Phosphoranimine compounds, electrolyte solutions including a phosphoranimine compound, and energy storage devices including same

Patent metadata

Field	Value
Publication number	US-10367229-B2
Application number	US-201514817511-A
Country	US
Kind code	B2
Filing date	Aug 4, 2015
Priority date	Aug 4, 2015
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

A phosphoranimine compound comprising a cationic portion bonded to a nitrogen atom of the phosphoranimine compound, a phosphorus atom bonded to the nitrogen atom, pendant groups bonded to the phosphorus atom, and a counterion. An electrolyte solution comprising at least one phosphoranimine compound is also disclosed, as is an energy storage device including the electrolyte solution.

First claim

What is claimed is:

1. A phosphoranimine compound comprising a cationic portion bonded to a nitrogen atom of the phosphoranimine compound, a phosphorus atom bonded to the nitrogen atom, pendant groups bonded to the phosphorus atom, and a counterion, the cationic portion comprising an imidazolinium group, an imidazolium group, a phosphonium group, an ammonium group, a sulfonium group, a triazolium group, a thiazolium group, a pyridium group, a pyridinium group, an isoquinolinium group, a pyrrolidinium group, a pyrrolium group, a piperidinium group, or a pyrazolium group.

2. The phosphoranimine compound of claim 1 , wherein the phosphoranimine compound is a liquid at a temperature from about 20° C. to about 25° C.

3. The phosphoranimine compound of claim 1 , wherein the phosphoranimine compound exhibits a viscosity of from about 1 centipoise at room temperature to less than or equal to about 10 centipoise at room temperature.

4. An electrolyte solution comprising:
at least one phosphoranimine compound comprising:
a cationic portion bonded to a nitrogen atom, a phosphorus atom bonded to the nitrogen atom, pendant groups bonded to the phosphorus atom, and a counterion; and

a metal salt comprising an alkali metal salt, an alkaline earth metal salt, or a combination thereof.

5. The electrolyte solution of claim 4 , wherein the cationic portion comprises an imidazolinium group, an imidazolium group, a phosphonium group, an ammonium group, a sulfonium group, a triazolium group, a thiazolium group, a pyridium group, a pyridinium group, an isoquinolinium group, a pyrrolidinium group, a pyrrolium group, a piperidinium group, or a pyrazolium group.

6. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises the chemical structure:

wherein + R 4 comprises the cationic portion.

7. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises the chemical structure:

wherein
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of an acyl group, an acylamino group, an acyloxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, an alkylamino group, an alkylarylamino group, a dialkylamino group, an alkylthio group, an alkarylthio group, an aryl group, an arylamino group, a diarylamino group, an aryloxy group, an aralkyl group, an alkaryl group, an aralkoxy group, an alkaryloxy group, an arylthio group, an arylthio acyl group, an amino acid group, a carbamoyl group, a carbonamido group, a carboxyl group, a cyano group, a formyl group, a glycol group, a heteroalkyl group, a heteroaralkyl group, a heteroaryl group, a hydroxyl group, a nitro group, an oxy(aliphatic) group, an oxy(aliphatic)hydroxyl group, an oxy(alkyl)hydroxyl group, an oxycarbonyl group, an oxysulfonyl group, a perfluoroalkyl group, a phosphate group, a saccharide group, a sulfamoyl group, a sulfonamido group, a sulfonylamino group, a sulfonyl group, a sulfoxide group, a thio group, a thioalkaryl group, a thioaralkyl group, a trifluoroalkyl group, or an ureido group;
R 4 is the cationic portion; and
X is the counterion.

8. The electrolyte solution of claim 7 , wherein each R 1 , R 2 , and R 3 is different.

9. The electrolyte solution of claim 7 , wherein at least two of R 1 , R 2 , and R 3 are the same.

10. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises

or combinations thereof.

11. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises from about 0.1% by weight to less than about 15% by weight of the electrolyte solution.

12. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises from greater than or equal to about 15% by weight to less than about 50% by weight of the electrolyte solution.

13. The electrolyte solution of claim 4 , wherein the at least one phosphoranimine compound comprises greater than or equal to about 50% by weight of the electrolyte solution.

14. An energy storage device, comprising:
a positive electrode, a negative electrode, a separator between the positive electrode and the negative electrode, and an electrolyte solution, the electrolyte solution comprising:
at least one phosphoranimine compound comprising a cationic portion bonded to a nitrogen atom, a phosphorus atom bonded to the nitrogen atom, pendant groups bonded to the phosphorus atom, and a counterion, the counterion comprising tetrauoroborate (BF 4 − ), hexafluorophosphate (PF 6 − ), bis(oxalate)borate (BOB − ), hexafluoroarsenate (AsF 6 − ), hexafluoroantimonate (SbF 6 − ), tetrachloroaluminate (AlCl 4 − ), hydrogen sulfate (HSO 4 − ), perchlorate (ClO 4 − ), mesylate (CH 3 SO 3 − ), chloride (Cl − ), bromide (Br − ), iodide (I − ), an alkyl halide, a perhalogenated alkyl halide of a group VA element, trifluoromethanesulfonyl imide (N(SO 2 CF 3 ) 2 − ), trifluoromethanesulfonate (CF 3 SO 3 − ), or trifluoroacetate (CF 3 CO 2 − ).

15. The energy storage device of claim 14 , wherein the at least one phosphoranimine compound comprises the chemical structure:

herein:
each of R 1 , R 2 , and R 3 is independently selected from the group consisting of an acyl group, an acylamino group, an acyloxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, an alkylamino group, an alkylarylamino group, a dialkylamino group, an alkylthio group, an alkarylthio group, an aryl group, an arylamino group, a diarylamino group, an aryloxy group, an aralkyl group, an alkaryl group, an aralkoxy group, an alkaryloxy group, an arylthio group, an arylthio acyl group, an amino acid group, a carbamoyl group, a carbonamido group, a carboxyl group, a cyano group, a formyl group, a glycol group, a heteroalkyl group, a heteroaralkyl group, a heteroaryl group, a hydroxyl group, a nitro group, an oxy(aliphatic) group, an oxy(aliphatic)hydroxyl group, an oxy(alkyl)hydroxyl group, an oxycarbonyl group, an oxysulfonyl group, a perfluoroalkyl group, a phosphate group, a saccharide group, a sulfamoyl group, a sulfonamido group, a sulfonylamino group, a sulfonyl group, a sulfoxide group, a thio group, a thioalkaryl group, a thioaralkyl group, a trifluoroalkyl group, or an ureido group;
R 4 comprises an imidazolinium group, an imidazolium group, a phosphonium group, an ammonium group, a sulfonium group, a triazolium group, a thiazolium group, a pyridium group, a pyridinium group, an isoquinolinium group, a pyrrolidinium group, a pyrrolium group, a piperidinium group, or a pyrazolium group; and
X comprises the counterion.

16. The energy storage device of claim 14 , wherein the electrolyte solution further comprises a metal salt and an organic solvent.

17. A phosphoranimine compound comprising a cationic portion bonded to a nitrogen atom of the phosphoranimine compound, a phosphorus atom bonded to the nitrogen atom, pendant groups bonded to the phosphorus atom, and a counterion, the counterion comprising tetrafluoroborate (BF 4 − ), hexafluorophosphate (PF 6 − ), bis(oxalate)borate (BOB − ), hexafluoroarsenate (

Assignees

• Battelle Energy Alliance Llc

Inventors

• Klaehn John R
• Dufek Eric J
• Mcnally Joshua S

Classifications

• H01M10/0567 Primary

  characterised by the additives · CPC title

• Y02E60/13

  Energy storage using capacitors · CPC title

• H01G11/64

  characterised by additives · CPC title

• H01G11/60

  characterised by the solvent · CPC title

• H01M10/0525

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