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Liquid crystal aligning agent, liquid crystal alignment film, manufacturing method of liquid crystal alignment film, and liquid crystal display element

A liquid crystal aligning agent and solvent technology, which is used in liquid crystal materials, chemical instruments and methods, instruments, etc.

Active Publication Date: 2020-07-07
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have the disadvantage of requiring additional structures

Method used

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  • Liquid crystal aligning agent, liquid crystal alignment film, manufacturing method of liquid crystal alignment film, and liquid crystal display element
  • Liquid crystal aligning agent, liquid crystal alignment film, manufacturing method of liquid crystal alignment film, and liquid crystal display element
  • Liquid crystal aligning agent, liquid crystal alignment film, manufacturing method of liquid crystal alignment film, and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0224] Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited to these examples.

[0225] (specific diamine)

[0226] W-A1: Compound represented by formula [W-A1], W-A2: Compound represented by formula [W-A2]

[0227] W-A3: Compound represented by formula [W-A3]

[0228] (Other side chain diamine compounds)

[0229] A1: Compound represented by formula [A1]

[0230]

[0231] C1: Compound represented by formula [C1], C2: Compound represented by formula [C2]

[0232] C3: Compound represented by formula [C3]

[0233]

[0234] (tetracarboxylic acid compound)

[0235] D1: 1,2,3,4-cyclobutanetetracarboxylic dianhydride

[0236] D2: Bicyclo[3,3,0]octane-2,4,6,8-tetracarboxylic dianhydride

[0237] D3: pyromellitic dianhydride

[0238]

[0239] (solvent)

[0240] NEP: N-ethyl-2-pyrrolidone, GVL: γ-valerolactone,

[0241] GBL: γ-butyrolactone NMP: N-methyl-2-pyrrolidone,

[0242] CHP: N-cyclohexy...

Synthetic example 1W-A1

[0271]

[0272]

[0273]

[0274] In a reaction vessel, 4,4'-dinitro-1,1'-biphenyl-2,2'-dimethanol (41.1 g, 135 mmol) and triethylamine (31.5 g ), and methanesulfonyl chloride (33.2 g) was added dropwise under ice-cooling under a nitrogen atmosphere, and reacted for 1 hour to obtain compound [1]. Next, p-(trans-4-heptylcyclohexyl)phenol (77.8 g) dissolved in tetrahydrofuran (246.6 g) was added, stirred at 40°C for 1 hour, and then added in pure water (233 g) at the same temperature. ) of potassium hydroxide (41.0 g) was allowed to react for 21 hours. After completion of the reaction, a 1.0M hydrochloric acid aqueous solution (311 ml) and pure water (1050 g) were added to precipitate a crude product, which was collected by filtration. The obtained crude product was heated and dissolved in tetrahydrofuran (574 g) at 50° C., methanol (328 g) was added to precipitate crystals, and compound [2] was obtained by filtering and drying (yield: 97.9 g, yield: 89%).

[0275] 1 H...

Synthetic example 2W-A2

[0279]

[0280]

[0281]

[0282] Tetrahydrofuran (327.2 g), 4,4'-dinitro-2,2'-biphenyl acid (40.9 g, 123 mmol) and p-(trans-4-heptylcyclohexyl)phenol ( 72.1g), 4-dimethylaminopyridine (1.50g), drop into 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (56.6g ), allowing it to react for 3 hours. After completion of the reaction, the reaction solution was poured into pure water (1226 g) to deposit a crude product, which was collected by filtration. Next, after slurry-washing the crude product with methanol (245g), it filtered, and the obtained crude product was heated and melt|dissolved in tetrahydrofuran (245g) at 60 degreeC. After removing the insoluble matter by filtration, after concentration under reduced pressure to make the internal total weight 232g, methanol (163g) was added to precipitate crystals, and after stirring under ice-cooling conditions, filtration and drying were carried out to obtain compound [3] (yield: 73.9 g, yield: 71%).

[0283] 1...

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Abstract

A liquid crystal aligning agent is provided which can suppress alignment film coating faults due to the influence of the wiring structure or contact holes, and which can suppress faults in which display of a liquid crystal display element becomes uneven; a liquid crystal alignment film and a liquid crystal display element are also provided. This liquid crystal aligning agent is characterized by containing: at least one polymer selected from the group consisting of a polyamic acid or a polyamic acid ester having the structure of formula [1] and a polyimide which is an imide compound thereof; and a solvent containing at least one solvent A selected from the group consisting of formulae (d-1) to (d-5), and at least one solvent B selected from a group consisting of formula (e), and alkylene glycol monoalkyl ether acetate, alkylene glycol diacetate, alkylene glycol monoalkyl ether and alkylene glycol dialkyl ether having a boiling point of 200-300 DEG C. (The symbols in the formulae are asdefined in the specification.)

Description

technical field [0001] The present invention relates to a liquid crystal aligning agent that has high dimensional stability during inkjet coating and is less prone to drying during flexographic printing, a liquid crystal aligning film obtained from the liquid crystal aligning agent, and a liquid crystal display element having the liquid crystal aligning film. Background technique [0002] As a liquid crystal aligning film in a liquid crystal display element, a liquid crystal aligning agent mainly composed of a polyimide precursor such as polyamic acid (polyamic acid) and a solution of a soluble polyimide is applied and fired. The so-called polyimide-based liquid crystal alignment film. As a film-forming method of the said liquid crystal aligning film, spin coating, dip coating, flexographic printing, etc. are known normally. Flexographic printing is easy to pattern the alignment film and has high productivity, but in order to form a uniform film, it is necessary to apply a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G02F1/1337C08G73/06
CPCC08G73/06G02F1/1337C08G73/10C08G73/1032C08L79/08C09K19/56
Inventor 芦泽亮一福田一平长谷川直史丰田美希藤枝司
Owner NISSAN CHEM IND LTD
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