Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues

Patent metadata

Field	Value
Publication number	US-10020455-B2
Application number	US-201514591188-A
Country	US
Kind code	B2
Filing date	Jan 7, 2015
Priority date	Jan 7, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

A phosphorescent emitter or delayed fluorescent and phosphorescent emitters represented by Formula 1 or Formula II, where M is platinum or palladium.

First claim

What is claimed is:

1. A compound of Formula I:

wherein M is platinum or palladium,
L 1 is diazolyl,
each L 2 and L 3 is phenyl,
L 4 is pyridyl,
each of F 1 and F 2 is independently present or absent, wherein at least one of F 1 and F 2 is present, and each of F 1 and F 2 present is independently selected from the following structures:

1. Aromatic Hydrocarbons and their Derivatives

2. Arylethylene, Arylacetylene and their Derivatives

3. Heterocyclic Compounds and their Derivatives

4. Other Fluorescent Luminophors

each of R 1l , R 2l , R 3l , R 4l , R 5l , R 6l , R 7l , R 8l , R 9l and R 10l is independently a mono-, di-, or tri-substitution, and each of R 1l , R 2l , R 3l , R 4l , R 5l , R 6l , R 7l , R 8l , R 9l and R 10l , if present, 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,
each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o , and Y p , if present, is independently C, N or B,
each of U a and U b , if present, is independently CH 2 , CR 1 R 2 , C═O, CH 2 , 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 W, W a , and W b , if present, is independently CH, CR 1 , SiR 1 , GeH, GeR 1 , N, P, B, Bi, or Bi═O,
A 1 is O,
A 2 is O, N, or NR 3 ,
each V 1 and V 4 is N;
each V 2 and V 3 is C,
each Y 1 , Y 2 , and Y 3 is C,
Y 4 is N,
R a is present or absent, wherein R b is present or absent, wherein R c is present or absent, wherein R d is present or absent, and if present each of R a , R b , R c , and R d independently represents mono-, di-, or tri-substitutions, and wherein each of R a , R b , R c , and R d 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, or two R a , two R b , two R c , or two R d optionally combine together form a ring; 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; wherein each pair of R 3 and R c , R 3 and R d , R 3 and L 3 , and R 3 and L 4 optionally combine together form a ring.

2. The compound of claim 1 , wherein the compound has the structure of Formula III or Formula V:

wherein each of 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.

3. The compound of claim 1 , wherein the compound has the structure of Formula VII:

wherein, if F 1 is present, R e and R f are on the ortho-positions of the bond between F 1 and L 1 ,
wherein, if F 2 is present, R g and R h are on the ortho-positions of the bond between F 2 and L 2 ,
wherein each of R e , R f , R g , and R h , if present, 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.

4. The compound of claim 1 , wherein the compound has the structure of anyone of Formulas A1-A23:

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Li Guijie

Classifications

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1062

  with oxygen · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title