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US5279918A Expired / Lapsed US ⏱️ 0.0 years remaining

Photoresist composition comprising a quinone diazide sulfonate of a novolac resin

Assignee: DuPont Electronic Materials International LLC
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Filing: 1991-04-30
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Granted: 1994-01-18
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Expires: 2011-04-30
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Abstract

Abstract A photoresist composition useful for the preparation of semiconductors and to be irradiated by light with a wavelength of from 330 to 450 nm, which comprises (1) an alkali-soluble resin, (2) a quinone-diazide type photosensitive compound and (3) a solvent, wherein (a) said quinone-diazide type photosensitive compound is composed mainly of a quinone-diazide sulfonate of a novolac resin produced by polycondensation of at least one phenolic compound of the following formula (A1) or (A2) and at least one ketone or aldehyde derivative of the following formula (B), (b) the weight-average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of said novolac resin is from 400 to 2,000 in the case of the novolac resin derived from the phenolic compound of the formula (A1) and from 600 to 2,200 in the case of the novolac resin derived from the phenolic compound of the formula (A2), and (c) the esterification ratio of said quinone-diazide sulfonate (the number of quinone-diazide sulfonyl groups per molecule of the quinone-diazide sulfonate*100/the number of hydroxyl groups per molecule of the novolac resin) is from 40 to 90%: (* CHEMICAL STRUCTURE *) (A1) (* CHEMICAL STRUCTURE *) (A2) (* CHEMICAL STRUCTURE *) (B) wherein R is an alkyl group or an aryl group, provided that a plurality of R may be the same or different, R1 is an alkyl group, provided that a plurality of R1 may be the same or different, each of R2 and R3 is a hydrogen atom, an alkyl group or an aryl group, l is an integer of from 0 to 3, m is an integer of from 0 to 2 and n is an integer of from 2 to 4, provided that the sum of m+n is from 2 to 4.

Inventors

  • 👤 Mineo Nishi
  • 👤 Koji Nakano
  • 👤 Tadashi Kusumoto
  • 👤 Keisuke Nakano
  • 👤 Yoshihiro Takada

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 14:05
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 226 words
A photoresist composition useful for the preparation of semiconductors and to be irradiated by light with a wavelength of from 330 to 450 nm, which comprises (1) an alkali-soluble resin, (2) a quinone-diazide type photosensitive compound and (3) a solvent, wherein (a) said quinone-diazide type photosensitive compound comprises a quinone-diazide sulfonate of a novolac resin produced by polycondensation of at least one phenolic compound of the following formula (A1a) and at least one member selected from the group consisting of acetaldehyde and acetone, (b) the weight-average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of said novolac resin is from 450 to 1,800, (c) the esterification ratio of said quinone-diazide sulfonate (the number of quinone-diazide sulfonyl groups per molecule of the quinone-diazide sulfonate×100/the number of hydroxyl groups per molecule of the novolac resin) is from 40 to 90%, and (d) the quinone-diazide sulfonate is composed mainly of 1,2-naphthoquinonediazide-5-sulfonate; ##STR6## wherein R' is a C 1-4 alkyl group, and l' is 1 or 2, wherein the alkali-soluble resin is a novolac resin having weight average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of from 3,000 to 20,000 and wherein alkali-soluble resin is a novolac resin obtained by polycondensation of a mixture comprising at least two phenol derivatives of m-cresol and p-cresol with one or more aldehydes or ketones.
Claim 2
Dependent Claim 226 words
A photoresist composition useful for the preparation of semiconductors and to be irradiated by light with a wavelength of from 330 to 450 nm, which comprises (1) an alkali-soluble resin, (2) a quinone-diazide type photosensitive compound and (3) a solvent, wherein (a) said quinone-diazide type photosensitive compound comprises a quinone-diazide sulfonate of a novolac resin produced by polycondensation of at least one phenolic compound of the following formula (A1a) and at least one member selected from the group consisting of acetaldehyde and acetone, (b) the weight-average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of said novolac resin is from 450 to 1,800, (c) the esterification ratio of said quinone-diazide sulfonate (the number of quinone-diazide sulfonyl groups per molecule of the quinone-diazide sulfonate×100/the number of hydroxyl groups per molecule of the novolac resin) is from 40 to 90%, and (d) the quinone-diazide sulfonate is composed mainly of 1,2-naphthoquinonediazide-5-sulfonate; ##STR6## wherein R' is a C 1-4 alkyl group, and l' is 1 or 2, wherein the alkali-soluble resin is a novolac resin having weight average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of from 3,000 to 20,000 and wherein alkali-soluble resin is a novolac resin obtained by polycondensation of a mixture comprising at least two phenol derivatives of m-cresol and p-cresol with one or more aldehydes or ketones.
Claim 3
Dependent Claim 43 words
The photoresist composition according to claim 1, wherein alkali-soluble resin is a novolac resin obtained by polycondensation of a mixture comprising m-cresol, p-cresol, 2,5-xylenol and resorcinol in a molar ratio of 1-7:3:-7:0.5-5:0-1 with one or more aldehydes or ketones comprising at least formaldehyde.
Claim 4
Dependent Claim 38 words
The photoresist composition according to claim 1, wherein the ratio of the weight-average molecular weight to the number average molecular weight of the novolac resin constituting the quinone-diazide sulfonate as the photosensitive compound is from 1.0 to 2.0.
Claim 5
Dependent Claim 24 words
The photosensitive composition according to claim 1, wherein the esterification ratio of the quinone-diazide sulfonate as the photosensitive compound is from 45 to 80%.
Claim 6
Dependent Claim 35 words
The photosensitive composition according to claim 1, wherein the solvent is a solvent having boiling point from 100° to 180° C. which is capable of dissolving the alkali-soluble resin and the quinone-diazide type photosensitive compound.
Claim 7
Dependent Claim 22 words
The photoresist composition according to claim 1, wherein the concentration of the alkali-soluble resin is from 1 to 30 % by weight.
Claim 8
Dependent Claim 21 words
The photoresist composition according to claim 1, wherein the concentration of the photosensitive compound is from 0.1 to 15% by weight.

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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) 1997-01-17 1997-07-19 1998-01-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-01-17 2001-07-19 2002-01-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-01-17 2005-07-19 2006-01-18 $7700.00 Window Closed / Lapsed

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