JP6242026B2 - Ald/cvdシリコン含有膜用のオルガノシラン前駆体 - Google Patents
Ald/cvdシリコン含有膜用のオルガノシラン前駆体 Download PDFInfo
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- JP6242026B2 JP6242026B2 JP2015523276A JP2015523276A JP6242026B2 JP 6242026 B2 JP6242026 B2 JP 6242026B2 JP 2015523276 A JP2015523276 A JP 2015523276A JP 2015523276 A JP2015523276 A JP 2015523276A JP 6242026 B2 JP6242026 B2 JP 6242026B2
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- thin film
- alkyl group
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- 239000002243 precursor Substances 0.000 title claims description 113
- 229910052710 silicon Inorganic materials 0.000 title claims description 37
- 150000001282 organosilanes Chemical class 0.000 title description 38
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title description 34
- 239000010703 silicon Substances 0.000 title description 29
- 238000000034 method Methods 0.000 claims description 49
- 239000000758 substrate Substances 0.000 claims description 39
- 239000000376 reactant Substances 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 238000000231 atomic layer deposition Methods 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- -1 alkyl metals Chemical class 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 239000010409 thin film Substances 0.000 claims description 23
- 238000000151 deposition Methods 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 238000005229 chemical vapour deposition Methods 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 238000005019 vapor deposition process Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 claims description 4
- 239000005046 Chlorosilane Substances 0.000 claims description 3
- 150000001343 alkyl silanes Chemical class 0.000 claims description 3
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 3
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 claims description 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 3
- FTZIQBGFCYJWKA-UHFFFAOYSA-N 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Chemical compound S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 FTZIQBGFCYJWKA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000003446 ligand Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000004215 Carbon black (E152) Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 22
- 229930195733 hydrocarbon Natural products 0.000 description 22
- 150000002430 hydrocarbons Chemical class 0.000 description 22
- 239000001301 oxygen Substances 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000008021 deposition Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229910052814 silicon oxide Inorganic materials 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000725 suspension Substances 0.000 description 9
- 229910004298 SiO 2 Inorganic materials 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052735 hafnium Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052758 niobium Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910052715 tantalum Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000000137 annealing Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012159 carrier gas Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- VEYJKODKHGEDMC-UHFFFAOYSA-N dichloro(trichlorosilyl)silicon Chemical compound Cl[Si](Cl)[Si](Cl)(Cl)Cl VEYJKODKHGEDMC-UHFFFAOYSA-N 0.000 description 5
- 229910052747 lanthanoid Inorganic materials 0.000 description 5
- 150000002602 lanthanoids Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 5
- 0 *C1N(*)[*-]N1* Chemical compound *C1N(*)[*-]N1* 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229910052788 barium Inorganic materials 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000005137 deposition process Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical group [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 241001168730 Simo Species 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 229910052745 lead Inorganic materials 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000012495 reaction gas Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011819 refractory material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZUJOACIBNBMMDN-UHFFFAOYSA-N 1,2,3,4,5,6-hexachlorohexasilinane Chemical group Cl[SiH]1[SiH]([SiH]([SiH]([SiH]([SiH]1Cl)Cl)Cl)Cl)Cl ZUJOACIBNBMMDN-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- BIVNKSDKIFWKFA-UHFFFAOYSA-N N-propan-2-yl-N-silylpropan-2-amine Chemical compound CC(C)N([SiH3])C(C)C BIVNKSDKIFWKFA-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 229910004541 SiN Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 2
- VYFXMIAQVGXIIN-UHFFFAOYSA-N trichloro(chlorosilyl)silane Chemical compound Cl[SiH2][Si](Cl)(Cl)Cl VYFXMIAQVGXIIN-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical group Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910015868 MSiO Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004200 TaSiN Inorganic materials 0.000 description 1
- 229910008482 TiSiN Inorganic materials 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- JFWLFXVBLPDVDZ-UHFFFAOYSA-N [Ru]=O.[Sr] Chemical compound [Ru]=O.[Sr] JFWLFXVBLPDVDZ-UHFFFAOYSA-N 0.000 description 1
- VOSJXMPCFODQAR-UHFFFAOYSA-N ac1l3fa4 Chemical compound [SiH3]N([SiH3])[SiH3] VOSJXMPCFODQAR-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052454 barium strontium titanate Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- FXMNVBZEWMANSQ-UHFFFAOYSA-N chloro(silyl)silane Chemical compound [SiH3][SiH2]Cl FXMNVBZEWMANSQ-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 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
- 239000007791 liquid phase Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IDVWLLCLTVBSCS-UHFFFAOYSA-N n,n'-ditert-butylmethanediimine Chemical compound CC(C)(C)N=C=NC(C)(C)C IDVWLLCLTVBSCS-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- GLTDLAUASUFHNK-UHFFFAOYSA-N n-silylaniline Chemical class [SiH3]NC1=CC=CC=C1 GLTDLAUASUFHNK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000004151 rapid thermal annealing Methods 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 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
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- 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
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- 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
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Description
本出願は、2012年7月20日付けで出願された米国仮出願第61/674,103号(その内容全体が引用することにより本明細書の一部をなすものとする)に対する優先権を主張するものである。
及びC6〜C13アリール基から選択することができ、Lはイソシアナト配位子、メチルエチルケトキシム配位子、トリフルオロ酢酸配位子、トリフレート配位子、アシルオキシ配位子、β−ジケチミネート配位子、β−ジイミネート配位子、アミジネート配位子、グアニジネート配位子、アルキルアミノ配位子、ヒドリド配位子、アルコキシド配位子又はギ酸配位子から選択することができる)を有するシリコン化合物を含む、広範なSi含有前駆体を開示している。Pinnavaia et al.は、シリコンアセチルアセトネート及びシリコン1,3−ジケトネート前駆体から多孔質の合成半結晶性ハイブリッドの有機−無機酸化シリコン組成物を調製する方法を特許請求している(特許文献6)。
或る特定の略語、記号及び用語を以下の明細書及び特許請求の範囲全体を通して使用する。
を有するオルガノシラン分子;
・R1とR2とが及び/又はR2とR3とが連結して環状鎖を形成している、上記オルガノシラン分子;
・下記式:
を有する、上記オルガノシラン分子;
・H3Si(NiPr−amd)である、上記オルガノシラン分子;
・下記式:
を有する、上記オルガノシラン分子;
・H3Si(−(iPr)N−C(NMe2)−N(iPr)−)である、上記オルガノシラン分子;
・下記式:
を有する、上記オルガノシラン分子;
・H3Si(−(iPr)N−C(OMe)−N(iPr)−)である、上記オルガノシラン分子;
・下記式:
を有する、上記オルガノシラン分子;及び、
・H3Si(−(iPr)N−C(Cl)−N(iPr)−)である、上記オルガノシラン分子、
が開示される。
を有するSi含有薄膜形成前駆体;
・R1とR2とが及び/又はR2とR3とが連結して環状鎖を形成している、上記Si含有薄膜形成前駆体;
・下記式:
を有する、上記Si含有薄膜形成前駆体;
・H3Si(NiPr−amd)である、上記Si含有薄膜形成前駆体;
・下記式:
を有する、上記Si含有薄膜形成前駆体;
・H3Si(−(iPr)N−C(NMe2)−N(iPr)−)である、上記Si含有薄膜形成前駆体;
・下記式:
を有する、上記Si含有薄膜形成前駆体;及び、
・H3Si(−(iPr)N−C(OMe)−N(iPr)−)である、上記Si含有薄膜形成前駆体;
・下記式:
を有する、上記Si含有薄膜形成前駆体;及び、
・H3Si(−(iPr)N−C(Cl)−N(iPr)−)である、上記Si含有薄膜形成前駆体、
も開示される。
・少なくとも1種の第2の前駆体を含む蒸気を反応器に導入すること;
・少なくとも1種の第2の前駆体の元素が、第2族、第13族、第14族、遷移金属、ランタニド及びそれらの組合せからなる群から選択されること;
・少なくとも1種の第2の前駆体の元素が、Mg、Ca、Sr、Ba、Zr、Hf、Ti、Nb、Ta、Al、Si、Ge、Y又はランタニドから選択されること;
・反応器に少なくとも1種の共反応物を導入すること;
・共反応物が、O2、O3、H2O、H2O2、NO、NO2、カルボン酸、それらのラジカル、及びそれらの組合せからなる群から選択されること;
・共反応物がプラズマ処理した酸素であること;
・共反応物がオゾンであること;
・Si含有層が酸化シリコン層であること;
・共反応物が、H2、NH3、(SiH3)3N、ヒドリドシラン(SiH4、Si2H6、Si3H8、Si4H10、Si5H10、Si6H12等)、クロロシラン及びクロロポリシラン(SiHCl3、SiH2Cl2、SiH3Cl、Si2Cl6、Si2HCl5、Si3Cl8等)、アルキルシラン(Me2SiH2、Et2SiH2、MeSiH3、EtSiH3等)、ヒドラジン(N2H4、MeHNNH2、MeHNNHMe等)、有機アミン(NMeH2、NEtH2、NMe2H、NEt2H、NMe3、NEt3、(SiMe3)2NH等)、ピラゾリン、ピリジン、B含有分子(B2H6、9−ボラビシクロ[3,3,1]ノン、トリメチルボロン、トリエチルボロン、ボラジン等)、アルキル金属(トリメチルアルミニウム、トリエチルアルミニウム、ジメチル亜鉛、ジエチル亜鉛等)、それらのラジカル種、並びにそれらの混合物からなる群から選択されること;
・共反応物が、H2、NH3、SiH4、Si2H6、Si3H8、SiH2Me2、SiH2Et2、N(SiH3)3、それらの水素ラジカル、及びそれらの混合物からなる群から選択されること;
・共反応物がプラズマ処理されていること;
・共反応物が遠隔プラズマ処理されていること;
・共反応物がプラズマ処理されていないこと;
・共反応物がH2であること;
・共反応物がNH3であること;
・共反応物がHCDSであること;
・共反応物がPCDSであること;
・共反応物がテトラクロロシランであること;
・共反応物がトリクロロシランであること;
・共反応物がヘキサクロロシクロヘキサシランであること;
・蒸着プロセスが化学蒸着プロセスであること;
・蒸着プロセスが原子層堆積(ALD)プロセスであること;
・蒸着プロセスが空間ALDプロセスであること;
・シリコン含有層がSiであること;
・シリコン含有層がSiO2であること;
・シリコン含有層がSiNであること;
・シリコン含有層がSiONであること;
・シリコン含有層がSiCNであること;及び、
・シリコン含有層がSiCOHであること。
(式中、R1及びR2はそれぞれ独立して、H、C1〜C6アルキル基、又はC3〜C20アリール基若しくは複素環基とすることができ、R3はH、C1〜C6アルキル基、C
3〜C20アリール基若しくは複素環基、アミノ基、アルコキシ基、又はハロゲンとすることができる)
を有する。R1とR2とが及び/又はR2とR3とが連結して環状鎖を形成してもよい。
を有するアミジネート含有化合物である。R1及びR2はそれぞれ独立してC1〜C6アルキル基であるのが好ましい。
によって合成することができる。
(式中、R1、R2、R3及びR4はそれぞれ独立して、H、C1〜C6アルキル基、C3〜C20アリール基又は複素環基とすることができる)
を有するグアニジネート含有化合物である。他の分子と比べて窒素含量が増大していることから、これらの分子を使用して、窒素を更に含むシリコン含有膜、例えばSiN若しくはSiONを作製するか、又はSiN若しくはSiON含有膜中の窒素量を調整することができる。
(式中、R1、R2、及びR3はそれぞれ独立して、H、C1〜C6アルキル基、C3〜C20アリール基又は複素環基とすることができる)
を有するイソウレエート含有化合物である。他の分子と比べて酸素含量が増大していることから、これらの分子を使用して、酸素を更に含むシリコン含有膜、例えばSiO2若しくはSiONを作製するか、又はSiO2若しくはSiON含有膜中の酸素量を調整することができる。
水蒸気の逆流を抑えるためにオイルバブラーに接続されている。
(式中、R1及びR2はそれぞれ独立して、H、C1〜C6アルキル基、又はC3〜C20アリール基若しくは複素環基とすることができ、XはCl、Br、I又はFとすることができる)
を有するα−ハロアミジネート含有化合物である。ハロゲン原子はアモルファスシリコンの原子層堆積におけるコンフォーマル性を改善することができる。
1232-1245)。1モル当量の適切な塩基(カリウムヘキサメチルジシラジド等)の炭化水素溶液を反応混合物に添加して、得られる懸濁液を濾過し金属塩副生成物を除去する。得られる溶液を、SiRH3(式中、Rはフェニル置換基、トリル置換基又は他の適切なアリール置換基である)で反応することができる。得られる混合物を分留によって精製することができる。これらの合成法に適した炭化水素溶液の例としては、ジエチルエーテル、ペンタン、ヘキサン又はトルエンが挙げられる。出発材料は全て市販されているものであ
る。
体的にはSiMOx膜(xは4であり、MはTa、Hf、Nb、Mg、Al、Sr、Y、Ba、Ca、As、Sb、Bi、Sn、Pb、Co、ランタニド(Er等)、又はそれらの組合せである)の堆積も提供する。開示の方法は半導体、光電池、LCD−TFT又はフラットパネル型デバイスの製造に有用であり得る。該方法は、基板を準備することと、開示のオルガノシラン前駆体の少なくとも1つを含む蒸気を準備することと、蒸気を基板に接触させ(典型的に蒸気を基板に当てて)、基板の少なくとも片面に二元金属含有層を形成することとを含む。酸素源、例えばO3、O2、H2O、NO、H2O2、酢酸、ホルマリン、パラ−ホルムアルデヒド、それらの酸素ラジカル、及びそれらの組合せ、ただし好ましくはO3又はプラズマ処理したO2を蒸気に与えてもよい。
ZrO2系材料、HfO2系材料、TiO2系材料、希土類酸化物系材料、三元酸化物系材料等)から又は銅と低k層との間の酸素障壁として使用される窒化物系膜(例えばTaN)から選ぶことができる。他の基板を半導体、光電池、LCD−TFT又はフラットパネルデバイスの製造に使用してもよい。このような基板の例としては、金属窒化物含有基板(例えば、TaN、TiN、WN、TaCN、TiCN、TaSiN及びTiSiN);絶縁体(例えば、SiO2、Si3N4、SiON、HfO2、Ta2O5、ZrO2、TiO2、Al2O3及びチタン酸バリウムストロンチウム);又はこれらの材料のあらゆる数の組合せを含む他の基板等の固体基板が挙げられるが、これらに限定されない。用いられる実際の基板は、用いられる特定の前駆体の実施形態によっても変わり得る。しかし、多くの例では、用いられる好ましい基板は、水素化炭素、TiN、SRO、Ru及びSi型の基板、例えばポリシリコン基板又は結晶性シリコン基板から選択される。
SiH2、(C2H5)2SiH2、(CH3)SiH3、(C2H5)SiH3等)、ヒドラジン(N2H4、MeHNNH2、MeHNNHMe等)、有機アミン(N(CH3)H2、N(C2H5)H2、N(CH3)2H、N(C2H5)2H、N(CH3)3、N(C2H5)3、(SiMe3)2NH等)、ピラゾリン、ピリジン、B含有分子(B2H6、9−ボラビシクロ[3,3,1]ノン、トリメチルボロン、トリエチルボロン、ボラジン等)、アルキル金属(トリメチルアルミニウム、トリエチルアルミニウム、ジメチル亜鉛、ジエチル亜鉛等)、それらのラジカル種、及びそれらの混合物の1つとすることができる。還元剤はH2、NH3、SiH4、Si2H6、Si3H8、SiH2Me2、SiH2Et2、N(SiH3)3、それらの水素ラジカル、又はそれらの混合物であるのが好ましい。還元剤を使用する場合、得られるシリコン含有膜は純Siとすることができる。
ャンバをパージ又は真空排気することによって、過剰なオルガノシラン前駆体を反応チャンバから取り除くことができる。酸素源を反応チャンバに導入し、そこで酸素源は吸収されたオルガノシラン前駆体と自己制限的に反応する。反応チャンバをパージ及び/又は真空排気することによって、任意の過剰な酸素源が反応チャンバから取り除かれる。所望の膜がシリコン酸化物膜である場合、この二段階プロセスは、所望の膜厚をもたらすか又は必要な厚さの膜が得られるまで繰り返すことができる。
)が含まれ得る。適切なオルガノシラン前駆体及び共反応物の公正な選択によって、所望の膜組成を得ることができることが当業者には認識される。
SiH3(NiPr−amd)の合成:
撹拌しながら、メチルリチウム(91mL、1.6M、0.146mol)のジエチルエーテル溶液を−40℃のN,N’−ジイソプロピルカルボジイミド(22.5mL、0.145mol)のジエチルエーテル溶液(150mL)にゆっくりと添加する。添加が完了した後、得られる無色の懸濁液を室温に加温し、3時間撹拌して無色の溶液を形成する。別のフラスコに−78℃(ドライアイス/アセトン)冷却器を取り付け、ジエチルエーテル(100mL)を充填し、−78℃に冷却する。撹拌しながら、モノクロロシラン(13.2g、0.198mol)を第2のフラスコへとゆっくりと凝縮し、その後第1の工程によるリチウムアミジネート溶液をゆっくりと添加する。初めに幾らかの煙霧が観察され、その後無色の沈殿物が形成された。添加が完了した後、懸濁液を一晩激しく撹拌しながらゆっくりと室温にした。懸濁液を、セライトパッドを含む中空隙率のガラスフリットに通して濾過し、得られる無色の溶液を、Vigreuxカラムを用いて大気圧で蒸留して溶媒を除去する。受けフラスコを交換して、−78℃の溶液槽にて冷却し、所望の生成物を無色の液体として25℃〜28℃/200mTorr〜300mTorrで蒸留する。収量:7.9g(31.6%)。図1は、この前駆体についての温度変化に伴う重量損失率をDiPASの重量損失率と比較して示すTGAグラフである。29Si NMR(80MHz,C6D6,25℃)δ(ppm)=−87.7;1H NMR(400MHz,C6D6,25℃)δ(ppm)=4.73(s,3H,SiH3)、3.38(sept.,2H,1JH−H=8.0Hz,NCH(CH3)2)、1.40(s,3H,CCH3)、1.12(d,12H,1JH−H=8.0Hz,NCH(CH3)2)。
SiH3(NtBu−amd)の合成:
フラスコに、−78℃(ドライアイス/アセトン)冷却器を取り付け、ジエチルエーテル(100mL)を充填し、−78℃に冷却する。撹拌しながら、モノクロロシラン(8.9g、0.134mol)をフラスコへとゆっくりと凝縮する。第2のフラスコ内で、メチルリチウム(101mL、1.6M、0.162mol)のジエチルエーテル溶液を
、−40℃のN,N’−ジ−tertブチルカルボジイミド(25g、0.162mol)のジエチルエーテル溶液(100mL)にゆっくりと添加する。添加が完了した後、得られる無色のリチウムアミジネート懸濁液を室温に加温し、1時間撹拌して無色の溶液を形成する。得られるLi−amd溶液を0℃に冷却して、カニューレによって−78℃のモノクロロシラン(MCS)のジエチルエーテル溶液へと添加する。初めに幾らかの煙霧が観察され、その後無色の沈殿物が形成された。添加が完了した後、懸濁液を激しく撹拌しながら室温にした。
NMR(80MHz,C6D6,25℃)δ(ppm)=−117.5;1H NMR(400MHz,C6D6,25℃)δ(ppm)=5.05(s,3H,SiH3)、1.79(s,3H,CCH3)、1.25(s,9H,NC(CH3)3)。
SiH3(NiPr−amd)のALD:
ALD試験を、室温の容器に入れられた実施例1で調製したSiH3(NiPr−amd)を用いて行った。およそ0.5Torrに固定した反応器圧でのオゾンの使用等といった典型的なALD条件を使用した。図2に示されるように、完全な表面飽和及び反応によるALD挙動を純シリコンウエハにおいて275℃で評価した。異なる堆積装置は異なる前駆体導入時間において表面飽和を示し得ることが当業者には認識される。屈折率はSiO2膜に特徴的なものである(純SiO2の屈折率は1.46である)。前駆体導入時間の変化による屈折率の変化は、膜における不純物の指標となる。
Claims (14)
- 前記分子がSiH3(NiPr−amd)である、請求項2に記載のSi含有薄膜形成前駆体。
- 基板上にSi含有層を堆積させる方法であって、
少なくとも1つの請求項1ないし請求項6のいずれか一項に記載のSi含有薄膜形成前駆体を少なくとも1つの基板が中に配置された反応器に導入する工程と、
蒸着法を用いて、前記Si含有薄膜形成前駆体の少なくとも一部を前記少なくとも1つの基板上に堆積して、それによりSi含有層を形成する工程と、
を含む、方法。 - 前記反応器に少なくとも1種の共反応物を導入することを更に含む、請求項7に記載の方法。
- 前記共反応物が、O2、O3、H2O、H2O2、NO、NO2、カルボン酸、それらのラジカル、及びそれらの組合せからなる群から選択される、請求項8に記載の方法。
- 前記共反応物が、H2、NH3、(SiH3)3N、ヒドリドシラン(SiH4、Si2H6、Si3H8、Si4H10、Si5H10、Si6H12等)、クロロシラン及びクロロポリシラン(SiHCl3、SiH2Cl2、SiH3Cl、Si2Cl6、Si2HCl5、Si3Cl8等)、アルキルシラン(Me2SiH2、Et2SiH2、MeSiH3、EtSiH3等)、ヒドラジン(N2H4、MeHNNH2、MeHNNHMe等)、有機アミン(NMeH2、NEtH2、NMe2H、NEt2H、NMe3、NEt3、(SiMe3)2NH等)、ピラゾリン、ピリジン、B含有分子(B2H6、9−ボラビシクロ[3,3,1]ノン、トリメチルボロン、トリエチルボロン、ボラジン等)、アルキル金属(トリメチルアルミニウム、トリエチルアルミニウム、ジメチル亜鉛、ジエチル亜鉛等)、それらのラジカル種、並びにそれらの混合物からなる群から選択される、請求項8に記載の方法。
- 前記共反応物が、H2、NH3、SiH4、Si2H6、Si3H8、SiH2Me2、SiH2Et2、N(SiH3)3、それらの水素ラジカル、及びそれらの混合物からなる群から選択される、請求項10に記載の方法。
- 前記共反応物が、SiHCl3、Si2Cl6、Si2HCl5、Si2H2Cl4及びシクロ−Si6H6Cl6からなる群から選択される、請求項10に記載の方法。
- 前記蒸着プロセスが化学蒸着プロセスである、請求項7に記載の方法。
- 前記蒸着プロセスが原子層堆積プロセスである、請求項7に記載の方法。
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EP2875166A1 (en) | 2015-05-27 |
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TWI579292B (zh) | 2017-04-21 |
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WO2014015237A1 (en) | 2014-01-23 |
TW201410689A (zh) | 2014-03-16 |
WO2014015232A1 (en) | 2014-01-23 |
JP2015525773A (ja) | 2015-09-07 |
JP2015525774A (ja) | 2015-09-07 |
TWI631129B (zh) | 2018-08-01 |
TWI586678B (zh) | 2017-06-11 |
WO2014015241A1 (en) | 2014-01-23 |
EP2875166B1 (en) | 2018-04-11 |
KR20150036114A (ko) | 2015-04-07 |
TW201412762A (zh) | 2014-04-01 |
US9593133B2 (en) | 2017-03-14 |
US20150004317A1 (en) | 2015-01-01 |
TWI620751B (zh) | 2018-04-11 |
KR20150034123A (ko) | 2015-04-02 |
CN104080944A (zh) | 2014-10-01 |
TW201410690A (zh) | 2014-03-16 |
KR20150036122A (ko) | 2015-04-07 |
WO2014015248A1 (en) | 2014-01-23 |
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