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US 2024/0190908 A1Published application
Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues
AssigneeArizona Board of Regents on behalf of Arizona State University
InventorsJian Li, Linyu Cao
Life of this patent
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Abstract
A series of functionalized imidazophenthridine analogue-based blue phosphorescent emitters have been designed, where bulky substituents (e.g., tetrabutyl, phenyl, mesityl, triisopropylbenzene, etc.) are introduced on an imidazophenthridine fragment of the emitters. Bulky substituents may suppress potential excimer formation, as well as improve the solubility of the complexes. This class of emitters may be utilized in luminescent labels, emitters for organic light emitting devices, and lighting applications.
Claims20
A compound of General formula II or General formula IV;
- wherein, in General formula II and IV,
- Y2a, Y2b, Y2c, Y2d, Y4a Y6a, and X2 each independently represent C or N;
- X1, V1, and V2 each independently represent no bond, O, S, Se, NR7, PR7, AsR7, SbR7, BiR7, R7P═O, R7As═O, R7Bi═O, BR7, AlR7, CR7R8, SiR7R8, GeR7R8, C═O, SO2, or SeO2;
- each occurrence of R2 independently represents 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;
- each of R1, R3, R4, R5, R6, R7 and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R, R1, R3, R4, R5, R6, R7, and R8 independently represents 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;
- each n is independently an integer, valency permitting;
- and
- L4, L5, and L6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl.
11 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode;
- wherein the organic layer comprises a compound of General formula II or General formula IV;
- wherein, in General formula II and IV,
- Y2a, Y2b, Y2c, Y2d, Y4a Y6a, and X2 each independently represent C or N;
- X1, V1, and V2 each independently represent no bond, O, S, Se, NR7, PR7, AsR7, SbR7, BiR7, R7P═O, R7As═O, R7Bi═O, BR7, AlR7, CR7R8, SiR7R8, GeR7R8, C═O, SO2, or SeO2;
- each occurrence of R2 independently represents 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;
- each of R1, R3, R4, R5, R6, R7 and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R, R1, R3, R4, R5, R6, R7, and R8 independently represents 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;
- each n is independently an integer, valency permitting;
- and
- L4, L5, and L6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl.
15 more elements
A formulation comprising a compound of General formula II or General formula IV;
- wherein, in General formula II and IV,
- Y2a, Y2b, Y2c, Y2d, Y4a Y6a, and X2 each independently represent C or N;
- X1, V1, and V2 each independently represent no bond, O, S, Se, NR7, PR7, AsR7, SbR7, BiR7, R7P═O, R7As═O, R7Bi═O, BR7, AlR7, CR7R8, SiR7R8, GeR7R8, C═O, SO2, or SeO2;
- each occurrence of R2 independently represents 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;
- each of R1, R3, R4, R5, R6, R7 and R8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R, R1, R3, R4, R5, R6, R7, and R8 independently represents 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;
- each n is independently an integer, valency permitting;
- and
- L4, L5, and L6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl.
10 more elements
Dependencies are inferred from the claim text.