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US4540650A Expired / Lapsed US ⏱️ 0.0 years remaining

Photoresists suitable for forming relief structures of highly heat-resistant polymers

Assignee: Novartis Corp
•
Filing: 1983-09-13
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Granted: 1985-09-10
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Expires: 2003-09-13
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Abstract

Abstract Photoresists suitable for use for forming relief structures of highly heat-resistant polymers and which contain soluble polymeric precursors which carry radiation-reactive radicals bonded through carboxylic ester groups have an increased light-sensitivity when they also contain at least one radiation-reactive, polymerizable allyl compound which has a boiling point above 180°, the allyl group thereof being bonded via an oxygen, sulfur and/or nitrogen atom. The highly heat-resistant polymers which can be prepared by means of these photoresists have excellent chemical, electrical and mechanical properties.

Inventors

  • 👤 Rudolf Klug
  • 👤 Hartmut Hartner
  • 👤 Hans-Joachim Merrem
  • 👤 Karl H. Neisius

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 21:29
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/26; G03F7/004; G03F7/027; C; C08; C08F; C08F291/00; C08F291/18

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 87 words
In a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages; said amide having the structure of the reaction product of a carboxylic aid and an amine, the improvement wherein said photoresist further comprises at least 3% by weight, relative to the weight of said soluble prepolymer, of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 2
Dependent Claim 87 words
In a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages; said amide having the structure of the reaction product of a carboxylic aid and an amine, the improvement wherein said photoresist further comprises at least 3% by weight, relative to the weight of said soluble prepolymer, of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 3
Dependent Claim 36 words
The photoresist of claim 1, wherein said allyl compound is a derivative of an hydroxylic compound, one or more hydroxyl groups of which are replaced by allyloxy, allylthio, allylsulfinyl or allylsulfonyl groups or a mixture thereof.
Claim 4
Dependent Claim 26 words
The photoresist of claim 2, wherein said hydroxylic compound is a C 2-8 unsubstituted or keto- or phenyl-substituted straight or branched chain aliphatic diol or polyol.
Claim 5
Dependent Claim 46 words
The photoresist of claim 3, wherein said hydroxylic compound is ethylene glycol, 1,2- or 1,3-propylene glycol, glycerol, 1,2-, 1,3-, 1,4 or 2,4-butanediol, 1,2,3- or 1,2,4-butanetriol, erythritol, xylitol, sorbitol, mannitol, dimethylolethane, trimethylolethane, pentaerythritol, phenylethylene glycol, 1-phenyl-2,3-dihydroxypropane, 1-phenyl-1,2-dihydroxypropane, 1- or 2-phenylglycerol, 1-phenylbutane-2,4-diol, dimethylolpropane, trimethylolpropane or a mixture thereof.
Claim 6
Dependent Claim 18 words
The photoresist of claim 2, wherein at least one of said hydroxyl groups is esterified with an acid.
Claim 7
Dependent Claim 31 words
The photoresist of claim 1, wherein said allyl compound is a mono- or polyester or thioester of benzoic acid, phthalic acid, terephthalic acid or pyromellitic acid with allyl alcohol or allylthiol.
Claim 8
Dependent Claim 35 words
The photoresist of claim 1, wherein said allyl compound is a derivative of a saturated or unsaturated five- or six-membered heterocyclic amine, one or more nitrogen atoms of which are substituted with an allyl group.
Claim 9
Dependent Claim 29 words
The photoresist of claim 7, wherein said heterocyclic amine is pyrrole, pyrroline, pyrrolidine, pyrazole, pyrazoline, pyrazolidine, imidazole, imidazoline, imidazolidine, oxazolidine, thiazolidine, triazole, piperidine, 1,4-dihydropyridine, piperazine, triazine or isocyanuric acid.
Claim 10
Dependent Claim 16 words
The photoresist of claim 1, wherein said allyl compound is an N-allyl substituted amide or imide.
Claim 11
Dependent Claim 111 words
The photoresist of claim 1, wherein said allyl compound is allyl phenyl ether, glycerol diallyl ether, erythritol triallyl ether, trimethylolpropane diallyl and triallyl ethers, pentaerythritol diallyl, triallyl and tetraallyl ethers, pentaerythritol triallyl ether benzoate, pentaerythritol triallyl ether monophthalate and diphthalate, pentaerythritol triallyl ether monoterephthalate and diterephthalate, pentaerythritol triallyl ether monopyromellitate, dipyromellitate, tripyromellitate and tetrapyromellitate, diallyl sulfoxide, diallyl sulfone, allyl benzoate, monoallyl and diallyl phthalate, monoallyl, diallyl, triallyl and tetraallyl pyromellitate, allyl phenyl thioether, 2,4,6-trisallyloxy-1,3,5-triazine, 2,4-diallyloxyimidazolidine, N-allylpyrrole, N-allylimidazole, N-allylpiperidine, N,N-diallylpiperazine, N,N,N-triallyltriazine, 2,4,6-tris(allylamino)triazine, triallyl-s-triazine-2,4,6-(1H,3H,5H)-trione, hexaallylmelamine, N,N'-diallylpyromellitic bisimide, N,N'-diallyl benzophenone-3,4,3',4'-tetracarboxylic bisimide, N-allylphthalimide, N-monoallylbenzamide, N,N-diallylbenzamide, N,N-diallylfumaric acid monoamide, N,N-diallylmaleic acid monoamide, N,N,N',N'-tetraallylfumaric acid bisamide, the monoethyl ester of N,N-diallylfumaric acid monoamide or a mixture thereof.
Claim 12
Dependent Claim 16 words
The photoresist of claim 1, wherein said allyl compound has a boiling point above 200° C.
Claim 13
Dependent Claim 26 words
The photoresist of claim 1, wherein the amount of said allyl compound is at least 10% by weight relative to the weight of said soluble prepolymer.
Claim 14
Dependent Claim 14 words
The photoresist of claim 12 wherein said amount is at least 15% by weight.
Claim 15
Dependent Claim 27 words
The photoresist of claim 1, wherein the amount of said allyl compound is between 3 and 30% by weight relative to the weight of said soluble prepolymer.
Claim 16
Dependent Claim 157 words
In a process for forming relief structures of highly heat-resistant polymers, comprising the steps of applying a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages, said amide having the structure of the reaction product of a carboxylic acid and an amine, said photoresist being applied in the form of a layer or sheet to a substrate, drying the layer or sheet, irradiating the dried, radiation-sensitive layer or sheet through a negative original or using a guided collimated beam, dissolving out or stripping off the non-irradiated portions of the layer or sheet to form a relief structure, the improvement wherein said photoresist further comprises at least 3% by weight, relative to the weight of said soluble prepolymer, of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 17
Dependent Claim 157 words
In a process for forming relief structures of highly heat-resistant polymers, comprising the steps of applying a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages, said amide having the structure of the reaction product of a carboxylic acid and an amine, said photoresist being applied in the form of a layer or sheet to a substrate, drying the layer or sheet, irradiating the dried, radiation-sensitive layer or sheet through a negative original or using a guided collimated beam, dissolving out or stripping off the non-irradiated portions of the layer or sheet to form a relief structure, the improvement wherein said photoresist further comprises at least 3% by weight, relative to the weight of said soluble prepolymer, of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 18
Dependent Claim 16 words
The process of claim 15, wherein said allyl compound has a boiling point above 200° C.
Claim 19
Dependent Claim 26 words
The process of claim 15, wherein the amount of said allyl compound is at least 10% by weight relative to the weight of said soluble prepolymer.
Claim 20
Dependent Claim 111 words
The process of claim 15, wherein said allyl compound is allyl phenyl ether, glycerol diallyl ether, erythritol triallyl ether, trimethylolpropane diallyl and triallyl ethers, pentaerythritol diallyl, triallyl and tetraallyl ethers, pentaerythritol triallyl ether benzoate, pentaerythritol triallyl ether monophthalate and diphthalate, pentaerythritol triallyl ether monoterephthalate and diterephthalate, pentaerythritol triallyl ether monopyromellitate, dipyromellitate, tripyromellitate and tetrapyromellitate, diallyl sulfoxide, diallyl sulfone, allyl benzoate, monoallyl and diallyl phthalate, monoallyl, diallyl, triallyl and tetraallyl pyromellitate, allyl phenyl thioether, 2,4,6-trisallyloxy-1,3,5-triazine, 2,4-diallyloxyimidazolidine, N-allylpyrrole, N-allylimidazole, N-allylpiperidine, N,N-diallylpiperazine, N,N,N-triallyltriazine, 2,4,6-tris(allylamino)triazine, triallyl-s-triazine-2,4,6-(1H,3H,5H)-trione, hexaallylmelamine, N,N'-diallylpyromellitic bisimide, N,N'-diallyl benzophenone-3,4,3',4'-tetracarboxylic bisimide, N-allylphthalimide, N-monoallylbenzamide, N,N-diallylbenzamide, N,N-diallylfumaric acid monoamide, N,N-diallylmaleic acid monoamide, N,N,N',N'-tetraallylfumaric acid bisamide, the monoethyl ester of N,N-diallylfumaric acid monoamide or a mixture thereof.
Claim 21
Dependent Claim 10 words
A relief structure formed by the process of claim 15.
Claim 22
Independent Claim 92 words
A method of reducing the irradiation time of a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages, said amide having the structure of the reaction product of a carboxylic acid and an amine, comprising incorporating in said photoresist at least 3% by weight, relative to the weight of said soluble prepolymer of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 23
Independent Claim 92 words
A method of reducing the irradiation time of a photoresist comprising a soluble polyamide-ester prepolymer containing radiation-reactive radicals bonded to the repeating unit of the prepolymer through carboxylic ester linkages, said amide having the structure of the reaction product of a carboxylic acid and an amine, comprising incorporating in said photoresist at least 3% by weight, relative to the weight of said soluble prepolymer of at least one radiation-reactive polymerizable allyl compound having a boiling point above 180° C., the allyl groups thereof being bonded through an oxygen, sulfur or nitrogen atom.
Claim 24
Dependent Claim 12 words
The process of claim 15, wherein the resultant relief structure is heat-treated.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-09-09 1989-03-11 1989-09-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-09-09 1993-03-11 1993-09-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-09-09 1997-03-11 1997-09-10 $7700.00 Window Closed / Lapsed

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