IP Library Granted Patent US 11,114,626
Granted Patent B2
US 11,114,626 · App. 16/834,229 · Granted Sep 7, 2021

Metal compounds, methods, and uses thereof

Inventors: Jian Li (Tempe, AZ); Guijie Li (Hangzhou Zhejiang, CN)
Assignee: Arizona Board of Regents on behalf of Arizona State University
H01L51/0087C07F15/0086C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/185H01L51/42H01L51/5012H01L51/5016H01L51/5036Y02E10/549
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Quick Facts
Patent No.
US 11,114,626
App. No.
16/834,229
Granted
Sep 7, 2021
Kind
B2
Abstract

Disclosed herein are metal compounds useful in devices, such as, for example, OLEDs.

Claims (30)

1. A compound having the formula

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

wherein each of Z 1 , Z 2 , and Z 3 independently is present or absent, and if present each of Z 1 , Z 2 , and Z 3 independently is A, A 1 , or A 2 ;

wherein each of A, A 1 , or A 2 independently 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 M is Pt, Pd, Au, Ir, Rh, Ru, Fe, Co, Ni, Cu, Zn, Ag, Hg, Cd, or Zr;

wherein at least one of L 1 , L 2 , L 3 , or L 4 comprises

wherein m and n independently is an integer from 0 to 4;

wherein each of V, X, and Y independently is V 1 , V 2 , V 3 , V 4 , O, S, S═O, SO 2 , Se, N, NR 3 , PR 3 , R 1 P═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 , or any one of

wherein at least one of V, X, or Y is V 1 , V 2 , V 3 , or V 4 ;

wherein m and n independently is an integer from 0 to 4;

wherein each of V 1 , V 2 , V 3 , and V 4 independently is coordinated to M;

wherein each of V 1 , V 2 , V 3 , and V 4 independently is N, C, CH, P, B, SiH, or Si; and

wherein each of R, R 1 , R 2 , R 3 , and R 4 , independently is 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, amercapto, sulfo, carboxyl, hydrzino, substituted silyl, or polymerizable, or any conjugate or combination thereof.

2. The compound of claim 1 , wherein one of Z 1 , Z 2 , or Z 3 is present and two of Z 1 , Z 2 , and Z 3 is not present.

3. The compound of claim 1 , wherein two of Z 1 , Z 2 , and Z 3 is present and one of Z 1 , Z 2 , or Z 3 is not present.

4. The compound of claim 1 , wherein each of Z 1 , Z 2 , and Z 3 independently is absent.

5. The compound of claim 1 , wherein the compound has the structure

6. The compound of claim 1 , wherein at least one of L 1 , L 2 , L 3 , or L 4 , together with V 1 , V 2 , V 3 , and V 4 , respectively, comprises one or more of the following structures:

7. The compound of claim 1 , wherein

has the structure

8. The compound of claim 1 , wherein

has the structure

9. The compound of claim 1 , wherein at least one of V 1 , V 2 , V 3 , or V 4 is N.

10. The compound of claim 1 , wherein at least one of V 1 , V 2 , V 3 , or V 4 is C.

11. The compound of claim 1 , wherein M is Pt or Pd.

12. The compound of claim 1 , wherein the compound is represented by one of the following structures:

13. An organic light emitting device comprising one or more compounds of claim 12 .

14. A full color display comprising one or more light emitting devices of claim 13 .

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

16. A full color display comprising one or more light emitting devices of claim 15 .

Continuity (4)
Continuation 15882358 · Jan 29, 2018
Continuation 14430454
Provisional Application 61704880 · Sep 24, 2012
Related Publication 20200227660A1 · Jul 16, 2020
Cited By (10)
US 12,193,327 US 12,232,411 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