Fluoro-containing fluorene oxime ester photoinitiator, photocurable composition containing the same, and application thereof

A technology of photoinitiator and ester, which is applied in the field of organic synthesis, can solve the problems of poor surface dryness and easy migration, and achieve the effects of high initiation efficiency, good surface dryness, and good surface curing effect

Active Publication Date: 2019-07-02
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main purpose of the present invention is to provide a fluorine-containing fluorene oxime ester photoinitiator, a photocurable composition containing it and its application, so as to solve the problems of poor surface dryness and easy migration of existing oxime ester photoinitiators

Method used

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  • Fluoro-containing fluorene oxime ester photoinitiator, photocurable composition containing the same, and application thereof
  • Fluoro-containing fluorene oxime ester photoinitiator, photocurable composition containing the same, and application thereof
  • Fluoro-containing fluorene oxime ester photoinitiator, photocurable composition containing the same, and application thereof

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preparation example Construction

[0039] According to another aspect of the present invention, the present invention also provides the preparation method of the fluorine-containing fluorene oxime ester photoinitiator shown in above-mentioned general formula (I), comprises the following steps:

[0040] (1) Preparation of intermediate a

[0041] Under the catalysis of aluminum trichloride or zinc chloride, raw material a and raw material b undergo Friedel-Crafts acylation reaction in an organic solvent to obtain intermediate a; the synthetic route is as follows:

[0042]

[0043] A is empty or methylene.

[0044] (2) Preparation of intermediate b

[0045] When intermediate a is subjected to oximation reaction under the action of hydroxylamine hydrochloride and sodium acetate, A is empty, and intermediate b is generated. The synthetic route is as follows:

[0046]

[0047] When intermediate a is oximated with nitrite or nitrite in the presence of concentrated hydrochloric acid at normal temperature, A is ...

Embodiment 1

[0064] (1) Synthesis of Intermediate 1a

[0065] Add 66.1 g of intermediate 1a, 27.0 g of aluminum trichloride, and 100 mL of dichloromethane into a 500 mL four-necked flask, and lower the temperature of the raw materials in the four-necked flask to 0° C. using an ice-water bath. Then, under stirring, a mixed solution of 57.0 g of raw material 1b and 50 mL of dichloromethane was added dropwise to the above raw material, while controlling the temperature of the reaction system below 10° C., and the dropwise addition was completed within 2 hours. After the dropwise addition, continue to stir for 2h, and follow the liquid phase to complete the reaction. Then the above reaction system is slowly poured into the dilute hydrochloric acid made of 400g ice water and 50mL concentrated hydrochloric acid (37%), stir while adding, then pour it into a separatory funnel, separate the lower dichloromethane layer, and use Continue to wash the aqueous layer with 50 mL of dichloromethane, and c...

Embodiment 2

[0080] (1) Synthesis of Intermediate 2a

[0081] Add 72.5 g of intermediate 2a, 27.0 g of aluminum trichloride, and 100 mL of dichloromethane into a 500 mL four-necked flask, and use an ice-water bath to lower the temperature of the raw materials in the four-necked flask to 0°C. Then, under stirring, a mixed solution of 54.5 g of raw material 2b and 50 mL of dichloromethane was added dropwise to the above raw material, while the temperature of the reaction system was controlled below 10° C., and the dropwise addition was completed within 2 hours. After the dropwise addition, continue to stir for 2h, and follow the liquid phase to complete the reaction. Then the above reaction system is slowly poured into the dilute hydrochloric acid made of 400g ice water and 50mL concentrated hydrochloric acid (37%), stir while adding, then pour it into a separatory funnel, separate the lower dichloromethane layer, and use Continue to wash the water layer with 50 mL of dichloromethane, combi...

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Abstract

The invention provides a fluoro-containing fluorene oxime ester photoinitiator, a photocurable composition containing the same, and an application thereof. The photoinitiator has a structure representby that general formula (I). In the fluoro-containing fluorene oxime ester photoinitiator provided in the present application, by introducing a polymerizable group at the 9-position of the fluorene structure, the formed photoinitiator can be polymerized with a substrate, and thus the photoinitiator has the advantage of being difficult to migrate. At that same time, the photoinitiator provide in the present application also has the advantage of high initiation efficiency due to the introduction of fluorine-containing groups. In addition, the special structure of the photoinitiator also has theadvantages of good surface drying performance, good surface curing effect and so on. On this basis, the photoinitiator has the advantages of not easy migration, high initiation efficiency, good surface drying performance and good surface curing effect, and has a broad application prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a fluorine-containing fluorene oxime ester photoinitiator, a photocurable composition containing the photoinitiator and its application. Background technique [0002] Compared with the traditional picture tube monitor, the liquid crystal display device has the advantages of low energy consumption, small size and no radiation, but still has the defects of too small viewing angle, image smearing, poor brightness and contrast. In recent years, with the continuous improvement of people's living standards, people have put forward higher requirements for liquid crystal display devices, such as large size, high brightness, high contrast, and wide viewing angles. The materials used in the process put forward higher requirements. [0003] Color and black photoresists and optical spacers are important components of liquid crystal flat panel displays, and are essential materials for high-g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48G03F7/027C07C251/66C07C255/64C07D303/16C07D305/06C07D333/22
CPCC07C251/66C07C255/64C07D303/16C07D305/06C07D333/22C08F2/48G03F7/027
Inventor 钱晓春胡春青于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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