JP4634800B2 - 気相化学金属堆積のためのフッ素を含まない金属錯体 - Google Patents
気相化学金属堆積のためのフッ素を含まない金属錯体 Download PDFInfo
- Publication number
- JP4634800B2 JP4634800B2 JP2004539140A JP2004539140A JP4634800B2 JP 4634800 B2 JP4634800 B2 JP 4634800B2 JP 2004539140 A JP2004539140 A JP 2004539140A JP 2004539140 A JP2004539140 A JP 2004539140A JP 4634800 B2 JP4634800 B2 JP 4634800B2
- Authority
- JP
- Japan
- Prior art keywords
- copper
- silver
- group
- precursor
- alkyl
- 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.)
- Expired - Fee Related
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 12
- 239000002184 metal Substances 0.000 title claims abstract description 12
- 239000012808 vapor phase Substances 0.000 title claims description 6
- 239000000126 substance Substances 0.000 title claims description 4
- 238000001465 metallisation Methods 0.000 title description 9
- 239000010949 copper Substances 0.000 claims abstract description 63
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052802 copper Inorganic materials 0.000 claims abstract description 36
- 229910052709 silver Inorganic materials 0.000 claims abstract description 15
- 239000004332 silver Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 29
- ZDWYFWIBTZJGOR-UHFFFAOYSA-N bis(trimethylsilyl)acetylene Chemical group C[Si](C)(C)C#C[Si](C)(C)C ZDWYFWIBTZJGOR-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002243 precursor Substances 0.000 claims description 16
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012691 Cu precursor Substances 0.000 claims description 5
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910017214 AsGa Inorganic materials 0.000 claims description 2
- 229910000577 Silicon-germanium Inorganic materials 0.000 claims description 2
- 229910004200 TaSiN Inorganic materials 0.000 claims description 2
- 229910008482 TiSiN Inorganic materials 0.000 claims description 2
- 229910008807 WSiN Inorganic materials 0.000 claims description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003378 silver Chemical group 0.000 claims description 2
- 238000005234 chemical deposition Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical class [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 125000005594 diketone group Chemical group 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- -1 tungsten nitride Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HFIWFHLNFISJEA-UHFFFAOYSA-N O.O.O.[Na+].[O-][N+]([O-])=O Chemical compound O.O.O.[Na+].[O-][N+]([O-])=O HFIWFHLNFISJEA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 0 *N([N+](*)[O-])[N+](*)[O-] Chemical compound *N([N+](*)[O-])[N+](*)[O-] 0.000 description 1
- XDBUHVQGOZJAHE-UHFFFAOYSA-N 1,2-dimethylcycloocta-1,5-diene Chemical compound CC1=C(C)CCC=CCC1 XDBUHVQGOZJAHE-UHFFFAOYSA-N 0.000 description 1
- WFLPGXDWMZEHGP-UHFFFAOYSA-N 1-methylcyclooctene Chemical compound CC1=CCCCCCC1 WFLPGXDWMZEHGP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XIJXCJCWHKUKAW-UHFFFAOYSA-N 2-isocyanoethylbenzene Chemical compound [C-]#[N+]CCC1=CC=CC=C1 XIJXCJCWHKUKAW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical group CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 description 1
- SGIUDYVHFNBYCV-UHFFFAOYSA-N 6-cycloheptylcyclohepta-1,4-diene Chemical compound C1(C=CCC=CC1)C1CCCCCC1 SGIUDYVHFNBYCV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- SDTNBEFXIYYWFQ-UHFFFAOYSA-N [Cu+2].[N+](=O)([O-])C(C(C)=O)C(C)=O.[N+](=O)([O-])C(C(C)=O)C(C)=O Chemical compound [Cu+2].[N+](=O)([O-])C(C(C)=O)C(C)=O.[N+](=O)([O-])C(C(C)=O)C(C)=O SDTNBEFXIYYWFQ-UHFFFAOYSA-N 0.000 description 1
- BULLHRADHZGONG-UHFFFAOYSA-N [cyclopenta-2,4-dien-1-ylidene(phenyl)methyl]benzene Chemical compound C1=CC=CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 BULLHRADHZGONG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001518 benzyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- NGHOLYJTSCBCGC-QXMHVHEDSA-N benzyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-QXMHVHEDSA-N 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- NGHOLYJTSCBCGC-UHFFFAOYSA-N cis-cinnamic acid benzyl ester Natural products C=1C=CC=CC=1C=CC(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-UHFFFAOYSA-N 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 150000004696 coordination complex Chemical group 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- XYZMOVWWVXBHDP-UHFFFAOYSA-N cyclohexyl isocyanide Chemical compound [C-]#[N+]C1CCCCC1 XYZMOVWWVXBHDP-UHFFFAOYSA-N 0.000 description 1
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- DGCTVLNZTFDPDJ-UHFFFAOYSA-N heptane-3,5-dione Chemical compound CCC(=O)CC(=O)CC DGCTVLNZTFDPDJ-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012705 liquid precursor Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- FSBLVBBRXSCOKU-UHFFFAOYSA-N n-butyl isocyanide Chemical compound CCCC[N+]#[C-] FSBLVBBRXSCOKU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Images
Classifications
-
- 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
-
- 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
-
- 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
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)
- Inorganic Compounds Of Heavy Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
2Cu(hfac)L → Cu(II)(hfac)2 + Cu(0) + 2L
ここで、hfacは、ヘキサフルオロアセチル−アセトナートアニオン(hexafluoroacetyl-acetonate anion)を表し、及びLは、ルイス塩基または配位子を表す。メカニズムは、他の銅(I)錯体及び銀(I)錯体のためのものと同じである。
1)フッ素豊富な膜の絶縁的な性質のために、接点の抵抗率が、全般にわたって増加し、ベーストランジスターと銅膜間の電気伝導性のブレーク;
2)バリア膜上の銅膜の不十分な付着
である。
−Mは、銅原子または銀原子を表し;
−R’及びR’’は、同じでも異なってもよく、:C1−C8アルキル;−OR’’’基(ここで、R’’’はC1−C8アルキルを表す)から選択される基を表し、
−Rは、−OR’’’’基(ここで、R’’’’はC1−C8アルキルを表す);ニトロ基:NO2;アルデヒド官能基:−CHO;−COOR’’’’’エステル官能基(ここでR’’’’’はC1−C8アルキル基を表す)から選択される基を表し;
−Lは、この錯体を安定化するための配位子を表す
Lは、銅(I)錯体の安定剤として先行技術で使用された配位子、特に、すでに上述した文献に記載された配位子、から選択され得る。
a− 一酸化炭素、
b− 少なくとも一つの非芳香族不飽和を含む不飽和炭化水素ベースの配位子、及び特に以下の中である:エチレン、アセチレン、1−オクテン、イソブチレン、1、5−シクロオクタジエン、スチルベン、ジフェニルアセチレン、スチレン、シクロオクテン、1、5、9−シクロドデカトリエン、1、3−ヘキサジエン、イソプロピルアセチレン、1−デセン、2、5−ビシクロヘプタジエン、1−オクタデセン、シクロペンテン、オクタリン、メチレン シクロヘキサン、ジフェニルフルベン、1−オクタデシン、ベンジルシンナメート(benzylcinnamate)、ベンザルアセトフェノン、アクリロニトリル、無水マレイン酸、オレイン酸、リノール酸、アクリル酸、メチルメタクリレート(methyl methacrylate)、マレイン酸ジエチル(diethyl maleate)、メチル−1、5−シクロオクタジエン、ジメチル−1、5−シクロオクタジエン、メチルシクロオクテン、シクロオクタテトラエン、ノルボレン、ノルボラジエン、トリシクロ[5.2.1.0]−デカ−2、6−ジエン、1、4−シクロヘキサジエンまたは[4,3,0]ビシクロ−ノナ−3、7−ジエン;
c− 特に、メチルイソシアニド、ブチルイソシアニド、シクロヘキシルイソシアニド、フェニルエチルイソシアニド、フェニルイソシアニドのようなイソニトリル;
d− 例えば、トリメチル−フォスフィンまたはトリエチルフォスフィンのようなフォスフィン、
e− 以下の式(II)に対応する化合物:
(R1)(R2)C=C(R3)Si(R4)(R5)(R6)
ここで、
−R1は、水素原子またはC1−C8アルキル基またはSiR4R5R6基を表し、
−R2及びR3は、同じでも異なってもよく、水素原子またはC1−C8アルキル基を表し、
−R4、R5及びR6は、同じでも異なってもよく、フェニル基またはC1−C8アルキル基を表し;
f− 以下の式(III)に対応する化合物:
R7−C≡C−Si(R8)(R9)(R10)
(III)
ここで、
−R7は、C1−C8アルキル、フェニルまたはSi(R8)(R9)(R10)基を表し、
−R8、R9及びR10は、同じでも異なってもよく、C1−C8アルキルまたはフェニル基を表し、
g− 以下の式(IV)、(V)及び(VI)のうち1つに対応する化合物:
−Mは、銅原子を表し、
−R’またはR’’は、CH3及びC2H5から選択される基を表し、
−Rは、NO2及びOCH3から選択される基を表し、
−Lは、1、5−シクロオクタジエン及びビス(トリメチルシリル)アセチレンから選択される配位子を表す。
使用される省略形:
acac: アセチルアセトンアニオン。
I−1. 3−NO 2 −acacの合成:
NO2−acacの合成は、Z. Yoshida, H. Ogoshi and T. Tokumitsu, Tetrahedron, 1970, 26, 5691の文献に記載された2段階で行う。第一段階は、銅(II)の錯体:ビス−(3−ニトロ−2,4−ペンタンジオン)−銅(II)(Cu(NO2−acac)2)を形成することからなり、第二段階は、EDTAを使用して分解することによりβ−ジケトンを単離することからなる。
I−2. 4−NO 2 −3、5−ヘプタンジオンの合成:
a− 4−Cu(NO 2 −3、5−ヘプタンジオン) 2 の合成:
手順は、Cu(NO2−acac)2を調製するための手順と同じである。
− 無水酢酸50ml中の3、5−ヘプタンジオン10g(78mmol)、
− 硝酸ナトリウム三水和物6.91g(29mmol)。
手順は、3−NO2−acacを調製するための手順と同じである:
−Cu(NO2−3、5−ヘプタンジオン)2 7.72g(17.7mmol)、
−ジクロロメタン100ml及び水100ml、
−EDTA。
I−3. 3−MeO−acacの合成:
本発明者は、R.M. Moriarty, R.K. Vaid, V.T. Ravikumar, B.K. Vaid and T.E. Hopkins, Tetrahedron, 1988, 44, 1603に記載されたこの配位子を調製するための手順に従った。
NO2−基または−OMe基を含む銅(I)錯体に関して、P. Doppelt, T.H. Baum, MRS Bulletin, 1994, XIX(8), 41にこれまでに記載されているように、対応するβ−ジケトンは、良い収率で反応を実施するために十分に酸性であるため、本発明者は、ルイス塩基存在下で銅(I)酸化物とβ−ジケトンの反応を使用する合成を選択した。いずれの場合でも、制御された雰囲気下(窒素下)で行うことが必要である。
融点=100℃。IR(cm−1):1582(γ C=O)、1511(γas NO2)、1349(γs NO2)。NMR(CDCl3、T=297K) 1H δ(ppm):2.26(s、6H、2−CH3 from NO2−acac)、0.31(s、18H、6−CH3 from BTMSA) 13C δ(ppm):189.0(s、−C=O)、139.0(s、=C−NO2)、27.6(s、−CH3 on NO2−acac)、0.0(s、−CH3 from BTMSA)。昇華は、P=5×10−2mbarでT=50℃から60℃。
(3−NO2−acac)Cu(BTMSA)の調製と同じ手順を使用する。
− Cu2O 0.83g(5.79mmol)、
− COD 0.7ml(5.64mmol)、
− 3−NO2−acac 0.8g(5.52mmol)、
− CH2Cl2 30ml。
(NO2−acac)Cu(BTMSA)の調製のために使用したのと同じ手順を使用する:
− Cu2O 0.598g(4.18mmol)、
− BTMSA 0.95ml(4.08mmol)、
− NO2−3、5−ヘプタンジオン 0.69g(3.99mmol)、
− CH2Cl2 20ml。
昇華は、P=5×10−2mbar下でT=60℃。
1H NMR (CDCl3、300MHz):3.45(s、3H、O−CH3)、2.05(s、6H、2x C−CH3)、0.2(s、18H、6x Si−CH3);IR(cm−1):1583(C=O)、1921(C≡C)。
ここで記載する銅錯体は固体であるため、これらはバブラー内で純粋な状態(pure)、あるいは、シクロヘキサンまたはテトラヒドロフランのような中性の溶媒、あるいはトルエン、キシレンまたはメシチレンのような芳香族溶媒中に好ましく溶解させることが可能である。
錯体分解反応は、次に示す不均化反応であり:
2(β−ジケトナート)CuL(I)→Cu(0)+Cu(β−ジケトナート)2(II)+2L
反応は、反応性ガスの作用を必要とせず、形成したCu(β−ジケトナート)2(II)及びL類は、揮発性があり、そしてシステムから排出する。
Claims (12)
- Mが銅原子を表すことを特徴とする、請求項1に記載の化合物。
- R’またはR’’は、CH3及びC2H5から選択される基を表すことを特徴とする請求項1又は請求項2に記載の化合物。
- Rは、NO2 及びOCH 3 から選択される基を表すことを特徴とする、請求項1〜3のいずれか一つに記載の化合物。
- 銅及び銀から選択される金属の気相化学成長のための方法であって、支持体上において、請求項1から4のいずれか一つに記載の化合物が銅前駆体または銀前駆体として使用されることを特徴とする方法。
- 前記支持体は、Si、AsGa、InP、SiC及びSiGeから選択される材料からなることを特徴とする請求項5に記載の方法。
- 前記支持体は、TiN、TiSiN、Ta、TaN、TaSiN、WN及びWSiNから選択される少なくとも一つの材料からなる一層以上の中間層を含むことを特徴とする請求項5及び6のいずれかに記載の方法。
- 120〜300℃の範囲の温度で行われることを特徴とする請求項5〜7のいずれか一つに記載の方法。
- 前記銅前駆体または銀前駆体は純粋な状態で(pure)使用されることを特徴とする請求項5〜8のいずれか一つに記載の方法。
- 前記銅前駆体または銀前駆体が炭化水素ベースの溶媒中で溶解状態で使用されることを特徴とする請求項5〜8のいずれか一つに記載の方法。
- 0.2〜500nmの範囲の厚みを持つ銅または銀の層を堆積させる請求項5〜10のいずれか一つに記載の方法。
- 集積回路を生産するための請求項5〜10のいずれか一つに記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0212059A FR2845088B1 (fr) | 2002-09-30 | 2002-09-30 | Nouveaux complexes metalliques exempts de fluor pour le depot chimique de metaux en phase gazeuse |
PCT/FR2003/002820 WO2004029061A1 (fr) | 2002-09-30 | 2003-09-25 | Complexes metalliques exempts de fluor pour le depot chimique de metaux en phase gazeuse |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2006501280A JP2006501280A (ja) | 2006-01-12 |
JP2006501280A5 JP2006501280A5 (ja) | 2010-04-30 |
JP4634800B2 true JP4634800B2 (ja) | 2011-02-16 |
Family
ID=31985326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004539140A Expired - Fee Related JP4634800B2 (ja) | 2002-09-30 | 2003-09-25 | 気相化学金属堆積のためのフッ素を含まない金属錯体 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7238820B2 (ja) |
EP (1) | EP1551851B1 (ja) |
JP (1) | JP4634800B2 (ja) |
AT (1) | ATE334990T1 (ja) |
AU (1) | AU2003276374A1 (ja) |
CA (1) | CA2500386C (ja) |
DE (1) | DE60307304T2 (ja) |
FR (1) | FR2845088B1 (ja) |
WO (1) | WO2004029061A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009039216A1 (en) * | 2007-09-17 | 2009-03-26 | L'air Liquide - Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Neutral ligand containing precursors and methods for deposition of a metal containing film |
CN103839604A (zh) * | 2014-02-26 | 2014-06-04 | 京东方科技集团股份有限公司 | 导电膜及其制备方法、阵列基板 |
JP7497022B2 (ja) | 2020-06-24 | 2024-06-10 | 国立研究開発法人産業技術総合研究所 | アルキニルシランの製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5085731A (en) * | 1991-02-04 | 1992-02-04 | Air Products And Chemicals, Inc. | Volatile liquid precursors for the chemical vapor deposition of copper |
FR2760743B1 (fr) * | 1997-03-13 | 1999-07-23 | Centre Nat Rech Scient | Nouveaux precurseurs de cuivre(i) pour depot chimique en phase gazeuse de cuivre metallique |
US6838573B1 (en) * | 2004-01-30 | 2005-01-04 | Air Products And Chemicals, Inc. | Copper CVD precursors with enhanced adhesion properties |
-
2002
- 2002-09-30 FR FR0212059A patent/FR2845088B1/fr not_active Expired - Fee Related
-
2003
- 2003-09-25 EP EP03798226A patent/EP1551851B1/fr not_active Expired - Lifetime
- 2003-09-25 JP JP2004539140A patent/JP4634800B2/ja not_active Expired - Fee Related
- 2003-09-25 AT AT03798226T patent/ATE334990T1/de active
- 2003-09-25 WO PCT/FR2003/002820 patent/WO2004029061A1/fr active IP Right Grant
- 2003-09-25 US US10/529,569 patent/US7238820B2/en not_active Expired - Fee Related
- 2003-09-25 DE DE60307304T patent/DE60307304T2/de not_active Expired - Lifetime
- 2003-09-25 AU AU2003276374A patent/AU2003276374A1/en not_active Abandoned
- 2003-09-25 CA CA2500386A patent/CA2500386C/fr not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
FR2845088B1 (fr) | 2004-12-03 |
WO2004029061A1 (fr) | 2004-04-08 |
CA2500386A1 (fr) | 2004-04-08 |
ATE334990T1 (de) | 2006-08-15 |
AU2003276374A1 (en) | 2004-04-19 |
EP1551851B1 (fr) | 2006-08-02 |
JP2006501280A (ja) | 2006-01-12 |
EP1551851A1 (fr) | 2005-07-13 |
DE60307304D1 (de) | 2006-09-14 |
FR2845088A1 (fr) | 2004-04-02 |
US20060121709A1 (en) | 2006-06-08 |
CA2500386C (fr) | 2012-03-13 |
US7238820B2 (en) | 2007-07-03 |
DE60307304T2 (de) | 2007-10-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4414397B2 (ja) | 揮発性金属β−ケトイミナート錯体 | |
JP3593051B2 (ja) | 金属及び金属含有フィルムの堆積のための揮発性先駆物質 | |
US7087774B2 (en) | Volatile copper(II) complexes and reducing agents for deposition of copper films by atomic layer deposition | |
JP2010180221A (ja) | 揮発性金属β−ケトイミナート及び金属β−ジイミナート錯体 | |
JP2009510074A (ja) | 有機金属化合物及びその使用方法 | |
US20130168614A1 (en) | Nickel allyl amidinate precursors for deposition of nickel-containing films | |
JP2004506594A (ja) | 銅ソース試薬組成物並びにこれをマイクロエレクトロニクス装置構造のために製造及び使用する方法 | |
US6589329B1 (en) | Composition and process for production of copper circuitry in microelectronic device structures | |
JP2008508427A (ja) | 原子層蒸着による銅フィルムの蒸着のための銅(ii)錯体 | |
JP4634800B2 (ja) | 気相化学金属堆積のためのフッ素を含まない金属錯体 | |
EP0966474B1 (fr) | Nouveaux precurseurs de cuivre(i) pour depot chimique en phase gazeuse de cuivre metallique | |
KR100298125B1 (ko) | 구리의 화학 증착에 유용한 유기 구리 전구체 | |
KR100296959B1 (ko) | 구리의 화학 증착에 유용한 유기 구리 전구체 | |
JP4125728B2 (ja) | 一価銅錯体 | |
KR102123331B1 (ko) | 코발트 전구체, 이의 제조방법 및 이를 이용한 박막의 제조방법 | |
US6281377B1 (en) | Substituted cycloalkene new copper precursors for chemical vapor deposition of copper metal thin films | |
JP3282392B2 (ja) | 蒸気圧の高い有機金属化学蒸着による銅薄膜形成用有機銅化合物 | |
JP2000143670A (ja) | アリルリガンド前駆体および合成方法 | |
KR100600468B1 (ko) | 시클로알켄 구리 전구체의 제조방법 | |
JPH0853470A (ja) | 蒸気圧の高い有機金属化学蒸着による銀薄膜形成用有機銀化合物 | |
EP1792907A1 (en) | Volatile metal beta-ketoiminate complexes | |
KR20160062675A (ko) | 신규 니켈-비스베타케토이미네이트 전구체 및 이를 이용한 니켈 함유 필름 증착방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060904 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20091118 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091202 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100302 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20100302 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100324 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100722 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20100723 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100928 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20101004 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20101026 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20101119 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131126 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |