Organic Electroluminescent Devices and Metal Complex Compounds

Abstract

An organic electroluminescent device, which has a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes, wherein at least one layer between the pair of electrodes comprises at least one metal complex having a tridentate- or higher polydentate-chain structure ligand.

1 .- 12 . (canceled) 
     
     
         13 . An organic electroluminescent device, comprising
 a pair of electrodes; and   at least one organic layer including a luminescent layer between the pair of electrodes;   wherein at least one layer between the pair of electrodes comprises at least one metal complex represented by formula (1):   
       
         
           
           
               
               
           
         
         
           wherein, 
           M 11  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
           L 11 , L 12 , L 13 , L 14 , and L 15  each represent a ligand to coordinate to M 11 ; 
           L 11  and L 14  do not combine together via an atomic group to form a cyclic ligand;
 L 15  does not bond to both L 11  and L 14  to form a cyclic ligand; 
 
           Y 11 , Y 12 , and Y 13  each represent a linking group, a single bond, or a double bond; 
           a bond between L 11  and Y 12 , a bond between Y 12  and L 12 , a bond between L 12  and Y 11 , a bond between Y 11  and L 13 , a bond between L 13  and Y 13 , and a bond between Y 13  and L 14  each represent a single bond or a double bond; 
           n 11  represents 0 to 4; and 
           wherein the compound comprises a metal-carbon bond. 
         
       
     
     
         14 . The organic electroluminescent device as claimed in  claim 13 , wherein L 11 , L 12 , L 13 , L 14 , and L 15  each independently coordinate to M 11  via a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. 
     
     
         15 . The organic electroluminescent device as claimed in  claim 13 , wherein L 11  and L 14  are each an aromatic carbocyclic ligand, an alkyloxy ligand, an aryloxy ligand, an ether ligand, an alkylthio ligand, an arylthio ligand, an alkylamino ligand, an arylamino ligand, an acylamino ligand, and a nitrogen-containing heterocyclic ligand, or a condensed ligand containing any of these ligands. 
     
     
         16 . The organic electroluminescent device as claimed in  claim 13 , wherein L 12  and L 13  are each a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, or a condensed ring containing any of these rings. 
     
     
         17 . The organic electroluminescent device as claimed in  claim 13 , wherein the metal complex is represented by formula (6): 
       
         
           
           
               
               
           
         
         wherein, 
         M 61  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
         L 65  represents a ligand to coordinate to M 61 ; 
         Y 61  represents a linking group, a single bond, or a double bond; 
         Y 62  and Y 63  each represent a linking group or a single bond; 
         Q 61  and Q 62  each represent a group to form a ring; 
         Z 61 , Z 62 , Z 63 , Z 64 , Z 65 , Z 66 , Z 67 , and Z 68  each represent a substituted or unsubstituted carbon atom or a nitrogen atom; 
         Z 61  and Z 62 , Z 62  and Z 63 , Z 63  and Z 64 , Z 65  and Z 66 , Z 66  and Z 67 , Z 67  and Z 68  each may bond to each other via a linking group to form a condensed ring; 
         the ring formed by Q 61  or Q 62  may bond to Z 61  or Z 68  respectively via a linking bond to form a ring; and 
         n 61  represents 0 to 4. 
       
     
     
         18 . The organic electroluminescent device as claimed in  claim 13 , wherein the metal complex is represented by formula (7): 
       
         
           
           
               
               
           
         
         wherein, 
         M 71  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
         L 75  represents a ligand to coordinate to M 71 ; 
         Y 71 , Y 72 , and Y 73  each represent a linking group, a single bond, or a double bond; 
         R 71 , R 72 , R 73 , and R 74  each represent a hydrogen atom or a substituent; 
         R 71  and R 72 , and R 73  and R 74  may bond to each other to form a condensed ring; 
         Z 71 , Z 72 , Z 73 , Z 74 , Z 75  and Z 76  each represent a substituted or unsubstituted carbon atom or a nitrogen atom; 
         Z 71  and Z 72 , Z 72  and Z 73 , Z 74  and Z 75 , and Z 75  and Z 76  may bond to each other via a linking group to form a condensed ring; and 
         n 71  represents 0 to 4. 
       
     
     
         19 . The organic electroluminescent device as claimed in  claim 13 , wherein the metal complex is a phosphorescent emissive metal complex, and said metal complex is incorporated in the luminescent layer. 
     
     
         20 . The organic electroluminescent device as claimed in  claim 13 , wherein the organic layer comprises at least one luminescent layer and a hole transporting layer, and the organic layer further comprises at least one layer selected from the group consisting of an exciton-blocking layer, a hole injection layer, a hole-blocking layer and an electron-transporting layer. 
     
     
         21 . The organic electroluminescent device as claimed in  claim 13 , wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is selected from the group consisting of an amine compound, a metal chelate oxynoid compound in which the metal is aluminum, zinc or transition metals, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound. 
     
     
         22 . The organic electroluminescent device as claimed in  claim 13 , wherein the organic layer comprises at least one electron-transporting layer in which an electron-transporting material is selected from the group consisting of a metal chelate oxynoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound and a non-complex aromatic heterocyclic compound. 
     
     
         23 . The organic electroluminescent device as claimed in  claim 13 , wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is composed of at least two compounds. 
     
     
         24 . A metal complex of formula (1) 
       
         
           
           
               
               
           
         
         wherein, 
         M 11  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
         L 11 , L 12 , L 13 , L 14 , and L 15  each represent a ligand to coordinate to M 11 ; 
         L 11  and L 14  do not combine together via an atomic group to form a cyclic ligand;
 L 15  does not bond to both L 11  and L 14  to form a cyclic ligand; 
 
         Y 11 , Y 12 , and Y 13  each represent a linking group, a single bond, or a double bond; 
         a bond between L 11  and Y 12 , a bond between Y 12  and L 12 , a bond between L 12  and Y 11 , a bond between Y 11  and L 13 , a bond between L 13  and Y 13 , and a bond between Y 13  and L 14  each represent a single bond or a double bond; 
         n 11  represents 0 to 4; and 
         wherein the compound comprises a metal-carbon bond. 
       
     
     
         25 . The metal complex as claimed in  claim 24 , wherein L 11 , L 12 , L 13 , L 14 , and L 15  each independently coordinate to M 11  via a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. 
     
     
         26 . The metal complex as claimed in  claim 24 , wherein L 11  and L 14  are each an aromatic carbocyclic ligand, an alkyloxy ligand, an aryloxy ligand, an ether ligand, an alkylthio ligand, an arylthio ligand, an alkylamino ligand, an arylamino ligand, an acylamino ligand, and a nitrogen-containing heterocyclic ligand, or a condensed ligand containing any of these ligands. 
     
     
         27 . The metal complex as claimed in  claim 24 , wherein L 12  and L 13  are each a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, or a condensed ring containing any of these rings. 
     
     
         28 . The metal complex claimed in  claim 24 , wherein the metal complex is represented by formula (6): 
       
         
           
           
               
               
           
         
         wherein, 
         M 61  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
         L 65  represents a ligand to coordinate to M 61 ; 
         Y 61  represents a linking group, a single bond, or a double bond; 
         Y 62  and Y 63  each represent a linking group or a single bond; 
         Q 61  and Q 62  each represent a group to form a ring; 
         Z 61 , Z 62 , Z 63 , Z 64 , Z 65 , Z 66 , Z 67 , and Z 68  each represent a substituted or unsubstituted carbon atom or a nitrogen atom; 
         Z 61  and Z 62 , Z 62  and Z 63 , Z 63  and Z 64 , Z 65  and Z 66 , Z 66  and Z 67 , Z 67  and Z 68  each may bond to each other via a linking group to form a condensed ring; 
         the ring formed by Q 61  or Q 62  may bond to Z 61  or Z 68  respectively via a linking bond to form a ring; and 
         n 61  represents 0 to 4. 
       
     
     
         29 . The metal complex claimed in  claim 24 , wherein the metal complex is represented by formula (7): 
       
         
           
           
               
               
           
         
         wherein, 
         M 71  represents a metal ion selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium, and copper ions; 
         L 75  represents a ligand to coordinate to M 71 ; 
         Y 71 , Y 72 , and Y 73  each represent a linking group, a single bond, or a double bond; 
         R 71 , R 72 , R 73 , and R 74  each represent a hydrogen atom or a substituent; 
         R 71  and R 72 , and R 73  and R 74  may bond to each other to form a condensed ring; 
         Z 71 , Z 72 , Z 73 , Z 74 , Z 75  and Z 76  each represent a substituted or unsubstituted carbon atom or a nitrogen atom; 
         Z 71  and Z 72 , Z 72  and Z 73 , Z 74  and Z 75 , and Z 76  and Z 76  may bond to each other via a linking group to form a condensed ring; and 
         n 71  represents 0 to 4.