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US4908096A Expired / Lapsed US ⏱️ 0.0 years remaining

Photodefinable interlevel dielectrics

Assignee: Honeywell International Inc
•
Filing: 1988-06-24
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Granted: 1990-03-13
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Expires: 2008-06-24
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Abstract

Abstract Ethers of oligomeric phenol-dialdehyde condensation products containing vinyl benzyl moieties in at least half of the ether moieties are excellent photosensitive prepolymers. Through simple masking and irradiation with a broad range of radiation types, such a resin as a coating can be selectively patterned by dissolving the non-irradiated and non-photocrosslinked portions of the prepolymer with a large variety of common solvents. The outstanding differential solubility between the photocrosslinked and non-crosslinked regions of the prepolymer allows excellent resolution with good edge sharpness. Subsequent thermal curing affords a void-free infusible glassy solid with minimum shrinkage, excellent planarity characteristics, and high resistance to cracking.

Inventors

  • 👤 Joseph J. Zupancic

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:15
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; G03F7/0388; Y; Y10; Y10S; Y10S438/00; Y10S438/942; Y10S438/948

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 226 words
A method of selectively forming a patterned polymeric resin on a substrate comprising: (a) coating a substrate with a prepolymer which is an oligomeric resin comprising ethers of the oligomeric condensation product of 1 molar proportion of a dialdehyde, with a dialdehyde selected from the group consisting of OHC(CH2)nCHO, where n=0 or an integer from 1 to 6, cyclopentanedione, cyclohexanedione, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde, with from about 3 to about 4 molar proportions of a phenol of structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms, and where the ether moiety is randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1; (b) irradiating the prepolymer coating through a masking pattern so as to selectively crosslink portions of the coating being irradiated; (c) selectively dissolving the non-irradiated parts of the prepolymer coating; and (d) curing the patterned photochemically crosslinked portion of the prepolymer coating by heating said portion at a temperature greater than about 110° C. for a time sufficient to further crosslink said coating and transform the prepolymer to an infusible glassy solid.
Claim 2
Independent Claim 226 words
A method of selectively forming a patterned polymeric resin on a substrate comprising: (a) coating a substrate with a prepolymer which is an oligomeric resin comprising ethers of the oligomeric condensation product of 1 molar proportion of a dialdehyde, with a dialdehyde selected from the group consisting of OHC(CH2)nCHO, where n=0 or an integer from 1 to 6, cyclopentanedione, cyclohexanedione, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde, with from about 3 to about 4 molar proportions of a phenol of structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms, and where the ether moiety is randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1; (b) irradiating the prepolymer coating through a masking pattern so as to selectively crosslink portions of the coating being irradiated; (c) selectively dissolving the non-irradiated parts of the prepolymer coating; and (d) curing the patterned photochemically crosslinked portion of the prepolymer coating by heating said portion at a temperature greater than about 110° C. for a time sufficient to further crosslink said coating and transform the prepolymer to an infusible glassy solid.
Claim 3
Dependent Claim 25 words
The method of claim 1 where the dialdehyde is OHC(CH 2 ) n CHO and n is 0 or an integer from 1 to 4.
Claim 4
Dependent Claim 9 words
The method of claim 2 where n is zero.
Claim 5
Dependent Claim 10 words
The method of claim 1 where the phenol is phenol.
Claim 6
Dependent Claim 10 words
The method of claim 1 where the phenol is cresol.
Claim 7
Dependent Claim 21 words
The method of claim 1 where each oligomeric condensation product has from about 4 to about 60 phenol moieties per molecule.
Claim 8
Dependent Claim 20 words
The method of claim 6 where the condensation product has from about 4 to about 22 phenolic moieties per molecule.
Claim 9
Dependent Claim 28 words
The method of claim 7 further characterized in that the mixture of oligomeric condensation products has an average from about 5 to about 8 phenolic moieties per molecule.
Claim 10
Dependent Claim 30 words
The method of claim 4 where the dialdehyde is glyoxal and further characterized in that the molecular weight of each oligomeric condensation product is from about 400 to about 6,000.
Claim 11
Dependent Claim 21 words
The method of claim 9 where the molecular weight of each oligomeric condensation product is from about 400 to about 2200.
Claim 12
Dependent Claim 27 words
The method of claim 9 further characterized in that the average molecular weight of the mixture of oligomeric condensation products is from about 500 to about 800.
Claim 13
Dependent Claim 26 words
The resin of claim 1 where the other ether moieties are selected from the group consisting of alkyl moieties having 1 through about 4 carbon atoms.
Claim 14
Dependent Claim 14 words
The method of claim 1 where the alkyl moiety is a primary alkyl moiety.
Claim 15
Dependent Claim 19 words
The method of claim 1 where irradiation is performed by x-ray, electron beam, ion beam, ultraviolet, or visible radiation.
Claim 16
Dependent Claim 19 words
The method of claim 1 where the radiation has a wave length between bout 200 and about 800 nanometers.
Claim 17
Dependent Claim 31 words
The method of claim 1 where the non-irradiated prepolymer coating is selectively dissolved using solvent selected from the group consisting of aprotic solvents, aromatic hydrocarbons, chlorinated hydrocarbons, esters, ketones, and Carbitols.
Claim 18
Dependent Claim 30 words
The method of claim 1 further characterized in that the prepolymer coating contains a photosensitizer in an amount from about 0.001 to about 5.0 weight percent, based on the resin.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-03-12 1993-09-11 1994-03-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-03-12 1997-09-11 1998-03-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-03-12 2001-09-11 2002-03-13 $7700.00 Window Closed / Lapsed

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