Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds

Abstract

The present invention is generally directed to electroluminescent Ir(III) compounds, the substituted 2-phenylpyridines, phenylpyrimidines, and phenylquinolines that are used to make the Ir(III) compounds, and devices that are made with the Ir(III) compounds.

What is claimed is:  
     
         1 . An organic electronic device comprising an emitting layer wherein at least 20% by weight of the emitting layer comprises at least one compound having a formula below:  
       IrL a L b L c   x L′ y L″ z ,  where: 
 x=0 or 1, y=0, 1 or 2, and z=0 or 1, with the proviso that: 
 x=0 or y+z=0 and  
 when y=2then z=0;  
 
 L′=a bidentate ligand or a monodentate ligand, and is not a phenylpyridine, phenylpyrimidine, or phenylquinoline; with the proviso that: 
 when L′ is a monodentate ligand, y+z=2, and when L′ is a bidentate ligand, z=0;  
 L″=a monodentate ligand, and is not a phenylpyridine, and phenylpyrimidine, or phenylquinoline; and  
 
 L a , L b  and L c  are alike or different from each other and each of L a , L b  and L c  has structure (I) below:  
                     
 wherein: 
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring,  
 at least one of R 1 -R 8  is selected from F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and  
 A=C or N, provided that when A=N, there is no R 1 .  
 
   
     
     
         2 . The device of  claim 1  wherein x=1, y=0, and z=0.  
     
     
         3 . The device of  claim 2  wherein A=C and none of R 1 -R 8  is selected from nitro.  
     
     
         4 . The device of  claim 1  wherein R 3  is CF 3 .  
     
     
         5 . The device of  claim 4  wherein at least one of R 5 -R 8  is selected from F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br.  
     
     
         6 . The device of  claim 2  wherein A=C, R 3 =CF 3 , R 7 =F, and R 1 , R 2 , R 4 -R 6  and R 8 =H.  
     
     
         7 . The device of  claim 2  wherein A=C, R 3  and R 6 =CF 3 , and R 1 , R 2 , R 4 , R 5 , R 7  and R 8 =H.  
     
     
         8 . The device of  claim 2  wherein A=C, R 3 =CF 3 , R 6  and R 8 =F, and R 1 , R 2 , R 4 , R 5 , and R 7 =H.  
     
     
         9 . The device of  claim 1  wherein x=0 and y=1 having a structure (VI) below:  
       
         
           
           
               
               
           
         
       
     
     
         10 . An organic electronic device comprising an emitting layer wherein the emitting layer comprises a diluent and less than 20% by weight of at least one compound that has a formula below:  
       IrL a L b L c ,  where: 
 L a , L b  and L c  are alike or different from each other and each of L a , L b  and L c  has structure (I) below:  
                     
 wherein: 
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring,  
 at least one of R 1 -R 8  is selected from F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and A=C or N, provided that when A=N, there is no R 1 .  
 
   
     
     
         11 . The device of  claim 10  wherein the diluent is selected from poly(N-vinyl carbazole), polysilane, 4,4′-N,N′-dicarbazole biphenyl, and tertiary aromatic amines.  
     
     
         12 . The device of  claim 1 , further comprising a hole transport layer selected from N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 1,1-bis[(di-4-tolylamino) phenyl]cyclohexane (TAPC), N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine (ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA), -phenyl-4-N,N-diphenylaminostyrene (TPS), p-(diethylamino)-benzaldehyde diphenylhydrazone (DEH), triphenylamine (TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane (MPMP), 1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl] pyrazoline (PPR or DEASP), 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB), N,N,N′,N′-tetrakis(4-methylphenyl)-(1, I′-biphenyl)-4,4′-diamine (TTB), porphyrinic compounds, and combinations thereof.  
     
     
         13 . The device of  claim 1 , further comprising an electron transport layer selected from tris(8-hydroxyquinolato)aluminum, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (DDPA), 4,7-diphenyl-1,10-phenanthroline (DPA), 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole (TAZ), and combinations thereof.  
     
     
         14 . A compound having a formula selected from fac-Ir(L) 3 , mer-Ir(L) 3 , and combinations thereof, where L is selected from group 1-a through 1-m and 1-q through 1-v, as shown in Table 1, and has structure (I) below:  
       
         
           
           
               
               
           
         
         wherein: 
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring, |at least one of R 1 -R 8  is selected from F, C n F 2n+1  , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and  
 A=C or N, provided that when A=N, there is no R 1 .  
 
       
     
     
         15 . A compound having a structure selected from structures (IV), (V), (VI), (IX) and (X) below: F 3 C Ir CF 3  (IV)  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         16 . An organic electronic device comprising an emitting layer that comprises a compound selected from the following (i) and (ii): 
 (i) a compound having a formula selected from fac-Ir(L) 3 , mer-Ir(L) 3 , and combinations thereof, where L is a group selected from 1-a through 1-m and 1-q through 1-v, as shown in Table 1 and has structure (I) below:                        wherein: 
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring,  
 at least one of R 1 -R 8  is selected from F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and  
 A=C or N, provided that when A N, there is no R 1 ;  
     (ii) a compound having one of structures (IV), (V), (VI), (IX), and (X) below:                                            
     
     
         17 . The device of  claim 16  wherein the emitting layer further comprises a diluent.  
     
     
         18 . The device of  claim 17  wherein the diluent is selected from poly(N-vinyl carbazole), polysilane, 4,4′-N,N′-dicarbazole biphenyl, and tertiary aromatic amines.  
     
     
         19 . A compound selected from compounds 2-a through 2-aa as shown in Table 2, having structure (II) below:  
       
         
           
           
               
               
           
         
         wherein: 
 R 9  is H;  
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring;  
 at least one of R 1 -R 8  is selected from F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and  
 A=C or N, provided that when A=N, there is no R 1 .  
 
       
     
     
         20 . A compound having structure (III) below:  
       
         
           
           
               
               
           
         
       
       wherein R 17 =CF 3  and R 10 -R 16  and R 18 -R 20 =H.  
     
     
         21 . A compound having structure VII below:  
       
         
           
           
               
               
           
         
         wherein: 
 B=H, CH 3 , or C 2 H 5 ;  
 L a , L b , L c , and L d  are the same or different from each other; and  
 each of L a , L b , L c , and L d  has structure (I) below:  
                     
 wherein: 
 adjacent pairs of R 1 -R 4  and R 5 -R 8  can be joined to form a five- or six-membered ring,  
 at least one of R 1 -R 8  is selected from F, C n F 2n+1a , OC n F 2n+1 , and OCF 2 X, where n=1-6 and X=H, Cl, or Br, and  
 A=C or N, provided that when A=N, there is no R 1 .  
 
 
       
     
     
         22 . The compound of  claim 21  wherein: 
 L a =L b =L c =L d ;  
 B=H;  
 R 3 =CF 3 ;  
 R 7 =F;  
 R 1 , R 2 , R 4 -R 6  and R 8 =H.