US5079131A
Expired / Lapsed
US
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Method of forming positive images through organometallic treatment of negative acid hardening cross-linked photoresist formulations
Assignee: Shipley Co Inc
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Filing: 1991-02-11
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Granted: 1992-01-07
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Expires: 2011-02-11
Abstract
Abstract The present invention is directed to negative cross-linking photoresist formulations containing nonphotoactive cross-linking agents, such as, but not limited to, the CYMEL 300 series, and to the use of these formulations specifically for the dry development of the so-treated resists as positive tone images following their vapor phase treatment with suitable organometallic materials, e.g., HMDS.
Inventors
- 👤 James W. Thackeray
- 👤 Andrew W. McCullough
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 11:46
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/022; G03F7/0226; G03F7/26; G03F7/265
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
141 words
A method of forming a patterned layer on a substrate comprising: (a) coating the substrate with a polymeric negative acid hardening cross-linking photoresist composition containing one or more nonphotoactive cross-linking agents and one or more photoacid generators; (b) drying the coating to form a resist film; (c) exposed selected portions of the coated film with a source of radiation, thereby producing acids in the exposed areas of the film; (d) baking the exposed film to cross-link the exposed areas and to remove sites capable of reacting with an organometallic reagent; (e) treating the baked resist film with a uniform thin layer of an organometallic reagent which is selectively enriched in the non-cross-linked, unexposed areas of the resist film; and (f) dry developing the resist film so as to remove the resist in the exposed, cross-linked areas, affording a positive image formation.
Claim 2
Independent Claim
141 words
A method of forming a patterned layer on a substrate comprising: (a) coating the substrate with a polymeric negative acid hardening cross-linking photoresist composition containing one or more nonphotoactive cross-linking agents and one or more photoacid generators; (b) drying the coating to form a resist film; (c) exposed selected portions of the coated film with a source of radiation, thereby producing acids in the exposed areas of the film; (d) baking the exposed film to cross-link the exposed areas and to remove sites capable of reacting with an organometallic reagent; (e) treating the baked resist film with a uniform thin layer of an organometallic reagent which is selectively enriched in the non-cross-linked, unexposed areas of the resist film; and (f) dry developing the resist film so as to remove the resist in the exposed, cross-linked areas, affording a positive image formation.
Claim 3
Dependent Claim
29 words
The method of claim 1, wherein the polymeric materials in the photoresist composition are selected from the group consisting of poly(p-vinyl)-phenols, the novolak resins, polyvinyl pyrollidones, and mixtures thereof.
Claim 4
Dependent Claim
58 words
The method of claim 1, wherein the photoacid generator is a halogenated aromatic compounds of the formula: ##STR4## wherein: X=Cl, Br, F, or I; n is an integer m is an integer from 1 to 10 inclusive; and the organic substituents R 1 -R 3 are each independently selected from the group consisting of alkyl or aryl groups.
Claim 5
Dependent Claim
22 words
The method of claim 3, wherein the organic substituents R 1 -R 3 are each independently C 1 -C 16 alkyl groups.
Claim 6
Dependent Claim
21 words
The method of claim 3, wherein the organic substituents R 1 -R 3 are each independently C 1 -C 10 groups.
Claim 7
Dependent Claim
21 words
The method of claim 3, wherein the organic substituents R 1 -R 3 are each independently C 1 -C 6 groups.
Claim 8
Dependent Claim
21 words
The method of claim 3, wherein the organic substituents R 1 -R 3 are each independently phenyl or alkyl substituted phenyl.
Claim 9
Dependent Claim
43 words
The method of claim 1, wherein the photoacid generator is a halogenated aromatic compounds of the formula: ##STR5## wherein: the substituents R 1 -R 3 are each independently selected from the group consisting of hydrogen, and halogenated (F, Br, Cl, I) alkyl groups.
Claim 10
Dependent Claim
19 words
The method of claim 8, wherein the halogenated alkyl groups are each independently C 1 -C 16 alkyl groups.
Claim 11
Dependent Claim
18 words
The method of claim 8, wherein the halogenated alkyl groups are each independently C 1 -C 10 groups
Claim 12
Dependent Claim
18 words
The method of claim 8, wherein the halogenated alkyl groups are each independently C 1 -C 6 groups.
Claim 13
Dependent Claim
73 words
The method of claim 1, wherein the organometallic compound is selected from the compounds having the formula: R.sub.1 R.sub.2 R.sub.3 R.sub.4 --M wherein; M is selected from the group consisting of Si, Sn, Ti, P, Ge, and Zr; and the organic substituents R 1 -R 4 are each independently selected from the group consisting of alkyl, aryl, and a suitable leaving group, with the proviso that one such substituent is a leaving group.
Claim 14
Dependent Claim
9 words
The method of claim 12, wherein M is Si.
Claim 15
Dependent Claim
31 words
The method of claim 12, wherein up to three of the organic substituents R 1 -R 4 are each independently selected from the group consisting of C 1 -C 16 alkyl.
Claim 16
Dependent Claim
31 words
The method of claim 12, wherein up to three of the organic substituents R 1 -R 4 are each independently selected from the group consisting of C 1 -C 10 alkyl.
Claim 17
Dependent Claim
31 words
The method of claim 12, wherein up to three of the organic substituents R 1 -R 4 are each independently selected from the group consisting of C 1 -C 6 alkyl.
Claim 18
Dependent Claim
31 words
The method of claim 12, wherein up to three of the organic substituents R 1 -R 4 are each independently selected from the group consisting of phenyl or alkyl substituted phenyl.
Claim 19
Dependent Claim
27 words
The method of claim 12, wherein at least one of the leaving groups is a halogen selected from the group consisting of F, Cl, Br, or I.
Claim 20
Dependent Claim
25 words
The method of claim 12, wherein at least one of the leaving groups is an amino group of the formula NR 1 R 2 .
Claim 21
Dependent Claim
23 words
The method of claim 12, wherein at least one of the leaving groups is an alkoxy group of the formula OR 1 .
Claim 22
Dependent Claim
60 words
The method of claim 1, wherein the organometallic compound is selected from the compounds having the formula: (R.sub.1 R.sub.2 R.sub.3 --M).sub.2+x -NH.sub.1-x wherein; x=0 or 1; M is selected from the group consisting of Si, Sn, Ti, Ge, and Zr; and the organic substituents R 1 -R 3 are each independently selected from the group consisting of alkyl and aryl.
Claim 23
Dependent Claim
9 words
The method of claim 19, wherein M is Si.
Claim 24
Dependent Claim
27 words
The method of claim 19, wherein the organic substituents R 1 -R 3 are each independently selected from the group consisting of C 1 -C 16 alkyl.
Claim 25
Dependent Claim
27 words
The method of claim 19, wherein the organic substituents R 1 -R 3 are each independently selected from the group consisting of C 1 -C 10 alkyl.
Claim 26
Dependent Claim
27 words
The method of claim 19, wherein the organic substituents R 1 -R 3 are each independently selected from the group consisting of C 1 -C 6 alkyl.
Claim 27
Dependent Claim
27 words
The method of claim 19, wherein the organic substituents R 1 -R 3 are each independently selected from the group consisting of phenyl and alkyl substituted phenyl.
Claim 28
Dependent Claim
44 words
The method of claim 1, wherein the photoactive compound is selected from compounds having the formula: ##STR6## wherein Y is selected from the group consisting of O, S, N, and C; and R is selected from the group consisting of alkyl and aryl substituents.
Claim 29
Dependent Claim
19 words
The method of claim 25, wherein R is selected from the group consisting of C 1 -C 16 alkyl.
Claim 30
Dependent Claim
19 words
The method of claim 25, wherein R is selected from the group consisting of C 1 -C 10 alkyl.
Claim 31
Dependent Claim
19 words
The method of claim 25, wherein R is selected from the group consisting of C 1 -C 6 alkyl.
Claim 32
Dependent Claim
19 words
The method of claim 25, wherein R is selected from the group consisting of phenyl and alkyl substituted phenyl.
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