Organic light-emitting devices

Abstract

Disclosed are electrophosphorescent organic metal complexes with formula (I), (H), (III) or (IV), of either geometrical isomers, comprising two bidentate NN-type ligands, or two NO-type ligands, or a tetradentate NNNN-type ligand or a tetradentate NOON-type ligand, and a transition metal. These electrophosphorescent materials are valuable to the application in organic light-emitting devices (OLEDs), including red-, orange-, or yellow-light OLEDs.

1 . A heterostructured organic light-emitting device comprising at least one emissive layer comprising at least one host material and at least one dopant complex, wherein the dopant complex comprises a transition metal atom coordinated to two bidentate NN ligands, or two bidentate NO ligands, or a tetradentate NNNN ligand, or a tetradentate NOON ligand.  
     
     
         2 . The heterostructured organic light-emitting device of  claim 1 , wherein the emissive layer comprises one dopant complex, which dopant complex dopes the host material.  
     
     
         3 . The heterostructured organic light-emitting device of  claim 2 , wherein the dopant complex is geometrically in the cis-configuration.  
     
     
         4 . The heterostructured organic light-emitting device of  claim 2 , wherein the dopant complex is geometrically in the trans-configuration.  
     
     
         5 . The heterostructured organic light-emitting device of  claim 1 , wherein the emissive layer is a sublimation, vacuum deposition, vapor deposition or spin-coating layer.  
     
     
         6 . The heterostructured organic light-emitting device of  claim 1 , wherein the dopant complex is:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a mixture thereof, wherein 
 M is a transition metal selected from the group consisting of Ni, Pd and Pt;  
 each R 1 -R 10  is independently —H, —OH, —NH 2 , -halogen, —CN, —NO 2 , —R 13 , —OR 14  —NHR 4 , or —N(R 14 ) 2 ;  
 R 11  is —(C(R 15 ) 2 ) n- ,  
                     
 each R 12  is independently —H, —(C 1 -C 6 )alkyl, -phenyl, -naphthyl; -halogen, or —CN;  
 R 13  is —(C 1 -C 6 )alkyl, -phenyl, or -naphthyl, each of which is unsubstituted or substituted with one or more —(C 1 -C 6 )alkyl, -phenyl, or -naphthyl;  
 R 14  is as defined above for R 13 ;  
 R 15  is as defined above for R 1 ;  
 each x is independently a carbon or nitrogen atom; and  
 n is an integer from 1 to 6.  
 
     
     
         7 . The heterostructured organic light-emitting device of  claim 6 , wherein M is Pt.  
     
     
         8 . The heterostructured organic light-emitting device of  claim 7 , having structure I or II.  
     
     
         9 . The heterostructured organic light-emitting device of  claim 7 , having structure III or IV.  
     
     
         10 . The heterostructured organic light-emitting device of  claim 7 , wherein the dopant complex is selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
       or a mixture thereof.  
     
     
         11 . The heterostructured organic light-emitting device of  claim 1 , wherein the emissive layer comprises 0.5 to 8.0 weight % dopant complex based on the weight of host material.  
     
     
         12 . The heterostructured organic light-emitting device of  claim 1 , wherein the emissive layer comprises a dopant complex exhibits an electroluminescence of visible color.  
     
     
         13 . The heterostructured organic light-emitting device of  claim 1 , wherein the emissive layer comprises a dopant complex which exhibits red, orange or yellow electroluminescence.  
     
     
         14 . The heterostructured organic light-emitting device of  claim 1 , wherein the host material is selected from the group consisting of beryllium bis(2-(2′-hydroxyphenyl)pyridine, 4,4′-bis(carbazol-9-yl)biphenyl (CBP), N,N′-diphenyl-N,N′-bis(1-naphthalene)benzidine (α-NPB), N,N′-diphenyl-N,N′-bis(2-naphthalene)benzidine (β-NPB), N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD), 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-TDATA) or tetrakis(diarylamino)-9,9′-spirobifluorene.  
     
     
         15 . A method for preparing a heterostructured organic light emitting devices which comprises providing an emissive layer, wherein the emissive layer comprising at least one host material and at least one dopant complex, the dopant complex comprising a transition metal coordinated to two bidentate NN ligands, or two bidentate NO ligands, or a tetradentate NNNN ligand, or a tetradentate NOON ligand.  
     
     
         16 . The method of  claim 15 , wherein the dopant complex in emissive layer is:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a mixture thereof, wherein 
 M is a transition metal selected from the group consisting of Ni, Pd and Pt;  
 each R 1 -R 10  is independently —H, —OH, —NH 2 , -halogen, —CN, —NO 2 , —R 13 , —OR 4 , —NHR 14 , or —N(R 4 ) 2 ;  
 R 11  is  13  (C(R 15 ) 2 ) n- ,  
                     
 each R 12  is independently —H, —(C 1 -C 6 )alkyl, -phenyl, -naphthyl; -halogen, or —CN;  
 R 13  is —(C 1 -C 6 )alkyl, -phenyl, or -naphthyl, each of which is unsubstituted or substituted with one or more —(C 1 -C 6 )alkyl, -phenyl, or -naphthyl;  
 R 14  is as defined above for R 13 ; and  
 R 15  is as defined above for R 1 ;  
 each x is independently a carbon or nitrogen atom; and  
 n is an integer number from 1 to 6.  
 
     
     
         17 . The method of  claim 15 , wherein M is Pt.  
     
     
         18 . The method of  claim 17 , wherein the dopant complex in emissive layer is selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
       or a mixture thereof  
     
     
         19 . The method of  claim 15 , wherein the emissive layer comprises 0.5 to 8.0 weight % dopant complex based on weight of host material.  
     
     
         20 . The method of  claim 15 , wherein the emissive layer comprises a dopant complex exhibits an electroluminescence of visible color.  
     
     
         21 . The method of  claim 20 , wherein the emissive layer comprises a dopant complex which exhibits red, orange or yellow electroluminescence.