IP Library Granted Patent US 12,388,114
Granted Patent B2
US 12,388,114 · App. 17/705,530 · Granted Aug 12, 2025

In situ generated solid electrolyte for energy storage

Inventors: Zhengcheng Zhang (Naperville, IL); Quinton James Meisner (Westmont, IL); Tobias Glossmann (Birmingham, MI)
Assignees: UCHICAGO ARGONNE, LLC; MERCEDES-BENZ RESEARCH & DEVELOPMENT NORTH AMERICA, INC.
H01M10/0567C07D331/02H01M4/382H01M10/052H01M10/0565H01M2300/0025H01M2300/0082H01M2300/0085H01M2300/0091
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Quick Facts
Patent No.
US 12,388,114
App. No.
17/705,530
Granted
Aug 12, 2025
Kind
B2
Abstract

A battery includes a cathode including a cathode active material, an anode comprising lithium, and an electrolyte including an aprotic solvent, a lithium salt, and a compound or mixture of two or more different compounds each containing at least one epi-sulfide group.

Claims (32)

1. A battery comprising a cathode comprising a cathode active material, an anode comprising lithium, and an electrolyte comprising an aprotic solvent, a lithium salt, and a compound containing at least one epi-sulfide group;

wherein:

the compound is represented as [epi-sulfide]-[L]-[epi-sulfide], wherein L is a linker; or

the compound is represented as by Formula I:

wherein:

each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is individually H, alkyl, alkoxy, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclylalkoxyl, heterocyclyl, or heterocyclylalkyl;

q is 0, 1, 2, or 3;

q′ is 1, 2, 3, or 4; and

r is at least 1.

2. The battery of claim 1 , wherein the electrolyte comprises a mixture of two or more different compounds each containing at least one epi-sulfide group.

3. The battery of claim 1 , wherein each L is alkyl, ether, polyether, aryl, heteroaryl, or heterocyclyl.

4. The battery of claim 1 , wherein the compound is represented by Formula I:

wherein:

each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is individually H, alkyl, alkoxy, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclylalkoxyl, heterocyclyl, or heterocyclylalkyl;

q is 0, 1, 2, or 3;

q′ is 1, 2, 3, or 4; and

r is at least 1.

5. The battery of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are H or alkyl, R 6 is H, alkyl or

q is 1 or 2, q′ is 1 or 2, and r is 0, 1, or 2.

6. The battery of claim 4 , wherein the electrolyte comprises a mixture of two or more different compounds of Formula I.

7. The battery of claim 6 , wherein the two or more different compounds of Formula I, represented as Formulae IA and IB:

wherein:

each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is individually H, alkyl, alkoxy, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclylalkoxyl, heterocyclyl, or heterocyclylalkyl;

each R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , R 6′ , and R 7′ is individually H, alkyl, alkoxy, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclylalkoxyl, heterocyclyl, or heterocyclylalkyl, with the proviso that at least one R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , R 6′ , and R 7′ contains a heterocyclyl group;

each q is individually 0, 1, 2, or 3;

each q′ is individually 1, 2, 3, or 4; and

each r individually is at least 1.

8. The battery of claim 7 , wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually H or alkyl; each q is individually 1 or 2; each q′ is individually 1 or 2; each r is individually 0, 1, or 2; and each R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , and R 6′ individually is H or alkyl, and R 7′ is heterocyclyl.

9. The battery of claim 7 , wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually H or alkyl; each q is individually 1 or 2; each q′ is individually 1 or 2; each r is individually 0, 1, or 2; and each R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , and R 6′ individually is H or alkyl, and R 7′ is

10. The battery of claim 7 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are H; each q is individually 1 or 2; each q′ is individually 1 or 2; and each r is individually 0, 1, or 2; R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , and R 6′ are H, and R 7 is

11. The battery of claim 1 , wherein the compound is a mixture of G 1 S and SG x S:

12. The battery of claim 1 , wherein the cathode active material comprises sulfur.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2023
From: GLOSSMANN, TOBIAS
To: MERCEDES-BENZ RESEARCH & DEVELOPMENT NORTH AMERICA, INC.
Reel/Frame 062329/0376 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2023
From: MEISNER, QUINTON JAMES; ZHANG, ZHENGCHENG
To: UCHICAGO ARGONNE, LLC
Reel/Frame 062329/0659 →
CONFIRMATORY LICENSE Recorded Sep 2, 2022
From: UCHICAGO ARGONNE, LLC
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 060979/0746 →
Continuity (1)
Related Publication 20230327197A1 · Oct 12, 2023
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