Materials for organic electroluminescent devices

A compound of the formula (1), formula (2), formula (3), or formula (4),

• wherein
• Y is C if a group X2 is bonded to this group Y, or is identically or differently on each occurrence CR or N if no group X2 is bonded to this group Y;
• E is a single bond or a divalent bridge selected from N(R1), B(R1), C(R1)2, O, Si(R1)2, C═NR1, C═C(R1)2, S, S═O, SO2, P(R1), and P(═O)R1;
• X1, X2 are identically or differently on each occurrence a divalent bridge selected from N(R1), B(R1), O, C(R1)2, Si(R1)2, C═NR', C═C(R1)2, S, S═O, SO2, P(R1), and P(═O)R1;
• with the proviso that X1 and X2 do not simultaneously stand for O;
• R, R1 are identically or differently on each occurrence H, D, F, Cl, Br, I, N(R2)2, N(Ar)2, C(═O)Ar, P(═O)Ar2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups are optionally replaced by R2C═CR2, C≡C, Si(R2)2, C═O, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S, or CONR2, and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R2, or a combination of these systems;
• two or more substituents R together with the atoms to which they are bonded, or two substituents R1 together with the atom to which they are bonded, optionally define a mono- or polycyclic, aliphatic or aromatic ring system;
• Ar is identically or differently on each occurrence an aromatic or heteroaromatic ring system, optionally substituted by one or more radicals R3;
• R2 is identically or differently on each occurrence H, D, F, Cl, Br, I, N(R3)2, N(Ar)2, C(═O)Ar, P(═O)Ar2, S(═O)Ar, S(═O)2Ar, CR3═CR3Ar, CN, NO2, Si(R3)3, B(OR3)2, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, where one or more non-adjacent CH2 groups are optionally replaced by R3C═CR3, C≡C, Si(R3)2, C═O, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3, and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R3, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R3, or a combination of these systems;
• R3 is identically or differently on each occurrence H, D, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aryl or heteroaryl group having 5 to 40 ring atoms, or a combination of these groups;
• n, m are identically or differently on each occurrence 0 or 1, with the proviso that n+m=1 or 2;
• wherein at least one group R and/or R1 is present and is a group of formula (5),
• where the dashed bond indicates the linking of the group of the formula (5), R2 has the meanings given above and furthermore:
• X is C if the group Ar1 or the remainder of the molecule is bonded to this X, and is otherwise identically or differently on each occurrence CR2 or N;
• Ar1 is a divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R2;
• p is identically or differently on each occurrence 0 or 1;
• q, r is identically or differently on each occurrence 0, 1, or 2.