Diamine compound, resin, photosensitive resin composition, and cured film

A technology of amine compounds and photosensitive resins, which is applied in the field of diamine compounds, resins, photosensitive resin compositions and cured films, can solve the problems of high thermal expansion coefficient of photosensitive resin cured films, reduced exposure sensitivity, and influence on transmittance, etc., to achieve Good photosensitive properties, excellent mechanical properties, and the effect of improving light transmittance

Active Publication Date: 2022-03-18
武汉柔显科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the way of introducing more phenolic hydroxyl groups in the prior art is to use biphenyl hydroxyl-containing monomers or alicyclic dianhydrides, but the use of biphenyl rigid monomer polymers in solvents and alkaline The poor solubility in the solution will lead to a decrease in exposure sensitivity and affect the transmittance; while the alicyclic structure chain links are relatively flexible, which will cause the problem of a high thermal expansion coefficient of the cured photosensitive resin film

Method used

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  • Diamine compound, resin, photosensitive resin composition, and cured film
  • Diamine compound, resin, photosensitive resin composition, and cured film
  • Diamine compound, resin, photosensitive resin composition, and cured film

Examples

Experimental program
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Effect test

preparation example Construction

[0037] for R 0 Indicates -Ph-SO 3 - the diamine compound, R 1 Indicates -CH 3The preparation method comprises the steps of: mixing the phenolic compound shown in formula (4) and p-nitrobenzenesulfonyl chloride in a solvent such as DMF according to a molar ratio of 1:2, adding potassium carbonate, and reacting to obtain a dinitro compound; the obtained The dinitro compound is reduced under the Pd-C catalyst / hydrogen atmosphere / ethylene glycol monomethyl ether solvent to obtain the diamine compound. The general reaction formula is shown in the following formula (5). for R 1 The formula (4) representing a hydrogen atom needs to first esterify the alcoholic hydroxyl group in the formula (4) to protect the hydroxyl group, then react with p-nitrobenzenesulfonyl chloride, and then restore the alcoholic hydroxyl group through the step of hydrolysis of the ester group.

[0038]

[0039] Furthermore, for R 0 A diamine compound representing -Ph-S-, wherein -Ph represents a pheny...

Embodiment

[0089] The above and other advantages of the present invention can be better understood through the following examples, but the following examples are not intended to limit the scope of the present invention.

[0090] Description of abbreviations:

[0091] ODA: 4,4'-diaminodiphenyl ether

[0092] 6FAP: 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane

[0093] SiDA: 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

[0094] 6FDA: 2,2'-bis(3,4-dicarboxylic acid phenyl)hexafluoropropane dianhydride

[0095] ODPA: 3,3’,4,4’-Diphenyl ether tetracarboxylic dianhydride

Synthetic example 1

[0097] Synthesize diamine compound Y1 according to the following route:

[0098]

[0099] The specific operation is: use 2,6-dimethylbromobenzene as the raw material, oxidize the methyl group to a carboxyl group, replace the benzene ring with a sulfonic acid group, and convert the sulfonic acid group into a sulfonyl chloride through phosphorus oxychloride After being reduced to thiophenol, react with m-nitrobromobenzene to generate thioether compounds, and then in bis(pinacolate) diboron (B 2 Pin 2 ) under the action of a Suzuki coupling reaction to obtain a thioether biphenyl compound, and finally to obtain a diamine compound Y1 through hydrolysis and reduction.

[0100] Or select the following route to synthesize the diamine compound Y1 derivative:

[0101]

[0102] The specific operation is: use 3,3',5,5'-tetraaldehyde-4,4'-dihydroxybiphenyl as the raw material, and react with phosphorus tribromide to obtain bromide, and then in the mixed solvent of quinoline and pyri...

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Abstract

The invention discloses a diamine compound, resin, a photosensitive resin composition and a cured film, and relates to the technical field of photosensitive resin materials. The general formula of the diamine compound is as shown in formula (1), wherein R represents a straight bond,-O-or an organic group with 1-20 carbon atoms; r0 is an organic group comprising a sulfonic acid group, a sulfonyl group or a thioether group, and R1 represents H or alkyl with the carbon atom number of 1-3; r2 is H, alkyl with 1-20 carbon atoms or an organic group containing O, S, N and Si; i is an integer greater than or equal to 1. The diamine compound provided by the invention simultaneously contains cross-linking groups such as alkoxy or hydroxymethyl and functional groups such as sulfuryl or sulfonic acid group, and the diamine compound provided by the invention is introduced into photosensitive resin, so that the photosensitive resin is good in photosensitive property and excellent in mechanical and thermal properties.

Description

technical field [0001] The invention relates to the technical field of photosensitive resin materials, in particular to diamine compounds, resins, photosensitive resin compositions and cured films. Background technique [0002] Polyimide (PI) is an ideal polymer material with excellent heat resistance, mechanical properties, electrical insulation properties and chemical stability. It is often used in the fields of aerospace, semiconductors, optoelectronics and microelectronics; photosensitive Permanent polyimide (PSPI) can realize image processing without the help of other photoresists, which further shortens the process route compared with traditional polyimide (PI), and is an ideal insulating material in the field of electronics and microelectronics. [0003] In the heat-resistant resin precursor composition that is dissolved and cleaned with an alkaline developer after exposure, because the solubility of the carboxyl group in the polyamic acid is too large, adding the pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/36
CPCC07C317/36C07C323/37C07C309/76C07F5/025C07C319/02C07C319/14C07C303/02C07C303/06C07C51/265C07C315/02C07C315/04C07C319/20C08G73/1064G03F7/004C07C63/70C07C309/58C07C309/89C07C317/22C07C323/62C07C323/19
Inventor 周小明肖桂林鲁丽平王元强朱双全
Owner 武汉柔显科技股份有限公司
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