Novel compound, and additive, electrolyte and lithium secondary battery which comprise same

Patent metadata

Field	Value
Publication number	US-2023402651-A1
Application number	US-202218013841-A
Country	US
Kind code	A1
Filing date	Feb 28, 2022
Priority date	Mar 16, 2021
Publication date	Dec 14, 2023
Grant date	—

Abstract

Provided are a novel compound, and an additive, an electrolyte and a lithium secondary battery, which include the same. The compound includes: a cyclic sulfonyl group; and a silyl group linked thereto, the silyl group containing an unsaturated hydrocarbon group, and when the compound is used as an additive in an electrolyte for a lithium secondary battery, resistance characteristics during high-temperature storage and low-temperature discharge capacity of a lithium secondary battery may be improved.

First claim

1 . A compound comprising: a cyclic sulfonyl group; and a silyl group linked thereto, the silyl group containing an unsaturated hydrocarbon group.

2 . The compound of claim 1 , wherein the compound is represented by Formula 1 below:

wherein in Formula 1, R 1 to R 9 are each independently selected from hydrogen, deuterium, a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ), wherein Q 1 to Q 7 are each independently selected from hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; L is selected from O, S, a carbonyl group, a substituted or unsubstituted C 1 -C 8 alkylene group, a substituted or unsubstituted C 2 -C 8 alkenylene group, a substituted or unsubstituted C 1 -C 8 alkynylene group, a substituted or unsubstituted C 2 -C 8 heteroalkenylene group, a substituted or unsubstituted C 2 -C 8 heteroalkenylene group, a substituted or unsubstituted C 2 -C 8 heteroalkynylene group, a substituted or unsubstituted C 3 -C 8 cycloalkyl group, a substituted or unsubstituted 3- to 10-membered heterocyclo group, a substituted or unsubstituted C 5 -C 10 aryl group, a substituted or unsubstituted 5- to 10-membered heteroaryl group, or —N(Q 1 )-, wherein Q 1 is as described above; m is 1, 2 or 3; and is 1 or 2.

3 . The compound of claim 2 , wherein R 1 to R 7 are each independently selected from hydrogen, deuterium, a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, or a substituted or unsubstituted C 1 -C 10 alkoxy group; R 8 and R 9 are each independently selected from a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, or a substituted or unsubstituted C 1 -C 10 alkoxy group; L is selected from O, S, a carbonyl group, a substituted or unsubstituted C 1 -C 4 alkylene group, a substituted or unsubstituted C 2 -C 4 alkenylene group, a substituted or unsubstituted C 2 -C 4 alkynylene group, a substituted or unsubstituted C 1 -C 4 heteroalkylene group, a substituted or unsubstituted C 2 -C 4 heteroalkenylene group, a substituted or unsubstituted C 2 -C 4 heteroalkynylene group, a substituted or unsubstituted C 3 -C 6 , cycloalkyl group, a substituted or unsubstituted 3- to 10-membered heterocyclo group, a substituted or unsubstituted C 5 -C 8 aryl group, a substituted or unsubstituted 5- to 8-membered heteroaryl group, or —N(Q 1 )-; m is 1; and n is 1.

4 . The compound of claim 2 , wherein R 1 to R 7 are each independently selected from hydrogen, an unsubstituted C 1 -C 8 alkyl group, an unsubstituted C 2 -C 8 alkenyl group, an unsubstituted C 2 -C 8 alkynyl group, or an unsubstituted C 1 -C 8 alkoxy group; R 8 to R 9 are each independently selected from an unsubstituted C 1 -C 8 alkyl group, an unsubstituted C 2 -C 8 alkenyl group, an unsubstituted C 2 -C 8 alkynyl group, or an unsubstituted C 1 -C 8 alkoxy group; L is selected from O, S, a carbonyl group, an unsubstituted C 1 -C 4 alkylene group, an unsubstituted C 2 -C 4 alkenylene group, an unsubstituted C 2 -C 4 alkynylene group, an unsubstituted C 1 -C 4 heteroalkylene group, an unsubstituted C 2 -C 4 heteroalkenylene group, an unsubstituted C 2 -C 4 heteroalkynylene group, or —N(Q 1 )-; m is 1; and n is 1.

5 . The compound of claim 2 , wherein the compound is represented by Formula 2 below:

wherein in Formula 2, R 8 to R 7 are each independently selected from hydrogen, an unsubstituted C 1 -C 4 alkyl group, an unsubstituted C 2 -C 4 alkenyl group, an unsubstituted C 2 -C 4 alkynyl group, or an unsubstituted C 1 -C 4 alkoxy group; R 8 and R 9 are each independently selected from an unsubstituted C 1 -C 4 alkyl group, an unsubstituted C 2 -C 4 alkenyl group, an unsubstituted C 2 -C 4 alkynyl group, or an unsubstituted C 1 -C 4 alkoxy group; L is selected from O, S, a carbonyl group, a substituted or unsubstituted C 1 -C 4 alkylene group, a substituted or unsubstituted C 2 -C 4 alkenylene group, a substituted or unsubstituted C 2 -C 4 alkynylene group, a substituted or unsubstituted C 1 -C 4 heteroalkylene group, a substituted or unsubstituted C 2 -C 4 heteroalkenylene group, a substituted or unsubstituted C 2 -C 4 heteroalkynylene group, a substituted or unsubstituted C 3 -C 6 cycloalkyl group, a substituted or unsubstituted 3- to 10-membered heterocyclo group, a substituted or unsubstituted C 5 -C 8 aryl group, a substituted or unsubstituted 5- to 8-membered heteroaryl group, or —N(Q 1 )-; and m is 1, 2, or 3.

6 . The compound of claim 1 , wherein the compound is represented by Formula 3 below:

7 . An additive for a lithium secondary battery, comprising a compound according to claim 1 .

8 . An electrolyte for a lithium secondary battery, comprising: a lithium salt; an organic solvent; and an additive, wherein the additive comprises a compound according to claim 1 .

9 . The electrolyte of claim 8 , wherein a content of the compound is in a range of about 0.001 wt % to about 20 wt %, with respect to the total weight of the electrolyte.

10 . The electrolyte of claim 8 , wherein the lithium salt includes at least one selected from the group consisting of LiPF 6 , LiBF 4 , LiSbF 6 , LiAsF 6 , LiClO 4 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, LiC 4 F 9 SO 3 , LiAlO 2 , LiAlCl 4 , LiN(C x F 2x+1 SO 2 )(C y F 2y+1 SO 2 ) (2≤x≤20, and 2≤y≤20), LiCl, LiI, lithium bis(fluorosulfonyl)imide (LiFSI), lit

Assignees

• Samsung Sdi Co Ltd

Inventors

• Park Sangwoo
• Park Hyejin
• Oh Seungyeop
• Woo Myungheui
• Cho Wonseok

Classifications

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• H01M10/0567 Primary

  characterised by the additives · CPC title

• H01M10/0568

  characterised by the solutes · CPC title

• H01M10/052

  Li-accumulators · CPC title

• C07F7/18

  Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages · CPC title