Non-fullerene acceptors (nfas) as interfacial layers in perovskite semiconductor devices

Abstract

A method for producing an organic non-fullerene electron transport compound includes mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in dimethylformamide. The method also includes heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours. The method further includes isolating an organic non-fullerene electron transport compound reaction product.

1 . A compound comprising:
 a compound of formula (I);   
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of formulas (II), (III), (IV), (V), (VIII), or (IX), 
       
       
         
           
           
               
               
           
         
       
     
     
         2 . The composition of  claim 1 , wherein R has formula (II) 
     
     
         3 . The composition of  claim 1 , wherein R has formula (III). 
     
     
         4 . The composition of  claim 1 , wherein R has formula (IV). 
     
     
         5 . The composition of  claim 1 , wherein R has formula (V). 
     
     
         6 . The composition of  claim 1 , wherein R has formula (VIII). 
     
     
         7 . The composition of  claim 1 , wherein R has formula (IX). 
     
     
         8 . A method for producing an organic non-fullerene electron transport compound comprising:
 mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in an organic solvent;   heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours; and   isolating an organic non-fullerene electron transport compound reaction product.   
     
     
         9 . The method of  claim 8 , wherein the organic solvent comprises dimethylformamide or imidazole. 
     
     
         10 . The method of  claim 8 , wherein the amine compound comprises formula (VII); and 
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVI), and (XVIII); 
       
       
         
           
           
               
               
           
         
       
     
     
         11 . The method of  claim 8 , wherein the amine compound comprises formula (VIII); and 
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVII), and (XVIII); 
       
       
         
           
           
               
               
           
         
       
     
     
         12 . The method of  claim 8 , wherein the mixture is heated to a temperature greater than or equal to 100° and less than or equal to 120° C. for an amount of time greater than or equal to 1 hour and less than or equal to 2 hours. 
     
     
         13 . The method of  claim 8 , wherein isolating the organic non-fullerene electron transport compound reaction product comprises:
 cooling the mixture;   introducing an alcohol into the mixture after cooling to precipitate the non-fullerene electron transport compound reaction product;   collecting the precipitated organic non-fullerene electron transport compound reaction product by filtration;   washing the collected organic non-fullerene electron transport compound reaction product with alcohol; and   recrystallizing the washed organic non-fullerene electron transport compound reaction product or isolating the organic non-fullerene electron transport compound reaction product by column chromatography.   
     
     
         14 . The method of  claim 13 , wherein the alcohol to precipitate or to wash the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof. 
     
     
         15 . The method of  claim 8 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio. 
     
     
         16 . A method for producing an organic non-fullerene electron transport compound comprising:
 mixing naphthalene-1,4,5,8-tetracarboxylic dianhydride and an amine compound in an organic solvent;   heating the mixture to a temperature greater than or equal to 70° and less than or equal to 160° C. for an amount of time greater than or equal to 1 hour and less than or equal to 24 hours;   cooling the mixture;   introducing an alcohol into the mixture after cooling to precipitate the non-fullerene electron transport compound reaction product;   collecting the precipitated organic non-fullerene electron transport compound reaction product by filtration;   washing the collected organic non-fullerene electron transport compound reaction product with alcohol; and   isolating an organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate by recrystallization or by column chromatography.   
     
     
         17 . The method of  claim 16 , wherein the organic solvent comprises dimethylformamide or imidazole. 
     
     
         18 . The method of  claim 16 , wherein the amine compound comprises formula (VII) or formula (VIII); and 
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of formulas of(XIV), (XV), (XVI), (XVII), and (XVIII); 
       
       
         
           
           
               
               
           
         
       
     
     
         19 . The method of  claim 16 , wherein the alcohol to precipitate the non-fullerene electron transport compound reaction product comprises methanol, ethanol, isopropanol, or any mixture thereof. 
     
     
         20 . The method of  claim 16 , wherein naphthalene-1,4,5,8-tetracarboxylic dianhydride and the amine compound are mixed at 1:2 molar ratio. 
     
     
         21 . The method of  claim 16 , wherein isolating the organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate comprises recrystallization. 
     
     
         22 . The method of  claim 16 , wherein isolating the organic non-fullerene electron transport compound reaction product from the organic non-fullerene electron transport compound reaction product precipitate comprises column chromatography. 
     
     
         23 . The method of  claim 16 , wherein the organic non-fullerene electron transport compound comprises a compound of formula (XIX) or an enantiomer of formula (XIX) 
       
         
           
           
               
               
           
         
       
     
     
         24 . The method of  claim 16 , wherein the organic non-fullerene electron transport compound comprises a compound of formula (XXI) or an enantiomer of formula (XXI)