JP2005225855A - Organic iridium compound, method for producing the compound and method for producing film - Google Patents
Organic iridium compound, method for producing the compound and method for producing film Download PDFInfo
- Publication number
- JP2005225855A JP2005225855A JP2004191388A JP2004191388A JP2005225855A JP 2005225855 A JP2005225855 A JP 2005225855A JP 2004191388 A JP2004191388 A JP 2004191388A JP 2004191388 A JP2004191388 A JP 2004191388A JP 2005225855 A JP2005225855 A JP 2005225855A
- Authority
- JP
- Japan
- Prior art keywords
- iridium
- compound
- group
- producing
- general formula
- 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.)
- Granted
Links
- 150000002504 iridium compounds Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 title claims abstract description 15
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 27
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- -1 ethylcyclopentadienyl Chemical group 0.000 abstract description 23
- 239000000758 substrate Substances 0.000 abstract description 10
- 230000008018 melting Effects 0.000 abstract description 7
- 238000002844 melting Methods 0.000 abstract description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000005977 Ethylene Substances 0.000 abstract description 4
- 150000002736 metal compounds Chemical class 0.000 abstract description 4
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 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
- 238000000034 method 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 10
- 238000005229 chemical vapour deposition Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000002902 organometallic compounds Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000000231 atomic layer deposition Methods 0.000 description 4
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 description 4
- 229910000457 iridium oxide Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 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
- 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
- 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
- ADUXGJUMXBHABJ-UHFFFAOYSA-N [Ir+].[Ir+].C=C Chemical compound [Ir+].[Ir+].C=C ADUXGJUMXBHABJ-UHFFFAOYSA-N 0.000 description 2
- SFGLQAJOHPDTPZ-UHFFFAOYSA-N [Ir].C(C)C1(C=CC=C1)C1=CCCC=CCC1 Chemical compound [Ir].C(C)C1(C=CC=C1)C1=CCCC=CCC1 SFGLQAJOHPDTPZ-UHFFFAOYSA-N 0.000 description 2
- SXGLKKKNPBOLIA-UHFFFAOYSA-N [Ir].C1(C=CC=C1)C1=CCCC=CCC1 Chemical compound [Ir].C1(C=CC=C1)C1=CCCC=CCC1 SXGLKKKNPBOLIA-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
- 230000005587 bubbling Effects 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
- UXDJAZOVQLXLJJ-UHFFFAOYSA-N cycloocta-1,5-diene;ethylcyclopentane;iridium Chemical group [Ir].CC[C]1[CH][CH][CH][CH]1.C1CC=CCCC=C1 UXDJAZOVQLXLJJ-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 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
- 229910052451 lead zirconate titanate Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 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
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- AZFHXIBNMPIGOD-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;iridium Chemical compound [Ir].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O AZFHXIBNMPIGOD-LNTINUHCSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- CUFDGKBZHJSRDZ-UHFFFAOYSA-N 1-cyclopenta-2,4-dien-1-ylcycloocta-1,5-diene Chemical compound C1(C=CC=C1)C1=CCCC=CCC1 CUFDGKBZHJSRDZ-UHFFFAOYSA-N 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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- ZAKSCXKVYUNNHM-UHFFFAOYSA-N 5-methylcyclopenta-1,3-diene Chemical compound C[C-]1C=CC=C1 ZAKSCXKVYUNNHM-UHFFFAOYSA-N 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- 239000007983 Tris buffer Substances 0.000 description 1
- VNSWULZVUKFJHK-UHFFFAOYSA-N [Sr].[Bi] Chemical compound [Sr].[Bi] VNSWULZVUKFJHK-UHFFFAOYSA-N 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
- 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
- 239000012159 carrier gas 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
- 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
- 238000000151 deposition 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
- 239000007772 electrode material Substances 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
- 238000007429 general method 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
- 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
- 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940117955 isoamyl acetate Drugs 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
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 239000003446 ligand Substances 0.000 description 1
- ZBDWUWNQBVXRMA-UHFFFAOYSA-N lithium;5-ethylcyclopenta-1,3-diene Chemical compound [Li+].CC[C-]1C=CC=C1 ZBDWUWNQBVXRMA-UHFFFAOYSA-N 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
- 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
- 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
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 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
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Landscapes
- Chemical Vapour Deposition (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は、基板表面にイリジウム含有膜を製造するための材料となりうる有機金属化合物およびその製造方法、またイリジウム含有膜の製造方法に関する。 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 same, and a method for producing an iridium-containing film.
近年の集積回路においては、強誘電体の残留分極を用いた強誘電体メモリが盛んに検討されている。具体的にはチタン酸ジルコン酸鉛(PZT:Pb(Ti,Zr)O3)、あるいはタンタル酸ビスマスストロンチウム(SBT:SrBi2Ta2O9)等が検討されており、これら強誘電体の電極材料としてルテニウム、白金、イリジウム等の貴金属薄膜、またはこれらの貴金属の酸化物薄膜が必要となる。特にイリジウムおよびイリジウム酸化物は今後の電極材料の中心になると注目されている。イリジウムおよびイリジウム酸化物薄膜の製造方法としては、スパッタリング法、化学気相蒸着法(Chemical Vapor Deposition法:CVD法)が用いられている。特に、CVD法は均一な皮膜を製造しやすい上にステップカバレッジ性(段差被覆能)に優れることから、近年の回路、電子部材に対するより一層の高密度化に対応できる為に今後の薄膜電極製造プロセスの主流になるものと考えられる。 In recent integrated circuits, ferroelectric memories using the remanent polarization of ferroelectrics have been actively studied. Specifically, lead zirconate titanate (PZT: Pb (Ti, Zr) O 3 ), bismuth strontium tantalate (SBT: SrBi 2 Ta 2 O 9 ), etc. have been studied, and these ferroelectric electrodes As a material, a noble metal thin film such as ruthenium, platinum, iridium, or an oxide thin film of these noble metals is required. In particular, iridium and iridium oxide are attracting attention as the center of future electrode materials. As a method for producing iridium and an iridium oxide thin film, a sputtering method or a chemical vapor deposition method (CVD method) is used. In particular, the CVD method makes it easy to produce a uniform film and is excellent in step coverage (step coverage). Therefore, in order to cope with higher density in recent circuits and electronic components, future thin film electrode production It is considered to become the mainstream of the process.
このCVD法を用いて薄膜を形成させるための原料物質としては、金属化合物の中でも融点が低く取り扱い性が容易である有機金属化合物が適していると考えられる。従来、イリジウムまたはイリジウム酸化物薄膜を析出させる為の有機金属化合物としてはトリス(ジピバロイルメタナト)イリジウムやトリス(アセチルアセトナト)イリジウムや(シクロペンタジエニル)(1,5−シクロオクタジエン)イリジウムなどが検討されている。これらのイリジウム化合物は大気中の安定性が高く、毒性も無いことからCVD原料としての適性を有するものの、常温では固体であり、原料の気化および基板への輸送が困難になるという問題点がある。 As a raw material for forming a thin film using this CVD method, among metal compounds, an organometallic compound having a low melting point and easy handling is considered suitable. Conventionally, as an organometallic compound for depositing iridium or an iridium oxide thin film, tris (dipivaloylmethanato) iridium, tris (acetylacetonato) iridium, or (cyclopentadienyl) (1,5-cyclooctadiene) ) Iridium is being studied. Although these iridium compounds have high stability in the air and are not toxic, they are suitable as CVD raw materials, but they are solid at room temperature, which makes it difficult to vaporize the raw materials and transport them to the substrate. .
そこで最近では融点の低いイリジウム錯体についての研究が活発に行われている。このイリジウム錯体の低融点化の手法としては、シクロペンタジエニル(1,5−シクロオクタジエン)イリジウムにおいてシクロペンタジエニル環の少なくとも一つの水素原子をアルキル基で置換した化合物とするものがある。 Therefore, recently, research on iridium complexes having a low melting point has been actively conducted. As a technique for lowering the melting point of this iridium complex, there is a method in which at least one hydrogen atom of a cyclopentadienyl ring is substituted with an alkyl group in cyclopentadienyl (1,5-cyclooctadiene) iridium. .
例えば、シクロペンタジエニル誘導体として、(1,5−シクロオクタジエン)(エチルシクロペンタジエニル)イリジウムがある(例えば特許文献1参照)。この金属化合物は常温で液体であり、その融点も(シクロペンタジエニル)(1,5−シクロオクタジエン)イリジウムに比して低いことから、CVD法に適用する原料物質として必要な特性を具備するものであるとされている。しかしこの化合物は安定性が極めて高いことから錯体の分解温度が高く、必然的に成膜時の基板温度を高くする必要があり、結果として成膜時の段差被覆性(ステップカバレッジ性)に劣るという問題点を抱えていた。またイリジウム酸化膜が生成しにくいというという問題点も抱えていた。また、エチレンとシクロペンタジエニル基を配位子として有するイリジウム錯体の報告例としては、(シクロペンタジエニル)ビス(エチレン)イリジウムの合成例がある(例えば非特許文献1参照)が、室温で固体の化合物でありCVD材料としては不適なものである。 For example, as a cyclopentadienyl derivative, there is (1,5-cyclooctadiene) (ethylcyclopentadienyl) iridium (see, for example, Patent Document 1). This metal compound is liquid at room temperature, and its melting point is lower than that of (cyclopentadienyl) (1,5-cyclooctadiene) iridium, so that it has characteristics necessary as a raw material applied to the CVD method. It is supposed to be. However, since this compound has extremely high stability, the decomposition temperature of the complex is high, and it is inevitably necessary to increase the substrate temperature during film formation, resulting in poor step coverage (step coverage) during film formation. It had the problem that. Another problem is that it is difficult to form an iridium oxide film. In addition, as a report example of an iridium complex having ethylene and a cyclopentadienyl group as a ligand, there is a synthesis example of (cyclopentadienyl) bis (ethylene) iridium (for example, see Non-Patent Document 1). It is a solid compound and is not suitable as a CVD material.
本発明は上記技術上の問題点に鑑みてなされたものである。即ちイリジウム含有膜を形成させる原料となりうる有機金属化合物に関し、融点が低く、気化特性に優れ、かつ基板上での成膜温度が低い有機金属化合物、その製造方法、およびその有機金属化合物を用いたイリジウム含有膜の製造方法を提供することを目的とする。 The present invention has been made in view of the above technical problems. That is, regarding an organometallic compound that can be a raw material for forming an iridium-containing film, an organometallic compound having a low melting point, excellent vaporization characteristics, and a low film formation temperature on a substrate, its production method, and its organometallic compound were used. It aims at providing the manufacturing method of an iridium containing film | membrane.
本発明者らは、先の課題を解決すべく検討を重ねた結果、(シクロペンタジエニル)ビス(エチレン)イリジウムのシクロペンタジエニル環(以後Cp環とする)またはエチレンに低級アルキル基を導入することにより、室温で液体の融点を示し、良好な気化特性、分解特性を有する新規なイリジウム錯体を開発するに至った。 As a result of repeated studies to solve the above-mentioned problems, the present inventors have determined that a cyclopentadienyl ring (hereinafter referred to as Cp ring) of (cyclopentadienyl) bis (ethylene) iridium or ethylene has a lower alkyl group. As a result, a new iridium complex having a liquid melting point at room temperature and having good vaporization and decomposition properties has been developed.
すなわち本発明は、
一般式[1]
That is, the present invention
General formula [1]
また本発明は、一般式[2] The present invention also provides a general formula [2].
さらに本発明は、一般式[1]で表される有機イリジウム化合物を原料とすることを特徴とする、イリジウム含有膜の製造方法である。以下、本発明を更に詳細に説明する。 Furthermore, 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. Hereinafter, the present invention will be described in more detail.
最初に本明細書で用いられる用語の定義ならびにその具体例について説明する。 First, definitions of terms used in the present specification and specific examples thereof will be described.
本明細書において、低級アルキル基とは、炭素数1個以上6個以下の直鎖状、分岐状、または環状のアルキル基を示す。よってR1またはR2において用いられる低級アルキル基としては、例えば、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基、tert−ペンチル基、1−メチルブチル基、2−メチルブチル基、1,2−ジメチルプロピル基、ヘキシル基、イソヘキシル基、1−メチルペンチル基、2−メチルペンチル基、3−メチルペンチル基、1,1−ジメチルブチル基、2,2−ジメチルブチル基、1,3−ジメチルブチル基、2,3−ジメチルブチル基、3,3−ジメチルブチル基、1−エチルブチル基、2−エチルブチル基、1,1,2−トリメチルプロピル基、1,2,2−トリメチルプロピル基、1−エチル−1−メチルプロピル基、1−エチル−2−メチルプロピル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロプロピルメチル基、1−シクロプロピルエチル基、2−シクロプロピルエチル基、およびシクロブチルメチル基等があげられる。 In the present specification, the lower alkyl group represents a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms. Accordingly, examples of the lower alkyl group used in R 1 or R 2 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and pentyl. Group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, hexyl group, isohexyl group, 1-methylpentyl group, 2-methylpentyl group, 3 -Methylpentyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1,2-trimethylpropyl group, 1,2,2-trimethylpropyl group, 1-ethyl 1-methylpropyl group, 1-ethyl-2-methylpropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopropylmethyl group, 1-cyclopropylethyl group, 2-cyclopropylethyl group, and cyclo Examples thereof include a butylmethyl group.
本発明においてR1は水素原子または低級アルキル基を示す。R1において好ましくはメチル基または水素原子であり、更に好ましくはR1が水素原子である。一方、本発明においてR2は低級アルキル基を示すが、好ましくはメチル基、エチル基、プロピル基またはブチル基であり、更に好ましくはメチル基またはエチル基である。また本発明においてXはハロゲン原子を示すが、ハロゲン原子としては例えばフッ素、塩素、臭素、ヨウ素原子などがあげられ、中でも塩素または臭素原子が好ましい。また本発明においてMはアルカリ金属を示すが、アルカリ金属としては例えばリチウム、ナトリウム、カリウムなどがあげられ、中でもリチウムまたはナトリウムが好ましい。 In the present invention, R 1 represents a hydrogen atom or a lower alkyl group. R 1 is preferably a methyl group or a hydrogen atom, and more preferably R 1 is a hydrogen atom. On the other hand, in the present invention, 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. In the present invention, X represents a halogen atom, and examples of the halogen atom include fluorine, chlorine, bromine, iodine atom, etc. Among them, chlorine or bromine atom is preferable. In the present invention, M represents an alkali metal, and examples of the alkali metal include lithium, sodium, potassium, etc. Among them, lithium or sodium is preferable.
本発明の一般式[1]で示される有機イリジウム化合物は、前述の一般式[2]または[3]で表される化合物に、一般式[4]で表される化合物を反応させることにより得ることができる。このときの反応条件は特に限定されないが、例えば両者をそれぞれ適当な溶媒に添加し、それらを低温で混合・反応させればよい。後処理は特に限定されないが、一般的な方法として、反応終了後の混合液を濃縮し、得られる混合物からペンタン、ヘキサン、エーテル等の有機溶媒で目的物を抽出した後に適当な担体を選択し、適当な有機溶媒を溶離液としてカラムクロマトグラフィーを行った後、蒸留することにより、目的とする有機イリジウム化合物を得ることが出来る。 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 mixed and reacted at a low temperature. Although the post-treatment is not particularly limited, as a general method, the mixture after completion of the reaction is concentrated, and the target product is extracted from the resulting mixture with an organic solvent such as pentane, hexane, ether, etc., and an appropriate carrier is selected. The target organic iridium compound can be obtained by performing column chromatography using an appropriate organic solvent as an eluent and then performing distillation.
本発明の一般式[1]で表される有機イリジウム化合物を原料としてイリジウム含有膜を製造することができる。製造方法の具体的手段については特に限定されないが、例えばCVD法を用いても良いし、原子層蒸着法(Atomic Layer Deposition法:ALD法)を用いても良いし、またスピンコート法などを用いても良い。 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, an atomic layer deposition method (ALD method) may be used, or a spin coating method may be used. May be.
また、本発明の一般式[1]で表される有機イリジウム化合物を用いてCVD法、ALD法などでイリジウム含有膜を製造する場合、成膜チャンバーへの原料供給方法は特に限定しないが、たとえば、ガスバブリング法を用いても良く、またリキッドインジェクション法を用いても良い。 Further, when an iridium-containing film is produced by the CVD method, the ALD method, or the like using the organic iridium compound represented by the general formula [1] of the present invention, the raw material supply method to the film formation chamber is not particularly limited. A gas bubbling method may be used, or a liquid injection method may be used.
さらに本発明においてCVD法またはALD法などでイリジウム含有膜を製造する場合、用いられる有機イリジウム化合物は、そのまま用いても良く、また有機溶媒に溶解した有機イリジウム化合物溶液として用いても良い。 Furthermore, when producing an iridium containing film | membrane by CVD method or ALD method in this invention, the organic iridium compound used may be used as it is, and may be used as an organic iridium compound solution melt | dissolved in the organic solvent.
溶液として使用する場合に用いられる有機溶媒としては、たとえば、メタノール、エタノール、イソプロパノール等のアルコール類、酢酸エチル、酢酸ブチル、酢酸イソアミル等のエステル類、エチレングリコールモノエチルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノブチルエーテル等のグリコールエーテル類、ジエチルエーテル、グライム、ジグライム、トリグライム、テトラヒドロフラン等のエーテル類、メチルブチルケトン、メチルイソブチルケトン、エチルブチルケトン、ジプロピルケトン、ジイソブチルケトン、メチルアミルケトン、シクロヘキサノン等のケトン類、ヘキサン、シクロヘキサン、エチルシクロヘキサン、ヘプタン、オクタン、ベンゼン、トルエン、キシレン等の炭化水素類が挙げられるがこれらに限定されるものではない。 Examples of the organic solvent used as a solution include alcohols such as methanol, ethanol and isopropanol, esters such as ethyl acetate, butyl acetate and isoamyl acetate, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether and ethylene. Glycol ethers such as glycol monobutyl ether, ethers such as diethyl ether, glyme, diglyme, triglyme, tetrahydrofuran, methyl butyl ketone, methyl isobutyl ketone, ethyl butyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, cyclohexanone, etc. Examples include ketones, hexane, cyclohexane, ethylcyclohexane, heptane, octane, benzene, toluene, xylene and other hydrocarbons. It is not limited to these.
本発明の有機イリジウム化合物は、イリジウム含有膜を製造する方法としてCVD法を用いた場合にガスバブリング条件において液体であることから、定量的に供給することができる。また従来の材料よりも低温で熱分解することができるので、基板上にステップカバレッジ性に優れるイリジウム含有膜を形成することが出来る。本発明により量産性に優れたイリジウム含有膜を形成できる。 The organic iridium compound of the present invention can be quantitatively supplied because it is a liquid under gas bubbling conditions when a CVD method is used as a method for producing an iridium-containing film. Further, since it can be thermally decomposed at a lower temperature than conventional materials, an iridium-containing film having excellent step coverage can be formed on the substrate. According to the present invention, an iridium-containing film excellent in mass productivity can be formed.
次に本発明を実施例によって詳細に説明するが、本発明はこれら実施例によって限定されるものではない。 EXAMPLES Next, although an Example demonstrates this invention in detail, this invention is not limited by these Examples.
実施例1 (エチルシクロペンタジエニル)ビス(エチレン)イリジウムの合成および熱分解特性
THF10ml中にジμ−クロロテトラキス(エチレン)二イリジウム(I)49mgを加え、反応フラスコを−78℃に冷却し、リチウムエチルシクロペンタジエニド17mgのTHF溶液10mlを添加した。−78℃で30分撹拌後、徐々に室温まで昇温し、1時間反応させ、濃縮して泥状混合物を得た。その泥状混合物からヘキサンを用いて抽出し、抽出溶液についてアルミナを用いたカラムクロマトグラフィー(溶離液;ヘキサン)を行い、目的物である(エチルシクロペンタジエニル)ビス(エチレン)イリジウムを14mg得た。
Example 1 Synthesis and Thermal Decomposition Properties of (Ethylcyclopentadienyl) bis (ethylene) iridium 49 mg of diμ-chlorotetrakis (ethylene) diiridium (I) was added to 10 ml of THF, and the reaction flask was cooled to −78 ° C. Then, 10 ml of a THF solution containing 17 mg of lithium ethylcyclopentadienide was added. After stirring at −78 ° C. for 30 minutes, the temperature was gradually raised to room temperature, reacted for 1 hour, and concentrated to obtain a mud mixture. The mud mixture was extracted with hexane, and the extracted solution was subjected to column chromatography using alumina (eluent: hexane) to obtain 14 mg of the target product (ethylcyclopentadienyl) bis (ethylene) iridium. It was.
淡黄色油状物
1H−NMR(500MHz,Benzene−d6,δppm)
4.78−4.77(m,2H),4.66−4.65(m,2H),2.60−2.58(m,4H),1.90(q,J=2.5Hz,2H),0.94(t,J=2.5Hz,3H),0.94−0.91(m,4H)
IR(neat,cm−1)
3040,2970,2920,2870,1480,1460,1435,1310,1165,1150,1035,1010,990,810,790
MS(GC/MS,EI)
193Irでの(エチルシクロペンタジエニル)ビス(エチレン)イリジウムの分子イオンピーク;m/z 342 (図1)
また、この化合物の分解特性を測定した結果を図2に示す。図2からも明らかなように、本発明の有機イリジウム化合物は分解開始温度がおよそ220℃付近にあり、後述の比較例1の化合物(従来品)よりも低温で熱分解することができる。
Pale yellow oil
1 H-NMR (500 MHz, Benzene-d6, δ ppm)
4.78-4.77 (m, 2H), 4.66-4.65 (m, 2H), 2.60-2.58 (m, 4H), 1.90 (q, J = 2.5 Hz) , 2H), 0.94 (t, J = 2.5 Hz, 3H), 0.94-0.91 (m, 4H)
IR (neat, cm −1 )
3040, 2970, 2920, 2870, 1480, 1460, 1435, 1310, 1165, 1150, 1035, 1010, 990, 810, 790
MS (GC / MS, EI)
Molecular ion peak of (ethylcyclopentadienyl) bis (ethylene) iridium at 193 Ir; m / z 342 (FIG. 1)
Moreover, the result of having measured the decomposition | disassembly characteristic of this compound is shown in FIG. As is clear from FIG. 2, the organic iridium compound of the present invention has a decomposition start temperature of about 220 ° C. and can be thermally decomposed at a lower temperature than the compound of Comparative Example 1 (conventional product) described later.
なお、この測定条件は以下の通りである。
測定方法: 入力補償示差走査熱量測定(DSC)
測定条件: 参照 アルミナ
不活性ガス 窒素 50ml/min
昇温 10℃/min。
The measurement conditions are as follows.
Measurement method: Input compensation differential scanning calorimetry (DSC)
Measurement conditions: Reference Alumina
Inert gas Nitrogen 50ml / min
Temperature increase 10 ° C./min.
比較例1 (エチルシクロペンタジエニル)(1,5−シクロオクタジエン)イリジウムの分解特性
実施例1と同様にして、(エチルシクロペンタジエニル)(1,5−シクロオクタジエン)イリジウム(従来品)の分解特性を測定した。結果を図3に示す。図3からも明らかなように、この従来品は分解開始温度がおよそ370℃付近にある。
Comparative Example 1 Decomposition characteristics of (ethylcyclopentadienyl) (1,5-cyclooctadiene) iridium In the same manner as in Example 1, (ethylcyclopentadienyl) (1,5-cyclooctadiene) iridium (conventional) Product) was measured. The results are shown in FIG. As is apparent from FIG. 3, this conventional product has a decomposition start temperature around 370 ° C.
実施例2 (メチルシクロペンタジエニル)ビス(エチレン)イリジウムの合成
THF50ml中にジμ−クロロテトラキス(エチレン)二イリジウム(I)0.97gを加え、反応フラスコを−78℃に冷却し、リチウムメチルシクロペンタジエニド178mgのTHF溶液50mlを添加した。−78℃で1時間40分撹拌後、徐々に室温まで昇温し、1時間反応させ、濃縮して泥状混合物を得た。その泥状混合物からヘキサンを用いて抽出し、抽出溶液についてアルミナを用いたカラムクロマトグラフィー(溶離液;ヘキサン)を行い、目的物である(メチルシクロペンタジエニル)ビス(エチレン)イリジウムを409mg得た。
Example 2 Synthesis of (methylcyclopentadienyl) bis (ethylene) iridium 0.97 g of di [mu] -chlorotetrakis (ethylene) diiridium (I) was added to 50 ml of THF, the reaction flask was cooled to -78 [deg.] C., and
乳白色固体
1H−NMR(500MHz,Benzene−d6,δppm)
4.84(t,J=2.0Hz,2H),4.59(t,J=2.0Hz,2H),2.55−2.44(m,4H),1.51(s,3H),0.95−0.93(m,4H)
MS(GC/MS,EI)
193Irでの(メチルシクロペンタジエニル)ビス(エチレン)イリジウムの分子イオンピーク;m/z 328 (図4)。
Milky white solid
1 H-NMR (500 MHz, Benzene-d6, δ ppm)
4.84 (t, J = 2.0 Hz, 2H), 4.59 (t, J = 2.0 Hz, 2H), 2.55-2.44 (m, 4H), 1.51 (s, 3H) ), 0.95-0.93 (m, 4H)
MS (GC / MS, EI)
Molecular ion peak of (methylcyclopentadienyl) bis (ethylene) iridium at 193 Ir; m / z 328 (FIG. 4).
実施例3 (エチルシクロペンタジエニル)ビス(エチレン)イリジウムを用いたイリジウム膜の製造
図5に示す装置を用い、基板4としては表面にSiO2幕が100nm形成されたSi基板を用いた。原料容器1内に(エチルシクロペンタジエニル)ビス(エチレン)イリジウム約10gを入れてオイルバスで加熱、50℃恒温状態にした。真空ポンプ11、圧力調製弁を用いて反応槽3を10Torr、原料容器内1を100Torrに調整した。キャリアガス7として窒素を用い、流量をマスフローコントローラー10で100sccmに設定した。酸化ガス5として酸素を用い、カウンターガス6として窒素を用いた。酸化ガス流量をマスフローコントローラー8で10sccmに設定し、カウンターガス流量をマスフローコントローラー9で90sccmに設定した。基板4を400℃に設定し、加熱保持した状態で60分間成膜を行った。成膜された膜は金属イリジウム膜であり、膜厚は300nmであった。
Example 3 Production of Iridium Film Using (Ethylcyclopentadienyl) bis (ethylene) iridium Using the apparatus shown in FIG. 5, a Si substrate having a SiO 2 curtain of 100 nm formed on the surface was used as the
1.原料容器
2.オイルバス
3.反応槽
4.基板
5.酸化ガス
6.カウンターガス
7.キャリアガス
8.マスフローコントローラー
9.マスフローコントローラー
10.マスフローコントローラー
11.真空ポンプ
12.排気
1. 1. Raw material container Oil bath 3.
Claims (6)
6. The method for producing an iridium-containing film according to claim 5, wherein R 1 represents a hydrogen atom.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004191388A JP4553642B2 (en) | 2003-08-19 | 2004-06-29 | Organic iridium compound, process for producing the same, and process for producing film |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003295329 | 2003-08-19 | ||
JP2003383169 | 2003-11-12 | ||
JP2004005503 | 2004-01-13 | ||
JP2004191388A JP4553642B2 (en) | 2003-08-19 | 2004-06-29 | Organic iridium compound, process for producing the same, and process for producing film |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005225855A true JP2005225855A (en) | 2005-08-25 |
JP4553642B2 JP4553642B2 (en) | 2010-09-29 |
Family
ID=35000849
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004191388A Expired - Fee Related JP4553642B2 (en) | 2003-08-19 | 2004-06-29 | Organic iridium compound, process for producing the same, and process for producing film |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4553642B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1750014A2 (en) | 2005-08-03 | 2007-02-07 | Mitsubishi Heavy Industries, Ltd. | Axial fan for heat exchanger of in-vehicle air conditioner |
JP2017008351A (en) * | 2015-06-19 | 2017-01-12 | 田中貴金属工業株式会社 | Raw material for chemical vapor deposition composed of organoiridium compound, chemical vapor deposition method, and manufacturing method of catalyst for electrochemistry |
JP6321252B1 (en) * | 2017-03-24 | 2018-05-09 | 田中貴金属工業株式会社 | Chemical vapor deposition material comprising iridium complex and chemical vapor deposition method using the chemical vapor deposition material |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11292888A (en) * | 1998-04-03 | 1999-10-26 | Kojundo Chem Lab Co Ltd | Ethylcyclopentadienyl (1, 5-cyclooctadiene) iridium and its production and production of iridium-containing thin film using the same |
-
2004
- 2004-06-29 JP JP2004191388A patent/JP4553642B2/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11292888A (en) * | 1998-04-03 | 1999-10-26 | Kojundo Chem Lab Co Ltd | Ethylcyclopentadienyl (1, 5-cyclooctadiene) iridium and its production and production of iridium-containing thin film using the same |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1750014A2 (en) | 2005-08-03 | 2007-02-07 | Mitsubishi Heavy Industries, Ltd. | Axial fan for heat exchanger of in-vehicle air conditioner |
JP2017008351A (en) * | 2015-06-19 | 2017-01-12 | 田中貴金属工業株式会社 | Raw material for chemical vapor deposition composed of organoiridium compound, chemical vapor deposition method, and manufacturing method of catalyst for electrochemistry |
JP6321252B1 (en) * | 2017-03-24 | 2018-05-09 | 田中貴金属工業株式会社 | Chemical vapor deposition material comprising iridium complex and chemical vapor deposition method using the chemical vapor deposition material |
WO2018173724A1 (en) * | 2017-03-24 | 2018-09-27 | 田中貴金属工業株式会社 | Chemical vapor deposition raw material comprising iridium complex, and chemical vapor deposition method in which said chemical vapor deposition raw material is used |
US11084837B2 (en) | 2017-03-24 | 2021-08-10 | Tanaka Kikinzoku Kogyo K.K. | Chemical deposition raw material including iridium complex and chemical deposition method using the chemical deposition raw material |
Also Published As
Publication number | Publication date |
---|---|
JP4553642B2 (en) | 2010-09-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5136576B2 (en) | Organoruthenium compound and method for producing the same | |
KR20180137064A (en) | Tungsten precursor and Method of forming a tungsten-containing layer using the same | |
TWI426150B (en) | Method for the deposition of a ruthenium containing film | |
US9416443B2 (en) | Method for the deposition of a ruthenium containing film using arene diazadiene ruthenium(0) precursors | |
JP2009503247A (en) | Beta-diketiminate ligand source and its metal-containing compounds, and systems and methods containing them | |
JP4517565B2 (en) | Ruthenium complex, method for producing the same, and method for producing the thin film | |
US20070069177A1 (en) | Organometallic compounds, processes for the preparation thereof and methods of use thereof | |
JP3321729B2 (en) | Trimethyl (ethylcyclopentadienyl) platinum, method for producing the same, and method for producing platinum-containing thin film using the same | |
JP4696454B2 (en) | Novel organic iridium compound, method for producing the same, and method for producing the film | |
JP4553642B2 (en) | Organic iridium compound, process for producing the same, and process for producing film | |
JP2822946B2 (en) | High purity Ti complex, method for producing the same, and liquid composition for forming BST film | |
WO2019097768A1 (en) | Ruthenium compound, raw material for forming thin film, and method for producing thin film | |
EP1657245B1 (en) | Organoiridium compound, process for producing the same, and process for producing film | |
JP5732772B2 (en) | Ruthenium complex mixture, production method thereof, film-forming composition, ruthenium-containing film and production method thereof | |
JP3511228B2 (en) | Ethylcyclopentadienyl (1,5-cyclooctadiene) iridium, method for producing the same, and method for producing iridium-containing thin film using the same | |
KR20210058289A (en) | Tungsten Precursor, Method for Preparation of the Same, and Tungsten-Containing Thin Film, Method of Manufacturing the Same | |
EP1471567B1 (en) | Organometallic iridium compounds, processes for producing the same, and processes for producing thin films | |
JP2006036780A (en) | Method for producing ruthenium complex | |
JP6429352B1 (en) | Ruthenium compound, raw material for thin film formation, and method for producing thin film | |
JP2005256058A (en) | Iridium-containing membrane forming material and method for manufacturing iridium-containing membrane |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070522 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100406 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100603 |
|
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: 20100629 |
|
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: 20100713 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130723 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4553642 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
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 |