Electrolyte for secondary battery and secondary battery including the same

Patent metadata

Field	Value
Publication number	US-9905884-B2
Application number	US-201615168465-A
Country	US
Kind code	B2
Filing date	May 31, 2016
Priority date	Sep 15, 2015
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

An electrolyte for a secondary battery includes a non-aqueous solvent; a lithium salt; and a heterocyclic compound represented by Formula 1:

wherein, in Formula 1, R 1 and R 2 are each independently selected from hydrogen, a halogen group, a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , —OCO(OR a ), —C═N(R a ), a substituted or unsubstituted C 1 -C 20 alkyl group, and a combination thereof, wherein R a is selected from hydrogen and a C 1 -C 10 alkyl group, and, provided that at least one selected from R 1 and R 2 is selected from a halogen group, a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , a substituted or unsubstituted C 1 -C 20 alkyl group, and a combination thereof.

First claim

What is claimed is:

1. An electrolyte for a secondary battery comprising:
a non-aqueous solvent;
a lithium salt; and
a heterocyclic compound represented by Formula 1:

wherein, in Formula 1,
R 1 and R 2 are each independently selected from hydrogen, a halogen group, a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , —OCO(OR a ), —C═N(R a ), a substituted or unsubstituted C 1 -C 20 alkyl group, and a combination thereof, wherein R a is selected from hydrogen and a C 1 -C 10 alkyl group, and
R 3 , R 4 , R 5 , and R 6 are each independently selected from hydrogen, a halogen group, a cyano group, a hydroxy group, —C(═O)R b , —C(═O)OR b , —OCO(OR b ), —C═N(R b ), —SR b , —S(═O)R b , —S(═O) 2 R b , —P(R b ) 2 , a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a C 2 -C 20 alkylene oxide group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 heteroaryl group, and a combination thereof, wherein R b is selected from hydrogen, a C 1 -C 10 alkyl group, and a C 6 -C 20 aryl group,
provided that at least one selected from R 1 and R 2 is selected from a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , a substituted C 1 -C 20 alkyl group, and a combination thereof.

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

wherein, in Formula 2,
R′ 1 and R′ 2 are each independently selected from hydrogen, a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , —OCO(OR c ), —C═N(R c ), a substituted C 1 -C 20 alkyl group, and a combination thereof, wherein R c is selected from hydrogen and a C 1 -C 10 alkyl group,
provided that R′ 1 and R′ 2 are not both hydrogen.

3. The electrolyte of claim 2 , wherein, in Formula 2,
R′ 1 is selected from a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , a substituted C 1 -C 20 alkyl group, and a combination thereof, and
R′ 2 is selected from hydrogen, a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , a substituted C 1 -C 20 alkyl group, and a combination thereof.

4. The electrolyte of claim 1 , wherein the heterocyclic compound comprises a compound selected from Compounds 1 to 4:

and
a combination thereof.

5. The electrolyte of claim 1 , wherein an amount of the heterocyclic compound is in a range of about 0.005 weight percent to about 10 weight percent, based on a total weight of the electrolyte.

6. The electrolyte of claim 1 , wherein an amount of the heterocyclic compound is in a range of about 0.05 weight percent to about 2 weight percent, based on a total weight of the electrolyte.

7. The electrolyte of claim 1 , wherein the lithium salt comprises a salt selected from LiSCN, LiN(CN) 2 , LiClO 4 , LiAlO 4 , LiAlCl 4 , LiBF 4 , LiAsF 6 , LiPF 6 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, LiC 4 F 9 SO 3 , Li(CF 3 SO 2 ) 3 C, LiN(SO 2 F) 2 , LiN(SO 2 CF 3 ) 2 , LiN(SO 2 CF 2 CF 3 ) 2 , LiSbF 6 , LiPF 3 (CF 2 CF 3 ) 3 , LiPF 3 (CF 3 ) 3 , LiB(C 2 O 4 ) 2 , and a combination thereof.

8. The electrolyte of claim 1 , wherein the non-aqueous organic solvent comprises a solvent selected from ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, fluoroethylene carbonate, fluoropropylene carbonate, difluoropropylene carbonate, trifluoropropylene glycol ester, γ-butyrolactone, chloro-γ-butyrolactone, dichloro-γ-butyrolactone, bromopropylene carbonate, dibromopropylene carbonate, tribromopropylene glycol ester, bromo-γ-butyrolactone, dibromo-γ-butyrolactone, nitropropylene carbonate, nitro-γ-butyrolactone, cyanopropylene carbonate, cyano-γ-butyrolactone, 1,2-dimethoxy ethane, diepoxy ethane, dimethylene glycol dimethyl ether, trimethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, polyethylene glycol dimethyl ether, succinonitrile, sulfolane, dimethyl sulfone, ethyl methyl sulfone, diethyl sulfone, adiponitrile, 1,1,2,2-tetrafluoroethyl 2,2,3,3-tetrafluoropropyl ether, tetraphenylethene, 2,2,2-trifluoroethanol, and a combination thereof.

9. A secondary battery comprising:
a positive electrode including a positive active material;
a negative electrode including a negative active material; and
an electrolyte between the positive electrode and the negative electrode,
wherein the electrolyte comprises a non-aqueous organic solvent, a lithium salt, and a heterocyclic compound represented by Formula 1,

wherein, in Formula 1,
R 1 and R 2 are each independently selected from hydrogen, a halogen group, a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , —OCO(OR a ), —C═N(R a ), a substituted or unsubstituted C 1 -C 20 alkyl group, and a combination thereof, wherein R a is selected from hydrogen and a C 1 -C 10 alkyl group, and
R 3 , R 4 , R 5 , and R 6 are each independently selected from hydrogen, a halogen group, a cyano group, a hydroxy group, —C(═O)R b , —C(═O)OR b , —OCO(OR b ), —C═N(R b ), —SR b , —S(═O)R b , —S(═O) 2 R b , —P(R b ) 2 , a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a C 2 -C 20 alkylene oxide group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 heteroaryl group, and a combination thereof, wherein R b is selected from hydrogen, a C 1 -C 10 alkyl group, and a C 6 -C 20 aryl group,
provided that at least one selected from R 1 and R 2 is selected from a cyano group, a hydroxy group, a nitro group, —C(═O)R a , —C(═O)OR a , a substituted, and a combination thereof.

10. The secondary battery of claim 9 , wherein the heterocyclic compound is represented by Formula 2:

wherein, in Formula 2,
R′ 1 and R′ 2 are each independently selected from hydrogen, a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , —OCO(OR c ), —C═N(R c ), a substituted C 1 -C 20 alkyl group, and a combination thereof, wherein R c is selected from hydrogen and a C 1 -C 10 alkyl group,
provided that R′ 1 and R′ 2 are not both hydrogen.

11. The secondary battery of claim 10 , wherein, in Formula 2,
R′ 1 is selected from a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , a substituted C 1 -C 20 alkyl group, and a combination thereof, and
R′ 2 is selected from hydrogen, a cyano group, a hydroxy group, a nitro group, —C(═O)R c , —C(═O)OR c , a substituted C 1 -C 20 alkyl group, and a combination thereof.

12. The secondary battery of claim 9 , wherein the heterocyclic com

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Park Insun
• Park Hosang
• Seo Jinah
• Kang Yoonsok
• Kim Dongyoung
• Park Minsik

Classifications

• H01M4/13

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

• H01M4/366

  as layered products · CPC title

• H01M10/0525 Primary

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M10/0567

  characterised by the additives · CPC title

• H01M10/0569

  characterised by the solvents · CPC title