Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11767299-B2
Application number	US-201816623633-A
Country	US
Kind code	B2
Filing date	Jun 20, 2018
Priority date	Jun 23, 2017
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

First claim

The invention claimed is:

1. An organic electroluminescent device (OLED) comprising a compound of the formula (2A),

where the following applies to the symbols and indices used:
R 1 stands on each occurrence, identically or differently, for H, D, F, CN, a straight-chain alkyl groups having 1 to 10 C, where one or more H atoms may be replaced by D or F;
R 2 stands on each occurrence, identically or differently, from the group consisting of F, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or a branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 3 , where in each case one or more non-adjacent CH 2 groups may be replaced by R 3 C═CR 3 , C═C, C═O, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy groups having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 3 ;
R 3 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 4 , where in each case one or more non-adjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, P(═O)(R 4 ), SO, SO 2 , O, S or CONR 4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 4 , where two adjacent substituents R 3 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R 4 ;
R 4 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, where in each case one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms;
Ar is on each occurrence, identically or differently, and aromatic of heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case also be substituted by one or more radicals R 4 ;
n is on each occurrence equal to 1 and
wherein the OLED comprising the compound of the formula (2A), is employed as an electron-acceptor material in a hole-injection layer.

2. A formulation comprising at least one compound according to claim 1 and at least one solvent.

3. The OLED according to claim 1 , wherein the compound is employed as the electron-acceptor material in the hole-injection layer as pure material, or in combination with one or more further compounds, where a proportion of the compound according to claim 1 is then comprised between 50.0 and 99.9% by vol. if the compounds are applied from a gas phase and 50.0 and 99.9% by weight if the compounds are applied from solution.

4. The OLED according to claim 3 , wherein the OLED further comprises at least one hole-transport layer and at least one emitting layer, where the hole-transport layer is located between the hole-injection layer and the emitting layer.

5. The OLED according to claim 3 , wherein the hole-injection layer comprising the compound has a thickness layer of from 0.5 nm to 50 nm.

6. The OLED according to claim 1 , wherein the compound is employed as a p-dopant in a hole-transporting layer selected from a hole-injection layer, a hole-transport layer and an electron-blocking layer.

7. The OLED according to claim 1 , wherein the compound is of the formula:

Assignees

• Merck Patent Gmbh

Inventors

• Stengel Ilona
• Vinokurov Kathy
• Voges Frank
• Ludemann Aurélie

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• C07D237/26 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• C07C49/597

  of a five-membered ring · CPC title

• C07C49/653

  polycyclic · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title