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Aromatic diamine compound, polyamic acid and polyimide prepared from aromatic diamine compound, and liquid crystal aligning agent

A liquid crystal alignment agent, aromatic diamine technology, applied in liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of image afterimage, difficult ionic charge separation, etc., to improve pretilt angle, low residual DC current load, enhance the effect of

Active Publication Date: 2012-07-11
DAXIN MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In the prior art, when a voltage is applied to the liquid crystal display, the generated ionic charges will be absorbed by the liquid crystal alignment film, and even after the applied voltage is released, it is difficult to detach the ionic charges from the liquid crystal alignment film , resulting in the problem of afterimages on the screen

Method used

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  • Aromatic diamine compound, polyamic acid and polyimide prepared from aromatic diamine compound, and liquid crystal aligning agent
  • Aromatic diamine compound, polyamic acid and polyimide prepared from aromatic diamine compound, and liquid crystal aligning agent
  • Aromatic diamine compound, polyamic acid and polyimide prepared from aromatic diamine compound, and liquid crystal aligning agent

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0091] Synthesis of 1-(2,4-diaminophenyl)-4-ethyl-piperazine (1-(2,4-diaminophenyl)-4-ethyl-piperazine)

[0092]

[0093] In a 2-liter reaction flask, add 2,4-dinitrofluorobenzene (2,4-dinitrofluorobenzene) (67 grams, 360 mmol), dimethylacetamide (dimethylacetamide) (500 grams) and potassium carbonate ( potassium carbonate) (72.5 g, 525 mmol), stirred for 5 minutes. Then, N-ethylpiperazine (40 g, 350 mmol) was slowly dropped into the reaction flask. After all the drops were finished, the temperature was raised to 80°C, and the reaction was carried out for 48 hours, and then returned to room temperature. Next, the reactant was poured into ice-pure water (2000 g) to precipitate a precipitate. Then, carry out suction filtration, the obtained filter cake is product 1-(2,4-dinitrobenzene)-4-ethyl-piperazine (1-(2,4-dinitrophenyl)-4-ethyl-piperazine ) (70.6 g, 252 mmol), yield 72%. Spectral data: 1H NMR (400MHz, CDCl 3 ) 8.6(1H), 8.2(1H), 7.1(1H), 3.3(4H), 2.6(4H), 2.5(2H), ...

experiment example 2

[0096] Synthesis of 1-(3,5-diaminobenzoyl)-4-ethyl-piperazine (1-(3,5-diaminobenzoyl)-4-ethyl-piperazine)

[0097]

[0098]In a 2-liter reaction flask, add 3,5-dinitrobenzoyl chloride (3,5-dinitrobenzoyl chloride) (115.3 grams, 500 mmol), anhydrous tetrahydrofuran (500 grams) and potassium carbonate (103.7 grams, 750 mmol), and stirred for 5 minutes after cooling to 10°C. Then, N-ethylpiperazine (74.2 g, 650 mmol) was slowly dropped into the reaction flask. After all the drops were finished, return to room temperature and stir for another 4 hours. The tetrahydrofuran was removed by concentration under reduced pressure, and the residue was poured into pure water (2000 g) until precipitation. Next, suction filtration is performed. Then, the filter cake was removed and methanol (100 g) was added. Then, heating to reflux was performed for 1 hour. Next, cool down to room temperature. Afterwards, carry out suction filtration and wash with methanol, to obtain product 1-(3,5-...

experiment example 3

[0101] Synthesis of 1-(2,4-diaminophenyl)-4-phenyl-piperazine (1-(2,4-diaminophenyl)-4-phenyl-piperazine)

[0102]

[0103] In a 2-liter reaction flask, add 1-phenylpiperazine (1-phenylpiperazine) (56.74 grams, 350 mmol), N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) (700 grams) and potassium carbonate (72.5 g, 525 mmol), and stirred at room temperature for 20 minutes, then heated to 70°C. Then, a mixed solution of 2,4-dinitrofluorobenzene (67.1 g, 360 mmol) and N-methylpyrrolidinone (175 g) was slowly dropped into the reaction flask. After all the drops were completed, the mixture was stirred for 6 hours. Next, the temperature of the reaction flask was lowered to room temperature, and the solution was poured into pure water (2625 g) until precipitation. Then, suction filtration is carried out to obtain a filter cake. Afterwards, the filter cake was taken out and methanol (525 g) was added, and heated to reflux for 1 hour. After cooling down, carry out suction filtrat...

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Abstract

The invention provides an aromatic diamine compound, polyamic acid and polyimide prepared from the aromatic diamine compound, and a liquid crystal aligning agent, wherein the liquid crystal aligning agent is suitable for a displayer. The liquid crystal aligning agent comprises the polyimide obtained by performing polymerization reaction on a diamine compound and tetracarboxylic acid or the dianhydride compound of the tetracarboxylic acid. The diamine compound contains the aromatic diamine compound expressed by the formula (I), wherein any two of R1 to R5 are primary amino groups, and the others are hydrogen atoms or univalent substituent groups except primary amino group independently; R6 is a C1-C20 alkyl group, a C3-C40 univalent cycloaliphatic substituent group, and a C6-C51 univalent aromatic substituent group or univalent heterocyclic substituent group; each of X1 and X2 is a single bond or a divalent binding group selected from a group consisting of free ether group, ketone group, ester group, acylamino group and secondary amino group independently; and each of X3 and X4 is a C1-C3 straight-chain alkylene group independently.

Description

technical field [0001] The present invention relates to an aromatic diamine compound, polyamic acid (polyamic acid) and polyimide (polyimide, PI) prepared by using the aromatic diamine compound, and a liquid crystal alignment agent, in particular to a liquid crystal alignment agent that can improve liquid crystal display Aromatic diamine compound for device performance, polyamic acid, polyimide and liquid crystal alignment agent prepared by using the aromatic diamine compound. Background technique [0002] A liquid crystal display (LCD) is a display that utilizes the photoelectric changes of liquid crystals. It has the advantages of small size, light weight, low power consumption, and good display quality. Therefore, it has become the mainstream of flat-panel displays in recent years. [0003] With the development of liquid crystal displays, along with the expansion of screen size, the requirements for high color saturation, high contrast and improved response speed, twisted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/135C07D295/192C09K19/56C08G73/10
Inventor 赖铭智张家文黄鼎棋王柏扬
Owner DAXIN MATERIALS
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