CN113206298A - Ether-group-containing dicarbonate compound for nonaqueous electrolyte, nonaqueous electrolyte containing ether-group-containing dicarbonate compound, and secondary battery - Google Patents
Ether-group-containing dicarbonate compound for nonaqueous electrolyte, nonaqueous electrolyte containing ether-group-containing dicarbonate compound, and secondary battery Download PDFInfo
- Publication number
- CN113206298A CN113206298A CN202110398537.8A CN202110398537A CN113206298A CN 113206298 A CN113206298 A CN 113206298A CN 202110398537 A CN202110398537 A CN 202110398537A CN 113206298 A CN113206298 A CN 113206298A
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- Prior art keywords
- lithium
- compound
- nonaqueous electrolyte
- electrolyte
- oxide
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- -1 dicarbonate compound Chemical class 0.000 title claims abstract description 62
- 239000011255 nonaqueous electrolyte Substances 0.000 title claims abstract description 46
- 125000001033 ether group Chemical group 0.000 title claims abstract description 34
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 20
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 13
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims description 18
- 239000002131 composite material Substances 0.000 claims description 10
- 239000008151 electrolyte solution Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000013538 functional additive Substances 0.000 claims description 9
- 229920000098 polyolefin Polymers 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910003481 amorphous carbon Inorganic materials 0.000 claims description 5
- 229910002804 graphite Inorganic materials 0.000 claims description 5
- 239000010439 graphite Substances 0.000 claims description 5
- 239000007773 negative electrode material Substances 0.000 claims description 5
- 239000007774 positive electrode material Substances 0.000 claims description 5
- 239000002033 PVDF binder Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- PBHYLKMSZFULFJ-UHFFFAOYSA-N [Co].[Ni].[Na] Chemical compound [Co].[Ni].[Na] PBHYLKMSZFULFJ-UHFFFAOYSA-N 0.000 claims description 3
- HGBJDVIOLUMVIS-UHFFFAOYSA-N [Co]=O.[Na] Chemical compound [Co]=O.[Na] HGBJDVIOLUMVIS-UHFFFAOYSA-N 0.000 claims description 3
- RLTFLELMPUMVEH-UHFFFAOYSA-N [Li+].[O--].[O--].[O--].[V+5] Chemical compound [Li+].[O--].[O--].[O--].[V+5] RLTFLELMPUMVEH-UHFFFAOYSA-N 0.000 claims description 3
- ZYXUQEDFWHDILZ-UHFFFAOYSA-N [Ni].[Mn].[Li] Chemical compound [Ni].[Mn].[Li] ZYXUQEDFWHDILZ-UHFFFAOYSA-N 0.000 claims description 3
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- 229910000625 lithium cobalt oxide Inorganic materials 0.000 claims description 3
- 229910002102 lithium manganese oxide Inorganic materials 0.000 claims description 3
- 229910000686 lithium vanadium oxide Inorganic materials 0.000 claims description 3
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 claims description 3
- VLXXBCXTUVRROQ-UHFFFAOYSA-N lithium;oxido-oxo-(oxomanganiooxy)manganese Chemical compound [Li+].[O-][Mn](=O)O[Mn]=O VLXXBCXTUVRROQ-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002210 silicon-based material Substances 0.000 claims description 3
- IKULXUCKGDPJMZ-UHFFFAOYSA-N sodium manganese(2+) oxygen(2-) Chemical compound [O-2].[Mn+2].[Na+] IKULXUCKGDPJMZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011366 tin-based material Substances 0.000 claims description 3
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- SOXUFMZTHZXOGC-UHFFFAOYSA-N [Li].[Mn].[Co].[Ni] Chemical compound [Li].[Mn].[Co].[Ni] SOXUFMZTHZXOGC-UHFFFAOYSA-N 0.000 claims description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims 1
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- 230000000052 comparative effect Effects 0.000 description 27
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- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 8
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- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- ZMQDTYVODWKHNT-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphate Chemical compound FC(F)(F)COP(=O)(OCC(F)(F)F)OCC(F)(F)F ZMQDTYVODWKHNT-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- FCTINJHSYHFASK-UHFFFAOYSA-N tris(prop-2-ynyl) phosphate Chemical compound C#CCOP(=O)(OCC#C)OCC#C FCTINJHSYHFASK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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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
- H01M10/0569—Liquid materials characterised by the solvents
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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
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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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
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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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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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
- H01M2300/00—Electrolytes
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- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
The invention relates to the field of lithium batteries, and discloses an ether group-containing dicarbonate compound for a nonaqueous electrolyte, a nonaqueous electrolyte containing the ether group-containing dicarbonate compound, and a secondary battery. The double carbonate compound of the present invention has two carbonate groups and 1 or more oxygen atoms in one molecule, and can raise dielectric constant and Li+Binding capacity, thus improving the solubility and conductivity of lithium salt, and also having the function of driving Li+The ability to move. The compound is an ether group formed by connecting an oxygen atom and an C, H atom outside a carbonate group, and has low viscosity. And the molecules are nonpolar molecules, so that the acting force between the molecules can be reduced. The compound can be used as a solvent and can also be used as an electrolyte according to different specific structures and different specific contents in the electrolyteAs an additive.
Description
Technical Field
The invention relates to the field of lithium batteries, in particular to an ether group-containing dicarbonate compound for a nonaqueous electrolyte, a nonaqueous electrolyte containing the ether group-containing dicarbonate compound and a secondary battery.
Background
Lithium ion secondary batteries have been successfully commercialized as an important invention in the energy field at the end of the 20 th century, and are widely applied to the fields of batteries for consumer products such as notebook computers, mobile phones and wearable devices, power batteries for buses, household automobiles, production vehicles and the like, and large-scale energy storage devices. As such, the nobel prize in 2019 awarded the father John b.goodenough, m.stanley Whittingham and Akira Yoshino of three-position lithium batteries to show their outstanding contributions. And the rapid development is achieved in the last 30 years, and the energy density is higher and higher, the service life is longer and longer, the safety is higher and higher. Of course, all lithium battery workers are always struggling and pursuing to further improve battery performance.
In general, optimizing cell design of lithium ion batteries and applying high performance battery materials are two common approaches. The design of the battery core mainly refers to the structure, the size, the coating thickness of the pole piece, the rolling thickness and the like of the battery. The battery material mainly refers to 4 main materials of a positive electrode, a diaphragm, a negative electrode and electrolyte. The positive electrode is used as a lithium source, and generally affects the upper limit voltage, the charge-discharge plateau, the gram-volume, the safety and the like of a battery cell. The negative electrode, which is a temporary receiving container for lithium ions, generally affects the lower limit voltage, energy density, safety, and the like of the cell. The diaphragm is used as a material for isolating the positive electrode and the negative electrode, so that the safety of the battery cell is influenced to a greater extent. The electrolyte as a transmitter of lithium ions has important influences on the safety performance, the rate capability, the low-temperature discharge performance, the high-temperature storage performance, the cycle life and the like of the battery cell. Meanwhile, the production of the electrolytes with different formulas has little difference on the process requirements, and the same equipment and even operation conditions can be adopted; when the method is applied to the production of the battery cell, the original formula can be easily replaced without obviously adjusting equipment and process. Therefore, compared with other 3 major materials, the method is most easily realized in industrial production. As such, the industry often desires to improve the overall cell performance through electrolyte improvement.
The organic nonaqueous electrolyte mainly comprises lithium salt (lithium hexafluorophosphate is mainly used at present), organic solvent and functional additive (film forming additive, flame retardant additive, overcharge prevention additive and the like). At present, most lithium battery workers put the development effort of the electrolyte into the additives. But in fact, the organic solvent is not only used in a large amount, but also has a large influence on the performance of the battery cell. The organic solvents used at present are mainly linear carbonates, carboxylic esters and cyclic carbonates. Although repeatedly tried, sulfones, phosphonates, ethers, alkanes and the like cannot be commercially used as a solvent. For example, japanese patents JP1998228928A and JP1999233141A disclose methods of improving incombustibility of an electrolyte by adding 5 to 100% of a phosphonate and/or phosphinate, respectively, but in fact, use in large amounts may deteriorate electrical properties.
On the other hand, linear carbonates mainly include dimethyl carbonate (DMC), Ethyl Methyl Carbonate (EMC), diethyl carbonate (DEC) and the like, cyclic carbonates mainly include Ethylene Carbonate (EC), Propylene Carbonate (PC) and the like, linear carboxylates mainly include methyl formate, ethyl acetate, methyl butyrate, ethyl propionate, methyl propionate and the like, and cyclic carboxylates mainly include γ -butyrolactone and the like. Although these solvents can now meet the basic performance requirements of the cell at the present time, they also have major drawbacks. For example, the EC has a high dielectric constant, can sufficiently dissolve or ionize a lithium salt, and is advantageous for improving the conductivity of an electrolyte, but has a high viscosity and a high melting point (m.p.36.4 ℃), and needs to be used in combination with a linear carbonate having a low viscosity and a low melting point. The low-temperature performance of the electrolyte can be obviously improved due to the low freezing point and low viscosity of the linear carboxylic ester, but the linear carboxylic ester has a lower boiling point and has poor high-temperature performance. Further, as shown in the Chinese patent (CN 101471459A), when the content of the tertiary carboxylic ester is more than 20% (volume), the self-discharge of the battery is serious, and the self-discharge phenomenon can be inhibited by adding an alkylbenzene compound and a halogenated benzene compound; however, when the content of the tertiary carboxylic ester exceeds 80% by volume, the self-discharge phenomenon cannot be suppressed even if the alkylbenzene compound or the halogenated benzene compound is contained.
Therefore, in order to meet the functional requirements of the electrolyte and simultaneously reduce the deterioration of other properties of the battery core, the development of a novel nonaqueous organic lithium ion secondary battery electrolyte solvent and the application of the novel nonaqueous organic lithium ion secondary battery electrolyte solvent to the lithium ion secondary battery are urgent and important.
Disclosure of Invention
In order to solve the above-mentioned technical problems, the present invention provides an ether group-containing dicarbonate compound for a nonaqueous electrolytic solution, a nonaqueous electrolytic solution containing the same, and a secondary battery. The dicarbonate compound of the present invention can increase the dielectric constant and Li+Binding capacity, thus improving the solubility and conductivity of lithium salt, and also having the function of driving Li+The ability to move. Meanwhile, the compound has lower viscosity, and can reduce intermolecular acting force.
The specific technical scheme of the invention is as follows:
in a first aspect, the present invention provides an ether group-containing dicarbonate compound for a nonaqueous electrolytic solution, having the following structural formula:
wherein x, n and m are independently selected from 1, 2, 3, 4 and 5.
Structurally, the ether group-containing dicarbonate compound has the characteristics that: two carbonate groups are contained in one molecule; ether groups are built up via alternating "-carbon-oxygen-carbon" bonds, which can serve both as a linking group between two carbonate groups and as an end group outside the carbonate groups.
Functionally, the ether group-containing dicarbonate compound is characterized in that: the structure of the whole linear molecule can reduce or even eliminate the defects that the viscosity of the cyclic carbonate is higher and the cyclic carbonate is easier to decompose on the surface of an electrode; the dicarbonate and ether groups contain a plurality of "C-O" and "C ═ O" bonds, and "O" has excess lone pair electrons and Li lacking electrons+Forming strong binding force and obviously increasing dielectric constant, thereby improving the dissolving capacity and conductivity of lithium salt and increasing Li+Mass transfer capacity; ③ two have strong electron-pulling capabilityThe introduction of the 'C ═ O' can make up the defect of insufficient electrochemical stability of ether compounds; ether-substituted alkyl or alkylene can improve the compatibility of the molecule with metal lithium electrodes and lithium-sulfur battery electrodes; the ether group substituted alkyl or alkylene can reduce the viscosity of the molecule and increase Li+Migration ability and battery low temperature performance; replacement of alkyl or alkylene groups with ether groups reduces the negative effect of the introduction of dicarbonates on the melting point of the molecule, maintaining a suitable value.
Further, in the ether group-containing dicarbonate compound, x is preferably 1 or 2, and n and m are preferably 2 to 4.
x, n and m in the above range can satisfy high dielectric constant and dissolving power required by design, and strong Li+Mass transfer capability and high electrode compatibility, and moderate molecular size, viscosity and melting point can be maintained. Conversely, if x ═ n ═ m ═ 5, then the molecular viscosity can increase rapidly, which is detrimental to the performance of the electrolyte.
In a second aspect, the invention provides a nonaqueous electrolyte for a lithium battery, which comprises the ether group-containing dicarbonate compound; the non-aqueous electrolyte also comprises a functional additive, a lithium salt and other organic solvents.
The weight of the ether group-containing dicarbonate compound is 5 to 85 wt% of the weight of the nonaqueous electrolyte. Preferably, the weight of the ether group-containing dicarbonate compound is 10 to 60 wt% of the weight of the nonaqueous electrolytic solution. More preferably, the weight of the ether group-containing dicarbonate compound is 15 to 30 wt% of the weight of the nonaqueous electrolytic solution.
When the content is too high, the content of lithium salt and additives is insufficient, and the performance requirements of battery multiplying power, low temperature and the like cannot be met. When the content is insufficient, the effective improvement of the dielectric constant, the dissolving capacity and the Li conduction of the electrolyte cannot be realized+Capability. And, when the content is more than 10 wt%, it is considered to function as a solvent; when the content is less than 10 wt%, it is considered to function as an additive, i.e., to adjust physical and chemical performance parameters of the electrolyte.
The mass of the functional additive is not more than 15% of the total mass of the nonaqueous electrolyte, the mass of the lithium salt is not more than 15% of the total mass of the nonaqueous electrolyte, and the mass of the other organic solvent is not more than 85% of the total mass of the nonaqueous electrolyte.
Preferably, the mass of the functional additive accounts for 3-12% of the total mass of the non-aqueous electrolyte, so that the action effect of the functional additive is ensured, and adverse results such as cost increase and electrolyte viscosity increase caused by high addition amount are avoided; preferably, the mass of the lithium salt accounts for 10-15% of the total mass of the non-aqueous electrolyte, and the content of the lithium fluoride salt is favorable for avoiding negative effects such as cost increase, electrolyte viscosity increase and thermal stability reduction caused by the increase of the content of the lithium salt on the premise of ensuring that enough lithium ions are provided for the electrolyte and the sufficient lithium ion conductivity of the electrolyte; preferably, the mass of the other organic solvents accounts for 40-70% of the total mass of the nonaqueous electrolyte, and the organic solvents with the content can ensure that the balance of physical property parameters such as reasonable viscosity and conductivity of the electrolyte is maintained while lithium salts and additives are fully dissolved.
As one embodiment of the present invention, the functional additive is selected from at least one of a film forming agent, an overcharge preventing additive, a flame retarding additive, a conductive additive, and an anti-stress additive.
As an embodiment of the present invention, the functional additive is selected from at least one of sulfite, sulfoxide, sulfonate, halocarbonate, halocarboxylate, halophosphate, borate and benzene and derivatives thereof.
As AN embodiment of the present invention, the functional additive is selected from the group consisting of Vinylene Carbonate (VC), Vinyl Ethylene Carbonate (VEC), vinylene sulfate, vinyl sulfate (DTD), vinyl sulfite (ES), fluoroethylene carbonate (FEC), 1, 3-propylene sultone, 1, 3-propane sultone (1, 3-PS), 1, 4-butane sultone (1, 4-BS), Adiponitrile (AN), Succinonitrile (SN), 1, 2-bis (2-cyanoethoxy) ethane (DENE), 1, 3, 6-Hexane Trinitrile (HTCN), glutaronitrile, pimelonitrile, sebaconitrile, propylene-1, 3-sultone, 4-methyl vinyl sulfate, 4-ethyl vinyl sulfate, 4-propyl vinyl sulfate, methane disulfonate, methylene methane disulfonate, At least one of tris (trimethylsilane) borate (TMSB), tris (trimethylsilane) phosphite (TMSPi), tris (trimethylsilane) phosphate (TMSPa), 2-fluorobiphenyl, 2, 4-difluorobiphenyl, p-fluorobiphenyl, triethyl phosphate, tripropyl phosphate, tris (2, 2, 2-trifluoroethyl) phosphate, trivinyl phosphate, triallyl phosphate, tripropargyl phosphate, and pentafluoroethoxyphosphazene.
In one embodiment of the present invention, the lithium salt is selected from LiPF6、LiN(SO2F)2(LiFSI)、LiN(SO2CF3)2、LiN(SO2C2F5)2、LiCF3SO3、LiC(SO2CF3)3、LiPF3(CF3)3、LiPF3(C2F5)3、LiPF3(iso-C3F7)3、LiPF5(iso-C3F7)、LiPF2(C2O4)2、LiPF4(C2O4)、LiPF2O2(LFP)、LiBF4、LiB(C2O4)2、LiBF2(C2O4)(LiODFB)、Li2B12F12、LiClO4And LiAsF6At least one of (1).
As an embodiment of the present invention, the other organic solvent is at least one selected from the group consisting of cyclic carbonates, linear carbonates, carboxylates, sulfites, sulfonates, sulfones, ethers, fluoroethers, organosilicon compounds, nitriles, aromatic hydrocarbons, ionic liquids, and cyclic phosphazene compounds.
As an embodiment of the present invention, the other organic solvent is at least one selected from the group consisting of Ethylene Carbonate (EC), Propylene Carbonate (PC), dimethyl carbonate (DMC), diethyl carbonate (DEC), Ethyl Methyl Carbonate (EMC), methyl propyl carbonate (PMC), Methyl Acetate (MA), Ethyl Acetate (EA), Propyl Acetate (PA), Methyl Propionate (MP), Ethyl Propionate (EP), Propyl Propionate (PP), Methyl Butyrate (MB), γ -butyrolactone, γ -valerolactone, fluorobenzene, toluene, xylene, 1, 2, 2-tetrafluoroethyl-2, 2, 3, 3-tetrafluoropropyl ether (TFETFP).
In a third aspect, the present invention provides a nonaqueous electrolyte secondary lithium battery comprising a positive electrode, a negative electrode, a separator and the above nonaqueous electrolyte.
Preferably, the positive electrode material is at least one selected from the group consisting of lithium nickel cobalt manganese complex oxide, sodium nickel cobalt complex oxide, lithium nickel cobalt aluminum complex oxide, lithium manganese nickel complex oxide, olivine-type lithium iron phosphorus oxide, lithium cobalt oxide, sodium cobalt oxide, lithium manganese oxide, and sodium manganese oxide. But are not limited to, the above materials.
In one embodiment of the present invention, the negative electrode material is at least one selected from graphite, mesocarbon microbeads, amorphous carbon, lithium titanium oxide, lithium vanadium oxide, silicon-based material, tin-based material, and transition metal oxide. The graphite comprises artificial graphite and natural graphite; the amorphous carbon includes hard carbon and soft carbon. But are not limited to, the above materials.
As an embodiment of the present invention, the separator is selected from a polyolefin melt-stretched separator; or the diaphragm is selected from at least one of PET (polyethylene terephthalate), polyvinylidene fluoride, aramid fiber and polyamide as a base material; or a separator selected from a high softening point porous matrix material coated with polyolefin. The polyolefin melt-stretched membrane can be a polypropylene single-layer membrane or a polyethylene single-layer membrane, or a polypropylene/polyethylene/polypropylene three-layer composite membrane and the like. The high-softening-point porous base material refers to a porous base material with a softening point higher than 150 ℃. But are not limited to, the above materials.
The structure of the lithium ion battery is selected from any one of a button battery, a soft package, an aluminum shell, a steel shell, a plastic shell and a cylinder 18650 type.
Compared with the prior art, the invention has the following technical effects:
(1) the ether-group-containing dicarbonate compound of the present invention contains two carbonate groups and 1 or more oxygen atoms in one molecule, has a high dielectric constant and contains Li+Binding capacity, high dissolving capacity and Li+Mass transfer capability and better electrode compatibilityAnd (4) compatibility.
(2) The oxygen atom and C, H atom outside the carbonate group of the ether-group-containing dicarbonate compound of the present invention are connected to form an ether group, which is beneficial to relieving the increase of molecular viscosity caused by the dicarbonate group.
(3) The ether-group-containing dicarbonate compound of the present invention can be used as a solvent and an additive depending on the specific structure and the specific content in the electrolyte.
Drawings
Fig. 1 is a graph of capacity retention rate versus cycle at room temperature for the batteries obtained in example 1 and comparative example 1.
Detailed Description
The present invention will be further described with reference to the following examples.
General examples
An ether group-containing dicarbonate compound for a nonaqueous electrolytic solution has the following structural formula:
wherein x, n and m are independently selected from 1, 2, 3, 4 and 5. Further, preferably 1 or 2, n and m are preferably 2 to 4.
A lithium battery non-aqueous electrolyte, which comprises the dicarbonate compound; the weight of the dicarbonate compound is 5-85 wt% of the weight of the nonaqueous electrolyte. Preferably, the weight of the dicarbonate compound is 10 to 60 wt% of the weight of the nonaqueous electrolyte. More preferably, the weight of the dicarbonate compound is 15 to 30 wt% of the weight of the nonaqueous electrolyte.
A non-aqueous electrolyte secondary lithium battery includes a positive electrode, a negative electrode, a separator and the non-aqueous electrolyte.
The positive electrode material is selected from at least one of lithium nickel cobalt manganese composite oxide, sodium nickel cobalt composite oxide, lithium nickel cobalt aluminum composite oxide, lithium manganese nickel composite oxide, olivine-type lithium iron phosphorus oxide, lithium cobalt oxide, sodium cobalt oxide, lithium manganese oxide and sodium manganese oxide. But are not limited to, the above materials.
Preferably, the negative electrode material is at least one selected from graphite, mesocarbon microbeads, amorphous carbon, lithium titanium oxide, lithium vanadium oxide, silicon-based material, tin-based material and transition metal oxide. The graphite comprises artificial graphite and natural graphite; the amorphous carbon includes hard carbon and soft carbon. But are not limited to, the above materials.
Preferably, the separator is selected from a polyolefin melt-drawn separator; or the diaphragm is selected from at least one of PET (polyethylene terephthalate), polyvinylidene fluoride, aramid fiber and polyamide as a base material; or a separator selected from a high softening point porous matrix material coated with polyolefin. The polyolefin melt-stretched membrane can be a polypropylene single-layer membrane or a polyethylene single-layer membrane, or a polypropylene/polyethylene/polypropylene three-layer composite membrane and the like. The high-softening-point porous base material refers to a porous base material with a softening point higher than 150 ℃. But are not limited to, the above materials.
The following specific examples describe the present invention in detail, however, the present invention is not limited to the following examples.
Example 1
The nonaqueous electrolyte is prepared from EC, EMC, compound A and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 8.9 mS/cm.
Manufacturing a battery: the 2Ah laminated aluminum plastic film flexible package battery adopts LiNi as the positive electrode material0.6Co0.2Mn0.2O2(NCM622), hard carbon is used as the negative electrode material.
And (3) testing the battery performance: the flexible package battery is charged and discharged in a voltage range of 3.00-4.40V at an ambient temperature of 25 ℃, namely, the flexible package battery is charged to 4.40V by a constant current (the charging multiplying factor is 1C), then is charged by a constant voltage of 4.40V (the cut-off current is 0.05C), and then is discharged to 3.00V by a constant current (the discharging multiplying factor is 1C). And carrying out normal-temperature rate discharge and normal-temperature cycle life test on the battery.
Performance results: the charging and discharging efficiency is basically stabilized at about 100%. The 2C discharge capacity at room temperature was 90.2% of the 0.2C discharge capacity, and the 1C discharge capacity was 96.4% of the 0.2C discharge capacity. The capacity retention rate of 200 cycles at room temperature under 1C is 97.5%.
Example 2
The nonaqueous electrolyte is prepared from EC, EMC, compound B and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 8.1 mS/cm.
Manufacturing a battery: the same as in example 1.
And (3) testing the battery performance: the same as in example 1.
Performance results: the charging and discharging efficiency is basically stabilized at about 100%. The 2C discharge capacity at room temperature was 88.0% of the 0.2C discharge capacity, and the 1C discharge capacity was 92.2% of the 0.2C discharge capacity. The capacity retention rate of 200 cycles of the 1C cycle at normal temperature is 92.9 percent.
Example 3
The non-aqueous electrolyte is prepared into EMC, compound C and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 5.8 mS/cm.
Manufacturing a battery: the same as in example 1.
And (3) testing the battery performance: the same as in example 1.
Performance results: the 2C discharge capacity at room temperature was 80.7% of the 0.2C discharge capacity, and the 1C discharge capacity was 85.8% of the 0.2C discharge capacity. Capacity retention rate of 90.4% after 200 cycles at normal temperature and 1C.
Example 4
The nonaqueous electrolyte is prepared from EC, EMC, compound D and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 7.8 mS/cm.
Manufacturing a battery: the same as in example 1.
And (3) testing the battery performance: the same as in example 1.
Performance results: the charging and discharging efficiency is basically stabilized at about 100%. The 2C discharge capacity was 91.6% of the 0.2C discharge capacity at room temperature, and the 1C discharge capacity was 96.9% of the 0.2C discharge capacity. The capacity retention rate of the product after 200 cycles of 1C at normal temperature is 88.6 percent.
Example 5
The non-aqueous electrolyte is prepared into a compound E and LiPF6VC: 1 and 3-PS in a mass ratio of 85: 13: 1. The conductivity of the electrolyte was 3.4 mS/cm.
The electrolyte was not used to prepare a battery.
Example 6
The non-aqueous electrolyte is prepared from EC, PP, compound F and LiPF6The mass ratio of LiODFB to VC to FEC to ADN is 20: 29: 20: 12: 0.5: 1: 5: 2.5. The conductivity of the electrolyte was 6.7 mS/cm.
Manufacturing a battery: the button half-cell assembly positive electrode material adopts lithium cobaltate (LiCoO)2LCO), the negative electrode material uses lithium metal (Li).
And (3) testing the battery performance: and (3) charging and discharging the button cell at the ambient temperature of 25 ℃ in a voltage range of 3.00-4.40V, namely, charging the button cell to 4.40V by a constant current (with the charging rate of 0.5C), and then discharging the button cell to 3.00V by the constant current (with the discharging rate of 0.5C). And carrying out normal-temperature rate test and normal-temperature cycle life test on the battery.
Performance results: the 2C discharge capacity at room temperature was 95.1% of the 0.2C discharge capacity, and the 1C discharge capacity was 97.7% of the 0.2C discharge capacity. Capacity retention rate of 90.2% at normal temperature and 0.5C cycle for 100 weeks.
Example 7
The non-aqueous electrolyte is prepared from EC, PP, compound G and LiPF6The mass ratio of LiODFB to VC to FEC to ADN is 20: 34: 15: 12: 0.5: 1: 5: 2.5. The conductivity of the electrolyte was 6.0 mS/cm.
Manufacturing a battery: the same as in example 6.
And (3) testing the battery performance: the same as in example 6.
Performance results: the 2C discharge capacity was 94.3% of the 0.2C discharge capacity at room temperature, and the 1C discharge capacity was 96.4% of the 0.2C discharge capacity. The capacity retention rate of the 100-week cycle at the normal temperature is 88.7 percent.
Comparative example 1
The nonaqueous electrolyte is prepared into EC, EMC and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 7.2 mS/cm.
Manufacturing a battery: the same as in example 1.
And (3) testing the battery performance: the same as in example 1.
Performance results: the charging and discharging efficiency is basically stabilized at about 100%. The 2C discharge capacity at room temperature was 86.3% of the 0.2C discharge capacity, and the 1C discharge capacity was 90.4% of the 0.2C discharge capacity. Capacity retention rate of 55.1% after 200 cycles at normal temperature and 1C.
Comparative example 2
Non-aqueous electrolyte formulationPrepared into EC, X and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 4.0 mS/cm.
Manufacturing a battery: the same as in example 1.
And (3) testing the battery performance: the same as in example 1.
Performance results: the 2C discharge capacity at room temperature was 70.5% of the 0.2C discharge capacity, and the 1C discharge capacity was 82.6% of the 0.2C discharge capacity. The capacity retention rate of the 1C circulation at normal temperature for 200 weeks is 73.9 percent.
Comparative example 3
The non-aqueous electrolyte is prepared into E: LiPF6VC: 1 and 3-PS in a mass ratio of 85: 13: 1. The conductivity of the electrolyte was 2.3 mS/cm.
The electrolyte was not used to prepare a battery.
Comparative example 4
The nonaqueous electrolyte is prepared into EC and LiPF6VC: 1, 3-PS in a mass ratio of 85: 13: 1. The solvent EC is solid at normal temperature and cannot be used for preparing electrolyte.
The electrolyte was not used to prepare a battery.
Comparative example 5
The non-aqueous electrolyte is prepared into EMC: LiPF6VC: 1, 3-PS in a mass ratio of 85: 13: 1. The solid is precipitated from the electrolyte at normal temperature because the LiPF cannot be completely dissolved in the EMC6。
The electrolyte was not used to prepare a battery.
Comparative example 6
The nonaqueous electrolyte is prepared into EC, Y and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 5.6 mS/cm.
Manufacturing a battery: the same as in example 6.
And (3) testing the battery performance: the same as in example 6.
Performance results: the 2C discharge capacity was 93.5% of the 0.2C discharge capacity and the 1C discharge capacity was 94.8% of the 0.2C discharge capacity at room temperature. Capacity retention rate of 66.7 percent at the room temperature after 0.5C circulation for 100 weeks.
Comparative example 7
The nonaqueous electrolyte is prepared into EC, Z and LiPF6Mixed solution of LiFSI, LFP, VC and 3-PS in the mass ratio of 24 to 30 to 12 to 1. The conductivity of the electrolyte was 4.5 mS/cm.
Manufacturing a battery: the same as in example 6.
And (3) testing the battery performance: the same as in example 6.
Performance results: the 2C discharge capacity at room temperature was 91.1% of the 0.2C discharge capacity, and the 1C discharge capacity was 89.5% of the 0.2C discharge capacity. The capacity retention rate of the 100-week cycle at the normal temperature is 42.4 percent at 0.5C.
TABLE 1 electrolyte formulations for the examples and comparative examples
TABLE 2 electrolyte and Battery Performance of examples and comparative examples
Data analysis
By comparing example 1 and comparative example 1, it can be found that when comparative example 1 replaces compound a with EMC, the conductivity is decreased, resulting in the rate capability and the normal temperature cycle capability (fig. 1) of comparative example 1 being inferior to example 1.
By comparing example 3 with comparative example 2, it can be seen that since there is an ether linkage composed of "C-O-C" in compound B compared to the comparative compound X without ether linkage, the conductivity of example 3 is significantly higher than that of comparative example 2 and the overall cell performance is better than that of comparative example 2, indicating the importance of the ether group in the ether group-containing dicarbonate compound.
Example 5 can find that compound D has a relatively high viscosity, but also has a strong lithium ion dissolving and complexing ability, so that a stable electrolyte can be formed and has a certain conductivity, while further increasing the content of compound D in comparative example 3 causes a decrease in conductivity, indicating that the content cannot be excessively high when an ether group-containing dicarbonate compound is used in the electrolyte. In addition, comparative examples 4 and 5, which cannot form a stable electrolyte using only EC (melting point 34 to 37 ℃ C., solid at ordinary temperature) or EMC (low dielectric constant, poor solvency) alone, also demonstrated the superior characteristics of the ether-group-containing dicarbonate compound compared to the cyclic carbonate or linear carbonate alone.
From comparison of example 6 with comparative example 6, it can be seen that the ether group-containing biscarbonate compound F, as well as in the lithium cobaltate/lithium metal coin cell, makes both the electrolyte conductivity and the cell performance of example 6 higher than comparative example 6 using a comparative compound Y containing only one carbonate group because it contains two carbonates. Illustrating the ability of the present invention to enhance the conductivity of ether group-containing bis-carbonate compounds and improve the performance of batteries by introducing two carbonate groups compared to carbonate compounds.
Similarly, it can be seen from a comparison of example 7 and comparative example 7 that comparative compound Z in comparative example 7 does not contain any carbonate group, resulting in a decrease in the conductivity of the electrolyte and deterioration in the battery performance. It is noted that comparative example 7 still had a certain conductivity because the electrolyte contained more EC, and the viscosity of the ether-based comparative compound Z was lower. This also laterally confirms the significance of introducing multiple ether groups into the ether-containing biscarbonate compound.
The raw materials and equipment used in the invention are common raw materials and equipment in the field if not specified; the methods used in the present invention are conventional in the art unless otherwise specified.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, alterations and equivalents of the above embodiments according to the technical spirit of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (10)
1. An ether group-containing dicarbonate compound for a nonaqueous electrolytic solution, characterized in that: the structural formula is as follows:
2. The bis-carbonate compound according to claim 1, wherein: x is 1 or 2, and n and m are 2-4.
3. A nonaqueous electrolyte for a lithium battery, characterized in that: comprising the dicarbonate compound of claim 1 or 2, a functional additive, a lithium salt and other organic solvents.
4. The nonaqueous electrolytic solution of claim 3, wherein: the weight of the dicarbonate compound is 0.5-85 wt% of the weight of the nonaqueous electrolyte.
5. The nonaqueous electrolytic solution of claim 4, wherein: the weight of the dicarbonate compound is 10-60 wt% of the weight of the nonaqueous electrolyte.
6. The nonaqueous electrolytic solution of claim 5, wherein: the weight of the dicarbonate compound is 15-30 wt% of the weight of the nonaqueous electrolyte.
7. A nonaqueous electrolyte secondary lithium battery comprising a positive electrode, a negative electrode, a separator and the nonaqueous electrolyte solution described in any one of claims 3 to 6.
8. A lithium secondary battery as claimed in claim 7, characterized in that: the positive electrode material is selected from at least one of lithium nickel cobalt manganese composite oxide, sodium nickel cobalt composite oxide, lithium nickel cobalt aluminum composite oxide, lithium manganese nickel composite oxide, olivine-type lithium iron phosphorus oxide, lithium cobalt oxide, sodium cobalt oxide, lithium manganese oxide and sodium manganese oxide.
9. A lithium secondary battery as claimed in claim 7, characterized in that: the negative electrode material is selected from at least one of graphite, mesocarbon microbeads, amorphous carbon, lithium titanium oxide, lithium vanadium oxide, silicon-based materials, tin-based materials and transition metal oxides.
10. A lithium secondary battery as claimed in claim 7, characterized in that: the separator is selected from a polyolefin melt-drawn separator; or at least one selected from polyethylene glycol terephthalate, polyvinylidene fluoride, aramid fiber and polyamide as a base material; or a separator selected from a high softening point porous matrix material coated with polyolefin.
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