Materials for organic light-emitting devices

Abstract

The invention relates to compounds which are suitable for use in electronic devices, and electronic devices, in particular organic electroluminescent devices, containing said compounds.

1 .- 17 . (canceled) 
     
     
         18 . A compound of formula (1) 
       
         
           
           
               
               
           
         
         wherein 
         X is the same or different at each instance and is CR or N or two adjacent X groups together are O, S or NR, so as to give a five-membered ring, or two adjacent X groups together are a group of the formula (2), (3) or (4)
 with the proviso that the compound of the formula (1) contains at least one group of the formula (2) 
 
       
       
         
           
           
               
               
           
         
         
           where ̂ indicates the positions to which the group of the formula (2) or (3) or (4) is fused to the compound of the formula (1); 
         
         A 1 , A 2  is the same or different at each instance and is a single bond, CR 2 , NR, O, S or C═O; 
         Z is the same or different at each instance and is C═O, C═S, CR 2 , BR, SiR 2 , P(═O)R, SO or SO 2 ; 
         Y is C when Ar 1  is a 6-membered aryl or heteroaryl group, or is C or N when Ar 1  is a 5-membered heteroaryl group; 
         E is the same or different at each instance and is a single bond, CR 2 , NR, O, S or C═O, with the proviso that E in formula (4) is not a single bond; 
         Ar 1  is the same or different at each instance and, together with the Y group and the carbon atom shown explicitly, is an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted by one or more R radicals; 
         Ar 2  is the same or different at each instance and, together with the three carbon atoms shown explicitly, is an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted by one or more R radicals; 
         G is the same or different at each instance and is CR or N; 
         R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 3 ) 2 , N(R 1 ) 2 , C(═O)Ar 3 , C(═O)R 1 , P(═O)(Ar 3 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 1  radicals, where one or more nonadjacent CH 2  groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1  and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 1  radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1  radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1  radicals, where it is optionally possible for two or more adjacent R substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 1  radicals; 
         Ar 3  is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5-30 aromatic ring atoms and may be substituted by one or more nonaromatic R 1  radicals; at the same time, two Ar 3  radicals bonded to the same nitrogen atom or phosphorus atom may also be bridged to one another by a single bond or a bridge selected from N(R 1 ), C(R 1 ) 2  and O; 
         R 1  is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(R 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2  radicals, where one or more nonadjacent CH 2  groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2  and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 2  radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2  radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2  radicals, where it is optionally possible for two or more adjacent R 1  substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 2  radicals; 
         R 2  is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, where two or more adjacent R 2  substituents together may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system. 
       
     
     
         19 . The compound as claimed in  claim 18 , wherein A 1  and A 2  are single bonds. 
     
     
         20 . The compound as claimed in  claim 18  comprising exactly one or two groups of the formula (2). 
     
     
         21 . The compound as claimed in  claim 18 , selected from the compounds of the formula (5) to (10) 
       
         
           
           
               
               
           
         
         where ∘ represents the linkage to the nitrogen atom in the group of the formula (2), and # represents the linkage to the E group in the group of the formula (2). 
       
     
     
         22 . The compound as claimed in  claim 18 , selected from the compounds of the formulae (5a) to (10a) 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 18 . 
       
     
     
         23 . The compound as claimed in  claim 18 , selected from compounds of the formulae (5b) to (10b) 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 18 . 
       
     
     
         24 . The compound as claimed in  claim 18 , wherein in the group of the formula (2), Z is the same or different and is C═O or C═S, and in that E is a single bond, CR 2 , C═O or NR. 
     
     
         25 . The compound as claimed in  claim 18 , wherein Ar 1  is a group of the formula (13), (14), (15), (16) or (17) 
       
         
           
           
               
               
           
         
         where the dotted bond indicates the linkage to Z and * indicates the position of the linkage to Ar 2 ; 
         and in that Ar 2  is a group of the formula (20), (21) or (22) 
       
       
         
           
           
               
               
           
         
         where the dotted bond indicates the linkage to N, # indicates the position of the linkage to E and * indicates the linkage to Ar 1 ; 
         and in addition: 
         W is the same or different at each instance and is CR or N, or two adjacent W groups are a group of the following formula (18) or (19) 
       
       
         
           
           
               
               
           
         
         where E is as defined in  claim 18 , but is not a single bond, G is the same or different at each instance and is CR or N and ̂ indicate the corresponding adjacent W groups in the formula (13) to (17); 
         V is NR, O or S. 
       
     
     
         26 . The compound as claimed in  claim 18 , wherein the group of the formula (2) is selected from the groups of the formulae (23) to (29): 
       
         
           
           
               
               
           
         
         where ̂ identifies the position of the linkage in formula (1) and the further symbols used are as defined in  claim 18 . 
       
     
     
         27 . The compound as claimed in  claim 18 , wherein the group of the formula (2) is selected from the groups of the formulae (23a) to (29a): 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 18 . 
       
     
     
         28 . The compound as claimed in  claim 18 , selected from the compounds of the formulae (5c) to (10c) 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where the symbols used are as defined in  claim 18 . 
       
     
     
         29 . The compound as claimed in  claim 18 , wherein all R radicals are H or in that one or two R radicals are an aromatic or heteroaromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted in each case by one or more R 1  radicals, and the other R radicals are H. 
     
     
         30 . An oligomer, polymer or dendrimer containing one or more of the compounds as claimed in  claim 18 , wherein one or more bonds of the compound to the polymer, oligomer or dendrimer are present in place of one or more R radicals. 
     
     
         31 . A formulation comprising at least one compound as claimed in  claim 18  and at least one further compound, especially a solvent or a mixture of two or more solvents. 
     
     
         32 . A method comprising incorporating the compound as claimed in  claim 18  in an electronic device. 
     
     
         33 . An electronic device comprising at least one compound as claimed in  claim 18 . 
     
     
         34 . The electronic device as claimed in  claim 33 , wherein the device is an organic electroluminescent device and the compound as claimed in  claim 18  is used in an emitting layer as matrix material for fluorescent or phosphorescent emitters and/or in a hole blocker layer and/or in an electron transport layer.