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US 12,193,325 B2Granted
Nitrogen-containing heterocycles for use in OLEDs
AssigneeMerck Patent GmbH
InventorsAmir Parham, Jonas Kroeber, Dominik Joosten, Aurélie Ludemann, Tobias Grossmann, Philipp Stoessel, Christian Eickhoff
Life of this patent
Estimating the term…
Abstract
The present invention describes nitrogen-containing heterocycles substituted by carbazole groups, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.
Claims13
Compound comprising at least one structure of the (IIIa), (IIIb), (IIIc) or (IIId)
- where in Formula (IIIa), (IIIb), (IIIc), and (IIId) W1 is SO, SO2, Si(R1)2 or C═O;
- where in Formulae (IIIa), (IIIb), (IIIc), and (IIId), the symbols used are as follows:
- X is the same or different at each instance and is N or CR1;
- X1 is N or CR1 where at least one X1 group is N;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, OAr1OR2, SAr1, SR2, C(═O)Ar1, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)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 group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, and where one or more nonadjacent CH2 groups may be replaced by -R2C═CR2-, —C≡C—, Si(R2)2, C═O, C═S, 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 and may be substituted in each case 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;
- at the same time, two or more R′ substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with the proviso that a substituent R1 does not form a ring system with a substituent R2;
- 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 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 H, D, F, Cl, Br, I, CN, B(OR3)2, OR3, SR3, NO2, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R13)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O) R3, S(═O)2R3, 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, and where one or more nonadjacent CH2 groups may be replaced by -R3C═CR3-, —C≡C—, Si(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;
- at the same time, two or more R2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with the proviso that a substituent R2 does not form a ring system with a substituent R1;
- 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, it is possible for two or more R3 substituents together to form a mono- or polycyclic, aliphatic ring system;
- where m is 4;
- wherein, if two adjacent substituents R1 form an aromatic or heteroaromatic ring system, at least one such ring system is selected from the groups of formula (DB-1)
- where X2 is the same or different at each instance and is N or CR2, Y1 is O, S, C(R2)2, or NR2 and the dotted lines represent direct bonds to the formula (IIIa), (IIIb), (IIIc), or (IIId);
- wherein if Y1 in DB-1 is C(R2)2, the R2 in the C(R2)2, in DB-1 does not form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.
13 more elements
Dependencies are inferred from the claim text.