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US5889141A
Expired / Lapsed
US
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Photoimageable compositions comprising polyquinoline polymer and diazo compound
Assignee: Resonac Corp
•
Filing: 1997-04-28
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Granted: 1999-03-30
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Expires: 2017-04-28
Abstract
Abstract Photoimageable polyquinoline compositions comprise a polyquinoline polymer, a diazonaphthoquinone and optionally a photosensitizer. The composition is prepared by dissolving the polyquinoline polymer, diazonaphthoquinone and photosensitizer in a solvent to form a solution, coating the solution onto a substrate and thereafter removing the solvent to form a film. The film is exposed to light through a photomask and developed by immersion in a selective solvent to yield a photopatterned dielectric film.
Inventors
- 👤 Matthew L. Marrocco, III
- 👤 Makoto Kaji
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:26
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0683; C08G73/0688; G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233
Claims Analysis
Total Claims: 64
Claim 1
Independent Claim
11 words
A photoimageable composition comprising a polyquinoline polymer and a diazonaphthoquinone unit.
Claim 2
Dependent Claim
11 words
A photoimageable composition comprising a polyquinoline polymer and a diazonaphthoquinone unit.
Claim 3
Dependent Claim
35 words
The composition of claim 1 wherein the amount of diazonaphthoquinone unit is from about 1 mol % to about 100 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 4
Dependent Claim
35 words
The composition of claim 1 wherein the amount of diazonaphthoquinone unit is from about 10 mol % to about 90 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 5
Dependent Claim
35 words
The composition of claim 1 wherein the amount of diazonaphthoquinone unit is from about 20 mol % to about 80 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 6
Dependent Claim
16 words
The composition of claim 1 wherein the diazonaphthoquinone unit is chemically bonded to the polyquinoline polymer.
Claim 7
Dependent Claim
116 words
The composition of claim 1 wherein the diazonaphthoquinone unit has the structural formula: ##STR30## wherein D may be on any of positions 3 to 8 of the naphthoquinone and is selected from the group consisting of H, alkyl groups having from about 1 to about 26 carbon atoms, aryl groups having from about 6 to about 30 carbon atoms, alkoxy groups having from about 1 to about 26 carbon atoms, aryloxy groups having from about 6 to about 30 carbon atoms, COX and SO 2 X wherein X is selected from the group consisting of OH, alkoxy, aryloxy, Cl or Br and wherein the naphthoquinone may be substituted by one or more independently selected R groups.
Claim 8
Dependent Claim
29 words
The composition of claim 1 wherein the diazonaphthoquinone unit has the following structure: ##STR31## wherein X is selected from the group consisting of OH, alkoxy, aryloxy, Cl and Br.
Claim 9
Dependent Claim
97 words
The composition of claim 1 wherein the diazonaphthoquinone unit has the following structure: ##STR32## wherein W is selected from the group consisting of nil, divalent alkyl groups having from 1 to about 26 carbon atoms, arylene groups having from about 6 to about 30 carbon atoms, oxy, esters having from 1 to about 24 carbon atoms, sulfonate esters having from 0 to about 24 carbon atoms, thio, sulfones having from 0 to about 24 carbon atoms, ketones having from 1 to about 24 carbon atoms, amides having from 1 to about 24 carbon atoms, and catenations thereof.
Claim 10
Dependent Claim
46 words
The composition of claim 1 wherein the diazonaphthoquinone unit has the following structure: ##STR33## wherein Z is selected from the group consisting of divalent alkyl groups having from 1 to about 26 carbon atoms and arylene groups having from about 6 to about 30 carbon atoms.
Claim 11
Dependent Claim
14 words
The composition of claim 1 wherein the diazonaphthoquinone unit has the following structure: ##STR34##
Claim 12
Dependent Claim
44 words
The composition of claim 1 wherein the diazonaphthoquinone unit is a mixture of diazo compounds having the structural formula: ##STR35## wherein A=H or A' and A' is represented by the formula: ##STR36## and the ratio of H/A' is from about 3.5/0.5 to about 0.5/3.5.
Claim 13
Dependent Claim
50 words
The composition of claim 1 where polyquinoline polymer has repeat units having the structure ##STR37## wherein Y is a divalent radical selected from the group consisting of nil, --O--, --N(H)--, --S--, carbonyl, sulfone, hexafluoroisopropylidine, 1-aryl-2,2,2-trifluoroethylidene, hexafluoroisopropylidene diphenoxy, 1-aryl-2,2,2-trifluoroethylidene diphenoxy, phenylene, phenylenedioxy, isopropylidene, isopropylidene diphenoxy, aryl ethylidene, and aryl ethylidene diphenoxy.
Claim 14
Dependent Claim
15 words
The composition of claim 1 where polyquinoline polymer has repeat units having the structure ##STR38##
Claim 15
Dependent Claim
15 words
The composition of claim 1 where polyquinoline polymer has repeat units having the structure ##STR39##
Claim 16
Dependent Claim
9 words
The composition of claim 1 further comprising a photosensitizer.
Claim 17
Dependent Claim
25 words
The composition of claim 15 wherein the photosensitizer is present in an amount of from about 0.001% to about 20% by weight of the polyquinoline.
Claim 18
Dependent Claim
25 words
The composition of claim 15 wherein the photosensitizer is present in an amount of from about 0.01% to about 10% by weight of the polyquinoline.
Claim 19
Dependent Claim
25 words
The composition of claim 15 wherein the photosensitizer is present in an amount of from about 0.1% to about 1% by weight of the polyquinoline.
Claim 20
Dependent Claim
54 words
The composition of claim 15 wherein the photosensitizer is selected from the group consisting of phenothiazine, benzo c!phenothiazine, benzophenone, 4,4'-bis(dimethylamino)bcnzophenone, xanthone, triphenylene, thioxanthone, anthraquinone, anthracene, 9,10-diphenylanthracene, 9,10-bis(phenylethynyl)anthracenc, 2-methoxyanthracene, 1,5-dimethoxyanthracene, 1,8-dimethoxyanthracene, 6-chloroanthracene, 1,5-dichloroanthracene, 5,12-bis(phenylethynyl)naphthacene, chrysene, pyrene, 1,3-dicyanobenzene, phenyl-3-cyanobenzoate, 2-chlorothioxanthane, 2-methylthioxanthane, 2,4-diethylthioxanthane, 7-diethylamino-3-(2-thenoyl) coumarin, 3,3'-carbonyl bis(7-diethylamino coumarin), 7-diethyl amino-3-benzoyl coumarin, 3,3'-carbonyl bis(7-dimethoxy coumarin) and 7-H-benzo c!phenothiazine.
Claim 21
Independent Claim
47 words
A method for preparing a photoimageable polyquinoline film comprising: dissolving a polyquinoline polymer and a diazonaphthoquinone unit in a solvent to form a solution; applying a coating of the solution to a substrate; and removing the solvent from the coated solution to thereby form a photoimageable film.
Claim 22
Independent Claim
47 words
A method for preparing a photoimageable polyquinoline film comprising: dissolving a polyquinoline polymer and a diazonaphthoquinone unit in a solvent to form a solution; applying a coating of the solution to a substrate; and removing the solvent from the coated solution to thereby form a photoimageable film.
Claim 23
Dependent Claim
26 words
The method of claim 20 wherein the concentration of polyquinoline polymer in the solution is from about 0.1% to about 60% by weight of the solution.
Claim 24
Dependent Claim
26 words
The method of claim 20 wherein the concentration of polyquinoline polymer in the solution is from about 1% to about 30% by weight of the solution.
Claim 25
Dependent Claim
26 words
The method of claim 20 wherein the concentration of polyquinoline polymer in the solution is from about 5% to about 25% by weight of the solution.
Claim 26
Dependent Claim
31 words
The method of claim 20 wherein the solvent is a polar solvent selected from the group consisting of amide solvents, ester solvents, ketone solvents, phenol solvents, alkylphenol solvents and formic acid.
Claim 27
Dependent Claim
35 words
The method of claim 20 wherein the amount of diazonaphthoquinone unit is from about 1 mol % to about 100 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 28
Dependent Claim
35 words
The method of claim 20 wherein the amount of diazonaphthoquinone unit is from about 10 mol % to about 90 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 29
Dependent Claim
35 words
The method of claim 20 wherein the amount of diazonaphthoquinone unit is from about 20 mol % to about 80 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 30
Dependent Claim
13 words
The method of claim 20 further comprising dissolving a photosensitizer in the solvent.
Claim 31
Dependent Claim
25 words
The method of claim 28 wherein the photosensitizer is present in an amount of from about 0.001% to about 20% by weight of the polyquinoline.
Claim 32
Dependent Claim
25 words
The method of claim 28 wherein the photosensitizer is present in an amount of from about 0.01% to about 10% by weight of the polyquinoline.
Claim 33
Dependent Claim
25 words
The method of claim 28 wherein the photosensitizer is present in an amount of from about 0.1% to about 1% by weight of the polyquinoline.
Claim 34
Independent Claim
91 words
A method for preparing a photoimageable polyquinoline film comprising: (a) mixing a polyquinoline polymer and a diazonaphthoquinone unit selected from the group consisting of alkyl halide derivatives of diazonaphthoquinones and sulfonyl chloride derivatives of diazonaphthoquinones, and a solvent at a temperature and for a time sufficient for at least a portion of the diazonaphthoquinone unit to chemically bond to the polyquinoline polymer; (b) applying a coating of the solution resulting from step (a) to a substrate; and (c) removing the solvent from the coated solution to thereby form a photoimageable film.
Claim 35
Independent Claim
91 words
A method for preparing a photoimageable polyquinoline film comprising: (a) mixing a polyquinoline polymer and a diazonaphthoquinone unit selected from the group consisting of alkyl halide derivatives of diazonaphthoquinones and sulfonyl chloride derivatives of diazonaphthoquinones, and a solvent at a temperature and for a time sufficient for at least a portion of the diazonaphthoquinone unit to chemically bond to the polyquinoline polymer; (b) applying a coating of the solution resulting from step (a) to a substrate; and (c) removing the solvent from the coated solution to thereby form a photoimageable film.
Claim 36
Dependent Claim
19 words
The method of claim 32 wherein the diazonaphthoquinonc unit chemically bonds to the polyquinoline polymer as a side unit.
Claim 37
Dependent Claim
19 words
The method of claim 32 wherein the diazonaphthoquinone unit chemically bonds to the polyquinoline polymer as an end unit.
Claim 38
Dependent Claim
32 words
The method of claim 32 wherein the polyquinoline polymer has a reactive group selected from the group consisting of OH and NH 2 and the diazonaphthoquinone unit reacts with said reactive group.
Claim 39
Dependent Claim
41 words
The method of claim 32 wherein the polyquinoline polymer has a reactive end group selected from the group consisting of OH and NH 2 and the diazonaphthoquinone unit reacts with said reactive end group to thereby form a diazonaphthoquinone end cap.
Claim 40
Dependent Claim
28 words
The method of claim 32 wherein the amount of polyquinoline polymer added in step (a) is from about 0.1% to about 60% by weight of the resulting solution.
Claim 41
Dependent Claim
28 words
The method of claim 32 wherein the amount of polyquinoline polymer added in step (a) is from about 1% to about 30% by weight of the resulting solution.
Claim 42
Dependent Claim
28 words
The method of claim 32 wherein the amount of polyquinoline polymer added in step (a) is from about 5% to about 25% by weight of the resulting solution.
Claim 43
Dependent Claim
31 words
The method of claim 32 wherein the solvent is a polar solvent selected from the group consisting of amide solvents, ester solvents, ketone solvents, phenol solvents, alkylphenol solvents and formic acid.
Claim 44
Dependent Claim
35 words
The method of claim 32 wherein the amount of diazonaphthoquinone unit is from about 1 mol % to about 100 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 45
Dependent Claim
35 words
The method of claim 32 wherein the amount of diazonaphthoquinone unit is from about 10 mol % to about 90 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 46
Dependent Claim
35 words
The method of claim 32 wherein the amount of diazonaphthoquinone unit is from about 20 mol % to about 80 mol % based on the molar concentration of quinoline repeat units in the polyquinoline polymer.
Claim 47
Dependent Claim
13 words
The method of claim 32 further comprising dissolving a photosensitizer in the solvent.
Claim 48
Dependent Claim
25 words
The method of claim 44 wherein the photosensitizer is present in an amount of from about 0.001% to about 20% by weight of the polyquinoline.
Claim 49
Dependent Claim
25 words
The method of claim 44 wherein the photosensitizer is present in an amount of from about 0.01% to about 10% by weight of the polyquinoline.
Claim 50
Dependent Claim
25 words
The method of claim 44 wherein the photosensitizer is present in an amount of from about 0.1% to about 1% by weight of the polyquinoline.
Claim 51
Independent Claim
80 words
A method for forming a photo-patterned polyquinoline-containing dielectric film comprising: providing a solution comprising a polyquinoline polymer, a diazonaphthoquinone unit and a solvent; applying a coating of the solution to a substrate; removing the solvent from the coated solution to thereby form a photoimageable film; exposing selected areas of the film with light; and developing the exposed film by immersion in a selective solvent which dissolves one of the exposed areas of the film or unexposed areas of the film.
Claim 52
Independent Claim
80 words
A method for forming a photo-patterned polyquinoline-containing dielectric film comprising: providing a solution comprising a polyquinoline polymer, a diazonaphthoquinone unit and a solvent; applying a coating of the solution to a substrate; removing the solvent from the coated solution to thereby form a photoimageable film; exposing selected areas of the film with light; and developing the exposed film by immersion in a selective solvent which dissolves one of the exposed areas of the film or unexposed areas of the film.
Claim 53
Dependent Claim
15 words
The method of claim 48 wherein the selective solvent dissolves unexposed areas of the film.
Claim 54
Dependent Claim
30 words
The method of claim 49 wherein the selective solvent is selected from the group consisting of anisole, benzene, chlorobenzene, toluene, xylene, mesitylene, 1,2,4-trimethylbenzene, dioxane, methyl acetate, acetone and mixtures thereof.
Claim 55
Dependent Claim
11 words
The method of claim 49 wherein the selective solvent comprises toluene.
Claim 56
Dependent Claim
12 words
The method of claim 49 wherein the selective solvent comprises an alkylketone.
Claim 57
Dependent Claim
13 words
The method of claim 49 wherein the selective solvent comprises an alkyl amide.
Claim 58
Dependent Claim
16 words
The method of claim 48 wherein the wavelength of light is between 230 and 600 nm.
Claim 59
Dependent Claim
16 words
The method of claim 48 wherein the wavelength of light is between 300 and 500 nm.
Claim 60
Dependent Claim
54 words
The method of claim 48 further comprising washing the developed film with a solvent capable of extracting diazonaphthoquinone unit and photogenerated by-products of diazonaphthoquinone unit for a time sufficient for the solvent to extract at least a portion of the diazonaphthoquinone unit and any photogenerated by-products of the diazonaphthoquinone unit present in the film.
Claim 61
Dependent Claim
62 words
A method for forming a photo-patterned polyquinoline-containing dielectric film, comprising the steps of: exposing selected areas of said photoimageable film formed by the method of claim 20 with light, to form an exposed film; and developing the exposed film by immersion in a selective solvent which dissolves one of (a) exposed areas of the film or (b) unexposed areas of the film.
Claim 62
Dependent Claim
15 words
The composition of claim 1 further comprising a solvent so as to form a solution.
Claim 63
Dependent Claim
16 words
The composition of claim 1 which consists essentially of the polyquinoline polymer and the diazonaphthoquinone unit.
Claim 64
Dependent Claim
11 words
The composition of claim 1 which is a negative photoimageable composition.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 2002-03-29 | 2002-09-28 | 2003-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-03-29 | 2006-09-28 | 2007-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-03-29 | 2010-09-28 | 2011-03-30 | $7700.00 | Window Closed / Lapsed |