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Azo compound, composition for optical alignment film using same, and method for producing optical alignment film

An azo compound and photo-alignment film technology, which is applied in acylation preparation, disazo dyes, optics, etc., can solve the problems of screen flicker and low voltage retention rate of photo-alignment film, and achieve high affinity and voltage retention. Good rate and high stability

Active Publication Date: 2010-01-06
DAINIPPON INK & CHEM INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, the liquid crystal device using the photo-alignment film obtained by this method has a problem of low voltage retention.
In the TFT liquid crystal cell, the input voltage must be maintained until the next writing, and if the voltage retention rate is low, there will be problems such as screen flickering

Method used

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  • Azo compound, composition for optical alignment film using same, and method for producing optical alignment film
  • Azo compound, composition for optical alignment film using same, and method for producing optical alignment film
  • Azo compound, composition for optical alignment film using same, and method for producing optical alignment film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] (Example 1) Synthesis of compound No.A-1

[0130] Dissolve 5.00 g (14.5 mmol) of 2,2'-benzidine disulfonic acid in 70 ml of 3.3% (w / v) sodium hydroxide aqueous solution, and stir at 0 to 5°C. Maintain the temperature, and add 2.10 g (30.5 mmol) of sodium nitrite dissolved in 60 ml of water, and then slowly drop in 22 ml of 8N aqueous hydrochloric acid. After the dripping, the temperature of the reaction solution was maintained and stirring was continued for 3 hours to prepare a diazonium salt mixture. Then, dissolve 4.0g (29.0mmol) of 2-ethoxyphenol in 140ml of 3.5% (w / v) sodium hydroxide aqueous solution, cool to 0~5℃, stir and slowly drop in the diazonium obtained by the above method Salt mixture. After the dropping, the temperature of the reaction liquid was maintained and stirring was continued for 2.5 hours. 70 g of sodium chloride was added to the reaction solution, stirred for a while at room temperature, and the formed precipitate was filtered to obtain a crude ...

Embodiment 2

[0131] (Example 2) Synthesis of Compound No. A-7

[0132] Dissolve 1.50 g (4.35 mmol) of 2,2'-benzidine disulfonic acid in 21 ml of 3.3% (w / v) sodium hydroxide aqueous solution, and stir at 0 to 5°C. The temperature was maintained, and 0.633 g (9.17 mmol) of sodium nitrite dissolved in 15 ml of water was added, and then 6.54 ml of 8N aqueous hydrochloric acid was slowly dropped. After the dropping, the temperature of the reaction solution was maintained and stirring was continued for 3 hours to prepare the diazonium salt. Then, 1.34g (8.70mmol) of 2-methoxyphenol dissolved in 2ml of tetrahydrofuran was dissolved in 85ml of 5% (w / v) sodium carbonate aqueous solution, then cooled to 0~5℃, stirred and slowly dripped The diazonium salt mixture obtained by the above method. After the dropping, the temperature of the reaction liquid was maintained and stirring was continued for 2.5 hours. 28 g of sodium chloride was added to the reaction solution, stirred for a while at room tempera...

Embodiment 3

[0133] (Example 3) Synthesis of Compound No. A-10

[0134] Dissolve 2.75g (3.83mmol) of compound No.A-7 obtained in Example 2 and 2.24g (7.67mmol) 4-(6-acryloyloxyhexyloxy) in 30ml of N,N-dimethylformamide Benzoic acid, 1.54g (8.02mmol) 1-ethyl-3-(3'-dimethylaminopropyl) carbodiimide hydrochloride, cool and stir in an ice bath, slowly add 330mg (2.70mmol) ) A solution of 4-(N,N-dimethylamino)pyridine dissolved in 5ml of N,N-dimethylformamide. The ice bath was removed, and after stirring for 3 hours at room temperature, the reaction solution was poured into water-0.5N hydrochloric acid water and extracted with dichloromethane. The organic layer was washed with half-saturated brine, and dried over anhydrous magnesium sulfate. The organic layer was filtered, and the remaining part obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (eluent dichloromethane / methanol / acetic acid = 40 / 1 / 1 to 20 / 1 / 1) and collected After the fr...

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Abstract

An azo compound of the present invention is represented by the general formula (1): (wherein, R 1 and R 2 each independently represents a hydroxy group, or a polymerizable functional group selected from the group consisting of a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acrylamide group, a vinyl group, a vinyloxy group, and a maleimide group; X 1 represents single bond when R 1 is a hydroxy group and represents a linking group represented by -(A 1 -B 1 ) m - when R 1 is a polymerizable functional group; X 2 represents a single bond when R 2 is a hydroxy group and represents a linking group represented by -(A 2 -B 2 ) n - when R 2 is a polymerizable functional group; R 3 and R 4 each independently represents -OR 7 , a hydroxyalkyl group having 1 to 4 carbon atoms, or - CONR 8 R 9 ; and R 5 and R 6 each independently represents a carboxy group, a sulfo group, a nitro group, amino group, or a hydroxy group).

Description

Technical field [0001] The present invention relates to a new azo compound, a composition for liquid crystal alignment film using the same, and a method for producing the same. More specifically, it relates to a liquid crystal alignment film capable of aligning liquid crystal molecules without rubbing by irradiation with light (hereinafter referred to as It is a photo-alignment film.) A new azo compound used, a photo-alignment film composition containing the same, and a photo-alignment film manufacturing method for manufacturing a photo-alignment film by coating the composition for a photo-alignment film. Background technique [0002] In the liquid crystal display device, the molecular arrangement state of the liquid crystal is changed by the action of an electric field or the like, so that the optical characteristic change accompanying it is utilized in the display. In most cases, the liquid crystal is used in a state of being sandwiched between two substrates, but in order to a...

Claims

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Application Information

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IPC IPC(8): C07C245/08G02F1/1337C09B35/14C09B43/22
Inventor 近藤仁桑名康弘高田宏和弗拉基米尔·格里戈里耶维奇·奇格里诺夫郭海成
Owner DAINIPPON INK & CHEM INC
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