Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole chromophores for small molecule or vapor processed solar cells

Abstract

Optoelectronic devices, such as photovoltaic devices, comprising a low band gap, solution processable diketopyrrolopyrrole or dithioketopyrrolopyrrole chromophore core or cores are disclosed. Also disclosed are methods of fabricating such optoelectronic devices.

What is claimed is: 
     
         1 . A optoelectronic device comprising:
 a) a first hole-collecting electrode;   b) an optional hole-transporting layer;   c) a layer comprising a mixture of an electron donor material and an electron acceptor material; and   d) a second electron-collecting electrode,   wherein the electron donor material comprises a compound of Formula (I):   
       
         
           
           
               
               
           
         
         wherein X is oxygen or sulfur; 
         A 1  and A 2  are independently selected from substituted and unsubstituted aryl or heteroaryl groups, wherein each individual A 1  within the (A 1 ) m  moiety can be independently selected from a substituted or unsubstituted aryl or heteroaryl group, and each individual A 2  within the (A 2 ) n  moiety can be independently selected from a substituted or unsubstituted aryl or heteroaryl group; 
         B 1  is independently selected from substituted and unsubstituted aryl or heteroaryl groups; 
         m is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; 
         n is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; 
         p is independently selected from 0 or 1; 
         E 1  and E 2  are independently selected from a nonentity, H, or a substituted or unsubstituted aryl or heteroaryl group or a C 1 -C 12  alkyl group; and 
         R 1 , R 2 , R 3 , and R 4  are independently selected from H, C 1 -C 12  alkyl, and —C(═O)—O—C 1 -C 12  alkyl. 
       
     
     
         2 . The device of  claim 1 , wherein X is oxygen. 
     
     
         3 . The device of  claim 1 , wherein p is 1. 
     
     
         4 . The device of  claim 1 , wherein A 1  and A 2  are independently selected from the group consisting of thiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, indole, benzene, naphthalene, anthracene, indene, fluorene, pyrene, azulene, furan, pyrrole, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, pyridothiadiazole, and carbazole. 
     
     
         5 . The device of  claim 1 , wherein B 1  is independently selected from the group consisting of thiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, indole, benzene, naphthalene, anthracene, indene, fluorene, pyrene, azulene, furan, pyrrole, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, pyridothiadiazole, carbazole, 
       
         
           
           
               
               
           
         
       
     
     
         6 . The device of  claim 1 , wherein A 1  is selected from 
       
         
           
           
               
               
           
         
       
       where m is independently 1, 2, or 3, and A 2  is selected from 
       
         
           
           
               
               
           
         
       
       here n is independently 1, 2, or 3. 
     
     
         7 . The device of  claim 1 , wherein m=n=1, m=n=2, or m=n=3. 
     
     
         8 . The device of  claim 1 , wherein R 1 , R 2 , R 3 , and R 4  are the same and are selected from hexyl, 2-ethylhexyl, t-butoxycarbonyl, and trimethylsilyl. 
     
     
         9 . The device of  claim 1 , wherein the first electrode comprises indium tin oxide and the second electrode comprises aluminum, silver or magnesium. 
     
     
         10 . The device of  claim 1 , wherein the optional hole transporting layer is present and comprises poly(3,4-ethylene dioxythiophene:poly(styrenesufonate) (PEDOT:PSS). 
     
     
         11 . The device of  claim 1 , wherein the electron acceptor is selected from the group consisting of fullerene electron acceptors, [6,6]-phenyl C61-butyric acid methyl ester (PCBM), PC 71 BM, titanium dioxide, and zinc oxide. 
     
     
         12 . A optoelectronic device comprising:
 a) a first hole-collecting electrode;   b) an optional hole-transporting layer;   c) a layer comprising a mixture of an electron donor material and an electron acceptor material;   and   d) a second electron-collecting electrode,   wherein the electron donor material comprises a compound of Formula (II):   
       
         
           
           
               
               
           
         
         wherein 
         X is oxygen or sulfur; 
         A 1  and A 2  are selected from substituted and unsubstituted aryl or heteroaryl groups, wherein each individual A 1  within the (A 1 ) m  moiety can be independently selected from a substituted or unsubstituted aryl or heteroaryl group, and each individual A 2  within the (A 2 ) n  moiety can be independently selected from a substituted and unsubstituted aryl or heteroaryl group; 
         m is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; 
         n is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; 
         E 1  and E 2  are independently selected from a nonentity, H, or a substituted or unsubstituted aryl or heteroaryl group or a C 1 -C 12  alkyl group; 
         and 
         R 1  and R 2  are independently selected from H, C 1 -C 12  alkyl, and —C(═O)—O—C 1 -C 12  alkyl. 
       
     
     
         13 . The device of  claim 12 , wherein X is oxygen. 
     
     
         14 . The device of  claim 12 , wherein A 1  and A 2  are independently selected from the group consisting of thiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, indole, benzene, naphthalene, anthracene, indene, fluorene, pyrene, azulene, furan, pyrrole, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, pyridothiadiazole, and carbazole. 
     
     
         15 . The device of  claim 12 , wherein A 1  is selected from 
       
         
           
           
               
               
           
         
       
       where m is independently 1, 2, or 3, and A 2  is selected from 
       
         
           
           
               
               
           
         
       
       where n is independently 1, 2, or 3. 
     
     
         16 . The device of  claim 12 , wherein m=n=1, m=n=2, or m=n=3. 
     
     
         17 . The device of  claim 12 , wherein R 1  and R 2  are the same and are selected from hexyl, 2-ethylhexyl, t-butoxycarbonyl, and trimethylsilyl. 
     
     
         18 . The device of  claim 12 , wherein the first electrode comprises indium tin oxide and the second electrode comprises aluminum, silver or magnesium. 
     
     
         19 . The device of  claim 12 , wherein the optional hole transporting layer is present and comprises poly(3,4-ethylene dioxythiophene:poly(styrenesufonate) (PEDOT:PSS). 
     
     
         20 . The device of  claim 12 , wherein the electron acceptor is selected from the group consisting of fullerene electron acceptors, [6,6]-phenyl C61-butyric acid methyl ester (PCBM), PC 71 BM, titanium dioxide, and zinc oxide.