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Synthesis of Novel Diamine and Its Liquid Crystal Alignment Agent

A side chain type diamine and vertical alignment technology, which is applied in the field of new diamine synthesis and liquid crystal aligning agent using the same, can solve the problems of low reactivity and the like

Active Publication Date: 2020-04-24
DONGJIN SEMICHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the prior art, diamines having side chains had the problems of low efficiency in controlling the pretilt angle to the amount introduced and low reactivity during polymerization.

Method used

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  • Synthesis of Novel Diamine and Its Liquid Crystal Alignment Agent
  • Synthesis of Novel Diamine and Its Liquid Crystal Alignment Agent
  • Synthesis of Novel Diamine and Its Liquid Crystal Alignment Agent

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0092] (Di-tert-butyl((2-(4-hydroxyphenyl)ethane-1,1-diyl)bis(4,1-phenylene))iminodicarboxylic acid)(di-tert-butyl(( Synthesis of 2-(4-hydroxyphenyl)ethane-1,1-diyl)bis(4,1-phenylene))dicarbamate)

[0093]

[0094] Add 4-(2,2-bis(4-aminophenyl)ethyl)phenol (4-(2,2-bis(4-aminophenyl)ethyl)phenol) (15.0g, 49.3mmol) in the reaction vessel, Further dichloromethane (200 mL) was added for dissolution. Di-tert-butyl dicarbonate (di-tert-butyl dicarbonate) (24.9 ml, 108.4 mmol) was added dropwise to the reaction vessel under an ice bath, followed by stirring at normal temperature for 12 hours. After adding water to the reaction vessel to complete the reaction, extraction was performed with dichloromethane to evaporate all the organic solvents. The resulting mixture was separated by column chromatography (silica gel, hexane / ethyl acetate=1 / 1) to obtain a pale yellow solid (14.9 g, 61%).

[0095] 1 H NMR (300MHz, CDCl 3 )δ7.20(d,4H),7.06(d,4H),6.81(d,2H),6.61(d,2H),6.35(s,2H),4....

Synthetic example 2

[0101] 4-(2,2-Bis(4-aminophenyl)ethyl)phenyl 2,3',4',5'-tetrafluoro-[1,1'-biphenyl]-4-carboxylate Synthesis of (4-(2,2-bis(4-aminophenyl)ethyl)phenyl 2,3',4',5'-tetrafluoro-[1,1'-biphenyl]-4-carboxylate)

[0102]

[0103] In a reaction vessel, di-tert-butyl((2-(4-hydroxyphenyl)ethane-1,1-diyl)bis(4,1-phenylene))iminodicarboxylic acid (9g, 17.86 mmol) was dissolved in dichloromethane (200mL), and 2,3',4',5'-tetrafluoro-[1,1'-biphenyl]-4-carboxylic acid (4.83g, 17.86mmol) was added , DCC (3.68g, 17.86mmol), DMAP (0.22g, 1.79mmol), reacted at room temperature for 12 hours to produce 4-(2,2-bis(4-((tert-butoxycarbonyl)amino)phenyl ) ethyl) phenyl 2,3',4',5'-tetrafluoro-[1,1'-biphenyl]-4-carboxylate (4-(2,2-bis(4-(( tert-butoxycarbonyl)amino)phenyl)ethyl)phenyl 2,3',4',5'-tetrafluoro-[1,1'-biphenyl]-4-carboxylate) (9g, 67%).

[0104] 4-(2,2-bis(4-((tert-butoxycarbonyl)amino)phenyl)ethyl)phenyl 2,3',4',5'-tetrafluoro-[1, 1'-biphenyl]-4-carboxylate (9g, 11.97mmol) was added to...

Synthetic example 3

[0107] 4,4'-(2-(4-(3,4,5-trifluorophenoxy)phenyl)ethane-1,1-diyl)diphenylamine (4,4'-(2-(4 -Synthesis of (3,4,5-trifluorophenoxy)phenyl)ethane-1,1-diyl)dianiline

[0108]

[0109] In a reaction vessel, di-tert-butyl((2-(4-hydroxyphenyl)ethane-1,1-diyl)bis(4,1-phenylene))iminodicarboxylic acid (5g, 9.9 mmol) was dissolved in DMF (100mL), NaOH (1.6g, 39.6mmol) was added, and the reaction was carried out at room temperature for 1 hour, and then 5-bromo-1,2,3-trifluorobenzene (2.1g, 9.9mmol) After being dissolved in DMF, the reaction was carried out for 5 hours to obtain di-tert-butyl ((2-(4-(3,4,5-trifluorophenoxy)phenyl)ethane-1,1-diyl)bis (4,1-phenylene))iminodicarboxylic acid (di-tert-butyl((2-(4-(3,4,5-trifluorophenoxy)phenyl)ethane-1,1-diyl)bis(4 ,1-phenylene)) dicarbamate) (5.5g, 87%). Di-tert-butyl((2-(4-(3,4,5-trifluorophenoxy)phenyl)ethane-1,1-diyl)bis(4,1-phenylene) at 0°C )) iminodicarboxylic acid (5.5g, 8.66mmol) was added into TFA (30mL) and reacted for 1 hour...

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Abstract

The present invention relates to a polyimide resin for a vertical alignment agent and a method for preparing same and provides a method for preparing a side-chain diamine polyimide compound, which exhibits a uniform and high pretilt angle and thus can be used as a material for a polyimide alignment layer, and a polyimide resin for a vertical alignment agent, which has uniform and stable orientation and is capable of exhibiting a pretilt angle of 90 degrees by using the method, and a method for producing same. To this end, the present invention provides a diaminobenzene derivative represented by chemical formula 1.

Description

technical field [0001] The invention relates to a polyimide resin used as a liquid crystal aligning agent and a manufacturing method thereof, in particular to a manufacturing method of a diamine compound. The diamine compound is easy to control the pretilt angle, exhibits good liquid crystal orientation, and can be used as a polyimide resin. A raw material for an amine alignment film, and a polyamic acid or polyimide used as a liquid crystal aligning agent using a diamine compound, and a liquid crystal aligning agent containing a diamine compound. Background technique [0002] In order to improve the display function, various liquid crystal driving modes have been proposed and developed. The driving methods of liquid crystal display elements can be divided into the following modes: Twisted nematic (hereinafter referred to as "TN") mode in which nematic liquid crystal molecules are arranged between two transparent electrode substrates coated with an orientation film on the tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/50C08G73/10G02F1/1333
Inventor 崔珍郁尹星壹姜少熙
Owner DONGJIN SEMICHEM CO LTD
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