Uchicago Argonne, LLC

Daniel Abraham

Chen Liao

Ilya A Shkrob

Zhengcheng Zhang

Cameron Peebles

Hakim H Iddir

Juan Garcia

Gang Cheng

Ye Zhu

This invention relates to an electrolyte composition for a lithium ion battery comprising a lithium salt in a non-aqueous solvent containing an additive comprising a compound of formula RSiOP(O)F; wherein each R independently is a hydrocarbyl group; and n is 0 or 1; and wherein the additive is substantially free from (RSiO)P(O)and (RSiO)P(O)F. Electrochemical cells and batteries also are described.

Additives for high voltage lithium ion batteries

Lithium tetrafluoro(malonato)phosphate compounds are useful as additives in lithium ion battery applications. The compounds are represented by Formula (I): MPF[&#x2014;O(C&#x2550;O)&#x2014;(CX'X&#x2033;)&#x2014;(C&#x2550;O)O&#x2014;]; wherein M is Li or Na; each X&#x2032; and X&#x2033; independently is selected from the group consisting of H, alkyl, fluoro-substituted alkyl, and F; or wherein the X&#x2032; and X&#x2033; together are &#x2014;CR&#x2014;(CR&#x2032;)&#x2014;CR&#x2033;&#x2014;; each R, R&#x2032; and R&#x2033; independently is selected from the group consisting of H methyl, trifluoromethyl, and F; and in is 0 or 1. These compounds can be prepared in high purity and a high yield by reaction of a metal hexafluorophosphate with a bis-silyl malonate compound. A similar oxalato compound, lithium tetrafluoro(oxalato)phosphate), can be made in the same manner, but using a bis-silyl oxalate in place of the bis-silyl malonate. Advantageously, the compounds can be formed, in situ, in a LiPF-containing electrolyte solution.

Additives for lithium batteries and methods

Lithium tetrafluoro(malonato)phosphate compounds are useful as additives in lithium ion battery applications. The compounds are represented by Formula (I): MPF[&#x2014;O(C&#x2550;O)&#x2014;(CX'X&#x2033;)&#x2014;(C&#x2550;O)O&#x2014;]; wherein M is Li or Na; each X&#x2032; and X&#x2033; independently is selected from the group consisting of H, alkyl, fluoro-substituted alkyl, and F; or wherein the X&#x2032; and X&#x2033; together are &#x2014;CR&#x2014;(CR&#x2032;)&#x2014;CR&#x2033;&#x2014;; each R, R&#x2032; and R&#x2033; independently is selected from the group consisting of H, methyl, trifluoromethyl, and F; and m is 0 or 1. These compounds can be prepared in high purity and a high yield by reaction of a metal hexafluorophosphate with a bis-silyl malonate compound. A similar oxalato compound, lithium tetrafluoro(oxalato)phosphate), can be made in the same manner, but using a bis-silyl oxalate in place of the bis-silyl malonate. Advantageously, the compounds can be formed, in situ, in a LiPF-containing electrolyte solution.

This invention relates to a method for preparing an electrochemical cell comprising the sequential steps of preparing a solution of a lithium salt in an non-aqueous solvent containing an additive compound, and maintaining the solution at a temperature in the range of about 20 to about 30&#xb0; C. for about 5 to 10 days to form an aged electrolyte; assembling an electrochemical cell from an anode, a cathode, and the aged electrolyte; and electrochemically subjecting the electrochemical cell to formation cycling. The additive compound comprises one or more compounds selected from the group consisting of: (RSiO)B, (RSiO)XY, (RSiO)P, (R'O)PO, (RSi)X&#x2032;, RSiOS(O)R&#x2032;; (RSi)OC(&#x2550;O)R&#x2032;; wherein each R and R&#x2032; independently is a hydrocarbyl group; X is P or B; Y is O or S; X is Ti or Al. Electrochemical cells and batteries also are described.

A non-aqueous electrolyte for a lithium-ion battery comprises a lithium salt and an additive in an organic solvent. The additive comprises a di-substituted malonate silyl ester compound, in which the hydrogens of the malonate methylene group are replaced by substituents R(e.g., alkyl) and X (e.g., halogen). Each of the carboxylic acid groups of the malonate are esterified by a monovalent silyl group such as &#x2014;Si(R); or the two carboxylic acid groups are esterified by a single divalent silylene group such as &#x2014;Si(R)&#x2014; to form a ring therewith. Each Rand Rindependently is alkyl, phenyl, or alkoxy; and each substituted-alkyl comprises an alkyl moiety substituted with one or more group selected from alkenyl, alkynyl, hydroxy, halogen, alkoxy, carboxylic acid, carboxylic ester, carboxylic amide, phenyl, sulfonic acid, and phosphonic acid.

Electrolyte additives for lithium-ion batteries under high-voltage operation

The present invention provides an electrolyte composition for a lithium-ion battery comprising LiPFin a liquid carrier comprising a carbonate ester and an unsaturated organoboron compound comprising two or three unsaturated hydrocarbon groups, each unsaturated hydrocarbon group being covalently bonded to a boron atom. The unsaturated hydrocarbon groups are independently selected from vinyl, allyl, propargyl, substituted vinyl, substituted allyl, and substituted propargyl. The substituents of the substituted vinyl, allyl and propargyl groups independently comprise one or more of alkyl and phenyl. The alkyl and phenyl groups optionally can bear one or more substituent selected from halogen (e.g., F), hydroxy, amino, alkoxy, and perfluoroalkoxy.

Electrolyte compositions for high voltage lithium-ion batteries

The present invention provides an electrolyte for lithium and/or lithium-ion batteries comprising a lithium salt in a liquid carrier comprising heteroaromatic compound including a five-membered or six-membered heteroaromatic ring moiety selected from the group consisting of a furan, a pyrazine, a triazine, a pyrrole, and a thiophene, the heteroaromatic ring moiety bearing least one carboxylic ester or carboxylic anhydride substituent bound to at least one carbon atom of the heteroaromatic ring. Preferred heteroaromatic ring moieties include pyridine compounds, pyrazine compounds, pyrrole compounds, furan compounds, and thiophene compounds.

Heteroaromatic-based electrolytes for lithium and lithium-ion batteries

The present invention provides an electrolyte composition for a lithium or lithium-ion battery comprising a lithium salt in a liquid carrier comprising (a) a linear alkyl carbonate solvent, a cyclic alkyl carbonate solvent, or a combination thereof, and (b) a glycerol carbonate derivative compound of Formula (I): wherein X is selected from O, O(CO)O, S, N, P, P(&#x2550;O), B, and Si; n is 1 when X is O, O(CO)O, or S; n is 2 when x is N, P, P(&#x2550;O), or B; n is 3 when X is Si; and each R independently is selected from alkyl, alkenyl, alkynyl, aryl, acyl, heteroaryl, a 5-member ring heterocyclic group, a 5-member ring heterocycle-substituted methyl group, trialkylsilyl, and any of the foregoing substituted with one or more fluoro substituents, provided that R is acyl only when X is O, S, or N, and R is not alkyl when X is O(CO)O.

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Bolingbrook, IL, United States of America

Daniel Abraham