# US 11,309,497 B2 · Materials for organic electroluminescent devices

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,309,497 B2
- Document ID: US11309497B2
- Status: Granted
- Kind: B2
- Application number: 15/329,099
- Filed: 2015-07-03
- Published: 2017-07-20
- Granted: 2022-04-19
- Earliest claimed: 2014-07-29
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Amir Hossain Parham; Tobias Grossmann; Thomas Eberle; Anja Jatsch; Jonas Valentin Kroeber; Lars Dobelmann-Mara
- Web page: https://patentgrep.com/patent/US11309497B2

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 471/14: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/18: Carrier blocking layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/624: {containing six or more rings}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 2101/10: Triplet emission
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The device according to claim 1 wherein the compound is of the formula (1a),
where symbols used have the meanings given in claim 1 and n stands, identically or differently on each occurrence, for 0, 1, 2 or 3.

### Claim 3 (depends on 1)

The device according to claim 1 of one of the formulae (1b) to (1g),
where the symbols used have the meanings given in claim 1.

### Claim 4 (depends on 1)

The device according to claim 1, wherein the groups of the formulae (2), (3) and (4) are selected from the groups of the formulae (2-1) to (2-10), (3-1) and (4-1),
where the dashed bond represents the linking of these groups and R2 has the meanings claim 1.

### Claim 5 (depends on 1)

The device according to claim 1, wherein the group of the formula (6) is selected from the groups of the formula (6-2),
where R1 has the meanings given in claim 1 and wherein
two adjacent groups W together stand for a group of the formula (7a) and the other two groups W stand for CR1,
where Y2 and R1 have the meanings given in claim 1;
m is, identically or differently on each occurrence, 0, 1, 2, 3 or 4.

### Claim 6 (depends on 1)

The device according to claim 1, wherein the group of the formula (6) is selected from the groups of the formulae (6-2a) to (6-2f),
where the symbols and indices used have the meanings given in claim 1;
m is, identically or differently on each occurrence, 0, 1, 2, 3 or 4.

### Claim 7 (depends on 1)

The device according to claim 1, wherein Y2 stand, identically or differently on each occurrence, for O, C(R4)2 or NR4, where the radical R4 which is bonded to the nitrogen is not equal to H.

### Claim 8 (depends on 1, 2)

The device according to claim 2 wherein the compound is of the formula (1a), where the symbols used have the meanings given in claim 1 and n stands, identically or differently on each occurrence, for 0, 1, 2 or 3, and wherein N1 is selected from the groups of the formula (6-2),
where R1 has the meanings given in claim 1 and wherein
two adjacent groups W together stand for a group of the formula (7a) and the other two groups W stand for CR1,
where Y2 and R1 have the meanings given in claim 1;
m is, identically or differently on each occurrence, 0, 1, 2, 3 or 4.

### Claim 9

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.