IP Library › Granted Patent US 11,799,131
Granted Patent B2
US 11,799,131 · App. 17/885,920 · Granted Oct 24, 2023

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 11,799,131
App. No.
17/885,920
Granted
Oct 24, 2023
Kind
B2
Abstract

An electrochemical device, including an electrode and an electrolyte. The 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 8. The electrode including a coating, which including a single-sided sub-coating and a double-sided coating, the electrode with the single-sided sub-coating has an electrode compaction density D1, and the electrode with the double-sided coating has an electrode compaction density D2, where about 0.8≤D1/D2≤ about 1.2. The electrolyte and D1/D2 of the electrodes has a significant effect on the cycle performance of the electrochemical device.

Claims (51)

1. An electrochemical device, comprising:

an electrode; and

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, and a weight percentage of the trinitrile compound is Y; wherein,

about 2 wt %≤(X+Y)≤about 8 wt %, and

about 0.1≤(X/Y)≤about 6; wherein,

the electrode 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; and

an electrode compaction density of the electrode corresponding to the first part with the single-sided coating is D1, and, an electrode compaction density of the electrode corresponding to the second part with the double-sided coating is D2, wherein, about 0.8≤D1/D2≤about 1.2;

wherein based on the total weight of the electrolyte, a weight percentage of the propyl propionate is Z; wherein,

about 0.01≤(Y/Z)≤about 0.3;

wherein the trinitrile compound is 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; 1,2,5-tris(cyanoethoxy)pentane; and any combination thereof.

2. The electrochemical device according to claim 1 , wherein the electrode is a cathode, and 3.5 g/cm 3 ≤D2≤4.3 g/cm 3 .

3. The electrochemical device according to claim 1 , wherein the electrode is an anode, and 1.2 g/cm 3 ≤D2≤1.8 g/cm 3 .

4. The electrochemical device according to claim 1 , wherein the dinitrile compound further comprises a compound of Formula (4):

CN—R 1 —CN  (4);

where R 1 selected from an alkylene group having 1-5 carbon atoms or an alkenylene group having 2-5 carbon atoms.

5. The electrochemical device 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 electrochemical device according to claim 1 , wherein the trinitrile compound comprises a compound of Formula (6)

CN—(CH 2 ) x —CH{(CH 2 ) y —CN}—(CH 2 ) z —CN  (6);

or a combination thereof,

where in Formula (6), x, y, and z represent an integer from 0 to 5, and x, y, and z are not 0 at the same time; and

in Formula (7), R 5 represents hydrogen or an alkyl group having 1-5 carbon atoms, R 6 , R 7 and R 8 are each independently an alkylene group having 1-5 carbon atoms, and X 4 , X 5 and X 6 are each independently —R 9 —CN, in which R 9 represents an alkylene group having 1-5 carbon atoms.

7. The electrochemical device according to claim 1 , wherein X is about 0.01-10 wt %, Y is about 0.01-10 wt %, and a weight percentage Z of the propyl propionate is about 5-50 wt %.

8. The electrochemical device according to claim 1 , wherein the electrolyte 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.

9. The electrochemical device 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 -.

10. The electrochemical device 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.

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

12. The electrochemical device according to claim 1 , wherein the electrolyte 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 electrochemical device according to claim 1 , wherein the electrolyte further comprising a cyclic carboxylate ester, including γ-butyrolactone or γ-valerolactone or a combination thereof.

14. An electrochemical device, comprising:

electrodes; and

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, and a weight percentage of the trinitrile compound is Y; wherein,

about 2 wt %≤(X+Y)≤about 8 wt %, and

about 0.1≤(X/Y)≤about 6; wherein,

the electrodes comprise a first electrode and a second electrode, wherein

the first electrode comprises a first current collector and a single-sided coating;

the second electrode comprises a second current collector and a double-sided coating; and

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

wherein based on the total weight of the electrolyte, a weight percentage of the propyl propionate is Z; wherein,

about 0.01≤(Y/Z)≤about 0.3;

wherein the trinitrile compound is 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; 1,2,5-tris(cyanoethoxy)pentane; and any combination thereof.

15. The electrochemical device according to claim 14 , wherein the first electrode is a cathode, the second electrode is a cathode, and 3.5 g/cm 3 ≤D2≤4.3 g/cm 3 .

16. The electrochemical device according to claim 14 , wherein the first electrode is an anode, the second electrode is an anode, and 1.2 g/cm 3 ≤D2≤1.8 g/cm 3 .

17. The electrochemical device according to claim 14 , 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2022
From: WANG, KEFEI; ZENG, QIAO; XIAO, LIANGZHEN; WU, FEI
To: NINGDE AMPEREX TECHNOLOGY LIMITED
Reel/Frame 060786/0449 →
Priority Claims (1)
CN 201811108529.X · Sep 21, 2018 · national
Continuity (3)
Continuation 17064782 · Oct 7, 2020
Continuation 16211853 · Dec 6, 2018
Related Publication 20220407109A1 · Dec 22, 2022
Cited By (1)
US 12,407,022