US 12,108,665 B2
Materials for organic electroluminescent devices
Amir Parham, Frankfurt am Main (DE); Philipp Stoessel, Frankfurt am Main (DE); and Christian Ehrenreich, Darmstadt (DE)
Assigned to Merck KGaA, Darmstadt (DE)
Appl. No. 17/639,348
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Aug. 31, 2020, PCT No. PCT/EP2020/074184
§ 371(c)(1), (2) Date Mar. 1, 2022,
PCT Pub. No. WO2021/043703, PCT Pub. Date Mar. 11, 2021.
Claims priority of application No. 19194922 (EP), filed on Sep. 2, 2019.
Prior Publication US 2022/0310932 A1, Sep. 29, 2022
Int. Cl. H10K 85/60 (2023.01); C07D 251/20 (2006.01); C07D 251/22 (2006.01); C07D 403/10 (2006.01); C07D 403/14 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 471/04 (2006.01); C07D 471/14 (2006.01); C07D 487/04 (2006.01); C07D 498/04 (2006.01); C07D 513/04 (2006.01); C07D 519/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 251/20 (2013.01); C07D 251/22 (2013.01); C07D 403/10 (2013.01); C07D 403/14 (2013.01); C07D 405/04 (2013.01); C07D 405/14 (2013.01); C07D 471/04 (2013.01); C07D 471/14 (2013.01); C07D 487/04 (2013.01); C07D 498/04 (2013.01); C07D 513/04 (2013.01); C07D 519/00 (2013.01); C09K 11/06 (2013.01); 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 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 14 Claims
 
1. An electronic device comprising at least one compound of formula (1)

OG Complex Work Unit Chemistry
wherein
Z is the same or different at each instance and is O or S;
A is R or Z;
Rb is Ar or a free electron pair;
where, when A=Z, the oxygen or sulfur atom represented by Z is bonded to the carbon atom via a double bond, and Rb is Ar;
in addition, Rb is a free electron pair when A=R, and there is a double bond between the carbon atom to which A is bonded and the nitrogen atom to which Rb is bonded;
Ra is the same or different and is R, or the two Ra groups together with the nitrogen atom and the carbon atom to which they bind form a group of one of the formulae (2), (3) and (4); R radical is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and which may be substituted by one or more R1 radicals;

OG Complex Work Unit Chemistry
where the dotted bond in each case indicates the linkage within formula (1);
X is the same or different at each instance and is CR or N; or two adjacent X groups are a group of the formula (5) or (6)

OG Complex Work Unit Chemistry
where the dotted bonds indicate the linkage of this group in the formula (2), formula (3) or formula (4);
Y is the same or different at each instance and is CR or N;
W is the same or different at each instance and is NAr, O, S or C(R)2;
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;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, Sar′, CN, NO2, OR1, SR1, COOR1, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1,P═(O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2, groups may be replaced by Si(R1)2, C═O, NR1, O, S or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R1 radicals; at the same time, two R radicals together may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
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 R1 radicals;
R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R2)2, C═O, NR2, O, S or CONR2 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, 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; at the same time, two or more R1 radicals together may form an aliphatic ring system;
R2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F.