IP Library Granted Patent US 10,522,765
Granted Patent B2
US 10,522,765 · App. 15/515,751 · Granted Dec 31, 2019

Organic electronic device having lithoxy group and phosphine oxide group material

Inventors: Omrane Fadhel (Dresden, DE); Julien Frey (Dresden, DE); Wylliam Delaunay (Rennes, FR); Muriel Hissler (Rennes, FR)
Assignees: Novaled GmbH; University of Rennes
H01L51/0071C07F9/65685H01L51/0562H01L51/424H01L51/5076H01L51/5092
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Quick Facts
Patent No.
US 10,522,765
App. No.
15/515,751
Granted
Dec 31, 2019
Kind
B2
Abstract

The present invention relates to an organic electronic device, comprising a first electrode ( 11 ), a second electrode ( 14 ), and, between the first and the second electrode, a substantially organic layer ( 13 ) comprising a heterocyclic compound bearing at least one lithoxy group and containing at least one heterocyclic ring comprising a phosphine oxide group directly bound to three carbon atoms; a compound for use in such an organic electronic device and to a semiconducting material comprising the respective compound.

Claims (19)

1. Organic electronic device, comprising a first electrode, a second electrode, and, between the first and the second electrode, a substantially organic layer comprising a heterocyclic compound bearing at least one lithoxy group and containing at least one heterocyclic ring comprising a phosphine oxide group directly bound to three carbon atoms.

2. Organic electronic device according to claim 1 , wherein the lithoxy group is directly attached to an aromatic or heteroaromatic structural moiety.

3. Organic electronic device according to claim 1 , wherein the heterocyclic ring comprising the phosphine oxide group is a five-, six- or seven-membered ring.

4. Organic electronic device according to claim 1 , wherein the heterocyclic compound bearing at least one lithoxy group and containing at least one heterocyclic ring comprising a phosphine oxide group directly bound to three carbon atoms has formula (I):

wherein A 1 is a C 6 -C 30 arylene or C 2 -C 30 heteroarylene, each of A 2 and A 3 is independently selected from a C 6 -C 30 aryl and C 2 -C 30 heteroaryl, and A 2 with A 3 are linked to each other.

5. Organic electronic device according to claim 1 , wherein the substantially organic layer comprises an electron transport matrix compound.

6. Organic electronic device according to claim 5 , wherein the electron transport matrix compound comprises an imidazole or a P═O functional group.

7. Organic electronic device according to claim 5 , wherein the heterocyclic compound and the electron transport matrix compound are present in the substantially organic layer in the form of a homogeneous mixture.

8. Organic electronic device according to claim 1 , wherein the device is an organic light emitting diode, an organic solar cell, or an organic field effect transistor.

9. Organic electronic device according to claim 8 , wherein the device is the organic light emitting diode with the first electrode being an anode, the second electrode being a cathode, and the device further comprising a light emitting layer between the anode and the cathode and wherein the substantially organic layer is arranged between the cathode and the light emitting layer.

10. Heterocyclic compound bearing at least one lithoxy group and containing at least one heterocyclic ring comprising a phosphine oxide group directly bound to three carbon atoms has formula (I)

wherein A 1 is a C 6 -C 30 arylene or C 2 -C 30 heteroarylene, each of A 2 and A 3 is independently selected from a C 6 -C 30 aryl and C 2 -C 30 heteroaryl, and A 2 with A 3 are linked to each other.

11. Compound according to claim 10 , wherein A 1 is C 6 -C 12 arylene or C 2 -C 12 heteroarylene.

12. Compound according to claim 10 , wherein each of A 2 and A 3 is independently selected from a C 6 -C 10 arylene or C 2 -C 12 heteroarylene.

13. Compound according to claim 10 , wherein A 1 is selected from phenylene and pyridyl-diyl.

14. Compound according to claim 10 , wherein A 1 , A 2 and A 3 are o-phenylene.

15. Compound having formula (Ia)

wherein A 1 is a C 6 -C 30 arylene or C 2 -C 30 heteroarylene, each of A 2 and A 3 is independently selected from a C 6 -C 30 aryl and C 2 -C 30 heteroaryl, and A 2 with A 3 are linked to each other, as a penultimate precursor for compound of claim 10 having formula (I).

16. Electrically doped semiconducting material comprising at least one electron transport matrix compound and at least one heterocyclic compound bearing at least one lithoxy group and containing at least one heterocyclic ring comprising a phosphine oxide group directly bound to three carbon atoms.

Assignments (3)
MERGER Recorded Oct 19, 2023
From: UNIVERSITE DE RENNES I
To: UNIVERSITE DE RENNES
Reel/Frame 065490/0667 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2017
From: DELAUNAY, WYLLIAM; HISSLER, MURIEL
To: UNIVERSITY OF RENNES
Reel/Frame 042928/0948 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2017
From: FADHEL, OMRANE; FREY, JULIEN
To: NOVALED GMBH
Reel/Frame 042928/0958 →