EP0611998A2
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EP
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Positive-working radiation-sensitive mixture
Assignee: Clariant Finance BVI Ltd
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Filing: 1994-02-15
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Granted: —
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Expires: 2014-02-15
Abstract
Abstract A novel positive-working radiation-sensitive mixture having a high sensitivity to radiation in a short-wavelength UV region is provided which can be developed in an aqueous alkaline solution, has a stable acid latent image and is used for the production of a semiconductor. The mixture comprises, as indispensable components, a) a binder insoluble in water but soluble in an aqueous alkaline solution, b) a compound having at least one bond cleavable with an acid, c) a compound capable of producing an acid upon radiation, and d₁) a basic ammonium compound or d₂) a basic sulfonium compound.
Inventors
- 👤 Klaus Jürgen Przybilla
- 👤 Ralph Dammel
- 👤 Georg Pawlowski
- 👤 Takanori Hoechst Japan Limited Kudo
- 👤 Seiya Hoechst Japan Limited Masuda
- 👤 Yoshiaki Hoechst Japan Limited Kinoshita
- 👤 Natsumi Hoechst Japan Limited Suehiro
- 👤 Munirathna Hoechst Japan Limited Padmanaban
- 👤 Hiroshi Hoechst Japan Limited Okazaki
- 👤 Hajime Hoechst Japan Limited Endo
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 22:58
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/039
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
55 words
A positive-working radiation-sensitive mixture comprising, as indispensable components, a) a binder insoluble in water but soluble in an aqueous alkaline solution, b) a compound having at least one bond cleavable with an acid, c) a compound capable of producing an acid upon radiation, and d₁) a basic ammonium compound or d₂) a basic sulfonium compound.
Claim 2
Dependent Claim
27 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound b) is a compound having at least one C-O-C or C-N-C bond cleavable with an acid.
Claim 3
Dependent Claim
40 words
A positive-working radiation-sensitive mixture according to claim 1, wherein the content of the basic ammonium compound as the component d₁) is 0.01 to 1.00 molar equivalent based on the maximum amount of an acid theoretically produceable from the compound c).
Claim 4
Dependent Claim
75 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said basic ammonium compound as the component d₁) is a compound represented by the following general formula I: [NR¹R²R³R⁴]⁺X₁₋ I wherein R¹ to R⁴ each independently represent a C₁-C₁₈ alkyl, cycloalkyl, alkylaryl or aryl group, provided that one or more aliphatic CH₂ group thereof may be substituted with an oxygen atom; and X₁ represents a basic anion having a pK B value of -3 to +5.
Claim 5
Dependent Claim
67 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said basic ammonium compound d₁) is a compound represented by the following general formula I: [NR¹R²R³R⁴]⁺X₁₋ I wherein R¹ to R⁴ each independently represent methyl, ethyl, propyl, isopropyl, butyl, dodecyl, phenyl or benzyl; and X₁ represents a hydroxyl group or OR' (wherein R' represents a C₁-C₄ alkyl), OCOR'' (wherein R'' represents a C₁-C₁₀ alkyl or aryl) or OCOO-.
Claim 6
Dependent Claim
40 words
A positive-working radiation-sensitive mixture according to claim 1, wherein the content of the basic sulfonium compound as the component d₂) is 0.01 to 2.00 molar equivalent based on the maximum amount of an acid theoretically produceable from the compound c).
Claim 7
Dependent Claim
135 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said basic sulfonium compound as the component d₂) is a member selected from the group consisting of compounds represented by the following formulae II to V: [SR⁵R⁶R⁷]⁺X₂₋ II wherein R⁵, R⁶ and R⁷ each independently represent a C₁-C₁₈ alkyl, aryl or heteroaryl group or an aryl group mono-, di- or tri-substituted with an alkyl, an alkylaryl, an aryl, a halogen, an alkoxy, a phenoxy, a thiophenol, a phenylsulfonyl or a phenylsulphenyl; Y represents [CH₂] n wherein n is 0 or 1, O or S; R⁸ and R⁹ represent a C₁-C₄ alkyl, alkoxy or a halogen; R¹⁰ and R¹¹ represent a C₁-C₄ alkyl, alkoxy or a halogen; n is 5 or 6; and X₂ represents a basic anion having a pK B value of -3 to +5.
Claim 8
Dependent Claim
133 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said basic sulfonium compound as the component d₂) is a member selected from the group consisting of compounds represented by the following formulae II to V: [SR⁵R⁶R⁷]⁺X₂₋ II wherein R⁵, R⁶ and R⁷ each independently represent methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzylbiphenyl, tolyl, xylyl, chlorophenyl, bromophenyl, methoxyphenyl, ethoxyphenyl, propyloxyphenyl, butyloxyphenyl, tert-butyloxyphenyl, phenoxyphenyl, thiophenoxyphenyl or phenylsulfonylphenyl; Y represents [CH₂] n wherein n is 0 or 1, O or S; R⁸ and R⁹ represent a C₁-C₄ alkyl, methoxy, ethoxy, chlorine or bromine; R¹⁰ and R¹¹ represent a C₁-C₄ alkyl, methoxy, ethoxy, chlorine or bromine; n is 5 or 6; and X₂ represents a hydroxyl group or OR (wherein R represents a C₁-C₄ alkyl), OCOR (wherein R represents a C₁-C₁₀ alkyl, aryl or alkylaryl) or OCOO-.
Claim 9
Dependent Claim
19 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said binder as component a) contains a phenolic hydroxyl group.
Claim 10
Dependent Claim
25 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said binder as the component a) comprises polyvinyl phenol, an alkyl-substituted polyvinyl phenol or its copolymer.
Claim 11
Dependent Claim
22 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said binder as the component a) comprises another phenolic binder besides polyvinyl phenol.
Claim 12
Dependent Claim
67 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound as the component b) is a compound represented by the following general formula VI: wherein R₁₂ represents a C₁-C₄ alkylene group, R₁₃ represents a C₁-C₄ alkyl group, R₁₄ represents a C₁-C₁₀ alkyl or aryl group, Z represents a group selected from the group consisting of -CO-, -O-CO- or -NH-CO-, and n is an integer exceeding 1.
Claim 13
Dependent Claim
25 words
A positive-working radiation-sensitive mixture according to claim 1, wherein the concentration of said compound as the component b) is 1 to 60 % by weight.
Claim 14
Dependent Claim
22 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound as the component c) produces a sulfonic acid upon being photodecomposed.
Claim 15
Dependent Claim
40 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound as the component c) is an α,α-bis-sulfonyldiazomethane derivative represented by the following general formula VII: wherein R and R' represent an alkyl, cycloalkyl, aryl, halogenated aryl or heteroaryl group.
Claim 16
Dependent Claim
27 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound as the component c) is a sulfonium salt, an α,α-bis-sulfonyldiazomethane derivative or a phenolic sulfonic ester.
Claim 17
Dependent Claim
28 words
A positive-working radiation-sensitive mixture according to claim 1, wherein the concentration of said compound as the component c) in said mixture is up to 10 % by weight.
Claim 18
Dependent Claim
31 words
A positive-working radiation-sensitive mixture according to claim 1, wherein said compound as the component c) is a salt of sulfonium-sulfonate produced by adding a sulfonic acid to a basic sulfonium salt.
Claim 19
Dependent Claim
44 words
A positive-working radiation-sensitive mixture according to claim 18, wherein said sulfonic acid is an alkylsulfonic acid, a partially or entirely fluorinated alkylsulfonic acid, an arylsulfonic acid or an arylsulfonic acid substituted with a halogen, an alkyl, an alkoxy, nitro, cyano or an alkyl halide.
Claim 20
Dependent Claim
24 words
A radiation-sensitive recording material comprising a layer substrate and a radiation-sensitive layer, wherein said radiation-sensitive layer comprises a radiation-sensitive mixture according to claim 1.
Claim 21
Dependent Claim
63 words
A process for producing a basic or nonbasic sulfonium compound by ion-exchange chromatography, wherein a) use is made of Amberlyst having a quaternary ammonium group as an ion-exchange resin, b) said ion-exchange resin is converted to an OH form by a polar or nonpolar eluent not containing a metallic ion, and c) said eluent is water or a polar or nonpolar organic solvent.
References Cited (Backward Citations)
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