IP Library › Granted Patent US 11,063,221
Granted Patent B2
US 11,063,221 · App. 15/304,118 · Granted Jul 13, 2021

Materials for electronic devices

Inventors: Holger Heil (Frankfurt am Main, DE); Lara-Isabel Rodriguez (Darmstadt, DE); Beate Burkhart (Darmstadt, DE); Sebastian Meyer (Acchaffenburg, DE)
Assignee: Merck Patent GmbH
H01L51/0058C07C1/30C07C13/28C07C13/465C07C13/62C07C15/38C07C253/30C07C255/50C07C255/52C07D213/16C07D235/18C07D239/26C07D251/24C09B1/00C09B57/00C09B57/001C09K11/025H01L51/0054C07C2601/02C07C2601/14C07C2602/08C07C2603/24C07C2603/26C07C2603/42C07C2603/50C07C2603/52H01L51/006H01L51/0545H01L51/42H01L51/50H01L51/5012H01L51/5016Y02E10/549
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Quick Facts
Patent No.
US 11,063,221
App. No.
15/304,118
Granted
Jul 13, 2021
Kind
B2
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.

Claims (25)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2016
From: HEIL, HOLGER; RODRIGUEZ, LARA-ISABEL; BURKHART, BEATE; MEYER, SEBASTIAN
To: MERCK PATENT GMBH
Reel/Frame 040013/0988 →
Priority Claims (1)
EP 14001391 · Apr 16, 2014 · regional
Continuity (1)
Related Publication 20170125686A1 · May 4, 2017