INDENOAZANAPHTHALENES

Abstract

The present invention relates indenoazanaphthalenes, particularly for use in electronic devices. The invention further relates to a method for producing the indenoazanaphthalenes according to the invention, and to electronic devices comprising the same.

Claims

1.-19. (canceled)

20. A compound having at least one structure of formula (Ia) and/or (Ib): ##STR00527## where the symbols used are as follows: X is the same or different at each instance and is N or CR; X.sup.a is the same or different at each instance and is N or CR.sup.a; R.sup.a is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.a).sub.2, N(R).sub.2, C(═O)Ar.sup.a, C(═O)R.sup.2, P(═O)(Ar.sup.a).sub.2, P(Ar.sup.a).sub.2, B(Ar.sup.a).sub.2, B(OR).sub.2, Si(Ar.sup.a).sub.3, Si(R).sub.3, Ge(R).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —RC═CR—, —C≡C—, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, —O—, —Se—, —S—, C═Se, —C(═O)O—, —C(═O)NR—, C═NR, NR, P(═O)(R), SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals, or a combination of these systems; at the same time, two or more, adjacent R.sup.a radicals may form a ring system with one another or with an R radical; Ar.sup.a 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, R radicals; at the same time, it is possible for two Ar.sup.a radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R), C(R).sub.2, Si(R).sub.2, Ge(R).sub.2, C═O, C═NR, C═C(R).sub.2, O, S, Se, S═O, SO.sub.2, N(R), P(R) and P(═O)R; R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R′, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR′, P(═O)(R′), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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, R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R′), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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, R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more adjacent R.sup.3 substituents to form a ring system with one another.

21. A compound as claimed in claim 20, comprising at least one structure of formula (II-1), (II-2), (II-3), (II-4), (II-5), (II-6), (II-7), (II-8), (II-9), (II-10), (II-11), (II-12), (II-13), (II-14), (II-15) or (II-16): ##STR00528## ##STR00529## ##STR00530## ##STR00531## where the symbols R and X have the definition given in claim 20, p is 0 or 1 and Y represents B(R), C(R).sub.2, Si(R).sub.2, C═O, C═NR, C═C(R).sub.2, O, S, Se, S═O, SO.sub.2, N(R), P(R) and P(═O)R, where, when p=0, there is a bond between the aromatic or heteroaromatic rings shown.

22. A compound as claimed in claim 20, comprising at least one structure of the formula (III-1), (III-2), (III-3), (III-4), (III-5), (III-6), (III-7), (III-8), (III-9), (III-10), (III-11), (III-12), (III-13), (III-14), (III-15) or (III-16): ##STR00532## ##STR00533## ##STR00534## ##STR00535## where the symbol R has the definition given in claim 20, the symbols p is 0 or 1, and Y represents B(R), C(R).sub.2, Si(R).sub.2, C═O, C═NR, C═C(R).sub.2, O, S, Se, S═O, SO.sub.2, N(R), P(R) and P(═O)R, where, when p=0, there is a bond between the aromatic or heteroaromatic rings shown, 1 is 1, 2, 3, 4 or 5, and m is 0, 1, 2, 3 or 4.

23. A compound as claimed in claim 20, wherein the compound comprises a hole transport group.

24. A compound as claimed in claim 20, that the compound comprises an electron transport group-comprising radical.

25. A compound as claimed in claim 20, wherein at least one R.sup.a or R group in the formulae (Ia), (Ib), (II-1), (II-2), (II-3), (II-4), (II-5), (II-6), (II-7), (II-8), (II-9), (II-10), (II-11), (II-12), (II-13), (II-14), (II-15), (II-16), (III-1), (III-2), (III-3), (III-4), (III-5), (III-6), (III-7), (III-8), (III-9), (III-10), (III-11), (III-12), (III-13), (III-14), (III-15) or (III-16) is a group that can be represented by the formula L.sup.1-Z in which L.sup.1 represents a bond or an aromatic or heteroaromatic ring system which has 5 to 40, aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, Z represents R.sup.1, Ar or a group of the formula Z.sup.a or Z.sup.b in which the symbols Ar and R.sup.1 have the definition given in claim 20 and Z.sup.a or Z.sup.b are ##STR00536## in which W 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 R.sup.1 radicals, a nitrogen atom, a boron atom, a phosphorus atom or a phosphane oxide group, the dotted bond marks the position of attachment and the symbols Ar and R.sup.1 have the definition given in claim 20.

26. A compound as claimed in claim 25, comprising at least one structure of the formula (IV-1), (IV-2), (IV-3), (IV-4), (IV-5), (IV-6), (IV-7), (IV-8), (IV-9), (IV-10), (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-16), (IV-17), (IV-18), (IV-19), (IV-20), (IV-21), (IV-22), (IV-23) or (IV-24): ##STR00537## ##STR00538## ##STR00539## ##STR00540## ##STR00541## ##STR00542## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X, R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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, R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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, R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more R.sup.3 substituents to form a ring system with one another. and the -L.sup.1-Z group has the definition given in claim 25.

27. A compound as claimed in claim 25, comprising at least one structure of the formula (V-1), (V-2), (V-3), (V-4), (V-5), (V-6), (V-7), (V-8), (V-9), (V-10), (V-11), (V-12), (V-13), (V-14), (V-15), (V-16), (V-17), (V-18), (V-19), (V-20), (V-21), (V-22), (V-23), (V-24), (V-25), (V-26), (V-27), (V-28), (V-29), (V-30), (V-31) or (V-32): ##STR00543## ##STR00544## ##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549## ##STR00550## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X, R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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 R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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, R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more R.sup.3 substituents to form a ring system with one another, and p is 0 or 1 and Y represents B(R), C(R).sub.2, Si(R).sub.2, C═O, C═NR, C═C(R).sub.2, O, S, Se, S═O, SO.sub.2, N(R), P(R) and P(═O)R, where, when p=0, there is a bond between the aromatic or heteroaromatic rings shown.

28. A compound as claimed in claim 27, comprising at least one structure of the formula (VI-1), (VI-2), (VI-3), (VI-4), (VI-5), (VI-6), (VI-7) or (VI-8): ##STR00551## ##STR00552## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X.

29. A compound as claimed in claim 25, comprising at least one structure of the formula (VII-1), (VII-2), (VII-3), (VII-4), (VII-5), (VII-6), (VII-7) or (VII-8): ##STR00553## ##STR00554## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X, R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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 R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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 R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more, adjacent substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more adjacent R.sup.3 substituents to form a ring system with one another.

30. A compound as claimed in claim 25, comprising at least one structure of the formula (VIII-9) or (VIII-10): ##STR00555## ##STR00556## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X, and R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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 R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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 R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more, adjacent substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more adjacent R.sup.3 substituents to form a ring system with one another.

31. A compound as claimed in claim 25, comprising at least one structure of the formula (IX-1), (IX-2), (IX-3), (IX-4), (IX-5), (IX-6), (IX-7) or (IX-8): ##STR00557## ##STR00558## where the symbol X represents N, CR or C if the -L.sup.1-Z group is bonded to X, and R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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 R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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 R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more, adjacent substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more adjacent R.sup.3 substituents to form a ring system with one another.

32. A compound as claimed in claim 25, comprising at least one structure of the formula (XII-1), (XII-2), (XII-3), (XII-4), (XII-5), (XII-6), (XII-7), (XII-8), (XII-9), (XII-10), (XII-11), (XII-12), (XII-13), (XII-14), (XII-15), (XII-16), (XII-17), (XII-18), (XII-19), (XII-20), (XII-21), (XII-22), (XII-23) or (XII-24): ##STR00559## ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## where R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.1).sub.2, C(═O)Ar, C(═O)R.sup.1, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, B(OR.sup.1).sub.2, Si(Ar).sub.3, Si(R.sup.1).sub.3, Ge(R.sup.1).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.1C═CR.sup.1—, —C≡C—, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, —C(═O)O—, —C(═O)NR.sup.1—, C═NR.sup.1, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a combination of these systems; at the same time, two or more R radicals together may form a ring system; Ar 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 R.sup.1 radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(═O)Ar.sup.1, C(═O)R.sup.2, P(═O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, Ge(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.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.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a ring system; Ar.sup.1 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 R.sup.2 radicals; at the same time, it is possible for two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another via a bridge by a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, Se, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, Ge(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, —Se—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more, adjacent substituents R.sup.2 together may form a with one another; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen 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; at the same time, it is possible for two or more adjacent R.sup.3 substituents to form a ring system with one another, p is 0 or 1 and Y represents B(R), C(R).sub.2, Si(R).sub.2, C═O, C═NR, C═C(R).sub.2, O, S, Se, S═O, SO.sub.2, N(R), P(R) and P(═O)R, where, when p=0, there is a bond between the aromatic or heteroaromatic rings shown.

33. An oligomer, polymer or dendrimer containing one or more compounds as claimed in claim 20, wherein, rather than a hydrogen atom or a substituent, the compounds have one or more bonds to the polymer, oligomer or dendrimer.

34. A composition comprising at least one compound as claimed in claim 20 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

35. A formulation comprising at least one compound as claimed in claim 20 and at least one solvent.

36. A method comprising incorporating the compound as claimed in claim 20 in an electronic device as host material.

37. A process for preparing a compound as claimed in claim 20 wherein, in a coupling reaction, a compound comprising at least one nitrogen-containing heterocyclic group is joined to a compound comprising at least one aromatic or heteroaromatic group.

38. An electronic device comprising at least one compound as claimed in claim 20, wherein the electronic device is selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells and organic laser diodes.

Description

SYNTHESIS EXAMPLES

a) 2-(4-Chlorophenyl)-3-phenylquinoline-4-carboxylic acid

[0284] ##STR00319##

[0285] In a 1 L flask, 14.0 g (93.3 mmol; 1.00 eq; 98% pure) of isatin [CAS 91-56-5], 24.2 g (103 mmol; 1.10 eq) of 1-(4-chlorophenyl)-2-phenylethanone [CAS 1889-71-0] and 15.7 g (280 mmol; 3.00 eq) of potassium hydroxide powder [CAS 1310-58-3] are suspended in 630 mL of ethanol [CAS 64-17-5]. The reaction mixture is stirred at 100° C. for 48 hours. After cooling to room temperature, the solvent is removed under reduced pressure. The residue is dissolved in 200 mL of ethyl acetate [CAS 141-78-6] and 200 mL of water, and the phases are separated. After extracting the organic phase has been extracted with water (2×100 mL), the combined aqueous phases are washed with ethyl acetate (3×100 mL). The aqueous phase is adjusted to pH=1 with 25 mL of fuming hydrochloric acid [CAS 7647-01-0], and the precipitated solids are filtered off. After subsequent washing with ethanol, 22.5 g (62.7 mmol; 67% of theory) of product is obtained in the form of a white solid.

[0286] The following compounds can be obtained analogously:

TABLE-US-00004 No. Reactant 1 Reactant 2 Product Yield 1a [00320]   [91-56-5] [00321]   [451-40-1] [00322] 73% 2a [00323]   [91-56-5] [00324]   [72867-72-2] [00325] 60% 3a [00326]   [91-56-5] [00327]   [62482-45-5] [00328] 69% 4a [00329]   [91-56-5] [00330]   [6332-83-8] [00331] 66% 5a [00332]   [91-56-5] [00333]   [27798-43-2] [00334] 58% 6a [00335]   [6341-92-0] [00336]   [451-40-1] [00337] 71% 7a [00338]   [7477-63-6] [00339]   [451-40-1] [00340] 65% 8a [00341]   [17630-76-1] [00342]   [451-40-1] [00343] 68%

b) 6-(4-Chlorophenyl)indeno[1,2-c]quinolin-11-one

[0287] ##STR00344##

[0288] In a 500 mL flask, 21.0 g (58.4 mmol; 1.00 eq.) of 2-(4-chlorophenyl)-3-phenylquinoline-4-carboxylic acid and 32.1 mL (350 mmol; 6.00 eq.) of phosphoryl chloride [CAS 10025-87-3] are dissolved in 183 mL of chlorobenzene [CAS 108-90-7] and heated to 150° C. for 24 h. After checking the conversion, the reaction mixture is cooled down to room temperature, 8.17 g (61.3 mmol; 1.05 eq.) of anhydrous aluminum chloride [CAS 7446-70-0] is added and the mixture is heated to reflux for 3 h. After cooling, the reaction mixture is precipitated in ice-water. The water is decanted off, and EtOH is added to the crude product. The solids that occur are filtered off and dried. 15.53 g (44.9 mmol, 77% of theory) of product is converted without further purification.

[0289] The following compounds can be obtained analogously:

TABLE-US-00005 No. Reactant 1 Product Yield 1b [00345] [00346] 82% 2b [00347] [00348] 75% 3b [00349] [00350] 86% 4b [00351] [00352] 63% 5b [00353] [00354] 71% 6b [00355] [00356] 80% 7b [00357] [00358] 69% 8b [00359] [00360] 77%

c) 11-Biphenyl-2-yl-6-(4-chlorophenyl)-11H-indeno[1,2-c]quinolin-11-ol

[0290] ##STR00361##

[0291] In a 500 mL flask, under protective gas, 13.0 g (53.3 mmol; 1.24 eq) of 2-bromobiphenyl [CAS 2052-07-5] is dissolved in 80 mL of dry THF [CAS 109-99-9] and cooled to −76° C. Then 20.7 mL (2.5 mol/L; 51.7 mmol; 1.20 eq) of n-butyllithium [CAS 109-72-8] is added dropwise and the mixture is stirred for a further 1 hour. A suspension of 14.8 g (43.1 mmol, 1.00 eq) of 6-(4-chlorophenyl)indeno[1,2-c]quinolin-11-one in 370 mL of dry THF [CAS 109-99-9] is added dropwise to this mixture at −40° C. The resulting mixture is warmed gradually to room temperature and stirred for a further 72 hours. The reaction is quenched by addition of 100 mL of water and the resultant phases are separated. After the aqueous phase has been extracted with ethyl acetate (3×150 mL) [CAS 141-78-6], the combined organic phases are washed with water (3×150 mL). The organic phase is concentrated under reduced pressure and precipitated in heptane [CAS 142-82-5]. The crude product is purified by means of column chromatography, and 7.65 g (15.4 mmol; 36% of theory) of the product is obtained in solid form.

[0292] The following compounds can be obtained analogously:

TABLE-US-00006 No. Reactant 1 Reactant 2 1c [00362] [00363] 2c [00364] [00365] 3c [00366] [00367] 4c [00368] [00369] 5c [00370] [00371] 6c [00372] [00373] 7c [00374] [00375] 8c [00376] [00377] 9c [00378] [00379] 10c  [00380] [00381] 11c  [00382] [00383] No. Product Yield 1c [00384] 55% 2c [00385] 40% 3c [00386] 47% 4c [00387] 33% 5c [00388] 51% 6c [00389] 48% 7c [00390] 30% 8c [00391] 27% 9c [00392] 35% 10c  [00393] 40% 11c  [00394] 51%

d) 6′-(4-Chlorophenyl)spiro[fluorene-9,11′-indeno[1,2-c]quinoline]

[0293] ##STR00395##

[0294] In a 500 mL flask, 7.50 g (15.1 mmol; 1.00 eq) of 11-biphenyl-2-yl-6-(4-chlorophenyl)-11H-indeno[1,2-c]quinolin-11-ol and 28.8 g (150 mmol; 10.0 eq) of toluenesulfonic acid monohydrate [CAS 6192-52-5] are suspended in 250 mL of toluene [CAS 108-88-3], and the mixture is stirred at 115° C. for 24 hours. On completion of conversion, the mixture is cooled down to room temperature and the reaction solution is admixed with water. After phase separation, the aqueous phase is extracted with dichloromethane [CAS 75-09-2] (3×150 mL). The combined organic phases are washed with water (3×150 mL). The organic solvent is removed on a rotary evaporator and the solids obtained are dried. 7.00 g of the product (14.6 mmol; 97% of theory) is converted without further purification.

[0295] The following compounds can be obtained analogously:

TABLE-US-00007 No. Reactant 1 Product Yield 1d [00396] [00397] 94% 2d [00398] [00399] 93% 3d [00400] [00401] 89% 4d [00402] [00403] 91% 5d [00404] [00405] 85% 6d [00406] [00407] 95% 7d [00408] [00409] 93% 8d [00410] [00411] 98% 9d [00412] [00413] 88% 10d  [00414] [00415] 87% 11d  [00416] [00417] 80%

e) 6′-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]spiro[fluorene-9,11′-indeno[1,2-c]quinoline]

[0296] ##STR00418##

[0297] In a 500 mL flask, under protective gas, 6.34 g (13.3 mmol; 1.00 eq.) of 6′-(4-chlorophenyl)spiro[fluorene-9,11′-indeno[1,2-c]quinoline] and 4.30 g (16.9 mmol; 1.28 eq) of bis(pinacolato)diborane [CAS 73183-34-3] are dissolved in 200 mL of dry dioxane [CAS 123-91-1] and the mixture is degassed for 45 min. Subsequently, 3.20 g (32.6 mmol; 2.46 eq.) of potassium acetate [CAS 127-08-2] and 510 mg (0.69 mmol; 0.05 eq.) of bis(tricyclohexylphosphine)palladium dichloride [CAS 29934-17-6] are added, and the mixture is heated to 110° C. overnight. On completion of conversion, and after cooling to room temperature, 300 mL of ethyl acetate [CAS 141-78-6] and 300 mL of water are added to the reaction. After phase separation and extraction of the aqueous phase with ethyl acetate, the combined organic phases are concentrated and washed with water. After the solvent has been removed, the desired product (7.60 g; 12.3 mmol; 93% of theory) is obtained.

[0298] The following compounds can be obtained analogously:

TABLE-US-00008 No. Reactant 1 Product Yield 1e [00419] [00420] 95% 2e [00421] [00422] 85% 3e [00423] [00424] 95% 4e [00425] [00426] 89% 5e [00427] [00428] 91% 6e [00429] [00430] 88% 7e [00431] [00432] 93% 8e [00433] [00434] 81% 9e [00435] [00436] 84% 10e  [00437] [00438] 95% 11e  [00439] [00440] 93%

f) 6′-[4-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]spiro[fluorene-9,11′-indeno[1,2-c]quinoline]

[0299] ##STR00441##

[0300] 7.00 g (11.3 mmol; 1.05 eq.) of 6′-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]spiro[fluorene-9,11′-indeno[1,2-c]quinoline], 2.89 g (10.8 mmol; 1.00 eq.) of 2-chloro-4,6-diphenyl-[1,3,5]triazine [CAS 3842-55-5] and 8.04 g (32.4 mmol; 3.00 eq.) of tripotassium phosphate [CAS 7778-53-2] are suspended in 75 mL of dioxane [CAS 123-91-1], 75 mL of toluene [CAS 108-88-3] and 75 mL of water. To this suspension are added 121 mg (0.54 mmol; 0.05 eq.) of palladium(II) acetate [CAS 3375-31-3] and 329 mg (1.08 mmol; 0.10 eq.) of triorthotolylphosphine [CAS 6163-58-2], and the reaction mixture is heated under reflux for 16 h. After cooling, the solvent is removed and the residue is dissolved in dichloromethane [CAS 75-09-2] and water, and the phases are separated. After the aqueous phase has been extracted with dichloromethane (2×150 mL), the combined organic phases are washed with water (2×150 mL) and then concentrated to dryness. Purification by means of Soxhlet extraction, washing with ethyl acetate [CAS 141-78-6] and vacuum sublimation gives the desired product (1.78 g; 2.64 mmol; 24% of theory).

[0301] The following compounds can be obtained analogously:

TABLE-US-00009 No. Reactant 1 Reactant 2  1f [00442] [00443]  2f [00444] [00445]  3f [00446] [00447]  4f [00448] [00449]  5f [00450] [00451]  6f [00452] [00453]  7f [00454] [00455]  8f [00456] [00457]  9f [00458] [00459] 10f [00460] [00461] 11f [00462] [00463] 12f [00464] [00465] 13f [00466] [00467] 14f [00468] [00469] 15f [00470] [00471] 16f [00472] [00473] 17f [00474] [00475] 18f [00476] [00477] 19f [00478] [00479] 20f [00480] [00481] 21f [00482] [00483] 22f [00484] [00485] No. Product Yield  1f [00486] 38%  2f [00487] 44%  3f [00488] 35%  4f [00489] 49%  5f [00490] 47%  6f [00491] 41%  7f [00492] 58%  8f [00493] 20%  9f [00494] 36% 10f [00495] 29% 11f [00496] 27% 12f [00497] 34% 13f [00498] 39% 14f [00499] 29% 15f [00500] 29% 16f [00501] 35% 17f [00502] 38% 18f [00503] 41% 19f [00504] 48% 20f [00505] 42% 21f [00506] 22% 22f [00507] 25%

[0302] Isoquinoline derivatives of formula (Ia) can be obtained in accordance with the above-cited examples, with some corresponding isoquinolines being commercially available, or these being obtainable via known reactions, for example the Bischler-Napieralski reaction, the Pictet-Gams reaction or the Pictet-Spengler reaction.

[0303] OLEDs

[0304] The compounds of the invention can be used in organic electroluminescent devices, especially in OLEDs. These are produced and characterized by methods that are well known to the person skilled in the art. OLEDs containing the compounds of the invention have the abovementioned advantages over known OLEDs. Especially the performance data such as voltage, lifetime, stability and efficiency of the OLEDs can be enhanced by using the compounds of the invention.

[0305] General production process for the OLEDs and characterization of the OLEDs: Glass plates which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm form the substrates to which the OLEDs are applied.

[0306] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/electron transport layer (ETL)/electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm. Table 1 shows typical materials that can be used for production of OLEDs.

TABLE-US-00010 TABLE 1 Materials used [00508] p-Dopant [00509] HTM [00510] EBM [00511] H [00512] SEB [00513] TMM-1 [00514] TMM-2 [00515] TEG [00516] ETM [00517] LiQ

[0307] All materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the emission layer consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as H:SEB (95%:5%) mean here that the material H is present in the layer in a proportion by volume of 95% and SEB in a proportion of 5%.

[0308] In an analogous manner, the electron transport layer and the hole injection layer also consist of a mixture of two materials.

[0309] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation characteristics, and the lifetime are determined. The parameter EQE @ 10 mA/cm.sup.2 refers to the external quantum efficiency which is attained at 10 mA/cm.sup.2. The parameter U @ 10 mA/cm.sup.2 refers to the operating voltage at 10 mA/cm.sup.2. The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion in the course of operation with constant current density. An LT80 figure means here that the lifetime reported corresponds to the time after which the luminance has dropped to 80% of its starting value. The figure @60 or 40 mA/cm.sup.2 means here that the lifetime in question is measured at 60 or 40 mA/cm.sup.2.

[0310] It is found that OLEDs containing the compounds of the invention have very good performance data; in particular, they show distinctly improved lifetimes over comparable OLEDs from the prior art. Moreover, voltages and efficiencies are at a very high level.

[0311] Device Examples: Production of the OLEDs

[0312] OLEDs of the invention and OLEDs according to the prior art are produced by a general method according to WO 04/058911, which is adapted to the circumstances described here (variation in layer thickness, materials).

[0313] In the examples which follow (see tables 2 to 4), the data of various OLEDs are presented. Substrates used are glass substrates coated with structured ITO (indium tin oxide) of thickness 50 nm. The OLEDs basically have the following layer structure: [0314] substrate, [0315] ITO (50 nm), [0316] buffer (20 nm), [0317] hole injection layer (HTL 95%, HIL 5%) (20 nm), [0318] hole transport layer (HTL) (195 nm), [0319] emission layer (EML) (20 nm), [0320] electron transport layer (ETL 50%, EIL 50%) (30 nm), [0321] electron injection layer (EIL) (1 nm), [0322] cathode.

[0323] The cathode is formed by an aluminum layer of thickness 100 nm. The buffer applied by spin-coating is a 20 nm-thick layer of Clevios P VP Al 4083 (sourced from Heraeus Clevios GmbH, Leverkusen). All the rest of the materials are applied by thermal vapor deposition in a vacuum chamber. The structure of the OLEDs is shown in table 2. The materials used are shown in table 4.

[0324] The emission layer always consists of at least one matrix material (host=H) and an emitting dopant (=D) which is added to the matrix material in a particular proportion by volume by co-evaporation. Details given in such a form as H:D (97%:3%) mean here that the material H is present in the layer in a proportion by volume of 97% and D in a proportion of 3%.

[0325] Analogously, the electron transport layer may also consist of a mixture of two materials.

[0326] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra are recorded, and the current efficiency (measured in cd/A) and the external quantum efficiency (EQE, measured in percent) are calculated as a function of luminance, assuming Lambertian emission characteristics, from current-voltage-luminance characteristics (IUL characteristics), and finally the lifetime of the components is determined. The electroluminescence spectra are recorded at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y color coordinates are calculated therefrom. The parameter EQE @ 1000 cd/m.sup.2 refers to the external quantum efficiency at an operating luminance of 1000 cd/m.sup.2. The lifetime is the time LD95 @ 1000 cd/m.sup.2 that elapses before the starting brightness of 1000 cd/m.sup.2 has fallen by 5%. The data obtained for the various OLEDs are collated in table 3.

[0327] Use of Materials of the Invention as Electron Transport Material in OLEDs

[0328] The materials of the invention are suitable for use as electron transport material (ETL) in OLEDs and result in excellent performance data; see examples E1 to E4.

TABLE-US-00011 TABLE 2 Structure of the OLEDs EML ETL Ex. Thickness/nm Thickness/nm E1 H(97%):D(3%) 20 nm EG1(50%):EIL(50%) E2 H(97%):D(3%) 20 nm EG2(50%):EIL(50%) E3 H(97%):D(3%) 20 nm EG3(50%):EIL(50%) E4 H(97%):D(3%) 20 nm EG4(50%):EIL(50%)

TABLE-US-00012 TABLE 3 Data of the OLEDs EQE LD95 @ @ 1000 1000 cd/m.sup.2 cd/m.sup.2 CIE Ex. % [h] x y E1 5.3 120 0.13 0.14 E2 5.9 90 0.13 0.14 E3 5.5 110 0.13 0.14 E4 5.2 100 0.13 0.14

TABLE-US-00013 TABLE 4 Structures of the materials used [00518] HIL [00519] HTL [00520] H [00521] D [00522] EG1 [00523] EG2 [00524] EG3 [00525] EG4 [00526] EIL