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Novel fluorenyl β-oxime ester compound, photopolymerization initiator and photoresist composition containing same

A photoresist and compound technology, applied in the fields of novel fluorenyl β-oxime ester compounds, photopolymerization initiators containing the same, and photoresist compositions, can solve the problem of reduced yield of by-products and low sensitivity , production reduction and other problems, to achieve the effect of highlighting the residual film thickness, excellent sensitivity, and minimizing defects

Active Publication Date: 2019-09-24
SAMSANG CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, when a conventional photopolymerization initiator is used to form a pattern, in the exposure process of pattern formation, the amount of the photopolymerization initiator or the exposure dose needs to be increased due to the low sensitivity, and it has the disadvantage of contaminating the mask during the exposure process. film and the by-products generated after the decomposition of the photopolymerization initiator during crosslinking at high temperature reduce the yield, and since the exposure process time increases as the exposure dose increases, there is a problem that the yield decreases, and efforts are being made to solve these problems

Method used

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  • Novel fluorenyl β-oxime ester compound, photopolymerization initiator and photoresist composition containing same
  • Novel fluorenyl β-oxime ester compound, photopolymerization initiator and photoresist composition containing same
  • Novel fluorenyl β-oxime ester compound, photopolymerization initiator and photoresist composition containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] [Example 1] Preparation of 1-(9,9-diethyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-acetate

[0092] Reaction 1. Synthesis of 9,9-diethyl-9H-fluorene (2)

[0093]

[0094] Under a nitrogen atmosphere, dissolve 200.0g (1.20mol) of fluorene (1), 268.8g (4.80mol) of potassium hydroxide and 19.9g (0.12mol) of potassium iodide in 1L of anhydrous dimethyl sulfoxide, and dissolve the reactants After holding at 15°C, 283.3 g (2.60 mol) of bromoethane were added slowly over 2 hours and the reaction was stirred at 15°C for 1 hour. Next, 2 L of distilled water was added to the reactant, and after stirring for 30 minutes, the product was extracted with 2 L of dichloromethane, and after the extracted organic layer was washed twice with 2 L of distilled water, the recovered organic layer was dried with anhydrous magnesium sulfate and dried under reduced pressure. The solvent was distilled off under reduced pressure, and the obtained product was distilled by fractional distillat...

Embodiment 2

[0112] [Example 2] Preparation of 1-(9,9-diethyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-propionate (6)

[0113]

[0114] Dissolve 89.0 g (0.29 mol) of 1-(9,9-diethyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime (4) in 1 L of N-methanol under a nitrogen atmosphere In base-2-pyrrolidone (NMP), after the reactant was kept at -5°C, 35.4g (0.35mol) trimethylamine was added, and the reaction solution was stirred for 30 minutes. Considering to avoid increasing the temperature of the reactant, slowly add the dissolved A solution of 32.4 g (0.35 mol) of propionyl chloride in 75 ml of N-methyl-2-pyrrolidone for 30 minutes and stirred for 30 minutes. Next, 1 L of distilled water was slowly added to the reactant and stirred for 30 minutes to separate the organic layer, and the recovered organic layer was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Recrystallized from 1 L of ethanol and dried the resulting solid product to give 95....

Embodiment 3

[0117] [Example 3] Preparation of 1-(9,9-diethyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-butyrate (7)

[0118]

[0119] Dissolve 29.8g (0.097mol) of 1-(9,9-diethyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime (4) in 300ml of N- In methyl-2-pyrrolidone (NMP), keep the reactant at -5°C, then add 11.7g (0.116mol) triethylamine, stir the reaction solution for 30 minutes, in order to avoid increasing the temperature of the reactant, carefully A solution of 12.4 g (0.116 mol) of butyryl chloride dissolved in 15 ml of N-methyl-2-pyrrolidone was added slowly over 30 minutes and stirred for 30 minutes. Next, 300 ml of distilled water was slowly added to the reactant and stirred for 30 minutes to separate the organic layer, and the recovered organic layer was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure, and the resulting product was purified by silica gel column chromatography. Product (elution solvent; ethyl acetate:n-hexane=1:4)...

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Abstract

The present invention relates to a novel ²-oximester fluorene derivative compound, a photopolymerization initiator comprising the same, and a photoresist composition.

Description

technical field [0001] The present disclosure relates to a novel fluorenyl β-oxime ester compound and a photopolymerization initiator and photoresist composition containing the same, and more particularly, to a novel fluorenyl β-oxime ester compound having remarkably excellent sensitivity even in a small amount , a photopolymerization initiator comprising the same, and a photoresist composition having outstanding properties such as residual film thickness, pattern stability, chemical resistance, and elasticity. [0002] This application claims priority to Korean Patent Application No. 10-2014-0006344 filed in Korea on Jan. 17, 2014, the disclosure of which is incorporated herein by reference. Background technique [0003] As typical examples of photopolymerization initiators used in photoresist compositions, various types such as acetophenone derivatives, benzophenone derivatives, triazine derivatives, biimidazole derivatives, acyl oxide derivatives, etc. Phosphine derivati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/66G03F7/004
CPCC07C251/66C07C2603/18G03F7/0045G03F7/031G02B5/003G02B5/223G03F7/0007G03F7/033
Inventor 吴泉林李敏善李元重赵镛一辛承林申钟一李相悟全根
Owner SAMSANG CORP