US 12,435,070 B2
Composition for organic electronic devices
Amir Parham, Frankfurt am Main (DE); Jonas Kroeber, Frankfurt am Main (DE); Tobias Grossmann, Shanghai (CN); Anja Jatsch, Darmstadt (DE); Christian Eickhoff, Darmstadt (DE); and Christian Ehrenreich, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on Dec. 29, 2022, as Appl. No. 18/090,711.
Application 18/090,711 is a continuation of application No. 16/628,280, granted, now 11,591,320, previously published as PCT/EP2018/067732, filed on Jul. 2, 2018.
Claims priority of application No. 17179775 (EP), filed on Jul. 5, 2017; and application No. 17195036 (EP), filed on Oct. 5, 2017.
Prior Publication US 2023/0150987 A1, May 18, 2023
Int. Cl. H01L 51/50 (2006.01); C07D 405/14 (2006.01); H10K 71/10 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 101/10 (2023.01)
CPC C07D 405/14 (2013.01) [H10K 71/10 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 50/11 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A composition comprising at least one compound of the formula (1b) or (1c) and at least one compound of the formula (2a)

OG Complex Work Unit Chemistry
where the following applies to the symbols and indices used:
X is on each occurrence, identically or differently, CR0 or N, with the proviso that at least one group X stands for N;
Y is selected from O or S;
L is on each occurrence, identically or differently a single bond and is linked in position 6 of the dibenzofuran ring or dibenzothiophene ring;
Ar1, Ar2 are in each case, independently of one another on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3;
Ar3 is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3;
Ar4 and Ar5 are in each case, independently of one another, an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3 with the proviso that Ar4 and Ar5 cannot simultaneously be phenyl;
R0, R, are selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R2)2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R2)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, which may in each case be substituted by one or more radicals R2, where one or more non-adjacent CH2 groups may be replaced by R2C═CR2, Si(R2)2, C═O, C═S, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 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 R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2; two substituents R0 and/or 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, which may be substituted by one or more radicals R2;
R1 is selected on each occurrence, identically or differently, from the group consisting of D, F, an alkyl group having 1 to 40 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2;
R2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar)2, NH2, N(R3)2, C(═O)Ar, C(═O)H, C(═O)R3, P(═O)(Ar)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by HC═CH, R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NH, NR3, O, S, CONH or CONR3 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 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of these systems, where two or more adjacent substituents R2 may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R3;
R3 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 R3 may form a mono- or polycyclic, aliphatic ring system with one another;
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 non-aromatic radicals R3; two radicals Ar which are bonded to the same N atom, P atom or B atom may also be bridged to one another by a single bond or a bridge selected from N(R3), C(R3)2, O or S, and
n and m, independently of one another, denote 0, 1, 2 or 3;
p and o in each case, independently of one another, denote 0, 1, 2, or 3;
q and t in each case, independently of one another, denote 0, 1, 2, 3, or 4 and r and s in each case, independently of one another, denote 0, 1, 2, or 3.