Deuterated compounds for electronic applications

Patent metadata

Field	Value
Publication number	US-9496506-B2
Application number	US-201313748883-A
Country	US
Kind code	B2
Filing date	Jan 24, 2013
Priority date	Oct 29, 2009
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

This invention relates to deuterated indolocarbazole compounds that are useful in electronic applications. It also relates to electronic devices in which the active layer includes such a deuterated compound.

First claim

What is claimed is:

1. An indolocarbazole compound having Formula I or Formula II:

wherein:
Ar 1 is an aromatic electron transporting group;
Ar 2 is selected from the group consisting of aryl groups and aromatic electron transporting groups; and
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of H, D and aryl;

wherein the compound has at least one D.

2. The compound of claim 1 , wherein Ar 1 is a nitrogen-containing heteroaromatic group.

3. The compound of claim 2 , wherein the nitrogen-containing heteroaromatic group is selected from the group consisting of

wherein:
Ar 3 is an aryl group;
R 3 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, aryl, aryloxy, siloxane, and silyl;
a is an integer from 0-4;
b is an integer from 0-3;
c is an integer from 0-2;
d is an integer from 0-5;
e is 0 or 1;
f is an integer from 0-6; and
the nitrogen-containing heteroaromatic group can be bonded to the nitrogen on the indolocarbazole core at any of the positions indicated with the wavy line.

4. The compound of claim 3 , wherein R 3 is selected from D and aryl.

5. The compound of claim 1 , wherein at least one of Ar 2 is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenylnaphthylene, naphthylphenylene, deuterated derivatives thereof, and a group having Formula III:

where:
R 4 is the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, alkoxy, siloxane and silyl, or adjacent R 4 groups may be joined together to form an aromatic ring; and
m is the same or different at each occurrence and is an integer from 1 to 6.

6. The compound of claim 1 , wherein R 1 and R 2 are aryl.

7. The compound of claim 1 , wherein R 1 and R 2 are H or D.

8. The compound of claim 1 , selected from Compounds H1 through H21

9. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and at least one active layer therebetween, wherein the active layer comprises an indolocarbazole compound having at least one deuterium substituent.

10. The device of claim 9 , wherein the indolocarbazole compound has Formula I or Formula II:

wherein:
Ar 1 is an aromatic electron transporting group;
Ar 2 is selected from the group consisting of aryl groups and aromatic electron transporting groups; and
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of H, D and aryl;

wherein the compound has at least one D.

11. The device of claim 9 , wherein the active layer is an electroactive layer which further comprises an electroactive dopant capable of electroluminescence having an emission maximum between 380 and 750 nm.

12. The device of claim 10 , wherein the active layer is an electroactive layer and consists essentially of a compound having Formula I or Formula II and an electroactive dopant compound.

13. The device of claim 11 , wherein the electroactive dopant is a cyclometalated complex of iridium or platinum.

Assignees

• Du Pont

Inventors

• Lecloux Daniel David
• Dogra Kalindi
• Wu Weishi
• Fennimore Adam
• Smith Eric Maurice

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0508

  Electricity · mapped topic

• H01L2251/308

  Electricity · mapped topic