US 12,329,026 B2
Materials for organic light emitting devices
Amir Hossain Parham, Darmstadt (DE); Anja Jatsch, Darmstadt (DE); Thomas Eberle, Darmstadt (DE); Tobias Grossmann, Darmstadt (DE); Jonas Valentin Kroeber, Darmstadt (DE); and Lars Dobelmann-Mara, Darmstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on Feb. 19, 2024, as Appl. No. 18/444,810.
Application 18/444,810 is a continuation of application No. 17/994,034, filed on Nov. 25, 2022, granted, now 11,991,924.
Application 17/994,034 is a continuation of application No. 16/808,515, filed on Mar. 4, 2020, granted, now 11,626,561.
Application 16/808,515 is a continuation of application No. 15/308,749, granted, now 10,622,565, previously published as PCT/EP2015/000705, filed on Apr. 1, 2015.
Claims priority of application No. 14001573 (EP), filed on May 5, 2014.
Prior Publication US 2024/0268222 A1, Aug. 8, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/50 (2006.01); C07D 251/24 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 405/04 (2006.01); C07D 405/10 (2006.01); C07D 405/14 (2006.01); C07D 407/14 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 487/04 (2006.01); C07D 491/06 (2006.01); C07D 495/04 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/16 (2023.01); H10K 50/18 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 251/24 (2013.01); C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 405/04 (2013.01); C07D 405/10 (2013.01); C07D 405/14 (2013.01); C07D 407/14 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 487/04 (2013.01); C07D 491/06 (2013.01); C07D 495/04 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/615 (2023.02); H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/121 (2023.02); H10K 50/16 (2023.02); H10K 50/18 (2023.02); H10K 2101/10 (2023.02)] 12 Claims
 
1. A compound of formula (1a) or (2a),

OG Complex Work Unit Chemistry
where the following applies to the symbols and indices used:
X is on each occurrence, identically or differently, CR or N, with the proviso that at least one group X stands for N;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
Y1 is O or S
Y2 is NR′;
R′ is a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R1, or is a phenylene group which is substituted with a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R1;
L is a single bond;
R is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R1)2, C(═O)Ar1, C(═O)R1, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, Si(R1)2, C═O, C═S, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1; two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system here, which may be substituted by one or more radicals R1;
Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R1; two radicals Ar1 which are bonded to the same N atom, P atom or B atom may also be bridged to one another here by a single bond or a bridge selected from N(R1), C(R1)2, O or S;
R1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H 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; two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic ring system with one another here.