US4564575A
Expired / Lapsed
US
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Tailoring of novolak and diazoquinone positive resists by acylation of novolak
Assignee: International Business Machines Corp
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Filing: 1984-01-30
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Granted: 1986-01-14
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Expires: 2004-01-30
Abstract
Abstract Reduction of the alkaline developer solubility of novolak-diazoquinone positive resists by acylation of phenolic hydroxyl groups of the novolak resin.
Inventors
- 👤 Stanley E. Perreault
- 👤 Robert L. Wood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:06
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233; G03F7/0236
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
108 words
A positive lithographic resist composition comprised of an admixture of a novolak resin, in sufficient quantity amount when combined with a photoactive component to be developable to form a positive image, and a radiation-sensitive diazoquinone in sufficient amount to function as the photoactive component in an electron bem or optical process, wherein said novolak resin has hydroxyl groups thereof acylated so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations in order to reduce solubility in alkaline developers, and where R is a saturated aliphatic group containing from 1 to 4 carbon atoms.
Claim 2
Dependent Claim
108 words
A positive lithographic resist composition comprised of an admixture of a novolak resin, in sufficient quantity amount when combined with a photoactive component to be developable to form a positive image, and a radiation-sensitive diazoquinone in sufficient amount to function as the photoactive component in an electron bem or optical process, wherein said novolak resin has hydroxyl groups thereof acylated so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations in order to reduce solubility in alkaline developers, and where R is a saturated aliphatic group containing from 1 to 4 carbon atoms.
Claim 3
Dependent Claim
12 words
The resist composition of claim 1 wherein said acyl group is acetyl.
Claim 4
Dependent Claim
13 words
The resist composition of claim 2 wherein said novolak is comprised of cresol-formaldehyde.
Claim 5
Dependent Claim
23 words
The resist composition of claim 3 wherein from about 1 to about 5% of the phenolic hydroxyl groups, of said novolak, are acylated.
Claim 6
Dependent Claim
13 words
The resist composition of claim 1 wherein said novolak is comprised of cresol-formaldehyde.
Claim 7
Dependent Claim
22 words
The resist composition of claim 5 wherein about 1 to about 5% of the phenolic hydroxyl groups of said novolak are acylated.
Claim 8
Dependent Claim
22 words
The resist composition of claim 1 wherein about 1 to about 5% of the phenolic hydroxyl groups, of said novolak, are acylated.
Claim 9
Dependent Claim
22 words
The resist composition of claim 1 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 10
Dependent Claim
22 words
The resist composition of claim 2 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 11
Dependent Claim
22 words
The resist composition of claim 3 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 12
Dependent Claim
22 words
The resist composition of claim 4 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 13
Dependent Claim
22 words
The resist composition of claim 5 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 14
Dependent Claim
22 words
The resist composition of claim 6 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 15
Dependent Claim
112 words
A substrate coated with a layer of a photoresist comprised of an admixture of a novolak resin, in sufficient quantity amount when combined with a photoactive component to be developable to form a positive image, and a radiation-sensitive diazoquinone in sufficient amount to function as the photosensitive component in an electron beam or optical process, wherein said novolak resin has phenolic hydroxyl groups acetylated so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations in order to reduce solubility in alkaline developers, and where R is a saturated aliphatic group containing from 1 to 4 carbon atoms.
Claim 16
Dependent Claim
112 words
A substrate coated with a layer of a photoresist comprised of an admixture of a novolak resin, in sufficient quantity amount when combined with a photoactive component to be developable to form a positive image, and a radiation-sensitive diazoquinone in sufficient amount to function as the photosensitive component in an electron beam or optical process, wherein said novolak resin has phenolic hydroxyl groups acetylated so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations in order to reduce solubility in alkaline developers, and where R is a saturated aliphatic group containing from 1 to 4 carbon atoms.
Claim 17
Dependent Claim
13 words
The structure of claim 14 wherein said substrate is comprised of semiconductor devices.
Claim 18
Dependent Claim
13 words
The structure of claim 15 wherein said devices are comprised of integrated circuits.
Claim 19
Dependent Claim
11 words
The structure of claim 16 wherein said acyl group is acetyl.
Claim 20
Dependent Claim
12 words
The structure of claim 17 wherein said novolak is comprised of cresol-formaldehyde.
Claim 21
Dependent Claim
21 words
The structure of claim 18 wherein said novolak has a molecular wight in the range of about 2000 to about 20000.
Claim 22
Dependent Claim
22 words
The structure of claim 19 wherein from about 1 to about 5% of the phenolic hydroxyl groups, of said novolak, are acylated.
Claim 23
Independent Claim
74 words
A method of reducing the dissolution rates of novolak-diazoquinone resists in alkaline solution, comprising: (a) providing said novolak resin; (b) acylating the phenolic hydroxyl groups of said novolak resin, so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations, and where R is an alkyl group containing from 1 to 4 carbon atoms; and (c) adding said diazoquinone thereto.
Claim 24
Independent Claim
74 words
A method of reducing the dissolution rates of novolak-diazoquinone resists in alkaline solution, comprising: (a) providing said novolak resin; (b) acylating the phenolic hydroxyl groups of said novolak resin, so that an acyl group having the structure RCO-- exists in place of the hydrogen at at least a portion of the phenolic hydroxyl locations, and where R is an alkyl group containing from 1 to 4 carbon atoms; and (c) adding said diazoquinone thereto.
Claim 25
Dependent Claim
25 words
The method of claim 21 where said hydroxyl groups are acylated with an anhydride of an aliphatic monoacid containing from 2 to 5 carbon atoms.
Claim 26
Dependent Claim
14 words
The method of claim 22 wherein said novolak is comprised of a cresol-formaldehyde resin.
Claim 27
Dependent Claim
21 words
The method of claim 23 wherein said resin has a molecular weight in the range of about 2000 to about 20000.
Claim 28
Dependent Claim
11 words
The method of claim 24 wherein said anhydride comprises acetic anhydride.
Claim 29
Dependent Claim
22 words
The method of claim 25 wherein from about 1 to about 5% of the phenolic hydroxyl groups of said novolak are acylated.
Claim 30
Dependent Claim
29 words
The method of claim 21 wherein said novolak resin is dissolved in a casting solvent at a concentration appropriate for the resist type prior to the step (b) acylation.
Claim 31
Dependent Claim
26 words
The method of claim 27 wherein said phenolic hydroxyl groups are acylated using an anhydride of an aliphatic monoacid containing from 2 to 5 carbon atoms.
Claim 32
Dependent Claim
36 words
The method of claim 28 wherein the solution of novolak resin combined with said anhydride of an aliphatic monoacid is mixed at about 50° C. for a period sufficient to effect the desired amount of acylation.
Claim 33
Dependent Claim
15 words
The resist composition of claim 3 wherein said diazoquinone is comprised of an o-quinone diazide.
Claim 34
Dependent Claim
17 words
The resist composition of claim 30 wherein said o-quinone diazide is comprised of 2-diazo-1-oxonaphtholene-5-sulfonate diester of (2,4)-dihydroxybenzophenone.
Claim 35
Dependent Claim
15 words
The resist composition of claim 4 wherein said diazoquinone is comprised of an o-quinone diazide.
Claim 36
Dependent Claim
17 words
The resist composition of claim 32 wherein said o-quinone diazide is comprised of 2-diazo-1-oxonaptholene-5-sulfonate diester of (2,4)-dihydroxybenzophenone.
Claim 37
Dependent Claim
14 words
The structure of claim 14 wherein said diazoquinone is comprised of an o-quinone diazide.
Claim 38
Dependent Claim
16 words
The structure of claim 34 wherein said o-quinone diazide is comprised of 2-diazo-1-oxynaptholone-5-sulfonate diester of (2,4)-dihydroxybenzophenone.
Claim 39
Dependent Claim
21 words
The structure of claim 35 wherein said novolak has a molecular weight in the range of about 2000 to about 20000.
Claim 40
Dependent Claim
22 words
The structure of claim 36 wherein from about 1 to about 5% of the phenolic hydroxyl groups, of said novolak, are acylated.
Claim 41
Dependent Claim
14 words
The method of claim 26 wherin said diazoquinone is comprised of an o-quinone diazide.
Claim 42
Dependent Claim
17 words
The method of claim 38 wherein said o-quinone diazide is comprised of a 2-diazo-1-oxonaptholene-5-sulfonate diester of (2,4)-dihydroxybenzophenone.
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) | 1989-01-13 | 1989-07-15 | 1990-01-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-13 | 1993-07-15 | 1994-01-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-13 | 1997-07-15 | 1998-01-14 | $7700.00 | Window Closed / Lapsed |