IP Library Granted Patent US 9,005,822
Granted Patent B2
US 9,005,822 · App. 13/787,433 · Granted Apr 14, 2015

Functional electrolyte for lithium-ion batteries

Inventors: Lu Zhang (Lisle, IL); Zhengcheng Zhang (Naperville, IL); Khalil Amine (Oak Brook, IL)
Assignee: UChicago Argonne, LLC
C07C43/2055H01M10/052H01M10/0569H01M10/0567
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Quick Facts
Patent No.
US 9,005,822
App. No.
13/787,433
Granted
Apr 14, 2015
Kind
B2
Abstract

Functional electrolyte solvents include compounds having at least one aromatic ring with 2, 3, 4 or 5 substituents, at least one of which is a substituted or unsubstituted methoxy group, at least one of which is a tert-butyl group and at least one of which is a substituted or unsubstituted polyether or poly(ethylene oxide) (PEO) group bonded through oxygen to the aromatic ring, are provided.

Claims (28)

1. A functional electrolyte solvent comprising a compound of formula

wherein:

R 2 is H, F, Cl, Br, I, alkyl, or a polyether group; and

R 3 is H, F, Cl, Br, I, alkyl, or a polyether group.

2. The functional electrolyte solvent of claim 1 , wherein the compound has the structure

3. The functional electrolyte solvent of claim 1 , wherein the compound has the structure:

4. The functional electrolyte solvent of claim 1 , wherein the compound is:

5. The functional electrolyte solvent of claim 1 , wherein the compound is:

6. An electrolyte comprising:

the functional electrolyte solvent of claim 1 ; and

an alkali metal salt.

7. The electrolyte of claim 6 , wherein the functional electrolyte solvent is a redox active material and has a redox potential of 3 to 5 V.

8. The electrolyte if claim 6 , wherein the functional electrolyte solvent is 1-methoxy-4-(2-methoxyethoxy)-2,5-di-tert-butyl-benzene, 1-methoxy-4-[2-(2-methoxyethoxyl)ethoxy]-2,5-di-tert-butyl-benzene, or a mixture thereof.

9. The electrolyte of claim 6 , wherein the concentration of the functional electrolyte solvent in the electrolyte is from 0.0005 wt % and 60 wt %.

10. The electrolyte of claim 6 , wherein the alkali metal salt is a lithium salt.

11. The electrolyte of claim 6 , wherein the alkali metal salt is Li[(C 2 O 4 ) 2 B], Li(C 2 O 4 )BF 2 , LiClO 4 , LiBF 4 , LiAsF 6 , LiPF 6 , LiCF 3 SO 3 , Li(CF 3 SO 2 )2N, Li(CF 3 SO 2 ) 3 C, LiN(SO 2 C 2 F 5 ) 2 , lithium alkyl fluorophosphates, or a mixture of any two or more thereof.

12. The electrolyte of claim 6 further comprising a polar aprotic solvent.

13. The electrolyte of claim 12 , wherein the polar aprotic solvent is selected from ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, dimethyl ether, gamma butyrolactone, or a mixture of any two or more thereof.

14. The electrolyte of claim 6 , wherein the alkali metal salt is other than Li[(C 2 O 4 ) 2 B], Li(C 2 O 4 )BF 2 , and the electrolyte further comprises about 0.001 wt % to about 8 wt % of an electrode stabilizing additive that is Li[(C 2 O 4 ) 2 B], Li(C 2 O 4 )BF 2 , or a mixture thereof.

15. The electrolyte of claim 6 further comprising an electrode stabilizing additive that is a substituted or unsubstituted spirocyclic hydrocarbon containing at least one oxygen atom and at least one alkenyl or alkynyl group.

16. An electrochemical device comprising:

a cathode

an anode; and

an electrolyte of claim 6 .

17. The electrochemical device of claim 16 , wherein the device is a lithium secondary battery; the cathode is a lithium metal oxide cathode; the anode is a carbon or lithium metal anode; and the anode and cathode are separated from each other by a porous separator.

18. An electrolyte comprising:

an alkali metal salt; and

at least one of 1-methoxy-4-(2-methoxyethoxy)-2,5-di-tert-butyl-benzene, 1-methoxy-4-[2-(2-methoxyethoxyl)ethoxy]-2,5-di-tert-butyl-benzene, 1-methoxy-4-[2-[2-(2-ethoxyethoxyl)ethoxy]ethoxy]-2,5-di-tert-butyl-benzene, 1-methoxy-4-[2-[2-[2-(2-methoxyethoxyl)ethoxy]ethoxy]ethoxy]-2,5-di-tert-butyl-benzene, 1-methoxy-4-[2-[2-[2-[2-(2-methoxyethoxyl)ethoxy]ethoxy]ethoxy]ethoxy]-2,5-di-tert-butyl-benzene, and 1-methoxy-4-[2-[2-[2-[2-[2-(2-methoxyethoxyl)ethoxy]ethoxy]ethoxy]ethoxy]ethoxyl-2,5-di-tert-butyl-benzene.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2013
From: ZHANG, LU; ZHANG, ZHENGCHENG; AMINE, KHALIL
To: UCHICAGO ARGONNE, LLC
Reel/Frame 031014/0638 →
CONFIRMATORY LICENSE Recorded Jun 3, 2013
From: UCHICAGO ARGONNE, LLC
To: ENERGY, UNITED STATES DEPARTMENT OF
Reel/Frame 030530/0866 →
Continuity (1)
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