WO2005124890A1

WO2005124890A1 - Electrolumineschent iridium complex and devices made with such compound

Info

Publication number: WO2005124890A1
Application number: PCT/US2005/020449
Authority: WO
Inventors: Norman Herron; Nora Sabina Radu; Klaus Mullen; Eric Maurice Smith
Original assignee: E.I. Dupont De Nemours And Company; Max Planck Institute For Polymer Research
Priority date: 2004-06-09
Filing date: 2005-06-08
Publication date: 2005-12-29
Also published as: EP1754267A1; KR101292376B1; JP2008504371A; JP2012107030A; KR20070033350A; WO2005124889A1; KR101233855B1; JP4934035B2; KR20120052425A

Abstract

The present invention is generally directed to the organometallic compound having the following formula and an organic electronic devices having an layer including such a compound.

Description

ELECTROLUMINESCHENT IRIDIUM COMPLEX AND DEVICES MADE WITH SUCH COMPOUND

BACKGROUND OF THE INVENTION Field of the Invention 5 This invention relates to organometallic compounds, and more particularly to semiconductor and photoactive organometallic compounds. It also relates to electronic devices in which an active layer includes at least one such organometallic compound. This application claims priority to United States Provisional 10 Application No. 60/545,596 filed June 9, 2004. Description of the Related Art Organic electronic devices that emit light, such as light-emitting diodes that make up displays, are present in many different kinds of electronic equipment. In all such devices, an organic active layer is 15 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. 20 It is well known to use 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. Semiconductive conjugated polymers have also been used as electroluminescent components, as has 25 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 30 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. 1999, 75, 4.) The performance is maximized when the iridium compound is present in a host conductive 35 material. Thompson has further reported devices in which the active layer is poly(N-vinyl carbazole) doped with fac-tris[2-(4^,,5'- difluorophenyl)pyridine-C^,2,N]iridium(lll). (Polymer Preprints 2000, 41 (1 ), 770.) Electroluminescent iridium complexes having fluorinated phenylpyridine, phenylpyrimidine, or phenylquinoline ligands have been disclosed in published application WO 02/02714. However, there is a continuing need for electroluminescent compounds. SUMMARY OF THE INVENTION The present invention is directed to a compound having Formula I, as follows:

In another embodiment, there are provided electronic devices containing at least one active layer comprising at least one invention compound. In another embodiment, there are provided organic light emitting diodes (OLEDs) containing at least one active layer including at least one invention compound. In another embodiment, there are provided electroluminescent devices containing at least one active layer including the invention compound.

The foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as defined in the appended claims. BRIEF DESCRIPTION OF THE DRAWINGS The invention is illustrated by way of example and not limitation in the accompanying figures. Figure 1 is a schematic diagram of one illustrative example of a light-emitting device. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The compound of the invention has the following formula which may exist in either facial (fac) or mehdonal (mer) isomeric forms:

The compound of the present invention can be formed into films by any conventional means and may be used in a composition. In one embodiment, the compound is deposited by solution processing. As used herein, "liquid or solution processing or solution deposition" refers to the formation of uniform films from a liquid medium. In one embodiment, 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. The term "layer" is used interchangeably with the term "film" and refers to a coating covering a desired area. The term is not limited by size. For example, in some embodiments, 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. For, example, in some embodiments, 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. The liquid medium for solution processing the new compound can be any organic or partially organic liquid in which the compound can be dissolved or dispersed. In general, the liquid medium is non-aqueous. Examples of suitable organic liquids which can be used as the liquid medium include, but are not limited to, toluene, xylenes, chlorinated hydrocarbons, ethylacetate, and 4-hydroxy-4-methyl-2-pentanone. The compound of Formula I can be prepared by the reaction of iridium trichloride hydrate, an excess of ligand, and silver trifluoroacetate. The ligand 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, and as further described in the example. The compounds of the invention, can be isolated, purified, and fully characterized by elemental analysis, ¹H and ¹⁹F NMR spectral data, and, for suitable crystalline compounds, single crystal X-ray diffraction. Electronic Device Another embodiment is a new organic electronic device comprising at least one layer comprising the above compound of Formula I. The compound can be in a separate layer or can be combined with other active or inactive materials in the device.

In the preparation of organic electronic devices, it is frequently desirable to form one or more layers using solution-processing techniques. In the field of OLEDs, the formation of highly efficient and long-lived multilayer solution processed devices is a difficult challenge. Some of the issues encountered in this area are thermal and morphological stability and film- forming ability of the organic materials. Of particular relevance is the solubility and film-forming ability of materials used in the active (e.g., emissive) layer. In certain embodiments, device performance is dependent on the quality of the deposited film. In the compound of the invention, the film-forming properties are improved by adding solvent- solubilizing phenyl substituents to the ligands on the metal. In somedevices, the emissive layer comprises a host transport material into which the electroluminescent material is doped at <20 wt %. In certain embodiments, good miscibility between the host and electroluminescent material is needed to obtain good film quality. In certain embodiments, the addition of at least one solvent-solubilizing substituent can improve compatibility of the metal compound and the host and result in high-quality films which retain amorphous character and inhibit phase segregation or emitter aggregation in the host. An illustration of one type of organic electronic device structure is shown in Figure 1. The device 100 has an anode layer 110 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. Depending upon the application of the device 100, 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). Electronic devices that benefit from the use of this invention 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). The compounds of the invention are particularly useful as the photoactive material in layer 130, or as electron transport material in layer 130 or layer 140. In one embodiment, the compounds of the invention are used as the light-emitting material in diodes. In one embodiment, 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 new compound, may decrease self-quenching in the new compound described herein, and/or may decrease the aggregation of the new compound described herein. In certain embodiment, the new compound of Formula I is present as a guest material in a host material. The term "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. The term "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. Non-limiting examples of suitable polymeric host materials include poly(N-vinyl carbazole), conjugated polymers, and polysilanes and mixtures thereof. Non-limiting examples of suitable small molecules host materials include 4,4'-N,N'-dicarbazole biphenyl (CBP), Bis(2-methyl-8- quinolinolato)(4-phenyIphenolato)aluminum (BAIQ) or tertiary aromatic amines and mixtures thereof. Examples of suitable conjugated polymers 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. In one embodiment, the host comprises homopolymers and copolymers of fluorine and substituted fluorenes. When a host is used, the compound of the invention is generally present in a small amount. In one embodiment, the new compound is less than 20% by weight, based on the total weight of the layer. In one embodiment, the new compound is less than 10% by weight, based on the total weight of the layer.

To achieve a high efficiency LED, the HOMO (highest occupied molecular orbital) of the hole transport material should align with the work function of the anode, the LUMO (lowest un-occupied molecular orbital) of the electron transport material should align with the work function of the cathode. Chemical compatibility and sublimation temp of the materials are also important considerations in selecting the electron and hole transport materials. 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. Commonly used hole transporting molecules are: N,N'-diphenyl-N,N'-bis(3-methylphenyl)- [1 ,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-Bis[N-(1-naphthyl)-N- phenylaminojbiphenyl (NPB, NPD) 1 ,1-bis[(di-4-tolylamino) phenyljcyclohexane (TAPC), N,N'-bis(4-methylphenyl)-N,N'-bis(4- ethylphenyl)-[1 ,iχ3,3'-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-(diethylamino)benzaldehyde diphenylhydrazone (DEH), triphenylamine (TPA), bis[4-(N,N- diethylamino)-2-methyIphenyl](4-methylphenyl)methane (MPMP), 1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl] pyrazoline (PPR or DEASP), 1 ,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB), N,N,N',N'-tetrakis(4-methylphenyl)-(1 ,1'-biphenyl)-4,4'-diamine (TTB), and porphyrinic compounds, such as copper phthalocyanine. Commonly used 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 (Alq₃); 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). Layer 140 can function both to facilitate electron transport, and also serve as a buffer layer or confinement layer to prevent quenching of the exciton at layer interfaces. Preferably, this layer promotes electron mobility and reduces exciton quenching. 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. Materials such as aluminum, indium, calcium, barium, samarium and magnesium, as well as combinations, can be used. 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 layerl 10 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. In addition, any of the above-described layers can be made of two or more layers. Alternatively, 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 material 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. Alternatively, the organic layers can be coated from solutions or dispersions in suitable solvents, using any conventional coating technique. In general, 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. Thus 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 compound 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 compound of the invention may be useful in applications other than OLEDs. For example, organometallic compounds have been used as oxygen sensitive indicators, as phosphorescent indicators in bioassays, and as catalysts. As used herein, the term "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. The term "ligand" is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion. The term "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 "group" is intended to mean a part of a compound, such as a substituent in an organic compound or a ligand in a complex. The phrase "adjacent to," when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer. On the other hand, the phrase "adjacent R groups," is used to refer to R groups that are next to each other in a chemical formula (i.e., R groups that are on atoms joined by a bond). The term "photoactive" refers to any material that exhibits electroluminescence and/or photosensitivity. As used herein, "liquid or solution processing or solution deposition" refers to the formation of uniform films from a liquid medium. In one embodiment, the film is robust. The terms include any continuous or discontinuous method of depositing a material that is in the form of a liquid medium. Liquid deposition techniques include, but are not limited to, continuous deposition techniques such as spin coating, gravure coating, curtain coating, dip coating, slot-die coating, casting, spray-coating, bar coating, roll coating, doctor blade coating and continuous nozzle coating; and discontinuous deposition techniques such as ink jet printing, gravure printing, and screen printing. The term "film" refers to a coating covering a desired area. The area can be as large as an entire display, or as small as a single pixel. Films can be formed by any conventional deposition technique, including vapor deposition and liquid deposition.

As used herein, the term "solvent-solubilizing" indicates that the solubility or dispersability of a material in at least one organic solvent has been increased. As used herein, the terms "comprises," "comprising," "includes,"

"including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, 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. Further, unless expressly stated to the contrary, "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). Also, use of the "a" or "an" are employed to describe elements and components of the invention. This is done merely for convenience and to give a general sense of the invention. This description should be read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting. It is to be appreciated that certain features of the invention which are, for clarity, described above and below in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any subcombination. Further, reference to values stated in ranges include each and every value within that range.

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. EXAMPLE 1 This example illustrates the preparation of a new organometallic compound having Formula I:

A mixture of 1-bromo-3-ethynylbenzene (6.60g, 36.5 mmol) and tetraphenylcyclopentadienone (14.5 g, 37.7 mmol) in o-xylene (10 mL) was heated at reflux for 16 h. The solvent was removed by distillation in vacuo, and the residue purified by column chromatography on silica gel with petroleum ether as the eluant. The fractions containing the major band were combined and taken to dryness to give 1-(3^'-bromophenyl)- 2,3,4, 5-tetraphenylbenzene as a white powder (16.34 g, 30.4 mmol, 83 %). 1 H-NMR (CDCI3): δ 7.54 (s, 1 H), 7.40 (br s, 1 H), 7.27 (m, 1 H), 7.17 (br s, 5H), 7.01-6.77 (m, 17H). 13C-NMR (CDCI3): .5144.1 , 142.2, 141.8, 141.3, 140.4, 140.2, 140.1 , 139.8, 139.6, 139.5, 133.2, 131.8, 131.7, 131.5, 130.2, 129.6, 129.3, 129.0, 128.0, 127.4, 127.3, 127.0, 126.7, 126.2, 126.0, 125.8, 122.1. MS (FD): 536 ([M]⁺, 100). A solution of 1~(3^'-bromophenyl)-2,3,4,5-tetraphenylbenzene

(2.01 g, 3.74 mmol) in THF (35 mL) was cooled to -78 ^°C and n- butyllithium (2.6 mL, 4.1 mmol) was added dropwise. After stirring for 20 min, 2-isopropoxy-4,4,5,5-tetramethyl-1 ,3,2~dioxaborolane (0.95 mL, 4.96 mmol) was added dropwise, the cooling bath removed and the mixture allowed to warm to RT over 20 h. The volume was reduced to ca 8 mL, dichloromethane added and the solution washed with brine. The organic phase was dried with magnesium sulfate, filtered and taken to dryness. The residue was purified by column chromatography on silica gel with petroleum ether/dichloromethane (1 :1 ) as eluant. Fractions containing the second and major band were combined and taken to dryness to give 1 -(3 ^'-boronpinacolatophenyl)-2,3,4, 5-tetraphenylbenzene as a white powder (1.70 g, 2.9 mmol, 78 %). H-NMR (CDCI3): δ 7.96 (br s, 1 H), 7.77 (s, 1 H), 7.74 (m, 1 H), 7.30 (br s, 4H), 7.22 (M, 2H), 7.08-6.91 (m, 16H), 1.46 (s, 12H). 13C-NMR (CDCI3): δ 142.1 , 142.0, 141.2, 141.0, 140.7, 140.4, 140.3, 139.6, 139.5, 136.6, 133.2, 132.9, 131.9, 131.8,

131.7, 130.3, 127.9, 127.2, 127.1 , 126.9, 126.5, 125.9, 125.8, 125.6, 84.0, 25.2. MS (FD): 584 ([M]⁺, 100). A suspension of iridium(III) j/s(2-(5^'-bromophenyl)pyridinato-Λ/,C^2') (350 mg, 0.39 mmol), 1-(3^'-boronpinacolatophenyl)-2,3,4,5- tetraphenylbenzene (1.37 g, 2.34 mmol), sodium carbonate (550 mg, 5.2 mmol) and Pd(PPh3)4 (42 mg, 36 μmol) in THF (25 mL) and water (9 mL) was purged with argon for 10 min, then heated at reflux for 16 h. During this time the solids dissolved to give an intensely colored yellow- orange organic layer which after cooling, was diluted with dichloromethane and washed twice with water, dried with magnesium sulfate, filtered and taken to dryness. The crude material was passed through a short silica column with dichloromethane, concentrated and precipitated from solution with hexane. After filtration, the solid was dissolved in chloroform, re- precipitated with hexane, filtered and dried in vacuo to afford fr/s(2-(5^'-(3^"- (2^"',3^'",4^'",5^'"-tetraphenyl)phenyl)phenyl)phenylpyridinato-/\/,C^2') (458 mg, 58 %) as a yellow powder. H-NMR (CDCI3): δ 7.90 (d, J = 8 Hz, 3H), 7.62-7.34 (m, 18H), 7.21-6.79 (m, 75H). 13_C-NMR (CDCI3): δ 166.8, 147.2, 144.6, 142.2, 142.1 , 142.0, 141.9, 141.4, 141.1 , 140.8, 140.5, 140.4, 139.6, 139.5, 137.7, 136.2, 132.1 , 131.9, 130.3, 129.1 , 128.6, 128.3, 127.9, 127.3, 127.2, 127.0, 126.5, 126.0, 125.9, 125.6, 124.7, 122.6, 122.4, 119.4. MS (MALDI): 2026 ([M]⁺, 100). UV-Vis (THF): 247 (175), 281 (123), 327sh (45), 390 (16), 412sh (6) (103 L moH cnΗ ).

Claims

CLAIMSWhat is claimed is:

1. An organic electronic device comprising at least one active layer comprising a compound having the following formula.

2. A compound of the formula.

in either its fac or mer isomeric forms

3. A composition comprising the compound of the following formula.

4. The composition of Claim 3 further comprising a host.

5. The composition of Clam 4 wherein the host is selected from poly(N-vinyl carbazole), conjugated polymers, polysilane, tertiary aromatic amines, and mixtures thereof.

6. The composition of Claim 4 wherein the host is selected from polyarylenevinylenes, polyfluorenes, polyoxadiazoles, polyanilines, polythiophenes, polyphenylenes, copolymers thereof and combinations thereof.