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Polyimide precursor, and liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element having precursor

A technology of polyimide precursor and liquid crystal aligning agent, which is applied in the direction of liquid crystal materials, organic chemistry, instruments, etc., can solve the problem of lower reliability of liquid crystal display elements, low solubility of polymeric compounds, and failure to obtain good polymeric compounds Orientation status and other issues

Active Publication Date: 2018-01-02
NISSAN CHEM IND LTD
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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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  • Polyimide precursor, and liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element having precursor
  • Polyimide precursor, and liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element having precursor
  • Polyimide precursor, and liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element having precursor

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Experimental program
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Embodiment

[0301] The present invention will be further specifically described below using examples, but the present invention is not limited by these examples.

[0302] In addition, the abbreviations and structures of the following compounds, and the measuring method of each characteristic are as follows.

[0303] (solvent)

[0304] DMF: N,N-Dimethylformamide

[0305] THF: Tetrahydrofuran

[0306] NMP: N-methyl-2-pyrrolidone

[0307] BCS: Butyl Cellosolve

[0308] (diamine)

[0309] DA-A: 1-(4-(2-(2,4-diaminophenoxy)ethoxy)phenyl)-2-methoxy-2-methylpropan-1-one

[0310] DA-1: 1-(4-(2-(2,4-diaminophenoxy)ethoxy)phenyl)-2-hydroxy-2-methylpropan-1-one

[0311] DA-2: 4-(4-(4-heptylcyclohexyl)phenoxy)benzene-1,3-diamine

[0312] 3AMPDA: 3,5-diamino-N-(pyridin-3-ylmethyl)benzamide

[0313] (acid dianhydride)

[0314] BODA: Bicyclo[3,3,0]octane-2,4,6,8-tetracarboxylic dianhydride

[0315] CBDA: 1,2,3,4-cyclobutanetetracarboxylic dianhydride

[0316] (additive)

[0317] 3AMP: 3-pyri...

Synthetic example 1

[0353] Aromatic diamine compound (DA-A): 1-(4-(2-(2,4-diaminophenoxy)ethoxy)phenyl)-2-methoxy-2-methylpropane- Synthesis of 1-keto

[0354] The aromatic diamine compound (DA-A) was synthesized according to the 5-step route shown below. In addition, an aromatic diamine compound (DA-A) corresponds to the said specific diamine compound.

[0355] Step 1: 2-Hydroxy-2-methyl-1-(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)propan-1-one Synthesis of (DA-A-1)

[0356]

[0357] Dissolve IRGACURE 2959 (2-hydroxy-1-(4-(2-hydroxyethoxy)phenyl)-2-methylpropan-1-one, 50.0 g, 223 mmol) in THF (200 g), add p-toluenesulfonate Acid monohydrate (0.424g, 2.23mmol) was added dropwise to 3,4-dihydro-2H-pyran (23.4g, 279mmol) over 10 minutes, and reacted at room temperature for 3 hours. Then, the reaction solution was filtered, and the filtrate was concentrated to obtain 2-hydroxy-2-methyl-1-(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy yl)phenyl)propan-1-one as a crude product (green liqu...

Embodiment 1 and 2

[0376]

[0377] BODA (10.01g, 40.0mmol), 3AMPDA (4.85g, 20.0mmol), DA-A (13.78g, 40.0mmol), DA-2 (15.22g, 40.0mmol) were dissolved in NMP (166.2g), in After reacting at 60 degreeC for 5 hours, CBDA (11.57g, 59.0mmol) and NMP (55.4g) were added, it was made to react at 40 degreeC for 10 hours, and the polyamic-acid solution was obtained.

[0378] After adding NMP to this polyamic-acid solution (250g) and diluting to 6.5 mass %, the acetic anhydride (45.9g) and pyridine (14.2g) 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 (3300 ml), and the obtained precipitate was collected by filtration. 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 14000, and the weight average molecular weight was 38000.

[0379] NMP (44.0...

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Abstract

The present invention provides a polyimide precursor in which the quantity of radicals generated is relatively large. Through this polyimide precursor, reaction of a polymerizable compound is accelerated, the pretilt angle in liquid crystals is efficiently set to the desired value, and a liquid crystal display element having enhanced response speed is provided. The present invention provides a polyimide precursor which uses a first photoradical generating diamine, the polyimide precursor being characterized in that the quantity of radicals generated during photoirradiation under the same conditions is greater than in a second polyimide precursor formed under the same conditions as the polyimide precursor except that the first photoradical generating diamine is replaced therein with a second photoradical generating diamine represented by formula (1).

Description

technical field [0001] The present invention relates to a polyimide precursor which generates a relatively large amount of free radicals and which can be used in a vertical alignment type liquid crystal display element produced by irradiating ultraviolet rays in a state where a voltage is applied to liquid crystal molecules. The liquid crystal aligning agent of an amine precursor, the liquid crystal aligning film formed with this liquid crystal aligning agent, and the liquid crystal display element formed with this liquid crystal aligning film. Background technique [0002] For the liquid crystal display element of the method in which the liquid crystal molecules aligned vertically with respect to the substrate respond by an electric field (also called the vertical alignment (VA) method), 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07C217/86G02F1/1337
CPCC07C217/86C08G73/10G02F1/1337C08G73/1025C09K19/56
Inventor 长尾将人近藤光正
Owner NISSAN CHEM IND LTD