US 12,336,428 B2
Materials for electronic devices
Amir Hossain Parham, Darmstadt (DE); Irina Martynova, Griesheim (DE); Anja Jatsch, Darmstadt (DE); Thomas Eberle, Darmstadt (DE); Jonas Valentin Kroeber, Darmstadt (DE); and Christof Pflumm, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on Nov. 20, 2023, as Appl. No. 18/513,954.
Application 18/513,954 is a continuation of application No. 16/543,685, filed on Aug. 19, 2019, granted, now 11,856,849.
Application 16/543,685 is a continuation of application No. 15/027,381, granted, now 10,529,930, issued on Jan. 7, 2020, previously published as PCT/EP2014/002496, filed on Sep. 16, 2014.
Claims priority of application No. 13004837 (EP), filed on Oct. 8, 2013.
Prior Publication US 2024/0130231 A1, Apr. 18, 2024
Int. Cl. H01L 51/54 (2006.01); A61K 41/00 (2020.01); A61N 5/06 (2006.01); C07D 403/08 (2006.01); C07D 403/10 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 491/048 (2006.01); C07D 495/14 (2006.01); C07F 5/02 (2006.01); C07F 7/08 (2006.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 85/30 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [A61K 41/00 (2013.01); A61N 5/0616 (2013.01); A61N 5/0621 (2013.01); C07D 403/08 (2013.01); C07D 403/10 (2013.01); C07D 403/14 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 491/048 (2013.01); C07D 495/14 (2013.01); C07F 5/025 (2013.01); C07F 7/0814 (2013.01); C07F 15/0033 (2013.01); C07F 15/0086 (2013.01); C09K 11/025 (2013.01); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); A61N 2005/0653 (2013.01); H10K 50/11 (2023.02); H10K 85/342 (2023.02); H10K 85/631 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02); Y02E 10/549 (2013.01)] 22 Claims
 
1. Compound of the general formula (1)

OG Complex Work Unit Chemistry
where the following applies to the symbols and indices used:
A and A′ are, identically or differently from one another, an aromatic or heteroaromatic ring having 5 or 6 ring atoms, which may be substituted by one or more radicals R1, which may be independent of one another;
ETG is an organic electron-transporting group (ETG) from the group of electron-deficient heteroaromatic groups, where the ETG is selected from the group consisting of triazines, pyrimidines, pyrazines, pyrazoles, pyridazines, quinoles, isoquinolines, thiazoles, benzothiazoles, oxazoles, benzoxazoles, imidazoles, benzimidazoles, and pyridines, and where the group ETG may be substituted by one or more radicals R1, which are independent of one another;
Z is a single bond or a divalent group; if Z is a single bond, the group ETG is then bonded directly to the carbon atom of ring A;
V is O;
W is a single bond;
m is 1;
n is 1,
where m=n;
Ar3 is an aromatic or heteroaromatic ring or ring system having 5 to 30 ring atoms, where the ring or ring system may in each case be substituted by one or more radicals R2 where two or more radicals R2 do not form a ring closure with one another;
R1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R2, where one or more non-adjacent CH2 groups may be replaced by R2C═CR2, C═C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, 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, or 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 R2, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of two or more of these groups or a crosslinkable group Q; two or more adjacent radicals R1 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred for two or more adjacent radicals R1 not to form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by 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, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups; two or more adjacent radicals R2 here do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another
R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R3 here do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
p is 1;
R4 is, identically or differently on each occurrence, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or a combination of two or more of these groups.