KR102233777B1 - 리튬 전지 전해질용 첨가제, 이를 포함하는 리튬 전지용 전해질 및 상기 전해질을 채용한 리튬 전지 - Google Patents
리튬 전지 전해질용 첨가제, 이를 포함하는 리튬 전지용 전해질 및 상기 전해질을 채용한 리튬 전지 Download PDFInfo
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- KR102233777B1 KR102233777B1 KR1020140111046A KR20140111046A KR102233777B1 KR 102233777 B1 KR102233777 B1 KR 102233777B1 KR 1020140111046 A KR1020140111046 A KR 1020140111046A KR 20140111046 A KR20140111046 A KR 20140111046A KR 102233777 B1 KR102233777 B1 KR 102233777B1
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- substituted
- unsubstituted
- electrolyte
- lithium battery
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- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 93
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 239000003792 electrolyte Substances 0.000 title claims abstract description 71
- 239000000654 additive Substances 0.000 title claims abstract description 28
- 230000000996 additive effect Effects 0.000 title claims abstract description 23
- -1 triazine triphosphonate compound Chemical class 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 229910003002 lithium salt Inorganic materials 0.000 claims description 11
- 159000000002 lithium salts Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims description 6
- QKBJDEGZZJWPJA-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound [CH2]COC(=O)OCCC QKBJDEGZZJWPJA-UHFFFAOYSA-N 0.000 claims description 6
- 150000007857 hydrazones Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 claims description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 claims description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910013870 LiPF 6 Inorganic materials 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 claims description 3
- 239000005456 alcohol based solvent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910010238 LiAlCl 4 Inorganic materials 0.000 claims description 2
- 229910010093 LiAlO Inorganic materials 0.000 claims description 2
- 229910015015 LiAsF 6 Inorganic materials 0.000 claims description 2
- 229910013188 LiBOB Inorganic materials 0.000 claims description 2
- 229910013684 LiClO 4 Inorganic materials 0.000 claims description 2
- 229910012513 LiSbF 6 Inorganic materials 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- MDOAAHGPXOGVQG-UHFFFAOYSA-N ethene;propane Chemical compound C=C.CCC MDOAAHGPXOGVQG-UHFFFAOYSA-N 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- 239000010410 layer Substances 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 239000011572 manganese Substances 0.000 description 12
- 239000007773 negative electrode material Substances 0.000 description 12
- 239000007774 positive electrode material Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 229910052759 nickel Inorganic materials 0.000 description 10
- 239000010936 titanium Substances 0.000 description 10
- 229910052719 titanium Inorganic materials 0.000 description 10
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 229910001416 lithium ion Inorganic materials 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
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- 238000004519 manufacturing process Methods 0.000 description 8
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
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- 238000000576 coating method Methods 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
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- 239000003960 organic solvent Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000003660 carbonate based solvent Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
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- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
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- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
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- 229910052696 pnictogen Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000973 polyvinylchloride carboxylated Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
도 2는 실시예 1 내지 3 및 비교예 1에서 제조된 리튬 전지의 사이클별 방전용량을 나타내는 그래프이다.
도 3은 실시예 1 내지 3 및 비교예 1에서 제조된 리튬 전지의 사이클별 용량유지율을 나타내는 그래프이다.
도 4는 실시예 1 내지 3 및 비교예 1에서 제조된 리튬 전지에 있어서 1번째 사이클에서의 미분충방전(dQ/dV) 곡선을 도시한 것이다.
22: 음극
23: 양극
24: 세퍼레이터
25: 전지 용기
26: 봉입 부재
Claims (17)
- 트리아진 트리포스포네이트(triazine triphosphonate) 화합물을 포함하고,
상기 트리아진 트리포스포네이트 화합물이 실릴화된 트리아진 트리포스포네이트 화합물인 리튬 전지 전해질용 첨가제. - 삭제
- 삭제
- 삭제
- 제1항에 있어서,
상기 트리아진 트리포스포네이트 화합물이 실릴화된 1,3,5-트리아진 2,4,6-트리포스포네이트 화합물인 리튬 전지 전해질용 첨가제. - 제1항에 있어서,
상기 트리아진 트리포스포네이트 화합물이 하기 화학식 2로 표시되는 리튬 전지 전해질용 첨가제:
[화학식 2]
상기 식에서,
R1 내지 R18은 각각 독립적으로 수소, 할로겐 원자, 치환된 또는 비치환된 C1-C30 알킬기, 치환된 또는 비치환된 C1-C30 알콕시기, 치환된 또는 비치환된 C2-C20 알케닐기, 치환된 또는 비치환된 C2-C20 알키닐기, 치환된 또는 비치환된 C6-C20 아릴기, 치환된 또는 비치환된 C6-C20 아릴옥시기, 치환된 또는 비치환된 C7-C20 아릴알킬기, 치환된 또는 비치환된 C2-C20 헤테로아릴기, 치환된 또는 비치환된 C2-C20 헤테로아릴옥시기, 치환된 또는 비치환된 C2-C20 헤테로아릴알킬기, 치환된 또는 비치환된 C4-C20 탄소고리기, 치환된 또는 비치환된 C4-C20 탄소고리알킬기, 치환된 또는 비치환된 C2-C20 헤테로고리기, 치환된 또는 비치환된 C2-C20 헤테로고리알킬기, 시아노기, 하이드록시기, 시아노기, 아미노기, 아미디노기, 히드라진, 히드라존, 니트로기, 티올, 카르복실기나 그의 염, 술포닐기, 설파모일(sulfamoyl)기, 술폰산기나 그의 염, 인산이나 그의 염이다. - 제6항에 있어서,
상기 화학식 2에서 R1 내지 R18은 치환된 또는 비치환된 C1-C30 알킬기인 리튬 전지 전해질용 첨가제. - 제6항에 있어서,
상기 화학식 2에서 R1 내지 R18은 서로 독립적으로 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, tert-부틸기, 트리플루오로메틸기, 또는 테트라플루오로에틸기인 리튬 전지 전해질용 첨가제. - 비수성 유기 용매;
리튬염; 및
제1항, 제5항 내지 제9항 중 어느 한 항에 따른 첨가제;를 포함하는 리튬 전지용 전해질. - 제10항에 있어서,
상기 첨가제의 함량은 상기 전해질 총 중량을 기준으로 0.001중량% 내지 10중량%인 리튬 전지용 전해질. - 제10항에 있어서,
상기 첨가제의 함량은 상기 전해질 총 중량을 기준으로 0.01중량% 내지 5중량%인 리튬 전지용 전해질. - 제10항에 있어서,
상기 비수성 유기 용매는 카보네이트계, 에스테르계, 에테르계, 케톤계, 알코올계 용매 및 비양성자성 용매 중에서 선택된 하나 이상을 포함하는 것인 리튬 전지용 전해질. - 제10항에 있어서,
상기 비수성 유기 용매는 디메틸 카보네이트(DMC), 디에틸 카보네이트(DEC), 디프로필 카보네이트(DPC), 메틸프로필 카보네이트(MPC), 에틸프로필 카보네이트(EPC), 메틸에틸 카보네이트(MEC), 에틸렌 카보네이트(EC), 프로필렌 카보네이트(PC), 부틸렌 카보네이트(BC), 플루오로에틸렌 카보네이트(FEC), 비닐렌 카보네이트(VC), 아세토니트릴, 숙시노니트릴(SN), 디메틸 술폭사이드, 디메틸 포름아미드, 디메틸 아세트아미드, 감마부티로락톤, 테트라하이드로퓨란, 에틸렌 프로판(EP) 중에서 선택된 하나 이상인 리튬 전지용 전해질. - 제10항에 있어서,
상기 리튬염은 LiPF6, LiBF4, LiSbF6, LiAsF6, LiC4F9SO3, LiClO4, LiAlO2, LiAlCl4, LiN(CxF2x+1SO2)(CyF2y+1SO2)(여기서, x 및 y는 자연수임), LiCl, LiI, LiB(C2O4)2(리튬 비스옥살레이토 보레이트(lithium bis(oxalato)borate; LiBOB) 또는 이들의 조합으로 이루어진 군에서 선택되는 적어도 하나인 것인 리튬 전지용 전해질. - 제10항에 있어서,
상기 리튬염의 농도는 0.1M 내지 2.0M인 리튬 전지용 전해질. - 양극;
음극; 및
제10항에 따른 전해질;을 포함하는 리튬 전지.
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