US4411978A
Expired / Lapsed
US
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Photoresist materials and processes of using with photosensitive naphthoquinone diazides and nitrones
Assignee: Agfa Gevaert NV
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Filing: 1978-03-13
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Granted: 1983-10-25
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Expires: 1998-03-13
Abstract
Abstract A photosensitive recording material which includes in a supported layer a mixture of photosensitive substances in admixture with one or more polymers that are soluble in an alkaline aqueous liquid, characterized in that such mixture of photosensitive substances essentially consists of: (A) at least one photosensitive nitrone of the formula: ##STR1## in which: R is an aromatic hydrocarbon group including a substituted aromatic hydrocarbon group, R 1 is an aromatic or heterocyclic group including these groups in substituted form, n represents zero or 1, and (B) at least one photosensitive naphthoquinone-(1,2)-diazide (2) compound, that has a higher ultraviolet absorption in the wavelength range of 350 to 400 nm and a higher visible light absorption above 400 nm than each such nitrone has, the (A) and (B) compounds being present in such relative quantities to each other that the layer exhibits a relative decrease in solubility in an alkaline aqueous liquid upon a sufficient exposure to a UV-light and a relative increase in solubilty in such alkaline aqueous liquid upon a lesser exposure to visible light or to UV-light.
Inventors
- 👤 Urbain L. Laridon
- 👤 Hendrik E. Kokelenberg
- 👤 Rafael P. Samijn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:11
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/095
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
167 words
A photosensitive recording material which comprises a supported layer containing a mixture of photosensitive substances in admixture with at least one polymer that is soluble in an alkaline aqueous liquid, characterized in that said mixture of photosensitive substances consists essentially of: (A) at least one negative-working photosensitive nitrone of the formula: ##STR17## in which: R is an aromatic hydrocarbon group R 1 is an aromatic or heterocyclic group, n represents zero or 1, and (B) at least one positive-working photosensitive naphthoquinone(1,2)-diazide (2) compound, having a higher ultraviolet absorption in the wavelength range of 350 to 400 nm and a higher visible light absorption above 400 nm than each such nitrone has, said (A) and (B) compounds being present in such relative quantities to each other that the layer exhibits a relative decrease in solubility in an alkaline aqueous liquid upon a sufficient exposure to a UV-light and a relative increase in solubility in an alkaline aqueous liquid upon a lesser exposure to visible light or to UV-light.
Claim 2
Dependent Claim
167 words
A photosensitive recording material which comprises a supported layer containing a mixture of photosensitive substances in admixture with at least one polymer that is soluble in an alkaline aqueous liquid, characterized in that said mixture of photosensitive substances consists essentially of: (A) at least one negative-working photosensitive nitrone of the formula: ##STR17## in which: R is an aromatic hydrocarbon group R 1 is an aromatic or heterocyclic group, n represents zero or 1, and (B) at least one positive-working photosensitive naphthoquinone(1,2)-diazide (2) compound, having a higher ultraviolet absorption in the wavelength range of 350 to 400 nm and a higher visible light absorption above 400 nm than each such nitrone has, said (A) and (B) compounds being present in such relative quantities to each other that the layer exhibits a relative decrease in solubility in an alkaline aqueous liquid upon a sufficient exposure to a UV-light and a relative increase in solubility in an alkaline aqueous liquid upon a lesser exposure to visible light or to UV-light.
Claim 3
Dependent Claim
26 words
A material according to claim 1, wherein in the nitrone R is phenyl and R 1 is phenyl, naphthyl, hydroxyphenyl, nitrophenyl, alkoxyphenyl, furyl, thienyl or bromothienyl.
Claim 4
Dependent Claim
54 words
A material according to claim 1 wherein the naphthoquinone-(1,2)-diazide (2) compound corresponds to one of the following general formulae (I) or (II): ##STR18## wherein: R 2 represents a fluorine atom, a chlorine atom, an aryl group, an aryloxy group or an arylamino group, and R 3 represents a fluorine atom or any aryloxy group.
Claim 5
Dependent Claim
19 words
A material according to claim 3, wherein the naphthoquinone-(1,2)-diazide(2) compound is naphthoquinone(1,2)-diazide-(2)-5-sulphonic acid ester of 2,3,4-trihydroxybenzophenone or naphthoquinone(1,2)-diazide(2)-5-sulphonyl fluoride.
Claim 6
Dependent Claim
13 words
A material according to claim 1, wherein the alkali-soluble polymer is a novolak.
Claim 7
Dependent Claim
18 words
A material according to claim 1, wherein the alkali-soluble polymer is a copolymer of an unsaturated carboxylic acid.
Claim 8
Dependent Claim
25 words
A material according to claim 1, wherein the weight ratio of alkali-soluble polymer to the mixture of said photosensitive compounds is between 1:1 and 7:1.
Claim 9
Dependent Claim
29 words
A material according to claim 1, wherein the layer contains from 2 to 6 parts by weight of nitrone with respect to 1 part by weight of naphthoquinone(1,2)-diazide(2) compound.
Claim 10
Dependent Claim
20 words
A material according to claim 1, wherein said layer has a thickness in the range of 0.5 to 20 μm.
Claim 11
Dependent Claim
15 words
A material according to claim 1, wherein said layer is present on a metal support.
Claim 12
Dependent Claim
23 words
A material according to claim 1, wherein said layer is present on a metallic layer that is present on a polymeric film support.
Claim 13
Dependent Claim
31 words
A material according to claim 11, wherein said metallic layer is made of tellurium or a tellurium alloy and has a thickness in the range of 50 nm to 500 nm.
Claim 14
Dependent Claim
27 words
A material according to claim 11, wherein said metallic layer is made of bismuth and has a thickness in the range of 25 nm to 300 nm.
Claim 15
Dependent Claim
76 words
A method for producing a positive photoresist comprising the steps of: (1) information-wise exposing the photosensitive layer of the material according to claim 1 to ultraviolet radiation and/or visible light of a dose sufficient to increase the solubility of the exposed portions by phototransformation of the naphthoquinone-(1,2)-diazide(2) compound without substantially affecting the nitrone, and (2) overall contacting the exposed photosensitive layer with an aqueous alkaline liquid to remove selectively the exposed portions of the photosensitive layer.
Claim 16
Dependent Claim
120 words
A method for producing a negative photoresist comprising the steps of: (1) information-wise exposing the photosensitive layer of the material according to claim 1 to ultraviolet radiation of a dose sufficient to decrease the solubility of the exposed portions by the photoproducts of the nitrone which are formed by such exposure in a higher amount than are the photoproducts of the naphthoquinone-(1,2)-diazide(2) compound(s), (2) overall exposing the photosensitive layer to ultraviolet radiation and/or visible light of a dose substantially less than that of step 1 but sufficient to improve the solubility of the initially non-exposed portions, and (3) overall contacting the exposed photosensitive layer with an aqueous alkaline liquid to remove selectively the initially non-exposed portions of the photosensitive layer.
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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) | 1986-10-24 | 1987-04-25 | 1987-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-24 | 1991-04-25 | 1991-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-24 | 1995-04-25 | 1995-10-25 | $7700.00 | Window Closed / Lapsed |