KR20000013302A - 화학 증착법을 위한 유기 구리 전구체 - Google Patents
화학 증착법을 위한 유기 구리 전구체 Download PDFInfo
- Publication number
- KR20000013302A KR20000013302A KR1019980032069A KR19980032069A KR20000013302A KR 20000013302 A KR20000013302 A KR 20000013302A KR 1019980032069 A KR1019980032069 A KR 1019980032069A KR 19980032069 A KR19980032069 A KR 19980032069A KR 20000013302 A KR20000013302 A KR 20000013302A
- Authority
- KR
- South Korea
- Prior art keywords
- copper
- oxobutanoate
- vapor deposition
- alkyl
- chemical vapor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000005229 chemical vapour deposition Methods 0.000 title description 18
- 239000012691 Cu precursor Substances 0.000 title description 5
- 239000011521 glass Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000010949 copper Substances 0.000 abstract description 72
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 57
- 229910052802 copper Inorganic materials 0.000 abstract description 57
- 239000002243 precursor Substances 0.000 abstract description 25
- 239000010409 thin film Substances 0.000 abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 abstract description 15
- 239000011737 fluorine Substances 0.000 abstract description 15
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- -1 Alkyl 3-oxobutanoate Chemical compound 0.000 abstract description 11
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 6
- WQRUFMHFJXVZMZ-UHFFFAOYSA-N tert-butyl 2-oxobutanoate Chemical compound CCC(=O)C(=O)OC(C)(C)C WQRUFMHFJXVZMZ-UHFFFAOYSA-N 0.000 abstract description 5
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011734 sodium Substances 0.000 abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract description 3
- 229910052708 sodium Inorganic materials 0.000 abstract description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000007740 vapor deposition Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 238000000151 deposition Methods 0.000 description 13
- 230000008021 deposition Effects 0.000 description 11
- 239000010408 film Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000002879 Lewis base Substances 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 150000007527 lewis bases Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 4
- 238000005137 deposition process Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- 239000005749 Copper compound Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000001493 electron microscopy Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- NHQSYENHCTXNIG-UHFFFAOYSA-N [Cu+3].[O-]P([O-])[O-] Chemical compound [Cu+3].[O-]P([O-])[O-] NHQSYENHCTXNIG-UHFFFAOYSA-N 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UHJVZKSMFPPYLY-UHFFFAOYSA-M sodium;3-oxobutanoic acid;chloride Chemical compound [Na+].[Cl-].CC(=O)CC(O)=O UHJVZKSMFPPYLY-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si 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
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/06—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
- C23C16/18—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Vapour Deposition (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrodes Of Semiconductors (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019980032069A KR20000013302A (ko) | 1998-08-06 | 1998-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
| EP99935166A EP1121474A2 (en) | 1998-08-06 | 1999-08-06 | Organocopper precursors for chemical vapor deposition |
| KR1020017001526A KR100582619B1 (ko) | 1998-08-06 | 1999-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
| PCT/KR1999/000438 WO2000008225A2 (en) | 1998-08-06 | 1999-08-06 | Organocopper precursors for chemical vapor deposition |
| US09/744,619 US6538147B1 (en) | 1998-08-06 | 1999-08-06 | Organocopper precursors for chemical vapor deposition |
| JP2000563846A JP2002522453A (ja) | 1998-08-06 | 1999-08-06 | 化学蒸着のための有機銅前駆体 |
| TW088115303A TW499497B (en) | 1998-08-06 | 1999-09-03 | Organocopper precursors for chemical vapor deposition and a method of depositing copper on a substrate using said precursors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019980032069A KR20000013302A (ko) | 1998-08-06 | 1998-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000013302A true KR20000013302A (ko) | 2000-03-06 |
Family
ID=19546633
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980032069A Abandoned KR20000013302A (ko) | 1998-08-06 | 1998-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
| KR1020017001526A Expired - Fee Related KR100582619B1 (ko) | 1998-08-06 | 1999-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020017001526A Expired - Fee Related KR100582619B1 (ko) | 1998-08-06 | 1999-08-06 | 화학 증착법을 위한 유기 구리 전구체 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6538147B1 (https=) |
| EP (1) | EP1121474A2 (https=) |
| JP (1) | JP2002522453A (https=) |
| KR (2) | KR20000013302A (https=) |
| TW (1) | TW499497B (https=) |
| WO (1) | WO2000008225A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10319454A1 (de) * | 2003-04-29 | 2004-11-18 | Merck Patent Gmbh | Dikupfer(I)oxalat-Komplexe als Precursor zur metallischen Kupferabscheidung |
| US8030833B2 (en) | 2003-09-19 | 2011-10-04 | The Board Of Trustees Of The University Of Illinois | Electron emission device incorporating free standing monocrystalline nanowires |
| US7344753B2 (en) * | 2003-09-19 | 2008-03-18 | The Board Of Trustees Of The University Of Illinois | Nanostructures including a metal |
| US7166732B2 (en) * | 2004-06-16 | 2007-01-23 | Advanced Technology Materials, Inc. | Copper (I) compounds useful as deposition precursors of copper thin films |
| US7205422B2 (en) * | 2004-12-30 | 2007-04-17 | Air Products And Chemicals, Inc. | Volatile metal β-ketoiminate and metal β-diiminate complexes |
| US7034169B1 (en) | 2004-12-30 | 2006-04-25 | Air Products And Chemicals, Inc. | Volatile metal β-ketoiminate complexes |
| US20090162550A1 (en) * | 2006-06-02 | 2009-06-25 | Advanced Technology Materials, Inc. | Copper (i) amidinates and guanidinates, mixed ligand copper complexes, and compositions for chemical vapor deposition, atomic layer deposition, and rapid vapor deposition of copper |
| US20110060165A1 (en) * | 2006-12-05 | 2011-03-10 | Advanced Technology Materials, Inc. | Metal aminotroponiminates, bis-oxazolinates and guanidinates |
| US8263795B2 (en) * | 2007-11-05 | 2012-09-11 | Air Products And Chemicals, Inc. | Copper precursors for thin film deposition |
| DE102007058571B4 (de) | 2007-12-05 | 2012-02-16 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Substrat mit einer Kupfer enthaltenden Beschichtung und Verfahren zu deren Herstellung mittels Atomic Layer Deposition und Verwendung des Verfahrens |
| WO2014047544A1 (en) * | 2012-09-21 | 2014-03-27 | Wayne State University | Deposition of metal films based upon complementary reactions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5098516A (en) * | 1990-12-31 | 1992-03-24 | Air Products And Chemicals, Inc. | Processes for the chemical vapor deposition of copper and etching of copper |
| AU662451B2 (en) | 1992-10-06 | 1995-08-31 | Walkerville Pty Ltd | Wood flooring system |
| US5441766A (en) * | 1994-08-25 | 1995-08-15 | Korea Institute Of Science And Technology | Method for the production of highly pure copper thin films by chemical vapor deposition |
| US5767301A (en) | 1997-01-21 | 1998-06-16 | Sharp Microelectronics Technology, Inc. | Precursor with (alkyloxy)(alkyl)-silylolefin ligand to deposit copper |
-
1998
- 1998-08-06 KR KR1019980032069A patent/KR20000013302A/ko not_active Abandoned
-
1999
- 1999-08-06 US US09/744,619 patent/US6538147B1/en not_active Expired - Fee Related
- 1999-08-06 EP EP99935166A patent/EP1121474A2/en not_active Withdrawn
- 1999-08-06 KR KR1020017001526A patent/KR100582619B1/ko not_active Expired - Fee Related
- 1999-08-06 WO PCT/KR1999/000438 patent/WO2000008225A2/en not_active Ceased
- 1999-08-06 JP JP2000563846A patent/JP2002522453A/ja active Pending
- 1999-09-03 TW TW088115303A patent/TW499497B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6538147B1 (en) | 2003-03-25 |
| EP1121474A2 (en) | 2001-08-08 |
| WO2000008225A3 (en) | 2000-05-11 |
| TW499497B (en) | 2002-08-21 |
| KR20010072258A (ko) | 2001-07-31 |
| JP2002522453A (ja) | 2002-07-23 |
| WO2000008225A2 (en) | 2000-02-17 |
| KR100582619B1 (ko) | 2006-05-23 |
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