JPH05132670A - Optically active compound and liquid crystal composition c0ntaining the same - Google Patents

Abstract

PURPOSE:To provide a new optically active compound useful as a component of a chiral smectic liquid crystal composition containing the specific fluorine- containing optically active compound, having a small viscosity, capable of attaining high response rates and used for ferroelectric liquid crystal displays. CONSTITUTION:Optically active epichlorohydrin is reacted with an alkoxy magnesium bromide of formula I (R<2> is alkyl; (m) is 4-11) in the presence of copper iodide, and the reaction product is dehydrated with a base to produce an epoxy compound. The epoxy compound is reacted with hydrogen fluoride- pyridine, and the resultant fluoroalcohol of formula II is reacted with p-toluene sulfonyl chloride to form a tosylate. The tosylate is reacted with a compound of formula III [A,B are (substituted)aromatic hydrocarbon ring, (substituted) aliphatic hydrocarbon ring, hetero rung; R<1> is (substrtuted)alkyl or alkoxyl to obtain the objective fluorine-containing optically active compound of formula IV useful as a component for chiral smectic liquid crystal compositions.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to novel optically active compounds useful as liquid crystal materials and liquid crystal compositions containing them.
More specifically, it relates to an optically active compound useful as a component of a chiral smectic liquid crystal composition for displaying a ferroelectric liquid crystal, and a liquid crystal composition containing them.

[0002]

2. Description of the Related Art As a display system of a liquid crystal display device, a twisted nematic (TN) type is generally used at present. However, since the driving is basically based on the anisotropy of the relative dielectric constant, there is a problem that the driving force is weak and the response speed is slow.

A display system using a ferroelectric liquid crystal has been reported by Clark and Ragawol et al. (Japanese Patent Publication No. 63-222).
87, U.S. Pat. No. 4,367,924, etc.), ferroelectric liquid crystals are next-generation liquid crystals because they have an excellent performance that they have a very fast response speed due to a relatively large driving force based on spontaneous polarization and have a memory property. It is attracting attention as a display element.

One of the liquid crystal phases of the ferroelectric liquid crystal is a chiral smectic C phase (hereinafter abbreviated as S _C ^* phase).
In order to use it as a display device, it has a wide range of S _C ^* phases and many characteristics such as high-speed response and low-temperature operation characteristics are required, but no single compound satisfies these characteristics. It is the current situation that the corresponding liquid crystal composition is used. A liquid crystal compound or a liquid crystal composition (hereinafter abbreviated as base liquid crystal) that exhibits a smectic C phase (hereinafter abbreviated as S _C phase) that does not exhibit ferroelectricity as one of the methods of constituting the composition.
There is a method of adding an optically active compound to (Mol.Cryst.Li
q. Cryst., 89, 327 (1982)).

On the other hand, in order to increase the response speed in the ferroelectric liquid crystal, there are methods (a) increasing the spontaneous polarization Ps and (b) decreasing the viscosity η. Generally, when spontaneous polarization is increased, viscosity is likely to be increased, and as a result, the response speed is not so fast. Further, it is necessary to have spontaneous polarization to make the viscosity extremely small, which is difficult in terms of molecular structure. As an attempt to solve these problems, a compound in which a fluorine atom is introduced into an alkyl chain having no substituent is disclosed in JP-A-63-2204.
2, as discussed in JP-A-1-246269. However, also regarding these, at present, an optically active compound as a constituent component of a ferroelectric liquid crystal composition showing a sufficient high speed response has not been obtained.

[0006]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel compound and a liquid crystal composition which are useful as a component of a liquid crystal material capable of realizing a high speed response.

[0007]

[Means for Solving the Problems] The above-mentioned problems include a liquid crystal composition containing at least one kind of an optically active compound represented by the following general formula (I) and a compound of the general formula (I). It was solved by developing things. General formula (I)

[0008]

[Chemical 2]

In the formula, A and B are each independently an aromatic hydrocarbon ring which may be substituted with halogen or cyano,
Represents an aliphatic hydrocarbon ring or a heterocycle, m is 4 to 1
Represents an integer of ¹ , and R ¹ represents a linear or branched alkyl or alkoxy group which may be substituted with halogen. However, one or more of non-adjacent methylene groups may be replaced with O, S or CO. R ² represents a substituted or unsubstituted alkyl group.

Further, the general formula (I) will be described in detail.
A, B and C are preferably 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 1,4-cyclohexylidene group, 2,5-pyrimidinylene group, 2,5-pyridinylene group and 3 , 6-pyridinylene group, 2,5-pyrazinylene group, 2,6-naphthylene group, 3,6-pyridazinylene group, 3,6-tetrazinylene group, 1,2,4-triazine-3,6-ylene group Is a group selected from. R
¹ preferably represents a straight-chain or branched alkyl or alkoxy group having 3 to 15 carbon atoms, which may be substituted with halogen, or one or more of non-adjacent methylene groups may be substituted with O, S or CO, Particularly preferably, pentyl group, hexyl group, heptyl group, octyl group, 7-methoxyheptyl group, nonyl group, decyl group, dodecyl group, 10
-Methoxydecyl group and undecyl group. R ² is a substituted or unsubstituted alkyl group, preferably having 1 to 4 carbon atoms.
An alkyl group of, particularly preferably a methyl group, an ethyl group,
It is a 2,2,2-trifluoroethyl group.

The inventors of the present invention have conducted extensive studies in search of a novel optically active compound, and as a result, by adding a compound represented by the general formula (I) to a base liquid crystal having an S _C phase, it is effective for high speed response. It was found that such a ferroelectric liquid crystal composition was obtained, and the present invention was completed. That is, the compound of the present invention is a liquid crystal material useful as a ferroelectric liquid crystal material.

Next, a method for producing the compound represented by the general formula (I) will be described. The compound represented by the general formula (I) can be produced, for example, by the route shown in the reaction formula described below.

[0013]

[Chemical 3]

That is, optically active epichlorohydrin (1)
Is reacted with alkoxyalkyl magnesium bromide (2) in the presence of copper iodide to give (3), which is dehydrated with a base to give epoxy (4). Hydrogen fluoride pyridine is caused to act on (4) to obtain fluoroalcohol (5). (5)
With p-toluenesulfonic acid chloride (TsCl)
After reaction with tosylate (6), compound (7)
To obtain a compound represented by the general formula (I) of the present invention.

Examples of the compound (5) include the following compounds. 2-Fluoro-6-methoxy-1-hexanol 2-Fluoro-6-ethoxy-1-hexanol 2-Fluoro-6- (2,2,2-trifluoroethyloxy) -1-hexanol 2-Fluoro-6- Vinyloxy-1-hexanol 2-fluoro-6-allyloxy-1-hexanol 2-fluoro-6-propyloxy-1-hexanol 2-fluoro-6- (1-methylethyloxy) -1-
Hexanol 2-fluoro-6-butyloxy-1-hexanol 2-fluoro-6- (2-methylpropyloxy) -1
-Hexanol 2-fluoro-6- (1-methylpropyloxy) -1
-Hexanol

2-fluoro-7-methoxy-1-heptanol 2-fluoro-7-ethoxy-1-heptanol 2-fluoro-7- (2,2,2-trifluoroethyloxy) -1-heptanol 2-fluoro -7-Vinyloxy-1-heptanol 2-Fluoro-7-allyloxy-1-heptanol 2-Fluoro-7-propyloxy-1-heptanol 2-Fluoro-7- (1-methylethyloxy) -1-
Heptanol 2-fluoro-7-butyloxy-1-heptanol 2-fluoro-7- (2-methylpropyloxy) -1
-Heptanol 2-fluoro-7- (1-methylpropyloxy) -1
-Heptanol 2-fluoro-7- (1,1-dimethylethyloxy)
-1-Heptanol

2-fluoro-8-methoxy-1-octanol 2-fluoro-8-ethoxy-1-octanol 2-fluoro-8- (2,2,2-trifluoroethyloxy) -1-octanol 2-fluoro -8-Vinyloxy-1-octanol 2-fluoro-8-allyloxy-1-octanol 2-fluoro-8-propyloxy-1-octanol 2-fluoro-8- (1-methylethyloxy) -1-
Octanol 2-fluoro-8-butyloxy-1-octanol 2-fluoro-8- (2-methylpropyloxy) -1
-Octanol 2-fluoro-8- (1-methylpropyloxy) -1
-Octanol 2-fluoro-8- (1,1-dimethylethyloxy)
-1-octanol

2-Fluoro-9-methoxy-1-nonanol 2-Fluoro-9-ethoxy-1-nonanol 2-Fluoro-9- (2,2,2-trifluoroethyloxy) -1-nonanol 2-fluoro -9- (1-methylethyloxy) -1-
Nonanol 2-Fluoro-10-methoxy-1-decanol 2-Fluoro-10-ethoxy-1-decanol 2-Fluoro-10- (2,2,2-trifluoroethyloxy) -1-decanol 2-Fluoro-10 -(1-Methylethyloxy) -1
-Decanol 2-fluoro-11-methoxy-1-undecanol 2-fluoro-11-ethoxy-1-undecanol 2-fluoro-11- (2,2,2-trifluoroethyloxy) -1-undecanol 2-fluoro- 11- (1-methylethyloxy) -1
-Undecanol

2-fluoro-12-methoxy-1-dodecanol 2-fluoro-12-ethoxy-1-dodecanol 2-fluoro-12- (2,2,2-trifluoroethyloxy) -1-dodecanol 2-fluoro -13- (1-methylethyloxy) -1
-Tridecanol 2-fluoro-13-methoxy-1-tridecanol 2-fluoro-13-ethoxy-1-tridecanol 2-fluoro-13- (2,2,2-trifluoroethyloxy) -1-tridecanol 2-fluoro- 13- (1-methylethyloxy) -1
-Tridecanol Examples of the compound represented by the general formula (I) include the following compounds.

[0020]

[Chemical 4]

[0021]

[Chemical 5]

[0022]

[Chemical 6]

[0023]

[Chemical 7]

[0024]

[Chemical 8]

The compound represented by the general formula (I) of the present invention can be combined with other liquid crystal compounds. For example, by combining with at least one kind of the following compounds, It is possible to obtain a ferroelectric liquid crystal composition having a wide S _C phase.

In this case, the compound represented by the general formula (I) is preferably used in an amount of 1 to 99% by weight of the obtained liquid crystal composition.

5-decyl-2- (4-octylphenyl) pyrimidine 5-undecyl-2- (4-octylphenyl) pyrimidine 5-dodecyl-2- (4-octylphenyl) pyrimidine 5-dodecyl-2- (4 -Nonylphenyl) pyrimidine 5-dodecyl-2- (4- (8-methylnonyl) phenyl) pyrimidine 5-dodecyl-2- (4- (9-methyldecyl) phenyl) pyrimidine

5-nonyloxy-2- (4-heptylphenyl) pyrimidine 5-octyl-2- (4-octyloxyphenyl) pyrimidine 5-nonyl-2- (4-octyloxyphenyl) pyrimidine 5-heptyl-2- (4-nonyloxyphenyl) pyrimidine 5-hexyl-2- (4'-pentylbiphenyl-4-
Il) pyrimidine 5-heptyl-2- (4'-pentylbiphenyl-4-
Il) pyrimidine 5-octyl-2- (4'-heptylbiphenyl-4-
Il) pyrimidine 5-heptyl-2- (4-heptyloxyphenyl) pyridine 5-heptyl-2- (4-octyloxyphenyl) pyridine 5-heptyl-2- (4-nonyloxyphenyl) pyridine

5-heptyl-2- (3-fluoro-4-)
Octyloxyphenyl) pyridine 5- (4-heptyloxyphenyl) -2- (4-heptylphenyl) pyridine 5-decyl-2- (4-decanoyloxyphenyl) pyrimidine 4-octyloxyphenyl 4-decyloxybenzoate 4 -Octyloxyphenyl 4-decylbenzoate 4-hexyloxyphenyl 4-octylbenzoate

The liquid crystal composition comprising a compound represented by the general formula (I) and a combination of the above compounds can be combined with other optically active compounds. For example, the optically active compounds as shown below can be used. It is possible to combine with a compound.

In this case, it is desirable to use the following optically active compounds in an amount of 0.1 to 90% by weight of the obtained liquid crystal composition.

5-octyl-2- [4-((2S) -2
-Fluorooctyloxy) phenyl] pyrimidine 5-[(2S) -2-((2S) -2-propyloxypropanoyloxy) propyloxy] -2- (4-octyloxyphenyl) pyrimidine 5-[(2S) -2-((2S) -2-propyloxypropanoyloxy) propyloxy] -2- (4'-
Heptylbiphenyl-4-yl) pyrimidine 5-((2S) -2-methylbutyl) -2- (4'-heptylbiphenyl-4-yl) pyrimidine

[0033]

The present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to the specific examples and examples.

Example 1 2-Fluoro-1- [4- (4-octyloxyphenyl) phenyloxy] -8-methoxyoctane (Exemplary Compound A02)

(R) -2-Fluoro-8-methoxyoctyl silate 332 mg, 4- (4-octyloxyphenyl) phenol 387 mg, and potassium carbonate 449 mg in DMF 2 ml were stirred at 100 ° C. for 10 hours. After completion of the reaction, 4 ml of water was added, and the mixture was extracted with ethyl acetate, washed with water and dehydrated, and then the solvent was distilled off. The crude product was purified by silica gel column chromatography (developing solvent chloroform) and recrystallized twice with ethanol-hexane to give 256 mg of 2-fluoro-1- [4- (4-octyloxyphenyl) phenyloxy]. -8-Methoxyoctane was obtained.

Phase transition temperature (° C.) Cryst. 104 Iso.

¹ H-NMR (δ, CDCl ₃ ) 0.89 (3H, t, J = 6.7 Hz) 1.2 to 1.7 (20H, m) 1.82 (2H, t J = 6. 5 Hz
) 3.34 (3H, s) 3.39 (2H, t, J = 6.4Hz) 4.00 (2H, tJ = 6.6Hz)
) 4.1 to 4.2 (2H, m) 4.85 (1H, brord d, J = 57Hz) 6.95 (2H, d, J = 6.0Hz) 6.98 (2H, d, J = 6.0 Hz) 7.45 (2H, d, J = 6.0 Hz) 7.49 (2H, d, J = 6.0 Hz)

Examples 2, 3, 4, 5, 6 4- (4-Used as compound (7) in Example 1
The following optically active compounds were synthesized by performing the same treatment as in Example 1 except that the following (a) to (e) were used instead of octyloxyphenyl) phenol.

Example 2 (a) 4- (5-octyl-2-pyrimidyl) phenol product 2-fluoro-8-methoxy-1- [4-
(5-octyl-2-pyrimidinyl) phenyloxy]
Octane (Exemplary compound A04) Phase transition temperature (° C.) Cryst. 49.9 (N ^* 49.8) Iso.

Example 3 (b) 4- (5-nonyl-2-pyrimidyl) phenol product 2-fluoro-8-methoxy-1- [4-
(5-nonyl-2-pyrimidinyl) phenyloxy] octane (Compound A09) Phase transition temperature _{(℃) Cryst. 44 S A} 54.7 N * 55.5 Iso.

Example 4 (c) 4- (trans-4-pentylcyclohexyl) phenol product 2-fluoro-8-methoxy-1- [4-
(Trans-4-pentylcyclohexyl) phenyl] octane (exemplary compound A10) Phase transition temperature (° C) Cryst. 33 Iso.

Example 5 (d) 5-hydroxy-2- (4-heptylphenyl) pyrimidine product 2-fluoro-1- [2- (4-heptylphenyl) -5-pyrimidyloxy] -8-methoxyoctane ( Exemplified Compound A12) Phase Transition Temperature (° C) Cryst. 49.2 (Sc ^* 41.8) S _A 68.
4 Iso.

Example 6 (e) 2-Fluoro-4- (5-octyl-2-pyrimidyl) phenol Product 2-Fluoro-1- [2-fluoro-4-
(5-octyl-2-pyrimidyl) phenyloxy]-
8-Methoxyoctane (Exemplary Compound A16) Phase Transition Temperature (° C) Cryst. 42.8 (N ^* 27.3) Iso.

Example 7 2-Fluoro-7-methoxy-1- [4- (5-octyl-2-pyrimidinyl) phenyloxy] heptane (Exemplary Compound A23)

(S) -2-Fluoro-7-methoxyheptylsilate 280 mg, 4- (5-octyl-2-
300 mg of potassium carbonate was added to 256 mg of pyrimidyl) phenol and 2 ml of DMF, and the mixture was stirred at 110 ° C. for 8 hours. After completion of the reaction, 5 ml of water was added, extracted with ethyl acetate, washed with water and dehydrated, and then the solvent was distilled off. The crude product was purified by silica gel column chromatography using a hexane / THF (4/1) mixed solvent, and recrystallized from ethanol to give 160 mg of 2-fluoro-7-methoxy-1- [4- (5. -Octyl-2
-Pyrimidinyl) phenyloxy] heptane was obtained.

[0046] Phase transition temperature (℃) Cryst. 47 (S C * 34 S A 41 N * 4
2) Iso.

¹ H-NMR (δ, CDCl ₃ ) 0.88 (3H, t, J = 6.7 Hz) 1.2 to 2.0 (20H, m) 2.60 (2H, t, J = 7) .6 Hz) 3.34 (3H, s) 3.38 (2H, t, J = 6.4Hz) 4.1-4.2 (2H, m) 4.85 (1H, brord d, J = 57Hz) 7.01 (2H, d, J = 8.9Hz) 8.37 (2H, d, J = 8.9Hz) 8.59 (2H, s)

Example 8 7-Ethoxy-2-fluoro-1- [4- (5-octyl-2-pyrimidyl) phenyloxy] heptane (Exemplary Compound A42)

(S) -7-Ethoxy-2-fluoroheptylsilate 248 mg, 4- (5-octyl-2-
480 mg of potassium carbonate was added to 420 mg of pyrimidyl) phenol and 3 ml of DMF, and the mixture was stirred at 100 ° C. for 6 hours. After completion of the reaction, 6 ml of water was added, extracted with ethyl acetate, washed with water and dehydrated, and then the solvent was distilled off. The crude product was purified by column chromatography using a hexane / ethyl acetate (8/1) mixed solvent, and recrystallized from ethanol to give 260 mg of 7-ethoxy-2-fluoro-1- [4- (5. -Octyl-2-pyrimidyl) phenyloxy] heptane was obtained.

Phase transition temperature (° C.) Cryst. 38.9 S _A 43.7 Iso.

¹ H-NMR (δ, CDCl ₃ ) 0.87 (3H, t, J = 6.7 Hz) 1.2 to 2.0 (23H, m) 2.60 (2H, t, J = 7) .6 Hz) 3.38 (2H, t, J = 6.4 Hz) 3.48 (2H, t) 4.1 to 4.2 (2H, m) 4.85 (1H, brord d, J = 57 Hz) 7.01 (2H, d, J = 8.9Hz) 8.37 (2H, d, J = 8.9Hz) 8.59 (2H, s)

Example 9 7-Ethoxy-2-fluoro-1- [4- (4-octyloxyphenyl) phenyloxy] heptane (Exemplary Compound A45)

The same treatment as in Example 8 except that 4- (4-octyloxyphenyl) phenol was used instead of 4- (5-octyl-2-pyrimidyl) phenol used as the compound (7) in Example 8. Was performed to synthesize 7-ethoxy-2-fluoro-1- [4- (4-octyloxyphenyl) phenyloxy] heptane.

Phase transition temperature (° C.) Cryst. 88.1 Sc ^* 90.1 S _A 93.0 Is
o.

Example 10 20% by weight of the compound of Example 5 (exemplary compound A12),
The liquid crystal composition composed of the following compounds showed a phase transition temperature (° C.) of S _C ^* 60.0 S _A 76.5 Iso.

[0056]

[Chemical 9]

This composition was coated with polyimide as an orientation treatment agent, and the surface was rubbed and injected into a cell having a thickness of 2 μm provided with a transparent electrode which was subjected to parallel treatment. When it was installed between the two and an electric field was applied, a change in transmitted light intensity was observed by applying ± 10 V. From the change in transmitted light intensity at this time, the spontaneous polarization value Ps was determined by the response time and the triangular wave method. The viscosity was determined according to the literature (Kimura et al., Jpn.J.Appl.Phys., 26, P.L255 (1987)), and the correction by the tilt angle was performed according to η ₀ = η / sin ² Θ.

Temperature Response time Ps Tilt angle Viscosity 25 ° C. 185 μs 4.8 nC / cm ² 23.1 ° 123 mPa · s

Example 11 A composition was prepared in the same manner as in Example 12 using the compound of Example 7 (exemplary compound A23).

The phase transition temperature (° C.) of S _C ^* 51.0 S _A 72.8 Iso was shown. The response time and other values were as follows. Temperature Response time Ps Tilt angle Viscosity 25 ° C 44.0 μs 21.4 nC / cm ² 19.0 ° 179 mPa · s

Comparative Example 1 A composition was prepared in the same manner as in Example 10 using the following compounds contained in the claims of JP-A-63-22042,

[0062]

[Chemical 10]

The phase transition temperature (° C.) of S _C ^* 60.2 S _A 76.8 Iso was shown. The response time and other values were as follows. Temperature Response time Ps Tilt angle Viscosity 25 ° C. 357 μs 2.8 nC / cm ² 18.1 ° 161 mPa · S Compared with Example 10, the compound of the present invention has a large spontaneous polarization and, in addition, has a significantly low viscosity It can be seen that is extremely excellent.

Comparative Example 2 A composition was prepared in the same manner as in Example 10 by using the following compound of Example 4 described in JP-A-63-22042.

[0065]

[Chemical 11]

The phase transition temperature (° C.) of S _C ^* 56.5 S _A 73.5 Iso was shown. The response time and other values were as follows. Temperature Response time Ps Tilt angle Viscosity 25 ° C. 62.0 μs 28.4 nC / cm ² 21.1 ° 296 mPa · S Compared with Example 11, the compound of the present invention has remarkably excellent responsiveness due to its remarkably small viscosity. I know that there is.

[0067]

INDUSTRIAL APPLICABILITY The present invention provides a novel compound which has not been disclosed hitherto, and by using the compound as a component of a ferroelectric liquid crystal composition, a liquid crystal composition excellent in high speed response is provided. Further, an excellent feature is that the viscosity is remarkably small, and even when it is combined with a high melting point compound or other optically active compound, which generally has a large viscosity, it has an effect of minimizing the decrease in responsiveness due to the increase in viscosity. ..

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[Procedure amendment]

[Submission date] January 21, 1992

[Procedure Amendment 1]

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[Correction content]

On the other hand, in order to increase the response speed in the ferroelectric liquid crystal, there are methods (a) increasing spontaneous polarization and (b) decreasing the viscosity η. Generally, when spontaneous polarization is increased, the viscosity is likely to be increased, and as a result, the response speed does not become very fast. Further, it is necessary to have spontaneous polarization to make the viscosity extremely small, which is difficult in terms of molecular structure. As an attempt to solve these problems, a compound in which a fluorine atom is introduced into an alkyl chain having no substituent is disclosed in JP-A-63-22042.
No. (US4867903-A), JP-A-63-1049.
49, JP-A-63-165343, JP-A-63-1.
90842, JP-A-63-216878, JP-A-6
No. 3-239275, JP-A-64-31740, JP-A-64-38077 (US4904410-A), JP-A-1-118593, JP-A-1-121244,
JP-A-1-128954, JP-A-1-213318
No. 1 / 246,269 (US Pat. No. 4,963,288-
A), JP-A-1-272571, JP-A-2-227 (US4917821-A), JP-A-2-228, JP-A-2-36154, JP-A-2-69427, JP-A-2-69467, A compound having an alkoxy substitution at the α-position of an asymmetric carbon to which a fluorine atom is bonded has been studied, which is examined in JP-A-2-115145, JP-A-2-250853, JP-A-2-279651, and JP-A-2-311431. It is examined in Kaihei 1-265052 and JP-A-2-279648. However, also regarding these, at present, an optically active compound as a constituent component of a ferroelectric liquid crystal composition showing a sufficient high speed response has not been obtained.

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Further, the general formula (I) will be described in detail.
A and B are preferably 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 1,4-cyclohexylidene group, 2,5-pyrimidinylene group, 2,5-pyridinylene group, and 2,5. -Pyrazinylene group, 2,6-naphthylene group, 3,6-pyridazinylene group, 3,6-tetrazinylene group, 1,2,4-triazine-3,6-ylene group. R ¹ preferably represents a straight-chain or branched alkyl or alkoxy group having 3 to 15 carbon atoms, which may be substituted with halogen, or one or more non-adjacent methylene groups may be substituted with O, S or CO. ,
Particularly preferred are butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, undecyl group, 2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5- Methoxypentyl group, 6-methoxyhexyl group, butyloxy group,
A pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a 3-methoxypropyloxy group, a 4-methoxybutyloxy group and a 5-methoxypentyloxy group. R
² is a substituted or unsubstituted alkyl group, preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group, an ethyl group or a 2,2,2-trifluoroethyl group.

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[0013]

Claims (2)

[Claims] 1. A liquid crystal composition comprising an optically active compound represented by the following general formula (I). General formula (I): In the formula, A and B each independently represent an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a heterocycle, which may be substituted with halogen or cyano, and m represents an integer of 4 to 11, R ¹ represents a linear or branched alkyl or alkoxy group which may be substituted with halogen. However, one or more of non-adjacent methylene groups may be replaced with O, S or CO. R ² represents a substituted or unsubstituted alkyl group. 2. An optically active compound represented by formula (I). However, the general formula (I) is the same as the general formula (I) of claim 1.