JP7027645B2 - 非水電解液添加剤、それを含むリチウム二次電池用非水電解液、およびリチウム二次電池 - Google Patents
非水電解液添加剤、それを含むリチウム二次電池用非水電解液、およびリチウム二次電池 Download PDFInfo
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- JP7027645B2 JP7027645B2 JP2019528061A JP2019528061A JP7027645B2 JP 7027645 B2 JP7027645 B2 JP 7027645B2 JP 2019528061 A JP2019528061 A JP 2019528061A JP 2019528061 A JP2019528061 A JP 2019528061A JP 7027645 B2 JP7027645 B2 JP 7027645B2
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- electrolytic solution
- lithium
- positive electrode
- aqueous electrolytic
- negative electrode
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- 229910052744 lithium Inorganic materials 0.000 title claims description 37
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims description 35
- 239000000654 additive Substances 0.000 title claims description 34
- 230000000996 additive effect Effects 0.000 title claims description 33
- 239000011255 nonaqueous electrolyte Substances 0.000 title description 7
- 239000008151 electrolyte solution Substances 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 34
- 239000007774 positive electrode material Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 11
- KLARSDUHONHPRF-UHFFFAOYSA-N [Li].[Mn] Chemical compound [Li].[Mn] KLARSDUHONHPRF-UHFFFAOYSA-N 0.000 claims description 8
- 229910003002 lithium salt Inorganic materials 0.000 claims description 8
- 159000000002 lithium salts Chemical class 0.000 claims description 8
- 229910002102 lithium manganese oxide Inorganic materials 0.000 claims description 6
- VGYDTVNNDKLMHX-UHFFFAOYSA-N lithium;manganese;nickel;oxocobalt Chemical class [Li].[Mn].[Ni].[Co]=O VGYDTVNNDKLMHX-UHFFFAOYSA-N 0.000 claims description 5
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 claims description 4
- VLXXBCXTUVRROQ-UHFFFAOYSA-N lithium;oxido-oxo-(oxomanganiooxy)manganese Chemical compound [Li+].[O-][Mn](=O)O[Mn]=O VLXXBCXTUVRROQ-UHFFFAOYSA-N 0.000 claims description 4
- QEXMICRJPVUPSN-UHFFFAOYSA-N lithium manganese(2+) oxygen(2-) Chemical class [O-2].[Mn+2].[Li+] QEXMICRJPVUPSN-UHFFFAOYSA-N 0.000 claims description 2
- -1 cyclic carbonate compound Chemical class 0.000 description 29
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 12
- 229910001416 lithium ion Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
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- 239000002131 composite material Substances 0.000 description 1
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- 230000007850 degeneration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- QKBJDEGZZJWPJA-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound [CH2]COC(=O)OCCC QKBJDEGZZJWPJA-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N germanium monoxide Inorganic materials [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910021473 hassium Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 1
- FRMOHNDAXZZWQI-UHFFFAOYSA-N lithium manganese(2+) nickel(2+) oxygen(2-) Chemical class [O-2].[Mn+2].[Ni+2].[Li+] FRMOHNDAXZZWQI-UHFFFAOYSA-N 0.000 description 1
- RSNHXDVSISOZOB-UHFFFAOYSA-N lithium nickel Chemical compound [Li].[Ni] RSNHXDVSISOZOB-UHFFFAOYSA-N 0.000 description 1
- 229910000686 lithium vanadium oxide Inorganic materials 0.000 description 1
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000006051 mesophase pitch carbide Substances 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229920001384 propylene homopolymer Polymers 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910021481 rutherfordium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 229910021477 seaborgium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
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Description
下記化学式1で表される化合物である非水電解液添加剤を提供する。
R1~R5は、それぞれ独立して、C‐(R)2またはC=Oであり、この際、Rは水素または炭素数1~3のアルキル基である。
リチウム塩と、有機溶媒と、前記本発明の非水電解液添加剤と、を含むリチウム二次電池用非水電解液を提供する。
負極と、正極と、前記負極と正極との間に介在されたセパレータと、非水電解液と、を含み、
前記正極は、リチウム‐ニッケル‐マンガン‐コバルト系酸化物およびリチウム‐マンガン系酸化物からなる群から選択される少なくとも1つ以上の正極活物質を含み、
前記非水電解液は、本発明のリチウム二次電池用非水電解液である、リチウム二次電池を提供する。
下記化学式1で表される化合物である非水電解液添加剤を提供する。
R1~R5は、それぞれ独立して、C‐(R)2またはC=Oであり、この際、Rは水素または炭素数1~3のアルキル基である。
リチウム塩と、有機溶媒と、本発明の非水電解液添加剤と、を含むリチウム二次電池用非水電解液を提供する。
負極と、正極と、前記負極と正極との間に介在されたセパレータと、非水電解液と、を含み、
前記正極は、リチウム‐ニッケル‐マンガン‐コバルト系酸化物およびリチウム‐マンガン系酸化物からなる群から選択される正極活物質を含み、
前記非水電解液は本発明の二次電池用非水電解液である、二次電池を提供する。
実施例1.
(非水電解液の製造)
1.0MのLiPF6が溶解された有機溶媒(エチレンカーボネート:エチルメチルカーボネート=30:70vol%)4.975gに、化学式1aの化合物0.025gを添加することで本発明の非水電解液を製造した。
正極活物質として、ニッケル、コバルト、マンガンを含む3成分系正極活物質(Li(Ni0.8Mn0.1Co0.1)O2)、導電材としてカーボンブラック、およびバインダーとしてポリビニリデンフルオライド(PVDF)を97.5:1:1.5(wt%)の割合で、厚さ20μmの正極集電体(Al箔)に塗布し、乾燥してロールプレス(roll press)を行って正極を製造した。このように製造した電極の表面上に、0.5mg/cm2~0.6mg/cm2程度の鉄粒子を塗布することで、低電圧不良の模擬実験用正極を準備した。
上述の方法により製造した不純物を含む正極、Li金属を用いた負極、および多孔性ポリエチレンセパレータを用いてコイン半電池を製造した。
非水電解液の製造時に、有機溶媒4.95gに化学式1aの化合物0.05gを添加したことを除き、前記実施例1と同様の方法により、非水電解液およびそれを含むコイン半電池をそれぞれ製造した。
非水電解液の製造時に、有機溶媒4.985gに化学式1aの化合物0.015gを添加したことを除き、前記実施例1と同様の方法により、非水電解液およびそれを含むコイン半電池をそれぞれ製造した。
非水電解液の製造時に、添加剤を含まないことを除き、前記実施例1と同様の方法により、非水電解液およびそれを含むコイン半電池を製造した(下記表1参照)。
非水電解液の製造時に、添加剤として下記化学式3の化合物を含むことを除き、前記実施例2と同様の方法により、非水電解液およびそれを含むコイン半電池を製造した(下記表1参照)。
非水電解液の製造時に、添加剤として、下記化学式4の化合物を含むことを除き、前記実施例2と同様の方法により、非水電解液およびそれを含むコイン半電池を製造した(下記表1参照)。
実験例1.
前記実施例1と比較例1で製造されたコイン半電池をそれぞれドライルームで製造した後、25℃の恒温槽内に24時間静置させた後、0.1C CC‐CV充放電を3.0V~4.25V(vs.Li/Li+)の電圧範囲で進行しながら、時間によるコイン半電池の電圧の変化を測定した。この際、CV電流終了条件を0.05Cと設定した。
実施例1~3で製造されたコイン半電池および比較例1~3で製造されたコイン半電池を、それぞれ6個ずつ、前記実験例1と同様の条件で充放電を進行しながら、コイン半電池の内部短絡の発生有無を確認した。このように得られた結果から、実施例1~3のコイン半電池と比較例1~3のコイン半電池のそれぞれの内部短絡の発生程度(不良率)を測定した後、その結果を下記表2に示した。この際、表2において、内部短絡発生率が高い場合、二次電池の低電圧発生率(不良率)が高いことを意味する。
正極活物質としてリチウム‐マンガン系活物質(LiMn2O4)、導電材としてカーボンブラック、およびバインダーとしてポリビニリデンフルオライド(PVDF)を90:7.5:2.5(wt%)の割合で混合して正極スラリーを製造した後、それを厚さ20μmの正極集電体(Al箔)に塗布し、乾燥してロールプレス(roll press)を行って正極を製造した。
Claims (5)
- 前記非水電解液添加剤は、非水電解液の全含量を基準として0.05重量%~5重量%で含まれる、請求項1に記載のリチウム二次電池。
- 前記非水電解液添加剤は、非水電解液の全含量を基準として0.5重量%~3重量%で含まれる、請求項2に記載のリチウム二次電池。
- 前記正極活物質がリチウム‐マンガン系酸化物である、請求項1に記載のリチウム二次電池。
- 前記リチウム‐マンガン系酸化物がLiMn2O4である、請求項4に記載のリチウム二次電池。
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KR1020180077559A KR102645104B1 (ko) | 2017-07-14 | 2018-07-04 | 비수전해액 첨가제, 이를 포함하는 리튬 이차전지용 비수전해액 및 리튬 이차전지 |
PCT/KR2018/007730 WO2019013502A1 (ko) | 2017-07-14 | 2018-07-06 | 비수전해액 첨가제, 이를 포함하는 리튬 이차전지용 비수전해액 및 리튬 이차전지 |
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JP2011060464A (ja) | 2009-09-07 | 2011-03-24 | Mitsubishi Chemicals Corp | 非水系電解液およびそれを用いた電池 |
WO2013151096A1 (ja) | 2012-04-05 | 2013-10-10 | 新神戸電機株式会社 | リチウム二次電池 |
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JP2020501303A (ja) | 2020-01-16 |
KR20190008099A (ko) | 2019-01-23 |
EP3509155B1 (en) | 2021-01-06 |
EP3509155A1 (en) | 2019-07-10 |
US20200044286A1 (en) | 2020-02-06 |
CN109891657B (zh) | 2022-03-01 |
EP3509155A4 (en) | 2019-11-06 |
CN109891657A (zh) | 2019-06-14 |
PL3509155T3 (pl) | 2021-05-17 |
US11081728B2 (en) | 2021-08-03 |
KR102645104B1 (ko) | 2024-03-08 |
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