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Antireflective photoresist composition

Assignee: Eastman Kodak Co
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Filing: 1986-12-29
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Granted: —
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Expires: 2006-12-29
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Abstract

Abstract There is disclosed a photoresist composition in which a dye is added to absorb radiation reflected from the support on which the photoresist is coated. The dye is selected for resistance to volatilization, enhanced developer solubility, and for the wavelengths of absorption. Preferred examples are chalcones.

Inventors

  • 👤 Thap Dominh
  • 👤 Donald Richard Diehl

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-30 23:38
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/091

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 233 words
A photoresist composition comprising a positive-working non-silver halide, photosensitive compound and an antireflective dye that absorbs at least some of the radiation that is effective to activate said compound, characterized in that said dye has the following structural formula: wherein: R is alkyl of 1-3 carbon atoms or R 1 is R 2 SO 2 NH-, R 2 NHSO 2 -, HO-, or HO 2 C-; R 2 is alkyl of 1-6 carbon atoms or such alkyl substituted with fluorine, or aryl of 6-10 carbon atoms; Q is =0 or =N- joined with R 3 to complete a pyrazolone ring; R 3 is -CN, -NO 2 , -CF 3 , or joined with Q to complete said pyrazolone ring; R 4 is H, alkyl of 1-6 carbon atoms; or R 5 and R 6 are individually alkyl or alkyl of 1-5 carbon atoms optionally substituted with fluorine, R 7 , or H; Q 1 and Q 2 are individually -CO 2 -, -O 2 C- or -SO 2 -; R 7 is alkyl of 1-3 carbon atoms or aryl of 6-10 carbon atoms; R 8 is H or alkyl of 1-3 carbon atoms; R 9 is H or alkyl of 1-7 carbon atoms; R 10 is NHSO 2 R 7 or H; m and n are individually an integer of from 1 to 5; and p and p' are individually 0 or 1.
Claim 2
Dependent Claim 233 words
A photoresist composition comprising a positive-working non-silver halide, photosensitive compound and an antireflective dye that absorbs at least some of the radiation that is effective to activate said compound, characterized in that said dye has the following structural formula: wherein: R is alkyl of 1-3 carbon atoms or R 1 is R 2 SO 2 NH-, R 2 NHSO 2 -, HO-, or HO 2 C-; R 2 is alkyl of 1-6 carbon atoms or such alkyl substituted with fluorine, or aryl of 6-10 carbon atoms; Q is =0 or =N- joined with R 3 to complete a pyrazolone ring; R 3 is -CN, -NO 2 , -CF 3 , or joined with Q to complete said pyrazolone ring; R 4 is H, alkyl of 1-6 carbon atoms; or R 5 and R 6 are individually alkyl or alkyl of 1-5 carbon atoms optionally substituted with fluorine, R 7 , or H; Q 1 and Q 2 are individually -CO 2 -, -O 2 C- or -SO 2 -; R 7 is alkyl of 1-3 carbon atoms or aryl of 6-10 carbon atoms; R 8 is H or alkyl of 1-3 carbon atoms; R 9 is H or alkyl of 1-7 carbon atoms; R 10 is NHSO 2 R 7 or H; m and n are individually an integer of from 1 to 5; and p and p' are individually 0 or 1.
Claim 3
Dependent Claim 85 words
The composition of claim 1 characterized in that said dye has one of the following structural formulae: or wherein: R 1 is R 2 SO 2 NH-; R 2 is alkyl of 1-6 carbon atoms; R 4 is H or alkyl of 1-6 carbon atoms; R 5 and R are individually alkyl of 1-3 carbon atoms or alkyl of 1-3 carbon atoms substituted with fluorine; R 11 is or H; m and n are 1 or 2; and p and p' are 0 or 1.
Claim 4
Dependent Claim 51 words
The composition of claim 1 wherein said dye is selected from the group consisting of: a) α-cyano-4-[N-ethyl-N-(2,2,2-trifluoroethoxy- carbonylmethyl)]amino-2-methyl-4'-propylsulfonamido- chalcone; b) a-cyano-4-[N,N-di(isopropoxycarbonylmethyl)]-amino-2-methyl-4'-methylsulfonamidochalcone; c) α-cyano-4-[N-ethyl-N-(2,2,2-trifluoroethoxy- carbonylmethyl)]amino-4'-butylsulfonamidochalcone; d) a-cyano-4-[N-ethyl-N-(2,2,2-trifluoroethoxy- carbonylmethyl)]amino-2-methyl-4'-butylsulfonamido- chalcone; e) a-cyano-4-[N-isopropyl-N-isopropoxycarbonyl- methyl]amino-4'-propylsulfonamidochalcone; f) α-cyano-4-[N,N-di(2-fluoroethyl)]amino-4'-butyl- sulfonamidochalcone; g) α-cyano-4-(N,N-di(2-fluoroethyl)]amino-4'-iso- butylsulfonamidochalcone; h) a-cyano-4-[N,N-di(2-fluoroethyl)]amino-4'-pentyl- sulfonamidochalcone; i) α-cyano-4-[N,N-di(2-fluoroethyl)]amino-4'-hexyl- sulfonamidochalcone; j) α-cyano-4-[N,N-di(isopropoxycarbonylmethyl)]-amino-2 methyl-4'-ethylsulfonamidochalcone; k) α-cyano-4-[N-(2-isopropoxycarbonylethyl)-N-isopropoxycarbonylmethyl]amino-4'-ethylsulfonamido- chalcone; 1) 4-[4-di-(isopropoxycarbonylmethyl)amino-2-benzylidene]-3-methyl-1-(4-phenylsulfonamido)phenyl-2-pyrazolin-5-one.
Claim 5
Dependent Claim 50 words
A method of preventing standing wave ripples and reflective notching in a photoresist composition from radiation reflected back from a support on which the photoresist is coated, the method characterized by the step of incorporating into said photoresist composition, a dye having the structural formula set forth in claim 1.

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