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US4985332A Expired / Lapsed US ⏱️ 0.0 years remaining

Resist material with carbazole diazonium salt acid generator and process for use

Assignee: EIDP Inc
•
Filing: 1990-04-10
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Granted: 1991-01-15
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Expires: 2010-04-10
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Abstract

Abstract Excellent resolution and sensitivity in the patterning of resists utilized in device and mask manufacture is obtained with a specific composition. In particular this composition involves polymers having recurring pendant acid labile α-alkoxyalkyl carboxylic acid ester and/or hydroxyaromatic ether moieties in the presence of an acid generator comprising a novel diazonium salt.

Inventors

  • 👤 Albert G. Anderson
  • 👤 Walter R. Hertler
  • 👤 Robert C. Wheland
  • 👤 Yuan Yu G. Chen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 01:58
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/039; G03F7/016; G03F7/021; G03F7/0212

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 219 words
A material comprising: a polymer chosen from the group consisting of compositions having a polymer backbone and pendant acid labile groups bound directly or indirectly to said backbone, said pendant groups represented by the formula: ##STR5## wherein n=0-4 R 1 is hydrogen or a C 1 -C 6 alkyl; R 2 is a C 1 -C 6 alkyl; and R 3 and R 4 independently are hydrogen or C 1 -C 6 alkyl where the definition of C 1 -D 6 alkyl includes the joining of R 1 and R 2 or R 1 and either R 3 or R 4 , or R 2 and either R 3 or R 4 to form a 5-, 6- or 7-membered ring; and material that forms an acid upon irradiation comprising carbazole diazonium salts of the structures: ##STR6## wherein: Y is PF 6 - , AsF 6 - , SbF 6 - , FeCl 4 - , SnCl 6 -2 , SbCl 6 - , BF 4 - or BiCl 5 -2 ; and R is selected from the group consisting of C x H 2x+1 where x is 1-16, benzyl, phenyl, substituted benzyl, substituted phenyl and cycloalkyl, provided, however, where N 2 Y is in the "1" position as in the second structure, R is not phenyl or substituted phenyl.
Claim 2
Dependent Claim 219 words
A material comprising: a polymer chosen from the group consisting of compositions having a polymer backbone and pendant acid labile groups bound directly or indirectly to said backbone, said pendant groups represented by the formula: ##STR5## wherein n=0-4 R 1 is hydrogen or a C 1 -C 6 alkyl; R 2 is a C 1 -C 6 alkyl; and R 3 and R 4 independently are hydrogen or C 1 -C 6 alkyl where the definition of C 1 -D 6 alkyl includes the joining of R 1 and R 2 or R 1 and either R 3 or R 4 , or R 2 and either R 3 or R 4 to form a 5-, 6- or 7-membered ring; and material that forms an acid upon irradiation comprising carbazole diazonium salts of the structures: ##STR6## wherein: Y is PF 6 - , AsF 6 - , SbF 6 - , FeCl 4 - , SnCl 6 -2 , SbCl 6 - , BF 4 - or BiCl 5 -2 ; and R is selected from the group consisting of C x H 2x+1 where x is 1-16, benzyl, phenyl, substituted benzyl, substituted phenyl and cycloalkyl, provided, however, where N 2 Y is in the "1" position as in the second structure, R is not phenyl or substituted phenyl.
Claim 3
Dependent Claim 15 words
The material of claim 1 wherein the polymer comprises a copolymer, terpolymer or block polymer.
Claim 4
Dependent Claim 17 words
The material of claim 2 wherein said material comprises a copolymer of benzyl methacrylate and tetrahydropyranyl methacrylate.
Claim 5
Dependent Claim 21 words
The material of claim 2 w herein a monomer used to form said copolymer, terpolymer or block polymer comprises 4-tetrahydropyranyloxybenzyl methacrylate.
Claim 6
Dependent Claim 14 words
The material of claim 1 wherein said polymer comprises a homopolymer of 4-tetrahydropyranyloxybenzyl methacrylate.
Claim 7
Dependent Claim 19 words
The material of claim 1 wherein said polymer is selected from the group consisting of polymethacrylates, polyacrylates and polystyrenes.
Claim 8
Dependent Claim 34 words
The material of claim 6 wherein said polymer comprises a polystyrene and said pendant acid labile group is bound to the polymer backbone at a carbon atom of a benzene ring within said polystyrene.
Claim 9
Dependent Claim 14 words
The material of claim 6 wherein said polymer comprises an acrylic or methacrylic polymer
Claim 10
Dependent Claim 14 words
The material of claim 1 wherein said polymer is prepared by group transfer polymerization.
Claim 11
Dependent Claim 14 words
The material of claim 1 wherein said polymer is prepared by free radical polymerization.
Claim 12
Dependent Claim 14 words
The material of claim 1 wherein said polymer has a polydispersity less than 1.75.
Claim 13
Dependent Claim 24 words
The material of claim 2 wherein the polymer contains some monomers having pendant acid labile groups and comonomers having no pendant acid labile groups.
Claim 14
Dependent Claim 27 words
The material of claim 12 wherein the comonomers having no pendant acid labile groups is selected from methyl methacrylate, butyl methacrylate, benzyl methacrylate, benzyl acrylate and styrene.
Claim 15
Dependent Claim 17 words
The material of claim 13 wherein glycidyl methacrylate is added in a quantity suitable for adhesion promotion.
Claim 16
Dependent Claim 20 words
The material of claim 14 wherein the quantity of glycidyl methacrylate added is no greater than about 5 mole %.
Claim 17
Dependent Claim 17 words
The material of claim 13 wherein the comonomer having no pendant acid labile groups is benzyl methacrylate.
Claim 18
Dependent Claim 9 words
The material of claim 1 further including a solvent.
Claim 19
Dependent Claim 10 words
The material of claim 15 wherein said solvent is cyclopentanone.
Claim 20
Dependent Claim 13 words
The material of claim 15 wherein said material is applied to a substrate.
Claim 21
Dependent Claim 20 words
The material of claim 2 wherein a monomer used to form said copolymer, terpolymer or block polymer comprises tetrahydropyranyl methacrylate.

References Cited (Backward Citations)

CA672947A Cited
US3062644A Cited
US3779778A Cited
US4417034A Cited
JPS58118641A Cited
US4491628A Cited
US4515885A Cited
US4686547A Cited
EP0264908A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-01-14 1994-07-16 1995-01-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-01-14 1998-07-16 1999-01-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-01-14 2002-07-16 2003-01-15 $7700.00 Window Closed / Lapsed

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