Substituted heteroaryls as thermally assisted delayed fluorescent materials

Patent metadata

Field	Value
Publication number	US-12534462-B2
Application number	US-202318169289-A
Country	US
Kind code	B2
Filing date	Feb 15, 2023
Priority date	May 19, 2017
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

Thermally assisted delayed fluorescent materials with triad-type materials for use in full color displays and lighting applications with the following generic structures are provided:

First claim

What is claimed is:

1 . A compound represented by any one of the following formulas:

wherein:

represents:

each R X independently represents hydrogen, deuterium, fluoro, bromo, iodo, cyano, isonitrile, nitro, alkyl, haloalkyl, aralkyl, alkenyl, alkynyl, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or heteroaryl;
each R 1 independently represents hydrogen, deuterium, halogen, cyano, isonitrile, nitro, alkyl, haloalkyl, aralkyl, alkenyl, alkynyl, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or heteroaryl; and
each R 2 independently represents hydrogen, deuterium, halogen, cyano, isonitrile, nitro, alkyl, haloalkyl, aralkyl, alkenyl, alkynyl, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or heteroaryl;
wherein the alkyl, haloalkyl, and aralkyl of each R X , R 1 , and R 2 is optionally and independently substituted with one or more substituents independently selected from the group consisting of deuterium, halogen, cyano, isonitrile, nitro, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl;
wherein the alkenyl and alkynyl of each R X , R 1 , and R 2 is optionally and independently substituted with one or more substituents independently selected from the group consisting of deuterium, halogen, cyano, isonitrile, nitro, haloalkyl, aralkyl, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl; and
wherein the carbamoyl, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, alkylsulfonylamino, arylsulfonylamino, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, alkylthio, sulfamoyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl of each R X , R 1 , and R 2 is optionally and independently substituted with one or more substituents independently selected from the group consisting of deuterium, halogen, cyano, isonitrile, nitro, alkyl, haloalkyl, aralkyl, alkenyl, alkynyl, carbamoyl, carboxy, alkoxycarbonyl, amino, monoalkylamino, monoarylamino, dialkylamino, diarylamino, acylamino, ureido, alkoxycarbonylamino, aryloxycarbonylamino, hydrazino, alkylsulfonylamino, arylsulfonylamino, hydroxy, alkoxy, aryloxy, trialkylsilyl, trialkoxysilyl, triarylsilyl, phosphoramide, thiol, alkylthio, alkylsulfinyl, sulfamoyl, sulfonic acid, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl.

2 . The compound of claim 1 , wherein

represents:

3 . The compound of claim 1 , wherein

represents:

4 . The compound of claim 1 , wherein

represents:

5 . The compound of claim 1 , wherein

represents:

6 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

Assignees

• Univ Arizona State

Inventors

• Li Jian

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title