HETEROCYCLIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Abstract

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

Claims

1.-19. (canceled)

20. A compound including at least one structure of formula (I) ##STR00301## where the rings Ar.sup.a and Ar.sup.b are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the rings Ar.sup.a and Ar.sup.b together may form a ring system; and where the further symbols and indices used are as follows: Z.sup.1, Z.sup.2, Z.sup.3 is the same or different at each instance and is N or B; W.sup.1, W.sup.2 is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) groups or the carbon atom and the nitrogen atom of the C═N group are each parts of the ring Ar.sup.a or Ar.sup.b, where the carbon atom of the C═N group binds to the V.sup.1 or V.sup.4 group; V.sup.1, V.sup.2 is the same or different at each instance and is —N═, —B═, ═C(Ar)— or ═C(R)—, or the V.sup.1, V.sup.2 groups form a ring of the formula ##STR00302## where the ring Ar.sup.c 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 Ar or R radicals, where the ring Ar.sup.c may form a ring system together with an X.sup.1 group or the rings Ar.sup.a and Ar.sup.c together may form a ring system, where W.sup.3 binds to the W.sup.1 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Ar.sup.c ring, where the carbon atom of the C═N group binds to the W.sup.1 group and the dotted lines represent the bonds to the W.sup.1 or Z.sup.2 group; V.sup.3, V.sup.4 is the same or different at each instance and is —N═, —B═, (Ar)C═C(Ar) or (R)C═C(R), or the V.sup.3, V.sup.4 groups form a ring of the formula ##STR00303## where the ring Ar.sup.d 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 Ar or R radicals, where the ring Ar.sup.d may form a ring system together with an X.sup.1 group or the rings Ar.sup.b and Ar.sup.d together may form a ring system, where W.sup.4 binds to the W.sup.2 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Ar.sup.a or Ar.sup.b ring, where the carbon atom of the C═N group binds to the W.sup.2 group and the dotted lines represent the bonds to the W.sup.2 or Z.sup.3 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 radicals; the Ar group here may form a ring system with at least one Ar, X.sup.1, R group or a further group; X.sup.1 is the same or different at each instance and is N, CR.sup.1 or C if a ring system is formed by a bond to one of the rings Ar.sup.c, Ar.sup.d or a further group, 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 or CR.sup.b, with the proviso that not more than two of the X.sup.1, X.sup.2 groups in one cycle are N; R, R.sup.a, R.sup.b 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)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, C(═O)Ar′, C(═O)R.sup.1, 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—, —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 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)OAr″, C(═O)OR.sup.2, C(═O)Ar″, C(═O)R.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 groups 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 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, 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; where at least one V.sup.1, V.sup.2, W.sup.1, W.sup.3 group represents N or B and at least one V.sup.3, V.sup.4, W.sup.2, W.sup.4 group represents N or B.

21. The compound as claimed in claim 20, comprising at least one structure of the formula (IIa), (IIb), (IIc), (IId) and/or (IIe): ##STR00304## where Z.sup.1, Z.sup.2, Z.sup.3, X.sup.1 and X.sup.2 have the definitions given in claim 20 and the further symbols are as follows: Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; W.sup.5, W.sup.6, W.sup.7, W.sup.8 is the same or different at each instance and is C(Ar) or X.sup.6, where Ar has the definition given in claim 20; X.sup.3 is the same or different at each instance and is N or CR.sup.1, with the proviso that not more than two of the X.sup.3, X.sup.5 groups in one cycle are N; X.sup.4 is the same or different at each instance and is N or CR.sup.d, with the proviso that not more than two of the X.sup.4, X.sup.6 groups in one cycle are N; X.sup.5 is the same or different at each instance and is N, CR.sup.c or C if a ring system is formed by a bond to an Ar group or an X.sup.5 group or an X.sup.6 group, with the proviso that not more than two of the X.sup.3, X.sup.5 groups in one cycle are N; X.sup.6 is the same or different at each instance and is N, CR.sup.f or C if a ring system is formed by a bond to an Ar group or an X.sup.5 group or an X.sup.6 group, with the proviso that not more than two of the X.sup.4, X.sup.6 groups in one cycle are N; R.sup.C, R.sup.d, R.sup.e, R.sup.f 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)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, C(═O)Ar′, C(═O)R.sup.1, 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 be substituted in each case 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—, —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.sup.c, R.sup.d, R.sup.e, R.sup.f radicals may also form a ring system together or with a further group, where the R.sup.1 radical has the definition given in claim 20.

22. The compound according to claim 20, including at least one structure of the formula (III-1) to (III-25): ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## where the symbols Z.sup.1, Z.sup.2, Z.sup.3, X.sup.1 and X.sup.2 have the definitions given in claim 20, Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; X.sup.3 is the same or different at each instance and is N or CR.sup.C, with the proviso that not more than two of the X.sup.3, X.sup.5 groups in one cycle are N; X.sup.4 is the same or different at each instance and is N or CR.sup.d, with the proviso that not more than two of the X.sup.4, X.sup.6 groups in one cycle are N; X.sup.5 is the same or different at each instance and is N, CR.sup.c or C if a ring system is formed by a bond to an Ar group or an X.sup.5 group or an X.sup.6 group, with the proviso that not more than two of the X.sup.3, X.sup.5 groups in one cycle are N; X.sup.6 is the same or different at each instance and is N, CR.sup.f or C if a ring system is formed by a bond to an Ar group or an X.sup.5 group or an X.sup.6 group, with the proviso that not more than two of the X.sup.4, X.sup.6 groups in one cycle are N; and the further symbols are defined as follows: p is 0 or 1, Y.sup.1 is the same or different at each instance and is a bond, N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20; Y.sup.2, Y.sup.3, Y.sup.4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20.

23. The compound as claimed in claim 20, including at least one structure of the formula (IV-1) to (IV-38): ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## where the symbols Z.sup.1, Z.sup.2, Z.sup.3, R.sup.a and R.sup.b have the definitions given in claim 20, Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; R.sup.c, R.sup.d, R.sup.e, R.sup.f 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)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, C(═O)Ar′, C(═O)R.sup.1, 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 be substituted in each case 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—, —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.sup.c, R.sup.d, R.sup.e, R.sup.f radicals may also form a ring system together or with a further group, where the R.sup.1 radical has the definition given in claim 20; yl is the same or different at each instance and is a bond, N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20; Y.sup.2, Y.sup.3, Y.sup.4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20; and the further symbols are defined as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2; k is 0 or 1.

24. The compound as claimed in claim 24, wherein Z.sup.1 is N and at least one of the Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 groups is B.

25. The compound as claimed in claim 21, wherein Z.sup.1 is N and at least one of the Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 groups is N.

26. The compound as claimed in claim 21, wherein Z.sup.1 is B and at least one of the Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 groups is N.

27. The compound as claimed in claim 20, wherein Z.sup.1 is B and at least one of the Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 groups is B.

28. The compound as claimed in claim 20, wherein at least two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals together with the further groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals bind form a fused ring, where the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals form at least one structure of the formulae (RA-1) to (RA-12): ##STR00323## ##STR00324## where R.sup.1 has the definition set out above, 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, R.sup.e, R.sup.f radicals bind, and the further symbols have the following definition: Y.sup.5 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.g 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 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 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.g radicals together or one R.sup.g 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.

29. The compound as claimed in claim 20, wherein at least two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals together with the further groups to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals bind form a fused ring, where the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals form the structures of the formula (RB): ##STR00325## where R.sup.1 has the definition set out in claim 20, the dotted bonds represent the sites of attachment to which the two R, R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e, R.sup.f radicals bind, the index m is 0, 1, 2, 3 or 4 and Y.sup.6 is C(R.sup.1).sub.2, NR.sup.1, NAr′, BR.sup.1, BAr′, O or S.

30. The compound as claimed in claim 20, comprising at least one structure of the formulae (V-1) to (V-10), where the compounds have at least one fused ring, ##STR00326## ##STR00327## where the symbols Z.sup.1, Z.sup.2, Z.sup.3, R.sup.a and R.sup.b have the definitions given in claim 20, Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; R.sup.c, R.sup.d, R.sup.e, R.sup.f 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)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, C(═O)Ar′, C(═O)R.sup.1, 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 be substituted in each case 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—, —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.sup.c, R.sup.d, R.sup.e, R.sup.f radicals may also form a ring system together or with a further group, where the R.sup.1 radical has the definition given in claim 20, Y.sup.3, Y.sup.4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20, the symbol o represents the sites of attachment, and the further symbols are defined as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2.

31. The compound as claimed in claim 20, comprising at least one structure of the formulae (VI-1) to (VI-9), where the compounds have at least one fused ring, ##STR00328## ##STR00329## where the symbols Z.sup.1, Z.sup.2, Z.sup.3, R.sup.a and R.sup.b have the definitions given in claim 20, Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; R.sup.c, R.sup.d, R.sup.e, R.sup.f 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)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, C(═O)Ar′, C(═O)R.sup.1, 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 be substituted in each case 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—, —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.sup.c, R.sup.d, R.sup.e, R.sup.f radicals may also form a ring system together or with a further group, where the R.sup.1 radical has the definition given in claim 20, Y.sup.3, Y.sup.4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20, the symbol o represents the sites of attachment, and the further symbols are defined as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2.

32. The compound as claimed in claim 20, comprising at least one structure of the formulae (VII-1) to (VII-9), where the compounds have at least one fused ring, ##STR00330## ##STR00331## where the symbols Z.sup.1, Z.sup.2, Z.sup.3, R.sup.a and R.sup.b have the definitions given in claim 20, Z.sup.4, Z.sup.5 is the same or different at each instance and is N or B; R.sup.c, R.sup.d, R.sup.e, R.sup.f 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)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, C(═O)Ar′, C(═O)R.sup.1, 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 be substituted in each case 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—, —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.sup.c, R.sup.d, R.sup.e, R.sup.f radicals may also form a ring system together or with a further group, where the R.sup.1 radical has the definition given in claim 20, Y.sup.3, Y.sup.4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R).sub.2, Si(R).sub.2, C═NR, C═NAr′, C═C(R).sub.2, O, S, Se, S═O, or SO.sub.2, where the symbols R and Ar′ have the definition set out in claim 20, the symbol o represents the sites of attachment, and the further symbols are defined as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2.

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, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

34. A formulation comprising at least one compound as claimed in claim 20 and at least one further compound.

35. 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, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

36. A process for preparing a compound as claimed in claim 20, comprising synthesizing a base skeleton having at least one of the Z.sup.2, Z.sup.3 groups or a precursor of one of the Z.sup.2, Z.sup.3 groups, and introducing the Z.sup.1 group by means of a metalation reaction, a nucleophilic aromatic substitution reaction or a coupling reaction.

37. A method comprising providing the compound as claimed in claim 20 and including the compound in an electronic device.

38. An electronic device comprising at least one compound as claimed in claim 20.

Description

EXAMPLES

[0239] 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

[0240] ##STR00195##

[0241] Preparation according to W. Wu et al., Organic Chemistry Frontiers, 2019, 6(13), 2200 using indole [120-72-9] and 2-iodo-4,6-dimethylaniline [4102-54-9], yield: 64%; purity: about 95% by .sup.1H NMR.

[0242] The following compounds can be prepared analogously:

TABLE-US-00002 Ex. Reactant Product Yield S2 [00196] [00197] 59% S3 [00198] [00199] 69% S4 [00200] [00201] 56% S5 [00202] [00203] 60% S6 [00204] [00205] 67% S7 [00206] [00207] 49% [00208]

Example S10

[0243] ##STR00209##

[0244] Preparation according to US2019/0252623, p. 62. Use of S1 rather than compound A, procedure from step 1 to 3, yield: 38%; purity: about 95% by .sup.1H NMR.

[0245] The following compounds can be prepared analogously:

TABLE-US-00003 Ex. Reactant Product Yield S11 [00210] [00211] 40% S12 [00212] [00213] 40% S13 [00214] [00215] 35% S14 [00216] [00217] 38% S15 [00218] [00219] 42% S16 [00220] [00221] 35% S17 [00222] [00223] 38% S18 [00224] [00225] 41% S19 [00226] [00227] 50%

Example S100

[0246] ##STR00228##

[0247] A mixture of 22.7 g (110 mmol) of 10H-indolo[1,2-a]benzimidazole [2345630-10-4], 11.3 g (50 mmol) of 1-bromo-2,3-dichlorobenzene [56691-77-4], 12.5 g (130 mmol) of sodium tert-butoxide [865-48-5], 354 mg (0.5 mmol) of (amphos).sub.2PdCl2 [887919-35-9] and 200 ml of o-xylene is stirred at 80° C. for 3 h and then at 130° 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 300 ml of ethanol, the solids are filtered off with suction, and these are washed twice with 50 ml of ethanol, dried under reduced pressure and recrystallized from dichloromethane/acetonitrile.

[0248] Yield: 15.2 g (29 dirndl) 58%; purity about 95% by .sup.1H NMR.

[0249] The following compounds can be prepared analogously:

TABLE-US-00004 Ex. Reactant Product Yield S101 [00229] [00230] 30% [00231] S102 [00232] [00233] 27% S103 [00234] [00235] 51% [00236] S104 [00237] [00238] 49% [00239] S105 [00240] [00241] 55% [00242] S106 [00243] [00244] 43% S107 [00245] [00246] 48% S108 [00247] [00248] 45% S109 [00249] [00250] 47% S110 [00251] [00252] 50% S111 [00253] [00254] 53% S112 [00255] [00256] 57% S113 [00257] [00258] 46% S114 [00259] [00260] 43%

Example, Dopant D100A and D100B and D100C

[0250] Step 1: Lithiation of S100

##STR00261##

[0251] Intermediate not Isolated

[0252] A baked-out, argon-inertized four-neck flask with magnetic stirrer bar, dropping funnel, water separator, reflux condenser and argon blanketing is charged with 26.1 g (50 mmol) of S100 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 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.

[0253] Step 2: Transmetalation and Cyclization

##STR00262##

[0254] 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 DCM onto ISOLUTE® and hot-filtered through a silica gel bed with an n-pentane-DCM mixture (10:1). The filtrate is concentrated to dryness. The residue is flash-chromatographed (silica gel, n-heptane/ethyl acetate, gradient, Torrent automated column system from A. Semrau), which separates the three isomeric dopants D100A, D100B and D1000. Each individual dopant can be further purified again by flash chromatography. Further purification is effected by repeated hot extraction crystallization with DCM/acetonitrile mixtures and final fractional sublimation or heat treatment under reduced pressure. Yields: D100A: 1.98 g (4.0 mmol) 8%, D100B: 4.60 g (9.3 mmol) 19%, D1000: 3.56 g (7.2 mmol) 14%; purity about 99.9% by .sup.1H NMR.

[0255] The following compounds can be prepared analogously:

TABLE-US-00005 Yield Ex. Reactant Products beute D101A S101 [00263] 4% D101B [00264] 9% D101C [00265] 5% D102A S102 [00266] 3% D103A S103 [00267] 10% D103B [00268] 17% D103C [00269] 17% D104A S104 [00270] 12% D104B [00271] 22% D104C [00272] 19% D105A S105 [00273] 36% D106A S106 [00274] 32% D107A S107 [00275] 33% D108A S108 [00276] 30% D109A S109 [00277] 18% D110A S110 [00278] 35% D111A [00279] 10% D111B S111 [00280] 18% D111C [00281] 17% D112A S112 [00282] 6% D112B [00283] 18% D112C [00284] 22% D113A S113 [00285] 12% D113B [00286] 23% D113C [00287] 18% D114C S114 [00288] 40% D115C 2373393- 86-1 [00289] 37%

Example, Dopant D200A

[0256] ##STR00290##

[0257] Preparation from D100A 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 25%.

Example, Dopant D215C

[0258] ##STR00291##

[0259] Preparation from D115C by flash vacuum pyrolysis, carrier gas: argon, reduced pressure about 10.sup.−2 torr, pyrolysis zone temperature 550° C., catalyst: 5% PdO on alumina. Yield 30%.

[0260] Production of Vacuum-Processed OLED Devices:

[0261] 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).

[0262] 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 Al 4083 from Heraeus Precious Metals GmbH Germany, 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.

[0263] 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.

[0264] 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 SMB1 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.

[0265] 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 Im/VV) 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).

[0266] Use of compounds of the invention as materials in OLEDs One use of the compounds of the invention is as 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-00006 TABLE 1 Structure of the OLEDs Ex. EML HBL ETL Blue OLEDs (420-499 nm) D-Ref. 1 SMB1:D-Ref. 1 ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D100A SMB1:D-D100A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D100B SMB1:D-D100B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D101A SMB4:D-D101A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D101B SMB1:D-D101B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D102A SMB1:D-D102A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D103A SMB1:D-D103A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D104A SMBW-D104A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D104B SMB1:D-D104B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D105A SMB1:D-D105A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D106A SMB1:D-D106A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D107A SMB1:D-D107A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D108A SMB1:D-D108A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D109A SMB1:D-D109A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D110A SMB1:D-D110A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D111A SMB1:D-D111A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D111B SMB1:D-D111B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D112A SMB1:D-D112A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D113A SMB1:D-D113A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D113B SMB1:D-D113B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) Green & yellow OLEDs (500-590 nm) D-D100C SMB1:D-D100C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D101C SMB1:D-D101C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D103B SMB1:D-D103B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D103C SMB1:D-D103C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D104C SMB1:D-D104C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D111C SMB1:D-D111C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D112B SMB1:D-D112B ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D112C SMB1:D-D112C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D113C SMB2:D-C113C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D114C SMB3:D-D114C ETM1 ETM1:ETM2 (95%:5%) (50%:50%) D-D115C SMB4:D-D115C ETM1 ETM1:ETM2 (93%:7%) (50%:50%) D-D210A SMB1:D-D210A ETM1 ETM1:ETM2 (95%:5%) (50%:50%) Red OLEDs (591-700 nm) D-D215C SMB1:D-D116C ETM1 ETM1:ETM2 (97%:3%) (50%:50%)

TABLE-US-00007 TABLE 2 Results for the vacuum-processed OLEDs EQE Voltage EL-max. EL-FWHM Ex. [%] [V] [nm] [eV] Ref. 1 6.3 4.6 464 0.17 D-D100A 6.0 4.6 438 0.17 D-D100B 7.4 4.4 484 0.31 D-D100C 7.9 4.3 540 0.18 D-D101A 5.1 4.6 423 0.15 D-D101B 7.2 4.4 476 0.28 D-D101C 7.8 4.3 527 0.19 D-D102A 6.3 4.5 442 0.15 D-D103A 7.1 4.5 462 0.14 D-D103B 6.7 4.4 502 0.30 D-D103C 7.0 4.5 564 0.19 D-D104A 6.8 4.5 456 0.16 D-D104B 6.9 4.4 499 0.28 D-D104C 7.5 4.1 550 0.27 D-D105A 6.7 4.4 477 0.16 D-D106A 6.8 4.4 482 0.15 D-D107A 6.2 4.5 441 0.15 D-D108A 6.3 4.5 445 0.16 D-D109A 6.3 4.5 440 0.16 D-D110A 6.6 4.4 462 0.15 D-D111A 6.5 4.4 458 0.16 D-D111B 6.9 4.3 486 0.29 D-D111C 7.4 4.2 542 0.20 D-D112A 6.9 4.5 447 0.16 D-D112B 7.3 4.3 533 0.30 D-D112C 7.6 3.9 596 0.20 D-D113A 5.9 4.5 436 0.16 D-D113B 6.7 4.4 482 0.29 D-D113C 7.5 4.1 537 0.19 D-D114C 7.7 3.9 573 0.18 D-D115C 7.0 4.3 564 0.18 D-D210A 6.1 4.2 540 0.35 D-D215C 3.8 3.5 686 0.22

TABLE-US-00008 TABLE 3 Structural formulae of the materials used [00292] [00293] [00294] [00295] [00296] [00297] [00298] [00299] [00300]

[0267] With the compounds of the invention of regioisomer type A, blue and deep blue OLEDs having better efficiency and operating voltage are obtainable, which leads to components having improved power efficiency. Moreover, deep blue OLEDs having an emission maxima of around 440 nm or lower are not obtainable with the compounds according to the prior art. Moreover, the compounds of the invention of regioisomer type A are notable for emission spectra having a very small half-height width EL-FWHM (ELectroluminescent Full Width Half Max), which leads to very pure-color emission and hence to very good CIE X and Y values.

[0268] Moreover, the compounds of the invention of regioisomer type C are notable for emission spectra having a very small half-height width EL-FWHM (ElectroLuminescent Full Width Half Max), which leads to very pure-color emission and hence to very good CIE X and Y values. With these, not only the blue but also the green and yellow spectral region is accessible. The high EQE values at reduced operating voltages lead to components having very good power efficiency.

[0269] Compounds of the invention of regioisomer type B show improved efficiency and operating voltage. Moreover, green, yellow and red components are achievable with these compounds.