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Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element using same

An amine compound and single bond technology, which is applied in the field of liquid crystal alignment treatment agent, liquid crystal alignment film and liquid crystal display elements using it, can solve problems such as circuit damage, dust generation, liquid crystal alignment film defects, etc., and achieve stable pretilt angle, reliable sex high effect

Inactive Publication Date: 2015-07-15
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, when the ability to align liquid crystals is imparted by rubbing, there are problems as follows: due to rubbing, defects in the liquid crystal alignment film occur, and display defects occur, or dust is generated, or TFT (thin film transistor) elements are damaged due to static electricity. the circuit is damaged, etc.
However, when a conventionally known liquid crystal aligning agent containing cinnamate or polyimide is applied to the photo-alignment method, there is a problem that the irradiation amount of radiation required to obtain liquid crystal aligning ability is large.
Problems caused by a large amount of irradiation include an increase in tact time in the manufacture of liquid crystal display elements, and defects in the liquid crystal alignment film due to long-term irradiation, and the reliability of the liquid crystal panel decreases with these problems.
[0011] In the liquid crystal display element of the vertical alignment mode, when there are unreacted photoreactive groups in the liquid crystal alignment film, there is also the following problem: because the liquid crystal panel is exposed to the light of the backlight (BL) for a long time, the unreacted light The reactive group reacts and the pretilt angle of the liquid crystal changes

Method used

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  • Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element using same
  • Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element using same
  • Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0463] Add 4-iodophenol 1 (22.0g, 0.100mol), potassium carbonate (20.7g, 0.150mol) and 130ml (mmol) of dimethylformamide in a four-necked flask, stir under nitrogen atmosphere, then heat up to 80 ℃. After reaching 80° C., 1-bromodecane (17.9 g, 0.0809 mol) was added dropwise over 30 minutes, and stirred for 1 hour after the dropwise addition was completed. After confirming the disappearance of 1-bromodecane by GC (gas chromatography), the solvent was distilled off, 120 ml of toluene and 150 g of pure water were added for extraction, and the aqueous layer was removed. Then, 100 ml of 1N NaOH was added to the organic layer for extraction, and the aqueous layer was removed. The obtained organic layer was dried with anhydrous magnesium sulfate, and then magnesium sulfate was filtered off, and the obtained organic layer was evaporated to remove the solvent under reduced pressure to obtain compound 2 (yield 26.9 g, 0.0747 mol, yield 92.3%). The structure of compound 2 is obtained ...

Embodiment 2

[0468]A solution obtained by mixing 3,5-dinitrobenzyl alcohol 3 (39.6g, 0.200mol), triethylamine (26.3g, 0.260mol) and 200ml of tetrahydrofuran was stirred at 0°C under a nitrogen atmosphere, and a 30-minute A solution obtained by mixing acryloyl chloride (21.7 g, 0.240 mol) and 40 ml of tetrahydrofuran was added dropwise to this solution. After the dropwise addition, the mixture was stirred for another 4 hours. After the reaction was completed, the solvent was distilled off, and 300 g of water was added to the obtained crude product, followed by stirring at 25° C. for 30 minutes in a slurry state. Then, the reaction solution was filtered, and the solid content was dried at 70° C. under reduced pressure for 3 hours to obtain compound 4 (yield 48.7 g, 0.193 mol, yield 96.5%). The structure of compound 4 is obtained by 1 H-NMR analysis to confirm.

[0469] 1 H-NMR (CDCl 3 ): δ9.02(t, 1H, J=2.4Hz, Ar-H), 8.58(m, 2H, Ar-H), 6.54(dd, 1H, J=17.6, 1.2Hz, -CH=CH 2 ),6.27-6.20(m,1...

Embodiment 3

[0473] Compound 2 (25.3g, 0.0702mol), compound 4 (21.1g, 0.0837mol), palladium chloride-acetonitrile complex (0.572g, 2.21mmol), tri(o-tolyl)phosphine (1.28g, 4.21mmol ), tripotassium phosphate (22.7g, 0.107mol), the suspension of dimethylacetamide 170g was decompressed to 50Torr with a diaphragm pump at room temperature, and the pressure was restored with nitrogen, and the above action was repeated 10 times, and the reactor was removed. and the oxygen contained in dimethylacetamide. Then, the temperature was raised, and the mixture was stirred at 110° C. for 3 hours under a nitrogen atmosphere. After the reaction, the solvent was distilled off, followed by extraction with 200 g of water and 250 g of chloroform. The separated aqueous layer was extracted twice with 250 g of chloroform, and the obtained organic layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the obtained organic layer was evaporated to remove the solvent under reduced pres...

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Abstract

A liquid crystal aligning agent is characterised in having at least one polymer selected from a group comprising: polyamic acids obtained by reacting a diamine component containing a diamine compound represented by formula [1] with a tetracarboxylic acid dianhydride; and polyimides obtained by the imidization of said polyamic acids. (In the formula, X1 represents a single bond, -CH2O-, -O-, -COO-, -OCO-, -NHCO-, or -CONH-, X2 represents a C1-3 alkylene group, X3 represents -O-, -NH-, or -N(R1)-, X4 represents a single bond, -O-, -S-, or -NH-. X5 represents a single bond or a carbon ring selected from the group [X5-1] - [X5-5], X6 represents a C1-18 straight-chain or branched alkyl group, X7 represents a hydrogen atom, -R2-, -OR3, -NHR4, -N(R5)2, or -SR6. Here, R1-R6 each independently represent a C1-5 alkyl group. n represents an integer of 1 or 2.) (In the carbon ring structure, an arbitrary hydrogen atom can be substituted by CH3.)

Description

[0001] The patent application of the present invention is the international application number PCT / JP2011 / 065400, the international application date is July 5, 2011, the application number entering the Chinese national stage is 201180042059.1, and the name is "liquid crystal alignment treatment agent, liquid crystal alignment film and its use A divisional application of the invention patent application for "liquid crystal display element". technical field [0002] This invention relates to the novel diamine compound suitable as a raw material of the polymer used for a liquid crystal aligning film etc., the polyamic acid obtained using this compound, a polyimide, and a liquid-crystal aligning agent. It is also related with the liquid crystal display element which has a liquid crystal aligning film obtained from the said liquid-crystal aligning agent. More specifically, it relates to a liquid crystal aligning treatment agent capable of forming a liquid crystal aligning film for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C219/32C07C229/60C08G73/10
CPCC07C229/60C08G73/10C07C219/32C07C217/90C08L79/08G02F1/1337
Inventor 芦泽亮一川野勇太原田佳和
Owner NISSAN CHEM IND LTD
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