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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 technology of heat-resistant resin and photosensitive resin, which is applied in the preparation of organic compounds, the preparation of aminohydroxyl compounds, and photosensitive materials used in optomechanical equipment, etc. It can solve the problem of reduced heat resistance and increased hygroscopicity of polyimide resins , unfavorable device applications and other issues

Active Publication Date: 2021-05-11
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

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preparation example Construction

[0045] The preparation method of structural formula A

[0046] The synthesis of diamine compounds shown in general formula (1) can be produced based on known diamine compound production methods, without special limitations; in general formula (1), especially the situation shown in structural formula A, the present invention The embodiment selects the nitro compound precursor to be obtained by hydrogen reduction under the catalysis of palladium carbon (Pd / C) or Raney nickel; then it is obtained by hydrolyzing the ester group in an acid solution, and representative compounds can be cited as examples, showing The following reduction reactions (as shown in Reaction Formulas B and C).

[0047]

[0048] Reaction B

[0049] The specific reaction conditions of reaction formula B are as follows: use methanol as solvent, dissolve 2,7-dinitro-3,4 benzocoumarin in it, and add 1 / 1000 to 10 / 1000 equivalent of 10wt % Pd / C, feed hydrogen, react at 20-50 ℃ for 5-48h. The Pd / C was then remo...

Synthetic example 1

[0135] Synthesis of 4,4'-diamino-2-hydroxy-2'-biphenylcarboxylic acid (a)

[0136]

[0137] Under the protection of dry nitrogen flow, 2,7-dinitro-3,4 benzocoumarin (20g, 69.9 mmol) was dissolved in 300mL tetrahydrofuran (THF), 80 g reduced iron powder was added, and 20 mL10wt % hydrochloric acid, heated to 80 ℃, stirred and reacted for 24h, adjusted the pH value to weak acidity with sodium carbonate, extracted with ethyl acetate, washed 3 times with water, separated the organic phase, concentrated, and recrystallized 4,4'-diamino-2- Hydroxy-2'-biphenylcarboxylic acid (a).

Synthetic example 2

[0139] Synthesis of 4,4'-bis(4-aminophenyloxy)-2-hydroxy-2'-carboxybiphenyl compound (b)

[0140]

[0141] Under the protection of dry nitrogen flow, 2,7-dihydroxy-3,4-benzocoumarin (20g, 87.6 mmol) was dissolved in 300mL N,N-dimethylpyrrolidone (NMP), and 4-fluoro - Nitrobenzene (24.7g, 175.3 mmol), potassium carbonate (48.5g, 350.6 mmol), react at 50°C for 10 h, pour into water, extract with ethyl acetate, concentrate the organic phase to obtain the nitro compound.

[0142]

[0143] Dissolve the obtained 2,7-bis(4-nitrophenyloxy)-3,4 benzocoumarin in 500 mL of ethanol, add 80 g of reduced zinc filings, add dropwise 20 mL of 10 wt% hydrochloric acid, and heat up to 50°C, stirred for 24 h, filtered off Pd / C, concentrated the filtrate, and recrystallized to obtain 2,7-bis(4-aminophenyloxy)-2-hydroxy-2'-carboxybiphenyl compound (b).

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Abstract

The invention provides a heat-resistant resin or precursor that can generate ester groups for cross-linking. The resin or precursor is combined with a photosensitizer to prepare a photosensitive resin composition with high sensitivity and high resolution, and the photosensitive resin composition After heat treatment, it has excellent thermal stability and chemical resistance. In addition, the present invention also provides diamine monomers represented by general formulas (1) and (2), and the above-mentioned heat-resistant resin or precursor that can generate ester groups for cross-linking contains the structure of the above-mentioned diamine monomers.

Description

technical field [0001] The present invention relates to a diamine monomer capable of generating ester groups, a heat-resistant resin or a heat-resistant resin precursor that can be cross-linked through an ester group based on the diamine monomer, a photosensitive resin composition and a cured film thereof, specifically the photosensitive resin The composition can be applied to an insulating layer, a planarization layer, a pixel definition layer of an organic light-emitting element in a display device, a protective film of a semiconductor element, an interlayer insulating film, and the like. Background technique [0002] In recent years, the development of photosensitive resin compositions whose solubility in the developer solution can change before and after exposure meets the needs of patterning and greatly promotes the rapid development of large-scale integrated circuits and display devices; For surface protection films, interlayer insulating films, etc., resolution and hi...

Claims

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Application Information

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Patent Type & Authority Patents(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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