US4737438A
Expired / Lapsed
US
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Negative-working photosensitive composition comprising a diphenylamine-melamine condensate and an azide compound
Assignee: Tokyo Ohka Kogyo Co Ltd
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Filing: 1986-10-21
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Granted: 1988-04-12
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Expires: 2006-10-21
Abstract
Abstract The negative-working photosensitive composition of the invention, which is suitable as a photoresist material in the photolithographic processing of semiconductor devices, comprises (a) a condensation product of a hydroxy-substituted diphenylamine compound such as 4-hydroxy diphenylamine and a methylol melamine or alkoxylated methylol melamine by the reaction in a medium of phosphoric or sulfuric acid and (b) an azide compound capable of strongly absorbing UV or far UV light. The composition gives a photoresist layer having high resistance against heat in the post-baking and the attack of gas plasma encountered in the dry etching for semiconductor processing.
Inventors
- 👤 Naoki Ito
- 👤 Koichiro Hashimoto
- 👤 Wataru Ishii
- 👤 Hisashi Nakane
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:29
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/008; G03F7/012
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
77 words
A negative-working photosensitive composition which comprises in admixture: (a) a condensation product of a hydroxy-substituted diphenylamine compound represented by the general formula C.sub.6 H.sub.5 --NH.sub.2 --C.sub.6 H.sub.5-n (OH).sub.n, in which n is 1 or 2, and a methylol melamine compound or an alkoxylated methylol melamine compound; and (b) a photosensitive azide compound, the amount of azide being in the range from 0.5 to 50 percent by weight of the amount of the condensation product of component (a).
Claim 2
Dependent Claim
77 words
A negative-working photosensitive composition which comprises in admixture: (a) a condensation product of a hydroxy-substituted diphenylamine compound represented by the general formula C.sub.6 H.sub.5 --NH.sub.2 --C.sub.6 H.sub.5-n (OH).sub.n, in which n is 1 or 2, and a methylol melamine compound or an alkoxylated methylol melamine compound; and (b) a photosensitive azide compound, the amount of azide being in the range from 0.5 to 50 percent by weight of the amount of the condensation product of component (a).
Claim 3
Dependent Claim
46 words
The negative-working photosensitive composition as claimed in claim 1 wherein the condensation product as the component (a) is prepared by the condensation reaction of a hydroxy-substituted diphenylamine compound and a methylol melamine compound or an alkoxylated methylol melamine compound in an acid as a reaction medium.
Claim 4
Dependent Claim
31 words
The negative-working photosensitive composition as claimed in claim 2 wherein the hydroxy-substituted diphenylamine compound is selected from the group consisting of 2-, 3-, and 4-hydroxy diphenylamines and 2,4- and 3,5-dihydroxy diphenylamines.
Claim 5
Dependent Claim
41 words
The negative-working photosensitive composition as claimed in claim 2 wherein the methylol melamine compound or the alkoxylated methylol melamine compound is selected from the group consisting of penta(butoxymethyl) monomethylol melamine, tri(methoxymethyl) monomethylol melamine, di(methoxymethyl) monomethylol melamine, trimethylol melamine and hexamethylol melamine.
Claim 6
Dependent Claim
22 words
The negative-working photosensitive composition as claimed in claim 2 wherein the acid as the reaction medium is phosphoric acid or sulfuric acid.
Claim 7
Dependent Claim
58 words
The negative-working photosensitive composition as claimed in claim 1 wherein the azide compound as the component (b) is selected from the group consisting of 4,4'-diazidodiphenyl ether, 4,4'-diazidodiphenyl methane, 3,3'-dichloro-4,4'-diazidodiphenyl methane, 4,4'-diazidodiphenyl sulfide, 4,4'- and 3,3'-diazidodiphenyl sulfones, 4,4'- and 2,2'-diazidostilbenes, 4,4'-diazidochalcone, 4,4'-diazidobenzal acetone, 4,4'-diazidobenzylidene acetone, 2,6-di(4'-azidobenzal) cyclohexanone, 2,6-di(4'-azidobenzal)-4-methyl cyclohexanone, 2,6-di(4'-azidocinnamylidene) cyclohexanone, 4,4'-diazidobiphenyl, 3,3'-dimethyl-4,4'-diazidobiphenyl, 1-azidonaphthalene, 1-azidoanthracene, 1-azidophenanthrene, 1-azidopyrene and 1,8-diazidonaphthalene.
Claim 8
Dependent Claim
31 words
The negative-working photosensitive composition as claimed in claim 6 wherein the azide compound is selected from the group consisting of 4,4'-diazidodiphenyl ether, 4,4'-diazidodiphenyl methane, 4,4'-diazidodiphenyl sulfide and 4,4'- and 3,3'-diazidodiphenyl sulfones.
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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) | 1991-04-12 | 1991-10-12 | 1992-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-12 | 1995-10-12 | 1996-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-12 | 1999-10-12 | 2000-04-12 | $7700.00 | Window Closed / Lapsed |