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(methyl)acrylamide derivative, polymer, chemically amplified photosensitive resin composition, and method for forming pattern

一种丙烯酰胺、聚合物的技术，应用在丙烯酰胺衍生物,聚合物领域，能够解决正型光敏树脂组合物不是令人满意等问题，达到高分辨率、优异膜性质的效果

Inactive Publication Date: 2008-05-07
NEC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of the positive-type photosensitive resin compositions described in the above references is satisfactory in view of the resolution requirement

Method used

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  • (methyl)acrylamide derivative, polymer, chemically amplified photosensitive resin composition, and method for forming pattern
  • (methyl)acrylamide derivative, polymer, chemically amplified photosensitive resin composition, and method for forming pattern
  • (methyl)acrylamide derivative, polymer, chemically amplified photosensitive resin composition, and method for forming pattern

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0227] N-(2-ethoxymethoxyphenyl)acrylamide (acrylamide derivative: A-1 in Table 1; in general formula (1), R 1 is a hydrogen atom, R 2 is ethoxymethyl, R 3 to R 6 is a hydrogen atom) synthetic method

[0228]

[0229] 20 g of N-(2-hydroxyphenyl)acrylamide and 23.76 g of N,N-diisopropylethylamine were dissolved in 150 mL of NMP, and 12.75 g of chloromethyl ethyl ether were added to the solution. The solution was stirred at room temperature. After 3 days, the solution was poured into 1000 mL of water, and the organic layer was extracted with 400 mL of ether. The organic layer was washed successively with 0.2N hydrochloric acid, brine, 3% aqueous sodium hydroxide solution and brine. The organic layer was dried over magnesium sulfate, and then diethyl ether was evaporated under reduced pressure. The residue was recrystallized from hexane / ethyl acetate (100 / 4) to obtain 13.23 g of the desired product (white solid, yield: 49%).

[0230] 1 H-NMR (THF-d 8 , δ): 1.19 (3H, t...

Embodiment 2

[0232] N-(2-(1-ethoxyethoxy) phenyl) acrylamide (acrylamide derivative: A-2 in Table 1; in general formula (1), R 1 is a hydrogen atom, R 2 is ethoxyethyl, R 3 to R 6 is a hydrogen atom) synthetic method

[0233]

[0234] 10 g of N-(2-hydroxyphenyl)acrylamide and 11.05 g of ethyl vinyl ether were dissolved in 50 mL of NMP, and 0.308 g of pyridinium p-toluenesulfonate was added to the solution. The solution was stirred at room temperature. After 6 days, the reaction mixture was poured into 300 mL of water, and the organic layer was extracted with 300 mL of diethyl ether. The organic layer was washed successively with 3% aqueous sodium hydroxide solution and brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 9.6 g of the desired product (yield: 67%).

[0235] 1 H-NMR (THF-d 8 , δ): 1.20 (3H, t), 1.53 (3H, d), 3.5-3.8 (2H, m), 5.38 (1H, q), 5.75 (1H, d), 6.29 (1H, dd), 6.41 ( 1H, d), 7.0-7.08...

Embodiment 3

[0237] N-(2-(1-ethoxyethoxy) phenyl) methacrylamide (methacrylamide derivative: A-6 in Table 1; in general formula (1), R 1 is methyl, R 2 is ethoxyethyl, R 3 to R 6 is a hydrogen atom) synthetic method

[0238]

[0239] 10 g of N-(2-hydroxyphenyl)methacrylamide and 10.17 g of ethyl vinyl ether were dissolved in 50 mL of NMP, and 0.284 g of pyridinium p-toluenesulfonate was added to the solution. The solution was stirred at room temperature. After 6 days, the reaction mixture was poured into 300 mL of water, and the organic layer was extracted with 300 mL of diethyl ether. The organic layer was washed successively with 3% aqueous sodium hydroxide solution and brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 10.2 g of the desired product (yield: 72%).

[0240] 1 H-NMR (THF-d 8 , δ): 1.18(3H, t), 1.54(3H, d), 2.08(3H, s), 3.49-3.72(2H, m), 5.36(1H, q), 5.47(1H, s), 5.87( 1H, s), 7.0-7.07 (...

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Abstract

The present invention relates to a novel (meth)acrylamide compound represented by the general formula (1), a (co)polymer of the (meth)acrylamide compound, and a chemically amplified photosensitive resin composition composed of the polymer and a photoacid generator. In the formula, R1 represents a hydrogen atom or a methyl group; R2 represents an acid-decomposable group; and R3 to R6 independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms.

Description

technical field [0001] The invention relates to a novel (meth)acrylamide derivative, a polymer, a chemically amplified photosensitive resin composition and a patterning method thereof. Specifically, the present invention relates to a (meth)acrylamide derivative, a polymer, a chemically amplified photosensitive resin composition and a patterning method thereof applicable to interlayer insulating films and surface protection films of semiconductor devices. Background technique [0002] Polyimide resins having excellent film properties such as heat resistance, mechanical properties and electrical properties have been conventionally applied to interlayer insulating films or surface protective films of semiconductor devices. However, when a non-photosensitive polyimide resin is used as an interlayer insulating film or the like, the patterning method uses a positive-type photoresist, which results in the need for an etching step and a photoresist removal step, resulting in a more ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/58C07C233/27C07C233/75C07D309/10C07F7/18G03F7/004G03F7/039G03F7/075G03F7/40
CPCC07C233/27Y10S430/107G03F7/0392C07F7/0854Y10S430/106Y10S430/115Y10S430/111C07D307/32C08F220/58C07D307/93C07D309/12C07F7/0838
Inventor 前田胜美中野嘉一郎
Owner NEC CORP
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