Oxime ester photoinitiator, preparation method, light-sensitive resin composition and application

A technology of photoinitiators and oxime esters, applied in the field of photocuring, can solve the problem of easy migration of photoinitiators

Active Publication Date: 2019-07-30
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 oxime ester photoinitiator, preparation method, photosensitive resin composition and application, to solve the problem that existing photoinitiator is easy to migrate

Method used

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  • Oxime ester photoinitiator, preparation method, light-sensitive resin composition and application
  • Oxime ester photoinitiator, preparation method, light-sensitive resin composition and application
  • Oxime ester photoinitiator, preparation method, light-sensitive resin composition and application

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preparation example Construction

[0063] In order to better achieve the above-mentioned purpose, another aspect of the present application also provides a preparation method of an oxime ester photoinitiator, the preparation method comprising:

[0064] S1, in the presence of the first catalyst, the raw material a and raw material b are subjected to Suzuki-Miyaura Cross Coupling (Suzuki-Miyaura Cross Coupling) to obtain intermediate a, the synthesis route is:

[0065]

[0066] R 1 Represents electron withdrawing group, R 4 Represents a monovalent organic group or hydrogen atom, R 6 One selected from an arylene group, a heteroarylene group, and a chain aliphatic hydrocarbon group containing at least one carbon-carbon double bond and / or at least one carbon-carbon triple bond, or the main chain end of the aforementioned aliphatic hydrocarbon group The group carbon atoms are respectively connected to the arylene group and / or heteroarylene group to form a group, or a group formed by connecting an arylene group and a hetero...

Embodiment 1

[0123] (1) Synthesis of Intermediate 1a

[0124] Into a 500mL four-necked flask was added 70.0g raw material 1a, 150mL tetrahydrofuran, 33.4g raw material 1b, 55.3g potassium carbonate, 3.2g (Pd(dppf)Cl 2 ·CH 2 Cl 2 ) And 15 mL of deionized water, heated to reflux at 70°C, and the liquid phase is tracked until the amount of raw material 1a no longer changes. Then the reaction system was cooled to room temperature, filtered to remove insoluble components, and then the filtrate was concentrated and dried, washed with water and recrystallized with ethyl acetate. Finally, the recrystallized product was dried in an oven at 80°C for 2 hours to obtain 59.6g of intermediate 1a. The rate is 76% by weight, and the purity is 98% by weight. The synthetic route is:

[0125]

[0126] Intermediate 1a was confirmed by proton nuclear magnetic resonance spectroscopy and mass spectrometry:

[0127] 1 H-NMR(CDCl 3 , 500MHz): 7.3006-7.3647 (3H, m), 7.4987-7.6235 (4H, m), 7.73976-7.7725 (4H, m), 7.9892-...

Embodiment 2

[0145] (1) Synthesis of intermediate 2a.

[0146] Add 73.9g of raw material 2a, 150mL of tetrahydrofuran, 29.4g of raw material 2b, 55.3g of potassium carbonate, 3.2g (Pd(dppf)Cl 2 ·CH 2 Cl 2 ) And 15mL of deionized water, heated to reflux at 70°C, the liquid phase is tracked until the amount of raw material 2a no longer changes, then the reaction solution is cooled to room temperature, filtered to remove insoluble components, then the filtrate is concentrated and dried, washed with water and recrystallized with acetone After drying in an oven at 80°C for 2 hours, 57.9 g of intermediate 2a was obtained, with a yield of 74 wt% and a purity of 98 wt%.

[0147] The synthetic route is:

[0148]

[0149] Intermediate 2a was confirmed by proton nuclear magnetic resonance and mass spectrometry:

[0150] 1 H-NMR(CDCl 3 , 500MHz): 1.4016 ~ 1.4448 (10H, m), 1.9688 ~ 1.9775 (1H, m), 2.4989 ~ 2.5206 (2H, dm), 3.8774 (2H, s), 7.5704 ~ 8.1935 (10H, m).

[0151] MS(m / z): 392(M+1) + .

[0152] (2) Synt...

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Abstract

The invention provides an oxime ester photoinitiator, a preparation method, a light-sensitive resin composition and application. The oxime ester photoinitiator contains polymerizable groups and is ofa structure shown in the general formula (I). Since the oxime ester photoinitiator contains the polymerizable groups, in the application process, the oxime ester photoinitiator can form a high molecule condensate with large molecular weight through a polymerization reaction, and the photo-initiation mobility can be effectively lowered. The oxime ester photoinitiator further contains electron-withdrawing groups, so that the electropositivity of the polymerizable groups is improved, which helps to further improve the initiation efficiency of the photoinitiator. In conclusion, the oxime ester photoinitiator of the structure has the advantages that the oxime ester photoinitiator is not easily migrated and is high in photo-initiation efficiency.

Description

Technical field [0001] The present invention relates to the field of light curing, in particular to an oxime ester photoinitiator, a preparation method, a photosensitive resin composition and application. Background technique [0002] Compared with traditional picture tube monitors, liquid crystal display devices have the advantages of low energy consumption, small size and no radiation, but still have the defects of too small visual angle, image smearing, poor brightness and contrast. In recent years, with the continuous improvement of people’s living standards, people have also put forward higher requirements for liquid crystal display devices. The requirements for large size, high brightness, high contrast, and wide viewing angle have been mentioned. The materials used in this set higher requirements. [0003] Color, black photoresist and optical spacers are important components of liquid crystal flat panel displays, and are essential materials for high-generation flat panel di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07C251/66C07D209/86C07D303/36C07D305/06C07D409/14C07D333/22C07C249/12G03F7/004G03F7/027
CPCC07C251/66C07D209/86C07D303/36C07D305/06C07D333/22C07D409/14C08F2/48G03F7/004G03F7/027
Inventor 钱晓春胡春青于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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