IP Library › Granted Patent US 10,978,741

Granted Patent B2

US 10,978,741 · App. 16/266,496 · Granted Apr 13, 2021

Non-aqueous electrolytes for electrochemical cells

Inventors: Chi Cheung Su (Westmont, IL); Khalil Amine (Oakbrook, IL); Meinan He (Willowbrook, IL)

Assignee: UCHICAGO ARGONNE, LLC

H01M10/0568 H01M10/0567 H01M10/0569 H01M10/0525 H01M2300/0025

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Quick Facts

Patent No.: US 10,978,741
App. No.: 16/266,496
Granted: Apr 13, 2021
Kind: B2

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Abstract

A non-aqueous electrolyte comprising a salt, a non-aqueous solvent, and a compound of Formula (I), (II), or (III), where E is —S(O)— or S(O) 2 —:

Claims (49)

1. A non-aqueous electrolyte comprising:

a salt; and

a compound of Formula (I), Formula (II), Formula (III), or a mixture of any two or more thereof:

wherein:

E is —S(O) 2 — or —S(O)—;

R 1 is H, F, —OR 6 , alkyl, alkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl, heterocyclylalkyl, cycloalkyl, cycloalkylalkyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

R 2 , R 3 , R 4 , and R 5 are individually H, F, alkyl, alkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl, heterocyclylalkyl, cycloalkyl, cycloalkylalkyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

R 6 is H, —C(O)R 7 , alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, alkynyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

R 7 is H, alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, alkynyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

q is 0, 1, or 2;

R 10 , R 10′ , R 11 and R 11′ are individually H, F, alkyl, alkenyl, alkynyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl, heterocyclylalkyl, cycloalkyl, cycloalkylalkyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 , or R 10 and R 11 or R 10′ and R 11′ may join to form a heterocycle with the nitrogen to which they are attached, with the proviso for Formula (III) that at least one of R 10 , R 10′ , R 11 and R 11′ is other than H; and

R 12 is H, —C(O)R 7 , alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ; and

wherein any of the alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, or alkynyl groups are substituted or unsubstituted.

2. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (I).

3. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (I); R 1 is C 1-6 alkyl, —(CR 20 2 ) p O(C 1 -C 6 alkyl), —(CR 20 2 ) p O(C 1 -C 6 aryl), or —(CR 20 2 ) p O(C 1 -C 6 aralkyl); R 2 , R 3 , R 4 , and R 5 are each H, F, OR 6 , or C 1-6 alkyl; each R 20 is individually H or F; and p is 1, 2, or 3.

4. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (I); R 1 is methyl, ethyl, or benzyl; and R 2 , R 3 , R 4 , and R 5 are each H.

5. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (I); R 1 is C 1-6 fluorinated alkyl, C 1-6 fluorinated alkenyl, or C 1-6 fluorinated alkynyl; and R 2 , R 3 , R 4 , and R 5 are C 1-6 fluorinated alkyl or H.

6. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (I); R 1 is —CH 3 , —CFH 2 , —CF 2 H, —CF 3 , —CH 2 CH 3 , —CFHCH 3 , —CH 2 CFH 2 , —CH 2 CF 2 H, —CH 2 CF 3 , —CFHCH 3 , —CFHCFH 2 , —CFHCF 2 H, —CFHCF 3 , —CF 2 CH 3 , —CF 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CF 3 , —CHCH 2 , —CFCH 2 , —CHCFH, —CHCF 2 , —CFCFH, —CFCF 2 , —CH 2 CF 2 CF 3 , —CF(CH 3 ) 2 , —CH 2 CF 2 CF 3 , —CF 2 CF(CF 3 ) 2 , —CH 2 CF 2 CF 2 H, —CH 2 OCF 3 , —CF 2 OCF 3 , —CH 2 OCF 2 CF 2 CF 3 , —CH 2 OCF 2 CF 2 CF 2 CF 3 , —CF 2 OCF 2 CF 2 CF 3 , —C 6 F 5 , —CH 2 OC 6 F 5 ; —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 (CH 3 ) 2 , —CH 2 OCH 3 , —C 6 H 5 , —CH 2 OC 6 H 5 , —CH 2 OCH 2 CH 3 , —CH 2 OCH(CH 3 ) 2 , —C(CH 3 )HOCH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 3 ; and R 2 , R 3 , R 4 , and R 5 are individually H, —CH 3 , —CFH 2 , —CF 2 H, —CF 3 , —CH 2 CH 3 , —CFHCH 3 , —CH 2 CFH 2 , —CH 2 CF 2 H, —CH 2 CF 3 , —CFHCH 3 , —CFHCFH 2 , —CFHCF 2 H, —CFHCF 3 , —CF 2 CH 3 , —CF 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CF 3 , —CHCH 2 , —CFCH 2 , —CHCFH, —CHCF 2 , —CFCFH, —CFCF 2 , —CH 2 CF 2 CF 3 , —CF(CH 3 ) 2 , —CH 2 CF 2 CF 3 , —CF 2 CF(CF 3 ) 2 , —CH 2 CF 2 CF 2 H, —CH 2 OCF 3 , —CF 2 OCF 3 , —CH 2 OCF 2 CF 2 CF 3 , —CH 2 OCF 2 CF 2 CF 2 CF 3 , —CF 2 OCF 2 CF 2 CF 3 , —C 6 F 5 , —CH 2 OC 6 F 5 ; —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 (CH 3 ) 2 , —CH 2 OCH 3 , —C 6 H 5 , —CH 2 OC 6 H 5 , —CH 2 OCH 2 CH 3 , —CH 2 OCH(CH 3 ) 2 , —C(CH 3 )HOCH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 3 .

7. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (II).

8. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (II); R 10 and R 11 are individually C 1-6 alkyl, —(CR 20 2 ) p O(C 1 -C 6 alkyl), —(CR 20 2 ) p O(C 1 -C 6 aryl), or —(CR 20 2 ) p O(C 1 -C 6 aralkyl); R 12 is C 1-6 alkyl, —(CR 20 2 ) p O(C 1 -C 6 alkyl), —(CR 20 2 ) p O(C 1 -C 6 aryl), or —(CR 20 2 ) p O(C 1 -C 6 aralkyl); each R 20 is individually H or F; and p is 1, 2, or 3.

9. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (II); R 10 and R 11 are individually methyl, ethyl, or benzyl; and R 12 is methyl, ethyl, or benzyl.

10. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (II); R 10 and R 11 are individually C 1-6 fluorinated alkyl, C 1-6 fluorinated alkenyl, or C 1-6 fluorinated alkynyl; and R 12 is fluorinated alkyl.

11. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (II); R 10 and R 11 are individually —CH 3 , —CFH 2 , —CF 2 H, —CF 3 , —CH 2 CH 3 , —CFHCH 3 , —CH 2 CFH 2 , —CH 2 CF 2 H, —CH 2 CF 3 , —CFHCH 3 , —CFHCFH 2 , —CFHCF 2 H, —CFHCF 3 , —CF 2 CH 3 , —CF 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CF 3 , —CHCH 2 , —CFCH 2 , —CHCFH, —CHCF 2 , —CFCFH, —CFCF 2 , —CH 2 CF 2 CF 3 , —CF(CH 3 ) 2 , —CH 2 CF 2 CF 3 , —CF 2 CF(CF 3 ) 2 , —CH 2 CF 2 CF 2 H, —CH 2 OCF 3 , —CF 2 OCF 3 , —CH 2 OCF 2 CF 2 CF 3 , —CH 2 OCF 2 CF 2 CF 2 CF 3 , —CF 2 OCF 2 CF 2 CF 3 , —C 6 F 5 , —CH 2 OC 6 F 5 ; —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 (CH 3 ) 2 , —CH 2 OCH 3 , —C 6 H 5 , —CH 2 OC 6 H 5 , —CH 2 OCH 2 CH 3 , —CH 2 OCH(CH 3 ) 2 , —C(CH 3 )HOCH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 3 ; and R 12 is —CH 3 , —CFH 2 , —CF 2 H, —CF 3 , —CH 2 CH 3 , —CFHCH 3 , —CH 2 CFH 2 , —CH 2 CF 2 H, —CH 2 CF 3 , —CFHCH 3 , —CFHCFH 2 , —CFHCF 2 H, —CFHCF 3 , —CF 2 CH 3 , —CF 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CF 3 , —CHCH 2 , —CFCH 2 , —CHCFH, —CHCF 2 , —CFCFH, —CFCF 2 , —CH 2 CF 2 CF 3 , —CF(CH 3 ) 2 , —CH 2 CF 2 CF 3 , —CF 2 CF(CF 3 ) 2 , —CH 2 CF 2 CF 2 H, —CH 2 OCF 3 , —CF 2 OCF 3 , —CH 2 OCF 2 CF 2 CF 3 , —CH 2 OCF 2 CF 2 CF 2 CF 3 , —CF 2 OCF 2 CF 2 CF 3 , —C 6 F 5 , —CH 2 OC 6 F 5 ; —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 (CH 3 ) 2 , —CH 2 OCH 3 , —C 6 H 5 , —CH 2 OC 6 H 5 , —CH 2 OCH 2 CH 3 , —CH 2 OCH(CH 3 ) 2 , —C(CH 3 )HOCH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 3 .

12. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (III).

13. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (III); R 10 , R 10′ , R 11 , and R 11′ are individually C 1-6 alkyl, —(CR 20 2 ) p O(C 1 -C 6 alkyl), —(CR 20 2 ) p O(C 1 -C 6 aryl), or —(CR 20 2 ) p O(C 1 -C 6 aralkyl); each R 20 is individually H or F; and p is 1, 2, or 3.

14. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (III); R 10 , R 10′ , R 11 , and R 11′ are individually methyl, ethyl, or benzyl.

15. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (III); and R 10 , R 10′ , R 11 , and R 11′ are individually C 1-6 fluorinated alkyl, C 1-6 fluorinated alkenyl, or C 1-6 fluorinated alkynyl.

16. The non-aqueous electrolyte of claim 1 , wherein the compound is of Formula (III); and R 10 , R 10′ , R 11 , and R 11′ are individually —CH 3 , —CFH 2 , —CF 2 H, —CF 3 , —CH 2 CH 3 , —CFHCH 3 , —CH 2 CFH 2 , —CH 2 CF 2 H, —CH 2 CF 3 , —CFHCH 3 , —CFHCFH 2 , —CFHCF 2 H, —CFHCF 3 , —CF 2 CH 3 , —CF 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CF 3 , —CHCH 2 , —CFCH 2 , —CHCFH, —CHCF 2 , —CFCFH, —CFCF 2 , —CH 2 CF 2 CF 3 , —CF(CH 3 ) 2 , —CH 2 CF 2 CF 3 , —CF 2 CF(CF 3 ) 2 , —CH 2 CF 2 CF 2 H, —CH 2 OCF 3 , —CF 2 OCF 3 , —CH 2 OCF 2 CF 2 CF 3 , —CH 2 OCF 2 CF 2 CF 2 CF 3 , —CF 2 OCF 2 CF 2 CF 3 , —C 6 F 5 , —CH 2 OC 6 F 5 ; —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 (CH 3 ) 2 , —CH 2 OCH 3 , —C 6 H 5 , —CH 2 OC 6 H 5 , —CH 2 OCH 2 CH 3 , —CH 2 OCH(CH 3 ) 2 , —C(CH 3 )HOCH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 3 .

17. The non-aqueous electrolyte of claim 1 further comprising an additive that is vinylene carbonate

methyl vinylene carbonate

fluoroethylene carbonate, difluoroethylene carbonate, lithium difluoro(oxalato)borate, lithium bis(oxalato)borate, dioxathiolane-2,2-dioxide, ethylene sulfite, 1,3-propane sultone, or dimethyl methyl phosphonate.

18. The non-aqueous electrolyte of claim 1 further comprising a non-aqueous solvent.

19. The non-aqueous electrolyte of claim 1 comprising from greater than 0 wt % up to 20 wt % of the compound, based upon the total weight of the electrolyte.

20. An electrochemical cell comprising:

an anode;

a cathode; and

a non-aqueous electrolyte comprising:

a salt;

a non-aqueous solvent; and

from greater than 0 wt % to about 20 wt % of a compound of Formula (I), Formula (II), Formula (III), or a mixture of any two or more thereof:

wherein:

R 1 is H, F, OR 6 , alkyl, alkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl, heterocyclylalkyl, cycloalkyl, cycloalkylalkyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

R 2 , R 3 , R 4 , and R S are individually H, F, alkyl, alkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl, heterocyclylalkyl, cycloalkyl, cycloalkylalkyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ;

q is 0, 1, or 2;

R 12 is H, —C(O)R 7 , alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, alkynyl, silyl, siloxy, an ether, a polyalkylene glycol, —CFH 2 , —CF 2 H, —CF 3 , —CF 2 CF 3 , —CF 2 CHF 2 , —CF 2 CH 3 , —CF 2 CH 2 F, —CHFCF 3 , —CHFCHF 2 , —CHFCH 3 , —CHFCH 2 F, —CH 2 CF 3 , —CH 2 CHF 2 , —CH 2 CH 2 F, —CF(CF 3 ) 2 , or —CH(CF 3 ) 2 ; and

wherein any of the alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, alkenyl, or alkynyl groups are substituted or unsubstituted.

Assignments (4)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2020

From: AMINE, KHALIL

To: UCHICAGO ARGONNE, LLC

Reel/Frame 051793/0735 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2020

From: HE, MEINAN

To: UCHICAGO ARGONNE, LLC

Reel/Frame 051793/0822 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2020

From: SU, CHI CHEUNG