US4732836A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel mixed ester O-quinone photosensitizers
Assignee: Clariant Finance BVI Ltd
•
Filing: 1986-05-02
•
Granted: 1988-03-22
•
Expires: 2006-05-02
Abstract
Abstract The invention relates to new mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitizer compositions exhibit excellent solution stability and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.
Inventors
- 👤 Robert E. Potvin
- 👤 Jonas O. St. Alban
- 👤 Chester J. Sobodacha
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:46
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
179 words
A photoresist composition having improved solution stability comprising an admixture of a novolak or polyvinyl phenol resin, a solvent and a photosensitizer composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR37## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH, and X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR38## n is 1 or 2, II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo); and III. An organic acid represented by the formula W--R.sub.3 wherein W is ##STR39## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo reacted to the amount of organic acid reacted is in the range of from about 1:1 to about 39:1, and the amount of Diazo and organic acid reacted with said phenolic compound being sufficient to produce a photosensitizer composition capable of inhibiting the dissolution rate of an alkali soluble resin in alkaline developing solution.
Claim 2
Dependent Claim
179 words
A photoresist composition having improved solution stability comprising an admixture of a novolak or polyvinyl phenol resin, a solvent and a photosensitizer composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR37## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH, and X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR38## n is 1 or 2, II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo); and III. An organic acid represented by the formula W--R.sub.3 wherein W is ##STR39## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo reacted to the amount of organic acid reacted is in the range of from about 1:1 to about 39:1, and the amount of Diazo and organic acid reacted with said phenolic compound being sufficient to produce a photosensitizer composition capable of inhibiting the dissolution rate of an alkali soluble resin in alkaline developing solution.
Claim 3
Dependent Claim
161 words
A photoresist composition having improved solution stability comprising an admixture of novolak or polyvinyl phenol resin, a solvent and a photosensitizer composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR40## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH; II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo); and III. An organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR41## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo reacted to the amount of organic acid reacted is in the range of from about 1:1 to about 39:1, and the amount of Diazo and organic acid reacted with said phenolic compound being sufficient to produce a photosensitizer composition capable of inhibiting the dissolution rate of an alkali soluble resin in alkaline developing solution.
Claim 4
Dependent Claim
161 words
A photoresist composition having improved solution stability comprising an admixture of novolak or polyvinyl phenol resin, a solvent and a photosensitizer composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR40## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH; II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo); and III. An organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR41## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo reacted to the amount of organic acid reacted is in the range of from about 1:1 to about 39:1, and the amount of Diazo and organic acid reacted with said phenolic compound being sufficient to produce a photosensitizer composition capable of inhibiting the dissolution rate of an alkali soluble resin in alkaline developing solution.
Claim 5
Dependent Claim
47 words
The composition of claim 2 containing from about 50% to about 97% by weight resin and from about 3% to about 50% by weight photosensitizer on a solids basis, mixed with solvent present in an amount of about 40% to 90% by weight of the overall composition.
Claim 6
Dependent Claim
48 words
The composition of claim 3 wherein the amount of resin is from about 65% to about 93% by weight, the amount of photosensitizer is from about 7% to about 35% by weight, and the solvent is mixed in an amount of about 65% to about 80% by weight.
Claim 7
Dependent Claim
35 words
A photoresist composition according to claim 2, wherein said ratio of said amount of Diazo reacted to said amount of organic acid halide reacted is in the range of from about 4:1 to about 19:1.
Claim 8
Dependent Claim
43 words
A photoresist composition according to claim 5, wherein said phenolic compound is a dihydroxybenzophenone, a trihydroxybenzophenone or a tetrahydroxybenzophenone; and said organic acid halide is a lower alkyl sulfonyl halide, a benzene sulfonyl halide, a lower alkyl acyl halide or a benzoyl halide.
Claim 9
Dependent Claim
13 words
A photoresist composition according to claim 5, wherein said phenolic compound is 2,3,4-trihydroxybenzophenone.
Claim 10
Dependent Claim
16 words
A photoresist composition according to claim 7, wherein said solvent is propylene glycol methyl ether acetate.
Claim 11
Dependent Claim
35 words
A photoresist composition according to claim 2, wherein said ratio of said amount of Diazo reacted to said amount of organic acid halide reacted is in the range of from about 93:7 to about 85:15.
Claim 12
Dependent Claim
43 words
A photoresist composition according to claim 9, wherein said phenolic compound is a dihydroxybenzophenone, a trihydroxybenzophenone or a tetrahydroxybenzophenone; and said organic acid halide is a lower alkyl sulfonyl halide, a benzene sulfonyl halide, a lower alkyl acyl halide or a benzoyl halide.
Claim 13
Dependent Claim
13 words
A photoresist composition according to claim 9, wherein said phenolic compound is 2,3,4-trihydroxybenzophenone.
Claim 14
Dependent Claim
16 words
A photoresist composition according to claim 11, wherein said solvent is propylene glycol methyl ether acetate.
Claim 15
Dependent Claim
43 words
A photoresist composition according to claim 2, wherein said phenolic compound is a dihydroxybenzophenone, a trihydroxybenzophenone or a tetrahydroxybenzophenone; and said organic acid halide is a lower alkyl sulfonyl halide, a benzene sufonyl halide, a lower alkyl acyl halide or a benzoyl halide.
Claim 16
Dependent Claim
13 words
A photoresist composition according to claim 2, wherein said phenolic compound is 2,3,4-trihydroxybenzophenone.
Claim 17
Dependent Claim
16 words
A photoresist composition according to claim 14, wherein said solvent is propylene glycol methyl ether acetate.
Claim 18
Dependent Claim
70 words
A method for producing an article which comprises coating a photoresist composition comprising a novolak or polyvinyl phenol resin, a solvent and a photosensitizer composition according to claim 2 onto a substrate; imagewise exposing said composition to sufficient ultraviolet radiation to render said imagewise exposed portions substantially soluble in an aqueous alkaline solution; and then removing the thusly exposed composition portions from said substrate with an aqueous alkaline developing solution.
References Cited (Backward Citations)
US3046118A
Cited
US3046115A
Cited
US3106465A
Cited
US3148983A
Cited
US3635709A
Cited
US3647443A
Cited
US3984250A
Cited
US3666473A
Cited
US3890152A
Cited
US3902906A
Cited
US4173470A
Cited
US4308368A
Cited
US4407926A
Cited
US4555469A
Cited
JPS57150944A
Cited
US4439511A
Cited
JPS5875149A
Cited
US4458000A
Cited
US4397937A
Cited
US4499171A
Cited
US4526856A
Cited
US4576901A
Cited
US4632900A
Cited
US4550069A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-03-22 | 1991-09-21 | 1992-03-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-22 | 1995-09-21 | 1996-03-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-22 | 1999-09-21 | 2000-03-22 | $7700.00 | Window Closed / Lapsed |