IP Library Granted Patent US 9,385,329
Granted Patent B2
US 9,385,329 · App. 14/513,506 · Granted Jul 5, 2016

Platinum complexes and devices

Inventors: Jian Li (Tempe, AZ); Guijie Li (Tempe, AZ); Jason Brooks (Philadelphia, PA)
Assignee: Arizona Board of Regents on behalf of Arizona State University and Universal Display Corporation
H01L51/0087C09K11/06C09K2211/185H01L51/5016Y02E10/549
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Quick Facts
Patent No.
US 9,385,329
App. No.
14/513,506
Granted
Jul 5, 2016
Kind
B2
Abstract

Platinum compounds of Formulas I and II useful in a variety of devices, such as, for example organic-light emitting diodes (OLEDs).

Claims (33)

1. A compound of Formula II2:

wherein L 1 is a five-membered heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene,

wherein L 2 is phenyl,

wherein A 1 is O, S, S═O, SO 2 , Se, NR 3 , PR 3 , RP═O, CR 1 R 2 , C═O, SiR 1 R 2 , GeR 1 R 2 , BH, P(O)H, PH, NH, CR 1 H, CH 2 , SiH 2 , SiHR 1 , BH, or BR 3 ,

wherein V 1 is N, V 2 is C, V 3 is C, and V 4 is N,

wherein each of Y 1 , Y 2 , Y 3 , and Y 4 is independently C, N, O, or S,

wherein X is N,

wherein each of R b , R 1 , R 2 , and R 3 of Formula II2 is independently present or absent and if present, each of R b , R 1 , R 2 , and R 3 present represents mono-, di-, or tri-substitutions, and each R b , R 1 , R 2 , and R 3 present is independently substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, mercapto, sulfo, carboxyl, hydrazino, or substituted silyl, and wherein two or more of R b are optionally linked together,

wherein each of R, R 1 , R 2 , and R 3 of variable A 1 is independently hydrogen, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, mercapto, sulfo, carboxyl, hydrazino, or substituted silyl, and wherein two or more of R, R 1 , R 2 , and R 3 are optionally linked together,

wherein each of

is independently:

and

wherein each of R, R 1 , and R 2 of

is independently hydrogen, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, mercapto, sulfo, carboxyl, hydrazino, or substituted silyl, and wherein two or more of R, R 1 , R 2 , and R 3 are optionally linked together.

2. The compound of claim 1 , wherein the compound has a neutral charge.

3. The compound of claim 1 , wherein the five-membered heterocyclyl

is one of the following structures:

4. The compound of claim 1 , wherein

is one of the following:

wherein each of

is independently:

wherein each of R, R 1 , R 2 , R 3 , and R 4 is independently a mono-, di-, tri, or tetra-substitution, wherein each of R, R 1 , R 2 , R 3 , and R 4 independently are substituted or unsubstituted hydrogen, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, heteroaryl, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrazino, or substituted silyl, and wherein two or more of R, R 1 , R 2 , R 3 , and R 4 are optionally linked together.

5. The compound of claim 1 , wherein the compound is selected from one of the following structures:

6. A composition comprising one or more compounds of claim 1 .

7. An emitter comprising one or more compounds of claim 1 , wherein the emitter is a phosphorescent emitter, a delayed fluorescent emitter, or a combination thereof.

8. A device comprising one or more compounds of claim 1 .

9. The device of claim 8 , wherein the device comprises an organic light emitting diode.

10. The device of claim 8 , wherein the device comprises a full color display.

11. The device of claim 8 , wherein the device comprises a phosphorescent OLED device.

12. The device of claim 8 , wherein the device comprises a fluorescent OLED device.

13. A photovoltaic device comprising one or more compounds of claim 1 .

14. A luminescent display device comprising one or more compounds of claim 1 .

15. A light emitting device comprising one or more compounds of claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2014
From: LI, JIAN; LI, GUIJIE
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 034195/0816 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2014
From: BROOKS, JASON
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 034196/0010 →
Continuity (3)
Provisional Application 61890545 · Oct 14, 2013
Provisional Application 61890580 · Oct 14, 2013
Related Publication 20150105556A1 · Apr 16, 2015