Metal-assisted delayed fluorescent emitters containing tridentate ligands
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.
1. A compound represented by Formula A-2:
wherein:
M is Pt or Pd
L 1 is pyridine,
L 2 is phenyl,
L 3 is pyridine,
R L4 is an inorganic anion or organic anion,
each of LP 1 , LP 2 , and LP 3 is independently a fluorescent luminophore, each of LP 1 , LP 2 , and LP 3 is independently present or absent, and at least one of LP 1 , LP 2 , or LP 3 is present,
LP 1 is covalently bonded to L 1 directly,
LP 2 is covalently bonded to L 2 directly,
LP 3 is covalently bonded to L 3 directly,
A is O,
each of V 1 and V 3 is N,
V 2 is C,
each of Y 1 , Y 2 , Y 3 , and Y 4 is C,
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.
2. The compound of claim 1 , wherein each of LP 1 , LP 2 , and LP 3 , if present, 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.
3. 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, dialkylamino, 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.
4. 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:
and derivatives thereof, and
other fluorescent luminophores selected from the group consisting of:
wherein:
each of R al , R bl , R cl , R dl , R el , R fl , R gl , R hl , and R il independently represents one of the following structures:
each R 1l , R 2l , R 3l , R 4l , R 5l , R 6l , R 7l , R 8l , R 9l , R 10l is independently hydrogen, and R 11l 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,
each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o , Y P is independently C, N or B,
each of U 2 , U a , and U b is independently CH 2 , CR 1 R 2 , C═O, CH 2 , SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 , and
each of W a and W b is independently CH, CR 1 , SiR 1 , GeH, GeR 1 , N, P, B, Bi, and Bi═O.
5. The compound of claim 1 , wherein the compound is represented by one of the following structures:
wherein each of R, R 1 , and R 2 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.
6. The compound of claim 1 , wherein the compound is a delayed fluorescent and phosphorescent emitter, a phosphorescent emitter, or a delayed fluorescent emitter.
7. A device comprising the compound of claim 1 , wherein the device is an organic light emitting diode or a full color display.
8. A device comprising the compound of claim 5 , wherein the device is an organic light emitting diode or a full color display.