JP6721906B2 - 縮環キノン置換ポリノルボルネン、電極活物質及び二次電池 - Google Patents
縮環キノン置換ポリノルボルネン、電極活物質及び二次電池 Download PDFInfo
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- JP6721906B2 JP6721906B2 JP2015200078A JP2015200078A JP6721906B2 JP 6721906 B2 JP6721906 B2 JP 6721906B2 JP 2015200078 A JP2015200078 A JP 2015200078A JP 2015200078 A JP2015200078 A JP 2015200078A JP 6721906 B2 JP6721906 B2 JP 6721906B2
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- methyl
- dimethyl
- ethyl
- propyl
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- 239000007772 electrode material Substances 0.000 title claims description 39
- 229920000636 poly(norbornene) polymer Polymers 0.000 title claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 239000010409 thin film Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 17
- 239000011232 storage material Substances 0.000 claims description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000011267 electrode slurry Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 6
- 229910001416 lithium ion Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004151 quinonyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- -1 nitroxy Chemical group 0.000 description 720
- 125000003277 amino group Chemical group 0.000 description 71
- 229920000642 polymer Polymers 0.000 description 71
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000008151 electrolyte solution Substances 0.000 description 24
- 238000002484 cyclic voltammetry Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000005259 measurement Methods 0.000 description 15
- 229910052744 lithium Inorganic materials 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 239000002134 carbon nanofiber Substances 0.000 description 5
- 239000003575 carbonaceous material Substances 0.000 description 5
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- FCDPQMAOJARMTG-UHFFFAOYSA-M benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphanium Chemical compound C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-M 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000007773 negative electrode material Substances 0.000 description 4
- WYQIVZKSGGKUAX-UHFFFAOYSA-N phenanthrene-3-carboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)=CC=C3C=CC2=C1 WYQIVZKSGGKUAX-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- BMQVXGRNMAVAEK-UHFFFAOYSA-N 2-iodoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(I)=CC=C3C(=O)C2=C1 BMQVXGRNMAVAEK-UHFFFAOYSA-N 0.000 description 3
- NKXXGBGMYWPUSM-UHFFFAOYSA-N 2-iodophenanthrene-9,10-dione Chemical compound C1=CC=C2C3=CC=C(I)C=C3C(=O)C(=O)C2=C1 NKXXGBGMYWPUSM-UHFFFAOYSA-N 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- 101150003085 Pdcl gene Proteins 0.000 description 3
- 229920002845 Poly(methacrylic acid) Chemical class 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001741 organic sulfur group Chemical group 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011986 second-generation catalyst Substances 0.000 description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000006230 acetylene black Substances 0.000 description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 2
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 2
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- OAEGRYMCJYIXQT-UHFFFAOYSA-N dithiooxamide Chemical compound NC(=S)C(N)=S OAEGRYMCJYIXQT-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- 125000004438 haloalkoxy 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
- 150000004694 iodide salts Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004676 n-butylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 2
- 125000006610 n-decyloxy group Chemical group 0.000 description 2
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 2
- 125000006609 n-nonyloxy group Chemical group 0.000 description 2
- 125000006608 n-octyloxy group Chemical group 0.000 description 2
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 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
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- 230000006866 deterioration Effects 0.000 description 1
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- 238000007646 gravure printing Methods 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
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- 125000005207 tetraalkylammonium group Chemical class 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- Chemical Kinetics & Catalysis (AREA)
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- Battery Electrode And Active Subsutance (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
1.下記式(1)及び/又は(2)で表される繰り返し単位を含む縮環キノン置換ポリノルボルネン。
2.前記芳香族炭化水素環がベンゼン環であり、前記芳香族複素環がチオフェン環である1の縮環キノン置換ポリノルボルネン。
3.下記式(1−1)、(1−2)及び/又は(1−3)で表される繰り返し単位を含む、2の縮環キノン置換ポリノルボルネン。
4.1〜3のいずれかの縮環キノン置換ポリノルボルネンからなる電荷貯蔵材料。
5.4の電荷貯蔵材料を含む電極活物質。
6.5の電極活物質、及び溶媒を含む電極スラリー。
7.5の電極活物質を含む薄膜。
8.6の電極スラリーから作製される薄膜。
9.5の電極活物質を含む電極。
10.7又は8の薄膜を含む電極。
11.9又は10の電極を含む二次電池。
12.9又は10の電極を含むリチウムイオン電池。
13.9又は10の電極を含む空気電池。
本発明の縮環キノン置換ポリノルボルネンは、下記式(1)及び/又は(2)で表される繰り返し単位を含む。
る。
本発明の縮環キノン置換ポリノルボルネンは、電荷貯蔵材料として好適に使用できる。電荷貯蔵材料とは電荷を貯蔵することができる材料のことであり、これは、例えば、二次電池の電極活物質として有用である。
本発明の二次電池は、前述した縮環キノン置換ポリノルボルネンからなる電荷貯蔵材料を電極活物質として用いることに特徴があり、その他の電池素子の構成部材は従来公知のものから適宜選択して用いればよい。
二次電池は、一般的に、正極層と、負極層と、正極層と負極層の間に配されるセパレータ層と、これら全てを含む電池素子内部に充填される電解液とから構成される。正極層及び負極層は、集電体である基板上に、電極活物質と、必要に応じて電極層の導電性向上のために炭素等からなる導電助剤と、更に必要に応じて成膜均一性向上、イオン伝導性向上、電解液への溶出抑制等のためにバインダーとを含む薄膜を形成することで構成される。電解液は、イオン伝導の本体である塩からなる電解質と溶媒等とから構成される。
日本電子(株)製、核磁気共鳴装置ECX-500(溶媒CDCl3、内標TMS)
(2)13C-NMR
日本電子(株)製、核磁気共鳴装置ECX-500(溶媒CDCl3、内標TMS)
(3)FAB-MS
日本電子(株)製、磁場形質量分析計JMS-GCMATE II GCMSシステム
(4)元素分析
Perkin Elmer社製、元素分析装置PE2400 II
(5)IRスペクトル
日本分光(株)製、フーリエ変換赤外分光光度計FT/IR-6100
(6)GPC測定
東ソー(株)製、HLC 8220
留出溶媒:クロロホルム
(7)CV測定、CP測定
ビー・エー・エス(株)製、ALS electrochemilas analyzer
[実施例1]ポリマーAの合成
[実施例1−1]2−ヨードアントラキノンの合成
1H-NMR (CDCl3, 500MHz, ppm) 8.64 (d, 1H, Ph), 8.29 (m, 2H, Ph), 8.14 (m, 1H, Ph), 7.98 (m, 1H, Ph), 7.81 (m, 2H, Ph)
FAB-MS (m/z):Calcd 334.11、Found 334.90
1H-NMR (CDCl3, 500MHz, ppm) 8.74 (s, 1H, Ph), 8.27 (m, 4H, Ph), 7.88 (m, 2H, Ph), 1.38 (s, 16H, CH3)
FAB-MS (m/z):Calcd 334.17、Found 335.19
1H-NMR (CDCl3, 500MHz, ppm) 8.18 (m, 4H, Ph), 7.95 (d, 2H, Ph), 7.88 (d, 2H, Ph), 7.71 (m, 4H, Ph), 7.32 (dd, 2H, Ph), 6.53 (m, 2H, HC=CH), 3.48 (m, 2H, CH), 3.29 (m, 2H, CH), 2.45 (d, 1H, CH2), 2.01 (d, 1H, CH2)
FAB-MS (m/z):Calcd 506.55、Found 507.11
1H-NMR (CDCl3, 500MHz, ppm) 8.20-7.31 (br, 14H, Ar), 5.86-5.01 (br, 2H, -CH=), 3.88-2.50 (br, 6H, aliphatic)
IR (KBr, cm-1):1675 (υ C=O)
GPC (CHCl3、40℃、RID):Mw=6.0×105, Mw/Mn=1.5
[実施例2−1]2−ヨード−9,10−フェナントレンキノンの合成
1H-NMR (CDCl3, 500MHz, ppm) 8.49 (d, 1H, Ph), 8.19 (dd, 1H, Ph), 8.03 (dd, 1H, Ph), 7.98 (d, 1H, Ph), 7.73 (m, 2H, Ph), 7.50 (t, 1H, Ph)
FAB-MS (m/z):Calcd 334.11、Found 334.89
1H-NMR (CDCl3, 500MHz, ppm) 8.15 (d, 1H, Ph), 8.08 (d, 1H, Ph), 7.96 (d, 1H, Ph), 7.91 (d, 1H, Ph), 7.68 (t, 1H, Ph), 7.61 (m, 1H, Ph), 7.43 (t, 1H, Ph), 6.27 (dd, 1H, HC=CH), 6.19 (dd, 1H, HC=CH), 3.02 (s, 1H, CH), 2.95 (s, 1H, CH), 2.75 (m, 1H, CH), 1.73 (m, 2H, CH2), 1.51 (m, 2H, CH2)
FAB-MS (m/z):Calcd 300.4、Found 301.3
GPC (CHCl3、40℃、RID):insoluble
[実施例3−1]9,10−フェナントレンキノン−3−カルボン酸の合成
続いて、100mLフラスコに、フェナントレン−3−カルボン酸489mg(2.20mmol)を添加し、酢酸20mLに溶解させた。別容器に酸化クロム(VI)808mg(8.80mmol、4eq)と18−クラウン−6 90mg(0.367mmol、0.167eq)とを加え、酢酸10mLと純水1mLとの混合溶媒に溶解させた。完全に溶解したところでフラスコに投入し、60℃で16時間反応させた。反応終了後、純水を添加し析出した黄色固体を酢酸/純水(1/1)の混合溶媒、及びジエチルエーテルにより洗浄し、黄色固体の9,10−フェナントレンキノン−3−カルボン酸を得た。1H-NMR及びFAB-MSの結果を以下に示す。
1H-NMR (DMSO-d6, 500MHz, ppm) 13.5 (s, 1H, OH), 8.66 (s, 1H, Ph), 8.30 (d, 1H, Ph), 8.09 (d, 1H, Ph), 8.03 (d, 1H, Ph), 7.99 (d, 1H, Ph), 7.76 (t, 1H, Ph), 7.54 (t, 1H, Ph)
FAB-MS (m/z):Calcd 252.0、Found 253.4
1H-NMR (CDCl3, 500MHz, ppm) 8.69 (d, 1H, Ph), 8.23 (m, 2H, Ph), 8.10 (m, 2H, Ph), 7.77 (m, 1H, Ph), 7.51 (m, 1H, Ph), 6.25-6.00 (br, 2H, HC=CH), 4.51-3.97 (br, 2H, CH2), 3.03-2.55 (br, 2H, CH2), 1.94 (m, 1H, CH), 1.55-0.65 (br, 4H, CH2)
FAB-MS (m/z):Calcd 358.12、Found 359.30
GPC (CHCl3、40℃、RID):Mw=1.1×104, Mw/Mn=1.8
[実施例4−1]化合物Dの合成
1H-NMR (CDCl3, 500MHz, ppm) 8.63 (s, 2H, Ph), 8.15 (m, 4H, Ph), 8.04 (m, 4H, Ph), 7.71 (t, 2H, Ph), 7.47 (t, 2H, Ph), 6.29 (m, 2H, HC=CH), 4.60 (m, 4H, CH2), 2.92 (m, 2H, CH), 2.20 (m, 2H, CH), 1.60 (dd, 2H, CH2)
FAB-MS (m/z):Calcd 622.16、Found 623.37
GPC (CHCl3、40℃、RID):insoluble
[実施例5]ポリマーAを用いた薄膜電極のCV測定
0.5mg/mLのポリマーAクロロホルム溶液300μLをGC基板上に滴下し、乾燥させて、ポリマーA薄膜電極を得た。
次に、得られた電極を電解液に浸して、電極中の空隙に電解液を染み込ませた。電解液としては、10mol/Lの水酸化ナトリウム水溶液を用いた。
前記薄膜電極11を作用極に、白金電極12を対極に、Ag/AgCl電極13を参照極に用い、これらをビーカー内に設置し、この中に前記と同様の電解液14を加えて、図1に示すようなビーカーセル1を作製した。
このビーカーセル1を用いて、スキャンレート5mV/secでCV測定を行った。結果を図2に示す。図2に示すように、ポリマーAを用いて作製した薄膜電極は、E1/2=−0.86Vに一段階4電子の酸化還元波が現れ、減衰、溶出は見られなかった。
実施例5で作製したポリマーA薄膜電極を負極、酸素還元触媒電極を正極とし、電解液は10mol/Lの水酸化ナトリウム水溶液を選択し空気二次電池を作製した。スキャンレート5mV/secでCV測定を行った。E1/2=−0.67V(vs. O2/O2 4-)に可逆な酸化還元波が現れた。また、−0.55Vから−1.1Vの範囲でCP測定を行ったところ、酸化還元波に合致するプラトーが観測され、100%のクーロン効率を示した。充放電を300サイクル繰り返した後でも初期容量の96%を維持し、ポリマーAが高いサイクル特性を示す物質であることがわかった。CV測定の結果を図3に、充放電容量を変化させた場合の基準電極との電位差の測定結果、及び充放電サイクル特性を示すグラフを図4に示す。
図1に示されるビーカーセルを用いて、CV測定を行った。
実施例2で合成したポリマーB(実施例7)又は実施例3で合成したポリマーC(実施例8)10mgに、気相成長炭素繊維80mg及びNMP1.5gに溶解させたポリフッ化ビニリデンバインダー10mgを加え、ボールミルを用いて混練した。15分程混合して得られた混合体をGC基板上に塗布し、これを室温(20℃)で12時間加熱真空乾燥して薄膜電極11を得た。
次に得られた電極を電解液に浸して、電極中の空隙に電解液を染み込ませた。電解液としては、1mol/Lの過塩素酸リチウムのγ−ブチロラクトン溶液を用いた。
前記薄膜電極11を作用極に、白金電極12を対極に、Ag/AgCl電極13を参照極に用い、これらをビーカー内に設置し、この中に前記と同様の電解液14を加えて、図1に示すようなビーカーセル1を作製した。
このビーカーセル1を用いて、スキャンレート10mV/secでCV測定を行った。結果を図5に示す。なお、図5中、実線は実施例7(ポリマーB)を、点線は実施例8(ポリマーC)を表す。図5に示すように、ポリマーCを用いた場合にエステルの電子吸引性に起因した、より貴な酸化還元電位が得られた。
実施例2及び3で合成したポリノルボルネン主鎖を有するポリマーB(実施例9)及びポリマーC(実施例10)を用い、ビーカーセル型の半電池を作製した。
ポリマーBを用いて作製した半電池を146μAの定電流で電圧が−0.8Vになるまで充電し、その後146μAで放電を行った。その結果、電圧が−0.5V及び−0.1V付近で50秒間ほぼ一定となった後、急激に上昇し放電容量は51mAh/gとなった。クーロン効率は88%であった。
また、ポリマーCを用いて作製した半電池を146μAの定電流で電圧が−0.75Vになるまで充電し、その後146μAで放電を行った。その結果、電圧が−0.4V及び0.1V付近で130秒間ほぼ一定となった後、急激に上昇し放電容量は87mAh/gとなった。クーロン効率は81%であった。
これにより、ポリマーB及びポリマーCが電荷貯蔵材料として動作していることを確認した。充放電容量を変化させた場合の基準電極との電位差の測定結果を図6に示す。なお、図6中、点線は実施例9(ポリマーB)を、実線は実施例10(ポリマーC)を表す。ポリマーCを用いた場合により高い充放電容量を示し、側鎖の高い自由度による溶媒への親和性の向上が示唆された。
実施例8で作製したポリマーC/炭素複合電極を正極、金属リチウムを負極とし、電解液は1mol/Lの過塩素酸リチウムのγ−ブチロラクトン溶液を選択しポリマーリチウム二次電池を作製した。なお、ポリマーリチウム二次電池は以下の手法で作製した。アルミ箔上にポリマー/炭素複合電極を作製し半径6mmに、セパレータは半径8.5mmにそれぞれ切り抜いた。プラス端子ケース上にプラスチック製ガスケット、炭素複合電極、セパレータ、金属リチウム、スペーサー及びワッシャーの順に積層し、キャップをはめカシメ機ホルダーを用いて充分にカシメることでポリマーリチウム二次電池を作製した。
スキャンレート5mV/secでCV測定を行ったところ、二段階の酸化還元波が現れた。また、293μAの定電流で電位が2Vから3.6Vの範囲でCP測定を行ったところ、二段階の酸化還元波が観測され、放電容量は65mAh/g、クーロン効率は84%であった。CV測定の結果を図7に、充放電量を変化させた場合の基準電極との電位差の測定結果を図8に示す。
図1に示されるビーカーセルを用いて、CV測定を行った。
実施例4で合成したポリマーD10mgに、炭素粉末80mg及びNMP1.5gに溶解させたポリフッ化ビニリデンバインダー10mgを加え、ボールミルを用いて混練した。15分程混合して得られた混合体をGC基板上に塗布し、これを室温(20℃)で12時間加熱真空乾燥して薄膜電極11を得た。
次に得られた電極を電解液に浸して、電極中の空隙に電解液を染み込ませた。電解液としては、1mol/Lの過塩素酸リチウムのγ−ブチロラクトン溶液を用いた。
前記薄膜電極11を作用極に、白金電極12を対極に、Ag/AgCl電極13を参照極に用い、これらをビーカー内に設置し、この中に前記と同様の電解液14を加えて、図1に示すようなビーカーセル1を作製した。
このビーカーセル1を用いて、スキャンレート10mV/secでCV測定を行った。結果を図9に示す。図9に示すように、ポリマーDを用いて作製した薄膜電極は、E1/2=0.02V、−0.40Vに可逆な酸化還元波が現れた。
実施例4で合成したポリマーDを用い、ビーカーセル型の半電池を作製した。
作製した半電池を240μAの定電流で電圧が−0.7Vになるまで充電し、その後240μAで放電を行った。その結果、−0.4V及び0V付近で140秒間ほぼ一定となった後、急激に上昇し、放電容量は108mAh/gとなった。クーロン効率は77%であった。これによりポリマーDが電荷貯蔵材料として動作していることを確認した。放電容量を変化させた場合の基準電極との電位差の測定結果を図10に示す。
また、同様にして480μA、720μA、960μA、1200μAの定電流で充放電を行い、20〜50Cでの放電容量を測定した。その結果、10Cの放電容量に対し50Cでも約70%の容量を示したことから、密な構造由来の電子交換が行われていることが予想される。放電レートが10〜50Cの時の放電曲線を図11に示す。
実施例12で作製したポリマーD/炭素複合電極を正極、金属リチウムを負極とし、電解液は1mol/Lの過塩素酸リチウムのγ−ブチロラクトン溶液を選択しポリマーリチウム二次電池を作製した。なお、ポリマーリチウム二次電池は、実施例11の方法に従って作製した。
スキャンレート5mV/secでCV測定を行ったところ、両極の電位差に相当する位置に酸化還元波が現れた。また、111μAの定電流で電位が1.8Vから3.6Vの範囲でCP測定を行ったところ、二段階の酸化還元波が観測され、放電容量は104mAh/g、クーロン効率は95%であった。CV測定の結果を図12に、充放電量を変化させた場合の基準電極との電位差の測定結果を図13に示す。
11 作用極
12 対極
13 参照極
14 電解液
Claims (12)
- 下記式(1)で表される繰り返し単位を含む縮環キノン置換ポリノルボルネン。
- 下記式(1−3)で表される繰り返し単位を含む、請求項1記載の縮環キノン置換ポリノルボルネン。
- 請求項1又は2記載の縮環キノン置換ポリノルボルネンからなる電荷貯蔵材料。
- 請求項3記載の電荷貯蔵材料を含む電極活物質。
- 請求項4記載の電極活物質、及び溶媒を含む電極スラリー。
- 請求項4記載の電極活物質を含む薄膜。
- 請求項5記載の電極スラリーから作製される薄膜。
- 請求項4記載の電極活物質を含む電極。
- 請求項6又は7記載の薄膜を含む電極。
- 請求項8又は9記載の電極を含む二次電池。
- 請求項8又は9記載の電極を含むリチウムイオン電池。
- 請求項8又は9記載の電極を含む空気電池。
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