JP2863794B2 - Optically active compound, polymer liquid crystal and liquid crystal composition containing the same - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to an optically active compound applicable to various optical elements, and relates to a polymer liquid crystal and a liquid crystal composition containing the same.

[Conventional technology and its problems]

A low-molecular ferroelectric liquid crystal that responds quickly to an electric field, and has excellent characteristics in view characteristics and contrast,
It is attracting attention as a material for realizing high-performance liquid crystal display devices. However, this liquid crystal is difficult to control a cell gap in a large area, and has problems such as weakness in bending and impact resistance, so that it is difficult to adapt to a large area display and a curved surface display. Therefore, as one of attempts to improve this point, it has been considered to polymerize a low-molecular ferroelectric liquid crystal to impart moldability and shape retention. However, the conventional polymer ferroelectric liquid crystal has a low operating speed and cannot be used for displaying moving images. Another problem is that the operating temperature is high.

An object of the present invention is to provide a polymer ferroelectric liquid crystal which exhibits a wide range of chiral smectic liquid crystal phases around room temperature, has a large spontaneous polarization, and therefore has a high response speed, and can be applied to a large screen curved display material. It is in.

[Means for solving the problem]

The present invention focuses on the fact that the optically active compounds represented by the general formulas (I) and (II) have a large spontaneous polarization, and obtains the following general formula (II) obtained by bonding this to a polysiloxane.
An object of the present invention is to provide a polymer liquid crystal having main repeating units represented by I) and (IV) and a liquid crystal composition containing at least one component of the polymer liquid crystal.

(Wherein, R ⁷ represents an alkyl group, and R ⁹ is (C ^* represents an asymmetric carbon; k is an integer of 2 or more;
Represents a methyl group or a halogen atom. X is Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ).

R ⁸ is (C ^* represents an asymmetric carbon, and R ¹⁰ is an alkyl chain having 3 or more carbon atoms.

Whether the absolute configuration of R ⁹ in which Z is a methyl group is (S),
When Z is a halogen atom, the absolute configuration of R ⁹ is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is an absolute configuration of (S), and Z is a methyl group. The absolute configuration of R ⁹ is (R),
When the absolute configuration of R ⁹ in which Z is a halogen atom is (S) The absolute configuration of (R) is The absolute configuration of (S) is Is (R). ) (Wherein, R ¹¹ represents an alkyl group, and R ¹² represents (C ^* represents an asymmetric carbon, R ¹⁴ represents an alkyl chain having 3 or more carbon atoms, Z represents a methyl group or a halogen atom.) Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ).

R ¹³ is (C ^* represents an asymmetric carbon, and m represents an integer of 2 or more.)
And when Z is a methyl group, the absolute configuration of R ¹² is (S), or when Z is a halogen atom, the absolute configuration of R ¹² is (R). The absolute configuration of (S) is The absolute configuration of (R) is When the absolute configuration of R ¹² in which Z is a methyl group is (S) or the absolute configuration of R ¹² in which Z is a halogen atom is (R) The absolute configuration of (R) is The absolute configuration of (S) is Represents the absolute configuration (R). In the optically active compounds according to claims 1 and 2 of the present invention, two optically active groups are introduced into one molecule with a core portion interposed therebetween, and the sign of spontaneous polarization based on the optically active groups is introduced. Are the same, a compound exhibiting a spontaneous polarization much larger than the sum of the spontaneous polarizations exhibited by the compound containing each optically active group alone can be realized. Further, the polymer liquid crystal according to claims 3 and 4 of the present invention exhibits a large spontaneous polarization by bonding the optically active compound according to claims 1 and 2 to a polysiloxane chain. A polymer liquid crystal that responds to an electric field at high speed can be realized.

 Hereinafter, the present invention will be described in detail.

It has already been reported by the present inventors that a compound having a partial structure consisting of a carbonyl group directly confined to a core and an asymmetric carbon exhibits large spontaneous polarization. (Japanese Patent Application No. 63-278618) Most of the ferroelectric liquid crystals reported so far use an ester- or ether-based dipole. However, a dipole sandwiched between a core and asymmetric carbon is ether-based. By replacing a group or ester group with a carbonyl group, spontaneous polarization can be increased almost in proportion to the group moment of these groups. When a methylene group is interposed between the carbonyl group and the asymmetric carbon, spontaneous polarization becomes extremely small.

An optically active compound obtained by combining the above partial structure containing a carbonyl group and another optically active group with a core interposed therebetween has 2
If the sign of the spontaneous polarization based on the two optically active groups is the same, a larger spontaneous polarization is exhibited by the spontaneous polarization of the compound containing each optically active group alone. However, the degree of the increase varies depending on the type of the other optically active group or the type of the core to be combined.

The present invention realizes a compound exhibiting a spontaneous polarization much larger than the sum of the spontaneous polarizations of the compound containing each optically active group alone by selecting the type of the other optically active group and the core to be combined. .

That is, in the optically active compound according to claim 1 of the present invention, as the optically active alkanoyl group R ² , (C ^* represents an asymmetric carbon, k represents an integer of 2 or more, and Z represents a methyl group or a halogen atom) as an optically active group R ¹ combined with a core interposed therebetween. (C ^* represents an asymmetric carbon, and R ³ is an alkenyl group having 3 or more carbon atoms having an unsaturated bond at the terminal). In the optically active compound according to claim 2 of the present invention, as the optically active alkanoyl group R ⁴ , (C ^* represents an asymmetric carbon; R ⁶ represents an alkenyl group having 3 or more carbon atoms having an unsaturated bond at the terminal; Z represents a methyl group or a halogen atom); as the active group R ⁵ (C ^* represents an asymmetric carbon, and m represents an integer of 2 or more.)
You need to choose one. In the polymer liquid crystal according to claim 3, as R ⁹ (C ^* represents an asymmetric carbon; k is an integer of 2 or more;
Represents a methyl group or a halogen atom. ), As R ⁸ (C ^* represents an asymmetric carbon, and R ¹⁰ is an alkyl chain having 3 or more carbon atoms).

Further, in the polymer liquid crystal according to claim 4, R ¹² is (C ^* represents an asymmetric carbon, R ¹² represents. A is .Z indicating the number 3 or more alkyl chain carbon methyl group or a halogen atom), and as R ¹³ (C ^* represents an asymmetric carbon, and m represents an integer of 2 or more.)
You need to choose one. At this time, R ¹ and R ² , R
^{The combination} of the absolute configurations of ⁴ and R ⁵ , R ⁹ and R ¹⁰ , and R ¹² and R ¹³ must be as follows in order to match the signs of the spontaneous polarization based on both.

That is, the absolute configuration of R ² where Z is a methyl group is (S)
Or the absolute configuration of R ² in which Z is a halogen atom is (R) The absolute configuration of (S) is The absolute configuration of (R) is Whether the absolute configuration of R ² in which Z is a methyl group is (R),
When the absolute configuration of R ² in which Z is a halogen atom is (S) The absolute configuration of (R) is The absolute configuration of (S) is Must be (R).

When the absolute configuration of R ⁴ in which Z is a methyl group is (S), or the absolute configuration of R ⁴ in which Z is a halogen atom is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is an absolute configuration of (S), and the absolute configuration of R ⁴ in which Z is a methyl group is (R),
When the absolute configuration of R ⁴ in which Z is a halogen atom is (S) The absolute configuration of (R) is The absolute configuration of (S) is Must be (R).

When the absolute configuration of R ⁹ in which Z is a methyl group is (S) or the absolute configuration of R ⁹ in which Z is a halogen atom is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is an absolute configuration of (S), and Z is a methyl group. The absolute configuration of R ⁹ is (R),
When the absolute configuration of R ⁹ in which Z is a halogen atom is (S) The absolute configuration of (R) is The absolute configuration of (S) is Must be (R). Furthermore,
Whether the absolute configuration of R ¹² in which Z is a methyl group is (S),
When Z is a halogen atom and the absolute configuration of R ¹² is (R) The absolute configuration of (S) is The absolute configuration of (R) is The absolute configuration of or a a (S) Z is the absolute configuration of R ¹² is a methyl group (R), R ¹² Z is a halogen atom
Is the absolute configuration of (S) The absolute configuration of (R) is The absolute configuration of (S) is Must be (R).

Introducing a halogen atom or nitrile group into the core
It is often used as a means for improving liquid crystallinity and as a means for increasing spontaneous polarization, but this method is also effective in the present invention. That is, introduction of a fluorine atom, a chlorine atom, a bromine atom, or a nitrile group enhances liquid crystallinity and is effective in increasing spontaneous polarization.

Since the polymer liquid crystal of the present invention has a large spontaneous polarization, it has a very useful property of responding to an electric field at a high speed. Furthermore, since it exhibits a Sc ^* phase in a wide temperature range including room temperature and is easy to mold, it can be used as various optoelectronic materials such as displays, optical switches, and optical modulators.

This polymer liquid crystal is mixed with low molecular weight ferroelectric liquid crystal or non-ferroelectric liquid crystal, or other kinds of polymer liquid crystal to obtain viscosity,
It is possible to obtain a material which is improved in response speed, helical pitch, etc., has excellent electro-optical properties, and is easily formed.

Among the optically active compounds represented by the general formulas (I) and (II), the compound wherein Y is -COO- is synthesized, for example, by the following route.

(6) (A ₁ ) or (A ₃ ) or (A ₅ ) + (B ₁ ) → (I) (A ₁ ) + (B ₃ ) → (I) (A ₂ ) or (A ₄ ) or ( A ₆ ) + (B ₂ ) → (II) (A ₂ ) + (B ₄ ) → (II) Among the optically active compounds represented by the general formulas (I) and (II), Y is —OCO—. The compound is synthesized, for example, by the following route.

(10) (A ₇ ) + (B ₅ ) or (B ₇ ) → (I) (A ₈ ) + (B ₆ ) or (B ₈ ) → (II) Represented by the general formulas (I) and (II) Of the compounds
Is synthesized by, for example, the following route.

^{(R 1, R 2, R} 3, R 4, R 5, R 6, k, m, Q, Z and Y are the same as above. l is 0 or 1. The polymer liquid crystal represented by the general formula (III) is obtained by reacting a polysiloxane with an optically active compound represented by the general formula (I).

The polymer liquid crystal represented by the general formula (IV) is obtained by reacting a polysiloxane with an optically active compound represented by the general formula (II).

〔Example〕

Hereinafter, the present invention will be described in more detail with reference to Examples.
The present invention is not limited to these examples. Table 1 summarizes the structures of the compounds of Examples 1 to 8, the phase transition temperature at the time of cooling, the spontaneous polarization at 10 ° C. below the Sc ^* phase upper limit temperature, and the response speed. The determination of the liquid crystal phase and the phase transition temperature were determined by differential scanning calorimetry (DSC) measurement and observation by a deflection microscope. In addition, Table 2 shows the results of spontaneous polarization and electric field response speed at 10 ° C. below the Sc ^* phase upper limit temperature of the compound having a chiral structure alone according to the present invention as a comparative example. Compared to the self-polarization in Table 1,
The effects of the present invention are clear. (Measurement of spontaneous polarization) A polymer liquid crystal was injected under reduced pressure between two 10 × 10 mm ITO substrates adjusted to 10 μm with a spacer to prepare a cell.
When a triangular wave with a frequency of 1 Hz and 150 V was applied to the cell, the value of the domain reversal current accompanying the reversal of the dipole of the molecule was measured.

(Measurement of Response Speed) An electric field (2 × 10 ⁷ V / m) was applied to the cell used for the measurement of spontaneous polarization, and the response time of a change in transmitted light amount (0 to 90%) at that time was measured.

[Example 1] (1) (R) -4--2- (7-octenyloxy) propanoyloxy-4'-hydroxybiphenol 1.51 g of triethylamine was added to a tetrahydrofuran solution of 2.05 g of p, p'-biphenol under ice cooling. To this solution was added dropwise a solution of 2.18 g of (R) -2- (7-octenyloxy) propanoic acid chloride in tetrahydrofuran, and the mixture was stirred for 12 hours. After the reaction, the reaction mixture was diluted with chloroform, and washed with pure water. After the solution was dried over magnesium sulfate, the solvent was distilled off, and the residue was purified by column chromatography.
Further, recrystallization from ethanol gave (R) -4--2-
(7-octenyloxy) propanoyloxy-4 '
-Hydroxybiphenyl was obtained.

(2) Synthesis of (S) -4- (1-oxo-2-methylbutyl) benzoic acid 1.87 g of 4-bumorobenzyl alcohol and 3.60 g of ethyl vinyl ether 0.09 g of fluoboric acid were heated and stirred in dimethylformamide. After reacting for 8 hours, the mixture was cooled to room temperature and diluted with 100 ml of ether. Washed with an aqueous sodium hydroxide solution and dried. After removing the solvent, purification was performed on a silica column to obtain 4-bromo- (2-ethoxyethoxymethyl) benzene.

A solution of (S) -2-methylbutyric acid chloride (2.41 g) in anhydrous tetrahydrofuran (50 ml) under a nitrogen stream at -76 to -78 ° C.
Then, 2.83 g of Grignard reagent of 4-bromo- (2-ethoxyethoxymethyl) benzene was added dropwise over 2 hours. Further, the mixture was stirred at room temperature for 2 hours. After the reaction, the mixture was washed with 100 ml of water and extracted with diethyl ether. Further, the extract was washed with an aqueous sodium hydroxide solution and a saturated saline solution and dried over sodium sulfate. After evaporating the solvent, the residue was separated by a silica column, and (S) -4- (1-oxo-2-methylbutyl)-
2-ethoxyethoxymethylbenzene was obtained.

(S) -4- (1-oxo-2-methylbutyl)-
2.64 g of (2-ethoxyethoxymethyl) benzene was stirred in trifluoroacetic acid at 0 to 20 ° C. for 10 hours, the solvent was removed, and the mixture was purified by a silica column to give (s) -4- (1-oxo-2-). Methylbutyl) benzyl alcohol was obtained.

(S) -4- (1-oxo-2-) was added to a 10% aqueous sulfuric acid solution.
After adding 2.00 g of methyl butyl) benzyl alcohol and slowly adding 4.74 g of potassium permanganate while maintaining the temperature at 20 to 30 ° C., the reaction mixture was added to an aqueous solution of sodium hydrogen sulfite and extracted with ether. After drying, the mixture was concentrated and separated by a silica column to obtain (s) -4- (1-oxo-2-methylbutyl) benzoic acid.

(3) (R, S) -4- (2- (7-octenyloxy)
Propanoyloxy) biphenyl 4- (1-oxo-
Synthesis of 2-methylbutyl) benzoate 2.27 g of (R) -4- (7-octenyloxy) propanoyloxy-4'-hydroxybiphenol and (s)
-4- (1-oxo-2-methylbutyl) benzoic acid 3.68
g was dissolved in 50 ml of anhydrous dichloromethane, and 0.02 g of dimethylaminopyridine and 2.27 g of dicyclohexylcarbodiimide were added thereto, followed by stirring at room temperature for 24 hours. After the reaction, the formed precipitate was separated by filtration and the solvent was distilled off. The crude product was purified by silica gel chromatography and further recrystallized from ethanol to give (R, S) -4- (2- (7-
Octenyloxy) propanoyloxy) biphenyl
4- (1-Oxo-2-methylbutyl) benzoate was obtained.

IR (cm ^-1 ); 2930,1760,1724,1684,1602,1270,1204,10
72,890,766 [Example 2] Synthesis of polymer liquid crystal using the compound of Example 1 (R, S) -4- obtained in (1) in 10 ml of toluene
(2- (7-octenyloxy) propanoyloxy)
A solution of 1.12 g of biphenyl 4- (1-oxo-2-methylbutyl) benzoate and 0.055 wt% of isopropyl alcohol platinate in 0.05 cc and 0.12 g of polysiloxane (Toshiba Silicone) was dissolved and completely degassed, and then sealed. After reacting this at 80 ° C for 15 hours, it was reprecipitated with methanol,
Gel filtration and drying yielded the desired polymer liquid.

Example 3 Synthesis of (R, S) -4- (2- (7-octenyloxy) propanoyloxy) biphenyl 4- (1-oxo-2-methyloctyl) benzoate (S) -4- (1) was obtained in exactly the same manner as in Example 1 (2) except that (S) -2-methyloctanoic acid chloride was used instead of (S) -2-methylbutyric acid chloride. −
(Oxo-2-methyloctyl) benzoic acid was obtained. Further, (R) -4- (7-octenyloxy) propanoyloxy-4'-hydroxybiphenol and (S) -4- (1-oxo-2-methyloctyl) were prepared in the same manner as in (3) of Example 1. ) Benzoic acid is reacted to give (R, S) -4- (2-
(7-octenyloxy) propanoyloxy) biphenyl 4- (1-oxo-2-methyloctyl) benzoate was obtained.

IR (cm ^-1 ); 2924,2848,1778,1734,1682,1602,1264,12
06,1064,760 [Example 4] Synthesis of polymer liquid crystal using the compound of Example 3 (R, S) -4- (2- (7-octenyloxy) propanoyl as in Example 2 Oxy) biphenyl 4
The reaction between-(1-oxo-2-methyloctyl) benzoate and polysiloxane was performed to obtain a polymer liquid crystal.

Example 5 (1) (R) -4- (2- (7-octenyloxy))
Synthesis of propanoyloxy) benzoic acid (R) -4- (2- (7-octenyloxy) propane was prepared in exactly the same manner as in Example 1 (1) except that 4-hydroxy-benzoic acid was used instead of p, p'-biphenol. Noyloxy) benzoic acid was obtained.

(2) Synthesis of (S) -4- (1-oxo-2-methylbutyl) phenol Anisole (8.25 g) was dissolved in anhydrous 1,2-dichloroethane (100 ml), cooled to 0 ° C., and 9.2 g of aluminum chloride was added little by little. Further, a solution prepared by dissolving 9.2 g of (R) -2-methylbutyric acid chloride in 50 ml was added dropwise. After the addition, the mixture was stirred at room temperature for 1 hour. Thereafter, a further 9.2 g of ground aluminum chloride was added and the reaction mixture was refluxed for 2 hours. After still cooling to room temperature, the mixture was poured on ice containing 10 ml of hydrochloric acid and extracted with chloroform. The extracted organic layer was washed with sodium hydrogen carbonate and water, and then dried. After evaporating the solvent, the crude product was purified by silica gel chromatography to obtain (S) -4- (1-oxo-2-methylbutyl) phenol.

IR (cm ^-1 ); 3305,1651,1602,1578,1221 (3) (S, R) -4- (1-oxo-2-methylbutyl) phenyl 4- (2- (7-octenyloxy) propa Synthesis of Noyloxy) benzoate (R) -4- (2- (7-octenyloxy) propanoyloxy) benzoic acid obtained by the above reaction, and (S)-
From (4- (1-oxo-2-methylbutyl) phenol), (S, R) -4-
(1-oxo-2-methylbutyl) phenyl 4- (2
-(7-octenyloxy) propanoyloxy) benzoate was obtained.

IR (cm ^-1 ); 2928,1770,1730,1682,1602,1210,1070,76
5 Example 6 Synthesis of Polymer Liquid Crystal Using Compound of Example 5 A target polymer liquid crystal was obtained in the same manner as in Example 2.

Example 7 (1) (S) -4- (1-oxo-2-methyl-9 '
-Decenyl) phenol synthesis In (2) of Example 5, (S) -2-methyl-9-decenoic acid chloride was used in place of (S) -2-methylbutyric acid chloride, and (S) -4- (1) was obtained by the same reaction. -Oxo-2-methyl-9-decenyl) phenol was obtained.

(2) Synthesis of (R) -4- (2-hexyloxypropanoyloxy) biphenyl-4'-carboxylic acid In (1) of Example 1, instead of (R) -2- (7-octenyloxy) propanoic acid chloride, (R)-
(R) -4- (2-Hexyloxypropanoyl ioxy) biphenyl-4'-carboxylic acid was obtained by a similar reaction using 2-hexyloxypropanoic acid chloride.

(3) Synthesis of (S, R) -4- (1-oxo-2- (7-octenylpropyl)) phenyl 4- (4 '-(2-hexyloxypropanoyloxy) phenyl) benzoate (S) -4- (1-oxo-2-methyl-9-decenyl) phenol obtained by the above reaction and (R) -4- (2
-Hexyloxypropanoyloxy) biphenyl-
(S, R) -4- (1-oxo-2- (7-octenylpropyl)) phenyl 4- (4 '-(2) from 4'-carboxylic acid by the same reaction as in (3) of Example 1. -Hexyloxypropanoyloxy) phenyl) benzoate was obtained.

IR (cm ^-1 ); 2930,1768,1730,1680,1602,1258,1208,10
70,766 [Example 8] Synthesis of polymer liquid crystal using compound of Example 7 A polymer liquid crystal was obtained by the same method as in Example 2 for the purpose.

[Effects of the Invention] The polymer liquid crystal of the present invention exhibits a chiral smectic phase at around room temperature, and has a larger spontaneous polarization than a conventionally reported polymer ferroelectric liquid crystal. And respond fast. Therefore, it is a very useful polymer liquid crystal capable of displaying a moving image on a large screen and a curved surface.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C09K 19/20 C09K 19/20 19/38 19/38 19/40 19/40 (58) Investigation field (Int.Cl. ⁶ , DB name) C07C 69/773 C07C 69/90-69/94 C09K 19/20-19/40 CA (STN) REGISTRY (STN) WPI / L (QUESTEL)

Claims (5)

(57) [Claims] 1. A compound of the general formula (I) R ¹ -X-R ² ... (I) wherein R ² is (C ^* represents an asymmetric carbon; k is an integer of 2 or more;
Represents a methyl group or a halogen atom. X is Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ). R ¹ (C ^* represents an asymmetric carbon, R ³ is an alkenyl group having 3 or more carbon atoms having an unsaturated bond at the terminal), and the absolute configuration of R ^{2 wherein} Z is a methyl group is (S) Yes, Z
Is a halogen atom, the absolute configuration of R ² is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is (S), the absolute configuration of R ^{2 wherein} Z is a methyl group is (R), or
Is a halogen atom, and the absolute configuration of R ² is (S) The absolute configuration of (R) is The absolute configuration of (S) is Is (R). ). ] The optically active compound represented by these. Wherein formula ^{(II) R 4 -X-R} 5 ... ‥ (II) [ wherein, R ⁴ is, (C ^* represents an asymmetric carbon; R ⁶ represents an alkenyl group having 3 or more carbon atoms having an unsaturated bond at the terminal; Z represents a methyl group or a halogen atom.) Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ). R ⁵ (C ^* represents an asymmetric carbon, and m represents an integer of 2 or more.)
Wherein Z is a methyl group, the absolute configuration of R ⁴ is (S),
Is a halogen atom, when the absolute configuration of R ⁴ is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is (S), the absolute configuration of R ⁴ in which Z is a methyl group is (R), or
Is a halogen atom, when the absolute configuration of R ⁴ is (S), The absolute configuration of (R) is The absolute configuration of (S) is Represents the absolute configuration (R). )] An optically active compound represented by the formula: 3. A compound of the general formula (III) Wherein, R ⁷ represents an alkyl group, R ⁹ is (C ^* represents an asymmetric carbon; k is an integer of 2 or more;
Represents a methyl group or a halogen atom. X is Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ). R ⁸ is (C ^* represents an asymmetric carbon, R ¹⁰ is an alkyl chain having 3 or more carbon atoms. The absolute configuration of R ⁹ in which Z is a methyl group is (S),
Is a halogen atom and the absolute configuration of R ⁹ is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is an absolute configuration of (S), and the absolute configuration of R ⁹ in which Z is a methyl group is (R),
Is a halogen atom, and the absolute configuration of R ⁹ is (S) The absolute configuration of (R) is The absolute configuration of (S) is Is (R). )] A polymer liquid crystal having a main repeating unit represented by the following formula: 4. A compound of the general formula (IV) (Wherein, R ¹¹ represents an alkyl group, and R ¹² is (C ^* represents an asymmetric carbon, R ¹⁴ represents an alkyl chain having 3 or more carbon atoms, Z represents a methyl group or a halogen atom.) Y is -COO -, - OCO -, - CH 2 O -, - OCH 2 - represents any. p is 1 or 2. Q is any of hydrogen, a halogen atom and a nitrile group. ). R ¹³ is (C ^* represents an asymmetric carbon, and m represents an integer of 2 or more.)
Wherein Z is a methyl group, and the absolute configuration of R ¹² is (S);
When Z is a halogen atom and the absolute configuration of R ¹² is (R) The absolute configuration of (S) is The absolute configuration of (R) is Is an absolute configuration of (S), and the absolute configuration of R ¹² in which Z is a methyl group is (S),
When Z is a halogen atom and the absolute configuration of R ¹² is (R) The absolute configuration of (R) is The absolute configuration of (S) is Represents the absolute configuration (R). )] A polymer liquid crystal having a main repeating unit represented by the following formula: 5. A liquid crystal composition comprising at least one component of the polymer liquid crystal according to claim 3 or 4.