US 12,193,325 B2
Nitrogen-containing heterocycles for use in OLEDs
Amir Parham, Frankfurt am Main (DE); Jonas Kroeber, Frankfurt am Main (DE); Dominik Joosten, Frankfurt am Main (DE); Aurélie Ludemann, Frankfurt am Main (DE); Tobias Grossmann, Darmstadt (DE); Philipp Stoessel, Frankfurt am Main (DE); and Christian Eickhoff, Mannheim (DE)
Assigned to MERCK PATENT GMBH, (DE)
Appl. No. 16/466,655
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Dec. 4, 2017, PCT No. PCT/EP2017/081292
§ 371(c)(1), (2) Date Jun. 5, 2019,
PCT Pub. No. WO2018/104195, PCT Pub. Date Jun. 14, 2018.
Claims priority of application No. 16202147 (EP), filed on Dec. 5, 2016.
Prior Publication US 2020/0066994 A1, Feb. 27, 2020
Int. Cl. H10K 85/60 (2023.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 471/06 (2006.01); C07D 471/16 (2006.01); C07D 491/06 (2006.01); C07D 491/16 (2006.01); C07D 495/06 (2006.01); C07D 495/16 (2006.01); C07D 495/22 (2006.01); C07D 519/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/657 (2023.02) [C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 471/06 (2013.01); C07D 471/16 (2013.01); C07D 491/06 (2013.01); C07D 491/16 (2013.01); C07D 495/06 (2013.01); C07D 495/16 (2013.01); C07D 495/22 (2013.01); C07D 519/00 (2013.01); C09K 11/06 (2013.01); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 13 Claims
 
1. Compound comprising at least one structure of the (IIIa), (IIIb), (IIIc) or (IIId)

OG Complex Work Unit Chemistry
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)

OG Complex Work Unit Chemistry
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.