CN115441053A - Electrolyte containing multi-heterocyclic organic phosphorus compound and lithium ion battery - Google Patents
Electrolyte containing multi-heterocyclic organic phosphorus compound and lithium ion battery Download PDFInfo
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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
- 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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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Abstract
The invention discloses an electrolyte containing a multi-heterocyclic organic phosphorus compound, which comprises a main lithium salt and a non-aqueous solvent, and further comprises: a first additive which is a polyheterocyclic organophosphorus compound represented by the following formula (I):
Description
Technical Field
The invention relates to the field of lithium ion battery electrolyte, in particular to electrolyte containing a multi-heterocyclic organic phosphorus compound and a lithium ion battery.
Background
The lithium ion battery has the characteristics of high energy density, long cycle life, good safety performance, environmental friendliness and the like, and is widely applied to the fields of smart phones, notebook computers, unmanned aerial vehicles, electric automobiles and the like.
In order to meet the requirements of people on the service life and the endurance mileage of electric automobiles, the development of lithium ion batteries with high energy density and long cycle life is a key research direction in recent years. For ternary materials, increasing the upper charging limit voltage of the battery and increasing the content of nickel in the ternary materials are more common means for increasing the energy density of the battery, but along with the increase of the upper charging limit voltage and the content of nickel, the instability of the materials is aggravated, and various problems are brought, for example, irreversible phase change occurs in the positive electrode material, dissolution of transition metals is aggravated, decomposition of electrolyte into gas and the like, so that the comprehensive performance of the lithium ion battery is seriously influenced.
At present, the development of novel electrolyte additives or the inhibition of the internal side reaction of the battery and the optimization of an electrode interface film through the synergistic action of different additive compositions is one of the main approaches for improving the performance of the lithium ion battery.
Disclosure of Invention
In order to solve the technical problems, the invention provides an electrolyte capable of improving the high-temperature cycle performance and the high-temperature storage performance of a lithium ion battery under high voltage.
The purpose of the invention is realized by the following technical scheme:
an electrolyte containing a polyheterocyclic organophosphorus compound, comprising a main lithium salt, a nonaqueous solvent, and further comprising:
a first additive which is a polyheterocyclic organophosphorus compound represented by the following formula (I):
in the formula, G 1 、G 2 、G 3 Independently selected from furan, thiophene, pyridine, pyrazine, pyridazine or s-triazine ring; xn represents G 1 、G 2 、G 3 Is independently substituted on the ring by n X substituents, wherein X is selected from hydrogen, halogen, cyano, sulfonyloxy, sulfonyl, C 1-12 Alkyl radical, C 1-12 Alkoxy radical, C 2-12 Ester group, C 2-12 Alkenyl radical, C 6-16 Aryl radical, C 6-16 Aryloxy, and C substituted by halogen, sulfonyloxy or sulfonyl 1-12 Alkyl radical, C 1-12 Alkoxy radical, C 2-12 Ester group, C 2-12 Alkenyl radical, C 6-16 Aryl or C 6-16 An aryloxy group; n is an integer of 1 to 4; the X substituents on the same ring may be the same or different, and the X substituents on different rings may be the same or different;
a second additive which is a boron trifluoride complex.
Preferably, in the formula, X is selected from hydrogen, halogen, cyano, sulfonyloxy, sulfonyl, C 1-6 Alkyl radical, C 1-6 Alkoxy radical, C 2-6 Ester group, C 2-6 An alkenyl group; n is an integer of 2 to 4.
More preferably, X is selected from hydrogen, methyl, fluorine.
Most preferably, the first additive is selected from at least one of the following structures:
further, the boron trifluoride complex is at least one selected from the group consisting of boron trifluoride carbonate complexes, boron trifluoride carboxylate complexes, boron trifluoride ether complexes, boron trifluoride nitrogen heterocyclic complexes, and boron trifluoride sulfone complexes. Wherein the boron trifluoride carbonate complex comprises a boron trifluoride chain carbonate complex and a boron trifluoride cyclic carbonate complex; the boron trifluoride nitrogen heterocyclic complexes comprise boron trifluoride pyridine complexes and boron trifluoride pyrrole complexes.
Preferably, the boron trifluoride complex is selected from at least one of the following structures:
when the first additive and the second additive exist in an electrolyte system at the same time, boron trifluoride can react with heterocycles in a multi-heterocycle organophosphorus compound, and a small amount of polymer is supposed to be generated in the system under high temperature to cover the surface of an electrode, so that the isolation effect of the electrode on the electrolyte is improved, and the decomposition reaction of the electrolyte on the electrode is inhibited; meanwhile, the polyheterocyclic organophosphorus compound serving as a common organic ligand can be complexed with transition metal at high temperature to form a complex, so that metal ions are inhibited from depositing on the surface of the electrode; the two functions jointly improve the high-temperature performance of the lithium ion battery.
Generally, the first additive and the second additive are present at the same time to exert a synergistic effect, but the synergistic effect is different depending on the amounts of the first additive and the second additive. Preferably, the first additive accounts for 0.1-5.0% of the total mass of the electrolyte, and the second additive accounts for 0.3-10.0% of the total mass of the electrolyte. More preferably, the first additive accounts for 0.3-3.0% of the total mass of the electrolyte, and the second additive accounts for 0.5-4.0% of the total mass of the electrolyte.
In the electrolyte of the present invention, the main lithium salt is selected from the common lithium salts in the electrolyte. Preferably, the main lithium salt is at least one selected from lithium hexafluorophosphate, lithium hexafluoroarsenate, lithium perchlorate, lithium tetrafluoroborate, lithium tetrafluorooxalate phosphate, lithium bistrifluoromethanesulfonate, lithium bisfluorosulfonylimide, lithium bisoxalato borate and lithium difluorooxalato borate, preferably at least one selected from lithium hexafluorophosphate and lithium difluorosulfonylimide, and the main lithium salt accounts for 7.0-20.0% by mass of the electrolyte. Preferably, the main lithium salt is at least one selected from lithium hexafluorophosphate and lithium bis-fluorosulfonyl imide, and accounts for 10.0-15.0% of the electrolyte by mass.
In the electrolyte of the present invention, the nonaqueous solvent may be a solvent commonly used in the electrolyte. Preferably, the nonaqueous solvent is at least one selected from the group consisting of ethylene carbonate, propylene carbonate, 1, 2-butylene carbonate, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, dipropyl carbonate, propyl methyl carbonate, propyl ethyl carbonate, vinylene carbonate, fluoroethylene carbonate, 1, 4-butyrolactone, methyl propionate, methyl butyrate, ethyl acetate, ethyl propionate, propyl propionate and ethyl butyrate.
In the electrolyte, in order to further improve the comprehensive performance of the electrolyte, the electrolyte further comprises a third additive, wherein the third additive is at least one selected from vinylene carbonate, fluoroethylene carbonate, vinyl ethylene carbonate, vinyl sulfate, methylene methanedisulfonate, 1, 3-propane sultone, 1, 3-propene sultone, tris (trimethylsilyl) phosphite and lithium difluorophosphate, and the third additive accounts for 0.5-5.0% of the total mass of the electrolyte. More preferably, the third additive accounts for 0.8-3.0% of the total mass of the electrolyte.
The invention also provides a lithium ion battery which comprises a positive plate, a negative plate, a diaphragm arranged between the positive plate and the negative plate at intervals, and any one of the electrolyte.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, through the synergistic effect of the multi-heterocyclic organic phosphorus compound and the boron trifluoride complex, the side reaction in the battery can be inhibited under the condition of high voltage and high temperature, the dissolution of transition metal is reduced, and the high-temperature cycle performance and the high-temperature storage performance of the lithium ion battery are further improved.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the invention to these embodiments. It will be appreciated by those skilled in the art that the present invention encompasses all alternatives, modifications and equivalents as may be included within the scope of the claims.
1. Electrolyte preparation
Example 1
This example provides an electrolyte containing a polyheterocyclic organophosphorus compound, which is prepared by the steps of:
s1, uniformly mixing Ethylene Carbonate (EC) and Ethyl Methyl Carbonate (EMC) in a glove box filled with argon according to a mass ratio of 3;
s2, drying LiPF 6 LiPF dissolved in a non-aqueous solvent to 12.4% 6 The solution is used as a basic electrolyte;
s3. Adding 0.5% by weight of I-1, 1.0% by weight of II-1 and 1.0% by weight of Vinylene Carbonate (VC) to the above-mentioned base electrolyte to obtain the electrolyte of the present example.
Example 2
The operation of this example is the same as example 1 except that: in the step S3, 0.5% by weight of I-1, 1.0% by weight of II-4, and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 3
The operation of this example is the same as example 1 except that: in the S3 step, 0.5% wt of I-1, 1.0% wt of II-5 and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte, resulting in the electrolyte of the present example.
Example 4
The operation of this example is the same as example 1 except that: in the S3 step, 0.1% by weight of I-1, 1.0% by weight of II-1 and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte, to obtain the electrolyte of the present example.
Example 5
The operation of this example is the same as example 1 except that: in the step S3, 2.0% by weight of I-1, 1.0% by weight of II-1, and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 6
The operation of this example is the same as example 1 except that: in the step S3, 4.0% by weight of I-1, 1.0% by weight of II-1, and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 7
The operation of this example is the same as example 1 except that: in the S3 step, 0.5% wt of I-2, 1.0% wt of II-1 and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte, resulting in the electrolyte of the present example.
Example 8
The operation of this example is the same as example 1 except that: in the step S3, 0.5% by weight of I-2, 1.0% by weight of II-4, and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 9
The operation of this example is the same as example 1 except that: in the S3 step, 0.5% wt of I-2, 1.0% wt of II-5 and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte, resulting in the electrolyte of the present example.
Example 10
The operation of this example is the same as example 1 except that: in the S3 step, 0.5% wt of I-1, 0.3% wt of II-1, and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 11
The operation of this example is the same as example 1 except that: in the step S3, 0.5% wt of I-1, 4.0% wt of II-1, and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Example 12
The operation of this example is the same as example 1 except that: in the step S3, 0.5% wt of I-1, 8.0% wt of II-1, and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present example.
Comparative example 1
The comparative example was conducted as in example 1 except that: in the S3 step, 1.0% by weight of Vinylene Carbonate (VC) was added to the base electrolyte to obtain an electrolyte of the present comparative example.
Comparative example 2
The comparative example was conducted as in example 1 except that: in the S3 step, 0.5% by weight of I-1 and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain an electrolyte of the present comparative example.
Comparative example 3
The comparative example was conducted as in example 1 except that: in the S3 step, 0.5% by weight of I-2 and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain an electrolyte of the present comparative example.
Comparative example 4
The comparative example was conducted as in example 1 except that: in the S3 step, 1.0% by weight of II-1 and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain an electrolyte of the present comparative example.
Comparative example 5
The comparative example was conducted as in example 1 except that: in the S3 step, 1.0% wt of II-4 and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte, resulting in the electrolyte of the present comparative example.
Comparative example 6
The comparative example was conducted as in example 1 except that: in the S3 step, 1.0% wt of II-5 and 1.0% wt of Vinylene Carbonate (VC) were added to the base electrolyte, resulting in the electrolyte of the present comparative example.
Comparative example 7
The comparative example was conducted as in example 1 except that: in the S3 step, 0.5% by weight of I-1, 1.0% by weight of pyridine and 1.0% by weight of Vinylene Carbonate (VC) were added to the base electrolyte to obtain the electrolyte of the present comparative example.
2. Battery fabrication and performance testing
The electrolytes prepared in the above examples and comparative examples were injected into lithium ion batteries, respectively, and performance tests were performed. The lithium ion battery comprises a positive pole piece, a negative pole piece, a diaphragm, electrolyte and battery auxiliary materials, wherein the positive active material is LiNi 0.73 Co 0.07 Mn 0.2O2 The negative active material is graphite. The preparation process of the battery is as follows:
preparing a lithium nickel manganese cobalt ternary material from a positive active material nickel cobalt lithium manganate ternary material, a conductive agent and a binder polyvinylidene fluoride according to the weight ratio: conductive agent: polyvinylidene fluoride =97.3:1.5:1.2, mixing, adding solvent N-methyl pyrrolidone, and fully stirring and mixing to form uniform anode slurry; and coating the slurry on an aluminum foil of the positive current collector, drying, rolling, slitting and die cutting to obtain the positive plate.
The negative active material graphite, the conductive agent, the binder styrene butadiene rubber and the thickener sodium carboxymethyl cellulose are mixed according to the weight ratio of graphite: conductive agent: styrene-butadiene rubber: sodium carboxymethylcellulose =96.4:0.6:1.8: 1.2, mixing, adding deionized water, and fully stirring to obtain uniform cathode slurry; and coating the slurry on a copper foil of a negative current collector, drying, rolling, slitting and die cutting to obtain a negative plate.
The negative pole piece, the diaphragm and the positive pole piece are sequentially stacked according to a rule, the diaphragm is placed between the positive pole and the negative pole to play an isolation role, a bare cell is obtained through one layer of lamination, the electrolyte is injected into the bare cell after the bare cell is assembled and baked, and then the battery is obtained through the procedures of infiltration, formation, packaging, capacity grading and the like.
The performance test method adopted is as follows:
(1) And (3) testing the high-temperature cycle performance at 45 ℃: charging the batteries after capacity grading to 4.35V at constant current and constant voltage of 1C in a constant temperature box at 45 ℃, stopping current at 0.05C, standing for 10min, and discharging to 2.8V at 1C; calculating the capacity retention rate after 500 th circulation according to the process steps after 500 cycles:
the 500 th cycle capacity retention ratio (%) = (500 th cycle discharge capacity/first cycle discharge capacity) × 100%.
(2) Volume expansion rate test of 30 days of high-temperature storage at 60 ℃: discharging the battery at 0.5 deg.C to 2.8V at constant current in 25 deg.C, standing for 10min, and then charging at 1C to 4.35V at constant current and constant voltage, and cutting off current at 0.05C. Standing at room temperature for 5h, and measuring initial volume V of the lithium ion battery by using a drainage method 1 . Storing in 60 deg.C environment for 30 days, and measuring the volume V of the lithium ion battery after high-temperature storage by drainage method 2 。
Volume change rate (%) after high-temperature storage of lithium ion battery (volume V after high-temperature storage of lithium ion battery) 2 Volume V of lithium-ion batteries before high-temperature storage 1 ) Volume V of lithium ion battery before high-temperature storage 1 ×
100％。
The results of the performance tests are shown in table 1 below:
TABLE 1 Performance test results
From the test results of examples 1 and 4 to 6 in table 1 above, it can be seen that when the addition amount of the polyheterocyclic organic phosphorus compound is too large or too small, the high-temperature cycle performance of the battery is deteriorated, which may be caused by too large system impedance due to the addition amount of the polyheterocyclic organic phosphorus compound, and insufficient film formation on the surface of the electrode sheet due to too small addition amount of the polyheterocyclic organic phosphorus compound, and thus, the battery performance is best when the addition amount of the polyheterocyclic organic phosphorus compound is about 0.5%. According to the test results of the embodiment 1 and the embodiments 10 to 12, when the content of the boron trifluoride complex compound is too high, the gas generation of the system is serious, and when the content is too low, the film cannot be formed on the electrode interface well, and the high-temperature cycle performance of the battery cannot be improved well. Therefore, the battery performance was best when the amount of boron trifluoride complex added was about 1.0%.
According to the results of the electrical properties test in table 1 above, the polyheterocyclic organophosphorus compound can effectively suppress the gas generation during storage of the battery at 60 ℃, whereas the boron trifluoride complex has an insignificant effect of suppressing the gas generation, and even there is a case of deterioration (comparative example 5). When the multi-heterocyclic organic phosphorus compound and the boron trifluoride complex are used independently, the cycle performance of the battery at 45 ℃ can be improved, but the effect is not obviously improved. When the two are used together, the high-temperature storage gas generation can be effectively inhibited, and the cycle performance of the battery at 45 ℃ is greatly improved. The results of electrical property tests according to example 3, comparative example 1, comparative example 2 and comparative example 7 show that the effect of enhancing the high temperature performance when a polyheterocyclic organophosphorus compound is combined with pyridine is inferior to that of combining the polyheterocyclic organophosphorus compound with boron trifluoride pyridine complex, indicating that boron trifluoride is a part of boron trifluoride pyridine complex which mainly functions.
Claims (12)
1. An electrolyte containing a multi-heterocyclic organic phosphorus compound, which comprises a main lithium salt and a non-aqueous solvent, and is characterized in that: the electrolyte further comprises:
a first additive which is a polyheterocyclic organophosphorus compound represented by the following formula (I):
in the formula, G 1 、G 2 、G 3 Independently selected from furan, thiophene, pyridine, pyrazine, pyridazine or s-triazine ring; xn represents G 1 、G 2 、G 3 Is independently substituted on the ring by n X, wherein X is selected from hydrogen, halogen, cyano, sulfonyloxy, sulfonyl, C 1-12 Alkyl radical, C 1-12 Alkoxy radical, C 2-12 Ester group, C 2-12 Alkenyl radical, C 6-16 Aryl radical, C 6-16 Aryloxy, and C substituted by halogen, sulfonyloxy or sulfonyl 1-12 Alkyl radical, C 1-12 Alkoxy radical, C 2-12 Ester group, C 2-12 Alkenyl radical, C 6-16 Aryl or C 6-16 An aryloxy group; n is an integer of 1 to 4;
a second additive that is a boron trifluoride complex.
2. The electrolyte containing a polyheterocyclic organophosphorus compound according to claim 1, wherein: x is selected from hydrogen, halogen, cyano, sulfonyloxy, sulfonyl, C 1-6 Alkyl radical, C 1-6 Alkoxy radical, C 2-6 Ester group, C 2-6 An alkenyl group; n is an integer of 2 to 4.
3. The electrolyte containing a polyheterocyclic organophosphorus compound according to claim 2, wherein: x is selected from hydrogen, methyl and fluorine.
4. The electrolyte containing a polyheterocyclic organophosphorus compound according to claim 3, wherein: the first additive is selected from at least one of the following structures:
5. the electrolyte containing a polyheterocyclic organophosphorus compound according to claim 1, wherein: the boron trifluoride complex is selected from at least one of boron trifluoride carbonate complex, boron trifluoride carboxylate complex, boron trifluoride ether complex, boron trifluoride nitrogen heterocyclic complex and boron trifluoride sulfone complex.
6. The electrolyte containing a polyheterocyclic organophosphorus compound according to claim 5, wherein: the boron trifluoride carbonate complex comprises a boron trifluoride chain carbonate complex and a boron trifluoride cyclic carbonate complex; the boron trifluoride nitrogen heterocyclic complexes comprise boron trifluoride pyridine complexes and boron trifluoride pyrrole complexes.
7. The electrolyte containing a polyheterocyclic organophosphorus compound according to claim 6, wherein: the boron trifluoride complex is selected from at least one of the following structures:
8. the electrolyte containing a polyheterocyclic organophosphorus compound according to any one of claims 1 to 7, wherein: the first additive accounts for 0.1-5.0%, preferably 0.3-3.0% of the total mass of the electrolyte; the second additive accounts for 0.3-10.0%, preferably 0.5-4.0% of the total mass of the electrolyte.
9. The electrolyte containing a polyheterocyclic organophosphorus compound according to any one of claims 1 to 8, wherein: the main lithium salt is selected from at least one of lithium hexafluorophosphate, lithium hexafluoroarsenate, lithium perchlorate, lithium tetrafluoroborate, lithium tetrafluoro oxalate phosphate, lithium bistrifluoromethanesulfonate, lithium bifluorosulfonate, lithium bisoxalato borate and lithium difluorooxalato borate, and preferably at least one of lithium hexafluorophosphate and lithium bifluorosulfonate; and the main lithium salt accounts for 7.0-20.0% of the electrolyte by mass.
10. The electrolyte containing a polyheterocyclic organophosphorus compound according to any one of claims 1 to 8, wherein: the non-aqueous solvent is at least one selected from ethylene carbonate, propylene carbonate, 1, 2-butylene carbonate, dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, dipropyl carbonate, methyl propyl carbonate, ethyl propyl carbonate, 1, 4-butyrolactone, methyl propionate, methyl butyrate, ethyl acetate, ethyl propionate, propyl propionate and ethyl butyrate.
11. The electrolyte containing a polyheterocyclic organophosphorus compound according to any one of claims 1 to 10, wherein: the electrolyte also comprises a third additive, and the third additive is selected from at least one of vinylene carbonate, fluoroethylene carbonate, vinyl ethylene carbonate, vinyl sulfate, methylene methanedisulfonate, 1, 3-propane sultone, 1, 3-propene sultone, tris (trimethyl silane) phosphite and lithium difluorophosphate.
12. The utility model provides a lithium ion battery, includes positive plate, negative pole piece, interval and sets up the diaphragm between positive plate and negative pole piece, its characterized in that: the lithium ion battery further comprising the electrolyte of any of claims 1-11.
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