Bisbenzofuran-fused indeno[1,2-B]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)

A compound of formula (1-1a)-(1-6a):

• wherein
• Z is on each occurrence, identically or differently, CR or N;
• E is on each occurrence, identically or differently, selected from the group consisting of —BR0—, —C(R0)2—, —C(R0)2—C(R0)2—, —C(R0)2—O—, —C(R0)2—S—, —R0C═CR0—, —R0C═N—, —Si(R0)2—, —Si(R0)2—Si(R0)2—, Ge(R0)2, —C(═O)—, —C(═NR0)—, —C(═C(R0)2)—, —O—, —S—, —Se—, —S(═O)—, —SO2—, —N(R0)—, —P(R0)— and —P((═O)R0)—,
• X is on each occurrence, identically or differently, selected from the group consisting of —O—, —S—, —S(═O)—, —SO2—, —N(R0)—, —BR0—, Si(R0)2, —P(R0)—, and —P((═O)R0)—;
• W is on each occurrence, identically or differently, CR or N;
• R and R0 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, wherein one or more non-adjacent CH2 groups are optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, P(═O)(R2), SO, SO2, O, S, or CONR2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, and wherein two adjacent substituents R and/or two adjacent substituents R0 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
• R1 is on each occurrence, identically or differently, D, F CN, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, —Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2,
• wherein one or more non-adjacent CH2 groups are optionally replaced by R2C═CR2, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, P(═O)(R2), SO, SO2, O, S, or CONR2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, and wherein two adjacent substituents R1 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
• R2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, NO2, Si(R3)3, B(OR3)2, OSO2R3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups are optionally replaced by R3C═CR3, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, P(═O)(R3), SO, SO2, O, S, or CONR3 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, and wherein two adjacent substituents R2 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R3;
• R3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by SO, SO2, O, S and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms;
• and
• Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3.