IP Library › Granted Patent US 11,799,130
Granted Patent B2
US 11,799,130 · App. 17/885,915 · 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 11,799,130
App. No.
17/885,915
Granted
Oct 24, 2023
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; where about 2 wt %≤(X+Y)≤about 11 wt %, about 0.1≤(X/Y)≤about 8, and about 0.01≤(Y/Z)≤about 0.3. The dinitrile compound comprises a compound of Formula (5): N—R 2 —(O—R 3 ) n —O—R 4 —CN (5). The electrolyte is capable of effectively inhibiting the increase in DC internal resistance of an electrochemical device so that the electrochemical device has excellent cycle and storage performance.

Claims (59)

1. An electrolyte, comprising a dinitrile compound, a trinitrile compound, and propyl propionate, wherein, based on a 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 8 wt %,

about 0.1≤(X/Y)≤about 6, and

about 0.01≤(Y/Z)≤about 0.3;

wherein the dinitrile compound comprises a compound of Formula (5):

CN—R 2 —(O—R 3 ) n —O—R 4 —CN  (5);

where 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; 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 electrolyte according to claim 1 , wherein the dinitrile compound is one selected from the group consisting of 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, and any combination thereof.

3. The electrolyte 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.

4. The electrolyte according to claim 3 , wherein the dinitrile compound represented by Formula (4) 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, 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.

5. The electrolyte according to claim 1 , wherein the trinitrile compound comprises a compound of Formula (6), (7) 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.

6. The electrolyte 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 %.

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 weight of the electrolyte, a content of cyclic phosphonic anhydride is about 0.01-10 wt %.

11. The electrolyte according to claim 1 , further comprising one selected from the 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.

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

13. An electrochemical device, comprising: an electrode; and an electrolyte comprising a dinitrile compound, a trinitrile compound, and propyl propionate, wherein, based on a 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 8 wt %,

about 0.1≤(X/Y)≤about 6, and

about 0.01≤(Y/Z)≤about 0.3;

wherein the dinitrile compound comprises a compound of Formula (5):

CN—R 2 —(O—R 3 ) n —O—R 4 —CN  (5);

where 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 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.

14. The electrolyte according to claim 1 , wherein the initrile compound comprises a compound of Formula (5):

CN—R 2 —(O—R 3 ) n —O—R 4 —CN  (5);

where 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 2 to 5.

15. The electrochemical device according to claim 13 , wherein the electrode comprising:

a current collector, a single-sided coating and a double-sided coating;

a first part of the current collector has the single-sided coating and a second part of the current collector has the double-sided coating; and

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

16. The electrochemical device according to claim 15 , wherein,

the electrode is a cathode, and 3.5 g/cm 3 ≤D2≤4.3 g/cm 3 ; or,

the electrode is an anode, and 1.2 g/cm 3 ≤D2≤1.8 g/cm 3 .

17. An electrochemical device, comprising: electrodes; and an electrolyte comprising a dinitrile compound, a trinitrile compound, and propyl propionate, wherein, based on a 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 8 wt %,

about 0.1≤(X/Y)≤about 6, and

about 0.01≤(Y/Z)≤about 0.3;

wherein the dinitrile compound comprises a compound of Formula (5):

CN—R 2 —(O—R 3 ) n —O—R 4 —CN  (5);

where 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 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.

18. The electrochemical device according to claim 17 , wherein the electrodes comprising:

a first electrode and a second electrode;

where 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.

19. The electrochemical device according to claim 17 , 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 ; or,

the first electrode is an anode, the second electrode is an anode, and 1.2 g/cm 3 ≤D2≤1.8 g/cm 3 .

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 060786/0391 →
Priority Claims (1)
CN 201811108529.X · Sep 21, 2018 · national
Continuity (3)
Continuation 17064782 · Oct 7, 2020
Continuation 16211853 · Dec 6, 2018
Related Publication 20220407108A1 · Dec 22, 2022