Electronic devices made with metal Schiff base complexes

Abstract

The present invention relates to new electronic devices including a layer comprising a photoactive material and metal Schiff base complex, wherein the metal Schiff base complex is present as a host for the photoactive material or in a layer between the cathode and the photoactive material containing layer, or both.

1 . An organic electronic device comprising a cathode, a layer comprising a photoactive material positioned there between and a metal Schiff base complex, wherein the metal Schiff base complex is present as a host for the photoactive material or in a layer between a cathode and the photoactive material containing layer or in both layers.  
   
   
       2 . An organic electronic device according to  claim 1 , wherein the metal Schiff base complex has Formula (I)  
       M(SB) a L 1   b    Formula (I)  
     wherein: 
 M is a metal in a +3 oxidation state;  
 SB is a Schiff base ligand;  
 L 1  is a ligand having the formula Ar—O, where Ar is selected from an aromatic group and a heteroaromatic group;  
 a is 1, 2, or 3;  
 b is 0, 1, or 2;  
 with the proviso that the metal Schiff base complex is electrically uncharged.  
 
   
   
       3 . An organic electronic device according to  claim 2 , wherein M is selected from Al, Zn, and Ga.  
   
   
       4 . An organic electronic device according to  claim 2 , wherein the Schiff base ligand is selected from Structure I, II, III, and IV, below:  
     
       
         
         
             
             
         
       
     
     wherein: 
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 Z is selected from alkylene, heteroalkylene, arylene, and heteroarylene;  
                     
 wherein:  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings;  
                     
 wherein:  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 Z is selected from alkylene, heteroalkylene, arylene, and heteroarylene;  
                     
 wherein:  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 R 4  is selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl.  
 
   
   
       5 . An organic electronic device according to  claim 1 , wherein the metal Schiff base complex has Formula I(a)  
       M(SB)L 1    Formula I(a)  
     wherein 
 M is a metal in a +3 oxidation state;  
 L 1  is a ligand having the formula Ar—O, where Ar is selected from an aromatic group and a heteroaromatic group;  
 SB is a Schiff base ligand having Structure I:  
                     
 wherein:  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 Z is selected from alkylene, heteroalkylene, arylene, and heteroarylene.  
 
   
   
       6 . A device according to  claim 5 , wherein in each instance adjacent R 1  and R 2  join together to form a 6-membered aromatic ring.  
   
   
       7 . A device according to  claim 6 , wherein the aromatic ring is further substituted with a group selected from alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, alkoxy, aryloxy, and halide.  
   
   
       8 . A device according to  claim 5 , wherein R 3  is selected from hydrogen, phenyl, and methyl.  
   
   
       9 . A device according to  claim 5 , wherein Z is selected from alkylene having from 1-20 carbon atoms, phenylene, arylene having from 2 to 4 fused rings, bi-arylene, and aza-alkylene having from 2-20 carbon atoms.  
   
   
       10 . A device according to  claim 5 , wherein Z is selected from alkylene having from 1-6 carbon atoms; 1,2-cyclohexylene; 1,2-phenylene; 4-methoxy-1,2-phenylene; 4,5-dimethyl-1,2-phenylene; o-binaphthalene-diyl; 3-aza-1,5-pentylene; 1,2-o-tolyl-1,2-ethylene; 1,2-dicyano-1,2-ethylene; and 2-p-t-butylbenzyl-1,3-propylene.  
   
   
       11 . A device according to  claim 5 , wherein Z is selected from ethylene, 1,2-cyclohexylene, and —CH 2 CH 2 NHCH 2 CH 2 —.  
   
   
       12 . A device according to  claim 5 , wherein Ar is selected from phenyl, biphenyl, and naphthyl.  
   
   
       13 . A device according to  claim 1 , wherein the metal Schiff base complex is selected from Complexes 1 through 6:  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       14 . A device according to  claim 1 , wherein the metal Schiff base complex has Formula I(b)  
       M(SB)   Formula I(b)  
     wherein: 
 M is a metal in a +3 oxidation state;  
 SB is a Schiff base ligand having Structure II:  
                     
 wherein  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings.  
 
   
   
       15 . A device according to  claim 14 , wherein in each instance adjacent R 1  and R 2  join together to form a 6-membered aromatic ring.  
   
   
       16 . A device according to  claim 15 , wherein the aromatic ring is further substituted with a group selected from alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, alkoxy, aryloxy, and halide.  
   
   
       17 . A device according to  claim 15 , wherein the aromatic ring is 3,5-di(t-butyl)phenyl or naphthyl.  
   
   
       18 . A device according to  claim 15 , wherein R 3  is selected from hydrogen, phenyl, and methyl.  
   
   
       19 . A device according to  claim 1 , wherein the metal Schiff base complex has Formula I(a)  
       M(SB)L 1    Formula I(a)  
     wherein 
 M is a metal in a +3 oxidation state;  
 L 1  is a ligand having the formula Ar—O, where Ar is selected from an aromatic group and a heteroaromatic group;  
 SB is a Schiff base ligand having Structure III:  
                     
 wherein:  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 Z is selected from alkylene, heteroalkylene, arylene, and heteroarylene.  
 
   
   
       20 . A device according to  claim 19 , wherein in each instance adjacent R 1  and R 2  join together to form a 6-membered aromatic ring.  
   
   
       21 . A device according to  claim 20 , wherein the aromatic ring is further substituted with a group selected from alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, alkoxy, aryloxy, and halide.  
   
   
       22 . A device according to  claim 19 , wherein R 3  is selected from hydrogen, phenyl, and methyl.  
   
   
       23 . A device according to  claim 19 , wherein Z is selected from alkylene having from 1-20 carbon atoms, phenylene, arylene having from 2 to 4 fused rings, bi-arylene, and aza-alkylene having from 2-20 carbon atoms.  
   
   
       24 . A device according to  claim 19 , wherein Z is selected from alkylene having from 1-6 carbon atoms; 1,2-cyclohexylene; 1,2-phenylene; 4-methoxy-1,2-phenylene; 4,5-dimethyl-1,2-phenylene; o-binaphthalene-diyl; 3-aza-1,5-pentylene; 1,2-o-tolyl-1,2-ethylene; 1,2-dicyano-1,2-ethylene; and 2-p-t-butylbenzyl-1,3-propylene.  
   
   
       25 . A device according to  claim 19 , wherein Z is selected from ethylene, 1,2-cyclohexylene, and —CH 2 CH 2 NHCH 2 CH 2 —.  
   
   
       26 . A device according to  claim 19 , wherein Ar is selected from phenyl, biphenyl, and naphthyl.  
   
   
       27 . A device according to  claim 1 , wherein the metal Schiff base complex has Formula I(c) or I(d),  
       M(SB) 2 L 1    Formula I(c)  M(SB) 3    Formula I(d)  
     wherein: 
 M is a metal in a +3 oxidation state;  
 SB is a Schiff base ligand having Structure IV:  
                     
 wherein  
 R 1 , R 2 , R 3  are the same or different and are independently selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl, or adjacent R groups can join together to form 5- or 6-membered rings; and  
 R 4  is selected from hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl.  
 
   
   
       28 . A device according to  claim 14 , wherein in each instance adjacent R 1  and R 2  join together to form a 6-membered aromatic ring.  
   
   
       29 . A device according to  claim 28 , wherein the aromatic ring is further substituted with a group selected from alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, alkoxy, aryloxy, and halide.  
   
   
       30 . A device according to  claim 28 , wherein the aromatic ring is dichlorophenyl or alkylphenyl.  
   
   
       31 . A device according to  claim 27 , wherein R 4  is selected from alkyl having 1-20 carbon atoms and phenyl.  
   
   
       32 . A device according to  claim 31 , wherein R 4  is further substituted with a halide group or alkoxy group.