JP2018530852A5 - - Google Patents
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- JP2018530852A5 JP2018530852A5 JP2017509778A JP2017509778A JP2018530852A5 JP 2018530852 A5 JP2018530852 A5 JP 2018530852A5 JP 2017509778 A JP2017509778 A JP 2017509778A JP 2017509778 A JP2017509778 A JP 2017509778A JP 2018530852 A5 JP2018530852 A5 JP 2018530852A5
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- lithium ion
- solvent
- ion battery
- high voltage
- electrolyte
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium Ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 58
- 229910001416 lithium ion Inorganic materials 0.000 claims description 58
- 239000003792 electrolyte Substances 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 32
- 239000003960 organic solvent Substances 0.000 claims description 31
- -1 propene sultone Chemical class 0.000 claims description 28
- 239000008151 electrolyte solution Substances 0.000 claims description 22
- 229910003002 lithium salt Inorganic materials 0.000 claims description 21
- 159000000002 lithium salts Chemical class 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 18
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 claims description 16
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 14
- 230000000996 additive Effects 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000012535 impurity Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000005676 cyclic carbonates Chemical group 0.000 claims description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002808 molecular sieve Substances 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 229910013870 LiPF 6 Inorganic materials 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- STSCVKRWJPWALQ-UHFFFAOYSA-N ethyl 2,2,2-trifluoroacetate Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- MCSINKKTEDDPNK-UHFFFAOYSA-N Propyl propanoate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- 229910013684 LiClO 4 Inorganic materials 0.000 claims description 3
- 229910012424 LiSO 3 Inorganic materials 0.000 claims description 3
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical group COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 claims description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N γ-lactone 4-hydroxy-butyric acid Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N Dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
- 229910013063 LiBF 4 Inorganic materials 0.000 claims description 2
- 229910013375 LiC Inorganic materials 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N Propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 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
- 239000000126 substance Substances 0.000 claims description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N γ-Valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 2
- 229940017219 METHYL PROPIONATE Drugs 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 description 24
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
- 229910052744 lithium Inorganic materials 0.000 description 11
- 230000001351 cycling Effects 0.000 description 7
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910002804 graphite Inorganic materials 0.000 description 5
- 239000010439 graphite Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reduced Effects 0.000 description 3
- 150000008053 sultones Chemical group 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 2
- KLLQVNFCMHPYGL-UHFFFAOYSA-N 5H-oxathiole 2,2-dioxide Chemical compound O=S1(=O)OCC=C1 KLLQVNFCMHPYGL-UHFFFAOYSA-N 0.000 description 2
- 229910013131 LiN Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004651 carbonic acid esters Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- VCYZVXRKYPKDQB-UHFFFAOYSA-N ethyl 2-fluoroacetate Chemical compound CCOC(=O)CF VCYZVXRKYPKDQB-UHFFFAOYSA-N 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-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 1
- PCRSJGWFEMHHEW-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1C#N PCRSJGWFEMHHEW-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 239000002000 Electrolyte additive Substances 0.000 description 1
- 210000002683 Foot Anatomy 0.000 description 1
- FRMOHNDAXZZWQI-UHFFFAOYSA-N [O-2].[Mn+2].[Ni+2].[Li+] Chemical compound [O-2].[Mn+2].[Ni+2].[Li+] FRMOHNDAXZZWQI-UHFFFAOYSA-N 0.000 description 1
- CLDYDTBRUJPBGU-UHFFFAOYSA-N butyl 2,2,2-trifluoroacetate Chemical compound CCCCOC(=O)C(F)(F)F CLDYDTBRUJPBGU-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002496 poly(ether sulfone) Polymers 0.000 description 1
- 229920003208 poly(ethylene sulfide) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Description
本発明はリチウムイオン電池の電解液の技術分野に含められ、具体的には高電圧広温度 The present invention is included in the technical field of electrolyte of lithium ion battery, and specifically, high voltage and wide temperature 範囲リチウムイオン電池の電解液の作り方と使用に関わる。本発明の電解液の安定性がよRange Involves how to make and use electrolytes in lithium ion batteries. The stability of the electrolyte of the present invention く、作り方も簡単であり、使用されれば高電圧広温度範囲リチウムイオン電池の循環寿命It is easy to make, and if it is used, the cycle life of high voltage wide temperature range lithium ion battery と高温性能を高める。And high temperature performance.
リチウムイオン電池は高エネルギー、小さいサイズ、軽い重量、無記憶、循環寿命など Lithium-ion batteries have high energy, small size, light weight, memorylessness, cycle life, etc. のメリットから、今まで一番早く発展して重視される新型の高エネルギー蓄電池になる。From the merits of the new high-energy storage battery that is the fastest growing and important to date. ここ数年、ポータブル電子デバイスは速く発展して、良いハードウエア構成、大きいサイIn the last few years, portable electronic devices have evolved rapidly to have good hardware configurations and large ズの画面、多様的な効能などの方面から、リチウムイオン電池のエネルギー密度に対するThe energy density of lithium-ion batteries from the perspective of 要求は厳しくなる。普通のリチウムイオン電池は既に人々の要求を満足できない。The demand becomes severe. Ordinary lithium ion batteries can not meet people's requirements already.
現在リチウムイオン電池のエネルギー密度を高めるために、研究者は普通に高容量、高 In order to increase the energy density of current lithium ion 電圧の陽極材料を開発する。例えば、リチウムコバルトの酸化物とリチウムマンガンの酸Develop an anode material for voltage. For example, lithium cobalt oxide and lithium manganese acid 化物の電圧を高め、高電圧のリチウムニッケルマンガンの酸化物などの開発をする。しかIncrease the voltage of the oxide and develop high-voltage lithium nickel manganese oxide etc. Only し、高電圧によって陽極材料の溶剤は構造が変わって、遷移金属は溶解しやすくて、さらThe high voltage causes the solvent of the anode material to change its structure, and the transition metal tends to dissolve easily. に陰極に沈殿する。それから、普通の電解液は4Vより大きい場合に分解し、気体が生じPrecipitate on the cathode. Then, ordinary electrolyte decomposes when it is higher than 4V, and gas is generated. る。それで、電池の性能が低くなる。以上の問題を解決するために、研究者は普通に陽極Ru. Thus, the performance of the battery is reduced. In order to solve the above problems, researchers usually 材料の表面を保護して、あるいはドーピングする。従って高電圧の場合で循環性能を高めProtect or dope the surface of the material. Therefore, the circulation performance is enhanced in the case of high voltage にする。だが、この方法によって電池の容量は消耗する。それにやり方は複雑で、コストMake it However, this method consumes battery capacity. And the way it is complicated and costly も高くなる。今までよく使っている電解液のシステムに替わる新型の高電圧電池の電解液Will also be high. New high-voltage battery electrolyte to replace the system of electrolytes often used so far を開発するには高電圧リチウムイオン電池を改善する方法がある。現在使っている電圧をThere is a way to improve high voltage lithium ion batteries to develop. The voltage currently used 高める電解液は、いつもは耐電圧を高めるにFEC(フッ素炭酸エチレン)の量を増加すElectrolyte to enhance, always increase the amount of FEC (Eurocarbonated Carbonate) to increase the withstand voltage る。しかし、電圧は4.5V以上になるとき、FECの量を増加すれば、電池の循環性能Ru. However, when the voltage goes above 4.5 V, if the amount of FEC is increased, the cycling performance of the battery は早く低くなる。だから高電圧の電解液添加剤を開発することは一刻の猶予も許さない。Will go lower quickly. Therefore, developing high-voltage electrolyte additives does not allow for a moment.
リチウムイオン電池のパワー密度を高め、現在の技術において電圧の電解液を高めるこ To increase the power density of lithium ion batteries and to increase the voltage electrolyte in current technology とによって電池の循環性能の低下を解決するため、本発明は高電圧広温度範囲リチウムイIn order to solve the deterioration of the cycling performance of the battery by オン電池の電解液、その調製方法及びその応用を提供する。Provided are an electrolyte solution of on-cell, a preparation method thereof and an application thereof.
本発明は、目的を実現するために採用する技術的解決法である。 The present invention is a technical solution adopted to realize the purpose.
有機溶剤、リチウム塩及び添加剤を含み、有機溶剤が環状炭酸エステル溶剤、含フッ素 The organic solvent contains an organic solvent, a lithium salt and an additive, and the organic solvent is a cyclic carbonate solvent, a fluorine-containing solvent
溶剤及び炭酸エステル溶剤を含む、高電圧広温度範囲リチウムイオン電池の電解液であっAn electrolyte of a high voltage wide temperature range lithium ion battery containing a solvent and a carbonic acid ester solvent
て、添加剤が3−フッ素−1,3プロペンスルトンであり、リチウムイオン電池の電解液, The additive is 3-fluorine-1,3 propene sultone, and the electrolyte of a lithium ion battery
中の添加剤の含有量が0.5%〜10%である。The content of the additive is 0.5% to 10%.
リチウム塩の有機溶剤中における濃度が1〜1.5mol/Lであり、電解液中におけ The concentration of lithium salt in the organic solvent is 1 to 1.5 mol / L, and る含フッ素溶剤の質量百分率が2〜50%である。The mass percentage of the fluorinated solvent is 2 to 50%.
環状炭酸エステル溶剤は、炭酸エチレン、炭酸プロピレン、γ−ブチロラクトン、γ− The cyclic carbonate solvent is ethylene carbonate, propylene carbonate, γ-butyrolactone, γ- バレロラクトンのうちの一種又は複数種から選ばれる。It is selected from one or more of valerolactone.
含フッ素溶剤は、トリフルオロ酢酸メチル、トリフルオロ酢酸エチル、トリフルオロ酢 Fluorinated solvents are methyl trifluoroacetate, ethyl trifluoroacetate, trifluorovinegar 酸ブチルのうちの一種又は複数種から選ばれる。It is selected from one or more of butyl acid.
炭酸エステル溶剤は、炭酸ジメチル、炭酸エチルメチル、炭酸ジエチル、プロピオン酸 Carbonic ester solvents are dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, propionic acid メチル、プロピオン酸エチル、プロピオン酸プロピルのうちの一種又は複数種から選ばれSelected from one or more of methyl, ethyl propionate and propyl propionate る。Ru.
リチウム塩は、LiPF Lithium salt is LiPF 66 、LiBF, LiBF 44 、LiSO, LiSO 33 CFCF 33 、LiClO, LiClO 44 、LiN(, LiN ( CFCF 33 SOSO 22 )) 22 、LiC(CF, LiC (CF 33 SOSO 22 )) 33 のうちの一種又は複数種から選ばれる。Selected from one or more of
上記高電圧広温度範囲リチウムイオン電池の電解液の調製方法であって、環状炭酸エス It is a preparation method of electrolyte solution of the above-mentioned high voltage wide temperature range lithium ion battery, and cyclic carbonate S テル溶剤、含フッ素溶剤及び炭酸エステル溶剤を均一に混合した後、不純物及び水を取りUniformly mix tellurium solvent, fluorine-containing solvent and carbonic acid ester solvent, remove impurities and water 除き、室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌し、その後3The lithium salt is dissolved in the mixed solvent at room temperature and uniformly stirred, and then −フッ素−1,3プロペンスルトンを加えて、透明になるまで溶解した後にろ過して、上-Add fluorine-1,3 propene sultone, dissolve until clear and then filter, 記高電圧広温度範囲リチウムイオン電池の電解液を得る。An electrolyte for a high voltage wide temperature range lithium ion battery is obtained.
環状炭酸エステル溶剤、含フッ素溶剤及び炭酸エステル溶剤を均一に混合した後、4Å After uniformly mixing cyclic carbonate solvent, fluorine-containing solvent and carbonate solvent, 4 Å 分子篩及び水素化リチウムを用いて、不純物及び水を取り除く。Remove impurities and water using molecular sieve and lithium hydride.
上記高電圧広温度範囲リチウムイオン電池の電解液における高電圧広温度範囲リチウム High voltage wide temperature range lithium in electrolyte of the above high voltage wide temperature range lithium ion battery イオン電池の調製への応用である。Application to the preparation of ion batteries.
添加剤である3−フッ素−1,3プロペンスルトンの構造式は、下記化学式のように示 The structural formula of the additive 3-fluorine-1,3 propene sultone is shown as the following chemical formula
される。Be done.
本発明の良い効果 Good effect of the present invention
電解液溶剤に含フッ素溶剤を混ぜれば、高電圧によって電解液の分解は少なくなるので If a fluorine-containing solvent is mixed with the electrolyte solvent, decomposition of the electrolyte is reduced due to the high voltage.
、電解液の酸化安定性が高まる。同時に、含フッ素溶剤はよい浸潤性を持つから、電解液The oxidation stability of the electrolyte is increased. At the same time, since fluorinated solvents have good infiltration properties, electrolytes
の浸潤性を改善できる。そして3−フッ素−1,3プロペンスルトンを加えるのは陽極をImprove the infiltration of And adding 3-fluorine-1,3 propene sultone is positive
よく保護して、陽極材料において遷移金属の溶出を減らすことができる。同時に、陰極にGood protection can reduce the elution of transition metals in the anode material. At the same time,
SEI膜ができ、遷移金属によって陰極に残っていた沈殿と還元を減らす。従って、陰極The SEI film is formed, reducing the precipitation and reduction left on the cathode by the transition metal. Therefore, the cathode
は安全に保護される。これは高電圧の場合での電池の循環安定性と高温性能を高めるのにAre safely protected. This is to enhance the cycling stability and high temperature performance of the battery in the case of high voltage
有利であり、さらにリチウムイオン電池がもたらす火災や爆発などの安全問題の発生を防It is also advantageous to prevent the occurrence of safety problems such as fires and explosions caused by lithium ion batteries.
止し、電池安定性を高める。リチウムイオン電池は充電する効率が高くて、循環性能がよStop and increase battery stability. Lithium-ion batteries have high charging efficiency and good circulation performance.
くて、500回で85%の充電放電の要求を満足できる。特にリチウムイオン電池の高温It can meet the requirement of 85% charge and discharge in 500 times. Especially high temperature of lithium ion battery
循環性能が改善できて、電池の貯蔵性能が良くなって、リチウムイオン電池の他の性能がThe circulation performance can be improved, the storage performance of the battery is improved, and the other performance of the lithium ion battery is
影響を受けない。Not affected
本発明の高電圧広温度範囲リチウムイオン電池の電解液の調製方法は簡単であり、同時 The method of preparing the electrolyte of the high voltage wide temperature range lithium ion battery of the present invention is simple and simultaneous に電池の陽陰極は電解液との表面性質を改善する。電解液の安定性は非常に良くて、高電The positive and negative electrodes of the cell improve the surface properties with the electrolyte. The stability of the electrolyte is very good. 圧リチウムイオン電池の循環寿命と高温性能を高める。Boost the cycle life and high temperature performance of high pressure lithium ion batteries.
本発明における高電圧広温度範囲リチウムイオン電池の電解液によって作られる高電圧 High voltage produced by the electrolyte of high voltage wide temperature range lithium ion battery in the present invention 広温度範囲リチウムイオン電池は循環寿命が高くて、膨張率、高温性能が良くて、電池のWide temperature range lithium ion battery has high circulation life, good expansion coefficient and high temperature performance, 電圧は4.5Vより高い。The voltage is higher than 4.5V.
それに、3−フッ素−1,3プロペンスルトンは、電解液は電極の表面で酸化して、あ In addition, 3-fluorine-1,3 propene sultone oxidizes the electrolyte at the surface of the electrode and るいは還元分解することを抑止できる。これは電極へのダメージを減らして、電解液と電It is possible to prevent reductive decomposition. This reduces damage to the electrode and 極とのコンパチビリティを高める。Improve compatibility with poles.
図の中に、▲は基礎電解液(EC:DMC=1:2,1M LiPF In the figure, ▲ indicates the base electrolyte (EC: DMC = 1: 2,1M LiPF 66 ,FEC1%), FEC 1%) を表して、■は本発明の電解液を表す。Represents the electrolytic solution of the present invention.
以下は具体的な実施例の上で本発明を説明する。 The invention will now be described on the basis of specific examples.
実施例1 Example 1
高電圧広温度範囲リチウムイオン電池の電解液は、有機溶剤、LiPF Electrolyte solution of high voltage wide temperature range lithium ion battery, organic solvent, LiPF
66
と3−フッ素And 3-fluorine
−1,3プロペンスルトンからなる。その中に、有機溶剤は重量比が1:2:0.2のエ-1, consisting of propene sultone. Among them, the organic solvent has a weight ratio of 1: 2: 0.2
チレンカーボネート、エチルメチルカーボネート及びトリフルオロ酢酸エチルからなる。It consists of thylene carbonate, ethyl methyl carbonate and ethyl trifluoroacetate.
本電解液において3−フッ素−1,3プロペンスルトンという添加剤の含有量が2wt%The content of additives such as 3-fluorine-1,3 propene sultone in this electrolytic solution is 2 wt%
である。有機溶剤において、リチウム塩の濃度が1mol/Lで、電解液におけるトリフIt is. In organic solvent, the concentration of lithium salt is 1 mol / L, and
ルオロ酢酸エチルの質量百分率が20%である。The mass percentage of ethyl fluoroacetate is 20%.
上記高電圧広範囲リチウムイオン電池の電解液の調製方法。 A method of preparing an electrolyte of the high voltage wide range lithium ion battery.
(1)有機溶剤を均一に混合した後、4Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, use 4 Å molecular sieves, lithium hydride, impurities, water
を取り除く。Get rid of
(2)室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌する。(2) Dissolve the lithium salt in the mixed solvent at room temperature and stir uniformly.
(3)その後、3−フッ素−1,3プロペンスルトンを加えて、透明になるまで溶解した(3) Then, 3-fluorine-1,3 propene sultone was added and dissolved until it became transparent
後にろ過して、上記高電圧広温度範囲リチウムイオン電池の電解液を得る。The solution is then filtered to obtain the electrolyte of the high voltage wide temperature range lithium ion battery.
上記3−フッ素−1,3プロペンスルトンの調製方法は、以下のように行う。 The preparation method of said 3-fluorine- 1,3 propene sultone is performed as follows.
1−プロペン1,3−スルトンを原料にして、600mLのジクロロメタンで1mol Starting from 1-propene 1,3-sultone, 1 mol with 600 mL of dichloromethane
の1−プロペン1,3−スルトンを溶解する。50℃下で1.05molのNBSをグルDissolve 1-propene 1,3-sultone of At 50 ° C, 1.05 mol NBS is
ープに分けて加える。10時間の後、中間物3−臭素−1,3プロペンスルトンを得る。Divide into pieces and add. After 10 hours, the intermediate 3-bromo-1,3 propene sultone is obtained.
そして中間物とフッ化ナトリウムをジクロロメタンに加えて、シクロデキストリンがあるThen add the intermediate and sodium fluoride to the dichloromethane, there is cyclodextrin
場合で交換反応ができ、3−フッ素−1,3プロペンスルトンを得る。F元素が存在するIn some cases exchange reactions can be performed to obtain 3-fluoro-1,3 propene sultone. F element exists
ので、1−プロペン1,3−スルトンより3−フッ素−1,3プロペンスルトンは更に電Therefore, 3-fluoro-1,3-propene sultone is more
池の電圧を高めて、リチウムイオン電池の高電圧の分野に広く応用される。同時に、3−It is widely applied to the high voltage field of lithium ion batteries by raising the voltage of the pond. At the same time, 3-
フッ素−1,3プロペンスルトンは、今まで使っている電池の三元系材料の高温循環性能Fluorine-1,3 propene sultone is the high temperature circulation performance of the battery ternary materials used so far
を改善できて、電池の循環寿命も改善できる。The cycle life of the battery can also be improved.
本実施例の高電圧広温度範囲リチウムイオン電池の電解液をコバルト酸リチウム/グラ The electrolyte solution of the high voltage wide temperature range lithium ion battery of this example is lithium cobaltate / gram ファイト電池に用い、常温でコバルト酸リチウム/グラファイト電池について3.0〜43.0 to 4 for lithium cobaltate / graphite battery at normal temperature .95V、1C倍率充電と放電の循環性能をテストする。200回の周期に循環した後、. Test the circulation performance of 95V, 1C magnification charge and discharge. After circulating for 200 cycles, 電気容量の保持率は94%以上であり、300回の周期に循環した後、電気容量の保持率The retention rate of the electrical capacity is 94% or more, and after cycling in 300 cycles, the retention rate of the electrical capacity は91%以上であり、400回の周期に循環した後、電気容量の保持率は約90%でありIs over 91%, and after being cycled 400 times, the capacity retention rate is about 90% and 、500回の周期に循環した後、電気容量の保持率は依然として85%以上に達する。After circulating for 500 cycles, the retention of the electrical capacity still reaches 85% or more.
実施例2 Example 2
高電圧広温度範囲リチウムイオン電池の電解液は、有機溶剤、LiN(CF The electrolyte of the high voltage wide temperature range lithium ion battery is an organic solvent, LiN (CF)
33
SOSO
22
))
22
及び3−フッ素−1,3プロペンスルトンからなる。その中に、有機溶剤は重量比が1And 3-fluorine-1,3 propene sultone. Among them, organic solvent weight ratio 1
:2:0.2のエチレンカーボネート、エチルメチルカーボネート及びトリフルオロ酢酸: 2: 0.2 ethylene carbonate, ethyl methyl carbonate and trifluoroacetic acid
メチルからなる。本電解液において3−フッ素−1,3プロペンスルトンという添加剤のIt consists of methyl. In the present electrolytic solution, an additive called 3-fluorine-1,3 propene sultone
含有量が4wt%である。有機溶剤において、リチウム塩の濃度が1.5mol/Lで、The content is 4 wt%. In the organic solvent, the concentration of lithium salt is 1.5 mol / L,
電解液におけるトリフルオロ酢酸エチルの質量百分率が30%である。The mass percentage of ethyl trifluoroacetate in the electrolyte is 30%.
上記高電圧広温度範囲リチウムイオン電池の電解液の調製方法 Method of preparing electrolyte of the above high voltage wide temperature range lithium ion battery
(1)有機溶剤を均一に混合した後、4Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, use 4 Å molecular sieves, lithium hydride, impurities, water
を取り除く。Get rid of
(2)室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌する。(2) Dissolve the lithium salt in the mixed solvent at room temperature and stir uniformly.
(3)その後、3−フッ素−1,3プロペンスルトンを加えて、透明になるまで溶解した(3) Then, 3-fluorine-1,3 propene sultone was added and dissolved until it became transparent
後にろ過して、上記高電圧広温度範囲リチウムイオン電池の電解液を得る。The solution is then filtered to obtain the electrolyte of the high voltage wide temperature range lithium ion battery.
本実施例の高電圧広温度範囲リチウムイオン電池の電解液をコバルト酸リチウム/グラ The electrolyte solution of the high voltage wide temperature range lithium ion battery of this example is lithium cobaltate / gram ファイト電池に用い、常温でコバルト酸リチウム/グラファイト電池について3.0〜43.0 to 4 for lithium cobaltate / graphite battery at normal temperature .95V、1C倍率充電と放電の循環性能をテストする。200回の周期に循環した後、. Test the circulation performance of 95V, 1C magnification charge and discharge. After circulating for 200 cycles, 電気容量の保持率は93%であり、300回の周期に循環した後、電気容量の保持率は9The retention rate of the electrical capacity is 93%, and after the cycle of 300 cycles, the retention rate of the electrical capacity is 9 0%であり、400回の周期に循環した後、電気容量の保持率は89%であり、500回The retention rate of the electrical capacity is 89%, and after 500 cycles, it is 0%. の周期に循環した後、電気容量の保持率は依然として85%以上に達する。After being cycled through, the retention of the electrical capacity still reaches 85% or more.
実施例3 Example 3
高電圧広温度範囲リチウムイオン電池の電解液は、有機溶剤、LiClO Electrolyte solution of high voltage wide temperature range lithium ion battery, organic solvent, LiClO
44
及び3−フAnd 3-f
ッ素−1,3プロペンスルトンからなる。その中に、有機溶剤は重量比が1:2:0.2It consists of nitrogen-1,3 propene sultone. Among them, the weight ratio of organic solvent is 1: 2: 0.2
のγ−ブチロラクトン、プロピオン酸プロピル及びトリフルオロ酢酸ブチルからなる。本Γ-butyrolactone, propyl propionate and butyl trifluoroacetate. Book
電解液において3−フッ素−1,3プロペンスルトンという添加剤の含有量が6wt%でThe content of additive of 3-fluorine-1,3 propene sultone in the electrolytic solution is 6wt%
ある。有機溶剤において、リチウム塩の濃度が1.2mol/Lで、電解液におけるトリis there. In the organic solvent, the concentration of lithium salt is 1.2 mol / L, and
フルオロ酢酸エチルの質量百分率が40%である。The mass percentage of ethyl fluoroacetate is 40%.
上記高電圧広温度範囲リチウムイオン電池の電解液の調製方法 Method of preparing electrolyte of the above high voltage wide temperature range lithium ion battery
(1)有機溶剤を均一に混合した後、4Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, use 4 Å molecular sieves, lithium hydride, impurities, water
を取り除く。Get rid of
(2)室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌する。(2) Dissolve the lithium salt in the mixed solvent at room temperature and stir uniformly.
(3)その後、3−フッ素−1,3プロペンスルトンを加えて、透明になるまで溶解した(3) Then, 3-fluorine-1,3 propene sultone was added and dissolved until it became transparent
後にろ過して、上記高電圧広温度範囲リチウムイオン電池の電解液を得る。The solution is then filtered to obtain the electrolyte of the high voltage wide temperature range lithium ion battery.
本実施例の高電圧広温度範囲リチウムイオン電池の電解液をコバルト酸リチウム/グラ The electrolyte solution of the high voltage wide temperature range lithium ion battery of this example is lithium cobaltate / gram ファイト電池に用い、常温でコバルト酸リチウム/グラファイト電池について3.0〜43.0 to 4 for lithium cobaltate / graphite battery at normal temperature .95V、1C倍率充電と放電の循環性能をテストする。200回の周期に循環した後、. Test the circulation performance of 95V, 1C magnification charge and discharge. After circulating for 200 cycles, 電気容量の保持率は94%であり、300回の周期に循環した後、電気容量の保持率は9The retention rate of the electrical capacity is 94%, and after cycling in 300 cycles, the retention rate of the electrical capacity is 9 1%であり、400回の周期に循環した後、電気容量の保持率は90%であり、500回1%, and after circulation in 400 cycles, the retention rate of electric capacity is 90%, 500 times の周期に循環した後、電気容量の保持率は依然として85%以上に達する。After being cycled through, the retention of the electrical capacity still reaches 85% or more.
実施例4 Example 4
高電圧広温度範囲リチウムイオン電池の電解液は、有機溶剤、LiSO Electrolyte solution of high voltage wide temperature range lithium ion battery, organic solvent, LiSO
33
CFCF
33
及び3And 3
−フッ素−1,3プロペンスルトンからなる。その中に、有機溶剤は重量比が1:2:0-Consisting of fluorine-1,3 propene sultone. Among them, the weight ratio of organic solvent is 1: 2: 0
.2のγ−バレロラクトン、プロピオン酸プロピル及びトリフルオロ酢酸メチルからなる. Consisting of 2 γ-valerolactone, propyl propionate and methyl trifluoroacetate
。本電解液において3−フッ素−1,3プロペンスルトンという添加剤の含有量が2.5. In this electrolytic solution, the content of an additive such as 3-fluorine-1,3 propene sultone is 2.5
wt%である。有機溶剤において、リチウム塩の濃度が1.2mol/Lで、電解液におIt is wt%. In the organic solvent, the concentration of lithium salt is 1.2 mol / L and
けるトリフルオロ酢酸エチルの質量百分率が35%である。The mass percentage of ethyl trifluoroacetate is 35%.
上記高電圧広温度範囲リチウムイオン電池の電解液の調製方法 Method of preparing electrolyte of the above high voltage wide temperature range lithium ion battery
(1)有機溶剤を均一に混合した後、4Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, use 4 Å molecular sieves, lithium hydride, impurities, water
を取り除く。Get rid of
(2)室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌する。(2) Dissolve the lithium salt in the mixed solvent at room temperature and stir uniformly.
(3)その後、3−フッ素−1,3プロペンスルトンを加えて、透明になるまで溶解した(3) Then, 3-fluorine-1,3 propene sultone was added and dissolved until it became transparent
後にろ過して、上記高電圧広温度範囲リチウムイオン電池の電解液を得る。The solution is then filtered to obtain the electrolyte of the high voltage wide temperature range lithium ion battery.
本実施例の高電圧広温度範囲リチウムイオン電池の電解液をコバルト酸リチウム/グラ The electrolyte solution of the high voltage wide temperature range lithium ion battery of this example is lithium cobaltate / gram ファイト電池に用い、常温でコバルト酸リチウム/グラファイト電池について3.0〜43.0 to 4 for lithium cobaltate / graphite battery at normal temperature .95V、1C倍率充電と放電の循環性能をテストする。200回の周期に循環した後、. Test the circulation performance of 95V, 1C magnification charge and discharge. After circulating for 200 cycles, 電気容量の保持率は94%であり、300回の周期に循環した後、電気容量の保持率は9The retention rate of the electrical capacity is 94%, and after cycling in 300 cycles, the retention rate of the electrical capacity is 9 1%であり、400回の周期に循環した後、電気容量の保持率は90%であり、500回1%, and after circulation in 400 cycles, the retention rate of electric capacity is 90%, 500 times の周期に循環した後、電気容量の保持率は依然として85%以上に達する。After being cycled through, the retention of the electrical capacity still reaches 85% or more.
対比実施例1 Comparative Example 1
高電圧リチウムイオン電池の電解液の原材料は、主に有機溶剤、電気伝導のリチウム塩 Raw materials for electrolytes of high-voltage lithium-ion batteries are mainly organic solvents, lithium salts for electrical conduction
、及び機能性添加剤を含む。前記有機溶剤は炭酸エチレン(EC)、炭酸エチルメチル(And functional additives. The organic solvent is ethylene carbonate (EC), ethyl methyl carbonate (EC
EMC)、フルオロエチレン・カーボネート(FEC)及び1,2,2−テトラフルオロEMC), fluoroethylene carbonate (FEC) and 1,2,2-tetrafluoro
エチル−2,2,3,3−テトラフルオロ・プロピルエーテル(CFEthyl-2,2,3,3-tetrafluoropropyl ether (CF
22
HCFHCF
22
CHCH
22
−-
O−CFO-CF
22
CFCF
22
H)からなる。その中で、ECとEMCの重量比は、EC:EMC=1H). Among them, the weight ratio of EC to EMC is EC: EMC = 1
:2である。EFCの含有量が10wt%で、1,2,2−テトラフルオロエチル−2,: 2. 1,2,2-Tetrafluoroethyl-2, at a content of EFC of 10 wt%
2,3,3−テトラフルオロ・プロピルエーテル(CF2,3,3-Tetrafluoropropyl ether (CF
22
HCFHCF
22
CHCH
22
−O−CF-O-CF
22
CC
FF
22
H)の含有量が5wt%である。リチウム塩がLiPFThe content of H) is 5 wt%. Lithium salt is LiPF
66
で、有機溶剤における濃度In the organic solvent
が1.2mol/Lである。機能性添加剤は、含有量が2wt%の1−プロペン1,3−Is 1.2 mol / L. The functional additive has a content of 2 wt% 1-propene 1,3-
スルトン(PES)である。It is sultone (PES).
上記高電圧リチウムイオン電池の電解液の調製方法 Method of preparing electrolyte of the above high voltage lithium ion battery
(1)有機溶剤を均一に混合した後、5Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, using 5 Å molecular sieves and lithium hydride, impurities, water
を取り除く。Get rid of
(2)室温下でリチウム塩を上記混合後の溶剤中に溶解させて、均一に撹拌する。(2) Dissolve the lithium salt in the mixed solvent at room temperature and stir uniformly.
(3)機能性添加剤を加えて、上記高電圧リチウムイオン電池の電解液を得る。(3) A functional additive is added to obtain an electrolyte solution of the high voltage lithium ion battery.
本実施例の高電圧リチウムイオン電池の電解液をリチウムニッケルマンガン(LiNi Lithium nickel manganese (LiNi) was used as the electrolyte for the high voltage lithium ion battery of this example. 0.50.5 MnMn 1.51.5 OO 44 )電池に用い、常温でLiNi) Used in batteries, LiNi at normal temperature 0.50.5 MnMn 1.51.5 OO 44 電池についてAbout battery 3.0〜4.95V、1C倍率充電と放電の循環性能をテストする。200回の周期に循Test the circulation performance of 3.0-4.95V, 1C magnification charge and discharge. Circulation in 200 cycles 環した後、電気容量の保持率は92%であり、300回の周期に循環した後、電気容量のAfter ringing, the retention rate of the electrical capacity is 92%, and after being circulated for 300 cycles, 保持率は90%であり、400回の周期に循環した後、電気容量の保持率は88%でありThe retention rate is 90%, and the retention rate of electrical capacity is 88% after circulation in 400 cycles. 、500の周期に循環した後、電気容量の保持率は80%に達する。After circulating for 500 cycles, the retention rate of the electrical capacity reaches 80%.
対比実施例2 Comparative Example 2
高電圧リチウムイオン電池の電解液の原材料は、主に有機溶剤、リチウム塩及び添加剤 Raw materials for electrolytes of high voltage lithium ion batteries mainly consist of organic solvents, lithium salts and additives
を含む。有機溶剤は、環状炭酸エステル溶剤(炭酸エチレンEC)及び線状炭酸エステルincluding. Organic solvents include cyclic carbonate solvents (ethylene carbonate EC) and linear carbonates
溶剤(炭酸エチルメチルEMC及び炭酸ジエチルDEC)からなる。ECと線状炭酸エスIt consists of solvents (ethyl methyl carbonate EMC and diethyl carbonate DEC). EC and linear carbon dioxide S
テルの重量比は、EC:EMC:DEC=1:1:1である。リチウム塩がLiPFThe weight ratio of tellurium is EC: EMC: DEC = 1: 1: 1. Lithium salt is LiPF
66
でso
、有機溶剤における濃度が1.0mol/Lである。普通の添加剤は、含有量が1.0wAnd the concentration in the organic solvent is 1.0 mol / L. Ordinary additives have a content of 1.0 w
t%の炭酸エチレン及びスルトンからなる。添加剤におけるテトラフルオロテレフタロニConsisting of t% ethylene carbonate and sultone. Tetrafluoroterephthaloni in additives
トリルの含有量が1.0wt%で、3−フルオロベンゾニトリルの含有量が2.0wt%The content of tolyl is 1.0wt% and the content of 3-fluorobenzonitrile is 2.0wt%
である。It is.
上記電解液の調製方法 Method of preparing the above electrolyte
(1)有機溶剤を均一に混合した後、5Å分子篩、水素化リチウムを用いて、不純物、水(1) After uniformly mixing the organic solvent, using 5 Å molecular sieves and lithium hydride, impurities, water
を取り除く。Get rid of
(2)炭酸ビニレンとスルトンというよく使用している添加剤を加えて、均一に撹拌する(2) Add commonly used additives such as vinylene carbonate and sultone and uniformly stir
。.
(3)テトラフルオロテレフタロニトリルと3−フルオロベンゾニトリルを加えて、上記(3) adding tetrafluoroterephthalonitrile and 3-fluorobenzonitrile,
高電圧リチウムイオン電池の電解液を得る。An electrolyte for a high voltage lithium ion battery is obtained.
本実施例の高電圧広温度範囲リチウムイオン電池の電解液をコバルト酸リチウム/グラ The electrolyte solution of the high voltage wide temperature range lithium ion battery of this example is lithium cobaltate / gram ファイト電池に用い、常温でコバルト酸リチウム/グラファイト電池について3.0〜43.0 to 4 for lithium cobaltate / graphite battery at normal temperature .5V、1C倍率充電と放電の循環性能をテストする。200回の周期に循環した後、電. Test circulation performance of 5V, 1C magnification charge and discharge. After circulating in 200 cycles, 気容量の保持率は90%であり、300回の周期に循環した後、電気容量の保持率は85The retention rate of air volume is 90%, and the retention rate of electrical capacity is 85 after circulation in 300 cycles. %であり、400回の周期に循環した後、電気容量の保持率は80%であり、500回の%, And after being circulated for 400 cycles, the retention rate of the electrical capacity is 80%, 500 cycles of 周期に循環した後、電気容量の保持率は70%に達する。After cycling through the cycle, the retention of the electrical capacity reaches 70%.
Claims (7)
前記添加剤が3−フッ素−1,3プロペンスルトンであり、 The additive is 3-fluorine-1,3 propene sultone,
前記リチウムイオン電池の電解液中の前記添加剤の含有量が質量百分率で0.5〜10 The content of the additive in the electrolyte of the lithium ion battery is 0.5 to 10 by mass percentage %であり、%,
前記含フッ素溶剤は、トリフルオロ酢酸メチル、トリフルオロ酢酸エチル、トリフルオ The fluorine-containing solvent is methyl trifluoroacetate, ethyl trifluoroacetate, trifluoro ロ酢酸ブチルのうちの一種又は複数種から選ばれ、It is selected from one or more of butyl loacetate,
前記炭酸エステル溶剤は、炭酸ジメチル、炭酸エチルメチル、炭酸ジエチル、プロピオ The said carbonate solvent is dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, propio ン酸メチル、プロピオン酸エチル、プロピオン酸プロピルのうちの一種又は複数種から選Selected from one or more of methyl propionate, ethyl propionate and propyl propionate ばれる、高電圧広温度範囲リチウムイオン電池の電解液。High-voltage wide-temperature range lithium-ion battery electrolyte.
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