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US4925770A Expired / Lapsed US ⏱️ 0.0 years remaining

Contrast-enhancing agent for photolithography

Assignee: National Institute of Advanced Industrial Science and Technology
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Filing: 1988-12-14
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Granted: 1990-05-15
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Expires: 2008-12-14
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Abstract

Abstract The invention provides a novel contrast-enhancing agent for photolithography which is used as an overcoating on a positive-working photoresist layer for enhancing the contrast of the photoresist in a low-contrast exposure to light. The composition comprises, in addition to a watersoluble polymer, e.g., poly(vinyl alcohol), poly(vinyl pyrroilidone) and pullulan, as the binder, a specific photo-bleachable organic compound having, in a molecule, at least one nitrogen-containing heterocyclic aromatic structure represented by the general formula <IMAGE> in which Z is a divalent group to form the heterocyclic aromatic ring with the nitrogen atom, X is an anionic group of monovalency and n is a positive integer of, e.g., 1 or 2.

Inventors

  • 👤 Kunihiro Ichimura
  • 👤 Teruhiko Yonezawa
  • 👤 Hideo Kikuchi
  • 👤 Nariaki Tochizawa
  • 👤 Keiichi Hayashi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 20:16
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/091

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 195 words
A contranst-enhancing agent for a photoresist layer which comprises, in admixture: (a) a photo-bleachable compound represented by the general formula ##STR17## in which A is an aromatic group selected from the class consisting of an unsubstituted or substituted phenyl group of the general formula ##STR18## unsubstituted or substituted α- or β-napthyl group of the general formula ##STR19## 9-anthranyl group, unsubstituted or substituted furyl group of the general formula ##STR20## unsubstituted or substituted benzofuryl group of the general formula ##STR21## and unsubstituted or substituted thienyl group of the general formula ##STR22## the subscript n is 1, 2 or 3, Z is a residue selected from the class consisting of pyridyl, quinolyl and benzothiazolyl groups forming a nitrogen-containing aromatic heterocyclic ring together with the nitrogen atom, X is an anionic group of monovalency and R 1 is a hydrogen atom or a group selected from the class consisting of alkyl, alkenyl and aralkyl groups, R 2 being an atom of hydrogen or a halogen or a group selected from the class consisting of alkyl, hydroxy, alkoxy, formyl and acyl groups; and (b) a water-soluble polymer selected from the class consisting of poly(vinyl alcohol), poly(vinyl pyrrolidone) and pullulan.
Claim 2
Dependent Claim 195 words
A contranst-enhancing agent for a photoresist layer which comprises, in admixture: (a) a photo-bleachable compound represented by the general formula ##STR17## in which A is an aromatic group selected from the class consisting of an unsubstituted or substituted phenyl group of the general formula ##STR18## unsubstituted or substituted α- or β-napthyl group of the general formula ##STR19## 9-anthranyl group, unsubstituted or substituted furyl group of the general formula ##STR20## unsubstituted or substituted benzofuryl group of the general formula ##STR21## and unsubstituted or substituted thienyl group of the general formula ##STR22## the subscript n is 1, 2 or 3, Z is a residue selected from the class consisting of pyridyl, quinolyl and benzothiazolyl groups forming a nitrogen-containing aromatic heterocyclic ring together with the nitrogen atom, X is an anionic group of monovalency and R 1 is a hydrogen atom or a group selected from the class consisting of alkyl, alkenyl and aralkyl groups, R 2 being an atom of hydrogen or a halogen or a group selected from the class consisting of alkyl, hydroxy, alkoxy, formyl and acyl groups; and (b) a water-soluble polymer selected from the class consisting of poly(vinyl alcohol), poly(vinyl pyrrolidone) and pullulan.
Claim 3
Dependent Claim 41 words
The contrast-enhancing agent as claimed in claim 1 wherein the amount of the water-soluble polymer as component (b) is in the range from 0.5 to 10 parts by weight per part by weight of the photo-bleachable compound as the component (a).
Claim 4
Dependent Claim 16 words
The contrast-enhancing agent as claimed in claim 1 wherein the subscript n is 1 or 2.
Claim 5
Dependent Claim 22 words
The contrast-enhancing agent as claimed in claim 1 wherein the nitrogen-containing aromatic heterocyclic ring is a pyridyl group or a quinolyl group.
Claim 6
Dependent Claim 48 words
The contrast-enhancing agent as claimed in claim 1 wherein the photo-bleachable compound is a compound represented by either one of the general formulas ##STR23## in which each R 1 is, independently from the others, an alkyl group selected from the class consisting of methyl, ethyl and propyl groups.
Claim 7
Independent Claim 244 words
A method for enhancing the contrast of an image of a photoresist layer on a substrate surface which comprises, prior to exposure of the photoresist layer to light, the step of coating the surface of the photoresist layer with a contrast-enhancing agent comprising, in admixture, (a) a photo-bleachable compound represented by the general formula ##STR24## in which A is an aromatic group selected from the class consisting of an unsubstituted or substituted phenyl group of the general formula ##STR25## unsubstituted or substituted α- or β-naphthyl group of the general formula substituted α- or β-naphthyl group of the general formula ##STR26## 9-anthranyl group, unsubstituted or substituted furyl group of the general formula ##STR27## unsubstituted or substituted benzofuryl group of the general formula ##STR28## and unsubstituted or substituted thienyl group of the general formula ##STR29## the subscript n is 1, 2 or 3, Z is a residue selected from the class consisting of pyridyl, quinolyl and benzothiazolyl groups forming a nitrogen-containing aromatic heterocyclic ring together with the nitrogen atom, X is an anionic group of monovalency and R 1 is a hydrogen atom or a group selected from the class consisting of alkyl, alkenyl and aralkyl groups, R 2 being an atom of hydrogen or a halogen or a group selected from the class consisting of alkyl, hydroxy, alkoxy, formyl and acyl groups; and (b) a water-soluble polymer selected from the class consisting of poly(vinyl alcohol), poly(vinyl pyrrolidone) and pullulan, to form a contrast-enhancing layer thereon.
Claim 8
Independent Claim 244 words
A method for enhancing the contrast of an image of a photoresist layer on a substrate surface which comprises, prior to exposure of the photoresist layer to light, the step of coating the surface of the photoresist layer with a contrast-enhancing agent comprising, in admixture, (a) a photo-bleachable compound represented by the general formula ##STR24## in which A is an aromatic group selected from the class consisting of an unsubstituted or substituted phenyl group of the general formula ##STR25## unsubstituted or substituted α- or β-naphthyl group of the general formula substituted α- or β-naphthyl group of the general formula ##STR26## 9-anthranyl group, unsubstituted or substituted furyl group of the general formula ##STR27## unsubstituted or substituted benzofuryl group of the general formula ##STR28## and unsubstituted or substituted thienyl group of the general formula ##STR29## the subscript n is 1, 2 or 3, Z is a residue selected from the class consisting of pyridyl, quinolyl and benzothiazolyl groups forming a nitrogen-containing aromatic heterocyclic ring together with the nitrogen atom, X is an anionic group of monovalency and R 1 is a hydrogen atom or a group selected from the class consisting of alkyl, alkenyl and aralkyl groups, R 2 being an atom of hydrogen or a halogen or a group selected from the class consisting of alkyl, hydroxy, alkoxy, formyl and acyl groups; and (b) a water-soluble polymer selected from the class consisting of poly(vinyl alcohol), poly(vinyl pyrrolidone) and pullulan, to form a contrast-enhancing layer thereon.
Claim 9
Dependent Claim 40 words
The method for enhancing the contrast of an image of a photoresist layer on a substrate surface as claimed in claim 6 wherein the contrast-enhancing agent is applied to the substrate surface as a solution in water as the solvent.

References Cited (Backward Citations)

US3104973A Cited
US3826656A Cited
US4677049A Cited
US4702996A Cited
US4745042A Cited
US4804614A Cited
US4816380A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-05-14 1993-11-13 1994-05-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-05-14 1997-11-13 1998-05-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-05-14 2001-11-13 2002-05-15 $7700.00 Window Closed / Lapsed

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