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US 10,020,455 B2Granted
Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues
AssigneeArizona Board of Regents on behalf of Arizona State University
InventorsJian Li, Guijie Li
Life of this patent
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Abstract
A phosphorescent emitter or delayed fluorescent and phosphorescent emitters represented by Formula 1 or Formula II, where M is platinum or palladium.
Claims20
A compound of Formula I:
- wherein M is platinum or palladium,
- L1 is diazolyl,
- each L2 and L3 is phenyl,
- L4 is pyridyl,
- each of F1 and F2 is independently present or absent, wherein at least one of F1 and F2 is present, and each of F1 and F2 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 R1l, R2l, R3l, R4l, R5l, R6l, R7l, R8l, R9l and R10l is independently a mono-, di-, or tri-substitution, and each of R1l, R2l, R3l, R4l, R5l, R6l, R7l, R8l, R9l and R10l, 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 Ya, Yb, Yc, Yd, Ye, Yf, Yg, Yh, Yi, Yj, Yk, Yl, Ym, Yn, Yo, and Yp, if present, is independently C, N or B,
- each of Ua and Ub, if present, is independently CH2, CR1R2, C═O, CH2, SiR1R2, GeH2, GeR1R2, NH, NR3, PH, PR3, R3P═O, AsR3, R3As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BH, BR3, R3Bi═O, BiH, or BiR3,
- each of W, Wa, and Wb, if present, is independently CH, CR1, SiR1, GeH, GeR1, N, P, B, Bi, or Bi═O,
- A1 is O,
- A2 is O, N, or NR3,
- each V1 and V4 is N;
- each V2 and V3 is C,
- each Y1, Y2, and Y3 is C,
- Y4 is N,
- Ra is present or absent, wherein Rb is present or absent, wherein Rc is present or absent, wherein Rd is present or absent, and if present each of Ra, Rb, Rc, and Rd independently represents mono-, di-, or tri-substitutions, and wherein each of Ra, Rb, Rc, and Rd 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 Ra, two Rb, two Rc, or two Rd optionally combine together form a ring;
- and
- each of R1, R2, and R3 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 R3 and Rc, R3 and Rd, R3 and L3, and R3 and L4 optionally combine together form a ring.
28 more elements
A compound represented by one of the following structures:
- wherein:
- M is platinum or palladium;
- n is an integer;
- and
- each of R, R1, and R2 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, 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 more elements
A compound represented by one of the following structures:
Dependencies are inferred from the claim text.