5,6-diphenyl-5,6-dihydro-dibenz[c,e][1,2]azaphosphorin and 6-phenyl-6h-dibenzo[c,e][1,2]thiazin-5,5-dioxide derivatives and similar compounds as organic electroluminescent materials for oleds

A compound of formula (1)

• where the symbols used are as follows:
• Z is the same or different at each instance and is PAr2 or S(═O);
• E is the same or different at each instance and is O or S when the symbol Z to which this E binds is PAr2, and O when the symbol Z to which this E binds is S(═O);
• L is selected from the group consisting of a single bond, NAr2, O, S, S(═O)2, P(═O)Ar2, —X═X— and —C(═O)—NAr2—;
• X is the same or different at each instance and is CR or N, where not more than two X groups per cycle are N;
• or two adjacent X are a group of the following formula (2), (3) or (4):
• where the dotted bonds indicate the linkage of this group in the formula (1);
• Y is the same or different at each instance and is CR or N, where not more than two Y groups per cycle are N;
• Ar1, Ar2 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals, where Ar1 and Ar2 are not joined to one another, with the proviso that the substituents R that bind to Ar1 are not fluorine;
• A is the same or different at each instance and is NAr2, O, S or CR2;
• V is the same or different at each instance and is —NAr2—Z(=E)-;
• R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar3)2, OAr3, SAr3, CN, NO2, NAr3R1, N(R1)2, OR1, SR1, COOR1, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1, P(═O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R1)2, C═O, NR1, O, S or CONR1, or 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 R1 radicals;
• at the same time, two R radicals together may also form an aliphatic or heteroaliphatic ring system;
• Ar3 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R1 radicals;
• R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, OSO2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R2)2, C═O, NR2, O, S or CONR2, or 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 R2 radicals;
• at the same time, two or more R1 radicals together may form an aliphatic ring system;
• R2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
• where the following compounds are excluded from the invention: