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US 10,377,766 B2Granted
Heterocyclic compounds with benzo(c)coumarin-structures
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Teresa Mujica-Fernaud, Thomas Eberle, Anja Jatsch, Jonas Valentin Kroeber, Tobias Grossmann
Life of this patent
Estimating the term…
Abstract
The invention relates to heterocyclic compounds with benzo[c]coumarin structures and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
Claims23
A compound having a molecular weight of not more than 5000 g/mol comprising structures of the formula (I)
- where the symbols used are as follows:
- R is the same or different at each instance and is H, D, F, Cl, Br, I, C(═O)Ar1, CN, Si(R2)3, B(OR2)2, a straight-chain alkyl, or alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or a branched or cyclic alkyl, or alkoxy group having 3 to 10 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more hydrogen atoms may be replaced by D or F or an aromatic or heteroaromatic ring system which has 5 to 30 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 30 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 adjacent R substituents may also form a mono- or polycyclic aliphatic or aromatic ring system with one another, with the ring to which R is bonded, with a ring to which R is adjacent or with an R1 radical;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, C(═O)Ar1, CN, Si(R2)3, B(OR2)2, a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms, which are each substituted by one or more R2 radicals, where one or more hydrogen atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms, each of which may be substituted by one or more R2 radicals;
- at the same time, two or more adjacent R1 substituents may also form a mono- or polycyclic aliphatic or aromatic ring system with one another, with the ring to which R1 is bonded, with a ring to which R1 is adjacent or with an R radical;
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)Ar1, P(═O)(Ar1)2, S(═O)Ar1, S(═O)2Ar1, CN, NO2, Si(R3)3, B(OR3)2, OSO2R3, 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 C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, P(═O)(R3), SO, SO2, O, S or CONR3 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, each of which may be substituted 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 adjacent R2 substituents may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- 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, it is also possible for two Ar1 radicals bonded to the same phosphorus atom to be joined to one another by a single bond or a bridge selected from B(R3), C(R3)2, Si(R3)2, C═O, C═NR3, C═C(R3)2, O, S, S═O, SO2, N(R3), P(R3) and P(═O)R3;
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F;
- at the same time, two or more adjacent R3 substituents may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- m, n are each independently 0, 1, 2, 3 or 4;
- with the proviso that
- the sum of m and n is not less than 1;
- at least one of the R and/or R1 groups in formula (I) is at least one L group;
- and
- L is selected from the group consisting of Formula (L-1) to (L-42)
- wherein the dashed bond marks the attachment position,
- g is 0, 1, 2, 3, 4 or 5,
- h is 0, 1, 2, 3 or 4,
- j is 0, 1, 2 or 3,
- Y is O, S or N(R1),
- k is 0, 1 or 2,
- Ar2, Ar3, Ar4 are each independently an aryl group of 6 to 40 carbon atoms or a heteroaryl group of 3 to 40 carbon atoms, each of which is optionally substituted by one or more R1;
- p is 0 or 1,
- X is a bond, CR12, C═O, N(R1), B(R1), SiR12, O or S.
24 more elements
Dependencies are inferred from the claim text.