Emissive aryl-heteroaryl compounds

Abstract

Disclosed herein are compounds represented by Formula 1, wherein R 1 , Ar 1 , X, Ar 2 , Ar a , and Het are described herein. Compositions and light-emitting devices related thereto are also disclosed.

1 . A compound represented by a formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is a C 1-10 O 1-4  ether attaching at an oxygen atom or —R 7 —NR 8 R 9 ;
 wherein R 7  is a single bond, optionally substituted C 6-10  aryloxy, or optionally substituted C 6-10  aryl; and 
 R 8  and R 9  are independently optionally substituted C 6-10  aryl, wherein R 8  and R 9  optionally link together form a third ring comprising N; 
 
         Ar 1  and Ar 2  are independently aryl having 0, 1, 2, 3, or 4 substituents independently selected from C 1-3  alkyl and F; 
         X is O or a single bond; 
         Ar 3  is aryl having 0, 1, 2, 3, or 4 substituents independently selected from C 1-3  alkyl and F; or Ar 3  is a single bond; 
         Z is independently NR 6 , wherein R 6  is optionally substituted phenyl, optionally substituted —CH 2 -phenyl, or optionally substituted (4-halophenyl)methyl; and 
         R 2 , R 3 , R 4 , and R 5  are independently H, optionally substituted C 6-30  aryl, C 1-10  alkyl, or C 1-10  alkoxy; 
         with the proviso that —Ar 1 —X—Ar 2 —Ar 3 — is not: 
       
       
         
           
           
               
               
           
         
       
     
     
         2 . The compound of  claim 1 , wherein R 1  is optionally substituted carbazolyl, optionally substituted carbazolylphenoxy, optionally substituted diphenyl amine, optionally substituted diphenylaminophenoxy, or C 1-10  alkoxy. 
     
     
         3 . The compound of  claim 2  wherein R 1  is methoxy, 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein Ar 1 , Ar 2 , and Ar 3  are optionally substituted p-interphenylene. 
     
     
         5 . The compound of  claim 1 , wherein at least one of Ar 1 , Ar 2 , and Ar 3  is unsubstituted p-interphenylene. 
     
     
         6 . The compound of  claim 1 , wherein X is O. 
     
     
         7 . The compound of  claim 6 , wherein Z is O. 
     
     
         8 . The compound of  claim 6 , wherein Z is NR 6  and R 6  is optionally substituted phenyl. 
     
     
         9 . The compound of  claim 8 , wherein R 1  is optionally substituted diphenyl amine. 
     
     
         10 . The compound of  claim 8 , wherein R 1  is optionally substituted carbazolyl. 
     
     
         11 . The compound of  claim 8 , wherein R 1  is optionally substituted p-carbazolylphenoxy. 
     
     
         12 . The compound of  claim 8 , wherein R 1  is optionally substituted p-diphenylaminophenoxy. 
     
     
         13 . The compound of  claim 1 , wherein X is a single bond. 
     
     
         14 . The compound of  claim 13 , wherein Ar 3  is a single bond. 
     
     
         15 . The compound of  claim 14 , wherein R 1  is optionally substituted diphenyl amine. 
     
     
         16 . The compound of  claim 14 , wherein R 1  is optionally substituted carbazolyl. 
     
     
         17 . The compound of  claim 13 , wherein Ar 3  is aryl having 0, 1, 2, 3 or 4 substituents independently selected from C 1-3  alkyl and F. 
     
     
         18 . The compound of  claim 17 , wherein R 1  is optionally substituted diphenyl amine. 
     
     
         19 . The compound of  claim 17 , wherein R 1  is optionally substituted carbazolyl. 
     
     
         20 . The compound of  claim 1 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         21 . A compound represented by a formula:
   R 1 —Ar 1 —X—Ar 2 —Ar 3 —Het
   wherein R 1  is C 1-10  alkoxy, substituted carbazolyl, substituted diphenylamino, optionally substituted carbazolylphenoxy, or optionally substituted diphenylaminophenoxy;   Ar 1  and Ar 2  are independently optionally substituted aryl; X is O or a single bond;   Ar 3  is optionally substituted aryl; or Ar 3  is a single bond; and   Het is optionally substituted benzoimidazolyl.   
     
     
         22 . A compound represented by a formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is C 1-10  alkoxy, substituted carbazolyl, substituted diphenylamino, optionally substituted carbazolylphenoxy, or optionally substituted diphenylaminophenoxy; and 
         Het is optionally substituted benzoimidazolyl. 
       
     
     
         23 . The compound of  claim 22 , wherein R 1  is substituted diphenylamino or substituted carbazolyl. 
     
     
         24 . The compound of  claim 22 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         25 . The compound of  claim 24 , wherein the compound is prepared by a process comprising:
 reacting a mixture comprising   
       
         
           
           
               
               
           
         
       
       and
 [1,1-bis(diphenylphosphino)ferrocene]palladium(II)dichloride to provide a composition comprising: 
 
       
         
           
           
               
               
           
         
       
       and
 reacting a mixture comprising 
 
       
         
           
           
               
               
           
         
       
       and
 tetrakis(triphenylphosphino)palladium(0) to provide a composition comprising: 
 
       
         
           
           
               
               
           
         
       
     
     
         26 . A compound represented by a formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is a C 1-10 O 1-4  ether attaching at an oxygen atom or —R 7 —NR 8 R 9 ;
 wherein R 7  is a single bond, optionally substituted C 6-10  aryloxy, or optionally substituted C 6-10  aryl; and 
 R 8  and R 9  are independently optionally substituted C 6-10  aryl, wherein R 8  and R 9  optionally link together form a third ring comprising N; 
 
         Ar 1  and Ar 2  are independently aryl having 0, 1, 2, 3, or 4 substituents independently selected from C 1-3  alkyl and F; 
         X is O or a single bond; 
         Ar 3  is aryl having 0, 1, 2, 3, or 4 substituents independently selected from C 1-3  alkyl and F; or Ar 3  is a single bond; 
         Z is independently O or S; and 
         R 2 , R 3 , R 4 , and R 5  are independently H, optionally substituted C 6-30  aryl, C 1-10  alkyl, or C 1-10  alkoxy. 
       
     
     
         27 . The compound of  claim 25 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         28 . A light-emitting device, comprising:
 a light-emitting layer comprising a compound according to  claim 1 .   
     
     
         29 . A method of converting an electric potential difference to light comprising exposing a composition comprising a compound according to  claim 1  to an electric potential difference to thereby produce light. 
     
     
         30 . A method of converting light to an electric potential difference comprising exposing a composition comprising a compound according to  claim 1  to light to thereby produce an electric potential difference.