IP Library › Granted Patent US 12,183,884
Granted Patent B2
US 12,183,884 · App. 18/626,697 · Granted Dec 31, 2024

Electrolyte and electrochemical device

Inventors: Kefei Wang (Ningde, CN); Qiao Zeng (Ningde, CN); Liangzhen Xiao (Ningde, CN); Fei Wu (Ningde, CN)
Assignee: Ningde Amperex Technology Limited
H01M10/0566H01M4/13H01M4/64H01M10/0525H01M10/0567H01M10/0569H01M2300/0025H01M2300/0034H01M2300/0037
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Quick Facts
Patent No.
US 12,183,884
App. No.
18/626,697
Granted
Dec 31, 2024
Kind
B2
Abstract

An electrolyte including a dinitrile compound, a trinitrile compound, and propyl propionate. Based on the total weight of the electrolyte, the weight percentage of the dinitrile compound is X, the weight percentage of the trinitrile compound is Y, and the weight percentage of the propyl propionate is Z, wherein, about 2 wt %<(X+Y)≤about 11 wt %, about 0.1≤(X/Y)≤about 4, about 30 wt %≤Z≤about 50 wt %, about 2 wt %<X≤about 6 wt %, and about 0.01<(Y/Z)≤about 0.3; wherein the trinitrile compound comprises at least one selected from the group consisting of 1,3,5-pentanetricarbonitrile; 1,2,3-propanetrinitrile, 1,3,6-hexanetricarbonitrile; 1,2,6-hexanetricarbonitrile, 1,2,3-tris(2-cyanoethoxy)propane; 1,2,4-tris(2-cyanoethoxy)butane, 1,1,1-tris(cyanoethoxymethylene)ethane, 1,1,1-tris(cyanoethoxymethylene)propane, 3-methyl-1,3,5-tris(cyanoethoxy)pentane, 1,2,7-tris(cyanoethoxy)heptane, 1,2,6-tris(cyanoethoxy)hexane, and 1,2,5-tris(cyanoethoxy)pentane.

Claims (75)

1. An electrolyte, comprising a dinitrile compound, a trinitrile compound, and propyl propionate; wherein, based on a total weight of the electrolyte, a weight percentage of the dinitrile compound is X, a weight percentage of the trinitrile compound is Y and a weight percentage of the propyl propionate is Z; wherein,

about 2 wt %<(X+Y)≤about 11 wt %,

about 0.1≤(X/Y)≤about 4,

about 30 wt %≤Z≤about 50 wt %,

about 2 wt %<X≤about 6 wt %, and

about 0.01<(Y/Z)≤about 0.3;

wherein the trinitrile compound comprises at least one selected from the group consisting of: 1,3,5-pentanetricarbonitrile; 1,2,3-propanetrinitrile; 1,3,6-hexanetricarbonitrile; 1,2,6-hexanetricarbonitrile; 1,2,3-tris(2-cyanoethoxy)propane; 1,2,4-tris(2-cyanoethoxy)butane; 1,1,1-tris(cyanoethoxymethylene)ethane; 1,1,1-tris(cyanoethoxymethylene)propane; 3-methyl-1,3,5-tris(cyanoethoxy)pentane; 1,2,7-tris(cyanoethoxy)heptane; 1,2,6-tris(cyanoethoxy)hexane; and 1,2,5-tris(cyanoethoxy)pentane.

2. The electrolyte according to claim 1 , wherein about 3 wt %≤X≤about 6 wt % or about 1 wt %<Y<about 5 wt % or 40 wt %≤Z≤about 50 wt %.

3. The electrolyte according to claim 1 , wherein about 3.5 wt %<(X+Y)<about 8 wt %, and about 0.1≤(X/Y)≤about 4.

4. The electrolyte according to claim 1 , wherein the dinitrile compound comprises a compound of Formula (4) or (5):

CN—R 1 —CN  (4);

CN—R 2 —(O—R 3 ) n —O—R 4 —CN  (5);

or a combination thereof,

where R 1 , R 2 , R 3 and R 4 are each independently an alkylene group having 1-5 carbon atoms or an alkenylene group having 2-5 carbon atoms,

and n represents an integer from 0 to 5.

5. The electrolyte according to claim 1 , wherein the dinitrile compound is one selected from the group consisting of butanedinitrile, glutaronitrile, adiponitrile, 1,5-dicyanopentane, 1,6-dicyanohexane, 1,7-dicyanoheptane, 1,8-dicyanooctane, 1,9-dicyanononane, 1,10-dicyanodecane, 1,12-dicyanododecane, tetramethylbutanedinitrile, 2-methylglutaronitrile, 2,4-dimethylglutaronitrile, 2,2,4,4-tetramethylglutaronitrile, 1,4-dicyanopentane, 2,6-dicyanoheptane, 2,7-dicyanooctane, 2,8-dicyanononane, 1,6-dicyanodecane, 1,2-dicyanobenzene, 1,3-dicyanobenzene, 1,4-dicyanobenzene, 3,5-dioxa-pimelonitrile, 1,4-bis(cyanoethoxy)butane, ethylene glycol bis(2-cyanoethyl)ether, diethylene glycol bis(2-cyanoethyl)ether, triethylene glycol bis(2-cyanoethyl)ether, tetraethylene glycol bis(2-cyanoethyl)ether, 3,6,9,12,15,18-hexaoxaeicosanoic dinitrile, 1,3-bis(2-cyanoethoxy)propane, 1,4-bis(2-cyanoethoxy)butane, 1,5-bis(2-cyanoethoxy)pentane, ethylene glycol bis(4-cyanobutyl)ether, 1,4-dicyano-2-butene, 1,4-dicyano-2-methyl-2-butene, 1,4-dicyano-2-ethyl-2-butene, 1,4-dicyano-2,3-dimethyl-2-butene, 1,4-dicyano-2,3-diethyl-2-butene, 1,6-dicyano-3-hexene, 1,6-dicyano-2-methyl-3-hexene, 1,6-dicyano-2-methyl-5-methyl-3-hexene, and any combination thereof.

6. The electrolyte according to claim 1 , further comprising a fluoroether comprising at least one of the compounds of Formula (8), Formula (9), Formula (10) or Formula (11):

Rf1-O-Rf2  (8);

Rf1-O—R  (9)

Rf1-O—(R′—O) n -Rf2  (10); and

Rf1-O—(R′—O) n —R  (11);

wherein Formulae (8), (9), (10), and (11), Rf1 and Rf2 are each independently a linear or branched C 1 to C 12 fluoroalkyl group having at least one hydrogen atom substituted with fluoro, R is a linear or branched C 1 to C 12 alkyl group, and R′ is a linear or branched C 1 to C 5 alkylene group, and n is an integer from 1 to 5.

7. The electrolyte according to claim 6 , wherein Rf1 or Rf2 is each independently a fluoroalkyl group selected from the group consisting of HCF 2 —, CF 3 —, HCF 2 CF 2 —, CH 3 CF 2 —, CF 3 CH 2 —, CF 3 CF 2 —, (CF 3 ) 2 CH—, HCF 2 CF 2 CH 2 —, CF 3 CH 2 CH 2 —, HCF 2 CF 2 CF 2 CH 2 —, HCF 2 CF 2 CF 2 CF 2 CH 2 —, CF 3 CF 2 CH 2 —, CF 3 CFHCF 2 CH 2 —, HCF 2 CF(CF 3 )CH 2 —, and CF 3 CF 2 CH 2 CH 2 —.

8. The electrolyte according to claim 6 , wherein the fluoroether is one selected from the group consisting of: HCF 2 CF 2 CH 2 OCF 2 CF 2 H, (CF 3 ) 2 CFCF(CF 2 CF 3 )(OCH 3 ), CF 3 CHFCF 2 CH(CH 3 )OCF 2 CHFCF 3 , HCF 2 CF 2 CH 2 OCF 2 CF 2 CF 2 CF 2 H, HCF 2 CF 2 OCH 2 CF 3 , HCF 2 CF 2 OCH 2 CH 2 OCF 2 CF 2 H, HCF 2 CF 2 OCH 2 CH 2 CH 2 OCF 2 CF 2 H, HCF 2 CF 2 CH 2 OCF 2 CF 2 CF 2 H, HCF 2 CF 2 OCH 2 CH 2 OCF 2 CF 2 CF 2 H, HCF 2 CF 2 OCH 2 CH 2 CH 2 OCF 2 CF 2 CF 2 H, CH 3 OCH 2 CH 2 OCH 2 CH 2 F, CH 3 OCH 2 CH 2 OCH 2 CF 3 , CH 3 OCH 2 CH(CH 3 )OCH 2 CH 2 F, FCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 F, CF 3 CH 2 O(CH 2 CH 2 O) 2 CH 2 CF 3 , CH 3 OCH 2 CH(CH 3 )OCH 2 CF 3 , FCH 2 CH 2 OCH 2 CH(CH 3 )OCH 2 CH 2 F, CF 3 CH 2 OCH 2 CH(CH 3 )OCH 2 CF 3 , and any combination thereof.

9. The electrolyte according to claim 1 , further comprising a cyclic phosphonic anhydride; based on the total weight of the electrolyte, a content of the cyclic phosphonic anhydride is about 0.01-10 wt %.

10. The electrolyte according to claim 1 , wherein the dinitrile compound comprises ethylene glycol bis(2-cyanoethyl) ether; based on the total weight of the electrolyte, a content of the ethylene glycol bis(2-cyanoethyl) ether is greater than 0.01 wt %, and less than 1 wt %.

11. The electrolyte according to claim 1 , wherein the dinitrile compound comprises ethylene glycol bis(2-cyanoethyl) ether; based on the total weight of the electrolyte, a content of the ethylene glycol bis(2-cyanoethyl) ether is M;

wherein,

about 2M<Y≤about 4M.

12. The electrolyte according to claim 1 , wherein the dinitrile compound comprises adiponitrile; based on the total weight of the electrolyte, a content of the adiponitrile is greater than 0.01 wt %, and less than 4 wt %.

13. The electrolyte according to claim 1 , wherein the dinitrile compound comprises butanedinitrile; based on the total weight of the electrolyte, a content of the butanedinitrile is greater than 0.3 wt %, and less than 6 wt %.

14. The electrolyte according to claim 1 , further comprising one selected from a group consisting of: a cyclic carbonate ester having a carbon-carbon double bond, a fluorinated chain carbonate ester, a fluorinated cyclic carbonate ester, a compound having a sulfur-oxygen double bond, and any combination thereof.

15. The electrolyte according to claim 1 , further comprising a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises 1,3-propanesultone; based on the total weight of the electrolyte, a content of the 1,3-propanesultone is greater than 0.01 wt %, and less than 3 wt %.

16. The electrolyte according to claim 1 , further comprising a fluorinated cyclic carbonate ester, wherein the fluorinated cyclic carbonate ester comprises fluoroethylene carbonate; based on the total weight of the electrolyte, a content of the fluoroethylene carbonate is greater than 0.1 wt %, and less than 4 wt %.

17. The electrolyte according to claim 1 , further comprising a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises ethylene sulfate; based on the total weight of the electrolyte, a content of the ethylene sulfate is greater than 0.5 wt %, and less than 2 wt %.

18. The electrolyte according to claim 1 , further comprising a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises ethylene sulfate; based on the total weight of the electrolyte, a content of the ethylene sulfate is greater than 0.01 wt %, and less than 0.5 wt %.

19. The electrolyte according to claim 1 , further comprising a cyclic carboxylate ester, including γ-butyrolactone or γ-valerolactone or a combination thereof.

20. An electrochemical device, wherein the electrochemical device comprises electrodes and an electrolyte comprising a dinitrile compound, a trinitrile compound, and propyl propionate; wherein, based on the total weight of the electrolyte, the weight percentage of the dinitrile compound is X and the weight percentage of the trinitrile compound is Y, and a weight percentage of the propyl propionate is Z; wherein,

About 2 wt %<(X+Y)≤about 11 wt %,

about 0.1≤(X/Y)≤about 4,

about 30 wt %≤Z≤about 50 wt %,

about 2 wt %<X≤about 6 wt %, and

about 0.01<(Y/Z)≤about 0.3;

wherein the trinitrile compound comprises at least one selected from the group consisting of: 1,3,5-pentanetricarbonitrile; 1,2,3-propanetrinitrile; 1,3,6-hexanetricarbonitrile; 1,2,6-hexanetricarbonitrile; 1,2,3-tris(2-cyanoethoxy)propane; 1,2,4-tris(2-cyanoethoxy)butane; 1,1,1-tris(cyanoethoxymethylene)ethane; 1,1,1-tris(cyanoethoxymethylene)propane; 3-methyl-1,3,5-tris(cyanoethoxy)pentane; 1,2,7-tris(cyanoethoxy)heptane; 1,2,6-tris(cyanoethoxy)hexane; and 1,2,5-tris(cyanoethoxy)pentane.

21. The electrochemical device according to claim 20 , wherein the electrode comprises a cathode,

the cathode comprises a current collector, a single-sided coating and a double-sided coating;

a first part of the current collector is provided with the single-sided coating and a second part of the current collector is provided with the double-sided coating;

an electrode compaction density of the single-sided coating is D1, and, an electrode compaction density of the double-sided coating is D2, wherein, about 0.8≤(D1/D2)≤about 1.2; and,

about 3.5 g/cm 3 ≤D2≤about 4.3 g/cm 3 .

22. The electrochemical device according to claim 20 , wherein,

both the single-sided coating and the double-sided coating are present on the same electrode; or,

only a single-sided coating or a double-sided coating present on the same electrode.

23. The electrochemical device according to claim 20 , wherein the electrode comprises an anode,

the anode comprises a current collector, a single-sided coating and a double-sided coating;

a first part of the current collector is provided with the single-sided coating and a second part of the current collector is provided with the double-sided coating;

an electrode compaction density of the single-sided coating is D1, and, an electrode compaction density of the double-sided coating is D2, wherein, about 0.8≤(D1/D2)≤about 1.2; and,

about 1.2 g/cm 3 ≤D2≤about 1.8 g/cm 3 .

24. The electrochemical device according to claim 20 , wherein the dinitrile compound comprises ethylene glycol bis(2-cyanoethyl) ether; based on the total weight of the electrolyte, a content of ethylene glycol bis(2-cyanoethyl) ether is greater than 0.01 wt %, and less than 1 wt %.

25. The electrochemical device according to claim 20 , wherein the dinitrile compound comprises ethylene glycol bis(2-cyanoethyl) ether; based on the total weight of the electrolyte, a content of ethylene glycol bis(2-cyanoethyl) ether is M; wherein,

about 2M<Y≤about 4M.

26. The electrochemical device according to claim 20 , wherein the electrochemical device satisfies at least one of the following conditions:

(1) the dinitrile compound comprises adiponitrile; based on the total weight of the electrolyte, a content of adiponitrile is greater than 0.01 wt %, and less than 4 wt %;

(2) the electrolyte further comprises a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises 1,3-propanesultone; based on the total weight of the electrolyte, a content of 1,3-propanesultone is greater than 0.01 wt %, and less than 3 wt %;

(3) the electrolyte further comprises a fluorinated cyclic carbonate ester, wherein the fluorinated cyclic carbonate ester comprises fluoroethylene carbonate; based on the total weight of the electrolyte, a content of fluoroethylene carbonate is greater than 0.1 wt %, and less than 4 wt %; or

(4) the dinitrile compound comprises butanedinitrile; based on the total weight of the electrolyte, a content of butanedinitrile is greater than 0.3 wt %, and less than 6 wt %.

27. The electrochemical device according to claim 20 , further comprising a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises ethylene sulfate; based on the total weight of the electrolyte, a content of ethylene sulfate is greater than 0.5 wt %, and less than 2 wt %.

28. The electrochemical device according to claim 20 , further comprising a compound having a sulfur-oxygen double bond, wherein the compound having a sulfur-oxygen double bond comprises ethylene sulfate; based on the total weight of the electrolyte, a content of ethylene sulfate is greater than 0.01 wt %, and less than 0.5 wt %.

29. The electrochemical device according to claim 20 , wherein about 1 wt %<Y<about 5 wt %, or about 40 wt %≤Z≤about 50 wt %.

30. An electronic device, comprising an electrochemical device that includes electrodes and an electrolyte comprising a dinitrile compound, a trinitrile compound, and propyl propionate; wherein, based on the total weight of the electrolyte, the weight percentage of the dinitrile compound is X and the weight percentage of the trinitrile compound is Y and a weight percentage of the propyl propionate is Z; wherein,

about 2 wt %<(X+Y)≤about 11 wt %;

about 0.1≤(X/Y)≤about 4,

about 30 wt %≤Z≤about 50 wt %,

about 2 wt %<X≤about 6 wt %, and

about 0.01<(Y/Z)≤about 0.3;

wherein the trinitrile compound comprises at least one selected from the group consisting of: 1,3,5-pentanetricarbonitrile; 1,2,3-propanetrinitrile; 1,3,6-hexanetricarbonitrile; 1,2,6-hexanetricarbonitrile; 1,2,3-tris(2-cyanoethoxy)propane; 1,2,4-tris(2-cyanoethoxy)butane; 1,1,1-tris(cyanoethoxymethylene)ethane; 1, 1,1-tris(cyanoethoxymethylene)propane; 3-methyl-1,3,5-tris(cyanoethoxy)pentane; 1,2,7-tris(cyanoethoxy)heptane; 1,2,6-tris(cyanoethoxy)hexane; and 1,2,5-tris(cyanoethoxy)pentane.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2024
From: WANG, KEFEI; ZENG, QIAO; XIAO, LIANGZHEN; WU, FEI
To: NINGDE AMPEREX TECHNOLOGY LIMITED
Reel/Frame 067007/0685 →
Priority Claims (1)
CN 201811108529.X · Sep 21, 2018 · national
Continuity (4)
Continuation 17990641 · Nov 18, 2022
Continuation 17064959 · Oct 7, 2020
Continuation 16211853 · Dec 6, 2018
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