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Oxime ester compound and photopolymerization initiator containing the same

A technology of photopolymerization initiators and compounds, which is applied to compounds, optics, and optical filters of elements in group 5/15 of the periodic table. It can solve problems such as pollution and residues in photomasks and heating furnaces, and improve heat resistance. The effect that there are few properties and sublimates

Active Publication Date: 2016-04-06
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, high concentrations of photopolymerization initiators cause residue generation due to deterioration of developability, and contamination of photomasks and heating furnaces due to sublimation products, etc.

Method used

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  • Oxime ester compound and photopolymerization initiator containing the same
  • Oxime ester compound and photopolymerization initiator containing the same
  • Oxime ester compound and photopolymerization initiator containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] [Example 1] Production of compound No.1

[0150] Methacrylate

[0151] 19.8g (65mmol) of 1-(4-(4-(2-hydroxyethoxy)phenylthio)phenyl)propane-1-one (hereinafter also referred to as ketone body a) and 56.2g of methacrylic acid (653 mmol), 5.0 g (26 mmol) of p-toluenesulfonic acid monohydrate, 1.2 g (5.6 mmol) of BHT and 121 g of dichloroethane were stirred and refluxed for 10.5 hours. After cooling, ethyl acetate and water were added for oil-water separation. The organic layer was washed sequentially with water, aqueous sodium bicarbonate solution, and water. After the organic layer was dried over anhydrous magnesium sulfate, solvent removal was performed to obtain 26.3 g of the following methacrylate body a.

[0152]

[0153] Oximation

[0154] Cool the solution containing 26.0g (70mmol) of methacrylate body a obtained in step 1, 7.3g (70mmol) of concentrated hydrochloric acid and 70g of dimethylformamide to 5°C, and add 10.8g of isobutyl nitrite ( 105mmol), sti...

Embodiment 2～4

[0158] [Examples 2-4] Production of Compound No.2, Compound No.3, and Compound No.4

[0159] Use the corresponding ketone body instead of ketone body a (and for compound No.3, use acrylic acid instead of methacrylic acid), except that, according to the method described in Example 1, compound No.2, compound No.3 and compound No.4. The analysis results are shown in [Table 1] to [Table 3]. lambda

[0160] Table 1

[0161]

[0162] *1: CHCl is used as the solvent 3

[0163] Table 2

[0164]

[0165] table 3

[0166]

[0167]

Embodiment 5

[0168] [Example 5] Manufacture of alkali-developable photosensitive resin composition No.1

[0169] Preparation of alkali-developable resin [alkali-developable (B) component]

[0170] Add 184g of bisphenol fluorene type epoxy resin (epoxy equivalent of 231, the epoxy compound represented by the above general formula (3)), 58g of acrylic acid, 0.26 of 2,6-di-tert-butyl-p-cresol into the reaction vessel g, 0.11 g of tetra-n-butylammonium bromide, and 23 g of propylene glycol-1-monomethyl ether-2-acetate were stirred at 120° C. for 16 hours. The reaction solution was cooled to room temperature, 35 g of propylene glycol-1-monomethyl ether-2-acetate, 59 g of biphenyltetracarboxylic anhydride, and 0.24 g of tetra-n-butylammonium bromide were added, and stirred at 120° C. for 4 hours. Furthermore, 20 g of tetrahydrophthalic anhydride was added, and stirred at 120° C. for 4 hours, at 100° C. for 3 hours, at 80° C. for 4 hours, at 60° C. for 6 hours, and at 40° C. for 11 hours. hour...

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Abstract

An oxime ester compound represented by the following general formula (1). In the formula, R1~R4 represents OR11, COOR11, etc., R11 represents a hydrogen atom, an alkyl group of C1~20, an aryl group of C6~30, an aralkyl group of C7~30 or a heterocyclic group of C2~20, these groups The hydrogen atom can also be replaced by -CR21=CR22R23, -CO-CR21=CR22R23, -O-CO-CR21=CR22R23, etc. (R21~R23 is the same as R11); X represents a sulfur atom, NR33 (R33 is a hydrogen atom, C1 ~20 alkyl, etc.); a represents an integer of 0 to 4; b represents an integer of 1 to 5, and at least one of R4 has -CR21=CR22R23, -CO-CR21=CR22R23, -O-CO-CR21 =Groups such as CR22R23.

Description

technical field [0001] The present invention relates to a novel oxime ester compound useful as a photopolymerization initiator used in a photosensitive composition, a photopolymerization initiator containing the compound, and a polymerizable compound having an ethylenically unsaturated bond containing the photopolymerization initiator The photosensitive composition formed and the cured product of the photosensitive composition. Background technique [0002] The photosensitive composition is obtained by adding a photopolymerization initiator to a polymerizable compound having an ethylenically unsaturated bond. Since it can be polymerized and cured by irradiating energy rays (light), it can be used for photocurable inks, Photosensitive printing plates, various photoresists, etc. [0003] Patent Documents 1 to 3 propose oxime ester compounds as photopolymerization initiators used in the photosensitive composition. [0004] However, among the oxime ester compounds described in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/47C07C323/62G02B5/20G03F7/031
CPCC07C251/66C07C323/47C07C323/62C07C323/65C07C327/28C07C391/02C07D303/23C07D307/42C07F9/5022C07C2601/14G03F7/0007G03F7/027G03F7/031G03F7/032G03F7/0388G02B5/20
Inventor 村田圣大石武雄君岛孝一
Owner ADEKA CORP
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