Organometallic compounds for use in metal-ion batteries

Abstract

Formula (I): [Case 1] TIFF2026502440000026.tif34155, wherein X is Al or B, and R 1 is, in each occurrence, independently a monovalent substituent; R 2 is a divalent organic group, and M + is a cation. The compounds of formula (I) can be used as electrolytes in metal or metal-ion batteries.

Description

[Background technology]

[0001] WO 00 / 53611 discloses compounds comprising the monoanion of formula (II). [ka]

[0002] WO 99 / 12938 discloses polyfluorinated alkoxides coordinated to a transition metal or an element of Group III, IV, or V. The use of the compounds in batteries is disclosed.

[0003] Nolan et al., "Nonaqueous Lithium Battery Electrolytes Based on Bis(polyfluorodiolato)borates," 2003 J. Electrochem. Soc. 150 A1726, discloses lithium salts for use as battery electrolytes.

[0004] JP 2002 / 260734 A discloses an electrolyte of formula (1). [ka]

[0005] US Pat. No. 6,783,896 discloses compounds of formula (I). [ka]

[0006] EP 1075036 discloses compounds of formula (1). [ka]

[0007] WO 2022 / 243470 discloses an electrolyte comprising solvated lithium ions. Summary of the Invention

[0008] The present disclosure provides a compound of formula (I): [ka] wherein X is Al or B and R 1 is, in each occurrence, independently a monovalent substituent; R 2 is a divalent organic group, and M + is a cation, compound.

[0009] Optionally, R 2 is represented by formula (II): [ka] where R 3 is independently, in each occurrence, H or a substituent; Ar 1 is C 6-20 It is an arylene group or a heteroarylene group.

[0010] Optionally, Ar 1 is unsubstituted or substituted 1,2-phenylene.

[0011] Optionally, each R 1 independently C 1-20 alkyl, OR 1 One or more atoms other than the C atom bonded to O or terminal C atoms may be substituted with O, and one or more H atoms may be substituted with F.

[0012] Optionally, X is B.

[0013] Optionally, M + is lithium ion.

[0014] The present disclosure provides an electrolyte comprising a compound of formula (I) and at least one of a solvent and a polymer.

[0015] Optionally, the electrolyte is C2-10 Alkylene carbonate; di(C 1-10 alkyl) carbonates; linear, branched, or cyclic compounds containing two or more ether groups; and mixtures thereof.

[0016] The present disclosure provides a metal or metal-ion battery comprising a negative electrode, a positive electrode, and an electrolyte described herein disposed between the negative electrode and the positive electrode. [Brief explanation of the drawings]

[0017] [Figure 1] FIG. 1 is a schematic diagram of a battery including compounds described herein. [Figure 2] FIG. 1 shows exemplary initial and steady-state Nyquist plots for a cell containing Comparative Compound 1. [Figure 3] FIG. 1 shows linear sweep voltammograms for Compound Example 1 and Comparative Compounds 1 and 2. DETAILED DESCRIPTION OF THE INVENTION

[0018] Unless the context clearly requires otherwise, throughout the specification and claims, words such as "comprise," "comprising," and the like, shall be construed in an inclusive sense, i.e., "including, but not limited to," as opposed to an exclusive or exhaustive sense. Furthermore, the words "herein," "on," "under," and words of similar import, when used in this application, refer to this application as a whole and not to particular portions of this application. Where the context permits, words in the Detailed Description using the singular or plural may also include the plural or singular, respectively. The word "or" in connection with a list of two or more items encompasses all of the following interpretations of that word: any of the items in the list, all of the items in the list, and any combination of the items in the list. As used in this application, a reference to a layer "over" another layer means that the layers may be in direct contact, or that there may be one or more intervening layers. As used in this application, a reference to a layer "on" another layer means that the layers are in direct contact. A reference to an element of the periodic table includes any isotopes of that element.

[0019] The teachings of the technology provided herein may be applied to other systems, not necessarily the systems described below. Elements and acts of the various examples described below can be combined to provide further implementations of the technology. Some alternative implementations of the technology may include additional elements as well as fewer elements relative to those implementations described below.

[0020] These and other changes can be made to the technology in light of the following detailed description. While the description illustrates certain examples of the technology and explains the best mode contemplated, no matter how detailed the description may appear, the technology can be practiced in many ways. As described above, a particular term used when describing a particular feature or aspect of the technology should not be construed as meaning that the term is redefined herein to be limited to any particular feature, characteristic, or aspect of the technology associated with that term. In general, the terms used in the following claims should not be construed to limit the technology to the particular embodiments disclosed herein, unless such terms are otherwise expressly defined in the Detailed Description section. Thus, the actual scope of the technology encompasses not only the disclosed embodiments but also all equivalent ways of practicing or implementing the technology according to the claims.

[0021] In order to reduce the number of claims, certain aspects of the technology are presented below in certain claim forms, but applicants contemplate various aspects of the technology in any number of claim forms.

[0022] In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of implementations of the disclosed technology. However, it will be apparent to one skilled in the art that embodiments of the disclosed technology may be practiced without some of these specific details.

[0023] Compounds of formula (I) The present inventors have surprisingly found that compounds of formula (I) can have both high ionic conductivity and / or high lithium transference number in addition to electrochemical stability. [ka]

[0024] X is Al or B.

[0025] R 1is, in each occurrence, independently a monovalent substituent; R 1 is R 1 by carbon atoms of OR 1 is bonded to O.

[0026] Preferably, each R 1 are independently linear, branched or cyclic C 1-40 alkyl, OR 1 C other than C atoms bonded to O 1-40 One or more C atoms of an alkyl, or C 1-40 The terminal C atom of the alkyl may be substituted with O and one or more H atoms may be substituted with F.

[0027] As used herein, the "terminal C atom" of an alkyl group means the methyl C atom of an n-alkyl chain or the methyl C atom of a branched alkyl chain.

[0028] Preferred groups R 1 teeth, -(CH2CH2O)nR 5 wherein R 5 is C 1-4 alkyl, n is 1 to 15, and one or more H atoms may be replaced by F; C in which one or more H atoms may be replaced by F 1-12 It is alkyl.

[0029] In some embodiments, R 1 The groups are identical.

[0030] In some embodiments, R 1 The groups are different.

[0031] R 2 is a divalent organic group, OR 2 Each O in -O is R 2 Preferably, R 2 is represented by formula (II): [ka] where R3 is independently, in each occurrence, H or a substituent; Ar 1 is C 6-20 It is an arylene group or a heteroarylene group.

[0032] Preferably, Ar 1 is unsubstituted or substituted 1,2-phenylene, or an unsubstituted or substituted 5- or 6-membered heteroaromatic ring. Particularly preferred heteroaromatic groups Ar 1 is a 6-membered heteroaromatic ring whose ring atoms consist only of C and N atoms, for example pyridine or pyrimidine.

[0033] If present, Ar 1 The substituents in are preferably, and independently, F and C 1-12 alkyl, and one or more non-adjacent C 1-12 Non-terminal C atoms of alkyl are O, S, NR 4 , CO COO or CONR 4 wherein R 4 is independently C 1-12 is a hydrocarbyl group, C 1-12 One or more H atoms of the alkyl group may be replaced with F.

[0034] C anywhere in this specification 1-12 The hydrocarbyl group is preferably C 1-12 Alkyl, phenyl, and one or more C 1-6 phenyl substituted with an alkyl group.

[0035] Preferably, R 3 is, at each occurrence, independently H, F, or C in which one or more H atoms may be replaced by F and one or more non-terminal C atoms may be replaced by O. 1-12 In a preferred embodiment, at least one R 3 , optionally each R 3 is C 1-6 It is a perfluoroalkyl group.

[0036] M +is a cation. + is preferably an alkali metal cation, more preferably Li + is.

[0037] A compound of formula (I) may be formed by reacting a compound of formula (III) with a compound selected from formulas (IVa) and (IVb), and a compound selected from formulas (Va), (Vb) and (Vc). [ka]

[0038] The compound of formula (IVa) may be a primary, secondary or tertiary alcohol.

[0039] The compound of formula (IVb) may be an aldehyde or a ketone.

[0040] Exemplary compounds of formula (III) include, but are not limited to, lithium aluminum hydride (LiAlH4) and lithium borohydride (LiBH4).

[0041] Exemplary compounds of formula (I) include, but are not limited to: [ka]

[0042] electrolyte The electrolyte comprising the compound of formula (I) preferably further comprises at least one of a polymer and a solvent. When both a polymer and a solvent are present, the electrolyte may be a gel.

[0043] The polymer may be selected from any known ion-conducting polymer, including, but not limited to, poly(ethylene oxide) and poly(propylene oxide), and fluorinated polymers such as PVDF, PVDF-HFP, PMMA, polyacrylonitrile, polycarbonate, polyethylene, polypropylene, poly(vinyl methyl ketone), polyvinylpyrrolidone, polyether ether ketone, polyisoprene, polybutadiene, polystyrene-block-polyisoprene-block-polystyrene, poly(1-vinylpyrrolidone-co-vinyl acetate), polystyrene-block-polybutadiene-block-polystyrene, polystyrene-block-poly(ethylene oxide)-block-polystyrene, copolymers, and mixtures thereof.

[0044] The polymer is preferably a neutral polymer, ie not a polymer substituted with ionic groups, and particularly preferably not a single-ion conducting polymer containing anionic groups.

[0045] The electrolyte may include one or more solvents, preferably C 10 carbonates such as propylene carbonate, ethylene carbonate, dimethyl carbonate, and diethyl carbonate. 2-10 Alkylene carbonate, di(C 1-10 alkyl) carbonates; linear, branched or cyclic compounds containing two or more ether groups, such as 1,3-dioxolane, 2,5-dimethoxytetrahydrofuran, glyme (dimethoxyethane), diglyme, triglyme and tetraglyme; cyclic lactones and mixtures thereof.

[0046] The compound of formula (I) may be a solvate M + It may contain cations.

[0047] Optionally, the electrolyte present in the battery contains 10 or fewer solvent molecules per M+ cation. The solvent / M+ ratio is the ratio of the solvent to the M+ cation of the electrolyte prior to incorporation into the battery. 1 as can be determined from the H NMR spectrum.

[0048] battery Figure 1 shows a battery comprising a compound of formula (I). The battery may be a metal battery or a metal ion battery, preferably a lithium battery or a lithium ion battery.

[0049] The battery includes an anode current collector 101 carrying an anode 103 on its surface, a cathode current collector 109 having a cathode 107 disposed thereon, and a layer 105 comprising an electrolyte including a compound described herein disposed between the anode and cathode.

[0050] Layer 105 may include a porous separator into which an electrolyte, e.g., a liquid or gel electrolyte, is absorbed. If the electrolyte comprises, for example, a gel including a polymer and a compound of formula (I), the porous separator may or may not be present.

[0051] In a metal battery, the negative electrode is a layer of metal (eg, lithium) that forms on the negative electrode current collector during charging of the battery and is removed during discharge of the battery.

[0052] In the case of metal ion batteries, such as lithium ion batteries, the negative electrode comprises an active material, such as graphite, for absorption of metal ions.

[0053] The positive electrode may be selected from any positive electrode known to those skilled in the art.

[0054] The negative and positive current collectors can be one or more layers of any suitable conductive material known to those skilled in the art, for example, a metal or metal alloy such as aluminum or copper.

[0055] A battery can be formed by providing an electrolyte described herein on the surface of one of the negative and positive electrodes, and providing the other of the negative and positive electrodes and associated current collectors above the electrolyte.

[0056] A metal battery precursor can be formed by disposing an electrolyte described herein on the surface of a negative electrode current collector, and disposing a positive electrode and a positive electrode current collector over the electrolyte. Upon application of a charging bias, a metal negative electrode can be formed between the electrolyte and the negative electrode current collector.

[0057] 1 shows a battery in which the negative and positive electrodes are separated only by a single layer containing or consisting of an electrolyte, such as a separator containing the electrolyte. In other embodiments, one or more additional layers may be disposed between the negative and positive electrodes.

[0058] For simplicity, FIG. 1 shows a battery in which the negative and positive electrodes are separated only by a single layer 105, although it will be understood that in use a solid electrolyte interface typically forms on the negative electrode surface. [Example]

[0059] Compound Example 1 Compound Example 1 was prepared according to the following reaction scheme. [ka]

[0060] To a solution of lithium borohydride (9.2 mL, 4.6 mmol, 0.5 M in THF) was added dropwise a solution of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (1 g, 3.84 mmol in 8 mL of THF) at -70°C. The mixture was stirred at -70°C to -60°C for 3 hours and then warmed to 0°C. A solution of 2,2,3,3,4,4,5,5-octafluoropentanol (1 mL, 7.68 mmol in 8 mL of THF) was added dropwise to the mixture, and the solution was stirred at room temperature for 1.75 hours. The temperature was raised to 60°C, and the mixture was stirred overnight. The reaction mixture was cooled to room temperature, and a solution of lithium borohydride (0.4 mL, 0.8 mmol, 2 M in THF) was added dropwise. The mixture was stirred at 60°C for 4 hours and then cooled to room temperature. Propylene carbonate (0.65 mL, 7.66 mmol) was added. Excess solvent was removed under vacuum (3.1 × 10 -2The reaction mixture was removed at 25° C. for 1 h at 37° C. and 40° C. for 2 h at 37° C. to give a thick white oil. Additional propylene carbonate (0.6 mL, 7.1 mmol) was added to give 3.8 g of a white oil (86% yield).

[0061] From the integration of the NMR peaks, it was calculated that for one molecule of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol corresponding to one molecule of lithium cation, there are 0.1 molecules of THF and 4.0 molecules of propylene carbonate (PC).

[0062] in deuterated THF 1 H NMR (600 MHz): δ (ppm), 1.39 (12H, d, J = 6.2 Hz, CH from PC), 1.78 (0.5H, m, CH from THF), 3.62 (0.5H, m, CH from THF), 3.90 (4H, m), 4.00 (4H, t, J = 8.0 Hz, CH from PC, 4H), 4.50 (4H, t, J = 8.1 Hz, CH from PC), 4.80 (m, CH from PC, 4H), 6.6–6.86 (4H, m), 7.15 (1H, td, J = 7.6 Hz, J = 1.4 Hz), 7.32 (1H, d, J = 7.6 Hz).

[0063] Compound Example 2 Compound Example 2 was prepared according to the following reaction scheme. [ka]

[0064] The number of repeating units is 1 Determined by 1 H NMR.

[0065] To a solution of lithium borohydride (9.2 mL, 4.6 mmol, 0.5 M in THF) was added dropwise a solution of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (1 g, 3.84 mmol in 8 mL of THF) at -90 to -80 °C. The mixture was stirred at -85 to -70 °C for 3 hours, and then warmed to 0 °C. A solution of MPEG 350 (2.87 g, 7.68 mmol in 8 mL of THF) was added dropwise to the mixture, and the solution was stirred at room temperature for 1 hour. The temperature was raised to 60 °C over 30 minutes, and the mixture was cooled to room temperature overnight. Propylene carbonate (0.62 mL, 7.31 mmol) was added. Excess solvent was removed under vacuum (3.2 × 10 -2 mbar) at 25° C. for 2 hours, followed by 40° C. for 4 hours to give 4.0 g of compound Example 2 as a colorless oil (85% yield).

[0066] From the integration of the NMR peaks, it was calculated that 1.88 molecules of propylene carbonate (PC) exist for one molecule of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol, which corresponds to one molecule of lithium cation.

[0067] Compound Example 3 Compound Example 3 was prepared according to the following reaction scheme. [ka]

[0068] To a solution of lithium borohydride in tetrahydrofuran (7.9 mL, 3.84 mmol, 0.5 M) was added dropwise a solution of 1,1,1,3,3,3-hexafluoropropan-2-ol (0.8 mL, 7.68 mmol) in 7 mL of anhydrous tetrahydrofuran at -70°C. The mixture was then stirred at -70°C to -60°C for 1 hour and then warmed to 0°C. A solution of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (1 g, 3.84 mmol) in 7 mL of anhydrous THF was added dropwise to the reaction mixture at room temperature. The mixture was stirred at 65°C for 4 hours and then overnight at room temperature. Additional lithium borohydride (0.23 mL, 0.46 mmol) and hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (0.1 g, 0.38 mmol) were added, and the reaction mixture was stirred at 65°C for 2 hours. The mixture was cooled to room temperature and propylene carbonate (0.96 mL, 11.5 mmol) was added, followed by the addition of more propylene carbonate to obtain a clear liquid.

[0069] in deuterated THF 1 H NMR (600 MHz): δ (ppm), 1.38 (d, CH of propylene carbonate, 15.6H), 3.97 (m, CH of propylene carbonate, 5.1H), 4.52 (t, CH of propylene carbonate and CH of HFP, 6.8H), 4.81 (m, CH of propylene carbonate, 4.7H), 6.67 (m, 2H), 7.12 (td, J = 7.7 Hz, J = 1.6 Hz, 1H), 7.29 (d, J = 7.9 Hz, 1H).

[0070] From the integration of the NMR peaks, it was calculated that 5.1 molecules of propylene carbonate exist for one molecule of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol corresponding to one molecule of lithium cation.

[0071] Compound Example 4 Compound Example 4 was prepared according to the following reaction scheme. [ka]

[0072] To a solution of lithium borohydride in tetrahydrofuran (7.9 mL, 3.84 mmol, 0.5 M) was added dropwise a solution of 2,2,3,3-tetrafluoropropan-1-ol (0.68 mL, 7.68 mmol) in 7 mL of anhydrous tetrahydrofuran at -70°C. The mixture was then stirred at -70°C to -60°C for 1 hour and then warmed to 0°C. A solution of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (1 g, 3.84 mmol) in 7 mL of anhydrous THF was added dropwise to the reaction mixture at room temperature. The mixture was stirred at 65°C for 4 hours and overnight at room temperature. Additional lithium borohydride (0.1 mL, 0.2 mmol) and hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (0.06 g, 0.23 mmol) were added, and the reaction mixture was stirred at 65°C for 1 hour. The mixture was cooled to room temperature and propylene carbonate (0.96 mL, 11.5 mmol) was added, followed by the addition of more propylene carbonate to obtain a clear liquid.

[0073] in deuterated THF 1 H NMR (600 MHz): δ (ppm), 1.38 (d, CH of propylene carbonate, 11.6H), 3.77 (m, 4.2H), 3.97 (m, CH of propylene carbonate, 3.7H), 4.52 (t, CH of propylene carbonate, 3.7H), 4.80 (m, CH of propylene carbonate, 3.3H), 6.10 (tt, J = 53.51 Hz, J = 5.97 Hz, 2H), 6.70 (m, 2H), 7.14 (td, J = 7.7 Hz, J = 1.6 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H).

[0074] From the integration of the NMR peaks, it was calculated that for one molecule of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol corresponding to one molecule of lithium cation, there are 3.70 molecules of propylene.

[0075] Compound Example 5 Compound Example 5 was prepared according to the following reaction scheme. [ka]

[0076] To a solution of lithium borohydride in tetrahydrofuran (7.9 mL, 3.84 mmol, 0.5 M) was added dropwise a solution of 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol (0.94 mL, 7.68 mmol) in 7 mL of anhydrous tetrahydrofuran at -70°C. The mixture was then stirred at -70°C to -60°C for 1 hour and then warmed to 0°C. A solution of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol (1 g, 3.84 mmol) in 7 mL of anhydrous THF was added dropwise to the reaction mixture at room temperature. The mixture was stirred at 65°C for 4 hours and at room temperature overnight. Additional lithium borohydride (0.04 mL, 0.08 mmol) was added, and the reaction mixture was stirred at 65°C for 5 hours and at room temperature overnight. Propylene carbonate (0.96 mL, 11.5 mmol) was added. Further propylene carbonate was added to obtain a stable, clear liquid.

[0077] in deuterated THF 1 H NMR (600 MHz): δ (ppm), 1.38 (d, CH of propylene carbonate, 15.4H), 1.61 (s, 5.3H), 3.97 (m, CH of propylene carbonate, 5.3H), 4.52 (t, CH of propylene carbonate, 5.3H), 4.80 (m, CH of propylene carbonate, 5.1H), 6.62 (m, 2H), 7.10 (td, J = 7.7 Hz, J = 1.6 Hz, 1H), 7.27 (d, J = 7.7 Hz, 1H).

[0078] From the integration of the NMR peaks, it was calculated that 5.2 molecules of propylene carbonate exist for one molecule of hexafluoro-2-(2-hydroxyphenyl)propan-2-ol corresponding to one molecule of lithium cation.

[0079] Cell Example 1 2032-type coin cells were fabricated in a rigorously dried, oxygen-free, argon-filled MBraun glovebox using casings purchased from Cambridge Energy Solutions.

[0080] A stainless steel spacer was inserted into the bottom of the coin cell, followed by a lithium disk and a fluorosilicone stencil (purchased from Silex Silicones). The stencil was molded as a 15.5 mm diameter disk with a 5 mm diameter circular hole cut in the center (the thickness of the stencil in the crimped cell was 360 μm). The hole was filled with 30 μL of electrolyte solution containing Compound Example 1. The solvents are listed in Table 1 below.

[0081] The lithium disk was placed on top of the stencil, followed by the stainless steel spacer, the wave spring, and the top of the coin cell. Finally, the coin cell was crimped.

[0082] Cell Example 2 A cell was prepared similar to Cell Example 1, except that Compound Example 3 was used instead of Compound Example 1.

[0083] Cell Example 3 A cell was prepared similar to Cell Example 1, except that Compound Example 4 was used instead of Compound Example 1.

[0084] Comparison cell 1 For comparative purposes, a cell was prepared similar to Cell Example 1, except that Comparative Compound 1 was used in place of Compound Example 1. [ka]

[0085] Comparison cell 2 For comparative purposes, a cell was prepared similar to Cell Example 1, except that Comparative Compound 2 was used in place of Compound Example 1. [ka]

[0086] measurement Electrochemical Impedance Spectroscopy (EIS) measurements were performed at room temperature. Electrolyte impedance was acquired over a frequency range of 1 Hz to 1 MHz with an amplitude of 5 mV.

[0087] From these data, the ionic conductivity was calculated using the following formula:

number

[0088] The electrolyte impedance is determined by estimating the intercept of the first semicircle of the Nyquist plot with the x-axis, which is the lower left corner of the exemplary Nyquist plot of Comparative Compound 1 in FIG.

[0089] The lithium transference number (LTN) was measured using the above-mentioned 2032 type coin cell according to the Evans method (J. Evans et al., POLYMER, 1987, Vol. 28).

[0090] To ensure stabilization of the interface between the electrolyte and the lithium disk, the device was allowed to rest overnight for approximately 19 hours before LTN measurements were performed.

[0091] After a break, 1. The first EIS spectrum was measured. 2. After this, DC current measurements were performed to achieve an initial current of approximately 0.5 μA (the applied constant voltage was adjusted individually for each cell). The measurements were terminated as soon as the current had decreased to a steady state. 3. The sequence was then completed by a second EIS measurement.

[0092] EIS measurements were performed at room temperature over a frequency range of 1 Hz to 1 MHz with an amplitude of 5 mV.

[0093] The LTN value was calculated according to the following formula, based on the model developed by Evans et al.

number

[0094] Ionic conductivity and LTN were calculated for various solvated ionic liquids, and representative values ​​are reported in Table 1, where "PC" is propylene carbonate and "DME" is dimethoxyethane. [Table 1]

[0095] Linear Sweep Voltammetry The oxidative stability of Compound Example 1 and Comparative Compounds 1 and 2 was measured using linear sweep voltammetry in asymmetric coin cells. The cells were assembled as described for Cell Example 1 and Comparative Cells 1 and 2, respectively, but without the top lithium disk.

[0096] Measurements were performed on Example Compound 1, which contained 0.1 moles of THF and 4.0 moles of propylene carbonate per mole of lithium, Comparative Compound 1, which contained 0.05 moles of THF and 1.9 moles of propylene carbonate per mole of lithium, and Comparative Compound 2, which contained 6.0 moles of propylene carbonate per mole of lithium.

[0097] Linear sweep voltammograms were acquired for each cell using a Gamry potentiostat. The sweep rate was 1 mV per second, sweeping the cells from the open circuit potential to 5 V vs. Li / Li, except for the cell containing comparative compound 1, which was swept to 6 V due to its high electrochemical stability. + Swept until.

[0098] The oxidation stability was calculated by fitting lines to the region below 4 V and above 5 μA and calculating the voltage value at the intersection between the two lines.

number

[0099] 3 shows the linear sweep voltammograms of the asymmetric cells containing Compound Example 1 and Comparative Compounds 1 and 2. The calculated oxidative stability is listed in Table 2. [Table 2]

[0100] As shown in Tables 1 and 2, Compound Example 1 has higher ionic conductivity and LTN than Comparative Compound 1 and higher oxidative stability than Comparative Compound 2, thereby providing a good combination of stability, ionic conductivity, and LTN.

Claims

1. Formula (I): 【Chemistry 1】 wherein X is Al or B and R １ is, in each occurrence, independently a monovalent substituent; R ２ is a divalent organic group, and M ＋ is a cation, compound.

2. R ２ is represented by formula (II): 【Chemistry 2】 where R ３ is independently, at each occurrence, H or a substituent; Ar １ is C ６－２０ The compound of claim 1 , which is an arylene group or a heteroarylene group.

3. Ar １ The compound of claim 2, wherein is unsubstituted or substituted 1,2-phenylene.

4. Each R １ However, independently C １－２０ alkyl, OR １ The compound according to any one of claims 1 to 3, wherein one or more C atoms other than the C atom bonded to O or a terminal C atom may be substituted with O, and one or more H atoms may be substituted with F.

5. The compound according to any one of claims 1 to 4, wherein X is B.

6. M ＋ The compound according to any one of claims 1 to 5, wherein is a lithium ion.

7. An electrolyte comprising the compound according to any one of claims 1 to 6 and at least one of a solvent and a polymer.

8. The electrolyte is C ２－１０ Alkylene carbonate; di(C １－１０ 8. The electrolyte of claim 7, comprising a solvent selected from: alkyl) carbonates; linear, branched, or cyclic compounds containing two or more ether groups; and mixtures thereof.

9. 9. A metal or metal-ion battery comprising a negative electrode, a positive electrode, and the electrolyte of claim 7 or 8 disposed between the negative electrode and the positive electrode.

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