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EP0523957A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Radiation-sensitive composition

Assignee: JSR Corp
•
Filing: 1992-07-14
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Granted: —
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Expires: 2012-07-14
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Abstract

Abstract A radiation-sensitive composition comprising a polymer having acid-decomposable silyl groups, a radiation-sensitive acid-forming agent and a weakly basic, nitrogen-containing compound. Said radiation-sensitive composition is suitable as a resist composition useful to superfine processing using radiations including far ultraviolet rays, X-rays and charged particle beams.

Inventors

  • 👤 Makoto Murata
  • 👤 Eiichi Kobayashi
  • 👤 Yoshiji Yumoto
  • 👤 Takao Miura

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-01 21:08
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0757; G03F7/0758

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 20 words
A radiation-sensitive composition comprising a polymer having acid-decomposable silyl groups, a radiation-sensitive acid-forming agent and a weakly basic, nitrogen-containing compound.
Claim 2
Dependent Claim 197 words
The radiation-sensitive composition according to Claim 1, wherein the polymer consists essentially of a recurring structure unit represented by formula (I) or a combination thereof with at least one recurring structure unit selected from those represented by formulas (II)(a), (II)(b) and (II)(c) and those corresponding to the structures formed by splitting the vinyl group of maleic anhydride, vinylpyridine, vinylpyrrolidone, vinylimidazole, vinylaniline, fumaronitrile, acrylamide and acrylonitrile: wherein R¹ , R² and R³, which may be the same or different, represent hydrogen atoms, alkyl groups having 1-4 carbon atoms, phenyl groups or benzyl groups; R⁴ and R⁵, which may be the same or different, represent hydrogen atoms, halogen atoms, hydroxyl groups or alkyl groups having 1-4 carbon atoms; R⁶ represents a hydrogen atom or a methyl group; R⁷, R⁸ and R⁹, which may be the same or different, represent hydrogen atoms, halogen atoms, hydroxyl groups, amino groups, alkyl groups having 1-4 carbon atoms or alkoxy groups having 1-4 carbon atoms; R¹⁰ represents a hydrogen atom or a methyl group; R¹¹ represents an alkyl group having 1-4 carbon atoms; R¹² represents a hydrogen atom or a methyl group; and R¹³ represents a hydrogen atom,.a phenyl group or a hydroxyphenyl group.
Claim 3
Dependent Claim 30 words
The radiation-sensitive composition according to Claim 2, wherein the polymer consists essentially of a recurring structure unit represented by formula (I) and a recurring structure unit represented by formula (II)(a).
Claim 4
Dependent Claim 55 words
The radiation-sensitive composition according to Claim 3, wherein the recurring structure unit represented by formula (II)(a) is that represented by formula (III): wherein R¹⁴ and R¹⁵, which may be the same or different, represent hydrogen atoms, halogen atoms or alkyl groups having 1-4 carbon atoms; and R¹⁶ represents a hydrogen atom or a methyl group.
Claim 5
Dependent Claim 513 words
The radiation-sensitive composition according to Claim 1, wherein the radiation-sensitive acid-forming agent is at least one member selected from the group consisting of (1) an onium salt represented by one of the following formulas: wherein R¹⁷, R¹⁸ and R¹⁹, which may be the same or different, represent hydrogen atoms, amino groups, nitro groups, cyano groups, alkyl groups having 1-4 carbon atoms or alkoxy groups having 1-4 carbon atoms; and X represents SbF₆, AsF₆, PF₆, BF₄, CF₃CO₂, ClO₄, CF₃SO₃, or in which R²⁰ represents a hydrogen atom, an amino group, an anilino group, an alkyl group having 1-4 carbon atoms or an alkoxy group having 1-4 carbon atoms; R²¹ represents an alkoxy group having 1-4 carbon atoms; and R²² represents a hydrogen atom, an amino group, an anillino group, an alkyl group having 1-4 carbon atoms or an alkoxy group having 1-4 carbon atoms, (2) a halogen-containing compound represented by one of the following formulas: wherein R²³ represents a trichloromethyl group, a phenyl group, a methoxyphenyl group, a naphthyl group or a methoxynaphthyl group; R²⁴, R²⁵ and R²⁶, which may be the same or different, represent hydrogen atoms, halogen atoms, alkyl groups having 1-4 carbon atoms, alkoxy groups having 1-4 carbon atoms or hydroxyl groups, (3) an o-quinonediazide compound represented by one of the following formulas: wherein Ar¹ is in which D is a hydrogen atom or a quinonediazidesulfonyl group and m and n are integers of 0-3; and Ar² is or in which D is as defined above, (4) a nitrobenzyl compound represented by the following formula: wherein R²⁷ represents an alkyl group having 1-4 carbon atoms; p represents an integer of 1-3; R²⁸ represents a hydrogen atom or a methyl group; and R²⁹ represents in which R³⁰ is a hydrogen atom or an alkyl group having 1-4 carbon atoms and R³¹ is an alkoxy group having 1-4 carbon atoms, (5) a sulfonic acid ester compound represented by one of the following formulas: wherein R³² and R³⁵, which may be the same or different, represent hydrogen atoms or alkyl groups having 1-4 carbon atoms; R³³ and R³⁴, which may be the same or different, represent hydrogen atoms, alkyl groups having 1-4 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms or substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, wherein R³⁶ represents a hydrogen atom or an alkyl group having 1-4 carbon atoms; R³⁷ and R³⁸, which may be the same or different, represent alkyl groups having 1-4 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, provided they may be bonded to each other to form a ring, and wherein R³⁹ represents a methyl group, a trichloromethyl group, a trifluoromethyl group, a phenyl group, a tolyl group, a cyanophenyl group, a trichlorophenyl group or a trifluoromethylphenyl group, and (6) a sulfone compound represented by the following formula: wherein Y represents or -SO₂-; R⁴⁰, R⁴¹, R⁴² and R⁴³, which may be the same or different, represent alkyl groups having 1-4 carbon atoms, aralkyl groups having 7-20 carbon atoms or halogen atoms; and m represents an integer of 0-3.
Claim 6
Dependent Claim 16 words
The radiation-sensitive composition according to Claim 5, wherein the radiation-sensitive acid-forming agent is the onium salt.
Claim 7
Dependent Claim 125 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is at least one member selected from the group consisting of a compound represented by formula (i): wherein R⁴⁴, R⁴⁵ and R⁴⁶, which may be the same or different, represent hydrogen atoms, alkyl groups having 1-6 carbon atoms, aminoalkyl groups having 1-6 carbon atoms, hydroxyalkyl groups having 1-6 carbon atoms or substituted or unsubstituted aryl groups having 6-20 carbon atoms, provided that R⁴⁵ and R⁴⁶ may be bonded to each other to form a ring, and a compound having at least one structure selected from those represented by formulas (ii) to (v): wherein R⁴⁷, R⁴⁸, R⁴⁹ and R⁵⁰, which may be the same or different, represent alkyl groups having 1-6 carbon atoms.
Claim 8
Dependent Claim 34 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is ammonia, triethylamine, tripropylamine, tributylamine, anillne, N-methylaniline, N,N-dimethylaniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-nitroaniline, 1-naphthylamine, 2-naphtylamine, diphenylamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, pyrrolidine or piperidine.
Claim 9
Dependent Claim 19 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is imidazole, 4-methylimidazole, 4-methyl-2-phenylimidazole or thiabendazole.
Claim 10
Dependent Claim 24 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is pyridine, 2-methylpyridine, 4-ethylpyridine, 1-methyl-4-phenylpyridine, 2-(1-ethylpropyl)pyridine, nicotinamide, dibenzoylthiamine or riboflavine tetrabutyrate.
Claim 11
Dependent Claim 27 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, 4,4′-diaminobenzophenone, 4,4′-diaminodiphenylamine, 2,2-bis(4-aminophenyl)propane, 2-(3-aminophenyl)-2-(4-aminophenyl)propane, 2-(4-aminophenyl)-2-(4-hydroxyphenyl)propane, 1,4-bis[1-(4-aminophenyl)-4-methylethyl]benzene or 1,3-bis[1-(4-aminophenyl)-1-methylethyl]benzene.
Claim 12
Dependent Claim 21 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate, poly{[6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidyl)imino]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]} or bis (1,2,2,6,6-pentamethyl-4-piperidyl)2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonate.
Claim 13
Dependent Claim 23 words
The radiation-sensitive composition according to Claim 1, wherein the polymer having acid-decomposable silyl groups has a polystyrene-reduced weight average molecular weight of 10,000-300,000.
Claim 14
Dependent Claim 24 words
The radiation-sensitive composition according to Claim 2, wherein the content of the recurring structure unit represented by formula (I) is 15 mole% or more.
Claim 15
Dependent Claim 34 words
The radiation-sensitive composition according to Claim 1, wherein the radiation-sensitive acid-forming agent is contained in a proportion of 0.1-20 parts by weight per 100 parts by weight of the polymer having acid-decomposable silyl groups.
Claim 16
Dependent Claim 35 words
The radiation-sensitive composition according to Claim 1, wherein the weakly basic, nitrogen-containing compound is contained in a proportion of 0.001-10 parts by weight per 100 parts by weight of the polymer having acid-decomposable silyl groups.

References Cited (Backward Citations)

EP0178208A1 Cited
DE3630693A1 Cited
EP0329610A2 Cited
EP0358517A2 Cited
EP0360618A2 Cited
EP0396254A2 Cited

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