9,9′-spirobixanthene derivatives for electroluminescent devices

A compound of the formula (1),

• where the following applies to the symbols and indices used:
• X is on each occurrence, identically or differently, CR1 or N;
• where a maximum of one group X per ring stands for N;
• or two adjacent X stand for a group of the following formula (3),
• where ^ indicates the corresponding adjacent groups X in the formula (1);
• X here stands for C if a group Ar or L is bonded to this group X;
• V is on each occurrence, identically or differently, C(R1)2, or NR1;
• Z is on each occurrence, identically or differently, CR1;
• Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R2;
• the group Ar and the adjacent group X, which in this case stands for C, can also be bridged to one another here by a single bond or a divalent group selected from C(R2)2, NR2, O or S;
• L is on each occurrence, identically or differently, a single bond or a divalent group;
• R1 and R2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R3)2, C(═O)Ar1, C(═O)R3, P(═O)(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R3)3, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which can be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups can be replaced by R3C═CR3, C≡C, Si(R3)2, C═O, C═S, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R3, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R3, where two or more adjacent substituents R1 or R2 can optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which can be substituted by one or more radicals R3;
• wherein if R1 or R2 stand for an aromatic or heteroaromatic ring system, this is selected, identically or differently on each occurrence, from benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta- para- or branched quaterphenyl, 1 or 2-naphthyl, pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, anthracene, phenanthrene, pyrene, benzanthracene or combinations of two or three of these groups, each of which can be substituted by one or more radicals R3,
• Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which can be substituted by one or more non-aromatic radicals R3;
• two radicals Ar1 here which are bonded to the same N atom or P atom can also be bridged to one another by a single bond or a bridge selected from N(R3), C(R3)2, O or S;
• R3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R4)2, C(═O)R4, P(═O)(R4)2, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which can be substituted by one or more radicals R4, where one or more non-adjacent CH2 groups can be replaced by R4C═CR4, C≡C, Si(R4)2, C═O, C═S, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R4, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R4, or a combination of these systems, where two or more adjacent substituents R3 can optionally form a monocyclic or polycyclic, aliphatic ring system, which can be substituted by one or more radicals R4;
• R4 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms can be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R4 can form a mono- or polycyclic, aliphatic ring system with one another;
• m is on each occurrence, identically or differently, 0 or 1;
• n is 0, 1, 2, 3, 4 or 5;
• with the proviso that for n=0, at least one substituent R1 is present which is selected from the group consisting of CN, N(Ar1)2, C(═O)Ar1, P(═O)(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R3)3 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R3;
• compounds of the formula (1) in which n=0 and four substituents R1 stand, identically or differently, for an optionally substituted carbazole or diphenylamine, which is in each case bonded to the skeleton via the nitrogen atom, are excluded.