WO2006041007A1 - イオン伝導体 - Google Patents
イオン伝導体 Download PDFInfo
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- WO2006041007A1 WO2006041007A1 PCT/JP2005/018541 JP2005018541W WO2006041007A1 WO 2006041007 A1 WO2006041007 A1 WO 2006041007A1 JP 2005018541 W JP2005018541 W JP 2005018541W WO 2006041007 A1 WO2006041007 A1 WO 2006041007A1
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- Prior art keywords
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- formula
- crosslinkable functional
- functional group
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- 239000010416 ion conductor Substances 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 49
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003792 electrolyte Substances 0.000 claims abstract description 31
- 239000011737 fluorine Substances 0.000 claims abstract description 31
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 22
- 229920000570 polyether Polymers 0.000 claims abstract description 22
- 229920001774 Perfluoroether Polymers 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000005518 polymer electrolyte Substances 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005587 carbonate group Chemical group 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 35
- 239000003990 capacitor Substances 0.000 abstract description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052744 lithium Inorganic materials 0.000 abstract description 6
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 150000002500 ions Chemical class 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- -1 alkali metal salt Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000007784 solid electrolyte Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229910013872 LiPF Inorganic materials 0.000 description 4
- 101150058243 Lipf gene Proteins 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229910013075 LiBF 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
- 150000005215 alkyl ethers Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 229910015013 LiAsF Inorganic materials 0.000 description 2
- 229910020808 NaBF Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011245 gel electrolyte Substances 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- CNJLMVZFWLNOEP-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(C)CCC2C(C)(C)C12 CNJLMVZFWLNOEP-UHFFFAOYSA-N 0.000 description 1
- SBUOHGKIOVRDKY-UHFFFAOYSA-N 4-methyl-1,3-dioxolane Chemical compound CC1COCO1 SBUOHGKIOVRDKY-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 102000018726 Host Cell Factor C1 Human genes 0.000 description 1
- 108010027310 Host Cell Factor C1 Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- QLKXXDJVUWMMDH-UHFFFAOYSA-N furan tetrahydrate Chemical compound O.O.O.O.O1C=CC=C1 QLKXXDJVUWMMDH-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002250 progressing effect Effects 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
- 230000000717 retained effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/56—Solid electrolytes, e.g. gels; Additives therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/60—Liquid electrolytes characterised by the solvent
-
- 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
-
- 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
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
-
- 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
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0569—Liquid materials characterised by the solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/02—Polyalkylene oxides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0085—Immobilising or gelification of electrolyte
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Definitions
- the present invention relates to an ionic conductor comprising an amorphous fluorine-containing polyether compound having a fluoroether group in the side chain.
- Powerful ion conductors are useful as lithium secondary batteries, solar cells, and polymer electrolytes for capacitors.
- Lithium secondary batteries, solar cells, and capacitor electrolytes are currently mainly organic molecules.
- the technology is aimed at polymer electrolytes in order to avoid leakage of electrolyte solutions. Development is progressing.
- a polymer electrolyte As such a polymer electrolyte, a polymer gel type that combines a polymer containing an ethylene oxide (EO) unit with an electrolyte salt (metal salt) and an organic solvent. Things are known.
- EO ethylene oxide
- metal salt electrolyte salt
- the EO-electrolyte salt ion conductor has a high viscosity, so the dissociated ions move smoothly! /, Kana! /, And the electrolyte salt dissolves in multiple phases. Because it is a crystalline polymer, its ionic conductivity is affected by the phase change, particularly the melting of the EO crystalline phase, so the ionic conductivity is low at room temperature1, and the crystallization rate is slow. There is an essential problem that the conductivity changes with time.
- a diatalylate containing a fluorine-containing polyether (n is 10 to 20) is crosslinked, and a metal salt and an organic solvent are disclosed.
- JP-A-11-53937 proposes the use of a copolymer of a fluorephrine unit and an alkyl butyl ether or alkyl allyl ether unit having a carbonate bond.
- An object of the present invention is to provide an ionic conductor capable of achieving a higher ionic conductivity than such a conventional one.
- the present inventors can further reduce the viscosity of the resulting fluorine-containing polyether compound by introducing a fluoroether unit into the side chain of the EO unit, and therefore, without using an organic solvent.
- the inventors have found that the ionic conductivity can be increased by about one order, and have completed the present invention.
- the present invention includes an ion conductive compound (I) and an electrolyte salt ( ⁇ ),
- the ion conductive compound (I) is represented by the formula (1):
- Rf is crosslinkable functional group which may have a Furuoroeteru group
- R 1 is a group or a bond that binds the Rf main chain
- ether having an Furuoroeteru group in the side chain represented by the unit
- AE is the formula (2b):
- R has a hydrogen atom, an alkyl group optionally having a crosslinkable functional group, a crosslinkable functional group! An aliphatic cyclic hydrocarbon group or a crosslinkable functional group. An aromatic hydrocarbon group; R 1 is an ether unit represented by a group or a bond that bonds R to the main chain);
- a and B are the same force or different and contain a hydrogen atom, a fluorine atom and Z or a crosslinkable functional group !, or an alkyl group, a fluorine atom and Z or a phenyl group which may contain a crosslinkable functional group , —COOH group, —OR 2 (R 2 is a hydrogen atom or fluorine atom and Z or an alkyl group which may contain a crosslinkable functional group), ester group or carbonate group].
- the present invention relates to an ionic conductor which is an amorphous fluorine-containing polyether compound having a fluoroether group or a cross-linked product thereof.
- the ionic conductor of the present invention comprises a specific polymer ion conductive compound (I) and an electrolyte salt (II).
- the specific polymer ion conductive compound (I) used in the present invention has the formula (1):
- Rf is crosslinkable functional group which may have a Furuoroeteru group
- R 1 is a group or a bond that binds the Rf main chain
- ether having an Furuoroeteru group in the side chain represented by the unit
- AE is the formula (2b):
- R has a hydrogen atom, an alkyl group optionally having a crosslinkable functional group, a crosslinkable functional group! An aliphatic cyclic hydrocarbon group or a crosslinkable functional group. An aromatic hydrocarbon group; R 1 is an ether unit represented by a group or a bond that bonds R to the main chain);
- a and B are the same force or different and contain a hydrogen atom, a fluorine atom and Z or a crosslinkable functional group !, or an alkyl group, a fluorine atom and Z or a phenyl group which may contain a crosslinkable functional group , —COOH group, —OR 2 (R 2 is a hydrogen atom or fluorine atom and Z or an alkyl group which may contain a crosslinkable functional group), ester group or carbonate group].
- Amorphous fluorine-containing polyether having fluoroether group Compound.
- the amorphous fluorine-containing polyether compound (1) having a fluoroether group in the side chain is obtained by introducing a fluoroether side chain into a conventional ethylene oxide (EO) unit. Increase the viscosity of the compound.
- EO ethylene oxide
- the fluoroether group Rf is excellent in acid resistance and nonflammability, it exhibits excellent stability for use at high temperatures.
- Rf is preferably represented by the formula (2a-1):
- Rf 1 is one (OCFCFCF) CFCFCFO)-,-(OCFZ'CF
- OCFCFCH OCHCHCF
- OCFCHCH OCFCHCH
- X is a hydrogen atom, a halogen atom, an ether bond having a carbon number of 120, and Z or a crosslinkable functional group, and may be at least one selected from fluorine-containing alkyl groups, provided that X In which Rf 1 does not exist, and Rf 1 does not contain an O—O 2 structure).
- Rf 1 is (OCFZ'CF) (OCF CF CF) (OCH CF
- One (OCFZtF) is preferred to be one or more repeating units.
- nl is preferably small.
- Preferable specific examples include, for example, — (OCF CF) —, — (OCF CF CF) —, — (OCF CF CF) —, — (OCF CF CF) —, — (OCF CF CF)
- CF) 0) — is preferable because it has excellent thermal stability and oxidation resistance and is easy to synthesize.
- X may include a hydrogen atom, a halogen atom, an ether bond having 120 carbon atoms, and Z or a crosslinkable functional group, and may be at least one selected from fluorine-containing alkyl groups.
- Rf 1 does not have, and Rf 1 does not contain —O—O structure.
- Rf in the formula (2a) examples include the formula (2a-2):
- n2 is an integer of 0 to 2). This product is easy to synthesize and is inexpensive in cost.
- n3 is 0 or 1
- n4 is 0 or 1
- n5 is an integer of 0 to 2).
- Preferred! / include the following (exemplified by Rf! /).
- Dl include, for example,
- n is an integer from 1 to 200, n2 is the same as above
- n is an integer from 1 to 200, n2 is the same as above
- n is an integer from 1 to 200, n2 is the same as above
- n is an integer from:! to 200, n2 is the same as above
- Rf—R 1 — is particularly excellent in reactivity and easy to synthesize.
- m is 0, that is, the compound (la) having only the fluoroether group-containing unit (D1), and m is There are compounds (lb) containing one or more, that is, both a fluoroether group-containing unit (D1) and an alkyl ether unit (AE).
- n is preferably 6 or less, more preferably 4 or less, and particularly 2 or less.
- an amorphous fluorine-containing polyether compound (lb) combined with an alkyl ether unit (AE) having a high dielectric constant can also be used. Incorporation of alkyl ether units (AE) increases the crystallinity, so nZm is about 0.1 / 99.9, or 1/99 to 50/50.
- R may have a hydrogen atom, a crosslinkable functional group, an alkyl group, or a crosslinkable functional group! /, May! It has an aromatic hydrocarbon group or a crosslinkable functional group, and may be an aromatic hydrocarbon group.
- the alkyl group is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, such as methyl, ethyl and the like.
- Preferred examples of the aliphatic cyclic hydrocarbon group include cycloalkyl groups having 4 to 8 carbon atoms. Examples thereof include cyclopentyl and cyclohexyl.
- Preferred examples of the aromatic hydrocarbon group include phenol and benzyl.
- Substituted by these groups is preferably a crosslinkable functional group U.
- Specific examples include X in the above formula (2a-1) (excluding H, F and fluorine-containing groups). Along with preferable examples.
- R are preferably a linear or branched alkyl group having 1 to 20 carbon atoms from the viewpoint of excellent polymerizability, strength, and electrolyte solubility, and particularly methyl and ethyl. preferable.
- the bondability with the main chain represented by R 1 is a force that can adopt the above four types, particularly the direct bond type and the ether type.
- a and B are the same or different and contain a hydrogen atom, a fluorine atom and a crosslinkable functional group.
- A Preferable specific examples of A include, for example,
- n 7 is an integer of 1 to: L 0), and from the viewpoint of improving crosslinking reactivity and dielectric constant,
- n 8 is an integer from 1 to 5)
- CH 3 is preferred.
- Preferable specific examples of B include, for example,
- n 9 is an integer from 1 to 10.
- n 10 is an integer from 1 to 5)
- CH 3 is preferred.
- the number average molecular weight of the amorphous fluorine-containing polyether compound (1) having a fluoroether group in the side chain is 500 or more, more preferably 1000 or more, particularly 1500 or more.
- the upper limit is preferably 100000, more preferably 80000, and especially 50000 in terms of the solubility of the electrolyte.
- the power to give a specific example of an amorphous fluorine-containing polyether compound having a fluoroether group in the side chain represented by the formula (1) is not limited thereto.
- Amorphous fluorine-containing polyether compound (lb) [0076] [Chemical 29]
- n is an integer from 1 to 200
- m is an integer from 1 to 20000
- the amorphous fluorine-containing polyether compound (1) having a fluorine-containing group in the side chain used in the present invention is, for example, an ion polymerization using a key-on such as O-, C-, and N as an initiator.
- the ion conductive compound (I) may be a crosslinked product! /.
- the cross-linked product can be produced by introducing a cross-linkable functional group into the amorphous fluorine-containing polyether compound (1) having a fluoro ether group in the side chain and, if necessary, cross-linking using a cross-linking agent. .
- a crosslinked product By using a crosslinked product, the mechanical strength of the ionic conductor is greatly improved.
- Examples of the crosslinkable functional group include a bur group, an acryl group, a glycidyl group, an epoxy group, a hydroxyl group, a carboxyl group, an allyloyl group, a cyano group, an alkoxysilyl group, and the like.
- Z or B, Rf in formula (2a), R in formula (2b) may be introduced.
- a method in which a compound having a crosslinkable functional group is reacted for post-modification can be employed.
- the crosslinking agent may be appropriately selected from polyfunctional compounds having two or more of the above-mentioned crosslinkable functional groups in one molecule.
- crosslinking agent examples include, for example,
- n 11 is an integer from 1 to 8)
- a cross-linking agent described in, for example, 79826 can also be used.
- Crosslinking may be performed by a known crosslinking system suitable for a combination of a crosslinkable functional group and a crosslinking agent.
- electrolyte (II) which is one component of the ionic conductor of the present invention will be described.
- Examples of the electrolyte (i) that can be used in the present invention include conventionally known metal salts, ionic liquids, inorganic polymer type salts, organic polymer type salts, and the like.
- electrolytes are particularly suitable compounds depending on the intended use of the ionic conductor.
- suitable electrolytes are exemplified for each application, but are not limited to the illustrated specific examples. In other applications, the following exemplified electrolytes can be appropriately used.
- the metal salt for the solid electrolyte of the lithium secondary battery includes boron-on type, oxygen-on type, nitrogen-on type, carbon-on type, and phosphorus-on type.
- Various organic metal salts can be used, and oxygen ion type and nitrogen ion type are preferable.
- oxygen-on type specifically, CF SO Li, C F SO Li, C F SO Li, CH
- Nitrogen-on types include (CF SO) NLi (TFSl), (C F SO) NLi (BETI), (C
- LiPF LiPF, LiBF, LiAsF, LiCIO and the like can be used.
- LiPF or LiBF LiPF or LiBF
- Et NBF Et is ethylene
- Et NC F SO is particularly preferable, Et NBF, Et NPF is preferably used
- LiPF LiPF, LiBF, LiAsF, LiCIO, NaPF, NaBF, NaAsF
- NaCIO, KPF, KBF, KAsF, KCIO, etc. can be used, especially LiPF, L
- R la R 2a R 3a R 4a NI (R la to R 1 ⁇ 2 are the same or different, and an alkyl group having 1 to 3 carbon atoms), Lil, Nal , KI,
- Etc. can be exemplified.
- an ionic liquid is used as the electrolyte (II), organic and inorganic ions and polyalkylimidazolium cations, N for lithium secondary batteries, capacitors, and solid electrolytes of dye-sensitized solar cells.
- examples include salts with alkylpyridium cation, tetraalkylammonium cation and tetraalkylphosphonium cation, with 1,3 dialkylimidazolium salt being particularly preferred! /.
- polyalkylimidazolium cations include 1,3-dialkylimidazolium cations such as 1-ethyl-3-methylimidazolium cation (EMI +) and 1-butyl-3-methylimidazolium cation (BMI +); 1,2 dimethyl 3 Trialkylimidazolium cations such as propylimidazolium cation (DMPI +) are preferred!
- 1,3-dialkylimidazolium cations such as 1-ethyl-3-methylimidazolium cation (EMI +) and 1-butyl-3-methylimidazolium cation (BMI +)
- EMI + 1-ethyl-3-methylimidazolium cation
- BMI + 1-butyl-3-methylimidazolium cation
- DMPI + propylimidazolium cation
- EMIA1C1 EMIBF, EMIPF, EMIAsF, EMII, EMICH C
- MI CF SO
- BMI C F SO
- DMPIAICI DMPIBF
- DMPIPF DMPIAICI
- PIAsF PIAsF
- DMPII DMPII
- DMPICH COO DMPICF COO
- DMPIC F COO DMPIC
- F SO examples include F SO, DMPIC F SO, DMPI (CF SO) N, DMPI (C F SO) N
- Oxides such as ⁇ , ⁇ and DMPII are particularly suitable for solid electrolytes in dye-sensitized solar cells.
- the amount of electrolyte ( ⁇ ) blended varies depending on the required current density, application, type of electrolyte, etc., but the polymer ion conductive compound (1) is 0.1 parts by weight per 100 parts by weight. Or even It is preferably 1 part by mass or more, particularly 2 parts by mass or more, 200 parts by mass or less, more preferably 100 parts by mass or less, particularly 50 parts by mass or less.
- the electrolyte ( ⁇ ⁇ ⁇ ) is retained by impregnating or dissolving it in the amorphous fluorine-containing polyether compound (1) constituting the polymer ion conductive compound (I).
- the amorphous fluorine-containing polyether compound (1) is solid but has a low viscosity, so that the ionic conductivity is high as it is.
- an aprotic organic solvent (III) is added to form a gel (plasticized) gel electrolyte.
- Examples of the organic solvent (III) used in the gel electrolyte include ethylene carbonate, propylene power carbonate, butylene carbonate, y butyrolatatane, 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,3 dioxolane, 4-Methyl-1,3- dioxolane, methyl formate, methyl acetate, methyl propionate, dimethyl carbonate, ethyl methyl carbonate, jetyl carbonate, acetonitrile, dimethyl sulfoxide, methyl pyrrolidone, etc., especially dielectric constant and oxidation resistance From the standpoint of improving the properties and electrochemical stability, ethylene carbonate, propylene carbonate, jetino carbonate, ⁇ -butylate ratatone, 1,2 dimethoxyethane, 1,3 dioxolan, and acetonitrile are preferred.
- the organic solvent (III) is preferably used in such an amount that the solid content in the ionic conductor is 10% by mass or more, more preferably 50% by mass or more, and particularly 100% by mass.
- the ionic conductor of the present invention may contain other additives as required.
- other additives include metal oxides and glass.
- the ion conductor of the present invention has high ion conductivity and is excellent in oxidation resistance and mechanical strength. Therefore, the polymer electrolyte of a lithium secondary battery, the polymer electrolyte of a capacitor, and a thick battery. It is particularly useful as a polymer electrolyte for positive cells (particularly dye-sensitized solar cells). It can also be used as electrolytes for various sensors, electrolytes for electochromic elements, and ion conductors used for various electrolysis.
- NMR BRUKER AC-300 is used.
- the number average molecular weight was determined by gel permeation chromatography (GPC) using Tosoh's GPC HLC-8020, Shodex column (one GPC KF-801 and one GPC KF-802). , GPC KF-806M connected in series) and tetrahydrate-furan (THF) as a solvent at a flow rate of 1 mlZ.
- GPC gel permeation chromatography
- T thermal decomposition temperature
- Viscosity Using a VISCONE CV series cone plate type rotational viscometer made by Tokai Yagami Co., Ltd., measuring cones with a viscosity range of 50 to 8000 mPa's, rotating at 94 rpm, and temperature of 80 ° C.
- a 100 ml glass eggplant-shaped flask equipped with a stirrer was thoroughly purged with nitrogen, then 0.19 g of CH ONa and 70 g of dimethylformamide were added under a nitrogen stream at room temperature.
- reaction solution was poured into pure water.
- the liquid separated into the lower layer was extracted using HCFC1 41b. After drying the extracted solution with MgSO, HCFC141b can be distilled off.
- the obtained high-viscosity liquid was vacuum-dried to obtain 12.3 g of the colorless and transparent homopolymer of the above compound (I 3).
- This polymer was analyzed by 19 F-NMR and —NMR analysis.
- the number average molecular weight measured by GPC analysis using tetrahydrofuran (THF) as a solvent was 5,830 and the weight average molecular weight was 8,567.
- a supersaturated amount of LiCIO as an electrolyte was dissolved in a mixture of 2 g of the polymer obtained in Synthesis Example 2 and 0.2 g of propylene carbonate, and left standing in a 6 ml sample bottle. -After the turn
- a solid was deposited in the transparent polymer mixture phase, lower layer.
- the upper layer was taken out, after manufactured create a rectangular film was measured for ionic conductivity was 7. 8 X 10- 4 SZcm.
- the polymer ion conductor of the present invention itself has high ion conductivity even near room temperature, is nonflammable with low viscosity, and has excellent acid resistance, and is a secondary lithium ion. It can satisfy the characteristics required as a polymer electrolyte for batteries, capacitors and solar cells.
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JPH07114941A (ja) * | 1993-08-26 | 1995-05-02 | Japan Energy Corp | イオン伝導体 |
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JPH0948832A (ja) * | 1995-08-03 | 1997-02-18 | Japan Energy Corp | イオン伝導体 |
JP2000234020A (ja) * | 1998-12-17 | 2000-08-29 | Nisshinbo Ind Inc | 高分子電解質用ポリマー及びイオン導電性高分子電解質用組成物 |
JP2003007337A (ja) * | 2001-06-21 | 2003-01-10 | Daiso Co Ltd | ポリマー二次電池 |
WO2004059664A1 (ja) * | 2002-12-25 | 2004-07-15 | Daikin Industries, Ltd. | 含フッ素エーテル鎖を含む含フッ素ポリマーからなる固体電解質 |
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JPH08183854A (ja) * | 1994-12-28 | 1996-07-16 | Japan Energy Corp | 含フッ素ポリエーテル、その製法、及びそれを含むイオン伝導体 |
JPH0948832A (ja) * | 1995-08-03 | 1997-02-18 | Japan Energy Corp | イオン伝導体 |
JP2000234020A (ja) * | 1998-12-17 | 2000-08-29 | Nisshinbo Ind Inc | 高分子電解質用ポリマー及びイオン導電性高分子電解質用組成物 |
JP2003007337A (ja) * | 2001-06-21 | 2003-01-10 | Daiso Co Ltd | ポリマー二次電池 |
WO2004059664A1 (ja) * | 2002-12-25 | 2004-07-15 | Daikin Industries, Ltd. | 含フッ素エーテル鎖を含む含フッ素ポリマーからなる固体電解質 |
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