Electronic devices using organic small molecule semiconducting compounds

Abstract

Small organic molecule semi-conducting chromophores containing a halogen-substituted core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

1 - 43 . (canceled) 
     
     
         44 . A small molecule compound having Formula B: 
       
         
           
           
               
               
           
         
         wherein M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R 1 )—, —C(R 2 ) 2 . —C(R 3 ) 2 —, —CR 1 ═CR 3 ; 
         wherein H 1  and H 2  are both H 3 , or 
         wherein H 2  is 
       
       
         
           
           
               
               
           
         
         wherein J 1  is a nonentity or 
       
       
         
           
           
               
               
           
         
         wherein Q is a bivalent, trivalent, or tetravalent aryl or heteroaryl group; 
         wherein p is 1, 2, or 3; 
         wherein each of X 1 , X 2 , Y 1 , and Y 2  is halogen or H, wherein in at least one of X 1  and Y 1  is halogen, and at least one of X 2  and Y 2  is halogen; 
         wherein each H 1 , H 3 , and L 1  are independently selected from -A 1 -B 1 , -A 1 -B 2   
       
       
         
           
           
               
               
           
         
         wherein n is an integer between 0 and 5, inclusive, and m is an integer between 0 and 5, inclusive, and 1≤m+n≤5 for each structure where m and n occur together; 
         wherein A 1  is independently selected from substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group except thiophene, 
       
       
         
           
           
               
               
           
         
         wherein A 2  is independently a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group; 
         wherein B 1  is an aryl or heteroaryl group optionally substituted with one, two or more B 2 ; 
         wherein each B 2  is independently selected from H, a substituent, and 
       
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4 , and R 5  are each independently H or a substituent. 
       
     
     
         45 . A small molecule compound according to  claim 44 , wherein M is selected from sulfur (S), oxygen (O), and —N(R 1 )—. 
     
     
         46 . A small molecule compound according to  claim 44 , wherein R 1  is H, alkyl, or haloalkyl. 
     
     
         47 . A small molecule compound according to  claim 44  having Formula I: 
       
         
           
           
               
               
           
         
         wherein Q is a bivalent aryl or heteroaryl group. 
       
     
     
         48 . A small molecule compound according to  claim 47 , wherein Q is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phosphole, benzodithiophene, spirofluorene, spirothiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, iluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole, carbazole, 9,9-RR′-9H-fluorene 
       
         
           
           
               
               
           
         
       
       9-R-9H-carbazole 
       
         
           
           
               
               
           
         
       
       3,3′-RR′silyiene-2,2′-bithiophene 
       
         
           
           
               
               
           
         
       
       3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene 
       
         
           
           
               
               
           
         
       
       where R and R′═C 1 -C 30  alkyl or C 6 -C 30  aryl. 
     
     
         49 . A small molecule compound according to  claim 47 , wherein B 1  is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienehithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole. 
     
     
         50 . A small molecule compound according to  claim 47 , wherein H 1  and L 1  are 
       
         
           
           
               
               
           
         
       
     
     
         51 . A small molecule compound according to  claim 50 , wherein Q is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phosphole, benzodithiophene, spirofluorene, spirothiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithie.nopyrrole, dithienophosphole, carbazole, 9,9-RR′-9H-fluorene 
       
         
           
           
               
               
           
         
       
       9-R-9H-carbazole 
       
         
           
           
               
               
           
         
       
       3,3′-RR′silylene-2,2′-bithiophene 
       
         
           
           
               
               
           
         
       
       3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene 
       
         
           
           
               
               
           
         
       
       where R and R′═C 1 -C 30  alkyl or C 6 -C 30  aryl. 
     
     
         52 . A small molecule compound according to  claim 51 , wherein B 1  is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyciopentadiene, silacydopentadienehithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, henzoxazoie, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole. 
     
     
         53 . A small molecule compound according to  claim 47 , where Q is RR′silylene-2,2′-bithiophene and R and R′ are both C 1 -C 10  alkyl. 
     
     
         54 . A small molecule compound according to  claim 53 , wherein Q is 
       
         
           
           
               
               
           
         
       
     
     
         55 . A small molecule compound according to  claim 54 , wherein n+m=1. 
     
     
         56 . A small molecule compound according to  claim 55  wherein B 1  is substituted or unsubstituted thiophene. 
     
     
         57 . A small molecule compound according to  claim 56 , wherein B 1  is alkyl substituted thiophene. 
     
     
         58 . A small molecule compound according to  claim 47 , wherein the small molecule compound of Formula I is 
       
         
           
           
               
               
           
         
       
     
     
         59 . A small molecule according to  claim 44  having Formula IV-V: 
       
         
           
           
               
               
           
         
         wherein X 3  is X 2  and Y 3  is X 2 ; 
         wherein Q is a trivalent aryl or heteroaryl group; 
         wherein each E 1  is J 1 ; 
         and wherein each L 3  is H 1  or L 1 . 
       
     
     
         60 . A small molecule according to  claim 44  having Formula VI-VII: 
       
         
           
           
               
               
           
         
       
       wherein the moiety 
       
         
           
           
               
               
           
         
       
       is a tetravalent aryl or heteroaryl group selected from 
       
         
           
           
               
               
           
         
       
       (2,2′,7,7′-yl-9,9′-spirobi[fluorene]), 
       
         
           
           
               
               
           
         
       
       (3,3′,7,7′-yl-5,5′-spirobi[dibenzo[b,d]silole]), 
       
         
           
           
               
               
           
         
       
       (2,2′,6,6′- yl-4,4″-spirobi[cyclopenta[1,2-b:5,4-b′]dithiophene]), or 
       
         
           
           
               
               
           
         
       
       (2,2′,6,6′ -yl-4,4′spirobi[silolo[3,2-b:4,5-b′]dithiophene]);
 wherein X 3  and are X 2,  and Y 3  and Y 4  are Y 2 ; 
 wherein each F 1  is J 1 ;
 and wherein each L 4  is H 1  or L 1 . 
 
 
     
     
         61 . A small molecule compound according to  claim 60  of Formula VIa: 
       
         
           
           
               
               
           
         
       
     
     
         62 . A small molecule compound according to  claim 60  of Formula VIIa: 
       
         
           
           
               
               
           
         
       
     
     
         63 . A small molecule according to  claim 44  selected from Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 9, or Formula 10: 
       
         
           
           
               
               
           
         
       
       wherein n is at least 2: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein H 1  and each L 1  are the same and are -A 1 -B 2 ; where A 1  is a DONOR; 
         wherein R 7  is selected from H or a substituent; 
         wherein R 8  is C 6 -C 30  aryl optionally substituted with one or more C 1 -C 16  alkyl groups; 
         and wherein each DONOR is an aryl or heteroaryl group independently selected from: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein for each DONOR, X is C or Si; 
         wherein A is N or P; 
         wherein R 11  is selected from C 1 -C 16  alkyl; 
         wherein R 12 , R 15 , and R 16  are independently selected from C 1 -C 16  alkyl, C 6 -C 20  unsubstituted aryl, or C 6 -C 20  aryl substituted with one or more groups selected from —F, C 1 -C 20  alkyl, C 1 -C 20  fluoroalkyl, —O-C 1 -C 20  alkyl, or -C 1 -C 20  fluoroalkyl; 
         wherein R 13  is selected from C 1 -C 16  alkyl or C 6 -C 20  aryl; and 
         wherein R 14  is selected from C 1 -C 16  alkyl, —O-C 1 -C 16  alkyl, —C(═O)—O-C 1 -C 16  alkyl, or —O—C(═O)-C 1 -C 16 alkyl. 
       
     
     
         64 . A small molecule according to  claim 44  having Formula III: 
       
         
           
           
               
               
           
         
       
     
     
         65 . The compound of  claim 64 , wherein H 3  is selected from -A 1 -B 2 , or 
       
         
           
           
               
               
           
         
         wherein n is an integer between 0 and 5, inclusive, and in is an integer between 0 and 5, inclusive, and 1≤m+n≤15 for each structure where m and n occur together; 
         wherein B 1  is an aryl or heteroaryl group optionally substituted with one, two or more B 2 ; 
         wherein each B 2  is independently selected from H, a substituent, and 
       
       
         
           
           
               
               
           
         
       
       and
 wherein R 1 , R 2 , R 3 , R 4 , and R 5  are each independently H or a substituent. 
 
     
     
         66 . The compound of claim  21 , wherein the compound of formula III is a compound of Formula 7 or Formula 8: 
       
         
           
           
               
               
           
         
         wherein each n is independently selected from an integer frons 1 to 5, inclusive; 
         wherein J is selected from CH and N; 
         wherein X is S, O, or NH when J is CH; and X is S when J is N; 
         wherein R 6  is selected from H, a substituent, aryl, perfluoroaryl, or C 6 -C 30  aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16  alkyl groups; 
         and wherein each DONOR is an aryl or heteroaryl group independently selected from: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein for each DONOR, X is C or Si; 
         wherein A is N or P; 
         wherein R 11  is selected from C 1 -C 16  alkyl; 
         wherein R 12 , R 15 , and R 16  are independently selected from C 1 -C 16 ; alkyl, C 6 -C 20  unsubstituted aryl, or C 6 -C 20  aryl substituted with one or more groups selected from —F, C 1 -C 20  alkyl, C 1 -C 20  fluoroalkyl, —O-C 1 -C 20  alkyl, or -C 1 -C 20  fluoroalkyl; 
         wherein R 13  is selected from C 1 -C 16  alkyl or C 6 -C 20  aryl; and 
         wherein R 14  is selected from C 1 -C 16  alkyl, —O-C 1 -C 16  alkyl, —C(═O)—C—O-C 1 -C 16  alkyl, or —O—C(═O)-C 1 -C 16  alkyl. 
       
     
     
         67 . An electronic or optoelectronic device comprising a compound of  claim 44 . 
     
     
         68 . The electronic or optoelectronic device of  claim 67 , comprising:
 a first electrode;   a second electrode spaced apart from said first electrode; and   an active layer between said first electrode and said second electrode, wherein said active layer comprises the compound of  claim 44 .   
     
     
         69 . An electronic or optoelectronic device according to  claim 68 , further comprising a hole transporting layer between said first electrode and said active layer.