IP Library Granted Patent US 8,221,903
Granted Patent B2
US 8,221,903 · App. 12/065,859 · Granted Jul 17, 2012

Materials for N-type doping of the electron transporting layers in organic electronic devices

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Quick Facts
Patent No.
US 8,221,903
App. No.
12/065,859
Granted
Jul 17, 2012
Kind
B2
Abstract

The invention pertains to new materials based on donor carbene intermediates for the improvement of electron injection and electron transport in organic electronic components like organic light-emitting diodes (OLED's), organic field effect transistors (OFET's), and components based on organic photovoltaics, in particular organic solar cells.

Claims (29)

1. A material for the n-doping of the electron-transporting layer in organic electronic components, comprising at least one compound of structures 1 to 3:

wherein:

X − is an anion,

Y is S or N—Ar,

R is alkyl, and,

Ar 1 , Ar 2 , and Ar 3 are each, independently, aryl moieties.

2. The material of claim 1 , wherein X − is chloride or formiate.

3. The material of claim 1 , wherein the Ar in N—Ar is phenyl or 1-naphthyl.

4. The material of claim 1 , wherein R is methyl.

5. The material of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently selected from the group consisting of phenyl, 1-naphthyl and 2-naphthyl.

6. A material for the n-doping of the electron-transporting layer in organic electronic components, the material comprising at least one compound of structures 1a to 3a:

wherein:

Y is S or N—Ar;

R is alkyl; and,

Ar 1 , Ar 2 , and Ar 3 are each, independently, aryl moieties.

7. The material of claim 6 , wherein the Ar in N—Ar is phenyl or 1-naphthyl.

8. The material of claim 6 , wherein R is methyl.

9. The material of claim 6 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently selected from the group consisting of phenyl, 1-naphthyl and 2-naphthyl.

10. An organic electronic component comprising at least two electrodes and an active layer, wherein located between at least one electrode and the active layer is an electron-transporting layer doped with a material of any one of claims 1 , 2 , or 3 - 9 .

11. A process for manufacturing one of the materials of claims 6 to 9 , wherein a compound of one of structures 1 to 3 is converted in high-vacuum to a corresponding compound of one of structures 1a to 3a:

wherein:

X − is an anion;

Y is S or N—Ar;

R is alkyl; and,

Ar 1 , Ar 2 , and Ar 3 are each, independently, aryl moieties.

12. The process of claim 11 , wherein the Ar in N—Ar is phenyl or 1-naphthyl.

13. The process of claim 11 , wherein X − is chloride or formiate.

14. The process of claim 11 , wherein R is methyl.

15. The process of claim 11 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently selected from the group consisting of phenyl, 1-naphthyl and 2-naphthyl.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2020
From: OSRAM OLED GMBH
To: DOLYA HOLDCO 5 LIMITED
Reel/Frame 053464/0374 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 11/658.772 REPLACED 11/658.772 PROPERTY NUMBERS PREVIOUSLY RECORDED AT REEL: 053464 FRAME: 0395. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 11, 2020
From: DOLYA HOLDCO 5 LIMITED
To: PICTIVA DISPLAYS INTERNATIONAL LIMITED
Reel/Frame 053464/0395 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2015
From: OSRAM OPTO SEMICONDUCTORS GMBH
To: OSRAM OLED GMBH
Reel/Frame 036527/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2008
From: KANITZ, ANDREAS
To: OSRAM OPTO SEMICONDUCTORS GMBH
Reel/Frame 021457/0365 →