# US 9,520,570 B2 · Organic electronic device and method for the production thereof

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- Number: US 9,520,570 B2
- Document ID: US9520570B2
- Status: Granted
- Kind: B2
- Application number: 13/499,542
- Filed: 2010-09-30
- Published: 2012-11-15
- Granted: 2016-12-13
- Earliest claimed: 2009-09-30
- Assignees: OSRAM OLED GmbH
- Applicants: Guenter Schmid; Jan Hauke Wemken; Andreas Kanitz
- Inventors: Guenter Schmid; Jan Hauke Wemken; Andreas Kanitz
- Web page: https://patentgrep.com/patent/US9520570B2

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 50/165: comprising dopants
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 10/462: {Insulated gate field-effect transistors [IGFETs]}
- H10K 50/171: {Electron injection layers}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An organic electronic device comprising: a substrate; (1), a first electrode; (2), a second electrode (4); and an electron-conducting region (3A, 3B) which is arranged between the first and; second electrodes and comprises an organic matrix material (3B) and a salt (3A) which comprises a metal cation and an at least trivalent anion.

## Claims

### Claim 1

An electron-conducting composition comprising:
an electron-conducting matrix material, and
a salt as an n-dopant,
wherein the organic matrix material is selected from materials with a repeating unit with the following general formula:
where:
the ring members A to F are each independently C or N, with the proviso that a maximum of two nitrogen atoms may be present,
n is an integer from 2 to 8, where the free valences of the ends of the chains of the repeat units may each independently be saturated by H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl,
R1 to R4 may each independently be H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and/or R1 and R2 or R3 and R4 may together form butadiene or azabutadiene units, such that a fused 6-membered ring system is formed and the repeating units may be bonded by ethylene or azomethine units between the nth and (n+1)th ring to form phenanthrene or azaphenanthrene units,
or wherein the organic matrix material is selected from the following compounds:
2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1Hbenzimidazole),
2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole,
2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),
4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole,
1,3-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]benzene,
4,7-diphenyl-1,10-phenanthroline,
3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole,
6,6′-bis[5-biphenyl-4-yl)-1,3,4-oxadiazo-2-yl]-2,2′-bipyridyl,
2-phenyl-9,10-di(naphthalen-2-yl)anthracene,
2,7-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]-9,9-dimethylfluorene,
1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl)benzene,
2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline,
2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline,
tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane,
1-methyl-2-(4-(naphthalen-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]-phenanthroline,
siloles with silacyclopentadiene units,
and wherein said salt consists of:
a metal cation selected from the group consisting of monovalent metal cations Rb+, Cs+, Ag+, Cu+, Tl+, alkaline-earth metal cations, and combinations thereof, and
at least one anion, of at least threefold negative valence, selected from the group consisting of: phosphate anions PO43− and anionic polyvalent organic anions.

### Claim 2

An organic electronic device comprising:
a substrate;
a first electrode;
a second electrode; and
an electron-conducting region which is arranged between the first and second electrodes and comprises:
an organic matrix material and a salt,
wherein the organic matrix material is selected from materials with a repeating unit with the following general formula:
where:
the ring members A to F are each independently C or N, with the proviso that a maximum of two nitrogen atoms may be present,
n is an integer from 2 to 8, where the free valences of the ends of the chains of the repeat units may each independently be saturated by H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl,
R1 to R4 may each independently be H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and/or R1 and R2 or R3 and R4 may together form butadiene or azabutadiene units, such that a fused 6-membered ring system is foinied and the repeating units may be bonded by ethylene or azomethine units between the nth and (n+1)th ring to form phenanthrene or azaphenanthrene units,
or wherein the organic matrix material is selected from the following compounds:
2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1Hbenzimidazole),
2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole,
2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),
4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole,
1,3-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]benzene,
4,7-diphenyl-1,10-phenanthroline,
3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole,
6,6′-bis[5-biphenyl-4-yl)-1,3,4-oxadiazo-2-yl]-2,2′-bipyridyl,
2-phenyl-9,10-di(naphthalen-2-yl)anthracene,
2,7-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]-9,9-dimethylfluorene,
1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl)benzene,
2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline,
2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline,
tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane,
1-methyl-2-(4-(naphthalen-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]-phenanthroline,
siloles with silacyclopentadiene units,
and wherein the salt consists of:
a metal cation selected from the group consisting of monovalent metal cations Rb+, Cs+, Ag+, Cu+, Tl+, alkaline-earth metal cations, and combinations thereof, and
at least one anion, of at least threefold negative valence, selected from the group consisting of: phosphate anions PO43− and anionic polyvalent organic anions.

### Claim 3 (depends on 2)

The electronic device according to claim 2, wherein the electron-conducting region comprises an electron-conducting layer which comprises the organic matrix material and in which the salt has been introduced as an n-dopant.

### Claim 4 (depends on 3)

The electronic device according to claim 3, wherein the n-dopant is present in the organic matrix material in a concentration of 1 to 50% by volume.

### Claim 5 (depends on 3)

The electronic device according to claim 3, wherein the salt is coordinated to the organic matrix material via the metal cation.

### Claim 6 (depends on 3)

The electronic device according to claim 3, wherein a coordination compound between the metal cation and the organic matrix material is present in the electron-conducting layer, into which compound the anion has been intercalated.

### Claim 7 (depends on 3)

The electronic device according to claim 3, wherein the electron-conducting layer is obtainable by covaporization of a salt of the anion and of the metal cation with the organic matrix material.

### Claim 8 (depends on 2)

The electronic device according to claim 2, wherein the organic matrix material comprises a heterocyclic nitrogen containing compound.

### Claim 9 (depends on 2)

The electronic device according to claim 2, wherein the organic matrix material is selected from:
or combinations thereof.

### Claim 10 (depends on 2)

The electronic device according to claim 2, in the form of an organic electroluminescent device, further comprising
an organic electroluminescent layer between the electron-conducting region and one of the electrodes.

### Claim 11 (depends on 2)

The electronic device according to claim 2, in the form of an organic photosensitive device, further comprising
an organic photoactive layer between the electron-conducting region and one of the electrodes.

### Claim 12 (depends on 2)

A process for producing an organic electronic device according to claim 2, comprising the process steps of:
A) providing a substrate with a first electrode;
B) applying an electron-conducting region to the first electrode;
C) applying a second electrode in electrically conductive contact with the electron-conducting region;
wherein the electron-conducting region is applied by vaporizing the organic matrix material and the salt.