CN109802177B - Electrolyte containing silicon solvent and pyridine additive and lithium ion battery using electrolyte - Google Patents
Electrolyte containing silicon solvent and pyridine additive and lithium ion battery using electrolyte Download PDFInfo
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- CN109802177B CN109802177B CN201811595743.2A CN201811595743A CN109802177B CN 109802177 B CN109802177 B CN 109802177B CN 201811595743 A CN201811595743 A CN 201811595743A CN 109802177 B CN109802177 B CN 109802177B
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- 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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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Abstract
The invention discloses an electrolyte containing a silicon solvent and a pyridine additive and a lithium ion battery using the electrolyte. The electrolyte comprises lithium salt, an organic solvent and an additive, and is characterized in that the organic solvent comprises a silicon-substituted organic solvent, the additive comprises a nitrile-group-containing pyridyl compound, and the organic solvent can also comprise one or more of a chain carbonate organic solvent and a cyclic carbonate organic solvent. According to the invention, a nitrile group-containing pyridine compound is used for forming a conductive electrolyte membrane on the surface of the anode of the electrode, so that metal dissolution is inhibited, the electrolyte membrane is complexed with HF in the electrolyte, the content of HF is reduced, the corrosion effect of HF on the anode material is reduced, and the cycle life and the capacity retention rate of the battery are finally improved; meanwhile, by adding the silicon solvent, the viscosity of the electrolyte is reduced while the anode is protected, the electrode interface is optimized, the increase of impedance is inhibited, and the low-temperature and rate performance of the battery are ensured.
Description
Technical Field
The invention relates to the field of batteries, in particular to an electrolyte containing a silicon solvent and a pyridine additive and a lithium ion battery using the electrolyte.
Background
With the increase of electric automobiles, cordless electric tools and military applications, higher requirements on the energy density of lithium ion batteries are increased. At present, the charge cut-off potential of the positive active material is mainly improved by selecting the positive active material and the negative active material with high capacity and high compaction. However, the latter can increase the oxidation activity of the positive electrode, aggravate the oxidative decomposition of the electrolyte and reduce the overall performance of the battery. When lithium ions are heated, continuously discharged and heated at high temperature, damage to active materials is accelerated, and a battery generates a large amount of gas, and even more, safety accidents such as explosion and combustion are caused. Under a high-voltage environment, a large amount of lithium ions in the positive electrode material can be extracted, and the safety performance and the cycling stability of the battery are influenced.
At present, the most used electrolyte lithium salt of the lithium ion battery is LiPF6Its advantages are high electric conductivity, wide electrochemical window and high-and low-temp performance; however, LiPF6Have disadvantages of sensitivity to water and thermal instability, and are easily decomposed in the presence of a trace amount of water or at a higher temperature to generate HF, which damages the SEI film and electrode materials, ultimately resulting in a decrease in battery capacity and deterioration in battery performance.
Many solutions to the above problems are available, and SK new technology corporation in patent WO2015088052 mentions that the complexation of the nitrile group of polynitrile compound and high valence metal ions can effectively reduce the dissolution of metal ions and inhibit the oxidative decomposition of electrolyte on the surface of the positive electrode; some traditional film forming additives of the positive electrode, such as benzene and thiophene with a large pi bond structure, unsaturated bond-containing PST and the like, can be polymerized to form a film on the surface of the positive electrode, cover active sites on the surface of the positive electrode, inhibit the oxidative decomposition of electrolyte and the like. To LiPF6By adding dehydration and acid suppression additives such as carbodiimide type additives, etc.
Disclosure of Invention
The invention provides an electrolyte containing a silicon solvent and a pyridine additive and a lithium ion battery using the electrolyte, aiming at the background technology and the existing defects.
In order to achieve the purpose of the invention, the electrolyte containing the silicon solvent and the pyridine additive comprises lithium salt, an organic solvent and the additive, wherein the organic solvent contains a silicon-substituted organic solvent, and the additive contains a nitrile-group-containing pyridyl compound.
Further, the organic solvent is represented by formula (I) or formula (II):
in the formula (I), M1And M2Each represents an alkyl group having 1 to 6 carbon atoms or a silane or siloxane having 1 to 4 carbon atoms, and M1And M2At least one of which is a silane or siloxane having 1 to 4 carbon atoms;
in the formula (II), X1And X2Each represents an alkyl group having 1 to 6 carbon atoms or a silane or siloxane having 1 to 4 carbon atoms, and X1And X2At least one of which is a silane or siloxane having 1 to 4 carbon atoms.
Preferably, according to some embodiments of the invention, the compound of formula (I) includes, but is not limited to, the following compounds:
preferably, according to some embodiments of the invention, the compound of formula (II) includes, but is not limited to, the following compounds:
more preferably, the organic solvent represented by formula (I) or formula (II) is 2-30%, for example 5-15% of the organic solvent.
In the invention, the silicon-substituted solvent has high oxidation resistance and chemical stability, improves the high-temperature performance of the lithium battery, and is suitable for a high-voltage lithium battery system. In addition, due to the reduction of the internal rotation potential barrier of the silicon-substituted back bond and the increase of the flexibility, the viscosity of the original solvent is reduced, the shuttling capacity of lithium ions in the solvent is improved, and the low-temperature performance and the rate capability of the lithium battery can be improved to a greater extent.
Further, the nitrile group-containing pyridyl compound is represented by general formula (III):
in the general formula (III), X1、X2、X3、X4And X5Each independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, a halogen atom, a nitrile group or an alkoxynitrile group of 1 to 5 carbon atoms, and X1、X2、X3、X4And X5In the formula (I), at least one is nitrile group or alkoxy nitrile group with 1-5 carbon atoms.
Preferably, according to some embodiments of the present invention, the nitrile group-containing pyridyl compound of the general formula (iii) includes, but is not limited to, the following compounds:
preferably, the nitrile group-containing pyridyl compound represented by the general formula (iii) is used in an amount of 0.1 to 10%, for example, 1 to 2% by mass of the electrolyte.
Further, the organic solvent further comprises one or more of a chain carbonate organic solvent and a cyclic carbonate organic solvent.
Still further, the chain carbonate organic solvent is selected from one or more of dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate and dipropyl carbonate, and the cyclic carbonate organic solvent is selected from one or more of ethylene carbonate, vinylene carbonate and propylene carbonate.
Preferably, the organic solvent comprises Ethylene Carbonate (EC), Propylene Carbonate (PC), Ethyl Methyl Carbonate (EMC) and diethyl carbonate (DEC), more preferably, Ethylene Carbonate (EC), Propylene Carbonate (PC), Ethyl Methyl Carbonate (EMC) and diethyl carbonate (DEC) are mixed in a weight ratio of (20-30): (3-8): (45-55): (15-25), e.g. 25:5:50: 20.
Further, the additive can also comprise a material selected from fluoroethylene carbonate (FEC), 1,3 propane sultone (1,3-PS), Propylene Carbonate (PC), lithium difluorophosphate (LiPO)2F2) One or more additives selected from Vinylene Carbonate (VC), Vinyl Ethylene Carbonate (VEC) and vinyl sulfate (DTD),
preferably, the additive also comprises 1, 3-propane sultone (1,3-PS) and lithium difluorophosphate (LiPO)2F2) Vinylene Carbonate (VC), fluoroethylene carbonate (FEC), more preferably 1,3 propane sultone (1,3-PS), lithium difluorophosphate (LiPO) among said additives2F2) The mass ratio of Vinylene Carbonate (VC) to fluoroethylene carbonate (FEC) is (2-4) to (1-3) to (0.5-1) to (1-3), for example 3:2:1: 2.
Preferably, the mass percentage of the additive in the electrolyte is 0.1-15%.
Further, the lithium salt may be selected from LiPF6、LiBF4、LiClO4、LiBOB、LiODFB、LiAsF6、LiN(SO2CF3)2、LiN(SO2F)2And the concentration of the lithium salt in the electrolyte is 0.5 to 2M, preferably 1 to 1.5M, in terms of lithium ions.
The present invention also provides a lithium ion battery using the high voltage electrolyte for lithium ion batteries of the present invention, and preferably, a method for preparing the lithium ion battery comprises injecting the high voltage electrolyte for lithium ion batteries of the present invention into a fully dried 4.35V nickel: cobalt: the manganese-5: 2:3 NCM/graphite soft package battery is subjected to the working procedures of standing at 45 ℃, high-temperature clamp formation and secondary sealing.
According to the invention, a nitrile group-containing pyridine compound is used for forming a conductive electrolyte membrane on the surface of the anode of the electrode, so that metal dissolution is inhibited, the electrolyte membrane is complexed with HF in the electrolyte, the content of HF is reduced, the corrosion effect of HF on the anode material is reduced, and the cycle life and the capacity retention rate of the battery are finally improved; meanwhile, by adding the silicon solvent, the viscosity of the electrolyte is reduced while the anode is protected, the electrode interface is optimized, the increase of impedance is inhibited, and the low-temperature and rate performance of the battery are ensured.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention. It is to be understood that the following description is only illustrative of the present invention and is not to be construed as limiting the present invention.
As used herein, the terms "comprises," "comprising," "includes," "including," "contains," "containing," or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
The conjunction "consisting of …" excludes any unspecified elements, steps or components. If used in a claim, the phrase is intended to claim as closed, meaning that it does not contain materials other than those described, except for the conventional impurities associated therewith. When the phrase "consisting of …" appears in a clause of the subject matter of the claims rather than immediately after the subject matter, it defines only the elements described in the clause; other elements are not excluded from the claims as a whole.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
The singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. "optional" or "any" means that the subsequently described event or events may or may not occur, and that the description includes instances where the event occurs and instances where it does not.
The indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the number clearly indicates the singular.
Further, the technical features of the embodiments of the present invention may be combined with each other as long as they do not conflict with each other.
Comparative example 1
The high-voltage electrolyte is prepared by the following method: in a glove box, Ethylene Carbonate (EC), Propylene Carbonate (PC), Ethyl Methyl Carbonate (EMC) and diethyl carbonate (DEC) were mixed in a weight ratio of 25:5:50:20, and then lithium hexafluorophosphate was added to dissolve them, to prepare an electrolyte solution having a lithium hexafluorophosphate concentration of 1M. Then, 0.5% by mass of Vinylene Carbonate (VC), 1% by mass of fluoroethylene carbonate (FEC), 1.5% by mass of 1,3 propane sulfonic acid lactone (1,3-PS), and 1% by mass of lithium difluorophosphate (LiPO) were added to the electrolyte2F2)。
The prepared nonaqueous electrolyte for the lithium ion battery was injected into a fully dried 4.35V NCM (nickel: cobalt: manganese ═ 5:2: 3)/graphite pouch battery, and after the procedures of standing at 45 ℃, high-temperature jig formation, secondary sealing and the like, a battery performance test was performed to obtain the battery used in comparative example 1.
Example 1
The high-voltage electrolyte is prepared by the following method: mixing Ethylene Carbonate (EC), Propylene Carbonate (PC), Ethyl Methyl Carbonate (EMC) and diethyl carbonate (DEC) in a weight ratio of 25:5:50:20 in a glove box, and adding a 5% by mass of a silico-organic solvent (1) to the mixed solvent; adding lithium hexafluorophosphate for dissolution to prepare an electrolyte solution with the concentration of lithium hexafluorophosphate being 1M. Then, 0.5% by mass of Vinylene Carbonate (VC), 1% by mass of fluoroethylene carbonate (FEC), 1.5% by mass of 1,3 propane sulfonic acid lactone (1,3-PS), and 1% by mass of lithium difluorophosphate (LiPO) were added to the electrolyte2F2) And 1% of nitrile group-containing pyridine compound (5) was added.
The prepared nonaqueous electrolyte solution for lithium ion batteries was injected into a fully dried 4.35V NCM (nickel: cobalt: manganese ═ 5:2: 3)/graphite pouch battery, and after the procedures of standing at 45 ℃, high-temperature jig formation, secondary sealing and the like, a battery performance test was performed to obtain the battery used in example 1.
The following is a table of electrolyte formulations for each example and comparative example:
TABLE 1 electrolyte formulations for the examples and comparative examples
Lithium ion battery performance testing
1. High temperature cycle performance
Under the condition of high temperature (45 ℃), the lithium ion battery is charged to 4.35V under the constant current and constant voltage of 1C, and then is discharged to 3.0V under the constant current of 1C. After 300 cycles of charge and discharge, the capacity retention rate after the 300 th cycle was calculated as:
2. high temperature storage Properties
The lithium ion battery was subjected to primary 1C/1C charging and discharging (discharge capacity is designated DC) at room temperature (25 ℃ C.)0) Then, the battery is charged to 4.35V under the condition of 1C constant current and constant voltage; storing the lithium ion battery in a 55 ℃ high-temperature box for 7 days, and takingAfter the discharge, 1C discharge (discharge capacity designated as DC) was carried out at ordinary temperature1) (ii) a Then, 1C/1C charging and discharging (discharge capacity is designated as DC) were carried out under ambient conditions2) Calculating the capacity retention rate and the capacity recovery rate of the lithium ion battery by using the following formulas:
3. low temperature cycle performance
Under the condition of low temperature (10 ℃), the lithium ion battery is charged to 4.35V under the constant current and constant voltage of 1C, and then is discharged to 3.0V under the constant current of 1C. After 50 cycles of charge and discharge, the capacity retention rate after the 50 th cycle was calculated as:
the results of the battery performance tests of the above examples and comparative examples are shown in table 2:
table 2 results of cell performance test of each example and comparative example
As can be seen from the above data, in comparative example 1, when applied to a high voltage 4.35VNCM (nickel: cobalt: manganese ═ 5:2:3)/AG pouch cell, 0.5% by mass of Vinylene Carbonate (VC), 1% by mass of fluoroethylene carbonate (FEC), 1.5% by mass of 1,3 propane sulfonic acid lactone (1,3-PS), and 1% by mass of lithium difluorophosphate (LiPO) were added2F2) Then, the high-temperature cycle performance of the battery is poor, the high-temperature storage performance is general, and the cycle performance of the battery under the low-temperature condition is general. When in an electrolyteAfter the novel silicon-substituted solvent with the content of 5 percent is added (comparative examples 2, 3, 4 and 5), the impedance of the battery is reduced due to the excellent fluidity and the low viscosity of the silicon-substituted solvent, so that the low-temperature cycle performance of the battery is greatly improved, and particularly the improvement effect of the compound (1) and the compound (3) is more obvious. But did not improve much in high temperature storage performance. 1% or 2% of the compound (5) or the compound (6) was added to comparative examples 6 to 9, respectively, and it can be seen from the above data that the high temperature storage performance was significantly improved after the additive was introduced into the electrolyte; however, the low-temperature cycle effect is poor due to the increase in resistance after film formation. When the addition amount of the additive is 1%, the high-temperature cycle performance of the additive tends to be improved, and when the addition amount is 2%, the high-temperature cycle performance of the additive is reduced, so that the addition amount of the additive is optimal when 1-2%, the internal resistance of the battery is increased when the addition amount is too much, and the introduction of too much pyridine compounds is not beneficial to the improvement of the high-temperature storage performance.
On the whole, the novel silicon-substituted solvent (the addition amount is 2-30% of the mass of the solvent) and the nitrile group-containing pyridine compound (the addition amount is 0.1-10% of the mass of the electrolyte) are matched for use, so that the high-temperature cycle and high-temperature storage performance of the battery can be obviously improved on the basis of ensuring the low-temperature cycle performance of the battery. The pyridine compound containing nitrile groups is introduced, the nitrile groups in the molecule of the pyridine compound can be polymerized on the surface of the anode to form a film, the activity of the anode is inhibited, the occurrence of side reaction is reduced, meanwhile, the nitrogen atom in the pyridine molecule has lone pair electrons to play a role of Lewis base, and the pyridine compound can be decomposed with the lithium hexafluorophosphate under the high-temperature condition to generate PF5Or POF3The compound forms a complex, so that the damage of an acid substance to a battery system is reduced, and the high-temperature performance of the battery is improved. It should be noted that the electron cloud density on nitrogen in pyridine is not too high, and when the electron cloud density is too high, the risk of oxidative decomposition exists, the lone pair electrons on nitrogen in pyridine can be reduced by introducing unsaturated nitrile group, fluorine atom and oxygen-containing electron withdrawing group into the molecular structure, so that the risk of oxidation is reduced, and when the electron donating methyl group is introduced into pyridine ring, pyridine can be oxidizedThe performance is enhanced, and in order to ensure that the addition of the compound can achieve the effect required by the invention, an electron-withdrawing group is usually introduced on the pyridine ring, so that the activity of the pyridine ring is reduced, and the occurrence of side reactions is inhibited.
It will be understood by those skilled in the art that the foregoing is only exemplary of the present invention, and is not intended to limit the invention, which is intended to cover any variations, equivalents, or improvements therein, which fall within the spirit and scope of the invention.
Claims (14)
1. An electrolyte containing a silicon solvent and a pyridine additive, which comprises a lithium salt, an organic solvent and an additive, and is characterized in that the organic solvent contains a silicon-substituted organic solvent, and the additive contains a nitrile group-containing pyridyl compound; the organic solvent is selected from one of the following compounds (1) to (4):
the pyridyl compound containing the nitrile group is shown as a general formula (III):
in the general formula (III), X1、X2、X3、X4And X5Each independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, a halogen atom, a nitrile group or an alkoxynitrile group of 1 to 5 carbon atoms, and X1、X2、X3、X4And X5In the formula (I), at least one is nitrile group or alkoxy nitrile group with 1-5 carbon atoms;
the additive also comprises 1,3 propane sultone, lithium difluorophosphate, vinylene carbonate and fluoroethylene carbonate.
2. The electrolyte of claim 1, wherein the organic solvent comprises 5-15% by mass of the organic solvent.
3. The electrolyte solution containing a silicon solvent and a pyridine additive according to claim 1, wherein the nitrile group-containing pyridine compound represented by the general formula (iii) is one of compounds (5) to (6):
4. the electrolyte solution containing a silicon solvent and a pyridine additive according to claim 1, wherein the amount of the nitrile group-containing pyridine compound represented by the general formula (III) is 1 to 2% by mass of the electrolyte solution.
5. The electrolyte solution containing the silicon solvent and the pyridine additive according to claim 4, wherein the organic solvent further contains one or more of a chain carbonate organic solvent and a cyclic carbonate organic solvent.
6. The electrolyte as claimed in claim 5, wherein the chain carbonate organic solvent is one or more selected from dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate and dipropyl carbonate, and the cyclic carbonate organic solvent is one or more selected from ethylene carbonate, vinylene carbonate and propylene carbonate.
7. The electrolyte of claim 6, wherein the organic solvent comprises ethylene carbonate, propylene carbonate, ethyl methyl carbonate, and diethyl carbonate.
8. The electrolyte solution containing a silicon solvent and a pyridine-based additive according to claim 7, wherein the ethylene carbonate, propylene carbonate, ethyl methyl carbonate and diethyl carbonate are mixed in a weight ratio of (20-30): (3-8): (45-55): (15-25).
9. The silicon solvent and pyridine additive-containing electrolyte according to claim 7, wherein ethylene carbonate, propylene carbonate, ethyl methyl carbonate and diethyl carbonate are mixed in a weight ratio of 25:5:50: 20.
10. The electrolyte solution containing a silicon solvent and a pyridine additive according to claim 1, wherein the additive comprises 1,3 propane sultone, lithium difluorophosphate, vinylene carbonate and fluoroethylene carbonate in a mass ratio of (2-4) to (1-3) to (0.5-1) to (1-3).
11. The electrolyte solution containing a silicon solvent and a pyridine additive according to claim 10, wherein the additive comprises 1,3 propane sultone, lithium difluorophosphate, vinylene carbonate and fluoroethylene carbonate in a mass ratio of 3:2:1: 2.
12. The electrolyte of claim 1, wherein the lithium salt is selected from LiPF6、LiBF4、LiClO4、LiBOB、LiODFB、LiAsF6、LiN(SO2CF3)2、LiN(SO2F)2And the concentration of the lithium salt in the electrolyte is 0.5 to 2M in terms of lithium ions.
13. The electrolyte of claim 1, wherein the concentration of the lithium salt in the electrolyte is 1-1.5M.
14. A lithium ion battery comprising the electrolyte containing the silicon-containing solvent according to any one of claims 1 to 13 and a pyridine-based additive.
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| CN108172901A (en) * | 2017-12-21 | 2018-06-15 | 江苏理工学院 | A kind of additive of high-voltage lithium ion battery electrolyte |
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| KR102130028B1 (en) * | 2014-05-09 | 2020-07-03 | 삼성에스디아이 주식회사 | Rechargeable lithium battery |
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| CN1328355A (en) * | 2000-06-07 | 2001-12-26 | 默克专利股份有限公司 | Silane compound used as additives of electrochemical accumulator electrolyte |
| CN102088111A (en) * | 2009-12-02 | 2011-06-08 | 索尼公司 | Nonaqueous electrolyte battery |
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