PHOSPHAZENE DERIVATIVE, COMPOSITION, AND AN ELECTROCHEMICAL DEVICE COMPRISING THE SAME

20240347783 ยท 2024-10-17

    Inventors

    Cpc classification

    International classification

    Abstract

    The present disclosure provides a phosphazene derivative, a composition for an electrochemical device and an electrochemical device containing the composition The composition includes an electrolyte, a non-aqueous solvent and an additive. The additive includes a phosphazene derivative of the formula (I), n, R.sub.1 and R.sub.2 are as defined herein:

    ##STR00001##

    The safety characteristics of the electrochemical device provided in the present disclosure are improved by adding the aforementioned additives to the composition in the electrochemical device.

    Claims

    1. A phosphazene derivative having a structure of Formula (I): ##STR00022## wherein n is an integer of 3 to 6, R.sub.1 and R.sub.2 are independently selected from a group represented by Formula (I-1) or Formula (I-2), ##STR00023## wherein A is R.sub.3OR.sub.4, R.sub.3CH.sub.3-m(OR.sub.4).sub.m, CH.sub.3-m(OR.sub.4).sub.m or ##STR00024## wherein R.sub.3 is unsubstituted C.sub.1-C.sub.8 alkylene or C.sub.1-C.sub.8 alkylene substituted with C.sub.1-C.sub.8 alkyl, R.sub.3is C.sub.1-C.sub.8 alkyl, R.sub.5 is C.sub.1-C.sub.3 alkyl, R.sub.6 is C.sub.1-C.sub.3 alkylene, R.sub.7 is C.sub.1-C.sub.3 alkyl, x is 1 or 2, m is 2 or 3, p is a number of the A bonded to a carbon in a benzene ring to which the A is attached, and p is an integer of 0 to 3; B is C.sub.1-C.sub.8 alkoxy or C.sub.1-C.sub.8 alkyl, and q is an integer of 0 to 3; and 0<p+q?5.

    2. The phosphazene derivative of claim 1, wherein R.sub.1 and R.sub.2 are groups represented by Formula (I-1), A is R.sub.3OR.sub.4, R.sub.3 is C.sub.1-C.sub.8 alkylene, R.sub.4 is C.sub.1-C.sub.8 alkyl, and p is 0 or 1; B is C.sub.1-C.sub.8 alkoxy, and q is 0 or 1; and 0<p+q?2.

    3. The phosphazene derivative of claim 2, which is one selected from the group consisting of compounds (1-1) to (1-4) below: ##STR00025## ##STR00026##

    4. A composition for an electrochemical device, comprising an electrolyte, a non-aqueous solvent and an additive, wherein the additive comprises the phosphazene derivative according to claim 1.

    5. The composition of claim 4, wherein R.sub.1 and R.sub.2 are groups represented by Formula (1-1), A is R.sub.3OR.sub.4, R.sub.3 is C.sub.1-C.sub.8 alkylene, R.sub.4 is C.sub.1-C.sub.8 alkyl, and p is 0 or 1; B is C.sub.1-C.sub.8 alkoxy, and q is 0 or 1; and 0<p+q?2.

    6. The composition of claim 5, which is one selected from the group consisting of compounds (1-1) to (1-4) below: ##STR00027## ##STR00028##

    7. The composition of claim 4, wherein the electrolyte is present at an amount of 9.95 to 19.95 wt. %, based on a total weight of the composition.

    8. The composition of claim 4, wherein the additive is present at an amount of 0.05 to 20.0 wt. %, based on a total weight of the composition.

    9. The composition of claim 4, wherein the electrolyte comprises at least one selected from the group consisting of lithium hexafluorophosphate (LiPF.sub.6), lithium fluoroborate (LiBF.sub.4), lithium bis (trifluoromethanesulfonyl) imide (LiN (CF.sub.3SO.sub.2).sub.2), and lithium trifluoromethanesulfonate (LiCF.sub.3SO.sub.3).

    10. The composition of claim 4, wherein the non-aqueous solvent comprises at least one selected from the group consisting of carbonates, furans, ethers, sulfides, and nitriles.

    11. The composition of claim 4, wherein the non-aqueous solvent comprises at least one selected from the group consisting of ether-based polymers, polymethacrylate-based polymers, polyacrylated polymers, and fluoropolymers.

    12. An electrochemical device, comprising an anode, a cathode, and the composition of claim 4 configured between the anode and the cathode.

    13. The electrochemical device of claim 12, which is a lithium-ion secondary battery.

    Description

    BRIEF DESCRIPTION OF THE DRAWINGS

    [0026] The present disclosure can be more fully understood by reading the following descriptions of the embodiments, with reference made to the accompanying drawings.

    [0027] FIGS. 1A to 1D are NMR spectra of the compounds of Formulae 1-1 to 1-4 of the present disclosure, respectively.

    [0028] FIGS. 2A to 2E show results of 1C cycle life tests under an environmental temperature of 25? C. for batteries having the electrolytes without addition of the compound of Formula 1-1 or with addition of the compound of Formula 1-1 at an amount of 5%, 10%, 15% and 20%, respectively.

    [0029] FIGS. 3A to 3E show results of charge-discharge rate tests under an environmental temperature of 25? C. with different rates of 0.1 C, 0.2 C, 0.3 C, 0.5 C and 1 C for batteries having the electrolyte without addition of the compound of Formula 1-1 or with addition of the compound of Formula 1-1 at an amount of 5%, 10%, 15% and 20%, respectively.

    [0030] FIGS. 4A to 4B show observation curves of a battery voltage and a temperature in nail penetration tests on NMC622 lithium ion batteries.

    DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

    [0031] The following examples are used for illustrating the present disclosure. A person skilled in the art can easily conceive the other advantages and effects of the present disclosure, based on the disclosure of the specification. The present disclosure can also be implemented or applied as described in different examples. It is possible to modify or alter the following examples for carrying out this disclosure without contravening its scope, for different aspects and applications.

    [0032] The present disclosure is directed to a phosphazene derivative having a structure of Formula (I):

    ##STR00009## [0033] wherein n is an integer of 3 to 6, R.sub.1 and R.sub.2 are independently selected from a group represented by Formula (I-1) or Formula (I-2),

    ##STR00010## [0034] wherein A is R.sub.3OR.sub.4, R.sub.3CH.sub.3-m(OR.sub.4).sub.m, CH.sub.3-m(OR.sub.4).sub.m or

    ##STR00011## R.sub.3 is unsubstituted C.sub.1-C.sub.8 alkylene or C.sub.1-C.sub.8 alkylene substituted with C.sub.1-C.sub.8 alkyl, R.sub.4 is C.sub.1-C.sub.8 alkyl, R.sub.5 is C.sub.1-C.sub.3 alkyl, R.sub.6 is C.sub.1-C.sub.3 alkylene, R.sub.7 is C.sub.1-C.sub.3 alkyl, x is 1 or 2, m is 2 or 3, p is a number of the A bonded to a carbon in a benzene ring to which the A is attached, and p is an integer of 0 to 3; [0035] B is C.sub.1-C.sub.8 alkoxy or C.sub.1-C.sub.8 alkyl, and q is an integer of 0 to 3; and 0<p+q?5.

    [0036] In one embodiment, a range of the number of carbon atoms of the present disclosure can extend from a lower limit to an upper limit, for example, C.sub.1-C.sub.8 refers to a number of the carbon atom(s) of 1, 2, 3, 4, 5, 6, 7, or 8.

    [0037] In some embodiments, the compound of the phosphazene derivative having the structure of Formula (I) of the present disclosure is selected from Table 1, but not limited thereto.

    TABLE-US-00001 TABLE 1 Compound of Formula 1-1 [00012]embedded image Compound of Formula 1-2 [00013]embedded image Compound of Formula 1-3 [00014]embedded image Compound Formula 1-4 [00015]embedded image

    [0038] In another embodiment, the compound of the phosphazene derivative having the structure of Formula (I) of the present disclosure is preferably the following compound:

    ##STR00016##

    [0039] In another embodiment, the present disclosure provides a composition for an electrochemical device, which comprises the novel phosphazene derivative-based additive of the present disclosure. The defect of the electrochemical device of poor safety can be improved by the use of the additive. In one embodiment, the composition of the present disclosure comprises an electrolyte, a non-aqueous solvent and an additive. The additive comprises the phosphazene derivative having the structure of Formula (I) of the present disclosure:

    ##STR00017## [0040] wherein n is an integer of 3 to 6, R.sub.1 and R.sub.2 are independently selected from a group represented by Formula (I-1) or Formula (I-2),

    ##STR00018## [0041] wherein A is R.sub.3OR.sub.4, R.sub.3CH.sub.3-m(OR.sub.4).sub.m, CH.sub.3-m(OR.sub.4).sub.m or

    ##STR00019## R.sub.3 is unsubstituted C.sub.1-C.sub.8 alkylene or C.sub.1-C.sub.8 alkylene substituted with C.sub.1-C.sub.8 alkyl, R.sub.4 is C.sub.1-C.sub.8 alkyl, R.sub.5 is C.sub.1-C.sub.3 alkyl, R.sub.6 is C.sub.1-C.sub.3 alkylene, R.sub.7 is C.sub.1-C.sub.3 alkyl, x is 1 or 2, m is 2 or 3, p is a number of the A bonded to a carbon in a benzene ring to which the A is attached, and p is an integer of 0 to 3; [0042] B is C.sub.1-C.sub.8 alkoxy or C.sub.1-C.sub.8 alkyl, and q is an integer of 0 to 3; and 0<p+q?5.

    [0043] In one embodiment, a range of the number of carbon atoms of the present disclosure can extend from a lower limit to an upper limit, for example, C.sub.1-C.sub.8 refers to a number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, or 8.

    [0044] In one embodiment, the phosphazene derivative having the structure of Formula (I) contained in the additive of the composition of the present disclosure is selected from Table 1 aforementioned, but not limited thereto.

    [0045] In another embodiment, the phosphazene derivative having the structure of Formula (I) contained in the additive of the composition of the present disclosure is preferably the following compound:

    ##STR00020##

    [0046] In the composition of the present disclosure, the contents of each component can vary depending on the actual application and is not limited to the contents described herein.

    [0047] In one embodiment, the amount of the electrolyte contained in the composition of the present application is about 9.95 to 19.95 wt. %, e.g., 9.95, 10.0, 11.0, 12.0, 13.0, 14.0, 15.0, 16.0, 17.0, 18.0, 19.0 or 19.95 wt. %, based on the total weight of the composition.

    [0048] In one embodiment, the amount of the additive contained in the composition of the present application is about 0.05 to 20.0 wt. %, e.g., 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, 11.0, 12.0, 13.0, 14.0, 15.0, 16.0, 17.0, 18.0, 19.0 or 20.0 wt. %, based on the total weight of the composition.

    [0049] In the composition of the present disclosure, the content of the non-aqueous solvent can vary corresponding to changes in the contents of other components in the composition, provided that the total amount of the non-aqueous solvent and the other components in the composition is 100 wt. % That is, one of the uses of the non-aqueous solvent is to complement the composition to 100 wt. %. In one embodiment, the non- aqueous solvent contained in the composition of the present disclosure is at an amount of about 65.0 to 90.0 wt. %, e.g., 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89 or 90 wt. %. In one embodiment, the composition of the present disclosure contains the non-aqueous solvent at an amount of about 80.0 to 90.0 wt. %.

    [0050] The electrolytes suitable for the present disclosure are those commonly used in the art. In one embodiment of the composition of the present disclosure, the electrolyte comprises at least one selected from the group consisting of lithium hexafluorophosphate (LiPF.sub.6), lithium fluoroborate (LiBF.sub.4), lithium bis (trifluoromethanesulfonyl) imide (LiN(CF.sub.3SO.sub.2).sub.2), and lithium trifluoromethanesulfonate (LiCF.sub.3SO.sub.3).

    [0051] The non-aqueous solvent in the composition of the present disclosure can be in a liquid or non-liquid form such as solid or gel, but not limited thereto.

    [0052] In one embodiment of the non-aqueous solvents in the liquid form, those commonly used in the art can be selected, such as at least one selected from the group consisting of carbonates (e.g., ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, or methylethyl carbonate), furans (e.g., tetrahydrofuran), ethers (e.g., diethyl ether), sulfides (e.g., methyl-sulfolane) and nitriles (e.g., acetonitrile, propionitrile). In one embodiment of the composition of the present disclosure, the non-aqueous solvent comprises at least one selected from the group consisting of carbonates, furans, ethers, sulfides and nitriles.

    [0053] In one embodiment, the non-aqueous solvents in the non-liquid form can be a polymer compound, e.g., at least one selected from the group consisting of ether-based polymers (e.g., polyethyleneoxide or a cross-linked product thereof), polymethacrylate- based polymers, polyacrylate-based polymers, fluoropolymers (e.g., polyvinylidene fluoride (PVDF) and vinylidene fluoride-hexafluoro propylene polymer). In one embodiment of the composition of the present disclosure, the non-aqueous solvent comprises at least one selected from the group consisting of ether-based polymers, polymethacrylate-based polymers, polyacrylated polymers, and fluoropolymers.

    [0054] The composition of the present disclosure can be obtained either by dissolving the aforementioned electrolyte and the phosphazene derivative-based additive of the present disclosure in a liquid non-aqueous solvent described above or by dissolving the electrolyte and the phosphazene derivative-based additive in liquid non-aqueous solvents, respectively, followed by mixing. If the used non-aqueous solvent is solid, the electrolyte, the phosphazene derivative-based additive and the solid non-aqueous solvent are first dissolved with organic solvents (e.g., alkanes, ketones, aldehydes, alcohols, ethers, benzene, toluene, xylene, kerosene, or the combination thereof), mixed thoroughly, and heated to evaporate the organic solvents to yield the composition of the present disclosure.

    [0055] In another embodiment, the electrochemical device different from the conventional devices is provided by applying the aforementioned composition therein. In other words, the present disclosure also provides an electrochemical device, comprising an anode, a cathode, and the composition of the present disclosure configured between the anode and the cathode.

    [0056] In one embodiment, the electrochemical device of the present disclosure is a lithium-ion secondary battery.

    EXAMPLES

    [0057] Various properties and efficacies will be illustrated by Examples below. The Examples set forth are used to illustrate the properties of the present disclosure which is not limited to those illustrated in the particular examples.

    Preparation Example 1

    1. Preparation of the Compound of Formula 1-1:

    [0058] The compound of Formula 1-1 of the present disclosure can be prepared by the following Scheme 1. Specifically, hexachlorophosphazene (1 g, 2.87 mmol, 1 eq) was mixed with acetone (20 mL) to form Solution a; 4-(2-methoxyethyl) phenol (3.94 g, 25.9 mmol, 9 eq) was mixed with acetone (60 mL) to form Solution b. Afterwards, K.sub.2CO.sub.3 (3.58 g, 25.9 mmol, 9 eq) was added to the Solution b to form Solution c. The Solution c was poured into the Solution a to perform a condensation and reflux reaction in an oil bath at 70? C. for 4 days. After the reaction was completed, the solid was removed, and the solvent was removed by distillation under a reduced pressure to yield a crude product. The crude product was washed with methanol and water repeatedly, and then freezing-dried to yield the compound of Formula 1-1 as a powder. The NMR spectrum of the compound of Formula 1-1 was shown in FIG. 1A.

    ##STR00021##

    2. Preparation of the Composition for the Electrochemical Device

    [0059] Ethylene carbonate (EC) was dissolved in diethyl carbonate (DEC) or dimethyl carbonate (DMC) at an equal weight ratio, to give a mixed solution of EC:DEC:DMC (1:1:1) or EC:DEC (1:1). Thereafter, 11.8 wt. % of LiPF.sub.6 electrolyte was added to the mixed solution aforementioned, after calculated based on the weight molar concentration. Finally, 5 wt. % or 7 wt. % of the additive (compound of Formula 1-1 prepared by the method described) was added and stirred to mix thoroughly, thereby forming the composition for the electrochemical device.

    Preparation Examples 2-4

    1. Preparation of the Compounds of Formula 1-2 to Formula 1-4:

    [0060] The compounds were prepared by the same procedures described in the preparation of the compound of Formula 1-1 in the Preparation Example 1, except that 4-(2-methoxyethyl) phenol is replaced with vanillyl butyl ether, vanillyl ethyl ether and 4-methoxyphenol), respectively, to prepare each compound of Formula 1-2, Formula 1-3, and Formula 1-4. The NMR spectra of the compounds of Formula 1-2 to Formula 1-4 were shown in FIGS. 1B-1D, respectively.

    Example 1: Fire-Retarding Tests on Electrolytes

    [0061] Fire-retarding tests were performed as below by using the compound of Formula 1-1 obtained in Preparative Example 1 in the electrolyte: [0062] 1. The compound of Formula 1-1 and the commercially available fire retardant PFPN (pentafluoroethoxycyclotriphosphazene) were dissolved in the commercially available electrolyte (EC:DEC=1:1; 1M LiPF.sub.6) at the amounts of 0 and 5 wt. %, respectively, to form electrolytes to be tested. [0063] 2. 10 ml of each electrolyte to be tested was taken into a 20 ml sample bottle. A fiberglass cloth of 4 cm long and 1 cm wide was soaked completely in the electrolyte for 10 sec, and then was removed and fixed at one end on the tube rack with the binder clip. [0064] 3. The fiberglass cloth was brought into contact with a fixed fire source (from a commercial butane lighter) at the non-fixed end opposite to the fixed end for 3 secs, then the fire source was removed, and the combustion phenomenon was observed until the flame completely extinguished and the combustion duration was recorded. The duration was recorded as the time from removal of the fire source to complete extinguishing (self-extinguishing time).

    [0065] Results of tests: The results of the fire-retarding tests were summarized in Table 2 below. It can be seen from the addition concentrations and the self-extinguishing times, the compound of Formula 1-1 did have the effect of improving the fire-retarding capability of the electrolyte, with the fire-retarding effect at an amount of 5% being better than that of PFPN, a commercially available fire-retardant.

    TABLE-US-00002 TABLE 2 Results of the fire-retarding tests on electrolytes (wt. %) 0 5 Sample Self-extinguishing time Fiberglass cloth 0 s Electrolyte (blank reagent) 24 s Electrolyte + PFPN 29 s Electrolyte + compound of Formula 1-1 19 s

    Example 2: Cycle life Tests on LiFePO.SUB.4 .coin cells

    1. Battery Assembling:

    [0066] Coin cells were assembled by using LiFePO.sub.4 as the cathode, lithium as the anode, and a commercial separator (Celgard? 2325) and an electrolyte (1 M LiPF6 in EC/DEC (1:1)).

    2. 1C Cycle Life Tests:

    [0067] Coin cells were charged and discharged by repeating (1) charging to 4.0V with 1C constant current and (2) discharging to 2.5V under the discharge condition of 1C constant current by using an electrolyte without the addition (0%, as a control group) or with the addition of 5%, 10%, 15% and 20% of the compound of Formula 1-1, under an environmental temperature of 25? C., and the degradation of capacitance in the first 250 cycles was recorded (Charge Discharge Test Instrument: Actech Systems BAT-750B). The results of the tests were shown in FIGS. 2A-2E, it can be seen that neither the addition nor the addition amount of the compound of Formula 1-1 showed an obvious effect on the cycle life of the battery within 250 cycles. Electric capacities during the first 5 cycles and the last 5 cycles as well as the electric capacity retention rates in the 250 cycles tests were recorded in Table 3 below, with different addition ratio of the compound of Formula 1-1.

    TABLE-US-00003 TABLE 3 Electric capacities during the first/last 5 cycles as well as the electric capacity retention rates in the 250 cycles tests with different addition ratio of the compound of Formula 1-1 Content of the compound of Formula 1-1 (%) 0 5 10 15 20 Electric capacity 144.6 ? 0.09 144.58 ? 0.26 133.69 ? 0.64 123.89 ? 0.30 130.57 ? 0.3 during the first 5 cycles (mAh/g) Electric capacity 145.2 ? 0.35 139.96 ? 0.24 135.42 ? 0.12 119.16 ? 0.12 128.16 ? 0.11 during the last 5 cycles (mAh/g) Electric capacity >100 96.8 >100 96.2 98.2 retention rate (%)

    Example 3: Charge-Discharge Tests at Different Rates

    [0068] Charge-discharge tests were performed on the coin cells assembled in Example 2 by using an electrolyte without the addition (0%, as the control group) or with the addition of 5%, 10%, 15% and 20% of the compound of Formula 1-1 aforementioned at an environmental temperature of 25? C. with different rates of 0.1 C, 0.2 C, 0.3 C, 0.5 C and 1 C (charge-discharge tester: Acutech Systems BAT-750B). The results of the tests were shown in FIGS. 3A-3E, it can be seen that there was no obvious difference in the specific capacity at the same charge-discharge rate, regardless of the addition and the addition amount of the compound of Formula 1-1. As examples, the discharge specific electric capacities at the rates of 0.1 C and 1 C with different addition amount of the compound of Formula 1-1 were recorded in Table 4 below.

    TABLE-US-00004 TABLE 4 Discharge specific electric capacities at the rates of 0.1 C and 1 C with different addition amounts of the compound of Formula 1-1 Discharge specific capacity (mAh/g) Sample wt. % 0.1 C 1 C Compound of 0 151.5 143.0 Formula 1-1 5 152.8 144.3 10 152.4 134.8 15 151.2 136.8 20 154.1 133.6

    Example 4: Performance Tests and nail penetration tests on NMC622 lithium ion batteries

    [0069] The type of batteries in the tests are punch cells employed with the cathode of LiNi.sub.0.6Mn.sub.0.2Co.sub.0.2O.sub.2 and the anode of artificial graphite (simplified as NMC622 lithium ion batteries), which were designed as shown in Table 5 below.

    TABLE-US-00005 TABLE 5 Designs of NMC622 lithium ion batteries Anode/cathode NiMnCo 622 cathode/ material artificial graphite anode Compositions 1M LiPF.sub.6 in electrolyte of electrolyte (EC:DEC:DMC = 1:1:1) Separator PP 20 um, without coating Battery size 3.5 ? 0.1 mm * 40 ? 1 mm * 60 ? 1 mm Battery capacity 1 Ah (energy density of about 220 Wh/kg

    [0070] A punch cell with the addition of 7 wt. % of the compound of Formula 1-1 as the experiment group, and one with no addition of a fire retardant as the control group, were tested for battery performances with a charger/discharger (CT-4008T-5V6A-S1, Neware Technology Co,. Ltd.) (Assayer: Keysight 34972A LXI) and subjected to nail penetration tests. The device for the nail penetration tests was customized by disposing of steel needles and the controller in the metal case and providing temperature and voltage monitors outside the case, with the sensing wiring inserted into the device. The nail penetration tests complied with the specifications for needle diameter and nail penetrating rate in standards such as IEC60086-4:2000, UL1642-2007, and UL2054. Cells were test for performance in steps shown in Table 6 below; and the parameters for nail penetration tests were shown in Table 7 below.

    TABLE-US-00006 TABLE 6 Steps for testing performance of batteries 1 Charging to 4.25 V with 1 C constant current 2 Charging with 1 C constant voltage to a current cutoff of 0.175 A 3 Resting for 2 minutes 4 Discharging to 2.8 V with 1 C constant current 5 Resting for 2 minutes and repeating the steps aforementioned

    TABLE-US-00007 TABLE 7 Parameters for nail penetration test Needle diameter 3 mm Nail penetrating rate 4.2 cm/s Initial height 24.5 cm

    [0071] The results from the battery performance test and the nail penetration test were shown in Table 8 below and FIGS. 4A and 4B. It was observed in the nail penetration test, for cells in the experiment group with the addition of the compound of Formula 1-1, no fire or smoke was seen, the surface temperature was maintained at 30? C. without evident increase, and there was no significant change in voltage of the cells; in contrast, fire and smoke were observed in the control group without the addition of any additive with a dramatic increase in surface temperature and reduction in the voltage to 0V. Changes in voltage and temperature of the experiment and control groups were shown in FIGS. 4A and 4B. It can be seen from the results presented above, the safety of battery containing the electrolyte formulated with the compound of Formula 1-1 of the present disclosure was improved in view of the results from the nail penetration test for battery safety relative to those containing the electrolyte without any additive.

    TABLE-US-00008 TABLE 8 The electronic properties of 1Ah punch cells and the results of nail penetration Inner Charging Median Factional resistance Additive voltage voltage capacity of product Results of nail (%) (V) (V) (mAh) (m?) penetration Control 4.25 3.64 1100.9 22.4 Dramatic rise group in temperature, firing, burning, dropping to zero in voltage Experiment 7 wt. % of 4.25 3.64 1104.4 25.7 No observation group the compound of burning, of Formula no significant 1-1 changes in temperature, voltage, appearance

    [0072] It can be seen from the examples above, by using the phosphazene derivative of the present disclosure as the additive to the electrolyte of a lithium-ion battery, in addition to no significant effect on the performance of the battery, the fire retardance effect better than PFPN, a commercially available fire retardant, can be achieved, and the safety of the battery upon external damages can be significantly enhanced. Therefore, the phosphazene derivative of the present disclosure is an inventive substance having excellent efficacies and can be utilized broadly.

    [0073] While some of the embodiments of the present disclosure have been described in detail above, it is, however, possible for those of ordinary skill in the art to make various modifications and changes to the particular embodiments shown without substantially departing from the teaching and advantages of the present disclosure. Such modifications and changes are encompassed in the scope of the present disclosure as set forth in the appended claims.