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New diamine, polymer, liquid crystal aligning agent, liquid crystal aligning film, and liquid crystal display element using the liquid crystal aligning film

A technology of liquid crystal alignment agent and polymer, which is applied in the field of polymers and new diamines. It can solve the problems of unreliable liquid crystal display elements and poor image retention, etc., and achieve good liquid crystal orientation, not easy to accumulate, and good printability. Effect

Active Publication Date: 2017-02-22
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, if the voltage holding ratio, which is one of the electrical characteristics, decreases due to light irradiation from the backlight, image sticking (line image sticking), which is one of display defects of the liquid crystal display element, is likely to occur, and cannot be achieved. Obtaining highly reliable liquid crystal display elements

Method used

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  • New diamine, polymer, liquid crystal aligning agent, liquid crystal aligning film, and liquid crystal display element using the liquid crystal aligning film
  • New diamine, polymer, liquid crystal aligning agent, liquid crystal aligning film, and liquid crystal display element using the liquid crystal aligning film
  • New diamine, polymer, liquid crystal aligning agent, liquid crystal aligning film, and liquid crystal display element using the liquid crystal aligning film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0244] (Example 1) Synthesis of N1,N4-bis[(2-tert-butoxycarbonylamino)-4-aminophenyl]succinamide [B-6]

[0245]

[0246] Step 14-Synthesis of nitro-2-tert-butoxycarbonylaminoaniline [NB-NA]

[0247] Weigh 200.0 g (1.31 mol) of 4-nitro-1,2-phenylenediamine in a 3L four-necked flask equipped with a stir bar and a nitrogen introduction tube, add 1L of THF and 300 mL of DMF, and heat to about 60 in a nitrogen atmosphere It was dissolved at °C, 285.2 g (1.44 mol) of tert-butyl dicarbonate was slowly added dropwise using a dropping funnel over 2 hours, and it was refluxed for 4 hours.

[0248] After the reaction, the reaction solution was concentrated using a rotary evaporator, the resulting residue was dissolved in THF, and poured into a mixed solvent of ethyl acetate: n-hexane (volume ratio 7:3) for recrystallization, thereby obtaining a yellow Solid 248g (about 75% yield). The resulting solid is 4-nitro-2-tert-butoxycarbonylaminoaniline. Using nuclear magnetic resonance spectroscopy ...

Embodiment 2

[0256] (Example 2) Synthesis of N1,N4-bis[(2-tert-butoxycarbonylamino)-4-aminophenyl]adipamide [B-7]

[0257]

[0258] Step 1 Synthesis of N1, N4-bis[(2-tert-butoxycarbonylamino)-4-nitrophenyl] adipamide

[0259] Weigh 20.0g (78.97mmol) of 2-tert-butoxycarbonylamino-4-nitroaniline and 15.6g (197.43mmol) of pyridine in a 500mL four-neck flask, and dissolve them in a mixed solvent of 300ml dehydrated THF and 100ml DMF. While keeping the bath below 10°C, a THF solution (20% by weight) of 6.5 g (35.54 mmol) of adipoyl chloride was slowly added dropwise using a dropping funnel under a nitrogen atmosphere, and the reaction was stirred at room temperature for 24 hours. As the reaction progressed, a solid precipitated out. After the reaction, 300 ml of pure water was added to the reaction solution and stirred for a period of time, and the reaction solution was poured into 1 L of methanol and stirred for a period of time. The solid was filtered and washed with 500 ml of methanol several t...

Embodiment 3

[0264] (Example 3) Synthesis of N1,N4-bis[(2-tert-butoxycarbonylamino)-4-aminophenyl]terephthalamide [B-8]

[0265]

[0266] Step 1 Synthesis of N1,N4-bis[(2-tert-butoxycarbonylamino)-4-nitrophenyl]terephthalamide

[0267] Weigh 20.0g (78.97mmol) of 2-tert-butoxycarbonylamino-5-nitroaniline and 15.6g (197.43mmol) of pyridine in a 500mL four-necked flask, and dissolve them in a mixed solvent of 300ml dehydrated THF and 100ml DMF. While keeping the bath below 10°C, a THF solution (20% by weight) of 7.2 g (35.54 mmol) of terephthaloyl chloride was slowly added dropwise using a dropping funnel under a nitrogen atmosphere, and the reaction was stirred at room temperature for 24 hours. As the reaction progressed, a solid precipitated out. After the reaction, 300 ml of pure water was added to the reaction solution and stirred for a period of time, and the reaction solution was poured into 1 L of methanol and stirred for a period of time. The solid was filtered and washed with 500 ml of ...

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PUM

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Abstract

A diamine represented by formula (1). (In the formula, A represents an organic group that can be eliminated by heat. B represents -CH2-, -O-, -S-, or -NH-. X represents a single bond or a divalent organic group. Y represents a single bond, -O-, -CONH-, -NHCO-, -OCO-, -COO-, -HN-CO-NH-, -NHCOO-, or -OCONH-. Z represents a single bond or alkylene group having 1-2 carbon atoms. R1 represents a hydrogen atom or alkyl group having 1-3 carbon atoms. R2 represents an -NH-A group when Y is -CONH- or -OCO- and represents a hydrogen atom, halogen atom, or alkyl group having 1-5 carbon atoms in other cases. k1 represents an integer of 0-3. R3 represents a halogen atom or alkyl group having 1-5 carbon atoms. -(R3)k1 represents the number k1 of substituents R3; however, the two or more R3 may be the same or different when k1 is 2 or higher. k2 represents an integer of 0-3. R4 is a halogen atom or alkyl group. -(R4)k2 represents the number k2 of substituents R4; however, the two or more R4 may be the same or different when k2 is 2 or higher.)

Description

Technical field [0001] The present invention relates to novel diamines, polymers, liquid crystal alignment agents for liquid crystal display elements, liquid crystal alignment films and liquid crystal display elements. Background technique [0002] In the liquid crystal display element, the liquid crystal alignment film functions to orient liquid crystal in a certain direction. At present, the main liquid crystal alignment film used in industry is produced as follows: a polyimide system composed of a polyimide precursor (also called polyamic acid) or a solution of polyimide The liquid crystal aligning agent of is apply|coated on a board|substrate, and a film is formed, and this liquid crystal aligning film is produced. In addition, when the liquid crystal is oriented in parallel or obliquely with respect to the substrate surface, the surface is stretched by rubbing after film formation. In addition, a method of using anisotropic photochemical reaction based on polarized ultravi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/43C08G73/10G02F1/1337
CPCC07C271/28C08G73/10G02F1/133711G02F1/133784
Inventor 野田尚宏金尔润
Owner NISSAN CHEM IND LTD
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