IP Library Granted Patent US 9,673,409
Granted Patent B2
US 9,673,409 · App. 14/300,832 · Granted Jun 6, 2017

Phosphorescent tetradentate metal complexes having modified emission spectra

Inventors: Jian Li (Tempe, AZ); Guijie Li (Tempe, AZ); Jason Brooks (Philadelphia, PA)
Assignees: Arizona Board of Regents on behalf of Arizona State University; Universal Display Corporation
H01L51/0087C07F15/0086C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/185H01L51/5016Y02E10/549
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Quick Facts
Patent No.
US 9,673,409
App. No.
14/300,832
Filed
Jun 10, 2014
Granted
Jun 6, 2017
Kind
B2
Art Unit
1624
USPC
540/145
Abstract

Multidentate metal complexes useful as phosphorescent emitters in display and lighting applications having the following structures:

Claims (29)

1. A composition comprising one or more compounds of the formula:

wherein

M represents platinum (Pt), gold (Au), iridium (Ir), rhodium (Rh), ruthenium (Ru), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), silver (Ag), mercury (Hg), cadmium (Cd), or zirconium (Zr),

R a and R b each independently represents mono-, di-, tri, or tetra-substitution, and each independently represents deuterium, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof,

V 3 is C,

V 4 is N,

X is N,

A 1 is O,

R 1 , R 2 , R 3 R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently represents hydrogen, deuterium, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof; and

at least one of R 1 , R 2 , R 3 , and R 4 is not hydrogen.

2. The composition of claim 1 , wherein the polymeric group comprises a polyalkylene, a polyether, or a polyester.

3. The composition of claim 1 , wherein the each of the one or more compounds has a neutral charge.

4. A composition comprising one or more of the following compounds:

5. A composition comprising one or more of the following compounds:

6. A device comprising the composition of claim 1 .

7. The device of claim 6 , wherein the device comprises a full color display.

8. The device of claim 6 , wherein the device is a photovoltaic device.

9. The device of claim 6 , wherein the device is a luminescent display device.

10. The device of claim 6 , wherein the device comprises an organic light emitting diode (OLED).

11. The device of claim 10 , wherein the device comprises a phosphorescent organic light emitting diode.

12. The device of claim 10 , wherein the device is a phosphorescent organic light emitting diode.

13. A light emitting device comprising the composition of claim 1 .

14. A light emitting device comprising the composition of claim 4 .

15. The composition of claim 1 , wherein R a represents mono- or di-substitution, and each independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

16. The composition of claim 1 , wherein R a represents mono-substitution and represents an unsubstituted aryl group; or R a represents di-substitution and each R a represents an unsubstituted alkyl group.

17. The composition of claim 1 , wherein R b represents mono-substitution and represents an unsubstituted alkyl group.

18. The composition of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently represents hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aryl group, a mono- or dialkylamino group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted heteroaryl group.

19. A device comprising the composition of claim 4 .

20. A device comprising the composition of claim 5 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 19, 2014
From: LI, JIAN; LI, GUIJIE
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 033561/0339 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 19, 2014
From: BROOKS, JASON
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 033561/0415 →
Continuity (2)
Provisional Application 61833091 · Jun 10, 2013
Related Publication 20140364605A1 · Dec 11, 2014