Patent EP0558280A1 successfully refreshed from Google Patents.
EP0558280A1
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Chemically amplified resist
Assignee: JSR Corp
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Filing: 1993-02-23
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Granted: —
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Expires: 2013-02-23
Abstract
Abstract A chemically amplified resist comprising an alkali-soluble resin or a resin having at least one acid-dissociable group which is alkali-insoluble or -sprairingly soluble but becomes alkali-soluble upon dissociation of said acid dissociable group due to an acid; a radiation-sensitive, acid-generating agent; and an optional component in which resist, the radiation-sensitive, acid-generating agent generates an acid upon irradiation with a radiation in the irradiated portion and the solubility of the resin component and optional component in a developing solution is varied in the irradiated portion by a chemical reaction caused by the catalytic action of the acid, whereby a pattern is formed, characterized in that a compound having a nitrogen-containing basic group is contained in the resist. Said resist is superior in developability, pattern form, resolution, focus tolerance and yield of residual film thickness, has good process stability, and can be suitably used even in irradiation with, in particular, a radiation having a wavelength equal to or smaller than far ultraviolet rays, for example, an excimer laser or the like.
Inventors
- 👤 Makoto Murata
- 👤 Takao Miura
- 👤 Yoshiji Yumoto
- 👤 Toshiyuki Ota
- 👤 Eiichi Kobayashi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 04:49
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0755; G03F7/04; G03F7/0045; G03F7/022; G03F7/039
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
108 words
A chemically amplified resist comprising an alkali-soluble resin or a resin having at least one acid-dissociable group which is alkali-insoluble or -spairingly soluble but becomes alkali-soluble upon dissociation of said acid-dissociable group due to an acid; a radiation-sensitive, acid-generating agent; a compound having a nitrogen-containing basic group; and an optional component, in which resist, the radiation-sensitive , acid-generating agent generates an acid upon irradiation with a radiation in the irradiated portion and the solubility of the resin component and optional component in a developing solution is varied in the irradiated portion by a chemical reaction caused by the catalytic action of the acid, whereby a pattern is formed.
Claim 2
Dependent Claim
73 words
The chemically amplified resist according to Claim 1, wherein the resin is an alkali-soluble resin and the composition further comprises a compound which has an effect of its controlling the alkali-solubility of the alkali-soluble resin, and exhibits, when it is decomposed in the presence of an acid, such properties that the effect of controlling the alkali-solubility of the alkali-soluble resin is reduced or lost or the alkali-solubility of the alkali-soluble resin is promoted.
Claim 3
Dependent Claim
56 words
The chemically amplified resist according to Claim 1, wherein the resin is an alkali-insoluble or -spairingly soluble resin having at least one acid-dissociable group selected from the group consisting of substituted methyl groups, 1-substituted ethyl groups, germyl groups, alkoxycarbonyl groups and acyl groups, said resin becoming alkali-soluble upon dissociation of the group due to an acid.
Claim 4
Dependent Claim
34 words
The chemically amplified resist according to Claim 1, wherein the resin is an alkali-soluble resin and the composition further comprises a compound capable of cross-linking the alkali-soluble resin in the presence of an acid.
Claim 5
Dependent Claim
24 words
The chemically amplified resist according to Claim 2, 3 or 4, wherein the compound having a nitrogen-containing basic group is a weakly basic compound.
Claim 6
Dependent Claim
35 words
The chemically amplified resist according to Claim 2, 3 or 4, wherein the compound having a nitrogen-containing basic group is a weakly basic or neutral compound having a nitrogen-containing basic group and an acidic group.
Claim 7
Dependent Claim
129 words
The chemically amplified resist according to Claim 5, wherein the compound having a nitrogen-containing basic group has, in the molecule, at least one structure selected from the structures represented by formulas (24) to (28): and wherein R⁵⁰, R⁵¹ and R⁵² are the same as or different from one another and each thereof represents a hydrogen atom, an alkyl group having 1-6 carbon atoms, an aminoalkyl group having 1-6 carbon atoms, a hydroxyalkyl group having 1-6 carbon atoms or a substituted or unsubstituted aryl group having 6-20 carbon atoms, provided that R⁵¹ and R⁵² may be bonded to each other to form a ring; and R⁵³, R⁵⁴, R⁵⁵ and R⁵⁶ are the same as or different from one another and each thereof represents an alkyl group having 1-6 carbon atoms.
Claim 8
Dependent Claim
85 words
The chemically amplified resist according to Claim 7, wherein the compound having a structure represented by formula (24), formula (25), formula (26), formula (27) or formula (28) in the molecule is ammonia, triethylamine, tripropylamine, tributylamine, aniline, N-methylaniline, N,N-dimethylaniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-nitroaniline, 1-naphthylamine, 2-naphthylamine, diphenylamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, pyrrolidine, piperidine, imidazole, 4-methylimidazole, 4-methyl-2-phenylimidazole, thiabendazole, 4,5-diphenylimidazole, 2,4,5-triphenylimidazole, pyridine, 2-methylpyridine, 4-ethylpyridine, 1-methyl-4-phenylpyridine, 2-(1-ethylpropyl)pyridine, nicotinamide, dibenzoylthiamine, riboflavine tetrabutyrate, 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-(3-hydroxyphenyl)propane, 2-(4-aminophenyl)-2-(4-hydroxyphenyl)propane, 1,4-bis-[1-(4-aminophenyl)-1-methylethyl]benzene, 1,3-bis-[1-(4-aminophenyl)-1-methylethyl]benzene, 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-tert-butyl-4-hydroxybenzyl)-2-n-butylmalonate.
Claim 9
Dependent Claim
63 words
The chemically amplified resist according to Claim 6, wherein the weakly basic or neutral compound having a nitrogen-containing basic group and an acidic group has, in the molecule, at least one acidic group and at least one structure selected from the group consisting of the structures represented by formulas (25) to (28) specified in Claim 7 and a structure represented by formula (29)
Claim 10
Dependent Claim
24 words
The chemically amplified resist according to Claim 9, wherein the acidic group is a carboxyl group, a sulfo group or a phenolic hydroxyl group.
Claim 11
Dependent Claim
50 words
The chemically amplified resist according to Claim 9, wherein the weakly basic or neutral compound is nicotinic acid, isoleucine, glycine, glutamic acid, threonine, theanine, tryptophane, L-valine, histidine hydrochloride, phenylalanine, methionine, folic acid, lysine, asparatic acid salt, glutamic acid salt, 3-aminopyrazine-2-carboxylic acid, 3-pyridinesulfonic acid, 2-hydroxypyridine, 3-hydroxypyridine, 4-hydroxypyridine, 2-amino-p-creaol, 5-amino-o-cresol or 6-amino-m-cresol.
Claim 12
Dependent Claim
34 words
The chemically amplified resist according to Claim 1, wherein the compound having a nitrogen-containing basic group is used in an amount of 0.001-10 parts by weight per 100 parts by weight of the resin.
Claim 13
Dependent Claim
143 words
The chemically amplified resist according to Claim 4, wherein the alkali-soluble resin is a resin having at least one repeating unit selected from the group consisting of a repeating unit represented by formula (1): wherein R a is a hydrogen atom or a methyl group; R b is a hydroxyl group, a carboxyl group, -R c COOH, -OR c COOH or (in which R c is -(CH₂) n - (n is an integer of 1-4), a repeating unit represented by formula (2): wherein R a is as defined above, a repeating unit represented by formula (3): and a repeating unit represented by formula (4): wherein R d , R e , R f , R g and R h are the same as or different from one another and each thereof is a hydrogen atom or an alkyl group having 1-4 carbon atoms.
Claim 14
Dependent Claim
42 words
The chemically amplified resist according to Claim 3, wherein the alkali-insoluble or -spairingly soluble resin having at least one acid-dissociable group selected from the group consisting of tert-butyl group, benzyl group, tetrahydrofuryl group, tetrahydropyranyl group, tetrahydrothiofuryl group, tetrahydrothiopyranyl group and tert-butoxycarbonyl group.
Claim 15
Dependent Claim
34 words
The chemically amplified resist according to Claim 1, wherein the radiation-sensitive, acid-generating agent is an onium salt, a halogen-containing compound, a quinonediazide compound, a sulfone compound, a sulfonic acid compound or a nitrobenzyl compound.
Claim 16
Dependent Claim
20 words
The chemically amplified resist according to Claim 1, wherein the radiation-sensitive, acid-generating agent is an onium salt or quinonediazide compound.
Claim 17
Dependent Claim
31 words
The chemically amplified resist according to Claim 1, wherein the radiation-sensitive, acid-generating agent is contained in an amount of 1-70 parts by weight per 100 parts by weight of the resin.
Claim 18
Dependent Claim
91 words
The chemically amplified resist according to Claim 2, wherein the compound which has an effect of its controlling the alkali-solubility of the alkali-soluble resin and exhibits, when it is decomposed in the presence of an acid, such properties that the effect of controlling the alkali-solubility of the alkali-soluble resin is reduced or lost or the alkali-solubility of the alkali-soluble resin is promoted is a compound having at least one group selected from the group consisting of substituted methyl groups, 1-substituted ethyl groups, silyl groups, germyl groups, alkoxycarbonyl groups and acyl groups.
Claim 19
Dependent Claim
29 words
The chemically amplified resist according to Claim 18, wherein the compound is contained in an amount of 5-150 parts by weight per 100 parts by weight of the resin.
Claim 20
Dependent Claim
72 words
The chemically amplified resist according to Claim 4, wherein the compound capable of cross-linking the alkali-soluble resin in the presence of an acid is an aromatic compound having a cross-linkable substituent selected from the group consisting of glycidyl ether group, glycidyl ester group, glycidylamino group, methylol group, methoxymethyl group, ethoxymethyl group, benzyloxymethyl group, dimethylaminomethyl group, diethoxymethylamino group, morpholinomethyl group, acetoxymethyl group, benzoyloxymethyl group, formyl group, acetyl group, vinyl group and isopropenyl group.
Claim 21
Dependent Claim
38 words
The chemically amplified resist according to Claim 4, wherein the aromatic compound having a cross-linkable substituent is a methylol group-containing phenolic resin, a methylol group-containing melamine compound, a methoxymethyl group-containing phenol compound or an acetoxymethyl group-containing phenol compound.
Claim 22
Dependent Claim
42 words
The chemically amplified resist according to Claim 4, wherein the compound capable of cross-linking the alkali-soluble resin in the presence of an acid is contained in an amount of 5-95 parts by weight per 100 parts by weight of the alkali-soluble resin.
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