JP2974827B2 - Optically active substance and liquid crystal composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel optically active substance having a .delta.-valerolactone ring in its structure and a ferroelectric liquid crystal composition containing the same.

[0002]

2. Description of the Related Art At present, liquid crystal widely used as a display material belongs to a nematic phase, and has characteristics such as a light-receiving type that does not cause eyestrain and extremely low power consumption. However, it has the drawbacks that the display is slow and the display becomes invisible depending on the viewing angle.

A display device using a ferroelectric liquid crystal as a device having characteristics of a nematic type liquid crystal that does not cause eyestrain and extremely low power consumption, and having a high-speed response and a high contrast comparable to a light emitting type display device. Printer heads are being considered.

[0004] Ferroelectric liquid crystals were first developed by Meyer (R.
B. Meyer) et al. (J. Physique 36, L-69 (1975)), which has a chiral smectic C phase (hereinafter abbreviated as Sm ^* C phase). A typical example is p-decyloxybenzylidene-p'-amino-2-methylbutylcinnamate (hereinafter abbreviated as DOBAMBC) represented by the following formula.

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[0005]

However, the above-mentioned DOBAM
Most of the BC and some of the ferroelectric liquid crystal materials proposed thereafter have a narrow temperature range exhibiting ferroelectricity (the temperature range in which the Sm ^* C phase exists), and have a short helical pitch of the chiral nematic phase and an orientation property. However, it is difficult to use it alone for practical use.

Therefore, in general, attempts have been made to mix various types of ferroelectric liquid crystals to extend the temperature range showing the Sm ^* C phase to the low temperature side and the high temperature side around room temperature. As for the helical pitch of the chiral nematic phase, attempts have been made to compensate for the helical pitch by mixing two or more kinds of ferroelectric liquid crystals in which the winding directions of the helix are opposite to each other. Further, for a printer head that requires an ultra-high-speed response, a ferroelectric liquid crystal having a spontaneous polarization larger than that of a conventionally developed ferroelectric liquid crystal is required.

It is an object of the present invention to provide a liquid crystal composition which is chemically stable, has no coloration, has excellent light stability, exhibits a large spontaneous polarization when blended with a liquid crystal composition, and has a helical pitch of a chiral nematic phase. It is to provide an optically active substance having a longer length and a liquid crystal composition obtained by blending the same.

[0008]

That is, the gist of the present invention resides in an optically active substance having a δ-valerolactone ring represented by the following formula (1) and a liquid crystal composition containing one or more kinds thereof.

Embedded image (In the formula, R ₁ is a linear or branched alkyl group having 1 to 18 carbon atoms, a linear or branched alkenyl group having 2 to 18 carbon atoms, a carbon atom having 1 to 3 carbon atoms in the alkoxy moiety, A linear or branched alkoxyalkyl group of the formulas 1 to 18, or one of the hydrogen atoms among these substituents
When at least one is halogen-substituted and has a structure capable of having an optically active group, it indicates that it may be an optically active group or a racemic form, and R ₂
Represents an alkyl group having 4 to 18 carbon atoms, X represents a single bond,
-O -, - CO ₂ - or -OCO- indicates, Y is a single _{bond, -CO 2 -, - O -} , - CH 2 O- or -OCH ₂ -
And A is

Embedded image And B, B ′ and B ″ each represent hydrogen, halogen, cyano group, methyl group, methoxy group or trihalomethyl group, V represents a single bond, —CH ₂ O—, —OCH ₂ —, —CO ₂
-Or -OCO-, and * indicates that the carbon to which it is attached is an asymmetric carbon. )

In the optically active substance of the present invention, R ₁ in Chemical formula ₁ is a straight-chain or branched-chain alkyl group having 4 to 14 carbon atoms, a straight-chain or branched-chain alkenyl group having 4 to 14 carbon atoms, A linear or branched alkoxyalkyl group having 4 to 14 carbon atoms can be exemplified as a preferable example,
Examples of such a linear alkyl group include n-butyl, n-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-butyl
- such as tetradecyl can be exemplified, and as the branched chain alkyl group _{- (CH 2) a C (} CH 3) H (CH 2) b CH 3 (a is an integer of 0, b is 1 to 11 integer And 1
≦ a + b ≦ 11. )). In the case of such a methyl-branched alkyl group, both those having optical activity and those having a racemic form can be suitably used.

Examples of those substituted with halogen by a linear alkyl group include-(CH ₂ ) _k C (W) H (CH ₂ ) _i CH ₃ (where W represents a fluorine, chlorine or bromine atom, and And i are each an integer of 0 to 12 and 2 ≦ k + i ≦ 12), and these are more preferably optically active groups. Examples of those substituted with a branched alkyl group by halogen include an alkyl group having a trifluoromethyl branch [— (CH ₂ ) _a C (CF ₃ ) H].
(CH ₂ ) _b CH ₃ ], which is more preferably an optically active group. (A and b represent the above-mentioned meaning.)

[0011] As an alkoxyalkyl group of straight chain _{- (CH 2) C OC j} H 2j + 1 Examples of the alkoxyalkyl group branched _{- (CH 2) k C (} CH 3) H (CH 2) j OC j H _{2j + 1-} (CH ₂ ) _k C (OC _j H _{2j + 1} ) H (CH ₂ ) _i CH ₃ (j is an integer of 1 to 3, c is an integer of 4 to 14, and k and i are as described above. In the case of a branched-chain alkoxyalkyl group, it may be a racemic mixture or an optically active group.

R ₂ is preferably an alkyl group having 4 to 12 carbon atoms because the compound must have low viscosity and increase spontaneous polarization. As A

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Embedded image Can be exemplified as preferable ones.

From the viewpoint of increasing the response speed of the liquid crystalline composition containing the optically active substance of the present invention, it is preferable to increase the dipole moment around the asymmetric carbon or to increase the rotation hindrance. the in Y single bond, -O- or -CO ₂ - is preferably, in terms of linearity, gradient liquid crystal phase Deeki of by induced dipole moment of the molecule -CO ₂ -, - O -, - OCH ₂ - or preferably -CH ₂ O-a is a single bond from the viewpoint of ease of synthesis, -CO ₂ -, - O-or -CH ₂ O-
It is preferred that

X is preferably a single bond, -O-, -CO ₂ -or -OCO- from the viewpoint of ease of synthesis, and V is the magnitude of the dipole moment;
-CO _2- , -O from the viewpoints of rotation hindrance, easy generation of a tilted liquid crystal phase due to induced dipole moment, and ease of synthesis.
CO -, - OCH ₂ - or is preferably -CH ₂ O-in which.

The compound of formula 1 can be prepared by the following method.・ When Y is -CO _2-

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The compound of formula 1 can also be synthesized by the following method.

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When Y is -O-

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When Y is -OCH _2-

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The one that is considered to contribute the most to the development of spontaneous polarization or potential spontaneous polarization in a ferroelectric liquid crystal or a compound as a compound material for the ferroelectric liquid crystal is rotation around asymmetric carbon. Is considered to be a regulated large permanent dipole moment.

The optically active compound represented by Chemical formula 1 of the present invention is δ-
Having an asymmetric carbon fixed by a valerolactone ring,
This can be considered as part of the mesogen.

In the case of the δ-valerolactone ring, the energy difference between the quasi-boat type and the quasi-chair type conformation is low at 0.54 kcal / mol without substitution, and it is said that the conformation changes easily. ing.
(T.Philip, NLAllinger, J.Am.Chem.Soc., 103
2151, 1981)

However, it is presumed that when substituents are introduced at the 2- and 5-positions of δ-valerolactone, the substituents easily take a pseudo-boat form in the cis configuration and a pseudo-chair form in the trans configuration. Is done. At this time, a larger dipole moment is expected because the lactone bond is closer to a plane in the pseudo chair type,
In the trans configuration, asymmetry is not given to rotation around the molecular long axis, so that a very large spontaneous polarization cannot be expected. However, when the 2,5,5-substituted δ-valerolactone as shown in Chemical formula 1 is used, the δ-valerolactone ring tends to have a more planar structure due to the interaction of the substituents at the 5,5-positions, and thus the equilibrium is pseudo. It is considered that the boat type has largely shifted to the pseudo chair type.

Further, by using the 5,5-disubstitution, one of the substituents is located at an axial position where the steric hindrance is greater with respect to rotation around the molecular long axis. Occurs. In other words, in the present invention, the use of the 5,5-disubstituted lactone has an excellent feature that the optically active substance for a ferroelectric liquid crystal having a low melting point and a large spontaneous polarization can be obtained while fixing the conformation. Having.

Some of the optically active substances of the present invention exhibit a liquid crystal phase, and others do not exhibit a liquid crystal phase by themselves.
Non-chiral liquid crystal or liquid crystal composition showing a phase sequence of isotropic phase-nematic phase-smectic A phase-smectic C phase or isotropic phase-nematic phase-smectic C phase, even though it does not show a liquid crystal phase by itself, It has a property of inducing a ferroelectric phase (chiral smectic C phase) by adding 0.1 to 90 mol% within a range not destroying the liquid crystallinity. Therefore, even those that do not exhibit a liquid crystal phase by themselves are useful as additives for the ferroelectric liquid crystal composition.

As the liquid crystal, for example, when a liquid crystal is used for a display device such as a display, it is more preferable to use a plurality of liquid crystal compounds or a mixture of these and a compound for compounding than to use a single liquid crystal compound. Advantageously, physical properties such as a temperature range (a temperature range showing ferroelectricity), a tilt angle, a helical pitch, a spontaneous polarization value, and a rotational viscosity can be changed.

The liquid crystal composition of the present invention may contain at least one kind of the optically active substance represented by the chemical formula (1), and may be mixed with the compound or composition exhibiting ferroelectricity. Preferred compounds that may contain a chiral liquid crystal or a liquid crystal composition, and which can be mixed with the optically active substance represented by Chemical Formula 1 as the liquid crystal composition include the following compounds.

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[0027]

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

Reference Example 1 t-butyl (S) -γ-butyrolactone-γ-carboxylate
Synthesis of glycol ester (S)-.gamma.-butyrolactone-.gamma.-carboxylic acid DLCo
ffen et al. (J. Org. Chem., 1988, 53, p47).
80-4786). That is, 500 ml
L-glutamic acid (147 g) was suspended in water and stirred vigorously, and sodium nitrite (104 g) was added thereto.
A solution dissolved in 4 ml and 250 ml of 5.6N hydrochloric acid were simultaneously added dropwise over 5 hours. During the dropwise addition, the reaction temperature was kept at 15 to 20C.

After completion of the dropwise addition, the mixture was stirred at room temperature overnight,
Water was distilled off under reduced pressure while keeping the temperature at not more than ° C, ethyl acetate was added, and the mixture was dried over magnesium sulfate. This is filtered and the filtrate is acid-ion exchange resin (Amberlite I).
R-120B) was added to remove 20 g of residual glutamic acid. Then, the mixture was filtered, the solvent was distilled off from the filtrate under reduced pressure, and the remaining water was removed by azeotropic distillation with benzene.

To this was added methylene chloride, which was crystallized in a refrigerator, and 74 g of (S) -γ-butyrolactone-γ-
A carboxylic acid was obtained. This was suspended in 200 ml of ether, and acid-type ion exchange resin (Amberlite IR-120) was suspended.
B) Add 25 g, cool to −20 ° C., add isobutylene 6
0 ml (1.2 equivalents) was added, and the mixture was stirred and reacted at 0 ° C. for 4 hours. After the reaction, the solid matter was filtered, and isobutylene and ether were distilled off from the filtrate.
-Butyrolactone-γ-carboxylic acid t-butyl ester was obtained. (120-123 ° C / 4mmHg, [α]
_D (23.5 ° C.) = + 4.81 (C = 0.935, CH
Cl ₃ ))

Example 1 (S) -2- (4′-octyloxybiphenyl-4-
Synthesis of (carboxy) -5,5-dihexyl-δ-valerolactone 5 g (27 mmol) of (S) -γ-butyrolactone carboxylic acid t-butyl ester was dried in diethyl ether 10
Dissolve in 0 ml, replace with argon, cool in a dry ice acetone bath, slowly add 30 ml (2.1 equivalents) of a 2 mol hexylmagnesium bromide ether solution, and after completion of the addition, stir at the same temperature for 2 hours. And reacted. Next, a saturated ammonium chloride solution was slowly added dropwise, and the mixture was extracted with diethyl ether.
Then, it was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off from the solution after drying, and the residue was purified by silica gel column chromatography to obtain 2.25 g of (S) -2,5-dihydroxy-5-hexyl-undecanecarboxylic acid t-butyl ester. Was.

This was dissolved in 50 ml of benzene, p-toluenesulfonic acid was added, and the mixture was refluxed for 5 hours. The obtained reaction product was purified by column chromatography to give 0.9
g of (S) -2-hydroxy-5,5- dihexyl- δ
-Valerolactone was obtained.

This 0.1 g and 0.2 g of 4'-octyloxybiphenyl-4-carboxylic acid were dissolved in methylene chloride, and the mixture was dissolved in 0.1 ml of dicyclohexylcarbodiimide (DCC).
2 g and dimethylaminopyridine 0.05 g were added, and reacted at room temperature overnight. The reaction solution after filtration was concentrated and purified by column chromatography to obtain 0.13 g of (S) -2-
(4'-octyloxybiphenyl-4-carboxy)
-5,5-Dihexyl-δ-valerolactone was obtained. Its melting point was 83 ° C. ₁ H-NMR = 8.1
0 (2H, d), 7.59 (4H, q), 6.95 (2
H, d), 5.46 (1H, t), 4.0 (2H,
t), 1.1 to 2.4 (36H, m), 0.90 (9
H, t)

A Grignard reagent is prepared by using alkyl bromide (n = 4 to 5) or alkyl bromide (n = 7 to 18) and magnesium in place of hexyl bromide. Among them, derivatives of R2 in which n = 4 to 5 or n = 7 to 18 can be synthesized.

Also, 4'-octyloxybiphenyl-4
1 to 7 or 9 to 18 carbon atoms in place of the carboxylic acid
Straight-chain alkoxybiphenyl-4-carboxylic acid, branched alkoxybiphenyl-4-carboxylic acid having 3 to 18 carbon atoms, and having 1 to 1 carbon atoms having an alkoxy group having 1 to 3 carbon atoms
8 alkoxyalkyloxybiphenyl-4-carboxylic acid, linear or branched alkenyloxybiphenyl-4-carboxylic acid having 2 to 18 carbon atoms, 1 to 18 carbon atoms
Linear or branched alkyl biphenyl-4-carboxylic acid, linear or branched alkenyl biphenyl-4-carboxylic acid having 2 to 18 carbon atoms, 1 to 18 carbon atoms having an alkoxy group having 1 to 3 carbon atoms Alkoxyalkylbiphenyl-4-carboxylic acid, linear or branched alkoxycarbonylbiphenyl-4-carboxylic acid having 1 to 18 carbon atoms,
C2-C18 linear or branched alkenyloxycarbonylbiphenyl-4-carboxylic acid, C1-C18 alkoxyalkyloxycarbonylbiphenyl-4-carboxylic acid having a C1-C3 alkoxy group, carbon Linear or branched alkylcarbonyloxybiphenyl-4-carboxylic acid having 1 to 18 carbon atoms, linear or branched alkenylcarbonyloxybiphenyl-4-carboxylic acid having 2 to 18 carbon atoms, alkoxy having 1 to 3 carbon atoms C1-C18 alkoxyalkylcarbonyloxybiphenyl-4-carboxylic acid having a group, halogen-substituted alkoxybiphenyl-4-carboxylic acid, halogen-substituted alkylbiphenyl-4-carboxylic acid, halogen-substituted alkoxycarbonylbiphenyl-4-carboxylic acid , Halogen-substituted alkyl carbonyl Oxybiphenyl-4-carboxylic acid, halogen-substituted alkenyloxybiphenyl-4-carboxylic acid or halogen-substituted alkoxyalkyloxybiphenyl-4-carboxylic acid is used in the same manner as described above to obtain a compound represented by the formula (1). Is a linear or branched alkyl or alkenyl group, an alkoxyalkyl group having 1 to 18 carbon atoms having an alkoxy group having 1 to 3 carbon atoms or a halogen-substituted one thereof, and X is an ether bond, A derivative having a single bond, a carbonyloxy group or an oxycarbonyl group, wherein A is biphenyl and Y is a carbonyloxy group can be synthesized.

Also, 4'-octyloxybiphenyl-4
A straight-chain or branched-chain alkoxyphenyloxymethylphenyl-4-carboxylic acid having 1 to 18 carbon atoms instead of a carboxylic acid, an alkoxyalkyloxyphenyloxy having 1 to 18 carbon atoms having an alkoxy group having 1 to 3 carbon atoms Methylphenyl-4-carboxylic acid, linear or branched alkenyloxyphenyloxymethylphenyl-4-carboxylic acid having 2 to 18 carbon atoms, linear or branched alkylphenyloxymethylphenyl having 1 to 18 carbon atoms 4
-Carboxylic acid, C1-C18 alkoxyalkylphenyloxymethylphenyl-4-carboxylic acid having a C1-C3 alkoxy group, C2-C18 linear or branched alkenylphenyloxymethylphenyl- 4-carboxylic acid, linear or branched alkoxycarbonylphenyloxymethylphenyl-4-carboxylic acid having 1 to 18 carbon atoms, alkoxyalkyloxycarbonylphenyl having 1 to 18 carbon atoms having an alkoxy group having 1 to 3 carbon atoms Oxymethylphenyl-4-carboxylic acid, linear or branched alkenyloxycarbonylphenyloxymethylphenyl-4-carboxylic acid having 2 to 18 carbon atoms, linear or branched alkylcarbonyloxyphenyl having 1 to 18 carbon atoms Oxymethylphenyl-4-carboxylic acid, carbon number 1 Carbon atoms having three alkoxy groups 1
To 18 alkoxyalkylcarbonyloxyphenyloxymethylphenyl-4-carboxylic acids having 2 to 1 carbon atoms
8 straight-chain or branched-chain alkenylcarbonyloxyphenyloxymethylphenyl-4-carboxylic acid, halogen-substituted alkoxyphenyloxymethylphenyl-4
-Carboxylic acid, halogen-substituted alkoxycarbonylphenyloxymethylphenyl-4-carboxylic acid, halogen-substituted alkenyloxyphenyloxymethylphenyl-
By using 4-carboxylic acid or halogen-substituted alkoxyalkyloxyphenyloxymethylphenyl-4-carboxylic acid in the same manner as described above, a derivative in which A in the compound represented by Chemical Formula 1 is phenyloxymethylphenyl can be synthesized. .

Further, the same benzyloxyphenyl-4-carboxylic acid derivative and phenyl as the above-mentioned phenyloxymethylphenyl-4-carboxylic acid derivative may be used in place of 4'-octyloxybiphenyl-4-carboxylic acid. When a carbonyloxyphenyl-4-carboxylic acid derivative or a phenyloxycarbonylphenyl-4-carboxylic acid derivative is used, compounds in which A is benzyloxyphenyl, phenylcarbonyloxyphenyl or phenyloxycarbonylphenyl Can be synthesized.

Similarly, when the same alcohol derivative is used in place of the carboxylic acid derivative, a compound in which Y is an ether bond in Chemical formula 1 can be synthesized.

Example 2 (S) -2- (4'-octyloxybiphenyl-4-)
Synthesis of carboxy) -5,5-didecyl-δ-valerolactone A Grignard reagent was prepared from 1.9 g of magnesium and 15.0 g of decyl bromide in 100 ml of diethyl ether and cooled in a stream of argon under cooling with dry ice. 2. The procedure of Example 1 was repeated, except that 5 g of (S) -6-butyrolactone-γ-carboxylic acid t-butyl ester was dissolved in 50 ml of diethyl ether.
3 g of (S) -2,5-dihydroxy-5-decylpentadecanecarboxylic acid t-butyl ester were obtained.

This was dissolved in 150 ml of benzene and p-
0.2 g of toluenesulfonic acid was added and the mixture was refluxed for 5 hours, and the reaction product was purified by column chromatography (S).
1 g of -2-hydroxy-5,5- didecyl -6-valerolactone was obtained. Example 2 except that 0.1 g was used.
0.1 g of (S) -2- (4'-octyloxybiphenyl-4-carboxy) -5,5 - didecyl
Le -6-valerolactone was obtained. Its melting point is 6
6.2 ° C. ¹ H-NMR = 8.10 (2H,
d), 7.56 (4H, q), 6.95 (2H, d),
5.45 (1H, t), 4.0 (2H, t), 1.1 to
2.4 (52H, m), 0.90 (9H, t)

Example 2 The following compounds were mixed at the following mixing ratio to obtain a liquid crystal composition.

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This composition shows the following phase transition:

(Equation 1)

In the above, Cryst is a crystal, SmC
Indicates a smectic C phase, SmA indicates a smectic A phase, N indicates a nematic phase, Iso indicates an isotropic phase, and a number near an arrow indicates a transition temperature (° C.) to the phase. This liquid crystal composition is not a ferroelectric liquid crystal and does not exhibit spontaneous polarization because it is composed only of a non-chiral compound.

By mixing 98 mol% of this composition with 2 mol% of the optically active substance obtained in Example 1, a ferroelectric liquid crystal composition was obtained. This ferroelectric liquid crystal composition has a temperature of around 0 ° C to 51 ° C.
Shows the Sm ^* C phase in the temperature range up to
A mA phase, a chiral nematic phase at 62 to 65 ° C., and an isotropic liquid at higher temperatures.

Separately, a 2 μm cell having a transparent electrode coated with polyimide as an alignment treatment agent, rubbed on its surface and subjected to parallel alignment treatment is prepared, and this ferroelectric liquid crystal composition is injected into the cell. A dielectric liquid crystal device was obtained. This element was placed between two orthogonal polarizers, and an electric field was applied. It was recognized that the intensity of the transmitted light was changed by the application of ± 20 V, and the time (response time) during which the transmitted light intensity changed from 0% to 50% was determined to be 70 μs (25 ° C.).
Was measured).

The liquid crystal composition was placed in an 8 μm cell treated in the same manner as in the response time measurement, and the spontaneous polarization value at 25 ° C. was measured by the triangular wave method.
It was 3 nC / cm ² .

Further, when the helical pitch of the chiral nematic phase of this liquid crystal composition was measured by a Cano-Wedge method using a wedge-shaped cell, it was impossible to measure (> 300 μm) at 63 ° C. near the transition to the SmA phase. It became longer.

Example 4 The following compounds obtained in Examples 1 and 2 were added in an amount of 2 mol% each to a liquid crystal composition comprising the following non-chiral compound.・ Compound 1

Embedded image (Compound obtained in Example 1) Compound 2

Embedded image (Compound obtained in Example 2)

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The liquid crystal composition comprising the above non-chiral compound exhibits the following phase transition.

(Equation 2) Compounds 1 and 2 were each added to the above achiral liquid crystal composition in an amount of 2 m
Table 1 shows the phase transition behavior, spontaneous polarization, and helical pitch of the chiral nematic phase of the liquid crystal composition to which ol% was added.

[Table 1]

As described above, the optically active substance of the present invention is mixed with a non-ferroelectric liquid crystal composition to form a ferroelectric liquid crystal composition, or as an additive. When it is used as a compounding component, the composition enhances spontaneous polarization and is effective in improving the response speed. Also, despite the induction of a sufficiently large spontaneous polarization, the helical pitch of the chiral nematic phase is extremely long, so that the helical pitch of the chiral nematic phase required for the preparation of the conventional composition is completely unnecessary. In addition, it does not color the composition upon addition or blending, and exhibits excellent properties of not reducing the chemical or light stability of the composition, and the liquid crystal composition of the present invention is also described above. As a result, the composition has excellent performance.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-59-164788 (JP, A) JP-A-1-199959 (JP, A) JP-A-2-294387 (JP, A) JP-A-3-3 20269 (JP, A) JP-A-3-72473 (JP, A) JP-A-3-95174 (JP, A) JP-A-3-128371 (JP, A) JP-A-4-211678 (JP, A) JP-A-4-364176 (JP, A) Jpn. J. Appl. Phys. , Part 2, 28 [7] (1989) pp. L1258-L1260. Chem. Soc. , Chem. Commun. , [5] (1991.3.1.) Pp. 311-312 (58) Fields investigated (Int. Cl. ⁶ , DB name) C07D 309/30 C07D 405/00-405/12 REGISTRY (STN) CA (STN)

Claims (2)

(57) [Claims] 1. An optically active compound having a δ-valerolactone ring represented by the following chemical formula 1. Embedded image (In the formula, R ₁ is a linear or branched alkyl group having 1 to 18 carbon atoms, a linear or branched alkenyl group having 2 to 18 carbon atoms, a carbon atom having 1 to 3 carbon atoms in the alkoxy moiety, A linear or branched alkoxyalkyl group of the formulas 1 to 18, or one of the hydrogen atoms among these substituents
When at least one is halogen-substituted and has a structure capable of having an optically active group, it indicates that it may be an optically active group or a racemic form, and R ₂
Represents an alkyl group having 4 to 18 carbon atoms, X represents a single bond,
-O -, - CO ₂ - or -OCO- indicates, Y is a single _{bond, -CO 2 -, - O -} , - CH 2 O- or -OCH ₂ -
And A represents And B, B ′ and B ″ each represent hydrogen, halogen, cyano group, methyl group, methoxy group or trihalomethyl group, V represents a single bond, —CH ₂ O—, —OCH ₂ —, —CO ₂
-Or -OCO-, and * indicates that the carbon to which it is attached is an asymmetric carbon. ) 2. A liquid crystal composition comprising at least one optically active substance according to claim 1.