US20150028290A1 - Heteroleptic osmium complex and method of making the same - Google Patents

Heteroleptic osmium complex and method of making the same Download PDF

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US20150028290A1
US20150028290A1 US13/950,591 US201313950591A US2015028290A1 US 20150028290 A1 US20150028290 A1 US 20150028290A1 US 201313950591 A US201313950591 A US 201313950591A US 2015028290 A1 US2015028290 A1 US 2015028290A1
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group
compound
independently selected
formula
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Chuanjun Xia
Jui-Yi Tsai
Beatriz Eguillor Armendáriz
Miguel A. Esteruelas Rodrigo
Roberto Gómez Alabau
Montserrat Oliván Esco
Enrique Oñate Rodriguez
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Universal Display Corp
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Assigned to UNIVERSAL DISPLAY CORPORATION reassignment UNIVERSAL DISPLAY CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Eguillor Armendariz, Beatriz, Esteruelas Rodrigo, Miguel A., Gomez Alabau, Roberto, OLIVAN ESCO, MONTSERRAT, ONATE RODRIGUEZ, ENRIQUE, TSAI, JUI-YI, XIA, CHUANJUN
Priority to KR1020140078833A priority patent/KR20150013009A/ko
Priority to JP2014150441A priority patent/JP2015024991A/ja
Priority to EP14178251.6A priority patent/EP2830109A1/en
Publication of US20150028290A1 publication Critical patent/US20150028290A1/en
Priority to US15/594,046 priority patent/US20170250354A1/en
Priority to US16/784,609 priority patent/US10930866B2/en
Priority to KR1020200145293A priority patent/KR102312243B1/ko
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Definitions

  • 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, 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.
  • the present invention relates to compounds for use as emitters and devices, such as organic light emitting diodes, including the same. More particularly, the compounds disclosed herein are novel heteroleptic bistridentate osmium carbene complexes and a novel synthetic method to make both homoleptic and heteroleptic bistridentate osmium carbene complexes.
  • 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 organic light emitting devices
  • 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.
  • 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.
  • these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
  • a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the following structure:
  • 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.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • 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.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • 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.
  • 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.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • 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.
  • 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.
  • L 1 -Os-L 2 wherein L 1 and L 2 are independently a biscarbene tridentate ligand, wherein L 1 and L 2 can be same or different is disclosed.
  • the method comprises: (a) reacting a precursor of ligand L 1 with an osmium precursor to form an intermediate product, wherein the osmium precursor having the formula OsH x (PR 3 ) y , wherein x is an integer from 2 to 6 and y is an integer from 2 to 5, and R is selected from the group consisting of aryl, alkyl and cycloalkyl; and (b) reacting a precursor of ligand L 2 with said intermediate product.
  • L 1 and L 2 are monoanionic ligands. In some embodiments, L 1 and L 2 are independently selected from ligands having Formula II:
  • Y 1 , Y 2 and Y 3 comprise C or N; wherein R 3 and R 4 may represent mono-, or di-substitutions, or no substitution; wherein R 5 may represent mono-, di-, or tri-substitutions, or no substitution; wherein R 1 , R 2 , R 3 , R 4 and R 5 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 any two adjacent substituents of R 1 , R 2 , R 3 , R
  • a first device comprising a first organic light emitting device.
  • the first organic light emitting device comprises an anode; a cathode; and an organic layer, disposed between the anode and the cathode.
  • the organic layer can comprise a compound having the structure according Formula I
  • novel compounds, heteroleptic bistridentate osmium carbene complexes, and a novel synthetic method to make both homoleptic and heteroleptic bistridentate osmium carbene complexes disclosed herein are useful as emitters in organic light emitting devices.
  • the inventors have discovered that the incorporation of these ligands can narrow the emission spectrum and improve device efficiency.
  • 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 molecular diagram of complex monohydride with X-ray diffraction analysis characterization.
  • FIG. 4 shows molecular diagram of Complex A with X-ray diffraction analysis characterization.
  • an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • the anode injects holes and the cathode injects electrons into the organic layer(s).
  • the injected holes and electrons each migrate toward the oppositely charged electrode.
  • an “exciton,” which is a localized electron-hole pair having an excited energy state is formed.
  • Light is emitted when the exciton relaxes via a photoemissive mechanism.
  • the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • the initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • FIG. 1 shows an organic light emitting device 100 .
  • 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 , a cathode 160 , and a barrier layer 170 .
  • 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.
  • each of these layers are available.
  • 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 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.
  • 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.
  • 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 .
  • FIGS. 1 and 2 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.
  • 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.
  • 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 .
  • 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.
  • PLEDs polymeric materials
  • 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 .
  • 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.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • 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. Pat. No. 7,431,968, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • 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.
  • 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 present invention may further optionally comprise a barrier layer.
  • a barrier layer One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc.
  • the barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge.
  • the barrier layer may comprise a single layer, or multiple layers.
  • the barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer.
  • the barrier layer may incorporate an inorganic or an organic compound or both.
  • the preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties.
  • the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time.
  • the weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95.
  • the polymeric material and the non-polymeric material may be created from the same precursor material.
  • the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
  • 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, medical 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, 3-D displays, vehicles, a large area wall, theater or stadium screen, or a sign.
  • PDAs personal digital assistants
  • 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.), but could be used outside this temperature range, for example, from ⁇ 40 degree C. to +80 degree C.
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • halo, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, 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.
  • substituted indicates that a substituent other than H is bonded to the relevant carbon.
  • R 2 is monosubstituted, then one R 2 must be other than H.
  • R 3 is disubstituted, then two of R 3 must be other than H.
  • R 2 is unsubstituted R 2 is hydrogen for all available positions.
  • novel heteroleptic bistridentate Os(II) complexes and a novel method for synthesizing both homoleptic and heteroleptic bistridentate Os(II) complexes is provided.
  • Heteroleptic osmium complexes provide great freedom of tuning emission color, electrochemical energy levels, and improving evaporation properties.
  • Osmium (II) complexes have been investigated for OLED applications.
  • the octahedral ligand arrangement of the Os(II) complexes resembles that of Ir(III) complexes.
  • Os(II) complexes generally exhibit low oxidation potential, i.e. shallow HOMO energy level than Ir(III) complexes.
  • bistridentate Os(II) carbene complexes offer performance advantages for OLED applications. Without being bound to a theory, the inventors believe that the rigid nature of the tridentate ligands are providing narrow emission line widths and short excited state lifetimes, which can result in better color purity and longer device lifetime, making them suitable for display applications.
  • the inventors have developed a new stepwise complexation method. This method is suitable for making both homoleptic and heteroleptic bistridentate Os(II) complexes.
  • This method is suitable for making both homoleptic and heteroleptic bistridentate Os(II) complexes.
  • an osmium precursor was first reacted with a bistridentate ligand to generate an intermediate that has one tridentate ligand coordinated to the metal.
  • the intermediate was then treated with another tridentate ligand to generate the final complex.
  • homoleptic or heteroleptic complexes can be synthesized. In addition, the yield was improved.
  • One example of the inventive synthetic method is shown below:
  • Coupling constants J and N are given in hertz. Attenuated total reflection infrared spectra (ATR-IR) of solid samples were run on a Perkin-Elmer Spectrum 100 FT-IR spectrometer. C, H, and N analyses were carried out in a Perkin-Elmer 2400 CHNS/O analyzer. High-resolution electrospray mass spectra were acquired using a MicroTOF-Q hybrid quadrupole time-of-flight spectrometer (Bruker Daltonics, Bremen, Germany). OsH 6 (P i Pr 3 ) 2 was prepared by the method published in Aracama, M.; Esteruelas, M. A.; Lahoz, F. J.; López, J. A.; Meyer, U.; Oro, L. A.; Werner, H. Inorg. Chem. 1991, 30, 288.
  • This monohydride compound can be prepared by using two different methods.
  • THF tetrahydrofuran
  • FIG. 3 shows the molecular structure of complex monohydride with the X-ray diffraction analysis characterization.
  • FIG. 4 shows molecular diagram of Complex A with X-ray diffraction analysis characterization.
  • the structure has two chemically equivalent but crystallographically independent molecules in the asymmetric unit.
  • L 1 -Os-L 2 wherein L 1 and L 2 are independently a biscarbene tridentate ligand, wherein L 1 and L 2 can be same or different is disclosed.
  • the method comprises: (a) reacting a precursor of ligand L 1 with an osmium precursor to form an intermediate product, wherein the osmium precursor having the formula OsH x (PR 3 ) y , wherein x is an integer from 2 to 6 and y is an integer from 2 to 5, and R is selected from the group consisting of aryl, alkyl and cycloalkyl; and (b) reacting a precursor of ligand L 2 with said intermediate product.
  • L 1 and L 2 are monoanionic ligands. In some embodiments, L 1 and L 2 are independently selected from ligands having Formula II:
  • Y 1 , Y 2 and Y 3 comprise C or N; wherein R 3 and R 4 may represent mono-, or di-substitutions, or no substitution; wherein R 5 may represent mono-, di-, or tri-substitutions, or no substitution; wherein R 1 , R 2 , R 3 , R 4 and R 5 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 any two adjacent substituents of R 1 , R 2 , R 3 , R
  • Y 1 , Y 2 and Y 3 comprise C. In one embodiment, Y 1 and Y 3 comprise C, and Y 2 is N. In one embodiment, Y 1 and Y 3 are N, and Y 2 comprise C. In one embodiment, R 1 and R 2 are independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and partially or fully deuterated variants thereof.
  • R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.
  • the osmium precursor having the formula OsH 6 (PR 3 ) 2 is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, cyclohexyl, phenyl, 2,6-dimethylphenyl, and 2-methylphenyl.
  • R is 1-methylethyl.
  • the ligands having Formula II are selected from the group consisting of:
  • a compound having a structure according to Formula I, L 1 -Os-L 2 is provided, wherein L 1 and L 2 are different; wherein L 1 and L 2 are independently selected from ligands having Formula II,
  • Y 1 , Y 2 and Y 3 comprise C or N; wherein R 3 and R 4 may represent mono-, or di-substitutions, or no substitution; wherein R 5 may represent mono-, di-, or tri-substitutions, or no substitution; wherein R 1 and R 2 are independently selected from the group consisting of alkyl and cycloalkyl; wherein R 3 , Wand R 5 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; wherein any two adjacent substituents of R 1 , R 2 , R 3 , R 4 and R 5 are optionally joined to condense into a fused ring; and wherein the dash lines show the connection points to osmium.
  • Y 1 , Y 2 and Y 3 comprise C. In one embodiment of the compound, Y 1 and Y 3 comprise C, and Y 2 is N. In some embodiments, Y 1 and Y 3 are N, and Y 2 comprise C. In one embodiment, R 1 and R 2 are independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and partially or fully deuterated variants thereof.
  • R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.
  • L 1 and L 2 are independently selected from ligands having Formula III:
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 comprise C or N.
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 comprise C.
  • the ligands having Formula II are selected from the group consisting of: L 101 to L 159 defined herein.
  • the compound having a structure according to Formula I, L 1 -Os-L 2 is selected from the group consisting of Compounds 1 to 1159 defined in Table 1 below:
  • L 101 L 102 1.
  • L 101 L 103 3.
  • L 101 L 104 4.
  • L 101 L 105 5.
  • L 101 L 106 6.
  • L 101 L 107 7.
  • L 101 L 108 8.
  • L 101 L 109 9.
  • L 101 L 110 10.
  • L 101 L 111 11.
  • L 101 L 112 12.
  • L 101 L 113 13.
  • L 101 L 114 14.
  • L 101 L 115 15.
  • L 101 L 116 16 L 101 L 117 17.
  • L 101 L 118 18.
  • L 101 L 119 19.
  • L 101 L 120 20.
  • L 101 L 121 21.
  • L 101 L 125 25.
  • L 101 L 126 26.
  • L 101 L 127 27.
  • L 101 L 129 29 19.
  • L 101 L 130 30.
  • L 101 L 140 40.
  • L 101 L 150 50.
  • L 103 L 110 123.
  • L 103 L 111 124.
  • L 103 L 112 125.
  • L 103 L 113 126.
  • L 103 L 114 127.
  • L 103 L 116 129.
  • L 103 L 118 131.
  • L 103 L 119 132.
  • L 103 L 120 133.
  • L 103 L 125 138.
  • L 103 L 128 141.
  • L 103 L 130 143 143.
  • L 105 L 110 232.
  • L 108 L 110 388. L 108 L 111 389. L 108 L 112 390. L 108 L 113 391. L 108 L 114 392. L 108 L 115 393. L 108 L 116 394. L 108 L 117 395. L 108 L 118 396. L 108 L 119 397. L 108 L 120 398. L 108 L 121 399. L 108 L 122 400. L 108 L 123 401. L 108 L 124 402. L 108 L 125 403. L 108 L 126 404. L 108 L 127 405. L 108 L 128 406. L 108 L 129 407. L 108 L 130 408. L 108 L 131 409.
  • L 122 L 140 1027.
  • L 122 L 150 1037.
  • L 122 L 152 1039.
  • L 125 L 140 1132. L 125 L 141 1133. L 125 L 142 1134. L 125 L 143 1135. L 125 L 144 1136. L 125 L 145 1137. L 125 L 146 1138. L 125 L 147 1139. L 125 L 148 1140. L 125 L 149 1141. L 125 L 150 1142. L 125 L 151 1143. L 125 L 152 1144. L 125 L 153 1145. L 125 L 154 1146. L 125 L 155 1147. L 125 L 156 1148. L 125 L 157 1149. L 125 L 158 1150. L 125 L 159
  • a first device comprising a first organic light emitting device.
  • the first organic light emitting device comprises an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound having the structure according Formula I, L 1 -Os-L 2 ; wherein L 1 and L 2 are different; wherein L 1 and L 2 are independently selected from ligands having Formula II:
  • Y 1 , Y 2 and Y 3 comprise C or N; wherein R 3 and R 4 may represent mono-, or di-substitutions, or no substitution; wherein R 5 may represent mono-, di-, or tri-substitutions, or no substitution; wherein R 1 and R 2 are independently selected from the group consisting of alkyl and cycloalkyl; wherein R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; wherein any two adjacent substituents of R 1 , R 2 , R 3 , R 4 and R 5 are optionally joined to condense into a fused ring; and wherein the dash lines show the connection points to osmium.
  • Y 1 , Y 2 and Y 3 comprise C. In one embodiment, Y 1 , Y 2 and Y 3 are N. In one embodiment, R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.
  • L 1 and L 2 are independently selected from ligands having Formula III:
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 comprise C or N.
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 comprise C.
  • the ligands having Formula II are selected from the group consisting of L 101 to L 159 defined herein.
  • the first emitting compound is selected from the group consisting of Compounds 1 to 1159 defined in Table 1.
  • the first device can be one or more of a consumer product, an organic light-emitting device, and/or a lighting panel.
  • the organic layer in the organic light emitting device can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.
  • the organic layer can also include a host.
  • the host can include a metal complex.
  • the host can be a metal 8-hydroxyquinolate.
  • the host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan.
  • Any substituent in the host can be an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2+1 , OAr 1 , N(C n H 2+1 ) 2 , N(Ar 1 )(Ar 2 ), CH ⁇ CH—C n H 2n+1 , C ⁇ C—C n H 2+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 , or no substitution.
  • n can range from 1 to 10; and Ar 1 and Ar 2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
  • the host can be a compound selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
  • the “aza” designation in the fragments described above, i.e., aza-dibenzofuran, aza-dibenzonethiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline.
  • azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline.
  • the host can include a metal complex.
  • the host can be a specific compound selected from the group consisting of:
  • a formulation comprising the compound having a structure according to Formula I, L 1 -Os-L 2 , as defined herein, is disclosed.
  • the formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, and an electron transport layer material, disclosed herein.
  • 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.
  • 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.
  • 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.
  • 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 silane derivatives; a metal oxide derivative, such as MoO x ; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.
  • aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
  • Each of Ar 1 to Ar 9 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, pyrim
  • 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.
  • 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, acy
  • Ar 1 to Ar 9 is independently selected from the group consisting of:
  • k is an integer from 1 to 20;
  • X 101 to X 108 is C (including CH) or N;
  • Z 101 is NAr 1 , O, or S;
  • Ar 1 has the same group defined above.
  • metal complexes used in HIL or HTL include, but not limit to the following general formula:
  • Met is a metal, which can have an atomic weight greater than 40;
  • (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 are independently selected from C, N, O, P, and S;
  • L 101 is an ancillary ligand;
  • k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and
  • k′+k′′ is the maximum number of ligands that may be attached to the metal.
  • (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another aspect, (Y 101 -Y 102 ) is a carbene ligand. In another aspect, Met 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.
  • 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.
  • 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. While the Table below categorizes host materials as preferred for devices that emit various colors, any host material may be used with any dopant so long as the triplet criteria is satisfied.
  • metal complexes used as host are preferred to have the following general formula:
  • Met is a metal
  • (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 are independently selected from C, N, O, P, and S
  • L 101 is an another ligand
  • k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal
  • k′+k′′ is the maximum number of ligands that may be attached to the metal.
  • the metal complexes are:
  • (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
  • Met is selected from Ir and Pt.
  • (Y 103 -Y 104 ) is a carbene ligand.
  • 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
  • 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.
  • 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, acy
  • host compound contains at least one of the following groups in the molecule:
  • R 101 to R 107 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.
  • X 101 to X 108 is selected from C (including CH) or N.
  • Z 101 and Z 102 is selected from NR 101 , O, or S.
  • a hole blocking layer 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.
  • a blocking layer may be used to confine emission to a desired region of an OLED.
  • compound used in HBL contains the same molecule or the same functional groups used as host described above.
  • compound used in HBL contains at least one of the following groups in the molecule:
  • Electron transport layer 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.
  • compound used in ETL contains at least one of the following groups in the molecule:
  • R 101 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, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
  • Ar 1 to Ar 3 has the similar definition as Ar's mentioned above.
  • k is an integer from 1 to 20.
  • X 101 to X 108 is selected from C (including CH) or N.
  • the metal complexes used in ETL contains, but not limit to the following general formula:
  • (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N,N; L 101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
  • the hydrogen atoms can be partially or fully deuterated.
  • any specifically listed substituent such as, without limitation, methyl, phenyl, pyridyl, etc. encompasses undeuterated, partially deuterated, and fully deuterated versions thereof.
  • classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also encompass undeuterated, partially deuterated, and fully deuterated versions thereof.
  • hole injection materials 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 2 below. Table 2 lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials.
  • Metal 8-hydroxyquinolates e.g., BAlq
  • Appl. Phys. Lett. 81, 162 (2002) 5-member ring electron deficient heterocycles such as triazole, oxadiazole, imidazole, benzoimidazole Appl. Phys. Lett. 81, 162 (2002) Triphenylene compounds US20050025993 Fluorinated aromatic compounds Appl. Phys. Lett.

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