Diketoxime ester compound, preparation method and applications thereof

A manufacturing method and compound technology, which are applied in the field of diketoxime ester compounds, can solve the problems that the yellowing of carbazole oxime ester cannot meet the requirements of color difference of color photoresists, etc., and achieve excellent anti-oxygen polymerization inhibition, high photosensitivity, clear imaging effect

Inactive Publication Date: 2019-04-23
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Various bis-oxime ester derivatives with phenylcarbazole as the parent disclosed in patent WO2008138732 have two oxime ester groups in one molecule. Experiments have proved that the yellowing of carbazole oxime esters cannot meet the requirements of color photoresists. Color difference requirements

Method used

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  • Diketoxime ester compound, preparation method and applications thereof
  • Diketoxime ester compound, preparation method and applications thereof
  • Diketoxime ester compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1 synthetic formula I compound

[0052] 1-1 Synthesis of 4,4'-dipropionyl diphenyl sulfide (compound of formula II)

[0053] Weigh 79.0g (0.424mol) of diphenyl sulfide and dissolve it in 600g of 1,2-dichloroethane, add 124.4g (0.933mol) of anhydrous aluminum trichloride, stir and cool down to 0°C; keep below 5°C , add propionyl chloride 82.4g (0.891mol) dropwise, after 2 hours of dropping, continue to keep stirring at 0°C for 2h; add the reaction liquid dropwise to 450ml of 10% dilute hydrochloric acid, control the temperature of the acid solution not higher than 30°C, and stir for 1h after adding , separate the lower organic phase; the organic phase is washed three times with 300ml of water successively; the organic phase is subjected to vacuum distillation to recover the solvent, and the residue is 126g; 240ml of n-hexane is added while it is hot, and the insulation makes the solution clear; natural cooling makes it crystallize, and the solution When the t...

Embodiment 2

[0058] Embodiment 2 Alkali-soluble resin preparation

[0059] Mix 180g of benzyl methacrylate, 60g of methacrylic acid, 60g of hydroxyethyl methacrylate, 15g of azobisisobutyronitrile, 6g of dodecanethiol and 1000ml of toluene and put them into a constant pressure dropping funnel; Put 1000ml of toluene into a three-necked flask, install stirring, a constant pressure dropping funnel and a thermometer, start stirring, and replace the gas in the flask with nitrogen; heat the flask to make the solvent temperature reach 80-85°C, keep it warm, and start adding the monomer mixed solution dropwise, about After 1 hour of dripping; continue to react for 6 hours; naturally cool down, stop stirring, and wait for the resin to settle, absorb the upper clear solution, filter the lower solvent-containing resin, and rinse the resin filter cake with 500ml of toluene; dry the filter cake under reduced pressure to obtain a white Powdered solid resin 250g; it is dissolved into 20% solution with PM...

Embodiment 3

[0060] Preparation and development of embodiment 3 photoresist

[0061] According to the weight ratio of formulations 3A, 3B, 3C, and 3D in Table 1, all components were prepared into photocurable compositions according to the ink preparation method, which were in fluid liquid state.

[0062] Each of the above-mentioned liquid compositions was coated on the glass surface by the wire rod method, and baked at 80° C. for 3 minutes to evaporate the solvent PMA, and the film thickness of the remaining film was measured to be 2 microns for later use.

[0063] First set of exposure tests

[0064] Place a 21-step gray gradient ruler on the film, filter the 2000W high-pressure mercury lamp light with a 365nm grating filter, and set the distance between the film and the grating at 10cm to make the exposure amount reach 200mJ / cm 2 .

[0065] Soak in a 1% sodium carbonate solution bath at 30°C for 1min, and record the maximum film retention order that can be displayed. The larger the numbe...

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Abstract

The present invention relates to a diketoxime ester compound represented by a formula I, and a preparation method thereof, and a photocurable composition using the compound represented by the formulaI as a photoinitiator. According to the present invention, with the application of the photocurable composition in the preparation of photoresist devices such as display screen color filter, the highexposure sensitivity and the relatively low yellowing property are achieved. The formula I is defined in the specification.

Description

technical field [0001] The invention relates to the technical field of photoinitiators, in particular to a diketoxime ester compound, which is characterized in that both esterified oxime groups in the molecule are at the α-position of carbonyl. Background technique [0002] Oxime ester compounds have been discovered as photoinitiators very early. Both US3558309 and US4255513 patents have disclosed oxime ester compounds as photoinitiators. However, the oxime esters of some structures have poor thermal stability or low sensitivity, so it is difficult to Thermal stability, sensitivity and other properties meet the requirements of the modern electronics industry. CN1241562A and CN1514845A disclose a series of oxime ester compounds, and two varieties OXE01 and OXE02 are on the market, and products with similar properties include oxime esters 305 and 304 disclosed in CN101565472B and CN101508744B. [0003] [0004] In the color photoresist, the color difference effect caused b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07C319/20C07C323/22C08F20/10C09D11/101C09D4/02C09D7/63C09J4/02C09J11/06G03F7/004G03F7/027G03F7/00
CPCG03F7/0007G03F7/004G03F7/027C09D11/101C09J4/00C09J11/06C07C323/22C08F2/48C08F20/10C09D4/00C09D7/63C09D11/38C09D11/03C07C323/47G03F7/031C08F220/1807G02B5/223C08F220/06C08F220/20C07C319/20C08F2/50
Inventor 赵文超李家齐王辰龙
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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