Electrolytes for electrochemical energy storage

1. An electrochemical device comprising a cathode, an anode, and an electrolyte solution comprising a lithium or sodium salt, a polar aprotic solvent, and from 0.005 M to 2 M of a compound of Formula I:

wherein:

R 1 is a substituted or unsubstituted alkoxy, a substituted or unsubstituted C 6 -C 20 aryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted heterocyclylalkyl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heteroaralkyl, silyl, linear carbonate group, cyano group, oligo (ethylene glycol), CH 2 C(O)NH(OH), or —CH 2 P(O)(OR 5 ) 2 ;

R 2 is H, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkenylalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted heterocyclylalkyl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heteroaralkyl, silyl, linear carbonate group, cyano group, or oligo (ethylene glycol);

R 3 is H, silyl, Li + , Na + , K + , or NH 4 + ;

each R 5 is individually a substituted or unsubstituted alkyl, —CH 2 (CF 2 ) q CF 3 , 2-furanyl, 3-furanyl, phenyl, or ethylene carbonate, wherein each q is from 0 to 20, inclusive; and

the polar aprotic solvent is selected from organic carbonates, fluorinated carbonates, ethers, fluorinated ethers, glymes, organic sulfates, esters, cyclic esters, fluorinated esters, nitriles, amides, dinitriles, fluorinated amides, carbamates, fluorinated carbamates, cyanoester compounds, or a mixture of any two or more thereof.

2. The electrochemical device of claim 1 , wherein R 1 is unsubstituted phenyl, substituted phenyl, unsubstituted naphthyl, substituted naphthyl, unsubstituted heterocyclyl, substituted heterocyclyl, unsubstituted heterocyclylalkyl, or substituted heterocyclylalkyl.

3. The electrochemical device of claim 1 , wherein R 1 is CH 2 C(O)NH(OH), O(CH 2 CH 2 O) q CH 3 , or —CH 2 P(O)(OR 5 ) 2 , wherein each R 5 is individually substituted or unsubstituted alkyl, —CH 2 (CF 2 ) q CF 3 , 2-furanyl, 3-furanyl, phenyl, or ethylene carbonate, wherein each q is from 0 to 20, inclusive.

4. The electrochemical device of claim 1 , wherein R 2 is H, unsubstituted C 1 -C 20 alkyl, substituted C 1 -C 20 alkyl, unsubstituted C 1 -C 20 alkenylalkyl, substituted C 1 -C 20 alkenylalkyl, unsubstituted phenyl, substituted phenyl, unsubstituted naphthyl, substituted naphthyl, unsubstituted heterocyclyl, substituted heterocyclyl, unsubstituted heterocyclylalkyl, substituted heterocyclylalkyl, or trimethylsilyl.

5. The electrochemical device of claim 1 , wherein R 2 is H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, trimethylsilyl, triethylsilyl, perfluoroethyl, perfluoropropyl, or 2-allyl.

6. The electrochemical device of claim 1 , wherein R 3 is H or Li + .

7. The electrochemical device of claim 1 , wherein R 3 is H, silyl, Li + , Na + , or K + .

8. The electrochemical device of claim 1 , wherein the electrolyte solution comprises the lithium salt and the lithium salt comprises a lithium alkyl fluorophosphate; lithium alkyl fluoroborate; lithium 4,5-dicyano-2-(trifluoromethyl)imidazole; lithium 4,5-dicyano-2-methylimidazole; trilithium 2,2′,2″-tris(trifluoromethyl)benzotris(imidazolate); LiN(CN) 2 ; Li(CF 3 CO 2 ); Li(C 2 F 5 CO 2 ); LiCF 3 SO 3 ; LiCH 3 SO 3 ; LiN(SO 2 CF 3 ) 2 ; LiN(SO 2 F) 2 ; LiC(CF 3 SO 2 ) 3 ; LiN(SO 2 C 2 F 5 ) 2 ; LiClO 4 ; LiBF 4 ; LiAsF 6 ; LiPF 6 ; LiBF 2 (C 2 O 4 ); LiB(C 2 O 4 ) 2 ; LiPF 2 (C 2 O 4 ) 2 ; LiPF 4 (C 2 O 4 ); LiAsF 6 ; CsF; CsPF 6 ; LiN(SO 2 CF 3 ) 2 ; LiN(SO 2 F) 2 ; Li 2 (B 12 X 12-p H p ); Li 2 (B 10 X 10-p′ H p′ ); or a mixture of any two or more thereof, wherein X may be independently at each occurrence a halogen, p may be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, and p′ may be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

9. The electrochemical device of claim 1 , wherein the lithium salt comprises LiPF 6 , LiBF 4 , LiN(SO 2 CF 3 ) 2 , or LiN(SO 2 F) 2 .

10. The electrochemical device of claim 1 that is a lithium ion battery or a sodium ion battery.

11. The electrochemical device of claim 1 , wherein the compound of Formula I is:

wherein:

each E is independently —OH, —O—Li + , —O—Na + , —O—K + , or —O—NH 4 + ;

R 10 is H, Cl, NO 2 , or OCH 3 ; and

each q is from 0 to 20, inclusive.

12. The electrochemical device of claim 11 further comprising a separator between the anode and the cathode.

13. The electrochemical device of claim 11 , wherein each E is independently —OH, —O—Li + , —O—Na + , or —O—K + .