WO2021240448A1 - Solution électrolytique pour batterie secondaire, et batterie secondaire la comprenant - Google Patents

Solution électrolytique pour batterie secondaire, et batterie secondaire la comprenant Download PDF

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Publication number
WO2021240448A1
WO2021240448A1 PCT/IB2021/054671 IB2021054671W WO2021240448A1 WO 2021240448 A1 WO2021240448 A1 WO 2021240448A1 IB 2021054671 W IB2021054671 W IB 2021054671W WO 2021240448 A1 WO2021240448 A1 WO 2021240448A1
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Prior art keywords
formula
carbonate
secondary battery
electrolyte
group
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PCT/IB2021/054671
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English (en)
Korean (ko)
Inventor
김동윤
박정현
김형락
Original Assignee
동화일렉트로라이트 주식회사
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Publication of WO2021240448A1 publication Critical patent/WO2021240448A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • H01M2300/0037—Mixture of solvents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • Electrolyte for secondary battery and field of invention of secondary battery comprising same
  • the present invention relates to electrolyte for secondary battery and secondary battery including the same, and more specifically, to lithium ion secondary battery It relates to a non-aqueous electrolyte solution for a secondary battery having the effect of improving lifespan and high-temperature storage characteristics by adding a salt represented by Formula 1 or Formula 2 to an aqueous electrolyte solution, and a secondary battery including the same.
  • BACKGROUND ART Recently, portable electronic devices have been widely distributed, and accordingly, these portable electronic devices are becoming thinner, smaller, and lighter.
  • Secondary batteries include a lead-acid battery, nickel-cadmium ( ⁇ (1) battery, nickel-hydrogen ⁇ ) battery, lithium battery, etc., depending on the material or positive electrode (0 ⁇ 110(16) material.
  • lithium secondary batteries have high energy density due to the low oxidation/reduction potential and molecular weight of lithium, so they are widely used as a driving power source for portable electronic devices such as notebooks, camcorders, or mobile phones.
  • the positive electrode active material of the non-aqueous electrolyte secondary battery is made of lithium and/or lithium-containing metal oxide capable of occluding and releasing lithium and/or lithium ions, such a positive electrode Active material is overcharged 2021/240448 1» (When 1'/18201/054671 lithium is released, it is transformed into a thermally unstable structure.
  • Japanese Patent Application Laid-Open No. 2013-157305 discloses an electrolyte solution containing a compound having two isocyanate groups
  • Korean Patent No. 10-0412522 discloses di-_butylsilylbis (tri Fluoromethane sulfonate), trimethylsilylmethanesulfonate, trimethylsilylbenzenesulfonate, trimethylsilyl trifluoromethanesulfonate, triethylsilyl trifluoromethanesulfonate, etc.
  • An object of the present invention is to provide a non-aqueous electrolyte for a secondary battery with improved lifespan characteristics at room temperature and high temperature and output characteristics before and after high temperature.
  • Another object of the present invention is to provide a secondary battery having excellent lifespan characteristics at room temperature and high temperature and output characteristics before and after high temperature.
  • (Si lithium salt; ) Non-aqueous organic solvent; And (0 provides a non-aqueous electrolyte for a secondary battery comprising at least one additive selected from the group consisting of salts represented by Formulas 1 and 2.
  • the seed is an alkenyl group having 2 to 9 carbon atoms
  • the present invention also provides (3) a positive electrode comprising a positive electrode active material capable of occluding and discharging lithium; (A negative electrode comprising a negative electrode active material capable of intercalating and releasing lithium; ((:) the electrolyte solution for the secondary battery; and (!) provides a secondary battery including a separator.
  • the present invention provides a non-aqueous organic solvent (0 compound represented by Formula 1 and a salt represented by Formula 2) It provides a non-aqueous electrolyte for a secondary battery comprising at least one additive selected from the group consisting of [Formula 1] 2021/240448 1 ⁇ (:1 ⁇ 2021/054671
  • urea is an alkenyl group having 2 to 9 carbon atoms, o
  • M + is imidazolium, pyridinium,
  • a positive electrode comprising a positive electrode active material capable of occluding and discharging lithium
  • a negative electrode comprising an anode active material capable of occluding and releasing lithium
  • the electrolyte solution for the secondary battery and (d) relates to a secondary battery comprising a separator.
  • the non-aqueous electrolyte for a secondary battery according to the present invention is (A) a lithium salt; (B) non-aqueous 2021/240448 1 ⁇ (:1 ⁇ 2021/054671 organic solvent; and ⁇ ) may include one or more additives selected from the group consisting of salts represented by Chemical Formulas 1 and 2. [Formula 1] [Formula 2] o
  • a key is an alkenyl group having 2 to 9 carbon atoms
  • M + is imidazolium, pyridinium, pyrrolidinium, ammonium, phosphonium ) or sulfonium (su 1fonium).
  • the alkenyl group having 2 to 9 carbon atoms may include, but is not limited to, vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl and isobutenyl groups.
  • the compound represented by Formula 1 is triethylammonium ethenesulfonate (1:) 3 ⁇ 4 ⁇ 13 ⁇ 4111111011 ⁇ 1111 Ethenesulfonate 2-ethyl 4-methyl imidazolium ( ]16]16311 0]1 6 2- ]3 ⁇ 4, 1 4_11161:]3 ⁇ 4, 1 (13 ⁇ 4 01 ⁇ 1111), a compound represented by Formula 1-2 Ethenesulfonate -methyl-2 -pyrrolidinium ( 116116311 011 6 - 1 1: ]3 ⁇ 4 ⁇ 1-2 0'01 1111 ⁇ ) as a compound represented by 1-3 or 1-to as a compound represented by Formula 1_4
  • Tenyl-111-imidazole- 3-ium ethenesulfonate (1_61:11613 ⁇ 4, 1-:na1-:11 (13 ⁇ 4 01-3 - : ⁇ 116116311 011 6) is preferably
  • the compound represented by Formula 2 is triethylammonium which is a compound represented by Formula 2 - 1 ⁇ ) 1103 to 11011 6), 2-ethyl-4 -methyl- 111-, which is a compound represented by Formula 2-2 vinylphosphonate) , 1-methyl-2oxopyrrolidine-!-um vinylphosphonate (1,61:]3 ⁇ 4,1-2-( «(3 ⁇ 4)71,1,01 111, a compound represented by Formula 2_3 -1-:1) ⁇ ⁇ 13 ⁇ 4, 1]]]]]]]] 103]]]] 1011 6) or 1-vinyl-111-imidazole-2-um vinylphosphonate (1- ⁇ 171-1 ⁇ 1-; [1111(13201-3-; [ ⁇ ⁇ 1711)11031)11011 6) is preferably used, but is not limited thereto.
  • it may further include one or more life performance enhancing additives selected from the group consisting of compounds represented by the following Chemical Formula Show-1, Chemical Formula / ⁇ 2 and Chemical Formula / ⁇ 3.
  • Chemical Formula Show-1 11 1 0 1) 011 6 ) 2021/240448 1 ⁇ (:1 ⁇ 2021/054671 vinyl ethylene carbonate)
  • At least one selected from the group consisting of compounds represented by Chemical Formula 0-1, Chemical Formula 0-2, Chemical Formula 0-3, and Chemical Formula 04 may further include an additive for improving performance.
  • One or more high temperature and output performance enhancing additives selected from the group consisting of compounds represented by -4 may be additionally included.
  • the lithium salt used as the solute of the electrolyte is Ni 1 ? 6 , Knee 8?4, Knee 3 ⁇ 43 ⁇ 4, 110104 Knee.23 ⁇ 4302)2 Knee 3 ⁇ 4302)2, ⁇ 0 3 Knee and It may be one or more types selected from the group consisting of 2021/240448 1» (G 1'/18201/054671 Ni 03 ⁇ 4302)3.
  • the concentration of lithium salt is
  • These lithium salts act as a source of lithium ions in the battery to enable the operation of a basic lithium secondary battery.
  • the non-aqueous organic solvent may be at least one selected from the group consisting of linear carbonate, cyclic carbonate, linear ester and cyclic ester, and the linear carbonate is dimethyl carbonate, diethyl carbonate, dipropyl carbonate, methyl Propyl carbonate, ethyl propyl carbonate, ethyl methyl carbonate, and at least one carbonate selected from the group consisting of mixtures thereof, the cyclic carbonate is ethylene carbonate (ethyl carbonate, EC), propylene carbonate (propylene carbonate, PC), 1, 2 -Butylene carbonate;
  • the non-aqueous organic solvent is a mixture of a linear carbonate solvent and a cyclic carbonate solvent.
  • the mixing volume ratio of the linear carbonate solvent: the cyclic carbonate solvent may be 1:1 to 9:1, preferably 1.5:1 to 4:1 It can be used by mixing in a volume ratio of
  • the content of one or more additives selected from the group consisting of the compound represented by Formula 1 or the compound represented by Formula 2 is 0.01 to 10% by weight, preferably 0.01 to 5% by weight, based on the non-aqueous electrolyte; More preferably, it can be added in an amount of 0.1 to 1% by weight, and when it is less than 0.01% by weight, there is a problem in that high-temperature battery characteristics are deteriorated, and when it exceeds 10% by weight, there is a problem in that the ionic conductivity is lowered.
  • the electrolyte of the lithium ion secondary battery of the present invention usually maintains stable characteristics in a temperature range of -20 to 501.
  • the electrolyte of the present invention may be applied to a lithium ion secondary battery, a lithium ion polymer battery, and the like.
  • a positive electrode material for a lithium secondary battery in the present invention you 0) 02, your ⁇ 02, needle 02, needle 20 4, or you ⁇ - control (0 ⁇ 1, 0 ⁇ 7 ⁇ 1, 0 ⁇ +7 ⁇ 1, Eun Si, , Yo,
  • a lithium metal oxide such as La) is used, and a crystalline or amorphous carbon, carbon composite, lithium metal, or lithium alloy is used as the negative electrode material.
  • the active material is applied to the current collector of a thin plate with an appropriate thickness and length, or the active material itself is coated in a film shape and wound or laminated together with a separator, which is an insulator, to make an electrode group, and then placed in a can or similar container, followed by trialkyl
  • a lithium ion secondary battery is manufactured by injecting a non-aqueous electrolyte containing silyl sulfate and a phosphite-based stabilizer.
  • the separator polyethylene, polypropylene, etc.
  • Example 1 LiNiuCotoMnto ⁇ as a positive electrode active material, polyvinylidene fluoride (PVdF) as a binder, and carbon black as a conductive material were mixed in a weight ratio of 95.6:2.2:2.2, then N-methyl-2-pyrrole A positive electrode slurry was prepared by dispersing it in money. This slurry was coated on an aluminum foil having a thickness of 20/ffli, dried and rolled to prepare a positive electrode.
  • PVdF polyvinylidene fluoride
  • a negative active material slurry was prepared by mixing natural graphite as an anode active material, acetylene black as a conductive material, and polyvinylidene fluoride (PVdF) as a binder in a weight ratio of 85:8:7 and dispersing it in N-methyl-2-pyrrolidone. did This slurry was coated on a thick copper foil, dried and rolled to prepare a negative electrode.
  • PE polyethylene
  • a lithium secondary battery was prepared by injecting the following non-aqueous electrolyte solution.
  • the electrolyte is ethylene carbonate (EC): ethylmethyl carbonate (EMC) 2021/240448 1» (The 1'/18201/054671 mixed solvent (3: 7 volume ratio) is dissolved in 1 ⁇ 6 to 1. Then, triethylammonium ethenesulfone ] 16116311 011 6) It was prepared by adding 0.1% by weight.
  • Example 2 Triethylammonium ethenesulfone in electrolyte for secondary battery of Example 1 ]16116311 011 6) A lithium secondary battery was manufactured in the same manner except for adding 0.3% by weight.
  • Example 3 Triethylammonium ethenesulfone in the electrolyte for a secondary battery of Example 1 ]16116311 011 6) A lithium secondary battery was manufactured in the same manner except for adding 0.5 wt%. Comparative Example 1 Triethylammonium ethenesulfone in the electrolyte for secondary batteries of Example 1 ] A lithium secondary battery was manufactured in the same manner except that 16116311 011 6) was not added.
  • Comparative Example 2 A lithium secondary battery was prepared in the same manner except for adding 0.1 wt% of 1,3-propane sultone (1,3_1)1'(3 ⁇ 4)3116 31111:0116) to the electrolyte solution for a secondary battery of Example 1 2021/240448 1» (The 1'/18201/054671 was manufactured.
  • Comparative Example 3 A lithium secondary battery was prepared in the same manner except for adding 0.3% by weight of .3-propane sultone (1,3_]]1,(3 ⁇ 4)3116 31111:0116) to the electrolyte solution for secondary batteries of Example 1. manufactured.
  • Comparative Example 4 .3-propane in the electrolyte solution for secondary batteries of Example 1 31111:0116
  • a lithium secondary battery was prepared in the same manner except for adding 0.5 wt%.
  • Comparative Example 5 .3-propane in the electrolyte solution for secondary batteries of Example 1 31111:0116
  • a lithium secondary battery was prepared in the same manner except for adding 2% by weight.
  • the thickness of the cell was measured and expressed as a percentage compared to the initial thickness.
  • EIS After charging 1C up to 4., apply an AC signal of 10mV to adjust the voltage frequency.
  • DC-IR The same method as for physical property evaluation 2, but after charging at 1C until 4. and then discharging to S0C50, the evaluation was performed and the percentage compared to the initial DC-IR was indicated.
  • Retention, Recovery capacity After charging up to 1C , store at high temperature (70 ° C) for 7 days, discharge at 1C, 2.75V to measure retention capacity (discharge capacity), again
  • the recovery capacity (discharge capacity) was measured and expressed as a percentage compared to the initial discharge capacity.
  • Example 22 In the electrolyte for a secondary battery of Example 1, triethylammonium ethenesulfonate (1:1 61:]1 1...)]! ⁇ 116116311 011 6) instead of ethenesulfonate 2 ethyl 4-methyl imidazolium ( ]16]16311 0]1 6 2- ]3 ⁇ 4, 1 4_11161:]3 ⁇ 4, 1 1!1 (13 ⁇ 4 011 ⁇ , Formula 1-2) Performed in the same manner as in Example 1, except for adding 0.1 wt%
  • Example 23 In the electrolyte solution for secondary batteries of Example 1, triethylammonium ethenesulfonate (1:1 61:]1 1 ⁇ )]! ⁇ 116116311 011 6) instead of ethenesulfonate-methyl-2-p Rollidinium ( ]16]1631G 0]1 6 161:]3 ⁇ 4,
  • Example 24 2021/240448 1 ⁇ (:1 ⁇ 2021/054671
  • 1-ethenyl-1H-imidazole-3 -ium ethenesulfonate (l -ethenyl-lH-imidazol-3-ium ethenesulfonate, Formula 1-4)
  • 0.1 wt% was added
  • Example 25 Triethylammonium in the electrolyte for a secondary battery of Example 1 It was carried out in the same manner as in Example 1, except that 0.1 wt% of triethylammonium vinylphosphonate (Formula 2-1) was added instead of ethenesulfonate (triethylammonium ethenesulfonate).
  • Example 28 Triethylammonium in the electrolyte for a secondary battery of Example 1 Instead of 1-vinyl-in-imidazole-2 -um vinylphosphonate (11 1-in- ⁇ 3201-3 - ⁇ ⁇ ⁇ 13 ⁇ 4, 1! 11031) 11011 6, Formula 2 4) 0.1 wt% Except for the addition, it was carried out in the same manner as in Example 1.
  • Example 1 showed excellent performance in high temperature storage evaluation, and as in Examples 4 to 21, when the life performance enhancing additive, high temperature improving additive, and output improving additive were additionally added, the battery performance was further improved. Examples 5 to 7, in which the life performance improving additive was additionally added, improved life efficiency compared to Example 1.
  • Examples 8 to 13 in which the high-temperature performance-improving additive was additionally added, improved seedlings after high-temperature storage compared to Example 1, and cell swelling was more suppressed.
  • Examples 18 to 21 in which an additive in the form of a salt that improves both high temperature and Joule force performance was additionally added, cell swelling after storage at a higher temperature than Example 1 was suppressed, and EIS and output It has a very good performance effect.
  • the non-aqueous electrolyte according to the present invention has improved lifespan characteristics and high temperature storage characteristics at room temperature and high temperature by adding a salt represented by Formula 1 or Formula 2 2021/240448 1» (That 1'/18201/054671 has an effect. Since a specific part of the present invention has been described in detail above, for those of ordinary skill in the art, it is clear that this specific description is only a preferred embodiment, and the scope of the present invention is not limited thereby. will be. Accordingly, the substantial scope of the present invention will be defined by the claims and their equivalents.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Condensed Matter Physics & Semiconductors (AREA)
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Abstract

La présente invention concerne une solution électrolytique non aqueuse pour une batterie secondaire, et une batterie secondaire la comprenant. L'ajout d'un sel représenté par la formule chimique 1 ou la formule chimique 2 à une solution électrolytique non aqueuse pour une batterie secondaire selon la présente invention a pour effet d'améliorer les caractéristiques de durée de vie et les caractéristiques de stockage à haute température.
PCT/IB2021/054671 2020-05-29 2021-05-28 Solution électrolytique pour batterie secondaire, et batterie secondaire la comprenant WO2021240448A1 (fr)

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KR10-2020-0065077 2020-05-29
KR20200065077 2020-05-29

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130057829A (ko) * 2011-11-24 2013-06-03 동우 화인켐 주식회사 리튬 이차전지용 전해액
KR20160145055A (ko) * 2014-04-03 2016-12-19 바스프 에스이 2차 리튬 이온 배터리에서 전해질용 첨가제로서의 반응성 이온성 액체의 용도
US20170054178A1 (en) * 2014-02-14 2017-02-23 Stella Chemifa Corporation Nonaqueous electrolyte solution for secondary batteries and secondary battery provided with same
KR20190143827A (ko) * 2018-06-21 2019-12-31 파낙스 이텍(주) 이차전지용 전해액 및 이를 포함하는 이차전지
KR20200018258A (ko) * 2018-08-09 2020-02-19 파낙스 이텍(주) 이차전지용 전해액 및 이를 포함하는 이차전지

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130057829A (ko) * 2011-11-24 2013-06-03 동우 화인켐 주식회사 리튬 이차전지용 전해액
US20170054178A1 (en) * 2014-02-14 2017-02-23 Stella Chemifa Corporation Nonaqueous electrolyte solution for secondary batteries and secondary battery provided with same
KR20160145055A (ko) * 2014-04-03 2016-12-19 바스프 에스이 2차 리튬 이온 배터리에서 전해질용 첨가제로서의 반응성 이온성 액체의 용도
KR20190143827A (ko) * 2018-06-21 2019-12-31 파낙스 이텍(주) 이차전지용 전해액 및 이를 포함하는 이차전지
KR20200018258A (ko) * 2018-08-09 2020-02-19 파낙스 이텍(주) 이차전지용 전해액 및 이를 포함하는 이차전지

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