US 12,219,874 B2
Materials for electronic devices
Elvira Montenegro, Weinheim (DE); Teresa Mujica-Fernaud, Darmstadt (DE); Florian Maier-Flaig, Weinheim (DE); Frank Voges, Bad Duerkheim (DE); and Christian Wirges, Weiterstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/415,990
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Dec. 17, 2019, PCT No. PCT/EP2019/085517
§ 371(c)(1), (2) Date Jun. 18, 2021,
PCT Pub. No. WO2020/127176, PCT Pub. Date Jun. 25, 2020.
Claims priority of application No. 18214579 (EP), filed on Dec. 20, 2018.
Prior Publication US 2022/0109116 A1, Apr. 7, 2022
Int. Cl. C07D 307/91 (2006.01); C07D 333/76 (2006.01); C07D 405/12 (2006.01); C07D 409/10 (2006.01); C07D 409/14 (2006.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC H10K 85/6574 (2023.02) [C07D 307/91 (2013.01); C07D 333/76 (2013.01); C07D 405/12 (2013.01); C07D 409/10 (2013.01); C07D 409/14 (2013.01); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 50/18 (2023.02)] 18 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
where:
FL is a group of formulae (FL-1)

OG Complex Work Unit Chemistry
where the dotted bond is the bond to the rest of formula (I);
Z is identically or differently at each occurrence, selected from CR1 and N;
Y is C if a group —[Ar2]n—N(Ar3)(Ar4) or —[Ar1]m-FL is bonded in this position; and Y is in all other cases selected, identically or differently at each occurrence, from CR3 and N;
X is O or S;
Ar1 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R4, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R4;
Ar2 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R5, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R5;
A corresponds to the following formula

OG Complex Work Unit Chemistry
which is bonded via the dotted line;
Ar3 and Ar4 are, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R6, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R6;
k is 0 which means that T does not occur and the groups Ar3 and Ar4 are not connected;
R1 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O) R7, S(═O)2R7, 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 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 are in each case substituted by radicals R7, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
R2 is selected, identically or differently at each occurrence, from straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 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 the said alkyl, groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R7;
R3 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O)R7, S(═O)2R7, 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 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 are in each case substituted by radicals R7, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
R4 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O)R7, S(═O)2R7, 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 are in each case substituted by radicals R7, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
R5 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O)R7, S(═O)2R7, 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 the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R7, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
R6 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O)R7, S(═O)2R7, 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 R6 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 are in each case be substituted by radicals R7, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
R7 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R8, CN, Si(R8)3, N(R8)2, P(═O)(R8)2, OR8, S(═O)R8, S(═O)2R8, 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 the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case be substituted by radicals R8, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R8C═CR8—, —C≡C—, Si(R8)2, C═O, C═NR8, —C(═O)O—, —C(═O)NR8—, NR8, P(═O)(R8), —O—, —S—, SO or SO2;
R8 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, 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; 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;
m is 1, 2, 3, or 4;
n is 0, 1, 2, 3, or 4.