JP5202952B2 - 有機金属化合物及びその製造のための方法 - Google Patents
有機金属化合物及びその製造のための方法 Download PDFInfo
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- JP5202952B2 JP5202952B2 JP2007536831A JP2007536831A JP5202952B2 JP 5202952 B2 JP5202952 B2 JP 5202952B2 JP 2007536831 A JP2007536831 A JP 2007536831A JP 2007536831 A JP2007536831 A JP 2007536831A JP 5202952 B2 JP5202952 B2 JP 5202952B2
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- Prior art keywords
- substituted
- carbon atoms
- ruthenium
- unsubstituted
- organometallic compound
- Prior art date
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- 239000002184 metal Substances 0.000 claims description 40
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000000151 deposition Methods 0.000 claims description 24
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 22
- 229910052707 ruthenium Inorganic materials 0.000 claims description 22
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 239000011733 molybdenum Substances 0.000 description 3
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
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- MHHJTGCFFQKJNC-UHFFFAOYSA-N CC(C)=CC(C)=C[Ru]C=1C=C(C)NC=1C Chemical compound CC(C)=CC(C)=C[Ru]C=1C=C(C)NC=1C MHHJTGCFFQKJNC-UHFFFAOYSA-N 0.000 description 1
- MCJRYSMOZBXXCY-UHFFFAOYSA-N CC1(C(N(C=C1)C)(C)[Ru])C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC1(C(N(C=C1)C)(C)[Ru])C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 MCJRYSMOZBXXCY-UHFFFAOYSA-N 0.000 description 1
- NDAORFLIOZGLQJ-UHFFFAOYSA-N CC1(C=C(C=C1)C)C1=C(NC=C1)[Ru](C)(C)(C)C Chemical compound CC1(C=C(C=C1)C)C1=C(NC=C1)[Ru](C)(C)(C)C NDAORFLIOZGLQJ-UHFFFAOYSA-N 0.000 description 1
- NNWIDWFUTZDYEY-UHFFFAOYSA-N CC=1C(=C(NC=1)[Ru](C)(C)(C)C)C1C=CC=C1 Chemical compound CC=1C(=C(NC=1)[Ru](C)(C)(C)C)C1C=CC=C1 NNWIDWFUTZDYEY-UHFFFAOYSA-N 0.000 description 1
- JZSALWMURWAJIQ-UHFFFAOYSA-N CC=1NC(=CC1[Ru])C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC=1NC(=CC1[Ru])C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 JZSALWMURWAJIQ-UHFFFAOYSA-N 0.000 description 1
- KCZSMMNVCJWTMK-UHFFFAOYSA-N CC=1NC(=CC=1C1=C(NC=C1)[Ru](C)(C)(C)C)C Chemical compound CC=1NC(=CC=1C1=C(NC=C1)[Ru](C)(C)(C)C)C KCZSMMNVCJWTMK-UHFFFAOYSA-N 0.000 description 1
- PKAXZQSISGMBBF-UHFFFAOYSA-N C[Ru](C)(C)(C)(c1ccc[nH]1)c1ccc[nH]1 Chemical compound C[Ru](C)(C)(C)(c1ccc[nH]1)c1ccc[nH]1 PKAXZQSISGMBBF-UHFFFAOYSA-N 0.000 description 1
- WOCXUGWFKVZNEH-UHFFFAOYSA-N C[Ru](C1=C(NC(=C1)C)C)C1C=CC=C1 Chemical compound C[Ru](C1=C(NC(=C1)C)C)C1C=CC=C1 WOCXUGWFKVZNEH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910019001 CoSi Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- SWTDBANWBQMCSC-UHFFFAOYSA-N N1C(=CC=C1)[Ru].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N1C(=CC=C1)[Ru].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 SWTDBANWBQMCSC-UHFFFAOYSA-N 0.000 description 1
- MVQWGMLACGPZDN-UHFFFAOYSA-N N1C(C)=CC([Ru]C=2CCCC=CC=2)=C1C Chemical compound N1C(C)=CC([Ru]C=2CCCC=CC=2)=C1C MVQWGMLACGPZDN-UHFFFAOYSA-N 0.000 description 1
- 229910005881 NiSi 2 Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910008484 TiSi Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- KLBIWNAWZPXRGM-UHFFFAOYSA-N [Ru]c1ccc[nH]1 Chemical compound [Ru]c1ccc[nH]1 KLBIWNAWZPXRGM-UHFFFAOYSA-N 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- DBKDYYFPDRPMPE-UHFFFAOYSA-N lithium;cyclopenta-1,3-diene Chemical compound [Li+].C=1C=C[CH-]C=1 DBKDYYFPDRPMPE-UHFFFAOYSA-N 0.000 description 1
- VCZAHNHXOPQWPZ-UHFFFAOYSA-N lithium;penta-1,3-diene Chemical compound [Li+].CC=CC=[CH-] VCZAHNHXOPQWPZ-UHFFFAOYSA-N 0.000 description 1
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 1
- PPRDIRBYCPOHPV-UHFFFAOYSA-M magnesium;cyclopenta-1,3-diene;bromide Chemical compound [Mg+2].[Br-].C=1C=C[CH-]C=1 PPRDIRBYCPOHPV-UHFFFAOYSA-M 0.000 description 1
- BCDGPAQPJYOHGM-UHFFFAOYSA-M magnesium;pyrrol-1-ide;bromide Chemical compound Br[Mg+].C=1C=C[N-]C=1 BCDGPAQPJYOHGM-UHFFFAOYSA-M 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- NNSSHRACPMBEBC-UHFFFAOYSA-N sodium penta-1,3-diene Chemical compound [Na+].CC=CC=[CH-] NNSSHRACPMBEBC-UHFFFAOYSA-N 0.000 description 1
- JQUZTGJSSQCTPV-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C1C=CC=[C-]1 JQUZTGJSSQCTPV-UHFFFAOYSA-N 0.000 description 1
- MFTDDEGCJOYPMG-UHFFFAOYSA-N sodium;pyrrol-1-ide Chemical compound [Na+].C=1C=C[N-]C=1 MFTDDEGCJOYPMG-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- C07F17/00—Metallocenes
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)
Description
本発明は、一つには、次の式:
から選択される有機金属化合物に関する。
上で示したように、本発明は、一つには、式LML’(式中、Mは金属又はメタロイドであり、Lは、置換又は無置換シクロペンタジエニル基、置換又は無置換シクロペンタジエニル類似基、置換又は無置換ペンタジエニル基、置換又は無置換ペンタジエニル類似基、置換又は無置換ピロリル基、又は置換又は無置換ピロリル類似基であり、L’は、置換又は無置換ピロリル基、又は置換又は無置換ピロリル類似基である)により表される有機金属化合物に関する。
から選択される有機金属ルテニウム化合物に関する。
クロロビス(トリフェニルホスフィン)(エチルシクロペンタジエニル)ルテニウム、
ブロモビス(トリフェニルホスフィン)(エチルシクロペンタジエニル)ルテニウム、
クロロビス(トリイソプロピルホスファイト)(エチルシクロペンタジエニル)ルテニウム、
クロロビス(トリエチルホスフィン)(エチルシクロペンタジエニル)ルテニウム、
クロロビス(トリフェニルホスフィン)(シクロペンタジエニル)ルテニウム、
クロロビス(トリフェニルホスフィン)(メチルシクロペンタジエニル)ルテニウム、
クロロビス(トリフェニルホスフィン)(2,4−ジメチルペンタジエニル)ルテニウム、
クロロビス(トリフェニルホスフィン)(ピロリル)ルテニウム、
クロロビス(トリフェニルホスフィン)(2,5−ジメチルピロリル)ルテニウム、
クロロビス(トリフェニルホスフィン)(テトラメチルピロリル)ルテニウム等が含まれる。
乾燥500mlの三口丸底フラスコに、(頂部に流量アダプターを有する)凝縮器を取り付け、撹拌棒を入れた。撹拌板上方の加熱マントル〔バリアック(variac)に取付けられている〕上に乗せたガスフード中にそのフラスコを留めた。そのフラスコにクロロビス(トリフェニルホスフィン)−(エチルシクロペンタジエニル)ルテニウム(14.8g、0.020モル)を添加し、その系を15分間窒素でパージした。パージ後、フラスコにガラスストッパー及び隔膜で蓋をし、油バブラーへ通じた凝縮器の頂部にあるアダプターを通してゆっくりした窒素の流れを確立した。カニュールを通して無水トルエン(150ml)を添加し、撹拌を開始した。リチウムピロリド(1.6g、0.022モル)のTHF(50ml)溶液をカニュールを通してトルエン懸濁物へ移した。褐色の溶液を穏やかに還流するまで加熱し、16時間撹拌した。室温へ冷却した後、減圧下で溶媒を除去した。得られた残留物をヘキサン(4×100ml)中で撹拌し、中程度の多孔率のフリットを通して濾過した。そのヘキサンを黄色の濾液から減圧下で除去し、得られた暗黄色の液体を、短路蒸留ヘッドを通して真空蒸留した(約0.3トール)。約100℃で生成物収集を行なった。収集された黄色液体をNMR及びGC−MSにより特徴付けた。MS(M+、相対的強度):260(100)、246(40)、193(33)、167(9)。1H NMR(300MHz、トルエン−d8、δ):5.64(t、α−ピロリル、J=1Hz)、4.62(t、β−ピロリル、J=1Hz)、4.38(t、Cp、J=2Hz)、4.30(t、Cp、J=2Hz)、2.04(q、CH2、J=8)、1.02(t、CH3、J=8)。生成物は、下の構造により表されるエチルシクロペンタジエニルピロリルルテニウムである。
リチウム2,5−ジメチルピロリドを、ヘキサン中n−ブチルリチウム及び2,5−ジメチルピロールを用いて標準リチオ化法を用いて別々に合成した。乾燥窒素雰囲気グラブボックス内で、大気遮断テフロン(登録商標)バルブを具えた乾燥1リットル一口丸底フラスコに撹拌棒を入れた。そのフラスコにリチウム2,5−ジメチルピロリド(6.0g、0.059モル)、無水THF(75ml)、及び無水ヘキサン(300ml)を添加した。トリス(トリフェニルホスフィン)−ジクロロルテニウム(14.3g、0.015モル)を添加した。フラスコに蓋をし、グラブボックスから取り出し、窒素パージ下に凝縮器を取付け、ガスフード中で窒素中で(撹拌しながら)還流した(14時間)。室温へ冷却した後、溶媒を減圧下で除去し、残留物をグラブボックスへ戻した。粗製物質をヘキサンと共に撹拌し、次に中程度の多孔率のフリットを通して濾過した。濾液を約10mlへ減少させ、次にシリカゲルカラムにかけた。無水ジエチルエーテルで溶離することにより残留トリフェニルホスフィンを除去した。無水THFによる溶離で、ブライトイエローの帯域を生じ、それを収集し、THFを除去し、ライトイエロー/ベージュ色の固体を得た。ビス(2,5−ジメチルピロリル)ルテニウムの純粋な化合物は、乾燥窒素雰囲気中で熱的に安定であった。GC/MS(M+、相対強度):289(100)、193(26)。1H NMR(300MHz、C6D6、δ):4.45(s、β−ピロリル、2H)、2.11(s、CH3、6H)。DSC:mp=73℃。
Claims (6)
- シクロペンタジエニルピロリルルテニウム、
メチルシクロペンタジエニルピロリルルテニウム、
エチルシクロペンタジエニルピロリルルテニウム、
イソプロピルシクロペンタジエニルピロリルルテニウム、
t−ブチルシクロペンタジエニルピロリルルテニウム、
1,2−ジメチルシクロペンタジエニルピロリルルテニウム、及び
1,3−ジメチルシクロペンタジエニルピロリルルテニウム
から選択される、請求項1に記載の有機金属化合物。 - 次の式:
(i)置換若しくは無置換シクロペンタジエニルハロゲン化物ルテニウム化合物、又は置換若しくは無置換ピロリルハロゲン化物ルテニウム化合物から選択されるルテニウム源化合物と、塩基材料とを、溶媒の存在下、必要な条件下で反応させ、前記有機金属化合物を含む反応混合物を生成させること、及び(ii)前記有機金属化合物を前記反応混合物から分離すること、を含む有機金属化合物の製造のための方法。 - 請求項1に記載の有機金属化合物を分解し、それにより膜、被覆、又は粉末を生成させる、膜、被覆、又は粉末の製造のための方法であって、前記有機金属化合物の分解が、熱的活性化、化学的活性化、光化学的活性化、又はプラズマ活性化による、膜、被覆、又は粉末の製造のための方法。
- 有機金属化合物を気化し、その蒸気を、基体を収容する堆積反応器中に送り、前記基体が、金属、金属珪化物、半導体、絶縁体、及び障壁材料からなる群より選択される材料を含む、請求項4に記載の方法。
- (i)請求項1に記載の第一有機金属化合物、及び(ii)一種以上の異なる有機金属化合物を含む混合物。
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US11/216,043 US7619093B2 (en) | 2004-10-15 | 2005-09-01 | Organometallic compounds and mixtures thereof |
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US20070054487A1 (en) * | 2005-09-06 | 2007-03-08 | Applied Materials, Inc. | Atomic layer deposition processes for ruthenium materials |
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US20090205968A1 (en) * | 2008-01-24 | 2009-08-20 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
US20090202740A1 (en) * | 2008-01-24 | 2009-08-13 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
DE102008026284A1 (de) * | 2008-06-02 | 2009-12-03 | Umicore Ag & Co. Kg | Verfahren zur Herstellung von Ruthenium-Dienyl-Komplexen |
US20130337192A1 (en) * | 2010-11-03 | 2013-12-19 | L'Air Liquide Société Anonyme pour I'Etude et I'Exploitation des Procédés Georges Claude | Bis-pyrroles-2-aldiminate manganese precursors for deposition of manganese containing films |
US8859045B2 (en) * | 2012-07-23 | 2014-10-14 | Applied Materials, Inc. | Method for producing nickel-containing films |
JP6178638B2 (ja) * | 2013-06-26 | 2017-08-09 | 東ソー株式会社 | ルテニウム錯体及びその製造方法、ルテニウム含有薄膜及びその作製方法 |
TWI610932B (zh) | 2012-12-07 | 2018-01-11 | 東曹股份有限公司 | 釕錯合物及其製造方法、陽離子性三腈錯合物及其製造方法、以及含釕薄膜的製造方法 |
US9994954B2 (en) | 2013-07-26 | 2018-06-12 | Versum Materials Us, Llc | Volatile dihydropyrazinly and dihydropyrazine metal complexes |
JP2015081246A (ja) * | 2013-10-24 | 2015-04-27 | 東ソー株式会社 | ルテニウム錯体及びその製造方法、ルテニウム含有薄膜及びその作製方法 |
KR101659610B1 (ko) * | 2014-03-18 | 2016-09-23 | 주식회사 유진테크 머티리얼즈 | 유기 게르마늄 아민 화합물 및 이를 이용한 박막 증착 방법 |
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KR101332070B1 (ko) | 2013-11-28 |
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CN101080415B (zh) | 2012-01-18 |
US20110206845A1 (en) | 2011-08-25 |
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