JPWO2020116574A1 - 電解液及び電気化学デバイス - Google Patents
電解液及び電気化学デバイス Download PDFInfo
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- JPWO2020116574A1 JPWO2020116574A1 JP2020560016A JP2020560016A JPWO2020116574A1 JP WO2020116574 A1 JPWO2020116574 A1 JP WO2020116574A1 JP 2020560016 A JP2020560016 A JP 2020560016A JP 2020560016 A JP2020560016 A JP 2020560016A JP WO2020116574 A1 JPWO2020116574 A1 JP WO2020116574A1
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000010280 constant potential charging Methods 0.000 description 1
- 238000010277 constant-current charging Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 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
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 229910021480 group 4 element Inorganic materials 0.000 description 1
- SDAXRHHPNYTELL-UHFFFAOYSA-N heptanenitrile Chemical compound CCCCCCC#N SDAXRHHPNYTELL-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000003273 ketjen black Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 1
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
- SBWRUMICILYTAT-UHFFFAOYSA-K lithium;cobalt(2+);phosphate Chemical compound [Li+].[Co+2].[O-]P([O-])([O-])=O SBWRUMICILYTAT-UHFFFAOYSA-K 0.000 description 1
- ILXAVRFGLBYNEJ-UHFFFAOYSA-K lithium;manganese(2+);phosphate Chemical compound [Li+].[Mn+2].[O-]P([O-])([O-])=O ILXAVRFGLBYNEJ-UHFFFAOYSA-K 0.000 description 1
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 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
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- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
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- 239000000565 sealant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- 229920006132 styrene block copolymer Polymers 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920006027 ternary co-polymer Polymers 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
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
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Abstract
Description
測定装置:Bruker Japan製Avance neo
測定方法:シングルパルス法
観測核:19F
スペクトル幅:90kHz
パルス幅:15μs(90°パルス)
パルス繰り返し時間:1s
基準物質:C6H5CF3(外部基準:−63.9ppm)
温度:23℃
試料回転数:20Hz
[電解液の調製]
1mol/LのLiPF6を含むエチレンカーボネート、ジメチルカーボネート及びジエチルカーボネートの混合溶液に、混合溶液全量に対してビニレンカーボネート(VC)を1質量%と、下記式(9)で表される化合物Aを1質量%(電解液全量基準)添加して、電解液を調製した。
調製した電解液について、上述した測定条件に従って19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、また、−180ppm以上−150ppm以下のケミカルシフトの範囲内に化合物A由来のピークを示すスペクトルが得られた。化合物A由来のピークを示すスペクトルを図3(a)に示す。
19F−NMR:−73.68ppm,−75.56ppm,−82.74ppm,−85.34ppm,−86.80ppm,−89.65ppm,−162.07ppm
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、また、−180ppm以上−150ppm以下のケミカルシフトの範囲内に化合物B由来のピークを示すスペクトルが得られた。化合物B由来のピークを示すスペクトルを図3(b)に示す。
19F−NMR:−73.26ppm,−75.14ppm,−82.65ppm,−85.26ppm,−86.79ppm,−89.64ppm,−162.02ppm
[電解液の調製]
実施例1において、化合物Aを使用しなかった以外は、実施例1と同様にして電解液を調製した。
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを示すスペクトルが得られた。
19F−NMR:−75.03ppm,−75.28ppm,−76.91ppm,−77.16ppm,−88.07ppm,−90.92ppm
[電解液の調製]
実施例1において、化合物Aを使用せず、4−フルオロ−1,3−ジオキソラン−2−オン(フルオロエチレンカーボネート;FEC)を1質量%(電解液全量基準)添加した以外は、実施例1と同様にして電解液を調製した。
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、また、−130ppmを超え−110ppm以下のケミカルシフトの範囲内にFEC由来のピークを示すスペクトルが得られた。FEC由来のピークを示すスペクトルを図4に示す。
19F−NMR:−73.69ppm,−75.57ppm,−82.62ppm,−85.22ppm,−86.82ppm,−89.67ppm,−121.30ppm
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、また、−150ppmを超え−110ppm以下のケミカルシフトの範囲内に化合物C由来のピークを示すスペクトルが得られた。化合物C由来のピークを示すスペクトルを図5(a)に示す。
19F−NMR:−73.66ppm,−75.54ppm,−82.65ppm,−85.25ppm,−86.81ppm,−89.66ppm,−135.13ppm
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、また、−150ppmを超え−110ppm以下のケミカルシフトの範囲内に化合物D由来のピークを示すスペクトルが得られた。化合物D由来のピークを示すスペクトルを図5(b)に示す。
19F−NMR:−73.62ppm,−75.49ppm,−82.76ppm,−85.37ppm,−86.78ppm,−89.63ppm,−136.60ppm
[電解液の調製]
実施例1において、化合物Aの含有量を0.5質量%に変更し、FECを0.5質量%(いずれも電解液全量基準)添加した以外は、実施例1と同様にして電解液を調製した。
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、−180ppm以上−150ppm以下のケミカルシフトの範囲内に化合物A由来のピークを、また、−130ppmを超え−110ppm以下のケミカルシフトの範囲内にFEC由来のピークを示すスペクトルが得られた。化合物A由来のピーク、及びFEC由来のピークを示すスペクトルを図6(a)に示す。
19F−NMR:−73.69ppm,−75.58ppm,−82.73ppm,−85.25ppm,−86.85ppm,−89.70ppm,−121.45ppm,−162.10ppm
[電解液の調製]
実施例3において、化合物Cの含有量を0.5質量%に変更し、FECを0.5質量%(いずれも電解液全量基準)添加した以外は、実施例3と同様にして電解液を調製した。
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、−150ppmを超え−130ppm以下のケミカルシフトの範囲内に化合物C由来のピークを、また、−130ppmを超え−110ppm以下のケミカルシフトの範囲内にFEC由来のピークを示すスペクトルが得られた。化合物C由来のピーク、及びFEC由来のピークを示すスペクトルを図6(b)に示す。
19F−NMR:−73.67ppm,−75.55ppm,−82.68ppm,−85.25ppm,−86.80ppm,−89.65ppm,−121.23ppm,−135.14ppm
[電解液の調製]
実施例4において、化合物Dの含有量を0.5質量%に変更し、FECを0.5質量%(いずれも電解液全量基準)添加した以外は、実施例4と同様にして電解液を調製した。
調製した電解液について19F−NMR測定を行った。その結果、−100ppm以上−70ppm以下のケミカルシフトの範囲内にPF6 −及びその反応物由来のピークを、−150ppmを超え−130ppm以下のケミカルシフトの範囲内に化合物D由来のピークを、また、−130ppmを超え−110ppm以下のケミカルシフトの範囲内にFEC由来のピークを示すスペクトルが得られた。化合物D由来のピーク、及びFEC由来のピークを示すスペクトルを図7(c)に示す。
19F−NMR:−73.68ppm,−75.57ppm,−82.57ppm,−85.17ppm,−86.83ppm,−89.68ppm,−121.35ppm,−136.69ppm
正極活物質としてのコバルト酸リチウム(95質量%)に、導電剤としての繊維状の黒鉛(1質量%)及びアセチレンブラック(AB)(1質量%)と、結着剤(3質量%)とを順次添加し、混合した。得られた混合物に対し、分散媒としてのNMPを添加し、混練することによりスラリー状の正極合剤を調製した。この正極合剤を正極集電体としての厚さ20μmのアルミニウム箔に均等且つ均質に所定量塗布した。その後、分散媒を揮発させてから、プレスすることにより密度3.6g/cm3まで圧密化して、正極を得た。
負極活物質としての黒鉛及びケイ素酸化物に、結着剤と、増粘剤としてのカルボキシメチルセルロースとを添加した。これらの質量比については、黒鉛:ケイ素酸化物:結着剤:増粘剤=92:5:1.5:1.5とした。得られた混合物に対し、分散媒としての水を添加し、混練することによりスラリー状の負極合剤を調製した。この負極合剤を負極集電体としての厚さ10μmの圧延銅箔に均等かつ均質に所定量塗布した。その後、分散媒を揮発させてから、プレスすることにより密度1.6g/cm3まで圧密化して、負極を得た。
13.5cm2の四角形に切断した正極を、セパレータであるポリエチレン製多孔質シート(商品名:ハイポア(登録商標)、旭化成株式会社製、厚さ30μm)で挟み、さらに14.3cm2の四角形に切断した負極を重ね合わせて電極群を作製した。この電極群を、アルミニウム製のラミネートフィルム(商品名:アルミラミネートフィルム、大日本印刷株式会社製)で形成された容器(電池外装体)に収容した。次いで、容器の中に調製した実施例1、実施例2、比較例1、又は比較例2の電解液をそれぞれ1mL添加し、容器を熱溶着させ、評価用のリチウムイオン二次電池を作製した。
作製したリチウムイオン電池について、以下に示す方法で初回充放電を実施した。まず、25℃の環境下において0.1Cの電流値で定電流充電を上限電圧4.2Vまで行い、続いて4.2Vで定電圧充電を行った。充電終止条件は、電流値0.01Cとした。その後、0.1Cの電流値で終止電圧2.5Vの定電流放電を行った。この充放電サイクルを3回繰り返した(電流値の単位として用いた「C」とは、「電流値(A)/電池容量(Ah)」を意味する。)。
初回充放電後、充放電を繰り返すサイクル試験によって、実施例1〜2及び比較例1〜2の電解液を用いた各二次電池のサイクル特性を評価した。充電パターンとしては、45℃の環境下で、二次電池を0.5Cの電流値で定電流充電を上限電圧4.2Vまで行い、続いて4.2Vで定電圧充電を行った。充電終止条件は、電流値0.05Cとした。放電については、1Cで定電流放電を2.5Vまで行い、放電容量を求めた。この一連の充放電を200サイクル繰り返し、充放電の度に放電容量を測定した。比較例1における1サイクル目の充放電後の放電容量を1として、各サイクルでの放電容量の相対値(放電容量比率)を求めた。サイクル数と放電容量の相対値との関係を、図7に示す。
Claims (7)
- 19F−NMRによる測定において、−180ppm以上−150ppm以下、及び−150ppmを超え−130ppm以下の少なくとも1つのケミカルシフトの範囲内にピークを示す、電解液。
- 19F−NMRによる測定において、−130ppmを超え−110ppm以下のケミカルシフトの範囲内にピークを更に示す、請求項1に記載の電解液。
- 正極と、負極と、請求項1又は2に記載の電解液と、を備える電気化学デバイス。
- 前記負極は炭素材料を含有する、請求項3に記載の電気化学デバイス。
- 前記炭素材料は黒鉛を含有する、請求項4に記載の電気化学デバイス。
- 前記負極は、ケイ素及びスズからなる群より選ばれる少なくとも1種の元素を含む材料を更に含有する、請求項4又は5に記載の電気化学デバイス。
- 前記電気化学デバイスは、非水電解液二次電池又はキャパシタである、請求項4〜6のいずれか一項に記載の電気化学デバイス。
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