Organic compounds with soluble groups

Patent metadata

Field	Value
Publication number	US-10683453-B2
Application number	US-201515534325-A
Country	US
Kind code	B2
Filing date	Nov 18, 2015
Priority date	Dec 12, 2014
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

The present invention relates to soluble organic compounds, to compositions comprising these compounds, to formulations comprising the compounds or compositions, and to electronic devices.

First claim

The invention claimed is:

1. An organic luminescent TADF compound which does not contain any metals and which has a gap between the first excited triplet state (T 1 ) and the first excited singlet state (S 1 ) of not more than 0.15 eV, characterized in that the organic compound contains at least one solubilizing group LG, wherein LG is selected from the following groups, where the groups may have further substitution by one or more identical or different R 1 radicals:

and
R 1 is the same or different at each instance and is hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or a silyl group or a substituted keto group having 1 to 40 carbon atoms, an alkoxycarbonyl group having 2 to 40 carbon atoms, an aryloxycarbonyl group having 7 to 40 carbon atoms, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where two or more of the R 1 groups together may form a mono- or polycyclic, aliphatic or aromatic ring system.

2. The compound according to claim 1 , wherein the compound is of the general formula (1)

where the symbols and indices used are as follows:
m is an integer selected from 1, 2, 3, 4 and 5;
n is an integer selected from 1, 2, 3, 4 and 5;
p is an integer greater than or equal to 1;
A is an acceptor group which may be substituted by one or more R 1 radicals which may be the same or different at each instance;
D is a donor group which may be substituted by one or more R 1 radicals which may be the same or different at each instance;
LG is as defined in claim 1 ;
V is any organic bridge between the A and D groups or a single bond, where, when V is a single bond, either m or n is 1, where V may be substituted by one or more R 1 radicals which may be the same or different at each instance;
R 1 is the same or different at each instance and is hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or a silyl group or a substituted keto group having 1 to 40 carbon atoms, an alkoxycarbonyl group having 2 to 40 carbon atoms, an aryloxycarbonyl group having 7 to 40 carbon atoms, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where two or more of the R 1 groups together may form a mono- or polycyclic, aliphatic or aromatic ring system.

3. The compound according to claim 2 , wherein
p is an integer from 1 to 4;
R 1 is the same or different at each instance and is hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or a silyl group or a substituted keto group having 1 to 40 carbon atoms, an alkoxycarbonyl group having 2 to 40 carbon atoms, an aryloxycarbonyl group having 7 to 40 carbon atoms, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where two or more of the R 1 groups together may form a mono- or polycyclic, aliphatic or aromatic ring system, and when no two or more of the R 1 groups together can form a mono- or polycyclic, aliphatic or aromatic ring system.

4. The compound according to claim 1 , wherein the TADF compound is an organic compound having a molecular weight of not more than 5000 g/mol.

5. The compound according to claim 1 , wherein the TADF compound is an organic compound having a molecular weight of not more than 1000 g/mol.

6. The compound according to claim 1 , wherein the A group contains a cyano, oxo or nitrile group or a pyrimidine or a pyrazine.

7. The compound according to claim 1 , wherein the D group contains a diarylamino, diarylheteroarylamino, carbazole, indenocarbazole or indolocarbazole group.

8. The compound according to claim 1 , wherein the bridge V is selected from the following formulae which may be substituted by one or more R 1 radicals which may be the same or different at each instance:

9. The compound according to claim 1 , wherein the compound contains at least 2, aromatic rings.

10. A composition comprising one or more of the compounds according to claim 1 and one or more functional materials selected from the group of the electron-conducting materials (ETM), electron-injecting materials (EIM), electron-blocking materials (EBM), hole-conducting materials (HTM), hole-injecting materials (HIM), hole-blocking materials (HBM), fluorescent emitters, phosphorescent emitters, matrix materials and inorganic nanoparticles.

11. The composition according to claim 8 , wherein the composition comprises two matrix materials.

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

13. A process for producing an organic electronic device which comprises producing at least one layer of the electronic device from solution with the aid of the formulation according to claim 12 .

14. An organic electronic device which comprises at least one compound according to claim 1 .

15. The organic electronic device as claimed in claim 14 , wherein the device is an organic light-emitting diode (OLED) or organic light-emitting electrochemical cell (OLEC, LEEC, LEC).

16. The device according to claim 14 , wherein the device is selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors or organic photoreceptors.

17. The device according to claim 14 , wherein the device is an organic electroluminescent device selected from the group consisting of the organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLETs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

18. An organic electroluminescent device comprising at least one compound according to claim 1 in an emission layer.

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Stoessel Philipp
• Pflumm Christof
• Jatsch Anja
• Kaiser Joachim
• Aydt Ewald
• Joosten Dominik

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/111 Primary

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title

• H10K85/6572

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

• H10K85/626

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

• H10K85/615

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