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Dioxime ester photoinitiator, preparation method, photosensitive resin composition and application

A technology of photoinitiators and esters, which is applied in the field of photocuring, can solve the problems of easy migration of photoinitiators, and achieve the effect of reducing migration and high initiation efficiency

Active Publication Date: 2019-07-30
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main purpose of the present invention is to provide a kind of double oxime ester photoinitiator, preparation method, photosensitive resin composition and application, to solve the problem that existing photoinitiator is easy to migrate

Method used

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  • Dioxime ester photoinitiator, preparation method, photosensitive resin composition and application
  • Dioxime ester photoinitiator, preparation method, photosensitive resin composition and application
  • Dioxime ester photoinitiator, preparation method, photosensitive resin composition and application

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preparation example Construction

[0056] The present application also provides a kind of preparation method of above-mentioned double oxime ester photoinitiator on the other hand, and this preparation method comprises:

[0057] S1, under the action of the first catalyst, use raw material a to react with raw material b to obtain intermediate a, the synthetic route is as follows:

[0058]

[0059] Among them, X 1 means halogen, A means -CH 2 -or-NH-, G' means R 5 or R 6 group, G means group, R 5 and R 6 represent independently of each other a polymerizable group;

[0060] S2, under the action of the second catalyst, intermediate a is subjected to Friedel-Crafts acylation reaction with raw material c and raw material d to obtain intermediate b. The synthetic route is as follows:

[0061]

[0062] Among them, X 2 and x 3 are independently selected from halogen;

[0063] J and Q represent linking bonds or carbonyl groups,

[0064] R 1 ’ for R 1 or R 1 -CH 2 -, R 2 ’ means R 2 or R 2 -CH 2 ...

Embodiment 1

[0118] (1) Synthesis of Intermediate 1a

[0119] Add 24.2g of raw material 1a, 10.8g of sodium methoxide, and 50mL of thionyl chloride (DMSO) into a 250mL four-necked flask, blow nitrogen into the above-mentioned four-necked flask, and stir at room temperature for 0.5h. Then, 21.3 g of the raw material 1b was slowly added dropwise to the above-mentioned four-neck flask, and the addition was controlled within 3 hours, and the liquid phase followed the reaction until the raw material no longer changed. The material obtained after the reaction was poured into deionized water, stirred, and the product was extracted with n-hexane, and the n-hexane product solution was dried with anhydrous magnesium sulfate, and the n-hexane was removed by rotary evaporation, and then recrystallized with methanol as a solvent to obtain 28.7g of yellow solid product, ie intermediate 1a, the yield is 75wt%, and the purity is 98wt%.

[0120] The synthetic route is:

[0121]

[0122] Intermediate 1...

Embodiment 2

[0141] (1) Synthesis of Intermediate 2a.

[0142] Add 24.3g of raw material 2a, 10.8g of sodium methoxide, and 50mL of thionyl chloride (DMSO) into a 250mL four-neck flask, blow in nitrogen gas, stir at room temperature for 0.5h, then slowly add 10.6g of epichlorobutane dropwise, and control the drop for 3h. After the addition, the liquid phase followed the reaction until the raw materials no longer changed. Pour the material obtained after the reaction into deionized water, stir, extract the product with n-hexane, dry the n-hexane product solution with anhydrous magnesium sulfate, remove the n-hexane by rotary evaporation, and recrystallize with methanol as a solvent to obtain 28.2 g of a white solid product , namely intermediate 2a, with a yield of 90wt% and a purity of 98wt%.

[0143] The synthetic route is:

[0144]

[0145] The structure of intermediate 2a was confirmed by H NMR and mass spectrometry:

[0146] 1 H-NMR (CDCl 3 , 500MHz): 1.8936-1.9451 (2H, m), 2.49...

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Abstract

The invention provides a dioxime ester photoinitiator, a preparation method, a photosensitive resin composition and application. The dioxime ester photoinitiator has a structure shown in a general formula (I). Since the dioxime ester photoinitiator contains a polymerizable group, the dioxime ester photoinitiator can form a polymer cured product with a large molecular weight by means of a polymerization reaction during application so that photoinduced migration can be effectively reduced. At the same time, due to the special structure, the dioxime ester photoinitiator has high initiation efficiency. Therefore, the dioxime ester photoinitiator having the structure above has the advantages of being unlikely to migrate, high in photoinitiation efficiency and the like.

Description

technical field [0001] The invention relates to the field of photocuring, in particular to a bis-oxime ester photoinitiator, a preparation method, a photosensitive resin composition and applications. Background technique [0002] Compared with the traditional picture tube monitor, the liquid crystal display device has the advantages of low energy consumption, small size and no radiation, but still has the defects of too small viewing angle, image smearing, poor brightness and contrast. In recent years, with the continuous improvement of people's living standards, people have put forward higher requirements for liquid crystal display devices, such as large size, high brightness, high contrast, and wide viewing angles. The materials used in the process put forward higher requirements. [0003] Color and black photoresists and optical spacers are important components of liquid crystal flat panel displays, and are essential materials for high-generation flat panel displays to a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/66C07C249/04C07C255/64C07C253/30C07D303/36C07D301/00C07D305/06C07D209/86C07D405/06G03F7/027G03F7/004
CPCC07C251/66C07C255/64C07D303/36C07D301/00C07D305/06C07D209/86C07D405/06G03F7/027G03F7/004
Inventor 钱晓春胡春青于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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