Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-11063221-B2
Application number	US-201515304118-A
Country	US
Kind code	B2
Filing date	Mar 17, 2015
Priority date	Apr 16, 2014
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

The present application relates to a substituted benzanthracene compound of a formula (I) or (II). The application furthermore relates to an electronic device which comprises the said benzanthracene compound.

First claim

The invention claimed is:

1. A compound of formula (I-1-1):

wherein
Ar 1 is an anthracene, which is optionally substituted by one or more radicals R 2 , wherein the group Ar 1 is present at a position on the benzanthracene in formula (I-1-1) selected from the group consisting of positions 4 and 5, as depicted below:

R 0 is a straight-chain alkyl group having 1 to 20 C atoms or a branched alkyl group having 3 to 20 C atoms, wherein said groups are each optionally substituted by one or more radicals R 3 ;
R 2 is on each occurrence, identically or differently, H, D, F, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R 3 an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 ; and
R 3 is on each occurrence, identically or differently, H, D or F.

2. The compound of claim 1 , wherein R 0 is selected from the group consisting of straight-chain alkyl groups having 1 to 10 C atoms or branched alkyl groups having 3 to 10 C atoms, wherein said groups are each optionally substituted by one or more radicals R 3 .

3. A process for preparing a compound of claim 1 , comprising:
A) steps 1) through 3) in the following sequence:
1) preparing a benzanthracene compound substituted by one or more aromatic or heteroaromatic ring systems via a coupling reaction between a benzanthracene derivative and an aromatic or heteroaromatic ring system;
2) halogenating the benzanthracene;
3) introducing a substituent into the halogenated position; or comprising

B) steps I) and II) in the following sequence:
I) preparing a substituted benzanthracene derivative from a naphthyl derivative and a phthalic anhydride;
II) coupling the substituted benzanthracene derivative with an aromatic or heteroaromatic ring system.

4. The process of claim 3 , wherein the halogenation is bromination.

5. An oligomer, polymer, or dendrimer comprising one or more compounds of claim 1 , wherein the bond(s) to the polymer, oligomer, or dendrimer are optionally localised at any positions in formula (I-1-1) substituted by R 0 , R 2 or R 3 .

6. A formulation comprising at least one compound of claim 1 , and at least one solvent.

7. A formulation comprising at least one oligomer, polymer, or dendrimer of claim 5 and at least one solvent.

8. An electronic device comprising at least one compound of claim 1 .

9. The electronic device of claim 8 , wherein the electronic device is selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices.

10. An electronic device comprising the least one oligomer, polymer, or dendrimer of claim 5 .

11. The electronic device of claim 10 , wherein the electronic device is selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices.

12. The electronic device of claim 9 , wherein the electronic device is an organic electroluminescent device comprising an anode, a cathode, an emitting layer, and optionally further organic layers, wherein the at least one compound is present in the emitting layer as a matrix compound in combination with one or more emitter compounds.

13. The electronic device of claim 11 , wherein the electronic device is an organic electroluminescent device comprising an anode, a cathode, an emitting layer, and optionally further organic layers, wherein the at least one oligomer, polymer, or dendrimer is present in the emitting layer as a matrix compound in combination with one or more emitter compounds.

Assignees

• Merck Patent Gmbh

Inventors

• Heil Holger
• Rodriguez Lara-Isabel
• Burkhart Beate
• Meyer Sebastian

Classifications

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• C07C15/38 Primary

  containing four rings · CPC title

• C07C13/62

  with more than three condensed rings · CPC title

• C09B57/001

  Pyrene dyes · CPC title