Indolo[3.2.1-jk]carbazole-6-carbonitrile derivatives as blue fluorescent emitters for use in OLEDS

A compound comprising at least one structure of the formula (I),

• where the symbols and indices used are as follows:
• X is the same or different at each instance and is N, C—CN, C—Y—Ry or CRb;
• Y is the same or different at each instance and is CO, P(═O)Ra, SO, SO2, C(O)O, C(S)O, C(O)S, C(═O)NRa, C(═O)NAr;
• R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(Re)2, C(═O)N(Ar)2, C(═O)N(Re)2, C(Ar)3, C(Re)3, Si(Ar)3, Si(Re)3, B(Ar)2, B(Re)2, C(═O)Ar, C(═O)Re, P(═O)(Ar)2, P(═O)(Re) 2, P(Ar)2, P(Re)2, S(═O)Ar, S(═O)Re, S(—O)2Ar, S(—O)2Re, OSO2ArRe, 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 each be substituted by one or more Re radicals, where one or more nonadjacent CH2 groups may be replaced by ReC═CRe, C≡C, Si(Re)2, C═O, C═S, C═Se, C═NRe, —C(═O)O—, —C(—O)Ne—, NRe, P(═O)(Re), —O—, —S—, SO or SO2, 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 Re radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more Re radicals, or an arylthio or heteroarylthio group which has 5 to 60 aromatic ring atoms and may be substituted by one or more Re radicals, or a diarylamino, arylheteroarylamino, diheteroarylamino group which has 5 to 60 aromatic ring atoms and may be substituted by one or more Re radicals, or an arylalkyl or heteroarylalkyl group which has 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl radical and may be substituted by one or more Re radicals;
• at the same time, any R radical may form a ring system 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 Re 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(Re), C(Re)2, Si(Re)2, C═O, C═NRe, C═C(Re)2, O, S, S═O, SO2, N(Re), P(Re) and P(═O)Re;
• Ra, Rb, Rc, Rd, Re is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar′)2, N(R1)2, C(═O)N(Ar′)2, C(═O)N(R1)2, C(Ar′)3, C(R1)3, Si(Ar′)3, Si(R1)3, B(Ar′)2, B(R1)2, C(═O)Ar′, C(═O)R1, P(═O)(Ar′)2, P(═O)(R1)2, P(Ar′)2, P(R1)2, S(═O)Ar′, S(═O)R1, S(═O)2Ar′, S(═O)2R1, OSO2Ar′, OSO2R1, 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 R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C═CR1, C═C, Si(R1)2, C═O, C═S, C═Se, C═NR1, —C(═O)O—, —C(═O)NR1—, NR1, P (═O) (R1), —O—, —S—, SO or SO2, 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 R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals;
• at the same time, two Ra, Rb, Rd, Re radicals may also form a ring system together or with a further group;
• Ry is the same or different at each instance and is C(Ar′)3, C(R1)3, Si(Ar′)3, Si(R1)3, N(Ar′)2, N(R1)2, 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 R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C═CR1, C═C, Si(R1)2, C═O, C═S, C═Se, C═NR1, —C(═O)O—, —C(═O)NR1—, NR1, P(═O)(R1), —O—, —S—, SO or SO2, where any CH2 group bonded to the Y radical may not be replaced by C═O, C═S, C═Se, C—NR1, —C(═O)O—, —C(═O)NR1—, P(═O)(R1), SO or SO2, where any CH2 group bonded to the Y radical may optionally not be replaced by Si(R1)2, C═O, C═S, C═Se, C═NR1, —C(═O)O—, —C(═O)NR1—, NR1, P(═O)(R1), —O—, —S—, SO or SO2, 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 R1 radicals;
• at the same time, two Ry radicals may also form a ring system with one another, or one Ry radical together with one Ra, Rb, Rc, Rc, Re radical;
• 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 R1 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(R1), C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1) and P(═O) R1;
• R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar″)2, N(R2)2, C(═O)Ar″, C(═O) R2, P(═O)(Ar″)2, P(Ar″)2, B(Ar″)2, B(R2)2, C(Ar″) 3, C(R2)3, Si(Ar″)3, Si(R2)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 R2 radicals, where one or more nonadjacent CH2 groups may be replaced by —R2C—CR2—, —C═C—, Si(R2)2, C═O, C—S, C═Se, C═NR2, —C(═O)O—, —C(═O)NR2—, NR2, P(═O)(R2), —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
• at the same time, two or more, R1 radicals together may form a ring system;
• at the same time, one or more R1 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 R2 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(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S—O, SO2, N(R2), P(R2) and P(═O)R2;
• R2 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 R2 together may form a ring system;
• wherein two Re radicals together with the further groups to which the two Re radicals bind form a fused ring, an aliphatic or heteroaliphatic ring having 3 to 20 ring atoms or an aromatic or heteroaromatic ring having 5 to 13 ring atoms.