Coordination Complex and Electronic Device Comprising the Same

Abstract

The present invention relates to an electronic device comprising a hole injection layer and/or a hole transport layer and/or a hole generating layer, wherein at least one of the hole injection layer, the hole transport layer and the hole generating layer comprises a coordination complex comprising at least one electropositive atom M having an electronegativity value according to Allen of less than 2.4 and at least one ligand L having the following structure: (I) wherein R 1 and R 2 are independently selected from the group, consisting of C 1 to C 30 hydrocarbyl groups and C 2 to C 30 heterocyclic groups, wherein R 1 and/or R 2 may optionally be substituted with at least one of CN, F, Cl, Br and I.

1 . Electronic device comprising a hole injection layer and/or a hole transport layer and/or a hole generating layer, wherein at least one of the hole injection layer, the hole transport layer and the hole generating layer comprises a coordination complex comprising at least one electropositive atom M having an electro-negativity value according to Allen of less than 2.4 and at least one ligand L having the following structure: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from the group consisting of C 1  to C 30  hydrocarbyl groups and C 2  to C 30  heterocyclic groups, wherein R 1  and/or R 2  may optionally be substituted with at least one of CN, F, Cl, Br and I. 
       
     
     
         2 . Electronic device according to  claim 1  wherein the coordination complex has the general formula (I)
   M n L m Q p O l   (I)
 
 wherein Q is a ligand different from L; 
 n is from 1 to 4; 
 m is from 1 to 6; 
 p is from 0 to 6; and 
 1 is 0 or 1. 
 
     
     
         3 . Electronic device according to  claim 1 , wherein M is selected from metals forming divalent and/or trivalent cations. 
     
     
         4 . Electronic device according to  claim 1 , wherein R 1  and/or R 2  are substituted with substituents selected from the group consisting of CN, F, Cl, Br, and I and in at least one of R 1  and R 2  the number ratio of substituents:hydrogen is ≥1. 
     
     
         5 . Electronic device according to  claim 2 , wherein m is 2 to 4. 
     
     
         6 . Electronic device according to  claim 1 , wherein the coordination complex is an inverse coordination complex comprising
 (i) a core consisting of one atom or a plurality of atoms forming a covalent cluster; and   (ii) a first coordination sphere consisting of at least four electropositive atoms M, wherein all core atoms have a higher electronegativity according to Allen than any of the electropositive atoms M in the first coordination sphere, and the at least one ligand L is coordinated to at least one atom of the first coordination sphere.   
     
     
         7 . Coordination complex having the general formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         M is an electropositive atom having an electro-negativity value according to Allen of less than 2.4; 
         n is 1 and m is 2 or 3; 
         and R 1  and R 2  are independently selected from the group consisting of C 1  to C 30  hydrocarbyl and C 2  to C 30  heterocyclic group, wherein R 1  and R 2  are each substituted with substituents selected from the group consisting of CN, F, Cl, Br and I and the ratio of substituents:hydrogen in each of the R 1  and R 2  is ≥1. 
       
     
     
         8 . Coordination complex comprising
 (i) a core consisting of one atom or a plurality of atoms forming a covalent cluster;   (ii) a first coordination sphere consisting of at least four electropositive atoms M; and   (iii) a second coordination sphere comprising a plurality of ligands,   wherein the first coordination sphere is closer to the core than the second coordination sphere,   all core atoms have a higher electronegativity according to Allen than any of the electropositive atoms comprised in the first coordination sphere,   the ligands of the second coordination sphere are coordinated to the electropositive atoms of the first coordination sphere, and   at least one ligand L of the plurality of ligands of the second coordination sphere has the following structure   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from the group consisting of C 1  to C 30  hydrocarbyl groups and C 2  to C 30  heterocyclic groups, wherein R 1  and/or R 2  may optionally be substituted with at least one of CN, F, Cl, Br and I. 
       
     
     
         9 . Method for preparing the coordination complex according to  claim 8 , the method comprising:
 heating a complex having the general formula ML 2 .   
     
     
         10 . Method for preparing an electronic device according to  claim 1 , comprising a step of heating the coordination complex. 
     
     
         11 . Method according to  claim 10 , further comprising the steps of
 (ii) vaporizing the coordination complex according to general formula (I); and   (iii) depositing the vapor of the coordination complex on a solid support.   
     
     
         12 . Method according to  claim 11 , wherein the vaporizing and the depositing respectively comprise co-vaporizing and co-deposition of the coordination complex with a matrix material. 
     
     
         13 . Electronic device obtainable by the method according to  claim 10 . 
     
     
         14 . Semiconducting material comprising a hole transport matrix material and a p-dopant which is the coordination complex as defined in  claim 1  or the coordination complex according to  claim 7 . 
     
     
         15 . Solid crystalline phase consisting of a compound having the chemical formula C 42 F 48 N 6 O 13 S 6 Zn 4 .