CN114583271A - Electrolyte additive, electrolyte and lithium secondary battery - Google Patents

Electrolyte additive, electrolyte and lithium secondary battery Download PDF

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Publication number
CN114583271A
CN114583271A CN202210143682.6A CN202210143682A CN114583271A CN 114583271 A CN114583271 A CN 114583271A CN 202210143682 A CN202210143682 A CN 202210143682A CN 114583271 A CN114583271 A CN 114583271A
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electrolyte
lithium
additive
carbonate
solvent
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曾荣华
林晓欣
曾启轩
刘秀博
邱景伟
范自强
张冬迎
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South China Normal University
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    • 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
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • 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
    • 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

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
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  • Secondary Cells (AREA)

Abstract

The invention discloses an electrolyte additive containing thiazolyl, amino and cyano, and a lithium ion battery containing the additive. The additive contains three effective groups, namely imidazolyl, amino and nitrile. The thiazolyl and the amino have alkalescence, so that HF in the electrolyte can be effectively reduced, the precipitation of transition metal ions in the anode of the lithium ion battery is reduced, and the stability of an interface film between the anode and the electrolyte is enhanced; the cyano group can complex with transition metal of the anode of the lithium ion battery, and a film is formed on the surface of the anode, and the interfacial film can effectively inhibit the decomposition of electrolyte and reduce the precipitation of transition metal ions. Therefore, the battery system containing the additive has better high-voltage resistance, normal-temperature and high-temperature cycle performance and high-temperature storage performance.

Description

Electrolyte additive, electrolyte and lithium secondary battery
Technical Field
The invention relates to the technical field of lithium ion batteries, in particular to an electrolyte additive containing thiazolyl, amino and cyano, and electrolyte and a lithium ion battery containing the additive.
Background
Since 1990, the lithium ion battery has been known to have the advantages of high energy density, long cycle life, little environmental pollution, no memory effect, etc., and has become one of the internationally recognized ideal secondary batteries, and has been widely used in electronic devices such as mobile communication, portable computers, electric bicycles, etc. With the development of the fields of hybrid electric vehicles and pure electric vehicles expanding day by day, the lithium ion battery as an ideal power source of the power vehicle faces an unprecedented challenge of improving the safety performance and energy density of the battery.
Improving the working voltage of the battery is one of effective ways to improve the energy density of the lithium ion battery. The negative electrode of the lithium ion battery which is commercialized at present mainly adopts graphite materials, and the lithium intercalation potential of the graphite materials is 0.1V (vs+) The left and right are already very close to the theoretical lithium intercalation potential of metallic lithium. Therefore, increasing the operating voltage of a lithium ion battery can only be achieved by increasing the lithium insertion/extraction potential of the positive electrode material. Several major high voltage positive electrode materials that have been reported to date include LiCoPO4(4.8V)、LiNi0.5Mn1.5O4(4.7V) ternary material LiNi1-x-yCoxMnyO2(x is more than or equal to 0, y is less than or equal to 1, and x + y is less than or equal to 1), and rich lithium and the like. These high voltage positive electrode materials have not been practically used until now, the biggest reason being the low electrochemical stability window of the currently commercially available carbonate-based electrolytes when the cell voltage reaches 4.5V (vs+) Around this time, the electrolyte begins to undergo a severe oxidative decomposition reaction, which results in failure of the lithium intercalation/deintercalation reaction of the battery. Secondly, part of the positive electrode material, for example, lini0.5mn1.5o4 material, may dissolve metal Mn and Ni ions under high voltage conditions, destroying the material structure, and causing severe battery capacity fading. It can be seen that the improved electrode/electrolyte (especially positive electrode/electrolyte) interface stability of the cell is a high voltage lithium ion cellBasic premise of exhibition.
A simple, easy to operate, and inexpensive method of improving the battery electrode/electrolyte interface-development and application of novel elegant electrolyte systems or high pressure film-forming additives has been reported. Generally, the additive containing thiazolyl and amino has alkalescence, so that the additive has the effect of reducing the content of HF (hydrogen fluoride) under high voltage, thereby reducing the precipitation of transition metal ions in the positive electrode of the lithium ion battery and enhancing the stability of an interface film between the positive electrode and electrolyte, and therefore, the high-temperature storage and high-voltage performance of the battery can be improved; the cyano group can complex the transition metal of the anode of the lithium ion battery, and a film is formed on the surface of the anode, and the interfacial film can effectively inhibit the decomposition of the electrolyte and reduce the precipitation of transition metal ions, so that the cycle performance of a high-voltage system can be improved.
Based on the background, the synergistic effect of the 3 groups is utilized to develop the additive with better high voltage resistance, high temperature resistance and excellent cycle, and the additive has important significance.
Disclosure of Invention
One of the objectives of the present invention is to provide an electrolyte additive for lithium ion battery electrolyte, which can form a film on a positive electrode, reduce the HF content in the electrolyte, and enhance the stability of the interface film between the positive electrode and the electrolyte.
The second object of the present invention is to provide an electrolyte for a lithium ion battery, which contains the above electrolyte additive and has high voltage resistance, high temperature resistance and excellent cycle performance.
The present invention also provides a lithium ion battery containing the electrolyte, and having high voltage resistance, high temperature resistance, and excellent cycle performance.
To achieve the above object, the present invention provides an electrolyte additive comprising a compound having a structure represented by the structural formula (i):
Figure BDA0003507784190000021
the invention also provides an electrolyte, which comprises lithium salt, a solvent and an additive, wherein the additive comprises the electrolyte additive.
Preferably, the mass percentage of the electrolyte additive in the invention in the total mass of the lithium salt and the solvent is 0.1-5.0%. Preferably, the amount of the additive can be selected to be 0.5% -5.0%; more preferably, the amount of the additive is selected from: 0.5%, 1.0%, 2.0%, 5.0%.
Preferably, the lithium salt of the electrolyte of the present invention is selected from the group consisting of the conductive lithium salt being lithium hexafluorophosphate (LiPF)6) Lithium tetrafluoroborate (LiBF)4) Lithium bis (oxalato) borate (LiBOB), lithium difluoro (oxalato) borate (LiODFB), lithium bis (fluorosulfonyl) imide (LiFSI), lithium bis (trifluoromethylsulfonyl) imide (LiTFSI).
Preferably, the concentration of the lithium salt in the electrolyte of the present invention is 0.5M to 1.5M. Specifically, the concentration of the lithium salt of the electrolyte of the present invention in the electrolyte may be, but is not limited to, 0.5M, 0.75M, 1M, 1.25M, 1.5M.
Preferably, the solvent is selected from one or more of chain and cyclic carbonates and carboxylic esters. The cyclic carbonate-based solvent refers to Ethylene Carbonate (EC), fluoroethylene carbonate (FEC), or Propylene Carbonate (PC); the chain carbonate solvent refers to dimethyl carbonate (DMC), diethyl carbonate (DEC) or Ethyl Methyl Carbonate (EMC); the carboxylic ester solvent refers to Propyl Acetate (PA), Ethyl Acetate (EA) or Propyl Propionate (PP).
In the invention, preferably, the additive also comprises an auxiliary additive, wherein the auxiliary additive is one or two of 1, 3-propane sultone and tri (trisilane) borate.
Preferably, the auxiliary additive accounts for 0.1-2% of the total mass of the lithium salt and the solvent.
The present invention also provides a lithium secondary battery comprising a positive electrode, a negative electrode and the lithium secondary battery electrolyte as described in any one of the above, wherein: the positive electrode material is selected from transition metal oxide of lithium, wherein the transition metal oxide of lithium is LiCoO2、LiMn2O4、LiMnO2、Li2MnO4、LiFePO4、Li1+aMn1-xMxO2、LiCo1-xMxO2、LiFe1- xMxPO4、Li2Mn1-xO4Wherein M is one or more selected from Ni, Co, Mn, Al, Cr, Mg, Zr, Mo, V, Ti, B and F, and a is more than or equal to 0<0.2，0≤x<1; the negative electrode material is selected from at least one of graphite, silicon-carbon composite material and lithium titanate.
Compared with the prior art, the electrolyte additive contains thiazole and amino groups, and both of the thiazole and the amino groups have alkalescence, so that the electrolyte additive has the function of reducing the content of HF (hydrogen fluoride) under high voltage, and the high-temperature storage and high-voltage performance of a battery are improved; secondly, it contains nitrile group, complex with the transition metal of the lithium ion battery anode, and forms a film on the anode surface, the interfacial film can effectively inhibit the decomposition of the electrolyte and reduce the precipitation of transition metal ions, so that the cycle performance of the high voltage system can be improved, thereby exerting the synergistic effect and better improving the high voltage resistance, high temperature resistance and cycle performance of the battery.
Detailed Description
The invention will now be further described with reference to the following examples, which are not to be construed as limiting the invention in any way, and any limited number of modifications which can be made within the scope of the claims of the invention are still within the scope of the claims of the invention.
In order to explain the technical contents of the present invention in detail, the following description is further made in conjunction with the embodiments.
Example one
1. Preparing an electrolyte: ethylene Carbonate (EC), diethyl carbonate (DEC) and Ethyl Methyl Carbonate (EMC) were mixed in a mass ratio of EC: DEC: EMC ═ 1:1:1, and 1mol of lithium hexafluorophosphate (LiPF) was added thereto6) After the lithium salt is completely dissolved, 0.5% of an additive represented by the structural formula I is added.
2. Preparing a positive plate: LiNi prepared from nickel cobalt lithium manganate ternary material0.6Co0.2Mn0.2O2The conductive agent SuperP, the adhesive PVDF and the Carbon Nano Tube (CNT) are mixed according to the mass ratio of 97.5:1.5:1Uniformly mixing to prepare lithium ion battery anode slurry with certain viscosity, and coating the slurry on aluminum foil for a current collector, wherein the coating weight is 324g/m2Drying at 85 ℃ and then carrying out cold pressing; and then trimming, cutting into pieces, slitting, drying for 4 hours at 85 ℃ under a vacuum condition after slitting, and welding tabs to prepare the lithium ion battery positive plate meeting the requirements.
3. Preparing a negative plate: preparing artificial graphite, conductive agent SuperP, thickening agent CMC and adhesive SBR (styrene butadiene rubber emulsion) into slurry according to the mass ratio of 95:1.5:1.0:2.5, uniformly mixing, coating the mixed slurry on two sides of copper foil, drying and rolling to obtain a negative plate, and preparing the lithium ion battery negative plate meeting the requirements.
4. Preparing a lithium ion battery: and (3) preparing the positive plate, the negative plate and the diaphragm prepared by the process into a lithium ion battery with the thickness of 4.7mm, the width of 55mm and the length of 60mm by a lamination process, wherein the capacity of the lithium ion battery is 1800mAh, vacuum baking is carried out at 85 ℃ for 48 hours, and the electrolyte is injected to complete the battery preparation.
Examples two to four
The preparation of the electrolyte, the preparation of the positive plate, the preparation of the negative plate and the preparation of the lithium ion battery are consistent with the embodiment, but the contents of the additive shown in the structural formula I are respectively 1.0%, 2.0% and 5.0%.
EXAMPLE five
The preparation of the electrolyte, the preparation of the positive plate, the negative plate and the lithium ion battery are consistent with the embodiment, but the content of the additive shown in the structural formula I is 0.7 percent; in addition, 0.3% of 1, 3-propane sultone was added.
EXAMPLE six
The preparation of the electrolyte, the preparation of the positive plate, the negative plate and the lithium ion battery are consistent with the embodiment, but the content of the additive shown in the structural formula I is 0.7 percent; in addition, 0.2% of 1, 3-propane sultone and 0.1% of tris (trimethylsilyl) borate were added.
EXAMPLE seven
1. Preparing an electrolyte: mixing Ethylene Carbonate (EC), diethyl carbonate (DEC)And Ethyl Methyl Carbonate (EMC) in a mass ratio of EC: DEC: EMC ═ 1:1:1, and 1mol of lithium hexafluorophosphate (LiPF) was added after mixing6) After the lithium salt is completely dissolved, 0.5% of an additive represented by the structural formula I is added.
2. Preparing a positive plate: preparing lithium cobaltate material LiCoO2Uniformly mixing the conductive agent SuperP, the adhesive PVDF and the Carbon Nano Tubes (CNT) according to the mass ratio of 97.5:1.5:1:1 to prepare lithium ion battery anode slurry with certain viscosity, and coating the lithium ion battery anode slurry on an aluminum foil for a current collector, wherein the coating weight is 316g/m2Drying at 85 ℃ and then carrying out cold pressing; and then trimming, cutting into pieces, slitting, drying for 4 hours at 85 ℃ under a vacuum condition after slitting, and welding tabs to prepare the lithium ion battery positive plate meeting the requirements.
3. Preparing a negative plate: preparing artificial graphite, conductive agent SuperP, thickening agent CMC and adhesive SBR (styrene butadiene rubber emulsion) into slurry according to the mass ratio of 95:1.5:1.0:2.5, uniformly mixing, coating the mixed slurry on two sides of copper foil, drying and rolling to obtain a negative plate, and preparing the lithium ion battery negative plate meeting the requirements.
4. Preparing a lithium ion battery: and (3) preparing the positive plate, the negative plate and the diaphragm prepared by the process into a lithium ion battery with the thickness of 4.7mm, the width of 55mm and the length of 60mm by a lamination process, wherein the capacity of the lithium ion battery is 2000mAh, vacuum baking is carried out for 48 hours at the temperature of 85 ℃, and the electrolyte is injected to complete the preparation of the battery.
Examples eight to ten
The preparation of the electrolyte, the preparation of the positive plate, the negative plate and the lithium ion battery are the same as those of the embodiment, but the contents of the additive shown in the structural formula I are respectively 1.0%, 2.0% and 5.0%.
Comparative examples one to four
Electrolyte preparation method and battery preparation method refer to examples one to four, additive is not added, comparative compound 1 to 3, additive addition amount is 1.0% respectively.
Comparative example five
Comparative compounds 1 to 3 were added, all with 1.0% additive, in a total amount of 3%.
Comparative example six
The preparation of the electrolyte, the preparation of the positive plate, the negative plate and the lithium ion battery are consistent with the embodiment, but the electrolyte does not contain the additive shown in the structural formula I; in addition, 1% of 1, 3-propane sultone was added in this example.
Comparative examples seven to ten
Electrolyte preparation method and battery preparation method refer to examples five to eight, additive is not added, comparative compound 1 to 3, additive addition amount is 1.0% respectively.
Comparative example eleven
Comparative compounds 1 to 3 were added, with 1.0% of the additive.
Comparative compounds 1 to 3 are as follows:
Figure BDA0003507784190000051
Figure BDA0003507784190000061
the electrolyte compositions and battery systems of the above examples and comparative examples are shown in table one.
Table one: electrolyte compositions and battery systems of examples and comparative examples.
Figure BDA0003507784190000062
Figure BDA0003507784190000071
Application experiment of examples and comparative examples
Normal temperature cycle test at 25 ℃ 1.0C/1.0C: charging to 4.5V at 25 deg.C under constant current of 1.0C and constant voltage of 4.5V to 0.05C at cut-off current, and discharging at constant current of 1.0C to obtain discharge capacity C0Repeating the charging and discharging steps for 1000 weeks to obtain the 10 th productDischarge capacity C at 00 weeks1000Capacity retention rate ═ C1000/C0*100％。
High temperature cycle test at 45 ℃ 1.0C/1.0C: charging to 4.5V at 45 deg.C under constant current of 1.0C, constant voltage charging to 0.05C at cut-off current, and discharging at constant current of 1.0C to obtain discharge capacity C0Repeating the charging and discharging steps for 1000 weeks to obtain the discharge capacity C at 1000 weeks1000Capacity retention rate ═ C1000/C0*100％
Capacity retention at 60 ℃ for 14 days: after the battery is cycled for 3 times at the charge-discharge rate of 1C, the battery is stored for 14 days at the high temperature of 60 ℃ in a full-charge state, and a discharge test is carried out, and the obtained discharge capacity is divided by the discharge capacity of the first cycle to obtain the capacity retention rate after high-temperature storage
-20 ℃ low temperature discharge test: the cell was charged at 25 ℃ to 4.5V at a constant current of 1.0C, charged at a constant voltage of 4.5V to a cutoff current of 0.05C, and then discharged at a constant current of 0.5C, and the discharge capacity was recorded as C0. At 25 ℃, the battery is charged to 4.5V at a constant current of 1.0C and charged at a constant voltage of 4.5V to a cutoff current of 0.05C, then the battery is transferred to-20 ℃ for holding for 240min, and then the battery is discharged at a constant current of 0.5C, and the discharge capacity is recorded as C1, and the discharge rate at-20 ℃ is recorded as C1/C0 as 100 percent.
After the electrolytes in the above examples and comparative examples are prepared into lithium ion batteries, the normal temperature cycle energy absorption, high temperature cycle performance, high temperature storage performance and low temperature discharge performance of the lithium ion batteries are tested, and the results are shown in table two:
table two: lithium ion battery performance test results
Figure BDA0003507784190000081
In high voltage systems, the optimum amount of the targeted additive was found to be 1.0% by comparison of examples one to four, and examples six to nine. When the amount of addition is 0.5%, the film density formed on the positive electrode is not sufficient due to an excessively small amount of addition, and the overall performance is inferior to 1.0%. When the addition amount exceeds 1.0%, the normal temperature cycle, high temperature cycle and high temperature storage performance are equivalent to 1.0%, which shows that when the addition amount is 1.0%, the formed film is sufficiently dense, and when the addition amount exceeds the addition amount, the effect is not great. The addition of the target additive can slightly improve the low-temperature performance, because the three components act synergistically, the dissolution of transition metal ions is better inhibited, and the phenomena that the transition metal ions are deposited on a negative electrode, catalyze the decomposition of an electrolyte and form a thinner film when the additive is not added are avoided. When the amount of the additive exceeds 1.0%, the density of the film formed on the positive electrode may be too dense, and the low-temperature performance may be slightly inferior to 1.0%. By comparing the examples with the comparative examples, it was found that the normal temperature, high temperature cycle and high temperature storage properties of the additive containing a single thiazolyl, amino and cyano group are better than those of the additive without the additive, but the three have little influence on the low temperature properties. The best performing is the nitrile group containing additive. When the three are used simultaneously, the overall performance of the battery is improved, but the difference is larger than that of a target additive, which proves that one additive contains three groups simultaneously, so that the synergistic effect can be better exerted, and the overall performance of the battery is improved.
Meanwhile, the fifth and sixth embodiments can find that when the electrolyte additive disclosed by the invention is matched with 1, 3-propane sultone, the normal-temperature and high-temperature circulation, high-temperature storage and low-temperature performance of the electrolyte additive disclosed by the invention can be better exerted.

Claims (9)

1. An electrolyte additive, characterized in that it has the structure shown in formula (I):
Figure FDA0003507784180000011
2. an electrolyte comprising a lithium salt, a solvent and an additive, wherein the additive comprises the electrolyte additive of claim 1.
3. The electrolyte according to claim 2, wherein the mass percentage of the electrolyte additive to the total mass of the lithium salt and the solvent is 0.1 to 5.0%.
4. The electrolyte of claim 2, wherein the lithium salt is selected from lithium hexafluorophosphate (LiPF)6) At least one of lithium tetrafluoroborate, lithium dioxalate borate, lithium difluorooxalate borate, lithium bis (fluorosulfonyl) imide and lithium bis (trifluoromethylsulfonyl) imide.
5. The electrolyte of claim 2, wherein the concentration of the lithium salt in the electrolyte is between 0.5M and 1.5M.
6. The electrolyte of claim 2, wherein the solvent is selected from one or more of chain and cyclic carbonates, and carboxylic acid ester solvents; the cyclic carbonate solvent is one or more of ethylene carbonate, fluoroethylene carbonate and propylene carbonate; the chain carbonate solvent is dimethyl carbonate, diethyl carbonate and methyl ethyl carbonate; the carboxylic ester solvent is one or more of propyl acetate, ethyl acetate and propyl propionate.
7. The electrolyte of any one of claims 2-6, further comprising an auxiliary additive, wherein the auxiliary additive is one or two of 1, 3-propane sultone and tris (trisilane) borate.
8. The electrolyte according to claim 7, wherein the auxiliary additive is 0.1 to 2 mass% based on the total mass of the lithium salt and the solvent.
9. A lithium secondary battery characterized in that: the lithium secondary battery comprises a positive electrode, a negative electrode and the lithium secondary battery electrolyte according to any one of claims 2 to 8, wherein: the positive electrode material is selected from transition metal oxide of lithium, wherein the transition metal oxide of lithium is LiCoO2、LiMn2O4、LiMnO2、Li2MnO4、LiFePO4、Li1+aMn1-xMxO2、LiCo1-xMxO2、LiFe1-xMxPO4、Li2Mn1-xO4Wherein M is one or more selected from Ni, Co, Mn, Al, Cr, Mg, Zr, Mo, V, Ti, B and F, and a is more than or equal to 0<0.2，0≤x<1; the negative electrode material is selected from at least one of graphite, silicon-carbon composite material and lithium titanate.
CN202210143682.6A 2022-02-16 2022-02-16 Electrolyte additive, electrolyte and lithium secondary battery Pending CN114583271A (en)

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