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

A liquid crystal aligning agent and component technology, applied in liquid crystal materials, chemical instruments and methods, instruments, etc., can solve the problems of reduced reliability, precipitation, low solubility of polymerizable compounds, etc., to improve the aggregation of polymers and improve the response. Speed, the effect of reducing the amount of import

Active Publication Date: 2021-07-09
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] On the other hand, in this PSA-type liquid crystal display element, the solubility of the polymerizable compound added to the liquid crystal is low, and there is a problem of precipitation at low temperature if the amount added is increased. not getting good orientation status
In addition, the unreacted polymerizable compound remaining in the liquid crystal becomes an impurity (contamination) in the liquid crystal, so there is also a problem of lowering the reliability of the liquid crystal display element.
In addition, if the amount of UV irradiation treatment necessary for the PSA method is large, the components in the liquid crystal will be decomposed, resulting in a decrease in reliability.

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

[0146] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the examples. The meanings of the abbreviations, measurement methods and the like in the following are as follows.

[0147] (acid dianhydride)

[0148] BODA: Bicyclo[3,3,0]octane-2,4,6,8-tetracarboxylic dianhydride

[0149] CBDA: 1,2,3,4-cyclobutanetetracarboxylic dianhydride

[0150] PMDA: pyromellitic dianhydride

[0151] (diamine)

[0152] p-PDA: p-phenylenediamine

[0153] DBA: 3,5-diaminobenzoic acid

[0154] 3AMPDA: 3,5-diamino-N-(pyridin-3-ylmethyl)benzamide

[0155]

[0156]

[0157] NMP: N-methyl-2-pyrrolidone, DMF: N,N-dimethylformamide

[0158] BCS: Butyl Cellosolve, THF: Tetrahydrofuran

[0159]

[0160] 3AMP: 3-pyridinemethylamine

[0161]

[0162] Apparatus: Normal temperature gel permeation chromatography (GPC): SSC-7200 manufactured by Senshu Scientific co., Ltd.),

[0163] Column: Shodex column (KD-803, KD-80...

manufacture example 1

[0209] BODA (1.20 g, 4.8 mmol), DA-1 (2.36 g, 4.8 mmol), p-PDA (0.39 g, 3.6 mmol), and 3AMPDA (0.87 g, 3.6 mmol) were dissolved in NMP (18.4 g), After reacting at 60 degreeC for 5 hours, CBDA (1.32g, 7.1mmol) and NMP (6.1g) were added, and it was made to react at 40 degreeC for 10 hours, and obtained the polyamic-acid solution.

[0210]After adding NMP to this polyamic-acid solution (27g) and diluting to 6.5 mass %, acetic anhydride (4.7g) and pyridine (1.5g) were added as an imidation catalyst, and it was made to react at 70 degreeC for 3 hours. This reaction solution was poured into methanol (400 ml), and the obtained precipitate was filtered off. This deposit was wash|cleaned with methanol, it dried under reduced pressure at 100 degreeC, and the polyimide powder (A) was obtained. The imidization rate of this polyimide was 72%, the number average molecular weight was 12000, and the weight average molecular weight was 53000.

[0211] NMP (22.0g) was added to the obtained po...

manufacture example 2

[0213] BODA (1.60, 6.4mmol), DA-2 (3.23g, 6.4mmol), 3AMPDA (1.16g, 4.8mmol), and p-PDA (0.52g, 4.8mmol) were dissolved in NMP (25.0g) to After reacting at 60° C. for 5 hours, CBDA (1.85 g, 9.4 mmol) and NMP (8.3 g) were added, and reacted at 40° C. for 10 hours to obtain a polyamic acid solution.

[0214] After adding NMP to this polyamic-acid solution (38g) and diluting to 6.5 mass %, the acetic anhydride (6.6g) and pyridine (2.0g) were added as an imidation catalyst, and it was made to react at 70 degreeC for 3 hours. This reaction solution was poured into methanol (500 ml), and the obtained precipitate was filtered off. This deposit was wash|cleaned with methanol, it dried under reduced pressure at 100 degreeC, and obtained the polyimide powder (B). The imidization rate of this polyimide was 73%, the number average molecular weight was 14000, and the weight average molecular weight was 44000.

[0215] NMP (44.0g) was added to the obtained polyimide powder (B) (6.0g), and ...

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Abstract

To provide a liquid crystal aligning agent which has a fast response speed and is especially suitable for a PSA type liquid crystal display element. A liquid crystal aligning agent containing at least one polymer selected from polyamic acid and polyimide-based polymers obtained by imidating it, wherein the polyamic acid is made of diamine compounds, It is preferably obtained by reacting a diamine component of a diamine represented by any of the following formulas with a tetracarboxylic dianhydride component. The diamine compound has a triplet bond dissociation energy barrier calculated by Gaussian09 of 30 kcal / mol the following keys. (X 1 ~X 3 、X 5 Indicates a single key, etc., X 4 Represents an alkyl group with 1 to 18 carbons, T represents an alkylene group with 1 to 6 carbons, R 1 Indicates OH groups, etc., R 2 ~R 5 stands for hydrogen, Y stands for ‑CH 2 -Wait)

Description

technical field [0001] The present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element suitable for a homeotropic alignment type liquid crystal display element produced by irradiating ultraviolet rays in a state where a voltage is applied to liquid crystal molecules. Background technique [0002] For liquid crystal display elements of a method (also called VA method, vertical alignment method) that responds to liquid crystal molecules vertically aligned with respect to the substrate by an electric field, the manufacturing process may include irradiating ultraviolet rays while applying a voltage to the liquid crystal molecules. process. [0003] For such a liquid crystal display element of the vertical alignment method, it is known that by adding a photopolymerizable compound to the liquid crystal composition in advance, and using a vertical alignment film such as a polyimide system, irradiating ultraviole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02F1/1337C08G73/10
CPCC08G73/10G02F1/1337C09K19/56G02F1/133723
Inventor 林爱子芦泽亮一
Owner NISSAN CHEM CORP
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