Tetradentate metal complexes with carbon group bridging ligands

Patent metadata

Field	Value
Publication number	US-10033003-B2
Application number	US-201514937318-A
Country	US
Kind code	B2
Filing date	Nov 10, 2015
Priority date	Nov 10, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Platinum, palladium, and gold complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters having one of the following structures:

First claim

What is claimed is:

1. A compound of Formula VI:

wherein:
M is Pt, Pd, or Au,
A is C, Si, or Ge,
each of L 1 and L 4 is a substituted or unsubstituted pyridyl group,
each of L 2 and L 3 is a substituted or unsubstituted phenyl group,
each of V 1 and V 4 is coordinated with M and is independently N or C,
each of V 2 and V 3 is coordinated with M and is C,
each of Y 1 and Y 2 is independently CH, CR, SiH, SiR, N, P, P═O, As, or As═O,
R La and R Lb are covalently bonded to form a fused ring, wherein the fused ring formed by R La and R Lb is substituted by one or more of 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,
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 is independently R is 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 the compound has a neutral charge.

3. The compound of claim 1 , wherein

is one of the following structures:

wherein:
each R 1 and R 2 present, valency permitting, is independently 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,
Z is CH 2 , CR x R y C═O, SiR x R y , GeH 2 , GeR x R y , NH, NR z , PH, PR z , R z P═O, AsR z , R z As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR z , R z Bi═O, BiH, or BiR z , and
each of R x , R y , and R z 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.

4. The compound of claim 1 , wherein each of

is independently one of the following structures:

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

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

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

8. A device comprising the compound of claim 1 .

9. The device of claim 8 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings.

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

11. The compound of claim 1 , wherein:
A is C or Si.

12. The compound of claim 1 , wherein Y 1 and Y 2 are N.

13. The compound of claim 1 , wherein A is C.

14. A compound selected from one of the following structures:

15. A compound selected from one of the following structures:

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Li Guijie

Classifications

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title

• C07F15/006 Primary

  Palladium compounds · CPC title

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0084

  Electricity · mapped topic