US4259430A
Expired / Lapsed
US
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Photoresist O-quinone diazide containing composition and resist mask formation process
Assignee: International Business Machines Corp
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Filing: 1976-06-25
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Granted: 1981-03-31
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Expires: 1996-06-25
Abstract
Abstract A resist composition includes an alkali soluble resin, a light sensitive diazo compound, and a thermally activated free radical initiator. Resist masks are formed from the above composition by providing a layer of resist on a substrate, exposing the layer patternwise to radiation, removing portions of the layer with a developing solution, and heating the remaining portions of the layer at a temperature which activates the initiator and cross-links the resist to improve the physical characteristics of the resist layer and minimize pattern distortion.
Inventors
- 👤 Leon H. Kaplan
- 👤 Steven M. Zimmerman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:56
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/0226
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
178 words
A process for forming a positive resist mask comprising: providing a layer which includes a mixture consisting essentially of an alkali soluble novolac or resole resin, a light sensitive diazo compound having the general formula; ##STR2## in which R 1 is a naphthoquinone-(1,2)-diazide radical, R 2 is selected from the group consisting of hydrogen and hydroxyl, and R 3 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino and heterocyclic groups, and from about 3 to 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical initiator selected from the group consisting of acyl peroxides, peresters, hydroperoxides, alkyl peroxides, and azo-bis-(isobutyronitrile) on a substrate, exposing said layer patternwise to actinic radiation, removing the exposed portions of said layer with an alkaline developer solution, to form a resist pattern on said substrate and heating said resist pattern at a temperature above the second order glass transition temperature of said resin which activates said initiator to cross link said layer so as to inhibit flow of said resist pattern.
Claim 2
Dependent Claim
178 words
A process for forming a positive resist mask comprising: providing a layer which includes a mixture consisting essentially of an alkali soluble novolac or resole resin, a light sensitive diazo compound having the general formula; ##STR2## in which R 1 is a naphthoquinone-(1,2)-diazide radical, R 2 is selected from the group consisting of hydrogen and hydroxyl, and R 3 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino and heterocyclic groups, and from about 3 to 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical initiator selected from the group consisting of acyl peroxides, peresters, hydroperoxides, alkyl peroxides, and azo-bis-(isobutyronitrile) on a substrate, exposing said layer patternwise to actinic radiation, removing the exposed portions of said layer with an alkaline developer solution, to form a resist pattern on said substrate and heating said resist pattern at a temperature above the second order glass transition temperature of said resin which activates said initiator to cross link said layer so as to inhibit flow of said resist pattern.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein said temperature is between about 150° and 200° C.
Claim 4
Dependent Claim
164 words
A process for forming a positive resist mask comprising providing a substrate with a layer of a photosensitive composition which includes a mixture consisting essentially of an alkali soluble novolac resin, a naphthoquinone-(1,2)-diazide sulfonic acid ester, and from about 3 to 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical forming initiator selected from the group consisting of acyl peroxides, peresters, hydroperoxides, alkyl peroxides, and azo-bis-(isobutyronitrile), exposing said layer patternwise to actinic radiation so as to react said diazo compound so as to render the exposed portion of said resist layer more soluble in base than the unexposed portion, removing the exposed portion of said layer with an alkaline developing solution, to form a resist pattern on said substrate and heating said resist pattern at a temperature above the second order glass transition temperature of said resin which activates said initiator to cross link said layer so as to inhibit flow of said resist pattern.
Claim 5
Dependent Claim
164 words
A process for forming a positive resist mask comprising providing a substrate with a layer of a photosensitive composition which includes a mixture consisting essentially of an alkali soluble novolac resin, a naphthoquinone-(1,2)-diazide sulfonic acid ester, and from about 3 to 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical forming initiator selected from the group consisting of acyl peroxides, peresters, hydroperoxides, alkyl peroxides, and azo-bis-(isobutyronitrile), exposing said layer patternwise to actinic radiation so as to react said diazo compound so as to render the exposed portion of said resist layer more soluble in base than the unexposed portion, removing the exposed portion of said layer with an alkaline developing solution, to form a resist pattern on said substrate and heating said resist pattern at a temperature above the second order glass transition temperature of said resin which activates said initiator to cross link said layer so as to inhibit flow of said resist pattern.
Claim 6
Dependent Claim
15 words
The process of claim 3 wherein said temperature is from about 150° to 200° C.
Claim 7
Dependent Claim
106 words
A positive-working photoresist composition consisting essentially of a mixture of an alkali soluble novolac or resole resin, a light sensitive diazo ketone having the general formula: ##STR3## in which R 1 is a naphthoquinone-(1,2)-diazide radical, R 2 is selected from the group consisting of hydrogen and hydroxyl, and R 3 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, aryloxy, amino and heterocyclic groups, and from about 3 to about 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical initiator selected from the group consisting of acyl peroxides, peresters, hydro peroxides, alkyl peroxides, and azo-bis-(isobutyronitrile).
Claim 8
Dependent Claim
106 words
A positive-working photoresist composition consisting essentially of a mixture of an alkali soluble novolac or resole resin, a light sensitive diazo ketone having the general formula: ##STR3## in which R 1 is a naphthoquinone-(1,2)-diazide radical, R 2 is selected from the group consisting of hydrogen and hydroxyl, and R 3 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, aryloxy, amino and heterocyclic groups, and from about 3 to about 30 percent by weight, based on the total weight of resist solids, of a thermally activated free radical initiator selected from the group consisting of acyl peroxides, peresters, hydro peroxides, alkyl peroxides, and azo-bis-(isobutyronitrile).
Claim 9
Dependent Claim
35 words
The composition of claim 5 wherein the peroxide is present in an amount of from about 3 percent to about 15 percent by weight based on the total weight of resin and light sensitive compound.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-30 | 1984-09-29 | 1985-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-30 | 1988-09-29 | 1989-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-30 | 1992-09-29 | 1993-03-31 | $7700.00 | Window Closed / Lapsed |