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US4524121A Expired / Lapsed US ⏱️ 0.0 years remaining

Positive photoresists containing preformed polyglutarimide polymer

Assignee: Rohm and Haas Co
•
Filing: 1983-11-21
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Granted: 1985-06-18
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Expires: 2003-11-21
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Abstract

Abstract This invention relates to a positive photoresist system possessing a high degree of thermal stability. The photoresist system contains a preformed polyglutarimide polymer dissolved in a non-reacting solvent. The positive resist is capable of achieving high resolution images by exposure to a wide range of wavelengths and development using an aqueous base developer. The photoresist system is also suitable for use as a planarizing layer in a multiple layer system.

Inventors

  • 👤 Robert D. Gleim
  • 👤 Mark P. de Grandpre

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 15:46
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/04; G03F7/0045; G03F7/022; G03F7/023; G03F7/0233; G03F7/09; G03F7/094

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 89 words
A positive photoresist comprising a preformed, non-crosslinked polyglutarimide polymer formed from an ester of (meth)acrylic acid and having at least five percent by weight glutarimide units of the structure ##STR5## where R 1 , R 2 and R 3 independently represent hydrogen or unsubstituted or substituted alkyl, aryl, aralky, or alkaryl hydrocarbons having from one to twenty carbon atoms and where at least 20 mole percent of the R 3 substituents are hydrogen, dissolved in a non-aqueous, spinning solvent, and where the photoresist is developable with an aqueous solution.
Claim 2
Dependent Claim 89 words
A positive photoresist comprising a preformed, non-crosslinked polyglutarimide polymer formed from an ester of (meth)acrylic acid and having at least five percent by weight glutarimide units of the structure ##STR5## where R 1 , R 2 and R 3 independently represent hydrogen or unsubstituted or substituted alkyl, aryl, aralky, or alkaryl hydrocarbons having from one to twenty carbon atoms and where at least 20 mole percent of the R 3 substituents are hydrogen, dissolved in a non-aqueous, spinning solvent, and where the photoresist is developable with an aqueous solution.
Claim 3
Dependent Claim 18 words
The positive photoresist of claim 1 further comprising a positive acting photosensitizer dissolved in said non-aqueous spinning solvent.
Claim 4
Dependent Claim 28 words
The positive photoresist of claim 1 comprising from about 5 to about 30 weight non-crosslinked polyglutarimide and from about 95 to about 70 weight percent non-aqueous, spinning solvent.
Claim 5
Dependent Claim 29 words
The positive photoresist of claim 3 comprising from about 10 to about 20 weight percent non-crosslinked polyglutarimide and from about 90 to about 80 weight percent non-aqueous, spinning solvent.
Claim 6
Dependent Claim 30 words
The positive photoresist of claim 2 where the concentration of said photosensitizer is from about 5 to about 30 weight percent based on the weight of said preformed, non-crosslinked polyglutarimide.
Claim 7
Dependent Claim 21 words
The positive photoresist of claim 2 wherein said photosensitizer is selected from the group consisting of diazooxides, and bis(o-nitrobenzyl)-1,7 heptane dioate.
Claim 8
Dependent Claim 31 words
The positive photoresist of claim 1 wherein the polyglutarimide has an atomic ratio of carbon to nitrogen of at least 8 and a glass transition temperature of at least 140° C.
Claim 9
Dependent Claim 20 words
The positive photoresist of claim 1 where said preformed polyglutarimide is formed by imidizing a polymethyl methacrylate polymer with ammonia.
Claim 10
Dependent Claim 35 words
The positive photoresist of claim 8 wherein said preformed polyglutarimide is formed by imidizing a polymethyl methacrylate polymer with a mixed reactant system comprising at least 20 weight percent ammonia and at least one alkylamine.
Claim 11
Dependent Claim 87 words
The positive photoresist of claim 1 wherein the non-aqueous, spinning solvent comprises a non-solvent for polyglutarimides selected from the group consisting of: acetyl acetone; 1-methoxy-2-propanol; cyclohexanone; chlorobenzene; mixtures of ethylene glycol monoethylether acetate, xylene and butyl acetate; xylene, toluene; butyl acetate; 1,2-dimethoxyethane; and ethylene glycol monomethyl ether in combination with one or more of the non-spinning solvents or mixtures thereof selected from the group consisting of: amide, polar, aprotic solvents; hydroxylic, polar, protic solvents; polar, aprotic, ketonic solvents; small chain, polar, carboxylic acids; and polar, basic, ethers.
Claim 12
Dependent Claim 15 words
The photoresist of claim 2 wherein the photosensitizer absorbs near, mid or deep UV radiation.
Claim 13
Dependent Claim 25 words
A surface comprising an adherent, uniform, aqueous base developable, film having a thickness of about one micrometer, of the photoresist of claims 1 or 2.
Claim 14
Dependent Claim 17 words
The surface film of claim 12 having a thickness of about 0.5 micrometer to about 3.0 micrometers.
Claim 15
Dependent Claim 27 words
A multilayer photoresist comprising as a planarizing layer the photoresist of claim 1 and at least one other layer capable of being imaged on said planarizing layer.
Claim 16
Dependent Claim 26 words
The multilayer photoresist of claim 14 in which the planarizing layer and the adjacent layer deposited on said planarizing layer do not form an interfacial scum.
Claim 17
Dependent Claim 19 words
The photoresist of claim 1 being thermally resistant to temperatures of from about 140° C. to about 240° C.
Claim 18
Dependent Claim 11 words
The photoresist of claim 1 being resistant to reactive ion etching.
Claim 19
Dependent Claim 62 words
A process for forming an image on a surface comprising depositing an adherent positive acting film on said surface from the photoresist of claim 1, exposing a portion of said film to a source of energy that increases the dissolution rate of said polyglutarimide in a developer, and developing the exposed portion of said film with said developer to form said image.
Claim 20
Dependent Claim 16 words
The process of claim 18 wherein said film is deposited from said photoresist of claim 2.
Claim 21
Dependent Claim 23 words
The process of claim 18 wherein said source of energy is selected from the group consisting of ultraviolet, e-beam, ion beam and x-ray.
Claim 22
Dependent Claim 20 words
The process of claim 18 further comprising softbaking said film prior to exposing said film to said source of energy.
Claim 23
Dependent Claim 160 words
A process for forming an image on a surface comprising depositing an adherent, planarizing film on said surface forming a second surface, said planarizing film comprising a preformed non-crosslinked polyglutarimide polymer formed from an ester of (meth)acrylic acid and having at least five percent by weight glutarimide units of the structure ##STR6## where R 1 , R 2 and R 3 independently represent hydrogen or unsubstituted or substituted alkyl, aryl, aralky, or alkaryl hydrocarbons having from one to twenty carbon atoms and where at least 20 mole percent of the R 3 substituents are hydrogen, dissolved in a non-aqueous, spinning solvent, depositing a second film capable of being imaged on said second surface, exposing a portion of said second film to a source of radiation, developing the exposed portion of said second film to create a mask on the planarizing film, and transferring said image from said second film through said mask and the planarizing film and onto said surface.
Claim 24
Dependent Claim 160 words
A process for forming an image on a surface comprising depositing an adherent, planarizing film on said surface forming a second surface, said planarizing film comprising a preformed non-crosslinked polyglutarimide polymer formed from an ester of (meth)acrylic acid and having at least five percent by weight glutarimide units of the structure ##STR6## where R 1 , R 2 and R 3 independently represent hydrogen or unsubstituted or substituted alkyl, aryl, aralky, or alkaryl hydrocarbons having from one to twenty carbon atoms and where at least 20 mole percent of the R 3 substituents are hydrogen, dissolved in a non-aqueous, spinning solvent, depositing a second film capable of being imaged on said second surface, exposing a portion of said second film to a source of radiation, developing the exposed portion of said second film to create a mask on the planarizing film, and transferring said image from said second film through said mask and the planarizing film and onto said surface.
Claim 25
Dependent Claim 14 words
The process of claim 22 wherein said second film comprises a positive acting photoresist.
Claim 26
Dependent Claim 26 words
The process of claim 22 wherein said image formed on said second film is transferred through said planarizing film onto said surface using reactive ion etching.
Claim 27
Dependent Claim 14 words
The process of claim 22 wherein said second film is a negative acting photoresist.
Claim 28
Dependent Claim 33 words
The process of claim 23 wherein said planarizing film is exposed to deep UV and developed using an aqueous base developer to transfer said image formed on said second film onto said surface.
Claim 29
Dependent Claim 17 words
The process of claim 26 wherein said planarizing film further comprises a photosensitizer sensitive to deep UV.
Claim 30
Dependent Claim 84 words
The process of claim 22 further comprising adding at least one layer, intermediate to said planarizing film and said second film, onto said planarizing film, said intermediate layer being resistant to said developing means used to create an image on said second film, and wherein said intermediate layer is developed through said mask formed on said second film to form a second image using plasma or wet etching to form a mask for transferring said second image onto said surface through said planarizing layer.
Claim 31
Dependent Claim 32 words
The process of claim 19 wherein said second image on said intermediate layer is transferred onto said surface by dry etching said planarizing layer through said mask formed on said intermediate layer.
Claim 32
Dependent Claim 85 words
The spinning solvent of the photoresist of claim 2 comprising a non-solvent for polyglutarimides selected from the group consisting of: acetyl acetone; 1-methoxy-2-propanol; cyclohexanone; chlorobenzene; mixtures of ethylene glycol monoethylether acetate, xylene and butyl acetate; xylene; toluene; butyl acetate; 1,2-dimethoxyethane; and ethylene glycol monomethyl ether, in combination with one or more of the non-spinning solvents or mixtures thereof selected from the group consisting of: amide, polar, aproptic solvents; hydroxylic, polar, protic solvents; polar, aprotic, ketonic solvents; small chain, polar, carboxylic acids; and polar, basic, ethers.

References Cited (Backward Citations)

US4079041A Cited
US3964908A Cited
US4121936A Cited
US4254232A Cited
US4246374A Cited
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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) 1988-06-17 1988-12-17 1989-06-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-06-17 1992-12-17 1993-06-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-06-17 1996-12-17 1997-06-18 $7700.00 Window Closed / Lapsed

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