CN111244547B - Electrolyte containing aromatic oxime additive and preparation method and application thereof - Google Patents

Electrolyte containing aromatic oxime additive and preparation method and application thereof Download PDF

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CN111244547B
CN111244547B CN202010070496.5A CN202010070496A CN111244547B CN 111244547 B CN111244547 B CN 111244547B CN 202010070496 A CN202010070496 A CN 202010070496A CN 111244547 B CN111244547 B CN 111244547B
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electrolyte
aromatic oxime
lithium
additive
oxime
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CN111244547A (en
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高剑
辜琴
冯有增
王铭
谭铁宁
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Sichuan Hongwei 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
    • 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
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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    • Y02E60/10—Energy storage using batteries

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Abstract

The invention discloses an electrolyte containing aromatic oxime additives and a preparation method and application thereof, wherein the aromatic oxime additives are aromatic oxime organic compounds and derivatives thereof, and have benzene rings and-C ═ N-OH functional groups; or having a benzene ring and
Figure DDA0002377173480000011
a functional group. The preparation method comprises the following steps: dissolving lithium salt in a solvent to prepare a solution with the concentration of 0.5-2mol/L as a basic electrolyte; adding 0.1-5 wt% of aromatic oxime organic compound and derivatives thereof serving as additives into the basic electrolyte, and uniformly mixing to obtain the electrolyte. The electrolyte is used as an electrolyte of a lithium ion battery. According to the invention, the aromatic oxime additive is added into the electrolyte of the battery, so that the stability of the SEI film is effectively improved, and the rate capability and the high-temperature storage performance of the battery are obviously improved.

Description

Electrolyte containing aromatic oxime additive and preparation method and application thereof
Technical Field
The invention relates to the technical field of lithium ion batteries, in particular to application of aromatic oximes and derivatives thereof in preparation of electrolyte of a lithium ion battery.
Background
The lithium ion battery has the advantages of high energy density, high voltage, safety, environmental protection and the like, and is commonly used in equipment such as electric automobiles, notebooks, mobile phones and the like. The lithium ion battery mainly comprises an anode, a cathode, a diaphragm, electrolyte and the like, wherein the anode mainly uses commercial lithium cobaltate, lithium iron phosphate and a ternary high-voltage material, the cathode mainly uses layered graphite, and a common system of the electrolyte is 1mol/L LiPF6Dissolving in organic solvent such as EC and EMC.
Currently, lithium batteries are widely used, but have limited applications in extreme environments and under conditions of high voltage and the like. This is because the electrolyte of a lithium battery is easily decomposed in a high temperature environment as follows:
LiPF6→PF5+LiF
Li2CO3+PF5→POF3+2LiF+CO2
ROCO2Li+PF5→RF+LiF+CO2+POF3
RCO2Li+PF5→RCOF+LiF+POF3
wherein the lithium salt in the electrolyte is easily decomposed to generate PF5And reacts with components in the SEI film on the surface of the electrode to destroy the stability of the SEI film, thereby corroding electrode materials and influencing the performance of the battery. The process is accompanied with a large amount of gas generation, causing the volume expansion of the battery, and easily causing safety accidents. To solve such problems, the simplest and most effective way of doing so is to modify the electrolyte composition, adding electrolyte additives to the electrolyte. Generally, the content of the additive is not more than 5%, but the battery performance can be greatly improved.
Currently, various additives have been extensively studied, among which film-forming additives, which are the most widely studied and can promote the formation of a stable interface (SEI film) inside a battery, vinylene carbonate, fluoroethylene carbonate, and the like have become commercial additives. However, the study of aromatic oxime additives is almost none. The aromatic oxime organic compound has lower reduction potential and lower LUMO orbital, and can be decomposed before a solvent to form a more stable interface.
Disclosure of Invention
In order to solve the problems, the invention starts from the direction of the lithium ion battery electrolyte, reduces the internal resistance of the whole battery, reduces the volume expansion of the battery and improves the high-temperature storage performance and the rate capability of the battery by adjusting the components of the electrolyte.
In order to achieve the above purpose, the invention provides a lithium ion battery electrolyte, which adopts the following technical scheme:
the electrolyte containing aromatic oxime additive includes aromatic oxime organic compound and its derivative.
More specifically, the aromatic oxime organic compound is an oxime organic compound with a benzene ring and a-C ═ N-OH functional group; or the aromatic oxime organic compound has benzene ring and
Figure GDA0003001955880000021
functional oxime organic compounds.
Further, the aromatic oxime organic compound can be selected from the following structures:
Figure GDA0003001955880000022
or
Figure GDA0003001955880000023
Or
Figure GDA0003001955880000024
Wherein R' is a hydrocarbon group or a carbonyl group having one or more carbon atoms;
r' is a hydrocarbon group of one or more carbon atoms, a hydrogen atom, a halogen atom or an amino group;
R1-R5 are hydrogen atoms, alkyl with 1-10 carbon atoms, halogen atoms, hydroxyl, methoxyl or benzene rings.
The electrolyte containing the aromatic oxime additive also comprises lithium salt, solvent and other components, wherein the lithium salt in the electrolyte comprises at least one of lithium hexafluorophosphate, lithium bistrifluoromethanesulfonylimide, lithium perchlorate and lithium bisoxalateborate.
The solvent in the electrolyte solution includes at least one of cyclic carbonates (PC, EC), chain carbonates (DEC, DMC, EMC), and carboxylates (MF, MA, EA, MA, MP, etc.). These solvents are common solvents for lithium ion battery electrolytes, and when a mixed solvent is used, it is possible to mix and formulate the respective solvents in a volume ratio of 1.
The concentration of solute lithium salt in the electrolyte is 0.5-2 mol/L.
Preferably, the amount of the aromatic oxime organic compound in the electrolyte is 0.1wt% to 5 wt%.
The invention also provides a preparation method of the electrolyte containing the aromatic oxime additive, which mainly comprises the following steps:
(1) dissolving lithium salt in a solvent to prepare a solution with the concentration of 0.5-2mol/L as a basic electrolyte;
(2) adding 0.1-5 wt% of aromatic oxime organic compound and derivatives thereof serving as additives into the basic electrolyte, and uniformly stirring and mixing by magnetic force to prepare the electrolyte containing the aromatic oxime additives. Generally, the electrolyte containing the aromatic oxime additive can be obtained by stirring for 5 hours by adopting a magnetic stirrer.
The application of the electrolyte containing the aromatic oxime additive is mainly used as the electrolyte of a lithium ion battery, but not limited to the electrolyte.
Compared with the prior art, the invention has at least the following beneficial effects:
according to the invention, the aromatic oxime additive is added into the electrolyte of the battery, so that the stability of the SEI film is effectively improved, and the rate capability and the high-temperature storage performance of the battery are obviously improved.
Drawings
FIG. 1 is a graph showing the comparison of the performance rate of the aromatic oxime additives in examples 1 to 10 when the amount of the aromatic oxime additives is 0.5 wt%.
FIG. 2 is a graph showing the comparison of the high temperature storage performance of examples 1 to 10 in which the amount of the aromatic oxime additive added was 0.5 wt%.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In order to improve the high-temperature safety and the rate performance of the battery, the patent discloses a preparation method of electrolyte of an electrolyte additive. The specific process is that one or more electrolyte additives are added into basic electrolyte, after being stirred uniformly, new electrolyte is prepared, the assembly of the full battery is carried out, and then the battery test is carried out.
Example 1 blank control
Preparing EC and DEC into a mixed solvent in a volume ratio of 1:1, adding lithium hexafluorophosphate into the mixed solvent, and preparing into 1mol/L LiPF6The lithium ion battery electrolyte.
The lithium ion battery electrolyte is used as a base electrolyte, and is used as a blank control sample without adding any additive.
The adopted anode active material is a ternary anode LiNi0.5Co0.2Mn0.3O2And the negative electrode is graphite. Wherein, the current collector of the anode material is aluminum foil, and the anode plate adopts 92 wt% LiNi0.5Co0.2Mn0.3 O 24 wt% of acetylene black and 4 wt% of binder PVDF; the current collector of the negative electrode material is copper foil, and the negative electrode is composed of 92 wt% of graphite, 4 wt% of acetylene black and 4 wt% of binder PVDF; the separator used was a PP separator.
And assembling the anode, the cathode, the diaphragm and the lithium ion battery electrolyte into the button type lithium ion battery. Wherein, a part of batteries are subjected to rate test by blue light test equipment, and are respectively cycled for 5 times under 0.1C/0.5C/1C/2C/3C/5C to obtain the rate performance of the batteries, as shown in figure 1. In addition, a part of the batteries was electrochemically tested by a blue test apparatus, the batteries were charged to 3.90V at 0.1C, and then the batteries were placed in an oven for high-temperature storage at 60℃, and the voltage of the batteries was periodically tested, thereby obtaining high-temperature storage performance of the batteries, as shown in fig. 2.
Example 2
0.5 wt%, 1wt%, 3 wt%, 5wt% of salicylhydroxamic acid was added to the base electrolyte described in example 1 to obtain a liquid, the specific structural formula of salicylhydroxamic acid being as follows:
Figure GDA0003001955880000051
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 3:
0.5 wt%, 1wt%, 3 wt%, 5wt% of α -benzaldoxime was added to the base electrolyte described in example 1 to obtain a liquid, the specific structural formula of α -benzaldoxime is shown below:
Figure GDA0003001955880000052
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 4:
0.5 wt%, 1wt%, 3 wt%, 5wt% of 4-pyridylamidoxime was added to the base electrolyte solution described in example 1 to obtain a liquid, the specific structural formula of 4-pyridylamidoxime being as follows:
Figure GDA0003001955880000061
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 5:
0.5 wt%, 1wt%, 3 wt%, 5wt% of pyridine-2-carbaldehyde oxime was added to the base electrolyte described in example 1 to obtain a liquid, and the specific structural formula of pyridine-2-carbaldehyde oxime is as follows:
Figure GDA0003001955880000062
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 6:
0.5 wt%, 1wt%, 3 wt%, 5wt% of benzohydroxamic acid was added to the base electrolyte described in example 1 to obtain a liquid, the specific structural formula of the benzohydroxamic acid being as follows:
Figure GDA0003001955880000063
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 7:
0.5 wt%, 1wt%, 3 wt%, 5wt% of 4-methylbenzamide oxime was added to the base electrolyte solution described in example 1 to obtain a liquid, and the specific structural formula of 4-methylbenzamide oxime is as follows:
Figure GDA0003001955880000071
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 8:
to the base electrolyte solution described in example 1, 0.5 wt%, 1wt%, 3 wt%, 5wt% of 2, 4-dimethoxybenzaldehyde oxime was added to obtain a liquid, and the specific structural formula of 2, 4-dimethoxybenzaldehyde oxime is as follows:
Figure GDA0003001955880000072
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 9:
0.5 wt%, 1wt%, 3 wt%, 5wt% of 1-phenyl-1, 2-propanedione oxime was added to the base electrolyte described in example 1 to obtain a liquid, and the specific structural formula of 1-phenyl-1, 2-propanedione oxime was as follows:
Figure GDA0003001955880000073
the above liquids were uniformly mixed by stirring in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate performance and high-temperature storage performance of the battery were as shown in fig. 1 and 2.
Example 10:
1wt% of VC additive and 1wt% of PS additive were added to the base electrolyte solution described in example 1, and 0.5 wt%, 1wt%, 3 wt%, and 5wt% of salicylhydroxamic acid was added to the base electrolyte solution, and the resulting solutions were uniformly mixed in a glove box for 5 hours, and then assembled and tested as in example 1, and the rate capability and high-temperature storage property of the battery were shown in FIGS. 1 and 2.
From fig. 1 and 2, it can be seen that the rate performance and high-temperature storage performance of the battery are improved obviously after the oxime additive is added. The lithium ion electrolyte prepared by taking aromatic oximes as additives can effectively improve the stability of the SEI film and improve the performance of the battery.
Although the invention has been described herein with reference to illustrative embodiments thereof, it should be understood that numerous other modifications and embodiments can be devised by those skilled in the art that will fall within the spirit and scope of the principles of this disclosure.

Claims (6)

1. The lithium ion battery electrolyte containing the aromatic oxime additive is characterized in that the additive of the electrolyte comprises an aromatic oxime derivative, and the aromatic oxime derivative has the following structure:
Figure DEST_PATH_IMAGE001
R1-R4 are hydrogen atoms, halogen atoms, hydroxyl groups or methoxy groups.
2. The electrolyte for lithium ion batteries containing aromatic oxime additives according to claim 1, wherein the lithium salt in the electrolyte comprises at least one of lithium hexafluorophosphate, lithium bistrifluoromethanesulfonylimide, lithium perchlorate and lithium bisoxalatoborate.
3. The electrolyte for lithium ion batteries containing aromatic oxime additives according to claim 1, wherein the solvent in the electrolyte comprises at least one of cyclic carbonates, chain carbonates, and carboxylates.
4. The electrolyte for lithium ion batteries containing aromatic oxime additives as claimed in claim 1, wherein the concentration of solute lithium salt in the electrolyte is 0.5-2 mol/L.
5. The electrolyte for lithium ion batteries containing aromatic oxime additives according to claim 1, wherein the amount of aromatic oxime derivatives in the electrolyte is 0.1wt% to 5 wt%.
6. The method of preparing the electrolyte for lithium ion batteries containing an aromatic oxime additive according to any one of claims 1 to 3, comprising the steps of:
(1) dissolving lithium salt in a solvent to prepare a solution with the concentration of 0.5-2mol/L as a basic electrolyte;
(2) adding 0.1-5 wt% of aromatic oxime derivative as an additive into the basic electrolyte, and uniformly stirring and mixing by magnetic force to prepare the electrolyte containing the aromatic oxime additive.
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