CN109467572B - 3, 5-diphosphazene p-phenylene diether additive and lithium ion battery electrolyte containing same - Google Patents

3, 5-diphosphazene p-phenylene diether additive and lithium ion battery electrolyte containing same Download PDF

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CN109467572B
CN109467572B CN201811361577.XA CN201811361577A CN109467572B CN 109467572 B CN109467572 B CN 109467572B CN 201811361577 A CN201811361577 A CN 201811361577A CN 109467572 B CN109467572 B CN 109467572B
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梁大宇
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    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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    • H01—ELECTRIC ELEMENTS
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    • 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
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Abstract

The invention discloses a 3, 5-diphosphazene p-phenylene diether additive and a lithium ion battery electrolyte containing the additive, wherein the lithium ion battery electrolyte consists of lithium salt, an organic solvent, the 3, 5-diphosphazene p-phenylene diether additive and a film forming additive. The 3, 5-diphosphazene p-phenylene diether additive has a high-efficiency flame retardant effect, and can play a role in effective overcharge protection through the reversible redox reaction of hydrogen atoms on a benzene ring, so that the using amount of a conventional safety additive is reduced, the influence on the electrochemical performance of a lithium ion battery is small, and the safety performance and the electrochemical performance of the lithium ion battery electrolyte are both considered.

Description

3, 5-diphosphazene p-phenylene diether additive and lithium ion battery electrolyte containing same
Technical Field
The invention relates to the field of lithium ion battery electrolyte, in particular to a 3, 5-diphosphazene p-phenylene diether additive and lithium ion battery electrolyte containing the same.
Background
The lithium ion battery has the remarkable advantages of high energy density, low self-discharge rate, wide use temperature range, long cycle life, no memory effect and the like, and is widely applied to the fields of 3C digital products, new energy automobiles, energy storage power stations, aerospace and the like. The electrolyte is an essential important component of the lithium ion battery, and has important influence on various performances such as capacity, internal resistance, circulation, multiplying power, safety and the like of the lithium ion battery, however, the current commercial electrolyte contains a large amount of carbonate organic solvents, so that the lithium ion battery can ensure higher ionic conductivity and electrochemical stability required by the normal work of the lithium ion battery, but usually has the defects of lower flash point, flammability and the like, and the lithium ion battery is easy to have safety accidents such as combustion, fire, even explosion and the like in the use process. In addition, rated working voltage and capacity can be reached only when a large number of lithium ion battery monomers are connected in series and parallel in a group, due to the difference of initial electrochemical performances such as different monomer cell voltages, capacities and the like and the attenuation rate of the electrochemical performances in the cyclic charge and discharge use process, part of the battery monomers with fast attenuation can have the risk of overcharge, due to the fact that the structure of a positive electrode material under the overcharge condition is more unstable, lithium is more easily separated from the surface of a negative electrode, the side reaction of the electrode material and electrolyte is more severe, and therefore safety accidents such as combustion, fire and even explosion can be caused.
In order to solve the potential safety hazard in the application process of the lithium ion battery, currently, a plurality of protection methods are researched, including measures of modifying positive and negative electrode materials, using a battery response protection device, adding a safety additive into an electrolyte and the like, wherein the addition of an overcharge prevention and flame retardant electrolyte additive is considered to be a more convenient, feasible and effective important method. The most studied flame retardant additives at present are organic phosphorus compounds, including phosphate esters, phosphite esters, halogenated phosphate esters, cyclic phosphazene compounds and the like, for example, the invention patent with the publication number of CN108365264A reports a ternary electrolyte of a lithium battery, including lithium salts, organic solvents, overcharge protection additives and flame retardant additives, wherein a small molecular linear phosphazene compound is used as the flame retardant additive to promote the formation of an SEI film and reduce the addition of film forming additives, and at least one overcharge prevention additive including xylene, bromoanisole, 4-bromo-2-fluorophenylmethyl ether, biphenyl, cyclohexylbenzene and the like is added, so that the safety of the lithium ion battery is improved; the invention patent with the publication number of CN 107946645A reports a novel flame-retardant overcharge protection additive with a structure of cyclotriphosphazene and p-phenylene diether, an electrolyte using the additive can provide voltage-limiting protection of 4.45-5V, and the electrolyte is flame-retardant or non-combustible, can provide overcharge-prevention and flame-retardant functions for a lithium battery, and does not influence the normal charge and discharge performance of the lithium battery. However, the types of the currently reported additives for simultaneously realizing high-efficiency flame retardance and overcharge protection are few, and most of the additives for flame retardance and overcharge protection are high in addition and can cause irreversible performance damage to the lithium ion battery, so that the research on the novel flame retardance and overcharge protection additive which is more efficient in flame retardance and has small influence on the electrochemical performance is of great significance for improving the safety of the lithium ion battery.
Disclosure of Invention
The invention aims to solve the technical problem of providing a 3, 5-diphosphazene p-phenylene diether additive and a lithium ion battery electrolyte containing the same, wherein the additive has the high-efficiency flame retardant effect of phosphate and phosphazene compounds, and improves the stability of an intermediate product of the phenylene diether additive through a steric hindrance effect, so that a stable overcharge protection effect is exerted at the same time.
The technical scheme of the invention is as follows:
a3, 5-diphosphazene p-phenylene diether additive is characterized in that: the 3, 5-diphosphazene p-phenylene diether additive is 3, 5-tris (trifluoromethyl) phosphonitrile p-xylylene ether or 3, 5-tris (perfluoro-tert-butoxy) phosphonitrile p-phenylenediethoxy methyl ether, the chemical formula of the 3, 5-tris (trifluoromethyl) phosphonitrile p-xylylene ether is shown in a formula (II), and the chemical formula of the 3, 5-tris (perfluoro-tert-butoxy) phosphonitrile p-phenylenediethoxy methyl ether is shown in a formula (III);
Figure GDA0002885662920000031
the lithium ion battery electrolyte containing the 3, 5-diphosphazene p-phenylene diether additive is prepared from the following components in parts by mass: 10-20 parts of lithium salt, 70-85 parts of organic solvent, 3-10 parts of 3, 5-diphosphazene p-phenylene diether additive and 1-10 parts of film-forming additive; the lithium salt is lithium hexafluorophosphate, the organic solvent is ethylene carbonate or diethyl carbonate, and the film forming additive is vinylene carbonate or ethylene sulfate.
The lithium salt is 10-15 parts by mass, the organic solvent is 70-80 parts by mass, the 3, 5-diphosphazene-p-phenylenediether additive is 5-10 parts by mass, and the film-forming additive is 1-5 parts by mass.
The invention has the advantages that:
the existing phosphate and phosphazene compounds have high-efficiency flame retardant effect and are common electrolyte flame retardant additives, and the p-phenylene diether compounds are typical redox shuttle overcharge protection additives, can play a role in discharging overcharge through reversible redox reaction and have small influence on the electrochemical performance of the battery, but can only play the role in overcharge protection in a short time due to the instability of intermediate products. The 3, 5-diphosphazene p-phenylene diether additive not only has the high-efficiency flame retardant effect of phosphate and phosphazene compounds, but also improves the stability of an intermediate product of the p-phenylene diether additive through a steric hindrance effect, thereby simultaneously playing a stable overcharge protection effect and reducing the using amount of a safety additive; the 3, 5-diphosphazene p-phenylene diether additive realizes long-term stable overcharge protection effect through reversible redox, and has little influence on electrochemical performance.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The preparation method of the electrolyte 1 and the experimental battery 1 specifically comprises the following steps:
(1) and preparing a positive plate:
the method comprises the following steps of mixing a silicon-based cathode material (NMC811) serving as a cathode active material, acetylene black serving as a conductive agent and polyvinylidene fluoride serving as a binder according to the following mass ratio NMC 811: acetylene black: mixing polytetrafluoroethylene (95: 2.5: 2.5), adding N-methyl pyrrolidone after mixing, fully stirring and uniformly mixing to form uniform anode slurry, uniformly coating the uniform anode slurry on a 15-micron-thick aluminum foil, and drying to obtain an anode sheet;
(2) preparation of electrolyte 1:
in an argon glove box with the water content controlled to be less than or equal to 10ppm, Ethylene Carbonate (EC) and Ethyl Methyl Carbonate (EMC) are mixed according to the mass ratio of EC to EMC of 3: 7, uniformly mixing to obtain an organic solvent, slowly adding lithium hexafluorophosphate into the organic solvent, adding 3, 5-tri (trifluoromethyl oxy) phosphonitrile-based p-phenyl dimethyl ether and a film forming additive vinylene carbonate after the lithium hexafluorophosphate is completely dissolved, and uniformly stirring to obtain an electrolyte 1, wherein the mass part ratio of the lithium hexafluorophosphate to the organic solvent to the 3, 5-tri (trifluoromethyl oxy) phosphonitrile-based p-phenyl dimethyl ether to the vinylene carbonate is 14:83:2: 1;
(3) preparation of experimental battery 1:
and (2) manufacturing a CR2016 type button cell containing a positive plate in a drying environment with the dew point temperature controlled below-40 ℃, stacking a negative cover, a foam nickel plate, a lithium plate, a diaphragm plate, the positive plate and the positive cover in sequence to ensure that the positive plate and the negative plate are completely separated by the diaphragm, dripping 10 mu L of the electrolyte 1 prepared in the step (2) by using a liquid-transferring gun after the positive plate is placed, and then sealing, forming and grading to obtain the experimental cell 1.
Example 2
An electrolyte 2 and an experimental battery 2 were prepared in the same manner as in example 1, except that 3, 5-tris (trifluoromethyloxy) phosphazenyl p-xylylene ether and a film forming additive vinylene carbonate were added after lithium hexafluorophosphate was completely dissolved during the preparation of the electrolyte, wherein the mass part ratio of lithium hexafluorophosphate, the organic solvent, 3, 5-tris (trifluoromethyloxy) phosphazenyl p-xylylene ether and vinylene carbonate was 14:75:10: 1.
Example 3
An electrolyte 3 and an experimental cell 3 were prepared in the same manner as in example 1, except that 3, 5-tris (perfluoro-tert-butoxy) phosphazenyl-p-phenylenediethoxymethyl ether and ethylene sulfate, which is a film forming additive, were added after lithium hexafluorophosphate was completely dissolved during the preparation of the electrolyte, wherein the mass part ratio of lithium hexafluorophosphate, the organic solvent, 3, 5-tris (perfluoro-tert-butoxy) phosphazenyl-p-phenylenediethoxymethyl ether and ethylene sulfate was 14:75:10: 1.
Comparative example 1
An electrolyte 4 and an experimental battery 4 were prepared in the same manner as in example 1, except that in the electrolyte preparation process, after lithium hexafluorophosphate was completely dissolved, tris (trifluoromethyl) methyl phosphate, p-xylylene ether and a film forming additive, vinylene carbonate were added, wherein the mass part ratio of lithium hexafluorophosphate, an organic solvent, tris (trifluoromethyl) methyl phosphate, p-xylylene ether and vinylene carbonate was 14:83:1:1: 1.
Comparative example 2
An electrolyte 5 and an experimental battery 5 were prepared in the same manner as in example 1, except that tris (trifluoromethyl) phosphate, p-xylylene ether and a film-forming additive vinylene carbonate were added after lithium hexafluorophosphate was completely dissolved during the preparation of the electrolyte, wherein the mass ratio of lithium hexafluorophosphate, the organic solvent, tris (trifluoromethyl) phosphate, p-xylylene ether and vinylene carbonate was 14:75:5:5: 1.
Comparative example 3
An electrolyte 6 and an experimental battery 6 were prepared in the same manner as in example 1, except that in the electrolyte preparation process, after lithium hexafluorophosphate was completely dissolved, linear polytriphosphazene, cyclohexylbenzene and the film forming additive ethylene sulfate were added, wherein the mass part ratio of lithium hexafluorophosphate, the organic solvent, linear polytriphosphazene, cyclohexylbenzene and ethylene sulfate was 14:75:5:5: 1.
The compositions and contents of the electrolytes of examples 1 to 3 and comparative examples 1 to 3 are shown in Table 1.
TABLE 1
Figure GDA0002885662920000061
The electrolyte flame retardant performance and overcharge performance tests of examples 1-3 and comparative examples 1-3 specifically comprise the following steps:
(1) and testing the flame retardance of the electrolyte:
the flame retardancy of the electrolyte samples obtained in examples 1 to 3 and comparative examples 1 to 3 was measured by a self-extinguishing method, which was carried out by mixing the electrolyte samples having a mass m1Soaking a glass cotton ball with the diameter of 0.3cm in the electrolyte of the lithium ion battery to be tested, weighing the mass m of the glass cotton ball after the glass cotton ball is fully wetted2Then placing the glass cotton ball in the iron wire ringIn the method, an ignition device is used for ignition, the time T from ignition to flame extinction is recorded, the self-extinction time T of unit mass of electrolyte is used as a standard for measuring the flame-retardant performance of the electrolyte, and the calculation formula is as follows: t is T/(m)2-m1) The results of each sample measurement were averaged over three measurements.
(2) And overcharge protection detection:
the experimental batteries of examples 1 to 3 and comparative examples 1 to 3 were overcharged to a state of charge (SOC) of 200% at a charge rate of 1C, respectively, and maintained for 1h, followed by 1C discharge to 3.0V, with a charge-discharge voltage interval set to 3.0 to 6.0V, and the test was repeated 3 times, and the voltage-time curve of the experimental battery was recorded, and if the voltage of the experimental battery could not be maintained below 4.8V during the test, the overcharge protection of the experimental battery was considered to have failed, and the positive electrode discharge gram capacity of the experimental battery after three overcharge experiments was recorded.
The electrolyte and experimental cell test results in examples 1-3 and comparative examples 1-3 are shown in table 2 below.
TABLE 2
Figure GDA0002885662920000071
As can be seen from the experimental data of the self-extinguishing time in Table 2, the flame retardant effect of the flame retardant additive used in examples 1-3 is better than that of the flame retardant additive used in comparative examples 1-3, and the electrolyte can be completely non-combustible by 10% of the addition amount; it can be seen from the capacity grading capacity that the conventional phosphate ester or linear polyphosphazene flame retardants in comparative examples 5 and 6 reduce the initial capacity grading capacity of the positive electrode material to 150-161mAh/g, with obvious negative effects, while the 3, 5-diphosphonite has less influence on the capacity of the battery, and the capacity grading capacity is at least 170mAh/g at 10% addition; in addition, although the cyclohexylbenzene in the electrolyte 6 can also enable the battery to pass an overcharge test as an overcharge additive, the overcharge test battery cannot be normally charged and discharged, and the 3, 5-diphosphazene p-phenylene diether additive in the examples 1 to 3 still has a discharge capacity of up to 150mAh/g after the overcharge test, which shows that the additive has a reversible overcharge protection effect and has less influence on the electrochemical performance of the battery under the practical application condition of the lithium ion battery.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (3)

1. A3, 5-diphosphazene p-phenylene diether additive is characterized in that: the 3, 5-diphosphazene p-phenylene diether additive is 3, 5-tris (trifluoromethyl) phosphonitrile p-xylylene ether or 3, 5-tris (perfluoro-tert-butoxy) phosphonitrile p-phenylenediethoxy methyl ether, the chemical formula of the 3, 5-tris (trifluoromethyl) phosphonitrile p-xylylene ether is shown in a formula (II), and the chemical formula of the 3, 5-tris (perfluoro-tert-butoxy) phosphonitrile p-phenylenediethoxy methyl ether is shown in a formula (III);
Figure FDA0002885662910000011
2. the electrolyte of the lithium ion battery containing the 3, 5-diphosphazene p-phenylene diether additive of claim 1, wherein the electrolyte comprises: the adhesive is prepared from the following components in parts by mass: 10-20 parts of lithium salt, 70-85 parts of organic solvent, 3-10 parts of 3, 5-diphosphazene p-phenylene diether additive and 1-10 parts of film-forming additive; the lithium salt is lithium hexafluorophosphate, the organic solvent is ethylene carbonate or diethyl carbonate, and the film forming additive is vinylene carbonate or ethylene sulfate.
3. The lithium ion battery electrolyte of claim 2, wherein: the lithium salt is 10-15 parts by mass, the organic solvent is 70-80 parts by mass, the 3, 5-diphosphazene-p-phenylenediether additive is 5-10 parts by mass, and the film-forming additive is 1-5 parts by mass.
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CN110265702B (en) * 2019-05-28 2022-06-17 合肥国轩高科动力能源有限公司 Flame-retardant and overcharge-proof electrolyte additive and electrolyte containing additive
CN113121602B (en) * 2019-12-30 2023-03-24 北京卫蓝新能源科技有限公司 Phosphonitrile phosphate ester additive, preparation method and lithium battery electrolyte
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