WO1999063010A1 - Composition pour revetement reduisant la reflexion - Google Patents
Composition pour revetement reduisant la reflexion Download PDFInfo
- Publication number
- WO1999063010A1 WO1999063010A1 PCT/JP1999/002803 JP9902803W WO9963010A1 WO 1999063010 A1 WO1999063010 A1 WO 1999063010A1 JP 9902803 W JP9902803 W JP 9902803W WO 9963010 A1 WO9963010 A1 WO 9963010A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- resist
- film
- coating
- water
- Prior art date
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 62
- 238000000576 coating method Methods 0.000 title claims abstract description 61
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 30
- -1 Perfluoroalkyl sulfone amide Chemical class 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 abstract description 26
- 230000000694 effects Effects 0.000 abstract description 18
- 238000011161 development Methods 0.000 abstract description 7
- 230000008859 change Effects 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 62
- 150000001875 compounds Chemical class 0.000 description 28
- 239000008199 coating composition Substances 0.000 description 26
- 230000008569 process Effects 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000006117 anti-reflective coating Substances 0.000 description 8
- 238000001459 lithography Methods 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002492 water-soluble polymer binding agent Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- IYNGLSRZLOHZJA-UHFFFAOYSA-N 1,4,7-triazabicyclo[5.2.2]undecane Chemical compound C1CN2CCN1CCNCC2 IYNGLSRZLOHZJA-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 description 1
- ZMIBIIAWFMCVFD-UHFFFAOYSA-N 2,2-difluoroacetamide Chemical class NC(=O)C(F)F ZMIBIIAWFMCVFD-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- 150000003867 organic ammonium compounds Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- RRRXPPIDPYTNJG-UHFFFAOYSA-N perfluorooctanesulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RRRXPPIDPYTNJG-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film 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
- 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
- C09D5/006—Anti-reflective coatings
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
Definitions
- the present invention relates to a composition for an antireflection coating, and more specifically, is provided on a photo resist film.
- a pattern is formed by photolithography technology, incident light and reflected light on a resist surface are reflected from a substrate.
- An anti-reflective coating composition for preventing a decrease in pattern dimensional accuracy (variation in pattern dimensional width) caused by interference with reflected light in a photoresist film, and a composition for the anti-reflective coating were used. It relates to a pattern formation method. Background art
- a photoresist film is formed on a substrate such as a silicon wafer, which is selectively irradiated with actinic rays, and then subjected to a development process to form a resist pattern on the substrate. Sography technology is applied.
- PE Bj Exposure Bake
- PED PostExposurDeLay
- the incident light and the reflected light at the photo-resist / substrate interface and the photo-resist Z air interface interfere with each other in the photo-resist film.
- a substantial exposure amount in the film is changed, which causes a problem that the resist pattern is adversely affected (standing wave effect, multiple reflection effect).
- ARC OR method a method of forming an antireflection film on a photo resist film
- a composition soluble in an organic solvent such as a halogen-based solvent has been proposed as a material for forming an anti-reflection film in the AR COR method.
- Many compositions that are soluble in aqueous solutions have been proposed. However, these previously proposed compositions are not sufficiently effective in eliminating PED and Z or standing wave effects. Or, even if these problems are solved, they have another new problem.
- Japanese Patent Application Laid-Open No. 5-188598 discloses an aqueous developable composition comprising a flow-opening carbon compound, a water-soluble polymer binder and an amine. If formed on a film, development residue (insolubilized layer) may occur in the upper layer of the resist pattern after development. This phenomenon is caused by the interaction between the components of the antireflection film and the novolak resin naphthoquinonediazide compound, which is a resist component, due to the presence of the quaternary ammonium salt in the developer, and the surface of the resist film is exposed to the developer. Probably because it was made insoluble.
- the refractive index of an antireflection film made of an aqueous developable composition comprising a fluorocarbon compound, a water-soluble polymer binder and an amine is far from an ideal refractive index.
- Japanese Unexamined Patent Publication (Kokai) No. 6-515253 discloses various water-soluble compounds having a solubility in water of 1% by weight or more such as N-propyl-1-N- (2-hydroxyhexyl) perfluorooctanesulfonamide. Although a composition comprising a fluorine-based compound is disclosed, this composition can achieve both dimensional stability when a low-wavelength light source is used and suitability for application to various resist materials and various substrates such as stepped substrates. Have difficulty.
- Japanese Patent Application Laid-Open No. 6-118630 proposes a chemically amplified resist coating solution composition containing a water-soluble film-forming component and a proton-generating substance.
- the antireflection effect is insufficient due to the high rate, and the ammonium weak acid salt exemplified as a proton generating substance deactivates the acid on the resist surface generated from the chemically amplified resist. Therefore, the problem of PED cannot be solved.
- Japanese Patent Application Laid-Open No. 6-148889 / 1996 discloses that a water-soluble film-forming component and a fluorine-based A composition comprising a surfactant is disclosed, and butylpyrrolidone homopolymer is preferred as a water-soluble film-forming component, and a fluorine-containing organic ammonium salt is preferred as a fluorine-containing surfactant.
- Japanese Patent Application Laid-Open No. 8-292562 also discloses a poly (vinylpyrrolidone) -based resin, a fluorinated surfactant, and a fluorinated aliphatic carboxylic acid such as 2-cyclo-1,2,2-difluoroacetamide.
- compositions containing a water-soluble fluorine compound of an acid amide are disclosed, these compositions are applied because of their poor applicability to various resist materials and various substrates such as stepped substrates. There is a problem that a resist material or a substrate to be coated is limited, or a large amount of an antireflection film liquid is required for coating. Furthermore, these compositions do not solve the problem of PED in chemically amplified resists.
- the present inventors have previously described a composition containing perfluoroalkylsulfonic acid, monoethanolamine, polyvinylpyrrolidone, a water-soluble alkylsiloxane polymer, and water (Japanese Patent Application Laid-Open No. 9-1291228). Or a combination of two or more fluorine compounds having different alkyl chain lengths and a perfluoroalkyl group-containing sulfonylamide compound (JP-A-10-301). It has been found that an antireflection coating composition having a low refractive index and excellent film stability can be obtained, but these compositions have a streak-like coating defect on stepped substrates such as logic ICs. It had the disadvantage of being generated.
- an object of the present invention is to provide a composition for antireflection coating which does not have the above-mentioned problems and a pattern forming method using the same, that is, a PED, a standing wave effect, and a multiple reflection effect. And good coating suitability for various resist materials and various substrates.Specifically, it is possible to coat various resist materials with a small amount of dripping, and to apply coating defects to stepped substrates. -Free antireflective coating composition And a pattern forming method using the same. Disclosure of the invention
- the present inventors have conducted intensive studies to solve the above-mentioned problems, and found that a composition containing at least the following (A) to (E) and having a pH of 1.3 to 3.3 is used. As a result, the above-mentioned problem is solved, and the present invention has been completed.
- the first invention contains at least the following (A), (B), (C), (D) and (E), and has a pH of 1.3 to 3.3.
- An object of the present invention is to provide a composition for an antireflection coating, which is a feature of the present invention.
- n an integer of 4 to 8.
- the second invention provides the antireflection coating composition according to the first invention, wherein the organic amine is monoethanolamine.
- the antireflection coating according to the first or second invention wherein the water-soluble polymer is polyvinylpyrrolidone and ⁇ or polyacrylic acid.
- the present invention provides a composition for anti-coating.
- the weight ratio of the perfluoroalkylsulfonic acid (A), the organic amine (B), the water-soluble polymer (C), and the perfluoroalkylsulfonamide (D) in the composition is as follows.
- the present invention provides the antireflection coating composition according to any one of the first, second and third inventions, wherein
- the fifth invention includes a step of applying the antireflection coating composition according to any one of the first to fourth inventions on a photoresist film, and heating as necessary. It is intended to provide a characteristic pattern forming method.
- the general method of forming a resist pattern by the ARC OR method includes, for example, a step of applying a photo resist composition on a semiconductor substrate, and forming a formed photo resist film as necessary.
- a step of baking a step of applying an antireflection coating composition on the photoresist film, a step of baking the photoresist film and the antireflection coating film as necessary, and a step of baking the photoresist.
- perfluoroalkylsulfonic acid used as the component (A) in the antireflection coating composition of the present invention is a component for reducing the refractive index of the antireflection coating. Is used.
- n tare indicates the refractive index of the antireflection film
- n resist indicates the refractive index of the resist .
- Equation 2 (where d tare is the thickness of the antireflection film, or the wavelength of the energy beam, and X is an odd integer)
- the antireflection performance is determined by the refractive index of the antireflection film and the refractive index and thickness of the resist at the wavelength of the target light source.
- the refractive index must be lower than the refractive index of the resist within a range satisfying the above conditions.
- a compound containing a fluorine atom has a low refractive index due to its large molecular volume and small atomic refraction of the fluorine atom, and the value of the refractive index is almost directly proportional to the fluorine content in the compound. It has been known.
- the compound represented by the above general formula C StephenF 2n + 1 S ⁇ 3 H is a compound having a low refractive index and effective as an aqueous developable fluorine-based compound, and is preferable for exhibiting antireflection performance. compounds.
- the refractive index increases, and the desired antireflection performance cannot be obtained.
- the R f group may be linear or branched.
- the organic amine as the component ( ⁇ ) of the antireflection coating composition of the present invention adjusts ⁇ in the coating composition to an optimal range, and forms a uniform film on various resists or substrates. It is an indispensable component for coating.
- the organic amine is not particularly limited as long as it is a known and used organic amine compound.
- organic ammonium compounds such as tetramethylammonium hydroxide and tetraethylammonium hydroxide are also included in the organic amine. Needless to say, the present invention is not limited by these specific examples.
- organic amines examples include monoethanolamine, diethanolamine, and triethanolamine from the viewpoints of eliminating PED, maintaining low refractive index, compatibility with other composition components, and stability with time of the film.
- alkanolamines such as propanolamine, and among them, monoethanolamine is preferred.
- the antireflection coating composition In the antireflection coating composition, adjusting the pH to a range of 1.3 to 3.3 using an organic amine can eliminate PED, and can be used in resists of various shapes or different types. It has been found that it is preferable in terms of developing suitability for application to the surface of the glass and developing stability with time of the film. This is because if the pH of the antireflection coating composition is not in this range, it is difficult to achieve at least one of the above-mentioned properties.
- the water-soluble polymer as the component (C) of the antireflection coating composition of the present invention is coated with the composition uniformly on the surface of the resist film, and then forms a stable film with time. It is a component for forming on a film.
- the water-soluble polymer any known and publicly used polymer can be used as long as it has a solubility in water of 0.1% by weight or more.
- Water-soluble polymer Specific examples of the monomer include vinyl alcohol, (meth) atalylic acid, 2-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and glycosyloxethyl (monomer) in the constituent monomer units.
- Homopolymers or copolymers containing hydrophilic units such as (meth) acrylate, vinylinolemethinoleate, vinylinolepyrrolidone, ethylene glycol, and glucose; Japanese Patent Application Laid-Open No. 199/1990, Japanese Patent Application Laid-Open No. Hei 7-234345 / 1992, Japanese Patent Application Laid-Open No. Hei 9-1501 / 1990 Water-soluble fluoropolymers used for antireflection coating agents disclosed in, for example, Patent Publication No. 623 are exemplified. Of course, the present invention is not limited by these specific examples.
- the water-soluble polymer of the component (C) may be produced by any method, and the method for producing the polymer is not limited.
- the method of introducing the hydrophilic unit into the water-soluble polymer is as follows: the hydrophilic monomer unit itself is subjected to bulk polymerization, emulsion polymerization, or suspension polymerization based on a polymerization mechanism such as radical polymerization, anion polymerization, or cationic polymerization.
- the polymerization may be performed by a polymerization method such as solution polymerization, or may be performed by a method of producing a polymer containing no hydrophilic unit and then substituting the polymer with a hydrophilic unit, or a combination thereof. It does not matter how.
- water-soluble polymer As a water-soluble polymer, it is suitable for application to resist surfaces of different shapes or types, stability with time of the film, dimensional stability of the resist, low refractive index, and high temperature of 150 to 160 ° C.
- Polyvinylpyrrolidone and / or polyacrylic acid are preferred from the viewpoint of solubility in water after the alkane treatment, and the molecular weight of the water-soluble polymer is 1.0000 in terms of weight average molecular weight. 1100, 000 is preferred, and 2,000 to 5,000, more preferred.
- the molecular weight is less than 1,000, it is difficult to obtain a uniform film, and the If the time stability is reduced, and if it exceeds 100, 000, stringing will occur during coating, spreading on the resist surface will be poor, and uniform application can be achieved with a small amount of dripping. Disappears.
- C a perfluoroalkyl sulfone represented by the general formula C
- C a perfluoroalkyl sulfone represented by the general formula C
- C a perfluoroalkyl sulfone represented by the general formula C
- C a perfluoroalkyl sulfone represented by the general formula C
- C is the most characteristic component in the present invention, and is suitable for application to a resist surface having a different shape or type by the introduction of the present compound, specifically, uniform applicability with a small amount of dripping, and step difference.
- the suitability for coating on the substrate is dramatically improved.
- the perfluoroalkylsulfonamide represented by the above general formula is a compound having an extremely low solubility in water of 0.055% or less in water.
- the solubility of the compound in the composition for antireflection coating can be raised to about 1.5%, and the compound can be uniformly dispersed at the time of addition. It becomes possible to adjust the coating liquid.
- the perfluoroalkylsulfonamide of the component (D) is added to the antireflection coating composition in which ⁇ 1 is adjusted to 1.3 to 3.3, the dynamic surface tension of the composition is increased. In addition, the static surface tension is reduced, and the wettability of the coating liquid on various resist surfaces is improved.
- the suitability for coating on stepped substrates is dramatically improved, and the amount of dripping is small. This also makes it possible to form a uniform and stable film over time. Further, after the lithography process, the film can be easily removed by a known and commonly used aqueous development.
- R f Purful with n in the chain between 1 and 8 O b alkyl sulfonamidyl but de it is necessary to use, C 6 F 13 S 0 2 NH 2, C 7 F 15 S_ ⁇ 2 NH 2, C 8 F 17 n among them is 6, 7 or 8 S 0 2 NH 2 is preferred, and C 6 F 13 S 0 2 NH 2 is particularly preferred.
- the perfluoroalkyl sulfone amide only one kind may be used, or two or more kinds may be used at the same time.
- the water of the component (E) used in the antireflection coating composition of the present invention is not particularly limited as long as it is water.However, organic impurities, metal ions, It is preferable to remove them.
- an organic solvent soluble in water can be used together with water.
- an organic solvent soluble in water As an organic solvent soluble in water,
- the solvent dissolves in an amount of 0.1% by weight or more.
- alcohols such as methyl alcohol, ethyl alcohol, and isopropyl alcohol
- ketones such as acetone and methyl ethyl ketone.
- Estenoles such as methylacetate, methyl acetate, ethinole acetate, dimethinolephonoremamide, dimethinolesnoreoxide, methinoreserosonolebu, cellosonoleb, butinoreserosonolebu, cellosolenoacetate, butyl carbitol, carbitol, etc.
- Polar solvents are merely examples of organic solvents, and the organic solvents used in the present invention are not limited to these solvents.
- a wide variety of components can be obtained by simultaneously including the components (A), (B), (C), (D) and (E) in the antireflection coating composition.
- the components (A) to (E) are essential. The effect of each component as well as the synergistic effect of each component solves the problem of the present invention.
- the pH of the antireflection coating composition is adjusted within the range of 1.3 to 3.3.
- the preferred range is that the water-soluble polymer (C) be in a weight ratio, although it depends on the desired resist material, exposure apparatus, antireflection performance, base material shape, and the like.
- perfluoroalkylsulfonic acid A
- Z organic amine B
- the resist material on which the antireflection coating composition of the present invention is applied may be any known one so far as it is conventionally known.
- a novolak resin soluble in an aqueous alkali solution and a naphthoquinonediazide may be used.
- Positive photoresist containing a derivative compound as the main component. Polyhydroxystyrene partially substituted with a protecting group that inhibits dissolution in a developer and is released by the presence of an acid.
- a chemically amplified positive resist composed of a photoacid generator that generates an acid, or a negative resist containing a binder polymer such as novolak resin and a photocrosslinking agent such as bisazide, and polyhydroxystyrene.
- the resin is a water-soluble resin such as novolak resin as the binder polymer, and the presence of acids such as melamine derivatives Chemically amplified negative registry like containing such triazine photoacid generator which generates an acid by light irradiation and bridges crosslinking agents.
- a photoresist is applied to a predetermined thickness on a semiconductor substrate by spin coating.
- the subsequent process is selected by the user depending on several conditions, but generally, the next process is a resist beta process using a hot plate. Depending on the registry used, or depending on the location of the applicator, the registry beta may be omitted.
- the antireflection coating composition is applied to a predetermined film thickness by spin coating in the same manner as when applying the photoresist.
- step of betaing the resist and the anti-reflection coating film on the resist there is a step of betaing the resist and the anti-reflection coating film on the resist, but this step may be omitted depending on conditions.
- beta When performing beta after forming an anti-reflection coating film, it is common to perform beta at a temperature equal to or lower than the beta condition of the resist alone.
- a predetermined pattern is exposed to the photo resist and the antireflection coating film through a mask using an exposure apparatus.
- an exposure apparatus an exposure apparatus using a g- line, an i-line, or an excimer laser light source is used, but the exposure apparatus is not limited to these.
- a baking process using a hot plate is generally performed to improve the resist pattern shape or to advance the reaction when a chemically amplified resist is used.
- this beta treatment may be omitted.
- the resist pattern after development may be deformed due to the influence of basic components in the standing environment due to leaving after exposure.
- the influence (PED) due to this leaving can be prevented by the antireflection coating film formed on the resist.
- the exposed resist and anti-reflection coating film are developed using an aqueous solution of water (a 2.38% aqueous solution of tetramethylammonium hydroxide at the mouth is often used). And a resist pattern is formed.
- the antireflection coating composition of the present invention can be uniformly coated with a small amount of dripping regardless of the type of the resist, such as a general-purpose resist or a chemically amplified resist, and the formed film has a standing wave effect. It effectively suppresses the multiple interference effect and PED, and realizes excellent dimensional stability of the resist.
- the weight average molecular weight 3, 0 00 poly Binirupiro Li pyrrolidone; 1.0 parts, C 8 F I7 S 0 3 H; 4. 0 parts of monoethanolamine ⁇ Mi emissions; 0.3 5 parts of C 6 F 13 SO 2 NH 2 ; 0.1 part was uniformly dissolved in 94.55 parts of pure water by heating to 70 ° C. After returning the dissolved solution to room temperature (23 ° C) and confirming that the solution is homogeneous, filter through a 0.05 m filter. The excess was used as an antireflection coating composition. The pH of this antireflection coating composition at 23 ° C was 1.63. Table 1 shows the values of the static surface tension and the dynamic surface tension of the obtained composition for antireflection coating, and the contact angle when the composition was dropped on a resist surface.
- the static surface tension, dynamic surface tension and contact angle were determined by the following measurement methods.
- the hysteresis of the surface tension formed when the solution area was continuously changed 10 times from 20 to 80 cm 2 at a rate of 10 sec./cycle with C was evaluated. Specifically, it was adopted as the hysteresis formed in 1 0-th surface loss energy (1 0- 5 m J).
- Example 1 was repeated using the compounds and amounts (parts) shown in Tables 1 and 2, to obtain the antireflection coating compositions of Examples 2 to 15.
- the pH of the obtained antireflection coating composition was as shown in Tables 1 and 2, respectively.
- Example 1 was repeated using the compounds and amounts (parts) described in Table 3 to obtain antireflection coating compositions of Comparative Examples 1 to 7.
- the ⁇ of the obtained composition for antireflection coating was as shown in Table 3.
- AZ®DX1100 manufactured by Clarianto Japan
- a chemically amplified resist was applied to an HMD S-treated 8-inch silicon wafer to a film thickness of 0.75 microns
- a baking process was performed at 110 ° C for 60 seconds using a hot plate, and a substrate for evaluation was prepared.
- a sample for anti-reflection coating was dropped on the above substrate using a resist coater L ARC—UL TI MA 100000 (manufactured by Lithotech) to form a uniform film on the entire surface of the 8-inch wafer. The minimum amount of drop required to perform the test was compared and evaluated.
- a resist AZ®DX110 was applied and beta-prepared on a 6-inch substrate with a 5,000 A silicon oxide film step, and this substrate was prepared.
- a resist coater LARC-ULTI MA1000 manufactured by Lithotech Co.
- a composition sample for antireflection coating was dropped, and the state of the coating film after spin coating was observed using a microscope.
- the coating film prepared by the coating property evaluation was stored in a clean room, and the state of the coating film was observed with time.
- the coating film stability was evaluated based on the following criteria.
- LAR C— ULTI on 6-inch silicon wafer Using MA 1 000 (manufactured by Lithotec), apply a sample of the anti-reflective coating composition to a film thickness of approximately 450 A, and apply a hot plate at 90 ° C for 60 seconds. After performing the above beta treatment, the refractive index was measured between 193 nm and 930 ⁇ m using a spectroscopic ellipsometer-ES5G (manufactured by Sopra).
- AZ®DX110 manufactured by Clariant Japan
- a chemically amplified resist is applied to a 6-inch silicon wafer that has been subjected to HMDS processing so that the film thickness becomes 0.75 microns, and a hot plate is applied.
- a composition sample for anti-reflection coating is applied so as to have an approximately predetermined film thickness based on the above formulas 1 and 2.
- the exposed wafer was exposed to the PEB for 12 hours after exposure, then developed similarly, and the PED (post exposure exposure) stabilizing effect was similarly evaluated (“P” in the table). Shape degradation due to ED ”).
- Example 16 In the same manner as in Example 16, the anti-reflection coating obtained in Comparative Example 7 was used.
- the coating composition was evaluated for coating properties, film stability, refractive index, and lithography. Table 6 shows the results.
- the comparative examples have problems in at least one of the coating properties, coating film stability, refractive index, and lithography characteristics.
- the anti-reflective coating composition of the present invention has excellent coating properties, coating stability, refractive index, and lithographic properties, and can be used to obtain a composition having no problems in use. I will. The invention's effect
- the antireflection coating composition of the present invention can be uniformly coated with a small amount of droplets regardless of the type of general-purpose resist, the type of resist such as a chemically amplified type, and the surface shape of the substrate to be coated.
- the film efficiently suppresses the multiple reflection effect, standing wave effect, and PED, thereby forming a resist pattern having excellent dimensional stability and excellent cross-sectional shape.
- composition for an antireflection coating according to the present invention is applied to a photoresist layer to form an antireflection film, for example, in the production of an ultrafine integrated circuit device such as an LSI. Used as
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Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69921603T DE69921603T2 (de) | 1998-06-03 | 1999-05-27 | Antireflexionsbeschichtungszusammensetzung |
US09/485,087 US6309789B1 (en) | 1998-06-03 | 1999-05-27 | Composition for reflection reducing coating |
KR1020007001148A KR100594708B1 (ko) | 1998-06-03 | 1999-05-27 | 반사 방지 코팅용 조성물 |
EP99922524A EP1026208B1 (en) | 1998-06-03 | 1999-05-27 | Anti-reflective coating composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10/154344 | 1998-06-03 | ||
JP15434498A JP3673399B2 (ja) | 1998-06-03 | 1998-06-03 | 反射防止コーティング用組成物 |
Publications (1)
Publication Number | Publication Date |
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WO1999063010A1 true WO1999063010A1 (fr) | 1999-12-09 |
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ID=15582114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1999/002803 WO1999063010A1 (fr) | 1998-06-03 | 1999-05-27 | Composition pour revetement reduisant la reflexion |
Country Status (9)
Country | Link |
---|---|
US (1) | US6309789B1 (ja) |
EP (1) | EP1026208B1 (ja) |
JP (1) | JP3673399B2 (ja) |
KR (1) | KR100594708B1 (ja) |
CN (1) | CN1169884C (ja) |
DE (1) | DE69921603T2 (ja) |
MY (1) | MY117818A (ja) |
TW (1) | TW556048B (ja) |
WO (1) | WO1999063010A1 (ja) |
Cited By (1)
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US7537882B2 (en) | 2004-06-30 | 2009-05-26 | Dainippon Ink And Chemicals, Inc. | Anti-reflective coating composition and production method for pattern using the same |
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JP4556251B2 (ja) * | 1998-04-17 | 2010-10-06 | Dic株式会社 | 被覆用組成物 |
US6984482B2 (en) * | 1999-06-03 | 2006-01-10 | Hynix Semiconductor Inc. | Top-coating composition for photoresist and process for forming fine pattern using the same |
JP2001142221A (ja) * | 1999-11-10 | 2001-05-25 | Clariant (Japan) Kk | 反射防止コーティング用組成物 |
KR100400331B1 (ko) * | 1999-12-02 | 2003-10-01 | 주식회사 하이닉스반도체 | 포토레지스트 오버코팅용 조성물 및 이를 이용한포토레지스트 패턴 형성방법 |
JP3320402B2 (ja) * | 2000-06-26 | 2002-09-03 | クラリアント ジャパン 株式会社 | 現像欠陥防止プロセス及び材料 |
JP2002148820A (ja) * | 2000-11-15 | 2002-05-22 | Clariant (Japan) Kk | パターン形成方法及びこの方法に使用される処理剤 |
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 |
US7265431B2 (en) * | 2002-05-17 | 2007-09-04 | Intel Corporation | Imageable bottom anti-reflective coating for high resolution lithography |
JP2003345026A (ja) * | 2002-05-24 | 2003-12-03 | Tokyo Ohka Kogyo Co Ltd | 反射防止膜形成用塗布液組成物およびこれを用いたホトレジスト積層体、並びにホトレジストパターンの形成方法 |
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US6740469B2 (en) * | 2002-06-25 | 2004-05-25 | Brewer Science Inc. | Developer-soluble metal alkoxide coatings for microelectronic applications |
JP3851594B2 (ja) * | 2002-07-04 | 2006-11-29 | Azエレクトロニックマテリアルズ株式会社 | 反射防止コーティング用組成物およびパターン形成方法 |
TWI347741B (en) | 2003-05-30 | 2011-08-21 | Asml Netherlands Bv | Lithographic apparatus and device manufacturing method |
US7833612B2 (en) * | 2003-09-12 | 2010-11-16 | Samsung Mobile Display Co., Ltd. | Substrate for inkjet printing and method of manufacturing the same |
DE10343351B4 (de) * | 2003-09-12 | 2017-01-05 | Samsung Display Co., Ltd. | Substrat zum Tintenstrahldrucken und Verfahren zu dessen Herstellung |
JP5368674B2 (ja) * | 2003-10-15 | 2013-12-18 | ブルーワー サイエンス アイ エヌ シー. | 現像液に可溶な材料および現像液に可溶な材料をビアファーストデュアルダマシン適用において用いる方法 |
US20050255410A1 (en) | 2004-04-29 | 2005-11-17 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
EP1818723B1 (en) * | 2004-12-03 | 2011-05-04 | JSR Corporation | Composition for forming antireflection film, layered product, and method of forming resist pattern |
US7205093B2 (en) * | 2005-06-03 | 2007-04-17 | International Business Machines Corporation | Topcoats for use in immersion lithography |
US7544750B2 (en) * | 2005-10-13 | 2009-06-09 | International Business Machines Corporation | Top antireflective coating composition with low refractive index at 193nm radiation wavelength |
US7759047B2 (en) * | 2006-05-26 | 2010-07-20 | Shin-Etsu Chemical Co., Ltd. | Resist protective film composition and patterning process |
US7635552B2 (en) * | 2006-07-25 | 2009-12-22 | Endicott Interconnect Technologies, Inc. | Photoresist composition with antibacterial agent |
US7914974B2 (en) | 2006-08-18 | 2011-03-29 | Brewer Science Inc. | Anti-reflective imaging layer for multiple patterning process |
CN101971102B (zh) | 2008-01-29 | 2012-12-12 | 布鲁尔科技公司 | 用来通过多次暗视场曝光对硬掩模进行图案化的在线法 |
US9640396B2 (en) | 2009-01-07 | 2017-05-02 | Brewer Science Inc. | Spin-on spacer materials for double- and triple-patterning lithography |
US8273997B2 (en) * | 2009-01-16 | 2012-09-25 | The Boeing Company | Antireflective apparatus with anisotropic capacitive circuit analog sheets |
JP5697523B2 (ja) | 2011-04-12 | 2015-04-08 | メルクパフォーマンスマテリアルズIp合同会社 | 上面反射防止膜形成用組成物およびそれを用いたパターン形成方法 |
CN114806394A (zh) * | 2022-04-28 | 2022-07-29 | 武汉工程大学 | 一种抗反射层涂料、抗反射层及其制备方法和应用 |
CN116875159B (zh) * | 2023-09-05 | 2023-11-21 | 甘肃华隆芯材料科技有限公司 | 顶部抗反射涂层材料及其制备方法和应用 |
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- 1999-05-25 TW TW088108546A patent/TW556048B/zh not_active IP Right Cessation
- 1999-05-27 DE DE69921603T patent/DE69921603T2/de not_active Expired - Lifetime
- 1999-05-27 CN CNB998008818A patent/CN1169884C/zh not_active Expired - Fee Related
- 1999-05-27 KR KR1020007001148A patent/KR100594708B1/ko not_active IP Right Cessation
- 1999-05-27 WO PCT/JP1999/002803 patent/WO1999063010A1/ja active IP Right Grant
- 1999-05-27 EP EP99922524A patent/EP1026208B1/en not_active Expired - Lifetime
- 1999-05-27 US US09/485,087 patent/US6309789B1/en not_active Expired - Lifetime
- 1999-05-28 MY MYPI99002142A patent/MY117818A/en unknown
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JPH103001A (ja) * | 1996-04-19 | 1998-01-06 | Dainippon Ink & Chem Inc | 反射防止膜用組成物 |
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Also Published As
Publication number | Publication date |
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EP1026208A1 (en) | 2000-08-09 |
CN1169884C (zh) | 2004-10-06 |
DE69921603T2 (de) | 2005-11-03 |
MY117818A (en) | 2004-08-30 |
TW556048B (en) | 2003-10-01 |
CN1272864A (zh) | 2000-11-08 |
JP3673399B2 (ja) | 2005-07-20 |
DE69921603D1 (de) | 2004-12-09 |
KR100594708B1 (ko) | 2006-07-03 |
KR20010022557A (ko) | 2001-03-26 |
EP1026208A4 (en) | 2003-04-16 |
EP1026208B1 (en) | 2004-11-03 |
JPH11349857A (ja) | 1999-12-21 |
US6309789B1 (en) | 2001-10-30 |
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