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Preparation method of light trigger of carbazole oxime ester

A technology of carbazole oxime and photoinitiation, which is applied in the field of photoinitiator preparation, can solve problems such as pattern shape defects, and achieve excellent linear pattern, high yield, and easy-to-obtain raw materials

Inactive Publication Date: 2017-12-15
南京法恩化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Photoactive compounds are materials that decompose to produce chemically active substances or molecules by absorbing light, and are widely used as initiators for various compounds such as photocurable inks, photosensitive printing plates, and photoresists; photoinitiators can be divided into There are many types, such as acetophenone compounds, benzophenone compounds, triazine compounds, non-imidazole compounds, acyl phosphorus oxide compounds, and oxime ester compounds. Among them, oxime ester compounds have the following advantages: such as absorbing ultraviolet rays almost No color, high free radical generation rate, excellent compatibility and stability with photoresist composition materials; since the oxime ester compound is irradiated to the photopolymerizable composition by light from 365nm to 435nm, it can make unsaturated Polymerization and curing of key polymerizable compounds, used for LCD rear light filter grating production and other electronic material processing, common known oxime ester compounds are oxime ester compounds with dialkylaminobenzene in US Patent 4255513, US Patent 4202697 acrylamide-substituted oxime ester compounds and benzophenone oxime ester compounds in US Patent No. 4,590,145; however, when using known oxime ester compounds as photoinitiators, when exposed to attach to the mask due to light The resulting degradation leads to pattern shape defects in the printing process; therefore, developing a new structure oxime ester compound that can overcome the above defects has become a technical problem to be solved urgently by those skilled in the art

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  • Preparation method of light trigger of carbazole oxime ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of preparation method of photoinitiator carbazole oxime ester, such as figure 1 As shown, it specifically includes the following steps:

[0031] (1) Add carbazole to the solvent, under the protection of nitrogen, add n-butylammonium bromide and alkyl reagent, add dropwise alkali solution, react for 5 hours, add ethyl acetate and water after the reaction, and react The liquid was separated, and the organic layer was dried and concentrated to obtain intermediate 1;

[0032] The solvent in step (1) is one of methanol, ethanol, DMF, 1,4-dioxane, DMSO or acetonitrile; the alkali solution in step (1) is potassium hydroxide, potassium carbonate, sodium carbonate, sodium methoxide , sodium ethoxide, sodium hydride, triethylamine or pyridine solution; the alkyl reagent in step (1) is 1,3-dibromopropane;

[0033] (2) Add the intermediate 1 obtained in step (1) to diethyl phosphite, raise the temperature to 120-180°C and react for 18 hours, TLC tracking, after the reactio...

Embodiment 2

[0044] This example provides a 3-(3-((acetoxyimine)(2-methoxyphenyl)methyl)-6-nitro-9H-carbazol-9-yl)propyl phosphate di The preparation method of ethyl ester specifically comprises the following steps:

[0045] (1) Add 33 grams of carbazole to 100ml of tetrahydrofuran, under nitrogen protection, add 1.3g of n-butylammonium bromide, 42g of 1-bromo-3-chloropropane, add dropwise 300ml of 50% sodium hydroxide solution, and then react at 40°C After 5 hours, 200ml of ethyl acetate and 300ml of water were added, the liquid was separated, the organic layer was dried and concentrated to obtain 47 grams of intermediate 1, which was directly used in the next step without purification, yield: 98%;

[0046] (2) Add 12 grams of intermediate 1 to 84 grams of diethyl phosphite, raise the temperature to 150 ° C for 18 hours, TLC tracking, after the reaction is completed, cool down to room temperature, concentrate to dryness under reduced pressure to obtain 10 g of intermediate 2, directly Fo...

Embodiment 3

[0052] This example provides a 3-(3-((acetoxyimine)(2-methylphenyl)methyl)-6-nitro-9H-carbazol-9-yl)propyl phosphate diethyl The preparation method of ester specifically comprises the following steps:

[0053] (1) Add 33 grams of carbazole to 100ml of tetrahydrofuran, under nitrogen protection, add 1.3g of n-butylammonium bromide, 42g of 1-bromo-3-chloropropane, add dropwise 300ml of 50% sodium hydroxide solution, and then react at 40°C After 5 hours, 200ml of ethyl acetate and 300ml of water were added, the liquid was separated, the organic layer was dried and concentrated to obtain 47 grams of intermediate 1, which was directly used in the next step without purification, yield: 98%;

[0054] (2) Add 12 grams of intermediate 1 to 84 grams of diethyl phosphite, raise the temperature to 150 ° C for 18 hours, TLC tracking, after the reaction is completed, cool down to room temperature, concentrate to dryness under reduced pressure to obtain 10 g of intermediate 2, directly For ...

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Abstract

The invention discloses a preparation method of a light trigger of carbazole oxime ester, and particularly relates to a method for preparing the carbazole oxime ester by using carbazole, nitric acid, 1-bromo-3-chloropropane, diethyl phosphite, o-Methoxybenzoyl chloride, hydroxylamine hydrochloride and acetic anhydride as raw materials through six steps of reactions including N-alkylation reaction, substitution reaction, nitratlon reaction, Friedel-Crafts reaction, and oxime and acetylation reaction. The preparation method of the carbazole oxime ester provided by the invention belongs to a preparation method with the advantages that the yield is high; the cost is low; the environment is protected; the operation is easy; the preparation method is suitable for industrialization.

Description

technical field [0001] The invention relates to a preparation method of a photoinitiator, in particular to a preparation method of a photoinitiator carbazole oxime ester. Background technique [0002] Photoactive compounds are materials that decompose to produce chemically active substances or molecules by absorbing light, and are widely used as initiators for various compounds such as photocurable inks, photosensitive printing plates, and photoresists; photoinitiators can be divided into There are many types, such as acetophenone compounds, benzophenone compounds, triazine compounds, non-imidazole compounds, acyl phosphorus oxide compounds, and oxime ester compounds. Among them, oxime ester compounds have the following advantages: such as absorbing ultraviolet rays almost No color, high free radical generation rate, excellent compatibility and stability with photoresist composition materials; since the oxime ester compound is irradiated to the photopolymerizable composition...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572C08F2/48
CPCC07F9/5728C08F2/48
Inventor 王坤鹏陈晨尚家磊
Owner 南京法恩化学有限公司