US5861235A
Expired / Lapsed
US
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Ultraviolet-curable composition and method for patterning the cured product therefrom
Assignee: DuPont Toray Specialty Materials KK
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Filing: 1997-06-24
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Granted: 1999-01-19
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Expires: 2017-06-24
Abstract
Abstract This invention pertains to a curable composition comprising a N-substituted 4-(o-nitrophenyl)dihydropyridine (a compound that generates base under the action of ultraviolet radiation) and a silanol-containing polymer that condenses under the action of the base generated to form a siloxane bond. The compositions of the instant invention cure by exposure to ultraviolet radiation. Cured patterns may be formed from the curable composition by interposing a mask between a film of the said composition and the radiation source during UV exposure, then dissolving and removing the uncured composition to form a pattern, and thereafter heating the residual material. The compositions can be cured by low-strength ultraviolet radiation and produce a highly heat-resistant cured product.
Inventors
- 👤 Brian R. Harkness
- 👤 Mamoru Tachikawa
- 👤 Kasumi Takei
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:44
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0757; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/12
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
235 words
An ultraviolet-curable composition comprising (a) 0.01 to 20% based on the total weight of the said composition of a N-substituted 4-(o-nitrophenyl)dihydropyridine and (b) a silanol-functional polymer of the formula (R.sub.2 SiO.sub.2/2).sub.a (RSiO.sub.3/2).sub.1-a wherein a is a number with a value from 0 to 0.5, inclusive and each R is independently selected from the group consisting essentially of C 1 to C 8 saturated and unsaturated hydrocarbyl groups that may contain at least one atom selected from oxygen, nitrogen, chlorine, silicon, and fluorine; wherein at least one of the divalent oxygen atoms bonded to silicon in each R 2 SiO 2/2 is bonded to another silicon to form a siloxane bond while the remaining oxygen may be bonded to another silicon to form a siloxane bond, or may be bonded to methyl or ethyl to form an alkoxy group, or may be bonded to hydrogen to form silanol; at least one of the divalent oxygen atoms bonded to silicon in each RSiO 3/2 is bonded to another silicon to form a siloxane bond while the remaining oxygen may be bonded to another silicon to form a siloxane bond, or may be bonded to methyl or ethyl to form an alkoxy group, or may be bonded to hydrogen to form silanol; with the proviso that RSiO 3/2 having at least one silanol accounts for at least 10 moles % of the total silicon in the polymer molecule.
Claim 2
Dependent Claim
235 words
An ultraviolet-curable composition comprising (a) 0.01 to 20% based on the total weight of the said composition of a N-substituted 4-(o-nitrophenyl)dihydropyridine and (b) a silanol-functional polymer of the formula (R.sub.2 SiO.sub.2/2).sub.a (RSiO.sub.3/2).sub.1-a wherein a is a number with a value from 0 to 0.5, inclusive and each R is independently selected from the group consisting essentially of C 1 to C 8 saturated and unsaturated hydrocarbyl groups that may contain at least one atom selected from oxygen, nitrogen, chlorine, silicon, and fluorine; wherein at least one of the divalent oxygen atoms bonded to silicon in each R 2 SiO 2/2 is bonded to another silicon to form a siloxane bond while the remaining oxygen may be bonded to another silicon to form a siloxane bond, or may be bonded to methyl or ethyl to form an alkoxy group, or may be bonded to hydrogen to form silanol; at least one of the divalent oxygen atoms bonded to silicon in each RSiO 3/2 is bonded to another silicon to form a siloxane bond while the remaining oxygen may be bonded to another silicon to form a siloxane bond, or may be bonded to methyl or ethyl to form an alkoxy group, or may be bonded to hydrogen to form silanol; with the proviso that RSiO 3/2 having at least one silanol accounts for at least 10 moles % of the total silicon in the polymer molecule.
Claim 3
Dependent Claim
65 words
The ultraviolet-curable composition as claimed in claim 1, wherein the silanol-functional polymer (b) is a polymer of the formula (RSiO 3/2 ) wherein R is selected from the group consisting essentially of methyl, ethyl, propyl, 3,3,3-trifluoropropyl, n-butyl, n-hexyl, n-octyl, vinyl, allyl, and 5-hexenyl; and RSiO 3/2 having at least one silanol accounts for at least 10 mole % of the total silicon in the polymer.
Claim 4
Dependent Claim
60 words
The ultraviolet-curable composition as claimed in claim 1, wherein the silanol-functional polymer (b) is a polymer having the formula (RSiO 3/2 ) wherein R is selected from the group consisting essentially of isopropyl, phenyl, m-tolyl, and p-tolyl; and RSiO 3/2 having at least one silanol accounts for at least 40 mole % of the total silicon in the polymer molecule.
Claim 5
Dependent Claim
78 words
The ultraviolet-curable composition as claimed in claim 1, wherein the silanol-functional polymer (b) is a polymer of the formula(R 2 SiO 2/2 ) a (RSiO 3/2 ) 1-a wherein a is a number with a value from 0.2 to 0.5; wherein each R is independently selected from the group consisting essentially of phenyl and methyl; and RSiO 3/2 carrying at least one silanol accounts for at least 15 mole % of the total silicon in the polymer molecule.
Claim 6
Dependent Claim
75 words
The ultraviolet-curable composition as claimed in claim 1 wherein the N-substituted 4-(o-nitrophenyl)dihydropyridine is selected from 4-(o-nitrophenyl)dihydropyridines in which the group bonded at position 1 on the dihydropyridine is selected from methyl, ethyl, n-propyl, n-butyl, allyl, 3-butenyl, or benzyl; the group bonded at position 3 and position 5 on the dihydropyridine is selected from methoxycarbonyl or ethoxycarbonyl; and the group bonded at position 2 and position 6 on the dihydropyridine is selected from methyl or ethyl.
Claim 7
Dependent Claim
32 words
The ultraviolet-curable composition as claimed in claim 1 wherein the N-substituted 4-(o-nitrophenyl)dihydropyridine is present in an amount of 0.1 to 10 wt % relative to the total weight of the curable composition.
Claim 8
Dependent Claim
58 words
A method for the formation of a cured product comprising: (a) forming a coating of the curable composition as claimed in claim 1 on a substrate; (b) exposing the coating to ultraviolet radiation at a temperature from 0° C. to 100° C.; and (c) thereafter heating said coating at a temperature of from 100° C. to 400° C.
Claim 9
Dependent Claim
24 words
The method as claimed in claim 7 wherein the coating is formed by applying the composition as claimed in claim 2 to the substrate.
Claim 10
Dependent Claim
24 words
The method as claimed in claim 7 wherein the coating is formed by applying the composition as claimed in claim 3 to the substrate.
Claim 11
Dependent Claim
24 words
The method as claimed in claim 7 wherein the coating is formed by applying the composition as claimed in claim 4 to the substrate.
Claim 12
Dependent Claim
100 words
A method for forming a cured pattern corresponding to the negative of a photomask comprising: (a) forming a coating of the curable composition as claimed in claim 1 on a substrate; (b) placing a masking pattern between the curable composition and an ultraviolet source; (c) exposing the coating to ultraviolet radiation across a masking pattern at a temperature from 0° C. to 100° C.; (d) heating the coating at a temperature of 0° C. to 250° C.; and (e) dissolving and removing any uncured curable composition by contacting the coating with a solvent thereby generating a pattern of cured product.
Claim 13
Dependent Claim
20 words
The method as claimed in claim 11 wherein the pattern of cured product is heated 50° C. to 400° C.
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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) | 2002-01-18 | 2002-07-20 | 2003-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-01-18 | 2006-07-20 | 2007-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-01-18 | 2010-07-20 | 2011-01-19 | $7700.00 | Window Closed / Lapsed |