KR100600468B1 - 시클로알켄 구리 전구체의 제조방법 - Google Patents
시클로알켄 구리 전구체의 제조방법 Download PDFInfo
- Publication number
- KR100600468B1 KR100600468B1 KR1020037013540A KR20037013540A KR100600468B1 KR 100600468 B1 KR100600468 B1 KR 100600468B1 KR 1020037013540 A KR1020037013540 A KR 1020037013540A KR 20037013540 A KR20037013540 A KR 20037013540A KR 100600468 B1 KR100600468 B1 KR 100600468B1
- Authority
- KR
- South Korea
- Prior art keywords
- copper
- cyclohexene
- methyl
- hfac
- addition
- Prior art date
Links
- 239000012691 Cu precursor Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 14
- 150000001925 cycloalkenes Chemical class 0.000 title 1
- 239000010949 copper Substances 0.000 claims abstract description 68
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229910052802 copper Inorganic materials 0.000 claims abstract description 39
- 238000005229 chemical vapour deposition Methods 0.000 claims abstract description 28
- 239000010409 thin film Substances 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 claims description 32
- 239000002184 metal Substances 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 10
- 230000006641 stabilisation Effects 0.000 claims description 6
- 238000011105 stabilization Methods 0.000 claims description 6
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 239000010408 film Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 8
- 150000004767 nitrides Chemical class 0.000 description 7
- FKCSKMKOJJBGNI-UHFFFAOYSA-N copper(1+) 1-methylcyclohexene Chemical compound [Cu+].CC1=CCCCC1 FKCSKMKOJJBGNI-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- -1 organometallic copper complexes Chemical class 0.000 description 3
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000012705 liquid precursor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical group [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XSBHQBGCXIMBNO-UHFFFAOYSA-N [Cu+].CC#CC Chemical compound [Cu+].CC#CC XSBHQBGCXIMBNO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- AGIFICBLANTEOD-UHFFFAOYSA-N copper(1+) 1,5-dimethylcycloocta-1,5-diene Chemical compound [Cu+].CC1=CCCC(C)=CCC1 AGIFICBLANTEOD-UHFFFAOYSA-N 0.000 description 1
- PFGMJBLQMLKUKN-UHFFFAOYSA-N copper(1+) 1,6-dimethylcycloocta-1,5-diene Chemical compound [Cu+].CC1=CCCC=C(C)CC1 PFGMJBLQMLKUKN-UHFFFAOYSA-N 0.000 description 1
- MUYKGFREZGMJSE-UHFFFAOYSA-N copper(1+);hex-1-yne Chemical compound [Cu+].CCCCC#C MUYKGFREZGMJSE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910001338 liquidmetal Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052709 silver Chemical class 0.000 description 1
- 239000004332 silver Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Images
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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/77—Preparation of chelates of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/92—Ketonic chelates
-
- 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)
- Chemical Vapour Deposition (AREA)
- Electrodes Of Semiconductors (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/JP2001/003257 WO2002086189A1 (fr) | 2001-04-16 | 2001-04-16 | Nouveaux precurseurs du cuivre a substitution cycloalcene pour depot chimique en phase vapeur de couches minces de cuivre |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030092077A KR20030092077A (ko) | 2003-12-03 |
| KR100600468B1 true KR100600468B1 (ko) | 2006-07-13 |
Family
ID=11737252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037013540A KR100600468B1 (ko) | 2001-04-16 | 2001-04-16 | 시클로알켄 구리 전구체의 제조방법 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1387898A4 (fr) |
| JP (1) | JP3998138B2 (fr) |
| KR (1) | KR100600468B1 (fr) |
| WO (1) | WO2002086189A1 (fr) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4385005A (en) * | 1981-07-13 | 1983-05-24 | Exxon Research And Engineering Co. | Process for separating unsaturated hydrocarbons using copper or silver complexes with fluorinated diketonates |
| US4425281A (en) * | 1981-07-13 | 1984-01-10 | Exxon Research And Engineering Co. | Copper or silver complexes with fluorinated diketones and unsaturated ligands |
| 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 |
| JP3840650B2 (ja) * | 1998-01-21 | 2006-11-01 | 株式会社トリケミカル研究所 | 配線用銅合金膜形成材料および配線用銅合金膜形成方法 |
| US6090963A (en) * | 1998-11-10 | 2000-07-18 | Sharp Laboratories Of America, Inc. | Alkene ligand precursor and synthesis method |
| JP2001140075A (ja) * | 1999-11-18 | 2001-05-22 | Ube Ind Ltd | 銅薄膜形成用有機銅錯体 |
-
2001
- 2001-04-16 WO PCT/JP2001/003257 patent/WO2002086189A1/fr active Application Filing
- 2001-04-16 KR KR1020037013540A patent/KR100600468B1/ko not_active IP Right Cessation
- 2001-04-16 JP JP2002583699A patent/JP3998138B2/ja not_active Expired - Fee Related
- 2001-04-16 EP EP01919965A patent/EP1387898A4/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP3998138B2 (ja) | 2007-10-24 |
| EP1387898A4 (fr) | 2008-08-13 |
| JP2004526867A (ja) | 2004-09-02 |
| WO2002086189A1 (fr) | 2002-10-31 |
| KR20030092077A (ko) | 2003-12-03 |
| EP1387898A1 (fr) | 2004-02-11 |
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| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
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| LAPS | Lapse due to unpaid annual fee |