Oxocarbon-, pseudooxocarbon- and radialene compounds and their use

Patent metadata

Field	Value
Publication number	US-9876172-B2
Application number	US-201414570443-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Apr 30, 2007
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

The present invention relates to oxocarbon-, pseudooxocarbon- and radialene compounds as well as to their use as doping agent for doping an organic semiconductive matrix material, as blocker material, as charge injection layer, as electrode material as well as organic semiconductor, as well as electronic components and organic semiconductive materials using them.

First claim

The invention claimed is:

1. A radialene compound having the following formula:

wherein n is 1, 3, or 4;
wherein X 1 , X 2 , and X 3 are independently selected from

wherein Y is independently selected from perhalogenated alkyl; aryl is independently selected from a substituted or unsubstituted, aromatic hydrocarbon or biaryl; and hetaryl is independently selected from a substituted or unsubstituted, aromatic heterocyclic compound or biheteroaryl.

2. The compound according to claim 1 , wherein Y is perfluroalkyl.

3. The compound according to claim 1 , wherein Y is CF 3 .

4. The compound according to claim 1 , wherein each hetaryl is pyridyl, pyrimidyl, triazine, or oxodiazole.

5. The compound according to claim 1 , wherein at least one hetaryl is an electron poor compound.

6. The compound according to 1 , wherein at least one hetaryl is polynuclear.

7. The compound according to 1 , wherein at least one hetaryl is at least partially fluorinated.

8. An organic semiconductive material, wherein the organic semiconductive material comprises at least one organic matrix compound and at least one doping agent, wherein the doping agent comprises at least one radialene compound, wherein the radialene compound has the following formula:

wherein n is 1, 3, or 4;
wherein X 1 , X 2 , and X 3 are independently selected from

wherein Y is independently selected from perhalogenated alkyl; aryl is independently selected from a substituted or unsubstituted, aromatic hydrocarbon or biaryl; and hetaryl is independently selected from a substituted or unsubstituted, aromatic heterocyclic compound or biheteroaryl.

9. The organic semiconductive material according to claim 8 , wherein the molar doping ratio of doping agent to matrix molecule or the doping ratio of doping agent to monomeric units of a polymeric matrix molecule is about 1:1 to about 1:100,000.

10. The organic semiconductive material according to claim 8 , wherein each hetaryl is pyridyl, pyrimidyl, triazine, or oxodiazole.

11. The organic semiconductive material according to claim 8 , wherein at least one hetaryl is an electron poor compound.

12. The organic semiconductive material according to claim 8 , wherein at least one hetaryl is polynuclear.

13. The organic semiconductive material according to claim 8 , wherein at least one hetaryl is at least partially fluorinated.

Assignees

• Novaled Gmbh

Inventors

• Hartmann Horst
• Zeika Olaf
• Lux Andrea
• Willmann Steffen

Classifications

• C07C255/51

  containing at least two cyano groups bound to the carbon skeleton · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C255/40

  the carbon skeleton being further substituted by doubly-bound oxygen atoms · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C07C261/04

  Cyanamides (unsubstituted cyanamide C01C3/16) · CPC title