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US 12,178,124 B2Granted
Compounds that can be used in an organic electronic device as active compounds
AssigneeMerck KGaA
InventorPhilipp Stoessel
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds that can be used in an organic electronic device as an active compound, in particular for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention, and to electronic devices comprising same.
Claims13
A compound usable with preference as active compound in an organic electronic device, wherein the compound has at least one aromatic or heteroaromatic ring system which has 5 to 60 carbon atoms and is fused to an aliphatic polycyclic ring system having at least 3 rings,
- wherein the aliphatic polycyclic ring system which has at least 3 rings and is fused to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms forms a substructure of the formulae (N-1) to (N-6)
- wherein
- R1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R2)2, C(═O)Ar1, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, B(OR2)2, Si(Ar1)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 or alkynyl 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, Ge(R2)2, Sn(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 40 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 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- Ar1 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, nonaromatic R2 radicals;
- at the same time, it is possible for two Ar1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another 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 H, D, F, Cl, Br, I, CN, B(OR3)2, NO2, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R3)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, 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, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C═C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —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 40 aromatic ring atoms and may be substituted in each case by one or more R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems;
- at the same time, two or more, adjacent substituents R2 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
- R3 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 having 5 to 30 aromatic ring atoms 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 adjacent substituents R3 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
- the index s is 0, 1, 2, 3, 4, 5 or 6;
- the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
- the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
- and the dotted lines represent the bonds of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the aliphatic polycyclic ring system having at least 3 rings is fused, and
- wherein the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the aliphatic polycyclic ring system having at least 3 rings is fused forms a substructure of the formulae (Ar-2) to (Ar-11) and (Ar-13) to (Ar-66)
- wherein X′ is N or CR1;
- Y′ is selected from O, S, C(R1)2, Si(R1)2, NR1 and NAr1;
- U is selected from O, S, C(R1)2, N(R1), B(R1), Si(R1)2, C═O, S═O, SO2, P(R1) and P(═O)R1;
- R1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R2)2, C(═O)Ar1, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, B(OR2)2, Si(Ar1)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 or alkynyl 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, Ge(R2)2, Sn(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 40 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 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- Ar1 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, nonaromatic R2 radicals;
- at the same time, it is possible for two Ar1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another 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 H, D, F, Cl, Br, I, CN, B(OR3)2, NO2, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R3)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, 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, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C═C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —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 40 aromatic ring atoms and may be substituted in each case by one or more R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems;
- at the same time, two or more, adjacent substituents R2 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
- R3 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 having 5 to 30 aromatic ring atoms 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 adjacent substituents R3 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
- and the aliphatic polycyclic ring system having at least 3 rings binds to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the respective positions identified by o to form a ring.
22 more elements
Dependencies are inferred from the claim text.