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HETEROAROMATIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

20230157170 · 2023-05-18

    Inventors

    Cpc classification

    International classification

    Abstract

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

    Claims

    1.-17. (canceled)

    18. A compound including at least one structure of the formula (I) ##STR00422## where the symbols used are as follows: Z is the same or different at each instance and is N or B; W.sup.1, W.sup.2, W.sup.3, W.sup.4 is the same or different at each instance and is N or CR, where at least one W.sup.1, W.sup.2, W.sup.3, W.sup.4 per ring is N; X.sup.1 is the same or different at each instance and is N, CR.sup.a or CAr, with the proviso that not more than two of the X.sup.1, X.sup.2 groups in one cycle are N; X.sup.2 is the same or different at each instance and is N, CR.sup.b or CAr, with the proviso that not more than two of the X.sup.1, X.sup.2 groups in one cycle are N; X.sup.3 is the same or different at each instance and is N, CR.sup.c or CAr, with the proviso that not more than two of the X.sup.3, X.sup.4 groups in one cycle are N; X.sup.4 is the same or different at each instance and is N, CR.sup.d, CAr or C if a ring system is formed by a bond to an X.sup.4 group, with the proviso that not more than two of the X.sup.3, X.sup.4 groups in one cycle are N; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, R group or a further group; R, R.sup.a, R.sup.b, R.sup.c, R.sup.d 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, C(═O)OAr′, C(═O)OR.sup.1, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 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, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, P(═O)(R.sup.1), —O—, —Se—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case 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; at the same time, two R, R.sup.a, R.sup.b, R.sup.d radicals may also form a ring system together or with a further group; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 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 carbon atom, 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, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, 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, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, C(═O)OAr″, C(═O)OR.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(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 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—, —C≡C—, Si(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—, 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.2 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.2 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.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; at the same time, one or more R.sup.1 radicals may form a ring system with a further part of the compound; 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.2 radicals; at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, 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.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, 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 selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and 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, two or more substituents R.sup.2 together may form a ring system.

    19. The compound as claimed in claim 18, comprising at least one structure of the formula (IIa), (IIb), (IIc) and/or (IId): ##STR00423## where Z, X.sup.1, X.sup.2, X.sup.3, X.sup.4, R, R.sup.a, R.sup.b, R.sup.c and R.sup.d have the definitions given in claim 18 and the further symbols and indices are as follows: Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), —(O)C—C(O)—, —N(Ar′)—C(O)—, —(R.sup.1).sub.2C—C(R.sup.1).sub.2—, —(R.sup.1)C═C(R.sup.1)—, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, where the aryl or heteroaryl group binds to the further parts of the structure via two adjacent and mutually joined carbon atoms and may be substituted by one or more R.sup.1 radicals, where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; j is 0, 1 or 2; p is 0 or 1, where p=0 means that the Y.sup.1 group is absent; k is 0 or 1, where k=0 if p=1.

    20. The compound according to claim 18, comprising at least one structure of the formula (IIIa) to (IIIv) ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## where Z, R, R.sup.a, R.sup.b, R.sup.c and R.sup.d have the definitions given in claim 18, Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), —(O)C—C(O)—, —N(Ar′)—C(O)—, —(R.sup.1).sub.2C—C(R.sup.1).sub.2—, —(R.sup.1)C═C(R.sup.1)—, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, where the aryl or heteroaryl group binds to the further parts of the structure via two adjacent and mutually joined carbon atoms and may be substituted by one or more R.sup.1 radicals, where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; j is 0, 1 or 2; k is 0 or 1, and the further symbols have the following definition: Y.sup.2, Y.sup.3 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; and m is 0, 1, 2, 3 or 4.

    21. The Compound according to claim 18, wherein at least two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals together with the further groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind form a fused ring, where the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals form at least one structure of the formulae (RA-1) to (RA-12): ##STR00430## ##STR00431## where R.sup.1 has the definition set out above, the dotted bonds represent the sites of attachment via which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind, and the further symbols have the following definition: Y.sup.4 is the same or different at each instance and is C(R.sup.1).sub.2, (R.sup.1).sub.2C—C(R.sup.1).sub.2, (R.sup.1)C═C(R.sup.1), NR.sup.1, NAr′, O or S; R.sup.e is the same or different at each instance and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkyl or alkenyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R.sup.2 radicals, where one or more adjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(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.1), —O—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 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.2 radicals; at the same time, it is also possible for two R.sup.e radicals together or one R.sup.e radical together with an R.sup.1 radical or together with a further group to form a ring system; s is 0, 1, 2, 3, 4, 5 or 6; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

    22. The compound as claimed in claim 18, wherein at least two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals together with the further groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind form a fused ring, where the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals form structures of the formulae (RA-1a) to (RA-4f): ##STR00432## ##STR00433## where the dotted bonds represent the sites of attachment via which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind, the index m is 0, 1, 2, 3 or 4 and the symbols R.sup.1, R.sup.2, R.sup.c and the indices s and t have the definition detailed above, especially in claim 18.

    23. The compound as claimed in claim 18, wherein at least two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals together with the further groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind form a fused ring, where the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals form structures of the formula (RB): ##STR00434## where R.sup.1 has the definition set out in claim 18, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals bind, the index m is 0, 1, 2, 3 or 4 and Y.sup.5 is C(R.sup.1).sub.2, NAr′, BAr′, O or S.

    24. The compound as claimed in claim 18, comprising at least one structure of the formulae (IV-1) to (IV-36), where the compounds have at least one fused ring, ##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440## ##STR00441## ##STR00442## where Z, R, R.sup.a, R.sup.c and R.sup.d have the definitions given in claim 18, Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), —(O)C—C(O)—, —N(Ar′)—C(O)—, —(R.sup.1).sub.2C—C(R.sup.1).sub.2—, —(R.sup.1)C═C(R.sup.1)—, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, where the aryl or heteroaryl group binds to the further parts of the structure via two adjacent and mutually joined carbon atoms and may be substituted by one or more R.sup.1 radicals, where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; j is 0, 1 or 2; k is 0 or 1, Y.sup.2, Y.sup.3 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; and the symbol o represents the attachment sites, and the index m is 0, 1, 2, 3 or 4.

    25. A compound as claimed in claim 18, comprising at least one structure of the formulae (V-1) to (V-22), where the compounds have at least one fused ring, ##STR00443## ##STR00444## ##STR00445## ##STR00446## ##STR00447## where Z, R, R.sup.a, R.sup.c and R.sup.d have the definitions given in claim 18, Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), —(O)C—C(O)—, —N(Ar′)—C(O)—, —(R.sup.1).sub.2C—C(R.sup.1).sub.2—, —(R.sup.1)C═C(R.sup.1)—, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, where the aryl or heteroaryl group binds to the further parts of the structure via two adjacent and mutually joined carbon atoms and may be substituted by one or more R.sup.1 radicals, where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; j is 0, 1 or 2; k is 0 or 1, Y.sup.2, Y.sup.3 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; the symbol o represents the attachment sites, and the index m is 0, 1, 2, 3 or 4.

    26. The compound as claimed in claim 21, wherein the compounds have at least two fused rings, wherein at least one fused ring comprises structures of the formulae (RA-1) to (RA-12) and a further ring comprises structures of the formulae (RA-1) to (RA-12) or (RB), comprising at least one structure of the formulae (VI-1) to (VI-22): ##STR00448## ##STR00449## ##STR00450## ##STR00451## ##STR00452## where Z is the same or different at each instance and is N or B; R, R.sup.a, R.sup.c, R.sup.d 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, C(═O)OAr′, C(═O)OR.sup.1, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 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, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, NR.sup.1, P(═O)(R.sup.1), —O—, —Se—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case 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; at the same time, two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d radicals may also form a ring system together or with a further group; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 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 carbon atom, 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, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, 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, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, C(═O)OAr″, C(═O)OR.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(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 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—, —C≡C—, Si(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—, 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.2 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.2 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.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; at the same time, one or more R.sup.1 radicals may form a ring system with a further part of the compound; 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.2 radicals; at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, 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.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, 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 selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and 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, two or more substituents R.sup.2 together may form a ring system, Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1), —(O)C—C(O)—, —N(Ar′)—C(O)—, —(R.sup.1).sub.2C—C(R.sup.1).sub.2—, —(R.sup.1)C═C(R.sup.1)—, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, where the aryl or heteroaryl group binds to the further parts of the structure via two adjacent and mutually joined carbon atoms and may be substituted by one or more R.sup.1 radicals, where the symbols R.sup.1 and Ar′ have the definition set out in claim 18; j is 0, 1 or 2; k is 0 or 1, Y.sup.2, Y.sup.3 is the same or different at each instance and is a bond, N(Ar′), N(R.sup.1), B(Ar′), B(R.sup.1), P(═O)(Ar′), P(═O)(R.sup.1), C(═O), C(Ar′).sub.2, C(R.sup.1).sub.2, Si(Ar′).sub.2, Si(R.sup.1).sub.2, O, S, Se, S═O, SO.sub.2, C(═O)N(Ar′), C(═O)N(R.sup.1), P(Ar′) or P(R.sup.1); and the symbol o represents the attachment sites.

    27. The compound as claimed in claim 18, wherein the compound comprises exactly two or exactly three structures of formula (I), (IIa) to (IId), (IIIa) to (IIIr), (IV-1) to (IV-36), (V-1) to (V-22) and/or (VI-1) to (VI-22).

    28. A compound as claimed in claim 27, selected from compounds of the formula (D-1) and (D-2): ##STR00453## where the L.sup.1 group represents a connecting group, Z is the same or different at each instance and is N or B; W.sup.1, W.sup.2, W.sup.3, W.sup.4 is the same or different at each instance and is N or CR, where at least one W.sup.1, W.sup.2, W.sup.3, W.sup.4 per ring is N; X.sup.1 is the same or different at each instance and is N, CR.sup.a or CAr, with the proviso that not more than two of the X.sup.1, X.sup.2 groups in one cycle are N; X.sup.2 is the same or different at each instance and is N, CR.sup.b or CAr, with the proviso that not more than two of the X.sup.1, X.sup.2 groups in one cycle are N; X.sup.3 is the same or different at each instance and is N, CR.sup.c or CAr, with the proviso that not more than two of the X.sup.3, X.sup.4 groups in one cycle are N; X.sup.4 is the same or different at each instance and is N, CR.sup.d, CAr or C if a ring system is formed by a bond to an X.sup.4 group, with the proviso that not more than two of the X.sup.3, X.sup.4 groups in one cycle are N; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, R group or a further group; R, R.sup.a, R.sup.b, R.sup.c, R.sup.d 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, C(═O)OAr′, C(═O)OR.sup.1, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 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, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, P(═O)(R.sup.1), —O—, —Se—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case 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; at the same time, two R, R.sup.a, R.sup.b, R.sup.d radicals may also form a ring system together or with a further group; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 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 carbon atom, 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, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, 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, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, C(═O)OAr″, C(═O)OR.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(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 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—, —C≡C—, Si(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—, 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.2 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.2 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.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; at the same time, one or more R.sup.1 radicals may form a ring system with a further part of the compound; 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.2 radicals; at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, 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.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, 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 selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and 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, two or more substituents R.sup.2 together may form a ring system.

    29. An oligomer, polymer or dendrimer containing one or more compounds as claimed in claim 18, wherein, in place of a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

    30. A formulation comprising at least one compound as claimed in claim 18 and at least one further compound.

    31. A composition comprising at least one compound as claimed in claim 18 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

    32. A process for preparing the compound as claimed in claim 18, wherein a base skeleton having at least one of the W.sup.1, W.sup.2, W.sup.3, W.sup.4 groups or a precursor of one of the W.sup.1, W.sup.2, W.sup.3, W.sup.4 groups is synthesized, and the Z group is introduced by means of a metalation reaction, a nucleophilic aromatic substitution reaction or a coupling reaction.

    33. A method comprising providing the compound as claimed in claim 18 and incorporating the compound in an electronic device.

    34. An electronic device comprising at least one compound as claimed in claim 18.

    Description

    EXAMPLES

    [0165] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The metal complexes are additionally handled with exclusion of light or under yellow light. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective figures in square brackets or the numbers quoted for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds that can have multiple enantiomeric, diastereomeric or tautomeric forms, one form is shown in a representative manner.

    Synthesis of Synthons S:

    Example S1

    [0166] ##STR00308##

    [0167] A mixture of 13.0 g (110 mmol) of benzimidazole [51-17-2], 11.3 g (50 mmol) of 1-bromo-2,3-dichlorobenzene [56691-77-4], 27.6 g (130 mmol) of tripotassium phosphate, anhydrous [7778-53-2], 240 mg (0.5 mmol) of tetramethyl-di-tBuXPhos [857356-94-6], 124 mg (0.5 mmol) of palladium(II) acetate [3375-31-3], 50 g of glass beads (diameter 3 mm) and 250 ml of toluene is stirred at 80° C. for 3 h and then at 110° C. for 6 h. After cooling, the mixture is admixed with 500 ml of ethyl acetate and 500 ml of water, and the organic phase is removed, washed once with 500 ml of water and twice with 300 ml each time of saturated sodium chloride solution, and dried over magnesium sulfate. The mixture is filtered through a silica gel bed in the form of an ethyl acetate slurry, the filtrate is concentrated to dryness, the residue is boiled with 50 ml of ethanol, the solids are filtered off with suction, and these are washed twice with 20 ml of ethanol, dried under reduced pressure and recrystallized from o-xylene. Yield: 14.7 g (42 mmol) 85%; purity about 95% by .sup.1H NMR.

    [0168] The following compounds can be prepared analogously:

    TABLE-US-00002 Ex. Reactant Product Yield S2 [00309]embedded image [00310]embedded image 70% [00311]embedded image S3 [00312]embedded image [00313]embedded image 30% S4 [00314]embedded image [00315]embedded image 65% [00316]embedded image S5 [00317]embedded image [00318]embedded image 68% S6 [00319]embedded image [00320]embedded image 61% S7 [00321]embedded image [00322]embedded image 63% [00323]embedded image S8 [00324]embedded image [00325]embedded image 78% S9 [00326]embedded image [00327]embedded image 80% S10 [00328]embedded image [00329]embedded image 78% [00330]embedded image S11 [00331]embedded image [00332]embedded image 80% S12 [00333]embedded image [00334]embedded image 44% S13 [00335]embedded image [00336]embedded image 81% S14 [00337]embedded image [00338]embedded image 67% S15 [00339]embedded image [00340]embedded image 70% S16 [00341]embedded image [00342]embedded image 67% S17 [00343]embedded image [00344]embedded image 69% S18 [00345]embedded image [00346]embedded image 62% S19 [00347]embedded image [00348]embedded image 55% S20 [00349]embedded image [00350]embedded image 65% S21 [00351]embedded image [00352]embedded image 53% S22 [00353]embedded image [00354]embedded image 49% S23A [00355]embedded image [00356]embedded image 35% S23B [00357]embedded image 25% S23C [00358]embedded image 18% S24 [00359]embedded image [00360]embedded image 65% S25 [00361]embedded image [00362]embedded image 63% S26 [00363]embedded image [00364]embedded image 70% S27 [00365]embedded image [00366]embedded image 66% S28 [00367]embedded image [00368]embedded image 70% S29 [00369]embedded image [00370]embedded image 72% S30 [00371]embedded image [00372]embedded image 78% S31 [00373]embedded image [00374]embedded image 73% S32 [00375]embedded image [00376]embedded image 48%

    Example, Dopant D1

    Step 1: Lithiation of S1

    [0169] ##STR00377##

    [0170] A baked-out, argon-inertized four-neck flask with magnetic stirrer bar, dropping funnel, water separator, reflux condenser and argon blanketing is charged with 15.5 g (50 mmol) of S1 and 200 ml of tert-butylbenzene, and cooled to −40° C. 64.7 ml (110 mmol) of tert-butyllithium, 1.7 M in n-pentane, is added dropwise to the reaction mixture over 10 min. The reaction mixture is allowed to warm up to room temperature and stirred at 60° C. for a further 3 h, in the course of which n-pentane is distilled off via the water separator.

    Step 2: Transmetalation and Cyclization

    [0171] ##STR00378##

    [0172] The reaction mixture is cooled back down to −40° C. 5.7 ml (60 mmol) of boron tribromide is added dropwise over a period of about 10 min. On completion of addition, the reaction mixture is stirred at RT for 1 h. Then the reaction mixture is cooled down to 0° C., and 21.0 ml (120 mmol) of di-iso-propylethylamine is added dropwise over a period of about 30 min. Then the reaction mixture is stirred at 130° C. for 5 h. After cooling, the mixture is diluted with 500 ml of toluene and hydrolyzed by addition of 300 ml of aqueous 10% by weight potassium acetate solution, and the organic phase is removed and concentrated to dryness under reduced pressure. The oily residue is absorbed with ECM onto ISOLUTE® and hot-filtered through a silica gel bed with an n-pentane-DCM mixture (5:1). The filtrate is concentrated to dryness. The residue is subjected to flash chromatography, silica gel, n-heptane/ethyl acetate, gradient, Torrent automated column system from A. Semrau. Further purification is effected by repeated hot extraction crystallization with DCM/acetonitrile mixtures and final fractional sublimation or heat treatment under reduced pressure. Yields: 5.5 g (17 mmol), 34%; purity: about 99.9% by .sup.1H NMR.

    [0173] The following compounds can be prepared analogously:

    TABLE-US-00003 Ex. Reactant Products Yield D2 S2 [00379]embedded image 27% D3 S3 [00380]embedded image  9% D4 S4 [00381]embedded image 36% D5 S5 [00382]embedded image 44% D6 S6 [00383]embedded image 28% D7 S7 [00384]embedded image 48% D8 S8 [00385]embedded image 45% D9 S9 [00386]embedded image 30% D10 S10 [00387]embedded image 46% D11 S11 [00388]embedded image 41% D12 S12 [00389]embedded image 36% D13 S13 [00390]embedded image 45% D14 S14 [00391]embedded image 40% D15 S15 [00392]embedded image 39% D16 S16 [00393]embedded image 31% D17 S17 [00394]embedded image 37% D18 S18 [00395]embedded image 37% D19 S19 [00396]embedded image 33% D20 S20 [00397]embedded image 29% D21 S21 [00398]embedded image 36% D22 S22 [00399]embedded image 34% D23A S23A [00400]embedded image 14% D23B S23B [00401]embedded image 15% D23C S23C [00402]embedded image  7% D100 S24 [00403]embedded image 25% D101 S25 [00404]embedded image 38% D102 S26 [00405]embedded image 40% D103 S27 [00406]embedded image 41% D104 S28 [00407]embedded image 23% D105 S29 [00408]embedded image 38% D106 S30 [00409]embedded image 40% D107 S31 [00410]embedded image 21% D200 S32 [00411]embedded image 24%

    Example, Dopant D18P

    [0174] ##STR00412##

    [0175] Preparation from D18 by flash vacuum pyrolysis, carrier gas: argon, reduced pressure about 10.sup.−2 torr, pyrolysis zone temperature 600° C., catalyst: 5% PdO on alumina. Yield 22%.

    1) Vacuum-Processed Devices:

    [0176] OLEDs of the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is adapted to the circumstances described here (variation in layer thickness, materials used).

    [0177] In the examples which follow, the results for various OLEDs are presented. Cleaned glass plates (cleaning in Miele laboratory glass washer, Merck Extran detergent) coated with structured ITO (indium tin oxide) of thickness 50 nm are pretreated with UV ozone for 25 minutes (PR-100 UV ozone generator from UVP) and, within 30 min, for improved processing, coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), purchased as CLEVIOS™ P VP AI 4083 from Heraeus Precious Metals GmbH Deutschland, spun on from aqueous solution) and then baked at 180° C. for 10 min. These coated glass plates form the substrates to which the OLEDs are applied.

    [0178] The OLEDs basically have the following layer structure: Substrate/hole injection layer 1 (HIL1) consisting of Ref-HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm/hole transport layer 1 (HTL1) composed of: 150 nm HTM1 for UV & blue OLEDs; 50 nm for green and yellow OLEDs; 110 nm for red OLEDs/hole transport layer 2 (HTL2) composed of: 10 nm for blue OLEDs; 20 nm for green & yellow OLEDs; 10 nm for red OLEDs/emission layer (EML): 25 nm for blue OLEDs; 40 nm for green & yellow OLEDs; 35 nm for red OLEDs/hole blocker layer (HBL) 10 nm/electron transport layer (ETL) 30 nm/electron injection layer (EIL) composed of 1 nm ETM2/and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm.

    [0179] First of all, vacuum-processed OLEDs are described. For this purpose, all the materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the emission layer always 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 SMB1:D1 (95:5%) mean here that the material SEB1 is present in the layer in a proportion by volume of 95% and D1 in a proportion of 5%. Analogously, the electron transport layer may also consist of a mixture of two materials. The exact structure of the OLEDs can be found in table 1. The materials used for production of the OLEDs are shown in table 3.

    [0180] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) are, as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming Lambertian radiation characteristics. The electroluminescent spectra are recorded at a luminance of 1000 cd/m.sup.2, and these are used to infer the emission color and the EL-FWHM values (ELectroluminescence—Full Width Half Maximum—width of the EL emission spectra at half the peak height in eV; for better comparability over the entire spectral range).

    Use of Compounds of the Invention as Materials in OLEDs:

    [0181] One use of the compounds of the invention is as hole transport material and dopant in the emission layer in OLEDs. The compounds D-Ref.1 according to table 3 are used as a comparison according to the prior art. The results for the OLEDs are collated in table 2.

    TABLE-US-00004 TABLE 1 Structure of the OLEDs Ex. EML HBL ETL Blue OLEDs (430 D-499 nm) D-Ref.1 SMB1:D-Ref.1 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D1 SMB1:D1 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D2 SMB1:D2 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D3 SMB1:D3 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D4 SMB1:D4 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D5 SMB1D5 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D6 SMB1:D6 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D7 SMB1:D7 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D8 SMB1:D8 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D11 SMB1:D11 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D12 SMB1:D12 ETM1 ETM1:ETM2 (97%:3%) (50%:50%) D-D13 SMB1:D13 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D14 SMB1:D14 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D15 SMB1:D15 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D16 SMB1:D16 ETM1 ETM1:ETM2 (97%:3%) (50%:50%) D-D17 SMB1:D17 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D18 SMB1:D18 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D19 SMB1:D19 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D23A SMB1:D23A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D23B SMB1:D23B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D200 SMB1:D200 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) Green & yellow OLEDs (500-590 nm) D-D9 SMB1:D9 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D10 SMB1:D10 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D20 SMB1:D20 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D21 SMB1:D21 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D1-D22 SMB1:D22 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D2-D22 SMB2:D22 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D3-D22 SMB3:D22 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D4-D22 SMB4:D22 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D23C SMB1:D23C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D100 SMB1:D100 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D101 SMB1:D101 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D102 SMB1:D102 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D103 SMB1:D103 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D105 SMB1:D105 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D107 SMB1:D107 ETM1 ETM1:ETM2 (97%:3%) (50%:50%) D-D18P SMB1:D18P ETM1 ETM1:ETM2 (97%:3%) (50%:50%) Red OLEDs (591-650 nm) D-D104 SMB1:D104 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D106 SMB1:D106 ETM1 ETM1:ETM2 (95%:5%) (50%:50%)

    TABLE-US-00005 TABLE 2 Results for the vacuum-processed OLEDs EQE (%) Voltage (V) EL-max. EL-FWHM Ex. 1000 cd/m.sup.2 1000 cd/m.sup.2 [nm] [eV] Ref. 1 6.1 4.6 462 0.17 D-D1 6.7 4.6 448 0.15 D-D2 6.5 4.6 450 0.15 D-D3 7.5 4.5 470 0.16 D-D4 7.8 4.6 451 0.15 D-D5 7.3 4.6 457 0.15 D-D6 7.0 4.5 455 0.15 D-D7 7.3 4.5 468 0.16 D-D8 7.1 4.5 465 0.16 D-D9 7.3 4.3 524 0.16 D-D10 7.6 4.4 519 0.16 D-D11 7.7 4.6 452 0.15 D-D12 7.5 4.6 455 0.15 D-D13 7.6 4.5 459 0.16 D-D14 7.6 4.5 458 0.15 D-D15 7.9 4.4 464 0.16 D-D16 7.6 4.5 460 0.15 D-D17 6.9 4.5 463 0.15 D-D18 7.3 4.4 478 0.16 D-D19 8.5 4.4 487 0.15 D-D20 7.5 4.3 501 0.13 D-D21 7.6 4.4 503 0.15 D1-D22 7.4 4.5 510 0.14 D2-D22 7.1 4.5 509 0.14 D3-D22 7.6 4.4 512 0.14 D4-D22 6.8 4.6 508 0.15 D-D23A 7.4 4.4 483 0.16 D-D23B 7.6 4.4 498 0.15 D-D23C 7.5 4.5 516 0.17 D-D100 7.5 4.5 508 0.17 D-D101 6.8 4.5 520 0.17 D-D102 7.7 4.4 543 0.17 D-D103 7.6 4.4 522 0.17 D-D104 7.2 4.2 610 0.17 D-D105 7.3 4.4 561 0.17 D-D106 7.0 4.3 596 0.16 D-D107 6.8 4.5 528 0.17 D-D200 6.5 4.4 484 0.19 D-D18P 6.3 4.4 523 0.17

    TABLE-US-00006 TABLE 3 Structural formulae of the materials used [00413]embedded image [00414]embedded image [00415]embedded image [00416]embedded image [00417]embedded image [00418]embedded image [00419]embedded image [00420]embedded image [00421]embedded image

    [0182] By comparison with the reference, some of the compounds of the invention show narrower or comparably narrow electroluminescence spectra, recognizable by the smaller or equal EL-FWHM values (ELectroluminescence—Full Width Half Maximum—width of the EL emission spectra in eV at half the peak height). Narrower electroluminescence spectra lead to a distinct improvement in color purity (lower CIE y values). Moreover, EQE values (External Quantum Efficiencies) of the inventive examples are distinctly greater and operating voltages are lower compared to the reference, which leads to a distinct improvement in power efficiencies of the device and hence to lower power consumption.