US 12,441,715 B2
Materials for organic electroluminescent devices
Amir Hossain Parham, Darmstadt (DE); Thomas Eberle, Darmstadt (DE); Anja Jatsch, Darmstadt (DE); Tobias Grossmann, Darmstadt (DE); Jonas Valentin Kroeber, Darmstadt (DE); Elvira Montenegro, Darmstadt (DE); and Caroline Wern, Darmstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on Jun. 7, 2024, as Appl. No. 18/736,626.
Application 18/736,626 is a continuation of application No. 17/564,289, filed on Dec. 29, 2021, granted, now 12,065,431.
Application 18/736,626 is a continuation of application No. 16/081,456, granted, now 11,608,327, previously published as PCT/EP2017/000154, filed on Feb. 6, 2017.
Claims priority of application No. 16158460 (EP), filed on Mar. 3, 2016; and application No. 16159829 (EP), filed on Mar. 11, 2016.
Prior Publication US 2024/0336600 A1, Oct. 10, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/50 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 495/04 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/18 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 101/10 (2023.01)
CPC C07D 405/04 (2013.01) [C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 495/04 (2013.01); C09K 11/06 (2013.01); H10K 50/11 (2023.02); H10K 50/18 (2023.02); H10K 85/626 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/1092 (2013.01); H10K 50/15 (2023.02); H10K 50/181 (2023.02); H10K 2101/10 (2023.02)] 15 Claims
 
1. A compound of formula (1)

OG Complex Work Unit Chemistry
where the symbols used are as follows:
X is O or S;
Y is S;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals, where Ar comprises only aryl groups or heteroaryl groups having up to 15 aromatic ring atoms and no carbazolyl groups as heteroaryl groups, and no 9,9′-spirobifluorene groups and wherein Ar does not comprise an anthracene group and wherein Ar as well as the substituents R bonded to Ar do not comprise a fluorene group;
R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R4)2, C(═O)Ar1, C(═O)R4, P(═O) (Ar1)2, P(Ar1)2, B(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by R4C═CR4, C═O, C═S, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals; at the same time, it is optionally possible for two R substituents bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic aliphatic ring system which may be substituted by one or more R4 radicals;
R1 is the same or different at each instance and is selected from the group consisting of H, D, F, CI, I, CN, NO2, N(Ar1)2, N(R4)2,C(═O)Ar1, C(═O)R4, P(═O) (Ar1)2, P(Ar1)2, B(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by R4C═CR4, C═O, C═S, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals; at the same time, it is optionally possible for two R1 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic or heteroaromatic ring system which may be substituted by one or more R4 radicals or for two R1 and R3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R4 radicals;
R2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R4)2, C(═O)Ar1, C(═O)R4, P(═O) (Ar1)2, P(Ar1)2, B(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by R4C═CR4, C═O, C═S, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals; at the same time, it is optionally possible for two R2 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic or heteroaromatic ring system which may be substituted by one or more R4 radicals;
R3 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R4)2, C(═O)Ar1, C(═O)R4, P(═O) (Ar1)2, P(Ar1)2, B(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R4 radicals, where one or more nonadjacent CH2 groups may be replaced by R4C═CR4, C═O, C═S, C═NR4, P(═O)(R4), SO, SO2, NR4, O, S or CONR4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R4 radicals; at the same time, it is optionally possible for two R1 and R3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R4 radicals;
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 R4 radicals; at the same time, two Ar1 radicals bonded to the same phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R4), C(R4)2, O and S;
R4 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R5)2, C(═O)R5, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R5 radicals, where one or more nonadjacent CH2 groups may be replaced by R5C═CR5, C═O, C═S, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R5 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals; at the same time, it is optionally possible for two R4 substituents bonded to the same carbon atom or adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R5 radicals;
R5 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 adjacent R5 substituents together to form a mono- or polycyclic, aliphatic ring system;
where, in one instance, the nitrogen atom is bonded to the corresponding carbon atom in place of R1 or R3.