TWI281921B - Novel cyclosilane compound, and solution composition and process for forming a silicon film - Google Patents
Novel cyclosilane compound, and solution composition and process for forming a silicon film Download PDFInfo
- Publication number
- TWI281921B TWI281921B TW090105731A TW90105731A TWI281921B TW I281921 B TWI281921 B TW I281921B TW 090105731 A TW090105731 A TW 090105731A TW 90105731 A TW90105731 A TW 90105731A TW I281921 B TWI281921 B TW I281921B
- Authority
- TW
- Taiwan
- Prior art keywords
- cyclopentane
- film
- forming
- ruthenium
- ruthenium film
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims description 34
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052710 silicon Inorganic materials 0.000 title abstract 3
- 239000010703 silicon Substances 0.000 title abstract 3
- -1 cyclosilane compound Chemical class 0.000 title description 63
- 239000000758 substrate Substances 0.000 claims abstract description 28
- 125000003003 spiro group Chemical group 0.000 claims abstract description 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 74
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 52
- 229910052707 ruthenium Inorganic materials 0.000 claims description 52
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 38
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 27
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000002079 cooperative effect Effects 0.000 claims description 5
- XMIJDTGORVPYLW-UHFFFAOYSA-N [SiH2] Chemical compound [SiH2] XMIJDTGORVPYLW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001339 silanediyl group Chemical group [H][Si]([H])(*)* 0.000 claims description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 2
- 241000237858 Gastropoda Species 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- DOBUHXUCKMAKSP-UHFFFAOYSA-N pentasilolanylsilane Chemical compound [SiH3][SiH]1[SiH2][SiH2][SiH2][SiH2]1 DOBUHXUCKMAKSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010408 film Substances 0.000 description 67
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 39
- 239000002904 solvent Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- 239000012300 argon atmosphere Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- WOUVLFFZQCUYOL-UHFFFAOYSA-N decylcyclopentane Chemical compound CCCCCCCCCCC1CCCC1 WOUVLFFZQCUYOL-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 6
- 229960005286 carbaryl Drugs 0.000 description 6
- 238000005229 chemical vapour deposition Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 150000003304 ruthenium compounds Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- 239000007795 chemical reaction product Substances 0.000 description 5
- CVXAAKMHIUMOBI-UHFFFAOYSA-N cyclopentylgermane Chemical group [GeH3]C1CCCC1 CVXAAKMHIUMOBI-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
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- 238000007639 printing Methods 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 238000000862 absorption spectrum Methods 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
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- OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 3
- BLRBGKYYWDBAQQ-UHFFFAOYSA-N dodecylcyclohexane Chemical compound CCCCCCCCCCCCC1CCCCC1 BLRBGKYYWDBAQQ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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
- C23C18/122—Inorganic polymers, e.g. silanes, polysilazanes, polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02518—Deposited layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02518—Deposited layers
- H01L21/02587—Structure
- H01L21/0259—Microstructure
- H01L21/02592—Microstructure amorphous
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02518—Deposited layers
- H01L21/02587—Structure
- H01L21/0259—Microstructure
- H01L21/02595—Microstructure polycrystalline
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02612—Formation types
- H01L21/02617—Deposition types
- H01L21/02623—Liquid deposition
- H01L21/02628—Liquid deposition using solutions
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02656—Special treatments
- H01L21/02664—Aftertreatments
- H01L21/02667—Crystallisation or recrystallisation of non-monocrystalline semiconductor materials, e.g. regrowth
- H01L21/02675—Crystallisation or recrystallisation of non-monocrystalline semiconductor materials, e.g. regrowth using laser beams
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/02104—Forming layers
- H01L21/02365—Forming inorganic semiconducting materials on a substrate
- H01L21/02612—Formation types
- H01L21/02617—Deposition types
- H01L21/0262—Reduction or decomposition of gaseous compounds, e.g. CVD
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Thermal Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Ceramic Engineering (AREA)
- Optics & Photonics (AREA)
- Silicon Compounds (AREA)
- Silicon Polymers (AREA)
- Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1281921 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明説明(1 ) 曼明詳細說明 本發明有關一種新穎的環矽烷化合物,一種用於形成 矽膜的溶液組成物,及一種用於形成矽膜之方法。 至目前爲止,熱化學蒸氣沉積法(CVD)、漿液CVD及光 學CVD(其係利用單矽烷氣體或二矽烷氣體之方法)已被用於 形成非晶形矽膜或聚矽膜,一般而言,熱CVDU. Vac. Sd. 技術,vol. 14,ρρ· 1082,1977)及漿液 CVD(固態 Com.,vol. Π,pp. 1193,1 975)已廣泛地分別用於聚矽膜及非晶形矽膜 之形成作用方面,且該類膜已被用於製造太陽能電池及具 有薄膜電晶體之液晶顯示元件。 然而,在按照該等CVD方法形成矽膜之方法上,已更 期待能夠改進下述缺點,(1)由於使用氣相反應,在氣相中 產生的砂顆粒會污染裝置及形成外來的物質,因而降低生 產率,(2)由於原料爲氣態,在具有不平坦表面的基質上很 難獲得均勻厚膜,(3)因爲低的膜形成速率而造成低的生產 力,(4)漿液CVD需要使用複雜及昂貴的高頻產生器及真空 裝置。 在原料方面,由於使用具有高反應性及毒性之氣態氫 化矽,使其不易控制及需使用氣密式真空裝置,且該項裝 置爲體積大與價昂,及真空或漿液系統常會消耗巨量的能 量,因而增加了產品成本。 近年來已提出一種不必使用真空系統之塗覆液體氫化 矽之方法,在JP-A 1 -2966 1 (“JP-A”一詞在此意指”未經審查 的曰本公開專利申請案”)揭示一種用於形成以矽爲主薄膜之 (請先閲讀背面之注意事項再填寫本頁) 衣. 訂
本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) · 4 - 1281921 A7 B7 五、發明説明(2) 方法,其藉在經冷卻基質上液化氣態原料、將其吸附至基 質及使其與化學活性原子態氫反應而製得薄膜,然而此方 法會有類如需要使用複雜裝置及因爲以氫化矽作爲原料經 連續蒸發與冷卻而不易控制膜厚度等問題發生。 JP-A 7_267 62 1揭示一種利用低重量分子量液體氫化矽 塗覆基質之方法,此方法會有類如不易操作氫化矽而使其 系統不安定,及當使用大面積基質時因爲氫化矽爲液體而 不易獲得均勻的膜厚度等問題發生。 同時,英國專利案GB-20777 10A記載有關固體氫化矽聚 合物實例,惟因爲其在溶劑中不溶解而無法形成塗膜。 又,JP-A-9 237927揭示一種形成矽膜之方法,其藉利 用聚矽烷溶液塗覆基質,及爲了製造太陽能電池而利用熱 分解聚砂烷而產生矽膜。然而,因爲熱分解反應及曝露於 紫外線輻射產生光分解反應,造成大量碳以雜質形式殘留 於膜中,使該方法不易從含碳之矽化合物中獲得具有優異 電性性質之非晶形或聚晶形矽膜。 再,JP-A 60-24261 2揭示一種藉熱CVD形成矽沉積膜之 方法,該方法包含在放置基質與提供熱能給該等化合物在 基質上形成含矽原子沉積膜之沉積室中,形成下式所示環 狀砂院化合物及鹵素化合物之氣態氛團,
.(SiHR)J (其中n爲3、4或5,R爲Η或SiH〇 (請先閲讀背面之注意事項再填寫本頁) 訂
經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中_國家標準(CNS ) A4規格(210X297公釐) -5 - 1281921 Α7 Β7 經濟部智慧財產局員工消費合作社印製 五、發明説明(3 ) 前述公開申請案中列舉的化合物係以如上式所示環狀 矽烷化合物之五個化學式表示,然而,該等環狀化合物並 無相關的辨識數據及用於製造該化合物之方法。通常聚矽 烷類可經由具有下列方法表示之構造單元的單體製造,例 如:U)於等重的鹼金屬與鹵素原子存在下,單體中的鹵砂 院經脫鹵化及聚縮合(即所謂K i p p i n g方法,J . A m. C h e m. Soc·,vol. 1 10,pp. 2342,( 1 988),巨分子類,vol. 23,pp. 3423,( 1 990)); (b)單體中的鹵矽烷藉由電極還原反應而脫 鹵化及聚縮合(J. Chem. Soc.,Chem,Commun.,ρρ· 1161,( 1990) ’ J. Chem. Soc·,Chem·,Commun·,ρρ· 896,(1992)) ;(c)在金屬觸媒存在下,單體中的氫矽烷經脫鹵化及聚縮 合(JP-A 4-33455 1 ); (d)單體中的由聯苯基交聯的二矽烷經 陰離子聚合(巨分子類,vol. 23,pp. 4494,(1990));及(e)單 體中的由苯基或烷基取代的環狀矽化合物藉由上述方法之 一者合成,及藉由已知方法(例如Z. Anorg. Allg. Chem. Vol. 459,pp. 123,( 1 979))導入經氫取代物質或經鹵素取 代物質。此類環矽烷鹵化物可藉由已知方法合成(例如Mh. Chem. Vol. 106, pp. 503, ( 1 975)) (Z. Anorg. Allg. Chem. Vol. 621, pp. 1 5 1 7, ( 1 995)) (J. Chem. Soc., Chem·,Commun·,pp. 777,( 1 984))。如上所述,一般係藉 由聚縮合反應合成製得聚矽烷,但在聚縮合反應副產生鹽 時,需要純化經合成的聚合物之步驟。近年來在”巨分子類, vol. 27,pp. 2360,(1 994))”中已揭示藉由苯基nano甲基環 戊矽烷1之陰離子開環聚合反應合成聚(苯基nano甲基戊亞矽 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) Γ<6^ " 一 (請先閱讀背面之注意事項再填寫本頁) 'Ψ' 訂
1281921 Α7 Β7 五、發明説明(4) 烷基)2之技術,該環狀單體之開環聚加成反應不像上述聚 縮合反應會產生副產物,及其乃係合成高純度聚矽烷之最 佳的方法,該開環加成聚合反應尤其適用於需要高純度材 料的應用領域上,例如電子材料。然而,由於上述單體具 有甲基(Me)或苯基(Ph)鍵結至矽原子的碳原子,即使當上述 聚矽烷爲經熱分解的,仍會形成含碳原子的聚碳矽烷( polycarbosilane),同時無法獲得適用於半導體之砂化合物。
anionic polymerization ^Me2 Me2 Me2 Μθ2
本發明目的係提供一種由矽原子與氫原子組成的新穎 環矽烷化合物。 (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 本發明 組成物,特 形矽膜之溶 環矽烷化合 其係藉由不 應而製得。 本發明 成具有均勻 而本發 著。 之另一目的係提 別是一種在基質 液組成物,而該 物所提供的高純 會副產生鹽之環 供一種適用於形成矽膜之溶液 表面上形成非晶形矽膜或聚晶 溶液組成物係以上述本發明之 度與溶劑溶解性聚矽烷爲主, 戊矽烷自由基開環加成聚合反 之再另一目的係提供一種短時間內在基質上形 厚度與鏡面之矽膜的方法。 明之其它目的及優點藉由下述說明將變得更顯 第一,根據本發明,上述本發明目的及優點可藉由下 本紙張尺度適用中國國家標準(CNS ) Α4規格(21〇Χ:297公釐) 1281921 A7 B7 五、發明説明(5 ) 式(A)所示甲矽烷基環戊矽烷而獲得: H2Si\ H2Si-
SiH- I -SiH.
SiH3 (A) 第二,根據本發明,上述本發明目的及優點可藉由用 於形成矽膜之溶液組成物而獲得,該溶液組成物係含有下 式(B)所示環戊矽烷及由上式(A)所示甲矽烷基環戊矽烷: H2sr\ H2Si- 广h2 -SiH, (B) (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 第三,根據本發明,上述本發明目的及優點可藉由在 基質表面上形成矽膜之方法而獲得,該方法包含步驟: (1) 製備上述本發明之用於形成矽膜之溶液組成物; (2) 將該溶液組成物塗覆於基質表面而形成塗膜;及 (3) 加熱該塗膜而形成矽膜。 又,根據本發明,亦提供一種由下式(C)所示螺[4.4]壬 矽烷,其具有類似於本發明甲矽烷基環戊矽烷之自由基開 環聚合環戊矽烷的功能: H2Si〆 、SiH2 、Si
Si .SiH2 (C) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) -8 - 1281921 A7 B7 五、發明説明(6) 圖示簡要說明 (請先閲讀背面之注意事項再填寫本頁) 第1圖’顯示甲矽烷基環戊矽烷之紅外線吸收光譜圖; 第2圖’顯示甲矽烷基環戊矽烷之質譜圖; 第3圖’顯示環戊矽烷之紅外線吸收光譜圖; 第4圖,顯示環戊矽烷之質譜圖; 第5圖,顯示環戊砍院與甲砂院基環戊砍院(重量比9/1) 之混合物的甲苯溶液氣相層析(GLC)圖; 第6圖’顯示環戊矽烷之甲苯溶液氣相層析(GLC)圖; 第7圖’顯示實例4所獲得的矽膜之ESCA光譜圖;及 第8圖’顯示實例6(1)所獲得的混合物之高速液體層析 圖。 發明詳細說明 下文更詳盡地說明本發明技術內容。 首先說明用於合成本發明之甲矽烷基環戊矽烷之方法 〇 經濟部智慧財產局員工消費合作社印製 至於用於合成甲矽烷基戊矽烷架構之方法,已記載於 J. Organomet. Chem. Vol· 100,ρρ· 127,( 1 975)中,其中十 二甲基環己矽烷可藉由以氯化鋁觸媒處理而定量地經再重 排成三甲基甲矽烷基壬甲基環戊矽烷,及該環己矽烷架構 經重排成熱動力穩定的甲矽烷基環戊矽烷架構。然而,該 甲矽烷基環戊砂烷架構之所有取代基爲甲基及不爲氫。已 知,藉由熱分解引起的脫氫反應,可將含有甲基鍵結至矽 之碳原子的聚矽烷轉變成含碳之碳矽烷(carbosUane),但不 -9 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X;297公釐) 1281921 A7 B7 五、發明説明(7 ) 會將其轉變成適用於半導體之金屬性矽化合物。 (請先閲讀背面之注意事項再填寫本頁) 已知有數種可將鍵結至矽原子之苯基轉變成氯原子及 氫原子之方法(例如 Mh. Chem. Vol. 106,ρρ· 503, ( 1 975)) J (Z. Anorg. Allg. Chem. vol. 621, pp. 1 5 1 7, ( 1 995))5 (J. Chem. Soc., Chem. Commun., 7 7 7, ( 1 984))。 本發明發明人已成功地將環己矽烷架構之所有苯基取 代基轉變成氫原子,及接著同時將環己矽烷架構轉變成甲 矽烷基環戊矽烷。而爲了將鍵結至十二苯基環己矽烷之矽 的苯基轉變成氫原子之進行,可利用氯化鋁觸媒作爲路易 氏酸處理轉換該架構、藉導入氯化氫氣體氫化、及以氫化 鋰鋁還原而完成。因此,本案發明人已成功地發展出本發 明之由矽原子與氫原子組成的甲矽烷基環戊矽烷。 經濟部智慧財產局員工消費合作社印製 本案發明人發現本發明之由矽原子與氫原子組成的甲 矽烷基環戊矽烷具有藉由自由基開環加成聚合反應將由矽 原子與氫原子組成的環戊矽烷轉變成溶劑溶解性聚矽烷之 化學性質。所得聚矽烷溶液具有優異共塗覆性,及能夠在 基質上形成適合的聚矽烷塗膜(其可藉由熱分解或光分解引 起的脫氫反應轉變成金屬性矽膜)。 本發明之甲矽烷基環戊矽烷可用作爲環戊矽烷的自由 基聚合反應起始劑,亦即,即使當環戊矽烷僅溶解於以烴 類爲主溶劑(例如甲苯)中及該溶液在溶劑沸點附近加熱時, 聚合反應不會進行。同時,當環戊矽烷與少量(例如1 wt%) 的甲矽烷基環戊矽烷溶解於以烴類爲主溶劑(例如甲苯)中時 ,環戊矽烷之聚合反應可平穩地進行。據推定其係由於甲 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -1〇 - 1281921 A7 B7 五、發明説明(8 ) 矽烷基環戊矽烷之甲矽烷基(SiH3)裂解成自由基及形成自由 基起始該環戊矽烷之聚合反應的機制所造成的結果。 (請先閱讀背面之注意事項再填寫本頁) 本發明之用於形成矽膜之溶液組成物含有甲矽烷基環 戊矽烷及環戊矽烷。 經濟部智慧財產局員工消費合作社印製 本發明之溶液組成物可藉由將該類化合物溶解於適當 的溶劑中而製備,任何一種溶劑若能溶解環戊矽烷及甲矽 烷基環矽烷且不會與溶劑反應之溶劑皆可被接受。較佳溶 劑實例包括以烴類爲主溶劑,例如η-庚烷、η-辛烷、癸烷、 甲苯、二甲苯、甲基·異丙基苯(cymene)、均四甲苯(durene) 、茚、二戊烯、四氫化萘、十氫化萘及環己基苯;以醚類 爲主的溶劑,例如乙二醇二甲基醚、乙二醇二乙基醚、乙 二醇甲基乙基醚、二乙二醇二甲基醚、二乙二醇二乙基醚 、二乙二醇甲基乙基醚、及p-二噁烷;及質子惰性的溶劑 ,例如亞丙基碳酸酯、r ·丁內酯、N-甲基-2-吡咯烷酮、二 甲基甲醯胺、二甲基亞硕、及環己酮。該類溶劑中,從環 狀矽化合物及溶液安定性的觀點來看,以烴類爲主溶劑及 醚類爲主溶劑爲較佳,又以醚類爲主溶劑爲更佳,及以烴 類爲主溶劑爲最佳。該類溶劑可單獨、或以二種或多種之 混合物形式使用。 本發明溶液組成物可藉使由環戊矽烷之合成反應副產 生的甲矽烷基環戊矽烷有效利用而製得,亦即,二苯基二 氯矽烷藉鎂或金屬性鋰於四氫呋喃中環化而形成十苯基環 戊矽烷與十二苯基環己矽烷,及該等化合物之混合物在甲 苯中以氯化鋁、氯化氫氣體處理,及然後與氫化鋰鋁與矽 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) _ 11 - 1281921 A7 __B7 五、發明説明(9 ) 膠混合,而從十苯基環戊矽烷與由十二苯基己矽烷轉變成 甲矽烷基環戊矽烷之架構形成環戊矽烷。甲矽烷基環戊矽 (請先閲讀背面之注意事項再填寫本頁) 垸與環戊砂院之混合物溶液可用作爲本發明之溶液組成物 〇 本發明溶液組成物之固體含量以0.01至30 wt %爲較佳 ,又以0.1至20 wt%爲更佳,以1至1〇 wt%爲最佳,其適當 的範圍依據形成的矽膜厚度而不同。 至於環戊矽烷與甲矽烷基環戊矽烷的比例,甲矽烷基 環戊砂院以0.01至30重量份爲較佳,又以〇.5至20重量份爲 更佳,以100重量份環戊矽院爲基準。 下文將說明本發明之矽膜形成方法。 經濟部智慧財產局員工消費合作社印製 步驟(1)中,例如依上述方式製備本發明溶液組成物。 接著,步驟(2)中,將該溶液組成物塗於基質上而形成塗膜 ,基質之材料、形狀等不特別受限制,惟材料以能忍受後 續步驟之熱處理者爲較佳。有塗膜形成的基質較佳爲平坦 的,該基質可由玻璃、金屬、塑膠或陶瓷製得,玻璃爲選 自石英玻璃、硼矽酸鹽玻璃、鈉玻璃與鉛玻璃,金屬爲選 自金、銀、銅、鎳、鋁、鐵與不銹鋼,及塑膠爲選自聚醯 亞胺與聚醚硕,材料形狀不特別受限制,可爲似板狀或似 膜狀。 爲了形成本發明溶液組成物之塗膜,該溶液組成物可 利用由鐵氟龍或再生的纖維素製得的隔膜濾器過濾而移除 固體外來物質。 爲了施塗本發明溶液組成物,塗覆方法不特別受限制 -12- 本紙張尺度適用中國國家標準(CNS ) A4規格(210x297公羡) 1281921 A7 B7 五、發明説明(10) (請先閲讀背面之注意事項再填寫本頁) ,可藉旋塗法、浸塗法、簾幕塗覆法、輥塗法、噴霧塗覆 法、或油墨噴射塗覆法等進行。塗覆可以一次或多次進行 。適合的塗膜厚度依據固體含量而變化,其在移除溶劑之 後的厚度以0.01至100# ΠΊ爲較佳,又以0.1至10// m爲更佳 〇 最後,在步驟(3)中,加熱塗膜。藉由加熱,將含於溶 液組成物中的溶劑揮發及將含於塗膜中的矽化合物分解而 形成矽膜。令人驚訝地是,由於步驟(3)中之塗膜含有甲矽 烷基環戊矽烷,形成的矽膜具有均勻厚度及鏡面,其乃因 爲某些情況下,由未含有甲矽烷基環戊矽烷之塗膜通常會 獲得具有非均勻厚度之矽膜或部分破裂的矽膜之故。 經濟部智慧財產局員工消費合作社印製 方法之加熱溫度以300°C或以上爲較佳,又以400至500 t爲更佳。加熱時間爲約30秒鐘至30分鐘。加熱氛團以在 惰性氣氛(例如氮氣、氨或氬氣氛團)中爲較佳,如需要可含 有還原氣體(例如氫)。本案發明人尙無法解釋所進行的硏究 ,據信該方法係首先藉加熱揮發溶劑,在同時或揮發作用 之後發生環戊矽烷之自由基開環反應,部分環戊矽烷轉變 成寡聚物,藉由該寡聚物之熱分解反應形成氫,及同時形 成矽膜。亦據信該方法即使當甲矽烷基被奪取時,含有甲 矽烷基環戊矽烷之物質可形成甲矽烷基自由基及環戊矽烷 基自由基。 於步驟(3)中,如需要在加熱之前該塗膜可利用紫外光 輻射照射,在365 nm需要紫外光輻射劑量爲〇.1至1〇〇 j/cm2 才足夠。紫外光輻射之光源可爲低壓或高壓汞燈、重質氫 本紙張尺度適财關家料(CNS ) A4驗(210X297公釐) 「13 -' — 1281921 A7 B7 五、發明説明(11) 燈、氬、氪或山等稀有氣體放電燈、YAG激光、氬激光、 碳酸氣激光、或 XeF、XeCl、XeBr、KrF、KrCM、ArF 或 ArCl 激子激光,該等光源通常具有輸出量爲10至5,000 W,而需 要輸出量爲100至1,000 W才足夠。 依據本發明之方法,矽膜(特別是非晶形矽膜)可有效地 在基質上形成,該矽膜厚度可爲0.001至10// m。 本發明之溶液組成物如需要可含有微量之以氟爲主、 以矽爲主或非離子性表面張力控制之物質,除非其無法賦 予本發明之目的。該非離子性表面張力控制物質可改進用 於本發明塗覆目的的溶液之濕潤性、塗膜之平準性質,及 避免在塗膜上形成凸塊。該非離子性界面劑爲以氟爲主界 面劑,其具有氟烷基基團或全氟烷基基團,或爲以聚醚烷 基爲主界面劑,其具有氧烷基激團,該以氟爲主界面劑實 ^!lfe®C9Fl9CONHCl2H25' C8Fl7S〇2NH-(C2H4〇)6H' C9Fl7〇( Pulronic L-SSWgFH、CgFuOiPulronic P-SWC^Fh、及 Tetronic-704)(C9Fi7)2(Pulronic L-35 :製自 Asahi Denka Kogyo股份有限公司’具有平均分子量1,900之聚氧丙儲-聚 氧乙烯嵌段共聚物;Pulronic P-84 :製自Asahi Denka Kogyo股份有限公司’具有平均分子量4,200之聚氧丙嫌-聚 氧乙烯嵌段共聚物;Tetronic-704:製自Asahi Denka Kogyo 股份有限公司,具有平均分子量5,000之N,N,N,N-肆(聚氧丙 烯-聚氧乙烯嵌段共聚物))。以氟爲主界面劑之商業購得產 物包括 F Top EF301、EF303 及 EF352(Shin Akita Kasei 股份 有限公司),Megafac F171及F173(大日本油墨化學品公司) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -14 - (請先閱讀背面之注意事項再填寫本頁) 訂 經濟部智慧財產局員工消費合作社印製 1281921 A7 B7 五、發明説明(12) ,八5&11丨〇1^(1八〇710(八8&111玻璃股份有限公司),?1〇^(^ FC-170C、FC430 及 FC431(Sumitomo 3M有限公司),Surflon S-382、SC101、SC102、SC103、SCI 04、SC105及SC106( Asahi玻璃股份有限公司),BM- 1 000及1100(B.M.化學股份有 限公司),及3仏8 6£0-?1110^(3〇1^6211^1111股份有限公司)。以 聚醚烷基爲主界面劑實例包括聚氧乙烯烷基醚類、聚氧乙 烯烯丙基醚類、聚氧乙烯烷基苯酚醚類、聚氧乙烯脂肪酸 酯類、山梨糖醇酐脂肪酸酯類、聚氧乙烯山梨糖醇酐脂肪 酸酯類及氧乙烯-氧丙烯嵌段共聚物。以聚醚烷基爲主界面 劑之商業購得產物包括Emulgen 105、430、810及920, Leodor SP-40S及 TW-L120,Emanol 3199及 4110,Excel P-40S,Bridge 30、52、72及 92,Arassel 20,Emasol 320, Tween 20及 60,及 Merge 45(Kao股份公司)及 Noniball 55( Sanyo化學工業股份有限公司)。除了上述之外的非離子性界 面劑包括聚氧乙烯脂肪酸酯類、聚氧乙烯山梨糖醇酐脂肪 酸酯類及聚亞烷基氧化物嵌段共聚物,及其商業購得產物 包括 Chemistat 2500(Sanyo 化學工業有限公司),SN-EX9228( SUN Nopco股份有限公司)及Nonale 530(Toho化學工業股份 有限公司)。 由本發明形成的非晶形矽膜可用於各種電子設備,例 如太陽能電池、光感應器、薄膜電晶體、光敏性輥箱(drums )及保護膜。 最後,依據本發明亦提供螺[4.4]壬矽烷化合物,其具 有類似本發明之甲矽烷基環戊矽烷之自由基開環聚合反應 本矣氏張尺度適用中國國家標準(CNS ) A4規格(210X29*7公釐) -15 - " (請先閲讀背面之注意事項再填寫本頁) 訂
經濟部智慧財產局員工消費合作社印製 1281921 A7 __B7 五、發明説明(13 ) 環戊矽烷的功能。 (請先閱讀背面之注意事項再填寫本頁) 本發明之螺[4·4]壬矽烷可藉由已知方法合成製得,該 方法中鍵結至十六苯基螺[4.4]壬矽烷之矽原子的苯基轉變 成氯原子,然後再轉變成氫原子(例如,Mh. Chem. vol. 106,ρρ· 503,(1 975)),(Z. Anorg. Allg· Chem. vol. 621, pp. 1517,( 1 995)),(J· Chem. Soc.,Chem. Commun.,777 ,(1984))。 例如,在路易氏酸觸媒(例如氯化鋁)存在下,十六苯基 螺[4.4]壬矽烷藉由引入氯化氫氣體進行氯化,及然後以氫 化鋰鋁進行氫化而將十六苯基螺[4.4]壬矽烷之全部苯基取 代基轉變成氫原子,以製造由矽原子與氫原子組成的螺[4.4 ]壬矽烷。 氯化反應可在0至80°C溫度進行1至12小時,路易氏酸 觸媒使用量可爲0」至20 wt%,以十六苯基螺[4.4]壬矽烷爲 基準。可使用有機溶劑(例如甲苯)作爲反應溶劑。 還原反應可在0至5CTC溫度進行1至24小時。 經濟部智慧財產局員工消費合作社印製 在金屬性鋰存在下,作爲原料之十六苯基螺[4.4]壬矽 烷可藉由二苯基二氯矽烷與四氯矽烷之脫鹵化反應及縮合 反應而獲得。 本發明之甲矽烷基環戊矽烷可用作爲環戊矽烷之自由 基聚合反應起始劑,及亦可作爲乙烯基單體之自由基起始 劑,此例中,可獲得在聚合物分子終端具有矽原子之乙烯 基聚合物,藉此使其可能地衍生乙烯基聚合物與以矽爲主 聚合物之嵌段或無規共聚物。 16- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 1281921 A7 ___B7___ 五、發明説明(14 ) 上述乙烯基單體實例包括芳族乙烯基化合物,例如苯 乙稀、α-甲基苯乙條、〇 -乙嫌基甲苯、m -乙烯基甲苯、p-乙烯基甲苯、P-氯苯乙烯-〇-甲氧基苯乙烯、m-甲氧基苯乙 烯及P-甲氧基苯乙烯;丙烯酸酯類及甲基丙烯酸酯類,例 如丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯 酸乙酯、丙烯酸η-丙酯、甲基丙烯酸η-丙酯、丙烯酸i-丙酯 、甲基丙烯酸i-丙酯、丙烯酸η-丁酯、甲基丙烯酸η-丁酯、 丙烯酸1-丁酯、甲基丙烯酸i-丁酯、丙烯酸sec-丁酯、甲基 丙烯酸sec-丁酯、丙烯酸t-丁酯、甲基丙烯酸t-丁酯、丙烯 酸2-羥基乙基酯及甲基丙烯酸2-羥基乙基酯;及脂族共軛二 烯,例如1,3-丁二烯、異丙烯及氯丙烯。 以下實例係提供進一步說明本發明之用,惟不作爲限 制本發明。 實例 實例1
(1)在配設有溫度計、冷凝管、滴漏斗及攪拌器之2升四 頸燒瓶內部以氬氣替代,及將1.5升乾燥的四氫呋喃與27.4 克金屬性鋰饋入燒瓶中及以氬氣起泡。於該懸浮液中藉由 滴漏斗添加500克二苯基二氯矽烷,同時冰冷卻下攪拌。在 繼續進行反應直到金屬性鋰完全消失爲止,將該反應混合 物倒入冰水中而沉澱出反應產物。該沉澱物藉過濾分離及 &水然後環己烷淸洗完全。又,該粗產物以乙酸乙酯再結 晶而獲得216克十二苯基環己矽烷。該產物結構藉由TOF-MS 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) (請先閲讀背面之注意事項再填寫本頁) ♦ 訂 經濟部智慧財產局員工消費合作社印製 -17- 1281921 A7 _ B7 五、發明説明(15 ) 、NMR及IR確認。隨後,100克該十二苯基環己矽烷及1,000 毫升甲苯饋入2升燒瓶中,添加50克氯化鋁,及在氬氣氛團 中室溫攪拌5小時,然後將氯化氫氣體引入直到苯基消失爲 止。由該反應獲得的產物藉由29Si-NMR與IR光譜實際測得係 爲十二氯環己矽烷。隨後,將上述反應混合物慢慢加至42 克氫化鋰鋁懸浮於500毫升乙醚之溶液中,及室溫攪拌12小 時。將該反應混合物過濾而獲得消色的及透明的甲矽烷基 環戊矽烷溶液。 (2)所得甲矽烷基環戊矽烷在室溫爲油狀,及其紅外線 吸收光譜如第1圖所示。該由矽原子與氫原子組成的甲矽烷 基環戊矽烷,其紅外線光譜相當簡單,在2,125 cnT1可觀察 到矽-氫鍵拉伸振動吸收尖峰,及在985cm·1至863cm·1觀察到 矽-矽鍵拉伸振動吸收峰。第2圖顯示甲矽烷基環戊矽烷之 質量光譜圖,由於在m/e爲180處觀察到分子離子峰,該物 質的分子量爲180,在m/e爲148處偵測到強吸收峰係爲由甲 矽烷基環戊矽烷分子之一個單矽烷(SiH4)之除去而形成的裂 片產生的吸收峰,及在m/e爲1 1 6處偵測到吸收峰係爲由甲 矽烷基環戊矽烷分子的二個單矽烷除去而形成的裂片產生 的吸收峰。 至於甲矽烷基環戊矽烷的化學性質,該甲矽烷基環戊 矽烷可容易地溶解於一般有機溶劑,例如烴類溶劑舉例說 明如苯、甲苯、二甲苯、己院、環己院、節及十氫化萘, 以乙醚爲主溶劑舉例說明如乙醚、四氫呋喃、monoglyme、 及diglyme,或以酮爲主溶劑舉例說明如丙酮、甲基乙基酮 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -18 · " (請先閱讀背面之注意事項再填寫本頁) ·#衣· 訂 經濟部智慧財產局員工消費合作社印製 1281921 A7 _B7 五、發明説明(16 ) 、甲基異丁基酮或甲基戊基酮,上述溶劑可爲任意比例。 (請先閱讀背面之注意事項再填寫本頁) 如上所述甲矽烷基環戊矽烷在室溫爲消色與透明油狀 物質,及在惰性氣氛(例如氬氣或氮氣)中極爲安定。然而, 當其留在空氣中時,其慢慢地氧化及易於轉變成矽氧烷結 構。當甲矽烷基環戊矽烷在惰性氣氛中於3〇〇°C或以上加熱 時,會發生脫氫反應而將其轉變成非晶形金屬性矽。又, 該甲矽烷基環戊矽烷藉由在約1 00°c加熱會產生自由基,而 將上述環戊矽烷自由基開環聚合,將其轉變成溶劑可溶解 的聚矽烷。又再,其可聚合自由基可聚合的單體,例如乙 烯基化合物(舉例說明如一般的丙烯酸化合物)。 在120°C藉由使用Chromosorb W(60至80篩目)作爲載體 、矽酮〇V-17(5%)作爲液相、及氦氣,而獲得甲矽烷基環戊 矽烷與環戊矽烷之氣相層析圖,(請參閱第5圖及第6圖)。 實例2 經濟部智慧財產局員工消費合作社印製 在配設有溫度計、冷凝管及攪拌器之2升四頸燒瓶內部 以氬氣替代,及將1.5升乾燥的四氫呋喃與3.8克金屬性鋰饋 入燒瓶中及以氬氣起泡。於該懸浮液中100克之藉由Hengge 等人之方法(J. Organomet. Chem·,vol. 212, pp. 155(1981)) 合成的八苯基環丁矽烷,同時室溫攪拌5小時,以開環八 苯基環丁矽烷而形成雙陰離子。將5 0克三苯基甲矽烷基苯 基二氯矽烷加入及進行反應,同時室溫攪拌該深褐色雙陰 離子溶液。將該反應混合物倒入2升冰水中而沉澱出反應產 物。該所得產物藉過濾分離,及以水然後環己烷淸洗,及 -19- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 1281921 A7 _B7__ 五、發明説明(17 ) 減壓乾燥而獲得108克三苯基甲矽烷基壬苯基環戊矽烷。又 ,將50克所得的三苯基甲矽烷基壬苯基環戊矽烷溶解於5〇〇 毫升甲苯中’及將5克無水氣化銘添加至氣化氯热體與二本 基甲矽烷基壬苯基環戊矽烷反應系統中,進行反應直到苯 基消失爲止。隨後,該反應產物添加至含有20克氫化鋰鋁 懸浮於100毫升乙醚之溶液中,及室溫攪拌12小時。該反應 混合物以矽膠處理及濃縮而獲得消色與透明的油狀物質。 該物質IR與MS光譜利用上述實例1產物之分析方法確認。 參考實例1 將50克十苯基環戊矽烷與500毫升甲苯饋入配設有溫度 計、冷凝管及攪拌器之2升四頸燒瓶中。將5克無水氯化鋁 添加至該反應溶液中,及進一步在室溫將氯化氫氣體與十 苯基環戊矽烷反應5小時。藉反應系統之NMR確認苯基之消 失。隨後,將該反應混合物添加至含有20克氫化鋰鋁分別 製備及懸浮於100毫升乙醚之溶液中,及室溫攪拌12小時。 該反應混合物以矽膠處理及濃縮而獲得消色與透明的油狀 環戊矽烷。該物質的IR光譜如第3圖所示,及其MS光譜如第 4圖所示。 實例3 (1)在配設有溫度計、冷卻冷凝管、滴漏斗及攪拌器之3 升四頸燒瓶內部以氬氣替代,及將1升乾燥的四氫呋喃與 1 8 · 3克金屬性鋰饋入燒瓶中及以氬氣起泡。於該懸浮液中藉 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 72〇Z ' (請先閲讀背面之注意事項再填寫本頁) ♦ 訂 經濟部智慧財產局員工消費合作社印製 1281921 A7 ___B7 五、發明説明(18 ) (請先閱讀背面之注意事項再填寫本頁) 由滴漏斗添加33 3克二苯基二氯矽烷,同時在〇°c攪拌,及 在加成反應末段進一步在室溫繼續攪拌1 2小時直到金屬性 鋰完全消失爲止。將該反應混合物倒入5升冰水中而沉澱出 反應產物。該沉澱物藉過濾分離,及以水然後環己烷淸洗 完全,及真空乾燥而獲得140克白色固體。該白色固體之IR 、^-NMR及29Si-NMR光譜顯示其爲二個組成的混合物(下文 係表示爲矽化合物混合物A)。當該矽化合物混合物A藉由高 速液體層析法分離時,主要產物與副產物之比例爲8 : 1。 當進一步測量主要產物與副產物之IR、W-NMR、29Si-NMR 及TOF-MS光譜時,確認得主要產物爲十苯基環戊矽烷(下文 表示爲矽化合物B)與副產物爲十二苯基環己矽烷(下文表示 爲矽化合物C)。 經濟部智慧財產局員工消費合作社印製 (2) 將5 0克上述矽化合物混合物A與500毫升乾燥的甲苯 饋入1升燒瓶中,添加2克氯化鋁,及室溫引入氯化氫,繼 續在氬氣氛團中反應5小時。將20克氫化鋰鋁與200毫升乙 醚分別饋入2升燒瓶中,及在氬氣氛團中0°C下攪拌添加上 述反應混合物,相同溫度下攪拌1小時,及進一步保持於室 溫攪拌1 2小時。將鋁化合物從反應混合物中移除,及將溶 劑蒸發除去,而獲得5克黏稠油狀產物。由其IR、W-NMR、 29Si-NMR與GC-MS光譜中實際測得該產物爲環戊矽烷(下文 表示爲矽化合物D)與甲矽烷基環戊矽烷(下文表示爲矽化合 物E)之混合物(下文表示爲矽化合物混合物F),混合比例爲8 :1 ° (3) 當85克矽化合物混合物A以4升乙酸乙酯再結晶時, -21 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X29?公釐) 1281921 A7 B7 五、發明説明(19 ) (請先閱讀背面之注意事項再填寫本頁) 可獲得55克純矽化合物B。當50克所得矽化合物B施以上述 步驟(2)時,可獲得5克純矽化合物D。藉氣相層析法可確認 該化合物具有99%或以上純度。 實例4 在氬氣氛團中,將在實例3之步驟(2)獲得的5克矽化合 物混合物F溶解於95克甲苯中,而製得溶液。在氬氣氛團中 該溶液旋塗在石英基質上而形成矽化合物混合物F膜。當在 氬氣氛團中該經塗覆基質於500°C加熱5分鐘時,矽膜會殘 留在基質上。由其拉曼散射光譜實際測得該矽膜爲100%非 晶形。當該非晶形矽以由XeCl激子體激光(308nm)產生的光 照射時,矽經聚結晶成75 %結晶度。當由該經聚結晶矽膜之 ESCA光譜測得該矽原子的2P軌域能量時,實際測得爲99.0 eV而證實爲矽。第7圖所示爲矽膜之ESCA光譜。 比較例2 經濟部智慧財產局員工消費合作社印製 在氬氣氛團中,將實例3中步驟(3)獲得的5克矽化合物 D溶解於9 5克甲苯中而製得溶液。在氬氣氛團中,將該溶液 旋塗於石英基質上,但由於溶液之縮邊(c1SS1ng)而無法獲得 均勻膜。 實例5 在氬氣氛團中,將在實例3之步驟(2)獲得的5克矽化合 物混合物F溶解於95克甲苯中而製得溶液。在氬氣氛團中該 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -22 _ 1281921 A7 B7 五、發明説明(2〇 ) (請先閲讀背面之注意事項再填寫本頁) 溶液旋塗在石英基質上而形成矽化合物混合物F膜。當該經 塗覆基質在氬氣氛團中以UV照射及於500°C加熱5分鐘時, 矽膜會殘留在基質上。由其拉曼散射光譜實際測得該矽膜 爲100%非晶形。當該非晶形矽以由XeCl激子體激光(308nm) 產生的光照射時,矽經聚結晶成75 %結晶度。當由該經聚結 晶矽膜之ESCA光譜測得該矽原子的2P軌域能量時,實際測 得爲99.0 eV而證實爲矽。 實例6 經濟部智慧財產局員工消費合作社印製 (1) 在配設有溫度計、冷卻冷凝管、滴漏斗及攪拌器之3 升四頸燒瓶內部以氬氣替代,及將1升乾燥的四氫呋喃與 2 0.3克金屬性鋰饋入燒瓶中及以氬氣起泡。於該懸浮液中藉 由滴漏斗添加296克二苯基二氯矽烷與24.8克四氯矽烷。在 添加結束後,另外於25 °C繼續攪拌1 2小時直到該金屬性鋰 完全消失爲止。將該反應混合物倒入5升冰水中而沉澱出反 應產物。該沉澱物藉過濾分離,以水然後環己烷淸洗完全 及真空乾燥而獲得180克白色固體。該白色固體之IR、4-NMR及29Si-NMR光譜顯示其爲二個成分之混合物。當該混合 物藉由高速液體層析法分離時,實際測得主要產物與副產 物之比例爲9 : 1。當進一步檢測該等產物之IR、^-NMR及 29Si-NMR及TOF-MS光譜時,確認主要產物爲十苯基環戊矽 烷,及副產物爲十六苯基螺[4.4]壬矽烷。第8圖所示爲上述 混合物之高速液體層析圖。 (2) 將上述步驟(1)中獲得的十苯基環戊矽烷與十六苯基 本ί氏張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -23- ' '~ 1281921 A7 B7 五、發明説明(21 ) 螺[4.4]壬矽烷之50克混合物(比例9 : 1)及500毫升乾燥的甲 苯饋入1升燒瓶中,添加2克氯化鋁,及在25 °C引入氯化氣 繼續在氬氣氛團中反應5小時。將20克氫化鋰鋁與200毫升 乙醚分別饋入2升燒瓶中,及於氬氣氛團中於〇°C攪拌添加 上述反應混合物,在相同溫度攪拌1小時及另外保持於25 t 下攪拌1 2小時。將鋁化合物從該反應混合物中移除,及將 溶劑蒸除,而獲得5克黏稠油狀產物。從產物之IR、iH-NMR 、29Si-NMR及GC-MS光譜實際測得產物爲環戊矽烷與螺[4.4] 壬矽烷之混合物,其比例爲9 : 1。 (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 -24- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)
Claims (1)
- A8 B8 C8 D8 ^、甲齋範圍 第90 1 0573 1號專利申請案 中文申請專利範圍修正本# 民國9 5年3 1·一種用於形成矽膜之溶液組成物,其係含有下式(A) 表示之甲矽烷基環戊矽烷: 月17曰瞻 S1H- H.Si\ / H2Si-'SxH2 及由下式(B)表示之環戊矽烷: •SiH3 (A) (請先聞脅背面之注意事項再填寫本頁) (B) 經濟部智慧財產局員工消費合作社印製 .¾ H2Si SiH2 H2Si-SiH2 其中每100重量份之環戊矽烷,含有0.01至30重量份之 甲矽烷基環戊矽烷。 2 . —種在基質表面上形成矽膜之方法,包含下列步驟 (1 )製備如申請專利範圍第1項之用於形成矽膜之溶液組 成物; (2) 在基質表面塗覆該溶液組成物以形成塗膜;及 (3) 加熱該塗膜以形成矽膜。 3 . —種用於形成矽膜之溶液組成物,其含有如申請專 本紙張尺度適用中國國家摞準(CNS ) A4規格(210X297公釐) 1281921 A8 B8 C8 D8 六、申請專利範圍 利範圍第1項所定義之式(B )所示的環戊矽烷及下式(C )所示的螺[4.4 ]壬矽烷, H2Si^ I H2Si、 、SiH2 、Si SiH, Si (C) 其中環戊矽烷和螺[4.4]壬矽烷的重量比爲9 : i。 4 · 一種在基質表面上形成矽膜之方法,其包含下列步 (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 驟: (1 )製備如申請專利範圍第3項之用於形成矽膜之溶 液組成物; (2 )在基質表面塗覆該溶液組成物以形成塗膜;及 (3 )加熱該塗膜以形成矽膜。 本紙張尺度適用中國國家襟準(CNS ) A4規格(210X297公釐) -2 -
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JP2000164102A JP4748288B2 (ja) | 2000-06-01 | 2000-06-01 | スピロ[4.4]ノナシランを含有する組成物 |
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TW090105731A TWI281921B (en) | 2000-03-13 | 2001-03-12 | Novel cyclosilane compound, and solution composition and process for forming a silicon film |
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US (1) | US6503570B2 (zh) |
EP (1) | EP1134224B1 (zh) |
KR (1) | KR100562815B1 (zh) |
DE (1) | DE60128611T2 (zh) |
TW (1) | TWI281921B (zh) |
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JP5580507B2 (ja) * | 2003-11-20 | 2014-08-27 | シグマ−アルドリッチ・カンパニー、エルエルシー | 吸着構造体 |
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US7485691B1 (en) | 2004-10-08 | 2009-02-03 | Kovio, Inc | Polysilane compositions, methods for their synthesis and films formed therefrom |
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WO2008045327A2 (en) | 2006-10-06 | 2008-04-17 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
US8530589B2 (en) * | 2007-05-04 | 2013-09-10 | Kovio, Inc. | Print processing for patterned conductor, semiconductor and dielectric materials |
WO2009026126A2 (en) * | 2007-08-17 | 2009-02-26 | Ndsu Research Foundation | Convergent-divergent-convergent nozzle focusing of aerosol particles for micron-scale direct writing |
SG2012070850A (en) * | 2007-10-01 | 2014-04-28 | Kovio Inc | Profile engineered thin film devices and structures |
US9564629B2 (en) * | 2008-01-02 | 2017-02-07 | Nanotek Instruments, Inc. | Hybrid nano-filament anode compositions for lithium ion batteries |
US20090283766A1 (en) * | 2008-05-19 | 2009-11-19 | Silexos, Inc. | Methods for increasing film thickness during the deposition of silicon films using liquid silane materials |
WO2009148878A2 (en) * | 2008-05-29 | 2009-12-10 | Ndsu Research Foundation | Method of forming functionalized silanes |
EP2301991A4 (en) * | 2008-07-11 | 2012-06-20 | Japan Science & Tech Agency | PROCESS FOR PRODUCING POLYSILANE |
US9336925B1 (en) * | 2008-11-26 | 2016-05-10 | Thin Film Electronics Asa | Siloxanes, doped siloxanes, methods for their synthesis, compositions containing the same, and films formed therefrom |
KR101175405B1 (ko) * | 2009-09-03 | 2012-08-20 | 신동윤 | 폴리실란계 화합물의 제조 방법 및 이에 따라 제조되는 폴리실란계 화합물, 이에 이용되는 탈수소화 촉매, 폴리실란계 화합물로 무정형 실리콘 박막을 제조하는 방법 |
DE102009053806A1 (de) | 2009-11-18 | 2011-05-19 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Siliciumschichten |
DE102009053805A1 (de) * | 2009-11-18 | 2011-05-26 | Evonik Degussa Gmbh | Siliziumschichten aus polymermodifizierten Flüssigsilan-Formulierungen |
US8624049B2 (en) * | 2010-01-18 | 2014-01-07 | Kovio, Inc. | Dopant group-substituted semiconductor precursor compounds, compositions containing the same, and methods of making such compounds and compositions |
JP5697692B2 (ja) | 2010-01-28 | 2015-04-08 | エヌディーエスユー リサーチ ファウンデーション | シクロヘキサシラン化合物を生成する方法 |
DE102010002405A1 (de) | 2010-02-26 | 2011-09-01 | Evonik Degussa Gmbh | Verfahren zur Oligomerisierung von Hydridosilanen, die mit dem Verfahren herstellbaren Oligomerisate und ihre Verwendung |
SG184020A1 (en) * | 2010-03-18 | 2012-10-30 | Univ Texas | Silicon-containing block co-polymers, methods for synthesis and use |
KR20130069611A (ko) | 2010-04-06 | 2013-06-26 | 엔디에스유 리서치 파운데이션 | 액체 실란계 조성물 및 실리콘계 물질의 제조 방법 |
JP5442572B2 (ja) | 2010-09-28 | 2014-03-12 | 株式会社日立ハイテクサイエンス | 荷電粒子ビーム装置、薄膜作製方法、欠陥修正方法及びデバイス作製方法 |
DE102011006307A1 (de) | 2011-03-29 | 2012-10-04 | Evonik Degussa Gmbh | Verfahren zum Herstellen von amorphen Halbleiterschichten |
JP5902572B2 (ja) | 2012-07-04 | 2016-04-13 | 株式会社日本触媒 | ケイ素−ハロゲン結合を有するハロゲン化環状シラン化合物またはその塩の製造方法 |
DE102012221669A1 (de) * | 2012-11-27 | 2014-05-28 | Evonik Industries Ag | Verfahren zum Herstellen kohlenstoffhaltiger Hydridosilane |
WO2016009827A1 (ja) | 2014-07-16 | 2016-01-21 | 日産化学工業株式会社 | 高分子量ポリシラン及びその製造方法 |
CN107431139B (zh) * | 2015-03-30 | 2020-12-01 | 默克专利有限公司 | 包含硅氧烷溶剂的有机功能材料的制剂 |
JP6534959B2 (ja) * | 2016-04-21 | 2019-06-26 | 信越化学工業株式会社 | 有機膜の形成方法及び半導体装置用基板の製造方法 |
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EP1085579B1 (en) * | 1999-03-30 | 2009-02-18 | Seiko Epson Corporation | Method of manufacturing solar cell |
EP1715509B1 (en) * | 1999-03-30 | 2011-08-24 | JSR Corporation | Method of forming silicon films |
DE60036449T2 (de) * | 1999-03-30 | 2008-06-19 | Seiko Epson Corp. | Verfahren zur hestellung eines dünnschichtfeldeffekttransistors |
KR100702555B1 (ko) * | 1999-03-30 | 2007-04-04 | 제이에스알 가부시끼가이샤 | 실리콘 산화막의 형성 방법 |
WO2000059014A1 (en) * | 1999-03-30 | 2000-10-05 | Seiko Epson Corporation | Method for forming a silicon film and ink composition for ink jet |
-
2001
- 2001-03-12 EP EP01106037A patent/EP1134224B1/en not_active Expired - Lifetime
- 2001-03-12 KR KR1020010012516A patent/KR100562815B1/ko not_active IP Right Cessation
- 2001-03-12 TW TW090105731A patent/TWI281921B/zh not_active IP Right Cessation
- 2001-03-12 DE DE60128611T patent/DE60128611T2/de not_active Expired - Lifetime
- 2001-03-12 US US09/802,918 patent/US6503570B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR100562815B1 (ko) | 2006-03-23 |
DE60128611T2 (de) | 2008-01-31 |
EP1134224B1 (en) | 2007-05-30 |
EP1134224A2 (en) | 2001-09-19 |
US6503570B2 (en) | 2003-01-07 |
KR20010091967A (ko) | 2001-10-23 |
US20010021760A1 (en) | 2001-09-13 |
DE60128611D1 (de) | 2007-07-12 |
EP1134224A3 (en) | 2003-01-15 |
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