US 11,917,906 B2
Compounds that can be used in an organic electronic device
Philipp Stoessel, Frankfurt am Main (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/291,352
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Nov. 4, 2019, PCT No. PCT/EP2019/080036
§ 371(c)(1), (2) Date May 5, 2021,
PCT Pub. No. WO2020/094539, PCT Pub. Date May 14, 2020.
Claims priority of application No. 18204339 (EP), filed on Nov. 5, 2018.
Prior Publication US 2021/0391538 A1, Dec. 16, 2021
Int. Cl. H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/633 (2023.02) [H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A compound usable as active compound in an organic electronic device, characterized in that the compound comprises at least one structure of the formula (I)

OG Complex Work Unit Chemistry
where:
l is an integer in the range from 1 to 8;
R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R1)2, C(═O)N(Ar)2, C(═O)N(R1)2, Si(Ar)3, Si(R1)3, B(Ar)2, B(R1)2, C(═O)Ar, C(═O)R1, P(═O)(Ar)2, P(═O)(R1)2, P(Ar)2, P(R1)2, S(═O)Ar, S(═O)R1, S(═O)2Ar, S(═O)2R1, OSO2Ar, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, 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 R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, —C(═O)O—, —C(═O)NR1—, NR1, P(═O)(R1), —O—, —S—, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; at the same time, two R radicals together may also form a ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; at the same time, it is possible for two Ar radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1) and P(═O)R1;
R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R2)2, C(═O)Ar1, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, B(R2)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent 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, —C(═O)O—, —C(═O)NR2—, NR2, P(═O)(R2), —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems; at the same time, two or more R1 radicals together may form a ring system; at the same time, one or more R1 radicals with a further part of the compound may form a ring system;
Ar1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R2 radicals; at the same time, two Ar1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom may also be joined together via a bridge by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S═O, SO2, N(R2), P(R2) and P(═O)R2;
R2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR3)2, NO2, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R3)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems; at the same time, two or more substituents R2 together may also form a ring system;
R3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen 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; at the same time, two or more substituents R3 together may form a ring system.