IP Library Granted Patent US 11,597,736
Granted Patent B2
US 11,597,736 · App. 16/630,633 · Granted Mar 7, 2023

Lithium boron fluorophosphate complex compound, lithium boron fluorophosphate-containing composition, lithium boron fluorophosphate, additive for lithium secondary battery, non-aqueous electrolytic solution for battery, and lithium secondary battery

Inventors: Han Zhang (Ichihara, JP); Yusuke Shimizu (Ichihara, JP); Kenichi Goto (Chiba, JP); Hitoshi Onishi (Chiba, JP); Gen Miyata (Ichihara, JP)
Assignee: MITSUI CHEMICALS, INC.
C07F9/14H01M4/131H01M10/0525H01M10/0567H01M2004/027H01M2004/028H01M2300/0025
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Quick Facts
Patent No.
US 11,597,736
App. No.
16/630,633
Granted
Mar 7, 2023
Kind
B2
Abstract

A lithium boron fluorophosphate complex compound including a compound A that is one selected from a group of lithium boron fluorophosphates represented by Formula (I), and a compound B that is one selected from a group of compounds represented by Formulae (II) to (IX). R 0 represents a hydrocarbon group, R 1 to R 7 each independently represent a hydrogen atom or a substituent, R 8 , R 9 , R 10 , R 11 , and R 13 to R 21 each independently represent a substituent, and R 12 , R 22 , and R 23 each independently represent a divalent linking group.

Claims (34)

1. A lithium boron fluorophosphate complex compound comprising:

a compound A that is one selected from a group of lithium boron fluorophosphates represented by the following Formula (I); and

a compound B that is one selected from a group of compounds represented by the following Formulae (II) to (IX):

wherein, in Formula (I), R 0 represents an aliphatic hydrocarbon group having from 1 to 12 carbon atoms,

wherein, in Formula (II), R 1 to R 3 each independently represent a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; and R 1 and R 3 , or R 2 and R 3 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms;

in Formula (III), R 4 to R 7 each independently represent a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; and R 4 and R 5 , R 6 and R 7 , or R 5 and R 6 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms;

in Formula (IV), R 8 and R 9 each independently represent an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; and R 8 and R 9 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms;

in Formula (V), R 10 and R 11 each independently represent an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; R 10 and R 11 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms or a sulfonylalkylenesulfonyl group having from 1 to 6 carbon atoms; and R 12 represents an alkylene group having from 1 to 4 carbon atoms, optionally substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, and an alkynyl group optionally substituted with a halogen atom;

in Formula (VI), R 13 and R 14 each independently represent an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; and R 13 and R 14 are optionally combined to represent a divalent aliphatic group having from 2 to 9 carbon atoms;

in Formula (VII), R 15 to R 17 each independently represent an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; and R 15 , R 16 and R 17 are optionally combined to represent a divalent aliphatic group having from 2 to 9 carbon atoms;

in Formula (VIII), R 18 to R 21 each independently represent an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, an alkynyl group optionally substituted with a halogen atom, or an aryl group; R 18 and R 21 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms, and R 19 and R 20 are optionally combined to represent an alkylene group having from 2 to 9 carbon atoms; and R 22 represents an alkylene group having from 1 to 4 carbon atoms, optionally substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, and an alkynyl group optionally substituted with a halogen atom; and

in Formula (IX), R 23 represents an alkylene group having from 2 to 9 carbon atoms, optionally substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, and an alkynyl group optionally substituted with a halogen atom.

2. The lithium boron fluorophosphate complex compound according to claim 1 , wherein:

the compound A is one selected from a group of lithium boron fluorophosphates represented by the following Formula (X), and

the compound B is one selected from the group consisting of N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethoxyethane, 1,3-dioxolane, 1,4-dioxane, dimethyl sulfoxide, 1,5,2,4-dioxadithiane-2,2,4,4-tetraoxide, diethyl ether, furan, tetrahydrofuran, triethylamine, pyridine, triethylenediamine, 1,3-dioxolan-2-one, 4-methyl-1,3-dioxolan-2-one, and 4-fluoro-1,3-dioxolan-2-one:

wherein, in Formula (X), R 00 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a vinyl group, an allyl group, or an ethynyl group.

3. The lithium boron fluorophosphate complex compound according to claim 1 , wherein:

the compound A is one selected from the group consisting of lithium boron fluorophosphates represented by the following Formulae (XI) to (XII); and

the compound B is one selected from the group consisting of N-methylpyrrolidone, 1,3-dioxolan-2-one, 4-fluoro-1,3-dioxolan-2-one, diethyl ether, dimethoxyethane, tetrahydrofuran, 1,3-dioxolane, and pyridine:

4. A lithium boron fluorophosphate complex compound comprising at least one compound A selected from a group of lithium boron fluorophosphates represented by the following Formula (I):

wherein, in Formula (I), R 0 represents an aliphatic hydrocarbon group having from 1 to 12 carbon atoms.

5. A lithium boron fluorophosphate-containing composition comprising at least one compound A selected from a group of lithium boron fluorophosphates represented by the following Formula (I):

wherein, in Formula (I), R 0 represents an aliphatic hydrocarbon group having from 1 to 12 carbon atoms.

6. A lithium boron fluorophosphate represented by the following Formula (I):

wherein, in Formula (I), R 0 represents an aliphatic hydrocarbon group having from 1 to 12 carbon atoms.

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

8. A non-aqueous electrolytic solution for a battery, the solution comprising the lithium boron fluorophosphate complex compound according to claim 1 .

9. The non-aqueous electrolytic solution for a battery according to claim 8 , the solution further comprising an additive C that is a compound represented by the following Formula (C):

wherein, in Formula (C), R c1 and R c2 each independently represent a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

10. A lithium secondary battery comprising:

a positive electrode;

a negative electrode comprising, as a negative electrode active material, at least one selected from the group consisting of metallic lithium, a lithium-containing alloy, a metal or alloy capable of alloying with lithium, an oxide capable of doping and dedoping a lithium ion, a transition metal nitride capable of doping and dedoping a lithium ion, and a carbon material capable of doping and dedoping a lithium ion; and

the non-aqueous electrolytic solution for a battery according to claim 8 .

11. A lithium secondary battery obtained by charging and discharging the lithium secondary battery according to claim 10 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2020
From: ZHANG, HAN; SHIMIZU, YUSUKE; GOTO, KENICHI; ONISHI, HITOSHI; MIYATA, GEN
To: MITSUI CHEMICALS, INC.
Reel/Frame 051496/0242 →
Priority Claims (2)
JP JP2017-137754 · Jul 14, 2017 · national
JP JP2018-015002 · Jan 31, 2018 · national
Continuity (1)
Related Publication 20200148710A1 · May 14, 2020