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Fluorene oxime ester compound, preparation method thereof and photosensitive resin composition

A technology of ester compound and fluorene oxime, applied in the fields of oxime preparation, optics, organic chemistry, etc., can solve the problems of insufficient sensitivity and poor performance of photocurable compositions, achieve good pattern effect, high sensitivity, and solve the problem of sensitivity insufficient effect

Pending Publication Date: 2021-05-28
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 fluorene oxime ester compound and its preparation method, photosensitive resin composition, in order to solve the problem in the prior art that the insufficient sensitivity of the photoinitiator easily leads to the poor performance of the photocurable composition

Method used

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  • Fluorene oxime ester compound, preparation method thereof and photosensitive resin composition
  • Fluorene oxime ester compound, preparation method thereof and photosensitive resin composition
  • Fluorene oxime ester compound, preparation method thereof and photosensitive resin composition

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preparation example Construction

[0032] According to another aspect of the present invention, a kind of preparation method of above-mentioned fluorene oxime ester compound is provided, it comprises the following steps:

[0033] Step S1, performing a Friedel-Crafts reaction on compound a and an acid halide compound under the action of a catalyst to obtain intermediate a; wherein compound a is Intermediate a is R a1 , R a2 , R a3 , R b1 , R b2 , R b3 , R b4 , Ar have the same definition as above; R 1 ' is the residue formed after removing the acid halide group from the acid halide compound;

[0034] In step S2, intermediate a is subjected to an oximation reaction to obtain intermediate b, and intermediate b is where R a1 , R a2 , R a3 , R b1 , R b2 , R b3 , R b4 , Ar, n, R 1 has the same definition as above;

[0035] In step S3, the intermediate b is subjected to an esterification reaction with an acylating agent or an acid anhydride to obtain a fluorene oxime ester compound.

[0036] The ...

Embodiment 1

[0058] Preparation of Compound A-1

[0059]

[0060] Step (1) Preparation of Intermediate A-1-1

[0061]

[0062] Under the protection of nitrogen, add raw material A-1-0 (103.9g, 0.30mol), aluminum chloride (252.0g, 1.89mol) and 800mL dichloromethane into a 2L reaction flask, stir in an ice bath, and reduce the temperature of the reaction solution to 5-10°C; butyryl chloride (95.9g, 0.90mol) was dissolved in 200mL of dichloromethane, slowly added dropwise to the above reaction solution, the temperature was controlled not to exceed 10°C, after the drop was complete, the reaction was continued for 3h. The reaction solution was slowly added to 1 kg of ice water, fully stirred for 30 minutes, allowed to stand for stratification, and the lower organic phase was separated. The organic phase was washed with water until neutral, and concentrated to obtain a residue. Added 320 g of methanol, stirred to precipitate a solid, and continued to cool down to 5 Continue to stir and cr...

Embodiment 2

[0073] The preparation of embodiment 2 compound A-2

[0074]

[0075] Step (1) Preparation of Intermediate A-2-1

[0076]

[0077] Under nitrogen protection, add raw material A-2-0 (103.9g, 0.30mol), aluminum chloride (336.0g, 2.52mol) and 1000mL dichloromethane into the 2L reaction flask, stir in an ice bath, and reduce the temperature of the reaction solution to 5-10°C; butyryl chloride (127.9g, 1.20mol) was dissolved in 200mL of dichloromethane, slowly added dropwise to the above reaction solution, the temperature was controlled not to exceed 10°C, after the drop was complete, the reaction was continued for 3h. Slowly add the reaction solution into 1 kg of ice water, stir thoroughly for 30 min, let stand to separate layers, separate the lower organic phase, wash the organic phase with water until neutral, concentrate to obtain a residue, add 400 mL of methanol, stir to precipitate a solid, and continue to cool down to 5 Continue to stir and crystallize at -10°C for 1...

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Abstract

The invention provides a fluorene oxime ester compound, a preparation method thereof and a photosensitive resin composition. The structure of the fluorene oxime ester compound is as follows: the fluorene oxime ester compound takes dibenzyl fluorene as a parent structure, and a plurality of oxime ester functional groups are introduced on the dibenzyl fluorene, so that the fluorene oxime ester compound has higher sensitivity. When the fluorene oxime ester compound is applied to the photosensitive composition as a photoinitiator, the problem of insufficient sensitivity of the current photosensitive composition can be effectively solved, and the photosensitive composition has a good pattern effect.

Description

technical field [0001] The invention relates to the technical field of photocuring, in particular to a fluorene oxime ester compound, a preparation method thereof, and a photosensitive resin composition. Background technique [0002] Compounds with oxime ester structure are widely used as photoinitiators in the field of photocuring. Designing and synthesizing new oxime ester photoinitiators with better application performance has always been a research hotspot in the field of photocuring. Due to the high sensitivity of oxime ester photoinitiators, it can be used for color filters, black matrices, etc. used in color televisions, liquid crystal displays, solid-state imaging elements, cameras, etc. in the polymer composition. Patent documents such as publication numbers CN99108598A, CN101508744A, CN10565472A, and CN103293855A disclose different carbazole oxime esters and ketoxime ester photoinitiators. These disclosed photoinitiators have good photosensitivity and storage stab...

Claims

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Application Information

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IPC IPC(8): C07C251/66C07C251/68C07C249/12C07D307/68C07D307/52C07D333/38C07D333/22G03F7/027
CPCC07C251/66C07C251/68C07D307/68C07D307/52C07D333/38C07D333/22G03F7/027C07C2603/18C07C2601/14C07C2601/08
Inventor 钱晓春汪雷于培培胡春青陈亮
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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