IP Library Granted Patent US 10,793,546
Granted Patent B2
US 10,793,546 · App. 15/503,690 · Granted Oct 6, 2020

Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes

Inventors: Jian Li (Tempe, AZ); Liang Huang (Mesa, AZ); Tyler Fleetham (Gilbert, AZ)
Assignee: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
C07D401/14C07F1/12C07F7/0803C07F9/5045C07F15/006C07F15/0033C07F15/0073C09K11/06H01L51/0067H01L51/0084H01L51/50C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1074C09K2211/1096C09K2211/18C09K2211/185H01L51/0081H01L51/5016Y02E10/549
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Quick Facts
Patent No.
US 10,793,546
App. No.
15/503,690
Granted
Oct 6, 2020
Kind
B2
Abstract

Complexes and devices, such as organic light emitting devices and full color displays, including a compound of the formula wherein: M is Pd 2+ , Ir + , Rh + , or Au 3+ ; each of V 1 , V 2 , V 3 , and V 4 is coordinated to M and is independently N, C, P, B, or Si; each of L 1 , L 2 , L 3 , and L 4 is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and Z is O, S, NR, CR 2 , SiR 2 , BR, PR, where each R is independently substituted or unsubstituted C1-C4 alkyl or substituted or unsubstituted aryl.

Claims (44)

1. A compound of General Formula I:

wherein:

M is Pd 2+ , Ir + , or Rh + ;

each of V 1 , V 2 , V 3 , and V 4 is coordinated to M and is independently N, C, P, B, or Si, wherein at least one of V 1 and V 2 is C;

each of L 1 , L 2 , L 3 , and L 4 is a six-membered ring and is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and

Z is O, S, NR, CR 2 , SiR 2 , BR, PR,

where each R is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl.

2. The compound of claim 1 , wherein the compound has one of the following structures:

3. A light emitting device comprising the compound of claim 1 .

4. An OLED device comprising the compound of claim 1 .

5. The OLED device of claim 4 , wherein the device is a phosphorescent OLED device.

6. A photovoltaic device comprising the compound of claim 1 .

7. A luminescent display device comprising the compound claim 1 .

8. The compound of claim 1 , wherein at least one of V 3 and V 4 is C.

9. A compound of General Formula I:

wherein:

M is Pd 2+ ;

each of V 1 and V 2 is N;

each of V 3 and V 4 is C;

each of L 1 , L 2 , L 3 , and L 4 is a six-membered ring and is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and

Z is BR, PR,

where each R is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl.

10. The compound of claim 9 , wherein the compound has one of the following structures:

11. A compound of General Formula I:

wherein:

M is Pd 2+ , Ir k , Rh + , or Au 3+ ;

each of V 1 and V 2 is N;

each of V 3 and V 4 is C;

each of L 1 , L 2 , L 3 , and L 4 is a six-membered ring and is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and

Z is CR 2 or SiR 2 , where R 2 represents a biphenyl group, and each of CR 2 and SiR 2 represents a fluorenyl group.

12. The compound of claim 11 , wherein the compound has one of the following structures:

13. A compound of General Formula I:

wherein:

M is Pd 2+ , Ir k , Rh + , or Au 3+ ;

V 1 and V 2 are coordinated to M and are each independently N, C, P, B, or Si, wherein at least one of V 1 and V 2 is C;

V 3 and V 4 are coordinated to M and are each N;

each of L 1 , L 2 , L 3 , and L 4 is a six-membered ring and is independently a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene; and

Z is O, S, NR, CR 2 , SiR 2 , BR, PR,

where each R is independently substituted or unsubstituted C 1 -C 4 alkyl or substituted or unsubstituted aryl.

14. A light emitting device comprising the compound of claim 13 .

15. An OLED device comprising the compound of claim 13 .

16. The OLED device of claim 15 , wherein the device is a phosphorescent OLED device.

17. A photovoltaic device comprising the compound of claim 13 .

18. A luminescent display device comprising the compound claim 13 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Jun 4, 2018
From: ARIZONA STATE UNIVERSITY-TEMPE CAMPUS
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 046291/0967 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2017
From: LI, JIAN; HUANG, LIANG; FLEETHAM, TYLER
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 042638/0126 →
Continuity (2)
Provisional Application 62037802 · Aug 15, 2014
Related Publication 20170305881A1 · Oct 26, 2017
Cited By (9)
US 12,193,327 US 12,302,745 US 12,312,366 US 12,448,405 US 12,503,644 US 12,534,462 US 12,545,678 US 12,565,486 US 12,643,919