Functionalized sulfonyl fluoride additives for electrolyte composition for lithium ion batteries

Patent metadata

Field	Value
Publication number	US-11145903-B2
Application number	US-201816479642-A
Country	US
Kind code	B2
Filing date	Feb 2, 2018
Priority date	Feb 7, 2017
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

An electrolyte composition containing at least one aprotic organic solvent; at least one conducting salt; at least one compound of formula (I) and (vi) optionally one or more additives.

First claim

The invention claimed is:

1. An electrolyte composition, comprising:
(i) at least one aprotic organic solvent;
(ii) at least one conducting salt;
(iii) at least one compound of formula (I)

wherein
L is a C 1 -C 4 hydrocarbon linker group wherein one or more hydrogen may be replaced by CN and/or F;
A is independently at each occurrence selected from (CH 2 ) m1 S(O) 2 (CH 2 ) m2 R 1 , (CH 2 ) m3 P(O)(OR 2 ) 2 , and (CH 2 ) m4 C(O)OR 3 ,
R 1 is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more substituents selected from F, CN, S(O) 2 F, S(O) 2 R 1a , OR 1a , and C(O)OR 1a· ;
R 1a is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more substituent selected from CN, F, S(O) 2 F, and non-fluorinated and fluorinated C 1 -C 4 alkyl;
R 2 is independently at each occurrence selected from Si(R 2 a) 3 , Si(OR 2a ) 3 , C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, wherein alkyl, (hetero)cycloalkyl, alkenyl, alkynyl, (hetero)aryl, and (hetero)aralkyl may be substituted by one or more substituents selected from F and non-fluorinated and fluorinated C 1 -C 4 alkyl;
R 2a is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more F;
R 3 is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, wherein alkyl, alkenyl, alkynyl, (hetero)aryl, and (hetero)aralkyl may be substituted by one or more substituents selected from CN, F and non-fluorinated and fluorinated C 1 -C 4 alkyl;
a is 1 or 2,
b is 1 or 2;
n and m2 are each independently at each occurrence an integer from 1 to 6; and
m 1, m3 and m4 are each independently at each occurrence 0 or an integer from 1 to 6;
wherein one or more H of the (CH 2 ) n , (CH 2 ) m1 , (CH 2 ) m2 , (CH 2 ) m3 , and (CH 2 ) m4 chains may be replaced by F; and
wherein if A is (CH 2 ) m4 C(O)OR 3 then b is 2; and
(iv) optionally one or more additives.

2. The electrolyte composition of claim 1 , wherein at least one A is (CH 2 ) m1 S(O) 2 (CH 2 ) m2 R 1 .

3. The electrolyte composition of claim 1 , wherein the compound of formula (I) is a compound of formula (II)
R 1 —(CH 2 ) m2 —S(O) 2 -(CH 2 ) m1 -L-[(CH 2 ) n —SO 2 F] b
(II)
wherein
L is a C 1 -C 4 hydrocarbon linker group wherein one or more hydrogen may be replaced by CN and/or F;
R 1 is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more substituents selected from F, CN, S(O) 2 F, S(O) 2 Rla, ORI-a, and C(O)OR 1 a;
R 1a is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more substituent selected from CN, F, S(O) 2 F, and non-fluorinated and fluorinated C 1 -C 4 alkyl;
b is 1 or 2;
n is 1, 2, 3 or 4;
m1 is 0, 1 or 2; and
m2 is 1, 2, 3 or 4; and
wherein one or more H of the (CH 2 ), (CH 2 ) m1 , and (CH 2 ) m2 chains may be replaced by F.

4. The electrolyte composition of claim 1 , wherein at least one A is (CH 2 ) m3 P(O)(OR 2 ) 2 .

5. The electrolyte composition of claim 1 , wherein the compound of formula (I) is a compound of formula (III)
(R 2 O) 2 P(O)—(CH 2 ) m3 -L-[(CH 2 ) n —SO 2 F] b
(III)
wherein
L is a C 1 -C 4 hydrocarbon linker group wherein one or more hydrogen may be replaced by CN and/or F;
R 2 is independently at each occurrence selected from Si(R 2a ) 3 , Si(OR 2a ) 3 , C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, wherein alkyl, (hetero)cycloalkyl, alkenyl, alkynyl, (hetero)aryl, and (hetero)aralkyl may be substituted by one or more substituents selected from F and non-fluorinated and fluorinated C 1 -C 4 alkyl;
R 2a is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, which may be substituted by one or more F;
b is 1 or 2;
n is 1, 2, 3 or 4; and
m3 is 0, 1, 2, 3 or 4; and
wherein one or more H of the (CH 2 ) n and (CH 2 ) m3 chains may be replaced by F.

6. The electrolyte composition of claim 1 , wherein at least one A is ( CH2 ) m4 C(O)OR 3 and b is 2.

7. The electrolyte composition of claim 1 , wherein the compound of formula (I) is a compound of formula (IV) R 3 OC(O)—(CH 2 ) m4 -L-[(CH 2 ) n —SO 2 ] 2
(IV)
wherein
L is a C 1 -C 4 hydrocarbon linker group wherein one or more hydrogen may be replaced by CN and/or F;
R 3 is independently at each occurrence selected from C 1 -C 10 alkyl, C 3 -C 6 (hetero)cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 5 -C 7 (hetero)aryl, and C 6 -C 13 (hetero)aralkyl, wherein alkyl, alkenyl, alkynyl, (hetero)aryl, and (hetero)aralkyl may be substituted by one or more substituents selected from CN, F and non-fluorinated and fluorinated C 1 -C 4 alkyl;
n is 1, 2, 3 or 4; and
m4 is 0, 1, 2, 3 or 4; and
wherein one or more H of the (CH 2 ) n and (CH 2 ) m4 chains may be replaced by F.

8. The electrolyte composition of claim 1 , wherein the compound of formula (1) is selected from

9. The electrolyte composition of claim 1 , wherein the electrolyte composition comprises 0.01 to 10 wt.-% of the compound of formula (I) based on a total weight of the electrolyte composition.

10. The electrolyte composition of claim 1 , wherein the electrolyte composition is non-aqueous.

11. The electrolyte composition of claim 1 , wherein the at least one aprotic organic solvent (i) is selected from fluorinated and non-fluorinated cyclic and acyclic organic carbonates, fluorinated and non-fluorinated ethers and polyethers, fluorinated and non-fluorinated cyclic ethers, fluorinated and non-fluorinated cyclic and acyclic acetales and ketales, fluorinated and non-fluorinated orthocarboxylic acids esters, fluorinated and non-fluorinated cyclic and acyclic esters and diesters of carboxylic acids, fluorinated and non-fluorinated cyclic and acyclic sulfones, fluorinated and non-fluorinated cyclic and acyclic nitriles and dinitriles, fluorinated and non-fluorinated cyclic and acyclic phosphates, and mixtures thereof.

12. The electrolyte composition of claim 1 , wherein the at least one aprotic organic solvent (i) is selected from fluorinated and non-fluorinated ethers and polyethers, fluorinated and non-fluorinated cyclic and acyclic organic carbonates, and mixtures thereof.

13. The electrolyte composition

Assignees

• Basf Se

Inventors

• Han Zhenji
• Fukuzumi Takeo
• Sawada Eri
• Schulz-Dobrick Martin
• Kim Jinbum

Classifications

• H01M2300/0017

  Non-aqueous electrolytes · CPC title

• H01M10/0567 Primary

  characterised by the additives · CPC title

• Y02E60/10

  Energy storage using batteries · CPC title

• H01M10/0569

  characterised by the solvents · CPC title

• H01M2300/0025

  Organic electrolyte · CPC title