US5178986A
Expired / Lapsed
US
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Positive photoresist composition with naphthoquinonediazidesulfonate of oligomeric phenol
Assignee: Shipley Co Inc
•
Filing: 1992-06-19
•
Granted: 1993-01-12
•
Expires: 2012-06-19
Abstract
Abstract A radiation sensitive oligomeric compound is described as the photoactive component with a base soluble phenolic matrix resin to provide improved photo-resist composition having high light-sensitivity, high resolution, excellent developer resistance and excellent resistance to thermal flow.
Inventors
- 👤 Anthony Zampini
- 👤 David C. Madoux
- 👤 Peter Trefonas, III
- 👤 Charles R. Szmanda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:15
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
153 words
A positive type photoresist composition comprising a mixture of an base-soluble resin and radiation sensitive oligomeric component consisting essentially of a compound of the formula ##STR5## where: X is hydrogen or a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; but at least one X is a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; R, R 1 , R 2 and R 4 are hydrogen, a halogen, an alkyl group free of a tertiary alpha-carbon atom, an alkoxy group having 1 to 4 carbon atoms, an aryl group or an arylalkyl group; in addition, R 2 and R 4 may be a nitro or an acyl group having 2 to 4 carbon atoms; R 3 is hydrogen, an alkyl, an aryl, or a heterocyclic group, but preferably is H; in addition, R 4 may be a tertiary alkyl group; wherein the weight ratio of the said resin to said radiation sensitive oligomeric compound is in the range of from about 1:1 to about 10:0.5.
Claim 2
Dependent Claim
153 words
A positive type photoresist composition comprising a mixture of an base-soluble resin and radiation sensitive oligomeric component consisting essentially of a compound of the formula ##STR5## where: X is hydrogen or a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; but at least one X is a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; R, R 1 , R 2 and R 4 are hydrogen, a halogen, an alkyl group free of a tertiary alpha-carbon atom, an alkoxy group having 1 to 4 carbon atoms, an aryl group or an arylalkyl group; in addition, R 2 and R 4 may be a nitro or an acyl group having 2 to 4 carbon atoms; R 3 is hydrogen, an alkyl, an aryl, or a heterocyclic group, but preferably is H; in addition, R 4 may be a tertiary alkyl group; wherein the weight ratio of the said resin to said radiation sensitive oligomeric compound is in the range of from about 1:1 to about 10:0.5.
Claim 3
Dependent Claim
103 words
A composition as claimed in claim 1 wherein R and R 1 are alkyl groups free of tertiary alpha-carbon atoms, one R 2 is hydrogen, and the other R 2 an alkyl group having 1 to 4 carbon atoms and being free of tertiary alpha-carbon atoms, an aryl, a halogen, or a nitro or acyl group having 2 to 4 carbon atoms, and R 4 is hydrogen, an alkyl group having 1 to 4 carbon atoms and being free of tertiary alpha-carbon atoms, an aryl, a halogen, a nitro, an acyl group having 2 to 4 carbon atoms or a tertiary alkyl group.
Claim 4
Dependent Claim
15 words
A composition as claimed in claim 2 wherein R and R 1 are methyl groups.
Claim 5
Dependent Claim
14 words
A composition as claimed in claim 3 wherein the other R 2 is methyl.
Claim 6
Dependent Claim
14 words
A composition as claimed in claim 3 wherein the other R 2 is hydrogen.
Claim 7
Dependent Claim
17 words
A composition as claimed in claim 3 wherein one R 4 is hydrogen and the other methyl.
Claim 8
Dependent Claim
11 words
The composition of claim 1 wherein X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue.
Claim 9
Dependent Claim
11 words
The composition of claim 1 wherein X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue.
Claim 10
Dependent Claim
13 words
The composition of claim 1 wherein said resin is a hydroxy aryl resin.
Claim 11
Dependent Claim
12 words
The composition of claim 9 wherein said resin is a novolac resin.
Claim 12
Dependent Claim
14 words
The composition of claim 10 wherein said resin is substantially a cresol-formaldehyde novolac resin.
Claim 13
Dependent Claim
35 words
The composition of claim 9 wherein said resin is formed by condensing in the presence of acid at least one bishydroxymethyl substituted phenolic compound and at least one reactive phenolic compound capable of sustaining polymerization.
Claim 14
Dependent Claim
39 words
The composition of claim 9 wherein said resin is substantially a block copolymer formed by condensing in the presence of acid the resin of claim 12 with formaldehyde and at least one reactive phenolic compound capable of sustaining polymerization.
Claim 15
Dependent Claim
23 words
The composition of claim 12 wherein said bishydroxymethyl substituted phenolic compound is 2,6-bis(hydroxymethyl)-p-alkylphenol wherein the alkyl group has 1 to 4 carbon atoms..
Claim 16
Dependent Claim
53 words
The composition of claim 9 wherein said resin is formed by condensing in the presence of acid and a divalent sulfur compound a mixture of at least one aromatic aldehyde with at least one reactive phenolic compound capable of sustaining polymerization, said polymer having a weight-average molecular weight of at least 1500 Daltons.
Claim 17
Dependent Claim
29 words
The composition of claim 15 wherein said aromatic aldehyde is selected from the group consisting of benzaldehyde, salicylaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde and 1-naphthaldehyde and said reactive phenolic compound is cresol.
Claim 18
Dependent Claim
48 words
The composition of claim 9 wherein said resin is an admixture of resin of claim 11 with resin of claim 15, and wherein the weight ratio of the said resin of claim 11 to said resin of claim 15 is in the range of 49:1 to about 1:49.
Claim 19
Dependent Claim
57 words
The composition of claim 9 wherein said resin is an admixture of the resin of claim 15 with the polycondensation product of phenol having two or more hydroxy groups and a ketone, and wherein the weight ratio of the said resin of claim 15 to said polycondensation product of phenol and ketone is 49:1 to about 20:30.
Claim 20
Dependent Claim
26 words
The composition of claim 18 wherein said phenol is pyrogallol and said ketone is selected from the group consisting of acetone, acetophenone, cyclohexanone, cyclopentanone and methylethylketone.
Claim 21
Dependent Claim
41 words
The composition of claim 1 wherein said resin is a cresol-formaldehyde novolac resin and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 22
Dependent Claim
41 words
The composition of claim 1 wherein said resin is a cresol-formaldehyde novolac resin and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 23
Dependent Claim
64 words
The composition of claim 1 wherein said resin is formed by condensing in the presence of acid at least one bishydroxymethyl substituted phenolic compound and at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range of from about 4:1 to about 10:0.5.
Claim 24
Dependent Claim
63 words
The composition of claim 1 wherein said resin is formed by condensing in the presence of acid at least one bishydroxymethyl substituted phenolic compound and at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 25
Dependent Claim
68 words
The composition of claim 1 wherein said resin is substantially a block copolymer formed by condensing in the presence of acid the resin of claim 12 with formaldehyde and at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range of from about 4:1 to about 10:0.5.
Claim 26
Dependent Claim
68 words
The composition of claim 1 wherein said resin is substantially a block copolymer formed by condensing in the presence of acid the resin composition of claim 12 with formaldehyde and at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 27
Dependent Claim
70 words
The composition of claim 1 wherein said resin is formed by condensing in the presence of acid and a divalent sulfur compound a mixture of at least one aromatic aldehyde with at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range of from about 4:1 to about 10:0.5.
Claim 28
Dependent Claim
69 words
The composition of claim 1 wherein said resin is formed by condensing in the presence of acid and a divalent sulfur compound a mixture of at least one aromatic aldehyde with at least one reactive phenolic compound capable of sustaining polymerization and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 29
Dependent Claim
79 words
The composition of claim 1 wherein said resin is an admixture of the resin of claim 11 with the resin of claim 15, and wherein the weight ratio of the said resin of claim 11 to said resin of claim 15 is in the range of 49:1 to 1:49 and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin admixture to said naphthoquinone derivative is in the range of from about 4:1 to about 10:0.5.
Claim 30
Dependent Claim
78 words
The composition of claim 1 wherein said resin is an admixture of the composition of claim 11 with the resin of claim 15, and wherein the weight ratio of the said resin of claim 11 to said resin of claim 15 is in the range of 49:1 to 1:49 and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin admixture to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 31
Dependent Claim
87 words
The composition of claim 1 wherein said resin is an admixture of the resin of claim 15 with the polycondensation product of phenol having two or more hydroxy groups and a ketone, and the weight ratio of the said resin of claim 15 to said polycondensation product of phenol and ketone is about 49:1 to about 20:30 and X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue and the ratio by weight of said resin admixture to said naphthoquinone derivative is in the range of from about 4:1 to about 10:0.5.
Claim 32
Dependent Claim
86 words
The composition of claim 1 wherein said resin is an admixture of the resin of claim 15 with the polycondensation product of phenol having two or more hydroxy groups and a ketone, and the weight ratio of the said resin of claim 15 to said polycondensation product of phenol and ketone is about 49:1 to about 20:30 and X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue and the ratio by weight of said resin admixture to said naphthoquinone derivative is in the range from about 4:1 to about 10:0.5.
Claim 33
Dependent Claim
13 words
The composition of claim 1 further comprising one or more other photosensitive additives.
Claim 34
Dependent Claim
15 words
The composition of claim 32, wherein said additive is the naphthoquinone diazide ester of trihydroxybenzophenone.
Claim 35
Dependent Claim
34 words
The composition of claim 33, wherein the weight ratio of the radiation sensitive oligomeric component of claim 1 to the naphthoquinone diazide ester of trihydroxybenzophenone is in the range of about 20:1 to 1:20.
Claim 36
Dependent Claim
23 words
The composition of claim 33, wherein said resin is an admixture of the resin of claim 11 with the resin of claim 15.
Claim 37
Dependent Claim
25 words
The composition of claim 1 further comprising one or more additives selected from the group consisting of pigments, dyes, anti-striation agents, resolution enhancers and solvent.
Claim 38
Dependent Claim
62 words
The composition of claim 36 wherein said dye is substantially an admixture of bis(phenylazo)resorcinol with one or more dye compounds selected from the group consisting of Coumarin 314, curcumin, Disperse Yellow 54, Macrolex 6G, 4-phenylazoresorcinol and Rhodamine B, and wherein the proportion by weight of said dye admixture to resin binder is in the range of about 0.4 to about 8 percent.
Claim 39
Dependent Claim
18 words
The composition of claim 36 wherein said solvent is an admixture of amyl acetate, anisole and ethyl lactate.
Claim 40
Dependent Claim
12 words
The composition of claim 36 wherein said solvent is substantially ethyl lactate.
Claim 41
Dependent Claim
56 words
A positive type photoresist which comprises the composition of claim 1 coated on a support wherein said support comprises one or more materials selected from the group consisting of polyester, polyimide, planarizing layer, silicon, gallium arsenide, silicon/silicon dioxide, doped silicon dioxide, silicon nitride, aluminum, tungsten, glass, boron nitride, aluminum/copper mixtures, tantalum, copper, polysilicon and superconducting materials.
Claim 42
Dependent Claim
134 words
A radiation sensitive oligomeric compound of the formula: ##STR6## where: X is hydrogen or a naphthoquinone-(1,2)-diazide-(2)sulfonyl residue; but at least one X is a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; R, R 1 , R 2 and R 4 are hydrogen, a halogen, an alkyl group free of tertiary alpha-carbon atom, and alkoxy group having 1 to 4 carbon atoms, an aryl group or an arylalkyl group; in addition R 2 and R 4 may be a nitro or an acyl group having 2 to 4 carbon atoms; R 3 is hydrogen, an alkyl, an aryl, or a heterocyclic group, but preferably is H; in addition R 4 may be a tertiary alkyl group, and the weight ratio of the said resin to said radiation sensitive oligomeric component is in the range from about 1:1 to about 10:0.5.
Claim 43
Dependent Claim
134 words
A radiation sensitive oligomeric compound of the formula: ##STR6## where: X is hydrogen or a naphthoquinone-(1,2)-diazide-(2)sulfonyl residue; but at least one X is a naphthoquinone-(1,2)-diazide-(2)-sulfonyl residue; R, R 1 , R 2 and R 4 are hydrogen, a halogen, an alkyl group free of tertiary alpha-carbon atom, and alkoxy group having 1 to 4 carbon atoms, an aryl group or an arylalkyl group; in addition R 2 and R 4 may be a nitro or an acyl group having 2 to 4 carbon atoms; R 3 is hydrogen, an alkyl, an aryl, or a heterocyclic group, but preferably is H; in addition R 4 may be a tertiary alkyl group, and the weight ratio of the said resin to said radiation sensitive oligomeric component is in the range from about 1:1 to about 10:0.5.
Claim 44
Dependent Claim
108 words
A radiation sensitive oligomeric compound as claimed in claim 41 wherein R and R 1 are alkyl groups free of tertiary alpha-carbon atoms, one R 2 is hydrogen, and the other R 2 is an alkyl group having 1 to 4 carbon atoms and being free of tertiary alpha-carbon atoms, an aryl, a halogen, a nitro or an acyl group having 2 to 4 carbon atoms and R 4 is hydrogen, an alkyl group having 1 to 4 carbon atoms and being free of tertiary alpha-carbon atoms, an aryl, a halogen, a nitro or an acyl group having 2 to 4 carbon atoms or a tertiary alkyl group.
Claim 45
Dependent Claim
17 words
A radiation sensitive oligomeric compound claimed in claim 42 wherein R and R 1 are methyl groups.
Claim 46
Dependent Claim
20 words
A radiation sensitive oligomeric compound claimed in claim 43 wherein a substantial portion of the other R 2 is methyl.
Claim 47
Dependent Claim
16 words
A radiation sensitive oligomeric compound claimed in claim 43 wherein the other R 2 is hydrogen.
Claim 48
Dependent Claim
19 words
A radiation sensitive oligomeric compound claimed in claim 43 wherein one R 4 is hydrogen and the other methyl.
Claim 49
Dependent Claim
11 words
The composition of claim 41 wherein X is a naphthoquinone-(1,2)-diazide-(2)-4-sulfonyl residue.
Claim 50
Dependent Claim
11 words
The composition of claim 41 wherein X is a naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl residue.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-01-12 | 1996-07-13 | 1997-01-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-01-12 | 2000-07-13 | 2001-01-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-01-12 | 2004-07-13 | 2005-01-12 | $7700.00 | Window Closed / Lapsed |