US4719166A
Expired / Lapsed
US
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Positive-working photoresist elements containing anti-reflective butadienyl dyes which are thermally stable at temperatures of at least 200° C.
Assignee: Eastman Kodak Co
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Filing: 1986-07-29
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Granted: 1988-01-12
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Expires: 2006-07-29
Abstract
Abstract Positive-working photoresist elements are protected against reflection of activating radiation from the substrate by incorporation of certain butadienyl dyes in a photoresist layer, an anti-reflective layer or a planarizing layer. These dyes have superior resistance to thermal degradation or volatilization at temperatures of as high as 200 DEG C. or more. The dyes also exhibit good solubility in solvents commonly employed in processing semiconductor devices, thus permitting the dyes to be incorporated in photoresist elements in an amount sufficient to prevent resist image distortion caused by backscattered or reflected light.
Inventors
- 👤 Richard W. Blevins
- 👤 Robert C. Daly
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 00:03
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/091; H; H10; H10P; H10P76/00; H10P76/20; H10P76/204; H10P76/2041; H10P76/2043
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
167 words
In a positive-working photosensitive element comprising a support, a photosensitive layer on said support comprising a photosensitive compound responsive to activating radiation, which results in the photosensitive layer having increased solubility to selected solvents in the radiation exposed areas, and an anti-reflective dye disposed in a layer between said photosensitive layer and said support in an amount effective to absorb radiation reflected from said support, the improvement wherein said anti-reflective dye is a butadienyl dye having the structural formula: ##STR13## whereby said anti-reflective dye is thermally stable at temperatures of at least 200° C., wherein R 1 is alkyl, cycloalkyl or aryl; and R 2 is a linking group selected from the group consisting of arylene, alkylene and arylenealkylene and arylene, alkylene, and arylenealkylene interrupted with one or more oxygen atoms or ##STR14## where R 3 is alkyl; provided that the sum of the carbon atoms for both R 1 groups plus the R 2 group is at least 13; and X is an electron withdrawing group.
Claim 2
Dependent Claim
167 words
In a positive-working photosensitive element comprising a support, a photosensitive layer on said support comprising a photosensitive compound responsive to activating radiation, which results in the photosensitive layer having increased solubility to selected solvents in the radiation exposed areas, and an anti-reflective dye disposed in a layer between said photosensitive layer and said support in an amount effective to absorb radiation reflected from said support, the improvement wherein said anti-reflective dye is a butadienyl dye having the structural formula: ##STR13## whereby said anti-reflective dye is thermally stable at temperatures of at least 200° C., wherein R 1 is alkyl, cycloalkyl or aryl; and R 2 is a linking group selected from the group consisting of arylene, alkylene and arylenealkylene and arylene, alkylene, and arylenealkylene interrupted with one or more oxygen atoms or ##STR14## where R 3 is alkyl; provided that the sum of the carbon atoms for both R 1 groups plus the R 2 group is at least 13; and X is an electron withdrawing group.
Claim 3
Dependent Claim
15 words
The element of claim 1 wherein said layer containing said anti-reflective dye comprises poly(methyl methacrylate).
Claim 4
Dependent Claim
17 words
The element of claim 1 wherein said anti-reflective dye is selected from the group consisting of: ##STR15##
Claim 5
Dependent Claim
28 words
The element of claim 1 wherein X is selected from the group consisting of CN, ##STR16## and SO 2 R 4 wherein R 4 is alkyl or aryl.
Claim 6
Dependent Claim
12 words
The element of claim 4 wherein R 4 is methyl or phenyl.
Claim 7
Dependent Claim
9 words
The element of claim 1 wherein X represents CN.
Claim 8
Dependent Claim
13 words
The element of claim 1 wherein said photosensitive compound comprises a quinone diazide.
Claim 9
Dependent Claim
161 words
A positive-working photosensitive element comprising a support, a photosensitive layer on said support comprising in admixture a photosensitive compound responsive to activating radiation, which results in the photosensitive layer having increased solubility to selected solvents in the radiation-exposed areas, and an anti-reflective dye disposed in said photosensitive layer in an amount effective to absorb radiation reflected from said support, characterized in that said anti-reflective dye is a butadienyl dye having the structural formula: ##STR17## whereby said anti-reflective dye is thermally stable at temperatures of at least 200° C., wherein R 1 is alkyl, cycloalkyl or aryl; and R 2 is a linking group selected from the group consisting of arylene, alkylene and arylenealkylene and arylene, alkylene and arylenealkylene interrupted with one or more oxygen atoms or ##STR18## where R 3 is alkyl; provided that the sum of the carbon atoms for both R 1 groups plus the R 2 group is at least 13; and X is an electron withdrawing group.
Claim 10
Dependent Claim
161 words
A positive-working photosensitive element comprising a support, a photosensitive layer on said support comprising in admixture a photosensitive compound responsive to activating radiation, which results in the photosensitive layer having increased solubility to selected solvents in the radiation-exposed areas, and an anti-reflective dye disposed in said photosensitive layer in an amount effective to absorb radiation reflected from said support, characterized in that said anti-reflective dye is a butadienyl dye having the structural formula: ##STR17## whereby said anti-reflective dye is thermally stable at temperatures of at least 200° C., wherein R 1 is alkyl, cycloalkyl or aryl; and R 2 is a linking group selected from the group consisting of arylene, alkylene and arylenealkylene and arylene, alkylene and arylenealkylene interrupted with one or more oxygen atoms or ##STR18## where R 3 is alkyl; provided that the sum of the carbon atoms for both R 1 groups plus the R 2 group is at least 13; and X is an electron withdrawing group.
Claim 11
Dependent Claim
12 words
The element of claim 8 wherein said photosensitive layer comprises poly(methyl methacrylate).
Claim 12
Dependent Claim
17 words
The element of claim 8 wherein said anti-reflective dye is selected from the group consisting of: ##STR19##
Claim 13
Dependent Claim
28 words
The element of claim 8 wherein X is selected from the group consisting of CN, ##STR20## and SO 2 R 4 wherein R 4 is alkyl or aryl.
Claim 14
Dependent Claim
12 words
The element of claim 8 wherein R 4 is methyl or phenyl.
Claim 15
Dependent Claim
9 words
The element of claim 8 wherein X represents CN.
Claim 16
Dependent Claim
13 words
The element of claim 8 wherein said photosensitive compound comprises a quinone diazide.
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