Organic electronic devices comprising a layer of a pyridine compound and a 8-hydroxypquinolinolato earth alkaline metal, or alkali metal complex

Abstract

The present invention provides an organic electronic device including a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an organic metal complex of formula and a compound of formula Organic light emitting devices (OLEDs) having superior life time, power efficiency, quantum efficiency and/or a low operating voltage are obtained, when the organic layer comprising the compounds of formula I and II constitutes the electron transport layer of an OLED.

1 . An organic electronic device including a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises 
       an organic metal complex of formula 
       
         
           
           
               
               
           
         
       
       and 
       a compound of formula 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  and R 2  are independently of each other F, C 1 -C 8 alkyl, or C 6 -C 18 aryl, which may optionally be substituted by one, or more C 1 -C 8 alkyl groups, or 
 two substituents R 1  and/or R 2  combine to form a fused benzene ring group, which may optionally be substituted by one, or more C 1 -C 8 alkyl groups, 
 a and b are independently of each other 0, or an integer 1 to 3, 
 R 81 , R 82 , R 83 , R 84 , R 81 ′, R 82 ′, R 83 ′, and R 84 ′ are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, 
 Q is an arylene or heteroarylene group, each of which may optionally be substituted by G; 
 D is —CO—; —COO—; —S—; —SO—; —SO 2 —; —O—; —NR 25 —; —SiR 30 R 31 —; —POR 32 —; —CR 23 ═CR 24 —; or —C≡C—; and 
 E is —OR 29 ; —SR 29 ; —NR 25 R 26 ; —COR 28 ; —COOR 27 ; —CONR 25 R 26 ; —CN; or F; G is E, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted by D, C 1 -C 18 perfluoroalkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, wherein 
 R 23  and R 24  are independently of each other H, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—; 
 R 25  and R 26  are independently of each other C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—; or 
 R 25  and R 26  together form a five or six membered ring, R 27  and R 28  are independently of each other C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—, 
 R 29  is C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—, 
 R 30  and R 31  are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, 
 R 32  is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl 
 M is an alkali metal atom, or an earth alkaline metal atom, 
 n is 1, if M is an alkali metal atom, n is 2, if M is an earth alkali metal atom. 
 
     
     
         2 . The organic electronic device according to  claim 1 , wherein Q is a group of formula 
       
         
           
           
               
               
           
         
       
       wherein R 85  is H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, and D, E and G are as defined in  claim 1 . 
     
     
         3 . The organic electronic device according to  claim 2 , wherein the compound of formula II is a compound of formula 
       
         
           
           
               
               
           
         
       
       wherein Q is 
       
         
           
           
               
               
           
         
       
       R 85  is H, or C 1 -C 18 alkyl and 
       R 85 ′ is H, C 1 -C 18 alkyl, or 
       
         
           
           
               
               
           
         
       
     
     
         4 . The organic electronic device according to  claim 3 , wherein the compound of formula IIb is a compound of formula 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . The organic electronic device according to  claim 1 , wherein M is Li, Na, or K and n is 1. 
     
     
         6 . The organic electronic device according to  claim 5 , wherein the compound of formula I is a compound of formula 
       
         
           
           
               
               
           
         
       
     
     
         7 . The organic electronic device according to  claim 1 , which is an organic light emitting device, comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, a hole and exciton blocking layer, an electron transport layer, an electron injection layer and a cathode, wherein the organic layer comprising the compounds of formula I and II constitutes the electron transport layer. 
     
     
         8 . The organic electronic device according to  claim 7 , wherein the electron transport layer comprises a mixture of a compound of formula 
       
         
           
           
               
               
           
         
       
       and a compound of formula (A-1). 
     
     
         9 . The organic electronic device according to  claim 7 , wherein the electron injection layer comprises, or consists of potassium fluoride. 
     
     
         10 . The organic electronic device according to any of  claim 7 , wherein the light emitting layer comprises a compound of the formula 
       
         
           
           
               
               
           
         
       
       wherein the symbols have the following meanings:
 M 1  is a metal atom selected from the group consisting of Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Os, Cr, Mo, W, Mn, Tc, Re, Cu, Ag and Au in any oxidation state possible for the respective metal atom; 
 carbene is a carbene ligand which may be uncharged or monoanionic and monodentate, bidentate or tridentate, with the carbene ligand also being able to be a biscarbene or triscarbene ligand; 
 L is a monoanionic or dianionic ligand, which may be monodentate or bidentate; 
 K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; phosphonates and derivatives thereof, arsenates and derivatives thereof; phosphites; CO; pyridines; nitriles and conjugated dienes which form a π complex with Ml; 
 n1 is the number of carbene ligands, where n1 is at least 1 and when n1>1 the carbene ligands in the complex of the formula I can be identical or different; 
 m is the number of ligands L, where m can be 0 or 1 and when m>1 the ligands L can be identical or different; 
 o is the number of ligands K, where o can be 0 or 1 and when o>1 the ligands K can be identical or different; 
 
       where the sum n1+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands, carbene and L, with the proviso that n1 is at least 1. 
     
     
         11 . The organic electronic device according to  claim 10 , wherein the compound of the formula IX is a compound of the formula 
       
         
           
           
               
               
           
         
       
     
     
         12 . The organic electronic device according to  claim 1 , wherein the hole transport layer comprises a compound of formula 
       
         
           
           
               
               
           
         
       
       doped with molybdenum oxide (MoO x ), especially MoO 3 , or rhenium oxide (ReO x ), especially ReO 3 . 
     
     
         13 . An organic electron transport layer, comprising an organic metal complex of formula I as defined in  claim 1  and a compound of formula II as defined in  claim 1 . 
     
     
         14 . A method of using the organic layer according to  claim 13  in an organic electronic device. 
     
     
         15 . An apparatus comprising an organic electronic device according to  claim 1 . 
     
     
         16 . An apparatus comprising an organic electron transport layer according to  claim 13 .