JPH1129581A - Liquid crystal compound with negative permitivity anisotropy value, liquid crystal composition containing the liquid crystal compound, and liquid crystal display element using the liquid crystal compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound capable of being applied to preparation of a liquid crystal composition for various kinds of display systems, including a vertical orientation system, etc., using a compound or composition having a permittivity anisotropy value being not only negative but also positive. SOLUTION: This compound is a liquid crystal one of formula I [R<1> and Y are an 1-30C straight chain or branched chain alkyl or the like.; rings A<1> to A<5> are separately a silacyclohexane ring, a ring of formula II (W<1> and W<2> are separately F or Cl) or the like; X<1> to X<4> are separately a single bond, an 1-4C alkylene; R<2> and R<3> are each H, halogen or the like; a<1> to a<5> are separately 0 or 1], e.g. a compound of formula III. A compound of formula I is obtained e.g. through the processes of a formation of the ring of formula II, formation of a silacyclohexane ring, introduction of a difluoromethyleneoxy, etc. According to this, there provides a liquid crystal compound having a low viscosity and negative permittivity anisotropy value whose absolute value is large, having a controlled optical anisotropy value and high specific resistance, etc., and stable against heat and ultraviolet irradiation.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention mainly relates to a liquid crystal display device, for example, a vertical alignment system, an in-plane switching (IPS) system, a thin film transistor (TFT) system, a twisted nematic (TN) system, or a super-twisted nematic (STN) system. A novel liquid crystal compound which develops various physical properties suitable for liquid crystal compositions for various display systems, in particular, a vertical alignment system and an IPS system, more specifically, a ring represented by the general formula (2), a silacyclohexane ring, The present invention relates to a liquid crystal compound having both a difluoromethyleneoxy group and a difluoromethyleneoxy group, a liquid crystal composition having suitable physical properties using the same, and a liquid crystal display device using the liquid crystal composition. Compounds that do not exhibit a liquid crystal phase but are useful as constituents of liquid crystal compositions. Used as a generic term of compounds.).

[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, TN
Active matrix (AM) method (thin film transistor (TF
T) method, metal / insulating film / metal (MIM) method, etc.). As a method of using a liquid crystal composition having a negative dielectric anisotropy value, ECB = electric field control birefringence effect (EC
B) method (including hybrid molecular arrangement (HAN) method or vertical molecular arrangement (DAP) method), dynamic scattering (D
S) method, guest host (GH) method, phase transition (PC) method, and the like. 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 a liquid crystal composition having a negative dielectric anisotropy value and the compound itself used for the same have also
In comparison with the development of a liquid crystal composition having a positive dielectric anisotropy value or a compound used for the composition, the situation is not sufficient.

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 the IPS method (R. Kiefer et al., JAPAN DISPLA
Y'92,547 (1992), M. Oh-e et al., ASIA DISPLAY'95,577 (19
95), JP-T 5-505247, JP-A 7-12
No. 8647). One of the features of the IPS system is that, in the conventional liquid crystal panel, electrodes are provided on the upper and lower substrates, respectively, whereas in the liquid crystal panel of the present system, interdigital electrodes are provided only on one substrate. Is a point. 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. Another example of an attempt to improve the narrow viewing angle is a method utilizing vertical alignment of liquid crystal molecules (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.

[0004] By the way, in any display method,
The liquid crystal composition used is not only a dielectric anisotropy value,
Refractive index anisotropy value (△ n), elastic constant ratio K ₃₃ / K
₁₁ (K _33: bend elastic constant, K _11: splay elastic constant)
It is necessary to adjust various physical property values such as the value of the above to each other, and further, it is required that the liquid crystal phase is in an appropriate temperature range and that the viscosity is low even at a low temperature.
None of the conventionally known liquid crystalline compounds satisfy all of these conditions alone. Therefore, the liquid crystal substance usually used is a liquid crystal composition 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 required to have properties such as good compatibility with other liquid crystal compounds and good compatibility in a low temperature region from a demand for use in a low temperature environment. I have.

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. Therefore, it cannot be said that the development of compounds and compositions which are not sufficient is not sufficient, and therefore, conventional liquid crystalline compounds and liquid crystal compositions cannot cope with diversifying display methods and various demanding characteristics that change accordingly. Was enough. 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 a liquid crystal compound having a negative dielectric anisotropy value known before the present invention,
Examples thereof include a liquid crystal compound having a 3-difluorophenylene skeleton (JP-A-2-4725).

[0006]

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However, the absolute value of the negative dielectric anisotropy value of these compounds is not always sufficiently large, and the elastic constant is small, the compatibility with other liquid crystal materials, and the refractive index anisotropy value. The characteristics such as flexibility, low viscosity, high electrical insulation, wide liquid crystal phase temperature range, and chemical / physical stability were not always satisfactory, and further improvement was required. Prior to the present invention, liquid crystalline compounds having a silacyclohexane ring have already been reported (for example, JP-A-7-70148, JP-A-7-252273).
And JP-A-7-173176).

[0008]

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However, physical properties required for using the compound disclosed herein in a liquid crystal composition, such as an appropriate refractive index anisotropy value, a small elastic constant, compatibility with other liquid crystal materials,
Characteristics such as low viscosity, high electrical insulation, wide liquid crystal phase temperature range, and chemical / physical stability are not always satisfactory.In particular, they do not have negative absolute dielectric anisotropy with a large absolute value. Improvement was required. Further, there is no idea here for inducing a compound having a silacyclohexane ring into a liquid crystal compound having a negative dielectric anisotropy value. Further, prior to the present invention, liquid crystalline compounds having a difluoromethyleneoxy group have already been reported (JP-A-2-289529, JP-A-5-112778, etc.).

[0010]

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However, physical properties required for using the compound disclosed herein in a liquid crystal composition, such as an appropriate refractive index anisotropy, a small elastic constant, compatibility with other liquid crystal materials,
Characteristics such as low viscosity, high electrical insulation, wide liquid crystal phase temperature range, and chemical / physical stability are not always satisfactory.In particular, they do not have negative absolute dielectric anisotropy with a large absolute value. Improvement was required. Further, there is no idea here for inducing a compound having a difluoromethyleneoxy group into a liquid crystal compound having a negative dielectric anisotropy value. As described above, conventionally, a liquid crystal compound having a negative dielectric anisotropy has not been sufficiently studied. In particular, studies on liquid crystal compounds having characteristics suitable for application to systems such as the IPS system and the vertical alignment system described in JP-A-2-176625 have not been sufficient. Above all, to achieve this goal,
There has been no idea to introduce, for example, a silacyclohexane ring and difluoromethyleneoxy into a compound having difluorophenylene. Thus, the compounds of the present invention are not readily conceivable from the prior art.

[0012]

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

[0013]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, the general formula (1)

[0014]

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(Wherein R ¹ and Y ^{1 each} represent a linear or branched alkyl group having 1 to 30 carbon atoms, and any methylene group in these groups may be -O-, -S-, -CO-, -CS-,
—CH ＝ CH—, —C≡C—, —SiR ² R ³ —, cyclopropane-1,2-diyl, cyclobutane-1,3-diyl, or bicyclo [1.1.1] pentane-1,3
-O- and -S optionally substituted with -diyl
Is not continuous, and one or more hydrogen atoms in R ¹ may be substituted with a halogen atom or a cyano group; ring A ¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ each independently represents a silacyclohexane ring, cyclohexane-1,4
-Diyl, 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, bicyclo [1. 1.1] Pentane-1,3-diyl or a ring represented by the general formula (2), and any one or two hydrogen atoms on these rings may be substituted with a halogen atom. Often,

[0016]

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(Wherein W ¹ and W ² each independently represent a fluorine atom or a chlorine atom), provided that ring A ¹ , ring A ² ,
At least one of ring A ³ , ring A ⁴ and ring A ^{5 is} a ring represented by formula (2), and at least one is a silacyclohexane ring; X ¹ , X ² , X ³ and X ^{And 4} each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms in which one or more hydrogen atoms in the group may be substituted with a halogen atom, and any methylene group in this alkylene group is -O-, -S-, -CO-, -CS-, -CH
ＣＨCH—, —C≡C—, or —SiR ² R ³ —, but —O— and —S— are not consecutive, provided that X ¹ , X ² , X ³ And at least one of X ⁴ is difluoromethyleneoxy; R ² and R ³ are a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms,
Or an alkoxy group having 1 to 3 carbon atoms; a ¹ , a ² ,
a ³ , a ⁴ and a ⁵ each independently represent 0 or 1;
Further, the atoms constituting these compounds may be substituted with their isotopes. ) Has not only a large absolute value of a negative dielectric anisotropy value but also an appropriate refractive index anisotropy value, a small elastic constant, good compatibility, low viscosity, By using the compound according to claim 1 or 2 in a liquid crystal composition, the elastic constant is small, the dielectric constant anisotropy value and the refractive index anisotropy are high. The value can be appropriately set, the viscosity is low, and a liquid crystal composition having excellent chemical and physical stability, in particular, a liquid crystal composition having a large absolute value of a negative dielectric anisotropy value can be obtained; and It has been found that a liquid crystal display device can be obtained using the composition, and the present invention has been completed. .

In the general formula (1), R ¹ and Y ¹ are a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
Propyl, butyl, pentyl, hexyl, heptyl, decyl, pentadecyl, and icosyl, and isopropyl, sec-butyl, tert.
-Butyl, 2-methylbutyl, isopentyl, isohexyl, 3-ethyloctyl, 3,8-dimethyltetradecyl, and 5-ethyl-5-methylnonadecyl can be respectively indicated. These alkyl groups are -O-
And -S- are not continuous, any methylene group in the group is -O-, -S-, -CO-, -CS-, -CH = C
H -, - C≡C -, - SiR 2 R 3 -, cyclopropane -
It may be substituted by 1,2-diyl, cyclobutane-1,3-diyl or bicyclo [1.1.1] pentane-1,3-diyl.

Examples of such groups include alkoxy groups,
Alkoxyalkyl group, alkenyl group, alkadienyl group, alkenyloxy group, alkoxyalkenyl group, alkynyl group, alkynyloxy group, alkoxyalkynyl group, silanyl group, alkylsilyl group, alkoxysilyl group, alkylsilylalkyl group, alkoxysilylalkyl group , An alkyldisilanyl group, an alkyldisilanylalkyl group, and an alkyltrisilanyl group. Further, one or more hydrogen atoms in these groups may be substituted with a halogen atom, and examples thereof include a halogen-substituted alkyl group, a halogen-substituted alkoxy group,
A halogen-substituted alkenyl group, a halogen-substituted alkenyloxy group, a halogen-substituted alkynyl group, and a halogen-substituted alkynyloxy group can be shown.

Among these, preferred groups are specifically exemplified. As it has been substituted with a -O- group, - -CH ₂ in the radical
Alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy or nonyloxy, methoxymethyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyoctyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, ethoxyhexyl, Propoxymethyl, propoxyethyl, propoxypropyl, propoxypentyl, butoxymethyl, butoxyethyl, butoxybutyl, pentyloxymethyl, pentyloxybutyl, hexyloxymethyl, hexyloxyethyl, hexyloxypropyl, heptyloxymethyl, octyloxymethyl, etc. Is converted as a branched alkoxy group to 2-methylpropoxy, 2-methylpentoxy, and 1- It can be shown Chiruheputokishi.

Examples of the group in which —CH ₂ — in the group is substituted with —S— include a methylthio, ethylthio, propylthio, butylthio and pentylthio group. -CH ₂ in the radical - as a group is substituted with -CH = CH-, vinyl, propenyl, butenyl, pentenyl, hexenyl, alkenyl groups decenyl, methoxy propenyl, ethoxy propenyl, pentyloxy propenyl,
Alkoxyalkenyl groups such as methoxybutenyl, ethoxybutenyl, pentyloxybutenyl, methoxypentenyl, propoxypentenyl, methoxyhexenyl, propoxyhexenyl, methoxyheptenyl and methoxyoctenyl, propenyloxy, butenyloxy, pentenyloxy, octenyloxy, propenyloxy Alkenyloxy groups such as methyl, propenyloxyethyl, propenyloxybutyl, butenyloxymethyl,
Groups such as butenyloxyethyl, butenyloxypentyl, pentenyloxymethyl, pentenyloxypropyl, hexenyloxymethyl, hexenyloxyethyl, heptenyloxymethyl, octenyloxymethyl, butadienyl, heptadienyl, hexadienyl, heptadienyl, octadienyl, icosadenyl And the like.

Examples of the group in which —CH ₂ — in the group is substituted with —C≡C— include alkynyl groups such as ethynyl, propynyl, butynyl, pentynyl and octynyl, ethynyloxy,
Alkynyloxy groups such as propynyloxy, butynyloxy, pentynyloxy, tetradecynyloxy, methoxypropynyl, methoxypentynyl, ethoxybutynyl, propoxypropynyl, hexyloxyheptynyl, methoxymethylbutynyl, methoxypropylethynyl, butoxymethyl An alkoxyalkynyl group such as propynyl can be shown.

Examples of the group in which -CH _2- in the group is substituted with -SiR ² R ^3- include alkylsilyl groups such as methylsilyl, ethylsilyl, propylsilyl, butylsilyl, pentylsilyl and nonylsilyl, methylsilylmethyl and methylsilyl. Ethyl, methylsilylpropyl, methylsilylbutyl, methylsilylheptyl, ethylsilylmethyl,
Ethylsilylethyl, ethylsilylpropyl, ethylsilylhexyl, propylsilylmethyl, propylsilylethyl, propylsilylpropyl, butylsilylmethyl, butylsilylethyl, butylsilylpropyl, pentylsilylmethyl, hexylsilylmethyl, hexylsilylethyl, heptylsilyl Methyl, alkylsilylalkyl groups such as octylsilylmethyl, methoxysilyl,
Ethoxysilyl, propoxysilyl, butoxysilyl,
Pentyloxysilyl, alkoxysilyl groups such as octyloxysilyl, silanyl groups such as silanyl, disilanyl, trisilanyl, tetrasilanyl, pentasilanyl, and decasilanyl;

Alkyldisilanyl groups such as methyldisilanyl, ethyldisilanyl, propyldisilanyl, butyldisilanyl, and pentyldisilanyl; methyltrisilanyl;
Alkyltrisilanyl groups such as ethyltrisilanyl, propyltrisilanyl and hexyltrisilanyl, methylnonasilanyl, methyldisilanylmethyl, methyldisilanylethyl, methyldisilanylpentyl, ethyldisilanylmethyl , Alkyl such as ethyldisilanylethyl, ethyldisilanylbutyl, ethyldisilanylhexyl, propyldisilanylmethyl, butyldisilanylpentyl, pentyldisilanylmethyl, hexyldisilanylethyl, heptyldisilanylmethyl Disilanylalkyl group, methyltrisilanylmethyl, methyltrisilanylpentyl, ethyltrisilanylmethyl, ethyltrisilanylpropyl, propyltrisilanylmethyl, propyltrisilanylbutyl, butyltrisilanylmethyl, pentyltri Silanylmethyl, hex Alkyltrisilanylalkyl groups such as rutosilanylmethyl, methylhexasilanylmethyl, ethylheptasilanylmethyl, methyloctasilanylmethyl, 2-fluoroethylsilyl, 3,3-difluoropropylsilyl, 1,2,3 , 3-tetrafluoropropylsilyl group, trimethylsilyl, dimethylethylsilyl, dimethylpropylsilyl, dimethylbutylsilyl, dimethylpentylsilyl, trimethylsilylmethyl and the like.

When --CH _2- in the group is --CO-- or --CS
As a group substituted with-methylcarbonyl, methylthiocarbonyl, ethylcarbonyl, propylcarbonyl,
Propylthiocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, heptyloxycarbonyl, 2-oxopropyl, 2-oxobutyl, 3-oxobutyl, 2-oxopentyl, 4-oxopentyl, 3-oxohexyl,
5-oxohexyl, 2-oxoheptyl, 3-oxoheptyl, 6-oxoheptyl, 2-oxooctyl,
Examples thereof include groups such as 4-oxooctyl, 7-oxooctyl, 3-oxononyl, 6-oxononyl, 8-oxononyl, 2-oxodecyl, 5-oxodecyl, and 9-oxodecyl.

The hydrogen atom in these groups may be substituted with a halogen atom or a cyano group, and specific examples include fluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-cyanoethyl, 1,2- Difluoroethyl,
Halogen-substituted alkyl groups such as 3-fluoropropyl, 3-chloropropyl, 3-cyanopropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 8,8-difluorooctyl, fluoromethoxy, 2
A halogen-substituted alkoxy group such as -fluoroethoxy, 3
-Fluoropropenyl, 4-fluoro-1-butenyl,
4-fluoro-2-butenyl, 5-fluoro-1-pentenyl, 5-fluoro-2-pentenyl, 5-fluoro-3-pentenyl, 6-fluoro-1-hexenyl, 6
-Fluoro-3-hexenyl, 7-fluoro-5-heptenyl, 3-fluoro-2-propenyl, 3-chloro-
1-propenyl, 4-fluoro-3-butenyl, 5,5
Halogen-substituted alkenyl groups such as -difluoro-4-pentenyl, 3,3-difluorohexenyl and 8,8-difluoro-7-octenyl can be shown.

A group in which -CH ₂ -in the group is substituted by cyclopropane-1,2-diyl, cyclobutane-1,3-diyl or bicyclo [1.1.1] pentane-1,3-diyl As cyclopropyl, 2-methylcyclopropyl, 2-ethylcyclohexyl, 2-propylcyclohexyl, 2-cyclohexylethyl, 3-cyclopropylpropyl, 3-methylcyclobutyl, 3-propylcyclobutyl, 3-propylbicyclo [1 1.1.
1] pentyl, 3-butylbicyclo [1.1.1] pentyl and the like. In the compound represented by the general formula (1), the compound wherein R ¹ is an optically active group is
Particularly useful as a chiral dopant. By using these, the occurrence of a reverse twist domain can be prevented.

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 include an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl A group, an alkoxyalkenyl group or an alkylsilyl group is more preferable, and a substituent having low polarity such as an alkyl group, an alkoxy group or an alkoxyalkyl group is more preferable. The elastic constant ratio K ₃₃ / K _{11 of the} compound represented by the general formula (1) (bend elastic constant /
When it is desired to increase the splay elastic constant), a double bond may be introduced into R ¹ and / or Y ¹ . When it is desired to lower the viscosity, a double bond, a triple bond or a di-substituted silyl group (—SiR ² R ³ —) is added to R ¹ and / or Y ^1.
Should be introduced. When you want to lower the threshold voltage, di-substituted silyl group (-SiR ² R ³ -) may be introduced.

When it is desired to improve the chemical stability and physical stability of the compound represented by the general formula (1), R ¹ and Y ¹ are an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkoxyalkenyl group. A group, an alkylsilyl group, a halogen-substituted alkyl group, a halogen-substituted alkoxy group or a halogen-substituted alkenyl group is more preferable, and an alkyl group, an alkoxy group, an alkoxyalkyl group, a halogen-substituted alkyl group or a halogen-substituted alkoxy group is more preferable. In the general formula (1), ring A ¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are mutually independently a ring represented by the general formula (2), a silacyclohexane ring, a cyclohexane- 1,4-diyl, 1,4-phenylene or bicyclo [1.1.1] pentane-1,
Although 3-diyl is shown, in order to achieve the object of the present invention,
At least one is a ring represented by the general formula (2), and at least one is a silacyclohexane ring.

[0030]

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In the ring represented by the general formula (2), W ¹
And W ² each independently represent a fluorine atom or a chlorine atom. Specific examples of the ring represented by the general formula (2) include 2,3-difluoro-1,4-phenylene, 2,3-dichloro-1,4-phenylene, and 2-chloro-3-
Fluoro-1,4-phenylene can be exemplified. The silacyclohexane ring is represented by the general formula (3-1)
The groups represented by the formulas (3-1) and (3-4) are used in order to exhibit low viscosity and high electrical insulation (high specific resistance or high voltage holding ratio).
-2) is particularly preferred. In the general formula (1), R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms, but have high electric insulation (high specific resistance or high voltage holding ratio). Is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom or a methyl group to develop a lower viscosity.

As the ring other than the ring represented by the general formula (2) and the silacyclohexane ring, preferred as the rings A ¹ to A ⁵ are cyclohexane-1,4-diyl, 1,4-phenylene, and Can be a ring in which carbon atoms constituting the ring are replaced with nitrogen atoms or non-adjacent carbon atoms are replaced with oxygen atoms. When cis-trans isomers are present in these six-membered rings, trans-form isomers are preferred.

Specifically, the following rings are exemplified. 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). The hydrogen atom on these rings is a fluorine atom,
It may be substituted with a chlorine atom or a cyano group. Specific examples of such rings include the rings shown below. 1-cyano-trans-cyclohexane-1,4
-Diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohexa-1
-Ene-1,4-diyl, 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl, fluoro-
1,4-phenylene, 3,5-difluoro-1,4-phenylene, chloro-1,4-phenylene, 3,5-dichloro-1,4-phenylene, and 3-fluoro-5-
Chlorophenylene.

Chemical formula of the compound represented by the general formula (1)
If paying attention, in particular, to physical stability, the preferred ring to ring A ¹ ~ ring A ⁵ are of the general formula is a ring and silacyclohexane ring represented by (2), in other ring, the ring A ¹ ~ ring shown below as preferred ring in the ring a ⁵ and the like. 1-cyano-trans-cyclohexane-1,4-diyl,
2,2-difluoro-trans-cyclohexane-1,
4-diyl, 2-fluorocyclohex-1-ene-
1,4-diyl and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. Further, as a ring in which a hydrogen atom of these rings is substituted with a fluorine atom, a chlorine atom or a cyano group, 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, pyridazine-3,6-diyl, 1,3
-Dithiane-2,5-diyl and 1,3-oxathiane-2,5-diyl.

When it is desired to increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), the ring A ^1-
Preferred ring in the ring A ⁵ are, is a ring and silacyclohexane ring represented by the general formula (2), in other rings, include the rings illustrated below as a preferred ring in the ring A ¹ ~ ring A ⁵ . 1-cyano-trans-cyclohexane-1,4
-Diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohexa-1
-En-1,4-diyl, and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. Also,
Trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,4 as a ring in which a hydrogen atom of these rings is substituted by a fluorine atom, a chlorine atom or a cyano group.
-Diyl and pyridazine-3,6-diyl.

In the general formula (1), X ¹ , X ² , X ³ and X ⁴ each independently represent a single bond or a carbon atom in which at least one hydrogen atom in the group may be substituted by a halogen atom. Represents an alkylene group of the formulas 1 to 4, wherein any methylene group in the alkylene group is -O-, -CO-, -CS-, -CH =
CH -, - C≡C- or -SiR ² R ³ -, in may be substituted, it never -O- is continuous, and,
In order to achieve the object of the present invention, at least one of X ^{1 to} X ⁴ is difluoromethyleneoxy. Preferred groups other than difluoromethyleneoxy for X ^{1 to} X ⁴ include alkylene groups such as ethylene and butylene,
-Disilanediyl, 1,1,2,2-tetramethyldisilanediyl, 1,4-tetrasilanediyl, 1-silaethylene, 1,1-dimethyl-1-silaethylene, 1-sila-1,4-butylene, 2- -SiR ² R ^3, such as sila-1,4-butylene - group having the methyleneoxy, 1-1,4 butylene, 2-oxy-1,4-butylene, an ester bond such as -O- and Having a group, vinylene, 1
-Butenylene, a group having -CH = CH- such as 2-butenylene,

A group having -C≡C-, such as ethynylene, 1-butynylene, 2-butynylene, and 3-butynylene, a group in which one or more hydrogen atoms in each of the above groups are substituted with a halogen atom, for example, fluoromethylene Oxy, oxyfluoromethylene, 1,1-difluoroethylene, 2,2-difluoroethylene, 1,2-difluorovinylene, 1-fluorovinylene, 1-chloro-2-fluorovinylene,
1,2-difluoro-1-butenylene, 2,3-difluoro-2-butenylene, 3,4-difluoro-3-butenylene, 3-oxy-1-butenylene, 4-oxy-1-butenylene, and Can indicate binding.

When it is desired to increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), X ¹ ,
A preferred group for X ² , X ³ and X ⁴ is difluoromethyleneoxy, but other groups which are preferred for X ¹ , X ² , X ³ and X ⁴ include a single bond, ethylene, butylene, and The methylene group in these alkylene groups is-
O-, -CO-, -CS-, -CH = CH-, -C≡C
And-or -SiR ² R ^3- . The elastic constant ratio K of the compound represented by the general formula (1)
₃₃ / K ₁₁ when it is desired to increase the (bend elastic constant / splay elastic ^{constant), X 1, X 2,} X 3 and any one of X ⁴
When it is desired to lower the viscosity, a double bond, a triple bond or a di-substituted silyl group (—SiR) is added to at least one of X ¹ , X ² , X ³ and X ^4.
2 R ³ -) may be introduced, when it is desired to lower the threshold voltage, di-substituted silyl group (-SiR ² R ³ -) may be introduced.

In order to improve the chemical stability and physical stability of the compound represented by the general formula (1), X ¹ , X ² ,
A preferred group for X ³ and X ⁴ is difluoromethyleneoxy, but other groups include X ¹ , X ² , X ³ and X ⁴
Preferably, a single bond, ethylene, butylene,
And a methylene group in these alkylene groups is -O-,-
CO -, - CS-, or -SiR ² R ³ - can exhibit substituted with.

The compound of the present invention has a large absolute value of a negative dielectric anisotropy value. Therefore, by using the compound of the present invention as a main component, a liquid crystal composition having a negative dielectric anisotropy value can be adjusted. This liquid crystal composition includes, in particular, a vertical alignment system described in JP-A-2-176625, an IPS system, and the like.
It is useful for producing a device using a liquid crystal composition having a negative dielectric anisotropy value. Further, by adding the compound of the present invention to another liquid crystal compound or liquid crystal composition, the dielectric anisotropy value can be adjusted, so that the applicable range of the liquid crystal composition can be expanded. The compounds of the present invention have 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 has good compatibility with other liquid crystal compounds. Therefore, when the compound of the present invention is blended in a liquid crystal composition,
Problems such as precipitation of crystals are unlikely to occur. Further, the compound of the present invention can be incorporated in a large amount into the liquid crystal composition, and 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 can have a desired magnitude of the 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 compounds of the present invention represented by the general formula (1) include R ^{1 to} R ⁵ , Y ¹ , ring A ¹ to ring A ⁵ , X ^{1 to} X ⁴
By appropriately selecting and a ^{1 to} a ⁵ , 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 rings A ¹ , A ² , A ³ , A ⁴ and 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 is chemically and physically stable, and the liquid crystal composition using the compound has high specific resistance and 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 can be adjusted by appropriately selecting the number of rings. That is, when a particularly high clearing point is required, a compound having four or more rings satisfying a ¹ + a ² + a ³ + a ⁴ + a ⁵ ≧ 4 is used. When a moderate clearing point is required, a ¹ + a ² + a ^{3 is used.} +
A three-ring compound where a ⁴ + a ⁵ = 3, and a two-ring compound where a ¹ + a ² + a ³ + a ⁴ + a ⁵ = 2 may be selected when a particularly low clearing point is required. Compounds in which the atoms constituting the compound of the present invention are substituted with isotopes thereof show exactly the same properties, and thus can be said to be similarly preferable.

As described above, the compound of the present invention 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, by appropriately designing the structure according to the application, a liquid crystal compound having desired characteristics, a liquid crystal composition and a device using the same can be obtained. For example, the compound of the present invention is characterized by exhibiting a large negative dielectric anisotropy value, but can be used as a component of a liquid crystal composition having a negative dielectric anisotropy value. Can be added to a composition having the above dielectric anisotropy value to adjust its dielectric anisotropy value and other properties. More specifically, the compound of the present invention and the 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, Japanese Patent Application Laid-Open No. 2-176).
No. 625, I.
PS system, ECB system (HAN system or DAP system, etc.), DS system, GH system, PC system, etc., particularly preferably used for vertical alignment system and IPS system as described in JP-A-2-176625. it can.
However, not only those methods, but also various display methods using compounds or compositions having a positive dielectric anisotropy value (for example,
Various characteristics (for example, a dielectric anisotropy value, an elastic constant, and the like) of a liquid crystal composition for a TN mode, an STN mode, or an AM mode (TFT mode or MIM mode) based on the TN mode.
Refractive index anisotropy, viscosity, or chemical and physical stability)
It can also be used for improvement and adjustment.

The above R ^{1 to} R ⁵ , Y ¹ , ring A ¹ to ring A ⁵ , X ¹
All the compounds of the present invention, suitably selected and combined from to X ⁵ and a ^{1 to} a ⁵ , are preferred compounds having the properties unique to the compounds of the present invention, and more preferably those of the general formula (2) ), A compound containing at least one silacyclohexane ring and at least one difluoromethyleneoxy. One group of such compounds having particularly favorable properties is represented by the following formula (1-
1) to (1-71).

[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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(Wherein R ¹ , Y ¹ , R ⁴ , R ⁵ , ring A ¹ to ring A ⁵ and X ^{1 to} X ⁴ have the same meanings as described above.

[0051]

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Is the following formula

[0053]

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And E is difluoromethyleneoxy. )

Among the compounds of the above formulas (1-1) to (1-71), the compounds of the formulas (1-1) to (1-2) show particularly low viscosity, and the compounds of the formulas (1-17) Compounds (1) to (1-71) exhibit particularly high transition temperatures of the nematic-isotropic liquid phase.

The liquid crystalline compound of the present invention represented by the general formula (1) can be produced by a general organic synthesis method. Specifically, the method for producing the liquid crystalline compound represented by the general formula (1) includes: 1) construction of a ring represented by the general formula (2);
2) Construction of a silacyclohexane ring and 3) Introduction of difluoromethyleneoxy. Of these methods,
Only one example is shown below. For example, the ring site represented by the general formula (2) can be constructed by the following method.

[0057]

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(Wherein, MG1 and MG2 represent organic compound residues (mesogens).) That is, 2,3-dihalogenobenzene derivative (15)
Is reacted with sec-butyllithium to lithiate, then reacted with trimethyl borate to form boronic acid, and then reacted with MG2-I in the presence of a catalyst to give a compound having a ring moiety represented by the general formula (2) (A) can be manufactured.

The silacyclohexane ring site can be prepared by a known method, for example, R. West, J. Am. Chem. Soc., 76 , 6012 (1954).
And JA Soderquist _{et al} ., J. Org _. Chem., 49 , 2565 (1984).

[0060]

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(Wherein MG1 and MG2 represent organic compound residues (mesogens), and R ⁴ has the same meaning as described above.) That is, the 3-substituted-1,5-dibromopentane derivative (16) After reacting with magnesium to produce a Grignard reagent, the ring is closed by the action of a chlorosilane derivative (17) to give a compound (18) (a ring in which the silacyclohexane ring is represented by the above formula (3-1) or (3-2)). Compounds having moieties) can be produced. Instead of the chlorosilane derivative (17), a dichlorosilane derivative (R ⁴ is a hydrogen atom), a trichlorosilane derivative (R ⁴
Is a chlorine atom), a dichlorofluorosilane derivative (R ⁴ is a fluorine atom), and an alkyldichlorosilane derivative (R ⁴ is an alkyl group), so that R ⁴ is a hydrogen atom and chlorine is Compound (18) which is an atom, a fluorine atom, or an alkyl group can be produced. Further, the 3-substituted-1,5-dibromopentane derivative (16) is replaced with a trichlorosilane derivative (19).
To give a compound having a chlorocyclohexane ring (2
0), to which a Grignard reagent (MG2-MgB
r) or by reacting with a lithium reagent (MG2-Li) to produce compound (18). Or,
Compound (21) is treated with 9-BBN (9-borabicyclo [3.
3.1] Nonane), BMS (borane-methyl sulfide complex), and then methanol are reacted in this order to obtain compound (22), to which dichloromethyl methyl ether,
Compound (23) is obtained by reacting lithium triethyl carboxide and then hydrogen peroxide in this order. Compound (2
Compound (18) can also be produced by reacting 3) a Grignard reagent (MG1-MgBr) or a lithium reagent (MG1-Li) and then an acid, followed by hydrogenation.

[0062]

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(Wherein, MG1 and MG2 represent organic compound residues (mesogens), and R ⁴ and R ⁵ have the same meaning as described above.) 1,4-Disubstituted-1,5-dibromopentane derivative (2
After reacting 4) with magnesium to give a Grignard reagent, the ring is closed by the action of a dichlorosilane derivative (25), and the compound (26) (the silacyclohexane ring forms the aforementioned formula (3-3) and the formula (3-4) A) having a ring site represented by the formula:

The difluoromethylene group is preferably introduced by converting the thiocarbonyl group of the corresponding thioester compound into a difluoromethylene group with an appropriate fluorinating agent according to the method described in Patent Publication WO 96/11897. it can.

[0065]

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(Wherein, MG1 and MG2 have the same meanings as described above.) That is, magnesium or lithium is allowed to act on the bromide (27) to obtain a corresponding Grignard reagent or lithium reagent, and carbon disulfide is acted upon. To give the dithioic acid derivative (28). Then, patent publication WO96 /
No. 11897 or Japanese Patent Application No. 08-191.
According to the method described in No. 530, a mixture of a phenol or an alcohol (29) and a dithioic acid derivative (28) is caused to act on sodium hydride, converted into a sodium salt and an alcoholate, and then reacted with iodine. The thioic acid-O-ester derivative (30) is obtained. Further, the thiocarbonyl group of the thioic acid-O-ester derivative (30) is replaced with diethylaminosulfur trifluoride (D
AST) or JP-A-5-255
In the presence of N-bromosuccinimide (NBS) or 1,3-dibromo-5,5-dimethylhydantoin (DBH), tetrabutylammonium dihydrogen fluoride or HF-pyridine complex is allowed to act in accordance with the method described in No. 165 Thereby, the compound (B) having a difluoromethylene group can be produced. Further, a compound having a difluoromethylene group can also be produced by converting an ester bond into a difluoromethyleneoxy group. That is, a thioester derivative (30) is produced by allowing a Lawson reagent to act on an ester derivative (31) that can be produced by a conventional method, and this can be derived into a compound (B) having a difluoromethylene group by the above-described method. .

All the compounds of the present invention can be produced by appropriately combining the above-mentioned various reactions according to the properties required of the compounds. In addition, all the above-mentioned reactions are known, but it goes without saying that other known reactions can be used if necessary.

Hereinafter, the liquid crystal composition of the present invention will be described. The liquid crystal composition according to the present invention contains 0.1 to 99.9% by weight of at least one compound represented by the general formula (1).
Is preferable 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 represented by the general formula (1), a compound represented by the general formula (4) depending on the purpose of the liquid crystal composition. It is completed by mixing the compounds selected from the compound group represented by (14) in an appropriate ratio.

[0069]

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(Wherein, R ^{6 to} R ¹² 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 2
= CH- may be substituted with, also, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom; 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 , Y ³ represents a cyano group or —C≡C—CN; L ^{1 to} L ⁷ each independently represent a hydrogen atom or a fluorine atom; ⁶ and L ⁷ are not indicate a hydrogen atom simultaneously; 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, Z ³ , Z ⁶ and Z ⁷ each independently represent — (CH ₂ ) ₂ —, —COO— or a single bond; Z ⁴ and Z ⁵ each independently -C≡C-, -CO
_{O -, - (CH 2)} 2 -, - CH = CH- or a single bond; the ring Q ¹ is trans - cyclohexane-1,4-diyl, 1,3-dioxane-2,5-diyl or hydrogen, The atom represents 1,4-phenylene in which an atom may be substituted by a fluorine atom, and the ring Q ² is trans-cyclohexane-
1,4-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, wherein ring Q ³ is trans-cyclohexane-1,4-diyl, 1,4-phenylene, 1,3 -Dioxane-2,5-diyl or pyrimidine-2,5-diyl, wherein ring Q ⁴ is ring Q ⁶ ,
Ring Q ⁷ and ring Q ⁸ are each independently 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. shown, ring Q ⁵ is trans - indicates cyclohexane-1,4-diyl or 1,4-phenylene, ring Q ⁹ and ring Q ¹⁰ are each independently trans - cyclohexane-1,4-diyl or 1,4 -Represents phenylene; b, c and d each independently represent 0 or 1; and the atoms constituting these compounds may be substituted with their isotopes. The compounds represented by formulas (4) to (6) used in the liquid crystal composition of the present invention preferably include the following compounds.

[0071]

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[0072]

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[0073]

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(R ⁶ and Y ² have the same meanings as described above.) The compounds represented by the general formulas (4) to (6) are compounds having a positive dielectric anisotropy value and have a high thermal stability. In particular, when preparing a liquid crystal composition for a TFT mode in which high reliability is required, such as a high voltage holding ratio or a large specific resistance value, a preferable compound is used. is there. When adjusting the liquid crystal composition for the TFT mode, the amount of the compound represented by the general formulas (4) to (6) is in the range of 0.1 to 99.9% by weight based on the total weight of the liquid crystal composition. , But is preferably from 10 to 97% by weight, more preferably from 40 to 95% by weight. In addition, general formulas (9) to
The compound represented by (11) may be further contained for the purpose of adjusting the viscosity. When preparing a liquid crystal composition for STN mode or TN mode, the compounds represented by formulas (4) to (6) can be used. In that case, the use amount of 50% by weight or less is preferable. As the compounds represented by the general formulas (7) and (8) used in the liquid crystal composition of the present invention, the following compounds can be preferably mentioned.

[0075]

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[0076]

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(R ⁷ , Y ³ and R ⁸ have the same meanings as described above.) The compounds represented by the general formulas (7) to (8) have a positive dielectric anisotropy value and a large value. In particular, it is used for the purpose of reducing the threshold voltage of the liquid crystal composition. It is also used for the purpose of adjusting the value of the refractive index anisotropy and expanding the nematic range such as increasing the clearing point. Furthermore, STN method or TN
It is also used for the purpose of improving the steepness of the VT curve of the liquid crystal composition for the system. The compounds represented by the general formulas (7) and (8) are preferred compounds particularly when preparing liquid crystal compositions for STN mode and TN mode. When the amount of the compound represented by any one of the general formulas (7) and (8) 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 it can be driven at low voltage. The amount of the compounds represented by the general formulas (7) to (8) can be used in the range of 0.1 to 99.9% by weight when a liquid crystal composition for STN mode or TN mode is prepared. Preferably 10-97% by weight, more preferably 4%
0 to 95% by weight.

The compounds represented by formulas (9) to (11) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ⁹ and R ¹⁰ have the same meaning as described above.)

[0079]

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The compounds represented by the general formulas (9) to (11) have a small absolute value of dielectric anisotropy and are almost neutral. The compound represented by the general formula (9) 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 (10) and (11) are used for the purpose of expanding the nematic range such as increasing the clearing point or adjusting the value of the refractive index anisotropy. When the amount of the compound represented by any one of the general formulas (9) to (11) 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.
The amounts of the compounds represented by the general formulas (9) to (11) are
When preparing a liquid crystal composition for a TFT mode, the content is preferably 40% by weight, more preferably 35% by weight or less. When adjusting the liquid crystal composition for the STN mode or the TN mode, the content is preferably 70% by weight or less, more preferably 60% by weight or less.

The compounds represented by formulas (12) to (14) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ¹¹ and R ¹²
Has the same meaning as described above. )

[0082]

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The compounds represented by the general formulas (12) to (14) are compounds having negative values of dielectric anisotropy, like the compounds described in claim 1 or 2 of the present invention. It is used as a base compound of a liquid crystal composition of a P type or for controlling the dielectric anisotropy of a liquid crystal composition of a P type. As another application, the compound represented by the general formula (12) is a bicyclic compound, and is mainly used for adjusting a threshold voltage, adjusting a viscosity, or adjusting a refractive index anisotropy value. The compound represented by the general formula (13) 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 (14) is used for the purpose of expanding the nematic range, reducing the threshold voltage, and increasing the refractive index anisotropy value.

The compounds represented by the general formulas (12) to (14) are mainly used in N-type liquid crystal compositions. Increasing the amount of the compounds decreases the threshold voltage of the liquid crystal composition, but increases the viscosity. growing. 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 (12) to (1)
The amount of the compound represented by 4) is preferably 40% by weight or more, more preferably 50 to 95% by weight, when a liquid crystal composition for an N-type TFT system is prepared. Also,
For the purpose of controlling the elastic constant and controlling the voltage-transmittance curve (VT curve) of the liquid crystal composition, the general formula (1)
The compounds shown in 2) to (14) may be mixed with the P-type composition in some cases. General formulas (12) to (14) in this case
Is preferably 30% by weight or less.

In the liquid crystal composition of the present invention, OCB
(Optically Compensated Birefringence) Except for special cases such as a liquid crystal composition for a method, for the purpose of inducing a helical structure of the liquid crystal composition to adjust a necessary twist angle and preventing reverse twist (reverse twist), An optically active compound is added. Although any known optically active compounds can be used for such a purpose, preferred examples include the following optically active compounds.

[0086]

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The liquid crystal composition of the present invention usually adjusts the twist pitch by adding these optically active compounds.
The pitch of the twist is preferably adjusted in the range of 40 to 200 μm for a liquid crystal composition for a TFT mode and a TN mode. 6 to 2 if the liquid crystal composition is for STN mode.
It is preferable to adjust to a range of 0 μm. In addition, bistable T
1.5 for N (Bistable TN) system
It is preferable to adjust the thickness to a range of 4 μm. Further, two or more optically active compounds may be added for the purpose of adjusting the temperature dependency of the pitch.

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. Further, the liquid crystal composition of the present invention is a merocyanine, styryl, azo, azomethine, azoxy, quinophthalone, anthraquinone,
Further, a dichroic dye such as a tetrazine-based dye can be added to use as a liquid crystal composition for GH mode. Alternatively, a liquid crystal composition for a polymer dispersed liquid crystal display (PDLCD) represented by an NCAP formed by microencapsulating a nematic liquid crystal or a polymer network liquid crystal display (PNLCD) formed by forming a three-dimensional network polymer in the liquid crystal. It can also be used as an object. In addition, it can be used as a liquid crystal composition for ECB mode and DS mode.

[0089]

EXAMPLES The production methods and use examples of the compounds 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 a specified concentration (gram equivalent / l),
M is molar concentration (mol / l), Δε is dielectric anisotropy value,
Δn indicates a refractive index anisotropy value. Composition of mother liquid crystal A:

[0090]

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Five types of ester compounds represented by the above general formula and having different alkyl groups (R ¹³ , R ¹⁴ ) at both ends are represented by the following formula:
The mixture was mixed at the following ratio to obtain mother liquid crystals A (% is% by weight). The dielectric anisotropy value of this composition was Δε = −1.5.

Example 1 trans-1-n-propyl-1-methyl-4- (trans-4- (2,3-difluoro-4-ethoxyphenyl) cyclohexyloxy) difluoromethylsilacyclohexane ( 13 , compound No. 2-65) Production

[0093]

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First Step Synthesis of 2,3-difluoroethoxybenzene ( 2 ) 2,3-difluorophenol (130.1 g, 1.0
0mol), ethyl bromide (130.8g, 1.20mo)
l), potassium carbonate (207.3 g, 1.50 mol)
And ethanol (1000 ml) were mixed and heated to reflux for 6 hours. After completion of the reaction, solids were removed by filtration, and the solvent was distilled off under reduced pressure. Water (500ml) in the residue
And extracted with hexane (800 ml). The obtained organic phase was washed three times with water (500 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent:
Hexane) to give 2,3-difluoroethoxybenzene ( 2 ) (133.3 g, 0.843 mol; 84% yield). MS / 158 (M ^<+> ).

Second step Synthesis of 4-hydroxy-4- (2,3-difluoro-4-ethoxyphenyl) cyclohexanone ethylene ketal ( 3 ) 2,3-difluoroethoxybenzene ( 2 ) ( 2 ) obtained in the first step 132.8 g, 0.840 mol) and TH
To a mixture of F (tetrahydrofuran) (600 ml)
A 1.06 M solution of sec-butyllithium in cyclohexane (0.924 mol, 871 ml) was added dropwise while maintaining -78 ° C, and the mixture was stirred at the same temperature for 1 hour. Then, THF (30 ml) of 1,4-cyclohexanedione monoethylene ketal (196.7 g, 1.26 mol) was added to the reaction solution.
0 ml) solution was added dropwise while maintaining the same temperature, and then the temperature was gradually raised and reacted at room temperature for 3 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure to about half the volume, and then water (80
0 ml) and then diethyl ether (1400 m
Extracted in l). The obtained organic phase was washed three times with water (800 ml) and dried over anhydrous magnesium sulfate.
The solvent was distilled off under reduced pressure to obtain 4-hydroxy-4- (2,
A crude product containing ( 3 -difluoro-4-ethoxyphenyl) cyclohexanone ethylene ketal ( 3 ) was obtained.

Third Step Synthesis of 4- (2,3-difluoro-4-ethoxyphenyl) cyclohex-3-en-1-one ethylene ketal ( 4 ) 4-hydroxy-4- ( A mixture of a crude product containing 2,3-difluoro-4-ethoxyphenyl) cyclohexanone ethylene ketal ( 3 ), paratoluenesulfonic acid monohydrate (7.99 g, 0.0420 mol) and toluene (600 ml) was refluxed. The mixture was reacted for 2 hours while distilling off water. After completion of the reaction, the reaction mixture was cooled to room temperature, and a 1N aqueous sodium hydrogen carbonate solution (500 m
l) was added, followed by extraction with toluene (800 ml). The obtained organic phase was washed three times with water (500 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 (elution solvent: toluene) to give 4- (2,3-difluoro-4-ethoxyphenyl) cyclohex-3-
En-1-one ethylene ketal ( 4 ) (155.0)
g, 0.523 mol; yield 62% from 2 ). MS / 296 (M ^<+> ).

Fourth Step Synthesis of 4- (2,3-difluoro-4-ethoxyphenyl) cyclohexanone ethylene ketal ( 5 ) 4- (2,3-difluoro-4-ethoxyphenyl) cyclohexa obtained in the third step -3-en-1-one ethylene ketal ( 4 ) (154.5 g, 0.521 mo)
l) A mixture of 5% palladium carbon (7.72 g) and ethanol (500 ml) was hydrogenated at room temperature and normal pressure for 5 hours with stirring. After completion of the reaction, palladium carbon was removed by filtration, the solvent was distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 4- (2,3-difluoro-4). (-Ethoxyphenyl) cyclohexanone ethylene ketal ( 5 ) (146.4 g, 0.491 mol, 94% yield) was obtained. MS / 298 (M ^<+> ).

Step 5 Synthesis of 1-ethoxy-2,3-difluoro-4- (4-oxocyclohexyl) benzene ( 6 ) 4- (2,3-difluoro-4-ethoxyphenyl) obtained in Step 4 ) Formic acid (300 ml) was added dropwise to a mixture of cyclohexanone ethylene ketal ( 5 ) (145.8 g, 0.489 mol) and toluene (450 ml). The mixture was heated and reacted for 1 hour under reflux. After completion of the reaction, the reaction solution was cooled to room temperature, and water (500
ml) and then extracted with toluene (800 ml). The obtained organic phase was washed three times with water (1000 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 (elution solvent: toluene) to give 1-ethoxy-
2,3-difluoro-4- (4-oxocyclohexyl) benzene ( 6 ) (116.4 g, 0.458 mo)
1; yield 94%). MS / 254 (M ^<+> ).

Sixth stage 1-ethoxy-2,3-difluoro-4- (trans-
Synthesis of 4-hydroxycyclohexyl) benzene ( 7 ) 1-ethoxy-2,3-difluoro- obtained in the fifth step
4- (4-oxocyclohexyl) benzene ( 6 ) (1
16.0 g (0.456 mol) of THF (600 m
l) The solution was cooled and LAH (lithium aluminum hydride) (17.46 g, 0.460 mol) was added at -10 <0> C. The reaction solution was gradually heated to room temperature and reacted at the same temperature for 7 hours. After the completion of the reaction, water (300 ml) under ice-cooling
And 1N diluted hydrochloric acid (150 ml) was further added.
After completion of the reaction, the reaction solution was concentrated under reduced pressure, and then ethyl acetate (1%) was added.
000 ml). The obtained organic phase was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: toluene / ethyl acetate = 1/1), and then recrystallized (solvent:
Purification with toluene / hexane = 1/1) gave 1-ethoxy-2,3-difluoro-4- (trans-4-hydroxycyclohexyl) benzene ( 7 ) (92.13 g,
0.359 mol; yield 79%). MS / 256 (M ^<+> ).

Seventh step Synthesis of 4-n-propyl-4-methyl-4-silacyclohexanol ( 9 ) 4-n-propyl-4-methyl-4-silacyclohexanone ( 8 ) (170.3 g, 1. (00 mol) in ethanol (900 ml) was cooled, and sodium borohydride (37.83 g, 1.00 mol) was added at -10 ° C. The reaction solution was gradually heated to room temperature and reacted at the same temperature for 10 hours. After completion of the reaction, water (450 ml) was added under ice cooling, and 1N diluted hydrochloric acid (230 ml) was further added. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and then ethyl acetate (90%).
0 ml). The obtained organic phase was washed with water (700 m
After washing three times in 1), the resultant was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 1/1) to give 4-n-propyl-4-methyl-4-silacyclohexanol ( 9 ) (124.8 g,
0.724 mol; yield 72%). MS / 172 (M ^<+> ).

Step 8 Synthesis of 1-n-propyl-1-methyl-4-bromosilacyclohexane ( 10 ) 4-n-propyl-4-methyl-4-silacyclohexanol ( 9 ) obtained in Step 7 (124.5 g, 0.722
mol), N, N-dimethylformamide (200 m
l) and phosphorus tribromide (293.2 g, 1.08 mol)
The mixture of 1) was heated to reflux for 2 hours. After cooling to room temperature, the mixture was extracted with toluene (1000 ml). The obtained organic phase was washed with a 1N aqueous solution of sodium hydrogen carbonate (700 ml).
And 3 times with water (700 ml), and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent:
Purification with toluene / ethyl acetate = 10/1) yielded 1-n
-Propyl-1-methyl-4-bromosilacyclohexane ( 10 ) (141.1 g, 0.600 mol; yield 8)
3%). MS / 235 (M ^<+> ).

Ninth Step Synthesis of 4-n-propyl-4-methyl-4-silacyclohexanedithioic acid ( 11 ) 1-n-propyl-1-methyl-4-bromosilacyclohexane ( 10 ) obtained in the eighth step ) (140.7 g, 0.5
98 mol), metallic lithium (4.16 g, 0.600)
mol) and THF (900 ml) were reacted in an ultrasonic bath for 6 hours. Next, carbon disulfide (84.69 g, 1.11 mol) was added to the reaction mixture, and the mixture was stirred for 2 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure to about half the volume, and water (500 ml) was added.
Extracted with diethyl ether (1000 ml). The obtained organic phase was washed three times with water (500 ml) and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure,
Crude 4-n-propyl-4-methyl-4-silacyclohexanedithioic acid ( 11 ) (43.1) as a red oil.
0 g, 0.185 mol; yield 31%). MS / 232 (M ^<+> ).

Step 10 4-n-propyl-4-methyl-4-silacyclohexanethioic acid = 0- (trans-4- (2,3-difluoro-4-ethoxyphenyl) cyclohexyl ester ( 1
2 ) Synthesis of crude 4-n-propyl-4-methyl-4 obtained in the ninth step
-Silacyclohexanedithioic acid ( 11 ) (42.75)
g, 0.184 mol) in thionyl chloride (21.88).
g, 0.184 mol) and stirred at 50 ° C. for 1 hour to obtain a brown solution. To this solution was added dry toluene (600
ml), pyridine (600 ml), 1-ethoxy-2,3-difluoro-4- (trans-4-hydroxycyclohexyl) benzene ( 7 ) obtained in the sixth step (91.90).
g, 0.359 mol), and the mixture was stirred at 50 ° C. for 5 hours. Toluene (600 ml) and water (1
200 ml), and the mixture was sufficiently stirred, and allowed to stand still to separate an organic phase. The organic phase was washed three times with water (1000 ml) and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: toluene) to give 4-n-propyl-4-methyl-4-silacyclohexanethioic acid = 0.
-(Trans-4- (2,3-difluoro-4-ethoxyphenyl) cyclohexyl ester ( 12 ) (35.
62 g, 0.0783 mol; yield 43%). MS / 455 (M ^<+> ).

Eleventh Step Synthesis of trans-1-n-propyl-1-methyl-4- (trans-4- (2,3-difluoro-4-ethoxyphenyl) cyclohexyloxy) difluoromethylsilacyclohexane ( 13 ) 4-n-propyl-4-methyl-4-silacyclohexanethioic acid obtained in 10 steps = 0- (trans-4- (2,
3-difluoro-4-ethoxyphenyl) cyclohexyl ester ( 12 ) (35.39 g, 0.0778 mo)
To a solution of 1) in dichloromethane (200 ml) was added DAST (16.13 g, 0.100 mol) at 0 ° C. or lower, and the mixture was stirred at the same temperature for 5 hours. Toluene (50
0 ml) and water (500 ml) were added, and the mixture was sufficiently stirred. The organic phase is washed with water (500m
After washing three times in 1), the resultant was dried with anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: heptane), followed by recrystallization (solvent: ethanol) to give the title compound ( 13 ) (14.23 g, 0.0309 mmol, Yield: 40%). MS / 461 (M ⁺ ) Extrapolation method from the dielectric anisotropy value and the refractive index anisotropy value measured at 25 ° C. of a composition obtained by adding 15 parts by weight of this compound to 85 parts by weight of the mother liquid crystal A. The physical property values of this compound determined by were Δ △ = −4.1 and Δn = 0.093.

The following compounds can be prepared by a method similar to that of Example 1.

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As described above, the present invention has a low viscosity, a large absolute value, a negative dielectric anisotropy value, a controlled optical anisotropy value, a high specific resistance value, and a high specific resistance value. 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 device manufactured using the liquid crystal composition. Was.

Claims (12)

[Claims] 1. A compound of the general formula (1) (Wherein, R ¹ and Y ^{1 each} represent a linear or branched alkyl group having 1 to 30 carbon atoms, and any methylene group in these groups may be -O-, -S-, -CO-, -CS- , -CH = CH
-, - C≡C -, - SiR 2 R 3 -, cyclopropane -
It may be substituted with 1,2-diyl, cyclobutane-1,3-diyl, or bicyclo [1.1.1] pentane-1,3-diyl, but -O- and -S- are consecutive. And one or more hydrogen atoms in R ¹ may be substituted with a halogen atom or a cyano group; ring A ¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are each independently To form a silacyclohexane ring, cyclohexane-1,4-diyl, 1,4-phenylene, pyridine-2,5-diyl,
Pyrimidine-2,5-diyl, 1,3-dioxane-
2,5-diyl, tetrahydropyran-2,5-diyl, bicyclo [1.1.1] pentane-1,3-diyl, or a ring represented by the general formula (2) is shown. Any one or two hydrogen atoms may be replaced by a halogen atom, (Wherein W ¹ and W ² each independently represent a fluorine atom or a chlorine atom), provided that ring A ¹ , ring A ² , ring A ³ , ring A ⁴
And at least one of the rings A ^{5 is} a ring represented by the general formula (2), and at least one is a silacyclohexane ring; X ¹ , X ² , X ³ and X ⁴ are each independently A bond or an alkylene group having 1 to 4 carbon atoms, in which one or more hydrogen atoms in the group may be substituted with a halogen atom, and any methylene group in this alkylene group is -O
-, -S-, -CO-, -CS-, -CH = CH-,-
It may be substituted by C≡C— or —SiR ² R ³ —, but —O— and —S— are not consecutive, provided that X ¹ , X ² , X ³ and X ⁴ At least one is difluoromethyleneoxy; R ² , R ³ are hydrogen atoms,
A ¹ , a ² , a ³ , a ⁴ and a ⁵ each independently represent 0 or 1; a halogen atom, an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms; The atoms constituting these compounds may be substituted with their isotopes. ). 2. A silacyclohexane ring represented by the general formula (3-
The liquid crystal compound according to claim 1, which has a structure represented by any one of (1) to (3-4). Embedded image (Wherein R ⁴ and R ⁵ are a hydrogen atom, a halogen atom,
An alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms. ) 3. A composition comprising at least one liquid crystalline compound according to claim 1 or 2.
A liquid crystal composition comprising at least two components. 4. A compound comprising at least one compound according to claim 1 or 2 as a first component, and represented by formulas (4), (5) and (6) as a second component. A liquid crystal composition comprising at least one compound selected from a compound group. Embedded image (Wherein, R ⁶ 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 replaced by a fluorine atom; Y ² is a fluorine atom,
Chlorine _{atom, -OCF 3, -OCF 2 H,} -CF 3, -CF 2
_{H, -CFH 2, -OCF 2 CF} 2 H or -OCF ₂ C,
Indicates FHCF _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-, -C
F ₂ O—, —OCF ₂ —, —CH ＝ CH—, or a single bond; ring Q ¹ is trans-cyclohexane-1,4-
Diyl, 1,3-dioxane-2,5-diyl, or 1,4-, in which a hydrogen atom may be replaced by a fluorine atom
Phenylene, ring Q ² represents trans-cyclohexane-1,4-diyl, or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, and each atom constituting these compounds is It may be substituted with the isotope. ) 5. A compound containing at least one compound according to claim 1 or 2 as a first component and a compound selected from the group of compounds represented by general formulas (7) and (8) as a second component. A liquid crystal composition comprising at least one compound represented by the formula: Embedded image (Wherein, R ⁷ and R ⁸ each independently represent an alkyl group having 1 to 10 carbon atoms;
One or more methylene groups may be substituted with an oxygen atom or -CH = CH-, and 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; ring Q ³ represents trans-cyclohexane-1,4-diyl, 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 replaced by a fluorine atom, wherein ring Q ⁵ is trans-cyclohexane-1,4-diyl or 1,4
-Phenylene, and Z ³ is — (CH ₂ ) ₂ —, —COO
-Or 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; May be substituted with its isotope. ) 6. A compound containing at least one compound according to claim 1 or 2 as a first component, and represented by the general formulas (4), (5) and (6) as a second component. At least one compound selected from the group of compounds represented by general formulas (9), (10) and (11) as a third component. A liquid crystal composition comprising: Embedded image (Wherein, R ⁹ and R ¹⁰ each independently represent a carbon number of 1 to 10)
Wherein at least one non-adjacent methylene group in the alkyl group is an oxygen atom or -CH = CH-
And may be substituted with 1 in this alkyl group.
More than one hydrogen atom may be replaced by a fluorine atom; ring Q ⁶ , ring Q ⁷ and ring Q ⁸ are each independently trans-cyclohexane-1,4-diyl, pyrimidine-
2,5-diyl or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom; Z ⁴ and Z ⁵ are each independently -C≡C-, -COO-,-( C
H ₂ ) ₂ —, —CH ＝ CH— or a single bond;
The atoms constituting these compounds may be substituted with their isotopes. ) 7. A compound containing at least one compound according to claim 1 or 2 as a first component, and represented by formulas (12), (13) and (14) as a second component. A liquid crystal composition comprising at least one compound selected from a compound group. Embedded image (Wherein, R ¹¹ and R ¹² each independently represent a carbon number of 1 to 10)
Wherein at least one non-adjacent methylene group in the alkyl group is an oxygen atom or -CH = CH-
And may be substituted with 1 in this alkyl group.
At least one hydrogen atom may be replaced by a fluorine atom; ring Q ⁹ and ring Q ¹⁰ each independently represent trans-cyclohexane-1,4-diyl or 1,4-phenylene; L ⁶ and L ⁷ each independently represents a hydrogen atom or a fluorine atom, but does not represent a hydrogen atom at the same time;
Z ⁶ and Z ⁷ are each independently — (CH ₂ ) ₂ —, —CO
It represents O- or a single bond; the atoms constituting these compounds may be substituted with their isotopes. ) 8. A compound containing at least one compound according to claim 1 or 2 as a first component, and represented by the general formulas (9), (10) and (11) as a second component. At least one compound selected from the group consisting of
Contains, as the third component, the general formula (12),
A liquid crystal composition comprising at least one compound selected from the group consisting of the compounds represented by (13) and (14). 9. A compound containing at least one compound according to claim 1 or 2 as a first component, and a compound represented by the general formulas (7) and (8) as a second component. Containing at least one compound selected,
A liquid crystal composition comprising, as a third component, at least one compound selected from the group of compounds represented by formulas (9), (10) and (11). 10. A compound containing at least one compound according to claim 1 or 2 as a first component, and represented by the general formulas (4), (5) and (6) as a second component. And at least one compound selected from the compound group represented by the general formulas (7) and (8) as a third component. A liquid crystal composition comprising, as a component, at least one compound selected from the group of compounds represented by formulas (9), (10) and (11). 11. A liquid crystal composition according to any one of claims 3 to 10, further comprising one or more optically active compounds. 12. A liquid crystal display device comprising the liquid crystal composition according to claim 3. Description: