US4650745A
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US
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Method of forming a resist pattern by radiation exposure of positive-working resist coating comprising a dye and a trihydroxybenzophenone compound and subsequent aqueous alkaline development
Assignee: OCG Microelectronic Materials Inc
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Filing: 1986-06-26
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Granted: 1987-03-17
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Expires: 2006-06-26
Abstract
Abstract Disclosed is a positive-working resist composition which demonstrates improved photospeed and rate of development. The resist composition contains a solvent and select proportions of a novolak resin, a naphthoquinone diazide sensitizer, a dye which absorbs light at a maximum wavelength of from about 330 to about 460 nm and an effective proportion of a trihydroxybenzophenone compound. Also disclosed is a method of forming a resist pattern on a substrate by employing the positive-working resist composition.
Inventors
- 👤 James N. Eilbeck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 12:00
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/0226
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
339 words
A method of forming a resist pattern on a substrate comprising: coating said substrate with a layer of a positive-working photoresist composition; exposing said layer patternwise to actinic radiation; and removing the exposed portions of said layer with an aqueous alkaline developer for the exposed resist composition to uncover the areas of the substrate beneath the exposed portions; said positive-working photoresist composition comprising a solvent and solid ingredients dissolved therein; said solids, whose proportions are based by weight on the total solids in said composition, comprise: (a) from about 63 to about 68 percent of a novolak resin; (b) from about 15 to about 22 percent of a naphthoquinone diazide sensitizer prepared by mono-, di- or tri-esterifying a low molecular weight phenol compound with 1,2-naphthoquinone-2-diazide-5-chloride, said phenol compound having the formula ##STR5## wherein: R is a single bond or one of the groups CO, S, 0, SO 2 or CR 6 R 7 ; R 1 , R 2 , R 3 , R 4 and R 5 are each independently H, X (where X is a halogen atom), OH, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms; and R 6 and R 7 are each independently H or a lower alkyl group having 1 to 4 carbon atoms; or wherein: two of the radicals R 3 , R 4 and R 5 or the two radicals R 1 and R 2 independently jointly form an aromatic ring, whereby at least one of the radicals R 1 , R 2 , R 3 , R 4 or R 5 is OH; (c) from about 0.1 to about 3 percent of a dye a which absorbs light at a maximum wavelength of from about 330 to about 460 nm; and (d) an effective proportion of an additive compound to increase the photospeed and rate of development of said composition, said additive compound being a trihydroxybenzophenone compound and said proportion ranging from about 10 to about 20 percent.
Claim 2
Independent Claim
339 words
A method of forming a resist pattern on a substrate comprising: coating said substrate with a layer of a positive-working photoresist composition; exposing said layer patternwise to actinic radiation; and removing the exposed portions of said layer with an aqueous alkaline developer for the exposed resist composition to uncover the areas of the substrate beneath the exposed portions; said positive-working photoresist composition comprising a solvent and solid ingredients dissolved therein; said solids, whose proportions are based by weight on the total solids in said composition, comprise: (a) from about 63 to about 68 percent of a novolak resin; (b) from about 15 to about 22 percent of a naphthoquinone diazide sensitizer prepared by mono-, di- or tri-esterifying a low molecular weight phenol compound with 1,2-naphthoquinone-2-diazide-5-chloride, said phenol compound having the formula ##STR5## wherein: R is a single bond or one of the groups CO, S, 0, SO 2 or CR 6 R 7 ; R 1 , R 2 , R 3 , R 4 and R 5 are each independently H, X (where X is a halogen atom), OH, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms; and R 6 and R 7 are each independently H or a lower alkyl group having 1 to 4 carbon atoms; or wherein: two of the radicals R 3 , R 4 and R 5 or the two radicals R 1 and R 2 independently jointly form an aromatic ring, whereby at least one of the radicals R 1 , R 2 , R 3 , R 4 or R 5 is OH; (c) from about 0.1 to about 3 percent of a dye a which absorbs light at a maximum wavelength of from about 330 to about 460 nm; and (d) an effective proportion of an additive compound to increase the photospeed and rate of development of said composition, said additive compound being a trihydroxybenzophenone compound and said proportion ranging from about 10 to about 20 percent.
Claim 3
Dependent Claim
11 words
The method of claim 1, wherein said additive compound is 2,3,4-trihydroxybenzophenone.
Claim 4
Dependent Claim
53 words
The method of claim 1, wherein said novolak resin is a cresol-formaldehyde novolak resin produced by condensing a mixture of cresol isomers with formaldehyde in the presence of acid, said mixture including from about 45 to about 60 percent of meta-cresol and from about 55 to about 40 percent of para-cresol, by weight.
Claim 5
Dependent Claim
22 words
The method of claim 3, wherein said dye absorbs light at a maximum wavelength of from about 400 to about 460 nm.
Claim 6
Dependent Claim
64 words
The method of claim 4, wherein said composition comprises: (a) from about 65 to about 68 percent of said novolak resin; (b) from about 16 to about 21 percent of said naphthoquinone diazide sensitizer; (c) from about 0.2 to about 1.5 percent of said dye; and (d) wherein said additive compound is 2,3,4-trihydroxybenzophenone and said proportion ranges from about 10 to about 15 percent.
Claim 7
Dependent Claim
146 words
The method of claim 5, wherein said composition comprises: (a) about 67.60 percent of said novolak resin, said mixture of cresol isomers including about 45 percent of meta-cresol and about 55 percent of para-cresol; (b) about 19.04 percent of said naphthoquinone diazide sensitizer, wherein said naphthoquinone diazide sensitizer is the esterification product of 1 mole of 2,3,4-trihydroxybenzophenone with 2 moles of naphthoquinone-(1,2)-diazide-5-sulfonyl chloride; (c) about 0.26 percent of said dye and wherein said dye absorbs light at a maximum wavelength of from about 400 to about 440 nm and is selected from the group consisting of anthraquinones, coumarins, diphenylmethanes, triphenylmethanes, phenazines, oxazines, xanthenes and azo compounds having the formula ##STR6## wherein: R 1 and R 2 are each independently an alkyl group having 1 to 12 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms; and (d) about 13.10 percent of said 2,3,4-trihydroxybenzophenone.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-03-16 | 1990-09-15 | 1991-03-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-16 | 1994-09-15 | 1995-03-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-16 | 1998-09-15 | 1999-03-17 | $7700.00 | Window Closed / Lapsed |