JP6671717B2 - リチウム空気電池用電解質、及びそれを含むリチウム空気電池 - Google Patents
リチウム空気電池用電解質、及びそれを含むリチウム空気電池 Download PDFInfo
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- JP6671717B2 JP6671717B2 JP2015107270A JP2015107270A JP6671717B2 JP 6671717 B2 JP6671717 B2 JP 6671717B2 JP 2015107270 A JP2015107270 A JP 2015107270A JP 2015107270 A JP2015107270 A JP 2015107270A JP 6671717 B2 JP6671717 B2 JP 6671717B2
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- lithium
- group
- electrolyte
- air battery
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- 239000003792 electrolyte Substances 0.000 title claims description 112
- 229910052744 lithium Inorganic materials 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 57
- 229910001416 lithium ion Inorganic materials 0.000 claims description 55
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 54
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 48
- -1 difluoropropyl Chemical group 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- 125000001153 fluoro group Chemical group F* 0.000 claims description 35
- 239000002241 glass-ceramic Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 229910003002 lithium salt Inorganic materials 0.000 claims description 25
- 159000000002 lithium salts Chemical class 0.000 claims description 25
- 239000011521 glass Substances 0.000 claims description 24
- 239000007784 solid electrolyte Substances 0.000 claims description 20
- 239000011737 fluorine Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000010936 titanium Substances 0.000 claims description 18
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 17
- 150000002500 ions Chemical class 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000010416 ion conductor Substances 0.000 claims description 12
- 229910021645 metal ion Inorganic materials 0.000 claims description 12
- 239000000919 ceramic Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000010954 inorganic particle Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 9
- 239000005518 polymer electrolyte Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910018068 Li 2 O Inorganic materials 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 229910003480 inorganic solid Inorganic materials 0.000 claims description 6
- 229910000664 lithium aluminum titanium phosphates (LATP) Inorganic materials 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 5
- 229910010093 LiAlO Inorganic materials 0.000 claims description 5
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims description 5
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- CVJYOKLQNGVTIS-UHFFFAOYSA-K aluminum;lithium;titanium(4+);phosphate Chemical compound [Li+].[Al+3].[Ti+4].[O-]P([O-])([O-])=O CVJYOKLQNGVTIS-UHFFFAOYSA-K 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- 239000002223 garnet Substances 0.000 claims description 4
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910018119 Li 3 PO 4 Inorganic materials 0.000 claims description 3
- 229910008550 Li2O—Al2O3—SiO2—P2O5—TiO2—GeO2 Inorganic materials 0.000 claims description 3
- MKGYHFFYERNDHK-UHFFFAOYSA-K P(=O)([O-])([O-])[O-].[Ti+4].[Li+] Chemical compound P(=O)([O-])([O-])[O-].[Ti+4].[Li+] MKGYHFFYERNDHK-UHFFFAOYSA-K 0.000 claims description 3
- PPVYRCKAOVCGRJ-UHFFFAOYSA-K P(=S)([O-])([O-])[O-].[Ge+2].[Li+] Chemical compound P(=S)([O-])([O-])[O-].[Ge+2].[Li+] PPVYRCKAOVCGRJ-UHFFFAOYSA-K 0.000 claims description 3
- 229910020213 PB(Mg3Nb2/3)O3-PbTiO3 Inorganic materials 0.000 claims description 3
- 229910020210 Pb(Mg3Nb2/3)O3—PbTiO3 Inorganic materials 0.000 claims description 3
- 229910020346 SiS 2 Inorganic materials 0.000 claims description 3
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 3
- 229910002367 SrTiO Inorganic materials 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 claims description 3
- 229910000659 lithium lanthanum titanates (LLT) Inorganic materials 0.000 claims description 3
- 229910001386 lithium phosphate Inorganic materials 0.000 claims description 3
- 229910003465 moissanite Inorganic materials 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 3
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 33
- 229910052760 oxygen Inorganic materials 0.000 description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 27
- 239000001301 oxygen Substances 0.000 description 27
- 239000013078 crystal Substances 0.000 description 26
- 230000003647 oxidation Effects 0.000 description 25
- 238000007254 oxidation reaction Methods 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000012528 membrane Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229910018071 Li 2 O 2 Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 11
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000004502 linear sweep voltammetry Methods 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 238000006056 electrooxidation reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910010238 LiAlCl 4 Inorganic materials 0.000 description 3
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 description 3
- 229910013372 LiC 4 Inorganic materials 0.000 description 3
- 229910013684 LiClO 4 Inorganic materials 0.000 description 3
- 229910013385 LiN(SO2C2F5)2 Inorganic materials 0.000 description 3
- 229910013870 LiPF 6 Inorganic materials 0.000 description 3
- 229910012513 LiSbF 6 Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- 238000006479 redox reaction Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000006738 (C6-C20) heteroaryl group Chemical group 0.000 description 2
- OXMIDRBAFOEOQT-UHFFFAOYSA-N 2,5-dimethyloxolane Chemical compound CC1CCC(C)O1 OXMIDRBAFOEOQT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KEQUNHIAUQQPAC-UHFFFAOYSA-N Dihydroxyacetone (dimer) Chemical compound OCC1(O)COC(O)(CO)CO1 KEQUNHIAUQQPAC-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229910015044 LiB Inorganic materials 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000001930 cyclobutanes Chemical class 0.000 description 2
- 150000001932 cycloheptanes Chemical class 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000001940 cyclopentanes Chemical class 0.000 description 2
- 150000001942 cyclopropanes Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000011267 electrode slurry Substances 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002641 lithium Chemical class 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
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- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 230000001681 protective effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material 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
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
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Description
R1及びR2は、互いに独立して、水素原子またはCR15R16R17であり、
R3ないしR17、並びにR20及びR21は、互いに独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、カルボン酸基、置換もしくは非置換のC1−C20アルキル基、置換もしくは非置換のC6−C30アリール基、または置換もしくは非置換のC3−C20ヘテロアリール基であり、
R18及びR19のうち少なくとも一つは、互いに独立して、フッ素原子、一部または全部がフッ素で置換もしくは非置換のC1−C10アルキル基、あるいは一部または全部がフッ素で置換されたC6−C30アリール基であり、残りのR18及びR19は、水素原子、置換もしくは非置換のC1−C10アルキル基、あるいは置換もしくは非置換のC6−C30アリール基であり、選択的に、R20とR21は、置換もしくは非置換のC3−C8環を形成することができ、
選択的に、R18及びR19は、全部または一部がフッ素で置換もしくは非置換のC3−C8環を形成することができ、
mは、1ないし1,000,000であり、nは、0ないし1,000,000であり、pは、0ないし1,000,000であり、m+n+p≧3である。
選択的に、R18及びR19、並びに/またはR20及びR21は、全部または一部がフッ素で置換されたシクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロノルボルナンまたはビシクロオクタンを形成し、残りのR18及びR19、あるいはR20及びR21は、非置換のシクロプロパン、非置換のシクロブタン、非置換のシクロペンタン、非置換のシクロヘキサン、非置換のシクロヘプタン、非置換のシクロノルボルナン、または非置換のビシクロオクタンを形成することが好ましい。
R15、R16、R17は、互いに独立して、水素、あるいは置換もしくは非置換のC1−C20アルキル基である。
R1及びR2は、互いに独立して、水素原子またはCR15R16R17であり、
R3ないしR17、並びにR20及びR21は、互いに独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、カルボン酸基、置換もしくは非置換のC1−C20アルキル基、置換もしくは非置換のC6−C30アリール基、あるいは置換もしくは非置換のC3−C20ヘテロアリール基であり、
R18及びR19のうち少なくとも一つは、互いに独立して、フッ素原子、一部または全部がフッ素で置換もしくは非置換のC1−C10アルキル基、あるいは一部または全部がフッ素で置換されたC6−C30アリール基であり、残りのR18及びR19は、水素原子、置換もしくは非置換のC1−C10アルキル基、あるいは置換もしくは非置換のC6−C30アリール基であり、選択的に、R20とR21は、置換もしくは非置換のC3−C8環を形成することができ、
選択的に、R18及びR19は、全部または一部がフッ素で置換もしくは非置換のC3−C8環を形成することができ、
mは、1ないし1,000,000であり、nは、0ないし1,000,000であり、pは、0ないし1,000,000であり、m+n+p≧3である。
選択的に、R18及びR19、並びに/またはR20及びR21は、全部または一部がフッ素で置換されたシクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロノルボルナンまたはビシクロオクタンを形成し、残りのR18及びR19、あるいはR20及びR21は、非置換のシクロプロパン、非置換のシクロブタン、非置換のシクロペンタン、非置換のシクロヘキサン、非置換のシクロヘプタン、非置換のシクロノルボルナン、または非置換のビシクロオクタンを形成することができる。
R15、R16、R17は、互いに独立して、水素、あるいは置換もしくは非置換のC1−C20アルキル基である。
[反応式1]
4Li+O2⇔2Li2O Eo=2.91V
2Li+O2⇔Li2O2 Eo=3.10V
[反応式2]
4Li+O2+2H2O⇔4LiOH Eo=3.45V
2,5−ビス(ヒドロキシメチル)−1,4−ジオキサン−2,5−ジオール(2, 5-bis(hydroxymethyl)-1, 4-dioxane-2, 5-diol)を、ピリジン5当量及び無水酢酸(acetic anhydride)4.1当量と反応させ、中間体1を合成した。
中間体1を、ジエチルアミノ硫黄トリフルオリド(DAST)3当量と反応させ、中間体2を合成した。
中間体2を、NaOMe 3当量と反応させ、中間体3を合成した。
中間体3を、Ag2O 1.5当量及び臭化ベンジル(benzyl bromide)1.2当量と反応させ、中間体4を合成した。中間体4において、Bnは、ベンジル基を意味する。
ジエチレングリコールを塩化トシル(TsCl)2当量及びKOH 4当量と反応させ、中間体5を合成した。
中間体4に中間体5を2当量添加し、KOH 5当量と共に反応させ、中間体6を合成した。
中間体6を、Pd/C触媒下でH2と反応させ、中間体7を合成した。
中間体7を、NaH 2.4当量、二黄化炭素(CS2)4当量及びヨード化メチル(MeI)2.4当量と反応させ、中間体8を合成した。
中間体8を、1,3−ブロモ−5,5’−ジメチルヒダントイン(1, 3-bromo-5, 5’-dimethylhydantoin)6当量及びHF/ピリジン120当量と反応させ、化合物A(化学式2の化合物)を合成した。
化学式2の化合物(化合物A)に、1MのLiTFSI(bis(trifluoromethanesulfonyl)imide)を添加して混合し、電解質を製造した。
カーボン(Super−P)40重量部、ポリテトラフルオロエチレン(PTFE)10重量部、及びN−メチルピロリドン(NMP)50重量部を混合し、正極スラリーを製造した後、スラリーをコーティング及び圧延し、正極合材シートを得た。正極合材シートをステンレスメッシュの上に圧着させた後、100℃オーブンで、120分間真空乾燥させて正極を得た。
化学式2の化合物(化合物A)の含量を、電解質総重量100重量部を基準にして、20重量部及び97重量部にそれぞれ変化させたことを除いては、実施例1と同一の方法によって電解質を製造した。
実施例1の電解質の代わりに、実施例3及び4の電解質をそれぞれ使用したことを除いては、実施例2と同一の方法を使用してリチウム空気電池を製造した。
下記のテトラグライム(TGM)に、1MのLiTFSIを添加して電解質を製造した。
化合物Bに、1MのLiTFSIを添加して電解質を製造した。
実施例1の電解質の代わりに、比較例1の電解質を使用したことを除いては、実施例2と同一の方法を使用してリチウム空気電池を製造した。
実施例1の電解質の代わりに、比較例2の電解質を使用したことを除いては、実施例2と同一の方法を使用してリチウム空気電池を製造した。
下記化学式6で表示される化合物に、1MのLiTFSIを添加して電解質を製造したる。
下記化学式8で表示される化合物に、1MのLiTFSIを添加して電解質を製造した。
下記化学式9で表示される化合物に、1MのLiTFSIを添加して電解質を製造した。
下記化学式10で表示される化合物に、1MのLiTFSIを添加して電解質を製造した。
実施例1、実施例3、実施例4、比較例1及び比較例2の電解質に対して、LSV(linear sweep voltammetry)を行った。
「化学的耐酸化性」とは、電解質の酸化に対する抵抗性を意味する。
60℃、1気圧、酸素雰囲気下で、実施例2,5−6、比較例3及び比較例4で製造されたリチウム空気電池を、0.24mA/cm2の定電流で、1.7V(Liに対して)まで放電させた後、同一の電流で4.2Vまで充電させ、その後、4.2V定電圧で、0.1mA/cm2の電流になるまで充電させた。1.7Vまでの放電時、経時的な電位差を測定した結果を図4に示した。図4のグラフを参照すれば、比較例3のリチウム空気電池は、電圧がいち早く低下するが、実施例2及び比較例4のリチウム空気電池は、電圧がさらに長い間維持されるということが分かる。また、実施例5−6のリチウム空気電池は、実施例2のリチウム空気電池と同等レベルの充放電特性を示した。
11 第1集電体
12 第2集電体
13 正極
14 負極
15,25 第1電解質
24 リチウムイオン伝導性層
26 第2電解質
Claims (16)
- 下記化学式1aで表示される化合物及び/又は化学式1bで表示される化合物、及びリチウム塩を含むリチウム空気電池用電解質:
R15、R16、及びR17は、互いに独立して、水素、あるいは置換もしくは非置換のC1−C20アルキル基であり、
- 前記R15ないしR17は、互いに独立して、水素、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基またはヘプチル基を含むことを特徴とする請求項1に記載のリチウム空気電池用電解質。
- 前記R18ないしR21は、互いに独立して、フッ素原子、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、フルオロエチル基、ジフルオロエチル基、トリフルオロエチル基、テトラフルオロエチル基、ペンタフルオロエチル基、フルオロプロピル基、ジフルオロプロピル基、トリフルオロプロピル基、テトラフルオロプロピル基、ペンタフルオロプロピル基、ヘキサフルオロプロピル基またはヘプタフルオロプロピル基を含み、選択的に、R18及びR19、並びに/またはR20及びR21は、全部または一部がフッ素で置換されたシクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロノルボルナンまたはビシクロオクタンを形成することを特徴とする請求項1又は2に記載のリチウム空気電池用電解質。
- 前記化学式1aで表示される化合物及び/又は化学式1bで表示される化合物の含量は、電解質総重量100重量部を基準にして、15ないし97重量部であることを特徴とする請求項1から4のいずれか一項に記載のリチウム空気電池用電解質。
- 前記リチウム塩は、リチウムスルホンイミド系化合物であることを特徴とする請求項1から5のいずれか一項に記載のリチウム空気電池用電解質。
- 前記リチウムスルホンイミド系化合物が、リチウムフルオロアルキルスルホンイミド、リチウムフルオロアリールスルホンイミドまたはリチウムフルオロアルキルアリールスルホンイミドを含むことを特徴とする請求項6に記載のリチウム空気電池用電解質。
- 前記リチウムスルホンイミド系化合物が、Li(FSO2)2N、Li(CF3SO2)2N、Li(C2F5SO2)2N、LiN(CpF2p+1SO2)(CqF2q+1SO2)(pとqは、互いに異なり、p及びqは、互いに独立して、1ないし20の整数である)、LiN((SO2)2CpF2p)(pは、1ないし10の整数である)、Li(C6F5SO2)2N、Li(C10F7SO2)2N、Li(C6F5SO2)(C10F7SO2)N、LiN(C6F5SO2)(CpF2p+1SO2)(pは、1ないし10の整数である)またはLiN(C10F7SO2)(CpF2p+1SO2)(pは、1ないし10の整数である)を含むことを特徴とする請求項6に記載のリチウム空気電池用電解質。
- 非水系有機溶媒をさらに含むことを特徴とする請求項1から8のいずれか一項に記載のリチウム空気電池用電解質。
- 負極と、
正極と、
リチウム塩、及び請求項1から9のいずれか一項に記載の電解質と、を含むリチウム空気電池。 - 前記電解質の一部または全部が、前記正極に含浸されたことを特徴とする請求項10に記載のリチウム空気電池。
- 前記負極と電解質との間に、イオン伝導性無機物粒子を含むリチウムイオン伝導性層がさらに含まれることを特徴とする請求項10または11に記載のリチウム空気電池。
- 前記イオン伝導性無機物粒子は、ガラス質活性金属イオン伝導体、非晶質活性金属イオン伝導体、セラミックス活性金属イオン伝導体、及びガラス−セラミックス活性金属イオン伝導体のうちから選択された一つ以上、またはそれらの組み合わせであることを特徴とする請求項12に記載のリチウム空気電池。
- 前記イオン伝導性無機物粒子は、Li1+x+yAlxTi2−xSiyP3−yO12(0<x<2、0≦y<3)、BaTiO3、Pb(Zr,Ti)O3(PZT)、Pb1−xLaxZr1−yTiyO3(PLZT)(O≦x<1、O≦y<1)、PB(Mg3Nb2/3)O3−PbTiO3(PMN−PT)、HfO2、SrTiO3、SnO2、CeO2、Na2O、MgO、NiO、CaO、BaO、ZnO、ZrO2、Y2O3、Al2O3、TiO2、SiO2、SiC、リチウムホスフェート(Li3PO4)、リチウムチタンホスフェート(LixTiy(PO4)3、0<x<2、0<y<3)、リチウムアルミニウムチタンホスフェート(LixAlyTiz(PO4)3、0<x<2、0<y<1、0<z<3)、Li1+x+y(Al,Ga)x(Ti,Ge)2−xSiyP3−yO12(O≦x≦1、O≦y≦1)、リチウムランタンチタネート(LixLayTiO3、0<x<2、0<y<3)、リチウムゲルマニウムチオホスフェート(LixGeyPzSw、0<x<4、0<y<1、0<z<1、0<w<5)、リチウムニトリド(LixNy)(0<x<4、0<y<2)、SiS2(LixSiySz)系ガラス(0<x<3、0<y<2、0<z<4)、P2S5(LixPySz)系ガラス(0<x<3、0<y<3、0<z<7)、Li2O、LiF、LiOH、Li2CO3、LiAlO2、Li2O−Al2O3−SiO2−P2O5−TiO2−GeO2系セラミックス、及びガーネット系セラミックス(Li3+xLa3M2O12)(0≦x≦5)(M=Te、NbあるいはZr)のうちから選択された一つ以上、またはそれらの組み合わせであることを特徴とする請求項12に記載のリチウム空気電池。
- 前記負極とリチウムイオン伝導性層との間に、第2電解質がさらに含まれることを特徴とする請求項12から14のいずれか一項に記載のリチウム空気電池。
- 前記第2電解質が、固体高分子電解質または無機固体電解質であることを特徴とする請求項15に記載のリチウム空気電池。
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