Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds

Abstract

The present invention is generally directed to electroluminescent Ir(III) complexes which have emission maxima in the red-orange to red region of the visible spectrum, and devices that are made with the Ir(III) complexes.

1 . An organic electronic device comprising an active layer comprising a light-emitting layer having an emission maximum in the range of 570 to 700 nm, wherein the active layer comprises at least one compound having a formula according to Formula I:  
       IrL 3    (I)  where:    L is selected from Formula III, Formula IV, Formula V, Formula VI, and Formula VII in  FIG. 1 , and Formula VIII, Formula IX and Formula X in  FIG. 2 , where:    in Formula III: 
 R 3  through R 6  are the same or different and at least one of R 3  through R 6  is selected from D, F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 Y;  
   at each occurrence in any of Formulae III through VII: 
 R 1  is the same or different at each occurrence and is selected from D, C n H 2n+1 , OR 11 , SR 11 , N(R 11 ) 2 , F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y, or adjacent pairs of R 1  can be joined to form a five- or six-membered ring;  
 Y is H, Cl, or Br; and  
 A is S or NR 11 ;  
   at each occurrence in any of Formulae III through X: 
 R 11  is the same or different at each occurrence and is H or C n H 2n+1 ;  
 n is an integer from 1 through 12; and  
 α is 0, 1 or 2;  
   at each occurrence in any of Formulae IV through X: 
 δ is 0 or an integer from 1 through 4;  
   in Formula VII: 
 E 1  through E 4  are the same or different and are N or CR 12 , with the proviso that at least one E is N; and  
 R 12  is the same or different at each occurrence and is selected from H, D, SR 11 , N(R 11 ) 2 , F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y, or adjacent pairs of R 12  can be joined to form a five- or six-membered ring, with the proviso that at least one of R 12  is selected from D, F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y;  
   at each occurrence in any of Formulae VIII through X: 
 R 2  and R 7  through R 10  are the same or different at each occurrence and are selected from H, D, C n H 2n+1 , OR 11 , SR 11 , and N(R 11 ) 2 , or adjacent pairs of R groups can be joined to form a five- or six-membered ring  
   provided that, where the active layer contains less than 20% by weight of the at least one compound, a diluent is also present.    
   
   
       2 . The device of  claim 1  wherein R 5  is CF 3 .  
   
   
       3 . The device of  claim 1  wherein R 8  is selected from OCH 3  and OH.  
   
   
       4 . The device of  claim 1  wherein R 9  is t-butyl.  
   
   
       5 . The device of  claim 1  wherein the diluent is selected from poly(N-vinyl carbazole); polysilane; 4,4′-N,N′-dicarbazole biphenyl; and tertiary aromatic amines.  
   
   
       6 . 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; 1,1-bis[(di-4-tolylamino) phenyl]cyclohexane; N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine; tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine; α-phenyl-4-N,N-diphenylaminostyrene; p-(diethylamino)benzaldehyde diphenylhydrazone; triphenylamine; bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane; 1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline; 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane; N,N,N′,N′-tetrakis(4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine; porphyrinic compounds; and combinations thereof.  
   
   
       7 . 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; 4,7-diphenyl-1,10-phenanthroline; 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole; 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole; and combinations thereof.  
   
   
       8 . A compound selected from complex 1-a through 1-f, as shown in Table 1.  
   
   
       9 . An organic electronic device comprising an active layer that comprises a compound selected from complex 1-a through 1-f, as shown in Table 1.  
   
   
       10 . The device of  claim 9  wherein the active layer further comprises a diluent.  
   
   
       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  wherein the diluent is a conjugated polymer selected from polyarylenevinylenes, polyfluorenes, polyoxadiazoles, polyanilines, polythiophenes, polypyridines, polyphenylenes, copolymers thereof, and combinations thereof.  
   
   
       13 . The device of  claim 12  wherein the diluent is a conjugated polymer selected from polyarylenevinylenes, polyfluorenes, polyoxadiazoles, polyanilines, polythiophenes, polypyridines, polyphenylenes, copolymers thereof, and combinations thereof.  
   
   
       14 . An active layer comprising at least one compound having a formula according to Formula I:  
       IrL 3    (I)  where:    L is selected from Formula III, Formula IV, Formula V, Formula VI, and Formula VII in  FIG. 1 , and Formula VIII, Formula IX and Formula X in  FIG. 2 , where:    in Formula III: 
 R 3  through R 6  are the same or different and at least one of R 3  through R 6  is selected from D, F, C n F 2n+1 , OC n F 2n+1 , and OCF 2 Y;  
   at each occurrence in any of Formulae III through VII: 
 R 1  is the same or different at each occurrence and is selected from D, C n H 2n+1 , OR 11 , SR 11 , N(R 11 ) 2 , F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y, or adjacent pairs of R 1  can be joined to form a five- or six-membered ring;  
 Y is H, Cl, or Br; and  
 A is S or NR 11 ;  
   at each occurrence in any of Formulae III through X: 
 R 11  is the same or different at each occurrence and is H or C n H 2n+1 ;  
 n is an integer from 1 through 12; and  
 α is 0, 1 or 2;  
   at each occurrence in any of Formulae IV through X: 
 δ is 0 or an integer from 1 through 4;  
   in Formula VII: 
 E 1  through E 4  are the same or different and are N or CR 12 , with the proviso that at least one E is N; and  
 R 12  is the same or different at each occurrence and is selected from H, D, SR 11 , N(R 11 ) 2 , F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y, or adjacent pairs of R 12  can be joined to form a five- or six-membered ring, with the proviso that at least one of R 12  is selected from D, F, C n (H+F) 2n+1 , OC n (H+F) 2n+1 , and OCF 2 Y;  
   at each occurrence in any of Formulae VIII through X: 
 R 2  and R 7  through R 10  are the same or different at each occurrence and are selected from H, D, C n H 2n+1 , OR 11 , SR 11 , and N(R 11 ) 2 , or adjacent pairs of R groups can be joined to form a five- or six-membered ring  
   provided that, where the active layer contains less than 20% by weight of the at least one compound, a diluent is also present.