JP2016532739A - 可溶性金属酸化物カルボキシレートのスピンオン組成物及びそれらの使用方法 - Google Patents
可溶性金属酸化物カルボキシレートのスピンオン組成物及びそれらの使用方法 Download PDFInfo
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- JP2016532739A JP2016532739A JP2016522511A JP2016522511A JP2016532739A JP 2016532739 A JP2016532739 A JP 2016532739A JP 2016522511 A JP2016522511 A JP 2016522511A JP 2016522511 A JP2016522511 A JP 2016522511A JP 2016532739 A JP2016532739 A JP 2016532739A
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- Prior art keywords
- metal oxide
- composition
- group
- dicarboxylate
- metal
- Prior art date
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- 229910044991 metal oxide Inorganic materials 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 38
- -1 metal oxide carboxylates Chemical class 0.000 title description 39
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 59
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 60
- 229920002120 photoresistant polymer Polymers 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 17
- 230000005855 radiation Effects 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 9
- 239000010936 titanium Substances 0.000 claims description 9
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- 150000007942 carboxylates Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000001787 chalcogens Chemical group 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002848 norbornenes Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
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- 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
- G03F7/092—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/06—Coating on selected surface areas, e.g. using masks
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
- C23C18/1204—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material inorganic material, e.g. non-oxide and non-metallic such as sulfides, nitrides based compounds
- C23C18/1208—Oxides, e.g. ceramics
- C23C18/1216—Metal oxides
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/14—Decomposition by irradiation, e.g. photolysis, particle radiation or by mixed irradiation sources
- C23C18/143—Radiation by light, e.g. photolysis or pyrolysis
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- 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
-
- 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
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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Abstract
Description
nc=n−jk
(Handbook of Semiconductor Manufacturing Technology,Yoshio Nishi et al,Marcel Dekker Inc,2000,第205頁(非特許文献1))。
Gelest Inc.,Morrisville PAからの20.0gのジルコニウム酸化物プロピオネートを反応容器中に入れ、そして180gのプロピレングリコールモノメチルエーテルアセテート(PGMEA)を加えた。一晩震盪後、この調合物を0.2μmフィルターに通して濾過した。
Aldrich Chemical Company,St.Louis,MOからの18.0gのアンモニウムジルコニウムカーボネート(ZrO2 20重量%)を反応容器中に入れ、そして18グラムのプロピオン酸をゆっくりと滴下した。これらの酸を添加する間、アンモニア及び二酸化炭素ガスを放出した。反応の完了時には、これは、フォーム状の白色の固形化合物を生成した。次いで、30グラムのPGMEAを加えた。2〜3時間震盪した後、この調合物を0.2μmフィルターに通して濾過した。
Nyacol Nano Technology,Inc.,Ashland,MAから入手した、酢酸イオンで安定化されたZrO2ナノパーティクル溶液(20重量%)(平均粒度 約5〜10nm、溶液の初期pHは3.5であった)20グラムを反応容器中に入れた。10グラムのアクリル酸を、一定に攪拌しながら滴下した。PGMEAとプロピレングリコールモノメチルエーテル(PGME)との70/30ブレンド30グラムを添加した。4〜5時間震盪した後、この調合物を0.2μmフィルターに通して濾過した。
Aldrich Chemical Companyから入手した、希酢酸中のジルコニウムアセテート溶液(Zr16重量%)15グラムを反応容器中に入れ、そして10グラムのアクリル酸を一定に攪拌しながら添加した。次いで、25グラムのArFシンナーを加えた。4〜5時間震盪した後、この溶液を0.2μmフィルターに通して濾過した。
エチレングリコール4グラムと、Aldrich Chemical Companyからの、希酢酸中のジルコニウムアセテート溶液(Zr16重量%)20グラムを反応容器に加え、そしてゆっくりと加熱して、この溶液から水を除去して、前駆体の粘度を高めて最終的にはゲルを形成した。2グラムのアクリル酸を添加し、その後40グラムのPGMEAを添加した。
Gelest Inc.,Morrisville PAからの20.0gのジルコニウム酸化物プロピオネートを反応容器中に入れ、そして180gのPGMEAを加えた。一晩震盪後、この調合物を0.2μmフィルターに通して濾過した。ArFシンナー中の例9のポリマーの10%溶液22.2gを加えて、金属酸化物とポリマーとの割合が90/10である組成物とし、これを再び0.2μmフィルターに通して濾過した。
Gelest Inc.,Morrisville PAからの20.0gのジルコニウム酸化物プロピオネートを反応容器中に入れ、そして180gのPGMEAを加えた。一晩震盪後、この調合物を0.2μmフィルターに通して濾過した。ArFシンナー中の例9のポリマーの10%溶液50.0gを加えて、金属酸化物とポリマーとの割合が80/20である組成物とし、これを再び0.2μmフィルターに通して濾過した。
Gelest Inc.,Morrisville PAからの20.0gのジルコニウム酸化物プロピオネートを反応容器中に入れ、そして180gのPGMEAを加えた。一晩震盪後、この調合物を0.2μmフィルターに通して濾過した。ArFシンナー中の例9のポリマーの10%溶液85.7gを加えて、金属酸化物とポリマーとの割合が70/30である組成物とし、これを再び0.2μmフィルターに通して濾過した。
9.7gの1,1,1−トリフルオロ−2−トリフロロメチル−2−ヒドロキシ−4−ペンチルメタクリレート、5.8gのベンジルメタクリレート、5.1gの2−ヒドロキシエチルメタクリレート、及び6.4gのグリシジルメタクリレートを、120gのテトラヒドロフラン(THF)溶媒中で混合した。重合反応を、1.0gのアゾビスブチロニトリル(AIBN)の存在下に75℃で窒素下に20時間行った。室温まで冷却した後、反応混合物を脱イオン(DI)水で析出させた。この白色のポリマー固形物を洗浄し、そして45℃で真空下に乾燥し、26.5g(99%)の収量を得た。GPCで測定したポリマーのMwは19,000であった。
プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノメチルエーテル(PEGMA/PGME)70:30溶媒を、表1に記載の温度で、組成物例1、6、7及び8からの材料でコーティングされたケイ素ウェハ上に供した。60秒後に溶媒を除去するために窒素ブローを使用した。大きな膜減り(film loss)は観察されなかった。同様の実験を、現像剤としての2.38%重量/重量テトラメチルアンモニウムヒドロキシド(TMAH)を用いて行った。表1及び表2からのフィルムは現像剤に対し良好な耐性を示した。
n及びk値は、エリプソメータ、例えばJ.A.Woollam WVASE VU−32TMエリプソメータを用いて計算することができる。k及びnの最適範囲の正確な値は、使用する暴露波長及び適用のタイプに依存する。典型的には、193nmの場合には好ましいkの範囲は約0.1〜約0.6、248nmの場合には好ましいkの範囲は約0.15〜約0.8であるが、他の暴露波長、例えばDUV及びビヨンドDUVも使用でき、組成物は、以下の表2に示されるように、それらと共同して作動するように調整される。
表3の硬化したフィルムのバルク耐エッチング性はCF4エッチング液を用いて行った。コーティングを、500ワットの電力及び137Paのベース圧で60または40秒間、エッチング液に曝した。エッチング速度は、二枚のウェハの平均に基づく。
250℃/120秒ベークした例1からの材料を用いた硬化フィルムのバルク耐エッチング性は、ULVAC Technologies,Inc.401 Griffin Brook Drive,Methuen,MAからのULVAC NE5000Nを用いて、2Pa/チャンバ500W/プラテン200W/40sccmCl2/4sccmCF4/25sccmAr/266Pa He.背圧/20℃電極温度の条件下に、様々なガスを使用して行った。
硬化した金属酸化物フィルム中の金属%重量/重量は、元素分析及びTGA重量損失測定によって測定した。二つの方法からの結果はつじつまの合うものであった。例1からのフィルムの金属含有率は、約60〜120秒間、200℃でフィルムを加熱した後に60重量%であった。
Zr金属製反射防止コーティング調合物の性能を、AZ(登録商標)2110Pフォトレジスト(AZ Electronic Materials USA Corp.,Somerville,NJの製品)を用いて評価した。ケイ素ウェハを組成物例1でコーティングし、そして240℃で60秒間ベークして、200nm厚のフィルムを形成した。次いで、AZ(登録商標)EXP AX2110Pを用いて、160nmのフォトレジストフィルムを上面にコーティングし、そして100℃で60秒間ベークした。次いで、0.85の開口数(NA)、0.85アウターシグマ及び0.55インナーシグマのYダイポール照明を用いて193nm Nikon 306D露光ツールを使用してウェハを画像形成した。次いで、露光されたウェハを110℃で60秒間ベークし、AZ(登録商標)300MIF現像剤(TMAH)(AZ Electronic Materials USA Corp.,Somerville,NJの製品)を用いて30秒間現像した。走査電子顕微鏡で観察した時、上から見たパターン及び断面パターンは、プロセスウィンドウ中で大きな崩壊を示さなかった。パターンプロフィルは、36mJ/cm2の感光速度(photospeed)でライン/スペース81.67nm 1:1で観察された。
Zr金属製反射防止コーティング調合物の性能を、AZ(登録商標)2110Pフォトレジスト(AZ Electronic Materials USA Corp.,Somerville,NJの製品)を用いて評価した。ケイ素ウェハを、例1からの調合物でコーティングし、そして350℃で120秒間ベークして200nm厚のフィルムを形成した。次いで、AZ(登録商標)EXP AX2110Pを用いて、160nmのフォトレジストフィルムを上面にコーティングし、そして100℃で60秒間ベークした。次いで、0.85の開口数(NA)、0.85アウターシグマ及び0.55インナーシグマのYダイポール照明を用いて193nm Nikon 306D露光ツールを使用してウェハを画像形成した。次いで、露光されたウェハを110℃で60秒間ベークし、AZ(登録商標)300MIF現像剤(TMAH)を用いて30秒間現像した。走査電子顕微鏡で観察した時、上から見たパターン及び断面パターンは、プロセスウィンドウ中で大きな崩壊を示さなかった。パターンプロフィルは、30mJ/cm2の感光速度でライン/スペース80nm、160nmピッチで観察された。
Claims (14)
- 少なくとも一種の金属酸化物ジカルボキシレート及び有機溶媒を含むスピンオン組成物であって、前記金属酸化物ジカルボキシレートが、前記溶媒中で可溶性かまたはコロイド安定性であり、及び前記金属酸化物ジカルボキシレートが熱処理の間に分解して硬化した金属酸化物フィルムを与えることができる、前記スピンオン組成物。
- ジカルボキシレートのカルボキシレートが、置換されたC3〜C6カルボキシレート、置換されていないC3〜C6カルボキシレート、飽和C3〜C6カルボキシレート、不飽和C3〜C6カルボキシレート、分枝状C3〜C6カルボキシレート、及び非分枝状C3〜C6カルボキシレートからなる群から選択され、そして大概はプロピオネートである、請求項1に記載の組成物。
- 金属酸化物ジカルボキシレート中の金属が、Ti、V、Cr、Zr、Nb、Mo、Ru、Rh、Hf、Ta、W、Re、及びIrから選択される少なくとも一種の高屈折性金属である、請求項1または2に記載の組成物。
- 金属酸化物ジカルボキシレートがナノパーティクルである、請求項1〜3のいずれか一つに記載の組成物。
- 金属酸化物ジカルボキシレートがジルコニウム酸化物ジカルボキシレートまたはチタン酸化物ジカルボキシレートである、請求項1〜4のいずれか一つに記載の組成物。
- 有機ポリマー、無機ポリマー及びこれらの混合物からなる群から選択される少なくとも一種のポリマーを更に含む、請求項1〜5のいずれか一つに記載の組成物。
- 電子デバイスを製造する方法であって、
a.請求項1〜7のいずれか一つに記載の組成物を施用して金属酸化物ジカルボキシレートフィルムを形成し、及び
b.コーティングされた基材を加熱して、それによって硬化された金属酸化物フィルムを形成する、
ことを含む、前記方法。 - 加熱ステップの後の金属酸化物フィルムの金属含有率が10〜85重量%の範囲である、請求項8に記載の方法。
- フォトレジストフィルムを、金属フィルム上に形成する、請求項8または9に記載の方法。
- フォトレジストフィルムを、約12nm〜約250nmの範囲の放射線で画像形成し、そして現像してパターンを形成する、請求項8〜10のいずれか一つに記載の方法。
- 加熱ステップが200℃〜500℃の範囲である、請求項8〜11のいずれか一つに記載の方法。
- 金属がジルコニウムまたはチタンである、請求項8〜12のいずれか一つに記載の方法。
- 加熱ステップの後の金属酸化物フィルムの金属含有率が10〜70重量%の範囲である、請求項8〜13のいずれか一つに記載の方法。
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TW201512325A (zh) | 2015-04-01 |
SG11201507487TA (en) | 2015-10-29 |
JP6342998B2 (ja) | 2018-06-13 |
US9201305B2 (en) | 2015-12-01 |
CN105209973A (zh) | 2015-12-30 |
US20150004801A1 (en) | 2015-01-01 |
WO2014207142A1 (en) | 2014-12-31 |
CN105209973B (zh) | 2019-08-13 |
EP3014358B1 (en) | 2017-08-16 |
TWI606098B (zh) | 2017-11-21 |
EP3014358A1 (en) | 2016-05-04 |
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KR20160025508A (ko) | 2016-03-08 |
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