IP Library › Granted Patent US 9,773,986
Granted Patent B2
US 9,773,986 · App. 14/060,006 · Granted Sep 26, 2017

Copper(I)-carbene complexes and organic electroluminescent devices

Inventors: Mark Thompson (Anaheim, CA); Peter Djurovich (Long Beach, CA); Valentina Krylova (Los Angeles, CA)
Assignee: THE UNIVERSITY OF SOUTHERN CALIFORNIA
H01L51/0091C07F1/08C09K11/06C09K2211/188H01L51/5016
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Quick Facts
Patent No.
US 9,773,986
App. No.
14/060,006
Granted
Sep 26, 2017
Kind
B2
Abstract

Devices comprising an organic light emitting device are provided. The devices can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode. The organic layer comprising at least one host material comprising a phosphorescent complex comprising novel phosphorescent trigonal copper carbene complexes. The complex comprise a carbene ligand coordinated to a three coordinate copper atom. The complex may be used in organic light emitting devices. In particular, the complexes may be especially useful in OLEDs used for lighting applications.

Claims (51)

1. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising an emissive dopant and a first host material comprising a carbene ligand coordinated to a three coordinate copper atom, wherein the first host material has the formula:

wherein Cu is a monovalent copper atom;

wherein the carbene represented by X 1 —C*—X 2 is a monodentate ligand selected from the group consisting of

wherein z is 1, 2, 3, or 4;

wherein each of Y 1 and Y 2 form a bond with Cu;

wherein at least one of (i) to (x) is true:

(i) Y 1 -Y 2 is selected from the group consisting of:

(ii) Y 1 -Y 2 is selected from the group consisting of:

(iii) Y 1 is

and

Y 2 is a monodentate ligand selected from the group consisting of

(iv) Y 1 -Y 2 is selected from the group consisting of:

(v) Y 1 -Y 2 is selected from the group consisting of:

(vi) Y 1 -Y 2 is selected from the group consisting of:

(vii) Y 1 -Y 2 is selected from the group consisting of:

(viii) Y 1 -Y 2 is selected from the group consisting of:

(ix) Y 1 -Y 2 is selected from the group consisting of:

and

(x) Y 1 -Y 2 is selected from the group consisting of:

wherein, when present,

X is selected from the group consisting of NR, O, S, Se, CR 2 , and CO;

each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl, and heteroaryl;

Y 3 and Y 4 are independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, and heteroaryl;

Y 3 and Y 4 are optionally joined to form a cycle, which may be extended by fusion

n is 0, 1, or 2, and

m is 0, 1, or 2.

2. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

3. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

4. The device of claim 1 , wherein Y 1 is

and

Y 2 is a monodentate ligand selected from the group consisting of

5. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

6. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

7. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

8. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

9. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

10. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

11. The device of claim 1 , wherein Y 1 -Y 2 is selected from the group consisting of:

12. The device of claim 1 , wherein the first host meets one of option (iv) and option (v), and Y 3 and Y 4 are selected from the group consisting of the following (a) to (e):

wherein, in each of (a) to (e), the dashed lines represent bonds to the boron (B).

13. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising an emissive dopant and a first host material selected from the group consisting of:

14. The device of claim 13 , wherein the first host material is selected from the group consisting of:

15. The device of claim 13 , wherein the first host material is selected from the group consisting of:

16. The device of claim 13 , wherein the first host material is selected from the group consisting of:

17. The device of claim 13 , wherein the first host material is selected from the group consisting of:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2013
From: THOMPSON, MARK; DJUROVICH, PETER; KRYLOVA, VALENTINA
To: THE UNIVERSITY OF SOUTHERN CALIFORNIA
Reel/Frame 031458/0352 →
Continuity (6)
Continuation 12948396 · Nov 17, 2010
Provisional Application 61402989 · Sep 9, 2010
Provisional Application 61398808 · Jul 1, 2010
Provisional Application 61301362 · Feb 4, 2010
Provisional Application 61262804 · Nov 19, 2009
Related Publication 20140125221A1 · May 8, 2014