Granted Patent B2

US 12,407,022 · App. 18/937,303 · Granted Sep 2, 2025

Inventors: Kefei Wang (Ningde, CN); Qiao Zeng (Ningde, CN); Liangzhen Xiao (Ningde, CN); Fei Wu (Ningde, CN)

Assignee: Ningde Amperex Technology Limited

H01M10/0566H01M4/13H01M4/64H01M4/70H01M10/0525H01M10/0567H01M10/0569H01M2300/0025H01M2300/0034H01M2300/0037

Abstract

Claims (258)

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

⁢

3

⁢

wt

⁢

%

≤

(

X

+

Y

)

≤

about

⁢

11

⁢

wt

⁢

%

,

about

⁢

1

≤

(

X

/

Y

)

≤

about

⁢

6

,

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 2 wt %<X≤about 7 wt %, or about 1 wt %<Y<about 5 wt %, about 0.025<(Y/Z)≤about 0.05, or about 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 1.5<(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 , wherein about 3 wt %≤X≤about 6 wt %.

7. 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.

8. The electrolyte according to claim 7 , 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 —.

9. The electrolyte according to claim 7 , 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, CH 3 OCH 2 CH(CH 3 )OCH 2 CF 3 , FCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 F, FCH 2 CH 2 OCH 2 CH(CH 3 )OCH 2 CH 2 F, CF 3 CH 2 O(CH 2 CH 2 O) 2 CH 2 CF 3 , CF 3 CH 2 OCH 2 CH(CH 3 )OCH 2 CF 3 , and any combination thereof.

10. 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 %.

11. The electrolyte according to claim 1 , wherein the electrolyte satisfies at least one of the following conditions:

(1) 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 %;

(2) 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 2 M<Y≤ about 4 M;

(3) 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 %; or

(4) 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 %.

12. 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.

13. 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 %.

14. 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 %.

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 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 %.

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

17. 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

⁢

3

⁢

wt

⁢

%

≤

(

X

+

Y

)

≤

about

⁢

11

⁢

wt

⁢

%

,

about

⁢

1

≤

(

X

/

Y

)

≤

about

⁢

6

,

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.

18. The electrochemical device according to claim 17 , 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

≤

D

⁢

2

≤

about

4.3

g

/

cm

3

.

19. The electrochemical device according to claim 17 , 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.

20. The electrochemical device according to claim 17 , 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

≤

D

⁢

2

≤

about

1.8

g

/

cm

3

.

21. The electrochemical device according to claim 17 , 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 %.

22. The electrochemical device according to claim 17 , 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

⁢

2

⁢

M

<

Y

≤

about

⁢

4

⁢

M

.

23. The electrochemical device according to claim 17 , 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 %.

24. The electrochemical device according to claim 17 , 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 %.

25. The electrochemical device according to claim 17 , 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 %.

26. The electrochemical device according to claim 17 , wherein about 3.5 wt %<(X+Y)<about 8 wt %, and about 1.5<(X/Y)<about 4.

27. The electrochemical device according to claim 17 , wherein about 2 wt %<X≤about 7 wt % or about 1 wt %<Y<about 5 wt %, or about 0.025<(Y/Z)≤about 0.05, or about 40 wt %≤Z≤about 50 wt %.

28. 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

⁢

3

⁢

wt

⁢

%

≤

(

X

+

Y

)

≤

about

⁢

11

⁢

wt

⁢

%

,

;

about

⁢

1

≤

(

X

/

Y

)

≤

about

⁢

4

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)

Priority Claims (1)

Continuity (5)

References Cited (315)