Polymerizable biphenyl compound

A technology of polymeric compounds and phenylene, applied in the fields of organic chemistry, nonlinear optics, chemical instruments and methods, etc., can solve the problems of low solubility, low heat resistance and mechanical strength of polymeric compounds, etc., Achieve excellent solubility, wide temperature range of liquid crystal phase, and high heat resistance

Active Publication Date: 2010-08-04
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the polymerizable compound described in this cited document has problems such as low solubility.
On the other hand, a polymerizable compound adopting an asymmetric structure for improving solubility is disclosed (Patent Document 3). Compared with the conventional polymerizable compound, although the solubility is improved, it is not sufficient, and there is a resistance Issues such as low thermal and mechanical strength

Method used

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  • Polymerizable biphenyl compound
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] 10 g (40.1 mmol) of 4-bromo-4′-hydroxybiphenyl, 6.2 g (48.2 mmol) of tert-butyl acrylate, and 4.8 g of triethylamine were placed in a reaction vessel equipped with a stirring device, a cooler, and a thermometer. (48 mmol), 530 mg of palladium acetate, and 300 ml of dimethylformamide, and the reaction was carried out by heating the reactor to 100° C. under a nitrogen atmosphere. After completion of the reaction, ethyl acetate and THF were added, and the organic layer was washed with 10% aqueous hydrochloric acid, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio) to obtain 11 g of the compound represented by the formula (1).

[0119] [chem 25]

[0120]

[0121] Then, 3 g (10.1 mmoles) of the compound represented by the above-mentioned formula (1), 1 g (11 mmoles) of acryloyl chloride, and 50 ml of dichloromethane were charged into a reaction vessel equipped with a ...

Embodiment 2

[0134] In the autoclave container equipped with stirring device, the intermediate 4.5g (15.2 mmoles) of embodiment 1 synthesis shown in the charging formula (1), 5% palladium carbon 250mg, tetrahydrofuran 50ml, ethanol 5ml, at 0.3MPa The reduction reaction was carried out in a hydrogen atmosphere (room temperature, 8 hours). After filtering the reaction liquid, the reaction solvent was distilled off to obtain 4.5 g of the compound represented by the formula (5).

[0135] [chem 29]

[0136]

[0137] Then, 4.5 g (15.1 mmoles) of the compound represented by the above-mentioned formula (5), 1.6 g (18 mmoles) of acryloyl chloride, and 50 ml of dichloromethane were charged into a reaction vessel equipped with a stirring device, a cooler, and a thermometer. The reactor was cooled to below 5°C under nitrogen atmosphere. Then, 1.8 g (18 mmol) of triethylamine was slowly added dropwise. After completion of the dropwise addition, the reaction was carried out at below 20° C. for 3 h...

Embodiment 3

[0151] 12.8 g (96 mmol) of aluminum trichloride and 100 ml of dichloromethane were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, followed by stirring. Then, 8.4 g (110 mmol) of acetyl chloride was slowly added dropwise over 90 minutes, and further, 80 ml of a dichloromethane solution of 20 g (80 mmol) of 4-bromo-2-fluorobiphenyl was slowly added dropwise over 2 hours. After the dropwise addition was completed, stirring was continued for 2 hours to complete the reaction. The reaction solution was slowly poured into 500 ml of ice water, extracted with dichloromethane, and the organic layer was washed with pure water and saturated brine. After distilling off the solvent, drying was performed to obtain 23 g of a compound into which an acetyl group was introduced. Next, 23 g of an acetyl group-introduced compound and 300 ml of formic acid were placed in a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and 20...

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Abstract

The problem that the invention object to resolve is to provide a polymerizable compound, which has excellent solubility with other liquid crystal compounds during constituting a polymerizable liquid crystal composition, and displays excellent heat-resistant quality and mechanical intensity during curing the polymerizable liquid crystal composition. The invention provides a polymerizable compound represented by formula (I), and a liquid crystal composition taking the compound as the constitution material, and further provides an optical anisotropy body or liquid crystal device using the liquid crystal composition. As the inventive polymerizable compound has excellent solubility with other liquid crystal compounds, it is useful as the constitution material of the polymerizable compound. In addition, the polymerizable composition containing the inventive polymerizable compound has wide liquid crystal phase temperature range; the optical anisotropy body of the polymerism composition has high heat-resistant quality, and is useful in phase difference plates and the like applications.

Description

technical field [0001] The present invention relates to a polymerizable biphenyl compound, a liquid crystal composition containing the compound, and an optically anisotropic body or a liquid crystal device which is a cured product of the liquid crystal composition. Background technique [0002] In recent years, with the progress of the information society, the importance of optical compensation films used for polarizers, retardation plates, etc. necessary for liquid crystal displays has increased, and high durability and high functional optical compensation films are required For example, an example of polymerizing a polymerizable liquid crystal composition is reported. Optically anisotropic materials used in optical compensation films, etc., not only have optical properties, but also polymerization speed, solubility, melting point, glass transition temperature, light transmittance of polymers, mechanical strength, surface hardness and heat resistance, etc. become an import...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/73C07C69/734C07C69/86C07C69/96C07C69/94C07D303/24C07D305/06C07D207/448C09K19/20C09K19/12C08F222/20C08F2/48C08F2/46G02F1/13363
CPCC07C69/618C09K19/20
Inventor 林正直楠本哲生
Owner DIC CORP
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