CN1166704C - 防反射性涂料聚合物及其制备方法 - Google Patents
防反射性涂料聚合物及其制备方法 Download PDFInfo
- Publication number
- CN1166704C CN1166704C CNB991249739A CN99124973A CN1166704C CN 1166704 C CN1166704 C CN 1166704C CN B991249739 A CNB991249739 A CN B991249739A CN 99124973 A CN99124973 A CN 99124973A CN 1166704 C CN1166704 C CN 1166704C
- Authority
- CN
- China
- Prior art keywords
- general formula
- anthracene
- carboxylic acid
- alkyl
- following formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920001688 coating polymer Polymers 0.000 title abstract description 5
- 238000000576 coating method Methods 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 6
- 238000000206 photolithography Methods 0.000 claims abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- 239000011248 coating agent Substances 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 17
- -1 acrylic ester Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 229920003986 novolac Polymers 0.000 claims description 11
- 150000008376 fluorenones Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000008199 coating composition Substances 0.000 claims description 9
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims description 8
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002220 fluorenes Chemical class 0.000 claims description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001459 lithography Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical group CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 2
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 claims 6
- 241001597008 Nomeidae Species 0.000 claims 6
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 3
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 claims 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 3
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 claims 3
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 claims 3
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 claims 3
- KEQZHLAEKAVZLY-UHFFFAOYSA-N anthracene-9-carbonitrile Chemical compound C1=CC=C2C(C#N)=C(C=CC=C3)C3=CC2=C1 KEQZHLAEKAVZLY-UHFFFAOYSA-N 0.000 claims 3
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims 3
- TZIQWQARHPGHIG-UHFFFAOYSA-N anthrarobin Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C(O)=C21 TZIQWQARHPGHIG-UHFFFAOYSA-N 0.000 claims 3
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims 3
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims 3
- 229960002311 dithranol Drugs 0.000 claims 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims 3
- 229960004985 lumefantrine Drugs 0.000 claims 3
- 229960001156 mitoxantrone Drugs 0.000 claims 3
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000006117 anti-reflective coating Substances 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 7
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000008030 elimination Effects 0.000 abstract description 2
- 238000003379 elimination reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000003667 anti-reflective effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000012954 diazonium Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000010748 Photoabsorption Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/16—Halogens
- C08F212/20—Fluorine
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-1998-0063695A KR100363695B1 (ko) | 1998-12-31 | 1998-12-31 | 유기난반사방지중합체및그의제조방법 |
| KR63695/1998 | 1998-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1260355A CN1260355A (zh) | 2000-07-19 |
| CN1166704C true CN1166704C (zh) | 2004-09-15 |
Family
ID=19570257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991249739A Expired - Fee Related CN1166704C (zh) | 1998-12-31 | 1999-12-23 | 防反射性涂料聚合物及其制备方法 |
Country Status (10)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1190277B1 (en) * | 1999-06-10 | 2009-10-07 | AlliedSignal Inc. | Semiconductor having spin-on-glass anti-reflective coatings for photolithography |
| US6824879B2 (en) | 1999-06-10 | 2004-11-30 | Honeywell International Inc. | Spin-on-glass anti-reflective coatings for photolithography |
| KR100557606B1 (ko) * | 1999-08-31 | 2006-03-10 | 주식회사 하이닉스반도체 | 유기 난반사 방지용 중합체 |
| KR100427440B1 (ko) * | 1999-12-23 | 2004-04-17 | 주식회사 하이닉스반도체 | 유기 반사방지 화합물 및 그의 제조방법 |
| US7132219B2 (en) * | 2001-02-02 | 2006-11-07 | Brewer Science Inc. | Polymeric antireflective coatings deposited by plasma enhanced chemical vapor deposition |
| JP3509760B2 (ja) * | 2001-02-08 | 2004-03-22 | 株式会社半導体先端テクノロジーズ | 半導体装置の製造方法 |
| KR100465866B1 (ko) * | 2001-10-26 | 2005-01-13 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| JP4381143B2 (ja) * | 2001-11-15 | 2009-12-09 | ハネウェル・インターナショナル・インコーポレーテッド | フォトリソグラフィー用スピンオン反射防止膜 |
| US6852474B2 (en) * | 2002-04-30 | 2005-02-08 | Brewer Science Inc. | Polymeric antireflective coatings deposited by plasma enhanced chemical vapor deposition |
| WO2004027850A1 (en) * | 2002-09-20 | 2004-04-01 | Honeywell International, Inc. | Interlayer adhesion promoter for low k materials |
| US7056826B2 (en) * | 2003-01-07 | 2006-06-06 | Taiwan Semiconductor Manufacturing Co., Ltd. | Method of forming copper interconnects |
| US8053159B2 (en) | 2003-11-18 | 2011-11-08 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
| US7078336B2 (en) * | 2003-11-19 | 2006-07-18 | Taiwan Semiconductor Manufacturing Co., Ltd. | Method and system for fabricating a copper barrier layer with low dielectric constant and leakage current |
| US20050255410A1 (en) * | 2004-04-29 | 2005-11-17 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
| US20060255315A1 (en) * | 2004-11-19 | 2006-11-16 | Yellowaga Deborah L | Selective removal chemistries for semiconductor applications, methods of production and uses thereof |
| JP4720988B2 (ja) * | 2005-07-11 | 2011-07-13 | 日産化学工業株式会社 | フルオレン構造を有する化合物を含むリソグラフィー用下層膜形成組成物 |
| KR100671114B1 (ko) | 2005-07-28 | 2007-01-17 | 제일모직주식회사 | 반사방지성을 갖는 하드마스크 조성물 |
| US7488771B2 (en) * | 2005-09-02 | 2009-02-10 | International Business Machines Corporation | Stabilization of vinyl ether materials |
| US7419611B2 (en) * | 2005-09-02 | 2008-09-02 | International Business Machines Corporation | Processes and materials for step and flash imprint lithography |
| US7914974B2 (en) | 2006-08-18 | 2011-03-29 | Brewer Science Inc. | Anti-reflective imaging layer for multiple patterning process |
| JP4952906B2 (ja) * | 2006-11-15 | 2012-06-13 | ソニーケミカル＆インフォメーションデバイス株式会社 | 封止樹脂組成物及び発光素子 |
| US8642246B2 (en) * | 2007-02-26 | 2014-02-04 | Honeywell International Inc. | Compositions, coatings and films for tri-layer patterning applications and methods of preparation thereof |
| JP5099140B2 (ja) * | 2007-08-24 | 2012-12-12 | 東レ株式会社 | 感光性組成物、それから形成された硬化膜、および硬化膜を有する素子 |
| EP2245512B1 (en) | 2008-01-29 | 2019-09-11 | Brewer Science, Inc. | On-track process for patterning hardmask by multiple dark field exposures |
| US9640396B2 (en) | 2009-01-07 | 2017-05-02 | Brewer Science Inc. | Spin-on spacer materials for double- and triple-patterning lithography |
| US8557877B2 (en) | 2009-06-10 | 2013-10-15 | Honeywell International Inc. | Anti-reflective coatings for optically transparent substrates |
| JP5842503B2 (ja) * | 2010-09-29 | 2016-01-13 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びその形成方法 |
| KR101811064B1 (ko) | 2010-09-29 | 2017-12-20 | 제이에스알 가부시끼가이샤 | 패턴형성 방법, 레지스트 하층막의 형성 방법, 레지스트 하층막 형성용 조성물 및 레지스트 하층막 |
| US8864898B2 (en) | 2011-05-31 | 2014-10-21 | Honeywell International Inc. | Coating formulations for optical elements |
| KR101993480B1 (ko) * | 2011-12-16 | 2019-06-26 | 제이에스알 가부시끼가이샤 | 레지스트 하층막 형성용 수지 조성물, 레지스트 하층막, 그의 형성 방법 및 패턴 형성 방법 |
| JP6160068B2 (ja) * | 2011-12-16 | 2017-07-12 | Jsr株式会社 | レジスト下層膜形成用樹脂組成物、レジスト下層膜、その形成方法及びパターン形成方法 |
| EP3194502A4 (en) | 2015-04-13 | 2018-05-16 | Honeywell International Inc. | Polysiloxane formulations and coatings for optoelectronic applications |
| CN107797384B (zh) * | 2016-09-07 | 2020-10-09 | 上海飞凯电子材料有限公司 | 一种感光树脂、正性光刻胶及应用 |
| CN117820910A (zh) * | 2022-06-30 | 2024-04-05 | 华为技术有限公司 | 涂层材料和集成电路及制备方法、电子设备 |
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| JPS5236043B2 (US06492441-20021210-C00072.png) * | 1974-02-21 | 1977-09-13 | ||
| DE3100077A1 (de) * | 1981-01-03 | 1982-08-05 | Hoechst Ag, 6000 Frankfurt | Lichtempfindliches gemisch, das einen naphthochinondiazidsulfonsaeureester enthaelt, und verfahren zur herstellung des naphthochinondiazidsulfonsaeureesters |
| US4822718A (en) | 1982-09-30 | 1989-04-18 | Brewer Science, Inc. | Light absorbing coating |
| US5674648A (en) | 1984-08-06 | 1997-10-07 | Brewer Science, Inc. | Anti-reflective coating |
| GB8430377D0 (en) * | 1984-12-01 | 1985-01-09 | Ciba Geigy Ag | Modified phenolic resins |
| GB8505402D0 (en) * | 1985-03-02 | 1985-04-03 | Ciba Geigy Ag | Modified phenolic resins |
| JP2740837B2 (ja) * | 1987-01-30 | 1998-04-15 | コニカ株式会社 | 多色転写画像形成方法 |
| JPH0210346A (ja) * | 1988-06-29 | 1990-01-16 | Matsushita Electric Ind Co Ltd | パターン形成材料 |
| CA2041434A1 (en) * | 1990-05-02 | 1991-11-03 | Teijiro Kitao | Resist composition |
| KR920005774B1 (ko) * | 1990-06-16 | 1992-07-18 | 제일합섬 주식회사 | 반도체용 포지티브 포토레지스트 조성물 |
| DE4106356A1 (de) * | 1991-02-28 | 1992-09-03 | Hoechst Ag | Strahlungsempfindliche polymere mit naphthochinon-2-diazid-4-sulfonyl-gruppen und deren verwendung in einem positiv arbeitenden aufzeichnungsmaterial |
| JPH05188588A (ja) * | 1992-01-08 | 1993-07-30 | Konica Corp | 感光性平版印刷版 |
| JP3192548B2 (ja) * | 1994-04-22 | 2001-07-30 | 東京応化工業株式会社 | ポジ型ホトレジスト組成物 |
| US6669995B1 (en) * | 1994-10-12 | 2003-12-30 | Linda Insalaco | Method of treating an anti-reflective coating on a substrate |
| US5525457A (en) * | 1994-12-09 | 1996-06-11 | Japan Synthetic Rubber Co., Ltd. | Reflection preventing film and process for forming resist pattern using the same |
| GB9426206D0 (en) * | 1994-12-23 | 1995-02-22 | Horsell Plc | Lithographic plate |
| US5529880A (en) * | 1995-03-29 | 1996-06-25 | Shipley Company, L.L.C. | Photoresist with a mixture of a photosensitive esterified resin and an o-naphthoquinone diazide compound |
| US5719004A (en) * | 1996-08-07 | 1998-02-17 | Clariant Finance (Bvi) Limited | Positive photoresist composition containing a 2,4-dinitro-1-naphthol |
| JP3823449B2 (ja) * | 1997-06-16 | 2006-09-20 | 住友化学株式会社 | フォトレジスト組成物 |
| TW457403B (en) | 1998-07-03 | 2001-10-01 | Clariant Int Ltd | Composition for forming a radiation absorbing coating containing blocked isocyanate compound and anti-reflective coating formed therefrom |
-
1998
- 1998-12-31 KR KR10-1998-0063695A patent/KR100363695B1/ko not_active IP Right Cessation
-
1999
- 1999-07-23 GB GB9917218A patent/GB2345289B/en not_active Expired - Fee Related
- 1999-07-30 FR FR9909924A patent/FR2788060B1/fr not_active Expired - Fee Related
- 1999-08-17 NL NL1012840A patent/NL1012840C2/nl not_active IP Right Cessation
- 1999-08-25 DE DE19940320A patent/DE19940320B4/de not_active Expired - Fee Related
- 1999-09-22 TW TW088116247A patent/TWI227259B/zh not_active IP Right Cessation
- 1999-10-07 US US09/413,679 patent/US6350818B1/en not_active Expired - Fee Related
- 1999-10-12 JP JP28983199A patent/JP4253088B2/ja not_active Expired - Fee Related
- 1999-11-24 IT IT1999TO001027A patent/IT1308658B1/it active
- 1999-12-23 CN CNB991249739A patent/CN1166704C/zh not_active Expired - Fee Related
-
2001
- 2001-12-11 US US10/015,333 patent/US6492441B2/en not_active Expired - Fee Related
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2007
- 2007-02-22 JP JP2007042141A patent/JP2007231270A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ITTO991027A0 (it) | 1999-11-24 |
| ITTO991027A1 (it) | 2001-05-24 |
| FR2788060A1 (fr) | 2000-07-07 |
| DE19940320B4 (de) | 2006-09-21 |
| GB9917218D0 (en) | 1999-09-22 |
| TWI227259B (en) | 2005-02-01 |
| GB2345289A (en) | 2000-07-05 |
| NL1012840C2 (nl) | 2001-06-07 |
| DE19940320A1 (de) | 2000-07-06 |
| CN1260355A (zh) | 2000-07-19 |
| KR100363695B1 (ko) | 2003-04-11 |
| FR2788060B1 (fr) | 2003-10-17 |
| NL1012840A1 (nl) | 2000-07-03 |
| JP2000204115A (ja) | 2000-07-25 |
| US6492441B2 (en) | 2002-12-10 |
| GB2345289B (en) | 2003-03-26 |
| KR20010016643A (ko) | 2001-03-05 |
| US20020120070A1 (en) | 2002-08-29 |
| JP2007231270A (ja) | 2007-09-13 |
| US6350818B1 (en) | 2002-02-26 |
| IT1308658B1 (it) | 2002-01-09 |
| JP4253088B2 (ja) | 2009-04-08 |
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