JP7368372B2 - 薄膜の製造方法 - Google Patents
薄膜の製造方法 Download PDFInfo
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- JP7368372B2 JP7368372B2 JP2020550313A JP2020550313A JP7368372B2 JP 7368372 B2 JP7368372 B2 JP 7368372B2 JP 2020550313 A JP2020550313 A JP 2020550313A JP 2020550313 A JP2020550313 A JP 2020550313A JP 7368372 B2 JP7368372 B2 JP 7368372B2
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- Japan
- Prior art keywords
- thin film
- raw material
- gallium
- atomic layer
- layer deposition
- Prior art date
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- 239000010409 thin film Substances 0.000 title claims description 210
- 238000004519 manufacturing process Methods 0.000 title claims description 65
- 239000002994 raw material Substances 0.000 claims description 132
- 238000000034 method Methods 0.000 claims description 94
- 238000000231 atomic layer deposition Methods 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000002243 precursor Substances 0.000 claims description 55
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 33
- 230000008016 vaporization Effects 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000151 deposition Methods 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000007789 gas Substances 0.000 description 56
- 239000010408 film Substances 0.000 description 44
- -1 tertiary-pentyl Chemical group 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 35
- 229910052733 gallium Inorganic materials 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 27
- 229910001195 gallium oxide Inorganic materials 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 26
- 239000002184 metal Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000007788 liquid Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 18
- 238000005229 chemical vapour deposition Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 16
- 239000012535 impurity Substances 0.000 description 14
- 239000012434 nucleophilic reagent Substances 0.000 description 14
- 238000009834 vaporization Methods 0.000 description 14
- 230000001590 oxidative effect Effects 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 239000011259 mixed solution Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 230000008021 deposition Effects 0.000 description 10
- 150000002259 gallium compounds Chemical class 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
- 239000013110 organic ligand Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 235000015067 sauces Nutrition 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
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- 239000010703 silicon Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 229910052752 metalloid Inorganic materials 0.000 description 5
- 150000002738 metalloids Chemical class 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 4
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 4
- KHZGUWAFFHXZLC-UHFFFAOYSA-N 5-methylhexane-2,4-dione Chemical compound CC(C)C(=O)CC(C)=O KHZGUWAFFHXZLC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 4
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- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 description 4
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- 229910052749 magnesium Inorganic materials 0.000 description 4
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- ZRXBTFLOBMVHAY-UHFFFAOYSA-N n-[bis(dimethylamino)gallanyl]-n-methylmethanamine Chemical compound [Ga+3].C[N-]C.C[N-]C.C[N-]C ZRXBTFLOBMVHAY-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 2
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 2
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 2
- 229950006800 prenderol Drugs 0.000 description 2
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000003304 ruthenium compounds Chemical class 0.000 description 2
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- RGGPNXQUMRMPRA-UHFFFAOYSA-N triethylgallium Chemical compound CC[Ga](CC)CC RGGPNXQUMRMPRA-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- ZVYYAYJIGYODSD-LNTINUHCSA-K (z)-4-bis[[(z)-4-oxopent-2-en-2-yl]oxy]gallanyloxypent-3-en-2-one Chemical compound [Ga+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O ZVYYAYJIGYODSD-LNTINUHCSA-K 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002737 metalloid compounds Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011224 oxide ceramic Substances 0.000 description 1
- 229910052574 oxide ceramic Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- 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
- C23C16/44—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 method of coating
- C23C16/455—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 method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
- C23C16/45523—Pulsed gas flow or change of composition over time
- C23C16/45525—Atomic layer deposition [ALD]
- C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD
-
- 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
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- 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)
Description
従来、特許文献1~4に開示されているトリメチルガリウムやトリエチルガリウムのようなトリアルキルガリウムを原子層堆積法用薄膜形成原料として用いて品質の良いガリウム原子含有薄膜を得るために、反応性ガスとしてオゾンガスを用いる方法が用いられてきた。これは、トリアルキルガリウムとオゾンガスとの反応性が高いことが理由であるが、オゾンガスは周辺の部材にも大きなダメージを与えてしまうことが問題となっていた。この問題に対応するためには、反応性に乏しく周辺部材への影響度が少ない水蒸気などの反応性ガスを用いることが考えられるが、トリアルキルガリウムを原子層堆積法用薄膜形成原料として用い、水蒸気を反応性ガスとして用いた場合には、得られる薄膜中に多量の残留炭素成分が混入してしまい、品質の良いガリウム原子含有膜を得ることができないことが問題だった。別の方法として、反応性ガスとして酸素を用い、さらにプラズマを作用させて薄膜を製造する方法も提案されているが、この場合においても、得られる薄膜中に多量の残留炭素成分が混入してしまうことが報告されている。
また、トリス(ジメチルアミノ)ガリウムやトリス(ジエチルアミノ)ガリウムのようなトリス(ジアルキルアミノ)ガリウムは、二量体を形成し、融点が高くなり、常温では固体となり、薄膜形成原料として好ましいものではない。
また、CVD法等の化合物を気化させて薄膜を形成する原料に適する化合物(プレカーサ)に求められる性質は、融点が低く液体の状態で輸送が可能であること、液体の粘度が低いこと、蒸気圧が大きく気化させやすいこと、熱安定性が高いことである。なかでも、ガリウム原子供給源となる薄膜形成用原料では、融点が低く、輸送性に優れる薄膜形成用原料が求められていた。
従って、本発明の第2の目的は、融点が低く、輸送性に優れた、特定の構造を有するガリウム化合物を含有してなる薄膜形成用原料を提供することにある。
即ち、本発明は、下記一般式(1)で表されるガリウム化合物を含有する原子層堆積法用薄膜形成原料を提供するものである:
尚、下記化学式中の「Me」はメチル基を表し、「Et」はエチル基を表す。
化合物を気化させる工程を有する薄膜の製造方法に用いる場合は、これらの組み合わせが、常温常圧下において液体状態となり、蒸気圧が大きくなるものが好ましい。具体的には、R5~R8が各々独立にメチルまたはエチルであるものは蒸気圧が高いことから好ましく、これらの中でもR5=R6であるものが特に好ましい。また、R5~R8およびA2の炭素原子数の和は、8~10の範囲であるものが好ましく、なかでもA2がプロピレン、2-メチルプロピレンであるものは融点が低く、輸送性が良好であることから好ましい。
また、堆積速度は、原料の供給条件(気化温度、気化圧力)、反応温度、反応圧力によりコントロールすることができる。堆積速度は、大きいと得られる薄膜の特性が悪化する場合があり、小さいと生産性に問題を生じる場合があるので、0.01nm/分~100nm/分が好ましく、1nm/分~50nm/分がより好ましい。
[実施例1]化合物No.25の合成
反応フラスコに3-ジメチルアミノ-2-メチルプロピルクロライド塩酸塩102gと超純水216gと脱水ペンタン78.7gを加え混合した。得られた溶液に、室温下、25%水酸化ナトリウム水溶液107gを滴下し、1時間撹拌した。得られた反応溶液は分液漏斗を用いて有機相と水相を分離した後、脱水ペンタンを各50mL用いて水相から抽出を3回行った。得られた有機相を合わせ、これに硫酸マグネシウムを添加し、室温にて30分撹拌を行い、脱水乾燥を行った。濾過を行い、硫酸マグネシウムを分離した後、濾液をオイルバス60℃にて脱溶媒を実施した。得られた配位子はオイルバス60℃にて減圧下蒸留を行い、3-ジメチルアミノ-2-メチルプロピルクロライドを無色透明液体として70.8g得た。
反応フラスコに、リボン状マグネシウム1.65gを加え、アルゴン雰囲気下とした後、脱水THF43.1g、ジブロモエタン1.16gを添加しオイルバス60℃にて撹拌を行った。この混合溶液に、加熱下、3-ジメチルアミノ-2-メチルプロピルクロライド11.7gを滴下し、5時間加熱還流を行い、グリニャール試薬の調整を行った。別途用意した反応フラスコへ塩化ガリウム10.6g、脱水トルエン50.8gを加え、混合溶液が10℃以下となるまで氷冷下にて撹拌を行った。氷冷下にて、この反応溶液に、先述したグリニャール試薬を滴下し、滴下終了後、室温に戻し18時間撹拌を行った。得られた反応溶液を濾過した後、オイルバス100℃にて脱溶媒を行った。生成したガリウム錯体の入ったフラスコを蒸留装置へ接続し、オイルバス150℃、12Paにて蒸留精製を行いN,N-ジメチルアミノ-2-メチルプロピルガリウムジクロライドを白色固体として6.22g得た。
Ar雰囲気下、反応フラスコに上記で得たN,N-ジメチルアミノ-2-メチルプロピルガリウムジクロライド3.77g、脱水ペンタン11.6gを加え、10℃以下になるまで氷冷下撹拌を行った。氷冷下、この混合溶液へ、メチルリチウム(1.16Mジエチルエーテル溶液)26.1gを滴下し、滴下終了後室温へ戻し、24時間撹拌を行った。得られた反応溶液の濾過を行い、オイルバス60℃にて脱溶媒を行った。生成したガリウム錯体の入ったフラスコを蒸留精製装置へ接続し、オイルバス60℃、130Paにて蒸留精製を行い、無色透明液体を1.07g得た。
(1)常圧TG-DTA
質量50%減少温度:119℃(760Torr、Ar流量:100ml/分、昇温10℃/分)
(2)1H-NMR(重ベンゼン)
-0.16ppm(6H,singlet)、0.53ppm(1H,d=7.98,triplet)、0.84ppm(1H,d=4.80,12.6,dublet)、0.93ppm(3H,d=6.00,dublet)、1.62-1.69ppm(1H,multiplet)、1.65ppm(2H,singlet)、1.67ppm(3H,singlet)、1.75ppm(3H,singlet)
(3)元素分析(理論値)
C:48.2%(48.05%)、H:9.8%(10.08%)、Ga:34.8%(34.87%)、N:7.1%(7.00%)
反応フラスコに3-ジメチルアミノプロピルクロライド塩酸塩59.7gと超純水133gと脱水ペンタン59.3gを加え混合した。得られた溶液に、室温下、22%水酸化ナトリウム水溶液130gを滴下し、1.5時間撹拌した。得られた反応溶液は分液漏斗を用いて有機相と水相を分離した後、脱水ペンタンを各50mL用いて水相から抽出を3回行った。得られた有機相を合わせ、これに硫酸マグネシウムを添加し、室温にて30分撹拌を行い、脱水乾燥を行った。濾過を行い、硫酸マグネシウムを分離した後、濾液をオイルバス50℃にて脱溶媒を実施した。得られた配位子はオイルバス65℃にて減圧下蒸留を行い、3-ジメチルアミノプロピルクロライドを無色透明液体として40.2g得た。
反応フラスコに、リボン状マグネシウム6.62gを加え、アルゴン雰囲気下とした後、脱水THF55.7g、ジブロモエタン4.86gを添加しオイルバス80℃にて撹拌を行った。この混合溶液に、加熱下、3-ジメチルアミノプロピルクロライド27.2gを滴下し、14時間加熱還流を行い、グリニャール試薬の調整を行った。別途用意した反応フラスコへ塩化ガリウム38.9g、脱水トルエン235gを加え、混合溶液が10℃以下となるまで氷冷下にて撹拌を行った。氷冷下にて、この反応溶液に、先述したグリニャール試薬を滴下し、滴下終了後、室温に戻し21時間撹拌を行った。得られた反応溶液を濾過した後、オイルバス100℃にて脱溶媒を行った。生成したガリウム錯体の入ったフラスコを蒸留装置へ接続し、オイルバス130℃、9Paにて蒸留精製を行いN,N-ジメチルアミノプロピルガリウムジクロライドを白色固体として40.8g得た。
Ar雰囲気下、反応フラスコに上記で得たN,N-ジメチルアミノプロピルガリウムジクロライド4.14g、脱水ヘキサン14.8gを加え、10℃以下になるまで氷冷下撹拌を行った。氷冷下、この混合溶液へ、メチルリチウム(1.16Mジエチルエーテル溶液)31.2gを滴下し、滴下終了後室温へ戻し、22時間撹拌を行った。得られた反応溶液の濾過を行い、オイルバス80℃にて脱溶媒を行った。生成したガリウム錯体の入ったフラスコを蒸留精製装置へ接続し、オイルバス85℃、微減圧下にて蒸留精製を行い、白色固体を1.87g得た。
(1)常圧TG-DTA
質量50%減少温度:116℃(760Torr、Ar流量:100ml/分、昇温10℃/分)
(2)1H-NMR(重ベンゼン)
-0.18ppm(6H,singlet)、0.54ppm(2H,d=7.20,triplet)、1.56-1.63ppm(2H,multiplet)、1.67ppm(6H,singlet)、1.79ppm(2H,d=5.60,triplet)
(3)元素分析(理論値)
C:45.%(45.21%)、H:9.8%(9.76%)、Ga:37.3%(37.50%)、N:7.2%(7.53%)
Ar雰囲気下、反応フラスコに製造例1で得たN,N-ジメチルアミノプロピルガリウムジクロライド5.31g、脱水ヘキサン20.0gを加え、10℃以下になるまで氷冷下撹拌を行った。氷冷下、この混合溶液へ、エチルマグネシウムクロリド(1.05MTHF溶液)46.62gを滴下し、滴下終了後室温へ戻し、20時間撹拌を行った。得られた反応溶液の濾過を行い、オイルバス90℃にて脱溶媒を行った。生成したガリウム錯体の入ったフラスコを蒸留精製装置へ接続し、オイルバス95℃、75Paにて蒸留精製を行い、無色透明液体を3.78g得た。
(1)常圧TG-DTA
質量50%減少温度:146℃(760Torr、Ar流量:100ml/分、昇温10℃/分)
(2)1H-NMR(重ベンゼン)
0.37-0.56ppm(6H,multiplet)、1.39ppm(6H,d=8.40,triplet)、1.56-1.63ppm(2H,multiplet)、1.73ppm(6H,singlet)、1.80ppm(2H,d=5.60,triplet)
(3)元素分析(理論値)
C:50.2%(50.51%)、H:10.5%(10.36%)、Ga:32.1%(32.58%)、N:6.8%(6.55%)
実施例1、製造例1および製造例2で得られた化合物No.25、13および16並びに下記の比較化合物1(トリメチルガリウム)および比較化合物2[ガリウム(III)アセチルアセトナート]について、常圧25℃における状態を目視で観測した。25℃において固体であるものについては、融点測定を行った。これらの結果を表1に示す。
化合物No.13を原子層堆積法用原料とし、図1に示す装置を用いて以下の条件のALD法により、シリコンウエハ上に酸化ガリウム薄膜を製造した。得られた薄膜の組成をX線光電子分光法により確認したところ、得られた薄膜は酸化ガリウムであり、残留炭素含有量は6.2atom%だった。また、X線反射率法による膜厚測定を行い、その平均値を算出したところ、膜厚は平均26.4nmであり、1サイクル当たりに得られる膜厚は平均0.05nmであった。
基板:シリコンウェハ
反応温度(シリコンウエハ温度):200℃
反応性ガス:水蒸気
下記(1)~(4)からなる一連の工程を1サイクルとして、500サイクル繰り返した。
(1)原料容器温度:100℃、原料容器内圧力:100Paの条件で気化させた原子層堆積法用原料を成膜チャンバーに導入し、系圧力:100Paで0.1秒間堆積させる;
(2)15秒間のアルゴンパージにより、堆積しなかった原料を除去する;
(3)反応性ガスを成膜チャンバーに導入し、系圧力:100Paで10秒間反応させる;
(4)15秒間のアルゴンパージにより、未反応の第一の反応性ガス及び副生ガスを除去する。
原子層堆積法用原料として化合物No.16を用いたこと以外は実施例2と同様の条件で酸化ガリウム薄膜を製造した。得られた薄膜の組成をX線光電子分光法により確認したところ、得られた薄膜は酸化ガリウムであり、残留炭素含有量は3.0atom%だった。また、X線反射率法による膜厚測定を行い、その平均値を算出したところ、膜厚は平均25.7nmであり、1サイクル当たりに得られる膜厚は平均0.05nmであった。
原子層堆積法用原料として化合物No.25を用いたこと以外は実施例2と同様の条件で酸化ガリウム薄膜を製造した。得られた薄膜の組成をX線光電子分光法により確認したところ、得られた薄膜は酸化ガリウムであり、残留炭素含有量は1.0atom%よりも少なかった。また、X線反射率法による膜厚測定を行い、その平均値を算出したところ、膜厚は平均26.3nmであり、1サイクル当たりに得られる膜厚は平均0.05nmであった。
反応性ガスとしてオゾンを用いたこと以外は実施例4と同様の条件で酸化ガリウム薄膜を製造した。得られた薄膜の組成をX線光電子分光法により確認したところ、得られた薄膜は酸化ガリウムであり、残留炭素含有量は1.0atom%よりも少なかった。また、X線反射率法による膜厚測定を行い、その平均値を算出したところ、膜厚は平均27.3nmであり、1サイクル当たりに得られる膜厚は平均0.05nmであった。
原子層堆積法用原料として比較化合物1を用いたこと以外は実施例2と同様の条件で酸化ガリウム薄膜を製造した。得られた薄膜の組成をX線光電子分光法により確認したところ、得られた薄膜は酸化ガリウムであり、残留炭素含有量は20.0atom%だった。また、X線反射率法による膜厚測定を行い、その平均値を算出したところ、膜厚は平均10nmであり、1サイクル当たりに得られる膜厚は平均0.02nmであった。
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