CN112271330A - Electrolyte additive, electrolyte and energy storage device - Google Patents

Electrolyte additive, electrolyte and energy storage device Download PDF

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CN112271330A
CN112271330A CN202011131716.7A CN202011131716A CN112271330A CN 112271330 A CN112271330 A CN 112271330A CN 202011131716 A CN202011131716 A CN 202011131716A CN 112271330 A CN112271330 A CN 112271330A
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electrolyte
fluorosulfonyl
carbonate
lithium
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CN112271330B (en
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曹哥尽
范伟贞
信勇
赵经纬
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Guangzhou Tinci Materials Technology Co Ltd
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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
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/64—Liquid electrolytes characterised by 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
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    • 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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Abstract

The invention relates to an electrolyte additive, an electrolyte and an energy storage device, wherein the electrolyte additive is a sulfonic acid ester compound with a structure shown in a formula (I):
Figure DDA0002735378340000011
a is a substituted or unsubstituted 5-6 membered aryl or heteroaryl; r1、R2Each independently is H, halogen or C1‑6An alkyl group. The electrolyte additive can reduce the DCIR of the battery and improve the high-low temperature performance of the battery.

Description

Electrolyte additive, electrolyte and energy storage device
Technical Field
The invention relates to the technical field of batteries, in particular to an electrolyte additive, an electrolyte and an energy storage device.
Background
In recent years, with market demands and policy guidance, lithium ion batteries are widely popularized, and the lithium ion batteries with the advantages of high energy density, high charging efficiency, long cycle life and the like are widely applied to the fields of power, energy storage, aerospace, digital and the like.
People are continuously demanding on the performance of batteries, and the direct-current internal resistance (DCIR) of batteries is more and more concerned by battery manufacturers as an important index for evaluating the performance of batteries. Generally, the sulfur-containing additives have some effect of reducing the impedance of the battery, thereby improving the high-temperature and low-temperature performance of the battery. 1, 3-propane sultone and vinyl sulfate are respectively used as representative additives of sulfonate and sulfate, so that the high-temperature performance and the low-temperature performance of the battery are improved, and the impedance of the battery is reduced to a certain extent. Compared with a cyclic sulfate structure of vinyl sulfate, the cyclic sulfonate structure of 1, 3-propane sultone has better stability, and the application of the 1, 3-propane sultone is limited by European regulation due to instability of the vinyl sulfate.
Therefore, new sulfur-containing additives that reduce the DCIR of the battery and improve the high and low temperature performance of the battery are still under development.
Disclosure of Invention
In view of the above, there is a need for an electrolyte additive, an electrolyte and an energy storage device, wherein the electrolyte additive can reduce the DCIR of a battery and improve the high and low temperature performance of the battery.
An electrolyte additive is a sulfonate compound having a structure represented by formula (I):
Figure BDA0002735378330000021
a is a substituted or unsubstituted 5-6 membered aryl or heteroaryl;
R1、R2each independently is H, halogen or C1-6An alkyl group.
In one embodiment, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following:
C1-6alkyl, halo C1-6Alkyl radical, C2-8Alkenyl radical, C3-8Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 3-to 8-membered cycloalkyl, 4-to 9-membered heterocyclyl, 6-to 20-membered aryl, 5-to 20-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid or fluorosulfonyl.
In one embodiment, the sulfonate compound has a structure represented by formula (II) or formula (III):
Figure BDA0002735378330000022
x is O, S, NR7Or CR7R8；
R3-R8Each independently is: H. c1-6Alkyl, halo C1-6Alkyl radical, C2-6Alkenyl radical, C3-6Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 6-to 10-membered aryl, 6-to 10-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid, or fluorosulfonic acid.
In one embodiment, R3、R4、R5And R6Each independently is: a hydrogen atom, a fluorine atom, a hydroxyl group, a nitrile group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, an ethylene group, a propylene group, a butenyl group, an acetylene group, a propynyl group, a butynyl group, a methoxy group, an ethoxy group, a propoxy group, a trifluoromethoxy group, a trifluoroethoxy group, a trifluoropropoxy group, a sulfonyl group, a fluorosulfonyl group, a sulfonic group, or a fluorosulfonyl group.
In one embodiment, R3、R4、R5And R6Each independently is: H. f, trifluoromethyl, trifluoroethyl, trifluoropropyl, trifluoromethoxy, trifluoroethoxy, trifluoropropoxy, fluorosulfonyl or fluorosulfonyl.
In one embodiment, the sulfonate compound is selected from any one of the following compounds:
Figure BDA0002735378330000031
an electrolyte comprises the electrolyte additive.
In one embodiment, in the electrolyte, the electrolyte additive is 0.01-10% by mass.
In one embodiment, the electrolyte further includes an electrolyte and a solvent, and the electrolyte is at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (oxalato) borate, lithium difluorophosphate, lithium difluoro (oxalato) phosphate and lithium bis (fluorosulfonyl) imide;
the solvent includes a cyclic solvent as well as a linear solvent.
In one embodiment, the cyclic solvent is at least one of ethylene carbonate, propylene carbonate, gamma-butyrolactone, phenyl acetate, 1, 4-butyl sultone, trifluoroethoxy ethylene carbonate and 3,3, 3-trifluoropropylene carbonate;
the linear solvent is at least one of dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, ethyl acetate, methyl propyl carbonate, propyl propionate, 1, 2, 2-tetrafluoroethyl-2, 2,3, 3-tetrafluoropropyl ether, 2, 2-difluoroethyl acetate, 2, 2-difluoroethyl propionate and 2, 2-difluoroethyl methyl carbonate.
An energy storage device comprises the electrolyte.
In one embodiment, the energy storage device is a lithium ion battery or a super capacitor.
Has the advantages that:
the sulfonate compound is a 1, 3-propane sultone aromatic derivative with a PS molecular skeleton, is applied to an energy storage device as an additive, is decomposed, and can form a stable, uniform, light and thin SEI film on the surface of a negative electrode of the energy storage device due to the existence of an aromatic ring or a heteroaromatic ring, so that the decomposition of a solvent in an electrolyte can be inhibited. In addition, S element is introduced into the SEI film by the alkylated lithium sulfate generated by the decomposition of the sulfonate compound, so that the ionic conductivity is increased, and the DCIR of the battery is reduced. On the other hand, the unsaturated bond in the sulfonate compound can passivate the surface of the positive electrode, inhibit the dissolution of metal ions of the positive electrode, and reduce the decomposition effect of active substances in a high oxidation state on the solvent, so that the electrochemical performance of the energy storage device under the high-temperature condition can be improved. In the energy storage device, the sulfonate compound can suppress an increase in DCIR, and thus can improve high-temperature and low-temperature properties of the energy storage device.
Detailed Description
In order that the invention may be more fully understood, a more particular description of the invention will now be rendered by reference to specific embodiments thereof that are illustrated in the appended drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
Term(s) for
Unless otherwise stated or contradicted, terms or phrases used herein have the following meanings:
in the present invention, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent.
The term "optionally" as used herein means that the defined group may be selected from a series of candidate groups, or may be selected from one or more groups;
in the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood to be optionally substituted with art-acceptable groups including, but not limited to: c1-20Alkyl, halo C1-20Alkyl, hydroxy substituted C1-20Alkyl and nitro substituted C1-20Alkyl and nitrile substituted C1-20Alkyl, sulfonyl substituted C1-20Alkyl, fluorosulfonyl substituted C1-20Alkyl, sulfonic substituted C1-20Alkyl, fluorosulfonic acid substituted C1-20Alkyl radical, C2-16Alkenyl radical, C3-16Alkynyl, C1-16Alkoxy, haloGeneration C1-16Alkoxy, 3-to 8-membered cycloalkyl, 4-to 9-membered heterocyclyl, 6-to 20-membered aryl, 5-to 20-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid, or fluorosulfonyl, and the like.
The term "alkyl" refers to a saturated hydrocarbon containing a primary (normal) carbon atom, or a secondary carbon atom, or a tertiary carbon atom, or a quaternary carbon atom, or a combination thereof. Phrases containing the term, e.g., "C1-16The alkyl group means an alkyl group having 1 to 16 carbon atoms. Suitable examples include, but are not limited to: methyl (Me, -CH)3) Ethyl (Et-CH)2CH3) 1-propyl (n-Pr, n-propyl, -CH)2CH2CH3) 2-propyl (i-Pr, i-propyl, -CH (CH)3)2) 1-butyl (n-Bu, n-butyl, -CH)2CH2CH2CH3) 2-methyl-1-propyl (i-Bu, i-butyl, -CH)2CH(CH3)2) 2-butyl (s-Bu, s-butyl, -CH (CH)3)CH2CH3) 2-methyl-2-propyl (t-Bu, t-butyl, -C (CH)3)3) 1-pentyl (n-pentyl, -CH)2CH2CH2CH2CH3) 2-pentyl (-CH (CH3) CH2CH2CH3), 3-pentyl (-CH (CH)2CH3)2) 2-methyl-2-butyl (-C (CH)3)2CH2CH3) 3-methyl-2-butyl (-CH (CH)3)CH(CH3)2) 3-methyl-1-butyl (-CH)2CH2CH(CH3)2) 2-methyl-1-butyl (-CH)2CH(CH3)CH2CH3) 1-hexyl (-CH)2CH2CH2CH2CH2CH3) 2-hexyl (-CH (CH)3)CH2CH2CH2CH3) 3-hexyl (-CH (CH)2CH3)(CH2CH2CH3) 2-methyl-2-pentyl (-C (CH))3)2CH2CH2CH3) 3-methyl-2-pentyl (-CH (CH)3)CH(CH3)CH2CH3) 4-methyl-2-pentyl (-CH (CH)3)CH2CH(CH3)2) 3-methyl-3-pentyl (-C (CH)3)(CH2CH3)2) 2-methyl-3-pentyl (-CH (CH)2CH3)CH(CH3)2) 2, 3-dimethyl-2-butyl (-C (CH)3)2CH(CH3)2) 3, 3-dimethyl-2-butyl (-CH (CH)3)C(CH3)3And octyl (- (CH)2)7CH3)。
The term "cycloalkyl" refers to a non-aromatic hydrocarbon containing ring carbon atoms and may be a monocycloalkyl, or spirocycloalkyl, or bridged cycloalkyl. Phrases comprising the term, for example, "3-8 membered cycloalkyl" refers to a cycloalkyl group containing 3 to 8 carbon atoms, which at each occurrence, independently of each other, may be C3Cycloalkyl radical, C4Cycloalkyl radical, C5Cycloalkyl radical, C6Cycloalkyl radical, C7Cycloalkyl or C8A cycloalkyl group. Suitable examples include, but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. In addition, "cycloalkyl" may also contain one or more double bonds, and representative examples of cycloalkyl groups containing a double bond include cyclopentenyl, cyclohexenyl, cyclohexadienyl, and cyclobutadienyl.
The term "alkoxy" refers to a group having an-O-alkyl group, i.e., an alkyl group as defined above attached to the parent core structure via an oxygen atom. Suitable examples include, but are not limited to: methoxy (-O-CH)3or-OMe), ethoxy (-O-CH)2CH3or-OEt) and tert-butoxy (-O-C (CH)3)3or-OtBu).
"alkenyl" means containing a moiety having at least one unsaturation, i.e., a carbon-carbon sp2A hydrocarbon of a positive carbon atom, a secondary carbon atom, a tertiary carbon atom or a ring carbon atom of a double bond. Phrases containing the term, e.g., "C2～C16The alkenyl group means an alkenyl group having 2 to 16 carbon atoms. Suitable examples include, but are not limited to: vinyl (-CH ═ CH)2) Allyl (-CH)2CH＝CH2) Cyclopentenyl (-C)5H7) And 5-hexenyl (-CH)2CH2CH2CH2CH＝CH2)。
"alkynyl" refers to a hydrocarbon containing a normal, secondary, tertiary, or ring carbon atom having at least one site of unsaturation, i.e., a carbon-carbon sp triple bond. Phrases containing the term, e.g., "C2-16The alkenyl group means an alkynyl group having 2 to 16 carbon atoms. Suitable examples include, but are not limited to: ethynyl (-C ≡ CH) and propargyl (-CH)2C≡CH)。
"aryl" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from the aromatic ring compound and may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for polycyclic ring species. For example, "6-20 membered aryl" refers to aryl groups containing 6 to 20 carbon atoms, suitable examples include, but are not limited to: benzene, biphenyl, naphthalene, anthracene, phenanthrene, perylene, triphenylene, and derivatives thereof.
"heteroaryl" means that on the basis of an aryl at least one carbon atom is replaced by a non-carbon atom which may be a N atom, an O atom, an S atom, etc. For example, "C3-20The "heteroaryl group" means a heteroaryl group having 3 to 20 carbon atoms, and suitable examples include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, primadine, quinazoline, and quinazolinone.
"Heterocyclyl" means that at least one carbon atom is replaced with a non-carbon atom, which may be a N atom, an O atom, an S atom, etc., and may be a saturated ring or a partially unsaturated ring, in addition to a cycloalkyl group. Phrases comprising this term, such as "4-9 membered heterocyclyl" refer to heterocyclyl groups comprising 4 to 9 carbon atoms, at each occurrence. Suitable examples include, but are not limited to: dihydropyridinyl, tetrahydropyridinyl (piperidinyl), tetrahydrothienyl, thiooxidised tetrahydrothienyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, indolinyl.
"halogen" or "halo" refers to F, Cl, Br, or I.
Sulfonyl means containing
Figure BDA0002735378330000071
A group of moieties;
the sulfonic acid group means containing
Figure BDA0002735378330000072
A moiety of (a).
Detailed explanation
One embodiment of the present invention provides a sulfonate compound having a structure represented by formula (I):
Figure BDA0002735378330000073
a is a substituted or unsubstituted 5-6 membered aryl or heteroaryl;
R1、R2each independently is H, halogen or C1-6An alkyl group; preferably R1、R2Each independently is H.
Further, a is a substituted or unsubstituted phenyl, or a substituted or unsubstituted 5-membered heteroaryl;
further, 5-membered heteroaryl contains 1, 2 or 3 heteroatoms; further, the 5-membered heteroaryl group contains 1 heteroatom; further, the heteroatom in the 5-membered heteroaryl group is O, N, S or SO2；
Further, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following groups:
C1-16alkyl, halo C1-16Alkyl radical, C2-16Alkenyl radical, C3-16Alkynyl, C1-16Alkoxy, halo C1-16Alkoxy, 3-to 8-membered cycloalkyl, 4-to 9-membered heterocyclyl, 6-to 20-membered aryl, 5-to 20-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid or fluorosulfonic acidAnd (4) a base.
Further, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following groups:
C1-6alkyl, halo C1-6Alkyl radical, C2-8Alkenyl radical, C3-8Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 3-to 8-membered cycloalkyl, 4-to 9-membered heterocyclyl, 6-to 10-membered aryl, 5-to 10-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid or fluorosulfonyl.
Further, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following groups:
C1-4alkyl, halo C1-4Alkyl radical, C2-6Alkenyl radical, C3-6Alkynyl, C1-4Alkoxy, halo C1-4Alkoxy, 3-to 8-membered cycloalkyl, 4-to 6-membered heterocyclyl, 6-to 10-membered aryl, 5-to 6-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid, or fluorosulfonyl.
Further, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more fluorine atom containing groups;
further, the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following groups: fluorine atom, fluoro C1-6Alkyl, fluorosulfonyl or fluorosulfonyl;
further, the above sulfonate compound has a structure represented by formula (II) or formula (III):
Figure BDA0002735378330000081
x is O, S, NR7Or CR7R8；
R3-R8Each independently is: H. c1-6Alkyl, halo C1-6Alkyl radical, C2-6Alkenyl radical, C3-6Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 6-10 membered aryl, 6-10 membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acidOr a fluorosulfonic acid group.
Further, R3、R4、R5And R6Each independently is: a hydrogen atom, a fluorine atom, a hydroxyl group, a nitrile group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, an ethylene group, a propylene group, a butenyl group, an acetylene group, a propynyl group, a butynyl group, a methoxy group, an ethoxy group, a propoxy group, a trifluoromethoxy group, a trifluoroethoxy group, a trifluoropropoxy group, a sulfonyl group, a fluorosulfonyl group, a sulfonic group, or a fluorosulfonyl group.
Further, R3、R4、R5And R6Each independently is: H. f, trifluoromethyl, trifluoroethyl, trifluoropropyl, trifluoromethoxy, trifluoroethoxy, trifluoropropoxy, fluorosulfonyl or fluorosulfonyl.
Further, R7Is H or C1-6An alkyl group; r8Is H;
further, the above sulfonate compound is selected from any one of the following compounds:
Figure BDA0002735378330000091
an embodiment of the present invention also provides a method for preparing the above sulfonate compound, comprising the steps of:
carrying out Friedel-crafts acylation reaction on the compound shown in the formula (I-1) and the compound shown in the formula (I-2) to prepare the compound shown in the formula (I).
Figure BDA0002735378330000092
Further, the molar ratio of the compound represented by the formula (I-1) to the compound represented by the formula (I-2) is 1 (0.8-1.2);
further, the reaction solvent for the above reaction is an aprotic solvent; further, the reaction solvent is at least one of DCM, diethyl ether, nitrobenzene, DMSO, DMF and THF; further, the reaction solvent is DCM; further, the reaction temperature of the reaction is 40-150 ℃; it will be appreciated that the reaction temperature may be adjusted depending on the reaction solvent selected and should not be construed as limiting the present invention.
One embodiment of the present invention provides an application of the above sulfonate compound as an electrolyte additive.
An embodiment of the present invention provides an application of the above sulfonate compound in preparing an electrolyte.
One embodiment of the present invention provides an electrolyte additive, which is a sulfonate compound having a structure represented by formula (I):
Figure BDA0002735378330000101
wherein the sulfonate compound is as described above and will not be described herein.
An embodiment of the present invention provides an electrolyte, including the above electrolyte additive.
The sulfonate compound is a 1, 3-propane sultone aromatic derivative with a PS molecular skeleton, is applied to an energy storage device as an additive, is decomposed, and can form a stable, uniform, light and thin SEI film on the surface of a negative electrode of the energy storage device due to the existence of an aromatic ring, so that the decomposition of a solvent in an electrolyte can be inhibited. In addition, S element is introduced into the SEI film by the alkylated lithium sulfate generated by the decomposition of the sulfonate compound, so that the ionic conductivity is increased, and the DCIR of the battery is reduced. On the other hand, the unsaturated bond in the sulfonate compound can passivate the surface of the positive electrode, inhibit the dissolution of metal ions of the positive electrode, and reduce the decomposition effect of active substances in a high oxidation state on the solvent, so that the electrochemical performance of the energy storage device under the high-temperature condition can be improved. In the energy storage device, the sulfonate compound can suppress an increase in DCIR, and thus can improve high-temperature and low-temperature properties of the energy storage device.
Further, the electrolyte additive is a sulfonic acid ester compound containing a fluorine atom;
because the surface of the negative electrode can form a stable, uniform and light SEI film, and fluorine atoms are introduced by the sulfonic acid ester compound, the freezing point of the electrolyte is reduced, the flash point is improved, the oxidation stability is improved, and the compatibility between the electrolyte and the electrode is enhanced, so that the lithium ion intercalation and deintercalation at low temperature become smooth, and the low-temperature performance of the energy storage device can be further improved.
Furthermore, in the electrolyte, the mass percentage of the electrolyte additive is 0.01-10%; furthermore, the electrolyte additive accounts for 0.01 to 8 percent by mass; furthermore, the electrolyte additive accounts for 0.03 to 5 percent by mass; furthermore, the electrolyte additive accounts for 0.01 to 4 percent by mass; furthermore, the electrolyte additive accounts for 0.05 to 3 percent of the mass percentage; further, the electrolyte additive is 0.05%, 0.5%, 1%, 2%, 3% or 8% by mass.
If the content of the electrolyte additive is too low, the improvement effect on the DCIR and high and low temperature performance of the energy storage device is not good, and if the content of the additive is too high (the additive accounts for more than 10% of the weight of the electrolyte), the formed SEI film is too thick, so that the impedance of the battery is increased; therefore, the comprehensive performance of the electrolyte can be ensured by controlling the content of the additive within the range.
Further, the electrolyte also comprises an electrolyte; further, the electrolyte is at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (oxalato) borate, lithium difluorophosphate, lithium difluoro (oxalato) phosphate and lithium bis (fluorosulfonyl) imide; in one embodiment, the electrolyte is lithium hexafluorophosphate; in one embodiment, the electrolyte is a combination of lithium hexafluorophosphate and lithium bis-fluorosulfonylimide;
furthermore, in the electrolyte, the mass percentage of the electrolyte is 5-20%; so that the positive and negative ions have higher transmission rate and the electrochemical performance of the energy storage device is improved. Furthermore, in the electrolyte, the mass percentage of the electrolyte is 8% -18%; furthermore, in the electrolyte, the mass percentage of the electrolyte is 10-15%; in one embodiment, the electrolyte is a combination of lithium hexafluorophosphate and lithium bis-fluorosulfonylimide in a mass ratio of (10-14): 1;
further, the electrolyte also comprises a solvent; further, the solvent is a cyclic solvent or a linear solvent; furthermore, the ring-shaped solvent is at least one of ethylene carbonate, propylene carbonate, gamma-butyrolactone, phenyl acetate, 1, 4-butyl sultone, trifluoroethoxy ethylene carbonate and 3,3, 3-trifluoropropylene carbonate; further, the linear solvent is at least one of dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, ethyl acetate, methyl propyl carbonate, propyl propionate, 1, 2, 2-tetrafluoroethyl-2, 2,3, 3-tetrafluoropropyl ether, 2, 2-difluoroethyl acetate, 2, 2-difluoroethyl propionate, and 2, 2-difluoroethyl methyl carbonate;
an embodiment of the invention provides an energy storage device, which includes the above electrolyte, and the electrolyte is specifically described above and is not described herein again.
Further, the energy storage device is a lithium ion battery or a super capacitor.
In one embodiment, the positive electrode material of the energy storage device comprises Li1+a(NixCoyM1-x-y)O2、Li(NipMnqCo2-p-q)O4And LiMh(PO4)mOne or more of the above; wherein a is more than or equal to 0 and less than or equal to 0.3, x is more than or equal to 0 and less than or equal to 1, y is more than or equal to 0 and less than or equal to 1, and x + y is more than 0 and less than or equal to 1; p is more than or equal to 0 and less than or equal to 2, q is more than or equal to 0 and less than or equal to 2, and p + q is more than 0 and less than or equal to 2; h is more than 0 and less than 5, m is more than 0 and less than 5; m is Fe, Ni, Co, Mn, Al or V.
In one embodiment, the negative electrode material of the energy storage device includes at least one of metallic lithium, lithium alloy, carbon, silicon-based negative electrode material, and tin-based negative electrode material.
By adopting the electrolyte containing the sulfonate compound, the surface of the negative electrode of the energy storage device can form a stable SEI film under the action of the sulfonate compound containing heterocyclic rings or aromatic rings, the surface of the positive electrode is passivated, and the increase of direct current internal resistance can be inhibited, so that the energy storage device has good high-temperature performance and low-temperature performance. The energy storage device has good high-temperature performance and low-temperature performance, and has good capacity retention rate when being stored or used under high-temperature and low-temperature conditions.
The present invention will be described below with reference to specific examples.
Example 1
(1) The structural formula of the sulfonate compound in this example is shown in formula (IV).
Figure BDA0002735378330000121
The synthetic route of the compound (IV) is as follows:
Figure BDA0002735378330000131
(2) assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate, and accounts for 13% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 2
(1) The structural formula of the sulfonate compound in this example is shown in formula (V).
Figure BDA0002735378330000132
Compound (V) was prepared according to example 1.
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate, and accounts for 13% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 3
(1) The structural formula of the sulfonate compound in this example is shown in formula (V).
(2) Assembling the lithium ion battery:
in this example, the disulfonate compound accounts for 0.5% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate, and accounts for 13% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 4
(1) The structural formula of the sulfonate compound in this example is shown in formula (VI).
Figure BDA0002735378330000141
Compound (VI) was prepared according to example 2.
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate, and accounts for 13% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 5
(1) The structural formula of the sulfonate compound in this example is shown in formula (VI).
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate and bifluorideLithium sulfonimide, lithium hexafluorophosphate and lithium bis-fluorosulfonimide respectively account for 12% and 1% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 6
(1) The structural formula of the sulfonate compound in this example is shown in formula (VI).
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate and lithium bifluorosulfonimide, and the lithium hexafluorophosphate and the lithium bifluorosulfonimide respectively account for 12% and 1% of the weight of the electrolyte; the solvent is formed by mixing ethylene carbonate and 2, 2-difluoroethyl acetate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 7
(1) The structural formula of the sulfonate compound in this example is shown in formula (VI).
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate and lithium bifluorosulfonimide, and the lithium hexafluorophosphate and the lithium bifluorosulfonimide respectively account for 12% and 1% of the weight of the electrolyte; the solvent is a solvent formed by mixing ethylene carbonate and dimethyl carbonate according to the weight ratio of 1: 2; the positive electrode material is LiNi0.6Co0.2Mn0.2O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Example 8
(1) The structural formula of the sulfonate compound in this example is shown in formula (VI).
(2) Assembling the lithium ion battery:
in this example, the sulfonate compound accounts for 1% of the weight of the electrolyte; the electrolyte is lithium hexafluorophosphate, and accounts for 13% of the weight of the electrolyte; the solvent is a solvent formed by mixing trifluoroethoxy ethylene carbonate and 2, 2-difluoroethyl acetate according to a weight ratio of 1: 2; the positive electrode material is LiNi0.8Co0.1Mn0.1O2(ii) a The negative electrode material is artificial graphite; the separator is a polyethylene film. And assembling the soft package battery according to a conventional method.
Comparative example 1
Comparative example 1 is different from example 1 in that the electrolyte does not contain a sulfonate compound.
Comparative example 2
Comparative example 2 is different from comparative example 1 in that the sulfonate compound of example 1 is replaced with a vinylene carbonate additive of 1% by weight of the electrolyte.
Comparative example 3
Comparative example 3 is different from comparative example 1 in that the sulfonic acid ester compound of example 1 is replaced with a vinyl sulfate additive of 1% by weight of the electrolyte.
Comparative example 4
Comparative example 4 is different from comparative example 1 in that the sulfonate compound of example 1 is replaced with 1% by weight of the electrolyte
Figure BDA0002735378330000161
And (3) an additive.
Comparative example 5
Comparative example 5 is different from comparative example 1 in that the sulfonate compound of example 1 is replaced with 1% by weight of the electrolyte
Figure BDA0002735378330000162
And (3) an additive.
High and low temperature performance test of lithium ion battery
The lithium ion batteries in the embodiments 1-8 and the comparative examples 1-5 are subjected to high and low temperature performance tests, and the test method comprises the following steps:
high temperature cycle performance: and (3) placing the lithium ion battery in a constant temperature box at 45 ℃, charging to 4.2V at a constant current and a constant voltage of 1C, then discharging to 3.0V at a constant current of 1C, circulating for 600 weeks, and determining the capacity retention rate of the lithium ion battery.
High temperature storage performance: charging the formed lithium ion battery to 4.2V at normal temperature by using a 1C current constant current and constant voltage, and measuring the initial capacity of the battery; then, after storing for 30 days in an environment of 60 ℃, the lithium ion battery was discharged to 3V at room temperature at 1C and recharged to 4.2V, and the capacity retention rate was measured.
DCIR performance: the battery, which completed the high-temperature storage performance test at 60 ℃ for 30 days, was charged to 4.2V at room temperature at 1C, then discharged at 1C for 30min, and then discharged at 2C for 10s, and the DCIR at 50% SOC of the battery was calculated.
Low-temperature discharge performance: charging the formed lithium ion battery to 4.2V at normal temperature by using a 1C constant current and constant voltage, and measuring the initial capacity of the battery; then, the battery was placed in a thermostat at-20 ℃ and discharged to 2.5V at 0.5C, and the capacity retention rate of the lithium ion battery was measured.
The test results are shown in table 1:
TABLE 1
Figure BDA0002735378330000171
As can be seen from Table 1, the high-temperature cycle performance, the high-temperature storage performance, the DCIR performance and the low-temperature discharge performance of the lithium ion batteries in the embodiments 1 to 8 are superior to those of the comparative examples 1 to 5, which shows that the electrolyte additives in the embodiments 1 to 8 can reduce the DCIR of the batteries and further effectively improve the high-temperature performance and the low-temperature performance of the lithium ion batteries.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (12)

1. An electrolyte additive, characterized by being a sulfonate compound having a structure represented by formula (I):
Figure FDA0002735378320000011
a is a substituted or unsubstituted 5-6 membered aryl or heteroaryl;
R1、R2each independently is H, halogen or C1-6An alkyl group.
2. The electrolyte additive of claim 1 wherein the 5-6 membered aryl or heteroaryl is optionally substituted with one or more of the following groups:
C1-6alkyl, halo C1-6Alkyl radical, C2-8Alkenyl radical, C3-8Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 3-to 8-membered cycloalkyl, 4-to 9-membered heterocyclyl, 6-to 20-membered aryl, 5-to 20-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid or fluorosulfonyl.
3. The electrolyte additive of claim 1, wherein the electrolyte additive has a structure represented by formula (II) or formula (III):
Figure FDA0002735378320000012
x is O, S, NR7Or CR7R8；
R3-R8Each independently is: H. c1-6Alkyl, halo C1-6Alkyl radical, C2-6Alkenyl radical, C3-6Alkynyl, C1-6Alkoxy, halo C1-6Alkoxy, 6-to 10-membered aryl, 6-to 10-membered heteroaryl, halogen, hydroxy, nitrile, sulfonyl, fluorosulfonyl, sulfonic acid, or fluorosulfonic acid.
4. The electrolyte additive of claim 3, wherein R is3、R4、R5And R6Each independently is: a hydrogen atom, a fluorine atom, a hydroxyl group, a nitrile group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, an ethylene group, a propylene group, a butenyl group, an acetylene group, a propynyl group, a butynyl group, a methoxy group, an ethoxy group, a propoxy group, a trifluoromethoxy group, a trifluoroethoxy group, a trifluoropropoxy group, a sulfonyl group, a fluorosulfonyl group, a sulfonic group, or a fluorosulfonyl group.
5. The electrolyte additive of claim 3, wherein R is3、R4、R5And R6Each independently is: H. f, trifluoromethyl, trifluoroethyl, trifluoropropyl, trifluoromethoxy, trifluoroethoxy, trifluoropropoxy, fluorosulfonyl or fluorosulfonyl.
6. The electrolyte additive of claim 1 wherein the sulfonate compound is selected from any one of the following compounds:
Figure FDA0002735378320000021
7. an electrolyte comprising the electrolyte additive of any one of claims 1 to 6.
8. The electrolyte of claim 7, wherein the electrolyte additive is present in the electrolyte in an amount of 0.01 to 10% by weight.
9. The electrolyte of claim 7, further comprising an electrolyte and a solvent, wherein the electrolyte is at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (oxalato) borate, lithium difluorophosphate, lithium difluorooxalato phosphate, and lithium bis (fluorosulfonylimide);
the solvent is at least one of a cyclic solvent and a linear solvent.
10. The electrolyte of claim 9, wherein the cyclic solvent is at least one of ethylene carbonate, propylene carbonate, γ -butyrolactone, phenyl acetate, 1, 4-butylsultone, trifluoroethoxy ethylene carbonate, and 3,3, 3-trifluoropropene carbonate;
the linear solvent is at least one of dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, ethyl acetate, methyl propyl carbonate, propyl propionate, 1, 2, 2-tetrafluoroethyl-2, 2,3, 3-tetrafluoropropyl ether, 2, 2-difluoroethyl acetate, 2, 2-difluoroethyl propionate and 2, 2-difluoroethyl methyl carbonate.
11. An energy storage device comprising the electrolyte of any one of claims 1 to 10.
12. The energy storage device of claim 11, wherein the energy storage device is a lithium ion battery or a supercapacitor.
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