Organic electronic device and method for the production thereof

Patent metadata

Field	Value
Publication number	US-9520570-B2
Application number	US-201013499542-A
Country	US
Kind code	B2
Filing date	Sep 30, 2010
Priority date	Sep 30, 2009
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

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

First claim

The invention claimed is:

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,
R 1 to R 4 may each independently be H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and/or R 1 and R 2 or R 3 and R 4 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 n th 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 PO 4 3− and anionic polyvalent organic anions.

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,
R 1 to R 4 may each independently be H, methyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and/or R 1 and R 2 or R 3 and R 4 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 n th 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 PO 4 3− and anionic polyvalent organic anions.

3. 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.

4. 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.

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

6. 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.

7. 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.

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

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

or combinations thereof.

10. 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.

11. 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.

12. 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.

Assignees

• Schmid Guenter
• Wemken Jan Hauke
• Kanitz Andreas
• Osram Oled Gmbh

Inventors

• Schmid Guenter
• Wemken Jan Hauke
• Kanitz Andreas

Classifications

• H01L51/5076

  Electricity · mapped topic

• H01L51/42

  Electricity · mapped topic

• H01L51/0512

  Electricity · mapped topic

• H01L51/5092

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic