US4959292A
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US
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Light-sensitive o-quinone diazide composition and product with phenolic novolak prepared by condensation with haloacetoaldehyde
Assignee: Olin Microelectronic Chemicals Inc
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Filing: 1988-07-11
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Granted: 1990-09-25
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Expires: 2008-07-11
Abstract
Abstract A phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR1## wherein R 1 , R 2 and R 3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R 1 , R 2 and R 3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1. These phenolic resins are suitable for use in light-sensitive compositions (e.g. positive-working photoresists).
Inventors
- 👤 Andrew J. Blakeney
- 👤 Thomas Sarubbi
- 👤 Joseph J. Sizensky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:54
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233; G03F7/0236; C; C08; C08G; C08G8/00; C08G8/04; C08K; C08K5/00; C08K5/36; C08K5/41; C08K5/42; C09; C09D; C09D167/00; C09D167/06
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
184 words
A light-sensitive composition comprising an admixture of at least one light-sensitive o-quinonediazide compound and a binder phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetoaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR3## wherein R 1 , R 2 and R 3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R 1 , R 2 and R 3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1, the amount of said o-quinonediazide compound or compounds being about 5% to about 40% by weight and the amount of said binder resin being about 60% to 95% by weight, based on the total nonvolatile solids content of said light-sensitive composition.
Claim 2
Dependent Claim
184 words
A light-sensitive composition comprising an admixture of at least one light-sensitive o-quinonediazide compound and a binder phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetoaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR3## wherein R 1 , R 2 and R 3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R 1 , R 2 and R 3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1, the amount of said o-quinonediazide compound or compounds being about 5% to about 40% by weight and the amount of said binder resin being about 60% to 95% by weight, based on the total nonvolatile solids content of said light-sensitive composition.
Claim 3
Dependent Claim
64 words
The light-sensitive composition of claim 1 wherein said o-quinonediazide compound or compounds are present in the amount of about 10% to about 30% by weight, based on the total nonvolatile solids content of said light-sensitive composition and said binder resin is present in the amount of about 70% to about 90% by weight, based on the total nonvolatile solids content of said light-sensitive composition.
Claim 4
Dependent Claim
23 words
The light-sensitive composition of claim 1 wherein said o-quinonediazide compound or compounds are selected from the o-naphthoquinone-(1,2)-diazide-4-sulfonic acid esters and o-naphthoquinone-(1,2)-diazide-5-sulfonic acid esters.
Claim 5
Dependent Claim
17 words
The light-sensitive composition of claim 3 wherein said esters are derived from polyhydric phenols, alkyl-polyhydroxyphenones an aryl-polyhydroxyphenones.
Claim 6
Dependent Claim
22 words
The light-sensitive composition of claim 4 wherein said esters are selected from the group consisting of polyhydroxybenzophenones and polyhydroxyacetophenones and mixtures thereof.
Claim 7
Dependent Claim
20 words
The light-sensitive composition of claim 1 wherein said binder resin has a molecular weight of about 1500 to about 7,000.
Claim 8
Dependent Claim
26 words
The light-sensitive composition of claim 1 further comprising at least one substance selected from solvents, actinic and visual contrast dyes, plasticizers, anti-striation agents and speed enhancers.
Claim 9
Dependent Claim
193 words
A coated substrate comprising a substrate coated with a film of a light-sensitive composition comprising an admixture of at least one light-sensitive o-quinonediazide compound and a binder novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR4## wherein R 1 , R 2 and R 3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R 1 , R 2 and R 3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1, the amount of said o-quinonediazide compound or compounds being about 5% to about 40% by weight and the amount of said binder resin being about 60% to 95% by weight, based on the total nonvolatile solids content of said light-sensitive composition.
Claim 10
Dependent Claim
193 words
A coated substrate comprising a substrate coated with a film of a light-sensitive composition comprising an admixture of at least one light-sensitive o-quinonediazide compound and a binder novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR4## wherein R 1 , R 2 and R 3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R 1 , R 2 and R 3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1, the amount of said o-quinonediazide compound or compounds being about 5% to about 40% by weight and the amount of said binder resin being about 60% to 95% by weight, based on the total nonvolatile solids content of said light-sensitive composition.
Claim 11
Dependent Claim
38 words
The coated substrate of claim 8 wherein said substrate comprises one or more compounds selected from the group consisting of polyester, polyolefin, silicon, gallium arsenide, silicon/silicon dioxide, doped silicon dioxide, silicon nitride, aluminum/copper mixtures, tantalum, copper and polysilicon.
Claim 12
Dependent Claim
17 words
The coated substrate of claim 8 wherein said substrate is a silicon wafer coated with silicon dioxide.
Claim 13
Dependent Claim
32 words
The light-sensitive composition of claim 1 wherein said haloacetaldehyde source is selected from the group consisting of chloroacetaldehyde diethyl acetal, chloroacetaldehyde dimethyl acetal, aqueous chloroacetaldehyde, and bromoacetaldehyde diethyl acetal and mixtures thereof.
Claim 14
Dependent Claim
14 words
The light-sensitive composition of claim 11 wherein said haloacetaldehyde source is chloroacetaldehyde diethyl acetal.
Claim 15
Dependent Claim
33 words
The light-sensitive composition of claim 1 wherein said phenolic monomer comprises a mixture of meta-cresol and para-cresol wherein the molar percent ratio of meta-cresol to para-cresol is from about 20:80 to about 100:0.
Claim 16
Dependent Claim
22 words
The light-sensitive composition of claim 13 wherein said molar percent ratio of meta-cresol to para-cresol is from about 25:75 to about 40:60.
Claim 17
Dependent Claim
20 words
The light-sensitive composition of claim 13 wherein said phenolic monomer further comprises 3,5-xylenol, 2,5-xylenol, phenol, or ortho-cresol as mixtures thereof.
Claim 18
Dependent Claim
19 words
The light-sensitive composition of claim 1 wherein the novolak-forming condensation reaction occurs in the presence of an acid catalyst.
Claim 19
Dependent Claim
26 words
The light-sensitive composition of claim 1 wherein said molar ratio of total aldehyde to total phenolic monomers being reacted is from about 0.35:1 to about 0.55:1.
Claim 20
Dependent Claim
20 words
The light-sensitive composition of claim 1 wherein said molecular weight of said resin is from about 2,000 to about 6,000.
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