Modified ionic liquids containing triazine
The present disclosure is directed to a triazine-modified ionic liquid compound, the synthesis thereof and an electrochemical cell electrolyte containing the triazine-modified ionic liquid compound.
1. An ionic liquid compound, comprising:
an anion; and
a cation attached to a triazine moiety according to the formula:
wherein:
R is a Q + or R 1 or R 2 ; Q + is an azepanium, sulfonium, phosphonium, or a 5- or 6-membered heterocyclic ring having 1 to 3 heteroatoms as ring members comprising nitrogen, oxygen, silicon or sulfur;
R 1 and R 2 are independently a C 1 -C 8 alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, silyl, thioether, sulfoxide, azo, silane or amino group, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide, alkyl, alkenyl, alkoxy, aryl, alkynyl, alkylsiloxy, silyl, thioether, sulfoxide, azo, or amino group; and
X is (a) a linker, comprising a C 1 -C 8 alkylene, alkenylene, alkynylene, alkyleneoxy, ester, carbonyl, thioether, sulfoxide, azo or arylene group, wherein any of the carbon or hydrogen atoms therein are optionally further substituted with a halide; (b) O, S; or (c) O, S attached to the linker, wherein when X is O, O attached to C 2 alkylene or C 2 alkylene then Q + is not imidazolium.
2. The compound of claim 1 , wherein the anion comprises a halide, aluminate, arsenide, cyanide, thiocyanate, nitrite, benzoate, chlorate, chlorite, chromate, sulfate, sulfite, silicate, thiosulfate, oxalate, acetate, formate, hydroxide, nitrate, phosphate, imide, or borate.
3. An electrical energy storage device electrolyte comprising:
a) an aprotic organic solvent system;
b) a metal salt;
c) an additive; and
d) an ionic liquid compound according to claim 1 .
4. The electrolyte of claim 3 , wherein the anion of either or both of the metal salt and ionic liquid comprises a halide, aluminate, arsenide, cyanide, thiocyanate, nitrite, benzoate, chlorate, chlorite, chromate, sulfate, sulfite, silicate, thiosulfate, oxalate, acetate, formate, hydroxide, nitrate, phosphate, imide, or borate.
5. The electrolyte of claim 3 , wherein the aprotic organic solvent comprises an open-chain or cyclic carbonate, carboxylic acid ester, nitrite, ether, sulfone, ketone, lactone, dioxolane, glyme, crown ether, siloxane, phosphoric acid ester, phosphite, mono- or polyphosphazene or mixtures thereof.
6. The electrolyte of claim 5 , wherein the phosphoric acid ester is 4-fluorophenyldiphenylphosphate, 3,5-difluorophenyldiphenylphosphate, 4-chlorophenyldiphenylphosphate, trifluorophenylphosphate, heptafluorobutyldiphenylphosphate, trifluoroethyldiphenylphosphate, bis(trifluoroethyl)phenylphosphate, or phenylbis(trifluoroethyl)phosphate.
7. The electrolyte of claim 3 , wherein the additive comprises a sulfur-containing compound, phosphorus-containing compound, boron-containing compound, silicon-containing compound, fluorine-containing compound, nitrogen-containing compound, compound containing at least one unsaturated carbon-carbon bond, carboxylic acid anhydride or the mixtures thereof.
8. The electrolyte of claim 3 , wherein the electrolyte comprises the ionic liquid compound in a concentration of from about 0.01 wt. % to about 50.0 wt. %.
9. An electrochemical device comprising:
a cathode;
an anode; and
an electrolyte according to claim 3 .
10. The device of claim 9 , wherein the cathode comprises a lithium metal oxide, spinel, olivine, carbon-coated olivine, vanadium oxide, lithium peroxide, sulfur, polysulfide, a lithium carbon monofluoride or mixtures of any two or more thereof.
11. The device of claim 10 , wherein the lithium metal oxide is LiCoO 2 , LiNiO 2 , LiNi x Co y Met z O 2 , LiMn 0.5 Ni 0.5 O 2 , LiMn 0.3 Co 0.3 Ni 0.3 O 2 , LiMn 2 O 4 , LiFeO 2 , Li 1+x′ Ni α Mn β Co γ Met′ δ O 2−z′ F z′ , where Met is Al, Mg, Ti, B, Ga, Si, Mn or Co; Met′ is Mg, Zn, Al, Ga, B, Zr or Ti; and wherein 0≤x≤0.3, 0≤y≤0.5, 0≤z≤0.5, 0≤x′≤0.4, 0≤α≤1, 0≤β≤1, 0≤γ≤1, 0≤δ≤0.4, and 0≤z′≤0.4.
12. The device of claim 9 , wherein the anode comprises lithium metal, graphitic material, amorphous carbon, Li 4 Ti 5 O 12 , tin alloy, silicon alloy, intermetallic compound or mixtures thereof.
13. The device of claim 9 , wherein the device comprises a lithium battery, lithium-ion battery, lithium-sulfur battery, lithium-air battery, sodium ion battery, magnesium battery, lithium/MnO 2 battery, or Li/poly(carbon monofluoride) battery.
14. The device of claim 9 , further comprising a porous separator separating the anode and cathode from each other.
15. The device of claim 14 , wherein the porous separator comprises an electron beam-treated micro-porous polyolefin separator or a microporous polymer film comprising nylon, cellulose, nitrocellulose, polysulfone, polyacrylonitrile, polyvinylidene fluoride, polypropylene, polyethylene, polybutene, or co-polymers or blends of any two or more such polymers.
16. The device of claim 9 , wherein the device comprises a capacitor or solar cell.
17. The device of claim 9 , wherein the cathode is LiFePO 4 or A n′ B 2 (XO 4 ) 3 , where A is Li, Ag, Cu, Na, Mn, Fe, Co, Ni, Cu or Zn; B is Ti, V, Cr, Fe or Zr; X is P, S, Si, W or Mo and wherein 0≤n′≤3.
18. The electrolyte of claim 3 , wherein the metal salt is an alkali metal salt.
19. The electrolyte of claim 18 , wherein the cation of the alkali metal salt comprises lithium or sodium.
20. The electrolyte of claim 3 , wherein the metal salt is an aluminum salt or a magnesium salt.
21. The compound of claim 1 , wherein the aryl is phenyl or benzyl.
22. The compound of claim 1 , wherein Q + is pyrrolidinium, piperdinium, imidazolium, or pyridine.
23. The compound of claim 1 , wherein R 1 and R 2 are independently a silane.
24. The compound of claim 1 , wherein X is phenylene.