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  • 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
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  • 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
• • 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
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  • 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
  • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
• • 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
  • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
• • 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
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  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1011—Condensed systems
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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  • 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
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  • 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
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K2101/00—Properties of the organic materials covered by group H10K85/00
  • H10K2101/10—Triplet emission
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K2101/00—Properties of the organic materials covered by group H10K85/00
  • H10K2101/90—Multiple hosts in the emissive layer
• • H—ELECTRICITY
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  • 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

• R 4 is the same or different at each occurrence and is H ,D, aryl, alkyl, silyl, deuterated aryl, deuterated alkyl, and deuterated silyl.
• an organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, the photoactive layer comprising the material having Formula I.
• aromatic compound is intended to mean an organic compound comprising at least one unsaturated cyclic group having delocalized pi electrons.
• charge transport when referring to a layer, material, member, or structure is intended to mean such layer, material, member, or structure facilitates migration of such charge through the thickness of such layer, material, member, or structure with relative efficiency and small loss of charge.
• Hole transport materials facilitate positive charge; electron transport materials facilitate negative charge.
• light-emitting materials may also have some charge transport properties, the term "charge transport layer, material, member, or structure” is not intended to include a layer, material, member, or structure whose primary function is light emission.
• electrostatic trap or “electron-trap material” is intended to mean a compound that possesses a lowest unoccupied molecular orbital (LUMO) lying further in energy from the vacuum level than the LUMO of any other material present in the layer in which it is embedded. As such, it is the preferred site for negative charge to reside in that layer and if the trap material is present below the percolation volume ( ⁇ 15%) such negative charge becomes localized upon molecules of the trap material presenting a hindrance to negative charge mobility within that layer.
• LUMO lowest unoccupied molecular orbital
• host material is intended to mean a material, usually in the form of a layer, to which a dopant may be added.
• the host material may or may not have electronic characteristic(s) or the ability to emit, receive, or filter radiation.
• Embodiment 1 The compound of Formula I, wherein the compound is deuterated.
• Embodiment 2 The compound of Formula I, wherein the compound is at least 10% deuterated. By “% deuterated” or “%
• Embodiment 29 The compound of Formula I, wherein R 2 is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, substituted derivatives thereof, and deuterated analogs thereof.
• Embodiment 33 The compound of Formula I, wherein R 3 is selected from the group consisting of methyl, ethyl, butyl, pentyl, hexyl, heptyl, octyl, and deuterated derivatives thereof.
• Organic electronic devices that may benefit from having one or more layers comprising the materials described herein include, but are not limited to, (1 ) devices that convert electrical energy into radiation (e.g., a light-emitting diode, light emitting diode display, lighting device, luminaire, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors, photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes, IR detectors, biosensors), (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).
• (1 ) devices that convert electrical energy into radiation e.g., a light-emitting diode, light emitting diode display, lighting device, luminaire, or diode laser
• devices that detect signals through electronics processes e.g., photodetec
• cathode 150 200-10000 A, in some embodiments, 300-5000 A.
• 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 desired ratio of layer thicknesses will depend on the exact nature of the materials used.
• the photoactive layer consists essentially of a compound having Formula I.
• the photoactive layer comprises a host material, a compound having Formula I as a dopant, and a second host material.
• luminescent compound a host material, a compound having Formula I as a hole-trap material, and a second host material.
• the photoactive layer consists essentially of a luminescent compound, a host material, and a compound having
• the photoactive layer consists essentially of a red luminescent compound, a host material, and a compound having Formula I as a hole-trap material.
• the hole-trap material of Formula I can be present in an amount of
• the compounds having Formula I can be used as a hole-trap for any kind of electroluminescent ("EL") layer for which any of the component HOMO levels are further from the vacuum level as compared to the HOMO level of the compound of Formula I.
• EL electroluminescent
• the emissive singlet energy level should be lower as compared to the singlet energy level of the compound of Formula I. This is discussed above in the definition section.
• metal complexes include, but are not limited to, metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq3); cyclometalated iridium and platinum electroluminescent compounds, such as complexes of iridium with phenylpyridine, phenylquinoline, or phenylpyrimidine ligands as disclosed in Petrov et al., U.S. Patent 6,670,645 and Published PCT Applications WO 03/063555 and WO 2004/016710, and organometallic complexes described in, for example, Published PCT Applications WO 03/008424, WO 03/091688, and WO 03/040257, and mixtures thereof.
• metal chelated oxinoid compounds such as tris(8-hydroxyquinolato)aluminum (Alq3)
• cyclometalated iridium and platinum electroluminescent compounds such as complexes of iridium with phenylpyridine
• red, orange and yellow light-emitting materials include, but are not limited to, complexes of Ir having phenylquinoline or
• phosphorescent compound a host material, and a compound having Formula I as an electron-trap material.
• luminescent compound a host material, a compound having Formula I as an electron-trap material, and a second host material.
• TAPC phenyljcyclohexane
• EPD phenyljcyclohexane
• PDA tetrakis-(3- methylphenyl)-N,N,N',N'-2,5-phenylenediamine
• TPS p-(diethylamino)benzaldehyde
• Carbazole (61 .4g, 0.368 mol), anhydrous zinc chloride (Strem, 100.0 g, 0.734 mol), and 1210 ml nitromethane that was dried over activated 4A sieves overnight, was charged to an oven dried 2 liter pot with a mechanical stirrer, addition funnel and nitrogen inlet, t-butyl chloride (81 .1 ml, 0.734mol) was added drop wise at room temperature and the reaction was stirred overnight. The reaction was tracked by LCMS. After completion 200ml methanol was added and the mixture was stirred for one hour. Solvent was removed by rotoevaporation and the mixture was taken up in methylene chloride and washed with water.
• Ligand for G9 This material was prepared as described above for ligand G1 except using 2-phenyl-4-chloro-pyridine in place of the 2-(4-t- butylphenyl)-4-chloropyridine from example 1 above.
• HIJ-1 is an electrically conductive polymer doped with a polymeric
• Host-1 is an indolocarbazole. Such materials have been described in, for example, published PCT application WO 2010/099534.
• Host-2 is a deuterated analog of Host-1 .
• Host-3 is a deuterated indolocarbazole. Such materials have been described in, for example, published PCT application WO
• Host-4 is an indolocarbazole. Such materials have been described in, for example, copending application [UC1006].
• ET-1 is a metal quinolate complex.
• Dopant-2 has the formula below, and can be made in an analogous
• ITO Indium Tin Oxide
• CE current efficiency
• E.Q.E. is the external quantum efficiency
• CIEx and CIEy are the x and y color coordinates according to the C LE. chromaticity scale (Commission Internationale de L'Eclairage, 1931 )
• T50 is to time to reach 50% of initial luminance at 1000 nits
• ADT50 is the adjusted time to reach 50% luminance at display luminance.
• Dopant-1 in Host-3 in a weight ratio of 16:84.
• CE current efficiency
• E.Q.E. is the external quantum efficiency
• CIEx and CIEy are the x and y color coordinates according to the C LE. chromaticity scale (Commission Internationale de L'Eclairage, 1931 )
• T50 is to time to reach 50% of initial luminance at 1000 nits
• ADT50 is the adjusted time to reach 50% luminance at display luminance.

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