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Novel diamine, polymer, liquid crystal alignment agent, and liquid crystal alignment film, and liquid crystal display element using same

A technology of liquid crystal alignment film and liquid crystal alignment agent, which is applied in the direction of instruments, optics, nonlinear optics, etc., can solve the problems of decreased liquid crystal orientation and easy accumulation of RDC, and achieve excellent abrasion resistance, good orientation of liquid crystal, Good solubility effect

Active Publication Date: 2014-12-17
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, although the polyimide film has improved abrasion resistance, the orientation of liquid crystals decreases on the contrary, and there is also a problem that RDC (residual DC voltage) tends to accumulate.

Method used

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  • Novel diamine, polymer, liquid crystal alignment agent, and liquid crystal alignment film, and liquid crystal display element using same
  • Novel diamine, polymer, liquid crystal alignment agent, and liquid crystal alignment film, and liquid crystal display element using same
  • Novel diamine, polymer, liquid crystal alignment agent, and liquid crystal alignment film, and liquid crystal display element using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0255] Synthesis of 2,5-diaminotert-butoxycarbonylaminobenzene[B-7]

[0256]

[0257] The first step of synthesis of 4-nitro 2-tert-butoxycarbonylaminoaniline

[0258] Measure 50.0g (326.5mmol) of 4-nitro-1,2-phenylenediamine in a 1L four-neck flask, add 500ml of THF and dissolve it, heat to about 60°C under a nitrogen atmosphere, use a drop 71.3 g (326.5 mmol) of tert-butyl dicarbonate was slowly dropped over a period of time through the funnel, and refluxed for 4 hours.

[0259] After the reaction, the reaction solution was concentrated with a rotary evaporator, and recrystallized in a mixed solvent of ethyl acetate:n-hexane (volume ratio 7:3) to obtain 62.0 g of an orange solid (yield 75%).

[0260] Synthesis of the second step [B-7]

[0261] In a four-necked flask of 1L, measure 60.0g (236.9mmol) of 2-tert-butoxycarbonylamino-5-nitroaniline, 6.0g of 10wt% palladium carbon, add 500ml of THF, and carry out decompression degassing and Hydrogen substitution, reaction at ...

Embodiment 2

[0265] Synthesis of 2,4-diamino-2-tert-butoxycarbonylaminobenzene[B-8]

[0266]

[0267] The first step of synthesis of 2,4-dinitro-tert-butoxycarbonylaminobenzene

[0268] Measure 22.8g (about 273.0mmol) of sodium hydride (purity: 50%) in a 1L four-necked flask, add 500ml of DMF, cool to about 0°C under a nitrogen atmosphere, and slowly drop 50.0g (273.0mmol) A DMF solution of 2,4-dinitroaniline was reacted for 1 hour, 59.6 g (273.0 mmol) of tert-butyl dicarbonate was slowly dropped over 1 hour using a dropping funnel, and reacted at room temperature for 2 hours.

[0269] After the reaction is over, add 500ml of ion-exchanged water and stir immediately to precipitate a solid. The solid is recovered by filtration, washed several times with methanol, and carried out in a mixed solvent of ethyl acetate and n-hexane (volume ratio 5:5). Recrystallization gave 60.3 g of a pale yellow solid (yield 78%).

[0270] Synthesis of the second step [B-8]

[0271] In a 1L four-necked fla...

Embodiment 3

[0275] Polymerization of polyamic acid [PAA-1:A-1 / B-7] and preparation of alignment agent [AL-1]

[0276] In a 50ml four-necked flask with a nitrogen inlet tube and a mechanical stirrer, measure 3.35g (15.00mmol) of B-7, add 34.8g of NMP and dissolve, cool to about 10°C under a nitrogen atmosphere, and gradually 2.85 g (14.60 mmol) of A-1 was added, and it returned to room temperature and was reacted for 6 hours to obtain a 15% by mass polyamic acid solution [PAA-1].

[0277] The number average molecular weight of the obtained PAA-1 was 11300, and the weight average molecular weight was 24500.

[0278] Measure 10.0 g of this polyamic acid solution in a 50 ml Erlenmeyer flask with a stirrer, add 7.5 g of NMP, 7.5 g of BCS, and stir at room temperature for 30 minutes to obtain 6.0 mass % of PAA-1 and 6.0 mass % of NMP. Alignment agent [AL-1] of 64 mass % and 30 mass % of BCS.

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PUM

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Abstract

A polymer comprising a polyimide obtained by dewatering cyclization (imidization) of a polyamide, polyamic acid, polyamic acid ester, or the polyamic acid and / or polyamic acid ester obtained using a diamine represented by general formula [1]. (In the formula, A represents a thermally desorbable organic group; n number of NHA groups are provided (n = 1 or 2), and the NHA groups are present at the ortho position with respect to the amino groups (NH2 groups); and the amino groups are present at the meta position or the para position.)

Description

technical field [0001] The invention relates to a novel diamine, a liquid crystal alignment agent used in a liquid crystal display element, a liquid crystal alignment film and a liquid crystal display element. Background technique [0002] In the liquid crystal display element, the liquid crystal alignment film is responsible for aligning the liquid crystal in a certain direction. At present, the main liquid crystal aligning film used in industry is formed by coating a polyimide-based liquid crystal aligning agent consisting of a polyimide precursor, polyamic acid (polyamic acid) and a polyimide solution, on a substrate. Produced by film formation. In addition, when aligning the liquid crystal in parallel or obliquely with respect to the substrate surface, after film formation, surface stretching treatment by rubbing is further performed. In addition, a method utilizing an anisotropic photochemical reaction using polarized ultraviolet irradiation or the like has been propo...

Claims

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Application Information

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IPC IPC(8): C08G73/10G02F1/1337
CPCC08G73/1042C08G73/1067C08G73/18C08G73/20G02F1/133723
Inventor 野田尚宏望月大佐久间大辅
Owner NISSAN CHEM IND LTD
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