (12) are compounds having a negative value of dielectric anisotropy similarly to the compound according to claim 1 or 2 of the present invention. It is used as a base compound of an N-type liquid crystal composition or for controlling the dielectric anisotropy of a P-type liquid crystal composition. As another application, the compound represented by the general formula (10) is a bicyclic compound, and is mainly used for adjusting a threshold voltage, adjusting a viscosity, or adjusting a refractive index anisotropy value. The general formula (1
The compound represented by 1) is used for the purpose of widening the nematic range such as increasing the clearing point or adjusting the refractive index anisotropy value. The compound represented by the general formula (12) is used for the purpose of increasing the nematic range, reducing the threshold voltage, and increasing the refractive index anisotropy value.

The compounds represented by the general formulas (10) to (12) are mainly used for N-type liquid crystal compositions. Increasing the amount of the compounds decreases the threshold voltage of the liquid crystal composition. Becomes larger. Therefore, it is desirable to use a small amount as long as the required value of the threshold voltage of the liquid crystal composition is satisfied. However, the absolute value of the negative dielectric anisotropy is 5
If the amount is less than 40% by weight, low-voltage driving may not be performed. General formulas (10) to (1)
The amount of the compound represented by 2) is preferably 40% by weight or more, more preferably 50 to 95% by weight, when a liquid crystal composition for an N-type TFT is prepared. In order to control the elastic constant and control the voltage-transmittance curve (VT curve) of the liquid crystal composition, the general formula (10) is used.
The compound represented by (12) may be mixed with the P-type composition. In this case, the amount of the compounds represented by the general formulas (10) to (12) is preferably 30% by weight or less.

The liquid crystal composition of the present invention contains OCB
(Optically Compensated Bi
Except for a special case such as a liquid crystal composition for reference, usually, a helical structure of the liquid crystal composition is induced to adjust a required twist angle, and reverse twist (reverse twist) is performed.
For the purpose of preventing ist), an optically active compound is added. In the present invention, any of the known optically active compounds used for such a purpose can be used. Preferred examples of the compound include the following optically active compounds.

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In the liquid crystal composition of the present invention, these optically active compounds are usually added to adjust the twist pitch. The twist pitch is preferably adjusted in the range of 40 to 200 μm for a liquid crystal composition for TFT and TN. In the case of a liquid crystal composition for STN, it is preferable to adjust the composition to a range of 6 to 20 μm. In addition, bistable TN (Bis
In the case of table TN), the thickness is preferably adjusted to a range of 1.5 to 4 μm. Further, two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the pitch.

The liquid crystal composition of the present invention comprises a merocyanine compound,
A dichroic dye such as a styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye can be added to be used as a liquid crystal composition for GH. Alternatively, NCAP prepared by microencapsulating nematic liquid crystal, or polymer network liquid crystal display device (PN
Polymer-dispersed liquid crystal display device (P
It can also be used as a liquid crystal composition for DLCD). In addition, it can be used as a liquid crystal composition for DS.

The liquid crystal composition of the present invention is prepared by a conventional method. Generally, a method of dissolving various components at a high temperature is used.

The compound of the present invention described in claim 1 or 2 can be easily produced by a known organic synthetic chemistry technique. One example of the production method is shown in Reaction Formula 1.

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Hereinafter, the above synthesis route will be described. Compounds of the formula 1, known techniques (e.g., Ch
em. Ber., 119 , 387 (1986), Sucrow, etc.). The compound represented by the formula 1 is reacted with trimethyl (trifluoromethyl) silane in the presence of TBAF (tetrabutylammonium fluoride) to be derived into the compound represented by the formula 2 . The compound represented by Formula 2 is
By the action of DAST (Et ₂ NSF ₃ ), it is derived to the target compound represented by the formula 3 .

[0080]

EXAMPLES The production method and use examples of the compound of the present invention will be described in more detail with reference to the following examples. The present invention is not limited by the embodiments. In the description of the examples, N is the specified concentration (gram equivalent / l), M
Represents a molar concentration (mol / l), and Δε of the liquid crystalline compound
(Dielectric anisotropy value) is an extrapolated value (2) from a composition comprising the following base liquid crystal A (85 wt%) and the compound (15 wt%).
Δn (measured at 5 ° C.)
Is the following mother liquid crystal B85wt% and the compound 15wt%
And the measured value (measured at 25 ° C.) of the composition consisting of: Composition of mother liquid crystal A

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Five types of ester compounds represented by the above general formula and having different alkyl groups (R ⁹ , R ¹⁰ ) at both ends are represented by the following formula:
The following mixture was mixed to obtain mother liquid crystal A.

Composition of Mother Liquid Crystal B

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Mother liquid crystals B were obtained by mixing four kinds of compounds represented by the above general formulas and having different terminal alkyl groups (R ¹¹ , R ¹² ) at the following ratios.

Example 1 Synthesis of 1- (trans-4- (trans-4-n-propylcyclohexyl) cyclohexyl) -2-trifluoromethyl-4-n-propylcyclohexene ( 3 ) First Step 1-Trifluoro Synthesis of methyl-2- (trans-4- (trans-4-n-propylcyclohexyl) cyclohexyl) -5-n-propylcyclohexanol ( 2 ) 2- (trans-4- (trans-4-n-propylcyclohexyl) ) Cyclohexyl) -5-n-propylcyclohexanone ( 1 ) (34.66 g, 0.100 mo)
l), TBAF (0.200 g, 0.000765 mo
l) and THF (tetrahydrofuran) (250 ml)
Was cooled to −3 ° C. and trimethyl (trifluoromethyl) silane (170.64 g, 1.20 m
ol) was dropped, and the mixture was reacted for 1 hour. After the reaction,
After adding 1N diluted hydrochloric acid (100 ml) and stirring for 10 minutes, the reaction solution was concentrated under reduced pressure. The mixture was extracted with t-butyl methyl ether (250 ml).
00 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate / ethanol = 20/1) to give 1-trifluoromethyl-2- (trans-4- (trans-4). -N-propylcyclohexyl) cyclohexyl) -5-n-propylcyclohexanol ( 2 ) (28.50 g, 0.068)
4 mol; yield 68%). MS / 417
(M ⁺ ).

Second Step Synthesis of 1- (trans-4- (trans-4-n-propylcyclohexyl) cyclohexyl) -2-trifluoromethyl-4-n-propylcyclohexene ( 3 ) Obtained in the first step 1-trifluoromethyl-2- (trans-4- (trans-4-n-propylcyclohexyl) cyclohexyl) -5-n-propylcyclohexanol ( 2 ) (28.36 g, 0.0681 mol) in methylene chloride (120 ml) ) Add DAST to the solution at 0 ° C
(16.46 g, 0.102 mol) was added dropwise in 30 minutes. After the completion of the dropwise addition, the temperature was raised to room temperature, 1 hour, and then 30 ° C.
For 3 hours. After completion of the reaction, water (200
ml) and then extracted with toluene (400 ml). After the obtained organic layer was washed with water (200 ml),
It was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane) and further recrystallized from hexane to give 1- (trans-4- (trans-4-n-propylcyclohexyl). (Cyclohexyl) -2-trifluoromethyl-4-n-propylcyclohexene ( 3 )
(11.40 g, 0.0286 mol; yield 42%) was obtained. MS / 399 (M ⁺ ), Δε = −2.0, Δn =
0.126.

The following compounds can be synthesized according to the method of Example 1.

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As described above, according to the present invention, a low-viscosity, large-value negative dielectric anisotropy value, a controlled optical anisotropy value, a high specific resistance value and a high It is possible to provide a liquid crystal compound which has a voltage holding ratio and is stable against heat or ultraviolet irradiation, a liquid crystal composition containing the same, and a liquid crystal display element manufactured using the liquid crystal composition. Was.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 239/26 C07D 239/26 C07F 7/08 C07F 7/08 C C09K 19/04 C09K 19/04 19/42 19/42 G02F 1/13 500 G02F 1/13 500 // C07M 7:00

Claims (12)

[Claims] 1. A liquid crystal compound having a 2-trifluoromethylcyclohexene-1,4-diyl group in a skeletal structure. 2. A compound of the general formula (1) (Wherein, R ¹ and Y ¹ each independently represent an alkyl group having 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a cyano group, a cyanate group, an isocyano group, or an isothiocyanate group; One or more methylene groups which are not adjacent to each other are an oxygen atom, a sulfur atom, a nitrogen atom, -C≡C-, and a silylene group in which one or more hydrogen atoms may be substituted by an alkyl group having 1 to 10 carbon atoms Or one or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or a chlorine atom, and these alkyl groups may be optically active. Well,
X ¹ , X ² , X ³ and X ⁴ are each independently a single bond,-(CH
₂ ) _2- , -CH = CH-, -C≡C-, -COO-,-
_{OCO -, - CH 2 O -} , - OCH 2 -, - (CH 2)
_{4 -, - (CH 2)} 3 O -, - O (CH 2) 3 -, - CH =
CHCH ₂ CH ₂ —, —CH ₂ CH = CHCH ₂ —, —CH
₂ CH ₂ CH = CH-, -CH = CHCH = CH-, -C
_{F 2 O -, - OCF 2} -, - CH = CHCH 2 O -, - O
_{CH 2 CH = CH -, -} CF = CF -, - CH 2 CF
_{2 -, - CF 2 CH 2} -, - (CF 2) 2 -, - (CF 2) 4
_{-, - (CH 2) 2} COO -, - OCO (CH 2) 2 -, -
CH = CHCOO-, -OCOCH = CH-, -CH =
CHC≡C— or —C≡CCH ＝ CH—, and a ring A
¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are each independently 2-
Trifluoromethylcyclohexene-1,4-diyl,
Bicyclo [1.1.1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,4-diyl or 1,4-phenylene, Is a nitrogen atom,
It may be substituted with an oxygen atom or a sulfur atom, and the hydrogen atom on these rings may be substituted with a halogen atom or a cyano group, and these ring A ¹ , ring A ² , ring A ³ , at least one of the rings a ⁴ and ring a ⁵ are a 2-trifluoromethyl-cyclohexene-1,4-diyl,
a ¹ , a ² , a ³ , a ⁴ and a ⁵ each independently represent 0 or 1, but a ¹ + a ² + a ³ + a ⁴ + a ⁵ ≧ 1, and each atom constituting the compound May be substituted with its isotope. The liquid crystalline compound according to claim 1, which is represented by the formula: 3. A liquid crystal composition comprising at least two components, comprising at least one kind of the liquid crystal compound according to claim 1. 4. A compound containing at least one compound according to claim 1 as a first component, and a compound represented by general formulas (2), (3) and (4) as a second component. A liquid crystal composition comprising at least one compound selected from the group consisting of: Embedded image (Wherein, R ² represents an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group may be substituted with an oxygen atom or —CH ＝ CH—,
One or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ² is a fluorine atom, a chlorine atom, —OCF ₃ , —OCF ₂ H, —CF ₃ , —CF ₂ H ,
-CFH _2, -OCF ₂ CF ₂ H or -OCF ₂ CFHCF
₃ represents, L ¹ and L ² represents a hydrogen atom or a fluorine atom each independently, Z ¹ and Z ² are each independently - (CH _{2) 2
-, - (CH 2) 4} -, - COO -, - CF 2 O -, - O
CF ₂ —, —CH ＝ CH— or a single bond, and ring Q ¹ is trans-cyclohexane-1,4-diyl, 1,3-dioxane-2,5-diyl, or a hydrogen atom is substituted by a fluorine atom. And ring Q ² is trans-cyclohexane-1,4-diyl or 1,4 optionally substituted with a hydrogen atom by a fluorine atom.
Represents phenylene, and each atom constituting these compounds may be substituted with its isotope. ) 5. A compound comprising at least one compound according to claim 1 or 2 as a first component, and
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (5) and (6). Embedded image (Wherein, R ³ and R ⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. may be, also, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y ³
Represents a cyano group or —C≡C—CN, and ring Q ³ represents trans-cyclohexane-1,4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5. A ring Q ⁴ represents trans-cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom; ⁵ represents trans-cyclohexane-1,4-diyl or 1,4-phenylene, Z ³ represents — (CH ₂ ) ₂ —, —COO— or a single bond, and L ³ , L ⁴ and L ⁵ each represent Each independently represents a hydrogen atom or a fluorine atom, and b, c and d each independently represent 0 or 1
And the atoms constituting these compounds may be substituted with their isotopes. ) 6. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (2), (3) and (4), and as a third component, consists of the general formulas (7), (8) and (9) A liquid crystal composition comprising at least one compound selected from a compound group. Embedded image (Wherein, R ⁵ and R ⁶ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. And at least one hydrogen atom in the alkyl group may be substituted with a fluorine atom.
^6, ring Q ⁷ and ring Q ⁸ are each independently trans - cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, or a hydrogen atom may be substituted with a fluorine atom 1,4 Represents phenylene, and Z ⁴ and Z ⁵ are each independently —C≡C—, —COO—, — (CH ₂ ) ₂ —, —CH
ＣＨCH— or a single bond, and the atoms constituting these compounds may be substituted with their isotopes. ) 7. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (10), (11) and (12). Embedded image (Wherein, R ⁷ and R ⁸ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. And at least one hydrogen atom in the alkyl group may be substituted with a fluorine atom.
⁹ and ring Q ¹⁰ are each independently trans - represents a cyclohexane-1,4-diyl or 1,4-phenylene, L
⁶ and L ⁷ each independently represent a hydrogen atom or a fluorine atom but do not represent a hydrogen atom at the same time, and Z ⁶ and Z ⁷ each independently represent-(CH ₂ ) _2- , -COO- or The atoms representing a bond and constituting these compounds may be substituted with their isotopes. ) 8. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (7), (8) and (9), and as a third component, the general formulas (10), (11) and (1)
A liquid crystal composition comprising at least one compound selected from the compound group consisting of 2). 9. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (5) and (6), and as a third component, a compound selected from the compound group consisting of the general formulas (7), (8) and (9). A liquid crystal composition comprising at least one selected compound. 10. A compound comprising at least one compound according to claim 1 or 2 as a first component, and a compound consisting of the general formulas (2), (3) and (4) as a second component. Containing at least one compound selected,
The third component contains at least one compound selected from the compound group consisting of the general formulas (5) and (6), and the fourth component contains the general formulas (7), (8) and (9) A liquid crystal composition comprising at least one compound selected from the group consisting of: 11. A liquid crystal composition comprising at least one optically active compound in addition to the liquid crystal composition according to claim 3. Description: 12. A liquid crystal display device comprising the liquid crystal composition according to claim 3. Description: