US 12,077,541 B2
Compounds for electronic devices
Ilona Stengel, Darmstadt (DE); Florian Maier-Flaig, Weinheim (DE); Philipp Harbach, Muehltal (DE); Elvira Montenegro, Weinheim (DE); and Aurélie Ludemann, Frankfurt am Main (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 16/979,259
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Mar. 6, 2019, PCT No. PCT/EP2019/055541
§ 371(c)(1), (2) Date Sep. 9, 2020,
PCT Pub. No. WO2019/170729, PCT Pub. Date Sep. 12, 2019.
Claims priority of application No. 18161099 (EP), filed on Mar. 9, 2018.
Prior Publication US 2020/0399251 A1, Dec. 24, 2020
Int. Cl. C07D 487/04 (2006.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01)
CPC C07D 487/04 (2013.01) [H10K 85/631 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 50/15 (2023.02)] 20 Claims
 
1. A compound according to formula (I) (II) or (III)

OG Complex Work Unit Chemistry
where the following applies to the variables occurring:
Z is on each occurrence, identically or differently, CR1 or N;
ArL is selected, identical or differently from benzene, biphenyl, terphenyl, and fluorene, where each of the above-mentioned groups may be substituted by one or more radicals R2;
Ar1 is on each occurrence, identically or differently, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3;
R1, R2, R3 is selected, identically or differently at each occurrence, from H, D, F, C(═O)R4, CN, Si(R4)3, N(R4)2, P(═O)(R4)2, OR4, S(═O)R4, S(═O)2R4, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R1, R2 and/or R3 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R4C═CR4—, —C≡C—, Si(R4)2, C═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(═O)(R4), —O—, —S—, SO or SO2;
with the proviso that in formula (I), a maximum of one group R3 is N(R4)2;
R4 is selected, identically or differently at each occurrence, from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R4 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R5, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R5C═CR5—, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5, NR5, P(═O)(R5), —O—, —S—, SO or SO2;
R5 is selected, identically or differently at each occurrence, from H, D, F, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms, or heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R5 may be connected to each other to form a ring; and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN;
i is, identically or differently on each occurrence, 1, 2, 3, 4 or 5.