Organic electron-conducting layer having N-dopant

Patent metadata

Field	Value
Publication number	US-11950441-B2
Application number	US-201716300663-A
Country	US
Kind code	B2
Filing date	Feb 21, 2017
Priority date	May 13, 2016
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

Various embodiments may include an organic electron-conducting layer comprising an n-dopant having the structure:

wherein L n denotes a number n of independently selected ligands L; M is a metal; R and R′ comprise compounds independently selected; n is from 0 to 5; m is from 1 to 6; n+m is from 2 to 6; and x has a value of 0, 1 or 2.

First claim

What is claimed is:

1. An organic electron-conducting layer comprising:
an n-dopant having the structure

wherein L n denotes a number n of ligands L, each ligand L independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, and alkyls, aryls, alkylaryls, or heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein M comprises a metal selected from the group consisting of: iron, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver, and gold, and M is connected directly by a double bond to a carbon atom;
wherein R and R′ comprise compounds connected by a single bond to a carbon atom and independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, heteroaryls, and alkyls, aryls, alkylaryls, or heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein n is from 0 to 5;
wherein m is from 1 to 6;
wherein n+m is from 2 to 6; and
wherein x has a value of 1 or 2.

2. The layer as claimed in claim 1 , wherein at least one of R and/or R′ comprises a substituted heteroatom.

3. The layer as claimed in claim 1 , wherein M comprises: palladium, platinum, silver, or gold.

4. The layer as claimed in claim 1 , comprising part of a charge generation layer.

5. The layer as claimed in claim 1 , having a thickness between 10 nanometers and 1000 nanometers.

6. The layer as claimed in claim 1 , wherein:
n is at least two; and
the ligands L are bridged to one another in the form of a higher ring structure.

7. The layer as claimed in claim 1 , further comprising a further electron transport material and/or electron acceptor material.

8. The layer as claimed in claim 7 , wherein the further electron transport material and/or electron acceptor material forms a matrix into which the n-dopant has been mixed.

9. The layer as claimed in claim 1 , wherein the n-dopant comprises between 70% and 100% by volume of the layer.

10. An organic electronic component comprising:
at least two electrodes; and
a layer of an n-dopant having the structure:

wherein L n denotes a number n of ligands L, each ligand L independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, heteroaryls, or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein M comprises a metal selected from the group consisting of: iron, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver, and gold, and M is connected directly by a double bond to a carbon atom;
wherein R and R′ comprise compounds connected by a single bond to a carbon atom and independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, heteroaryls, or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein n is from 0 to 5;
wherein m is from 1 to 6;
wherein n+m is from 2 to 6; and
wherein x has a value of 1 or 2.

11. The organic electronic component as claimed in claim 10 , wherein the component comprises an organic light-emitting diode, an organic solar cell, an organic photodetector, and/or an organic transistor.

12. The organic electronic component as claimed in claim 11 , comprising an organic light-emitting diode with a separate emitter layer disposed between an electron-conducting layer and at least one of the electrodes.

13. A process for producing an organic electron-conducting layer, the process comprising:
depositing a layer of an n-dopant by sublimation;
wherein the n-dopant has the structure:

wherein L n denotes a number n of ligands L, each ligand L independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein M comprises a metal selected from the group consisting of: iron, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver, and gold, and M is connected directly to a carbon atom by a double bond;
wherein R and R′ comprise compounds connected by a single bond to a carbon atom and independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein n is from 0 to 5;
wherein m is from 1 to 6;
wherein n+m is from 2 to 6; and
wherein x has a value of 1 or 2.

14. The process as claimed in claim 13 , wherein the n-dopant is deposited within the layer together with at least one electron transport material.

15. A method comprising using an n-dopant for increasing the electron conductivity of an organic layer;
wherein the n-dopant has the structure:

wherein L n denotes a number n of ligands L, each ligand L independently selected from the group consisting of: alkyls, aryls, alkylaryls, heteroalkyls, or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein M comprises a metal selected from the group consisting of: iron, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver, and gold, and M is connected directly to a carbon atom by a double bond;
wherein R and R′ comprise compounds connected to a carbon atom by a single bond and independently selected from the group consisting of: alkyls, aryls, alkylaryls, and heteroalkyls or alkyls, aryls, alkylaryls, and heteroalkyls substituted by functional groups, and substituted heteroatoms;
wherein n is from 0 to 5;
wherein m is from 1 to 6;
wherein n+m is from 2 to 6; and
wherein x has a value of 1 or 2.

Assignees

• Siemens Ag

Inventors

• Kessler Florian

Classifications

• H10K50/165 Primary

  comprising dopants · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/166

  comprising a multilayered structure · CPC title

• H10K71/30 Primary

  Doping active layers, e.g. electron transporting layers · CPC title

• H10K85/341

  Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence) · CPC title