Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11737352-B2
Application number	US-201816479662-A
Country	US
Kind code	B2
Filing date	Jan 22, 2018
Priority date	Jan 23, 2017
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

The present invention relates to compounds of the formulae (1) to (4), which are suitable for use in electronic devices, in particular organic electroluminescent devices, to intermediate compounds for the compounds or formulae (1) to (4) and to electronic devices, which comprise the compounds of formulae (1) to (4).

First claim

The invention claimed is:

1. A compound of one of the formulae (1) to (4),

where the following applies to the symbols and indices used:
Y is selected from the group consisting of fluorescent emitting groups, phosphorescent emitting groups, host groups for fluorescent emitting compounds and host groups for phosphorescent emitting compounds, having a molecular weight equal or less than 3000 g/mol, and which may in each case be substituted by one or more radicals R 1 ;
Ar is on each occurrence, identically or differently, selected from the group consisting of aromatic ring systems having 6 to 18 aromatic ring atoms, which may in each case also be substituted by one or more radicals R, where two groups Ar are allowed to be connected via a single bond or a divalent bridge;
T is on each occurrence, identically or differently selected from the group consisting of T1 to T19,

where the symbol(s) * in T1 to T19 indicates the bonding to the group(s) —(Ar) m —Y in formulae (1) to (4);
R and R 1 stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, NO 2 , a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where in each case one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡, C═O, C═S, SO, SO 2 , O or S 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 2 , or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , where two adjacent substituents R and/or two adjacent substituents R 1 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R 2 ;
R 2 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched or cyclic 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;
m is on each occurrence, identically or differently, 1, 2, 3 or 4;
n is an integer from 1 to 8; and
p is on each occurrence, identically or differently, 0 or 1, with the proviso that at least one p is equal to 1 in formulae (1) and (2).

2. The compound according to claim 1 , wherein m is on each occurrence, identically or differently, 1 or 2.

3. The compound according to claim 1 , wherein the group Y is a phosphorescent emitting group selected from the group consisting of iridium, platinum and copper complexes.

4. The compound according to claim 1 , wherein the group Y is a fluorescent emitting group selected from the group consisting of arylamines, indenofluorene derivatives and anthracene derivatives.

5. The compound according to claim 1 , wherein the group Y is a host group for a phosphorescent emitting compound selected from spirobifluorene amines, aromatic ketones, aromatic phosphine oxides or aromatic sulfoides or sulfones, triarylamines, carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, fluorene derivatives, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives or bridged carbazole derivatives.

6. The compound according to claim 1 , wherein the group Y is a host group for a fluorescent emitting compound selected from the group consisting of oligoarylenes comprising naphthalene, anthracene, benzanthracene, benzophenanthrene, pyrene, oligoarylenevinylenes, indenofluorene derivatives, ketones, phosphine oxides and sulfoxides.

7. The compound according to claim 1 , wherein the group T has a molecular weight equal or superior to 350 g/mol.

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

9. The formulation according to claim 8 , wherein the solvents is selected from the group consisting of aromatics, alkylaromatics, cyclohexanes, ketones, ethers, esters, amides, sulfones, sulfoxides and mixtures thereof.

10. A process for the preparation of the compound according to claim 1 , which comprises bonding group T to a group Y, or in which a group T, which is previously substituted by a group Ar, is bonded to a group Y via the group Ar, where T, Y and Ar have the same meaning as in claim 1 .

11. An electronic device comprising at least one compound according to claim 1 , wherein the electronic device is selected from the group consisting of organic electroluminescent device, organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, dye-sensitised organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode, organic plasmon emitting device and liquid-crystal device.

12. An organic electroluminescent device which comprises an emitting layer, where the said emitting layer comprises at least one compound according to claim 1 .

13. The compound according to claim 1 , wherein the group T is selected from the group consisting of T1, T2, T6, T9, T10, T11, T12, T15, T16 and T18.

14. The compound according to claim 1 , wherein the group T is selected from the group consisting of T1, T2 and T6.

15. The compound according to claim 1 , wherein the group T is selected from the group consisting of T1 and T2.

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils
• Ehrenreich Christian
• Harbach Philipp
• Rodriguez Lara-Isabel
• Linge Rouven
• Meyer Sebastian
• Lackner Aaron

Classifications

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/626 Primary

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

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title