US5733714A
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Antireflective coating for photoresist compositions
Assignee: Merck Patent GmbH
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Filing: 1996-09-30
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Granted: 1998-03-31
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Expires: 2016-09-30
Abstract
Abstract The present invention relates to a novel antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and an organic solvent or a mixture of organic solvents, where the novel polymer comprises a unit containing a dye that absorbs from about 180 nm to about 450 nm and a unit containing a crosslinking group.
Inventors
- 👤 Iain McCulloch
- 👤 Ralph R. Dammel
- 👤 Anthony J. Corso
- 👤 Shuji Ding
- 👤 Dana L. Durham
- 👤 Ping-Hung Lu
- 👤 Ming Kang
- 👤 Dinesh N. Khanna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:20
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03C; G03C1/00; G03C1/76; G03C1/825; G03C1/835; G03F7/091; Y; Y10; Y10S; Y10S430/00; Y10S430/151
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
233 words
An antireflecting coating composition for use in photolithography, comprising a) a polymer comprising at least one dye unit having a structure, ##STR10## where R 1 -R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, X 1 is C═O, OCO, CONH, O, aryl, (C 1 -C 10 ) alkyl, cyclohexyl, pyridine or pyrollidone, X 2 is S, S(C 1 -C 10 ) alkyl, O, O(C 1 -C 10 ) alkyl, NH, N(C 1 -C 10 ) alkyl, alkyl, or hydroxyalkyl(C 1 -C 10 ), n=0-2, A is an electronwithdrawing group, R 4 is H, (C 1 -C 10 ) alkyl, (C 1 -C 10 ) alkoxy, nitro, halide, cyano, aryl, alkylaryl, alkenyl, dicyanovinyl or SO 2 CF 3 , COOZ, SO 3 Z, COZ, OZ, NZ 2 , SZ, SO 2 Z, NHCOZ, or SO 2 NZ 2 , where Z is H or (C 1 -C 10 ) alkyl, Y is a conjugated moiety N═N, CW═CW, CW═N, or N═CW, where W is H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, m=1-5, and at least one unit capable of crosslinking the polymer having a structure ##STR11## where G contains a crosslinking functionality and R 1 to R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, and b) a suitable solvent.
Claim 2
Dependent Claim
233 words
An antireflecting coating composition for use in photolithography, comprising a) a polymer comprising at least one dye unit having a structure, ##STR10## where R 1 -R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, X 1 is C═O, OCO, CONH, O, aryl, (C 1 -C 10 ) alkyl, cyclohexyl, pyridine or pyrollidone, X 2 is S, S(C 1 -C 10 ) alkyl, O, O(C 1 -C 10 ) alkyl, NH, N(C 1 -C 10 ) alkyl, alkyl, or hydroxyalkyl(C 1 -C 10 ), n=0-2, A is an electronwithdrawing group, R 4 is H, (C 1 -C 10 ) alkyl, (C 1 -C 10 ) alkoxy, nitro, halide, cyano, aryl, alkylaryl, alkenyl, dicyanovinyl or SO 2 CF 3 , COOZ, SO 3 Z, COZ, OZ, NZ 2 , SZ, SO 2 Z, NHCOZ, or SO 2 NZ 2 , where Z is H or (C 1 -C 10 ) alkyl, Y is a conjugated moiety N═N, CW═CW, CW═N, or N═CW, where W is H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, m=1-5, and at least one unit capable of crosslinking the polymer having a structure ##STR11## where G contains a crosslinking functionality and R 1 to R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, and b) a suitable solvent.
Claim 3
Dependent Claim
177 words
The antireflective coating composition according to claim 1, wherein the dye unit has a structure ##STR12## where R 1 -R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, X 1 is C═O, OCO, CONH, O, aryl, (C 1 -C 10 ) alkyl, cyclohexyl, pyridine or pyrollidone, X 2 , is S, S(C 1 -C 10 ) alkyl, O, O(C 1 -C 10 ) alkyl, NH, N(C 1 -C 10 ) alkyl, alkyl, or hydroxyalkyl(C 1 -C 10 ), n=0-2, R 4 is H, (C 1 -C 10 ) alkyl, (C 1 -C 10 ) alkoxy, nitro, halide, cyano, aryl, alkylaryl, alkenyl, dicyanovinyl or SO 2 CF 3 , COOZ, SO 3 Z, COZ, OZ, NZ 2 , SZ, SO 2 Z, NHCOZ, or SO 2 NZ 2 , where Z is H or (C 1 -C 10 ) alkyl, Y is a conjugated moiety N═N, CW═CW, CW═N, or N═CW, where W is H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy, and m=1-5.
Claim 4
Dependent Claim
16 words
The antireflective composition according to claim 1, wherein the solvent comprises a mixture of organic solvents.
Claim 5
Dependent Claim
33 words
The antireflective composition according to claim 1, wherein the solvent is selected from a group consisting of propylene glycol monomethyl ether, propylene glycol monomethyl etheracetate, ethyl lactate, heptanone, cyclopentanone, cyclohexanone, and gamma butyrolactone.
Claim 6
Dependent Claim
12 words
The antireflective composition according to claim 1, wherein the solvent comprises water.
Claim 7
Dependent Claim
31 words
The 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 8
Dependent Claim
17 words
The antireflective composition according to claim 1, wherein Y in the dye unit is an azo moiety.
Claim 9
Dependent Claim
35 words
The antireflective composition of claim 1, wherein the dye unit ranges from about 5 to about 95 mole percent and the crosslinking unit ranges from about 1 to about 50 mole percent of the polymer.
Claim 10
Dependent Claim
22 words
The antireflective composition according to claim 1, wherein the polymer further comprises one or more vinyl monomers that are nonabsorbing and noncrosslinking.
Claim 11
Dependent Claim
36 words
The antireflective composition according to claim 9, wherein the vinyl monomer is selected from a group consisting of maleic anhydride, vinyl acrylates, vinyl phenolics, vinyl ethers, vinyl acrylamides, vinyl carboxylic acids, vinyl sulphonic acids and N-(3-Hydroxyphenylmethacrylamide).
Claim 12
Dependent Claim
27 words
The antireflective composition according to claim 1, further comprising at least one unit derived from a hydrophilic vinyl monomer or a vinyl monomer capable of becoming hydrophilic.
Claim 13
Dependent Claim
43 words
The antireflective composition according to claim 11, where the hydrophilic vinyl monomer has a structure: ##STR13## where R 1 -R 3 are independently H, (C 1 -C 10 ) alkyl or (C 1 -C 10 ) alkoxy and W is a hydrophilic group.
Claim 14
Dependent Claim
60 words
The aqueous antireflective composition according to claim 12, 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 15
Dependent Claim
28 words
The antireflective composition according to claim 11, where the hydrophilic vinyl monomer is selected from a group consisting of maleic anhydride, fumaric anhydride, vinyl pyridines, and vinyl pyrollidones.
Claim 16
Dependent Claim
49 words
The antireflective composition according to claim 11, 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 17
Dependent Claim
11 words
The antireflective composition according to claim 1, further comprising a dye.
Claim 18
Dependent Claim
12 words
The antireflective composition according to claim 1, further comprising a crosslinking agent.
Claim 19
Dependent Claim
12 words
The antireflective composition according to claim 1, further comprising an acid generator.
Claim 20
Dependent Claim
17 words
The antireflective composition according to claim 18, wherein the acid generator is a thermally activated acid generator.
Claim 21
Dependent Claim
21 words
The antireflective composition according to claim 19, wherein the thermally activated acid generator is a diazo naphthoquinone ester of a multihydroxybenzophenone.
Claim 22
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 23
Dependent Claim
20 words
The antireflective composition according to claim 1, wherein metal ion levels are less than 50 ppb for each metal ion.
Claim 24
Dependent Claim
85 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 top of the antireflective coating, d) heating the photoresist coating to substantially remove solvent from the photoresist 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 25
Dependent Claim
19 words
The process of claim 23, wherein the photoresist solution comprises a novolak resin, a photosensitive compound and a solvent.
Claim 26
Dependent Claim
19 words
The process of claim 23, wherein the photoresist solution comprises a substituted polyhydroxystyrene, a photoactive compound and a solvent.
Claim 27
Dependent Claim
20 words
The process of claim 23, wherein the photoresist solution comprises polyhydroxystyrene, a photoactive compound, a dissolution inhibitor and a solvent.
Claim 28
Dependent Claim
22 words
The process of claim 23, wherein the heating temperature for the antireflective coating ranges from about 70° C. to about 250° C.
Claim 29
Dependent Claim
18 words
The process of claim 23, wherein the developer is an aqueous solution of metal ion free alkaline hydroxide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-03-30 | 2001-09-29 | 2002-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-03-30 | 2005-09-29 | 2006-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-03-30 | 2009-09-29 | 2010-03-31 | $7700.00 | Window Closed / Lapsed |