WO2014031977A1 - Metal compounds and methods and uses thereof - Google Patents
Metal compounds and methods and uses thereof Download PDFInfo
- Publication number
- WO2014031977A1 WO2014031977A1 PCT/US2013/056426 US2013056426W WO2014031977A1 WO 2014031977 A1 WO2014031977 A1 WO 2014031977A1 US 2013056426 W US2013056426 W US 2013056426W WO 2014031977 A1 WO2014031977 A1 WO 2014031977A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- independently
- cycloalkane
- substituted
- heterocyclyl
- aryl
- Prior art date
Links
- 0 CC(CC*)(C1)C2C3C1=C(C)C3C2 Chemical compound CC(CC*)(C1)C2C3C1=C(C)C3C2 0.000 description 54
- OMHCUOVXQHMVTH-UHFFFAOYSA-N C1c(cccc23)c2[n]2c4c1cccc4c1cccc3c21 Chemical compound C1c(cccc23)c2[n]2c4c1cccc4c1cccc3c21 OMHCUOVXQHMVTH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/006—Palladium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/331—Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- Cyclometalated metal complexes can be used for many applications including host materials and emitters for OLEDs.
- One of most important factors dictating the quantum efficiency of emission, is proportional to the integral of wavefunction of ground state and excited state, which favors a small difference in their equilibrium geometry.
- the present invention relates to, in one aspect, to metal compounds that can be useful as host materials in, for example, full color displays.
- the present invention also relates, in one aspect to metal compounds that can be useful as emitters for devices, such as OLEDs
- M comprises Pt, Pd, Ir, Rh, or Au; wherein each of R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Y la , Y lb , and Y lc independently is O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkan
- M comprises Ir, Rh, Pt, Ru, or Os; wherein each of R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Y la , Y lb , Y lc , Y ld , and Y le independently is O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl,
- M represents a metal cation with three positive charges, which include, but are not limited to Gold(III) (Au 3+ ), silver(III) (Ag 3+ ), wherein each E 1 , E 2 , and E independently represent a linking atom comprising O, NR , CR R , S, BR ,
- M represent a metal cation with one positive charges, which include, but is not limited to, iridium (I) (Ir 1+ ), Rhodium (I) (Rh 1+ ), etc., wherein E 1 , E 2 , and E 3
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ), Aluminum(III) (Al 3+ ),and Gallium(III) (Ga 3+ ), wherein E 1 , E 2 , E 3 , and E 4
- 2 2 3 2 2 independently represent a linking atom,comprising O, NR , CR R , S, BR , PR , 2 2 3 2 3
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ), Aluminum(III) (Al 3+ ),Gallium(III) (Ga 3+ ), wherein E 1 , E 2 , E 3 , E 4 , and E 5
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ), Aluminum(III) (Al 3+ ),Gallium(III) (Ga 3+ ), wherein E 1 , E 2 , E 3 , E 4 , and E 5
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
- M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd 4+ ), Platinum(IV) (Pt 4+ ), wherein E 1 , E 2 , E 3 , and E 4 , independently represent a linking atom comprising O, NR 2 , CR 2 R 3 , S, BR 2 ,
- M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd 4+ ), Platinum(IV) (Pt 4+ ), wherein E 1 , E 2 , E 3 , E , and E independently represent a linking atom comprising O, NR , CR R , S, BR , 2 2 2 3 2 3
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ),
- M represent a metal cation with two positive charges, which include,
- compositions comprising one or more of the disclosed compounds.
- Suitable devices include, but are not limited to, OLEDs and full color displays.
- Figure 1 shows the absorption spectra of the compound Pt-OOO (inset) in dichloromethane at room temperature, and the emission spectra at 77K in 2- methy ltetrahyrdo furan .
- Figure 2 shows the I-V curve of a device with PtOOO have the structure
- Figure 3 shows the EL spectrum of devices using mCPy (dashed line) and PtOOO(solid line) as host materials.
- Figure 4 shows the EQE of devices using mCPy (dashed line) and PtOOO(solid line) as host materials.
- Figure 5 shows the emission spectra of PfNON in dichloromethane at room temperature (solid line) and in 2-methyl THF at 77 K (dashed line).
- Figures 6A-6C show plots of (6A) current density vs. voltage, (6B) external quantum efficiency vs. brightness and (6C) EL spectra for the devices of ITO/HATCN (10nm)/NPD (40nm)/TAPC (lOnm)/ x% PtNON:26mCPy
- Figure 7 shows the emission spectra of PtNNN in dichloromethane at room temperature.
- Figure 8 shows the emission spectra of PtNOO in dichloromethane at room temperature.
- Figure 9 shows the emission spectra of PtNON-bph in dichloromethane at room temperature.
- Figure 10 shows the emission spectra of PdNON-bph in dichloromethane at room temperature.
- Figure 1 1 shows the emission spectra of Pt ON-ph in dichloromethane at room temperature.
- Figure 12 shows the emission spectra of PdNON-ph in dichloromethane at room temperature.
- Figure 13 shows the emission spectra of PfNNO in dichloromethane at room temperature.
- compositions of the invention Disclosed are the components to be used to prepare the compositions of the invention as well as the compositions themselves to be used within the methods disclosed herein. These and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds cannot be explicitly disclosed, each is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and a number of modifications that can be made to a number of molecules including the compounds are discussed, specifically contemplated is each and every combination and permutation of the compound and the modifications that are possible unless specifically indicated to the contrary.
- a linking atom connect two groups such as, for example, a and C group.
- the linking atom can, if valency permits, have other chemical moieties attached.
- an oxygen would not have any other chemical groups attached as the valency is satisfied once it is bonded to the two groups (N and/or C groups).
- carbon is the linking atom
- two additional chemical moieties would be attached to the carbon as valency would require such.
- alkyl as used herein is a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl, ethyl, w-propyl, isopropyl, w-butyl, isobutyl, s-butyl, ?-butyl, w-pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like.
- the alkyl group can be cyclic or acyclic.
- the alkyl group can be branched or unbranched.
- the alkyl group can also be substituted or unsubstituted.
- the alkyl group can be substituted with one or more groups including, but not limited to, optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol, as described herein.
- a "lower alkyl” group is an alkyl group containing from one to six (e.g., from one to four) carbon atoms.
- a , A , and A can be, independently, hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.
- halide refers to the halogens fluorine, chlorine, bromine, and iodine.
- hydroxyl as used herein is represented by the formula— OH.
- nitro as used herein is represented by the formula— O 2 .
- nitrile as used herein is represented by the formula— CN.
- heterocyclyl refers to cyclic structures including a heteroatom.
- heterocyclyl includes both aromatic and non- aromatic ring structures with one or more heteroatoms.
- Non-limiting examples of heterocyclic includes, pyridine, isoquinoline, methylpyrrole and thiophene etc.
- Heteroaryl specifically denotes an aromoatic cyclic structure including a heteroatom.
- N nitrogen
- valency is indicated to be neutral in the structure it can if appropriate, as appreciated by those skilled in the art, be a cationic species having a net positive charge due to the coordination.
- nitrogen can be shown in the structures to have neutral charge or a positive charge and in some cases these structures can be used interchangeably as appropriate and as recognized by one skilled in the art.
- references to such "metals” oin this application does NOT imply a particular valence, chemical, or physical state of those elements, or that those elements are necessarily in a zero valent state, or metallic solid physical state or alloy (although they could be in such states), but rather that the term "metal” or “metals” can also be present in a compound with other elements or groups wherein the metal can be present in any energetically feasible positive oxidation state (i.e. cationic oxidation states).
- a reference to platinum (Pt) includes the cationic form Pt 2+ of platinum or Pt 4+ of platinum.
- the present invention is directed to metal compounds or complexes, such as platinum, palladium, gold, silver, ruthenium, iridium, rhodium, aluminum, gallium, cobalt, and osmium compounds.
- the compositions disclosed here can provide emission spectra of platinum, palladium, gold, silver, ruthenium, iridium, rhodium, aluminum, gallium, cobalt, and osmium.
- the compositions disclosed herein can provide tunable emission spectra.
- the disclosed compounds are useful as host materials in devices, such as full color displays.
- the disclosed compounds are useful as emitters in devices, such as OLEDs.
- Cyclometalated metal complexes can be used for many applications including emitters for OLEDs.
- an efficient emitter requires a rigid planar chemical structure, which has 5- membered coordination rings (Scheme 1).
- emitters containing unplanar lumophore do not have strong emission at the room temperature due to their distorted molecular geometry, which has 6-membered coordination rings (Scheme lb).
- This invention provides a materials design route which enables the emitters with 6-membered coordination rings to be efficient emitters and have tunable emission wavelength in the visible range.
- This class of emitters can be utilized as emitters for full color displays and lighting applications. To make this work, one condition needs to be satisfied: the molecular geometry needs to be very rigid. The molecular structure of four-coordinating ligands will be preferred which ensures the
- PtNON is an emitter with 6-membered coordination rings, which has demonstrated an electron-to-photon conversion efficiency over 20% in the device settings
- the invention also relates to metal compounds that can be useful as emitters in devices, such as OLEDs.
- the emission (and absorption) profile of the compounds can be tuned by varying the structure of the ligand surrounding the metal center.
- compounds having a ligand with electron withdrawing substituents will generally exhibit different optical properties, including emission and absorption, than compounds having a ligand with electron donating substituents.
- a chemical structural change affects the electronic structure of the compound, which thereby affects the absorption and emission of the compound.
- the compounds of the present invention can be tailored or tuned to a specific application that desires a particular emission or absorption characteristic.
- the emission spectrum of any of the compositions of the present disclosure can be tuned to a desired and/or customized spectrum.
- the complexes disclosed herein can provide a narrow bandwidth, enabling their use in, for example, applications in which broad spectrum emitters are not suitable.
- the excited state dynamics of the complex can be described by the scheme: 1 M LCT
- 3 LC represents the energy of the ligand centered triplet state
- ⁇ LCT represents the energy of the metal-to-ligand charge transfer singlet state
- Ti represents the energy of the emissive triplet state
- So represents the energy of the ground state
- ⁇ represents the difference in energy between ⁇ LCT and 3 LC.
- an expansion utilizing different emitting portions and linking groups should provide narrow emitting complexes covering a wide range of the visible spectrum.
- the emission energy of a certain complex can be tuned by modifying the ligand centered triplet state of the emitting fragment ( 3 LC). This can be accomplished through changes in structure that modify the energy of the donating or accepting portion of the emitting fragment.
- the nature of the ⁇ LCT transitions can be controlled by modifying the ancillary portion of the complex (L A X), through changes in the cyclometalating portion, the linking portions, or both.
- the inventive compositions are useful as emitters for full color display application.
- the geometry of cyclometalating ligands can be rigid. This rigidity can allow for similar geometry between the ground and excited state, resulting in a narrow emission spectra dominated by the transition from the lowest vibrational level in the excited state to the lowest vibrational level in the ground state.
- complexes can be designed to tune the values of the emitting fragment centered 3 LC state and the metal to ancillary ligand ⁇ LCT states independently. Reduction in the differences in energy between these states ( ⁇ ) will improve mixing between them, improve the radiative decay rate, and suppress transitions that occur from the emissive state (Ti) to excited vibrational levels in the ground state (So). As a consequence, the vibrational shoulders of the emission spectra can be reduced, resulting in a more narrow emission profile.
- the molecular structure having four coordinating ligands to a metal center can be preferred.
- a four ligand coordinated structure can at least partially ensure the electrochemical and/or photophysical stability of the complex during, for example, fabrication and operation of a color display device.
- the inventive compositions can provide improved efficiency and/or operational lifetimes in lighting devices, such as, for example, organic light emitting devices, such as OLEDs, as compared to conventional materials.
- OLEDs organic light emitting devices
- devices comprising the complexes described herein.
- One application for phosphoresent emissive complexes, such as those described herein, is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
- M can comprise Pt. In another aspect, M can comprise Pd. In yet another aspect, M can comprise Rh. In yet another aspect, M can comprise Ir. In yet another aspect, M can comprise Au. In yet another aspect, M can comprise Ag. In yet another aspect, M can comprise Cu. In yet another aspect, M can comprise Zr. In yet another aspect, M can comprise Hg. In yet another aspect, M can comprise Ga. In yet another aspect, M can comprise Co. In yet another aspect, M can comprise Os. In yet another aspect, M can comprise Ru.
- At least one of Y la , Y lb , and Y lc is NR 2 . In another aspect, at least two of Y la , Y lb , and Y lc are NR 2 . In yet another aspect, Y la , Y lb , and Y lc are NR 2 .
- At least one of Y la , Y lb , Y lc , Y ld , and Y le is NR 2 .
- at least two of Y la , Y lb , Y lc , Y ld , and Y le are NR 2 .
- at least three of Y la , Y lb , Y lc , Y ld , and Y le are NR 2 .
- Y lc , Y ld , and/or Y le can independently comprise O.
- at least one of yla ylb Y lc ; yld yle can independently comprise NR 2 .
- at least one of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise CR 2 R 3 .
- at least one of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise S.
- At least one of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise BR 2 . In yet another aspect, at least one of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise PR 2 . In yet another aspect, at least one of Y la , yib Yid j and/or Y ie can independently comprise P(0)R 2 . In yet another aspect, at least one of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise SiR 2 R 3 . In one aspect, Y la , Y lb , Y lc , Y ld , and/or Y le can be oxygen
- each of R 2 and R 3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, or heterocyclyl, wherein each R 2 and R 3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
- each of R 2 and R 3 independently is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl, wherein each of R 2 and R 3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
- one of R 2 or R 3 is aryl, wherein each of R 2 and R 3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure. In one aspect, each of R 2 and R 3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
- each of Y la , Y lb , Y lc , Y ld , and/or Y le can to ring structure
- each of Y la , Y lb , Y lc , to ring structure is a ring structure, for example or .
- each of Y la , Y lb , Y lc , to ring structure is a ring structure, for example or .
- Y ld , and/or Y le can independently compris , for
- each of Y la , Y lb , Y lc , Y ld , and/or Y le can linked to ring to ring structure independently comprise
- each of Y la Y l ,
- ylb Y l Cj Y ld and/or Y le can independently comprise
- Y le can independently comprise Pn .
- each of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise ⁇ .
- each of ⁇ ", ⁇ ", ⁇ ' ⁇ , Y la , and/or ⁇ ] ⁇ can independently comprise Ph .
- each of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise ⁇ S ⁇ - .
- each of Y la , Y lb , Y lc , Y ld , and/or Y le can independently comprise O
- each of Y 2a , Y 2b , Y 2c , and Y 2d independently is N, NR 6a , or CR 6b , wherein each of R 6a and R 6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene.
- At least one of Y 2a , Y 2b , Y 2c , and Y 2d is CR*. In another aspect, at least two of Y 2a , Y 2b , Y 2c , and Y 2d is CR 6b . In yet another aspect, at least three of Y 2a , Y 2b , Y 2c , and Y 2d is CR 6b . In yet another aspect, at least one of Y 2a , Y 2b , Y 2c , and Y 2d is NR 6a .
- each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , and Y 4d independently is N, O, S, NR 6a , CR* wherein each of R 6a and R 6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 6c )2, wherein Z is C or Si, and wherein each R 6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cyclo
- At least four of Y 3a , Y 3b , Y 3c , and Y 3d are CR 6b . In another aspect, at least three of Y 3a , Y 3b , Y 3c , and Y 3d are CR 6b . In another aspect, at least one of Y 3a , Y 3b , Y 3c , and Y 3d is N or NR 6a . In another aspect, at least four of Y 4a , Y 4b , Y 4c , and Y 4d are CR 6b . In another aspect, at least three of Y 4a , Y 4b , Y 4c , and Y 4d are CR 6h . In another aspect, at least one of Y 4a , Y 4b , Y 4c , and Y 4d is N or NR 6a .
- each of Y 5a , Y 5b , Y 5c , Y 5d , Y 6a , Y 6b , Y 6c , and Y 6d independently is N, O, S, NR 6a , or CR 6b .
- at least four of Y 5a , Y 5b , Y 5c , and Y 5d are CR 6b .
- at least three of Y 5a , Y 5b , Y 5c , and Y 5d are CR 6b .
- At least one of Y 5a , Y 5b , Y 5c , and Y 5d is N or NR 6a .
- at least four of Y 6a , Y 6b , Y 6c , and Y 6d are CR 6b .
- at least three of Y 6a , Y* Y 6c , and Y 6d are CR 6b .
- at least one of Y 6a , Y 6b , Y 6c , and Y 6d is or R 6a .
- R 6b is hydrogen. In another aspect, at least one R 6b is hydrogen. In another aspect, at least one R 6b is alkyl or aryl. [0081] In one aspect, R a is hydrogen. In another aspect, at least one R a is hydrogen. In another aspect, at least one R 6a is alkyl or aryl.
- m is 1. In another aspect, m is 2. In one aspect, at least one m is 1. In another aspect, at least one m is 2. In one aspect, n is 1. In another aspect, n is 2. In yet another aspect, at least one m is 1 and at least one m is 2. In yet another aspect, at least one m is 1 and n is 1. In yet another aspect, at least one m is 1 and n is 2. In yet another aspect, at least one m is 2 and « is 2. In yet another aspect, at least one m is 2 and n is 2.
- the compounds disclosed herein can have a structure where m is 2, n is 2, Y 2b is CH, Y 3b , Y 2c and Y 4b is N, Y lb is NR 2 , CR 2 R 3 , AsR 2 , BR 2 ,
- the compounds disclosed herein can have a structure where at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C, at least one of Y lb and Y lc is NR 2 , CR 2 R 3 , AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R 2 is covalently linked to at least one of Y 2a , Y 2d , Y 3d and Y 4d , thereby forming
- the compounds disclosed herein can have a structure where at least of one of Y 2a and Y 3d is C, Y lb is NR 2 , CR 2 R 3 , AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R 2 is covalently linked to at least one of Y 2a and Y 3d , thereby forming a cyclic structure, and M is Ir or Rh.
- the compounds disclosed herein can have a structure where at least of one of Y 2a and Y 3d is C, Y lb is NR 2 , CR 2 R 3 , AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R 2 is covalently linked to at least one of Y 2a and Y 3d , thereby forming a cyclic structure, and wherein M is Au.
- the compounds disclosed herein can have a structure where at least of one of Y 2a , Y 2d , Y 3d and Y 4d is C, at least one of Y lb and Y lc is NR 2 , CR 2 R 3 , AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R 2 is covalently linked to at least one of Y 2a , Y 2d , Y 3d and Y 4d , thereby forming
- the compounds disclosed herein can have a structure where m is 2, n is 2, Y 2b and Y 2c is CH, Y 3b and Y 4b is N. In yet another aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, and Y 2b and Y 2c is CH. In another aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, and Y 3b and Y 4b is N.
- At least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise O. In another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can
- At least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise CR 2 R 3 . In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise S. In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise BR 2 . In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise PR 2 .
- At least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise P(0)R 2 . In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise P(0)R 2 . In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise P(0)R 2 . In yet another aspect, at least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can
- E , E , E , and E can be oxygen.
- At least one of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently can be absent from a structure recited herein, whereby a bond is then directly present between any Ns and/or Cs.
- each of R 2 and R 3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, or heterocyclyl, wherein each of R 2 and R 3 independently is optionally linked to a C and/or N, thereby forming a cyclic structure.
- each of R 2 and R 3 independently is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl, wherein each of R 2 and R 3 independently is optionally linked to a C or N, thereby forming a cyclic structure.
- one of R 2 or R 3 is aryl, wherein each of R 2 and R 3 independently is optionally linked to a C or N, thereby forming a cyclic structure. In one aspect, each of R 2 and R 3 independently is linked to a C or N, thereby forming a cyclic structure.
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently be linked
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise
- E 3 , E 4 , and/or E 5 can independently comprise , for example,
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can inkM to C As ink to independently comprise , for example,
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise , for example, . In yet another aspect, each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise
- E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise Pn .
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise / ⁇ .
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise ph .
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise .
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise p h h .. ;
- each of E 1 , E 2 , E 3 , E 4 , and/or E 5 can independently comprise p h h .. ;
- At least one of E , E , and E is O. In another aspect, at
- E , E , and E are O.
- E , E , and E can be oxygen.
- E , E , and E can comprise O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a
- E 1 and E 3 can be oxygen.
- E 2 comprise O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 ,
- At least one of E , E , and E is
- At least one of E , E , and E is . In yet another aspect, at least one of E 1 , E 2 , and E 3 is Pn . In yet another aspect, at least one of
- E 1 , E 2 , and E 3 is Ph . In yet another aspect, at least one of E 1 , E 2 , and E 3 is
- At least one of E 1 , E 2 , and E 3 is Pn . In yet another aspect, at least one of E 1 , E 2 , and E 3 is ⁇ S ⁇ - . in yet another aspect, at least one of
- E 1 , E 2 , and E 3 is Ph .
- At least one of E 1 , E 2 , E 3 , and E 4 is O. In another aspect, at least two of E 1 , E 2 , E 3 , and E 4 are O. In yet another aspect, at least three of E 1 , E 2 , E 3 , and E 4 are O. In yet another aspect, E 1 , E 2 , and E 3 can be oxygen. In yet another aspect, E 1 , E 2 , E 3 , and E 4 can be oxygen. In yet another aspect, E 1 , E 2 , E 3 , E 4 , and E 5 can be oxygen.
- At least one of E 1 , E 2 , E 3 , and E 4 is NR 2 . In another aspect, at least two of E 1 , E 2 , E 3 , and E 4 are NR 2 . In yet another aspect, at least three
- E , E , and E are NR .
- E , E , and E can be NR .
- E 1 , E 2 , E 3 , and E 4 can be NR 2 .
- E 1 , E 2 , E 3 , E 4 , and E 5 can be NR 2 .
- At least one of E 1 , E 2 , E 3 , and E 4 is NR 2 , CR 2 R 3 , S, BR 2 ,
- At least two of E 1 , E 2 , E 3 , and E 4 is NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R , or SiR R J , or a combination thereof, wherein each of R and R
- At least one in one aspect, at least one . In another aspect, at
- At least one N is .
- At least one N is . In yet another aspect, at least one N is In yet another aspect, at least one N is . In another aspect, the
- N groups can be substituted heterocyclyl.
- the N groups can be unsubstituted heterocyclyl.
- the N groups can be pyridine.
- At least one C is . In another aspect, at least one C is .
- At least one C is . In yet another aspect, at least one C is . In yet another aspect, at least one C is . In yet another aspect, at least one C is . In yet
- At least one C is . In yet another aspect, at least one C is . In yet another aspect, at least one C is . In yet another aspect, at least one C . In one aspect, C can be an unsubstituted aromatic ring or heterocyclic group. In another aspect, C can be a unsubstituted aromatic ring or heterocyclic group. In another aspect, C can be a substituted aromatic ring or heterocyclic group. In one aspect, the C groups can be phenyl.
- R which can represent R 2 or R 3 as defined herein.
- X, A, and A can have the meaning of Y lb , Y la , and Y lc as described herein.
- V and W could be the same or different atoms like carbon (C) nitre sulfur (S), phosphorus (P), silicon (Si), boron (B) and others.
- U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si)
- the compounds can have the structure:
- M is Ir or Rh.
- U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), boron (B) and other atoms.
- the compounds can have the structure:
- U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), boron (B) and other atoms.
- the compound can have the structure:
- M can be Pt or Pd.
- M comprises Pt, Pd, Ir, Rh, or Au; wherein each of R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Y la , Y lb , and Y lc independently is O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkan
- M comprises Ir, Rh, Pt, Os, or Ru
- R 1 and R 2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
- each of Y la , Y lb , Y lc , Y ld , and Y le independently is O, NR 2 , CR 2 R 3 , S, AsR 2 , BR 2 , PR 2 , P(0)R 2 , or SiR 2 R 3 , or a combination thereof, wherein each of R 2 and R 3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl,
- M represent a metal cation with two positive charges, which include, but are not limited to Platinum(II) (Pt 2+ ), Palladium(II) (Pd 2+ ), wherein
- M can be Platinum (II). In one aspect, M can be Palladium (II).
- the compound can be:
- each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl.
- M represents a metal cation with three positive charges, which include, but are not limited to Gold(III) (Au 3+ ), silver(III) (Ag 3+ ), wherein each E 1 , E 2 ,
- 3 2 2 3 2 and E independently represent a linking atom comprising O, NR , CR R , S, BR ,
- E 1 , E 2 , and E 3 can be oxygen.
- E 1 and E 3 can be oxygen.
- E 2 can be nitrogen, oxygen, carbon, silicon,
- M can be Au (III). In one aspect, M can be Ag (III).
- the compound can have the structure:
- M represent a metal cation with one positive charges, which include, but is not limited to, iridium (I) (Ir 1+ ), Rhodium (I) (Rh 1+ ), etc., wherein E 1 , E 2 , and E 3
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
- M can be Rhodium (I). In one aspect, M can be Iridium
- the compound can have the structure:
- each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl.
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ),
- 2 2 3 2 2 independently represent a linking atom,comprising O, NR , CR R , S, BR , PR ,
- M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
- M can be gallium (III).
- the compound can have the structure
- each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ),
- M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
- M can be gallium (III).
- the compound has the structure:
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ),
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
- M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
- M can be gallium (III).
- the compound has the structure:
- M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd 4+ ), Platinum(IV) (Pt 4+ ), wherein E 1 , E 2 , E 3 , and E 4 ,
- 2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR R J , or a combination thereof, wherein each of R and R
- M can be Platinum (VI). In one aspect, M can be Palladium (VI).
- the compound can have the structure:
- each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
- M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd 4+ ), Platinum(IV) (Pt 4+ ), wherein E 1 , E 2 , E 3 , E 4 , and
- E independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR R J , or a combination thereof, wherein each of R and R
- M can be Platinum (VI). In one aspect, M can be Palladium (VI).
- the compound can have the structure:
- M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir 3+ ), Rhodium(III) (Rh 3+ ), Cobalt (III) (Co 3+ ),
- the C groups can be phenyl.
- the N groups can be pyridine.
- E 1 , E 2 , E 3 , and E 4 can be oxygen.
- M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
- M can be gallium (III).
- the compound has the structure:
- R is hydrogen, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di- alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
- M represent a metal cation with two positive charges, which include, but are
- E independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR R J , or a combination thereof, wherein each of R and R
- the C groups can be phenyl.
- the N groups can be pyridine.
- E 1 , E 2 , E 3 , E 4 , and E 5 can be oxygen.
- M can be Iridium (III).
- M can be Rhodium (III).
- M can be Cobalt (III).
- M can be
- M can be gallium (III).
- the present invention is directed to metal compounds. Also disclosed are compositions comprising one or more of the disclosed compounds.
- the present invention is directed to metal compounds.
- the compounds or compositions disclosed here can be used as host materials for OLED applications, such as full color displays.
- the compounds or compositions disclosed here can be used a emitter materials for OLED applications or displays.
- the compounds can be the host material in the device.
- device can be a lighting device.
- the disclosed compounds of the present disclosure can be useful in a wide variety of applications, such as, for example, lighting devices.
- one or more of the compounds can be useful as host materials for an organic light emitting display device.
- the disclosed compounds are useful in a variety of applications.
- the compounds can be useful in organic light emitting diodes (OLED)s, luminescent devices and displays, and other light emitting devices.
- OLED organic light emitting diodes
- the energy profile of the compounds can be tuned by varying the structure of the ligand surrounding the metal center. For example, compounds having a ligand with electron withdrawing substituents will generally exhibit different properties, than compounds having a ligand with electron donating substituents. Generally, a chemical structural change affects the electronic structure of the compound, which thereby affects the electrical transport and transfer functions of the material. Thus, the compounds of the present invention can be tailored or tuned to a specific application that desires an energy or transport characteristic.
- disclosed compound can provide improved efficiency and/or operational lifetimes in lighting devices, such as, for example, organic light emitting devices, as compared to conventional materials.
- the disclosed compounds can be useful as, for example, host materials for organic light emitting diodes, lighting applications, and combinations thereof.
- the device is an electro-optical device.
- Electro-optical devices include, but are not limited to, photo-absorbing devices such as solar- and photo-sensitive devices, organic light emitting diodes (OLEDs), photo-emitting devices, or devices capable of both photo-absorption and emission and as markers for bio-applications.
- the device can be an OLED.
- OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
- an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
- the anode injects holes and the cathode injects electrons into the organic layer(s).
- the injected holes and electrons each migrate toward the oppositely charged electrode.
- an "exciton” which is a localized electron-hole pair having an excited energy state, is formed.
- Light is emitted when the exciton relaxes via a photoemissive mechanism.
- the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
- the initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No.
- Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
- phosphorescent emissive molecules are full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art. Such devices are disclosed herein which comprise one or more of the compounds or composition disclosed herein.
- the OLED can be produced by methods known to those skilled in the art.
- the OLED is produced by successive vapor deposition of the individual layers onto a suitable substrate.
- Suitable substrates are, for example, glass, inorganic materials such as ITO or IZO or polymer films.
- customary techniques may be used, such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) and others.
- the organic layers may be coated from solutions or dispersions in suitable solvents, in which case coating techniques known to those skilled in the art are employed. Suitable coating techniques are, for example, spin-coating, the casting method, the Langmuir-Blodgett ("LB") method, the inkjet printing method, dip-coating, letterpress printing, screen printing, doctor blade printing, slit-coating, roller printing, reverse roller printing, offset lithography printing, flexographic printing, web printing, spray coating, coating by a brush or pad printing, and the like.
- LB Langmuir-Blodgett
- the coating can be obtained using a solution prepared by dissolving the composition in a concentration of 0.0001 to 90% by weight in a suitable organic solvent such as benzene, toluene, xylene, tetrahydrofuran, methyltetrahydrofuran, ⁇ , ⁇ -dimethylformamide, acetone, acetonitrile, anisole, dichloromethane, dimethyl sulfoxide, water and mixtures thereof
- Scheme 1 shows the general scheme for the synthesis of the compounds disclosed herein.
- PtOOO was tested as a host material in a device having the following structure: ITO/HATCN (10nm)/ NPD (40nm)/ TAPC (lOnm)/ 6% Pt003: Host/ DPPS (10nm)/BmPyPB (40nm)/LiF/Al.
- the I-V curve for this device compared to a device using mCPy as a host material is shown in figure 2.
- the EL spectrum this device compared to a device using mCPy as a host material is shown in figure 3.
- the EQE for this device compared to a device using mCPy as a host material is shown in figure 4.
- the precipitate was collected through filtration, washed with water for three times then dried in air and purified through column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in dichloromethane and ether at refrigerator to get the desired platinum compound PtNOO as a bright yellow solid 72 mg in 23 % yield.
Abstract
Disclosed herein are metal compounds, compositions, and devices related thereto, such as full color displays or OLEDs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Description
METAL COMPOUNDS AND METHODS AND USES THEREOF
STATEMENT OF GOVERNMENT SUPPORT
[0001] The present invention was made with financial support from the National Science Foundation (NSF) under Career Grant No. 0748867 and from a NSF GK-12 fellowship and from Department of Energy SSL Core Technology under Grant No. DE-EE0005075. The U.S. government has certain rights in this invention.
TECHNICAL BACKGROUND
[0002] Compounds capable of hole and electron conduction and efficient energy transfer are ideally suited for use in a wide variety of applications, including optical and electro-optical devices, and photo-absorbing devices. Much research has been devoted to the discovery and optimization of organic and organometallic materials for use in such applications. Generally, research in this area aims to accomplish a number of goals, including improvements in hole and electron transport and energy level tuning, as well as improvements in processing ability, among others.
[0003] Despite significant advances in research devoted to optical and electro- optical materials, existing host materials have a number disadvantages, including poor processing ability, poor energy matching to certain emissive materials, poor charge carrier mobility, among others. Thus, a need exists for new materials which exhibit improved performance. This need and other needs are satisfied by the present invention.
[0004] Cyclometalated metal complexes can be used for many applications including host materials and emitters for OLEDs. One of most important factors dictating the quantum efficiency of emission, is proportional to the integral of wavefunction of ground state and excited state, which favors a small difference in their equilibrium geometry.
[0005] Despite significant advances in research devoted to optical, electro- optical, and marker materials, existing materials have a number disadvantages, including poor processing ability, inefficient emission or absorption, and less than ideal stability, among others. Thus, a need exists for new materials which exhibit
improved performance in optical emitting and absorbing applications. This need and other needs are satisfied by the present invention.
SUMMARY
[0006] The present invention relates to, in one aspect, to metal compounds that can be useful as host materials in, for example, full color displays. The present invention also relates, in one aspect to metal compounds that can be useful as emitters for devices, such as OLEDs
[0007] In one aspect, disclosed herein is a compound having the structure:
wherein M comprises Pt, Pd, Ir, Rh, or Au; wherein each of R1 and R2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Yla, Ylb, and Ylc independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure; wherein each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR* wherein each of R6a and R6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio,
alkoxy, haloalkyl, arylalkane, or arylalkene; each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR6b, wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of m and n independently are an integer 1 or 2; wherein each of - ' independently is partial or full unsaturation of the ring with which it is associated.
[0008] In one aspect, disclosed herein is a compound having the structure:
[0009] wherein M comprises Ir, Rh, Pt, Ru, or Os; wherein each of R1 and R2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Yla, Ylb, Ylc, Yld, and Yle independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3
independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure; wherein each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR6b, wherein each of R6a and R6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR* wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein in each of each of y5a Y5b Y5Cj y5d γ& ^b^ Y6Cj ^ y6d independently ig N> Q § > & Qr CR6b; wherein each of m and n independently are an integer 1 or 2; wherein each of independently is partial or full unsaturation of the ring with which it is associated.
[0010] In one aspect, disclosed herein is a compound having the structure:
wherein the formula, M represent a metal cation with two positive charges, which include, but are not limited to Platinum(II) (Pt2+), Palladium(II) (Pd2+), wherein E , E , and E independently represent a linking atom comprising O, NR , CR R , S, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3
independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0011] In one aspect, disclosed herein is a compound having the structure:
wherein M represents a metal cation with three positive charges, which include, but are not limited to Gold(III) (Au3+), silver(III) (Ag3+), wherein each E1, E2, and E independently represent a linking atom comprising O, NR , CR R , S, BR ,
2 2 2 3 2 3
PR", P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein N represents a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0012] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with one positive charges, which include, but is not limited to, iridium (I) (Ir1+), Rhodium (I) (Rh1+), etc., wherein E1, E2, and E3
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein C represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N
independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0013] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+), Aluminum(III) (Al3+),and Gallium(III) (Ga3+), wherein E1, E2, E3, and E4
2 2 3 2 2 independently represent a linking atom,comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0014] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+), Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, E4, and E5
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)R% or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0015] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+), Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, E4, and E5
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)R% or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0016] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd4+), Platinum(IV) (Pt4+), wherein E1, E2, E3, and E4, independently represent a linking atom comprising O, NR2, CR2R3, S, BR2,
2 2 2 3 2 3
PR", P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0017] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd4+), Platinum(IV) (Pt4+), wherein E1, E2, E3, E , and E independently represent a linking atom comprising O, NR , CR R , S, BR ,
2 2 2 3 2 3
PR , P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0018] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+),
Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, and E4, independently represent a linking atom comprising O, NR2, CR2R3, S, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0019] In one aspect, disclosed herein is a compound having the structure:
2 1 2 ^ but are not limited to, Ruthenium (II) (Ru ), Osmium (II) (Os ), wherein E , E , E , E , and E independently represent a linking atom comprising O, NR , CR R , S, BR , PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[0020] Also disclosed herein are compositions comprising one or more of the disclosed compounds.
[0021] Also disclosed herein are devices comprising one or more of the disclosed compounds. Suitable devices include, but are not limited to, OLEDs and full color displays.
BRIEF DESCRIPTION OF THE FIGURES
[0022] The accompanying figures, which are incorporated in and constitute a part of this specification, illustrate several aspects and together with the description serve to explain the principles of the invention.
[0023] Figure 1 shows the absorption spectra of the compound Pt-OOO (inset) in dichloromethane at room temperature, and the emission spectra at 77K in 2- methy ltetrahyrdo furan .
[0024] Figure 2 shows the I-V curve of a device with PtOOO have the structure
ITO/HATCN (lOnm)/ NPD (40nm)/ TAPC (lOnm)/ 6% Pt003: Host/ DPPS
(10nm)/BmPyPB (40nm)/LiF/Al.
[0025] Figure 3 shows the EL spectrum of devices using mCPy (dashed line) and PtOOO(solid line) as host materials.
[0026] Figure 4 shows the EQE of devices using mCPy (dashed line) and PtOOO(solid line) as host materials.
[0027] Figure 5 shows the emission spectra of PfNON in dichloromethane at room temperature (solid line) and in 2-methyl THF at 77 K (dashed line).
[0028] Figures 6A-6C show plots of (6A) current density vs. voltage, (6B) external quantum efficiency vs. brightness and (6C) EL spectra for the devices of ITO/HATCN (10nm)/NPD (40nm)/TAPC (lOnm)/ x% PtNON:26mCPy
(25nm)/DPPS (10nm)/BmPyPB(40nm)/LiF/Al.
[0029] Figure 7 shows the emission spectra of PtNNN in dichloromethane at room temperature.
[0030] Figure 8 shows the emission spectra of PtNOO in dichloromethane at room temperature.
[0031] Figure 9 shows the emission spectra of PtNON-bph in dichloromethane at room temperature.
[0032] Figure 10 shows the emission spectra of PdNON-bph in dichloromethane at room temperature.
[0033] Figure 1 1 shows the emission spectra of Pt ON-ph in dichloromethane at room temperature.
[0034] Figure 12 shows the emission spectra of PdNON-ph in dichloromethane at room temperature.
[0035] Figure 13 shows the emission spectra of PfNNO in dichloromethane at room temperature.
[0036] Additional aspects of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or can be learned by practice of the invention. The advantages of the invention will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as claimed.
DESCRIPTION
[0037] The present invention can be understood more readily by reference to the following detailed description of the invention and the Examples included therein.
[0038] Before the present compounds, devices, and/or methods are disclosed and described, it is to be understood that they are not limited to specific synthetic methods unless otherwise specified, or to particular reagents unless otherwise specified, as such can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, example methods and materials are now described.
Definitions
[0039] As used in the specification and the appended claims, the singular forms "a,""an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes mixtures of two or more components.
[0040] Ranges can be expressed herein as from "about" one particular value, and/or to "about" another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent "about," it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as "about" that particular value in addition to the value itself. For example, if the value "10" is disclosed, then "about 10" is also disclosed. It is also understood that each unit between two particular units are also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.
[0041] As used herein, the terms "optional" or "optionally" means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.
[0042] Disclosed are the components to be used to prepare the compositions of the invention as well as the compositions themselves to be used within the methods disclosed herein. These and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds cannot be explicitly disclosed, each is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and a number of modifications that can be made to a number of molecules including the compounds are discussed, specifically contemplated is each and every combination and permutation of the compound and the modifications that are possible unless specifically indicated to the contrary. Thus, if a class of molecules A, B, and C are disclosed as well as a class of molecules D, E, and F and an example of a combination molecule, A-D is disclosed, then even if each is not individually recited each is individually and collectively contemplated meaning combinations, A-E, A-F, B-D, B-E, B-F, C-D, C-E, and C-F are considered disclosed. Likewise, any subset or combination of these is also disclosed. Thus, for example, the
sub-group of A-E, B-F, and C-E would be considered disclosed. This concept applies to all aspects of this application including, but not limited to, steps in methods of making and using the compositions of the invention. Thus, if there are a variety of additional steps that can be performed it is understood that each of these additional steps can be performed with any specific embodiment or combination of
embodiments of the methods of the invention.
[0043] As referred to herein, a linking atom connect two groups such as, for example, a and C group. The linking atom can, if valency permits, have other chemical moieties attached. For example, an oxygen would not have any other chemical groups attached as the valency is satisfied once it is bonded to the two groups (N and/or C groups). In another example, when carbon is the linking atom, two additional chemical moieties would be attached to the carbon as valency would require such. Suitable chemical moieties includes, but are not limited to, hydrogen, hydroxyl, alkyl, alkoxy, =0, halogen, nitro, amine, amide, thiol, aryl, heteroaryl, cycloalkyl, and heterocyclyl.
[0044] The term "alkyl" as used herein is a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl, ethyl, w-propyl, isopropyl, w-butyl, isobutyl, s-butyl, ?-butyl, w-pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. The alkyl group can be cyclic or acyclic. The alkyl group can be branched or unbranched. The alkyl group can also be substituted or unsubstituted. For example, the alkyl group can be substituted with one or more groups including, but not limited to, optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol, as described herein. A "lower alkyl" group is an alkyl group containing from one to six (e.g., from one to four) carbon atoms.
[0045] The terms "amine" or "amino" as used herein are represented by the
1 2 3 1 2 3
formula NA A A , where A , A , and A can be, independently, hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.
[0046] The term "halide" as used herein refers to the halogens fluorine, chlorine, bromine, and iodine.
[0047] The term "hydroxyl" as used herein is represented by the formula— OH.
[0048] The term "nitro" as used herein is represented by the formula— O2.
[0049] The term "nitrile" as used herein is represented by the formula— CN.
[0050] The term "thiol" as used herein is represented by the formula— SH.
[0051] The term "heterocyclyl" or the like terms refer to cyclic structures including a heteroatom. Thus, "heterocyclyl" includes both aromatic and non- aromatic ring structures with one or more heteroatoms. Non-limiting examples of heterocyclic includes, pyridine, isoquinoline, methylpyrrole and thiophene etc.
"Heteroaryl" specifically denotes an aromoatic cyclic structure including a heteroatom.
[0052] As used herein the terms "compound" and "complex" are used interchangeably.
[0053] Several structures herein show a nitrogen (N) coordinated to a metal. It is understood that the although the valency is indicated to be neutral in the structure it can if appropriate, as appreciated by those skilled in the art, be a cationic species having a net positive charge due to the coordination. Thus, nitrogen can be shown in the structures to have neutral charge or a positive charge and in some cases these structures can be used interchangeably as appropriate and as recognized by one skilled in the art.
The compounds and compositions disclosed herein are described as containing a "metal" or "metals." Examples of such "metal" components include, but are not limited to Pt, Pd, Ir, Rh, Au, Os, or Ru. It should be understood that references to such "metals" oin this application does NOT imply a particular valence, chemical, or physical state of those elements, or that those elements are necessarily in a zero valent state, or metallic solid physical state or alloy (although they could be in such states), but rather that the term "metal" or "metals" can also be present in a compound with other elements or groups wherein the metal can be present in any energetically feasible positive oxidation state (i.e. cationic oxidation states). For example, a
reference to platinum (Pt) includes the cationic form Pt2+ of platinum or Pt4+ of platinum.
Compounds
[0054] As briefly described above, the present invention is directed to metal compounds or complexes, such as platinum, palladium, gold, silver, ruthenium, iridium, rhodium, aluminum, gallium, cobalt, and osmium compounds. In one aspect, the compositions disclosed here can provide emission spectra of platinum, palladium, gold, silver, ruthenium, iridium, rhodium, aluminum, gallium, cobalt, and osmium. In another aspect, the compositions disclosed herein can provide tunable emission spectra.
[0055] In one aspect, the disclosed compounds are useful as host materials in devices, such as full color displays.
[0056] In another aspect, the disclosed compounds are useful as emitters in devices, such as OLEDs.
[0057] Cyclometalated metal complexes can be used for many applications including emitters for OLEDs. One of most important factors dictating the quantum efficiency of emission, is proportional to the integral of wavefunction of ground state and excited state, which favors a small difference in their equilibrium geometry. Typically, an efficient emitter requires a rigid planar chemical structure, which has 5- membered coordination rings (Scheme 1). On the other hand, emitters containing unplanar lumophore do not have strong emission at the room temperature due to their distorted molecular geometry, which has 6-membered coordination rings (Scheme lb). This invention provides a materials design route which enables the emitters with 6-membered coordination rings to be efficient emitters and have tunable emission wavelength in the visible range. This class of emitters can be utilized as emitters for full color displays and lighting applications. To make this work, one condition needs to be satisfied: the molecular geometry needs to be very rigid. The molecular structure of four-coordinating ligands will be preferred which ensures the
electrochemical and photophysical stability of metal complexes.
[0058] As illustrated in Scheme 1, PtNON is an emitter with 6-membered coordination rings, which has demonstrated an electron-to-photon conversion efficiency over 20% in the device settings
SCHEME 1
[0059] Accordingly, the invention also relates to metal compounds that can be useful as emitters in devices, such as OLEDs.
[0060] The emission (and absorption) profile of the compounds can be tuned by varying the structure of the ligand surrounding the metal center. For example, compounds having a ligand with electron withdrawing substituents will generally exhibit different optical properties, including emission and absorption, than compounds having a ligand with electron donating substituents. Generally, a chemical structural change affects the electronic structure of the compound, which thereby affects the absorption and emission of the compound. Thus, the compounds of the present invention can be tailored or tuned to a specific application that desires a particular emission or absorption characteristic.
[0061] In another aspect, the emission spectrum of any of the compositions of the present disclosure can be tuned to a desired and/or customized spectrum. In another aspect, the complexes disclosed herein can provide a narrow bandwidth, enabling their use in, for example, applications in which broad spectrum emitters are not suitable.
[0062] In one aspect, the excited state dynamics of the complex can be described by the scheme:
1M LCT
So where 3LC represents the energy of the ligand centered triplet state, ^LCT represents the energy of the metal-to-ligand charge transfer singlet state, Ti represents the energy of the emissive triplet state, So represents the energy of the ground state, and ΔΕ represents the difference in energy between ^LCT and 3LC.
[0063] In still another aspect, an expansion utilizing different emitting portions and linking groups should provide narrow emitting complexes covering a wide range of the visible spectrum. The emission energy of a certain complex can be tuned by modifying the ligand centered triplet state of the emitting fragment (3LC). This can be accomplished through changes in structure that modify the energy of the donating or accepting portion of the emitting fragment.
[0064] In another aspect, the nature of the ^LCT transitions can be controlled by modifying the ancillary portion of the complex (LAX), through changes in the cyclometalating portion, the linking portions, or both.
[0065] In one aspect, the inventive compositions are useful as emitters for full color display application. In such an aspect, the geometry of cyclometalating ligands can be rigid. This rigidity can allow for similar geometry between the ground and excited state, resulting in a narrow emission spectra dominated by the transition from the lowest vibrational level in the excited state to the lowest vibrational level in the ground state.
[0066] In another aspect, complexes can be designed to tune the values of the emitting fragment centered 3LC state and the metal to ancillary ligand ^LCT states
independently. Reduction in the differences in energy between these states (ΔΕ) will improve mixing between them, improve the radiative decay rate, and suppress transitions that occur from the emissive state (Ti) to excited vibrational levels in the ground state (So). As a consequence, the vibrational shoulders of the emission spectra can be reduced, resulting in a more narrow emission profile.
[0067] In a further aspect, the molecular structure having four coordinating ligands to a metal center can be preferred. In such an aspect, a four ligand coordinated structure can at least partially ensure the electrochemical and/or photophysical stability of the complex during, for example, fabrication and operation of a color display device.
[0068] In another aspect, the inventive compositions can provide improved efficiency and/or operational lifetimes in lighting devices, such as, for example, organic light emitting devices, such as OLEDs, as compared to conventional materials. Thus, also disclosed herein are devices comprising the complexes described herein. One application for phosphoresent emissive complexes, such as those described herein, is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
[0069] In one aspect, for the formulas described herein, M can comprise Pt. In another aspect, M can comprise Pd. In yet another aspect, M can comprise Rh. In yet another aspect, M can comprise Ir. In yet another aspect, M can comprise Au. In yet another aspect, M can comprise Ag. In yet another aspect, M can comprise Cu. In yet another aspect, M can comprise Zr. In yet another aspect, M can comprise Hg. In yet another aspect, M can comprise Ga. In yet another aspect, M can comprise Co. In yet another aspect, M can comprise Os. In yet another aspect, M can comprise Ru.
[0070] In one aspect, for the formulas described herein, each of Yla, Ylb, and Ylc independently can be O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3
independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
[0071] In one aspect, for the formulas described herein, each of Yla, Ylb, Ylc, Yld, and Yle independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
[0072] In one aspect, at least one of Yla, Ylb, and Ylc is NR2. In another aspect, at least two of Yla, Ylb, and Ylc are NR2. In yet another aspect, Yla, Ylb, and Ylc are NR2.
[0073] In one aspect, at least one of Yla, Ylb, Ylc, Yld, and Yle is NR2. In another aspect, at least two of Yla, Ylb, Ylc, Yld, and Yle are NR2. In yet another aspect, at least three of Yla, Ylb, Ylc, Yld, and Yle are NR2.
[0074] In one aspect, for the formulas disclosed herein, at least one of Yla, Ylb,
Ylc, Yld, and/or Yle can independently comprise O. In another aspect, at least one of yla ylb Ylc; yld yle can independently comprise NR2. In yet another aspect, at least one of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise CR2R3. In yet another aspect, at least one of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise S. In yet another aspect, at least one of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise BR2. In yet another aspect, at least one of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise PR2. In yet another aspect, at least one of Yla, yib Yidj and/or Yie can independently comprise P(0)R2. In yet another aspect, at least one of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise SiR2R3. In one aspect, Yla, Ylb, Ylc, Yld, and/or Yle can be oxygen
[0075] In one aspect, each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to
an adjacent ring structure, thereby forming a cyclic structure. In another aspect, each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, or heterocyclyl, wherein each R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure. In yet another aspect, each of R2 and R3 independently is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure. In yet another aspect, one of R2 or R3 is aryl, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure. In one aspect, each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
[0076] For each structure shown herein, it is appreciated that if an R2 or R3 group is shown to be linked to an adjacent ring structure, such as a six or five membered ring. In one aspect, each of Yla, Ylb, Ylc, Yld, and/or Yle can to ring structure
. Thus, forming a cyclic
structure, for example or . In another aspect, each of Yla, Ylb, Ylc, to ring structure
exampel, . In another aspect, each of Yla, Ylb, Ylc, Yld, and/or Y le
to ring structure
. In yet another aspect, each of Yla, Ylb, Ylc, Yld, and/or Yle can linked to ring to ring structure independently comprise
wherein X is N, B, P, or As. In yet another aspect, each of Yla, Ylb, Ylc, Yld, and/or
Yle can independently comprise Pn . In yet another aspect, each of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise \ . In yet another aspect, each of ϊ", ϊ", ϊ'·, Yla, and/or Υ]ί can independently comprise Ph . In yet another aspect, each of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise ^S^- . in yet another aspect, each of Yla, Ylb, Ylc, Yld, and/or Yle can independently comprise O
P I '
Ph
[0077] In one aspect, for the formulas described herein, each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR6b, wherein each of R6a and R6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene. In one aspect, at least one of Y2a, Y2b, Y2c, and Y2d is CR*. In another aspect, at least two of Y2a, Y2b, Y2c, and Y2d is CR6b. In yet another aspect, at least three of Y2a, Y2b, Y2c, and Y2d is CR6b. In yet another aspect, at least one of Y2a, Y2b, Y2c, and Y2d is NR6a.
[0078] In one aspect, each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR* wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene. In another aspect, at least four of Y3a, Y3b, Y3c, and Y3d are CR6b. In another aspect, at least three of Y3a, Y3b, Y3c, and Y3d are CR6b. In another aspect, at least one of Y3a, Y3b, Y3c, and Y3d is N or NR6a. In another aspect, at least four of Y4a, Y4b, Y4c, and Y4d are CR6b. In another aspect, at least three of Y4a, Y4b, Y4c, and Y4d are CR6h. In another aspect, at least one of Y4a, Y4b, Y4c, and Y4d is N or NR6a.
[0079] In one aspect, of each of Y5a, Y5b, Y5c, Y5d, Y6a, Y6b, Y6c, and Y6d independently is N, O, S, NR6a, or CR6b. In another aspect, at least four of Y5a, Y5b, Y5c, and Y5d are CR6b. In another aspect, at least three of Y5a, Y5b, Y5c, and Y5d are CR6b. In another aspect, at least one of Y5a, Y5b, Y5c, and Y5d is N or NR6a. In another aspect, at least four of Y6a, Y6b, Y6c, and Y6d are CR6b. In another aspect, at least three of Y6a, Y* Y6c, and Y6d are CR6b. In another aspect, at least one of Y6a, Y6b, Y6c, and Y6d is or R6a.
[0080] In one aspect, R6b is hydrogen. In another aspect, at least one R6b is hydrogen. In another aspect, at least one R6b is alkyl or aryl.
[0081] In one aspect, R a is hydrogen. In another aspect, at least one R a is hydrogen. In another aspect, at least one R6a is alkyl or aryl.
[0082] In one aspect, m is 1. In another aspect, m is 2. In one aspect, at least one m is 1. In another aspect, at least one m is 2. In one aspect, n is 1. In another aspect, n is 2. In yet another aspect, at least one m is 1 and at least one m is 2. In yet another aspect, at least one m is 1 and n is 1. In yet another aspect, at least one m is 1 and n is 2. In yet another aspect, at least one m is 2 and « is 2. In yet another aspect, at least one m is 2 and n is 2.
[0083] In one aspect, is partial unsaturation of the ring with which it is associated. In another aspect, is full unsaturation of the ring with which it is associated. In another aspect, at least one - - ' is full unsaturation of the ring with which it is associated and at least one - - ' is partial unsaturation of the ring with which it is associated.
[0084] In one aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, Y2b and Y2c is CH, Y3b and Y4b is N, at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and M is Pt or Pd.
[0085] In one aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, Y2b is CH, Y3b , Y2c and Y4b is N, Ylb is NR2, CR2R3, AsR2, BR2,
2 2 2 3 2 3
PR", P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and M is Ir or Rh.
[0086] In one aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, Y2b, Y2c and Y4b is CH, Y3b is N, Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and M is Au.
[0087] In one aspect, the compounds disclosed herein can have a structure where at least of one of Y2a, Y2d, Y3d and Y4d is C, at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a, Y2d, Y3d and Y4d, thereby forming a cyclic structure, and M is Pt or Pd.
[0088] In another aspect, the compounds disclosed herein can have a structure where at least of one of Y2a and Y3d is C, Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a and Y3d, thereby forming a cyclic structure, and M is Ir or Rh.
[0089] In another aspect, the compounds disclosed herein can have a structure where at least of one of Y2a and Y3d is C, Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a and Y3d, thereby forming a cyclic structure, and wherein M is Au.
[0090] In another aspect, the compounds disclosed herein can have a structure where m is 2, Y2b and Y2c is CH, Y3b and Y4b is N, at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and M is Ir or Rh.
[0091] In another aspect, the compounds disclosed herein can have a structure where at least of one of Y2a, Y2d, Y3d and Y4d is C, at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a, Y2d, Y3d and Y4d, thereby forming a cyclic structure, and M is Ir or Rh
[0092] In another aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, Y2b and Y2c is CH, Y3b and Y4b is N. In yet another aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, and Y2b and Y2c is CH. In another aspect, the compounds disclosed herein can have a structure where m is 2, n is 2, and Y3b and Y4b is N.
[0093] In one aspect, for the formulas described herein, each of E1, E2, E3, E4, and/or E5 can independently comprise O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure.
[0094] In one aspect, at least one of E1, E2, E3, E4, and/or E5 can independently comprise O. In another aspect, at least one of E1, E2, E3, E4, and/or E5 can
independently comprise NR2. In yet another aspect, at least one of E1, E2, E3, E4,
and/or E5 can independently comprise CR2R3. In yet another aspect, at least one of E1, E2, E3, E4, and/or E5 can independently comprise S. In yet another aspect, at least one of E1, E2, E3, E4, and/or E5 can independently comprise BR2. In yet another aspect, at least one of E1, E2, E3, E4, and/or E5 can independently comprise PR2. In yet another aspect, at least one of E1, E2, E3, E4, and/or E5 can independently comprise P(0)R2. In yet another aspect, at least one of E1, E2, E3, E4, and/or E5 can
2 3 1 2 3 4 5
independently comprise SiR R . In one aspect, E , E , E , E , and E can be oxygen.
[0095] In one aspect, at least one of E1, E2, E3, E4, and/or E5 can independently can be absent from a structure recited herein, whereby a bond is then directly present between any Ns and/or Cs.
[0096] In one aspect, each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C and/or N, thereby forming a cyclic structure. In another aspect, each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, or heterocyclyl, wherein each of R2 and R3 independently is optionally linked to a C and/or N, thereby forming a cyclic structure. In yet another aspect, each of R2 and R3 independently is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure. In yet another aspect, one of R2 or R3 is aryl, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure. In one aspect, each of R2 and R3 independently is linked to a C or N, thereby forming a cyclic structure.
[0097] For each structure shown herein, it is appreciated that if an R2 or R3 group is shown to be linked to a N, then it can also be bound to C in a similar type structure. In one aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise
. Thus, forming a cyclic structure, for example
It is also understood that each of E1, E2, E3, E4, and/or E5 can independently be linked
to C in a similar manner, thereby forming, for example,
. In another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise
, for exampel, . In another aspect, each of E1,
2, E3, E4, and/or E5 can independently comprise , for example,
. In yet another aspect, each of E1, E2, E3, E4, and/or E5 can inkM to C As ink to independently comprise , for example,
In yet another aspect, each of E1, E2, E3, E4, and/or E5 can
independently comprise
, for example, . In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise
J, . in s C
, wherein X is N, B, P, or As. In yet another aspect, each of
E1, E2, E3, E4, and/or E5 can independently comprise Pn . In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise / \ . In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise ph . In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise . In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently comprise ph h .. ; In yet another aspect, each of E1, E2, E3, E4, and/or E5 can independently
[0098] In one aspect, at least one of E , E , and E is O. In another aspect, at
1 2 3 1 2 3 2 least two of E , E , and E are O. In one aspect, at least one of E , E , and E is NR , CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure.
[0099] In one aspect, E , E , and E can be oxygen. In one aspect, E , E , and E can comprise O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a
combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure. In another aspect, E1 and E3 can be oxygen. In yet another aspect E2 comprise O, NR2, CR2R3, S, AsR2, BR2, PR2,
2 2 3 2 3
P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure.
[00100]
another aspect, at least one of E , E , and E is
. In yet another aspect, at least one of E1, E2, and E3 is Pn . In yet another aspect, at least one of
E1, E2, and E3 is Ph . In yet another aspect, at least one of E1, E2, and E3 is
/ \ . In yet another aspect, at least one of E1, E2, and E3 is Pn . In yet another aspect, at least one of E1, E2, and E3 is ^S^- . in yet another aspect, at least one of
E1, E2, and E3 is Ph .
31
[00102] In one aspect, at least one of E1, E2, E3, and E4 is O. In another aspect, at least two of E1, E2, E3, and E4 are O. In yet another aspect, at least three of E1, E2, E3, and E4 are O. In yet another aspect, E1, E2, and E3 can be oxygen. In yet another aspect, E1, E2, E3, and E4 can be oxygen. In yet another aspect, E1, E2, E3, E4, and E5 can be oxygen.
[00103] In one aspect, at least one of E1, E2, E3, and E4 is NR2. In another aspect, at least two of E1, E2, E3, and E4 are NR2. In yet another aspect, at least three
1 2 3 4 2 1 2 3 2 of E , E , E , and E are NR . In yet another aspect, E , E , and E can be NR . In yet another aspect, E1, E2, E3, and E4 can be NR2. In yet another aspect, E1, E2, E3, E4, and E5 can be NR2.
[00104] In one aspect, at least one of E1, E2, E3, and E4 is NR2, CR2R3, S, BR2,
2 2 2 3 2 3
PR", P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure. In one aspect, at least two of E1, E2, E3, and E4 is NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R , or SiR RJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure.
least one N is . In yet
another aspect,
at least one N is . In yet another aspect, at least one N is
In yet another aspect, at least one N is . In another aspect, the
N groups can be substituted heterocyclyl. In another aspect, the N groups can be unsubstituted heterocyclyl. In another aspect, the N groups can be pyridine.
another aspect, at least one C is
. In yet another aspect, at least one C is
. In yet another aspect, at least one C . In one aspect, C can be an unsubstituted aromatic ring or heterocyclic group. In another aspect, C can be a unsubstituted aromatic ring or heterocyclic group. In another aspect, C can be a substituted aromatic ring or heterocyclic group. In one aspect, the C groups can be phenyl.
[00107] Some structures recited herein refer to "R" which can represent R2 or R3 as defined herein.
[00108] The following structures can as appropriate be a subgenus and/or individual compound of the disclosed generic structures disclosed herein. It is appreciated that some of these structures have different indicators, i.e. R1, A, U etc. than those in the corresponding in the generic structure. For example, it is appreciated
that X, A, and A in , would correspond to Ylb, Yla, and Ylc
[00109] Specific compounds include but are not limited to:
40
41
Where U, V and W could be the same or different atoms like carbon (C) nitre sulfur (S), phosphorus (P), silicon (Si), boron (B) and others.
Where U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si)
[00110] In one aspect, the compounds can have the structure:
[00111] In one aspect, M is Ir or Rh.
[00112] Specific compounds include but are not limited to:
53
Where U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), boron (B) and other atoms.
[00113] In one aspect, the compounds can have the structure:
[00114] Specific compounds include, but are not limited to:
Where U, V, W could be the same or different atoms like carbon (C), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), boron (B) and other atoms.
[00116] Specific compounds include, but are not limited to:
[00118] In one aspect, M can be Pt or Pd. In another aspect, each of X, A, and U independently can be O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3
independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure.
[00119] In one aspect,
[00120] In one aspect,
[00121] In one aspect,
[00122] It is appreciated that some of the generic structures disclosed herein can be a subgenus of another generic structure disclosed herein. For example, a generic structure containing C, N, E1, E2, E3, E4, and/or E5 can in some cases, as appropriate and as recognized by those skilled in the art, be a subgenus of:
[00123] In one aspect, disclosed herein is a compound having the structure:
wherein M comprises Pt, Pd, Ir, Rh, or Au; wherein each of R1 and R2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Yla, Ylb, and Ylc independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure; wherein each of Y2a,
Y , Υ , and Y independently is , NR , or CR , wherein each of Rba and Rbb independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR6b, wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of m and n independently are an integer 1 or 2; wherein each of - ' independently is partial or full unsaturation of the ring with which it is associated.
[00124] In one aspect, disclosed herein is a compound having the structure:
wherein M comprises Ir, Rh, Pt, Os, or Ru, wherein each of R1 and R2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Yla, Ylb, Ylc, Yld, and Yle independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen,
substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure; wherein each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR6b, wherein each of R6a and R6b independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR*, wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; wherein in each of each of Y5a, Y5b, Y5c, Y5d, Y6a, Y6b, Y6c, and Y6d independently is N, O, S, NR6a, or CR6b; wherein each of m and n independently are an integer 1 or 2; wherein each of independently is partial or full unsaturation of the ring with which it is associated.
[00125] In one aspect, disclosed herein is a compound having the structure:
wherein the formula, M represent a metal cation with two positive charges, which include, but are not limited to Platinum(II) (Pt2+), Palladium(II) (Pd2+), wherein
1 2 3 2 2 3
E , E , and E independently represent a linking atom comprising O, NR , CR R , S, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00126] In one aspect, M can be Platinum (II). In one aspect, M can be Palladium (II).
[00127] In one aspect, the compound can be:
wherein each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl.
[00128] In one aspect, disclosed herein is a compound having the structure:
wherein M represents a metal cation with three positive charges, which include, but are not limited to Gold(III) (Au3+), silver(III) (Ag3+), wherein each E1, E2,
3 2 2 3 2 and E independently represent a linking atom comprising O, NR , CR R , S, BR ,
2 2 2 3 2 3
PR", P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein N
represents a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00129] In one aspect, E1, E2, and E3 can be oxygen. In one aspect, each of E1, E2, and E3 can independently comprise O, NR2, CR2R3, S, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure In another aspect, E1 and E3 can be oxygen. In yet another aspect, E2 can be nitrogen, oxygen, carbon, silicon, phosphorous, or sulfur.
[00130] In one aspect, M can be Au (III). In one aspect, M can be Ag (III).
[00131] In one aspect, the compound can have the structure:
alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl.
[00132] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with one positive charges, which include, but is not limited to, iridium (I) (Ir1+), Rhodium (I) (Rh1+), etc., wherein E1, E2, and E3
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)Rz, or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein C represents a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N
independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00133] In one aspect, M can be Rhodium (I). In one aspect, M can be Iridium
(I).
[00134] In one aspect, the compound can have the structure:
wherein each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl.
[00135] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+),
Aluminum(III) (Al3+),and Gallium(III) (Ga3+), wherein E1, E2, E3, and E4
2 2 3 2 2 independently represent a linking atom,comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)R% or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00136] In one aspect, M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
Aluminum (III). In another aspect, M can be gallium (III).
[00137] In one aspect, the compound can have the structure;
90
wherein each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
[00138] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+),
Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, E4, and E5
independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
P(0)R , or SiR RJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00139] In one aspect, M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
Aluminum (III). In another aspect, M can be gallium (III).
[00140] In one aspect, the compound has the structure:
[00141] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+),
Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, E4, and E5
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR ,
2 2 3 2 3
P(0)R% or SiRzRJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00142] In one aspect, M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
Aluminum (III). In another aspect, M can be gallium (III).
[00144] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd4+), Platinum(IV) (Pt4+), wherein E1, E2, E3, and E4,
2 2 3 2 2 independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR RJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00145] In one aspect, M can be Platinum (VI). In one aspect, M can be Palladium (VI).
[00146] In one aspect, the compound can have the structure:
95
96
wherein each R independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
[00147] In one aspect, disclosed herein is a compound having the structure:
where M represent a metal cation with four positive charges, which include, but are not limited to, Palladium(IV) (Pd4+), Platinum(IV) (Pt4+), wherein E1, E2, E3, E4, and
5 2 2 3 2 2
E independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR RJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00148] In one aspect, M can be Platinum (VI). In one aspect, M can be Palladium (VI).
[00149] In one aspect, the compound can have the structure:
[00150] In one aspect, disclosed herein is a compound having the structure:
wherein M represent a metal cation with three positive charges, which include, but are not limited to, iridium (III) (Ir3+), Rhodium(III) (Rh3+), Cobalt (III) (Co3+),
Aluminum(III) (Al3+),Gallium(III) (Ga3+), wherein E1, E2, E3, and E4, independently represent a linking atom comprising O, NR2, CR2R3, S, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00151] In one aspect, the C groups can be phenyl. In another aspect, the N groups can be pyridine.
[00152] In one aspect, E1, E2, E3, and E4 can be oxygen.
[00153] In one aspect, M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
Aluminum (III). In another aspect, M can be gallium (III).
101
102
103
wherein R is hydrogen, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di- alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, ester, nitrile,
isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, or substituted silyl,
[00155] In one aspect, disclosed herein is a compound having the structure:
2_|_ 1 2 3 4 not limited to, Ruthenium (II) (Ru ), Osmium (II) (Os ), wherein E , E , E , E , and
5 2 2 3 2 2
E independently represent a linking atom comprising O, NR , CR R , S, BR , PR , P(0)R , or SiR RJ, or a combination thereof, wherein each of R and R
independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure; wherein each C independently represent a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal, wherein each N independently represent a substituted or unsubstituted aromatic ring or heterocyclic group with a nitrogen atom coordinated to the metal.
[00156] In one aspect, the C groups can be phenyl. In another aspect, the N groups can be pyridine.
[00157] In one aspect, E1, E2, E3, E4, and E5 can be oxygen.
[00158] In one aspect, M can be Iridium (III). In one aspect, M can be Rhodium (III). In another aspect, M can be Cobalt (III). In another aspect, M can be
Aluminum (III). In another aspect, M can be gallium (III).
Compositions
[00159] As briefly described above, the present invention is directed to metal compounds. Also disclosed are compositions comprising one or more of the disclosed compounds.
Devices
[00160] As briefly described above, the present invention is directed to metal compounds. In one aspect, the compounds or compositions disclosed here can be used as host materials for OLED applications, such as full color displays. In another aspect, the compounds or compositions disclosed here can be used a emitter materials for OLED applications or displays.
[00161] In one aspect, the compounds can be the host material in the device. In another aspect, device can be a lighting device.
[00162] In one aspect, wherein the compound is used as a phosphorescent emitter in the device.
[00163] In one aspect, wherein the compound is used as a delayed fluorescent and phosphorescent emitter in the device.
[00164] The disclosed compounds of the present disclosure can be useful in a wide variety of applications, such as, for example, lighting devices. In a particular aspect, one or more of the compounds can be useful as host materials for an organic light emitting display device.
[00165] The disclosed compounds are useful in a variety of applications. As light emitting materials, the compounds can be useful in organic light emitting diodes (OLED)s, luminescent devices and displays, and other light emitting devices.
[00166] The energy profile of the compounds can be tuned by varying the structure of the ligand surrounding the metal center. For example, compounds having a ligand with electron withdrawing substituents will generally exhibit different properties, than compounds having a ligand with electron donating substituents. Generally, a chemical structural change affects the electronic structure of the compound, which thereby affects the electrical transport and transfer functions of the material. Thus, the compounds of the present invention can be tailored or tuned to a specific application that desires an energy or transport characteristic.
[00167] In another aspect, disclosed compound can provide improved efficiency and/or operational lifetimes in lighting devices, such as, for example, organic light emitting devices, as compared to conventional materials.
[00168] In other various aspects, the disclosed compounds can be useful as, for example, host materials for organic light emitting diodes, lighting applications, and combinations thereof.
[00169] In one aspect, the device is an electro-optical device. Electro-optical devices include, but are not limited to, photo-absorbing devices such as solar- and photo-sensitive devices, organic light emitting diodes (OLEDs), photo-emitting devices, or devices capable of both photo-absorption and emission and as markers for bio-applications. For example, the device can be an OLED.
[00170] OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
[00171] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an "exciton," which is a localized electron-hole pair having an excited energy state, is formed. Light
is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
[00172] The initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No.
4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
[00173] More recently, OLEDs having emissive materials that emit light from triplet states ("phosphorescence") have been demonstrated. Baldo et al, "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, vol. 395, 151-154, 1998; ("Baldo-I") and Baldo et al, "Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No.
7,279,704 at cols. 5-6, which are incorporated by reference.
[00174] One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art. Such devices are disclosed herein which comprise one or more of the compounds or composition disclosed herein.
[00175] The OLED can be produced by methods known to those skilled in the art. In general, the OLED is produced by successive vapor deposition of the individual layers onto a suitable substrate. Suitable substrates are, for example, glass, inorganic materials such as ITO or IZO or polymer films. For the vapor deposition, customary techniques may be used, such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) and others.
[00176] In an alternative process, the organic layers may be coated from solutions or dispersions in suitable solvents, in which case coating techniques known to those skilled in the art are employed. Suitable coating techniques are, for example,
spin-coating, the casting method, the Langmuir-Blodgett ("LB") method, the inkjet printing method, dip-coating, letterpress printing, screen printing, doctor blade printing, slit-coating, roller printing, reverse roller printing, offset lithography printing, flexographic printing, web printing, spray coating, coating by a brush or pad printing, and the like. Among the processes mentioned, in addition to the
aforementioned vapor deposition, preference is given to spin-coating, the inkjet printing method and the casting method since they are particularly simple and inexpensive to perform. In the case that layers of the OLED are obtained by the spin- coating method, the casting method or the inkjet printing method, the coating can be obtained using a solution prepared by dissolving the composition in a concentration of 0.0001 to 90% by weight in a suitable organic solvent such as benzene, toluene, xylene, tetrahydrofuran, methyltetrahydrofuran, Ν,Ν-dimethylformamide, acetone, acetonitrile, anisole, dichloromethane, dimethyl sulfoxide, water and mixtures thereof
[00177] The disclosed compounds can be made using a variety of methods, including, but not limited to those recited in the examples provided herein. In other aspects, one of skill in the art, in possession of this disclosure, could readily determine an appropriate method for the preparation of an iridium compound as recited herein.
Examples
[00178] The following examples are put forth so as to provide those of ordinary skill in the art with a complete disclosure and description of how the compounds, compositions, articles, devices and/or methods claimed herein are made and evaluated, and are intended to be purely exemplary of the invention and are not intended to limit the scope of what the inventors regard as their invention. Efforts have been made to ensure accuracy with respect to numbers (e.g., amounts, temperature, etc.), but some errors and deviations should be accounted for. Unless indicated otherwise, parts are parts by weight, temperature is in °C or is at ambient temperature, and pressure is at or near atmospheric.
Example 1 - synthesis of PtOOO
[00179] Scheme 1 shows the general scheme for the synthesis of the compounds disclosed herein.
Scheme 1
[00180] The reaction details for the synthesis is as follows:
[00181] (a)Resocinol (1.5 mmol), 2-bromopyridine (1 mmol), 1 -methylimidazole (0.5mmol), copper(I) iodide (0.1 mmol), potassium carbonate (2 mmol),
dimethylformamide (15 mL). Sealed, degassed tube stirred at 130° C, 3 days. 3- (pyridin-2-yloxy)phenol produced in 40% yield.
[00182] (b)3-bromophenol (1 mmol), 2-bromopyridine (2 mmol), 1- methylimidazole (0.5mmol), copper(I) iodide (0.1 mmol), potassium carbonate (2 mmol), dimethylformamide (15 mL). Sealed, degassed tube stirred at 130° C, 3 days. 2-(3-bromophenoxy)pyridine produced in 50% yield.
[00183] (c)3-(pyridin-2-yloxy)phenol (1 mmol), 2-(3-bromophenoxy)pyridine (1 mmol), 1 -methylimidazole (0.5mmol), copper(I) iodide (0.1 mmol), potassium carbonate (2 mmol), dimethylformamide (15 mL). Sealed, degassed tube stirred at 130° C, 3 days. 2,2'-(3,3'-oxybis(3, l-phenylene)bis(oxy))dipyridine produced in 50% yield.
[00184] (d) 2,2'-(3,3'-oxybis(3, l-phenylene)bis(oxy))dipyridine (1 mmol), potassium tetrachloroplatinate (1 mmol), and nBu4NBr(0.1mmol) were charged into a 100ml three necked flask, then 60ml acetic acid was added. The mixture was
degassed with Nitrogen and stirred at ambient temperature for 12 hours. The mixture was heated in an oil bath at a temperature of 110 °C for another 36 hours. 100 ml of water was added after the mixture was cooled down to room temperature. The precipitate was collected through filtration, washed with water for three times then dried in air and purified through column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in dichloromethane and ether at refrigerator to get the desired platinum compound PtOOO as a yellow solid in 82% yield. (DMSO-d6, 400 MHz): δ 6.82 (m, 4H), 7.02 (t, 2H), 7.24 (dd, 2H), 7.47(d, 2H), 8.12 (dd, 2H), 8.34(d, 2H)
[00185] PtOOO was tested as a host material in a device having the following structure: ITO/HATCN (10nm)/ NPD (40nm)/ TAPC (lOnm)/ 6% Pt003: Host/ DPPS (10nm)/BmPyPB (40nm)/LiF/Al. The I-V curve for this device compared to a device using mCPy as a host material is shown in figure 2. The EL spectrum this device compared to a device using mCPy as a host material is shown in figure 3. The EQE for this device compared to a device using mCPy as a host material is shown in figure 4.
Example 2 synthesis of PdOOO
[00186] 2,2'-(3,3'-oxybis(3, l-phenylene)bis(oxy))dipyridine (1 mmol),
Palladium(II) acetate (1 mmol) , and nBu4NBr(0.1mmol) were charged into a 100ml three necked flask, then 30 ml acetic acid was added. The mixture was degassed with Nitrogen and stirred at ambient temperature for 12 hours. The mixture was heated in an oil bath at a temperature of 1 10 °C for another 36 hours. 100 ml of water was added after the mixture was cooled down to room temperature. The precipitate was collected through filtration, washed with water for three times then dried in air and purified through column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in
dichloromethane and ether at refrigerator to get the desired platinum compound PdOOO as a white solid in 80% yield. (DMSO-d6, 400 MHz): δ 6.83 (d, 2H), δ 6.88 (d, 2H), 7.07 (t, 2H), 7.31 (dd, 2H), 7.44(d, 2H), 8.08 (dd, 2H), 8.42(d, 2H).
Example 3 - Synthesis of PtNON
[00187] 9-(pyridin-2-yl)-2-(9-(pyridin-2-yl)-9H-carbazol-2-yloxy)-9H- carbazole(240 mg, 0.48 mmol), K2PtCl4(208mg, 0.50 mmol), and nBu4NBr(15.4mg, 0.048mmol) were charged into a 100ml three necked flask, then 30ml acetic acid was added. The mixture was degassed with Nitrogen and stirred at ambient temperature for 12 hours. The mixture was heated in an oil bath at a temperature of 1 10 °C for another 36 hours. 100 ml of water was added after the mixture was cooled down to room temperature. The precipitate was collected through filtration, washed with water for three times then dried in air and purified through column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in dichloromethane and ether at refrigerator to get the desired platinum compound PtNON as a bright yellow solid 280 mg in 84.8% yield. 1H NMR (DMSO-d6, 400 MHz): δ 7.16 (d, 2H), 7.25-7.30 (m, 2H), 7.39 (t, 2H), 7.46(t, 2H), 7.89 (d, 2H), 8.05(d, 2H), 8.13-8.18(m, 6H), 9.0(d, 2H).
Example 4 - Synthesis of PtNNN
[00188] 9-(9-(9-(pyridin-2-yl)-9H-carbazol-2-yl)-9H-carbazol-2-yl)-9H- pyrido[2,3-b]indole (288 mg, 0.50 mmol), K2PtCl4(228 mg, 0.55 mmol), and nBu4NBr(16.1 mg, 0.05 mmol) were charged into a 100ml three necked flask, then 30ml acetic acid was added. The mixture was degassed with Nitrogen and stirred at ambient temperature for 12 hours. The mixture was heated in an oil bath at a temperature of 110 °C for another 36 hours. 100 ml of water was added after the mixture was cooled down to room temperature. The precipitate was collected through filtration, washed with water for three times then dried in air and purified through
column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in dichloromethane and ether at refrigerator to get the desired platinum compound Pt N as a bright yellow solid 100 mg in 26 % yield. 1H NMR (DMSO-d6, 400 MHz): 9.17 (m, 1H), 9.04 (m, 1H), 8.78 (m, 1H), 8.43 (d, J=7.6Hz 1H), 8.25-8.30(m, 2H), 8.04-8.19(m, 6H), 7.82- 7.88 (m, 3H), 7.64(M, 1H), 7.36-7.55(m, 6H), 7.31(dd, J=9.6Hz, J=4.8Hz, 1H).
Example 5 - Synthesis of PtNOO
[00189] 9-(pyridin-2-yl)-2-(3-(pyridin-2-yloxy)phenoxy)-9H-carbazole (215 mg, 0.50 mmol), K2PtCl4(228 mg, 0.55 mmol), and nBu4 Br (16.1 mg, 0.05 mmol) were charged into a 100ml three necked flask, then 30 ml acetic acid was added. The mixture was degassed with Nitrogen and stirred at ambient temperature for 12 hours. The mixture was heated in an oil bath at a temperature of 1 10 °C for another 36 hours. 100 ml of water was added after the mixture was cooled down to room temperature. The precipitate was collected through filtration, washed with water for three times then dried in air and purified through column chromatography on silica gel using dichloromethane as eluent to obtain a crude product which was further purified by recrystallization in dichloromethane and ether at refrigerator to get the desired platinum compound PtNOO as a bright yellow solid 72 mg in 23 % yield. 1H NMR (DMSO-d6, 400 MHz): 8.53-8.61 (m, 2H), 8.10-8.19 (m, 4H), 8.01 (d, J=8.4, 1H), 7.87 (d, , J=8.4, 1H), 7.51(d, , J=8.4, 1H), 7.44(m, 1H), 7.37 (dd, J=7.6 Hz, J=6.8 Hz, 1H), 7.28 (dd, , J=6.0 Hz, J=6.8 Hz 1H), 7.21 (m, 1H), 7.05-7.10(m, 2H), 6.87(dd, , J=7.2 Hz, J=7.6 Hz 2H).
Example 6 - Synthesis of PtNON-bph
[00190] To a solution of NON-bph (52 mg) in HOAc (8 mL) were added K2PtCl4 (35 mg) and «-Bu4NBr (3 mg). The mixture was heated to reflux for 3 days. The reaction mixture was cooled to rt, filtered through a pad of silica gel, and
concentrated. Purification by column chromatography (hexanes:DCM = 1 : 1 to 1 :2) gave PtNON-bPh (49 mg, yield: 72%). ¾ NMR (400 MHz, DMSO-d6) δ 9.13 (d, J = 5.5 Hz, 1 H), 9.07 (d, J= 6.7 Hz, 1 H), 8.38 (d, J= 1.6 Hz, 1 H), 8.26-8.17 (m, 5 H), 8.12 (d, J= 8.1 Hz, 1 H), 8.01 (d, J= 8.6 Hz, 2 H), 7.96 (d, J= 8.3 Hz, 1 H), 7.94 (d, J= 8.2 Hz, 1 H), 7.87 (d, J= 8.1 Hz, 2 H), 7.79-7.73 (m, 2 H), 7.69 (dd, J= 6.3, 1.6
Hz, 1 H), 7.58-7.39 (m, 7 H), 7.35 (td, J= 5.9, 2.8 Hz, 1 H), 7.21 (dd, J= 8.2, 2.7 Hz, 2 H).
Example 7- Synthesis of PdNON-bph
[00191] To a solution of NON-bPh (39 mg) in HOAc (6 mL) were added Pd(OAc)2 (14 mg) and w-Bu4NBr (2 mg). The mixture was heated to reflux for 2 days. The reaction mixture was cooled to rt, filtered through a pad of silica gel, and concentrated. Purification by column chromatography (hexanes:DCM = 1 : 1 to 1 :2) gave PdNON-bPh (32 mg, yield: 70%). XH NMR (400 MHz, DMSO-d6) δ 9.00 (d, J=
5.9 Hz, 1 H), 8.94 (d, J= 6.5 Hz, 1 H), 8.33 (d, J= 1.5 Hz, 1 H), 8.24-8.14 (m, 5 H),
8.10 (d, J= 8.2 Hz, 1 H), 8.03-7.97 (m, 4 H), 7.87 (d, J= 8.2 Hz, 2 H), 7.79-7.71 (m, 3 H), 7.57-7.36 (m, 8 H), 7.23 (dd, J= 8.2, 2.7 Hz, 2 H).
Example 8 - Synthesis of PtNON-ph
[00192] To a solution of NON-Ph (65 mg) in HOAc (5 mL) were added K2PtCl4 (44 mg) and w-Bu4NBr (3 mg). The mixture was heated to reflux for 2 days. The reaction mixture was cooled to rt, filtered through a pad of silica gel, and
concentrated. Purification by column chromatography (hexanes:DCM = 1 : 1 to 1 :2) gave PfNON-Ph (65 mg, yield: 84%).
Example 9 - Synthesis of PdNON-ph
[00193] To a solution of NON-Ph (58 mg) in HOAc (5 mL) were added
Pd(OAc)2 (24 mg) and «-Bu4NBr (3 mg). The mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, filtered through a pad of silica gel, and concentrated. Purification by column chromatography (hexanes:DCM = 1 : 1 to 1 :2) gave PdNON-Ph (50 mg, yield: 73%).
Example 10 - Synthesis of PdNNO
[00194] To a solution of NNO (75 mg) in HOAc (10 mL) were added K2PtCl4 (65 mg) and «-Bu4NBr (5 mg). The mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, filtered through a pad of silica gel,
and concentrated. Purification by column chromatography (hexanes:DCM = 1:1 to 1:2) gave PtNON-Ph (42 mg, yield: 40%).
Claims
1. A compound having the structure:
wherein M comprises Pt, Pd, Ir, Rh, or Au; wherein each of R1 and R2 independently are hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
wherein each of Yla, Ylb, and Ylc independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure;
wherein each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR* wherein each of R6a and R* independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR*, wherein each of R6a and R* independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
wherein each of m and n independently are an integer 1 or 2; wherein each of - ' independently is partial or full unsaturation of the ring with which it is associated.
2. The compound of claim 1,
wherein m is 2,
wherein n is 2,
wherein Y2b and Y2c is CH,
wherein Y3b and Y4b is N,
wherein at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and
wherein M is Pt or Pd.
3. The compound of claim 1 ,
wherein m is 2,
wherein n is 2,
wherein Y2b is CH,
wherein Y3b , Y2c and Y4b is N,
wherein Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl,
cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure;
wherein M is Ir or Rh.
4. The compound of claim 1,
wherein m is 2,
wherein n is 2,
wherein Y2b, Y2c and Y4b is CH,
wherein Y3b is N,
wherein Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure;
wherein M is Au..
5. The compound of claim 1, wherein each of R2 and R3 independently is linked to an adjacent ring structure.
6. The compound of claim 2,
wherein at least of one of Y2a, Y2d, Y3d and Y4d is C,
wherein at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a, Y2d, Y3d and Y4d, thereby forming a cyclic structure, and wherein M is Pt or Pd
7. The compound of claim 3,
wherein at least of one ofY2a and Y3d is C,
wherein Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a and Y3d, thereby forming a cyclic structure, and
wherein M is Ir or Rh.
8. The compound of claim 4,
wherein at least of one ofY2a and Y3d is C,
wherein Ylb is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a and Y3d, thereby forming a cyclic structure, and
wherein M is Au.
9. A compound having the structure:
wherein M comprises Ir, Rh, Pt, Os, or Ru; wherein each of R1 and R2 independently are hydrogen, substituted or
unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, nitro hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
wherein each of Yla, Ylb, Ylc, Yld, and Yle independently is O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure;
wherein each of Y2a, Y2b, Y2c, and Y2d independently is N, NR6a, or CR* wherein each of R6a and R* independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
wherein each of Y3a, Y3b, Y3c, Y3d, Y3e, Y4a, Y4b, Y4c, and Y4d independently is N, O, S, NR6a, CR6b, wherein each of R6a and R6b independently hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R6c)2, wherein Z is C or Si, and wherein each R6c independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, or arylalkene;
wherein in each of each of Y5a, Y5b, Y5c, Y5d, Y6a, Y6b, Y6c, and Y6d independently is N, O, S, NR6a, or CR6b;
wherein each of m and n independently are an integer 1 or 2; wherein each of * - ' independently is partial or full unsaturation of the ring with which it is associated.
10. The compound of claim 9,
wherein m is 2,
wherein Y2b and Y2c is CH,
wherein Y3b and Y4b is N,
wherein at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2,
or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to an adjacent ring structure, thereby forming a cyclic structure, and
wherein M is Ir or Rh.
1 1. The compound of claim 9, wherein each of R2 and R3 independently is linked to an adjacent ring structure.
12. The compound of claim 10,
wherein at least of one of Y2a, Y2d, Y3d and Y4d is C,
wherein at least one of Ylb and Ylc is NR2, CR2R3, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, wherein R2 is covalently linked to at least one of Y2a, Y2d, Y3d and Y4d, thereby forming a cyclic structure, and wherein M is Ir or Rh.
13. A compound having the formula:
Pd (ii);
wherein E1, E2, and E3 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each
of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group wherein a nitrogen atom coordinated to the metal.
14. A compound having the formula:
wherein E1, E2, and E3 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein N is selected from a substituted or unsubstituted heterocyclic group wherein a nitrogen atom coordinated to the metal.
15. A compound having the formula:
wherein E1, E2, and E3 independently represent a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein C is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group wherein a nitrogen atom is coordinated to the metal.
16. A compound having the formula:
Rh (III), Co (III), Al (III), or Ga (III),
wherein E1, E2, E3, and E4 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.
17. A compound having the formula:
wherein M is a metal cation with three positive charges selected from Ir (III), Rh (III), Co (III), Al (III), or Ga (III);
wherein E1, E2, E3, E4, and E5 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted
aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.
18. A compound having the formula:
wherein E1, E2, E3, and E4 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.
19. A compound having the formula:
wherein E1, E2, E3, E4, and E5 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.
20. A compound having the formula:
(Π);
wherein E1, E2, E3, E4, and E5 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom coordinated to the metal.
21. A compound having the formula:
wherein M is a metal cation with two positive charges selected from Ru (II), or Os (II);
wherein E1, E2, E3, and E4 independently is a linking atom comprising O, NR2, CR2R3, S, AsR2, BR2, PR2, P(0)R2, or SiR2R3, or a combination thereof, wherein each of R2 and R3 independently is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, hydroxyl, halogen, thio, alkoxy, haloalkyl, arylalkane, arylalkene, or R2 and R3 together form C=0, wherein each of R2 and R3 independently is optionally linked to a C or N, thereby forming a cyclic structure;
wherein each C independently is selected from a substituted or unsubstituted aromatic ring or heterocyclic group, wherein a carbon atom is coordinated to the metal; and
wherein each N independently is selected from a substituted or unsubstituted heterocyclic group, wherein a nitrogen atom is coordinated to the metal.
22. A device comprising one or more compounds of claims 1-21.
23. The device of claim 22, wherein the device is an organic light emitting diode.
24. The device of claim 22, wherein the device comprises a full color display.
25. The device of claim 22, wherein the one or more compounds is used as a host material.
26. The device of claim 22, wherein the device can be a lighting device.
27. A device comprising one or more compounds of claims 1-12, wherein the compound is used as a phosphorescent emitter in the device.
28. A device comprising one or more compounds of claims 1-12, wherein the compound is used as a delayed fluorescent and phosphorescent emitter in the device.
29. A composition comprising one or more compounds of claims 1-19.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/421,634 US9711741B2 (en) | 2012-08-24 | 2013-08-23 | Metal compounds and methods and uses thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261692937P | 2012-08-24 | 2012-08-24 | |
US61/692,937 | 2012-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014031977A1 true WO2014031977A1 (en) | 2014-02-27 |
Family
ID=50150407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2013/056426 WO2014031977A1 (en) | 2012-08-24 | 2013-08-23 | Metal compounds and methods and uses thereof |
Country Status (2)
Country | Link |
---|---|
US (1) | US9711741B2 (en) |
WO (1) | WO2014031977A1 (en) |
Cited By (117)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130168656A1 (en) * | 2012-01-03 | 2013-07-04 | Universal Display Corporation | Cyclometallated tetradentate platinum complexes |
US9224963B2 (en) | 2013-12-09 | 2015-12-29 | Arizona Board Of Regents On Behalf Of Arizona State University | Stable emitters |
US9238668B2 (en) | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US9324957B2 (en) | 2010-04-30 | 2016-04-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Synthesis of four coordinated gold complexes and their applications in light emitting devices thereof |
US9382273B2 (en) | 2010-04-30 | 2016-07-05 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
US9385329B2 (en) | 2013-10-14 | 2016-07-05 | Arizona Board of Regents on behalf of Arizona State University and Universal Display Corporation | Platinum complexes and devices |
EP3056504A1 (en) | 2015-02-16 | 2016-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9425415B2 (en) | 2011-02-18 | 2016-08-23 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Four coordinated platinum and palladium complexes with geometrically distorted charge transfer state and their applications in light emitting devices |
EP3061763A1 (en) | 2015-02-27 | 2016-08-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3098229A1 (en) | 2015-05-15 | 2016-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3101021A1 (en) | 2015-06-01 | 2016-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9550801B2 (en) | 2009-04-06 | 2017-01-24 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof |
EP3124488A1 (en) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3133078A1 (en) * | 2015-08-18 | 2017-02-22 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US9617291B2 (en) | 2015-06-03 | 2017-04-11 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
EP3159350A1 (en) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9673409B2 (en) | 2013-06-10 | 2017-06-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
US9711739B2 (en) | 2015-06-02 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes containing indoloacridine and its analogues |
US9711741B2 (en) | 2012-08-24 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal compounds and methods and uses thereof |
EP3205658A1 (en) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3231809A2 (en) | 2016-04-11 | 2017-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
EP3261146A2 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261147A1 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3270435A2 (en) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9882150B2 (en) | 2012-09-24 | 2018-01-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
US9920242B2 (en) | 2014-08-22 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
EP3297051A1 (en) | 2016-09-14 | 2018-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3301088A1 (en) | 2016-10-03 | 2018-04-04 | Universal Display Corporation | Condensed pyridines as organic electroluminescent materials and devices |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
EP3305796A1 (en) | 2016-10-07 | 2018-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3321258A1 (en) | 2016-11-09 | 2018-05-16 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3323822A1 (en) | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
EP3345914A1 (en) | 2017-01-09 | 2018-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
EP3354654A2 (en) | 2016-11-11 | 2018-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10056567B2 (en) | 2014-02-28 | 2018-08-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
EP3381927A1 (en) | 2017-03-29 | 2018-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3401318A1 (en) | 2017-05-11 | 2018-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10158091B2 (en) | 2015-08-04 | 2018-12-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
EP3418286A1 (en) | 2017-06-23 | 2018-12-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10177323B2 (en) | 2016-08-22 | 2019-01-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
EP3444258A2 (en) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3489243A1 (en) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492528A1 (en) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3492480A2 (en) | 2017-11-29 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN110240606A (en) * | 2018-03-09 | 2019-09-17 | 亚利桑那州立大学董事会 | Blue light and narrowband green light and red emission metal complex, and Organic Light Emitting Diode and light emitting device comprising it |
US10414785B2 (en) | 2011-04-14 | 2019-09-17 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Pyridine-oxyphenyl coordinated iridium (III) complexes and methods of making and using |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
EP3613751A1 (en) | 2018-08-22 | 2020-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3689889A1 (en) | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3690973A1 (en) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organic electroluminescent materials and devices |
EP3715353A1 (en) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10793546B2 (en) | 2014-08-15 | 2020-10-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
US10822363B2 (en) | 2016-10-12 | 2020-11-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Narrow band red phosphorescent tetradentate platinum (II) complexes |
US10851106B2 (en) | 2017-05-19 | 2020-12-01 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Substituted benzo[4,5]imidazo[1,2-F]phenanthridines, dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzofurophenanthridines and dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzo[4,5]thienophenanthridines as thermally assisted delayed fluorescent materials |
EP3750897A1 (en) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3771717A1 (en) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3778614A1 (en) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10964897B2 (en) | 2014-07-28 | 2021-03-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
US10991897B2 (en) | 2014-11-10 | 2021-04-27 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US10995108B2 (en) | 2012-10-26 | 2021-05-04 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal complexes, methods, and uses thereof |
EP3816175A1 (en) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3845545A1 (en) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN113087707A (en) * | 2021-04-09 | 2021-07-09 | 浙江工业大学 | 6/6/6-fused tetracyclic cyclometalated platinum (II) complex phosphorescent material based on aza-pyrazole-carbazole and application thereof |
EP3858945A1 (en) | 2020-01-28 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
CN113354688A (en) * | 2021-05-24 | 2021-09-07 | 浙江工业大学 | 6/6/6 tetradentate ring metal palladium (II) complex luminescent material based on azacarbazole-carbazole and application thereof |
US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US11245078B2 (en) | 2015-08-25 | 2022-02-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity |
US11329244B2 (en) | 2014-08-22 | 2022-05-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
EP4001286A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001287A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4016659A1 (en) | 2020-11-16 | 2022-06-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4019526A1 (en) | 2018-01-26 | 2022-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
EP4039692A1 (en) | 2021-02-03 | 2022-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4053137A1 (en) | 2021-03-05 | 2022-09-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4056578A1 (en) | 2021-03-12 | 2022-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11450816B2 (en) | 2017-05-19 | 2022-09-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Donor-acceptor type thermally activated delayed fluorescent materials based on imidazo[1,2-f]phenanthridine and analogues |
EP4059915A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059941A1 (en) | 2021-03-15 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075530A1 (en) | 2021-04-14 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4074723A1 (en) | 2021-04-05 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
EP4079743A1 (en) | 2021-04-23 | 2022-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4086266A1 (en) | 2021-04-23 | 2022-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4112701A2 (en) | 2021-06-08 | 2023-01-04 | University of Southern California | Molecular alignment of homoleptic iridium phosphors |
US11594688B2 (en) | 2017-10-17 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters |
US11594690B2 (en) | 2017-12-14 | 2023-02-28 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex, and polymer, mixture and formulation comprising same, and use thereof in electronic device |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
EP4185086A1 (en) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11674080B2 (en) | 2017-12-14 | 2023-06-13 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex, polymer, mixture, formulation and use thereof |
US11680059B2 (en) | 2017-12-21 | 2023-06-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture and application thereof in organic electronic devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11708385B2 (en) | 2017-01-27 | 2023-07-25 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
EP4231804A2 (en) | 2022-02-16 | 2023-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4242285A1 (en) | 2022-03-09 | 2023-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
EP4265626A2 (en) | 2022-04-18 | 2023-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4282863A1 (en) | 2022-05-24 | 2023-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4299693A1 (en) | 2022-06-28 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
EP4326030A1 (en) | 2022-08-17 | 2024-02-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11930662B2 (en) | 2015-06-04 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Transparent electroluminescent devices with controlled one-side emissive displays |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
EP4362645A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362630A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362631A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3140871B1 (en) | 2014-05-08 | 2018-12-26 | Universal Display Corporation | Stabilized imidazophenanthridine materials |
US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11152579B2 (en) | 2016-12-28 | 2021-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102390378B1 (en) | 2017-03-03 | 2022-04-26 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
US11084838B2 (en) | 2017-04-21 | 2021-08-10 | Universal Display Corporation | Organic electroluminescent materials and device |
KR102429875B1 (en) * | 2017-04-21 | 2022-08-05 | 삼성전자주식회사 | Organometallic compound and organic light emitting device including the same |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006067074A1 (en) * | 2004-12-23 | 2006-06-29 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with nucleophilic carbene ligands |
WO2008101842A1 (en) * | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
US20110062858A1 (en) * | 2006-07-28 | 2011-03-17 | Novaled Ag | Oxazole Triplet Emitters for OLED Applications |
WO2011064335A1 (en) * | 2009-11-27 | 2011-06-03 | Cynora Gmbh | Functionalized triplet emitters for electro-luminescent devices |
US20120199823A1 (en) * | 2009-10-14 | 2012-08-09 | Basf Se | Dinuclear platinum-carbene complexes and the use thereof in oleds |
Family Cites Families (180)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
US5318912A (en) | 1989-11-08 | 1994-06-07 | British Technology Group Limited | Gas sensors and compounds suitable therefor |
US5641878A (en) | 1991-05-15 | 1997-06-24 | Diatron Corporation | Porphyrin, azaporphyrin, and related fluorescent dyes free of aggregation and serum binding |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
EP3321954A1 (en) | 1999-05-13 | 2018-05-16 | The Trustees of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
US6821645B2 (en) | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
JP4154140B2 (en) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | Metal coordination compounds |
JP4460743B2 (en) | 2000-09-29 | 2010-05-12 | 富士フイルム株式会社 | Method for producing iridium complex or tautomer thereof |
JP5329734B2 (en) | 2001-08-15 | 2013-10-30 | スリーエム イノベイティブ プロパティズ カンパニー | Curable self-supporting structure and method |
JP4166455B2 (en) | 2001-10-01 | 2008-10-15 | 株式会社半導体エネルギー研究所 | Polarizing film and light emitting device |
GB0215153D0 (en) | 2002-07-01 | 2002-08-07 | Univ Hull | Luminescent compositions |
DE10238903A1 (en) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | New heteroaromatic rhodium and iridium complexes, useful in electroluminescent and/or phosphorescent devices as the emission layer and for use in solar cells, photovoltaic devices and organic photodetectors |
US20060094875A1 (en) | 2002-11-01 | 2006-05-04 | Hisanori Itoh | Platinum complexes |
US7037599B2 (en) | 2003-02-28 | 2006-05-02 | Eastman Kodak Company | Organic light emitting diodes for production of polarized light |
JP5095206B2 (en) | 2003-03-24 | 2012-12-12 | ユニバーシティ オブ サザン カリフォルニア | Phenyl and fluorenyl substituted phenyl-pyrazole complexes of iridium (Ir) |
US6998492B2 (en) | 2003-05-16 | 2006-02-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex and light-emitting element containing the same |
JP4460952B2 (en) | 2003-06-02 | 2010-05-12 | 富士フイルム株式会社 | Organic electroluminescent device and complex compound |
CN101667626B (en) | 2003-06-02 | 2012-11-28 | 富士胶片株式会社 | Organic electroluminescent devices and metal complex compounds |
US7569692B2 (en) | 2003-06-02 | 2009-08-04 | Fujifilm Corporation | Organic electroluminescent devices and metal complex compounds |
US6917159B2 (en) | 2003-08-14 | 2005-07-12 | Eastman Kodak Company | Microcavity OLED device |
US7268485B2 (en) | 2003-10-07 | 2007-09-11 | Eastman Kodak Company | White-emitting microcavity OLED device |
DE10350722A1 (en) | 2003-10-30 | 2005-05-25 | Covion Organic Semiconductors Gmbh | metal complexes |
KR101044087B1 (en) | 2003-11-04 | 2011-06-27 | 다카사고 고료 고교 가부시키가이샤 | Platinum complex and luminescent element |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
JP2005267557A (en) | 2004-03-22 | 2005-09-29 | Ntt Docomo Inc | Server device |
US20050211974A1 (en) | 2004-03-26 | 2005-09-29 | Thompson Mark E | Organic photosensitive devices |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
WO2005113704A2 (en) | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
JP4576605B2 (en) | 2004-08-09 | 2010-11-10 | 独立行政法人産業技術総合研究所 | Identification method of oligosaccharide |
JP4500735B2 (en) | 2004-09-22 | 2010-07-14 | 富士フイルム株式会社 | Organic electroluminescence device |
US7002013B1 (en) | 2004-09-23 | 2006-02-21 | National Tsing Hua University | Pt complexes as phosphorescent emitters in the fabrication of organic light emitting diodes |
JP4531509B2 (en) | 2004-09-27 | 2010-08-25 | 富士フイルム株式会社 | Light emitting element |
US7489074B2 (en) | 2004-09-28 | 2009-02-10 | Osram Opto Semiconductors Gmbh | Reducing or eliminating color change for microcavity OLED devices |
CN100348594C (en) | 2005-01-12 | 2007-11-14 | 武汉大学 | Bidentate ligand and its iridium complex and electroluminescent device therewith |
JP4773109B2 (en) | 2005-02-28 | 2011-09-14 | 高砂香料工業株式会社 | Platinum complex and light emitting device |
JP2006242080A (en) | 2005-03-02 | 2006-09-14 | Denso Corp | Abnormality diagnostic device for exhaust gas recirculating device |
JP4425816B2 (en) | 2005-03-02 | 2010-03-03 | 富士重工業株式会社 | Electronically controlled throttle device |
JP4727262B2 (en) | 2005-03-16 | 2011-07-20 | 富士フイルム株式会社 | Organic electroluminescence device |
JP4399382B2 (en) | 2005-03-16 | 2010-01-13 | 富士フイルム株式会社 | Organic electroluminescence device |
JP4399429B2 (en) | 2005-03-16 | 2010-01-13 | 富士フイルム株式会社 | Organic electroluminescence device |
EP2562840A1 (en) | 2005-03-16 | 2013-02-27 | UDC Ireland Limited | Platinum complex compound and organic electroluminescent device |
EP1866982A2 (en) | 2005-04-07 | 2007-12-19 | The Regents Of The University Of California | Highly efficient polymer solar cell by polymer self-organization |
JP4790298B2 (en) | 2005-04-08 | 2011-10-12 | 日本放送協会 | Good solubility iridium complex and organic EL device |
TWI418606B (en) | 2005-04-25 | 2013-12-11 | Udc Ireland Ltd | Organic electroluminescent device |
JP2006303394A (en) | 2005-04-25 | 2006-11-02 | Fuji Photo Film Co Ltd | Organic electroluminescent element |
JP4934346B2 (en) | 2005-04-25 | 2012-05-16 | 富士フイルム株式会社 | Organic electroluminescence device |
US7758971B2 (en) | 2005-04-25 | 2010-07-20 | Fujifilm Corporation | Organic electroluminescent device |
JP5046548B2 (en) | 2005-04-25 | 2012-10-10 | 富士フイルム株式会社 | Organic electroluminescence device |
TWI391027B (en) | 2005-04-25 | 2013-03-21 | Fujifilm Corp | Organic electroluminescent device |
JP4533796B2 (en) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2006351638A (en) | 2005-06-13 | 2006-12-28 | Fujifilm Holdings Corp | Light emitting device |
JP2007031678A (en) | 2005-07-29 | 2007-02-08 | Showa Denko Kk | Polymeric luminescent material and organic electroluminescence element using the polymeric luminescent material |
JP2007042875A (en) | 2005-08-03 | 2007-02-15 | Fujifilm Holdings Corp | Organic electroluminescence element |
JP4796802B2 (en) | 2005-08-15 | 2011-10-19 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2007066581A (en) | 2005-08-29 | 2007-03-15 | Fujifilm Holdings Corp | Organic electroluminescent element |
JP2007073620A (en) | 2005-09-05 | 2007-03-22 | Fujifilm Corp | Organic electroluminescent element |
JP5076900B2 (en) | 2005-09-06 | 2012-11-21 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element, display device and lighting device |
JP2007073845A (en) | 2005-09-08 | 2007-03-22 | Fujifilm Holdings Corp | Organic laser oscillator |
JP2007073900A (en) | 2005-09-09 | 2007-03-22 | Fujifilm Corp | Organic electroluminescent element |
JP2007080593A (en) | 2005-09-12 | 2007-03-29 | Fujifilm Corp | Electrochemical light-emitting element |
JP2007080677A (en) | 2005-09-14 | 2007-03-29 | Fujifilm Corp | Organic electroluminescent element and its manufacturing method |
JP2007110067A (en) | 2005-09-14 | 2007-04-26 | Fujifilm Corp | Composition for organic electroluminescence element, method of manufacturing organic electroluminescence element, and organic electroluminescence element |
JP2007110102A (en) | 2005-09-15 | 2007-04-26 | Fujifilm Corp | Organic electroluminescence element |
US7839078B2 (en) | 2005-09-15 | 2010-11-23 | Fujifilm Corporation | Organic electroluminescent element having a luminescent layer and a buffer layer adjacent thereto |
JP2007088105A (en) | 2005-09-20 | 2007-04-05 | Fujifilm Corp | Organic electroluminescence element |
TWI268952B (en) | 2005-09-21 | 2006-12-21 | Au Optronics Corp | Spiro silane compound and organic electroluminescent device using the same |
JP4789556B2 (en) | 2005-09-21 | 2011-10-12 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2007186490A (en) | 2005-12-14 | 2007-07-26 | Sumitomo Seika Chem Co Ltd | Compound for electroluminescent element and method for producing the same |
JP4945156B2 (en) | 2006-03-24 | 2012-06-06 | 富士フイルム株式会社 | Organic electroluminescence device |
JP5144034B2 (en) | 2006-05-31 | 2013-02-13 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2008010353A (en) | 2006-06-30 | 2008-01-17 | Seiko Epson Corp | Manufacturing method of mask, manufacturing method of wiring pattern, and manufacturing method of plasma display |
JP2008037848A (en) | 2006-08-10 | 2008-02-21 | Takasago Internatl Corp | Platinum complex and light-emitting element |
JP5205584B2 (en) | 2006-09-06 | 2013-06-05 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device and display device |
US7598381B2 (en) | 2006-09-11 | 2009-10-06 | The Trustees Of Princeton University | Near-infrared emitting organic compounds and organic devices using the same |
JP5049711B2 (en) | 2006-09-27 | 2012-10-17 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2008109085A (en) | 2006-09-29 | 2008-05-08 | Fujifilm Corp | Organic electroluminescent element |
JP2008103535A (en) | 2006-10-19 | 2008-05-01 | Takasago Internatl Corp | Light emitting element |
JP2008108617A (en) | 2006-10-26 | 2008-05-08 | Fujifilm Corp | Organic electroluminescent element |
JP2008117545A (en) | 2006-11-01 | 2008-05-22 | Nix Inc | Joint device for liquid feeding and receiving and fuel cell system equipped with this |
JP4924878B2 (en) | 2006-11-06 | 2012-04-25 | 株式会社ニコン | Absolute encoder |
JP4478166B2 (en) | 2006-11-09 | 2010-06-09 | 三星モバイルディスプレイ株式會社 | Organic light-emitting device provided with organic film containing organometallic complex |
JP5282260B2 (en) | 2006-11-27 | 2013-09-04 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
JP5187493B2 (en) | 2006-11-27 | 2013-04-24 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescent devices and novel indole derivatives |
JP2009076834A (en) | 2006-11-27 | 2009-04-09 | Fujifilm Corp | Organic electroluminescednt device, and new indole derivative |
US8273599B2 (en) | 2006-12-01 | 2012-09-25 | The Regents Of The University Of California | Enhancing performance characteristics of organic semiconducting films by improved solution processing |
KR101117006B1 (en) | 2006-12-26 | 2012-04-12 | 아사히 가세이 케미칼즈 가부시키가이샤 | Resin composition for printing plate |
JP4833106B2 (en) | 2007-02-13 | 2011-12-07 | 富士フイルム株式会社 | Organic light emitting device |
JP5230218B2 (en) | 2007-03-26 | 2013-07-10 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
JP5081010B2 (en) | 2007-03-26 | 2012-11-21 | 富士フイルム株式会社 | Organic electroluminescence device |
US20080241518A1 (en) | 2007-03-26 | 2008-10-02 | Tasuku Satou | Organic electroluminescence element |
US20100084967A1 (en) | 2007-03-28 | 2010-04-08 | Fujifilm Corporation | Organic electroluminescent device |
JP5430073B2 (en) | 2007-03-30 | 2014-02-26 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
EP1988079A1 (en) | 2007-04-25 | 2008-11-05 | Lonza Ag | Process for the preparation of optically active ethenylphenyl-alcohols |
JP5084361B2 (en) | 2007-06-18 | 2012-11-28 | 株式会社リコー | Image forming apparatus |
JP2009016184A (en) | 2007-07-04 | 2009-01-22 | Fujifilm Corp | Organic electroluminescent element |
JP2009016579A (en) | 2007-07-04 | 2009-01-22 | Fujifilm Corp | Organic electroluminescent element and manufacturing method |
JP5255794B2 (en) | 2007-07-27 | 2013-08-07 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
JP2009032989A (en) | 2007-07-27 | 2009-02-12 | Fujifilm Corp | Organic electroluminescent element |
JP5497259B2 (en) | 2007-07-27 | 2014-05-21 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
JP2009055010A (en) | 2007-07-27 | 2009-03-12 | Fujifilm Corp | Organic electroluminescent device |
KR101548382B1 (en) | 2007-09-14 | 2015-08-28 | 유디씨 아일랜드 리미티드 | Organic electroluminescence device |
JP5014036B2 (en) | 2007-09-18 | 2012-08-29 | 富士フイルム株式会社 | Organic electroluminescence device |
GB0718577D0 (en) | 2007-09-24 | 2007-10-31 | Acal Energy Ltd | Fuel cells |
JP5438941B2 (en) | 2007-09-25 | 2014-03-12 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
KR100905951B1 (en) | 2007-12-06 | 2009-07-06 | 주식회사 잉크테크 | Iridium Complex Containing Carbazole-Substituted Pyridine and Phenyl Derivatives as Main Ligand and Organic Light-Emitting Diodes Containing The Same |
US9293720B2 (en) | 2008-02-19 | 2016-03-22 | New Jersey Institute Of Technology | Carbon nanotubes as charge carriers in organic and hybrid solar cells |
JP5243972B2 (en) | 2008-02-28 | 2013-07-24 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
US8389725B2 (en) | 2008-02-29 | 2013-03-05 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Tridentate platinum (II) complexes |
JP2009211892A (en) | 2008-03-03 | 2009-09-17 | Fujifilm Corp | Organic electroluminescent element |
DE102008015526B4 (en) | 2008-03-25 | 2021-11-11 | Merck Patent Gmbh | Metal complexes |
JP4531836B2 (en) | 2008-04-22 | 2010-08-25 | 富士フイルム株式会社 | Organic electroluminescent device, novel platinum complex compound and novel compound that can be a ligand |
JP2009266943A (en) | 2008-04-23 | 2009-11-12 | Fujifilm Corp | Organic field light-emitting element |
JP4531842B2 (en) | 2008-04-24 | 2010-08-25 | 富士フイルム株式会社 | Organic electroluminescence device |
JP2009267171A (en) | 2008-04-25 | 2009-11-12 | Fujifilm Corp | Organic electric field light emitting element |
JP2009267244A (en) | 2008-04-28 | 2009-11-12 | Fujifilm Corp | Organic electroluminescent element |
JP2009272339A (en) | 2008-04-30 | 2009-11-19 | Fujifilm Corp | Organic electric field light-emitting element |
KR20110031387A (en) | 2008-07-16 | 2011-03-25 | 솔베이(소시에떼아노님) | Light-emitting material comprising multinuclear complexes |
JP2012500500A (en) | 2008-08-20 | 2012-01-05 | プレックストロニクス インコーポレーティッド | Improved solvent system for the manufacture of organic solar cells |
AU2009282691A1 (en) | 2008-08-21 | 2010-02-25 | Tpk Holding Co., Ltd. | Enhanced surfaces, coatings, and related methods |
US7635792B1 (en) | 2008-10-14 | 2009-12-22 | General Electric Company | 2,5-linked polyfluorenes for optoelectronic devices |
JP5854839B2 (en) | 2008-11-11 | 2016-02-09 | ユニバーサル ディスプレイ コーポレイション | Phosphorescent emitter |
WO2010059240A1 (en) | 2008-11-21 | 2010-05-27 | Plextronics, Inc. | Doped interfacial modification layers for stability enhancement for bulk heterojunction organic solar cells |
JP5497284B2 (en) | 2008-12-08 | 2014-05-21 | ユー・ディー・シー アイルランド リミテッド | White organic electroluminescence device |
US8420234B2 (en) | 2009-01-06 | 2013-04-16 | Udc Ireland Limited | Organic electroluminescent device |
JP5627883B2 (en) | 2009-01-07 | 2014-11-19 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
KR101066743B1 (en) | 2009-02-13 | 2011-09-21 | 부산대학교 산학협력단 | Iridium complex and organic light-emitting diodes |
JP5644143B2 (en) | 2009-03-25 | 2014-12-24 | 住友化学株式会社 | Coating method and manufacturing method of organic electroluminescence element |
JP5604505B2 (en) | 2009-04-06 | 2014-10-08 | アリゾナ ボード オブ リージェンツ アクティング フォー アンド オン ビハーフ オブ アリゾナ ステイト ユニバーシティ | Synthesis of four-coordinate platinum complexes and their application to light-emitting devices |
CN102396250A (en) | 2009-04-17 | 2012-03-28 | 松下电器产业株式会社 | Apparatus for management of local ip access in segmented mobile communication system |
WO2010135701A1 (en) | 2009-05-21 | 2010-11-25 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
JP2010185068A (en) | 2009-08-31 | 2010-08-26 | Fujifilm Corp | Organic electroluminescent device |
JP5770441B2 (en) | 2009-09-30 | 2015-08-26 | ユー・ディー・シー アイルランド リミテッド | Material for organic electroluminescence device and organic electroluminescence device |
CN102576805A (en) | 2009-10-30 | 2012-07-11 | 住友化学株式会社 | Organic photoelectric conversion element and process for production thereof |
EP2497130B1 (en) | 2009-11-06 | 2018-01-24 | Nano-C, Inc. | Fullerene-functionalized particles, methods for making the same and their use in bulkheterojunction organic photovoltaic devices |
JP5495746B2 (en) | 2009-12-08 | 2014-05-21 | キヤノン株式会社 | Novel iridium complex and organic light emitting device having the same |
CN102668152A (en) | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | Compositions comprising polymeric binders |
KR20130109947A (en) | 2010-04-30 | 2013-10-08 | 아리조나 보드 오브 리젠츠 퍼 앤 온 비하프 오브 아리조나 스테이트 유니버시티 | Synthesis of four coordinated gold complexes and their applications in light emitting devices thereof |
JP2013530135A (en) | 2010-04-30 | 2013-07-25 | アリゾナ ボード オブ リージェンツ アクティング フォー アンド オン ビハーフ オブ アリゾナ ステイト ユニバーシティ | Synthesis of tetracoordinate palladium complex and its application in light-emitting devices |
JP5601505B2 (en) | 2010-06-16 | 2014-10-08 | 清水建設株式会社 | Damping beam consisting of precast formwork and construction method of damping beam |
TWI541247B (en) | 2011-02-18 | 2016-07-11 | 美國亞利桑那州立大學董事會 | Four coordinated platinum and palladium complexes with geometrically distorted charge transfer state and their applications in light emitting devices |
CN103476781B (en) | 2011-02-23 | 2017-02-15 | 通用显示公司 | Novel tetradentate platinum complexes |
JP5794813B2 (en) | 2011-04-12 | 2015-10-14 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescent element, organic electroluminescent element material, film, and method for producing organic electroluminescent element |
WO2012142387A1 (en) | 2011-04-14 | 2012-10-18 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Pyridine-oxyphenyl coordinated iridium (iii) complexes and methods of making and using |
WO2012162488A1 (en) | 2011-05-26 | 2012-11-29 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
CN103619860B (en) | 2011-06-03 | 2016-08-17 | 默克专利有限公司 | Metal complex |
US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101897044B1 (en) | 2011-10-20 | 2018-10-23 | 에스에프씨 주식회사 | Organic metal compounds and organic light emitting diodes comprising the same |
US9461254B2 (en) * | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN104272487B (en) | 2012-02-27 | 2017-09-01 | 李坚 | With arrowband phosphorescent emissive material in the Organic Light Emitting Diode for possessing micro chamber structure |
CN202549937U (en) | 2012-05-10 | 2012-11-21 | 京东方科技集团股份有限公司 | Organic light-emitting diode (OLED) display structure and OLED display device |
US9502672B2 (en) | 2012-06-21 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9231218B2 (en) | 2012-07-10 | 2016-01-05 | Universal Display Corporation | Phosphorescent emitters containing dibenzo[1,4]azaborinine structure |
US9059412B2 (en) | 2012-07-19 | 2015-06-16 | Universal Display Corporation | Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs |
GB201213392D0 (en) | 2012-07-27 | 2012-09-12 | Imp Innovations Ltd | Electroluminescent compositions |
US9312502B2 (en) | 2012-08-10 | 2016-04-12 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Iridium complexes demonstrating broadband emission through controlled geometric distortion and applications thereof |
WO2014031977A1 (en) | 2012-08-24 | 2014-02-27 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds and methods and uses thereof |
WO2014047616A1 (en) | 2012-09-24 | 2014-03-27 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
US9312505B2 (en) | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2014109814A2 (en) | 2012-10-26 | 2014-07-17 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Metal complexes, methods, and uses thereof |
WO2015027060A1 (en) | 2013-08-21 | 2015-02-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
CN110003279A (en) | 2013-06-10 | 2019-07-12 | 代表亚利桑那大学的亚利桑那校董会 | Four tooth metal complex of phosphorescence with improved emission spectrum |
US9735378B2 (en) | 2013-09-09 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6804823B2 (en) | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーArizona Board of Regents on behalf of Arizona State University | Platinum complex and device |
US9224963B2 (en) | 2013-12-09 | 2015-12-29 | Arizona Board Of Regents On Behalf Of Arizona State University | Stable emitters |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
WO2015131158A1 (en) | 2014-02-28 | 2015-09-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
EP3140871B1 (en) | 2014-05-08 | 2018-12-26 | Universal Display Corporation | Stabilized imidazophenanthridine materials |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
WO2016025921A1 (en) | 2014-08-15 | 2016-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
US9920242B2 (en) | 2014-08-22 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
US9865825B2 (en) | 2014-11-10 | 2018-01-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US9711739B2 (en) | 2015-06-02 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes containing indoloacridine and its analogues |
US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
-
2013
- 2013-08-23 WO PCT/US2013/056426 patent/WO2014031977A1/en active Application Filing
- 2013-08-23 US US14/421,634 patent/US9711741B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006067074A1 (en) * | 2004-12-23 | 2006-06-29 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with nucleophilic carbene ligands |
US20110062858A1 (en) * | 2006-07-28 | 2011-03-17 | Novaled Ag | Oxazole Triplet Emitters for OLED Applications |
WO2008101842A1 (en) * | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
US20120199823A1 (en) * | 2009-10-14 | 2012-08-09 | Basf Se | Dinuclear platinum-carbene complexes and the use thereof in oleds |
WO2011064335A1 (en) * | 2009-11-27 | 2011-06-03 | Cynora Gmbh | Functionalized triplet emitters for electro-luminescent devices |
Non-Patent Citations (3)
Title |
---|
BO YAO ET AL., THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, 6 April 2012 (2012-04-06), pages 3336 - 3340 * |
HAN-YUAN GONG ET AL., TETRAHEDRON, vol. 65, 2009, pages 87 - 92 * |
ZU-LI WANG ET AL., CHEM.COMMUN., vol. 48, 14 August 2012 (2012-08-14), pages 9418 - 9420 * |
Cited By (180)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9550801B2 (en) | 2009-04-06 | 2017-01-24 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof |
US10263197B2 (en) | 2010-04-30 | 2019-04-16 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
US9755163B2 (en) | 2010-04-30 | 2017-09-05 | Arizona Board Of Regents Acting For Or On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
US10727422B2 (en) | 2010-04-30 | 2020-07-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
US9324957B2 (en) | 2010-04-30 | 2016-04-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Synthesis of four coordinated gold complexes and their applications in light emitting devices thereof |
US9382273B2 (en) | 2010-04-30 | 2016-07-05 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
US9711742B2 (en) | 2011-02-18 | 2017-07-18 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Four coordinated platinum and palladium complexes with geometrically distorted charge transfer state and their applications in light emitting devices |
US9425415B2 (en) | 2011-02-18 | 2016-08-23 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Four coordinated platinum and palladium complexes with geometrically distorted charge transfer state and their applications in light emitting devices |
US10414785B2 (en) | 2011-04-14 | 2019-09-17 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Pyridine-oxyphenyl coordinated iridium (III) complexes and methods of making and using |
US9238668B2 (en) | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US10804476B2 (en) | 2011-05-26 | 2020-10-13 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US9698359B2 (en) | 2011-05-26 | 2017-07-04 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US11121328B2 (en) | 2011-05-26 | 2021-09-14 | Arizona Board Of Regents On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US20130168656A1 (en) * | 2012-01-03 | 2013-07-04 | Universal Display Corporation | Cyclometallated tetradentate platinum complexes |
US9461254B2 (en) * | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9711741B2 (en) | 2012-08-24 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal compounds and methods and uses thereof |
US10622571B2 (en) | 2012-09-24 | 2020-04-14 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
US11114626B2 (en) | 2012-09-24 | 2021-09-07 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
US9882150B2 (en) | 2012-09-24 | 2018-01-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
US10995108B2 (en) | 2012-10-26 | 2021-05-04 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal complexes, methods, and uses thereof |
US9673409B2 (en) | 2013-06-10 | 2017-06-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
US9899614B2 (en) | 2013-06-10 | 2018-02-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
US10211414B2 (en) | 2013-06-10 | 2019-02-19 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
US9947881B2 (en) | 2013-10-14 | 2018-04-17 | Arizona Board Of Regents On Behalf Of Arizona State University | Platinum complexes and devices |
US9385329B2 (en) | 2013-10-14 | 2016-07-05 | Arizona Board of Regents on behalf of Arizona State University and Universal Display Corporation | Platinum complexes and devices |
US11189808B2 (en) | 2013-10-14 | 2021-11-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Platinum complexes and devices |
US10566553B2 (en) | 2013-10-14 | 2020-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Platinum complexes and devices |
US9224963B2 (en) | 2013-12-09 | 2015-12-29 | Arizona Board Of Regents On Behalf Of Arizona State University | Stable emitters |
US10937976B2 (en) | 2014-01-07 | 2021-03-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
US11930698B2 (en) | 2014-01-07 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
US10056567B2 (en) | 2014-02-28 | 2018-08-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
US11839144B2 (en) | 2014-06-02 | 2023-12-05 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
US11011712B2 (en) | 2014-06-02 | 2021-05-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
US10886478B2 (en) | 2014-07-24 | 2021-01-05 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
US10964897B2 (en) | 2014-07-28 | 2021-03-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
US10790457B2 (en) | 2014-07-29 | 2020-09-29 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
US11145830B2 (en) | 2014-07-29 | 2021-10-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
US10793546B2 (en) | 2014-08-15 | 2020-10-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
US10745615B2 (en) | 2014-08-22 | 2020-08-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US11339324B2 (en) | 2014-08-22 | 2022-05-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US11795387B2 (en) | 2014-08-22 | 2023-10-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US10294417B2 (en) | 2014-08-22 | 2019-05-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDS |
US11329244B2 (en) | 2014-08-22 | 2022-05-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
US9920242B2 (en) | 2014-08-22 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US11653560B2 (en) | 2014-11-10 | 2023-05-16 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
US10991897B2 (en) | 2014-11-10 | 2021-04-27 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US11856840B2 (en) | 2014-11-10 | 2023-12-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
US10944064B2 (en) | 2014-11-10 | 2021-03-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
EP3056504A1 (en) | 2015-02-16 | 2016-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3061763A1 (en) | 2015-02-27 | 2016-08-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3098229A1 (en) | 2015-05-15 | 2016-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3101021A1 (en) | 2015-06-01 | 2016-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10056564B2 (en) | 2015-06-02 | 2018-08-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes containing indoloacridine and its analogues |
US9711739B2 (en) | 2015-06-02 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes containing indoloacridine and its analogues |
US9617291B2 (en) | 2015-06-03 | 2017-04-11 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US11472827B2 (en) | 2015-06-03 | 2022-10-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US10836785B2 (en) | 2015-06-03 | 2020-11-17 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US11930662B2 (en) | 2015-06-04 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Transparent electroluminescent devices with controlled one-side emissive displays |
EP3124488A1 (en) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10930865B2 (en) | 2015-08-04 | 2021-02-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
US10158091B2 (en) | 2015-08-04 | 2018-12-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
EP3133078A1 (en) * | 2015-08-18 | 2017-02-22 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US11211571B2 (en) | 2015-08-18 | 2021-12-28 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US11245078B2 (en) | 2015-08-25 | 2022-02-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity |
EP3159350A1 (en) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3760635A1 (en) | 2015-09-03 | 2021-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3205658A1 (en) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858842A1 (en) | 2016-02-09 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4122941A1 (en) | 2016-04-11 | 2023-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3231809A2 (en) | 2016-04-11 | 2017-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
EP4349935A2 (en) | 2016-06-20 | 2024-04-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3270435A2 (en) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261147A1 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3758084A1 (en) | 2016-06-20 | 2020-12-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3843171A1 (en) | 2016-06-20 | 2021-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3261146A2 (en) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3920254A1 (en) | 2016-06-20 | 2021-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10566554B2 (en) | 2016-08-22 | 2020-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
US10177323B2 (en) | 2016-08-22 | 2019-01-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
EP3297051A1 (en) | 2016-09-14 | 2018-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3323822A1 (en) | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3301088A1 (en) | 2016-10-03 | 2018-04-04 | Universal Display Corporation | Condensed pyridines as organic electroluminescent materials and devices |
EP3858844A1 (en) | 2016-10-07 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3305796A1 (en) | 2016-10-07 | 2018-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10822363B2 (en) | 2016-10-12 | 2020-11-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Narrow band red phosphorescent tetradentate platinum (II) complexes |
EP3321258A1 (en) | 2016-11-09 | 2018-05-16 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3789379A1 (en) | 2016-11-09 | 2021-03-10 | Universal Display Corporation | 4-phenylbenzo[g]quinazoline or 4-(3,5-dimethylphenylbenzo[g]quinazoline iridium complexes for use as near-infrared or infrared emitting materials in oleds |
EP3354654A2 (en) | 2016-11-11 | 2018-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4092036A1 (en) | 2016-11-11 | 2022-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
EP3345914A1 (en) | 2017-01-09 | 2018-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3689890A1 (en) | 2017-01-09 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212540A1 (en) | 2017-01-09 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11708385B2 (en) | 2017-01-27 | 2023-07-25 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
EP3730506A1 (en) | 2017-03-29 | 2020-10-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3985012A1 (en) | 2017-03-29 | 2022-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3381927A1 (en) | 2017-03-29 | 2018-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4141010A1 (en) | 2017-05-11 | 2023-03-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3401318A1 (en) | 2017-05-11 | 2018-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
US10851106B2 (en) | 2017-05-19 | 2020-12-01 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Substituted benzo[4,5]imidazo[1,2-F]phenanthridines, dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzofurophenanthridines and dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzo[4,5]thienophenanthridines as thermally assisted delayed fluorescent materials |
US11603370B2 (en) | 2017-05-19 | 2023-03-14 | Arizona Board Of Regents On Behalf Of Arizona State University | Substituted heteroaryls as thermally assisted delayed fluorescent materials |
US11063228B2 (en) | 2017-05-19 | 2021-07-13 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing benzo-imidazo-phenanthridine and analogues |
US11450816B2 (en) | 2017-05-19 | 2022-09-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Donor-acceptor type thermally activated delayed fluorescent materials based on imidazo[1,2-f]phenanthridine and analogues |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
US11974495B2 (en) | 2017-05-19 | 2024-04-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
EP3418286A1 (en) | 2017-06-23 | 2018-12-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4185086A1 (en) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3783006A1 (en) | 2017-08-10 | 2021-02-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3444258A2 (en) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11594688B2 (en) | 2017-10-17 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
EP3878855A1 (en) | 2017-11-28 | 2021-09-15 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3489243A1 (en) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480A2 (en) | 2017-11-29 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3492528A1 (en) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11594690B2 (en) | 2017-12-14 | 2023-02-28 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex, and polymer, mixture and formulation comprising same, and use thereof in electronic device |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
US11674080B2 (en) | 2017-12-14 | 2023-06-13 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex, polymer, mixture, formulation and use thereof |
US11680059B2 (en) | 2017-12-21 | 2023-06-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture and application thereof in organic electronic devices |
EP4019526A1 (en) | 2018-01-26 | 2022-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN110240606A (en) * | 2018-03-09 | 2019-09-17 | 亚利桑那州立大学董事会 | Blue light and narrowband green light and red emission metal complex, and Organic Light Emitting Diode and light emitting device comprising it |
EP4206210A1 (en) | 2018-08-22 | 2023-07-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3613751A1 (en) | 2018-08-22 | 2020-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
EP3690973A1 (en) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organic electroluminescent materials and devices |
EP3689889A1 (en) | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4301117A2 (en) | 2019-02-01 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3715353A1 (en) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4134371A2 (en) | 2019-03-26 | 2023-02-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3750897A1 (en) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4219515A1 (en) | 2019-07-30 | 2023-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3771717A1 (en) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3778614A1 (en) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
EP3816175A1 (en) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3845545A1 (en) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4151644A1 (en) | 2020-01-06 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4294157A2 (en) | 2020-01-28 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3858945A1 (en) | 2020-01-28 | 2021-08-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
EP4016659A1 (en) | 2020-11-16 | 2022-06-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4329463A2 (en) | 2020-11-24 | 2024-02-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001286A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4001287A1 (en) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4039692A1 (en) | 2021-02-03 | 2022-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A2 (en) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4053137A1 (en) | 2021-03-05 | 2022-09-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4056578A1 (en) | 2021-03-12 | 2022-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059941A1 (en) | 2021-03-15 | 2022-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4074723A1 (en) | 2021-04-05 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN113087707A (en) * | 2021-04-09 | 2021-07-09 | 浙江工业大学 | 6/6/6-fused tetracyclic cyclometalated platinum (II) complex phosphorescent material based on aza-pyrazole-carbazole and application thereof |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
EP4075530A1 (en) | 2021-04-14 | 2022-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4079743A1 (en) | 2021-04-23 | 2022-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4086266A1 (en) | 2021-04-23 | 2022-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN113354688A (en) * | 2021-05-24 | 2021-09-07 | 浙江工业大学 | 6/6/6 tetradentate ring metal palladium (II) complex luminescent material based on azacarbazole-carbazole and application thereof |
EP4112701A2 (en) | 2021-06-08 | 2023-01-04 | University of Southern California | Molecular alignment of homoleptic iridium phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4231804A2 (en) | 2022-02-16 | 2023-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4242285A1 (en) | 2022-03-09 | 2023-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4265626A2 (en) | 2022-04-18 | 2023-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4282863A1 (en) | 2022-05-24 | 2023-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4299693A1 (en) | 2022-06-28 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4326030A1 (en) | 2022-08-17 | 2024-02-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362645A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362630A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4362631A2 (en) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
Also Published As
Publication number | Publication date |
---|---|
US20150207086A1 (en) | 2015-07-23 |
US9711741B2 (en) | 2017-07-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2014031977A1 (en) | Metal compounds and methods and uses thereof | |
JP5466005B2 (en) | Oxazole-triplet-emitters for OLED applications | |
CN101654466B (en) | Transition metal complexes comprising carbene ligands serving as emitters for organic light-emitting diodes (OLED's) | |
CN104540840B (en) | Transient metal complex with carbene ligands and its purposes in OLED | |
EP1856227B1 (en) | Red phosphorescence compounds and organic electroluminescence devices using the same | |
JP5722220B2 (en) | Organic electroluminescence device | |
WO2014047616A1 (en) | Metal compounds, methods, and uses thereof | |
JP5266203B2 (en) | Luminescent substance | |
EP2417217A2 (en) | Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof | |
WO2007078183A1 (en) | Metallic compound and organic electroluminescence device comprising the same | |
JP2007302565A (en) | Metal complex, light-emitting element and image-displaying element | |
CN102399244B (en) | Dihydro acridine derivatives, application thereof and organic electroluminescent device applying same | |
Han et al. | Efficient orange-red electroluminescence of iridium complexes with 1-(2, 6-bis (trifluoromethyl) pyridin-4-yl) isoquinoline and 4-(2, 6-bis (trifluoromethyl) pyridin-4-yl) quinazoline ligands | |
CN109153913A (en) | For luminous four-coordination fund (III) compound of organic light emitting apparatus and its preparation | |
US7939663B2 (en) | Metallic compound and organic electroluminescence device comprising the same | |
US9000157B2 (en) | Metallic compound and organic electroluminescence device comprising the same | |
CN107722059B (en) | Cycloaryl iridium complex compound and organic electroluminescent device using the same | |
Zhang et al. | Synthesis, characterization, photo-and electro-luminescent properties of blue cationic iridium complexes with nonconjugated bis (pyrazole-1-yl) methane as the ancillary ligand | |
CN109790195A (en) | Iridium complex compound and composition, organic electroluminescent device, display device and lighting device containing above compound | |
EP3266788B1 (en) | Metal complex and manufacturing method and usage, display device thereof | |
Wang et al. | Dinuclear cyclometalated platinum (II) complexes: Synthesis, photophysics, and monomolecular electroluminescence | |
CN113527372A (en) | Divalent platinum metal complex, organic light-emitting device, and display or lighting device | |
Li et al. | High-efficient phosphorescent iridium (III) complexes with benzimidazole ligand for organic light-emitting diodes: Synthesis, electrochemistry and electroluminescent properties | |
US20090306395A1 (en) | Metallic compound and organic electroluminescence device comprising the same | |
JP2013545754A (en) | Metal complexes containing ligands with a combination of donor and acceptor substituents |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13830708 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14421634 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 13830708 Country of ref document: EP Kind code of ref document: A1 |