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Diamine compound, heat resistant resin or heat resistant resin precursor using same, photosensitive resin composition, cured film, and display device

A heat-resistant resin, amine compound technology, applied in the preparation of organic compounds, the preparation of aminohydroxy compounds, photosensitive materials for optomechanical equipment, etc. Reduce heat resistance and other problems, to achieve the effect of improving heat resistance, increasing cross-linking density, and reducing outgassing

Active Publication Date: 2021-03-19
武汉柔显科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the publication numbers are CN1275094C, CN105820338A patents and journal documents Hydroxyanide-containing Positive-type Photosensitive Polyimides. Masatoshi Hasegawa .et al, J. Photopolym. Sci. Tech ., 2007, 20, 175. and other reports; but the introduction of these groups inevitably leads to the reduction of heat resistance and the increase of hygroscopicity of polyimide resin, which is not conducive to its application in devices

Method used

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  • Diamine compound, heat resistant resin or heat resistant resin precursor using same, photosensitive resin composition, cured film, and display device
  • Diamine compound, heat resistant resin or heat resistant resin precursor using same, photosensitive resin composition, cured film, and display device
  • Diamine compound, heat resistant resin or heat resistant resin precursor using same, photosensitive resin composition, cured film, and display device

Examples

Experimental program
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Effect test

preparation example Construction

[0045] Preparation method of structural formula A

[0046] The synthesis of the binary amine compound shown in the formula (1) can be produced based on the method for producing known diamine compounds; in the formula (1), in particular, the present invention, the present invention EXAMPLES Select the use of nitro compound precursors in palladium carbon (PD / C) or Lani nickel to catalyzes hydrogen reduction; then hydrolyzing the ester group in the acid solution, can be mentioned as an example, showing The following reduction reactions (as shown in the reaction formula B and C).

[0047]

[0048] Reactive B

[0049] The specific reaction conditions of the reaction B are as follows: a solvent is made of methanol, and 2,7-dinitropyl-3, 4 benzoxin is dissolved therein, and the mixture is added to 10% 10 wt. % PD / C, in-house hydrogen, at 20-50 ° C, reaction 5-48 h. Then, PD / C was removed, and the concentrated concentrated filtrate was rotated.

[0050]

[0051] Reactive C

[005...

Synthetic example 1

[0135] Synthesis of 4,4'-diaminosome-2-hydroxy-2'-biphenyl carbonate (A)

[0136]

[0137] Under dry nitrogen gas protection, 2,7-dinitropyl-3, 4 benzoxin (20 g, 69.9 mmol) was dissolved in 300 ml of tetrahydrofuran (THF), and 80 g of reduction iron powder was added, and 20 ml 10 wt was added dropwise. % Hydrochloric acid, warmed to 80 ° C, stirring reaction for 24 h, adjusting pH to weak acidity with sodium carbonate, ethyl acetate extraction, water was washed 3 times, separated from organic phases, concentrated, recrystallized 4,4'-diamino-2 Hydroxy-2'-Benzoic acid (A).

Synthetic example 2

[0139] Synthesis of 4,4'-di (4-amine-based phenyloxy) -2-hydroxy-2'-carboxybenzene compound (b)

[0140]

[0141] Under dry nitrogen stream, 2,7-dihydroxy-3,4 benzoxin (20 g, 87.6 mmol) was dissolved in 300 ml N, N-dimethylpyrrolidone (NMP), and 4-fluorine - Nitrobenzene (24.7 g, 175.3 mmol), potassium carbonate (48.5 g, 350.6 mmol), 50 ° C reaction 10 h, poured into water, ethyl acetate extraction, concentrated organic phase, to obtain a nitro compound.

[0142]

[0143] The resulting 2,7-b (4-nitrophenyloxy) -3, 4 benzoxin was dissolved in 500 mL of ethanol, add 80 g of zinc shavitation, dripping 20 ml 10 wt% hydrochloric acid, warming up to 50 ° C, stirring reaction 24 h, filtered off Pd / C, concentrated filtrate, recrystallized 2,7-di (4-aminophenyloxy) -2-hydroxy-2'-carboxybenzene compound (b) .

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Abstract

The present invention provides a heat-resistant resin or precursor capable of generating an ester group for crosslinking, a photosensitive resin composition having high sensitivity and high resolutionis prepared after the resin or precursor is blended with a photosensitizer, and the photosensitive resin composition has excellent thermal stability and chemical resistance after heat treatment. In addition, the invention also provides diamine monomers represented by general formulas (1) and (2), and a structure of the diamine monomer contained in the heat-resistant resin or precursor capable ofgenerating ester groups for cross-linking.

Description

Technical field [0001] The present invention relates to a diamine monomer having a ester group, and based on its heat-resistant resin or heat resistant resin precursor that can be crosslinked by an ester group, and a photosensitive resin composition and a cured film thereof, specific photosensitive resin. The composition can be applied to the insulating layer of the organic light emitting element in the display device, a flat layer, a pixel definition layer, and a protective film of the semiconductor element, an interlayer insulating film, and the like. Background technique [0002] In recent years, the development of photosensitive resin compositions that can change in the developer before and after exposure, meet the needs of patterned production, greatly promoting the rapid development of large-scale integrated circuits and display devices; with the semiconductor components The surface protective film, the interlayer insulating film, etc. also requires the μm level or even the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/64C07C227/12C07C217/90C07C213/02C07D311/80C07C229/46C07C227/02C07D493/04C07C227/04C07C201/12C07C205/59C08G73/10G03F7/004H01L51/52H01L51/54
CPCC07C229/64C07C227/12C07C217/90C07C213/02C07D311/80C07C229/46C07C227/02C07D493/04C07C227/04C07C201/12C08G73/1078C08G73/1039C08G73/105C08G73/1042G03F7/004C07C2601/04H10K85/00H10K50/8428C07C205/59
Inventor 王元强肖桂林朱双全
Owner 武汉柔显科技股份有限公司
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