Materials for organic electroluminescent devices

Abstract

The present invention describes dibenzofuran and dibenzothiophene derivatives, in particular for use as triplet matrix materials in organic electroluminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising same.

1 .- 14 . (canceled) 
     
     
         15 . Compound of the formula (1), 
       
         
           
           
               
               
           
         
         where the following applies to the symbols used: 
         A is on each occurrence, identically or differently, CR 1  or N, where a maximum of two groups A per ring stand for N; 
         Y 1  is O or S; 
         L is on each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; 
         HetAr is a group of the formula (2), (3) or (4), 
       
       
         
           
           
               
               
           
         
         where the dashed bond represents the linking of this group; 
         X is on each occurrence, identically or differently, CR 2  or N, with the proviso that at least one symbol X stands for N; 
         N 1  is a group of the formula (6), 
       
       
         
           
           
               
               
           
         
         where the dashed bond represents the linking of this group; 
         W is on each occurrence, identically or differently, CR 1  or N, where a maximum of two groups W stand for N; 
         R 1 , R 2  are selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 2 ) 2 , N(R 5 ) 2 , C(═O)Ar 2 , C(═O)R 5 , P(═O)(Ar 2 ) 2 , P(Ar 2 ) 2 , B(Ar 2 ) 2 , Si(Ar 2 ) 3 , Si(R 5 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which may be substituted by one or more radicals R 5 , where one or more non-adjacent CH 2  groups may be replaced by R 5 C═CR 5 , Si(R 5 ) 2 , C═O, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5  and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 5 , an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 5 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 5 ; two adjacent substituents R 1  or two adjacent substituents R 3  here may optionally form an aliphatic ring system, which may be substituted by one or more radicals R 5 , and two adjacent substituents R 4  may form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R 5 ; 
         Ar 2  is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 5 ; two radicals Ar 2  which are bonded to the same N atom, P atom or B atom here may also be bridged to one another by a single bond or a bridge selected from N(R 5 ), C(R 5 ) 2 , O or S; 
         R 5  is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups, each having 1 to 4 carbon atoms; two or more adjacent substituents R 5  here may form an aliphatic ring system with one another. 
       
     
     
         16 . Compound according to  claim 15  of the formula (1a), 
       
         
           
           
               
               
           
         
         where the symbols used have the meanings given in  claim 15  and n stands, identically or differently on each occurrence, for 0, 1, 2 or 3. 
       
     
     
         17 . Compound according to  claim 15  of one of the formulae (1b) to (1g), 
       
         
           
           
               
               
           
         
         where the symbols used have the meanings given in  claim 15 . 
       
     
     
         18 . Compound according to  claim 15 , characterised in that the groups of the formulae (2), (3) and (4) are selected from the groups of the formulae (2-1) to (2-10), (3-1) and (4-1), 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where the dashed bond represents the linking of these groups and R 2  has the meanings given in  claim 15 . 
       
     
     
         19 . Compound according to  claim 15 , characterised in that the group of the formula (6) is selected from the groups of the formulae (6-1), 
       
         
           
           
               
               
           
         
         where R 1  has the meanings given in  claim 15  and furthermore m is, identically or differently on each occurrence, 0, 1, 2, 3 or 4. 
       
     
     
         20 . Process for the preparation of a compound according to  claim 15  starting from 1-halodibenzofuran or 1-halodibenzothiophene, characterised by the following steps:
 (1) optionally conversion of the halogen group into a boronic acid or a boronic acid derivative; 
 (2) introduction of the group HetAr by a coupling reaction; 
 (3) halogenation, in particular bromination, of the dibenzofuran or dibenzothiophene in the 8-position; 
 (4) introduction of the group N 1  by a coupling reaction. 
 
     
     
         21 . Formulation comprising at least one compound according to  claim 15  and at least one solvent. 
     
     
         22 . Use of a compound according to  claim 15  in an electronic device. 
     
     
         23 . Electronic device comprising at least one compound according to  claim 15 . 
     
     
         24 . Electronic device according to  claim 23 , which is an organic electroluminescent device, characterised in that the at least one compound is employed as matrix material for fluorescent or phosphorescent emitters and/or in an electron-transport layer and/or in an electron-blocking or exciton-blocking layer and/or in a hole-transport layer.