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US 11,895,913 B2Granted
Materials for organic light emitting devices
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Anja Jatsch, Thomas Eberle, Tobias Grossmann, Jonas Valentin Kroeber, Lars Dobelmann-Mara
Life of this patent
Estimating the term…
Abstract
The present invention describes carbazole, dibenzofuran, dibenzothiophene and fluorene derivatives which are substituted by electron-deficient heteroaryl groups, 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 these compounds.
Claims16
A mixture comprising at least one compound of the formula (2a),
- where the following applies to the symbols and indices used:
- A is on each occurrence, identically or differently, CR or N, where a maximum of two groups A per ring stand for N and where A stands for C if the group comprising Y2 is bonded at this position;
- W is on each occurrence, identically or differently, CR or N, where a maximum of two groups W stand for N, or two adjacent groups W together stand for a group of the following formula (3), where the compound of the formula (1a) contains a maximum of one group of the formula (3),
- X is on each occurrence, identically or differently, CR or N, with the proviso that at least one group X stands for N;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
- Y1, Y2, Y3 are on each occurrence, identically or differently, O, NR, S or CR2, where the radical R which is bonded to N is not equal to H;
- L is on each occurrence, identically or differently, a single bond or an aromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
- R is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R1)2, C(═O)Ar1, C(═O)R1, P(═O)(Ar)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, Si(R1)2, C═O, C═S, C═NR, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R1, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R′, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1;
- two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system here, which may be substituted by one or more radicals R1;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R1;
- two radicals Ar1 which are bonded to the same N atom, P atom or B atom may also be bridged to one another here by a single bond or a bridge selected from N(R′), C(R1)2, O or S;
- m is 0, 1, 2 or 3;
- R1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having t 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 carbatoms;
- two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic ring system with one another here;
- and at least one further compound, wherein the further compound is a matrix material and wherein the matrix material is a hole-transporting compound.
12 more elements
A mixture comprising at least one compound of the formula (2a),
- where the following applies to the symbols and indices used:
- A is on each occurrence, identically or differently, CR or N, where a maximum of two groups A per ring stand for N and where A stands for C if the group comprising Y2 is bonded at this position;
- W is on each occurrence, identically or differently, CR or N, where a maximum of two groups W stand for N, or two adjacent groups W together stand for a group of the following formula (3), where the compound of the formula (1a) contains a maximum of one group of the formula (3),
- X is on each occurrence, identically or differently, CR or N, with the proviso that at least one group X stands for N;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
- Y1 is NR, S or CR2, where the radical R which is bonded to N is not equal to H;
- Y2, Y3 are on each occurrence, identically or differently, O, NR, S or CR2, where the radical R which is bonded to N is not equal to H;
- L is on each occurrence, identically or differently, a single bond or an aromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
- R is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R1)2, C(═O)Ar1, C(═O)R1, P(═O)(Ar)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, Si(R1)2, C═O, C═S, C═NR, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R1, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1;
- two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system here, which may be substituted by one or more radicals R1;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R1;
- two radicals AO which are bonded to the same N atom, P atom or B atom may also be bridged to one another here by a single bond or a bridge selected from N(R1), C(R1)2, O or S;
- m is 0, 1, 2 or 3;
- R1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having t 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 carbatoms;
- two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic ring system with one another here;
- and at least one further compound, wherein the further compound is a matrix material.
13 more elements
Dependencies are inferred from the claim text.