JP2019530959A - 電解液及び電気化学装置 - Google Patents
電解液及び電気化学装置 Download PDFInfo
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- JP2019530959A JP2019530959A JP2019516201A JP2019516201A JP2019530959A JP 2019530959 A JP2019530959 A JP 2019530959A JP 2019516201 A JP2019516201 A JP 2019516201A JP 2019516201 A JP2019516201 A JP 2019516201A JP 2019530959 A JP2019530959 A JP 2019530959A
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- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- OJKANDGLELGDHV-UHFFFAOYSA-N disilver;dioxido(dioxo)chromium Chemical compound [Ag+].[Ag+].[O-][Cr]([O-])(=O)=O OJKANDGLELGDHV-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- HHEIMYAXCOIQCJ-UHFFFAOYSA-N ethyl 2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)C HHEIMYAXCOIQCJ-UHFFFAOYSA-N 0.000 description 1
- NZDGNIJHHWDSIW-UHFFFAOYSA-N ethyl acetate;methyl acetate Chemical compound COC(C)=O.CCOC(C)=O NZDGNIJHHWDSIW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- CYEDOLFRAIXARV-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound CCCOC(=O)OCC CYEDOLFRAIXARV-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910021385 hard carbon Inorganic materials 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
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910000339 iron disulfide Inorganic materials 0.000 description 1
- GNVXPFBEZCSHQZ-UHFFFAOYSA-N iron(2+);sulfide Chemical compound [S-2].[Fe+2] GNVXPFBEZCSHQZ-UHFFFAOYSA-N 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 1
- 229910002102 lithium manganese oxide Inorganic materials 0.000 description 1
- FRMOHNDAXZZWQI-UHFFFAOYSA-N lithium manganese(2+) nickel(2+) oxygen(2-) Chemical compound [O-2].[Mn+2].[Ni+2].[Li+] FRMOHNDAXZZWQI-UHFFFAOYSA-N 0.000 description 1
- 229910021437 lithium-transition metal 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
- VLXXBCXTUVRROQ-UHFFFAOYSA-N lithium;oxido-oxo-(oxomanganiooxy)manganese Chemical compound [Li+].[O-][Mn](=O)O[Mn]=O VLXXBCXTUVRROQ-UHFFFAOYSA-N 0.000 description 1
- URIIGZKXFBNRAU-UHFFFAOYSA-N lithium;oxonickel Chemical compound [Li].[Ni]=O URIIGZKXFBNRAU-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RCIJMMSZBQEWKW-UHFFFAOYSA-N methyl propan-2-yl carbonate Chemical compound COC(=O)OC(C)C RCIJMMSZBQEWKW-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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical group 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QMKUYPGVVVLYSR-UHFFFAOYSA-N propyl 2,2-dimethylpropanoate Chemical compound CCCOC(=O)C(C)(C)C QMKUYPGVVVLYSR-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing 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
- 239000002153 silicon-carbon composite material Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 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 Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
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Abstract
Description
置換基はハロゲン、シアノ、C1〜C6アルキル基、C2〜C6アルケニル基、C1〜C6アルコキシ基から選ばれる少なくとも1種であり、
x、y、zはそれぞれ独立に、0〜8の整数から選ばれるものであり、
m、n、kはそれぞれ独立に、0〜2の整数から選ばれるものであり、好ましくは、m、n、kはそれぞれ独立に、1または2から選ばれるものである。]
[添加剤A]
置換基はハロゲン、シアノ、C1〜C6アルキル基、C2〜C6アルケニル基、C1〜C6アルコキシ基から選ばれる少なくとも1種である。
x、y、zはそれぞれ独立に0〜8から選ばれる整数である。
m、n、kはそれぞれ独立に0〜2から選ばれる整数である。]
式I−1で示される化合物の改良態様として、R1、R2、R3、およびR4はそれぞれ独立に、水素、ハロゲン、置換あるいは無置換のC1〜C6直鎖又は分岐鎖アルキル基、置換あるいは無置換のC5〜C9シクロアルキル基、置換あるいは無置換のC1〜C6アルコキシ基、置換あるいは無置換のC1〜C6アミン基、置換あるいは無置換のC2〜C6アルケニル基、置換あるいは無置換のC2〜C6アルキニル基、置換あるいは無置換のC6〜C12アリール基、及び、置換あるいは無置換のC4〜C12ヘテロ環基から選ばれるものであり、また、置換基はハロゲンから選ばれるものである。
式I−2で示される化合物の改良態様として、R1、R2、R3、およびR4はそれぞれ独立に、水素、ハロゲン、置換あるいは無置換のC1〜C6直鎖又は分岐鎖アルキル基、置換あるいは無置換のC5〜C9シクロアルキル基、置換あるいは無置換のC1〜C6アルコキシ基、置換あるいは無置換のC1〜C6アミン基、置換あるいは無置換のC2〜C6アルケニル基、置換あるいは無置換のC2〜C6アルキニル基、置換あるいは無置換のC6〜C12アリール基、及び、置換あるいは無置換のC4〜C13ヘテロ環基から選ばれるものであり、置換基はハロゲンから選ばれるものである。
式I−3で示される化合物の改良態様として、R1、R2、およびR3はそれぞれ独立に、水素、ハロゲン、置換あるいは無置換のC1〜C6直鎖又は分岐鎖アルキル基、置換あるいは無置換のC5〜C9シクロアルキル基、置換あるいは無置換のC1〜C6アルコキシ基、置換あるいは無置換のC1〜C6アミン基、置換あるいは無置換のC2〜C6アルケニル基、置換あるいは無置換のC2〜C6アルキニル基、置換あるいは無置換のC6〜C12アリール基、及び、置換あるいは無置換のC4〜C13ヘテロ環基から選ばれるものであり、置換基はハロゲンから選ばれるものである。
[添加剤B]
具体的に、スルトン化合物は、式II−1で示される化合物から選ばれる少なくとも1種である。
メチレンジスルホネート化合物は、メチレンメタンジスルホン酸エステル(MMDSと略称する)から選ばれるものである。
[添加剤C]
[有機溶剤]
[電解質塩]
[Li塩−1類]
[Li塩−2類]
[Li塩−3類]
[Li塩−4類]
[Li塩−5類]
[電解液の製造]
[ポリシアノ基含有6員窒素ヘテロ環化合物の合成]
(一)一般式I−1の化合物の製造
1、迅速に撹拌しながら20〜60分間にわたって原料P−1に濃度30〜40%のP−2水溶液を滴下し、滴下が完了した後で15〜30h(時間)迅速に撹拌し、70〜90℃のオイルバス中で3〜5h還流撹拌し、発煙性無色粘調状液体の中間生成物I−1−1を得る。
(二)一般式I−2の化合物の製造
(三)一般式のI−3化合物の製造
無水エタノールにおいて、無水炭酸ナトリウムと、原料P−5と、原料P−3とを混合し、2〜5h撹拌しながら反応させる。熱エタノールで洗浄することを複数回繰り返して粗生成物を得て、再結晶して式I−3で示された化合物を得る。
実施例
25℃で、リチウムイオン電池をまず1Cの定電流で電圧が4.35Vになるまで充電し、さらに4.35Vの定電圧で電流が0.05Cになるまで充電した。次に1Cの定電流で電圧が3.0Vになるまで放電した。これを1つの充放電サイクル過程とし、今回の放電容量は初回サイクルの放電容量である。リチウムイオン電池を上記方法によって200サイクル充放電テストを行い、200サイクル目の放電容量を検出した。
45℃で、リチウムイオン電池をまず1Cの定電流で電圧が4.35Vになるまで充電し、さらに4.35Vの定電圧で電流が0.05Cになるまで充電した。次に1Cの定電流で電圧が3.0Vになるまで放電した。これを1つの充放電サイクル過程とし、今回の放電容量は初回サイクルの放電容量である。リチウムイオン電池を上記方法によって200サイクル充放電テストを行い、200サイクル目の放電容量を検出した。
85℃で、リチウムイオン電池をまず0.5Cの定電流で電圧が4.35Vになるまで充電し、さらに4.35Vの定電圧で電流が0.05Cになるまで充電した。この時のリチウムイオン電池の厚さを測定してh0と記す。その後、リチウムイオン電池を85℃の恒温箱に入れ、24h保存した後に取り出し、この時のリチウムイオン電池の厚さを測定してh1と記す。
他の実施例
Claims (13)
- 式I−1、式I−2又は式I−3で示されるポリシアノ基含有6員窒素ヘテロ環化合物から選ばれる少なくとも1種である添加剤Aと、
置換基はハロゲン、シアノ、C1〜C6アルキル基、C2〜C6アルケニル基、C1〜C6アルコキシ基から選ばれる少なくとも1種であり、
x、y、zはそれぞれ独立に、0〜8の整数から選ばれ、
m、n、kはそれぞれ独立に、0〜2の整数から選ばれ、好ましくは、m、n、kはそれぞれ独立に、1又は2から選ばれる。]
スルホン酸エステル化合物から選ばれる少なくとも1種である添加剤Bと、
ハロゲンで置換された環状カーボネート化合物から選ばれる少なくとも1種である添加剤Cと、を含むことを特徴とする電解液。 - R1、R2、R3、及びR4はそれぞれ独立に、水素、ハロゲン、置換あるいは無置換のC1〜C3直鎖または分岐鎖アルキル基、置換あるいは無置換のC5〜C7シクロアルキル基、置換あるいは無置換のC1〜C3アルコキシ基、置換あるいは無置換のC1〜C3アミン基、置換あるいは無置換のC2〜C3アルケニル基、置換あるいは無置換のC2〜C3アルキニル基、置換あるいは無置換のC6〜C8アリール基、及び、置換あるいは無置換のC4〜C7ヘテロ環基から選ばれるものであり、
置換基は、ハロゲンから選ばれる、ことを特徴とする請求項1に記載の電解液。 - 式I−1において、R1及びR3は同一の基であり、好ましくは、R1、R3及びR4は同一の基であり、
式I−2において、R1、R2、R3及びR4のうち、少なくとも2つが同一の基であり、好ましくは、R1、R2、R3及びR4のうち、少なくとも3つが同一の基であり、
式I−3において、R1、R2及びR3のうち、少なくとも2つが同一の基である、ことを特徴とする請求項1又は2に記載の電解液。 - 式I−1において、R1及びR3は水素であり、好ましくは、R1、R3及びR4はいずれも水素であり、
式I−2において、R1、R2、R3及びR4のうち、少なくとも2つが水素であり、好ましくは、R1、R2、R3及びR4のうち、少なくとも3つが水素であり、
式I−3において、R1、R2及びR3のうち、少なくとも2つが水素である、ことを特徴とする請求項3に記載の電解液。 - 前記電解液における前記添加剤Aの質量百分率は0.001%〜10%であり、好ましくは0.01%〜6%であり、より好ましくは0.1%〜3.5%である、ことを特徴とする請求項1に記載の電解液。
- 前記スルホン酸エステル化合物は、スルトン化合物及びジスルホン酸エステル化合物から選ばれる少なくとも1種であり、
前記スルトン化合物は、式II−1で示される化合物から選ばれる少なくとも1種であり、
前記ジスルホン酸エステル化合物は、式II−2で示される化合物から選ばれる少なくとも1種である、ことを特徴とする請求項1に記載の電解液。
- 前記電解液における前記添加剤Bの質量百分率は0.1%〜10%であり、好ましくは0.5%〜7%であり、より好ましくは1%〜4%である、ことを特徴とする請求項1または7に記載の電解液。
- 前記電解液における前記添加剤Cの質量百分率は0.1%〜10%であり、好ましくは0.5%〜5%であり、より好ましくは1%〜4%である、ことを特徴とする請求項1に記載の電解液。
- 正極シートと、負極シートと、前記正極シートと前記負極シートとの間に配置されたセパレータと、電解液とを含む電気化学装置であって、
前記電解液は、請求項1〜10のいずれか1項に記載の電解液である、ことを特徴とする電気化学装置。 - 前記電気化学装置はリチウムイオン二次電池、リチウム一次電池又はリチウムイオンキャパシタである、ことを特徴とする請求項11に記載の電気化学装置。
- 前記電気化学装置がリチウムイオン二次電池である場合には、前記電気化学装置の充電カットオフ電圧が4.2V以上である、ことを特徴とする請求項11に記載の電気化学装置。
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