Metal-assisted delayed fluorescent emitters containing tridentate ligands

Patent metadata

Field	Value
Publication number	US-9818959-B2
Application number	US-201514809981-A
Country	US
Kind code	B2
Filing date	Jul 27, 2015
Priority date	Jul 29, 2014
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

Tridentate platinum, palladium, and gold complexes of Formulas A-I and A-II and tridentate iridium and rhodium compounds of Formulas B-I, B-II, and B-III suitable for delayed fluorescent and phosphorescent or phosphorescent emitters in display and lighting applications.

First claim

What is claimed is:

1. A compound represented by Formula A-1:

wherein:
M is Pt, Pd, or Au,
L 1 is a five-membered heterocyclyl, five-membered heteroaryl, five-membered carbene, or five-membered N-heterocyclic carbene,
L 2 is phenyl,
L 3 is pyridyl,
R L4 is an inorganic anion or organic anion,
each of LP 1 , LP 2 , and LP 3 is independently present or absent, wherein at least one of LP 1 , LP 2 , or LP 3 is present and is independently an aromatic hydrocarbon, an aromatic hydrocarbon derivative, a polyphenyl hydrocarbon, a hydrocarbon with condensed aromatic nuclei, naphthalene, anthracene, phenanthrene, chrysene, pyrene, triphenylene, perylene, acenaphthene, tetracene, pentacene, tetraphene, coronene, fluorene, biphenyl, p-terphenyl, o-diphenylbenzene, m-diphenylbenzene, p-quaterphenyl, benzo[a]tetracene, benzo[k]tetraphene, indeno[1,2,3-cd]fluoranthene, tetrabenzo[de,hi,op,st]pentacene, arylethylene, arylacetylene, an arylacetylene derivative, a diarylethylene, a diarylpolyene, a diaryl-substituted vinylbenzene, a distyrylbenzene, a trivinylbenzene, an arylacetylene, a functional substitution product of stilbene, a five-, six- or seven-membered heterocyclic compound derivative, a furan derivative, a thiophene derivative, a pyrrole derivative, an aryl-substituted oxazole, a 1,3,4-oxadiazole, a 1,3,4-thiadiazole, an aryl-substituted 2-pyrazoline, an aryl-substituted pyrazole, a benzazole, 2H-benzotriazole, a substitution product of 2H-benzotriazole, a heterocycle with one, two or three nitrogen atoms, an oxygen-containing heterocycle, a coumarin, a coumarin derivative, a dye, an acridine dye, a xanthene dye, an oxazine, a thiazine, or a derivative thereof,
A is O,
V 1 is N, C, P, B, or Si,
V 2 is C,
V 3 is N,
each of Y 1 , Y 2 , Y 3 , and Y 4 is independently C, N, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , PR 3 , R 3 P═O, AsR 3 , R 3 As═O, or BR 3 ,
each of R a , R b , and R c is independently present or absent, and if present each of R a , R b and R c is independently a mono-, di-, tri-, or tetra-substitution, valency permitting, and each R a , R b , and R c 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
each of R 3 is independently hydrogen, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl, thiol, nitro, cyano, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, heteroaryl, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, mercapto, sulfo, carboxyl, hydrazino, substituted silyl, or polymeric; or any conjugate or combination thereof.

2. The compound of claim 1 , wherein M-R L4 is one of:

wherein each of R p , R q , and R r 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, di alkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, and polymeric; or any conjugate or combination thereof.

3. The compound of claim 1 , wherein the five-membered heterocyclyl

represents one of the following structures:

4. The compound of claim 1 , wherein:

represents one of the following structures:

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

5. The compound of claim 1 , wherein each of LP 1 , LP 2 and LP 3 , if present, independently represents one of the following structures:
aromatic hydrocarbons selected from the group consisting of:

and derivatives thereof,
arylethylenes and arylacetylenes selected from the group consisting of:

and derivatives thereof,
heterocyclic compounds selected from the group consisting of:

Assignees

• Univ Arizona State
• Arizona Board Of Regents On Behlaf Of Arizona State Univ

Inventors

• Li Jian
• Li Guijie

Classifications

• C09K2211/1033

  with oxygen · CPC title

• C07F15/006

  Palladium compounds · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title

• C09K2211/1011

  Condensed systems · CPC title