Silicone-containing compound, electrolyte for lithium secondary battery, lithium secondary battery including the same, and the method of preparing the silicone-containing compound

Patent metadata

Field	Value
Publication number	US-9735447-B2
Application number	US-201414286914-A
Country	US
Kind code	B2
Filing date	May 23, 2014
Priority date	Jul 8, 2013
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

A silicone-containing compound is an additive for a lithium secondary battery electrolyte for improving high-temperature lifetime characteristics and/or high-temperature stability of a lithium secondary battery. An electrolyte for a lithium secondary battery includes the silicon-containing compound. A lithium secondary battery includes the electrolyte. A method of preparing the silicon-containing compound is also provided.

First claim

What is claimed is:

1. An electrolyte for a rechargeable lithium battery comprising:
a lithium salt; and
a silicone-containing compound represented by Formula 1:

wherein:
X is nitrogen (N) or phosphorous(P);
R and R 1 are each independently selected from the group consisting of a hydrogen atom, a hydroxy group, a cyano group, —OR x (where R x is a C1-C6 alkyl group or a C6-C20 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C1-C6 alkoxy group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 aryloxy group, and a substituted or unsubstituted C6-C20 heteroaryl group;
R 2 , R 3 , and R 4 are each independently selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group;
at least one of R 2 , R 3 , and R 4 is selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C12alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group;
R a is selected from the group consisting of a hydrogen atom, an unsubstituted C1-C10 alkyl group, a C1-C10 alkyl group substituted with a halogen atom, an unsubstituted C6-C12 aryl group, a C6-C12 aryl group substituted with a halogen atom, an unsubstituted C6-C12 heteroaryl group, and a C6-C12 heteroaryl group substituted with a halogen atom; and
R b and R c are each independently selected from the group consisting of a hydrogen atom, an unsubstituted C1-C10 alkyl group, a C1-C10 alkyl group substituted with a halogen atom, an unsubstituted C2-C10 alkenyl group, a C2-C10 alkenyl group substituted with a halogen atom, an unsubstituted C3-C12 cycloalkyl group, a C3-C12 cycloalkyl group substituted with a halogen atom, an unsubstituted C6-C12 aryl group, a C6-C12 aryl group substituted with a halogen atom, an unsubstituted C6-C12 heteroaryl group, a C6-C12 heteroaryl group substituted with a halogen atom, and —Si(R d ) 3 , wherein R d in —Si(R d ) 3 is a C1-C10 alkyl group,
and wherein, when R is CF 3 :
all of R 2 to R 4 are the same and are selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group;
one or more of R 2 to R 4 is selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group; or
R 2 to R 4 are each independently selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OC(═O)(OR a ), —NR b R c , a primary substituted or unsubstituted C1-C12 alkyl group, a secondary substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group; wherein at least one of R 2 , R 3 , and R 4 is selected from the group consisting of a cyano group, —OR y (where R y is a C1-C12 alkyl group, or a C6-C12 aryl group), —C(═O)R a , —C(═O)OR a , —OC(═O)R a , —OR(═O)(OR a ), —NR b R c , a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C2-C12 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C6-C12 aryloxy group, and a substituted or unsubstituted C6-C12 heteroaryl group.

2. The electrolyte for a rechargeable lithium battery according to claim 1 , wherein X is nitrogen (N).

3. The electrolyte for a rechargeable lithium battery according to claim 1 , wherein when one or more of R, R 1 , R 2 , R 3 , or R 4 is a substituted group, a substituent of the substituted group is selected from the group consisting of a halogen atom, a C1-C10 alkyl group substituted with a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, and a C1-C10 heteroalkyl group.

4. The electrolyte for a rechargeable lithium battery according to claim 1 , wherein:
X is nitrogen (N);
R and R 1 are each independently selected from the group consisting of a C1-C6 alkyl group, and a C1-C6 alkyl group substituted with one or more of a halogen atom; and
R 2 , R 3 , and R 4 are each independently selected from the group consisting of a C1-C12 alkyl group, a C1-C12 alkyl group substituted with one or more of a halogen atom, a C2-C12 alkenyl group, and a C2-C12 alkenyl group substituted with one or more of a halogen atom.

5. The electrolyte for a rechargeable lithium battery according to claim 4 , wherein the silicone-containing compound represented by Formula 1 is selected from the group consisting of Compounds 3 to 4:

6. The electrolyte for a rechargeable lithium battery according to claim 1 , wherein one or more of R, R 1 , R 2 , R 3 , or R 4 comprises an alkene group.

7. The electrolyte for a rechargeable lithium battery according to claim 1 , wherein one or more of R, R 1 , R 2 , R 3 , or R 4 is an electron-withdrawing group.

8. The electrolyte for a rechargeable lithium battery according to cl

Assignees

• Samsung Sdi Co Ltd

Inventors

• Egorov Vladimir
• Shin Woo-Cheol
• Kim Soo-Jin
• Woo Myung-Heui
• Park Hye-Jin
• Cha Si-Young

Classifications

• H01M10/0567 Primary

  characterised by the additives · CPC title

• H01M10/052

  Li-accumulators · CPC title

• H01M4/13 Primary

  Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof · CPC title

• H01M2300/0025

  Organic electrolyte · CPC title

• Y02T10/7011

  Cross-Sectional Technologies · mapped topic