EP1754267A1 - Organometallic compounds and devices made with such compounds - Google Patents

Organometallic compounds and devices made with such compounds

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Publication number
EP1754267A1
EP1754267A1 EP05759481A EP05759481A EP1754267A1 EP 1754267 A1 EP1754267 A1 EP 1754267A1 EP 05759481 A EP05759481 A EP 05759481A EP 05759481 A EP05759481 A EP 05759481A EP 1754267 A1 EP1754267 A1 EP 1754267A1
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Prior art keywords
compound
ligands
ligand
layer
formula
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German (de)
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French (fr)
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Norman Herron
Nora Sabina Radu
Eric Maurice Smith
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • 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 Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • 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
    • 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
    • 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
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • This invention relates to organometallic compounds, and more particularly to electrically active organometallic compounds. It also relates to electronic devices in which an active layer includes at least one such organometallic compound.
  • Organic electronic devices that emit light such as light-emitting diodes that make up displays, are present in many different kinds of electronic equipment.
  • an organic active layer is sandwiched between two electrical contact layers. At least one of the electrical contact layers is light-transmitting so that light can pass through the electrical contact layer.
  • the organic active layer emits light through the light-transmitting electrical contact layer upon application of electricity across the electrical contact layers.
  • organic electroluminescent compounds as the active component in light-emitting diodes. Simple organic molecules such as anthracene, thiadiazole derivatives, and coumarin derivatives are known to show electroluminescence.
  • Electroluminescent components Semiconductive conjugated polymers have also been used as electroluminescent components, as has been disclosed in, for example, Friend et al., U.S. Patent 5,247,190, Heeger et al., U.S. Patent 5,408,109, and Nakano et al., Published European Patent Application 443 861.
  • Complexes of 8-hydroxyquinolate with trivalent metal ions, particularly aluminum, have been extensively used as electroluminescent components, as has been disclosed in, for example, Tang et al., U.S. Patent 5,552,678. Burrows and Thompson have reported that fac-tris(2- phenylpyridine) iridium can be used as the active component in organic light-emitting devices. (Appl. Phys. Lett.
  • L 1 is selected from an aryl-N-heterocycle ligand and a heteroaryl-N- heterocycle ligand
  • L 2 is an anionic ligand
  • L 3 is a nonionic ligand
  • L 4 is selected from L 1 and L 2 M is a metal selected from Re, Ru, Os, Rh, Ir, Pd, Pt, and Au FW is a moiety capable of bearing at least two (L 4 -Y e ) groups
  • Y is a group selected from alkylene, heteroalkylene, alkenylene, heteroalkenylene, and alkynylene
  • a is selected from 1 and 2 b is selected from 0 and 1 c is selected from 0, 1
  • 2 d is selected from an integer from 1 through 8
  • e is selected from 0 and 1 f is selected from 0 and 1
  • g is an integer from 1 through 4
  • h is selected from land 2.
  • a composition comprises at least one of the above compounds of Formula I, II, or 111.
  • electronic devices containing at least one active layer comprising at least one invention compound.
  • OLEDs organic light emitting diodes
  • electroluminescent devices containing at least one active layer including at least one invention compound.
  • methods for improving solution processability of electroluminescent organometallic compounds are performed by assembling monometallic groups into polymetallic compounds by covalently attaching at least two monometallic groups to a framework structure, wherein the monometallic groups are either directly attached to the framework structure through a ligand or indirectly attached through a linker, thereby improving solution processability.
  • such methods are performed by attaching at least one solvent-solubilizing substituent to at least one ligand of an organomonometallic compound.
  • OLEDs organic light emitting diodes
  • photoactive devices containing at least one active layer including a compound of the above Formulae.
  • the emissive layer comprises a host transport material into which the electroluminescent material is doped at ⁇ 20 wt %. In one embodiment there is excellent miscibility between the host and electroluminescent material and a quality film may be deposited by a liquid deposition technique.
  • the compounds of the invention have Formula I, Formula II, or Formula III, described above.
  • M is a metal selected from Re, Ru, Os, Rh, Ir, Pd, Pt, and Au.
  • Pd, Pt, and Au have a +2 oxidation state and are typically tetra-coordinate.
  • the L 1 ligand described below, occupies two of the coordination positions. The other two are occupied by L 4 and, when L 4 is monodentate, also by L 3 .
  • Re, Ru, Os, Rh, and Ir have a +3 oxidation state and are typically hexacoordinate.
  • M is selected from Os, Ir, and Pt.
  • L 1 is selected from an aryl-N-heterocycle ligand and a heteroaryl-N- heterocyle ligand.
  • the ligand has an aromatic or heteroaromatic ring joined to a N-heteroaromatic ring by a single bond.
  • the aromatic or heteroaromatic ring may comprise a single ring or a fused ring system. Examples of aromatic rings include, but are not limited to phenyl, naphthyl, and anthracenyl. Examples of heteroaromatic rings include, but are not limited to, rings derived from thiophene, dithiole pyridine.
  • the N- heteroaromatic ring may comprise a single ring or fused ring system.
  • N-heteroaromatic groups include, but are not limited to, pyridine, pyrazine, pyrimidine, and quinolines.
  • L 1 is selected from a phenyl-pyridine, phenyl-pyrimidine, phenyl-quinoline, bipyridine and thienyl-pyridine.
  • Ligand L 1 is coordinated to the metal by two points of attachment and is a monoanionic, bidentate ligand. The two points of attachment are through the nitrogen atom of the N- heteroaromatic ring and to a carbon of the aromatic or heteroaromatic ring.
  • L 2 is a monoanionic ligand. L 2 can be monodentate, bidentate or tridentate.
  • monodentate L 2 ligands include, but are not limited to, H- ("hydride") and ligands having C, O or S as coordinating atoms. Coordinating groups include, but are not limited to alkoxide, carboxylate, thiocarboxylate, dithiocarboxylate, sulfonate, thiolate, nitrile, aryl, carbamate, dithiocarbamate, thiocarbazone anions, sulfonamide anions, and the like. In some cases, ligands discussed below as bidentate, such as ⁇ -enolates and phosphinoakoxides, can act as monodentate ligands.
  • the monodentate ligand can also be a coordinating anion such as halide, nitrate, sulfate, hexahaloantimonate, and the like. These ligands are generally available commercially.
  • the bidentate L 2 ligands generally have N, O, P, or S as coordinating atoms and form 5- or 6-membered rings when coordinated to the metal. Suitable coordinating groups include amino, imino, amido, alkoxide, carboxylate, phosphino, thiolate, and the like.
  • Suitable parent compounds for these ligands include, but are not limited to ?-dicarbonyls ( ?-enolate ligands), and their N and S analogs; amino carboxylic acids (aminocarboxylate ligands); pyridine carboxylic acids (iminocarboxylate ligands); salicylic acid derivatives (salicylate ligands); hydroxyquinolines (hydroxyquinolinate ligands) and their S analogs; and phosphinoalkanols (phosphinoalkoxide ligands).
  • the ?-enolate ligands generally have the FormulalV: R 2 ⁇ (-i)
  • R 2 is the same or different at each occurrence.
  • the R 2 groups can be hydrogen, halogen, substituted or unsubstituted alkyl, aryl, alkylaryl or heterocyclic groups. Adjacent R 2 and R 3 groups can be joined to form five- and six-membered rings, which can be substituted.
  • R 2 groups are selected from C n (H+F) 2n+ -i , -C 6 H 5 , C-C4H3S, and C-C4H3O, where n is an integer from 1 through 20.
  • the R 3 group can be H, substituted or unsubstituted, alkyl, aryl, alkylaryl, heterocyclic groups or fluorine.
  • Suitable ?-enolate ligands include the compounds listed below. The abbreviation for the ?-enolate form is given below in brackets. 2,4-pentanedionate [acac] 1 ,3-diphenyl-1 ,3-propanedionate [Dl] 2,2,6,6-tetramethyl-3,5-heptanedionate [TMH] 4,4,4-trifluoro-1-(2-thienyl)-1 ,3-butanedionate [TTFA] 7,7-dimethyl-1 ,1 ,1 ⁇ .S ⁇ -heptafluoro ⁇ . ⁇ -octanedionate [FOD] 1 ,1 ,1 ,3,5,5,5-heptafluoro-2,4-pentanedionate [F7acac] 1 ,1 ,1 ,5,5,5-hexafluoro-2,4-pentanedionate [F6acac] 1 -phen
  • the parent compound 1 ,1 ,1 ,3,5,5,5-heptafluoro-2,4- pentanedione, CF 3 C(O)CFHC(O)CF 3 can be prepared using a two-step synthesis, based on the reaction of perfluoropentene-2 with ammonia, followed by a hydrolysis step according to the procedure published in Izv. AN USSR. Ser. Khim. 1980, 2827. This compound should be stored and reacted under anhydrous conditions as it is susceptible to hydrolysis.
  • the hydroxyquinolinate ligands can be substituted with groups such as alkyl or alkoxy groups which may be partially or fully fluorinated.
  • Suitable hydroxyquinolinate ligands include (with abbreviation provided in brackets): 8-hydroxyquinolinate [8hq] 2-methyl-8-hydroxyquinolinate [Me-8hq] 10-hydroxybenzoquinolinate [10-hbq]
  • the parent hydroxyquinoline compounds are generally available commercially.
  • Phosphino alkoxide ligands generally have Formula V:
  • R 4 can be the same or different at each occurrence and is selected from H and C n (H+F) n +i
  • R 5 can be the same or different at each occurrence and is selected from C n (H+F) 2n+1 and C 6 (H+F) 5 , or C 6 H 5 .
  • m (R6) m , R6 CF 3 , C 2 F 5 , ⁇ -C 3 F 7 , /-C 3 F 7 , C 4 F 9 , CF 3 SO 2> and ⁇ is 2 or 3
  • m is 0 or an integer from 1 through 5
  • n is an integer from 1 through 20.
  • Suitable phosphino alkoxide ligands include (with abbreviation provided in brackets): 3-(diphenylphosphino)-1 -oxypropane [dppO]; 1 ,1-bis(trifluoromethyl)-2-(diphenylphosphino)-ethoxide [tfmdpeO]; 1 ,1-bis(trifluoromethyl)-2-(bis(3'5'- ditrifluoromethylphenyl)phosphino)ethoxide [PO-2]; 1 ,1-bis(trifluoromethyl)-2-(bis(4'- trifluoromethylphenyl)phosphino)ethoxide [PO-3]; and 1 ,1-bis(trifluoromethyl)-2- (bis(pentafluorophenyl)phosphino)ethoxide [PO-4].
  • L 2 is a ligand coordinated through a carbon atom which is part of an aromatic group.
  • the ligand can have Formula VI: Ar[-(CH 2 ) q -Q] p (VI)
  • Ar is an aryl or heteroaryl group
  • Q is a group having a heteroatom capable of coordinating to a metal
  • q is 0 or an integer from 1 through 20
  • p is an integer from 1 through 5
  • one or more of the carbons in (CH 2 ) q can be replaced with a heteroatom and one or more of the hydrogens in (CH 2 ) q can be replaced with D or F.
  • ⁇ is selected from N(R 7 ) 2 , OR 7 , SR 7 , and P(R 8 ) 2 , wherein R 7 is the same or different at each occurrence and is H, C n H 2n+1 or C n (H+F) n+1 and R 8 is the same or different at each occurrence and is selected from H, R 7 , Ar and substituted Ar.
  • Ar is phenyl
  • q is 1
  • Q is P(Ar) 2
  • p is 1 or 2.
  • Tridentate L 2 ligands are similar to bidentate ligands, but include an additional nonionic group capable of coordinating to the metal.
  • nonionic groups include, but are not limited to amino, imino, and phosphino groups.
  • the L 3 ligand is non-ionic and can be monodentate or bidentate.
  • L 3 ligands include, but are not limited to CO, mono- and bidentate phosphine ligands, isonitriles, imines, and diimines.
  • the phosphine ligands can have Formula VII or Formula Vlll
  • Ar represents an aryl or heteroaryl group and Z represents an alkylene, heteroalkylene, arylene or heteroarylene group.
  • the Ar group can be unsubstituted or substituted with alkyl, heteroalkyl, aryl, heteroaryl, halide, carboxyl, sulfoxyl, or amino groups.
  • the phosphine ligands are generally available commercially.
  • L 4 is an anionic ligand.
  • L 4 is also attached to a central framework.
  • L 4 can be an aryl N- heterocycle, which is the same as or different from L .
  • the solution processability of an electrically active organometallic compound is increased by assembling monometallic groups into polymetallic compounds.
  • Fw represents a chemical framework onto which one, or more than one, metal unit can be attached. A myriad of possible framework structures exist for use in constructing invention compounds.
  • the number of metal units that may be attached to the framework structure is shown as “d” in Formula I, as “g” in Formula II, and as “h” in Formula III. The number varies depending on the type of framework structure, the nature of the L 4 ligand, and the nature of the other ligands on the metal. In some embodiments, the number of metal units attached to the framework varies from two up to about six. In other embodiments, the number of metal units attached to the framework can be greater than six, provided that frameworks with branching points are employed. In one embodiment, the framework structure is a hydrocarbyl moiety having at least one aryl ring. Exemplary framework structures containing aryl rings are set forth below, wherein " " represents a point of attachment for a metal unit:
  • the framework structure is a cyclic aliphatic moiety such as a cyclohexyl ring.
  • a variety of inorganic materials may also be employed as framework structures in invention polymetallic complexes.
  • the invention compound is a siloxane.
  • the framework structure is a silsesquioxane.
  • An exemplary silsesquioxane having an alkynylene linker is set forth below:
  • Si-Si denotes Si-O-Si. Any of the above framework structures can be further substituted.
  • substitutuents include, but are not limited to, groups such as alkyl, aryl, heteroalkyl, heteroaryl, alkoxy, and aryloxy, where such groups may be partially or fully fluorinated. By “fluorinated” it is meant that one or more hydrogens in the groups is replaced by fluorine.
  • Y represents an optional linking group between the framework structure and the attaching ligand L 4 . If utilized in invention compounds, linkers can be any group that does not detrimentally affect the desired properties of the metal compound. Examples include, but are not limited to O, S, alkylene, heteroalkylene, alkenylene, heteroalkenylene, alkynylene, and heteroalkynylene.
  • the linking group should not perturb the emission characteristics of each electroluminescent metal center attached to the framework.
  • the linkers can be chosen so that each metal group is oriented in space so as to optimize electroluminescent efficiency.
  • the linker is an alkylene, alkenylene, or alkynylene moiety having from 1 to 6 carbons.
  • the solution processability is increased by incorporating at least one solvent solubilizing substituent, R 1 , on at least one aryl or heteroaryl group.
  • R 1 is selected from alkyl, fluoroalkyl, aryl, fluoroaryl, alkylaryl, alkoxy, aryloxy, fluoroalkoxy, fluoraryloxy, and their hetero-analogs.
  • R is selected from phenyl, fluorophenyl, alkylphenyl, fluoroalkylphenyl, alkoxy phenyl, and fluoroalkoxyphenyl.
  • R 1 is an aryl substituted aryl group.
  • R 1 is a tetraphe-nyl phenyl group.
  • the structures set forth below depict exemplary ?-enolates as L 4 ligands linked to aryl framework structures via a CH 2 linking group. Also shown below is an example of a ?-enolate ligand attached to a cyclohexyl framework structure via an oxygen atom.
  • Exemplary invention compounds having Ir as the metal, phenylpyridine or phenyl-quinoline as L 1 , ?-enoIates as L 4 ligands, and an aryl ring as Fw are set forth in Figure 1.
  • R 1 is selected from alkyl, fluoroalkyl, aryl, fluoroaryl, alkylaryl, alkoxy, aryloxy, fluoroalkoxy, fluoraryloxy, and their hetero-analogs.
  • R 1 is selected from phenyl, fluorophenyl, alkylphenyl, fluoroalkylphenyl, alkoxy phenyl, and fluoroalkoxyphenyl. In one embodiment R 1 is an aryl-substituted aryl group.
  • the organometallic compounds of the invention are non-ionic. They can be formed into films by any conventional means. They can be formed into pure films, or they can be combined with other materials in films. The lower molecular weight compounds can, in some cases, be sublimed intact.
  • the liquid medium for solution processing the new organometallic compounds can be any organic or partially organic liquid in which the compounds can be dissolved or dispersed. In general, the liquid medium is non-aqueous.
  • suitable organic liquids which can be used as the liquid medium include, but are not limited to, toluene, fluorinated toluenes, xylenes, fluorinated xylenes, chlorinated hydrocarbons, ethylacetate, and 4-hydroxy-4-methyl-2-pentanone, and mixtures thereof.
  • the new organometallic compounds may be synthesized in a variety of ways using synthetic organic and organometallic techniques well-known to those skilled in the art. Some exemplary syntheses are set forth below for compounds where M is Ir. Analogous reactions can be carried out for other metals.
  • Steps A and B depict the synthesis of an aryl framework structure bearing 4 suitable bidentate, monoanionic ligands L 4 .
  • Reaction of 2,4- pentanedione with 1 ,2,4,5-tetra-bromomethylbenzene in the presence of a strong base such as lithium diisopropylamide (“LDA”) affords 1 ,2,4,5-tetra- (3,5-dioxo-hexyl)benzene.
  • LDA lithium diisopropylamide
  • This framework structure bears four ?-dicarbonyl moieties, which, after deprotonation to form ?-dienolates, are suitable for coordinating up to four monometallic groups. This is accomplished as shown, for example, in Step B.
  • the framework structure with four ⁇ -dicarbonyl moieties is reacted with NaH to produce the acetylacetonate moieties, L 4 , which then react with a precursor Ir complex to form an example of an invention compound.
  • the precursor organometallic complex can be prepared via an intermediate dimer, such as
  • L is the same or different and is typically a ligand of type L 1 , and Z is Cl or OR 9 , where R 9 is H, CH 3 , or C 2 Hs.
  • the iridium dimers can generally be prepared by first reacting iridium trichloride hydrate with the ligands L 1 and optionally adding NaOR 9 .
  • the aryl-N-heterocycle and heteroaryl-N-heterocyle ligands can generally be prepared using the Suzuki coupling of the component groups, as described in O. Lohse, P.Thevenin, E. Waldvogel Synlett, 1999, 45-48.
  • the compounds of the invention can be isolated, purified, and fully characterized by elemental analysis, 1 H and 19 F NMR spectral data, and, for suitable crystalline compounds, single crystal X-ray diffraction. In some cases, mixtures of isomers are obtained. Often the mixture can be used without isolating the individual isomers. If individual isomers are desired they are often separable by liquid chromatography on silica or alumina media using standard techniques.
  • the device 100 has an anode layer 1 10 and a cathode layer 150. Adjacent to the anode is a layer 120 comprising hole transport material. Adjacent to the cathode is a layer 140 comprising an electron transport material. Between the hole transport layer and the electron transport layer is the photoactive layer 130.
  • the photoactive layer 130 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell, light-emitting display), a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
  • an applied voltage such as in a light-emitting diode or light-emitting electrochemical cell, light-emitting display
  • a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
  • Electronic devices that have utility for the compounds disclosed herein include: (1 ) devices that convert electrical energy into radiation (e.g., a light- emitting diode, light-emitting diode display, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes), IR detectors), (3) devices that convert radiation into electrical energy (e.g., a photovoltaic device or solar cell), and (4) devices that include one or more electronic components that include one or more organic semi-conductor layers (e.g., a transistor or diode).
  • radiation e.g., a light- emitting diode, light-emitting diode display, or diode laser
  • devices that detect signals through electronics processes e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes), IR detector
  • the compounds of the invention are particularly useful as the photoactive material in layer 130, or as an electron transport material in layer 130 or layer 140.
  • the compounds of the invention are used as the light-emitting material in diodes.
  • a layer that is greater than 20% by weight new compound, based on the total weight of the layer, up to 100% new compound, can be used as the emitting layer. Additional materials can be present in the emitting layer with the compound of the invention. For example, a fluorescent dye may be present to alter the color of emission.
  • a diluent may also be added and such diluent may be a charge transport material or an inert matrix.
  • a diluent may comprise polymeric materials, small molecule or mixtures thereof.
  • a diluent may act as a processing aid, may improve the physical or electrical properties of films containing the metal compound, may decrease self-quenching in the metal compounds described herein, and/or may decrease the aggregation of the metal compounds described herein.
  • the new compound described herein is present as a guest material in a host material.
  • guest material is intended to mean a material, within a layer including a host material, that changes the electronic characteristic(s) or the targeted wavelength(s) of radiation emission, reception, or filtering of the layer compared to the electronic characteristic(s) or the wavelength(s) of radiation emission, reception, or filtering of the layer in the absence of such material.
  • host material is intended to mean a material, usually in the form of a layer, to which a guest material may or may not be added.
  • the host material may or may not have electronic characteristic(s) or the ability to emit, receive, or filter radiation.
  • suitable polymeric host materials include poly(N-vinyl carbazole), conjugated polymers, and polysilane, and mixtures thereof.
  • suitable small molecule host materials include 4,4'-N,N , -dicarbazole biphenyl (CBP), Bis(2-methyl-8- quinolinolato)(4-phenylphenolato)aluminum (BAIQ) or tertiary aromatic amines and mixtures thereof.
  • conjugated polymers examples include polyarylenevinylenes, polyfluorenes, polyoxadiazoles, polyanilines, polythiophenes, polyphenylenes, copolymers thereof and combinations thereof.
  • the conjugated polymer can be a copolymer having non- conjugated portions, for example, acrylic, methacrylic, or vinyl monomeric units.
  • the diluent comprises homopolymers and copolymers of fluorene and substituted fluorenes. When a diluent is used, the compound of the invention is generally present in a small amount. In one embodiment, the metal compound is less than 20% by weight, based on the total weight of the layer.
  • the metal compound is less than 10% by weight, based on the total weight of the layer.
  • the compounds of the invention may be present in more than one isomeric form, or mixtures of different complexes may be present. It will be understood that in the above discussion of OLEDs, the term "compound of the invention" is intended to encompass mixtures of compounds and/or isomers.
  • the HOMO highest occupied molecular orbital
  • the LUMO lowest un-occupied molecular orbital
  • the other layers in the OLED can be made of any materials which are known to be useful in such layers.
  • the anode 110 is an electrode that is particularly efficient for injecting positive charge carriers. It can be made of, for example materials containing a metal, mixed metal, alloy, metal oxide or mixed-metal oxide, or it can be a conducting polymer. Suitable metals include the Group 11 metals, the metals in Groups 4, 5, and 6, and the Group 8-10 transition metals. If the anode is to be light-transmitting, mixed-metal oxides of Groups 12, 13 and 14 metals, such as indium-tin- oxide, are generally used.
  • the IUPAC numbering system is used throughout, where the groups from the Periodic Table are numbered from left to right as 1-18 (CRC Handbook of Chemistry and Physics, 81 st Edition, 2000).
  • the anode 110 may also comprise an organic material such as polyaniline as described in "Flexible light-emitting diodes made from soluble conducting polymer," Nature vol. 357, pp 477-479 (11 June 1992). At least one of the anode and cathode should be at least partially transparent to allow the generated light to be observed. Examples of hole transport materials for layer 120 have been summarized for example, in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, p. 837-860, 1996, by Y. Wang. Both hole transporting molecules and polymers can be used.
  • hole transporting molecules are: N,N'-diphenyl-N,N'-bis(3-methylphenyl)- [l (TPD), 4,4'-Bis[N-(1-naphthyl)-N- phenylaminojbiphenyl (NPB, NPD), 1 ,1-bis[(di-4-tolylamino) phenyfjcyclohexane (TAPC), N,N'-bis(4-methylphenyl)-N,N'-bis(4- ethylphenyl)-[1 ,1'-(3,3'-dimethyl)biphenyl]-4,4'-diamine (ETPD), tetrakis-(3- methylphenyl)-N,N,N',N'-2,5-phenylenediamine (PDA), a-phenyl-4-N,N- diphenylaminostyrene (TPS), p-(diethyl)
  • hole transporting polymers are polyvinylcarbazole, (phenylmethyl)polysilane, and polyaniline. It is also possible to obtain hole transporting polymers by doping hole transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate.
  • Examples of other electron transport materials for layer 140 include metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq 3 ); phenanthroline-based compounds, such as 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline (DDPA) or 4,7-diphenyl-1 ,10-phenanthroline (DPA), and azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (PBD) and 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1 ,2,4-triazole (TAZ).
  • metal chelated oxinoid compounds such as tris(8-hydroxyquinolato)aluminum (Alq 3 )
  • phenanthroline-based compounds such as 2,9-dimethyl-4,7-diphenyl-1
  • the cathode 150 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
  • the cathode can be any metal or nonmetal having a lower work function than the anode.
  • Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides.
  • Li-containing organometallic compounds can also be deposited between the organic layer and the cathode layer to lower the operating voltage. It is known to have other layers in organic electronic devices. For example, there can be additional layers (not shown) between the anode layer 110 and the active layer 130 to facilitate positive charge transport and/or band-gap matching of the layers, or to function as a protective layer. Similarly, there can be additional layers (not shown) between the active layer 130 and the cathode layer 150 to facilitate negative charge transport and/or band-gap matching between the layers, or to function as a protective layer. Layers that are known in the art can be used.
  • any of the above-described layers can be made of two or more layers.
  • some or all of inorganic anode layer 110, the hole transporting layer 120, the active layer 130, and cathode layer 150 may be surface treated to increase charge carrier transport efficiency.
  • the choice of materials for each of the component layers is preferably determined by balancing the goals of providing a device with high device efficiency. It is understood that each functional layer may be made up of more than one layer.
  • the device can be prepared by sequentially vapor depositing the individual layers on a suitable substrate. Substrates such as glass and polymeric films can be used. Conventional vapor deposition techniques can be used, such as thermal evaporation, chemical vapor deposition, and the like.
  • the organic layers can be coated from solutions or dispersions in suitable solvents, using any conventional coating technique.
  • the different layers will have the following range of thicknesses: anode 110, 500-5000A, preferably 1000-2000A; hole transport layer 120, 50-1000A, preferably 200-800A; light-emitting layer 130, 10-1000 A, preferably 100-800A; electron transport layer 140, 50-1 OOOA, preferably 200-800A; cathode 150, 200-1 OOOOA, preferably 300-5000A.
  • the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer.
  • the thickness of the electron-transport layer should be chosen so that the electron-hole recombination zone is in the light-emitting layer.
  • the desired ratio of layer thicknesses will depend on the exact nature of the materials used. It is understood that the efficiency of devices made with the compounds of the invention, can be further improved by optimizing the other layers in the device. For example, more efficient cathodes such as Ca, Ba or LiF can be used. Shaped substrates and novel hole transport materials that result in a reduction in operating voltage or increase quantum efficiency are also applicable. Additional layers can also be added to tailor the energy levels of the various layers and facilitate electroluminescence. The compounds of the invention often are phosphorescent and photoluminescent and may be useful in applications other than OLEDs.
  • phosphorescent organometallic compounds have been used as oxygen sensitive indicators, as phosphorescent indicators in bioassays, and as catalysts.
  • compound is intended to mean an electrically uncharged substance made up of molecules that further consist of atoms, wherein the atoms cannot be separated by physical means.
  • ligand is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion.
  • complex when used as a noun, is intended to mean a compound having at least one metallic ion and at least one ligand.
  • the term "monodentate ligand” refers to a ligand that occupies one coordination site in the coordination sphere of a metallic ion.
  • the terms “bidentate ligand” and “tridentate ligand” refer to ligands that occupy two and three coordination sites, respectively, in the coordination sphere of a metallic ion.
  • group is intended to mean a part of a compound, such a substituent in an organic compound or a ligand in a complex.
  • hexacoordinate is intended to mean that six groups or points of attachment are coordinated to a central metal.
  • the term “tetracoordinate” is intended to mean that four groups or points of attachment are coordinated to a central metal.
  • adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
  • photoactive is intended to mean any material that exhibits electroluminescence or photosensitivity.
  • active or “electrically active”, when referring to a layer or material is intended to mean a layer or material that exhibits electronic or electro-radiative properties. An active layer material may emit radiation or exhibit a change in concentration of electron-hole pairs when receiving radiation.
  • the letters L, M, Q, R, Y, Z, and Fw are used to designate atoms or groups which are defined within. All other letters are used to designate conventional atomic symbols.
  • liquid or solution processing or solution deposition refers to the formation of uniform films from a liquid medium.
  • the film is robust.
  • the deposition techniques include any continuous or discontinuous method of depositing a material that is in the form of a liquid medium.
  • layer is used interchangeably with the term “film” and refers to a coating covering a desired area.
  • the term is not limited by size.
  • the area can be as large as an entire device. In other embodiments, the area can be as small as a specific functional area such as the actual visual display, or as small as a single sub-pixel. In addition, the area can be continuous or discontinuous.
  • Layers can be formed by any conventional deposition technique, including, but not limited to, vapor deposition, liquid deposition, and thermal transfer.
  • the layer may be made by] spin coating, gravure coating, curtain coating, dip coating, slot- die coating, spray coating, continuous nozzle coating, and discontinuous deposition techniques such as ink jet printing, contact printing such as gravure printing, screen printing, and the like, or indeed, any other way which is effective in causing a layer to come into existence.
  • alkyl is intended to mean a group derived from an aliphatic hydrocarbon having one point of attachment, which group may be linear, branched or cyclic.
  • alkylene is intended to mean a group derived from an alkyl group and having two or more points of attachment.
  • alkenyl is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon double bonds and having one point of attachment, which group may be linear, branched or cyclic.
  • alkenylene is intended to mean a group derived from an alkenyl group and having one or more carbon-carbon double bonds and having two or more points of attachment.
  • alkynyl is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon triple bonds and having one point of attachment, which group may be linear, branched or cyclic.
  • alkynylene is intended to mean a group derived from an alkynyl group and having two or more points of attachment.
  • aryl is intended to mean a group derived from an aromatic hydrocarbon having one point of attachment.
  • arylene is intended to mean a group derived from an aryl group and having two points of attachment.
  • arylalkylene is intended to mean a group derived from an alkyl group having an aryl substituent.
  • arylenealkylene is intended to mean a group having both aryl and alkyl groups and having one point of attachment on an aryl group and one point of attachment on an alkyl group.
  • hydrocarbyl refers to a moiety that is composed primarily of carbon and hydrogen atoms.
  • a “hydrocarbyl” moiety may also contain heteroatoms, e.g., N, O, P, and the like.
  • inorganic refers to a moiety that is composed primarily of atoms other than carbon.
  • solvent-solubilizing indicates that the solubility or dispersability of a material in at least one organic solvent has been increased.
  • fluoro is intended to mean that one or more hydrogens has been replace by fluorine, including completely hydrogenated, partially fluorinated and perfluorinated substituents.
  • hetero indicates that at least one of the carbon atoms forming the group has been replaced by a heteroatom. Such heteroatoms include, e.g., N, O, P, and the like, see page 16 Unless otherwise indicated, all groups can be unsubstituted or substituted.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
  • “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • EXAMPLES The following examples illustrate certain features and advantages of the present invention. They are intended to be illustrative of the invention, but not limiting. All percentages are by weight, unless otherwise indicated.
  • aryl framework structure with acetylacetonate (acac) as ligands (Y) was prepared as follows. Inside a N2 ⁇ filled glove box, a 100 cc glass pot, equipped with a dropping funnel, rubber-covered stoppers and stir bar, was charged with 3.20 g(32 equiv.) of 2,4-pentanedione and 35 cc THF. A glass bottle, with a septum seal, was charged with 1.83 g (4.17 equiv.) of 1 ,2,4,5-tetra-bromomethylbenzene and 25 cc THF.
  • a dry ice-acetone cooling bath was used to cool the pot and stirring was started. After 15 min., low N2 pressure was used with a cannula to transfer the solution from the bottle to the pot.
  • the solution in the syringe was injected into the pot over about 15 min. with stirring.
  • a 1.03 g portion of crude product was purified by elution from a 2 cm diam. x 4 cm column of silica gel, using successively: methylene chloride, methylene chloride/ethyl acetate (50/50), ethyl acetate, and finally methanol. Upon evaporation of solvent, methylene chloride afforded 0.062g of final product and the methylene chloride/ ethyl acetate fraction eluted 0.233g of final product. The combined yield of 0.295g of final product was 28%, based on starting 1 ,2,4,5-tetra-bromomethylbenzene.
  • r is 1 or 2.
  • 1.0 g of the phenylpyridine ligand 2-(3-phenyl)-phenylpyridine (prepared as in example 2 above except substituting phenylboronic acid for 3-trifluoromethylboronic acid) was mixed with 0.76g iridium chloride in 10mL 2-ethoxyethanol and 1 mL water. This mixture was refluxed under nitrogen for 30mins then cooled to room tmeperature and evaporated to dryness in a nitrogen stream. The yellow solid was extracted into methylene chloride and filtered. The resulting yellow solution was evaporated to dryness to isolate chloro dimer in 85% yield.
  • the chlorodimer (0.69 g) was mixed with 2 eq (0.58 g) of the ligand 2-(3-(4-t-butylphenyl))-phenylpyridine prepared in example 3c above and 1q silver trifluoroacetate in 2-ethoxyethanol.
  • the mixture was refluxed for 2 hrs then evaporated to dryness and extracted into methylene chloride. Chromatography on silica using methylene chloride as eluent produced a fast running green luminescent band. Collection of this band, evaporation and recrystallization from methylene chloride/methanol gave a bright yellow powdery solid.
  • EXAMPLE 16 This example illustrates the fabrication of an organic light emitting diode (OLED) using a polymetallic red-emissive material (compound 9 from example 9, illustrated below) as a dopant in a poly(fluorene) matrix. The resulting blend is used as the active red-emissive layer in an OLED. The electrical performance of this device is compared to an identical OLED, except that the second device contains the analogous monometallic compound (compound 11 from example 11 , illustrated below) as the red dopant instead of the polymetallic compound.
  • the film was dried on a hotplate at 200 °C for 3 min.
  • the substrate was then transferred to a nitrogen-filled glovebox, at which point a solution of poly(fluorene) (75 mg), the red-emissive polymetallic compound (1.5 mg), and anhydrous toluene (7.5 mL) were spin coated on the substrate to a thickness of 70 nm.
  • the substrate was then transferred to a high vacuum chamber, where LiF (2.0 nm) followed by Ca (20.0 nm) and then Al (400 nm) were thermally deposited at 2.0 x 10 -6 torr.
  • the resulting OLED device was then sealed from air by gluing a glass slide on top of the cathode with the use of a UV-curable epoxy resin.
  • OLED with the Analogous Monometallic Red-Emissive Compound The organic film components in this OLED example were all solution processed.
  • the substrate was then transferred to a nitrogen-filled glovebox, at which point a solution of poly(fluorene) (75 mg), the red-emissive monometallic compound (1.5 mg), and anhydrous toluene (7.5 mL) were spin coated on the substrate to a thickness of 70 nm.
  • the substrate was then transferred to a high vacuum chamber, where LiF (2.0 nm) followed by Ca (20.0 nm) and then Al (400 nm) were thermally deposited at 2.0 x 10" 6 torr.
  • the resulting OLED device was then sealed from air by gluing a glass slide on top of the cathode with the use of a UV-curable epoxy resin.

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