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US4931381A Expired / Lapsed US ⏱️ 0.0 years remaining

Image reversal negative working O-quinone diazide and cross-linking compound containing photoresist process with thermal curing treatment

Assignee: EMD Performance Materials Corp
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Filing: 1988-11-08
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Granted: 1990-06-05
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Expires: 2008-11-08
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Abstract

Abstract A process for converting a normally positive working photosensitive composition to a negative working composition. One forms a composition containing an alkali soluble resin, a 1,2 quinone diazide-4-sulfonyl compound and an acid catalyzed crosslinker in a solvent mixture. After drying and imagewise exposing, the composition is baked and developed to produce a negative image.

Inventors

  • 👤 Mark A. Spak
  • 👤 Donald Mammato
  • 👤 Dana Durham
  • 👤 Sangya Jain

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 02:12
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/0226; G03F7/26; G03F7/38; Y; Y10; Y10S; Y10S430/00; Y10S430/143; Y10S430/167; Y10S430/168

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 328 words
A process for preparing a negative working photographic element which consists essentially of in order: (a) forming a composition which consists essentially of in admixture (i) from about 1% to about 25% based on the weight the solid parts of the composition of a photosensitive compound having the formula ##STR15## wherein R 1 =1,2 benzoquinone-2-diazide-4-sulfonyl; 1,2 naphthoquinone-2-diazide-4-sulfonyl; or 1,2 anthraquinone-2-diazide-4-sulfonyl R 2 =H, R 7 , OR 6 or ##STR16## R 3 =H, R 7 , OR 6 or ##STR17## R 4 =H, R 7 , OR 6 or ##STR18## R 6 =H, alkyl, aryl, aralkyl or R 1 R 7 =alkyl, aryl or aralkyl (ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and (iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which has the formula ##STR19## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 )cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl or arylalkyl; and (iv) sufficient solvent to dissolve the foregoing composition components; and (b) coating said composition on a substrate; and (c) heating said coated substrate at a temperature of from about 20° to about 100° until substantially all of said solvent is dried off; and (d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and (e) heating said coated substrate at a temperature of at least about 95° C. to about 160° for from about 10 seconds or more to crosslink said resin; and (f) removing the radiation unexposed non-image areas of said composition with a developer wherein the process is conducted in the absence of a flood exposure after heating step (e).
Claim 2
Dependent Claim 328 words
A process for preparing a negative working photographic element which consists essentially of in order: (a) forming a composition which consists essentially of in admixture (i) from about 1% to about 25% based on the weight the solid parts of the composition of a photosensitive compound having the formula ##STR15## wherein R 1 =1,2 benzoquinone-2-diazide-4-sulfonyl; 1,2 naphthoquinone-2-diazide-4-sulfonyl; or 1,2 anthraquinone-2-diazide-4-sulfonyl R 2 =H, R 7 , OR 6 or ##STR16## R 3 =H, R 7 , OR 6 or ##STR17## R 4 =H, R 7 , OR 6 or ##STR18## R 6 =H, alkyl, aryl, aralkyl or R 1 R 7 =alkyl, aryl or aralkyl (ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and (iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which has the formula ##STR19## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 )cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl or arylalkyl; and (iv) sufficient solvent to dissolve the foregoing composition components; and (b) coating said composition on a substrate; and (c) heating said coated substrate at a temperature of from about 20° to about 100° until substantially all of said solvent is dried off; and (d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and (e) heating said coated substrate at a temperature of at least about 95° C. to about 160° for from about 10 seconds or more to crosslink said resin; and (f) removing the radiation unexposed non-image areas of said composition with a developer wherein the process is conducted in the absence of a flood exposure after heating step (e).
Claim 3
Dependent Claim 12 words
The process of claim 1 wherein said photosensitizer is 2,3,4-trihydroxybenzophenone-1,2-naphthoquinone-2-diazide-4-sulfonic acid trisester.
Claim 4
Dependent Claim 11 words
The process of claim 1 wherein said crosslinker is dimethylol paracresol.
Claim 5
Dependent Claim 13 words
The process of claim 1 wherein said crosslinker is methyl methoxy diphenyl ether.
Claim 6
Dependent Claim 27 words
The process of claim 1 wherein said crosslinking compound is one or more compounds selected from the group consisting of benzene, 1-methoxy-2,6-bis(hydroxymethyl-4-methyl-; phenol, 2,6-bis(methoxymethyl)-4-methyl-; and benzene, 1-methoxy-2,6-bis(methoxymethyl)-4-methyl-.
Claim 7
Dependent Claim 14 words
The process of claim 1 wherein said solvent comprises propylene glycol alkyl ether acetate.
Claim 8
Dependent Claim 34 words
The process of claim 1 wherein said substrate is selected from the group consisting of silicon, aluminum or polymeric resins, silicon dioxide, doped silicon dioxide, silicon nitride, tantalum, copper, polysilicon, ceramics and aluminum/copper mixtures.
Claim 9
Dependent Claim 33 words
The process of claim 1 wherein said composition further comprises one or more compounds selected from the group consisting of colorants, dyes, anti-striation agents, leveling agents, plasticizers, adhesion promoters, speed enhancers, and surfactants.
Claim 10
Dependent Claim 23 words
The process of claim 1 wherein said step (e) is conducted at a temperature of from about 95° C. to about 150° C.
Claim 11
Dependent Claim 20 words
The process of claim 9 wherein said step (e) is conducted for from about 10 seconds to about 90 seconds.
Claim 12
Dependent Claim 23 words
The process of claim 1 wherein said step (e) is conducted at a temperature of from about 112° C. to about 120° C.
Claim 13
Dependent Claim 20 words
The process of claim 11 wherein said step (e) is conducted for from about 10 seconds to about 90 seconds.
Claim 14
Dependent Claim 13 words
The process of claim 1 wherein said developer is an aqueous alkaline solution.
Claim 15
Dependent Claim 15 words
The process of claim 13 wherein said developer comprises sodium hydroxide and/or tetramethyl ammonium hydroxide.
Claim 16
Dependent Claim 20 words
The process of claim 1 wherein said step (e) is conducted for from about 10 seconds to about 90 seconds.
Claim 17
Dependent Claim 48 words
The process of claim 1 wherein, said crosslinker comprises dimethylol paracresol, said heating step (e) is conducted at a temperature of from about 112° C. to about 120° C. for up to 90 seconds, and said developer comprises an aqueous solution of sodium hydroxide and/or tetramethyl ammonium hydroxide.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-06-04 1993-12-04 1994-06-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-06-04 1997-12-04 1998-06-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-06-04 2001-12-04 2002-06-05 $7700.00 Window Closed / Lapsed

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