Tetradentate metal complexes with carbon group bridging ligands

Patent metadata

Field	Value
Publication number	US-12302745-B2
Application number	US-202318302995-A
Country	US
Kind code	B2
Filing date	Apr 19, 2023
Priority date	Nov 10, 2014
Publication date	May 13, 2025
Grant date	May 13, 2025

Abstract

Platinum, palladium, and gold complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters in organic light emitting materials (OLEDs) having a structure of Formula VII or Formula IX

First claim

What is claimed is:

1. A compound of Formula VII or Formula IX:

wherein:
M is Pt, Pd, or Au,
A is C, Si, or Ge,
L 1 and L 4 are each independently a substituted or an unsubstituted phenyl;
L 2 and L 3 are each independently a substituted or an unsubstituted pyridine;
V 1 and V 4 are each C:
V 2 and V 3 are each N;
the compound has a neutral charge;
each of Y 1 and Y 2 is independently CH, CR 1 , SiH, SiR 1 , GeH, GeR 1 , N, P, P═O, As, As═O, B, Bi, or Bi═O, S
each of Z 1 and Z 2 is independently CH 2 , CR 1 R 2 , C═O, SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 ,
each of R La and R Lb is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof, and R La and R Lb are optionally joined to form a fused ring,
each of R a , R b , R c , R d , R e , and R f is independently present or absent, and if present each of R b , R c , R e and R f independently represents mono-, di-, or tri-substitutions, each of R a and R d independently represents mono-, di-, tri-, or tetra-substitutions, and each of R a , R b , R c , R d , R e and R f is independently deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof, and
R 1 , R 2 , and R 3 are each independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

2. The compound of claim 1 , wherein

is one of the following structures:

wherein:
Z is CH 2 , CR 1 R 2 , C═O, SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 , and
each of R 1 , R 2 , and R 3 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

3. The compound of claim 1 , wherein each of

is independently

4. The compound of claim 1 , wherein each of

is independently

5. The compound of claim 1 , wherein each of

is independently one of the following structures:

6. The compound of claim 1 , wherein each of

is independently one of the following structures:

wherein each of R, R 1 , and R 2 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

7. The compound of claim 1 , wherein R La and R Lb are joined to form a fused ring.

8. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter.

9. An emitter comprising the compound of claim 1 , wherein the emitter is a phosphorescent emitter.

10. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent emitter.

11. A device comprising the compound of claim 1 .

12. The device of claim 11 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings.

13. The device of claim 11 , wherein the device is an organic light emitting diode.

14. The comp

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Li Guijie

Classifications

• C07F9/80

  Heterocyclic compounds · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/371

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K85/341

  Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence) · CPC title