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Di-oxime ester photoinitiator containing thiophene ring as well as preparation method and application thereof

A technology of photoinitiator and thiophene ring, which is applied in the field of photoinitiator, can solve the problems such as difficult curing of color resist, achieve the effects of improving sensitivity and thermal stability, good light absorption properties, and simple preparation method

Inactive Publication Date: 2017-03-08
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the increase of the pigment content, the curing of the color resist becomes more difficult, and the clarity and integrity of the cured image also have higher requirements, which requires a higher sensitivity initiator to solve the above problems

Method used

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  • Di-oxime ester photoinitiator containing thiophene ring as well as preparation method and application thereof
  • Di-oxime ester photoinitiator containing thiophene ring as well as preparation method and application thereof
  • Di-oxime ester photoinitiator containing thiophene ring as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preferred photoinitiator compounds of the present invention include the preparation of the following compound (1).

[0036] (1)

[0037] The initial substance is 1,3-benzenediacetonitrile, the intermediate oxime is obtained by reacting with and, and then the intermediate oxime is reacted with acid chloride by esterification to obtain the product. The used synthetic route of this preparation method is expressed as follows:

[0038]

[0039] a: Potassium hydroxide, methanol, tetrahydrofuran, room temperature, 24h;

[0040] b: Anhydrous tetrahydrofuran, anhydrous triethylamine, ice-water bath, dark, N 2 Protection, 2h.

[0041] (1) Synthesis of intermediate oxime: Dissolve nitrothiophene (3.23g, 0.02mol) in 120mL of methanol, add 6.8g of potassium hydroxide at room temperature, fully dissolve; Dissolve in 60ml of tetrahydrofuran, add dropwise to the methanol solution of nitrothiophene in a constant pressure dropping funnel, adjust the pH value to 5 with concentrat...

Embodiment 2

[0050] The preferred photoinitiator compounds of the present invention include the preparation of the following compound (2).

[0051] (2)

[0052] The initial substance is 1,3-benzenediacetonitrile, the intermediate oxime is obtained by reacting with and, and then the intermediate oxime is reacted with acid chloride by esterification to obtain the product. The used synthetic route of this preparation method is expressed as follows:

[0053]

[0054] a: Potassium hydroxide, methanol, tetrahydrofuran, room temperature, 24h;

[0055] b: Anhydrous tetrahydrofuran, anhydrous triethylamine, ice-water bath, dark, N 2 Protection, 2h.

[0056] (1) Step a is the same as (1) intermediate oxime synthesis in Preparation Example 1.

[0057] (2) Synthesis of the target molecule: under the protection of an inert gas, put 0.20 g (0.5 mmol) of the intermediate oxime obtained in step (1) into a dry flask, add 5 ml of anhydrous tetrahydrofuran, wrap it in aluminum foil to avoid light, a...

Embodiment 3

[0062] Preferred photoinitiator compounds of the present invention include the preparation of the following compound (3).

[0063] (3)

[0064] The preparation method was the same as in Example 2, except that in the process of preparing the photoinitiator, 2,4-difluorobenzenesulfonyl chloride was used instead of p-toluyl chloride in the second step, and the other preparation methods remained unchanged, with a yield of 40%. The specific NMR characterization results are as follows:

[0065] 1 H NMR (400 MHz, CDCl 3 ) δ: 8.12 (ddd, J = 14.0, 8.7, 5.8 Hz, 2H), 7.52 –7.38 (m, 4H), 7.05 – 6.97 (m, 2H), 6.97 – 6.88 (m, 4H), 6.47 (t, J = 4.2 Hz, 2H);

[0066] 13 C NMR (101 MHz, CDCl 3 ) δ: 164.93, 163.71, 160.64, 143.15, 141.28, 134.25, 131.33, 128.54, 126.13, 125.66, 124.62, 122.81, 118.81, 112.43, 106.57, 106.01.

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Abstract

The invention relates to a di-oxime ester photoinitiator having high light sensitivity in a near ultraviolet-visible light zone as well as a preparation method and an application thereof. The di-oxime ester photoinitiator is the nonionic and halogen-free photoinitiator which is effective in the ultraviolet-visible light zone of 365 nm-425 nm, an oxime esters group having strong electron-withdrawing capability is taken as an electron-withdrawing group, and forms a conjugated system with thiophene through connection, and the di-oxime ester photoinitiator has a disubstituted symmetrical structure. The photoinitiator has excellent performaces of storage stability, sensitivity, development performance and pattern integrity, compared with the same kind photoinitiator, the preparation method in the invention is simple, the applicable light source scope is wide, and the toxicity is low; disubstituted characteristic on the structure of the photoinitiator increases the acid generation performance by several times, and compared with the current single oxime esters photoinitiator products, the performance of the photoinitiator is better.

Description

technical field [0001] The invention belongs to the technical field of photoinitiators, and in particular relates to a class of high-sensitivity photoinitiators of bis-oxime esters containing thiophene rings which are highly sensitive to ultraviolet-visible light, specifically bis-oximes containing thiophene rings with different substitution positions and different ester groups Ester photoinitiator and its preparation method and application. Background technique [0002] Compounds with an oxime ester structure are widely known as photoinitiators in the art. Patent documents such as publication numbers CN99108598A, CN101508744A, CN10565472A, and CN104672354A disclose different carbazole oxime esters and ketoxime ester photoinitiators. Our photoinitiators can meet the application requirements of current display panels, color filters and photocuring or photoresists to varying degrees. [0003] UV-visible light curing technology is an environmentally friendly technology in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48G03F7/004C07D333/36
CPCC07D333/36C08F2/48G03F7/004
Inventor 金明孙新万德成
Owner TONGJI UNIV
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