Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element

A technology of liquid crystal alignment agent and structural unit, applied in liquid crystal materials, chemical instruments and methods, instruments, etc., can solve problems such as brightness reduction, gray scale display obstacles, long-term reliability reduction, etc., and achieve the effect of promoting movement and promoting relaxation

Active Publication Date: 2022-04-19
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the ion density is too high, the voltage applied to the liquid crystal during the frame period will decrease, and as a result, the brightness may decrease, which may hinder normal grayscale expression.
In addition, even if the initial ion density is low, the ion density after the high-temperature accelerated test may become high
The reduction in long-term reliability and the occurrence of image sticking associated with residual charges and ionic impurities will cause the deterioration of the display quality of liquid crystals.

Method used

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  • Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element
  • Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element
  • Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0202] Synthesis of (DA-1-1)

[0203]

[0204]After adding 15.00 g (68.8 mmol) of N-(4-nitrophenyl)maleimide and 300 g of tetrahydrofuran (hereinafter referred to as THF) to the flask, it was cooled with ice. To the mixture was added 10.84 g (72.2 mmol) of 4-(2-methylaminoethyl)aniline. Then, after gradually returning to room temperature, it stirred at room temperature for 3 hours. After confirming the completion of the reaction, THF was distilled off under reduced pressure. To the obtained residue was added n-hexane, followed by stirring. The obtained precipitate was filtered. When the obtained crystal was dried at 50°C, 21.7 g of the target nitro body intermediate (DA-1-1-1) was obtained (yield: 84%).

[0205] 1H-NMR (D6-DMSO, δppm): 8.36 (d, 2H), 7.61 (d, 2H), 6.88 (d, 2H), 6.49 (d, 2H), 4.84 (brs, 2H), 4.20-4.25 ( m, 1H), 2.91-3.00 (m, 1H), 2.65-2.83 (m, 3H), 2.54-2.61 (m, 2H), 2.37 (s, 3H)

[0206] Into the nitrogen-substituted flask, 10 g (27.1 mmol) of (DA1-1-1...

Embodiment 2

[0209] Synthesis of (DA-1-2)

[0210]

[0211] After adding 10.00 g (45.8 mmol) of N-(4-nitrophenyl)maleimide and 200 g of THF to the flask, it was cooled with ice. To the mixture was added dropwise 22.4 g (50.0 mmol) of a 7%-methylamine-THF solution. Then, it stirred under ice cooling for 3 hours. After confirming the completion of the reaction, when THF was distilled off under reduced pressure, the target intermediate (DA-1-2-1) was quantitatively obtained as white crystals.

[0212] 1H-NMR (D6-DMSO, δppm): 8.38 (d, 2H), 7.62 (d, 2H), 3.81-3.87 (m, 1H), 3.03-3.14 (m, 1H), 2.56-2.66 (m, 1H) ), 2.66(brs, 1H), 2.42(s, 3H)

[0213] After adding 11.4 g (45.7 mmol) of (DA-1-2-1), 200 g of THF, and 5.10 g (50.4 mmol) of triethylamine to the flask, it was cooled with ice. To the mixture was added 8.08 g (43.5 mol) of 4-nitrobenzoyl chloride, followed by stirring under ice-cooling for 3 hours. After confirming the completion of the reaction, the precipitate was filtered. Whe...

Embodiment 3

[0218] Synthesis of (DA-1-3)

[0219]

[0220] After adding 15.66 g (71.8 mmol) of N-(4-nitrophenyl) maleimide and 300 g of THF to the flask, it was cooled with ice. To the mixture was added dropwise 35.0 g (78.9 mmol) of a 7%-methylamine-THF solution. Then, it stirred under ice cooling for 3 hours. After confirming the completion of the reaction, when THF was distilled off under reduced pressure, the target intermediate (DA-1-2-1) was quantitatively obtained as white crystals.

[0221] After adding 17.8 g (71.4 mmol) of (DA-1-2-1) obtained above, 300 g of THF, and 7.99 g (79.0 mmol) of triethylamine to the flask, it was cooled with ice. To the mixture was added 15.1 g (68.1 mol) of 4-nitrobenzenesulfonyl chloride, followed by stirring at 40°C for 14 hours. After confirming the completion of the reaction, the precipitate was filtered. When the obtained filtrate was distilled off under reduced pressure, the crude product (DA-1-3-1) was obtained. To the obtained crude pr...

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Abstract

A liquid crystal aligning agent containing a polymer obtained from diamine having a structure represented by the following formula (1). R represents a hydrogen atom or a monovalent organic group; R 1 Represents a hydrogen atom or an optional linear or branched alkyl or aryl group with 1 to 5 carbons, and two Rs present on the same maleimide ring 1 are optionally the same or different from each other, the presence of 2 R 1 Optionally bonded to each other to form an alkylene group with 3 to 6 carbons; W 1 represents a single bond or a divalent organic group; W 2 Represents a divalent organic group; Ar 1 represents an aromatic ring; L 1 represents a single bond, a carbonyl group, a sulfonyl group, or an alkylene group having 1 to 20 carbon atoms.

Description

technical field [0001] The present invention relates to a novel diamine compound (also simply referred to as "diamine" in this specification) useful as a raw material of a polymer used for a liquid crystal aligning film, and a polymer (polyamic acid, polyamide) obtained by using the diamine acid, polyimide, etc.), liquid crystal aligning agents, liquid crystal aligning films, and liquid crystal display elements. Background technique [0002] Liquid crystal display elements have been widely used as display parts of personal computers, mobile phones, television cameras, etc., and as their driving methods, vertical electric field methods such as TN method and VA method; IPS method, Fringe Field Switching (Fringe Field Switching) are known. : hereinafter referred to as a transverse electric field method such as the "FFS") method. Generally speaking, compared with the vertical electric field method in which the liquid crystal is driven by applying a voltage to the electrodes for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02F1/1337C08G73/10
CPCC08G73/10G02F1/1337C09K19/56C09K19/542
Inventor 北浩结城达也
Owner NISSAN CHEM IND LTD
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