Materials for electronic devices

A process for preparing

• a compound of formula (I)
• where the variables that occur are as follows:
• Z, when the -[Ar1]k-N(Ar2)(Ar3) group is bonded thereto, is C, and Z, when the -[Ar1]k-N(Ar2)(Ar3) group is not bonded thereto, is the same or different at each instance and is CR1 or N;
• Ar1 is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R3 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R3 radicals;
• Ar2 is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R4 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R4 radicals;
• Ar3 is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R4 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R4 radicals;
• provided that at least one group selected from the Ar2 and Ar3 groups is phenyl substituted by R4 radicals that are selected from H, D, F, CN and alkyl groups having 1 to 10 carbon atoms;
• Ar4 is phenyl which may be substituted by R2 radicals or naphthyl which may be substituted by R2 radicals;
• R1 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
• where two or more R1 radicals may be joined to one another and may form a ring;
• where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R5 radicals;
• and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5-, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5-, NR5, P(═O)(R5), —O—, —S—, SO or SO2;
• R2 is the same or different at each instance and is selected from D, F, CN, Si(R5)3, N(R5)2, aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R5 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are substituted by R5 radicals;
• R3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
• where two or more R3 radicals may be joined to one another and may form a ring;
• where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R5 radicals;
• and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5-, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5-, NR5, P(═O)(R5), —O—, —S—, SO or SO2;
• R4 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
• where two or more R4 radicals may be joined to one another and may form a ring;
• where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R5 radicals;
• and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5-, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5-, NR5, P(═O)(R5), —O—, —S—, SO or SO2;
• R5 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R6, CN, Si(R6)3, N(R6)2, P(═O)(R6)2, OR6, S(═O)R6, S(═O)2R6, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
• where two or more R5 radicals may be joined to one another and may form a ring;
• where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R6 radicals;
• and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R6C═CR6-, —C≡C—, Si(R6)2, C═O, C═NR6, —C(═O)O—, —C(═O)NR6-, NR6, P(═O)(R6), —O—, —S—, SO or SO2;
• R6 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
• where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN;
• k is 0, 1, 2, 3 or 4, where, in the case that k=0, the Ar1 group is absent and the groups that bind to Ar1 in formula (I) are bonded directly to one another;
• i is 0, 1, 2, 3, 4 or 5;
• n is 0, 1, 2, 3 or 4;
• where the two groups
• in formula (I), each as a whole including their substituents, are not the same;
• wherein a biphenyl derivative bearing two reactive groups, at least one of which is in the ortho position, is metallated and then is added onto a carbonyl derivative containing a phenyl- or naphthyl-substituted phenyl group and a phenyl group bonded to the carbonyl group.