Fluorene oxime ester compound as well as preparation method and application thereof

A technology of ester compounds and compounds, applied in the field of photoinitiators and photosensitive resin compositions, and new fluorene oxime ester compounds, can solve the problems of poor permeability of exposure sources, adhesion of photocurable compositions, alkali resistance and Problems such as decreased transparency, alkali resistance and decreased transparency

Active Publication Date: 2021-02-09
CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when using the known oxime ester compound as a photoinitiator, there are still defects, such as: the decomposition products caused by exposure are attached to the mask and cause pattern shape defects in the printing process; the exposure source has poor permeability, and the bottom of the photoresist The photoinitiator cannot be initiated. After the development process, in the thermal curing step, the photoinitiator decomposes and causes the adhesion, alkali resistance and transparency of the photocurable composition to decrease, thereby causing pattern defects
[0003] Therefore, it is necessary to develop an oxime ester compound with a new structure and improved properties to solve the problems of poor permeability of the exposure source resulting in a decrease in the adhesion, alkali resistance and transparency of the composition, as well as the decomposition of the photoinitiator caused by light irradiation. Problems such as volatilization and contamination of compositions or devices

Method used

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  • Fluorene oxime ester compound as well as preparation method and application thereof
  • Fluorene oxime ester compound as well as preparation method and application thereof
  • Fluorene oxime ester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149]Example 1 Preparation of Compound A-1

[0150]

[0151]Preparation of intermediate A-1-1

[0152]

[0153]Add 2-nitro-9H-fluorene (63.3g, 0.3mol), potassium tert-butoxide (77.3g, 0.7mol) and dimethyl sulfoxide (500mL) into a 2000mL round-bottom flask, and slowly add to it under a nitrogen atmosphere Bromobutane (95.6g, 0.7mol) was added dropwise, and after the addition was completed, the reaction was stirred at room temperature. After the reaction is complete, add 1500mL distilled water to quench, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, distill under reduced pressure to remove the organic solvent, use silica gel column chromatography to purify with ethyl acetate: petroleum ether=1:4, and dry , 70.3 g of intermediate A-1-1 was obtained, with a yield of 72.5%.

[0154]Preparation of intermediate A-1-2

[0155]

[0156]Add Intermediate A-1-1 (32.3g, 0.1mol) and carbon disulfide (1000mL) to a 2000mL round bottom flask, add 2-bromopropionyl bromide (21.6g, 0....

Embodiment 2

[0165]Example 2 Preparation of Compound A-17

[0166]

[0167]The intermediate A-1-3 was synthesized according to the same method as in Example 1 above.

[0168]

[0169]

[0170]Add Intermediate A-1-3 (40.6g, 0.1mol), dichloromethane (1000mL), and triethylamine (20.2g, 0.2mol) to a 2000mL round-bottomed flask. Under the protection of nitrogen, control the temperature at -5 Naphthoyl chloride (38.2g, 0.2mol) was added dropwise at ~0°C, and the reaction was incubated for 5h after the addition was completed. Subsequently, 500 mL of saturated sodium bicarbonate aqueous solution was added to the reaction solution, extracted with dichloromethane, the organic phase was washed with saturated sodium bicarbonate aqueous solution and saturated common salt solution in sequence, dried with anhydrous sodium sulfate, filtered, concentrated, and used on a silica gel column. After purification, 49.9 g of compound A-17 was obtained with a yield of 89.0%.

[0171]The structural characterization data of the product are...

Embodiment 3

[0173]Example 3 Preparation of other compounds

[0174]With reference to the methods of Examples 1 and 2, the corresponding raw materials were replaced to synthesize other compounds of formula A as shown in Table 1 below.

[0175]Table 1

[0176]

[0177]

[0178]

[0179]

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PUM

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Abstract

The invention discloses a novel fluorene oxime ester compound, a preparation method thereof, a photoinitiator containing the fluorene oxime ester compound, and a photosensitive resin composition containing the fluorene oxime ester compound. The fluorene oxime ester compound has a chemical structure as shown in A, B, C, D or E, can prevent decomposers caused by exposure from being attached to a mask when used as a photoinitiator, has a good pattern effect, and is excellent in adhesiveness, alkali resistance and transparency.

Description

Technical field[0001]The invention belongs to the technical field of photosensitive materials, and specifically relates to a novel fluorenoxime ester compound, a preparation method thereof, and a photoinitiator and photosensitive resin composition containing the fluorenoxime ester compound.Background technique[0002]The oxime ester photoinitiator is a new type of cracking free radical photoinitiator that has emerged in recent years. It has high sensitivity, good compatibility and stability with the photoresist composition material, and the polymerization rate of the photosensitive material , High conversion rate and transparency, less lithography residue and other advantages, has been widely used in photoresist. Existing technologies, such as CN101014569A, CN102112438A, CN102093282A, CN101735344A, CN101525393A, CN101528694A, CN102015633A, CN101048377A, CN101243057A, and CN103998422A, have introduced suitable substituents in oxime ester compounds to meet industrial needs for various p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/66C07C251/68C07D333/22C07C249/12C08F2/48G03F7/027
CPCC07C251/66C07C251/68C07D333/22C08F2/48G03F7/027C07C249/12G03F7/00
Inventor 钱晓春胡春青徐丽萍于培培
Owner CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS
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