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Polymerizable compound

A technology of polymeric compounds and optical anisotropy, applied in organic chemistry, nonlinear optics, chemical instruments and methods, etc., can solve problems such as disordered orientation, low solubility of polymeric compounds, improvement of heat resistance or mechanical strength, etc. , to achieve the effect of wide temperature range of liquid crystal phase, excellent solubility and fast curing speed

Active Publication Date: 2011-04-27
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the polymeric compound described in the cited document has problems such as low solubility
On the other hand, in order to improve the solubility, a polymerizable compound forming a cinnamic acid structure is disclosed (see Patent Document 3), but it is a compound for the purpose of carrying out photoanisotropy and disordering the orientation, and it may be caused by heat and light. Because of cis-trans isomerization, it is not possible to improve the heat resistance of the original target retardation, and the mechanical strength such as surface hardness.
It is a polymeric compound that can be anisotropized by light, but cannot improve heat resistance or mechanical strength by heat and light

Method used

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Examples

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Embodiment 1

[0096] Add 12.8g (96mmol) of aluminum (III) chloride and 100ml of dichloromethane into a reaction vessel equipped with a stirring device, a cooler and a thermometer, and stir. Then, 8.4 g (110 mmol) of acetyl chloride was slowly added dropwise over 90 minutes, and then 80 ml of a dichloromethane solution of 20 g (80 mmol) 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, it was dried to obtain 23 g of an acetyl group-introduced compound. Then, 23 g of an acetyl group-introducing compound and 300 ml of formic acid were put into a reaction vessel with a stirring device, a cooler, and a thermometer, and 20 ml of 34.5% hydrogen peroxide was added, and heated to ref...

Embodiment 2

[0111] Add 30 g (120 mmol) of 4-bromo-2-fluorobiphenyl and 120 ml of dichloromethane into a reaction vessel equipped with a stirring device, a cooler and a thermometer, and stir. The reaction vessel was cooled to 0° C., 18 g of aluminum(III) chloride was added, and 17 g of oxalyl chloride was slowly added dropwise within 30 minutes.

[0112] After the dropwise addition, the reaction container was returned to room temperature, stirred for 2 hours, and the reaction was terminated. The reaction solution was slowly poured into 500 ml of ice water, extracted with dichloromethane, and the organic layer was dried over sodium sulfate. After distilling off the solvent, the reactant was dissolved in 200 ml of toluene, 7 ml of ethanol was added, and the reaction container was cooled to 0°C. Then, 15 g (150 mmol) of triethylamine was slowly added dropwise. After the dropwise addition, the reaction container was returned to room temperature, stirred for 2 hours, and the reaction was term...

Embodiment 3

[0126] A polymerizable liquid crystal composition (composition 1) having the composition shown below was prepared.

[0127]

[0128] The polymerizable liquid crystal composition has good compatibility stability and exhibits a nematic liquid crystal phase. To this composition, 3% of a photopolymerization initiator Irgacure-907 (IRGACURE-907) (manufactured by Ciba Specialty Chemicals Co., Ltd.) was added to prepare a polymerizable liquid crystal composition (composition 2). The cyclohexanone solution of this composition 2 was spin-coated on glass with polyimide, and irradiated with 4 mW / cm using a high-pressure mercury lamp 2 UV rays for 120 seconds were used to polymerize Composition 2 while maintaining a uniform orientation state to obtain an optically anisotropic body. The surface hardness (according to JIS-S-K-5400) of this optically anisotropic body was H. When the phase difference before heating of the obtained optical anisotropic body was 100%, the phase difference a...

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Abstract

A task of the invention is to provide a polymerizable compound which has excellent solvability with other liquid crystal compounds at a state of forming a polymerizable liquid cystal composition and represents excellent heat resistance and mechanical strength in solidifying the polymerizable liquid crystal composition. The invention provides the polymerizable compound represented by a general formula (I), and a liquid crystal composition with the compound as the component, and an optical anisotropic body with the liquid crystal composition, or a liquid crystal device. As the polymerizable compound has excellent solvability better than other that of other liquid crystal compound, and the polymerizable compound can be used as the compound of the polymerizable composition. Additionally, the liquid crystal phase temperature range of the polymerizable composition which comprises the polymerizable compound of the invention is wide, and the optical anisotropic body with the polymerizable composition has high heat resistance. Therefore the polymerizable compound can be widely used in the objects such as polarizing plate and phase difference plate.

Description

technical field [0001] The present invention relates to a polymerizable compound, a liquid crystal composition containing the same, 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, along with the development of the information society, the importance of optical compensation films used in polarizers and retardation plates, etc., which are necessary for liquid crystal displays has increased, and it has been reported that optical compensation films that require high durability and high functionality An example of a polymer of a polymerizable liquid crystal composition used in the film. Optically anisotropic substances used in optical compensation films, etc. are not only optical properties, but also polymerization speed, solubility, melting point, glass transition temperature, transparency of polymers, mechanical strength, surface hardness, and heat resistance ...

Claims

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Application Information

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IPC IPC(8): C07C69/92C07C69/94C07C69/757C07D239/34C07D239/52C07C69/734C07D303/24C07D303/22C07D305/06C07D207/448C07C233/20C09K19/20C09K19/32C09K19/30C09K19/34C09K19/12C08F222/20C08F222/18C08F220/36G02F1/1335G02F1/13363
Inventor 林正直楠本哲生
Owner DIC CORP