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Styrene derivative, styrene polymer, photosensitive resin composition, and method for forming pattern

A technology of styrene polymer and resin composition, applied in the field of new styrene derivatives, can solve problems such as safety and environmental problems, and achieve the effect of increasing solubility difference and high resolution

Inactive Publication Date: 2009-02-18
NEC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the developing step in the patterning process of photosensitive polyimide resin requires organic solvents (for example, N-methyl-2-pyrrolidone and ethanol), which can cause safety and environmental problems

Method used

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  • Styrene derivative, styrene polymer, photosensitive resin composition, and method for forming pattern
  • Styrene derivative, styrene polymer, photosensitive resin composition, and method for forming pattern
  • Styrene derivative, styrene polymer, photosensitive resin composition, and method for forming pattern

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] Synthesize a styrene derivative having the following structure, that is, a styrene derivative represented by general formula I, wherein, R 1 —R 9 is a hydrogen atom, X is -CONH-, and A is a hydrogen atom.

[0169]

[0170] 50 g of 4-vinylbenzoic acid and 62.1 g of pentafluorophenol were dissolved in a mixed solvent of 500 mL of ethyl acetate and 150 mL of tetrahydrofuran, and the solution was cooled with ice. 69.65 g of dicyclohexylcarbodiimide was added to the above solution, and the mixture was stirred under ice-cooling for 1 hour and then at room temperature for 1 hour. The precipitated dicyclohexylurea was filtered off, and the filtrate was concentrated under reduced pressure. 150 mL of heptane was added to the residue, and the precipitated dicyclohexylurea was filtered off. Then, the filtrate was concentrated under reduced pressure to obtain 99 g of pentafluorophenyl 4-vinylbenzoate.

[0171] Then, 10 g of pentafluorophenyl 4-vinylbenzoate and 4.17 g of orth...

Embodiment 2

[0174] Synthesize a styrene derivative having the following structure, that is, a styrene derivative represented by general formula I, wherein, R 1 —R 9 is a hydrogen atom, X is -CH=N-, and A is a hydrogen atom.

[0175]

[0176] 5 g of 4-vinylbenzaldehyde and 4.54 g of o-aminophenol were dissolved in 100 mL of toluene, and the solution was stirred at 80-85° C. for 4 hours. After cooling the solution, the solution was concentrated to half under reduced pressure, and the precipitated ortho-aminophenol was filtered off. The residue was recrystallized from hexane / toluene (4 / 1) to obtain 5.42 g of the desired product (yield: 64%).

[0177] of the resulting compound 1 H-NMR (THF-d 8 ) results are as follows: δ 5.38 (1H, d), 5.87 (1H, d), 6.77 (1H, dd), 6.91 (1H, t), 7.02 (1H, d), 7.18—7.32 (3H, m), 7.52 (2H,d), 7.88(1H,d), 8.68(1H,s).

Embodiment 3

[0179] Synthesize a styrene derivative having the following structure, that is, a styrene derivative represented by general formula I, wherein, R 1 —R 9 is a hydrogen atom, X is -CONH-, and A is ethoxymethyl.

[0180]

[0181] 10 g of the styrene derivative obtained in the examples and 8.1 g of N-ethyldiisopropylamine were dissolved in 90 mL of N-methyl-2-pyrrolidone. 4.346 g of chloromethyl ethyl ether was added to the solution, and the mixture was reacted at room temperature for 20 hours. 200 mL of diethyl ether was added to the reaction solution, and the mixture was washed successively with 0.2N hydrochloric acid, 3% aqueous sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from hexane to obtain 8.76 g of the desired styrene derivative (yield: 70%).

[0182] of the resulting compound 1 H-NMR (THF-d 8 ) results are as follows: δ 1.19 (3H, t), 3.74 (2H, q), 5...

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Abstract

Disclosed is a photosensitive resin composition used for interlayer insulating films or surface protection films which has excellent resolution and can be developed with an aqueous alkaline solution. The photosensitive resin composition is prepared using a polymer at least having a constitutional repeating unit represented by the following general formula (II). (In the formula, R<1> represents a hydrogen atom or a methyl group; R<2>-R<9> independently represent a hydrogen atom, a halogen atom or an alkyl group having 1-4 carbon atoms; X represents -CH=N-, -CONH-, -(CH2)n-CH=N-, or -(CH2)n-CONH- and the N atom in X is bonded to a carbon atom in the benzene ring having an AO- group at the o-position; A represents a hydrogen atom or an acid decomposable group; and n represents a positive integer of 1-3.

Description

technical field [0001] The invention relates to a novel styrene derivative, a styrene polymer, a photosensitive resin composition and a patterning method. Specifically, the present invention relates to a styrene derivative, a styrene polymer, a photosensitive resin composition, and a patterning method, which can be applied to interlayer insulating films, surface protection films, and the like in semiconductor devices. Background technique [0002] In semiconductor devices, polyimide resins having excellent film properties (for example, heat resistance, mechanical properties, and electrical properties) are generally used for interlayer insulating films or surface protective films. However, when a non-photosensitive polyimide resin is used as an interlayer insulating film, etc., the patterning process requires the use of a positive photoresist, which causes additional processes (such as etching and removal of etchant), resulting in a more complex manufacturing process. Compli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F12/32C07C233/75C07C251/24G03F7/022G03F7/033H01L21/027
Inventor 前田胜美中野嘉一郎
Owner NEC CORP
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