US20130032785A1 - Materials for organic light emitting diode - Google Patents

Materials for organic light emitting diode Download PDF

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US20130032785A1
US20130032785A1 US13195544 US201113195544A US2013032785A1 US 20130032785 A1 US20130032785 A1 US 20130032785A1 US 13195544 US13195544 US 13195544 US 201113195544 A US201113195544 A US 201113195544A US 2013032785 A1 US2013032785 A1 US 2013032785A1
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hydrogen
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deuterium
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Bin Ma
Alan DeAngelis
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Universal Display Corp
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    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0085Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising Iridium
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033Iridium compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/185Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0079Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3)
    • H01L51/0081Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3) comprising aluminium, e.g. Alq3
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer
    • H01L51/5016Triplet emission

Abstract

Organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via two carbon atoms. These compounds also comprise a substituent other than hydrogen and deuterium on the quinoline, isoquinoline or linker. These compounds may be used as red emitters in phosphorescent OLEDs. In particular, these compounds may provide stable, narrow and efficient red emission.

Description

  • The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.
  • FIELD OF THE INVENTION
  • The present invention relates to organic light emitting devices (OLEDs). More specifically, the present invention is related to organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively. The ligand also contains a bulky substituent on the quinoline, isoquinoline or two carbon atom linker. These compounds may be used in OLEDs to provide devices with improved lifetime and color. In particular, these compounds may be especially useful as stable, narrow and efficient red emissive compounds.
  • BACKGROUND
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • 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.
  • 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.
  • One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the following structure:
  • Figure US20130032785A1-20130207-C00001
  • In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.
  • As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
  • As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • As used herein, “solution processible” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
  • A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
  • As used herein, and as would be generally understood by one skilled in the art, a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.
  • As used herein, and as would be generally understood by one skilled in the art, a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
  • More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.
  • SUMMARY OF THE INVENTION
  • Organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via a carbon linker are provided. The compounds also comprise a bulky substituent on the quinoline, isoquinoline, or linker. The compounds have the formula M(L1)x(L2)y(L3)z.
  • The ligand L1 is
  • Figure US20130032785A1-20130207-C00002
  • The ligand L2 is
  • Figure US20130032785A1-20130207-C00003
  • The ligand L3 is a third ligand.
  • Each L1, L2 and L3 can be the same or different. M is a metal having an atomic number greater than 40. Preferably, M is Ir. x is 1, 2, or 3. y is 0, 1, or 2. z is 0, 1, or 2. x+y+z is the oxidation state of the metal M. R is a carbocyclic or heterocyclic ring fused to the pyridine ring. R is optionally further substituted with R′. A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring. R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions. Each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium. Any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  • In one aspect, at least one of R1, R2, R3, R4, and R′ is an alkyl. In another aspect, R′ is not hydrogen or deuterium. Preferably, at least one of R1, R2, R3, R4, and R′ is an alkyl having more than 2 carbon atoms. More preferably, at least one of R1, R2, R3, R4, and R′ is isobutyl.
  • In one aspect, L3 is a monoanionic bidentate ligand.
  • In another aspect, L3 is
  • Figure US20130032785A1-20130207-C00004
  • and R′1, R′2, and R′3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. Preferably, R′2 is hydrogen. More preferably, at least one of R′1, R′2, and R′3 contains a branched alkyl moiety with branching at a position further than the α position to the carbonyl group. Most preferably, at least one of R′1 and R′3 is isobutyl.
  • In one aspect, the compound has the formula:
  • Figure US20130032785A1-20130207-C00005
  • R5 and R6 may represent mono, di, tri, or tetra substitutions. Each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium. m is 1, 2, or 3.
  • in another aspect, the compound has the formula:
  • Figure US20130032785A1-20130207-C00006
  • R5 and R6 may represent mono, di, tri, or tetra substitutions. Each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium. m is 1, 2, or 3.
  • In one aspect, the compound is homoleptic. In another aspect, the compound is heteroleptic.
  • Specific non-limiting examples of organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, are provided. These compounds also have a bulky substituent on the quinoline, isoquinoline, or linker. In one aspect, the compound is selected from the group consisting of:
  • Figure US20130032785A1-20130207-C00007
    Figure US20130032785A1-20130207-C00008
    Figure US20130032785A1-20130207-C00009
    Figure US20130032785A1-20130207-C00010
    Figure US20130032785A1-20130207-C00011
    Figure US20130032785A1-20130207-C00012
    Figure US20130032785A1-20130207-C00013
    Figure US20130032785A1-20130207-C00014
    Figure US20130032785A1-20130207-C00015
    Figure US20130032785A1-20130207-C00016
    Figure US20130032785A1-20130207-C00017
    Figure US20130032785A1-20130207-C00018
  • Preferably, the compound is:
  • Figure US20130032785A1-20130207-C00019
  • Additionally, a first device comprising a first organic light emitting device is provided. The organic light emitting device further comprises an anode, a cathode, and an organic layer, disposed between the anode and the cathode. The organic layer further comprises a compound having the formula M(L1)x(L2)y(L3)z, as described above.
  • The ligand L1 is
  • Figure US20130032785A1-20130207-C00020
  • The ligand L2 is
  • Figure US20130032785A1-20130207-C00021
  • The ligand L3 is a third ligand.
  • Each L1, L2 and L3 can be the same or different. M is a metal having an atomic number greater than 40. x is 1, 2, or 3. y is 0, 1, or 2. z is 0, 1, or 2. x+y+z is the oxidation state of the metal M. R is a carbocyclic or heterocyclic ring fused to the pyridine. R is optionally further substituted with R′. A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring. R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions. Each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium. Any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  • The various specific aspects discussed above for compounds having the formula M(L1)x(L2)y(L3)z are also applicable to a compound having M(L1)x(L2)y(L3)z that is used in the first device. In particular, specific aspects of L1, L2, L3, A, B, C, RA, RB, RC, RZ, R, R′, R1, R2, R3, R4, R5, R6, R′1, R′2, R′3, M, m Formula III and Formula IV of the compound having the formula M(L1)x(L2)y(L3)z are also applicable to a compound having M(L1)x(L2)y(L3)z that is used in the first device.
  • In one aspect, the first device is a consumer product. In another aspect, the first device is an organic light emitting device. In yet another aspect, the first device comprises a lighting panel.
  • In one aspect, the organic layer is an emissive layer and the compound is an emissive dopant. In another aspect, the organic layer further comprises a host. Preferably, the host is a metal 8-hydroxyquinolate.
  • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 shows an organic light emitting device.
  • FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
  • FIG. 3 shows a phenylquinoline or phenylisoquinoline ligand with the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, and comprising a bulky substituent.
  • FIG. 4 shows exemplary organometallic compounds comprising phenylquinoline or phenylisoquinoline ligand with the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, and comprising a bulky substituent.
  • DETAILED DESCRIPTION
  • 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.
  • 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.
  • 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.
  • FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.
  • More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.
  • FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
  • The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.
  • Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
  • Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.).
  • The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.
  • The terms halo, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, arylkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in U.S. Pat. No. 7,279,704 at cols. 31-32, which are incorporated herein by reference.
  • A novel class of organometallic compounds is provided. The compounds comprise a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via two carbon atoms, e.g., a linked phenylquinoline or linked phenylisoquinoline (as illustrated in FIG. 3). In addition, the ligand also includes at least one substituent other than hydrogen and deuterium on the quinoline, isoquinoline or two carbon atoms linking the quinoline or isoquinoline to the aromatic ring, i.e., bulky substituent. These compounds may be used as red emitters in phosphorescent OLEDs. In particular, these compounds may provide stable, narrow and efficient red emission as a result of the rigidification and addition of a bulky substituent.
  • The compounds disclosed herein may provide narrow red emission as a result of rigidification, which may narrow the EL spectrum. The spectrum at half maximum (FWHW) of an organic molecule may narrow as the molecules become more rigid. The compounds disclosed herein are made more rigid by linking the top portion of the ligand, e.g., a quinoline or isoquinoline, to the bottom portion of the ligand, e.g., phenyl ring. For example, the compounds may include a linked phenylquinoline or linked phenylisoquinoline. In particular, a compound comprising a 2-phenylquinoline ligand in which the quinoline has been linked to the phenyl ring may have a narrower EL spectrum. A narrow EL spectrum is a desirable property of electroluminescent materials for use in an OLED.
  • As discussed above, a two carbon atom linker links the quinoline or isoquinoline to the phenyl ring of the phenylquinoline or phenylisoquinoline. Without being bound by theory, it is believed that using only carbon atoms as linkers may provide better device stability, i.e., longer device lifetime, when compared to other linkers, such as those with oxygen atoms. Additionally, it is believed that two atoms in the linker backbone, rather than one atom, is desirable. One atom linker may be too small, resulting in an increased coordinating binding angle of the ligand to metal on the other side of the ligand, which may reduce the bond strength of metal to ligand, and, in turn, decrease the stability of the metal complex.
  • Moreover, the compounds disclosed herein may provide stable and efficient red emission as a result of having a substituent other than hydrogen and deuterium on the quinoline, isoquinoline or two carbon atoms in the linked ligand. Without being bound by theory, it is believed that the addition of a bulky substituent to the linked ligand may prevent aggregation and self quenching in the compound, thereby providing higher device efficiency.
  • Without being bound by theory, it may be particularly advantageous to have an alkyl substituent as the bulky group on the linked ligand because alkyls offer a wide range of tunability. In particular, an alkyl substituent may be useful for tuning the evaporation temperature, solubility, energy levels, device efficiency and narrowness of the emission spectrum of the compound. Additionally, alkyl groups can be stable functional groups chemically and in device operation. For example, a linked ligand comprising an alkyl substituent on the quinoline may provide increased efficiency.
  • Organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand containing a quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via two carbon atoms are provided (as illustrated in FIG. 4).
  • The compounds also comprise a bulky substituent, i.e., not hydrogen or deuterium, on the quinoline, isoquinoline, or linker. The compounds have the formula M(L1)x(L2)y(L3)z.
  • The ligand L1 is
  • Figure US20130032785A1-20130207-C00022
  • The ligand L2 is
  • Figure US20130032785A1-20130207-C00023
  • The ligand L3 is a third ligand.
  • Each L1, L2 and L3 can be the same or different. M is a metal having an atomic number greater than 40. Preferably, M is Ir. x is 1, 2, or 3. y is 0, 1, or 2. z is 0, 1, or 2. x+y+z is the oxidation state of the metal M. R is a carbocyclic or heterocyclic ring fused to the pyridine. R is optionally further substituted with R′. A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring. R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions. Each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium. Any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  • For the compounds disclosed herein, a bulky substituent is present on the quinoline, isoquinoline or two carbon atoms in the linked ligand. The bulky group may be a halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, i.e., bulky group is a substituent other than hydrogen or deuterium. Without being bound by theory, it is believed that the bulky substituent is least likely to affect the emission color of the compound If it is placed at one or more of the R1, R2, R3, R4, and R′ positions.
  • In one aspect, at least one of R1, R2, R3, R4, and R′ is an alkyl. In another aspect, R′ is not hydrogen or deuterium. Preferably, at least one of R1, R2, R3, R4, and R′ is an alkyl having more than 2 carbon atoms. More preferably, at least one of R1, R2, R3, R4, and R′ is isobutyl.
  • In one aspect, L3 is a monoanionic bidentate ligand.
  • In another aspect, L3 is
  • Figure US20130032785A1-20130207-C00024
  • and R′1, R′2, and R′3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. Preferably, R′2 is hydrogen. More preferably, at least one of R′1, R′2, and R′3 contains a branched alkyl moiety with branching at a position further than the α position to the carbonyl group. Most preferably, at least one of R′1 and R′3 is isobutyl.
  • In one aspect, the compound has the formula:
  • Figure US20130032785A1-20130207-C00025
  • R5 and R6 may represent mono, di, tri, or tetra substitutions. Each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium. m is 1, 2, or 3.
  • In another aspect, the compound has the formula:
  • Figure US20130032785A1-20130207-C00026
  • R5 and R6 may represent mono, di, tri, or tetra substitutions. Each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium. m is 1, 2, or 3.
  • Generally, it is desirable to maintain red emission while improving other properties of these compounds, such as evaporation temperature and solubility. In some instances, it may be desirable for the compound to have a less bulky substituent on ring A. Ring A, e.g., benzene, may be substituted with hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, as discussed above. However, it is thought that placing a bulky substituent on ring A may cause a pronounced shift in the emission color of the compound. In some aspects, then, it is preferable to substitute ring A with less bulky chemical substituents to maintain good red emission while improving other properties of the compound, such as evaporation temperature and solubility.
  • In one aspect, the compound is homoleptic. In another aspect, the compound is heteroleptic.
  • Specific non-limiting examples of organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl of the phenylquinoline or phenylisoquinoline, respectively, via a 2 carbon atom linker are provided. These compounds also comprise a bulky substituent on the quinoline, isoquinoline, or linker. In one aspect, the compound is selected from the group consisting of:
  • Figure US20130032785A1-20130207-C00027
    Figure US20130032785A1-20130207-C00028
    Figure US20130032785A1-20130207-C00029
    Figure US20130032785A1-20130207-C00030
    Figure US20130032785A1-20130207-C00031
    Figure US20130032785A1-20130207-C00032
    Figure US20130032785A1-20130207-C00033
    Figure US20130032785A1-20130207-C00034
    Figure US20130032785A1-20130207-C00035
    Figure US20130032785A1-20130207-C00036
    Figure US20130032785A1-20130207-C00037
    Figure US20130032785A1-20130207-C00038
  • Preferably, the compound is:
  • Figure US20130032785A1-20130207-C00039
  • Additionally, a first device comprising a first organic light emitting device is provided. The organic light emitting device further comprises an anode, a cathode, and an organic layer, disposed between the anode and the cathode. The organic layer further comprises a compound having the formula M(L1)x(L2)y(L3)z.
  • The ligand L1 is
  • Figure US20130032785A1-20130207-C00040
  • The ligand L2 is
  • Figure US20130032785A1-20130207-C00041
  • The ligand L3 is a third ligand.
  • Each L1, L2 and L3 can be the same or different. M is a metal having an atomic number greater than 40. x is 1, 2, or 3. y is 0, 1, or 2. z is 0, 1, or 2. x+y+z is the oxidation state of the metal M. R is a carbocyclic or heterocyclic ring fused to the pyridine ring. R is optionally further substituted with R′. A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring. R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions. Each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. At least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium. Any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  • The various specific aspects discussed above for compounds having the formula M(L1)x(L2)y(L3)z are also applicable to a compound having M(L1)x(L2)y(L3)z that is used in the first device. In particular, specific aspects of L1, L2, L3, A, B, C, RA, RB, Rc, RZ, R, R′, R1, R2, R3, R4, R5, R6, R′1, R′2, R′3, M, m Formula III and Formula IV of the compound having the formula M(L1)x(L2)y(L3)z are also applicable to a compound having M(L1)x(L2)y(L3)z that is used in the first device.
  • In one aspect, the first device is a consumer product. In another aspect, the first device is an organic light emitting device. In yet another aspect, the first device comprises a lighting panel.
  • In one aspect, the organic layer is an emissive layer and the compound is an emissive dopant. In another aspect, the organic layer further comprises a host. Preferably, the host is a metal 8-hydroxyquinolate.
  • Combination with Other Materials
  • The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
  • HIL/HTL:
  • A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but not limit to: a phthalocyanine or porphryin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and sliane derivatives; a metal oxide derivative, such as MoOx; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.
  • Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
  • Figure US20130032785A1-20130207-C00042
  • Each of Ar1 to Ar9 is selected from the group consisting aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; group consisting aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and group consisting 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Wherein each Ar is further substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • In one aspect, Ar1 to Ar9 is independently selected from the group consisting of:
  • Figure US20130032785A1-20130207-C00043
  • k is an integer from 1 to 20; X1 to X8 is C (including CH) or N; Ar1 has the same group defined above.
  • Examples of metal complexes used in HIL or HTL include, but not limit to the following general formula:
  • Figure US20130032785A1-20130207-C00044
  • M is a metal, having an atomic weight greater than 40; (Y1-Y2) is a bidentate ligand, Y1 and Y2 are independently selected from C, N, O, P, and S; L is an ancillary ligand; m is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and m+n is the maximum number of ligands that may be attached to the metal.
  • In one aspect, (Y1-Y2) is a 2-phenylpyridine derivative.
  • In another aspect, (Y1-Y2) is a carbene ligand.
  • In another aspect, M is selected from Ir, Pt, Os, and Zn.
  • In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc+/Fc couple less than about 0.6 V.
  • Host:
  • The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant.
  • Examples of metal complexes used as host are preferred to have the following general formula:
  • Figure US20130032785A1-20130207-C00045
  • M is a metal; (Y3-Y4) is a bidentate ligand, Y3 and Y4 are independently selected from C, N, O, P, and S; L is an ancillary ligand; m is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and m+n is the maximum number of ligands that may be attached to the metal.
  • In one aspect, the metal complexes are:
  • Figure US20130032785A1-20130207-C00046
  • (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
  • In another aspect, M is selected from Ir and Pt.
  • In a further aspect, (Y3-Y4) is a carbene ligand.
  • Examples of organic compounds used as host are selected from the group consisting aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; group consisting aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and group consisting 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Wherein each group is further substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
  • In one aspect, host compound contains at least one of the following groups in the molecule:
  • Figure US20130032785A1-20130207-C00047
    Figure US20130032785A1-20130207-C00048
  • R1 to R7 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
  • k is an integer from 0 to 20.
  • X1 to X8 is selected from C (including CH) or N.
  • HBL:
  • A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED.
  • In one aspect, compound used in HBL contains the same molecule used as host described above.
  • In another aspect, compound used in HBL contains at least one of the following groups in the molecule:
  • Figure US20130032785A1-20130207-C00049
  • k is an integer from 0 to 20; L is an ancillary ligand, m is an integer from 1 to 3.
  • ETL:
  • Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.
  • In one aspect, compound used in ETL contains at least one of the following groups in the molecule:
  • Figure US20130032785A1-20130207-C00050
  • R1 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfanyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
  • Ar1 to Ara has the similar definition as Ar's mentioned above.
  • k is an integer from 0 to 20.
  • X1 to X8 is selected from C (including CH) or N.
  • In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:
  • Figure US20130032785A1-20130207-C00051
  • (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N;
  • L is an ancillary ligand; m is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
  • In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated.
  • In addition to and/or in combination with the materials disclosed herein, many hole injection materials, hole transporting materials, host materials, dopant materials, exiton/hole blocking layer materials, electron transporting and electron injecting materials may be used in an OLED. Non-limiting examples of the materials that may be used in an OLED in combination with materials disclosed herein are listed in Table 1 below. Table 1 lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials.
  • TABLE 1
    MATERIAL EXAMPLES OF MATERIAL PUBLICATIONS
    Hole injection materials
    Phthalocyanine and porphryin compounds
    Figure US20130032785A1-20130207-C00052
    Appl. Phys. Lett. 69, 2160 (1996)
    Starburst triarylamines
    Figure US20130032785A1-20130207-C00053
    J. Lumin. 72-74, 985 (1997)
    CFx Fluorohydrocarbon polymer
    Figure US20130032785A1-20130207-C00054
    Appl. Phys. Lett. 78, 673 (2001)
    Conducting polymers (e.g., PEDOT:PSS, polyaniline, polypthiophene)
    Figure US20130032785A1-20130207-C00055
    Synth. Met. 87, 171 (1997) WO2007002683
    Phosphonic acid and sliane SAMs
    Figure US20130032785A1-20130207-C00056
    US20030162053
    Triarylamine or polythiophene polymers with conductivity dopants
    Figure US20130032785A1-20130207-C00057
    Figure US20130032785A1-20130207-C00058
    Figure US20130032785A1-20130207-C00059
    EP1725079A1
    Arylamines complexed with metal oxides such as molybdenum and tungsten oxides
    Figure US20130032785A1-20130207-C00060
    SID Symposium Digest, 37, 923 (2006) WO2009018009
    p-type semiconducting organic complexes
    Figure US20130032785A1-20130207-C00061
    US20020158242
    Metal organometallic complexes
    Figure US20130032785A1-20130207-C00062
    US20060240279
    Cross-linkable compounds
    Figure US20130032785A1-20130207-C00063
    US20080220265
    Hole transporting materials
    Triarylamines (e.g., TPD, α-NPD)
    Figure US20130032785A1-20130207-C00064
    Appl. Phys. Lett. 51, 913 (1987)
    Figure US20130032785A1-20130207-C00065
    U.S. Pat. No. 5,061,569
    Figure US20130032785A1-20130207-C00066
    EP650955
    Figure US20130032785A1-20130207-C00067
    J. Mater. Chem. 3, 319 (1993)
    Figure US20130032785A1-20130207-C00068
    Appl. Phys. Lett. 90, 183503 (2007)
    Figure US20130032785A1-20130207-C00069
    Appl. Phys. Lett. 90, 183503 (2007)
    Triaylamine on spirofluorene core
    Figure US20130032785A1-20130207-C00070
    Synth. Met. 91, 209 (1997)
    Arylamine carbazole compounds
    Figure US20130032785A1-20130207-C00071
    Adv. Mater. 6, 677 (1994), US20080124572
    Triarylamine with (di)benzothiophene/ (di)benzofuran
    Figure US20130032785A1-20130207-C00072
    US20070278938, US20080106190
    Indolocarbazoles
    Figure US20130032785A1-20130207-C00073
    Synth. Met. 111, 421 (2000)
    Isoindole compounds
    Figure US20130032785A1-20130207-C00074
    Chem. Mater. 15, 3148 (2003)
    Metal carbene complexes
    Figure US20130032785A1-20130207-C00075
    US20080018221
    Phosphorescent OLED host materials
    Red hosts
    Arylcarbazoles
    Figure US20130032785A1-20130207-C00076
    Appl. Phys. Lett. 78, 1622 (2001)
    Metal 8-hydroxyquinolates (e.g., Alq3, BAlq)
    Figure US20130032785A1-20130207-C00077
    Nature 395, 151 (1998)
    Figure US20130032785A1-20130207-C00078
    US20060202194
    Figure US20130032785A1-20130207-C00079
    WO2005014551
    Figure US20130032785A1-20130207-C00080
    WO2006072002
    Metal phenoxybenzothiazole compounds
    Figure US20130032785A1-20130207-C00081
    Appl. Phys. Lett. 90, 123509 (2007)
    Conjugated oligomers and polymers (e.g., polyfluorene)
    Figure US20130032785A1-20130207-C00082
    Org. Electron. 1, 15 (2000)
    Aromatic fused rings
    Figure US20130032785A1-20130207-C00083
    WO2009066779, WO2009066778, WO2009063833, US20090045731, US20090045730, WO2009008311, US20090008605, US20090009065
    Zinc complexes
    Figure US20130032785A1-20130207-C00084
    WO2009062578
    Green hosts
    Arylcarbazoles
    Figure US20130032785A1-20130207-C00085
    Appl. Phys. Lett. 78, 1622 (2001)
    Figure US20130032785A1-20130207-C00086
    US20030175553
    Figure US20130032785A1-20130207-C00087
    WO2001039234
    Aryltriphenylene compounds
    Figure US20130032785A1-20130207-C00088
    US20060280965
    Figure US20130032785A1-20130207-C00089
    US20060280965
    Figure US20130032785A1-20130207-C00090
    WO2009021126
    Donor acceptor type molecules
    Figure US20130032785A1-20130207-C00091
    WO2008056746
    Aza-carbazole/DBT/DBF
    Figure US20130032785A1-20130207-C00092
    JP2008074939
    Polymers (e.g., PVK)
    Figure US20130032785A1-20130207-C00093
    Appl. Phys. Lett. 77, 2280 (2000)
    Spirofluorene compounds
    Figure US20130032785A1-20130207-C00094
    WO2004093207
    Metal phenoxybenzooxazole compounds
    Figure US20130032785A1-20130207-C00095
    WO2005089025
    Figure US20130032785A1-20130207-C00096
    WO2006132173
    Figure US20130032785A1-20130207-C00097
    JP200511610
    Spirofluorene-carbazole compounds
    Figure US20130032785A1-20130207-C00098
    JP2007254297
    Figure US20130032785A1-20130207-C00099
    JP2007254297
    Indolocabazoles
    Figure US20130032785A1-20130207-C00100
    WO2007063796
    Figure US20130032785A1-20130207-C00101
    WO2007063754
    5-member ring electron deficient heterocycles (e.g., triazole, oxadiazole)
    Figure US20130032785A1-20130207-C00102
    J. Appl. Phys. 90, 5048 (2001)
    Figure US20130032785A1-20130207-C00103
    WO2004107822
    Tetraphenylene complexes
    Figure US20130032785A1-20130207-C00104
    US20050112407
    Metal phenoxypyridine compounds
    Figure US20130032785A1-20130207-C00105
    WO2005030900
    Metal coordination complexes (e.g., Zn, Al with N{circumflex over ( )}N ligands)
    Figure US20130032785A1-20130207-C00106
    US20040137268, US20040137267
    Blue hosts
    Arylcarbazoles
    Figure US20130032785A1-20130207-C00107
    Appl. Phys. Lett, 82, 2422 (2003)
    Figure US20130032785A1-20130207-C00108
    US20070190359
    Dibenzothiophene/ Dibenzofuran-carbazole compounds
    Figure US20130032785A1-20130207-C00109
    WO2006114966, US20090167162
    Figure US20130032785A1-20130207-C00110
    US20090167162
    Figure US20130032785A1-20130207-C00111
    WO2009086028
    Figure US20130032785A1-20130207-C00112
    US20090030202, US20090017330
    Silicon aryl compounds
    Figure US20130032785A1-20130207-C00113
    US20050238919
    Figure US20130032785A1-20130207-C00114
    WO2009003898
    Silicon/Germanium aryl compounds
    Figure US20130032785A1-20130207-C00115
    EP2034538A
    Aryl benzoyl ester
    Figure US20130032785A1-20130207-C00116
    WO2006100298
    High triplet metal organometallic complex
    Figure US20130032785A1-20130207-C00117
    U.S. Pat. No. 7,154,114
    Phosphorescent dopants
    Red dopants
    Heavy metal porphyrins (e.g., PtOEP)
    Figure US20130032785A1-20130207-C00118
    Nature 395, 151 (1998)
    Iridium(III) organometallic complexes
    Figure US20130032785A1-20130207-C00119
    Appl. Phys. Lett. 78, 1622 (2001)
    Figure US20130032785A1-20130207-C00120
    US2006835469
    Figure US20130032785A1-20130207-C00121
    US2006835469
    Figure US20130032785A1-20130207-C00122
    US20060202194
    Figure US20130032785A1-20130207-C00123
    US20060202194
    Figure US20130032785A1-20130207-C00124
    US20070087321
    Figure US20130032785A1-20130207-C00125
    US20070087321
    Figure US20130032785A1-20130207-C00126
    Adv. Mater. 19, 739 (2007)
    Figure US20130032785A1-20130207-C00127
    WO2009100991
    Figure US20130032785A1-20130207-C00128
    WO2008101842
    Platinum(II) organometallic complexes
    Figure US20130032785A1-20130207-C00129
    WO2003040257
    Osminum(III) complexes
    Figure US20130032785A1-20130207-C00130
    Chem. Mater. 17, 3532 (2005)
    Ruthenium(II) complexes
    Figure US20130032785A1-20130207-C00131
    Adv. Mater. 17, 1059 (2005)
    Rhenium (I), (II), and (III) complexes
    Figure US20130032785A1-20130207-C00132
    US20050244673
    Green dopants
    Iridium(III) organometallic complexes
    Figure US20130032785A1-20130207-C00133
      and its derivatives
    Inorg. Chem. 40, 1704 (2001)
    Figure US20130032785A1-20130207-C00134
    US20020034656
    Figure US20130032785A1-20130207-C00135
    U.S. Pat. No. 7,332,232
    Figure US20130032785A1-20130207-C00136
    US20090108737
    Figure US20130032785A1-20130207-C00137
    US20090039776
    Figure US20130032785A1-20130207-C00138
    U.S. Pat. No. 6,921,915
    Figure US20130032785A1-20130207-C00139
    U.S. Pat. No. 6,687,266
    Figure US20130032785A1-20130207-C00140
    Chem. Mater. 16, 2480 (2004)
    Figure US20130032785A1-20130207-C00141
    US20070190359
    Figure US20130032785A1-20130207-C00142
    US20060008670 JP2007123392
    Figure US20130032785A1-20130207-C00143
    Adv. Mater. 16, 2003 (2004)
    Figure US20130032785A1-20130207-C00144
    Angew. Chem. Int. Ed. 2006, 45, 7800
    Figure US20130032785A1-20130207-C00145
    WO2009050290
    Figure US20130032785A1-20130207-C00146
    US20090165846
    Figure US20130032785A1-20130207-C00147
    US20080015355
    Monomer for polymeric metal organometallic compounds
    Figure US20130032785A1-20130207-C00148
    U.S. Pat. No. 7,250,226, U.S. Pat. No. 7,396,598
    Pt(II) organometallic complexes, including polydentated ligands
    Figure US20130032785A1-20130207-C00149
    Appl. Phys. Lett. 86, 153505 (2005)
    Figure US20130032785A1-20130207-C00150
    Appl. Phys. Lett. 86, 153505 (2005)
    Figure US20130032785A1-20130207-C00151
    Chem. Lett. 34, 592 (2005)
    Figure US20130032785A1-20130207-C00152
    WO2002015645
    Figure US20130032785A1-20130207-C00153
    US20060263635
    Cu complexes
    Figure US20130032785A1-20130207-C00154
    WO2009000673
    Gold complexes
    Figure US20130032785A1-20130207-C00155
    Chem. Commun. 2906 (2005)
    Rhenium(III) complexes
    Figure US20130032785A1-20130207-C00156
    Inorg. Chem. 42, 1248 (2003)
    Deuterated organometallic complexes
    Figure US20130032785A1-20130207-C00157
    US20030138657
    Organometallic complexes with two or more metal centers
    Figure US20130032785A1-20130207-C00158
    US20030152802
    Figure US20130032785A1-20130207-C00159
    U.S. Pat. No. 7,090,928
    Blue dopants
    Iridium(III) organometallic complexes
    Figure US20130032785A1-20130207-C00160
    WO2002002714
    Figure US20130032785A1-20130207-C00161
    WO2006009024
    Figure US20130032785A1-20130207-C00162
    US20060251923
    Figure US20130032785A1-20130207-C00163
    U.S. Pat. No. 7,393,599, WO2006056418, US20050260441, WO2005019373
    Figure US20130032785A1-20130207-C00164
    U.S. Pat. No. 7,534,505
    Figure US20130032785A1-20130207-C00165
    U.S. Pat. No. 7,445,855
    Figure US20130032785A1-20130207-C00166
    US20070190359, US20080297033
    Figure US20130032785A1-20130207-C00167
    US7338722
    Figure US20130032785A1-20130207-C00168
    US20020134984
    Figure US20130032785A1-20130207-C00169
    Angew. Chem. Int. Ed. 47, 1 (2008)
    Figure US20130032785A1-20130207-C00170
    Chem. Mater. 18, 5119 (2006)
    Figure US20130032785A1-20130207-C00171
    Inorg. Chem. 46, 4308 (2007)
    Figure US20130032785A1-20130207-C00172
    WO2005123873
    Figure US20130032785A1-20130207-C00173
    WO2005123873
    Figure US20130032785A1-20130207-C00174
    WO2007004380
    Figure US20130032785A1-20130207-C00175
    WO2006082742
    Osmium(II) complexes
    Figure US20130032785A1-20130207-C00176
    U.S. Pat. No. 7,279,704
    Figure US20130032785A1-20130207-C00177
    Organometallics 23, 3745 (2004)
    Gold complexes
    Figure US20130032785A1-20130207-C00178
    Appl. Phys. Lett. 74, 1361 (1999)
    Platinum(II) complexes
    Figure US20130032785A1-20130207-C00179
    WO2006098120, WO2006103874
    Exciton/hole blocking layer materials
    Bathocuprine compounds (e.g., BCP, BPhen)
    Figure US20130032785A1-20130207-C00180
    Appl. Phys. Lett. 75, 4 (1999)
    Figure US20130032785A1-20130207-C00181
    Appl. Phys. Lett. 79, 449 (2001)
    Metal 8-hydroxyquinolates (e.g., BAlq)
    Figure US20130032785A1-20130207-C00182
    Appl. Phys. Lett. 81, 162 (2002)
    5-member ring electron deficient heterocycles such as triazole, oxadiazole, imidazole, benzoimidazole
    Figure US20130032785A1-20130207-C00183
    Appl. Phys. Lett. 81, 162 (2002)
    Triphenylene compounds
    Figure US20130032785A1-20130207-C00184
    US20050025993
    Fluorinated aromatic compounds
    Figure US20130032785A1-20130207-C00185
    Appl. Phys. Lett. 79, 156 (2001)
    Phenothiazine-S-oxide
    Figure US20130032785A1-20130207-C00186
    WO2008132085
    Electron transporting materials
    Anthracene- benzoimidazole compounds
    Figure US20130032785A1-20130207-C00187
    WO2003060956
    Figure US20130032785A1-20130207-C00188
    US20090179554
    Aza triphenylene derivatives
    Figure US20130032785A1-20130207-C00189
    US20090115316
    Anthracene-benzothiazole compounds
    Figure US20130032785A1-20130207-C00190
    Appl. Phys. Lett. 89, 063504 (2006)
    Metal 8-hydroxyquinolates (e.g., Alq3, Zrq4)
    Figure US20130032785A1-20130207-C00191
    Appl. Phys. Lett. 51, 913 (1987) U.S. Pat. No. 7,230,107
    Metal hydroxybenoquinolates
    Figure US20130032785A1-20130207-C00192
    Chem. Lett. 5, 905 (1993)
    Bathocuprine compounds such as BCP, BPhen, etc
    Figure US20130032785A1-20130207-C00193
    Appl. Phys. Lett. 91, 263503 (2007)
    Figure US20130032785A1-20130207-C00194
    Appl. Phys. Lett. 79, 449 (2001)
    5-member ring electron deficient heterocycles (e.g., triazole, oxadiazole, imidazole, benzoimidazole)
    Figure US20130032785A1-20130207-C00195
    Appl. Phys. Lett. 74, 865 (1999)
    Figure US20130032785A1-20130207-C00196
    Appl. Phys. Lett. 55, 1489 (1989)
    Figure US20130032785A1-20130207-C00197
    Jpn. J. Apply. Phys. 32, L917 (1993)
    Silole compounds
    Figure US20130032785A1-20130207-C00198
    Org. Electron. 4, 113 (2003)
    Arylborane compounds
    Figure US20130032785A1-20130207-C00199
    J. Am. Chem. Soc. 120, 9714 (1998)
    Fluorinated aromatic compounds
    Figure US20130032785A1-20130207-C00200
    J. Am. Chem. Soc. 122, 1832 (2000)
    Fullerene (e.g., C60)
    Figure US20130032785A1-20130207-C00201
    US20090101870
    Triazine complexes
    Figure US20130032785A1-20130207-C00202
    US20040036077
    Zn (N{circumflex over ( )}N) complexes
    Figure US20130032785A1-20130207-C00203
    U.S. Pat. No. 6,528,187
  • EXPERIMENTAL Compound Examples Example 1 Synthesis of Compound 9
  • Figure US20130032785A1-20130207-C00204
  • Synthesis of (2-amino-6-chlorophenyl)methanol
  • 2-Amino-6-chlorobenzoic acid (25.0 g, 143 mmol) was dissolved in 120 mL of anhydrous THF in a 500 mL 2 neck round bottom flask. The solution was cooled in an ice-water bath. 215 mL of 1.0 M lithium aluminum hydride (LAH) THF solution was then added dropwise. After all of the LAH was added, the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for overnight. ˜10 mL of water was added to the reaction mixture followed by 7 g 15% NaOH. An additional 20 g of water was added to the reaction mixture. Decant the organic THF phase and the solid was added with ethyl acetate. ˜200 mL and stirring and combined ethyl acetate organic portion and THF portion and added Na2SO4 drying agent. The mixture was filtered and evaporated. ˜20 g yellow solid was obtained without further purification for next step reaction.
  • Figure US20130032785A1-20130207-C00205
  • Synthesis of 8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c] acridine
  • (2-Amino-6-chlorophenyl)methanol (16 g, 101 mmol), 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one (20.0 g, 111 mmol), RuCl2(PPh3)3 (0.971 g, 1.01 mmol), and KOH (5.7 g, 101 mmol) were refluxed in 200 mL of toluene for 12 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with dichloromethane. The product was washed by methanol and recrystallized from hexane to obtain ˜20 gram of the desired product which was confirmed by GC-MS.
  • Figure US20130032785A1-20130207-C00206
  • Synthesis of 8-isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine
  • 8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine (15.0 g, 51.1 mmol), isobutylboronic acid (7.8 g, 77 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.6 g, 4.08 mmol) potassium phosphate monohydrate (41.2 g, 179 mmol) were mixed in 300 mL of toluene. The system was degassed for 20 minutes. Pd2(dba)3 (0.93 g, 1.02 mmol) was then added and the system was refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with 30% ethyl acetate in toluene. ˜19.5 crude liquid was obtained. The crude product was recystalized from 5% acetone in hexane to obtain ˜14.9 g pure product (99.6%) which was confirmed by GC-MS.
  • Figure US20130032785A1-20130207-C00207
  • Synthesis of Iridium Dimer.
  • A mixture of 8-isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine (11.5 g, 36.5 mmol), IrCl3.4H2O (4.5 g, 12.2 mmol), 2-ethoxyethanol (90 mL) and water (30 mL) was refluxed under nitrogen overnight. The reaction mixture was filtered and washed with MeOH (3×20 mL). ˜9 g of dimer was obtained after vacuum drying. The dimer was used for the next step without further purification.
  • Figure US20130032785A1-20130207-C00208
  • Synthesis of Compound 9.
  • Dimer (3.5 g, 2.07 mmol), pentane-2,4-dione (2.07 g, 20.7 mmol), Na2CO3 (2.19 g, 20.7 mmol) and 2-ethoxyethanol (100 mL) were stirred at room temperature for 24 h. The precipitate was filtered and washed with methanol. The solid was further purified by passing it through a silica gel plug (that was pretreated with 15% TEA in hexanes) and eluted with methylene chloride. 0.6 g of product Compound 9 was obtained after purification. The compound was confirmed by LC-MS.
  • Example 2 Synthesis of Compound 10
  • Compound 10 was synthesized in same way as Compound 9, and confirmed by LC-MS.
  • Device Examples
  • All example devices were fabricated by high vacuum (<10−7 Ton) thermal evaporation. The anode electrode is 1200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of LiF followed by 1,000 Å of Al. All devices are encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package.
  • The organic stack of the Device Examples consisted of sequentially, from the ITO surface, 100 Å of Compound A as the hole injection layer (HIL), 300 Å of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD) as the hole transporting layer (HTL), 300 Å of the invention compound doped in BAlq as host with 4, 6 or 8 wt % of an Ir phosphorescent compound as the emissive layer (EML), 500 or 550 Å of Alg3 (tris-8-hydroxyquinoline aluminum) as the ETL.
  • Comparative Device Examples with Compound B was fabricated similarly to the Device Examples, except that Compound B is used as the emitter in the EML.
  • As used herein, Compound A, Compound B and other compounds used in the device examples have the following structures:
  • Figure US20130032785A1-20130207-C00209
  • The device structures are summarized in Table 2, and the device data is summarized in Table 3. Cmpd. is an abbreviation of Compound. Ex. is an abbreviation of Example. Comp. Ex. is an abbreviation of Comparative Example.
  • TABLE 2
    Example HIL HTL EML (doping %) ETL
    Ex. 1 Compound NPD Balq Compound 10 Alq
    A 7%
    Ex. 2 Compound NPD Balq Compound 9 Alq
    A 8%
    Comp. Compound NPD Balq Compound B Alq
    Ex. 1 A 8%
  • TABLE 3
    At 2000
    At 1000 nits nits
    λmax FWHM Voltage LE EQE PE LT97%
    Cmpd. x y [nm] [nm] [V] [cd/A] [%] [lm/W] [Hr]
    Ex. 1 0.649 0.348 612 54 8.9 12.5 10.1 4.4 29.9
    Ex. 2 0.656 0.341 616 62 8.8 8.5 8.0 3.0 8.5
    Comp. Ex. 1 0.651 0.346 612 60 9.7 9.9 8.6 3.2 9.5
  • Table 3 is a summary of the device data. The luminous efficiency (LE), external quantum efficiency (EQE) and power efficiency (PE) were measured at 1000 nits, while the lifetime (LT97%) was defined as the time required for the device to decay to 97% of its initial luminance at 2000 nits under a constant current density.
  • As seen from Table 3, the EQE measured at 1000 nits for a device comprising Compound 10 is 17% higher than the EQE measured for a device comprising Compound B. Additionally, the EL spectral full width at half maximum (FWHW) of Compound 10 is also narrower than the FWHM of Compound B, i.e, FWHM of Compound 10 is 54 nm, while the FWHM of Compound B is 60 nm. The FWHM of Compound 9, however, is similar to the FWHM of Compound B. It is a desirable device property to have a narrow FWHM. These results indicate that Compound 10 is a more efficient red emitter than Compounds B with a desirable narrower FWHM.
  • Compound 10 also has a longer lifetime than Compound B, i.e., the LT97% measured at room temperature for Compound 10 is about three times as long as the LT97% measured at room temperature for Compound B. Compound 10 differs from Compound B in that it has a bulkier substituent on quinoline ring. Therefore, devices comprising a compound with a substituent on the quinoline ring may have significantly improved performance.
  • It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

Claims (24)

  1. 1. A compound having the formula M(L1)x(L2)y(L3)z:
    wherein the ligand L1 is
    Figure US20130032785A1-20130207-C00210
    wherein the ligand L2 is
    Figure US20130032785A1-20130207-C00211
    wherein the ligand L3 is a third ligand;
    wherein each L1, L2 and L3 can be the same or different;
    wherein M is a metal having an atomic number greater than 40;
    wherein x is 1, 2, or 3;
    wherein y is 0, 1, or 2;
    wherein z is 0, 1, or 2;
    wherein x+y+z is the oxidation state of the metal M;
    wherein R is a carbocyclic or heterocyclic ring fused to the pyridine ring;
    R is optionally further substituted with R′;
    wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
    wherein R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions;
    wherein each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfonyl, sulfonyl, phosphino, and combinations thereof;
    wherein at least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium; and
    wherein any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  2. 2. The compound of claim 1, wherein M is Ir.
  3. 3. The compound of claim 1, wherein at least one of R1, R2, R3, R4, and R′ is an alkyl.
  4. 4. The compound of claim 1, wherein at least one of R1, R2, R3, R4, and R′ is an alkyl having more than 2 carbon atoms.
  5. 5. The compound of claim 1, wherein at least one of R1, R2, R3, R4, and R′ is isobutyl.
  6. 6. The compound of claim 1, wherein R′ is not hydrogen or deuterium.
  7. 7. The compound of claim 1, wherein L3 is a monoanionic bidentate ligand.
  8. 8. The compound of claim 1, wherein L3 is
    Figure US20130032785A1-20130207-C00212
    and
    wherein R′1, R′2, and R′3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfanyl, sulfonyl, phosphino, and combinations thereof.
  9. 9. The compound of claim 8, wherein at least one of R′1, R′2, and R′3 contains a branched alkyl moiety with branching at a position further than the α position to the carbonyl group.
  10. 10. The compound of claim 8, wherein at least one of R′1 and R′3 is isobutyl.
  11. 11. The compound of claim 8, wherein R′2 is hydrogen.
  12. 12. The compound of claim 1, wherein the compound has the formula:
    Figure US20130032785A1-20130207-C00213
    wherein R5 and R6 may represent mono, di, tri, or tetra substitutions;
    wherein each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
    wherein at least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium; and
    wherein m is 1, 2, or 3.
  13. 13. The compound of claim 1, wherein the compound has the formula:
    Figure US20130032785A1-20130207-C00214
    wherein R5 and R6 may represent mono, di, tri, or tetra substitutions;
    wherein each of R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
    wherein at least one of R1, R2, R3, R4, and R6 is not hydrogen or deuterium; and
    wherein m is 1, 2, or 3.
  14. 14. The compound of claim 1, wherein the compound is homoleptic.
  15. 15. The compound of claim 1, wherein the compound is heteroleptic.
  16. 16. The compound of claim 1, wherein the compound is selected from the group consisting of:
    Figure US20130032785A1-20130207-C00215
    Figure US20130032785A1-20130207-C00216
    Figure US20130032785A1-20130207-C00217
    Figure US20130032785A1-20130207-C00218
    Figure US20130032785A1-20130207-C00219
    Figure US20130032785A1-20130207-C00220
    Figure US20130032785A1-20130207-C00221
    Figure US20130032785A1-20130207-C00222
    Figure US20130032785A1-20130207-C00223
    Figure US20130032785A1-20130207-C00224
    Figure US20130032785A1-20130207-C00225
    Figure US20130032785A1-20130207-C00226
  17. 17. The compound of claim 1, wherein the compound is selected from the group consisting of:
    Figure US20130032785A1-20130207-C00227
  18. 18. A first device comprising a first organic light emitting device, further comprising:
    an anode;
    a cathode; and
    an organic layer, disposed between the anode and the cathode, comprising a compound having the formula M(L1)x(L2)y(L3)z:
    wherein the ligand L1 is
    Figure US20130032785A1-20130207-C00228
    wherein the ligand L2 is
    Figure US20130032785A1-20130207-C00229
    wherein the ligand L3 is a third ligand;
    wherein each L1, L2 and L3 can be the same or different;
    wherein M is a metal having an atomic number greater than 40;
    wherein x is 1, 2, or 3;
    wherein y is 0, 1, or 2;
    wherein z is 0, 1, or 2;
    wherein x+y+z is the oxidation state of the metal M;
    wherein R is a carbocyclic or heterocyclic ring fused to the pyridine ring;
    R is optionally further substituted with R′;
    wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
    wherein R′, RZ, RA, RB, and RC may represent mono, di, tri, or tetra substitutions;
    wherein each of R1, R2, R3, R4, R′, RZ, RA, RB, and RC are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
    wherein at least one of R1, R2, R3, R4, and R′ is not hydrogen or deuterium; and
    wherein any two adjacent R1, R2, R3, R4, and R′ are optionally linked to form an alkyl ring.
  19. 19. The first device of claim 18, wherein the first device is a consumer product.
  20. 20. The first device of claim 18, wherein the first device is an organic light emitting device.
  21. 21. The first device of claim 18, wherein the first device comprises a lighting panel.
  22. 22. The first device of claim 18, wherein the organic layer is an emissive layer and the compound is an emissive dopant.
  23. 23. The first device of claim 18, wherein the organic layer further comprises a host.
  24. 24. The first device of claim 23, wherein the host is a metal 8-hydroxyquinolate.
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US20130032785A1 (en) * 2011-08-01 2013-02-07 Universal Display Corporation Materials for organic light emitting diode
JP6119375B2 (en) * 2013-03-29 2017-04-26 コニカミノルタ株式会社 The organic electroluminescent element, a display device and a lighting device
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
CN105368446B (en) * 2015-12-19 2018-06-29 江西冠能光电材料有限公司 Furan-containing electroluminescent material and a preparation of an organic electroluminescent device
WO2018108109A1 (en) * 2016-12-13 2018-06-21 广州华睿光电材料有限公司 Transition metal complex and application thereof, mixture and organic electronic device

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030235712A1 (en) * 2001-06-25 2003-12-25 Takao Takiguchi Metal coordination compound and electroluminescence device
US20070034863A1 (en) * 2003-09-29 2007-02-15 Rocco Fortte Metal complexes

Family Cites Families (125)

* Cited by examiner, † Cited by third party
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
GB8909011D0 (en) 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
US5061569A (en) 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
DE69412567D1 (en) 1993-11-01 1998-09-24 Hodogaya Chemical Co Ltd Amine compound and electroluminescent device containing
US5707745A (en) 1994-12-13 1998-01-13 The Trustees Of Princeton University Multicolor organic light emitting devices
US5703436A (en) 1994-12-13 1997-12-30 The Trustees Of Princeton University Transparent contacts for organic devices
US6939625B2 (en) 1996-06-25 2005-09-06 Nôrthwestern University Organic light-emitting diodes and methods for assembly and enhanced charge injection
US6013982A (en) 1996-12-23 2000-01-11 The Trustees Of Princeton University Multicolor display devices
US5834893A (en) 1996-12-23 1998-11-10 The Trustees Of Princeton University High efficiency organic light emitting devices with light directing structures
US5844363A (en) 1997-01-23 1998-12-01 The Trustees Of Princeton Univ. Vacuum deposited, non-polymeric flexible organic light emitting devices
US6091195A (en) 1997-02-03 2000-07-18 The Trustees Of Princeton University Displays having mesa pixel configuration
US6337102B1 (en) 1997-11-17 2002-01-08 The Trustees Of Princeton University Low pressure vapor phase deposition of organic thin films
US6303238B1 (en) 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
US6087196A (en) 1998-01-30 2000-07-11 The Trustees Of Princeton University Fabrication of organic semiconductor devices using ink jet printing
US6528187B1 (en) 1998-09-08 2003-03-04 Fuji Photo Film Co., Ltd. Material for luminescence element and luminescence element using the same
US6830828B2 (en) 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6097147A (en) 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
US6294398B1 (en) 1999-11-23 2001-09-25 The Trustees Of Princeton University Method for patterning devices
US6458475B1 (en) 1999-11-24 2002-10-01 The Trustee Of Princeton University Organic light emitting diode having a blue phosphorescent molecule as an emitter
KR100377321B1 (en) 1999-12-31 2003-03-26 주식회사 엘지화학 Electronic device comprising organic compound having p-type semiconducting characteristics
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US6579630B2 (en) 2000-12-07 2003-06-17 Canon Kabushiki Kaisha Deuterated semiconducting organic compounds used for opto-electronic devices
JP3812730B2 (en) 2001-02-01 2006-08-23 富士写真フイルム株式会社 Transition metal complexes and the light emitting element
JP4307000B2 (en) 2001-03-08 2009-08-05 キヤノン株式会社 Metal coordination compounds, electroluminescent device and a display device
JP4310077B2 (en) 2001-06-19 2009-08-05 キヤノン株式会社 Metal coordination compounds and organic light emitting devices
KR100925409B1 (en) 2001-06-20 2009-11-06 쇼와 덴코 가부시키가이샤 Light emitting material and organic light-emitting device
US7071615B2 (en) 2001-08-20 2006-07-04 Universal Display Corporation Transparent electrodes
US7250226B2 (en) 2001-08-31 2007-07-31 Nippon Hoso Kyokai Phosphorescent compound, a phosphorescent composition and an organic light-emitting device
US7431968B1 (en) 2001-09-04 2008-10-07 The Trustees Of Princeton University Process and apparatus for organic vapor jet deposition
US6835469B2 (en) 2001-10-17 2004-12-28 The University Of Southern California Phosphorescent compounds and devices comprising the same
US7166368B2 (en) 2001-11-07 2007-01-23 E. I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
US6863997B2 (en) 2001-12-28 2005-03-08 The Trustees Of Princeton University White light emitting OLEDs from combined monomer and aggregate emission
KR100691543B1 (en) 2002-01-18 2007-03-09 주식회사 엘지화학 New material for transporting electron and organic electroluminescent display using the same
US20030230980A1 (en) 2002-06-18 2003-12-18 Forrest Stephen R Very low voltage, high efficiency phosphorescent oled in a p-i-n structure
JP4211433B2 (en) * 2002-08-14 2009-01-21 三菱化学株式会社 Organometallic complexes, luminescent dyes, organic electroluminescence element material and organic electroluminescent devices
US7189989B2 (en) 2002-08-22 2007-03-13 Fuji Photo Film Co., Ltd. Light emitting element
EP2261301A1 (en) 2002-08-27 2010-12-15 Fujifilm Corporation Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays
US6687266B1 (en) 2002-11-08 2004-02-03 Universal Display Corporation Organic light emitting materials and devices
JP4365199B2 (en) 2002-12-27 2009-11-18 富士フイルム株式会社 The organic electroluminescent device
JP4365196B2 (en) 2002-12-27 2009-11-18 富士フイルム株式会社 The organic electroluminescent device
EP3109238A1 (en) 2003-03-24 2016-12-28 University of Southern California Phenyl-pyrazole complexes of iridium
US7090928B2 (en) 2003-04-01 2006-08-15 The University Of Southern California Binuclear compounds
JP5318347B2 (en) 2003-04-15 2013-10-16 メルク パテント ゲーエムベーハー Capable of emitting light, a mixture of matrix material and an organic semiconductor, use thereof, and an electronic component comprising the mixture
US7029765B2 (en) 2003-04-22 2006-04-18 Universal Display Corporation Organic light emitting devices having reduced pixel shrinkage
KR101032355B1 (en) 2003-05-29 2011-05-03 신닛테츠가가쿠 가부시키가이샤 Organic electroluminescent element
JP2005011610A (en) 2003-06-18 2005-01-13 Nippon Steel Chem Co Ltd Organic electroluminescent element
US20050025993A1 (en) 2003-07-25 2005-02-03 Thompson Mark E. Materials and structures for enhancing the performance of organic light emitting devices
DE10338550A1 (en) 2003-08-19 2005-03-31 Basf Ag Transition metal-carbene complexes as emitters for organic light emitting diodes (OLEDs)
US20060269780A1 (en) 2003-09-25 2006-11-30 Takayuki Fukumatsu Organic electroluminescent device
JP4822687B2 (en) 2003-11-21 2011-11-24 富士フイルム株式会社 The organic electroluminescent device
US7279232B2 (en) * 2004-01-26 2007-10-09 Universal Display Corporation Electroluminescent stability
US7332232B2 (en) 2004-02-03 2008-02-19 Universal Display Corporation OLEDs utilizing multidentate ligand systems
KR20080064201A (en) 2004-03-11 2008-07-08 미쓰비시 가가꾸 가부시키가이샤 Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same, and method for manufacturing organic electroluminescent device and method for producing charge-transporting film
JP4869565B2 (en) 2004-04-23 2012-02-08 富士フイルム株式会社 The organic electroluminescent device
US7491823B2 (en) 2004-05-18 2009-02-17 The University Of Southern California Luminescent compounds with carbene ligands
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
US7534505B2 (en) 2004-05-18 2009-05-19 The University Of Southern California Organometallic compounds for use in electroluminescent devices
US7393599B2 (en) 2004-05-18 2008-07-01 The University Of Southern California Luminescent compounds with carbene ligands
US7154114B2 (en) 2004-05-18 2006-12-26 Universal Display Corporation Cyclometallated iridium carbene complexes for use as hosts
WO2005123873A1 (en) 2004-06-17 2005-12-29 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
US20060008670A1 (en) 2004-07-06 2006-01-12 Chun Lin Organic light emitting materials and devices
KR101214539B1 (en) * 2004-07-07 2012-12-24 유니버셜 디스플레이 코포레이션 Stable and efficient electroluminescent materials
US7504657B2 (en) 2004-07-23 2009-03-17 Konica Minolta Holdings, Inc. Organic electroluminescent element, display and illuminator
DE102004057072A1 (en) 2004-11-25 2006-06-01 Basf Ag Use of transition metal-carbene complexes in organic light-emitting diodes (OLEDs)
WO2006072002A3 (en) 2004-12-30 2007-03-01 Du Pont Organometallic complexes
WO2006082742A1 (en) 2005-02-04 2006-08-10 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
KR100803125B1 (en) 2005-03-08 2008-02-14 엘지전자 주식회사 Red phosphorescent compounds and organic electroluminescence devices using the same
WO2006098120A1 (en) 2005-03-16 2006-09-21 Konica Minolta Holdings, Inc. Organic electroluminescent device material and organic electroluminescent device
DE102005014284A1 (en) 2005-03-24 2006-09-28 Basf Ag The use of compounds comprising aromatic or heteroaromatic groups containing certain carbonyl-containing groups linked rings, as matrix materials in organic light emitting diodes
JPWO2006103874A1 (en) 2005-03-29 2008-09-04 コニカミノルタホールディングス株式会社 The organic electroluminescence device material, an organic electroluminescence device, a display device and a lighting device
GB2439030B (en) 2005-04-18 2011-03-02 Konica Minolta Holdings Inc Organic electroluminescent device, display and illuminating device
US7807275B2 (en) 2005-04-21 2010-10-05 Universal Display Corporation Non-blocked phosphorescent OLEDs
US9051344B2 (en) 2005-05-06 2015-06-09 Universal Display Corporation Stability OLED materials and devices
JP4533796B2 (en) 2005-05-06 2010-09-01 富士フイルム株式会社 The organic electroluminescent device
CN101203583A (en) 2005-05-31 2008-06-18 通用显示公司 Triphenylene hosts in phosphorescent light emitting diodes
WO2006132173A1 (en) 2005-06-07 2006-12-14 Nippon Steel Chemical Co., Ltd. Organic metal complex and organic electroluminescent device using same
WO2007002683A3 (en) 2005-06-27 2007-09-20 Du Pont Electrically conductive polymer compositions
WO2007004380A1 (en) 2005-07-01 2007-01-11 Konica Minolta Holdings, Inc. Organic electroluminescent element material, organic electroluminescent element, display device, and lighting equipment
WO2007028417A1 (en) 2005-09-07 2007-03-15 Technische Universität Braunschweig Triplett emitter having condensed five-membered rings
JP4887731B2 (en) 2005-10-26 2012-02-29 コニカミノルタホールディングス株式会社 The organic electroluminescent element, a display device and a lighting device
US7993760B2 (en) 2005-12-01 2011-08-09 Nippon Steel Chemical Co., Ltd. Compound for use in organic electroluminescent device and organic electroluminescent device
WO2007095118A3 (en) 2006-02-10 2007-12-06 Universal Display Corp METAL COMPLEXES OF CYCLOMETALLATED IMIDAZO[1,2-f]PHENANTHRIDINE AND DIIMIDAZO[1,2-A:1',2'-C]QUINAZOLINE LIGANDS AND ISOELECTRONIC AND BENZANNULATED ANALOGS THEREOF
US8142909B2 (en) 2006-02-10 2012-03-27 Universal Display Corporation Blue phosphorescent imidazophenanthridine materials
JP4823730B2 (en) 2006-03-20 2011-11-24 新日鐵化学株式会社 Emitting layer compound and an organic light emitting element
EP2011790B1 (en) 2006-04-26 2016-06-29 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescence element using the same
WO2007132678A1 (en) 2006-05-11 2007-11-22 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
CN101461074B (en) 2006-06-02 2011-06-15 出光兴产株式会社 Material for organic electroluminescence element, and organic electroluminescence element using the material
WO2008023549A1 (en) 2006-08-23 2008-02-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and organic electroluminescent devices made by using the same
JP5589251B2 (en) 2006-09-21 2014-09-17 コニカミノルタ株式会社 The organic electroluminescent device material
CN101511834B (en) 2006-11-09 2013-03-27 新日铁化学株式会社 Compound for organic electroluminescent device and organic electroluminescent device
KR101370183B1 (en) 2006-11-24 2014-03-05 이데미쓰 고산 가부시키가이샤 Aromatic amine derivative and organic electroluminescent element using the same
US8119255B2 (en) 2006-12-08 2012-02-21 Universal Display Corporation Cross-linkable iridium complexes and organic light-emitting devices using the same
WO2009073245A1 (en) 2007-12-06 2009-06-11 Universal Display Corporation Light-emitting organometallic complexes
US9362510B2 (en) 2007-02-23 2016-06-07 Basf Se Electroluminescent metal complexes with benzotriazoles
KR101634392B1 (en) * 2007-03-08 2016-06-28 유니버셜 디스플레이 코포레이션 Phosphorescent materials
KR101502187B1 (en) 2007-04-26 2015-03-16 바스프 에스이 Phenothiazine or phenothiazine -s- oxide -s, and their use in the s- silane oled containing an dioxide
WO2009000673A3 (en) 2007-06-22 2009-02-19 Ciba Holding Inc Light emitting cu(i) complexes
CN101878552B (en) 2007-07-05 2015-07-15 巴斯夫欧洲公司 Organic light-emitting diodes containing carbene transition metal complex emitters and at least one compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophene s-oxides a
KR20100031723A (en) 2007-07-07 2010-03-24 이데미쓰 고산 가부시키가이샤 Chrysene derivative and organic electroluminescent device using the same
US8025815B2 (en) 2007-07-07 2011-09-27 Idemitsu Kosan Co., Ltd. Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same
WO2009008205A1 (en) 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and material for organic electroluminescent device
US20090045731A1 (en) 2007-07-07 2009-02-19 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
US8779655B2 (en) 2007-07-07 2014-07-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
US8080658B2 (en) 2007-07-10 2011-12-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent element and organic electroluminescent element employing the same
EP2166584B1 (en) 2007-07-10 2016-06-08 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element prepared by using the material
JP2010534739A (en) 2007-07-27 2010-11-11 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company Aqueous dispersion of a conductive polymer containing an inorganic nanoparticles
KR101565724B1 (en) 2007-08-08 2015-11-03 유니버셜 디스플레이 코포레이션 Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group
US20090039776A1 (en) 2007-08-09 2009-02-12 Canon Kabushiki Kaisha Organometallic complex and organic light-emitting element using same
US20090101870A1 (en) 2007-10-22 2009-04-23 E. I. Du Pont De Nemours And Company Electron transport bi-layers and devices made with such bi-layers
US7914908B2 (en) 2007-11-02 2011-03-29 Global Oled Technology Llc Organic electroluminescent device having an azatriphenylene derivative
DE102007053771A1 (en) 2007-11-12 2009-05-14 Merck Patent Gmbh organic electroluminescent
KR101353635B1 (en) 2007-11-15 2014-01-20 이데미쓰 고산 가부시키가이샤 Benzochrysene derivative and organic electroluminescent device using the same
CN101874316B (en) 2007-11-22 2012-09-05 出光兴产株式会社 Organic EL element and solution containing organic EL material
WO2009066779A1 (en) 2007-11-22 2009-05-28 Idemitsu Kosan Co., Ltd. Organic el element
JP5258271B2 (en) * 2007-11-28 2013-08-07 キヤノン株式会社 Organometallic complexes and the light-emitting element and a display apparatus using the same
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8471248B2 (en) 2008-02-12 2013-06-25 Basf Se Electroluminiscent metal complexes with dibenzo[f,h] quinoxalines
JP4564584B1 (en) * 2009-08-31 2010-10-20 富士フイルム株式会社 The organic electroluminescent device
GB2484253B (en) * 2010-05-14 2013-09-11 Cambridge Display Tech Organic light-emitting composition and device
DE102010046512A1 (en) * 2010-09-24 2012-03-29 Merck Patent Gmbh Phosphorus-containing metal complexes
US9130177B2 (en) * 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US20130032785A1 (en) * 2011-08-01 2013-02-07 Universal Display Corporation Materials for organic light emitting diode
CN102690293A (en) * 2012-06-03 2012-09-26 南京师范大学 Electro-phosphorescent material and preparation method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030235712A1 (en) * 2001-06-25 2003-12-25 Takao Takiguchi Metal coordination compound and electroluminescence device
US20070034863A1 (en) * 2003-09-29 2007-02-15 Rocco Fortte Metal complexes

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