JP2017522698A - レドックスシャトルを含む再充電可能なリチウムイオンセル - Google Patents
レドックスシャトルを含む再充電可能なリチウムイオンセル Download PDFInfo
- Publication number
- JP2017522698A JP2017522698A JP2017502961A JP2017502961A JP2017522698A JP 2017522698 A JP2017522698 A JP 2017522698A JP 2017502961 A JP2017502961 A JP 2017502961A JP 2017502961 A JP2017502961 A JP 2017502961A JP 2017522698 A JP2017522698 A JP 2017522698A
- Authority
- JP
- Japan
- Prior art keywords
- group
- lithium ion
- rechargeable lithium
- ion cell
- alkyl
- 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
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 51
- 239000003792 electrolyte Substances 0.000 claims abstract description 35
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 11
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 49
- 125000001188 haloalkyl group Chemical group 0.000 claims description 37
- -1 arylcarboxyl group Chemical group 0.000 claims description 34
- 125000005011 alkyl ether group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000005252 haloacyl group Chemical group 0.000 claims description 18
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 18
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 17
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 17
- 229950000688 phenothiazine Drugs 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000005179 haloacetyl group Chemical group 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
- 125000003106 haloaryl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 10
- 229910010707 LiFePO 4 Inorganic materials 0.000 claims description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 239000006163 transport media Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 7
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000006184 cosolvent Substances 0.000 claims description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 5
- 239000002609 medium Substances 0.000 claims description 5
- 229910015014 LiNiCoAlO Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910000733 Li alloy Inorganic materials 0.000 claims description 3
- 229910015015 LiAsF 6 Inorganic materials 0.000 claims description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 claims description 3
- 229910013684 LiClO 4 Inorganic materials 0.000 claims description 3
- 229910013210 LiNiMnCoO Inorganic materials 0.000 claims description 3
- 229910013870 LiPF 6 Inorganic materials 0.000 claims description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 239000001989 lithium alloy Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- 210000004027 cell Anatomy 0.000 description 87
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 230000003647 oxidation Effects 0.000 description 39
- 238000007254 oxidation reaction Methods 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 150000002990 phenothiazines Chemical class 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 230000000670 limiting effect Effects 0.000 description 19
- 150000001716 carbazoles Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 150000002988 phenazines Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000002390 rotary evaporation Methods 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- 239000002274 desiccant Substances 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000003335 steric effect Effects 0.000 description 7
- 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 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000002829 reductive effect Effects 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- KBGPFZUZKTUOII-UHFFFAOYSA-N 1,3,6,8-tetramethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC(C)=C3NC2=C1C KBGPFZUZKTUOII-UHFFFAOYSA-N 0.000 description 3
- ZEKIROJZBKYFCP-UHFFFAOYSA-N 9h-carbazole;methoxymethane Chemical compound COC.C1=CC=C2C3=CC=CC=C3NC2=C1 ZEKIROJZBKYFCP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 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
- 238000004364 calculation method Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 3
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 2
- QDZLSMJMIJRYPH-UHFFFAOYSA-N 1,3,6,8,9-pentamethylcarbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC(C)=C3N(C)C2=C1C QDZLSMJMIJRYPH-UHFFFAOYSA-N 0.000 description 2
- IWZUNMYOCJJVGN-UHFFFAOYSA-N 1,3,6,8-tetratert-butyl-9-methylcarbazole Chemical compound C(C)(C)(C)C1=CC(=CC=2C3=CC(=CC(=C3N(C1=2)C)C(C)(C)C)C(C)(C)C)C(C)(C)C IWZUNMYOCJJVGN-UHFFFAOYSA-N 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 2
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000011530 conductive current collector Substances 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002641 lithium Chemical class 0.000 description 2
- DGFLVXIQGRFWHJ-UHFFFAOYSA-N methoxymethane;4-methylbenzenesulfonic acid Chemical compound COC.CC1=CC=C(S(O)(=O)=O)C=C1 DGFLVXIQGRFWHJ-UHFFFAOYSA-N 0.000 description 2
- CSSYKHYGURSRAZ-UHFFFAOYSA-N methyl 2,2-difluoroacetate Chemical compound COC(=O)C(F)F CSSYKHYGURSRAZ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- OVSGNPWPCZRNKI-UHFFFAOYSA-N 1,3,6,8-tetratert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3NC2=C1C(C)(C)C OVSGNPWPCZRNKI-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- YSFLQVNTBBUKEA-UHFFFAOYSA-N 1-bromo-2,4-dimethylbenzene Chemical compound CC1=CC=C(Br)C(C)=C1 YSFLQVNTBBUKEA-UHFFFAOYSA-N 0.000 description 1
- QXBUYALKJGBACG-UHFFFAOYSA-N 10-methylphenothiazine Chemical compound C1=CC=C2N(C)C3=CC=CC=C3SC2=C1 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 description 1
- LWZOWYWLKIVOQY-UHFFFAOYSA-N 10-methylphenothiazine-3,7-dicarbonitrile Chemical compound C(#N)C=1C=CC=2N(C3=CC=C(C=C3SC=2C=1)C#N)C LWZOWYWLKIVOQY-UHFFFAOYSA-N 0.000 description 1
- YOSJCQJJIHEUKA-UHFFFAOYSA-N 2-bromo-4,6-dimethylaniline Chemical compound CC1=CC(C)=C(N)C(Br)=C1 YOSJCQJJIHEUKA-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- YEDILFJEHDIGMZ-UHFFFAOYSA-N 3,7,10-trimethylphenothiazine Chemical compound CC1=CC=C2N(C)C3=CC=C(C)C=C3SC2=C1 YEDILFJEHDIGMZ-UHFFFAOYSA-N 0.000 description 1
- MCAPNDGAMBCNKU-UHFFFAOYSA-N 3,7-dibromo-10-methylphenothiazine Chemical compound BrC1=CC=C2N(C)C3=CC=C(Br)C=C3SC2=C1 MCAPNDGAMBCNKU-UHFFFAOYSA-N 0.000 description 1
- 101100502324 Arabidopsis thaliana FAD6 gene Proteins 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910011458 Li4/3 Ti5/3O4 Inorganic materials 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910011281 LiCoPO 4 Inorganic materials 0.000 description 1
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 description 1
- 229910013086 LiNiPO Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910020810 Sn-Co Inorganic materials 0.000 description 1
- 229910018757 Sn—Co Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000004429 atom 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
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Substances OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001903 differential pulse voltammetry Methods 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 239000002931 mesocarbon microbead Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 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 1
- 239000007773 negative electrode material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/26—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom without other substituents attached to the ring system
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- 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
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- H01M10/00—Secondary cells; Manufacture thereof
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- 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
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Abstract
Description
本特許出願は、2014年7月18日出願の米国仮特許出願番号62/026,212の優先権及び全ての利益を主張し、この開示は、参照によりその全体が本明細書に組み込まれる。
開示分野
背景技術
開示の概要
開示の詳細な説明
正極:
負極:
電荷運搬電解質:
電荷運搬媒体:
リチウム塩:
レドックスシャトル:
置換フェノチアジン:
これとは別に、上記の値内の全ての値及び値の範囲は、これにより、多様な無限定の実施態様において明示的に考慮される。
置換フェナジン:
置換カルバゾール:
Imax=FADC/d
実施例
置換フェノチアジンの計算値:
3,7,10−トリメチルフェノチアジン(B)の製造:
3,7−ジシアノ−10−メチルフェノチアジン(C)の製造:
カルバゾールの計算値:
1,3,6,8−テトラ(t−ブチル)カルバゾール(I)の製造:
1,3,6,8−テトラ(t−ブチル)−9−メチルカルバゾール(II)の製造:
1,3,6,8−テトラメチルカルバゾール(III)の製造
1,3,6,8,9−ペンタメチルカルバゾール(IV)の製造:
3,6−ジ−t−ブチルカルバゾール(V)の製造:
ビス(エチレングリコール)モノメチルエーテルモノトシラート(VI)の製造:
3,6−ジ−t−ブチル−9−ジエチレングリコールモノメチルエーテル−カルバゾール(VII)の製造:
1−アセチル−3,6−ジ−t−ブチル−9−(ジエチレングリコールモノメチルエーテル)カルバゾール(VIII)の製造:
3,6−ジ−t−ブチル−1,8−ジヨード−9−(ジエチレングリコールモノメチルエーテル)−カルバゾール(IX)の製造:
3,6−ジ−t−ブチル−1,8−ジトリフルオロメチル−9−(ジエチレングリコールモノメチルエーテル)カルバゾール(X)の製造:
3,6−ジ−t−ブチル−1,8−ジブロモ−9−(ジエチレングリコールモノメチルエーテル)カルバゾール(XI)の製造:
1−アセチル−8−ブロモ−3,6−ジ−t−ブチル−9−(ジエチレングリコールモノメチルエーテル)カルバゾール(XII)の製造:
フェナジンの計算値:
Claims (25)
- セル容量を示し、かつ:
A.再充電された電位を示す正極;
B.負極;
C.電荷運搬媒体及びリチウム塩を含む電荷運搬電解質;及び
D.次の構造:
- 前記レドックスシャトルは、更に、次の構造:
R3及びR4の各々は、無関係に、1〜12の炭素原子を有するアルキル基、又は1〜12の炭素原子を有するハロアルキル基、及び/又はR3及びR4の一方は、水素原子であり;及び
R5は、1〜12の炭素原子を有するアルキル基、1〜12の炭素原子を有するハロアルキル基、1〜12の炭素原子を有するペルハロアルキル基、1〜12の炭素原子を有するアルキルエーテル基、又は1〜12の炭素原子を有するトリアルキルアンモニウムアルキル基である]を示す置換フェノチアジンとして定義される、請求項1に記載の再充電可能なリチウムイオンセル。 - R1及びR2の各々は、無関係に、1〜12の炭素原子を有するアルキル基又は1〜12の炭素原子を有するハロアルキル基である、請求項1又は2に記載の再充電可能なリチウムイオンセル。
- R1及びR2の各々は、無関係に1〜6の炭素原子を有するアルキル基である、請求項1又は2に記載の再充電可能なリチウムイオンセル。
- R3及びR4の各々は、無関係に、1〜12の炭素原子を有するアルキル基、1〜12の炭素原子を有するハロアルキル基、アセチル基、ハロアセチル基、又は水素原子である、請求項1から4までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- R3及びR4の各々は、無関係に、1〜6の炭素原子を有するアルキル基である、請求項1から4までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- R3及びR4の一方は、水素原子であり、R3及びR4の他方は、水素原子ではない、請求項1から4までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- R5は、1〜12の炭素原子を有するアルキル基、1〜12の炭素原子を有するアルキルエーテル基、又は1〜12の炭素原子を有するトリアルキルアンモニウムアルキル基である、請求項1から7までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- R5は、1〜6の炭素原子を有するアルキル基である、請求項1から7までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、前記電荷運搬電解質中に溶解されている、請求項1から9までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記電荷運搬電解質は助溶媒を含む、請求項1から10までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、Li/Li+と比べて、3.5〜5Vの酸化還元電位を示す、請求項1から11までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、少なくとも10回の充放電サイクルの後で、前記レドックスシャトルを酸化するために十分な充電電圧で、かつ各充放電サイクルの間にセル容量の100%に等しい過充電の充電流で、前記再充電可能なリチウムイオンセルに対して過充電保護を提供する、請求項1から12までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、少なくとも500回の充放電サイクルの後で、前記レドックスシャトルを酸化するために十分な充電電圧で、かつ各々の充放電サイクルの間のセル容量の100%に等しい過充電の充電流で、前記再充電可能なリチウムイオンセルに対して過充電保護を提供する、請求項1から12までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、前記電荷運搬電解質の全質量を基準として1〜10質量%の量で存在する、請求項1から14までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記正極は、LiFePO4、Li2FeSiO4、MnO2、LixMnO2、LiNiMnCoO2及び/又はLiNiCoAlO2を含み、ここで、xは0.3〜0.4である、請求項1から15までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記正極は、Li[B(C2O4)2]、Li[BF2(C2O4)]、Li[PF2(C2O4)2]、LiClO4、LiBF4、LiAsF6、LiPF6、Li[CF3SO3]、Li[N(CF3SO2)2]、Li[C(CF3SO2)3]、Li[N(SO2C2F5)2]、リチウムアルキルフルオロホスファート、又はこれらの組み合わせを含む、請求項1から15までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記負極は、黒鉛状炭素、リチウム金属又はリチウム合金を含む、請求項1から17までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記電荷運搬媒体は、炭酸エチレン、炭酸プロピレン、炭酸ジメチル、炭酸ジエチル、炭酸エチルメチル又はこれらの組み合わせを含む、請求項1から18までのいずれか1項に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、置換フェノチアジンである、請求項1に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、置換カルバゾールである、請求項1に記載の再充電可能なリチウムイオンセル。
- 前記レドックスシャトルは、置換フェナジンである、請求項1に記載の再充電可能なリチウムイオンセル。
- 請求項1から23までのいずれか1項に記載の再充電可能なリチウムイオンセルを含む物品。
- 請求項1から23までのいずれか1項に記載の前記再充電可能なリチウムイオンセルの2つ以上を含むアレイ。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462026212P | 2014-07-18 | 2014-07-18 | |
US62/026,212 | 2014-07-18 | ||
PCT/US2015/040970 WO2016011393A1 (en) | 2014-07-18 | 2015-07-17 | Rechargeable lithium-ion cell comprising a redox shuttle additive |
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DE102016217820A1 (de) | 2016-09-16 | 2018-03-22 | Robert Bosch Gmbh | Hybridsuperkondensator mit Additiven zum Überladungsschutz |
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KR102629756B1 (ko) | 2024-01-29 |
US20190305381A1 (en) | 2019-10-03 |
DE112015003328T5 (de) | 2017-04-13 |
JP6679564B2 (ja) | 2020-04-15 |
KR20170030544A (ko) | 2017-03-17 |
CN107078345B (zh) | 2020-03-20 |
KR20230023044A (ko) | 2023-02-16 |
WO2016011393A1 (en) | 2016-01-21 |
US11177513B2 (en) | 2021-11-16 |
CN107078345A (zh) | 2017-08-18 |
US20170162916A1 (en) | 2017-06-08 |
USRE48859E1 (en) | 2021-12-21 |
US10249910B2 (en) | 2019-04-02 |
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