Back to results
US 11,309,497 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Tobias Grossmann, Thomas Eberle, Anja Jatsch, Jonas Valentin Kroeber, Lars Dobelmann-Mara
Life of this patent
Estimating the term…
Abstract
The present invention describes dibenzofuran and dibenzothiophene derivatives, in particular for use as triplet matrix materials in organic electroluminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising same.
Claims9
An organic electroluminescent device comprising in the emissive layer a mixture of a phosphorescent emitter and a compound of the formula (1),
- where the following applies to the symbols used:
- A is on each occurrence, identically or differently, CR1;
- Y1 is O or S;
- L is on each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R1;
- HetAr is a group of the formula (2), (3) or (4),
- where the dashed bond represents the linking of this group;
- X is on each occurrence, identically or differently, CR2 or N, with the proviso that at least one symbol X stands for N;
- N1 is a group of formula (6),
- where the dashed bond represents the linking of this group;
- precisely two adjacent groups W together stand for a group of the formula (7), and the remaining groups W stand, identically or differently on each occurrence, for CR1 or N,
- where the dashed bonds indicate the linking of this group;
- Y2 are, identically or differently on each occurrence, O, NR4, S, C(R4)2, Si(R4)2, BR4 or C═O, where the radical R4 which is bonded to N is not equal to H for the groups of formulae (7) and (8);
- R1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R5, where one or more H atoms may be replaced by D, F, or CN or, an aromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R5;
- R2, R4 are selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R5, where one or more H atoms may be replaced by D, F, or CN or, 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 R5;
- two adjacent substituents R4 may form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R5;
- R5 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 or an aromatic or heteroaromatic ring system having 5 to 30 aromatic 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 R5 here may form an aliphatic ring system with one another.
14 more elements
A compound of formula (1),
- where the following applies to the symbols used:
- A is on each occurrence, identically or differently, CR1;
- Y1 is O or S;
- L is on each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R1;
- HetAr is a group of the formula (2), (3) or (4),
- where the dashed bond represents the linking of this group;
- X is on each occurrence, identically or differently, CR2 or N, with the proviso that at least one symbol X stands for N;
- N1 is a group of formula (6),
- where the dashed bond represents the linking of this group;
- precisely two adjacent groups W together stand for a group of the formula (7), and the remaining groups W stand, identically or differently on each occurrence, for CR1 or N,
- where the dashed bonds indicate the linking of this group;
- Y2 are, identically or differently on each occurrence, O, NR4, S, C(R4)2, Si(R4)2, BR4 or C═O, where the radical R4 which is bonded to N is not equal to H for the groups of formulae (7) and (8);
- R1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R5, where one or more H atoms may be replaced by D, F, or CN or, an aromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R5;
- R2, R4 are selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R5, where one or more H atoms may be replaced by D, F, or CN or, 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 R5, two adjacent substituents R4 may form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R5;
- R5 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 or an aromatic or heteroaromatic ring system having 5 to 30 aromatic 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 R5 here may form an aliphatic ring system with one another.
13 more elements
Dependencies are inferred from the claim text.