IP Library Granted Patent US 9,711,741
Granted Patent B2
US 9,711,741 · App. 14/421,634 · Granted Jul 18, 2017

Metal compounds and methods and uses thereof

Inventors: Jian Li (Tempe, AZ); Eric Turner (Chandler, AZ); Liang Huang (Mesa, AZ)
Assignee: Arizona Board of Regents on behalf of Arizona State University
H01L51/0087C07F15/006C07F15/0086C09K11/06H01L51/0083H01L51/0084H05B33/14C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096C09K2211/185C09K2211/188H01L51/5016
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Quick Facts
Patent No.
US 9,711,741
App. No.
14/421,634
Granted
Jul 18, 2017
Kind
B2
Abstract

Disclosed herein are metal compounds, compositions, and devices related thereto, such as full color displays or OLEDs.

Claims (51)

1. A compound having the structure:

wherein M comprises Pt, Pd, Ir, Rh, or Au;

wherein each of R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each Y 1a independently is O, NR 2 , or S, or a combination thereof, wherein each R 2 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene;

wherein each of Y 1b and Y 1c independently is O or S, or a combination thereof;

wherein each of Y 2a , Y 2b , Y 2c , and Y 2d independently is CR 6b , wherein each R 6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3c , Y 3d , Y 4a , Y 4c and Y 4d independently is CR 6b , wherein each R 6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each of Y 3b and Y 4b are N or NR 6a , wherein each R 6a independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each of m and n independently are 2;

wherein each of

independently is partial or full unsaturation of the ring with which it is associated.

2. The compound of claim 1 ,

wherein m is 2,

wherein n is 2,

wherein Y 2b and Y 2c is CH,

wherein Y 3b and Y 4b is N,

and

wherein M is Pt or Pd.

3. The compound of claim 2 ,

wherein at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C,

and

wherein M is Pt or Pd.

4. A compound having the structure:

wherein M comprises Ir, Rh, Pt, Os, or Ru;

wherein each of R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each Y 1a independently is O, NR 2 , or S, wherein Y 1d , and Y 1e independently is, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(O)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R 2 and R 3 together form C═O, wherein each of R 2 and R 3 independently is linked to an adjacent ring structure, thereby forming a cyclic structure;

wherein each of Y 1b and Y 1c independently is O or S, or a combination thereof;

wherein each of Y 2a , Y 2b , Y 2c , and Y 2d independently is CR 6b , wherein each R 6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each of Y 3a , Y 3c , Y 3d , Y 4a , Y 4c , and Y 4d independently is CR 6b , wherein each R 6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each of Y 3b and Y 4b are N or NR 6a , wherein each R 6a independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein in each of each of Y 5a , Y 5b , Y 5c , Y 5d , Y 6a , Y 6b , Y 6c , and Y 6d independently is N, O, S, NR 6a , or CR 6b ; wherein each of R 6a and R 6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;

wherein each m independently is 2;

wherein each of

independently is partial or full unsaturation of the ring with which it is associated.

5. The compound of claim 4 ,

wherein m is 2,

wherein Y 2b and Y 2c is CH,

wherein Y 3b and Y 4b is N,

and

wherein M is Ir or Rh.

6. The compound of claim 5 ,

wherein at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C, and

wherein M is Ir or Rh.

7. A device comprising the compound of claim 1 .

8. The device of claim 7 , wherein the device is an organic light emitting diode.

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

10. The device of claim 7 , wherein the one or more compounds is used as a host material.

11. The device of claim 7 , wherein the device can be a lighting device.

12. A device comprising the compound of claim 1 , wherein the compound is used as a phosphorescent emitter in the device.

13. A device comprising the compound of claim 1 , wherein the compound is used as a delayed fluorescent and phosphorescent emitter in the device.

14. A composition comprising the compound of claim 1 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Dec 11, 2017
From: ARIZONA STATE UNIVERSITY, TEMPE
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 044815/0165 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2015
From: LI, JIAN; TURNER, ERIC; HUANG, LIANG
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 036566/0198 →
Continuity (2)
Provisional Application 61692937 · Aug 24, 2012
Related Publication 20150207086A1 · Jul 23, 2015