Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-12342718-B2
Application number	US-202117912872-A
Country	US
Kind code	B2
Filing date	Mar 22, 2021
Priority date	Mar 24, 2020
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

The application relates to heterocyclic compounds of formulae (IV) to (VII), to the use of said compounds in an electronic device, and to methods for producing said compounds.

First claim

The invention claimed is:

1. A compound according to one of the formulae (IV) to (VI)

and where the variables that occur are as follows:
X is N or CAr 3 ;
Z is O;
Ar 1 is the same or different at each instance and is selected from fused-on aromatic ring systems having 6 to 18 aromatic ring atoms; where the aromatic ring systems are each substituted by R 1 radicals;
Ar 2 is selected from phenyl, pyridine, naphthalene, triphenylene, carbazole, pyrimidine, triazine, triazinylphenylene and biphenyl, each substituted by one or more R 2 radicals;
Ar 3 is selected from H, D, and aromatic ring systems having 6 to 40 aromatic ring atoms; where the aromatic ring systems are each substituted by R 3 radicals;
R 1 is the same or different at each instance and is selected from H, D, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 4 radicals;
R 2 is the same or different at each instance and is selected from H, D, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 4 radicals;
R 3 is the same or different at each instance and is selected from H, and D;
R 4 is the same or different at each instance and is selected from H, and D, and;
excluding the following compounds:

2. The compound as claimed in claim 1 , wherein X is N.

3. The compound as claimed in claim 1 , wherein Ar 1 is the same or different at each instance and is selected from #phenyl, naphthalene, phenanthrene, anthracene: where the aromatic ring systems are each substituted by R 1 radicals.

4. The compound as claimed in claim 1 , wherein Ar 2 is selected from each substituted by R 2 radicals.

5. The compound as claimed in claim 1 , wherein the compound conforms to one of the formulae (X) and (XI):

where the variables are as defined in claim 1 .

6. A process for preparing the compound as claimed in claim 1 , comprising preparing first an intermediate of one of the formulae (IV-Int) to (VI-Int)

by a ring closure reaction,
introducing in an Ullmann reaction or a Buchwald reaction an aromatic or heteroaromatic system in the position of the Ar 2 group in the formulae (IV) to (VI), and
conducting a halogenation reaction on one of the Ar 1 rings, which introduces a halogen substituent in one of the Ar 1 rings, and then conducting a Suzuki reaction in which an aromatic system is introduced in the position of the halogen substituent.

7. A formulation comprising a compound according to one of the formulae (IV) to (VI)

and where the variables that occur are as follows:
X is N or CAr 3 ;
Z is O;
Ar 1 is the same or different at each instance and is selected from fused-on aromatic ring systems having 6 to 18 aromatic ring atoms, where the aromatic ring systems are each substituted by R 1 radicals;
Ar 2 is selected from phenyl, pyridine, naphthalene, triphenylene, carbazole, pyrimidine, triazine, triazinylphenylene and biphenyl, each substituted by one or more R 2 radicals;
Ar 3 is selected from H, D and aromatic ring systems having 6 to 40 aromatic ring atoms; where the aromatic ring systems are each substituted by R 3 radicals;
R 1 is the same or different at each instance and is selected from H, D, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 4 radicals;
R 2 is the same or different at each instance and is selected from H, D, E, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 4 radicals;
R 3 is the same or different at each instance and is selected from H, and D;
R 4 is the same or different at each instance and is selected from H, and D, and excluding the following compound:

8. A method comprising utilizing the compound according to one of the formula (IV) to (VI) as defined in claim 7 in an electronic device.

9. An electronic device comprising at least one compound according to one of the formulae (IV) to (VI) as defined in claim 7 .

10. The electronic device as claimed in claim 9 , wherein the device is an organic electroluminescent device, and wherein the compound is used in an emitting layer as matrix material for one or more phosphorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), and/or is used in an electron transport layer and/or is used in a hole blocker layer.

Assignees

• Merck Patent Gmbh
• Merck Kgaa

Inventors

• Parham Amir Hossain
• Ehrenreich Christian
• Engelhart Jens

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D495/14

  Ortho-condensed systems · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title