Materials for Battery Electrolytes and Methods for Use

Abstract

Described herein are materials for use in electrolytes that provide a number of desirable characteristics when implemented within batteries, such as high stability during battery cycling up to high temperatures high voltages, high discharge capacity, high coulombic efficiency, and excellent retention of discharge capacity and coulombic efficiency over several cycles of charging and discharging. In some embodiments, a high voltage electrolyte includes a base electrolyte and a set of additive compounds, which impart these desirable performance characteristics.

1 .- 23 . (canceled) 
     
     
         24 . A battery comprising:
 a cathode, the cathode comprising a material selected from the group consisting of high voltage phosphates, high voltage fluorophosphates, high voltage fluorosilicates, high voltage Li-rich layered oxides, NMC-type cathode material, and high voltage spinels, with the proviso that the high voltage spinel is not an LMO-type LiM 2 O 4 ; and   an electrolyte solution, the electrolyte solution comprising:
 a lithium salt; 
 a solvent; and 
 a compound represented by the formula (I): 
   
       
         
           
           
               
               
           
         
         
           
             wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 20  alkyl groups, substituted and unsubstituted C 1 -C 20  alkenyl groups, substituted and unsubstituted C 1 -C 20  alkynyl groups, and substituted and unsubstituted C 5 -C 20  aryl groups; and 
             X is selected from the group consisting of carbon, substituted and unsubstituted C 3 -C 20  alkyl groups, substituted and unsubstituted C 2 -C 20  alkenyl groups, and substituted and unsubstituted C 4 -C 20  alkynyl groups; and 
           
           wherein the electrolyte solution is characterized by electrochemical stability when the battery is operated at voltages above 4.2V. 
         
       
     
     
         25 . The battery of  claim 24  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 20  alkyl groups. 
     
     
         26 . The battery of  claim 24  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 6  alkyl groups. 
     
     
         27 . The battery of  claim 24  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1  alkyl groups. 
     
     
         28 . The battery of  claim 24  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are each C 1  alkyl groups. 
     
     
         29 . The battery of  claim 24  wherein the compound is represented by the formula (II): 
       
         
           
           
               
               
           
         
       
     
     
         30 . The battery of  claim 24  wherein the battery retains at least 90% of its capacity after 100 cycles when cycled to voltages above 4.2 V. 
     
     
         31 . The battery of  claim 24  wherein the battery retains at least 80% of its capacity after 200 cycles when cycled to voltages above 4.2 V. 
     
     
         32 . The battery of  claim 24  wherein the cathode comprises a high voltage phosphate material. 
     
     
         33 . The battery of  claim 24  wherein the cathode comprises a high voltage fluorophosphate material. 
     
     
         34 . The battery of  claim 24  wherein the cathode comprises a high voltage fluorosilicate material. 
     
     
         35 . The battery of  claim 24  wherein the cathode comprises a high voltage Li-rich layered oxide material. 
     
     
         36 . The battery of  claim 24  wherein the cathode comprises a NMC-type cathode material. 
     
     
         37 . The battery of  claim 24  wherein the cathode comprises a high voltage spinel material, with the proviso that the high voltage spinel is not an LMO-type LiM 2 O 4 . 
     
     
         38 . A method of using a battery comprising:
 charging a voltage above 4.2 V into the battery, the battery comprising:
 a cathode; and 
 an electrolyte solution, the electrolyte solution comprising:
 a lithium salt; 
 a solvent; and 
 a compound represented by the formula (I): 
 
   
       
         
           
           
               
               
           
         
         
           
             wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from group consisting of substituted and unsubstituted C 1 -C 20  alkyl groups, substituted and unsubstituted C 1 -C 20  alkenyl groups, substituted and unsubstituted C 1 -C 20  alkynyl groups, and substituted and unsubstituted C 5 -C 20  aryl groups; and 
             X is selected from the group consisting of carbon, substituted and unsubstituted C 3 -C 20  alkyl groups, substituted and unsubstituted C 2 -C 20  alkenyl groups, and substituted and unsubstituted C 4 -C 20  alkynyl groups; and 
           
         
         wherein the electrolyte solution is characterized by electrochemical stability when the battery is operated at voltages above 4.2V. 
       
     
     
         39 . A method of using a battery comprising:
 providing a cathode, the cathode comprising a material selected from the group consisting of high voltage phosphates, high voltage fluorophosphates, high voltage fluorosilicates, high voltage Li-rich layered oxides, NMC-type cathode material, and high voltage spinels, with the proviso that the high voltage spinel is not an LMO-type LiM2O4; and   providing an electrolyte solution, the electrolyte solution comprising:
 a lithium salt; 
 a solvent; and 
 a compound represented by the formula (I): 
   
       
         
           
           
               
               
           
         
         
           wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 20  alkyl groups, substituted and unsubstituted C 1 -C 20  alkenyl groups, substituted and unsubstituted C 1 -C 20  alkynyl groups, and substituted and unsubstituted C 5 -C 20  aryl groups; and 
           X is selected from the group consisting of carbon, substituted and unsubstituted C 3 -C 20  alkyl groups, substituted and unsubstituted C 2 -C 20  alkenyl groups, and substituted and unsubstituted C 4 -C 20  alkynyl groups. 
         
         forming the battery from the cathode and the electrolyte solution; and 
         charging the battery. 
       
     
     
         40 . The method of  claim 39  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 20  alkyl groups. 
     
     
         41 . The method of  claim 39  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1 -C 6  alkyl groups. 
     
     
         42 . The method of  claim 39  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from the group consisting of substituted and unsubstituted C 1  alkyl groups. 
     
     
         43 . The method of  claim 39  wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are each C 1  alkyl groups. 
     
     
         44 . The method of  claim 39  wherein X is selected from the group consisting of substituted and unsubstituted C 3 -C 6  alkyl groups. 
     
     
         45 . The method of  claim 39  wherein X is selected from the group consisting of substituted and unsubstituted C 2 -C 6  alkenyl groups. 
     
     
         46 . The method of  claim 39  wherein X is selected from the group consisting of substituted and unsubstituted C 4 -C 12  alkynyl groups. 
     
     
         47 . The method of  claim 39  wherein the compound is represented by the formula (II):