JP7446656B2 - 複合膜、それを含んだ負極構造体及びリチウム電池、並びに複合膜製造方法 - Google Patents
複合膜、それを含んだ負極構造体及びリチウム電池、並びに複合膜製造方法 Download PDFInfo
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- JP7446656B2 JP7446656B2 JP2019001039A JP2019001039A JP7446656B2 JP 7446656 B2 JP7446656 B2 JP 7446656B2 JP 2019001039 A JP2019001039 A JP 2019001039A JP 2019001039 A JP2019001039 A JP 2019001039A JP 7446656 B2 JP7446656 B2 JP 7446656B2
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- composite membrane
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- 229910052731 fluorine Inorganic materials 0.000 claims description 57
- 239000011737 fluorine Substances 0.000 claims description 56
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 55
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- 239000007789 gas Substances 0.000 claims description 30
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- 239000002904 solvent Substances 0.000 claims description 28
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- 238000000034 method Methods 0.000 claims description 19
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- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
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- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 11
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- BWTMTZBMAGYMOD-UHFFFAOYSA-N (2,2,3,3,4,4,5,5-octafluoro-6-prop-2-enoyloxyhexyl) prop-2-enoate Chemical compound C=CC(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C BWTMTZBMAGYMOD-UHFFFAOYSA-N 0.000 claims description 10
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- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002222 fluorine compounds Chemical class 0.000 claims description 6
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 5
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- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
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- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 2
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- 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 2
- 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 2
- 229910020213 PB(Mg3Nb2/3)O3-PbTiO3 Inorganic materials 0.000 claims description 2
- 229910020210 Pb(Mg3Nb2/3)O3—PbTiO3 Inorganic materials 0.000 claims description 2
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- 229910002367 SrTiO Inorganic materials 0.000 claims description 2
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- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical group C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229910000659 lithium lanthanum titanates (LLT) Inorganic materials 0.000 claims description 2
- 229910001386 lithium phosphate Inorganic materials 0.000 claims description 2
- 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 claims description 2
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- 238000004528 spin coating Methods 0.000 claims description 2
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- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 claims description 2
- 229910005793 GeO 2 Inorganic materials 0.000 claims 1
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- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 claims 1
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- URZWHNFFWSYUMB-UHFFFAOYSA-B aluminum lithium silicon(4+) titanium(4+) tetraphosphate Chemical compound P(=O)([O-])([O-])[O-].[Si+4].[Ti+4].[Al+3].[Li+].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-] URZWHNFFWSYUMB-UHFFFAOYSA-B 0.000 description 1
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- WUFQNPMBKMKEHN-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;diethyl-(2-methoxyethyl)-methylazanium Chemical compound CC[N+](C)(CC)CCOC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F WUFQNPMBKMKEHN-UHFFFAOYSA-N 0.000 description 1
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
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- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical class [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- BXHHZLMBMOBPEH-UHFFFAOYSA-N diethyl-(2-methoxyethyl)-methylazanium Chemical compound CC[N+](C)(CC)CCOC BXHHZLMBMOBPEH-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
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- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
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- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
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- 229910021389 graphene Inorganic materials 0.000 description 1
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- 229910021473 hassium Inorganic materials 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- HZNPCLUBXJLRAA-UHFFFAOYSA-N iron;oxomolybdenum Chemical class [Fe].[Mo]=O HZNPCLUBXJLRAA-UHFFFAOYSA-N 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000006132 parent glass Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
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- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
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- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 239000002733 tin-carbon composite material Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- BHZCMUVGYXEBMY-UHFFFAOYSA-N trilithium;azanide Chemical compound [Li+].[Li+].[Li+].[NH2-] BHZCMUVGYXEBMY-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/446—Composite material consisting of a mixture of organic and inorganic materials
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- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
- H01M4/134—Electrodes based on metals, Si or alloys
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0079—Manufacture of membranes comprising organic and inorganic components
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
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- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M12/00—Hybrid cells; Manufacture thereof
- H01M12/08—Hybrid cells; Manufacture thereof composed of a half-cell of a fuel-cell type and a half-cell of the secondary-cell type
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/38—Selection of substances as active materials, active masses, active liquids of elements or alloys
- H01M4/381—Alkaline or alkaline earth metals elements
- H01M4/382—Lithium
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/403—Manufacturing processes of separators, membranes or diaphragms
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/411—Organic material
- H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/411—Organic material
- H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
- H01M50/426—Fluorocarbon polymers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/431—Inorganic material
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/44—Fibrous material
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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Description
[反応式1]:
4Li+O2→2Li2O Eo=2.91V
2Li+O2→Li2O2 Eo=3.10V
実施例1:TTT+4T+PFDA(6:9:7.4)
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mg、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)(4T)900mg及び1,3,5-トリアリル-1,3,5-トリアジン-2,4,6-トリオン(TTT)600mg、及び光開始剤である下記化学式で表示されるIrgacure 369(BASF)30mgを混合して撹拌を実施し、高分子膜形成用組成物を得た。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mgの代りに、Fomblin(登録商標)MT70(Solvay)400mgを使用したことを除いては、実施例1と同一方法で有機膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mgの代りに、2,2’-(2,2,3,3,4,4,5,5,6,6-デカフルオロヘプタン-1,7-ジイル)ビス(オキシラン)50mgを使用したことを除いては、実施例1と同一方法で有機膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)を添加しないことを除いては、実施例1と同一方法で有機膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mg、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)(4T)900mg及び1,3,5-トリアリル-1,3,5-トリアジン-2,4,6-トリオン(TTT)600mgの代わりに、Fomblin(登録商標)MT70(Solvay)500mgだけを単独で使用したことを除いては、実施例1と同一方法で有機膜を製造した。
実施例4:TTT+4T+PFDA(6:9:7.4)
リチウム-チタン-アルミニウム-リン酸塩(LTAP:Li1.4Ti1.6Al0.4P3O12)膜(Ohara glass、Ohara corporation)を粉砕した後、該粉砕物に対して、気孔径が約20μmx25μmである網シーブでシービングを実施し、約22μmサイズ(平均粒径)を有するLTAP粒子を得た。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mgの代わりに、Fomblin(登録商標)MT70(Solvay)400mgを使用したことを除いては、実施例1と同一方法で複合膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mgの代わりに、2,2’-(2,2,3,3,4,4,5,5,6,6-デカフルオロヘプタン-1,7-ジイル)ビス(オキシラン)50mgを使用したことを除いては、実施例1と同一方法で複合膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)を添加しないことを除いては、実施例1と同一方法で複合膜を製造した。
2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート(PFDA)740mg、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)(4T)900mg及び1,3,5-トリアリル-1,3,5-トリアジン-2,4,6-トリオン(TTT)600mgの代わりに、Fomblin(登録商標)MT70(Solvay)500mgだけを単独で使用したことを除いては、実施例1と同一方法で複合膜を製造した。
実施例7:リチウム空気電池の製造
多重壁カーボンナノチューブ(XinNano社)、イオン性液体である1Mのリチウムビス(トリフルオロスルホニルイミド)(LiTFSI)を含むN,N-ジエチル-N-メチル-N-(2-メトキシエチル)アンモニウムビス(トリフルオロメチルスルホニル)イミド(DEME-TFSI)、及びポリフッ化ビニリデンを5:25:1重量比で混合し、シート状のカソードを製造した。シート状のカソードを切断し、カソードを直径8mmのディスク状に得た。
実施例4の複合膜の代わりに、実施例5及び6の複合膜をそれぞれ使用したことを除いては、実施例7と同一方法によって実施し、リチウム空気電池を製造した。
実施例4の複合膜の代わりに、比較例3及び4の複合膜をそれぞれ使用したことを除いては、実施例7と同一方法によって実施し、リチウム空気電池を製造した。
実施例1ないし3、及び比較例1及び2で製造された有機膜に対して、酸素透過度を下記方法によって評価した。
実施例1及び比較例1で製造された高分子膜に対して、Universal Test Machine(LLOYD LS100)を使用し、引っ張り強度(tensile strength)及び伸率(yield strain)を測定し、その結果の一部を下記表2に示した。
実施例1ないし3、並びに比較例1及び2で製造された有機膜に対して、膨潤率(swelling ratio)を下記方法によって評価した。
[数式1]
膨潤率(%)=[(含浸後の有機膜重量-含浸前の有機膜重量)/含浸前の有機膜重量]×100
実施例4ないし6、並びに比較例3及び4で製造された複合膜に対して、充放電安定性を評価した。
実施例7で製造されたリチウム空気電池が、温度約60℃、酸素雰囲気下で維持されるチャンバ内に配置された。該リチウム空気電池は、酸素1気圧で、0.24mA/cm2のCCモード(constant current mode)で放電させ、4.3V CVモード(constant voltage mode)で充電させた。
11,21 イオン伝導性無機粒子
12,22 有機膜
13 貫通ホール
30 リチウム空気電池
31 ケース
32 基材
33,62,310 負極
34,36,320 電解質
37,63 正極
38a 空気注入口
38b 空気排出口
39 押さえ部材
61 リチウムイオン電池
64 セパレータ
65 電池ケース
66 キャップアセンブリ
Claims (30)
- 有機膜と、
複数個のイオン伝導性無機粒子と、
を含む複合膜であって、
前記有機膜が架橋共重合体を含み、
前記架橋共重合体が、1以上の第1反復単位と、1以上のフッ素非含有第2反復単位と、1以上のフッ素非含有第3反復単位と、を含み、
前記1以上の第1反復単位のうちの少なくとも1つがフッ素含有反復単位であり、
前記第1反復単位が、下記化学式1ないし3のいずれかで表示され:
A1、A2、A3及びA4は、互いに独立して、共有結合、-C(=O)-O-、-C(=O)-、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
R1及びR2は、互いに独立して、ハロゲンで置換もしくは非置換の炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;-(-Ra-O-)k-(ここで、kは、2ないし100の数であり、Raは、ハロゲンで置換もしくは非置換のC2-C10アルキレン基である);ハロゲンで置換もしくは非置換のC6-C10シクロアルキレン基;ハロゲンで置換もしくは非置換のC6-C10アリーレン基;またはハロゲンで置換もしくは非置換のC2-C10ヘテロアリーレン基であり、
但し、第1反復単位がフッ素含有反復単位である場合には、R1及びR2は、それぞれ1以上のフッ素原子を含み、
X1及びX2は、互いに独立して、共有結合、-NH-C(=O)-、-CH2CH(OH)-、-CF2CF(OH)-、-O-または-S-であり、
a1、a2、及びbは、モル分率であり、あり、0≦a1<1、0≦a2<1、0≦b<1及び0<a1+a2+b<1であり、
前記フッ素非含有第2反復単位が、下記化学式4で表示され:
A5、A6、A7及びA8は、互いに独立して、共有結合、-C(=O)-O-、-C(=O)-、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
R 4、R5 、R 8、及びR 9 は、互いに独立して、炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;-(-Ra-O-)k-(ここで、kは、2ないし100の数であり、Raは、C2-C10アルキレン基である);C6-C10シクロアルキレン基;C6-C10アリーレン基;またはC2-C10ヘテロアリーレン基であり、
R 3 、R 6 、R 7 及びR 10 は、互いに独立して、炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;またはC 6 -C 10 シクロアルキレン基であり、
X 3、X4、X5、及びX 6 は、-S-であり、
cは、モル分率であり、0≦c<1であり、
前記フッ素非含有第3反復単位が、下記化学式8ないし10のいずれかで表示され:
A9、A10、及びA11 は、互いに独立して、共有結合、-O-、-C(=O)-O-、-C(=O)-、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
R11、R12、R13、R14、R15、及びR16は、互いに独立して、共有結合、炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;-(-Ra-O-)k-(ここで、kは、2ないし100の数であり、Raは、C2-C10アルキレン基である);C6-C10シクロアルキレン基;C6-C10アリーレン基;またはC2-C10ヘテロアリーレン基であり、
CY1は、1以上の置換基で置換もしくは非置換のC2-C20ヘテロ環;1以上の置換基で置換もしくは非置換のC5-C20脂肪族炭化水素環;1以上の置換基で置換もしくは非置換のC6-C20アリール環;または1以上の置換基で置換もしくは非置換のC2-C20ヘテロアリール環であり、
X10、X11、及びX12 は、互いに独立して、共有結合、-NH-C(=O)-、-CH2CH(OH)-、-CF2CF(OH)-、-O-または-S-であり、
g、h、及びiは、モル分率であり、0≦g<1、0≦h<1、0≦i<1であり、0<g+h+i<1である、複合膜。 - 前記CY1が、下記化学式14ないし17のいずれかで表示されることを特徴とする請求項1に記載の複合膜:
R15は、互いに独立して、水素原子、炭素数1ないし10の直鎖状あるいは分枝状のアルキル基であり、
R27は、互いに独立して、水素原子、-C(=O)-、または炭素数1ないし10の直鎖状あるいは分枝状のアルキル基であり、
Y2、Y3及びY4は、互いに独立して、C、N、またはPであり、
ただし、Y2、Y3及びY4が、互いに独立して、N、またはPである場合、Y2、Y3及びY4は、R15、R27、または他の連結基に結合されず、
mは、0ないし10であり、nは、0ないし9であり、qは、0ないし4であり、かつrは、0ないし3である。 - 前記フッ素含有第1反復単位の含量の和が、架橋共重合体全体を基準として、1ないし50wt%であり、前記フッ素非含有第2反復単位及び前記フッ素非含有第3反復単位の含量の和が、架橋共重合体全体を基準として、50ないし99wt%であることを特徴とする請求項1または2に記載の複合膜。
- 前記架橋共重合体が
重合可能な含フッ素化合物と、重合可能な非フッ素系化合物と、4個のチオール基を有するポリチオールとの重合生成物
を含むことを特徴とする請求項1から3のいずれか一項に記載の複合膜。 - 前記架橋共重合体が、
多官能性アクリル系モノマー、多官能性ビニル系モノマー及び多官能性イソシアネート系モノマーのうちから選択された1以上の多官能性非フッ素系モノマーと、4個のチオール基を有するポリチオールと、多官能性含フッ素アクリル系モノマー、多官能性含フッ素ビニル系モノマー、多官能性含フッ素イソシアネート系モノマー、多官能性含フッ素エポキシド系モノマーのうちから選択された1以上の多官能性含フッ素モノマーとの重合生成物
を含む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複合膜。 - 前記多官能性含フッ素モノマーが下記化学式18、20、及び21のいずれかで表示されることを特徴とする請求項5に記載の複合膜:
A1 及びA 2 は、互いに独立して、共有結合、-C(=O)-O-、-C(=O)-、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、 B1、B2、B3及びB4は、互いに独立して、共有結合、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
R 1 は、ハロゲンで置換もしくは非置換の炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;-(-Ra-O-)k-(ここで、kは、2ないし100の数であり、Raは、ハロゲンで置換もしくは非置換のC2-C10アルキレン基である);ハロゲンで置換もしくは非置換のC6-C10シクロアルキレン基;ハロゲンで置換もしくは非置換のC6-C10アリーレン基;またはハロゲンで置換もしくは非置換のC2-C10ヘテロアリーレン基であり、
但し、R 1は、それぞれ1以上のフッ素原子を含む。 - 前記多官能性非フッ素系モノマーが、トリメチロールプロパントリアクリレート、トリメチロールプロパントリメタクリレート、1,3,5-トリアリル-1,3,5-トリアジン-2,4,6-トリオン、及び2,4,6-トリス(アリルオキシ)-1,3,5-トリアジンのうちから選択された1以上であり、
前記ポリチオールが、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)、及びペンタエリトリトールテトラキス(2-メルカプトアセテート)のうちから選択された1以上であり、
前記多官能性含フッ素モノマーが、2,2,3,3,4,4,5,5-オクタフルオロヘキサン-1,6-ジイルジアクリレート、及び2,2’-(2,2,3,3,4,4,5,5,6,6-デカフルオロヘプタン-1,7-ジイル)ビス(オキシラン)のうちから選択された1以上であることを特徴とする請求項5に記載の複合膜。 - 前記有機膜の水分遮断特性及びガス遮断特性が、ASTM(D3985)による連続的フローテスト方法によって測定して1.1cm3・cm/(m2・日・atm)以下であることを特徴とする請求項1から7のいずれか一項に記載の複合膜。
- 前記有機膜のガス透過度が、10-3ないし2,000cm3・cm/(m2・日・atm)である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複合膜。
- 前記有機膜が、折り曲げ可能である柔軟性膜であることを特徴とする請求項1から9のいずれか一項に記載の複合膜。
- 前記有機膜の引っ張り強度が10MPa以上であり、伸率が1%以上であることを特徴とする請求項1から10のいずれか一項に記載の複合膜。
- 前記有機膜を80℃の電解液〔1-エチル-3-メチルイミダゾリウムビス(トリフルオロメタンスルホニル)イミド(EMI)[EMIM][N(Tf)2]に1M LiTFSIを溶解させた液体電解質、又はプロピレンカーボネート(PC)溶媒に、1M LITFSIを溶解させた液体電解質〕に24時間含浸した後の膨潤率が、30%以下であることを特徴とする請求項1から11のいずれか一項に記載の複合膜。
- 前記有機膜が、複数個の貫通ホールを有し、前記複数個のイオン伝導性無機粒子が前記貫通ホールに配置されることを特徴とする請求項1から12のいずれか一項に記載の複合膜。
- 前記複合膜の表面が、連続的な有機膜内にイオン伝導性無機粒子が不連続的に配置された海島構造を含むか、あるいは、前記複合膜の断面が、有機膜とイオン伝導性無機粒子とが相互に整列された構造を含むことを特徴とする請求項1から12のいずれか一項に記載の複合膜。
- 前記有機膜内に埋め込まれた複数個のイオン伝導性無機粒子が、単一層に配置されることを特徴とする請求項1から14のいずれか一項に記載の複合膜。
- 前記複数個のイオン伝導性無機粒子が、粒子間境界がない単一粒子であることを特徴とする請求項1から15のいずれか一項に記載の複合膜。
- 前記複数個のイオン伝導性無機粒子の含量は、複合膜総重量100重量部を基準にして、10ないし90重量部であることを特徴とする請求項1に記載の複合膜。
- 前記複数個のイオン伝導性無機粒子は、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1以上、またはそれらの組み合わせ物であることを特徴とする請求項1に記載の複合膜。
- 前記複数個のイオン伝導性無機粒子は、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)、窒化リチウム系ガラス(LixNy、0<x<4、0<y<2)、SiS2系ガラス(LixSiySz、0<x<3、0<y<2、0<z<4)、P2S5系ガラス(LixPySz、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、ガーネット系セラミックス(Li3+xLa3M2O12(M=Te、NbまたはZr、xは、1ないし10の整数である))のうちから選択された1以上、またはそれらの組み合わせ物であることを特徴とする請求項1に記載の複合膜。
- 前記イオン伝導性無機粒子の平均粒径が、電子走査顕微鏡(SEM)によって測定して、1ないし300μmであることを特徴とする請求項1に記載の複合膜。
- 前記複合膜のガス透過度が、10-3ないし2,000cm3・cm/(m2・日・atm)であり、
前記複合膜において、複数個のイオン伝導性無機粒子の露出面積が、複合膜総面積を基準にして、30ないし80%であることを特徴とする請求項1に記載の複合膜。 - 負極と、
請求項1ないし21のうちいずれか1項に記載の複合膜と、を含む負極構造体。 - 請求項22に記載の負極構造体を含むリチウム電池。
- 前記リチウム電池が、リチウム金属電池またはリチウム空気電池であることを特徴とする請求項23に記載のリチウム電池。
- 基材上にイオン伝導性無機粒子を配置する段階と、
前記イオン伝導性無機粒子間に、重合可能な化合物、及び溶媒を含む混合物を配置する段階と、
前記混合物から溶媒を除去する段階と、
前記重合可能な化合物を重合させて複合膜を形成する段階と、
を含む、請求項1~24のいずれか一項に記載の複合膜の製造方法であって、
前記重合可能な化合物が、
前記1以上の第1反復単位を形成する、1以上の多官能性含フッ素モノマーおよび任意の多官能性非フッ素系モノマーと、
前記1以上のフッ素非含有第2反復単位及び1以上のフッ素非含有第3反復単位を形成する、2以上の多官能性非フッ素系モノマーと、
を含み、
但し、前記重合可能な化合物が、前記第1反復単位を形成する多官能性含フッ素モノマーを少なくとも1つ含むことを条件とする、複合膜の製造方法。 - 前記基材が、接着性基材であることを特徴とする請求項25に記載の複合膜の製造方法。
- 前記混合物を配置する段階が、スピンコーティングによって遂行されることを特徴とする請求項25に記載の複合膜の製造方法。
- 前記重合可能な化合物が、下記化学式18ないし21のいずれかで表示される、1以上の多官能性含フッ素モノマーおよび任意の多官能性非フッ素系モノマーを含むことを特徴とする請求項25に記載の複合膜の製造方法:
A1 及びA 2 は、互いに独立して、共有結合、-C(=O)-O-、-C(=O)-、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
A 3 及びA 4 は、互いに独立して、炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
B1、B2、B3及びB4は、互いに独立して、共有結合、または炭素数1ないし5の直鎖状あるいは分枝状のアルキレン基であり、
R1及びR2は、互いに独立して、ハロゲンで置換もしくは非置換の炭素数1ないし10の直鎖状あるいは分枝状のアルキレン基;-(-Ra-O-)k-(ここで、kは、2ないし100の数であり、Raは、ハロゲンで置換もしくは非置換のC2-C10アルキレン基である);ハロゲンで置換もしくは非置換のC6-C10シクロアルキレン基;ハロゲンで置換もしくは非置換のC6-C10アリーレン基;またはハロゲンで置換もしくは非置換のC2-C10ヘテロアリーレン基であり、
但し、多官能性含フッ素モノマーである場合には、R1及びR2は、それぞれ1以上のフッ素原子を含み、
X1a及びX2aは、-S-であり、
Z1及びZ2は、水素原子である。 - 前記溶媒を除去する段階が、25ないし60℃で実施されることを特徴とする請求項25に記載の複合膜の製造方法。
- 前記重合可能な化合物の含量は、前記イオン伝導性無機粒子100重量部を基準にして、10ないし1,000重量部であることを特徴とする請求項25に記載の複合膜の製造方法。
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US10930913B2 (en) | 2021-02-23 |
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