EP0628876A1
Expired / Lapsed
EP
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Environmentally stable highly sensitive acid amplifier photoresists
Assignee: International Business Machines Corp
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Filing: 1994-05-25
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Granted: —
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Expires: 2014-05-25
Abstract
Abstract Acid sensitive polymeric compositions, and improved chemically amplified microlithographic resist compositions comprising the acid sensitive polymeric compositions, and methods for the preparation and use thereof are disclosed. The compositions comprise, in admixture, a polymeric binder, an acid labile moiety which provides selective aqueous base solubility upon cleavage, and a compound that generates acid upon exposure of the resist composition to imaging radiation. More particularly, the compositions have one or more acid labile ketal groups, which may be chemically linked to a polymeric resin or which may be incorporated into a separate component to form a dissolution inhibitor. The compositions exhibit reduced sensitivity to environmental contaminants when compared to known acid amplified resist compositions, and may optionally be processed without a post exposure bake step. Such compositions are especially useful in the fabrication of integrated circuit devices by microlithographic techniques.
Inventors
- 👤 Kim Yang Lee
- 👤 Krishna Gandi Sachdev
- 👤 Harbans Singh Sachdev
- 👤 Ratnam Sooriyakumaran
- 👤 Premlatha Jagannathan
- 👤 Mahmoud M. Khojasteh
- 👤 Ahmad Dauod Katnani
- 👤 Ranee Wai-Ling Kwong
- 👤 William Ross Brunsvold
- 👤 James Thomas Fahey
- 👤 George Joseph Hefferon
- 👤 Wu-Song Huang
- 👤 Robert Lavin Wood
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-31 08:24
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/039; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
85 words
An aqueous base developable microlithographic resist composition comprising in admixture: (a) a film forming polymer having recurrent hydroxyl groups chemically linked thereto, (b) an acid labile compound comprising a ketal moiety, and (c) an acid generating compound which forms an acid upon exposure to actinic radiation, wherein the acid generated upon exposure causes the cleavage of at least a portion of said compound comprising a ketal moiety and wherein the exposed composition is rendered selectively more soluble in aqueous base compared to the unexposed composition.
Claim 2
Dependent Claim
44 words
The composition of claim 1 wherein at least a portion of the film forming polymer hydroxyl groups are O-substituted with said acid labile compound comprising a ketal moiety, and wherein the degree of O-substitution is in the range from about 5% to about 100%.
Claim 3
Dependent Claim
19 words
The composition of claim 1 wherein the film forming polymer having recurrent hydroxyl groups further comp rises hydroxyaromatic groups.
Claim 4
Dependent Claim
28 words
The composition of claim 1 wherein the film forming polymer having recurrent hydroxyl groups is the condensation reaction product of a substituted or unsubstituted phenol with an aldehyde.
Claim 5
Dependent Claim
21 words
The composition of claim 4 wherein the hydroxyaromatic polymer is the condensation reaction product of formaldehyde with phenol or an alkylphenol.
Claim 6
Dependent Claim
36 words
The composition of claim 1 wherein the hydroxyaromatic polymer is a polymer selected from the group consisting of polymers and copolymers derived from a substituted or unsubstituted hydroxystyrene and polysilsesquioxanes having hydroxyaromatic groups chemically linked thereto.
Claim 7
Dependent Claim
11 words
The composition of claim 6 wherein the hydroxyaromatic polymer is polyhydroxystyrene.
Claim 8
Dependent Claim
63 words
The composition of claim 6 wherein the hydroxyaromatic polymer is a copolymer derived from a substituted or unsubstituted hydroxystyrene and a cyclic alcohol of the form where X is, independently, a hydrogen or an alkyl group having 1 to 8 carbons, and m is in the range of about 0.8 to 1, and n is in the range of about 0 to 0.2.
Claim 9
Dependent Claim
57 words
The composition of claim 1 wherein said acid labile compound comprising a ketal moiety further comprises a compound of the form wherein X, Y, and Z, are selected, independently, from the group consisting of non-bridging alkyl, aryl, alicyclic, and O-heterocyclic groups, and bridging groups comprising 2 to 8 carbons between any two of X, Y, and Z.
Claim 10
Dependent Claim
25 words
The acid labile compound of claim 9 wherein the ketal moiety is selected from the group consisting of 2-(2-methyl-tetrahydrofuranyl)oxy, 2-(2-methyl-tetrahydropyranyl)oxy, 1-(1-methoxycyclohexyl)oxy, 2-(2-methoxypropyl)oxy, 4-(4-methoxy-tetrahydropyranyl)oxy, and (1-phenoxy-1-phenylethyl)oxy.
Claim 11
Dependent Claim
13 words
The acid labile compound of claim 10 wherein the ketal moiety is 2-(2-methoxypropyl)oxy.
Claim 12
Dependent Claim
44 words
The composition of claim 1 wherein the acid generating compound is selected from the group consisting of metallic, metalloid, and non-metallic onium salts, aryl sulfonates, 2-nitrobenzyl esters, beta-ketosulfones, disulfones, bis-arylsulfonyl diazomethanes, alpha-keto diazides, alpha-carboxyl diazides, precursors of substituted and unsubstituted sulfonic acids, and diazonapthoquinones.
Claim 13
Dependent Claim
16 words
The composition of claim 1 wherein the acid generating compound is chemically linked to a polymer.
Claim 14
Dependent Claim
35 words
The composition of claim 13 wherein the acid generating compound is a polymer having hydroxyl groups, and wherein at least a portion of the hydroxyl groups are O-substituted with substituted or unsubstituted diazoacetoacetate ester groups.
Claim 15
Dependent Claim
11 words
The composition of claim 1 additionally comprising a residual acid scavenger.
Claim 16
Dependent Claim
32 words
The composition of claim 15 wherein the residual acid scavenger is selected from the group consisting of tetraalkylammonium hydroxides, tetraalkanol ammonium hydroxides, dimethylaminopyridines, and ethylene oxide / propylene oxide block copolymer surfactants.
Claim 17
Dependent Claim
9 words
The composition of claim 1 additionally comprising a surfactant.
Claim 18
Dependent Claim
9 words
The composition of claim 1 additionally comprising a dye.
Claim 19
Dependent Claim
44 words
The composition of claim 18 wherein the dye absorbs energy from actinic radiation having one or more wavelengths in the range from about 180 nm to about 400 nm and said dye transfers absorbed energy to the acid generating compound to form an acid.
Claim 20
Dependent Claim
32 words
The composition of claim 18 wherein the dye is selected from the group consisting of 9-anthracenemethanol, 9-phenoxymethylanthracene, 9,10-diphenylanthracene, substituted phenanthracenes, substituted biphenyls, substituted and unsubstituted 4-phenylazoresorcinol, crystal violet base, and coumarin dyes.
Claim 21
Dependent Claim
9 words
The composition of claim 1 additionally comprising a solvent.
Claim 22
Dependent Claim
55 words
The method for forming a microlithographic relief image comprising the steps of applying, to a microlithographic substrate, a radiation sensitive thin film of the composition according to claim 1, patternwise exposing the radiation sensitive thin film to form a latent image, and developing the latent image to form a relief image in the thin film.
Claim 23
Dependent Claim
26 words
The method of claim 22 wherein the radiation sensitive thin film is patternwise exposed to radiation from an electron beam, ion beam, ultraviolet, or x-ray source.
Claim 24
Dependent Claim
35 words
An acid sensitive polymeric composition comprising the ketal reaction product of a polymer having recurrent hydroxyl groups chemically linked thereto and a reactant selected from the group consisting of substituted vinyl ethers and ortho esters.
Claim 25
Dependent Claim
27 words
An acid sensitive polymeric composition comprising the ketal reaction product of a transetherification reaction between a ketal and a polymer having recurrent hydroxyl groups chemically linked thereto.
References Cited (Backward Citations)
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