US 12,250,880 B2
Compounds for electronic devices
Amir Parham, Frankfurt am Main (DE); Jonas Kroeber, Frankfurt am Main (DE); Jens Engelhart, Darmstadt (DE); Anja Jatsch, Frankfurt am Main (DE); Christian Eickhoff, Mannheim (DE); Christian Ehrenreich, Darmstadt (DE); and Jens Kaiser, Frankfurt am Main (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/298,555
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Nov. 28, 2019, PCT No. PCT/EP2019/082821
§ 371(c)(1), (2) Date May 29, 2021,
PCT Pub. No. WO2020/109434, PCT Pub. Date Jun. 4, 2020.
Claims priority of application No. 18209646 (EP), filed on Nov. 30, 2018.
Prior Publication US 2022/0013730 A1, Jan. 13, 2022
Int. Cl. H10K 85/60 (2023.01); C07D 471/04 (2006.01); C07D 471/14 (2006.01); C07D 519/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/657 (2023.02) [C07D 471/04 (2013.01); C07D 471/14 (2013.01); C07D 519/00 (2013.01); C09K 11/06 (2013.01); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02); H10K 2101/10 (2023.02)] 19 Claims
 
1. A compound of a formula (I)

OG Complex Work Unit Chemistry
where
G is the same or different at each instance and is selected from a group of the formula (G-1)

OG Complex Work Unit Chemistry
attached via the dotted bond,
where, in formula (G-1), W is the same or different at each instance and is CR2 or N; or one or more units from any two adjacent W groups are the same or different at each instance and are selected from units of the formulae (W-1) to (W-2)

OG Complex Work Unit Chemistry
where the dotted bonds represent the bonds to the rest of the formula (G-1);
where U is the same or different at each instance and is selected from O, S, NR3 and C(R3)2; and
where, in formula (W-1) to (W-2), V is the same or different at each instance and is CR2 or N; or one or more units from any two adjacent V groups are the same or different at each instance and are selected from units of the formulae (V-1) to (V-2)

OG Complex Work Unit Chemistry
where the dotted bonds represent the bonds to the rest of the formulae (W-1) to (W-2);
where Z is the same or different at each instance and is CR2 or N;
X, when no G or Tis bonded thereto, is the same or different at each instance and is N or CR1; and X, when G or Tis bonded thereto, is C;
T is a single bond that connects the X groups in question;
R1 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, 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 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R1 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R4 radicals; and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may 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;
R2 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, 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 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R2 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R4 radicals; and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may 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;
R3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, Si(R4)3, N(R4)2, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon 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 R3 radicals may be joined to one another and may form a ring; where the alkyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R4 radicals;
R4 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, 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 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R5 radicals; and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups may 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 the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R5 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN;
k is 0 or 1, where, when k is 0, T is absent, and the X groups in question are not bonded to one another;
m, n, o is the same or different at each instance and is selected from 0 and 1, where at least one of the indices m, n and o must be 1;
where at least one X group in at least one of the rings to which a G group is bonded is N.