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Diazanaphthoquinone sulfonate compound and resin composition

A technology of naphthoquinone sulfonate and compound is applied in the field of photolithography technology and can solve problems such as unfavorable long-term stability of devices and incomplete reaction.

Pending Publication Date: 2022-05-06
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduced cross-linking agent will also have new adverse effects on the physicochemical properties of the cured resin film (such as, due to incomplete reaction, part of the cross-linking agent will be in a free small molecular state in the film, which is not conducive to the long-term stability of the device. ), therefore, the industry urgently needs to develop a material that has excellent performance as a PAC and is difficult to produce outgassing, sublimation, migration and dissolution in the final cured film of photoresist, and also urgently hopes to reduce the amount of crosslinking agent

Method used

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  • Diazanaphthoquinone sulfonate compound and resin composition
  • Diazanaphthoquinone sulfonate compound and resin composition
  • Diazanaphthoquinone sulfonate compound and resin composition

Examples

Experimental program
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Effect test

Embodiment

[0075] The resins, compounds and compositions of the present invention were synthesized representatively, and the properties of each resin composition were tested.

[0076] The following synthesis examples of the present invention exemplarily provide specific synthetic methods of representative compounds. Solvents and reagents used in the following synthesis examples can be purchased or customized from the domestic chemical product market, such as purchased from Sinopharm Group Reagent Company, Sigma-AldRich Company, Bailingwei Reagent Co., Ltd., etc.

preparation example 1

[0078] Synthesis of diamine intermediate 1:

[0079] Synthetic intermediate 4-(2-(4-hydroxyphenyl)propan-2-yl)benzene (form)aldehyde:

[0080] Argon atmosphere, POCl at -5°C 3 (11.2 mL, 0.12 mol) was slowly added dropwise into 60 mL of DMF. Add the DMF solution of 4-cinnamon phenol dropwise into the reaction system, slowly raise the temperature of the reaction system to 60°C, and keep it warm for 3 hours. After the temperature of the reaction system drops to room temperature, pour the reaction mixture into ice cubes, and the system After neutralization to neutrality, extract with ethyl acetate, collect the organic phase, wash with saturated sodium chloride and deionized water, and remove most of the solvent by rotary evaporation. After vacuum drying at 50°C, pass the crude product of the target product through the column layer The target product was purified by analytical method.

[0081]

[0082] ZAB-HS mass spectrometer (manufactured by Micromass, UK), M / Z (M+1): 241. ...

preparation example 2

[0087] Synthesis of diamine intermediate 2:

[0088] Under nitrogen protection, weigh 18.62g (0.1mol) 6-methoxy-2-naphthaldehyde in a 100mL three-necked flask, weigh 36.9g (0.3mol) o-methoxyaniline and add it to the three-necked flask, and heat up to React at 150°C for 3 hours, recrystallize the obtained crude product with ethanol, azeotrope with hydroiodic acid for 2 hours under nitrogen protection, then add sodium bicarbonate to neutralize hydroiodic acid, collect the precipitate, and obtain diamine intermediate 2.

[0089]

[0090] ZAB-HS mass spectrometer (manufactured by Micromass, UK), M / Z (M+1): 373.

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Abstract

The invention provides a diazo naphthoquinone sulfonic acid ester compound and a resin composition protecting the diazo naphthoquinone sulfonic acid ester compound, the diazo naphthoquinone sulfonic acid ester compound is represented by a general formula I, R9 is an m + q + 2-valent C6-C100 aromatic organic group, (OH) q represents q phenolic hydroxyl groups connected to an aromatic ring of R9, OQ represents a residue of a reaction between the diazo naphthoquinone sulfonic acid compound and the phenolic hydroxyl groups connected to R9, q is an integer, qgt; 0 and m are integers, m is greater than or equal to 0, the value of m + q is 1-8, L is a C2-C50 monovalent organic group, L contains an olefinic unsaturated double bond or an acetylenic bond or-CH2OCiH2i + 1, i is an integer of 1-20, and R12 is a C1-C20 monovalent organic group.

Description

technical field [0001] The invention relates to the technical field of photolithography, in particular to a diazonaphthoquinone sulfonate compound and a resin composition containing the diazonaphthoquinone sulfonate compound. Background technique [0002] Organic electroluminescent display (OLED) has the characteristics of thinness, wide angle, high contrast, and flexibility, and is one of the mainstream flat panel display technologies at present. From the perspective of improving consumer experience, improving the long-term reliability of display devices is a long-term topic in this field. Generally speaking, organic light-emitting molecules have low tolerance to water molecules, air, impurity molecules, etc. When exposed to harsh environments, they are prone to adverse phenomena such as pixel shrinkage and failure to light up. In order to improve the OLED panel To improve reliability, improving the quality of packaging materials is one of the feasible methods. [0003] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/76G03F7/016
CPCC07C309/76G03F7/0163
Inventor 韩红彦刘永祥王旭刘嵩
Owner BEIJING ETERNAL MATERIAL TECH
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