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Coating solution for forming polyimide film, liquid crystal alignment agent, polyimide film, liquid crystal alignment film, and liquid crystal display element

A polyimide film, polyimide technology, applied in coatings, instruments, optics, etc., can solve problems such as poor printing, inability to freely use diamine components, and burn-in

Active Publication Date: 2013-11-27
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, when the liquid crystal aligning agent is applied to the substrate, problems such as deposition and separation caused by prolonged takt time, printing defects, and screen burn-in caused by accumulated charge (RDC) have become problems. It is difficult to solve both problems at the same time
[0009] As mentioned above, in the polyimide liquid crystal aligning film, various diamine components are used as part of the raw materials in order to improve the desired characteristics, but due to the relationship with other characteristics, the desired diamine components may not be freely used.
[0010] In addition, due to its characteristics, that is, high mechanical strength, heat resistance, and solvent resistance, polyimide is not only used as a liquid crystal alignment film, but also widely used as a protective material and insulating material in the electrical and electronic fields. When used as such a material, the diamine component that is the raw material of polyimide is similarly improved, but the same is true for the fact that the desired diamine component cannot be used freely.

Method used

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  • Coating solution for forming polyimide film, liquid crystal alignment agent, polyimide film, liquid crystal alignment film, and liquid crystal display element
  • Coating solution for forming polyimide film, liquid crystal alignment agent, polyimide film, liquid crystal alignment film, and liquid crystal display element
  • Coating solution for forming polyimide film, liquid crystal alignment agent, polyimide film, liquid crystal alignment film, and liquid crystal display element

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Experimental program
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Effect test

Embodiment

[0140] Hereinafter, although an Example and a comparative example are given and this invention is demonstrated in more detail, explanation of this invention is not limited to these Examples.

[0141] [Synthesis of bifunctional compound represented by the above formula [A]]

Synthetic example 1

[0143] The compound 5,5'-(1,4-phenylenebis(azanediyl))bis(methane-1-yl-1-ylidene)bis(2,2-dimethylene) represented by the following formula [4] Synthesis of 1,3-dioxane-4,6-dione)

[0144] [chem 22]

[0145]

[0146] Michaelis' acid [1] (14.7 g, 102 mmol) and trimethyl orthoformate [2] (147 g) were added to a 300 mL four-necked flask, and heated to reflux for 1 hour. Thereafter, p-phenylenediamine [3] (5.09, 46 mmol) was added, followed by heating to reflux for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated solid was filtered, washed with hexane, and then dried to obtain 15.8 g of compound [4] (yield 82%).

[0147] 1 H-NMR (400MHz, DMSO-d6, δppm): 11.29(2H,d), 8.56(2H,d), 7.64(4H,s), 1.68(12H,s).

Synthetic example 2

[0149] The compound 5,5'-(1,3-phenylenebis(azanediyl))bis(methane-1-yl-1-ylidene)bis(2,2-dimethylene) represented by the following formula [6] Synthesis of 1,3-dioxane-4,6-dione)

[0150] [chem 23]

[0151]

[0152] Michaelis' acid [1] (14.R, 102 mmol) and trimethyl orthoformate [2] (1479) were added to a 300 mL four-neck flask, and heated to reflux for 1 hour. Then, m-phenylenediamine [5] (5.09, 46 mmol) was added, followed by heating to reflux for another 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated solid was filtered, washed with hexane, and then dried to obtain 14.1 g of compound [6] (yield 72%).

[0153] 1 H-NMR (400MHz, DMSO-d6, δppm): 11.28(2H,s), 8.74(2H,s), 7.98(1H,s), 7.44(3H,s), 1.68(12H,s).

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Abstract

Provided is a coating solution for forming a polyimide film, said coating solution comprising: a polymer of a polyimide precursor obtained by polymerizing a tetracarbonate component and a diamine component, and / or a polyimide formed by the imidization of the polyimide precursor; and a bifunctional compound represented by formula [A] and having a Meldrum's acid structure introduced into each of two amino groups of a diamine compound. Also provided are: a liquid crystal alignment agent comprising said coating solution; a polyimide film obtained by firing a substrate coated using said coating solution; a polyimide film comprising a polyimide in which the polymer is crosslinked using the bifunctional compound represented by formula [A]; a liquid crystal alignment film comprising the polyimide film; and a liquid crystal display element equipped with said liquid crystal alignment film. (In the formula, Y, R1 and R2 are groups specified in claims 1 and 4.)

Description

technical field [0001] The present invention relates to a novel coating liquid for polyimide film formation, a liquid crystal aligning agent, a polyimide film formed using them, a liquid crystal aligning film, and a liquid crystal display element. Background technique [0002] In a liquid crystal display element, a liquid crystal alignment film is responsible for aligning liquid crystals in a certain direction. At present, the main liquid crystal aligning film used in industry is coated with a polyimide-based liquid crystal aligning agent composed of a solution of polyamic acid, polyamic acid ester or polyimide as a polyimide precursor. Substrates are manufactured by film-forming methods. In addition, when aligning the liquid crystal in parallel or obliquely with respect to the substrate surface, surface stretching treatment is further performed by rubbing after film formation. In addition, as an alternative method of rubbing treatment, a method using an anisotropic photoc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09D179/08C08G73/10G02F1/1337
CPCC09D179/08C08G73/10G02F1/1337
Inventor 南悟志
Owner NISSAN CHEM IND LTD
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