Cyclic sulfate compound, non-aqueous electrolyte solution containing same, and lithium secondary battery

Patent metadata

Field	Value
Publication number	US-9227950-B2
Application number	US-201113820969-A
Country	US
Kind code	B2
Filing date	Oct 21, 2011
Priority date	Oct 22, 2010
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

A non-aqueous electrolyte solution containing a cyclic sulfate compound represented by formula (I) is provided, wherein in formula (I), R 1 represents a group represented by formula (II) or a group represented by formula (III); R 2 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a group represented by formula (II), or a group represented by formula (III); and in formula (II), R 3 represents a halogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogenated alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or a group represented by formula (IV).

First claim

The invention claimed is:

1. A non-aqueous electrolyte solution, comprising:
a cyclic sulfate compound represented by the following formula (I):

wherein, in formula (I), R 1 represents a group represented by the above formula (II) or a group represented by the above formula (III); and R 2 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a group represented by formula (II), or a group represented by formula (III);
in formula (II), R 3 represents a halogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogenated alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or a group represented by the above formula (IV); and the wavy line in formula (II), formula (III) and formula (IV) represents the position of bonding; and
in a case in which there are two groups represented by formula (II) in the cyclic sulfate compound represented by formula (I), the two groups represented by formula (II) may be the same as or different from each other.

2. The non-aqueous electrolyte solution according to claim 1 , wherein in formula (I), R 1 represents a group represented by formula (II) (provided that in formula (II), R 3 represents a fluorine atom, an alkyl group having from 1 to 3 carbon atoms, a halogenated alkyl group having from 1 to 3 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms, or a group represented by formula (IV)), or a group represented by formula (III); and R 2 represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms, a group represented by formula (II) (provided that in formula (II), R 3 represents a fluorine atom, an alkyl group having from 1 to 3 carbon atoms, a halogenated alkyl group having from 1 to 3 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms, or a group represented by formula (IV)), or a group represented by formula (III).

3. The non-aqueous electrolyte solution according to claim 2 , wherein in formula (I), R 1 represents a group represented by formula (II) (provided that in formula (II), R 3 represents a fluorine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, or a group represented by formula (IV)), or a group represented by formula (III); and R 2 represents a hydrogen atom or a methyl group.

4. The non-aqueous electrolyte solution according to claim 3 , wherein in formula (I), R 1 represents a group represented by formula (III), and R 2 represents a hydrogen atom.

5. The non-aqueous electrolyte solution according to claim 1 , further comprising at least one of an electrolyte compound represented by the following formula (V) or lithium difluorophosphate:

wherein, in formula (V), M represents an alkali metal; Y represents a transition element, or an element of Group 13, Group 14 or Group 15 of the Periodic Table of Elements; b represents an integer from 1 to 3; m represents an integer from 1 to 4; n represents an integer from 0 to 8; q represents 0 or 1; R 11 represents an alkylene group having from 1 to 10 carbon atoms, a halogenated alkylene group having from 1 to 10 carbon atoms, an arylene group having from 6 to 20 carbon atoms, or a halogenated arylene group having from 6 to 20 carbon atoms, wherein such groups may each contain a substituent or a heteroatom in the structure, and when q is 1 and m is 2 to 4, m units of R 11 may be bonded to each other; R 12 represents a halogen atom, an alkyl group having from 1 to 10 carbon atoms, a halogenated alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 20 carbon atoms, a halogenated aryl group having from 6 to 20 carbon atoms, or -Q 3 R 13 , wherein such groups, other than -Q 3 R 13 , may each contain a substituent or a heteroatom in the structure, and when n represents an integer from 2 to 8, n units of R 12 may be bonded to each other to form a ring; Q 1 , Q 2 , and Q 3 each independently represent 0, S or NR 14 ; and R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, a halogenated alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 20 carbon atoms, or a halogenated aryl group having from 6 to 20 carbon atoms, wherein such groups may each contain a substituent or a heteroatom in the structure, and when plural R 13 's or plural R 14 's are present, the respective groups may be bonded to each other to form a ring.

6. The non-aqueous electrolyte solution according to claim 5 , wherein the electrolyte compound represented by formula (V) is at least one compound selected from the group consisting of a compound represented by the following formula (VI), a compound represented by the following formula (VII), a compound represented by the following formula (VIII), and a compound represented by the following formula (IX):

wherein, in formulae (VI) to (IX), M has the same definition as M in formula (V).

7. The non-aqueous electrolyte solution according to claim 1 , further comprising a compound represented by the following formula (X):

wherein, in formula (X), Y 1 and Y 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

8. The non-aqueous electrolyte solution according to claim 1 , further comprising a compound represented by the following formula (XI):

wherein, in formula (XI), X 1 , X 2 , X 3 and X 4 each independently represent an alkyl group, having from 1 to 3 carbon atoms, that may be substituted with a fluorine atom; a hydrogen atom; a fluorine atom; or a chlorine atom, provided that X 1 to X 4 are not both hydrogen atoms at the same time.

9. The non-aqueous electrolyte solution according to claim 1 , wherein the content of the cyclic sulfate compound represented by formula (I) is from 0.001 mass % to 10 mass %.

10. The non-aqueous electrolyte solution according to claim 5 , wherein the content of at least one of the electrolyte compound represented by formula (V) or the lithium difluorophosphate is from 0.001 mass % to 10 mass %.

11. The non-aqueous electrolyte solution according to claim 7 , wherein the content of the compound represented by formula (X) is from 0.001 mass % to 10 mass %.

12. The non-aqueous electrolyte solution according to claim 8 , wherein the content of the compound represented by formula (XI) is from 0.001 mass % to 10 mass %.

13. An additive for a lithium secondary battery, the additive comprising a cyclic sulfate compound represented by the following formula (I) as an active ingredient:

wherein, in formula (I), R 1 represents a group represented by the above formula (II) or a group represented by the above formula (III); and R 2 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a group represented by formula (II), or a group represented by formula (III);
in formula (II), R 3 represents a halogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogenated alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or a g

Assignees

• Mio Shigeru
• Nakamura Mitsuo
• Haruta Kaichiro
• Nogi Hidenobu
• Fujiyama Satoko
• Hayashi Takashi
• Tsunoda Hidetoshi
• Mitsui Chemicals Inc

Inventors

• Mio Shigeru
• Nakamura Mitsuo
• Haruta Kaichiro
• Nogi Hidenobu
• Fujiyama Satoko
• Hayashi Takashi
• Tsunoda Hidetoshi

Classifications

• Y02E60/122

  Cross-Sectional Technologies · mapped topic

• Y02T10/7011

  Cross-Sectional Technologies · mapped topic

• H01M10/0567

  characterised by the additives · CPC title

• H01M10/0525

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

• C07D327/10 Primary

  two oxygen atoms and one sulfur atom, e.g. cyclic sulfates · CPC title