Blue thermally activated delayed fluorescent emitters and hosts based on functionalized imidazolyl groups

Patent metadata

Field	Value
Publication number	US-12545678-B2
Application number	US-202117470092-A
Country	US
Kind code	B2
Filing date	Sep 9, 2021
Priority date	Sep 9, 2020
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

Abstract

Compounds of General Formula I may act as thermally activated delayed fluorescent emitters in organic electroluminescent devices. Compounds of General Formula I have donor and acceptor groups part of the same conjugated system. Devices incorporating compounds of General Formula I may have higher EQE and longer material lifetimes.

First claim

We claim:

1 . A compound of General Formula I:

wherein:
Y 1a , Y 1b , Y 1c , Y 2a Y 2b , Y 2c , and Y 2d each independently represents C or N;

C and E each represent N;
each A, B, and D independently represent C or N;
each of Y 1 and Y 2 is independently absent or present, valency permitting;
Y 1 and Y 2 independently represent 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; or Y 1 and Y 2 may together form a ring;
R 1 and R 2 are independently absent or present, valency permitting, and each R 1 and R 2 independently represents 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; any two adjacent R 1 and R 2 may together form a ring;
provided that at least two adjacent R 2 together represent a group of Formula A:

wherein:
waved lines indicate bonds to the respective Y 2a , Y 2b , Y 2c , or Y 2d ;
Y 3a Y 3b , Y 3c , and Y 3d each independently represents C or N;
X 1 independently represents C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, X 1 independently represents CR 4 , SiR 4 , GeR 4 , NR 4 , P═O, As═O, B, BR 4 , AlR 4 , Bi═O, CR 4 R 5 , C═O, SiR 4 R 5 , GeR 4 R 5 , PR 4 , PR 4 R 5 , R 4 P═O, AsR 4 , R 4 As═O, S═O, SO 2 , Se═O, SeO 2 , BR 4 , BR 4 R 5 , AlR 4 , AlR 4 R 5 , R 4 Bi═O, or BiR 4 ;
R 3 , R 4 , and R 5 are independently absent or present, valency permitting, and each R 3 , R 4 and R 5 independently represents 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; any two of R 1 , R 2 , R 3 , R 4 , and R 5 may together form a ring;
each n is an integer, valency permitting; and
wherein at least two adjacent R 3 together represent a group of Formula B:

wherein waved lines indicate bonds to the respective Y 3a , Y 3b , Y 3c , and Y 3d ;
Y 4a , Y 4b , Y 4c , and Y 4d each independently represents C or N;
X 2 independently represents C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, X 2 independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , PR 7 , PR 7 R 8 , R 7 P═O, AsR 7 , R 7 As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
each of R 6 , R 7 , and R 8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 6 , R 7 , and R 8 independently represents 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; any two of R 6 , R 7 , and R 8 may together form a ring; and
n is an integer, valency permitting.

2 . The compound of claim 1 , wherein the compound is represented by General Formula 1:

wherein, in General Formula 1:
Y 1a , Y 1b , Y 1c , Y 2a , Y 2b , Y 3a Y 3b Y 3c , and Y 3d each independently represents C or N;
C and E each represent N;
each A, B, and D independently represent C or N;
X 1 independently represents C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, X 1 independently represents CR 4 , SiR 4 , GeR 4 , NR 4 , P═O, As═O, B, BR 4 , AlR 4 , Bi═O, CR 4 R 5 , C═O, SiR 4 R 5 , GeR 4 R 5 , PR 4 , PR 4 R 5 , R 4 , P═O, AsR 4 , R 4 As═O, S═O, SO 2 , Se═O, SeO 2 , BR 4 , BR 4 R 5 , AlR 4 , AlR 4 R 5 , R 4 Bi═O, or BiR 4 ;
each of Y 1 and Y 2 is independently absent or present, valency permitting; Y 1 and Y 2 independently represent 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; or Y 1 and Y 2 may together form a ring;
each of R 1 , R 2 , R 3 , R 4 , and R 5 is independently absent or present, valency permitting, and each of R 1 , R 2 , R 3 , R 4 , and R 5 independently represents 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, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, A sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, or polymeric; or any combination thereof; any two of R 1 , R 2 , R 3 , R 4 , and R 5 may together form a ring; and
n is an integer, valency permitting.

3 . The compound of claim 1 , wherein the compound is represented by General Formula 2:

wherein, in General Formula 2:
Y 1a , Y 1b , Y 1c , Y 2a Y 2b Y 3a Y 3b Y 3c , and Y 3d each independently represents C or N;

C and E each represent N;
each A, B, and D independently represent C or N;
X 1 independently represents C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, X 1 independently represents CR 4 , SiR 4 , GeR 4 , NR 4 , P═O, As═O, B, BR 4 , AlR 4 , Bi═O, CR 4 R 5 , C═O, SiR 4 R 5 , GeR 4 R 5 , P

Assignees

• Univ Arizona State
• Arizona Board Of Regents On Behalf Of Arizon State Univ

Inventors

• Li Jian
• Wu Jiang

Classifications

• C07D493/22

  in which the condensed system contains four or more hetero rings · CPC title

• C07D493/14

  Ortho-condensed systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• H05K2201/10106

  Light emitting diode [LED] · CPC title

• H10K85/6572

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