JP5140991B2 - Polymerizable liquid crystal compound - Google Patents

Description

  The present invention relates to a polymerizable liquid crystal compound.

  In recent years, with the progress of the information society, the importance of optical compensation films used for deflecting plates, retardation plates and the like essential for liquid crystal displays has been increasing. In addition, there has been reported an example in which a polymerizable liquid crystal composition is polymerized in an optical compensation film that is highly durable and requires high functionality. Since the optical anisotropic body used for the optical compensation film or the like varies depending on the purpose, a compound having characteristics suitable for the purpose is required. In addition to the optical properties, the polymerization rate, solubility, melting point, glass transition point, transparency of the polymer, mechanical strength of the polymer, etc. are important factors.

  Conventionally, a compound having a structure in which 1,4-phenylene groups are linked by an ester bond has been mainly used as a compound constituting the polymerizable liquid crystal composition (see Patent Document 1). However, the polymerizable liquid crystal compound described in the cited document has problems such as low solubility and large refractive index anisotropy. On the other hand, a polymerizable liquid crystal compound having an asymmetric structure in order to improve solubility is disclosed (see Patent Document 2), which is improved in terms of solubility compared to conventional polymerizable liquid crystal compounds. . However, an asymmetric compound has a problem in that the manufacturing process is complicated, which causes an increase in the cost of the optically anisotropic material.

Japanese National Patent Publication No. 10-513457 JP-T-2001-527570

  The problem to be solved by the present invention is to provide a polymerizable liquid crystal compound having a small refractive index anisotropy and excellent solubility with other liquid crystal compounds.

As a result of studying various substituents in the polymerizable compound, the present inventors have found that a polymerizable compound having a specific structure can solve the above-described problems, and have completed the present invention.
The present invention relates to the general formula (I)

(Wherein R ¹ and R ² each independently represent a polymerizable group, S ¹ and S ² each independently represent a spacer group or a single bond, and X ¹ and X ⁴ each independently represent —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, —OCOO—, —CO—NR ¹¹ —, —NR ¹¹ —CO—, — _{SCH 2 -, - CH 2 S} -, - CH = CH-COO -, - OOC-CH = CH -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - C 2 H 4 OCO -, - C ₂ H ₄ COO—, —OCOCH ₂ —, —CH ₂ COO—, —CH═CH—, —CF═CH—, —CH═CF—, —C≡C—, or a single bond, , ^{R 11} represents an alkyl group having carbon atoms 1 to 4.) ^{a 1} and ^{a 2} are independently from each other, 1, -Phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, tetrahydronaphthalene-2,6-diyl group or 1 , 3-dioxane-2,5-diyl group, A ¹ and A ² may be unsubstituted or substituted with an alkyl group, a halogenated alkyl group, an alkoxy group, a halogen group, a cyano group, or a nitro group. B preferably represents a 1,4-cyclohexylene group or a 4,4′-bicyclohexylene group, and the carbon atom in the cyclohexyl group is unsubstituted or an alkyl group, a halogenated alkyl group, or an alkoxy group. , halogen group, may be substituted by a cyano group or a nitro group, and ^{X 2} and ^{X 3} independently of one another, are a -COO -, - OCO -, - CH 2 O -, - O _{H 2 -, - COOC 2 H} 4 -, - OCOC 2 H 4 -, - C 2 H 4 OCO- or _-C 2 _H 4 at least one of represents a COO- ,, ^{X 2} and ^{X 3} -COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, —C ₂ H ₄ OCO— or —C ₂ H ₄ COO—, m represents an integer of 1, 2 or 3, and n represents an integer of 1, 2 or 3 And a polymerizable liquid crystal composition using the compound.

  The polymerizable liquid crystal compound of the present invention is useful as a constituent member of a liquid crystal composition because of its low refractive index anisotropy and excellent solubility with other liquid crystal compounds. In addition, the polymerizable liquid crystal composition comprising the polymerizable liquid crystal compound of the present invention as a constituent member can produce an optical anisotropic body having optical characteristics excellent in wavelength dispersion since the refractive index anisotropy is small. It is useful for applications such as a deflection plate and a phase difference plate.

In the general formula (1), R ¹ and R ² each independently represent a polymerizable group, and specific examples of the polymerizable group include the structures shown below.

These polymerizable groups are cured by radical polymerization, radical addition polymerization, cationic polymerization, and anionic polymerization. In particular, when performing ultraviolet polymerization as a polymerization method, the formula (R-1), formula (R-2), formula (R-4), formula (R-5), formula (R-7), formula (R -11), formula (R-13) or formula (R-15) are preferred, and formula (R-1), formula (R-2), formula (R-7), formula (R-11) or formula ( R-13) is more preferred.

S ¹ and S ² each independently represent a spacer group or a single bond. The spacer group is preferably an alkylene group having 2 to 10 carbon atoms, and the alkylene group is a carbon atom on the assumption that oxygen atoms are not directly bonded to each other. May be replaced by an oxygen atom, and an alkylene group having 3 to 8 carbon atoms is more preferable from the viewpoint of liquid crystallinity and compatibility with other liquid crystal compounds.

X ¹ and X ⁴ are, independently of each other, —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, —OCOO—, —CO—NR. ^{11 -,} - NR ¹¹ -CO- ^{(wherein, R 11} represents an alkyl group having a carbon _{1~4, -. SCH 2 -,} - CH 2 S -, - CH = CH-COO -, - OOC- CH═CH—, —COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, —C ₂ H ₄ OCO—, —C ₂ H ₄ COO—, —OCOCH ₂ —, —CH ₂ COO—, —CH═CH -, -CF = CH-, -CH = CF-, -C≡C-, or a single bond, preferably -O-, -COO-, -OCO-, -OCOC ₂ H ₄ -,- _{C 2 H 4 OCO -, -} C 2 H 4 COO -, - OCOCH 2 - or _-CH 2 COO-, der , More preferably -O -, - COO- or -OCO-. A ¹ and A ² are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6- A diyl group, a tetrahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group is represented, but A ¹ and A ² are unsubstituted or an alkyl group, a halogenated alkyl group, an alkoxy group, a halogen A group, a cyano group, or a nitro group may be substituted, but a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group is preferable. B represents a 1,4-cyclohexylene group or a 4,4′-bicyclohexylene group, and the carbon atom in the cyclohexyl group is unsubstituted or an alkyl group, a halogenated alkyl group, an alkoxy group, a halogen atom. Group, cyano group, or nitro group may be substituted, but preferably, an unsubstituted 1,4-cyclohexylene group or a carbon atom in the cyclohexyl group is substituted with an alkyl group, an alkoxy group, or a halogen group. 1,4-cyclohexylene group. X ² and X ³ are independently of each other —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, —C ₂ H ₄ OCO. - or _-C 2 _H 4 at least one of represents a COO- ,, ^{X 2} and ^{X 3} _{-COOC 2 H 4 -, - OCOC} 2 H 4 -, - C 2 H 4 OCO- or _-C 2 _{H 4} Represents COO-
A combination in which X ² is OCO and X ³ is C ₂ H ₄ COO or X ² is C ₂ H ₄ OCO and X ³ is COOC ₂ H ₄ is preferable. m represents an integer of 1, 2 or 3, and n represents an integer of 1, 2 or 3, but m + n is preferably an integer of 2 to 5 from the viewpoint of liquid crystallinity and heat resistance. An integer is more preferable.
More specifically, the compound represented by the general formula (I) is represented by the following general formula (I-1) to general formula (I-16).

The compound of the present invention can be synthesized by the following synthesis method.
(Production method 1) Production of compound represented by formula (I-2)
4-Hydroxybenzoic acid and 6-chlorohexanol are etherified in the presence of a suitable base such as sodium hydroxide, and then benzoic acid derivative having a polymerizable group by esterification with acrylic acid using an acid catalyst ( S-3) is obtained.

  On the other hand, 1,4-cyclohexanedione monoethylene acetal in tetrahydrofuran (hereinafter THF) was added dropwise to an ethanol solution of sodium borohydride to reduce to alcohol, and then in the presence of a suitable base such as benzyl bromide and sodium hydroxide. After etherification with a hydroxyl group to bond a protective group to the hydroxyl group, the deprotection reaction of the ethylene acetal group is performed using formic acid to obtain a cyclohexanone derivative (S-7). Further, Wittig reaction is performed using methoxymethyltriphenylphosphonium chloride. Further, it is reacted with hydrochloric acid to obtain a cyclohexyl aldehyde derivative (S-9). An isomerization reaction of a cyclohexane ring is performed under alkaline conditions, and a similar Wittig reaction is further performed, followed by a reduction reaction with sodium borohydride to obtain a compound (S-12). Further, a palladium catalyst is added to the product, and the alcohol protecting group is removed by a reduction reaction by hydrogenation to obtain a cyclohexanol derivative (S-13).

The obtained benzoic acid derivative (S-3) and cyclohexanol derivative (S-13) can be esterified using a dehydration condensing agent such as dicyclohexylcarbodiimide to obtain the target compound (I-2).

(Production method 2) Production of compound represented by formula (I-6)
4-Hydroxyphenethyl alcohol is etherified with 6-chlorohexyl acrylate, which is a reaction product of 6-chlorohexanol and acrylic acid, in the presence of a suitable base such as potassium carbonate to obtain a phenethyl alcohol derivative (S-15) Get.

Furthermore, the target compound (I-10) can be obtained by subjecting the phenethyl alcohol derivative (S-15) and trans-1,4-cyclohexanedicarboxylic acid to an esterification reaction using a dehydrating condensing agent such as dicyclohexylcarbodiimide.

  The compound of the present invention can be suitably used for chiral nematic, chiral smectic, and cholesteric liquid crystal compositions. In the liquid crystal composition using the compound of the present invention, the addition amount of the polymerizable chiral compound is preferably 0.1 to 40% by mass.

Moreover, the optical anisotropic body manufactured by polymerizing the liquid-crystal composition using the polymeric liquid crystal compound of this invention can be utilized for various uses. For example, when the polymerizable liquid crystal composition of the present invention is polymerized without being oriented, it can be used as a light scattering plate, a depolarizing plate, or a moire fringe prevention plate. Moreover, the optically anisotropic body produced by polymerizing the polymerizable liquid crystal composition of the present invention in an aligned state has optical anisotropy in physical properties and is useful. Such an optical anisotropic body is, for example, a substrate obtained by rubbing the surface of the polymerizable liquid crystal composition of the present invention with a cloth or the like, a substrate obtained by rubbing a substrate surface on which an organic thin film is formed with a cloth, or SiO _2. Can be produced by polymerizing the liquid crystal of the present invention after it is supported on a substrate having an orientation film deposited obliquely or sandwiched between the substrates. In order to further improve the applicability of the polymerizable liquid crystal material, it is also effective to provide an intermediate layer such as a polyimide thin film on the substrate or to add a leveling agent to the polymerizable liquid crystal material. Providing an intermediate layer such as a polyimide thin film on the substrate is also effective as a means for improving the adhesion when the adhesion between the optically anisotropic substance obtained by polymerizing the polymerizable liquid crystal material and the substrate is not good. .

EXAMPLES Hereinafter, although an Example is given and this invention is further explained in full detail, this invention is not limited to these Examples. Further, “%” in the compositions of the following examples and comparative examples means “mass%”.
Example 1
A reaction vessel equipped with a stirrer, a cooler, and a thermometer was charged with 13.8 g (100 mmol) of 4-hydroxybenzoic acid, 2.5 g of potassium iodide, 0.7 g of tetrabutylammonium bromide, and 400 ml of ethanol and stirred at room temperature. did. A 25% aqueous solution of 12 g of sodium hydroxide was slowly added dropwise. After completion of the dropping, the reaction vessel was kept at 50 ° C., and 14.2 g (150 mmol) of 3-chloropropanol was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was further heated to 70 ° C. and further reacted for 3 hours. After completion of the reaction, the mixture was neutralized with 10% hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate, and the solvent was concentrated to synthesize 16 g of the compound represented by formula (1) (intermediate 1).

Subsequently, 16 g (81 mmol) of the above synthesized (Intermediate 1), 10 g (140 mmol) of acrylic acid, 1 g of p-toluenesulfonic acid, 100 ml of toluene were added to a reaction vessel equipped with a stirrer, a cooler and a Dean stack. Was charged. The reaction vessel was heated to reflux with toluene and allowed to react for 4 hours. After completion of the reaction, the reaction solution was washed with saturated sodium hydrogen carbonate, neutralized with 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 20 g of a compound (intermediate 2) represented by the formula (2).

Further, 1.89 g (50 mmol) of sodium borohydride and 200 ml of ethanol were charged into a reaction vessel equipped with a stirrer, a cooler and a thermometer, and the reaction vessel was kept at 5 ° C. or lower with an ice-cooled bath. -A solution of 15.6 g (100 mmol) of cyclohexanedione monoethylene acetal in 50 ml of THF was slowly added dropwise. After completion of dropping, the reaction vessel was returned to room temperature and reacted for 3 hours. To the reaction solution, 200 ml of a saturated aqueous solution of ammonium chloride was added, extracted with 500 ml of toluene, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 15.5 g of a cyclohexanol derivative (intermediate 3). Further, after that, a reaction vessel equipped with a stirrer, a cooler, and a thermometer was charged with 15.5 g (98 mmol) of the intermediate 3, 27 g (196 mmol) of potassium carbonate, and 500 ml of toluene, and the reaction vessel was kept at 50 ° C. 20 g (117 mmol) of benzyl bromide was slowly added dropwise. After completion of the dropping, the reaction vessel was heated to 70 ° C. and reacted for 3 hours. After completion of the reaction, the mixture was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 24 g of a compound (intermediate 4) represented by the formula (3).

A reaction vessel equipped with a stirrer, a cooler and a thermometer was charged with 24 g (98 mmol) of the intermediate (4), 22 g (500 mmol) of formic acid and 300 ml of toluene, and the reaction vessel was heated to 70 ° C. for 5 hours. I let you. After completion of the reaction, 200 ml of toluene was added, washed with saturated sodium hydrogen carbonate and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 18 g of intermediate (5) from which the acetal protecting group was eliminated.
Further, 42.3 g (123 mmol) of methoxymethyltriphenylphosphonium chloride and 300 ml of THF were charged into a reaction vessel equipped with a stirrer, a cooler, a thermometer, and a nitrogen introduction tube, and the reaction vessel was cooled to 5 ° C. or less with an ice-cooled bath. Then, a solution of 13.8 g (123 mmol) of tertiary butoxy potassium in 100 ml of THF was slowly added dropwise. After completion of dropping, the reaction vessel was kept at 0 ° C. and stirred for 2 hours. Further, a solution of 18 g of the intermediate (5) in 100 ml of THF was slowly added dropwise. After completion of the dropping, the reaction vessel was kept at 0 ° C. and reacted for 2 hours. After completion of the reaction solution, 100 ml of pure water was added, followed by extraction with 500 ml of toluene, further washing with saturated saline, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain an intermediate (6). This intermediate (6) was dispersed in 60/40 ml of hexane / methanol, 5 g of hydrogen peroxide was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added with 40 ml of pure water and 100 ml of hexane, washed with a mixed solution of methanol / pure water = 2/1, further washed with saturated saline, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. Purification was performed with a silica gel column to obtain 18.4 g of a compound (intermediate 7) represented by the formula (4).

  Into a reaction vessel equipped with a stirrer, a cooler and a thermometer, 18.4 g (79 mmol) of the intermediate (7) and 100 ml of THF were charged, and 30 ml of 10% hydrochloric acid solution was slowly added dropwise at room temperature. After completion of dropping, the mixture was heated to 30 ° C. and reacted for 2 hours. After completion of the reaction, 200 ml of toluene was added and washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 17 g of intermediate (8). Further, 17 g of the intermediate (8), 100 ml of methanol, and 5 g of triethylamine were charged into the flask, 10 ml of 20% sodium hydroxide solution was added dropwise, and then the flask was cooled to −10 ° C. to carry out an isomerization reaction. After the isomerization was completed, the reaction solution was neutralized with 10% hydrochloric acid, 200 ml of toluene was added to the reaction solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 17 g of a compound (intermediate 9) represented by the formula (5).

  A reaction vessel equipped with a stirrer, a cooler, a thermometer, and a nitrogen introduction tube was charged with 37.3 g (108 mmol) of methoxymethyltriphenylphosphonium chloride and 300 ml of THF, and the reaction vessel was kept at 5 ° C. or lower with an ice-cooled bath. A solution of 12.1 g (108 mmol) of tertiary butoxypotassium in 100 ml of THF was slowly added dropwise. After completion of dropping, the reaction vessel was kept at 0 ° C. and stirred for 2 hours. Further, a solution of 17 g of the intermediate (9) in 100 ml of THF was slowly added dropwise. After completion of the dropping, the reaction vessel was kept at 0 ° C. and reacted for 2 hours. After completion of the reaction solution, 100 ml of pure water was added, followed by extraction with 500 ml of toluene, washing with saturated saline, and drying the organic layer with anhydrous sodium sulfate. The solvent was distilled off to obtain an intermediate (10). This intermediate (10) was dispersed in 60/40 ml of hexane / methanol, 5 g of hydrogen peroxide was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added with 40 ml of pure water and 100 ml of hexane, washed with a mixed solution of methanol / pure water = 2/1, further washed with saturated saline, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. Purification was performed with a silica gel column to obtain 17.2 g of a compound (intermediate 11) represented by the formula (6).

  Into a reaction vessel equipped with a stirrer, a cooler and a thermometer, 18.4 g (70 mmol) of the intermediate (11) and 100 ml of THF were charged, and 30 ml of 10% hydrochloric acid solution was slowly added dropwise at room temperature. After completion of dropping, the mixture was heated to 30 ° C. and reacted for 2 hours. After completion of the reaction, 200 ml of toluene was added and washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 16 g of intermediate (12).

  Further, 1.28 g (34 mmol) of sodium borohydride and 200 ml of ethanol were charged into a reaction vessel equipped with a stirrer, a cooler and a thermometer, and the reaction vessel was kept at 5 ° C. or lower with an ice-cooled bath. 12) A solution of 16 g of THF in 50 ml was slowly added dropwise. After completion of dropping, the reaction vessel was returned to room temperature and reacted for 3 hours. To the reaction solution, 200 ml of a saturated aqueous solution of ammonium chloride was added, extracted with 500 ml of toluene, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 16.1 g of intermediate (13).

  Next, 16.1 g of the intermediate (13) synthesized above, 800 mg of palladium carbon, and 150 ml of ethanol were charged in an autoclave container equipped with a stirrer, and a reduction reaction (reaction temperature 50 ° C., 3 hours) was performed with 1 atmosphere of hydrogen. It was. After the reaction solution was filtered, the reaction solvent was distilled off to obtain 9.9 g of a compound (intermediate 14) represented by the formula (7). The cis-trans ratio of intermediate 14 was 1/9.

Furthermore, in a reaction vessel equipped with a stirrer, a cooler, a thermometer and a nitrogen introduction tube, 20 g (80 mmol) of the intermediate (2) synthesized above, 5.7 g (40 mmol) of intermediate (14), dimethyl Charge 820 mg of aminopyridine and 200 ml of methylene chloride and keep the reaction vessel at 5 ° C. or lower with an ice-cooled bath. In an atmosphere of nitrogen gas, 10 g (80 mmol) of diisopropylcarbodiimide was slowly added dropwise. After completion of dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After the reaction solution was filtered, 100 ml of methylene chloride was added to the filtrate, washed with a 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column and recrystallization to obtain 19 g of the desired compound represented by the formula (8). The melting point of this compound was 74 ° C., and it could be dissolved at a low temperature.

(Physical property value)
¹ H-NMR (solvent: deuterated chloroform): δ: 7.9 (m, 4H), 6.96 (d, 4H), 6.39 (d, 2H), 6.13 (q, 2H), 5 .85 (d, 2H), 4.98 (m, 1H), 4.38 (m, 6H), 4.12 (m, 4H), 2.25-2.20 (m, 4H), 2. 10 (m, 4H), 1.88 (m, 2H), 1.55 (s, 1H), 1.4 (m, 4H)
¹³ C-NMR (solvent: deuterated chloroform): δ: 166.1, 165.9, 162.3, 162.1, 1301.4, 130.8, 128.1, 113.9, 113.8, 73 4, 64.5, 62.9, 61.2, 35.3, 33.9, 31.6, 30.9, 28.6,
Infrared absorption spectrum (IR) (KBr): 2925, 2855, 1765, 1652-1622, 810
(Melting point) 74 ° C

(Example 2)
A reaction vessel equipped with a condenser and a thermometer was charged with 19 g (100 mmol) of 6-chlorohexyl acrylate, 27 g (200 mmol) of potassium carbonate and 200 ml of dimethylformamide (hereinafter DMF), and stirred at room temperature for 1 hour. Then, a DMF solution (30 ml) of 13.8 g (100 mmol) of hydroxyphenethyl alcohol was slowly added dropwise. After completion of dropping, the reaction vessel was heated to 90 ° C. and reacted for 5 hours. After completion of the reaction, 500 ml of ethyl acetate was added, washed with pure water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 15 g of intermediate (15) represented by formula (9).

Into a reaction vessel equipped with a stirrer, a cooler, a thermometer and a nitrogen introduction tube, 20 g (51 mmol) of the intermediate (15) synthesized above, 4.3 g (25 mmol) of 1,4-cyclohexyldicarboxylic acid, dimethyl Charge 610 mg of aminopyridine and 200 ml of methylene chloride and keep the reaction vessel at 5 ° C. or lower with an ice-cooled bath. Under an atmosphere of nitrogen gas, 7.3 g (51 mmol) of diisopropylcarbodiimide was slowly added dropwise. After completion of dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After the reaction solution was filtered, 100 ml of methylene chloride was added to the filtrate, washed with a 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, purification was performed by silica gel column and recrystallization to obtain 14 g of the desired compound represented by the formula (10). The melting point of this compound was 69 ° C., and it could be dissolved at a low temperature.

(Physical property value)
¹ H-NMR (solvent: deuterated chloroform): δ: 7.11 (d, 4H), 6.83 (d, 4H), 6.37 (d, 2H), 6.13 (q, 2H), 5 .85 (d, 2H), 4.23 (t, 4H), 4.18 (t, 4H), 3.92 (t, 4H), 2.85 (m, 4H), 2.28 (m, 2H), 2.00 (m, 4H), 1.78 (m, 4H), 1.69 (m, 4H), 1.55-1.39 (m, 12H)
¹³ C-NMR (solvent: deuterated chloroform): δ: 175.1, 166.0, 157.6, 130.4, 129.7, 129.5, 128.4, 114.4, 67.8, 65 0.0, 64.5, 42.5, 34.3, 29.2, 28.6, 28.0, 25.8
Infrared absorption spectrum (IR) (KBr): 2925, 2855, 1765, 1652-1622, 810
(Melting point) 69 ° C

(Example 3)
20% by weight of the compounds represented by the formulas (8) and (10) was added to UCL-001 (Dainippon Ink Chemical Co., Ltd.), but it was easily dissolved and did not precipitate even when cooled to room temperature.
(Comparative example)
The melting point of the compound represented by the formula (11) was 87 ° C., and 20% by weight was added to UCL-001. However, the solubility was poor and crystals were deposited at room temperature for 30 minutes.

Claims (3)

General formula (1)

(Wherein R ¹ and R ² are independently of each other, the formulas (R-1) to (R-3)

S ¹ and S ² each independently represent an alkylene group having 2 to 10 carbon atoms , and X ¹ and X ⁴ each independently represent —O—, —OCH ₂ —. , —CH ₂ O— or a single bond , A ¹ and A ² each independently represent a 1,4-phenylene group , and A ¹ and A ² are unsubstituted or an alkyl group, a halogenated alkyl group, An alkoxy group, a halogen group, a cyano group, or a nitro group may be substituted, and B is a 1,4-cyclohexylene group,
4,4′-bicyclohexylene group, in which the carbon atom in the cyclohexyl group is unsubstituted or substituted with an alkyl group, a halogenated alkyl group, an alkoxy group, a halogen group, a cyano group, or a nitro group. X ² and X ³ may be independently of each other —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, —C ₂ H ₄ OCO— or —C ₂ H ₄ COO—, wherein at least one of X ² and X ³ is —COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, —C ₂ H ₄ OCO— or —C ₂ represents H ₄ COO—, m represents an integer of 1 , and n represents an integer of 1 . ) A polymerizable liquid crystal compound represented. A polymerizable liquid crystal composition comprising the polymerizable liquid crystal compound according to claim 1. An optical anisotropic body using the polymerizable liquid crystal composition according to claim 4.