IP Library › Granted Patent US 10,388,992
Granted Patent B2
US 10,388,992 · App. 15/304,726 · Granted Aug 20, 2019

Alkylbenzoate derivatives as electrolyte additive for lithium based batteries

Inventors: Rene Schmitz (Mannheim, DE); Diana Fuerst (Ludwigshafen, DE); Lucas Montag (Buerstadt, DE)
Assignee: Gotion Inc.
H01M10/4235H01M10/0525H01M10/0567H01M10/0568H01M10/0569H01M2300/0025
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Quick Facts
Patent No.
US 10,388,992
App. No.
15/304,726
Granted
Aug 20, 2019
Kind
B2
Abstract

The invention relates to an electrolyte composition containing at least one compound of (I) wherein R 1 is selected from C 1 to C 10 alkyl, and R 2 is selected from O(C 1 to C 10 alkyl), OC(O)(C 1 to C 10 alkyl), OC(O)O(C 1 to C 10 alkyl), OS(O)2(C 1 to C 10 alkyl) and S(O) 2 O(C 1 to C 10 alkyl), wherein C 1 to C 10 alkyl may be substituted by one or more F and wherein one or more CH 2 — groups of C 1 to C 10 alkyl which are not bound directly to O may be replaced by O.

Claims (51)

1. An electrolyte composition comprising at least one compound of formula (I)

wherein

R 1 represents a C 1 to C 10 alkyl, and

R 2 represents a OC(O)(C 1 to C 10 alkyl),

wherein C 1 to C 10 alkyl may be substituted by one or more F atoms, and

wherein one or more CH 2 -groups of the C 1 to C 10 alkyl which are not bound directly to O may be replaced by O.

2. The electrolyte composition according to claim 1 , wherein

R 1 represents a C 1 to C 6 alkyl, and

R 2 represents a OC(O)(C 1 to C 6 alkyl),

wherein the C 1 to C 6 alkyl may be substituted by one or more F atoms, and

wherein one or more CH 2 -groups of the C 1 to C 6 alkyl which are not bound directly to 0 may be replaced by 0.

3. The electrolyte composition according to claim 1 , wherein the concentration of the at least one compound of formula (I) in the electrolyte composition is in the range of from 0.1 to 20 wt.-%, based on the total weight of the electrolyte composition.

4. The electrolyte composition according to claim 1 , wherein the electrolyte composition contains further comprises at least one further additive.

5. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises at least one SEI forming additive and/or at least one additional overcharge protection additive.

6. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises at least one SEI forming additive selected from the group consisting of a vinylene carbonate; a vinylene carbonate derivative; a fluorinated ethylene carbonate; a fluorinated ethylene carbonate derivative; propane sultone; a derivative of propane sultone; ethylene sulfite; a derivative of ethylene sulfite; an oxalate comprising compound; a derivative of an oxalate comprising compound; and an

ionic compound comprising a cation of formula (II)

wherein

X is CH 2 or NR′,

R 3 is selected from represents a C 1 to C 6 alkyl,

R 4 is selected from represents a —(CH 2 ) u —SO 3 —(CH 2 ) v —R″,

—SO 3 — is —O—S(O) 2 — or —S(O) 2 —O—,

u is an integer from 1 to 8 and wherein one or more CH 2 groups of the —(CH 2 ) u — alkylene chain which are not directly bound to the N-atom and/or the SO 3 group may be replaced by O and wherein two adjacent CH 2 groups of the (CH 2 )— alkylene chain may be replaced by a C—C double bond,

v is an integer from 1 to 4,

R′ represents a C 1 to C 6 alkyl,

R″ represents a C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -C 12 aryl, and C 6 -C 24 aralkyl, which may comprise one or more F atoms, and wherein one or more CH 2 groups of alkyl, alkenyl, alkynyl and aralkyl which are not directly bound to the SO 3 group may be replaced by O,

and an anion selected from bis(oxalato) borate, di:fluoro (oxalato) borate, [F z B(C m F 2m+1 ) 4-z ] − , [F y P(C m F 2m+1 ) 6-y ] − , (C m F 2m+1 ) 2 P(O)O] − , [C m F 2m+1 P(O)O 2 ] 2− , [O—C(O)—C m F 2m+1 ] − , [O—S(O) 2 —C m F 2m+1 ] − , [N(C(O)—C m F 2m+1 ) 2 ] − , [N(S(O) 2 —C m F 2m+1 ) 2 ] − , [N(C(O)—C m F 2m+1 )(S(O) 2 —C m F 2m+1 )] − , [N(C(O)—C m F 2m+1 )(C(O)F)] − , [(N(S(O) 2 —C m F 2m+1 )(S(O) 2 F)] − , [N(S(O) 2 F) 2 ] − , [C(C(O)—C m F 2m+1 ) 3 ] − , [C(S(O) 2 —C m F 2m+1 ) 3 ] − ,

wherein m is an integer from 1 to 8, z is an integer from 1 to 4, and y is an integer from 1 to 6.

7. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises an additional overcharge protection additive represented by formula (III)

wherein

R 5 is cyclohexyl or C 6 -C 12 aryl, which may be substituted by one or more substituent selected independently from each other from F, Cl, Br, I, C 6 -C 12 aryl, and C 1 -C 6 alkyl, wherein C 6 -C 12 aryl and C 1 -C 6 alkyl may be substituted by one or more substituent

selected independently from each other from F, Cl, Br and I; and

R 6 , R 7 , R 8 , R 9 and R 10 may be same or different and are independently from each other selected from H, F, Cl, Br, I, C 6 -C 12 aryl, and C 1 -C 6 alkyl, wherein C 6 -C 12 aryl and C 1 -C 6 alkyl may be substituted by one or more substituent selected independently from each other from F, Cl, Br and I.

8. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises at least one aprotic organic solvent.

9. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises at least one aprotic organic solvent selected from the group consisting of a cyclic carbonate; an acyclic carbonate; a di-C 1 -C 10 -alkylether; a di-C 1 -C 4 -alkyl-C 2 -C 6 -alkylene ether; a di-C 1 -C 4 -alkyl-C 2 -C 6 -alkylene polyether; a cyclic ether; a cyclic acetal; an acyclic acetal; a cyclic ketal; an acyclic ketal; an orthocarboxylic acids ester; a cyclic ester of a carboxylic acid; an acyclic ester of a carboxylic acid; a cyclic sulfone; an acyclic sulfone; a cyclic nitrile; an acyclic nitrile; a cyclic dinitrile; and an acyclic dinitrile.

10. A method of making an electrolyte composition according to claim 1 , the method comprising:

adding at least one compound of formula (I)

to a solution comprising a conductive salt and a solvent,

wherein

R 1 represents a C 1 to C 10 alkyl, and

R 2 represents OC(O)(C 1 to C 10 alkyl),

wherein the C 1 to C 10 alkyl may be substituted by one or more F atoms, and

wherein one or more CH 2 -groups of the C 1 to C 10 alkyl which are not bound directly to O may be replaced by O.

11. An electrochemical cell comprising the electrolyte composition according to claim 1 .

12. The electrochemical cell according to claim 11 , wherein the electrochemical cell is a lithium battery.

13. A method of forming a passivating layer on an electrode, the method comprising:

decomposing at least one compound of formula (I)

in the presence of the electrode, the electrode being present in the electrochemical cell, wherein

R 1 represents a C 1 to C 10 alkyl, and

R 2 represents a OC(O)(C 1 to C 10 alkyl),

wherein the C 1 to C 10 alkyl may be substituted by one or more F atoms, and

wherein one or more CH 2 -groups of the C 1 to C 10 alkyl which are not bound directly to O may be replaced by O.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 9432529 ERRONEOUSLY ENTER IN THE PROPERTIES DATA PREVIOUSLY RECORDED ON REEL 043577 FRAME 0521. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 3, 2017
From: BASF SE
To: GOTION, INC.
Reel/Frame 044103/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2017
From: BASF SE
To: GOTION, INC.
Reel/Frame 043577/0521 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2017
From: SCHMITZ, RENE; FUERST, DIANA; MONTAG, LUCAS
To: BASF SE
Reel/Frame 041152/0417 →
Priority Claims (1)
EP 14165148 · Apr 17, 2014 · regional
Continuity (1)
Related Publication 20170040650A1 · Feb 9, 2017