US5652297A
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Aqueous antireflective coatings for photoresist compositions
Assignee: Clariant Finance BVI Ltd
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Filing: 1996-08-16
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Granted: 1997-07-29
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Expires: 2016-08-16
Abstract
Abstract The present invention relates to a novel aqueous antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and water, where the novel polymer of the antireflective coating comprises at least one unit containing a dye that absorbs from about 180 nm to about 450 nm, at least one unit containing a crosslinking group and at least one unit derived from a hydrophilic vinyl monomer or a vinyl monomer capable of becoming hydrophilic.
Inventors
- 👤 Iain McCulloch
- 👤 Ralph R. Dammel
- 👤 Dana L. Durham
- 👤 Ping-Hung Lu
- 👤 Ming Kang
- 👤 Dinesh N. Khanna
- 👤 Shuji Ding
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:52
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/091; C; C08; C08F; C08F20/00; C08F20/02; C08F20/52; C08F20/54; C08F20/60; C08F8/00; C08F8/30; C08F2800/00; C08F2800/10; C08F2800/20; C08F2810/00; C08F2810/20
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
202 words
An aqueous antireflective coating composition for use in photolithography, comprising water and a polymer containing: a) at least one dye unit having the structure: ##STR1## where R 1 -R 4 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, R 5 is OH, NH 2 , OCH 3 or OCH 2 CH 3 , R 6 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, R 7 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, or nitro, R 8 is nitro, SONH 2 , COOY, SO 3 Y, where Y is H, alkali metal, ammonium or alkyl ammonium, X is a conjugated moiety e.g. N═N, CZ═CZ, CZ═N, N═CZ, where Z is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, m=1-3, and n=1-4; b) at least one unit having the structure ##STR2## where R 1 -R 4 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy and Y contains a crosslinking group; and c) at least one unit derived from a hydrophilic vinyl monomer or a vinyl monomer capable of becoming hydrophilic.
Claim 2
Dependent Claim
202 words
An aqueous antireflective coating composition for use in photolithography, comprising water and a polymer containing: a) at least one dye unit having the structure: ##STR1## where R 1 -R 4 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, R 5 is OH, NH 2 , OCH 3 or OCH 2 CH 3 , R 6 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, R 7 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, or nitro, R 8 is nitro, SONH 2 , COOY, SO 3 Y, where Y is H, alkali metal, ammonium or alkyl ammonium, X is a conjugated moiety e.g. N═N, CZ═CZ, CZ═N, N═CZ, where Z is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, m=1-3, and n=1-4; b) at least one unit having the structure ##STR2## where R 1 -R 4 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy and Y contains a crosslinking group; and c) at least one unit derived from a hydrophilic vinyl monomer or a vinyl monomer capable of becoming hydrophilic.
Claim 3
Dependent Claim
43 words
The aqueous antireflective composition according to claim 1, where the hydrophilic vinyl monomer has the structure: ##STR3## where R 1 -R 3 is H, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy and W is a hydrophilic group.
Claim 4
Dependent Claim
60 words
The aqueous antireflective composition according to claim 2, wherein the hydrophilic group is selected from a group consisting of O(CH 2 ) 2 --O--(CH 2 )--OH, O(CH 2 ) 2 --OH, (CH 2 ) n --OH (where n=1-4), COO(C 1 -C 4 )alkyl, COOX, SO 3 X (where X is H, alkali metal, ammonium, alkyl ammonium) and CONHCH 2 OH.
Claim 5
Dependent Claim
29 words
The aqueous antireflective composition according to claim 1, where the hydrophilic vinyl monomer is selected from a group consisting of maleic anhydride, fumaric anhydride, vinyl pyridines, and vinyl pyrollidones.
Claim 6
Dependent Claim
32 words
The aqueous antireflective composition according to claim 1, wherein the crosslinking group is selected from a group consisting of carbodiimide, isocyanate, blocked isocyanate, glycidyl methacrylate, alkylol acrylamide, alkylol methacrylamide and methyl acrylamidoglycolate.
Claim 7
Dependent Claim
18 words
The aqueous antireflective composition according to claim 1, wherein X in the dye unit is an azo group.
Claim 8
Dependent Claim
16 words
The aqueous antireflective composition according to claim 1, further comprising a water miscible alcohol or acetate.
Claim 9
Dependent Claim
50 words
The aqueous antireflective composition according to claim 1, wherein the dye unit ranges from about 5 to about 95 mole percent, the crosslinking unit ranges from about 1 to about 50 mole percent and the hydrophilic vinyl monomer ranges from about 1 to about 50 mole percent of the polymer.
Claim 10
Dependent Claim
24 words
The aqueous antireflective composition according to claim 1, wherein the polymer further comprises one or more vinyl monomers that are nonabsorbing, noncrosslinking and nonhydrophilic.
Claim 11
Dependent Claim
16 words
The aqueous antireflective composition according to claim 1, wherein the composition further comprises a crosslinking agent.
Claim 12
Dependent Claim
15 words
The aqueous antireflective composition according to claim 1, wherein the composition further comprises a dye.
Claim 13
Dependent Claim
25 words
The antireflective composition according to claim 1, wherein the polymer has a weight average molecular weight in the range of about 2,500 to about 1,000,000.
Claim 14
Dependent Claim
20 words
The antireflective composition according to claim 1, wherein the metal ion level is less than 50 ppb each metal ion.
Claim 15
Dependent Claim
81 words
The process of forming an image on a substrate comprising the steps of: a) coating the substrate with the antireflective coating composition of claim 1, b) heating the antireflective coating, c) coating a photoresist solution on the substrate, d) heating the photoresist coating to substantially remove solvent from the coating, e) imagewise exposing the photoresist coating, f) developing an image using an aqueous alkaline developer, g) optionally, heating the substrate prior to and after development, h) dry etching the antireflective coating.
Claim 16
Dependent Claim
19 words
The process of claim 14, wherein the photoresist solution comprises a novolak resin, a photosensitive compound and a solvent.
Claim 17
Dependent Claim
19 words
The process of claim 14, wherein the photoresist solution comprises a substituted polyhydroxystyrene, a photoactive compound and a solvent.
Claim 18
Dependent Claim
20 words
The process of claim 14, wherein the photoresist solution comprises polyhydroxystyrene, a photoactive compound, a dissolution inhibitor and a solvent.
Claim 19
Dependent Claim
24 words
The process of claim 14, wherein the heating temperature for hardening of the antireflective coating ranges from about 70° C. to about 250° C.
Claim 20
Dependent Claim
14 words
The process of claim 14, wherein the aqueous alkaline developer comprises tetramethyl ammonium hydroxide.
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) | 2000-07-28 | 2001-01-27 | 2001-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-07-28 | 2005-01-27 | 2005-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-07-28 | 2009-01-27 | 2009-07-29 | $7700.00 | Window Closed / Lapsed |