EP0366590A2
Expired / Lapsed
EP
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Highly sensitive positive photoresist compositions
Assignee: International Business Machines Corp
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Filing: 1989-10-10
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Granted: —
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Expires: 2009-10-10
Abstract
Abstract Positive resists sensitive to UV, electron beam, and x-ray radiation which are alkaline developable are formulated from a polymer material comprising recurrent structures having alkaline soluble groups pendent to the polymer backbone, a portion of which groups are substituted with acid labile groups. The attached drawing shows comparative spectral compositions of 1,4 µm resist films of various compositions according to the present invention.
Inventors
- 👤 David Paul Merritt
- 👤 Robert Lavin Wood
- 👤 Wayne Martin Moreau
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 18:00
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/039
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
74 words
An improved positive working resist composition comprising a polymeric material having functional groups pendent thereto which contribute to the solubility of the polymer in alkaline developers and a portion of which functional groups are substituted with acid labile groups which inhibit the alkaline solubility of the polymer, and a photoinitiator which generates a strong acid upon radiolysis to remove the acid labile groups from the functional groups in the exposed areas of the polymer.
Claim 2
Dependent Claim
74 words
An improved positive working resist composition comprising a polymeric material having functional groups pendent thereto which contribute to the solubility of the polymer in alkaline developers and a portion of which functional groups are substituted with acid labile groups which inhibit the alkaline solubility of the polymer, and a photoinitiator which generates a strong acid upon radiolysis to remove the acid labile groups from the functional groups in the exposed areas of the polymer.
Claim 3
Dependent Claim
14 words
The resist composition of Claim 1 wherein the polymeric material comprises an aromatic polymer.
Claim 4
Dependent Claim
13 words
The resist composition of Claim 2 wherein the aromatic material is a polystyrene.
Claim 5
Dependent Claim
25 words
The resist composition of Claim 1 wherein the alkaline soluble functional groups are selected from the group consisting of hydroxyl, amine, carboxyl, and imide NH.
Claim 6
Dependent Claim
14 words
The resist composition of Claim 4 wherein the alkaline soluble functional group is hydroxyl.
Claim 7
Dependent Claim
21 words
The resist composition of Claim 1 wherein the acid labile group is selected from the group of alkyloxycarbonyl, aryloxycarbonyloxy, and alkyloxycarbonyloxy.
Claim 8
Dependent Claim
23 words
The resist composition of Claim 6 wherein the alkyl portion of the acid labile group has an available hydrogen on an carbon atom.
Claim 9
Dependent Claim
21 words
The resist composition of Claim 7 where the alkyl portion of the acid labile group is secondary alkyl or tertiary alkyl.
Claim 10
Dependent Claim
23 words
The resist composition of Claim 1 wherein from about 20% to about 50% of the pendent groups are substituted with acid labile groups.
Claim 11
Dependent Claim
30 words
The resist composition of Claim 1 wherein the polymer is a polystyrene, the functional group is hydroxyl, and the acid labile group is a secondary or tertiary alkyloxy carbonyloxy group.
Claim 12
Dependent Claim
19 words
The resist composition of Claim 11 wherein the polymer is a p-hydroxystyrene and the acid labile group is t-butyloxycarbonyloxy.
Claim 13
Independent Claim
101 words
The method of making a substituted polymeric material for use in resist compositions, comprising the steps of: (a) dissolving a polymer having acid labile groups pendent to the polymer backbone thereof in an acid stable solvent, (b) heating the solution with stirring under an unreactive atmosphere to a temperature in the range 20 to 70°C, (c) adding concentrated mineral acid to the stirred solution in an amount sufficient to remove acid labile groups from the polymer, (d) continuing the reaction until the desired degree of substitution is achieved, (e) quenching the reaction with base, and (f) precipitating the substituted polymeric material.
Claim 14
Independent Claim
101 words
The method of making a substituted polymeric material for use in resist compositions, comprising the steps of: (a) dissolving a polymer having acid labile groups pendent to the polymer backbone thereof in an acid stable solvent, (b) heating the solution with stirring under an unreactive atmosphere to a temperature in the range 20 to 70°C, (c) adding concentrated mineral acid to the stirred solution in an amount sufficient to remove acid labile groups from the polymer, (d) continuing the reaction until the desired degree of substitution is achieved, (e) quenching the reaction with base, and (f) precipitating the substituted polymeric material.
Claim 15
Dependent Claim
10 words
The method of claim 12 wherein the polymer is polystyrene.
Claim 16
Dependent Claim
21 words
The method of claim 12 wherein the acid labile groups are selected from the group consisting of alkyloxycarbonyl, aryloxycarbonyloxy and alkyloxycarbonyloxy.
Claim 17
Dependent Claim
22 words
The method of claim 14 wherein the alkyl portion of the acid labile group has an available hydrogen on an carbon atom.
Claim 18
Dependent Claim
20 words
The method of claim 15 wherein the alkyl portion of the acid labile group is secondary alkyl or tertiary alkyl.
Claim 19
Dependent Claim
12 words
The method of claim 16 wherein the acid labile group is t-butyloxycarbonyloxy.
Claim 20
Dependent Claim
16 words
The method of claim 12 wherein the pKa of the acid is less than about 4.
Claim 21
Dependent Claim
12 words
The method of claim 18 wherein the mineral acid is sulfuric acid.
Claim 22
Dependent Claim
15 words
The method of claim 12 wherein the reaction temperature is in the range of 50-60°C.
Claim 23
Dependent Claim
13 words
The method of claim 12 wherein the reaction is quenched with ammonium hydroxide.
Claim 24
Dependent Claim
15 words
The method of claim 12 wherein the substituted polymeric material is precipitated in ammonium acetate.
References Cited (Backward Citations)
No citation records indexed.
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