Organic electronic device and method for the production thereof

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.