US 11,993,572 B2
Composition for organic electronic devices
Amir Parham, Frankfurt am Main (DE); Jonas Kroeber, Frankfurt am Main (DE); Tobias Grossmann, Darmstadt (DE); Anja Jatsch, Frankfurt am Main (DE); Christian Eickhoff, Mannheim (DE); and Christian Ehrenreich, Darmstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 16/628,297
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Jul. 2, 2018, PCT No. PCT/EP2018/067734
§ 371(c)(1), (2) Date Jan. 3, 2020,
PCT Pub. No. WO2019/007867, PCT Pub. Date Jan. 10, 2019.
Claims priority of application No. 17179785 (EP), filed on Jul. 5, 2017.
Prior Publication US 2020/0216391 A1, Jul. 9, 2020
Int. Cl. C07D 209/82 (2006.01); C07D 403/04 (2006.01); C07D 403/06 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 407/14 (2006.01); C07D 409/14 (2006.01); H01L 51/00 (2006.01); H01L 51/42 (2006.01); H01L 51/50 (2006.01); H10K 85/60 (2023.01); H10K 30/30 (2023.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01); H10K 101/00 (2023.01)
CPC C07D 209/82 (2013.01) [C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 407/14 (2013.01); C07D 409/14 (2013.01); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 30/353 (2023.02); H10K 50/15 (2023.02); H10K 50/171 (2023.02); H10K 2101/90 (2023.02)] 20 Claims
 
1. A composition comprising at least one compound of the formula (1a) and at least one compound of the formula (2)

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
where the following applies to the symbols and indices used:
V is a bond, C(R0)2, O or S;
v is 0 or 1;
X2 is on each occurrence, identically or differently, CR1 or N;
Z is C(R0)2, NR1, O or S;
N is 0 or 1;
Ar1 and Ar2 are in each case, independently of one another, selected from aromatic or heteroaromatic ring systems from Ar-1 to Ar-15 and Ar-20 to Ar-22

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
Y3 on each occurrence, identically or differently, denotes O, NR#, S or C(#)2, where the radical
R# is on each occurrence, identically or differently, 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 maybe 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,
dashed bond represents the bond to the C atom which carries the respective substituent R;
R0 is on each occurrence, identically or differently, a straight-chain or branched alkyl group having 1 to 4 C atoms or both R0 form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R2;
R is 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, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms and 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 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 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, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms and 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, where the heteroaromatic ring system having 5 to 40 aromatic ring atoms in R1 is dibenzofuran, dibenzothiophene or 9-phenylcarbazole, 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, a branched or cyclic alkyl, alkoxy or thioalkyl group thioalkyl group having 3 to 40 C atoms and 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, an aromatic ring system having 6 to 30 ring atoms and a heteroaromatic ring system having 10 to 30 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; and
with the proviso the substituent R3 in structures Ar-1 to Ar-15 and Ar-20 to Ar-22 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 and an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, in which one or more H atoms maybe 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 and where the heteroaromatic ring system is selected from dibenzofuran, dibenzothiophene or 9-phenylcarbazole;
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.