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EP0140273A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Positive photoresist compositions having deep UV response, photosensitive elements and thermally stable photochemically imaged systems containing same

Assignee: CNA Holdings LLC
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Filing: 1984-10-16
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Granted: —
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Expires: 2004-10-16
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Abstract

Abstract Actinic (deep ultraviolet, ultraviolet and visible light sensitive positive photoresist compositions containing a mixture of an alkali-insoluble photoactive compound capable of being transformed into an alkali-soluble species upon exposure to actinic radiation, in an amount sufficient to render the mixture relatively alkali insoluble and a polymer comprising an amount of tCO-NH-COt groups, such as maleimide and especially maleimide - substituted styrene copolymers, sufficient to render the mixture readily alkali soluble upon exposure to actinic radiation are disclosed. The preferred copolymers include maleimide/styrene or a-methylstyrene in a 1:1 molar ratio. The preferred photoactive compound suitable for a positive photoresist composition responsive to deep UV actinic radiation has the formula 18-8 in Table I. The present invention also contemplates photosensitive elements and thermally stable photochemically imaged systems based on the actinic light sensitive positive photoresist compositions. The positive photoresist compositions are coated onto a substrate to produce a photosensitive element, which upon exposure to a pattern of actinic radiation of wavelength in the range of about 200-700 nm produces a photochemically imaged system that can be treated with an alkaline developer to form highly resolved patterns, by highly selective removal of exposed areas. After development, preferred embodiments of the photochemically images systems exhibit insignificant changes in the highly resolved features (one micron) in the patterned image upon postbaking at temperatures of about 230°C and is, thereafter readily stripped. The high thermal stability exhibited by the photochemically imaged systems formed from the positive photoresist compositions of the present invention allows faster processing at higher temperatures, on equipment like plasma etchers and ion implanters; the developed photochemically imaged systems of the present invention retain high resolution, i.e., retain sharp, steep patterned image profiles.

Inventors

  • 👤 F. R. Hopf
  • 👤 C. E. Osuch
  • 👤 M. J. Mcfarland

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-03 12:05
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03C; G03C1/00; G03F7/022; G03F7/023; G03F7/0233

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 63 words
An alkali-insoluble positive photoresist composition comprising a mixture of (a) an alkali-insoluble photoactive compound, capable of being transformed into an alkali-soluble species upon exposure to actinic radiation, in an amount sufficient to render the mixture relatively alkali-insoluble before exposure to actinic radiation; and (b) a polymer comprising an amount of (̵CO-NH-CO)̵ groups sufficient to render the mixture alkali-soluble upon exposure to actinic radiation.
Claim 2
Dependent Claim 63 words
An alkali-insoluble positive photoresist composition comprising a mixture of (a) an alkali-insoluble photoactive compound, capable of being transformed into an alkali-soluble species upon exposure to actinic radiation, in an amount sufficient to render the mixture relatively alkali-insoluble before exposure to actinic radiation; and (b) a polymer comprising an amount of (̵CO-NH-CO)̵ groups sufficient to render the mixture alkali-soluble upon exposure to actinic radiation.
Claim 3
Dependent Claim 20 words
The alkali-insoluble positive photoresist composition of claim 1 wherein the polymer comprises a copolymer containing an effective amount of residues
Claim 4
Dependent Claim 78 words
The alkali insoluble positive photoresist composition of claim 2 wherein the copolymer is formed from polymerization of a film-forming monomer selected from styrene, a-methylstyrene, 4-(C 1 -C 5 alkyl)styrene, 2-(C 1 -C 5 alk y l)styrene, 2,4-di(C 1 -C 5 alkyl)styrene or a monomer having the formula H 2 C=Cr a M and maleimide, wherein M is CN or C0 2 R b wherein R b is methyl or allyl and wherein R a is H or methyl.
Claim 5
Dependent Claim 68 words
A positive photoresist composition comprising a mixture of (a) about 65-99 weight percent of a copolymer prepared from and, optionally, an effective amount of wherein R 1 and R 4 are independently H or (C 1 -C 5 ) alkyl and wherein R 5 is (C 1 -C 5 ) alkyl; and (b) about 1-35 weight percent of a photoactive compound becoming alkali-soluble upon exposure to actinic radiation.
Claim 6
Dependent Claim 68 words
A positive photoresist composition comprising a mixture of (a) about 65-99 weight percent of a copolymer prepared from and, optionally, an effective amount of wherein R 1 and R 4 are independently H or (C 1 -C 5 ) alkyl and wherein R 5 is (C 1 -C 5 ) alkyl; and (b) about 1-35 weight percent of a photoactive compound becoming alkali-soluble upon exposure to actinic radiation.
Claim 7
Dependent Claim 25 words
The positive photoresist composition of claim 4 wherein the photoactive compound upon exposure to actinic radiation is converted into a compound containing carboxylic acid moieties.
Claim 8
Dependent Claim 33 words
The positive photoresist composition of claim 4 wherein the copolymer comprises about 40 mole % of maleimide, about 10 mole % of N-(C 1 -C 5 alkyl)maleimide, and the balance a styrene unit.
Claim 9
Dependent Claim 82 words
A photosensitive element comprising a substrate bearing a layer of a photoresist composition comprising a mixture of (a) about 65-99 percent of a copolymer prepared from and, optionally, an effective amount of: wherein R 1 to R 4 are independently H or (C 1 -C 5 alkyl) and wherein R 5 is (C 1 -C 5 alkyl) and (b) about 1-35 weight percent of a photoactive compound wherein the photoresist composition upon exposure to actinic radiation is rendered soluble in alkaline solution.
Claim 10
Dependent Claim 82 words
A photosensitive element comprising a substrate bearing a layer of a photoresist composition comprising a mixture of (a) about 65-99 percent of a copolymer prepared from and, optionally, an effective amount of: wherein R 1 to R 4 are independently H or (C 1 -C 5 alkyl) and wherein R 5 is (C 1 -C 5 alkyl) and (b) about 1-35 weight percent of a photoactive compound wherein the photoresist composition upon exposure to actinic radiation is rendered soluble in alkaline solution.
Claim 11
Dependent Claim 39 words
An alkali soluble composition comprising a copolymer formed by polymerization of at least about 10 mole % of maleimide and the balance being N-(C l -C 5 alkyl)maleimide and styrene, or a-methylstyrene, or 2,4-di(C l -C 5 alkyl) styrene.
Claim 12
Dependent Claim 39 words
An alkali soluble composition comprising a copolymer formed by polymerization of at least about 10 mole % of maleimide and the balance being N-(C l -C 5 alkyl)maleimide and styrene, or a-methylstyrene, or 2,4-di(C l -C 5 alkyl) styrene.
Claim 13
Dependent Claim 157 words
A method of preparing a photochemical image which comprises (a) depositing on a face of a substrate a solution of the positive photoresist composition of claim 8 and a suitable organic solvent under conditions and in an amount sufficient to produce a uniform deposit having a thickness on the order of about 0.1 micron to about 20 microns of the composition of claim 1 on a face of the substrate; (b) treating said deposit under conditions of temperature and pressure sufficient to remove substantially all the suitable organic solvent; (c) image wise exposing through a mask said film to actinic radiation in the range of about 200-700 nm for a time sufficient to render the exposed areas of the film soluble in alkaline solution; and (d) contacting the exposed film with a developer solution comprising an alkaline material having a pH greater than about 10 for a time sufficient to remove the exposed areas of the film.
Claim 14
Dependent Claim 19 words
The method of claim 9 which further comprises heating said developed film at a temperature of at about 250°C.

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