Polymerizable chiral compound

A chiral compound and polymerizable technology, applied in the field of polymerizable liquid crystal compositions and optical anisotropic bodies, can solve the problems of low compatibility, complicated manufacturing, high price of optical anisotropic bodies, etc., and achieve excellent optical properties, Simple production method and excellent solubility

Active Publication Date: 2013-04-24
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these optically active compounds all have problems such as high melting point, poor solubility, and low compatibility with some liquid crystal compounds (Citation Document 1)
In addition, compounds whose structures are asymmetric to improve solubility have been observed to improve solubility to some extent, but due to complicated production, there are problems of high production costs and high prices of optically anisotropic bodies (cited Document 2)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0138] Add 33.2g (240mmol) of 3-(p-hydroxyphenyl)benzoic acid, 4g of potassium iodide, 1g of tetrabutylammonium bromide, 400ml of ethanol to a reaction vessel equipped with a stirring device, a cooler and a thermometer, and heat at room temperature Stir. A 25% aqueous solution of 24 g of sodium hydroxide was slowly added dropwise. After the dropwise addition, the reaction vessel was kept at 50° C., and 50 g (288 mmol) of benzyl bromide was slowly added dropwise. After completion of the dropwise addition, the reaction container was heated to 70° C. and further reacted for 3 hours. After the reaction, neutralize with 10% hydrochloric acid, extract with ethyl acetate, dry with sodium sulfate, and then concentrate the solvent to synthesize 38 g of the compound represented by formula (1).

[0139] [chem 27]

[0140]

[0141] Next, 28 g (123 mmol) of the compound represented by the formula (1) synthesized above, 7.7 g (55 mmol) of isosorbide, 1.8 g of dimethyl Aminopyridine, ...

Embodiment 2）

[0159] Add 4g (10.3 mmol) of the compound represented by formula (3) synthesized in Example 1 and 4.6 g (24 mmol) of 4-acryloyloxybenzoic acid to a reaction vessel equipped with a stirring device, a cooler and a thermometer , 200 mg dimethylaminopyridine, 500 ml dichloromethane, and keep the reaction vessel below 5° C. with an ice bath. 3.6 g (28 mmol) of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the dropwise addition was completed, the reaction container was returned to room temperature, and reacted for 5 hours. After filtering the reaction solution, 200 ml of dichloromethane was added to the filtrate, washed with 10% aqueous hydrochloric acid, and then washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified through a 5-fold amount (weight ratio) of silica gel column to obtain 5.2 g of the target compound represented by the formula (5).

[0160...

Embodiment 3）

[0169] Add 4g (10.3 mmol) of the compound represented by formula (3) synthesized in Example 1, 7.4g (24 mmol) of 4-(4-methylpropene) into a reaction vessel equipped with a stirring device, a cooler and a thermometer Acyloxy)phenyl cinnamic acid, 200mg dimethylaminopyridine, 500ml dichloromethane, keep the reaction vessel below 5°C with an ice bath. 3.6 g (28 mmol) of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the dropwise addition was completed, the reaction container was returned to room temperature, and reacted for 5 hours. After filtering the reaction solution, 200 ml of dichloromethane was added to the filtrate, washed with 10% aqueous hydrochloric acid, and then washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified through a 5-fold amount (weight ratio) of silica gel column to obtain 6.4 g of the target compound represented by the formula (...

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Abstract

The invention provides a polymerizable chiral compound which has strong HTP and is excellent in solubility. The polymerizable chiral compound shown in a general form (I) has strong HTP and a low melting point. As the melting point is low, the polymerizable chiral compound has excellent solubility with other liquid crystal compounds and is useful to be a composition material of polymerizable liquid crystal composition. In addition, as the polymerizable chiral compound has a strong torque force, the polymerizable chiral compound can be used to manufacture optical anisotropy of excellent optical properties. The optical anisotropy can be used in deflection plates, phase difference plates, selective reflection plates, etc.

Description

technical field [0001] The present invention relates to a polymerizable chiral compound, a polymerizable liquid crystal composition containing the compound, and an optically anisotropic body that is a cured product of the polymerizable liquid crystal composition. Background technique [0002] In recent years, with the development of the information society, the importance of optically anisotropic bodies used in deflection plates, retardation plates, etc. required for displays has increased. Since the optical properties required for an optically anisotropic body vary depending on the purpose, a compound having the desired properties is required. In addition to optical properties, polymerization rate, solubility, melting point, glass transition point of the compound, transparency of the polymer, mechanical strength of the polymer, and the like become important factors. [0003] In recent years, circularly polarized light separating functional elements using polymerizable chol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C07C69/86C07C255/55C07C69/94C07D303/24C07D207/448C09K19/58C08F222/20C08F2/48G02B5/30
CPCC07D493/04C08G61/12C08G61/125
Inventor 林正直堀口雅弘楠本哲生
Owner DIC CORP
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