WO2005017950A2 - 有機イリジウム化合物、その製法、及び膜の製造方法 - Google Patents
有機イリジウム化合物、その製法、及び膜の製造方法 Download PDFInfo
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- WO2005017950A2 WO2005017950A2 PCT/JP2004/011796 JP2004011796W WO2005017950A2 WO 2005017950 A2 WO2005017950 A2 WO 2005017950A2 JP 2004011796 W JP2004011796 W JP 2004011796W WO 2005017950 A2 WO2005017950 A2 WO 2005017950A2
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- WO
- WIPO (PCT)
- Prior art keywords
- iridium
- producing
- compound
- general formula
- film
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 16
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 29
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 150000002504 iridium compounds Chemical class 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 10
- 230000008018 melting Effects 0.000 abstract description 6
- 238000002844 melting Methods 0.000 abstract description 6
- 150000002902 organometallic compounds Chemical class 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 238000009834 vaporization Methods 0.000 abstract description 3
- 230000008016 vaporization Effects 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000010408 film Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- -1 methylcyclopentadienyl Chemical group 0.000 description 14
- 238000005229 chemical vapour deposition Methods 0.000 description 12
- PBCXUKQXHYONMW-UHFFFAOYSA-N ethene iridium Chemical compound [Ir].C=C.C=C PBCXUKQXHYONMW-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000000231 atomic layer deposition Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910000457 iridium oxide Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- ADUXGJUMXBHABJ-UHFFFAOYSA-N [Ir+].[Ir+].C=C Chemical compound [Ir+].[Ir+].C=C ADUXGJUMXBHABJ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JJQVHODEIZDXSW-UHFFFAOYSA-N cycloocta-1,5-diene iridium Chemical compound [Ir].C1CC=CCCC=C1 JJQVHODEIZDXSW-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 1
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 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
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([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
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 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
- 150000002576 ketones Chemical class 0.000 description 1
- HFGPZNIAWCZYJU-UHFFFAOYSA-N lead zirconate titanate Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Zr+4].[Pb+2] HFGPZNIAWCZYJU-UHFFFAOYSA-N 0.000 description 1
- 229910052451 lead zirconate titanate Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 231100000956 nontoxicity Toxicity 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
-
- 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
-
- 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
Definitions
- the present invention relates to an organometallic compound that can be a material for producing an iridium-containing film on a substrate surface, a method for producing the compound, and a method for producing an iridium-containing film.
- step coverage Since it is easy to manufacture and has excellent step coverage (step coverage), it is expected to become the mainstream of the thin film electrode manufacturing process in the future because it can respond to the recent increase in the density of circuits and electronic components. .
- an organic metal compound having a low melting point and easy handling is considered to be suitable among metal compounds.
- an organic metal compound for depositing an iridium or iridium oxide thin film tris (dipivaloymethanato) iridium ⁇ tris (acetylacetylacetonato) iridium or (cyclopentagenenyl) (1,5-cyclooctadiene) is used.
- N) Iridium and others are being considered. These iridium compounds are highly stable in the atmosphere and have no toxicity, so they are suitable as raw materials for CVD. At temperatures, it is a solid, which makes it difficult to vaporize the raw material and transport it to the substrate.
- One method for lowering the melting point of this iridium complex is to use a compound in which at least one hydrogen atom of the cyclopentagenenyl ring has been substituted with an alkyl group in the pentagenenyl (1,5-cyclooctadiene) iridium. is there.
- (Ethylcyclopentagenenyl) iridium (for example, see JP-A-11-292888). Since this metal compound is liquid at room temperature and its melting point is lower than that of (cyclopentagenenyl) (1,5-cyclooctadiene) iridium, it has the characteristics necessary as a raw material applied to the CVD method. It is said to be. However, since this compound has extremely high stability, the decomposition temperature of the complex is high, and it is necessary to raise the substrate temperature during film formation.
- the present invention has been made in view of the above technical problems. That is, with respect to an organometallic compound that can be a raw material for forming a film containing a iridium, an organometallic compound having a low melting point, excellent vaporization characteristics, and a low deposition temperature on a substrate, a method for producing the same, and a method using the organometallic compound It is an object of the present invention to provide a method for producing a film containing a contaminant.
- Cp ring cyclopentagenenyl ring
- R 2 represents a lower alkyl group.
- It is an organic iridium compound characterized by being represented by these.
- R 2 represents a lower alkyl group.
- M represents an alkali metal.
- the present invention is a method for producing an iridium-containing film, characterized by using an organic iridium compound represented by the general formula [1] as a raw material.
- FIG. 1 is a diagram showing a GC / MS chart 1 of the iridium compound obtained in Example 1,
- FIG. 2 is a graph showing the decomposition characteristics of the iridium compound obtained in Example 1
- FIG. 3 is a graph showing the decomposition characteristics of (1,5-cyclooctadiene) (ethylcyclopentagenyl) iridium obtained in Comparative Example 1.
- FIG. 4 is a diagram showing a chart of GC-MS of (methylcyclopentadienyl) bis (ethylene) iridium obtained in Example 2,
- FIG. 5 is a schematic diagram of a CVD method apparatus used in Example 3.
- 1 is a raw material container
- 2 is an oil bath
- 3 is a reaction tank
- 4 is a substrate
- 5 is an oxidizing gas
- 6 is a counter gas
- 7 is a carrier gas
- 8 is a mass flow controller
- 9 is a mass flow.
- Controller 10 is a mass flow controller
- 11 is a vacuum pump
- 12 is exhaust.
- a lower alkyl group refers to a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms.
- the lower alkyl group used in or R 2 includes, for example, a methyl group, an ethyl group, an n-propyl group, an isopropynole group, an n-butynole group, an isoptinole group, a sec-butynole group, a tert-butyl group, Pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methynolebutynole group, 2-methylbutyl group, 1,2-dimethynolepropyl group, hexinole group, isohexyl group, 1-methynole Pentynole, 2-methynolep
- R i represents a hydrogen atom or a lower alkyl group.
- R i is preferably a methyl group or a hydrogen atom, and more preferably 1 is a hydrogen atom.
- R 2 represents a lower alkyl group, preferably a methyl group, an ethyl group, a propyl group or a butyl group, and more preferably a methyl group or an ethyl group.
- X represents a halogen atom. Examples of the halogen atom include fluorine, chlorine, bromine, and iodine atoms, and among them, a chlorine or bromine atom is preferable.
- M represents an alkali metal. Examples of the alkali metal include lithium, sodium, and potassium, and among them, lithium or sodium is preferable.
- the organic iridium compound represented by the general formula [1] of the present invention is obtained by reacting the compound represented by the general formula [2] or [3] with the compound represented by the general formula [4]. be able to.
- the reaction conditions at this time are not particularly limited. For example, both may be added to an appropriate solvent, and they may be mixed and reacted at a low temperature.
- the post-treatment is not particularly limited, but as a general method, the mixture after completion of the reaction is concentrated, and the resulting mixture is extracted with an organic solvent such as pentane, hexane, or ether, and then a suitable carrier is selected. After performing column chromatography using an appropriate organic solvent as an eluent, distillation is performed to obtain a desired organic iridium compound.
- An iridium-containing film can be produced using the organic iridium compound represented by the general formula [1] of the present invention as a raw material.
- the specific means of the manufacturing method is not particularly limited. For example, a CVD method may be used, and an atomic layer deposition method (Atomic Layer Deposition method: ALD method) may be used. Alternatively, a spin coating method or the like may be used.
- a method of supplying a raw material to the film forming chamber is not particularly limited.
- a gas publishing method may be used, or a liquid injection method may be used.
- the organic iridium compound used when a film containing iridium is produced by a CVD method or an ALD method, the organic iridium compound used may be used as it is, or may be used as a solution of the organic iridium compound dissolved in an organic solvent.
- organic solvent used when used as a solution examples include alcohols such as methanol, ethanol, and isopropanol; esters such as ethyl acetate, butyl acetate, and isoamyl acetate; ethylene glycol monoethyl ether; Glycol ethers such as renglycone monomethinoleate and ethylene glycolone monobutynoate, and ethers such as diglyme, triglyme, and tetrahydrofuran, methyl butyl ketone, and methyl isobute Tolke 1, n, ethyl butyl ketone 1, di, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, ketones such as cyclohexanone, hexane, cyclohexane, ethynolecyclohexane, heptane, octane, ve Zen, Ton
- FIG. 2 shows the results of measuring the decomposition characteristics of this compound.
- the organic iridium compound of the present invention has a decomposition onset temperature of about 220 ° C., and can be thermally decomposed at a lower temperature than the compound of Comparative Example 1 described below (conventional product). You.
- the device shown in FIG. 5 was used, and as the substrate 4, a Si substrate having a 100 nm SiO 2 curtain formed on the surface was used.
- a Si substrate having a 100 nm SiO 2 curtain formed on the surface was used.
- About 10 g of (ethylcyclopentagenenyl) bis (ethylene) iridium was placed in the raw material container 1 and heated in an oil bath to be kept at a constant temperature of 50 ° C.
- the reactor 3 was adjusted to 1 OT orr, and the inside of the raw material container 1 was adjusted to 100 Torr.
- Nitrogen was used as the carrier gas 7 and the flow rate was set to 100 sccm using a mass flow controller 10.
- Oxygen was used as oxidizing gas 5 and nitrogen was used as counter gas 6.
- the oxidizing gas flow rate was set to 10 sccm by the mass flow controller 8 and the counter gas flow rate was set to 90 sccm by the mass flow controller 9.
- the substrate 4 was set at 400 ° C., and the film was formed for 60 minutes while being heated and held.
- the formed film was a metal iridium film, and the film thickness was 300 nra.
- the organic iridium compound of the present invention can be supplied quantitatively because it is a liquid under gas bubbling conditions when the CVD method is used as a method for producing an iridium-containing film.
- it can be thermally decomposed at a lower temperature than conventional materials, it is possible to form an iridium-containing film having excellent step coverage on a substrate. According to the present invention, a film containing iridium having excellent mass productivity can be formed.
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- Engineering & Computer Science (AREA)
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Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020067002922A KR101126141B1 (ko) | 2003-08-19 | 2004-08-11 | 유기 이리듐 화합물, 그의 제법 및 막의 제조방법 |
EP04771757A EP1657245B1 (en) | 2003-08-19 | 2004-08-11 | Organoiridium compound, process for producing the same, and process for producing film |
US10/568,388 US7265233B2 (en) | 2003-08-19 | 2004-08-11 | Organometallic iridium compound, process for producing the same and process for preparing film |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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JP2003295329 | 2003-08-19 | ||
JP2003-295329 | 2003-08-19 | ||
JP2003-383169 | 2003-11-12 | ||
JP2003383169 | 2003-11-12 | ||
JP2004-005503 | 2004-01-13 | ||
JP2004005503 | 2004-01-13 |
Publications (2)
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WO2005017950A2 true WO2005017950A2 (ja) | 2005-02-24 |
WO2005017950A3 WO2005017950A3 (ja) | 2005-03-31 |
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PCT/JP2004/011796 WO2005017950A2 (ja) | 2003-08-19 | 2004-08-11 | 有機イリジウム化合物、その製法、及び膜の製造方法 |
Country Status (5)
Country | Link |
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US (1) | US7265233B2 (ja) |
EP (1) | EP1657245B1 (ja) |
KR (1) | KR101126141B1 (ja) |
TW (1) | TW200517984A (ja) |
WO (1) | WO2005017950A2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8309174B2 (en) | 2008-04-15 | 2012-11-13 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Heteroleptic iridium precursors to be used for the deposition of iridium-containing films |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20080096381A1 (en) * | 2006-10-12 | 2008-04-24 | Han Joseph H | Atomic layer deposition process for iridium barrier layers |
JP6321252B1 (ja) | 2017-03-24 | 2018-05-09 | 田中貴金属工業株式会社 | イリジウム錯体からなる化学蒸着用原料及び該化学蒸着用原料を用いた化学蒸着法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5130172A (en) | 1988-10-21 | 1992-07-14 | The Regents Of The University Of California | Low temperature organometallic deposition of metals |
Family Cites Families (5)
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US4670621A (en) * | 1986-05-05 | 1987-06-02 | Ethyl Corporation | Catalytic synthesis of olefins from paraffins |
US4751344A (en) * | 1986-05-05 | 1988-06-14 | Ethyl Corporation | Catalytic synthesis of olefins from paraffins |
US4992305A (en) * | 1988-06-22 | 1991-02-12 | Georgia Tech Research Corporation | Chemical vapor deposition of transistion metals |
US6319832B1 (en) * | 1999-02-19 | 2001-11-20 | Micron Technology, Inc. | Methods of making semiconductor devices |
JP4696454B2 (ja) * | 2003-04-24 | 2011-06-08 | 東ソー株式会社 | 新規有機イリジウム化合物、その製造方法、及び膜の製造方法 |
-
2004
- 2004-08-11 KR KR1020067002922A patent/KR101126141B1/ko active IP Right Grant
- 2004-08-11 EP EP04771757A patent/EP1657245B1/en not_active Expired - Fee Related
- 2004-08-11 US US10/568,388 patent/US7265233B2/en active Active
- 2004-08-11 WO PCT/JP2004/011796 patent/WO2005017950A2/ja active Application Filing
- 2004-08-13 TW TW093124361A patent/TW200517984A/zh unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5130172A (en) | 1988-10-21 | 1992-07-14 | The Regents Of The University Of California | Low temperature organometallic deposition of metals |
Non-Patent Citations (4)
Title |
---|
COHAN, JUDSON S. ET AL., APPLIED PHYSICS LETTERS, vol. 60, no. 11, 1992, pages 1402 - 3 |
M.DZIALLAS,A.HOHN AND H.WERNER, J.ORGANOMET.CHEM., vol. 330, 1987, pages 207 - 219 |
See also references of EP1657245A4 |
WERNER, HELMUT ET AL., CANADIAN JOURNAL OF CHEMISTRY, vol. 73, no. 7, 1995, pages 1050 - 7 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8309174B2 (en) | 2008-04-15 | 2012-11-13 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Heteroleptic iridium precursors to be used for the deposition of iridium-containing films |
US8658249B2 (en) | 2008-04-15 | 2014-02-25 | L'Air Liquide, SociétéAnonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Heteroleptic iridium precursors to be used for the deposition of iridium-containing films |
Also Published As
Publication number | Publication date |
---|---|
EP1657245A2 (en) | 2006-05-17 |
EP1657245B1 (en) | 2012-07-25 |
TWI293743B (ja) | 2008-02-21 |
TW200517984A (en) | 2005-06-01 |
KR101126141B1 (ko) | 2012-03-23 |
US20060204660A1 (en) | 2006-09-14 |
US7265233B2 (en) | 2007-09-04 |
WO2005017950A3 (ja) | 2005-03-31 |
EP1657245A4 (en) | 2009-07-08 |
KR20060060023A (ko) | 2006-06-02 |
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