JP2018131387A - 有機化合物、電極活物質及びこれを用いた二次電池 - Google Patents
有機化合物、電極活物質及びこれを用いた二次電池 Download PDFInfo
- Publication number
- JP2018131387A JP2018131387A JP2017023740A JP2017023740A JP2018131387A JP 2018131387 A JP2018131387 A JP 2018131387A JP 2017023740 A JP2017023740 A JP 2017023740A JP 2017023740 A JP2017023740 A JP 2017023740A JP 2018131387 A JP2018131387 A JP 2018131387A
- Authority
- JP
- Japan
- Prior art keywords
- secondary battery
- active material
- electrode active
- organic compound
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 65
- 239000007772 electrode material Substances 0.000 title claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229910052751 metal Chemical class 0.000 claims abstract description 13
- 239000002184 metal Chemical class 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 239000008151 electrolyte solution Substances 0.000 claims description 16
- 229910001416 lithium ion Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 11
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910001415 sodium ion Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract description 2
- -1 radical compounds Chemical class 0.000 description 31
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 21
- 239000003792 electrolyte Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910052744 lithium Inorganic materials 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229920001940 conductive polymer Polymers 0.000 description 10
- 238000006479 redox reaction Methods 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007774 positive electrode material Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 239000007773 negative electrode material Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000002033 PVDF binder Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000011255 nonaqueous electrolyte Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 239000007769 metal material Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 229910000314 transition metal oxide Inorganic materials 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- FDSRSUAVHPFWGT-UHFFFAOYSA-N (3,5-dibenzoylphenyl)-phenylmethanone Chemical compound C=1C(C(=O)C=2C=CC=CC=2)=CC(C(=O)C=2C=CC=CC=2)=CC=1C(=O)C1=CC=CC=C1 FDSRSUAVHPFWGT-UHFFFAOYSA-N 0.000 description 2
- JTRVXIZNCRODHQ-UHFFFAOYSA-N 5-phenyl-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1C1=CC=CC=C1 JTRVXIZNCRODHQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910000676 Si alloy Inorganic materials 0.000 description 2
- 229910001128 Sn alloy Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000006230 acetylene black Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002134 carbon nanofiber Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910021385 hard carbon Inorganic materials 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- KFCDDRTYJQZGKK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enenitrile Chemical compound C=CC#N.CC(=C)C(O)=O KFCDDRTYJQZGKK-UHFFFAOYSA-N 0.000 description 1
- KSONICAHAPRCMV-UHFFFAOYSA-N 5-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2C(=O)CCC2=C1 KSONICAHAPRCMV-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- XDJQVCIRFIRWKY-UHFFFAOYSA-N C=C.C(=C)(F)F Chemical group C=C.C(=C)(F)F XDJQVCIRFIRWKY-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-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
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 1
- 229910015645 LiMn Inorganic materials 0.000 description 1
- 229910013290 LiNiO 2 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910021314 NaFeO 2 Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- OFQYTFGQKLIGRD-UHFFFAOYSA-N O=C(C(Cc1c2)(Br)Br)c1ccc2-c1ccc(-c(cccc2)c2C2=O)c2c1 Chemical compound O=C(C(Cc1c2)(Br)Br)c1ccc2-c1ccc(-c(cccc2)c2C2=O)c2c1 OFQYTFGQKLIGRD-UHFFFAOYSA-N 0.000 description 1
- BWDUNPXGFSRQDG-UHFFFAOYSA-N O=C(C(Cc1c2)(Br)Br)c1ccc2-c1ccccc1 Chemical compound O=C(C(Cc1c2)(Br)Br)c1ccc2-c1ccccc1 BWDUNPXGFSRQDG-UHFFFAOYSA-N 0.000 description 1
- BPOYSULDYKGEBJ-UHFFFAOYSA-N O=C(CCc1c2)c1ccc2-c1ccc(-c(cccc2)c2C2=O)c2c1 Chemical compound O=C(CCc1c2)c1ccc2-c1ccc(-c(cccc2)c2C2=O)c2c1 BPOYSULDYKGEBJ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 230000010757 Reduction Activity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- BMWYMEQOMFGKSN-UHFFFAOYSA-N benzo[g]cinnoline Chemical compound N1=NC=CC2=CC3=CC=CC=C3C=C21 BMWYMEQOMFGKSN-UHFFFAOYSA-N 0.000 description 1
- SLSPYQCCSCAKIB-UHFFFAOYSA-N bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F SLSPYQCCSCAKIB-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000002482 conductive additive Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 238000003411 electrode reaction Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011245 gel electrolyte Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000006713 insertion reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000010220 ion permeability Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002116 nanohorn Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- CVSGFMWKZVZOJD-UHFFFAOYSA-N pyrazino[2,3-f]quinoxaline Chemical compound C1=CN=C2C3=NC=CN=C3C=CC2=N1 CVSGFMWKZVZOJD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001256 stainless steel alloy Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical group S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Images
Classifications
-
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Secondary Cells (AREA)
- Battery Electrode And Active Subsutance (AREA)
Abstract
Description
示されている。これは導電性高分子の酸化還元に伴うリチウムイオンなどの電解質イオンのドープ、脱ドープ反
応を原理とした二次電池である。
単位質量当たりの理論容量の向上が期待される。
[1]下記式(1)で表される構造を有する、有機化合物、
[2]下記式(2)で表される構造を有する、有機化合物、
[3]下記式(5)で表される構造を有する、有機化合物、
[4]下記式(6)で表される構造を有する、前項[3]に記載の有機化合物、
[6]正極、負極、及び電解液を備え、前記正極および前記負極から選ばれる少なくとも1つが、前項[1]〜[4]のいずれか一項に記載の有機化合物又は前項[5]に記載の二次電池用電極活物質を含む、二次電池、
[7]ナトリウムイオンもしくはリチウムイオンである前項[6]に記載の二次電池、
に関する。
本発明の有機化合物は、トルキセノン構造を構成単位中に含有する上記特定の有機化合物を主体としているので、多電子反応が可能であり、しかも酸化還元反応に対する安定性も優れるため、これを二次電池用電極活物質に用いることで、少ない分子量で高容量密度のサイクル特性が良好な電極活物質を得ることが出来る。
上記のような置換基を選択することで、化合物の固体状態における分子間力が増大する。そのため、本発明の一つの形態である有機化合物を二次電池用電極活物質として用いた場合、充放電中に電解液に溶解を抑制できる。その結果、高容量密度でサイクル特性の高い二次電池を得ることが出来る。
プロトン核磁気共鳴分光(以下、適宜、「1H−NMR」という)スペクトル:核磁気共鳴装置(日本電子株式会社製、型式名「JNM−Lambda 400」)
(工程1)中間体化合物(a)の合成
中間体化合物(a)のプロトン核磁気共鳴分光スペクトルの測定結果は以下のとおりであった。
1H−NMR(400MHz,CDCl3):δ=4.34(s,2H),7.41−7.53(m,3H),7.59(s,1H),7.63(d,2H),7.72(d,1H),8.01(d,1H)
化合物(7A)のES−MSスペクトルの測定結果は以下のとおりであった。
ES−MS(70eV):m/z=612(M+)
(工程3)中間体化合物(b)の合成
中間体化合物(b)のプロトン核磁気共鳴分光スペクトルの測定結果は以下のとおりであった。
1H−NMR(400MHz,CDCl3):δ=2.77(quart,2H),3.22(t,2H),7.34(td,1H),7.51−7.74(m,6H),7.78(dd,1H),7.85(d,1H),7.95(d,1H)
中間体化合物(c)のプロトン核磁気共鳴分光スペクトルの測定結果は以下のとおりであった。
1H−NMR(400MHz,CDCl3):δ=4.35(s,2H),7.36(td,1H),7.52−7.80(m,7H),7.94(d,1H),8.03(d,1H)
(工程3)式(5)で表される有機化合物の合成
実施例1で得られた化合物(7A)と、導電補助剤としてのアセチレンブラック粉末(電気化学工業社製)と、結着剤としてのポリテトラフルオロエチレン樹脂(ダイキン社製)を用い、それぞれ質量比で、化合物(7A):導電補助剤:結着剤=70:25:5の比になるように秤量した。その後、化合物(7A)と導電補助剤をメノウ乳鉢で十分に混合し、さらに結着剤を加え、引き続き均一になるように混合した後、その混合物を薄く延ばしてシート化した。これを直径1cmに打抜いたペレットを第1電極(正極)とした。
詳細には、正負極、隔膜、電解質等の一連の電池組み立てを、アルゴン雰囲気下のグローブボックス内で行った。
正極側パーツは、まずスペーサー(宝泉社製)に正極ペレットを乗せ、その上から集電体として金属チタン網(サンク社製)を圧着させた。さらにそれらをステンレス製コイン電池ケース(宝泉社製、型番CR2032)にスポット溶接した。負極側パーツは、グローブボックス内でナトリウム金属を圧着するため、金属ニッケル網(サンク社製)をスペーサーに溶接後、さらにステンレス製コイン電池ケース(宝泉社製、型番CR2032)にスポット溶接した。完成したコインセルパーツは、ガラスチューブオーブン(柴田科学社製、SIBATAGTO−200)を用いて120℃で15時間程度真空乾燥してアルゴン充填のグローブボックス(露点−80℃以下)に移動させた。
なお、ナトリウムイオン電池の組み立ては、グローブボックス(MBraun製、labmaster)中で行った。非水電解液として1MのNaPF6を溶解したジメチルカルボネート(DMC)とエチレンカルボネート(EC)とが、体積比で1:1の混合溶媒(富山薬品工業社製)、セパレーターには多孔質ポリエチレン製隔膜(セルガード3501、セルガード社製)を使用した。金属ナトリウム(Aldrich社製)を負極パーツ上に圧着した後、ガスケットを取り付けた。正極パーツと負極パーツにポリスポイトを用いて非水電解液を約1ml滴下し、負極パーツの上にセパレーターを乗せ、最後に正極パーツを被せて自動コインカシメ機(宝泉社製)を用いてかしめた。
以上のようにして得られたナトリウム二次電池の充放電容量を測定した。具体的な測定方法としては、以下の通りである。まず、レストポテンシャルから1.0Vまで0.2mA/cm2でCC(コンスタントカレント:定電流)放電を行った。次に、放電速度と同じ速度で、CC充電を行い、電圧4.0Vでカットオフすることにより、1サイクル目の充放電を行った。この1サイクル目の放電容量は、化合物(7A)の質量に対して、174mAh/gであった。
化合物(7A)のかわりに、上記式(5)で表される化合物を正極活物質に使用した以外は、実施例4と同様にして二次電池を作製し、同様に評価した。当該二次電池の放電容量は、化合物(5)の質量に対して、70mAh/gであった。
化合物(7A)のかわりに、ベンゾフェノン(和光純薬工業(株)製)を正極活物質に使用した以外は、実施例4と同様にして比較例1の二次電池を作製し、同様に評価した。当該電池の放電容量は、ベンゾフェノンの質量に対して、3mAh/gであった。
化合物(7A)のかわりに、9−フルオレノン(東京化成(株)製)を正極活物質に使用した以外は、実施例4と同様にして比較例2の二次電池を作製し、同様に評価した。
当該電池の放電容量は、9−フルオレノンの質量に対して、2mAh/gであった。
化合物(7A)のかわりに、1,3,5−トリスベンゾイルベンゼン(Fluorochem製)を正極活物質に使用した以外は、実施例1と同様にして比較例1の電池を作製し、同様に評価した。
当該電池の放電容量は、1,3,5−トリスベンゾイルベンゼンの質量に対して、47mAh/gであった。
2:負極
3:セパレーター
4:正極集電体
5:負極集電体
6:電池ケース
7:電解質
10:電池缶
Claims (7)
- 請求項1〜4のいずれか一項に記載の有機化合物を有する、二次電池用電極活物質。
- 正極、負極、及び電解液を備え、前記正極および前記負極から選ばれる少なくとも1つが、請求項1〜4のいずれか一項に記載の有機化合物又は請求項5に記載の二次電池用電極活物質を含む、二次電池。
- リチウムイオンまたはナトリウムイオンである請求項6に記載の二次電池。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017023740A JP6814064B2 (ja) | 2017-02-13 | 2017-02-13 | 有機化合物、電極活物質及びこれを用いた二次電池 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017023740A JP6814064B2 (ja) | 2017-02-13 | 2017-02-13 | 有機化合物、電極活物質及びこれを用いた二次電池 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018131387A true JP2018131387A (ja) | 2018-08-23 |
JP6814064B2 JP6814064B2 (ja) | 2021-01-13 |
Family
ID=63249440
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017023740A Active JP6814064B2 (ja) | 2017-02-13 | 2017-02-13 | 有機化合物、電極活物質及びこれを用いた二次電池 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6814064B2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109293886A (zh) * | 2018-09-30 | 2019-02-01 | 河北科技大学 | 微孔聚合物的制备方法和应用 |
CN110590642A (zh) * | 2019-09-23 | 2019-12-20 | 大连理工大学 | 一类以三聚茚酮为电子受体的电致发光材料及其应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002329582A (ja) * | 2001-04-27 | 2002-11-15 | Canon Inc | 有機発光素子 |
JP2002329580A (ja) * | 2001-02-22 | 2002-11-15 | Canon Inc | 有機発光素子 |
JP2012222255A (ja) * | 2011-04-12 | 2012-11-12 | Fujifilm Corp | 有機電界発光素子、有機電界発光素子用材料、膜、及び有機電界発光素子の作製方法 |
JP2014175211A (ja) * | 2013-03-11 | 2014-09-22 | Panasonic Corp | 蓄電デバイス用電極活物質および蓄電デバイス |
JP2016008227A (ja) * | 2014-06-23 | 2016-01-18 | 株式会社リコー | ポリキノン誘導体、及びそれを用いた二次電池用電極活物質 |
JP2018133126A (ja) * | 2017-02-13 | 2018-08-23 | 国立大学法人九州大学 | 二次電池用電極活物質およびそれを用いた二次電池 |
-
2017
- 2017-02-13 JP JP2017023740A patent/JP6814064B2/ja active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002329580A (ja) * | 2001-02-22 | 2002-11-15 | Canon Inc | 有機発光素子 |
JP2002329582A (ja) * | 2001-04-27 | 2002-11-15 | Canon Inc | 有機発光素子 |
JP2012222255A (ja) * | 2011-04-12 | 2012-11-12 | Fujifilm Corp | 有機電界発光素子、有機電界発光素子用材料、膜、及び有機電界発光素子の作製方法 |
JP2014175211A (ja) * | 2013-03-11 | 2014-09-22 | Panasonic Corp | 蓄電デバイス用電極活物質および蓄電デバイス |
JP2016008227A (ja) * | 2014-06-23 | 2016-01-18 | 株式会社リコー | ポリキノン誘導体、及びそれを用いた二次電池用電極活物質 |
JP2018133126A (ja) * | 2017-02-13 | 2018-08-23 | 国立大学法人九州大学 | 二次電池用電極活物質およびそれを用いた二次電池 |
Non-Patent Citations (5)
Title |
---|
ISODA, K. ET AL.: "Truxene-Based Columnar Liquid Crystals: Self-Assembled Structures and Electro-Active Properties", CHEMISTRY - AN ASIAN JOURNAL, vol. 4(10), JPN6020031738, 2009, pages 1619 - 1625, ISSN: 0004333333 * |
KOEHLER, J. ET AL.: "Ultrafast charge-transfer dynamics of donor-substituted truxenones", PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 14(31), JPN6020031740, 2012, pages 11081 - 11089, ISSN: 0004333334 * |
NIELSEN, C. B. ET AL.: "Efficient truxenone-based acceptors for organic photovoltaics", JOURNAL OF MATERIALS CHEMISTRY A, vol. 1(1), JPN6020031744, 2013, pages 73 - 76, ISSN: 0004333336 * |
NIELSEN, C. B. ET AL.: "Electron-deficient truxenone derivatives and their use in organic photovoltaics", JOURNAL OF MATERIALS CHEMISTRY A, vol. 2(31), JPN6020031741, 2014, pages 12348 - 12354, XP002804234, ISSN: 0004333335, DOI: 10.1039/C4TA01653J * |
TSUJI, H. ET AL.: "Tripyridyltruxenes: Thermally Stable Cathode Buffer Materials for Organic Thin-Film Solar Cells", ASIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 1(1), JPN6020031745, 2012, pages 34 - 37, ISSN: 0004333337 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109293886A (zh) * | 2018-09-30 | 2019-02-01 | 河北科技大学 | 微孔聚合物的制备方法和应用 |
CN110590642A (zh) * | 2019-09-23 | 2019-12-20 | 大连理工大学 | 一类以三聚茚酮为电子受体的电致发光材料及其应用 |
CN110590642B (zh) * | 2019-09-23 | 2022-06-07 | 大连理工大学 | 一类以三聚茚酮为电子受体的电致发光材料及其应用 |
Also Published As
Publication number | Publication date |
---|---|
JP6814064B2 (ja) | 2021-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4913266B2 (ja) | 蓄電デバイス用電極活物質およびそれを用いた蓄電デバイス | |
JP5531424B2 (ja) | 電極活物質及びそれを用いた二次電池 | |
JP5625151B2 (ja) | ラジカルを有する化合物、重合体、およびその重合体を用いた蓄電デバイス | |
JP6456282B2 (ja) | 蓄電デバイス用電極活物質および蓄電デバイス | |
JP5488799B2 (ja) | 電極活物質及び二次電池 | |
JP6667178B2 (ja) | 非水二次電池用電解液及びそれを用いた非水二次電池 | |
JP2010080343A (ja) | 電極活物質、及び二次電池 | |
JP2014175211A (ja) | 蓄電デバイス用電極活物質および蓄電デバイス | |
EP2308912B1 (en) | Polymer, semiconductor film, electrode, electrode active material, electrochemical element and electricity storage device | |
JP6814064B2 (ja) | 有機化合物、電極活物質及びこれを用いた二次電池 | |
JP2007227186A (ja) | 分子結晶性二次電池 | |
JP6846757B2 (ja) | 二次電池用電極活物質およびそれを用いた二次電池 | |
JP6179233B2 (ja) | 非水電解液二次電池 | |
JP2013134947A (ja) | 電極活物質およびそれを含む二次電池 | |
JP6175703B2 (ja) | 非水電解液二次電池 | |
JP2021163558A (ja) | 二次電池用電極活物質及びそれを用いた二次電池 | |
JP2019087363A (ja) | 電極活物質、及び二次電池 | |
JP5282259B2 (ja) | 分子クラスター二次電池 | |
US20160359168A1 (en) | High voltage organic materials for energy storage applications | |
JP5536519B2 (ja) | 電極活物質及び二次電池 | |
JP6332634B2 (ja) | コポリマー、電極用活物質、及び二次電池 | |
WO2021106834A1 (ja) | 電極材料 | |
JP2010113840A (ja) | 電極活物質及び電池 | |
JP2019186145A (ja) | 二次電池用電極活物質およびそれを用いた二次電池 | |
JP2022022781A (ja) | テトラジン系活物質を用いたナトリウムイオン二次電池 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190823 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200827 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200827 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200915 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20201217 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20201218 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6814064 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |