Electrolytic solution, secondary battery, battery pack, electric vehicle, electric power storage system, electric power tool, and electronic apparatus
View Patent ↗A secondary battery includes: a cathode; an anode; and an electrolytic solution. The electrolytic solution includes an unsaturated cyclic ester carbonate and one or more selected from a group configured of aromatic compounds, dinitrile compounds, sulfinyl compounds, and lithium salts.
1. A secondary battery comprising:
a cathode;
an anode; and
an electrolytic solution, wherein:
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of: aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
2. The secondary battery according to claim 1 , wherein
the halogen group includes a fluorine group, a chlorine group, a bromine group, and an iodine group,
the monovalent hydrocarbon group, the monovalent halogenated hydrocarbon group, the monovalent oxygen-containing hydrocarbon group, and the monovalent halogenated oxygen-containing hydrocarbon group include an alkyl group with carbon number from 1 to 12 both inclusive, an alkenyl group with carbon number from 2 to 12 both inclusive, an alkynyl group with carbon number from 2 to 12 both inclusive, an aryl group with carbon number from 6 to 18 both inclusive, a cycloalkyl group with carbon number from 3 to 18 both inclusive, an alkoxy group with carbon number from 1 to 12 both inclusive, groups each obtained by bonding two or more of the foregoing groups to one another, groups each obtained by substituting each of part or all of hydrogen groups of any of the foregoing groups by a halogen group, and
the divalent hydrocarbon group and the divalent halogenated hydrocarbon group include an alkylene group with carbon number from 1 to 12 both inclusive, an alkenylene group with carbon number from 2 to 12 both inclusive, an alkynylene group with carbon number from 2 to 12 both inclusive, an arylene group with carbon number from 6 to 18 both inclusive, a cycloalkylene group with carbon number from 3 to 18 both inclusive, groups each obtained by bonding two or more of the foregoing groups to one another, and groups each obtained by substituting each of part or all of hydrogen groups of any of the foregoing groups by a halogen group.
3. The secondary battery according to claim 1 , wherein the unsaturated cyclic ester carbonate is represented by one of the following Formula (18) to Formula (20),
where R5 to R14 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; the R5 and the R6 may be bonded to each other; any two or more of the R7 to the R10 may be bonded to one another; and any two or more of the R11 to the R14 may be bonded to one another.
4. The secondary battery according to claim 1 , wherein the unsaturated cyclic ester carbonate is represented by one of the following Formula (1-1) to Formula (1-56)
5. The secondary battery according to claim 1 , wherein the aromatic compounds are each represented by one of the following Formula (2-1) to Formula (2-14), Formula (3-1), and Formula (4-1), and a content of the aromatic compounds in the electrolytic solution is from about 0.1 weight percent to about 10 weight percent both inclusive
6. The secondary battery according to claim 1 , wherein the dinitrile compounds are each represented by one of the following Formula (6-1) to Formula (6-11), and a content of the dinitrile compounds in the electrolytic solution is from about 0.1 weight percent to about 10 weight percent both inclusive
7. The secondary battery according to claim 1 wherein, the sulfinyl compounds are each represented by one of the following Formula (7-1) to Formula (7-10), Formula (8-1) to Formula (8-6), Formula (9-1) to Formula (9-5), Formula (10-1) to Formula (10-17), Formula (11-1) to Formula (11-18), Formula (12-1) to Formula (12-9), and Formula (13-1) to Formula (13-14), and a content of the sulfinyl compounds in the electrolytic solution is from about 0.1 weight percent to about 5 weight percent both inclusive
8. The secondary battery according to claim 1 , wherein the lithium salts are each represented by one of the following Formula (15-1) to Formula (15-4), Li[N(SO 2 F) 2 ], and Li(SO 3 F)
9. The secondary battery according to claim 1 , wherein the secondary battery is a lithium ion secondary battery.
10. An electrolytic solution comprising:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
11. A battery pack comprising:
a secondary battery;
a control section controlling a used state of the secondary battery; and
a switch section switching the used state of the secondary battery according to an instruction of the control section, wherein:
the secondary battery includes a cathode, an anode, and an electrolytic solution, and
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
12. An electric vehicle comprising:
a secondary battery;
a conversion section converting electric power supplied from the secondary battery into drive power;
a drive section operating according to the drive power; and
a control section controlling a used state of the secondary battery, wherein:
the secondary battery includes a cathode, an anode, and an electrolytic solution, and
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
13. An electric power storage system comprising:
a secondary battery;
one or more electric devices supplied with electric power from the secondary battery; and
a control section controlling the supplying of the electric power from the secondary battery to the one or more electric devices, wherein:
the secondary battery includes a cathode, an anode, and an electrolytic solution, and
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; arbitrary two or more of the R21 to the R26 may be bonded to one another; arbitrary two or more of the R27 to the R34 may be bonded to one another; arbitrary two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) and the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; arbitrary two or more of the R58 to the R60 may be bonded to one another; and arbitrary two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65 or the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
14. An electric power tool comprising:
a secondary battery; and
a movable section supplied with electric power from the secondary battery, wherein:
the secondary battery includes a cathode, an anode, and an electrolytic solution, and
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).
15. An electronic apparatus comprising
a secondary battery as an electric power supply source, wherein:
the secondary battery includes a cathode, an anode, and an electrolytic solution, and
the electrolytic solution includes:
0.01 weight percent to 10 weight percent of an unsaturated cyclic ester carbonate represented by the following Formula (1), and
one or more selected from a group consisting of aromatic compounds represented by the following Formula (2) to Formula (5), dinitrile compounds represented by the following Formula (6), sulfinyl compounds represented by the following Formula (7) to Formula (14), and 0.01 moles per kilogram to 1.0 moles per kilogram of lithium salts represented by the following Formula (15) to Formula (17),
where X is a divalent group in which m-number of >C═CR1-R2 and n-number of >CR3R4 are bonded to one another in any order; R1 to R4 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R1 to the R4 may be bonded to one another; and m and n satisfy m≧1 and n≧0,
where R21 to R44 are each one of a hydrogen group, a halogen group, a monovalent hydrocarbon group, a monovalent halogenated hydrocarbon group, a monovalent oxygen-containing hydrocarbon group, and a monovalent halogenated oxygen-containing hydrocarbon group; any two or more of the R21 to the R26 may be bonded to one another; any two or more of the R27 to the R34 may be bonded to one another; any two or more of the R35 to the R44 may be bonded to one another; and total number of carbon atoms in each of the aromatic compounds represented by the Formula (2) to the Formula (4) is from 7 to 18 both inclusive,
NC—R45-CN (6)
where R45 is one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group,
where R46 to R59, R61, and R62 are each one of a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; R60 and R63 are each one of a divalent hydrocarbon group and a divalent halogenated hydrocarbon group; the R46 and the R47 may be bonded to each other; the R48 and the R49 may be bonded to each other; the R50 and the R51 may be bonded to each other; the R52 and the R53 may be bonded to each other; the R54 and the R55 may be bonded to each other; the R56 and the R57 may be bonded to each other; any two or more of the R58 to the R60 may be bonded to one another; and any two or more of the R61 to the R63 may be bonded to one another,
where R64 is a divalent halogenated hydrocarbon group,
Li[N(SO 2 R65)(SO 2 R66)] (16)
where R65 and R66 are each one of a halogen group, a monovalent hydrocarbon group, and a monovalent halogenated hydrocarbon group; and the R65, the R66, or both are each one of a halogen group and a monovalent halogenated hydrocarbon group,
Li(SO 3 F) (17).