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

A technology of liquid crystal alignment agent and structural unit, which is applied in the direction of instruments, optics, nonlinear optics, etc., can solve the problems of reduced brightness, increased ion density, interference with grayscale display, etc., and achieves the effect of promoting movement and relaxation

Active Publication Date: 2022-03-22
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 high, the voltage applied to the liquid crystal decreases, resulting in a decrease in brightness, which sometimes interferes with normal grayscale display
In addition, even if the initial ion density is low, there are cases where the ion density increases after the high-temperature accelerated test
The long-term reliability reduction associated with residual charges and ionic impurities, and the generation of afterimages will reduce 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 1A

[0213] Synthesis of (DA-1-1)

[0214]

[0215] After adding 15.00 g (68.8 mmol) of N-(4-nitrophenyl)maleimide and 300 g of tetrahydrofuran (hereinafter referred to as THF) into the flask, it was ice-cooled. To this mixture was added 3.37 g (33.0 mmol) of N,N'-dimethyl-1,3-propanediamine. Then, after slowly returning to room temperature, the mixture was stirred at room temperature for 1 day. After confirming that the reaction was complete, 200 g of ethyl acetate was added to the reaction mixture and stirred. The resulting crystals were filtered and then dried at 50°C to obtain 11.1 g (yield 62%) of the target nitro compound intermediate (DA-1-1-1).

[0216] 1 H-NMR (D6-DMSO, δppm): 8.37 (d, 4H), 7.62 (d, 4H), 4.15-4.21 (m, 1H), 2.93-3.03 (m, 2H), 2.80-2.89 (m, 2H) ),2.53-2.70(m,4H),2.32(s,6H),1.57-1.67(m,2H)

[0217] DA-1-1-1 11.1 g (20.6 mmol), 5% Pd-C 1 g (STD type, wet product, manufactured by N.E. CHEMCAT Corporation) and N,N-dimethylformamide were charged into a ni...

Embodiment 2A

[0220] Synthesis of (DA-1-2)

[0221]

[0222] After adding 0.1246 g (0.662 mmol) of N-(4-aminophenyl)maleimide and 3 g of THF into the flask, it ice-cooled. To this mixture was added piperazine 0.0285 g (0.331 mmol). Then, after slowly returning to room temperature, the mixture was stirred at room temperature for 3 days. After confirming the completion of the reaction, the precipitated crystals were filtered and washed with diisopropyl ether (hereinafter referred to as IPA). The resulting crystals were dried at 50°C to obtain 0.067 g of the target DA-1-2 (yield 47%).

[0223] 1H-NMR (D6-DMSO, δppm): 6.82 (d, 4H), 6.59 (d, 4H), 5.30 (brs, 4H), 3.92-3.98 (m, 2H), 2.70-2.95 (m, 8H), 2.40-55(m,2H)

Embodiment 3A

[0225] Synthesis of (DA-1-3)

[0226]

[0227] After adding 2.90 g (15.4 mmol) of N-(4-aminophenyl)maleimide and 30 g of tetrahydrofuran (hereinafter referred to as THF) into the flask, it was ice-cooled. To this mixture was added 1.00 g (7.34 mmol) of 4-(aminomethyl)benzylamine. Then, after slowly returning to room temperature, the mixture was stirred at room temperature for 3 hours. After confirming the completion of the reaction, the reaction mixture was cooled again, and the precipitated crystals were filtered. The obtained crystals were dried at 45° C. under reduced pressure to obtain 1.59 g (yield 42%) of the target compound (DA-1-3) as yellow crystals.

[0228] 1H-NMR (D6-DMSO, δppm): 7.32 (s, 4H), 6.84 (d, 4H), 6.59 (d, 4H), 5.31 (brs, 4H), 3.82-3.95 (m, 4H), 3.74- 3.82(m,2H),2.91-3.01(m,2H),2.94(brs,2H),2.53-2.56(m,1H),2.48-2.51(m,1H)

[0229] [Viscosity determination]

[0230] The viscosity of the polyamic acid solution was measured using an E-type viscometer...

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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 1 Represents a hydrogen atom, an optionally straight-chain or branched-chain alkyl or aryl group with 1 to 5 carbons, and two Rs present on the same maleimide ring 1 optionally the same or different from each other, the presence of 2 R 1 Optionally together form an alkylene group with 3 to 6 carbons, W 2 Indicates a divalent organic group, W 1 Indicates a single bond or carbonyl, L 1 Represents a group selected from linear alkylene groups with 1 to 20 carbons, branched alkylene groups with 3 to 20 carbons, cyclic alkylene groups with 3 to 20 carbons, phenylene and heterocyclic groups A divalent group, or a group formed by bonding a plurality of the divalent groups, the phenylene group and the heterocyclic group are each independently selected from the group consisting of alkyl, alkoxy, haloalkyl, haloalkoxy, The same or different substituents in the halogen group and the cyano group are substituted, and the bond between the divalent groups is selected from a single bond, an ester bond, an amide bond, a urea bond, an ether bond, and a thioether At least one of bond, amino bond and carbonyl group, in the case of multiple such divalent groups, the divalent groups are optionally the same or different from each other, and in the case of multiple above-mentioned combinations, the bonds are optionally mutually The same or different, R represents a hydrogen atom or a monovalent organic group, the two Rs that exist are optionally different from each other, the two Rs that exist are optional to form an alkylene group with 1 to 6 carbons, and the two Rs that exist Both or either party can choose to cooperate with L 1 Bond.

Description

technical field [0001] The present invention relates to polyamic acid, polyamic acid ester, polyimide, polyamic acid ester, polyimide, Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element. Background technique [0002] Liquid crystal display elements have been widely used as display parts of personal computers, mobile phones, and televisions. As their driving methods, vertical electric field methods such as TN method and VA method, IPS method, and Fringe Field Switching (Fringe Field Switching: the following are known) A transverse electric field method such as an FFS method is called. [0003] In general, the lateral electric field method, in which electrodes are formed on only one side of the substrate and an electric field is applied in a direction parallel to the substrate, is easier to obtain with a wider viewing angle than the vertical electric field method in which voltage is applied to electrodes formed on the upper and lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02F1/1337C08G73/10
CPCC08G73/10G02F1/1337Y02P20/55
Inventor 北浩结城达也
Owner NISSAN CHEM IND LTD
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