Organic electroluminescent materials and devices

Abstract

To provide metal complexes useful as a phosphorescent emitter in organic light emitting devices.SOLUTION: For example, metal complexes are represented by formulas in the figure.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The claimed invention was made by, for the benefit of, and / or in connection with one or more of the following parties to a University-Corporate Collaborative Research Agreement: University of Michigan, Princeton University, University of Southern California, and the Regents of Universal Display Corporation, which agreement was in effect on or before the date on which the claimed invention was made, and which claimed invention was made as a result of activities conducted within the scope of such agreement.

[0002] The present invention relates to novel ligands for metal complexes for use as emitters, and devices such as organic light emitting diodes comprising said ligands. [Background technology]

[0003] Optoelectronic devices that utilize organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as flexibility, may make them well suited for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic light-emitting layer emits light can generally be easily tuned with appropriate dopants.

[0004] OLEDs utilize thin organic films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting. Several OLED materials and configurations are described in U.S. Patent Nos. 5,393, 6,433, 6,511, 6,671, 6,781, and 7,933, 7,825, which are incorporated herein by reference in their entireties.

[0005] One application of phosphorescent emissive molecules is full color displays. Industry standards for such displays require pixels adapted to emit specific colors, referred to as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Color can be measured using CIE coordinates, which are well known in the art.

[0006] An example of a green emitting molecule has the following structure: [ka] The compound is tris(2-phenyl)iridium, denoted as Ir(ppy)3.

[0007] In this figure and later figures herein, we depict the coordinate bond from nitrogen to the metal (here Ir) as a straight line.

[0008] As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" can actually be quite large. Small molecules can include repeat units in some circumstances. For example, the use of long chain alkyl groups as a substituent does not remove a molecule from the "small molecule" class. Small molecules can be incorporated into polymers, for example, as pendant groups on a polymer backbone or as part of the backbone. Small molecules can 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 the dendrimer can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

[0009] As used herein, "top" means furthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as "disposed over" a second layer, the first layer is disposed further from the substrate. There may be other layers between the first and second layers, 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.

[0010] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium, either in the form of a solution or suspension.

[0011] A ligand may be referred to as "photoactive" if it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" if it is believed that the ligand does not contribute to the photoactive properties of the emissive material, although the ancillary ligand may modify the properties of the photoactive ligand.

[0012] As used herein, and as would be generally understood by one of ordinary skill 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 (IPs) are measured as negative energies relative to the vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (a less negative EA). In 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.

[0013] As used herein, as would be generally understood by one of ordinary skill 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. Since work functions are generally measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. In a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being further away from the vacuum level in a downward direction. Thus, the definition of the HOMO and LUMO energy levels follows a different convention than work functions.

[0014] Further details regarding OLEDs and the above definitions can be found in US Pat. No. 6,399,633, which is incorporated herein by reference in its entirety. Summary of the Invention

[0015] The present invention discloses novel ligands for metal complexes that are useful as phosphorescent emitters in organic light emitting devices. Applicants believe that the incorporation of new side chains on the ligands allows fine tuning of the emission of the metal complexes while maintaining good device efficiency and device lifetime.

[0016] According to an embodiment, a composition is disclosed that includes a novel compound, which can function as a phosphorescent emitter in an organic light-emitting device at room temperature. The compound has at least one aromatic ring and at least one substituent R, each of which is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of which is directly bonded to one of the aromatic rings, and in each of which, the C having F bonded thereto is separated from the aromatic ring by at least one carbon atom.

[0017] According to another embodiment, a first device is also provided, comprising a first organic light-emitting device. The first organic light-emitting device can include an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer can include the compound having at least one aromatic ring and at least one substituent R, wherein the at least one substituent R is selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; the at least one substituent R is directly bonded to one of the aromatic rings, and in each of the at least one substituent R, the C having F bonded thereto is separated from the aromatic ring by at least one carbon atom. The first device can be a consumer product, an organic light-emitting device, and / or a lighting panel. [Brief description of the drawings]

[0018] [Figure 1] FIG. 1 shows an organic light emitting device.

[0019] [Diagram 2] FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0020] In general, 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 migrate to the oppositely charged electrode, respectively. When an electron and hole localize on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. Light is emitted via a photoemissive mechanism when the exciton relaxes. In some cases, the exciton may be localized on an excimer or exciplex. Non-radiative mechanisms such as thermal relaxation may also occur, but are generally considered undesirable.

[0021] Early OLEDs used emissive molecules that emitted light from their singlet state ("fluorescence"), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs on a time frame of less than 10 nanoseconds.

[0022] More recently, OLEDs have been demonstrated that have emissive materials that emit light from triplet states ("phosphorescence"). Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Vol. 395, pp. 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, pp. 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entireties. Phosphorescence is described in further detail in U.S. Pat. No. 7,279,704, columns 5-6, which are incorporated by reference.

[0023] FIG. 1 shows an organic light-emitting device 100. The figures are not necessarily drawn to scale. The 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. The cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. The 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 US Pat. No. 7,279,704, columns 6-10, which are incorporated by reference.

[0024] Further examples are available for each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent 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 F4-TCNQ in 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. Patent 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 in 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. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. 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 can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0025] 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 the cathode disposed above the anode, and device 200 has the cathode 215 disposed below the 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 an example of how some layers may be omitted from the structure of device 100.

[0026] The simple layer structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and it is understood that embodiments of the present invention may be used in conjunction 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. A functional OLED may be achieved by combining the various layers described in various 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. While many of the examples provided herein describe the various layers as including a single material, it is understood that combinations of materials, such as mixtures of hosts and dopants, or more generally mixtures, may be used. Layers may also 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. The organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials, for example, as described with respect to Figures 1 and 2.

[0027] Structures and materials not specifically described may be used, such as OLEDs (PLEDs) composed of polymeric materials such as those disclosed in U.S. Patent No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. As a further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from the simple layered structures illustrated in Figures 1 and 2. For example, the substrate may include angled reflective surfaces to improve outcoupling, such as mesa structures as described in U.S. Patent No. 6,091,195 to Forrest et al. and / or dimple structures as described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

[0028] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include deposition by thermal evaporation, such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety, inkjet, organic vapor phase deposition (OVPD), such as those described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and organic vapor jet printing (OVJP), such as those described in U.S. Pat. No. 7,431,968, 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 a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition via mask, cold welding, such as those described in U.S. Patent Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety, and patterning associated with some of the deposition methods, such as inkjet and OVJD. Other methods may be used. The material to be deposited may be modified to be compatible with the 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 with 20 or more carbons may be used, with 3-20 carbons being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures, as asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

[0029] Devices fabricated according to embodiments of the invention may further include 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, vapors and / or gases, etc. The barrier layer may be deposited on, under or next to the substrate, the electrodes, or on any other portion of the device, including the edges. The barrier layer may include 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 and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferred barrier layers include mixtures of polymeric and non-polymeric materials, as described in U.S. Pat. No. 7,968,146, PCT Patent Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, which are incorporated herein by reference in their entireties. To be considered a "mixture," the polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same reaction conditions and / or simultaneously. The weight ratio of polymeric to non-polymeric materials can be in the range of 95:5 to 5:95. The polymeric and non-polymeric materials can be made from the same precursor materials. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0030] Devices made according to embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into various electrical products or intermediate components. Such electrical products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels) that can be utilized by end-user product manufacturers. Such electronic component modules can optionally include driving electronics and / or power sources. Devices made according to embodiments of the invention can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Such consumer products include any type of product that includes one or more light sources and / or one or more display devices of some kind. Some examples of such consumer products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, cars, large area walls, theater or stadium screens, or signs. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices made according to the invention. Many of the devices are intended for use within a temperature range that is comfortable for humans, such as 18 degrees Celsius to 30 degrees Celsius, and more preferably room temperature (20-25 degrees Celsius), but can also be used outside this temperature range, for example, from -40 degrees Celsius to +80 degrees Celsius.

[0031] 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 use the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.

[0032] As used herein, the terms "halo," "halide," or "halogen" include fluorine, chlorine, bromine, and iodine.

[0033] As used herein, the term "alkyl" refers to both straight and branched chain alkyl groups. Preferred alkyl groups are those containing 1 to 15 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, etc. Additionally, the alkyl groups may be substituted.

[0034] As used herein, the term "cycloalkyl" refers to a cyclic alkyl group. Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, etc. Furthermore, the cycloalkyl groups may be substituted.

[0035] In the present specification, the term "alkenyl" refers to both straight-chain and branched-chain alkenyl groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Furthermore, the alkenyl groups may be substituted.

[0036] As used herein, the term "alkynyl" refers to both straight and branched chain alkyne groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Furthermore, said alkynyl groups may be substituted.

[0037] As used herein, the terms "aralkyl" and "arylalkyl" are used interchangeably and refer to an alkyl group having an aromatic group as a substituent. Additionally, said aralkyl group may be optionally substituted.

[0038] In this specification, the term "heterocyclic group" refers to aromatic and non-aromatic ring groups. Heteroaromatic ring groups also refer to heteroaryl. Preferred hetero non-aromatic ring groups are at least one heteroatom containing 3 or 7 ring atoms, and include cyclic amines such as morpholino, piperidino, pyrrolidino, and cyclic ethers such as tetrahydrofuran, tetrahydropyran, and the like. Furthermore, the heterocyclic group may be substituted.

[0039] As used herein, "aryl" or "aromatic group" refers to monocyclic and polycyclic ring systems. A polycyclic ring can have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), at least one of the rings being aromatic, e.g., the other rings being cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Additionally, the aryl group may be substituted.

[0040] As used herein, "heteroaryl" refers to a monocyclic heteroaromatic group containing 1-3 heteroatoms, such as, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, and pyrimidine. The term heteroaryl also includes polycyclic heteroaromatic systems having two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), at least one of the rings being heteroaryl, and the other rings being, for example, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Additionally, the heteroaryl may be substituted.

[0041] The alkyl, the cycloalkyl, the alkenyl, the alkynyl, the aralkyl, the heterocycle, the aryl, and the heteroaryl may be optionally substituted with one or more substituents selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0042] As used herein, "substituted" indicates that a substituent other than H is attached to the relevant position, such as a carbon. Thus, for example, R 1 is monosubstituted, R 1 must be something other than H. Similarly, R 1 When is disubstituted, R 1 Two of the must be non-H. Similarly, R 1 If is unsubstituted, R 1 is hydrogen at all substitution positions.

[0043] The designation "aza" in the fragments described herein, such as aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the CH groups in each fragment can be replaced by a nitrogen atom, for example, but not by way of limitation, azatriphenylene includes both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can easily imagine other nitrogen analogs of the above-mentioned aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0044] It is understood that when a molecular fragment is described as a substituent or as being attached to another moiety, the name may be described as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the entire molecule (benzene, naphthalene, dibenzofuran). Different designations of the substituents or attached fragments are considered equivalent herein.

[0045] According to an embodiment, a composition is disclosed that includes a novel first compound, which can function as a phosphorescent emitter in an organic light-emitting device at room temperature. The first compound has at least one aromatic ring and at least one substituent R, each of which is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of which is directly bonded to one of the aromatic rings, and in each of which, the C having F bonded thereto is separated from the aromatic ring by at least one carbon atom.

[0046] Each of the at least one substituent R is directly bonded to one of the aromatic rings, meaning that each R can be bonded to a different aromatic ring or some of the R can be bonded to the same aromatic ring. A partially fluorinated group means that not all carbon-hydrogen bonds in the group are replaced by carbon-fluorine bonds, in other words at least one carbon-hydrogen bond remains in the group.

[0047] In one embodiment, the first compound is capable of emitting from a triplet excited state to a ground singlet state at room temperature.

[0048] In one embodiment, the first compound is a metal coordination complex having a metal-carbon bond. The metal may be selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In one preferred embodiment, the metal is Ir. In another preferred embodiment, the metal is Pt.

[0049] In one embodiment of the first compound, the C having F bonded thereto is separated from the aromatic ring by at least two carbon atoms. In another embodiment, the C having F bonded thereto is separated from the aromatic ring by at least three carbon atoms.

[0050] In one embodiment of the first compound, the at least one substituent R each comprises at least one CF group. In a preferred embodiment, the at least one substituent R each comprises only CF groups and does not comprise any CF or CF groups. In another embodiment, the at least one substituent R does not comprise any CF groups.

[0051] In one embodiment, the first compound has no F atoms other than the F atom in the at least one substituent R.

[0052] In one embodiment of the first compound, the aromatic ring comprises the LUMO electron density of the first compound.

[0053] In one embodiment of the first compound, the compound has the formula C n H 2n+1-m F m and C q H 2q-1-m F m In other embodiments, m is not a multiple of 3. In other embodiments, m is a multiple of 3.

[0054] According to an embodiment of the present disclosure, the first compound as defined above is M(L 1 ) x (L 2 ) y(L 3 ) z It is expressed by the formula: L 1 , L 2 , and L 3 may be the same or different. wherein 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; L 1 , L 2 , and L 3 are each independently selected from the group consisting of: [ka] [ka] In the formula, R a , R b , R c , and R d independently represent mono-, di-, tri-, or tetra-substitution, or unsubstituted; R a , R b , R c , and R d 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R a , R b , R c , and R d Two adjacent substituents of may be linked to form a ring or a polydentate ligand; a , R b , R c , and R d At least one of contains at least one R.

[0055] In one embodiment of the first compound defined above, M is Ir and the first compound is Ir(L 1 )2(L 2 ) is represented by the formula Ir(L 1 )2(L 2 In the first compound represented by the formula: 1 is represented by a formula selected from the group consisting of: [ka] L 2 is expressed by the following formula: [ka] In the formula, R a , R b , and R c independently represent mono-, di-, tri-, or tetra-substitution, or unsubstituted; R a , R b , and R c 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R a , R b , and R c Two adjacent substituents of may be linked to form a ring or a polydentate ligand; a , R b , and R c At least one of contains at least one R.

[0056] In another embodiment of the first compound as defined above, M is Ir and the first compound has the formula Ir(L 1 )2(L 2) and L 1 is selected from the group consisting of: [ka] L 2 is expressed by the following formula: [ka] R a and R b is defined above, and R e , R f , R h , and R i is independently selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl; R e , R f , R h , and R i at least one of has at least two carbon atoms; R g 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R a and R b At least one of contains at least one R.

[0057] Ir(L 1 )2(L 2 In another embodiment of the first compound represented by the formula 1 and L 2 are different and each independently selected from the group consisting of: [ka] R a and R bAt least one of contains at least one R.

[0058] Ir(L 1 )2(L 2 In another embodiment of the first compound represented by the formula 1 and L 2 are each independently selected from the group consisting of: [ka] In the formula, R a , R b , and R c At least one of contains at least one R.

[0059] The first compound has the formula M(L 1 ) x (L 2 ) y (L 3 ) z In an embodiment represented by the structure 1 )2 or Pt(L 1 )(L 2 ) is expressed as Pt(L 1 In the compound represented by the formula 1 is another L 1 It can be combined with the formula Pt(L 1 )(L 2 In the compound represented by the formula: L 1 L 2 and can combine to form a tetradentate ligand. a , R b , R c , and R d At least one of comprises an alkyl or cycloalkyl group comprising CD, CD2, or CD3, and D is deuterium.

[0060] According to another aspect of the present disclosure, M(L 1 ) x (L 2 ) y (L 3 ) zIn the first compound represented by the formula: L 1 , L 2 , and L 3 may be the same or different; 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; L 1 , L 2 , and L 3 are each independently selected from the group consisting of: [ka] [ka] [ka] [ka] In the formula, R A1 ~R A41 is expressed by the following formula: [ka]

[0061] In one embodiment, the first compound is Ir(L 1 )2(L 2 ) and L 1 L A1 ~L A450 , and L A451 and L 2 is selected from the group consisting of: [ka]

[0062] In the above structures, the dashed line represents the bond between the current group and the next group to which it is attached. For example, L A1 In the formula (I), the dashed line represents the bond between M and the ligand; A1 In the formula (I), the dashed line represents the bond between R and the aromatic ring.

[0063] In another embodiment, the first compound is selected from the group consisting of compounds 1 to 5,863, each of which is represented by formula Ir(L Ak )2(L Bj ), where x=451j+k-451, k is an integer from 1 to 451, and j is an integer from 1 to 13. A1 ~L A451 and L B1 ~L B13 is defined above.

[0064] Examples of the first compounds disclosed herein are metal complexes based on ligands including 1-phenylisoquinoline, 2-phenylquinoline, 8-(quinolin-2-yl)benzofuro[2,3-b]pyridine, 8-(isoquinolin-1-yl)benzofuro[2,3-b]pyridine, 4-(4-fluorophenyl)quinazoline, or 2-phenylpyridine. The ligands each include an alkylated side chain that is not benzyl and contains at least one fluorine atom. The presence of these side chains provides fine tuning of the color of the metal complex, mainly as a slight red shift. The shorter the spacer between the aromatic unit and the fluorine atom, the greater the red shift in the final complex. Good efficiency was observed from these compounds. More importantly, it was unexpectedly observed that the inventive compounds showed better lifetime than compounds with fluorine in the benzyl moiety. Conventional compounds with trifluoromethyl and perfluoroalkyl substitutions showed very poor device stability.

[0065] According to another aspect, a first device is disclosed, comprising a first organic light emitting device. The first organic light emitting device can include an anode; a cathode; and an organic layer disposed between the anode and the cathode. The organic layer can include the first compound disclosed herein. The first compound incorporated in the first device can be any one or more of the embodiments and specific compounds of the first compound described herein. For example, the first compound can function as a phosphorescent emitter at room temperature, the first compound has at least one aromatic ring and at least one substituent R, each of the at least one substituent R being independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of the at least one substituent R is directly bonded to one of the aromatic rings, and in each of the at least one substituent R, the C having F bonded thereto is separated from the aromatic ring by at least one carbon atom.

[0066] According to an embodiment, the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light emitting device, and a lighting panel.

[0067] In the first device, the organic layer is an emissive layer and the compound is an emissive dopant.

[0068] In one embodiment of the first device, the organic layer further comprises a host; the host comprises a triphenylene containing benzo-fused thiophene or a benzo-fused furan; and any substituents in the host material are independently selected from the group consisting of C n H 2n+1 , O.C. n H 2n+1 , OAr1, N(C n H 2n+1 )2, N(Ar1)(Ar2), CH=CH-C n H 2n+1 , C≡CC n H 2n+1 , Ar1, Ar1-Ar2, and C n H2n -Ar1 is a non-fused substituent selected from the group consisting of, or is unsubstituted; n is 1 to 10; Ar1 ​​and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

[0069] The host in the first device can include at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

[0070] The host may be selected from the group consisting of: [ka]

[0071] 7. The first device of claim 6, wherein the host material comprises a metal complex.

[0072] In yet another embodiment of the present disclosure, n H 2n+1-m F m and C q H 2q-1-m F m A composition is disclosed that includes a compound having at least one non-conjugated substituent R selected from the group consisting of: R is directly bonded to the aromatic ring. n is an integer greater than 1, q is an integer greater than 2, m is an integer greater than 0, and C having F attached thereto is separated from the aromatic ring by at least one carbon atom. The composition can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, a hole transport material, and an electron transport layer material described herein.

[0073] Material Synthesis

[0074] All reactions were carried out under nitrogen protection unless otherwise noted. All solvents for reactions were anhydrous and were used as obtained from commercial sources.

[0075] Synthesis of comparative compound 1

[0076] Synthesis of (2-amino-6-(trifluoromethyl)phenyl)methanol [ka] 2-Amino-6-(trifluoromethyl)benzoic acid (20 g, 97 mmol) was dissolved in tetrahydrofuran (120 mL) in a three-necked RB flask equipped with an addition funnel and a condenser. The solution was cooled in an ice-water bath. LiAlH4 (83 mL, 166 mmol) (2 M solution in THF) was then added dropwise. After all the LiAlH4 solution was added, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction was quenched by adding 10 mL of water, followed by 10 mL of 15% NaOH, followed by 25 mL of water. The salts were filtered and the solvent was evaporated under vacuum. The product was used as is (18 g, 97% yield).

[0077] Synthesis of 2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline [ka] A mixture of (2-amino-6-(trifluoromethyl)phenyl)methanol (18 g, 94 mmol), 1-(3,5-dimethylphenyl)ethanone (19.5 ml, 130 mmol), powdered potassium hydroxide (0.90 g, 16.0 mmol), and RuCl2(PPh3)3 (0.45 g, 0.47 mmol) in toluene (310 ml) was refluxed overnight. Upon cooling to room temperature, the mixture was washed with water and extracted with ethyl acetate (3 times). The crude product was applied to Celite and purified by CC starting with 5% EA in heptane. The resulting product was recrystallized from methanol to give 2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline as yellow crystals (10 g, 35% yield).

[0078] Synthesis of Ir(III) dimer [ka] 2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline (3.00 g, 9.96 mmol) was dissolved in ethoxyethanol (30 mL) and water (10 mL) and degassed with nitrogen for 30 minutes. Iridium chloride (0.92 g, 2.49 mmol) was then added to the solution and the reaction was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solid was filtered, washed with methanol, and dried to give the Ir(III) dimer as a brown powder (1.0 g, 49% yield).

[0079] Synthesis of comparative compound 1 [ka] Ir(III) dimer (1.08 g, 0.65 mmol) and 3,7-diethylnonane-4,6-dione (1.38 g, 6.52 mmol) were diluted in ethoxyethanol (22 mL) and the mixture was degassed by bubbling nitrogen gas for 15 min. K2CO3 (0.90 g, 6.52 mmol) was then added and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane ("DCM") and filtered through a pad of Celite, washing with DCM. The crude product was purified by column chromatography (silica pretreated with triethylamine (TEA)) using a solvent system of 80 / 20 heptane / DCM. The collected pure fractions were triturated from methanol and the solid was recrystallized from dichloromethane / methanol to give comparative compound 1 as a dark red powder (0.85 g, 65% yield).

[0080] Synthesis of compound 453

[0081] Synthesis of 2-(3,5-dimethylphenyl)-5-(3,3,3-trifluoropropyl)quinoline [ka] 5-Bromo-2-(3,5-dimethylphenyl)quinoline (1.15 g, 3.68 mmol), palladium(II) acetate (0.017 g, 0.074 mmol), and CPhos (0.064 g, 0.147 mmol) were charged to a flask and diluted with 100 mL of tetrahydrofuran. The mixture was degassed with nitrogen and (3,3,3-trifluoropropyl)zinc(II) iodide (1.07 g, 3.68 mmol) was added via syringe. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride solution, then extracted twice with 200 mL of ethyl acetate and dried over sodium sulfate. The crude product was applied to Celite and purified by column chromatography using a 20% DCM in heptane solvent system. The product was recrystallized in heptane to give 0.90 g of the desired compound (81% yield).

[0082] Synthesis of Ir(III) dimer [ka] 2-(3,5-Dimethylphenyl)-5-(3,3,3-trifluoropropyl)quinoline (1.80 g, 5.47 mmol) was dissolved in ethoxyethanol (15 mL) and water (5 mL) and degassed with nitrogen for 30 minutes. Iridium chloride (0.54 g, 1.46 mmol) was then added to the solution and the reaction was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solid was filtered, washed with methanol, and dried to give the Ir(III) dimer as a brown powder (0.95 g, 74% yield).

[0083] Synthesis of compound 453 [ka] Ir(III) dimer (0.95 g, 0.537 mmol) and 3,7-diethylnonane-4,6-dione (1.14 g, 5.37 mmol) were diluted in ethoxyethanol (15 mL) and the mixture was degassed by bubbling nitrogen gas for 15 min. K2CO3 (0.74 g, 5.37 mmol) was then added and the reaction was stirred at room temperature overnight. The mixture was diluted with DCM and filtered through a pad of Celite, washing with DCM. The crude product was purified by column chromatography (silica pretreated with TEA) using a solvent system of heptane / DCM (100 / 0 to 97 / 3). The collected pure fractions were triturated from methanol and the solid was recrystallized from dichloromethane / methanol to give compound 453 as a dark red powder (0.83 g, 73% yield).

[0084] Synthesis of compound 781

[0085] Synthesis of 2,6-dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine [ka] 8-(5-chloroquinolin-2-yl)-2,6-dimethylbenzofuro[2,3-b]pyridine (3.40 g, 9.48 mmol), 2'-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine (0.33 g, 0.76 mmol), and diacetoxypalladium (0.09 g, 0.38 mmol) were added to a flask and diluted with THF (150 mL). The mixture was degassed by bubbling nitrogen, and then (3,3,3-trifluoropropyl)zinc(II) iodide (40 mL, 11.8 mmol) was added via syringe. The mixture was stirred overnight at room temperature. Upon completion of the reaction, it was quenched with aqueous ammonium chloride solution and then extracted with two 200 mL portions of ethyl acetate. These extracts were dried over magnesium sulfate, then filtered and concentrated under vacuum. The crude residue was purified by column chromatography using 20 / 80 ethyl acetate / heptane. The combined fractions were triturated with heptane to give 2,6-dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine as an off-white powder (2.55 g, 64% yield).

[0086] Synthesis of Ir(III) dimer [ka] 2,6-Dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine (2.55 g, 6.07 mmol) was dissolved in 2-ethoxyethanol (19 mL) and water (6 mL) and degassed by bubbling with nitrogen for 30 minutes. Iridium chloride (0.56 g, 1.52 mmol) was then added to the solution (some of the ligand precipitated) and the reaction was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solid was filtered and washed with methanol to give the Ir(III) dimer as a red powder (1.10 g, 68% yield).

[0087] Synthesis of compound 781 [ka] Ir(III) dimer (1.00 g, 0.47 mmol) and 3,7-diethylnonane-4,6-dione (0.91 g, 4.26 mmol) were diluted in 2-ethoxyethanol (14 mL) and the mixture was degassed by bubbling nitrogen gas for 15 min. K2CO3 (0.59 g, 4.26 mmol) was then added and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and filtered through a pad of celite, washing with DCM. The crude product was purified by column chromatography (TEA-pretreated silica) using a solvent system of 80 / 20 heptane / dichloromethane. The combined fractions were triturated from methanol and the solid was recrystallized once from dichloromethane / methanol. The title product was obtained as a red powder (0.8 g, 76% yield).

[0088] Synthesis of compound 699

[0089] Synthesis of 2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ka] 5-Bromo-2-fluoro-1,3-dimethylbenzene (20 g, 100 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (51 g, 200 mmol), Pd2(dba)3 (1.83 g, 2.00 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos) (3.28 g, 8.00 mmol), potassium acetate (24.5 g, 250 mmol), and dioxane (600 mL) were combined in a three-neck round-bottom flask. A condenser was attached and the system was evacuated and purged with nitrogen three times. The reaction was heated to reflux overnight. Upon completion, the reaction was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated to a dark red oil, dissolved in 400 mL of heptane, and loaded onto a plug of silica gel in a sintered filter funnel. The silica gel was washed with 2 L of heptane, followed by the addition of 1 L of 98 / 2 heptane / ethyl acetate to recrystallize much of the product and remove the bis-pinocholate. These portions were combined and concentrated to give 30 g of a yellow oil that was purified on silica gel using a heptane to 95 / 5 heptane / ethyl acetate solvent system. Fractions containing the desired product were combined and concentrated to give 17.5 g of a pale yellow solid in 70% yield.

[0090] Synthesis of 7-chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline [ka] 4,7-Dichloroquinazoline (4.0 g, 20.1 mmol), 2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.53 g, 22.1 mmol), sodium carbonate (5.33 g, 50.2 mmol), palladium tetrakis (0.70 g, 0.60 mmol), dimethoxyethane (“DME”) (160 mL), and water (40 mL) were combined in a three-neck round-bottom flask. A condenser was attached, then the system was evacuated and purged with nitrogen three times. The reaction was refluxed vigorously overnight. The reaction was diluted with ethyl acetate, water, and brine. The aqueous solution was partitioned and the organics were washed once with brine, dried over sodium sulfate, and then concentrated to a yellow solid. The yellow solid was purified on silica gel using DCM-85 / 15 DCM / ethyl acetate solvent system to give 4.1 g of a pale yellow solid in 71% yield.

[0091] Synthesis of 4-(4-fluoro-3,5-dimethylphenyl)-7-(3,3,3-trifluoropropyl)quinazoline [ka] 7-Chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline (2.75 g, 9.59 mmol), 2'-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine (CPhos) (0.34 g, 0.77 mmol), and diacetoxypalladium (0.090 g, 0.38 mmol) and 100 mL of anhydrous THF were placed in an oven-dried three-neck round-bottom flask. The system was evacuated and purged with nitrogen three times. (3,3,3-trifluoropropyl)zinc(II) iodide (86 ml, 19.2 mmol) was added via syringe. Once the reaction was complete, it was quenched with ammonium chloride solution and transferred to a separatory funnel containing ethyl acetate. The aqueous solution was separated and the organics were washed once with brine, dried over sodium sulfate, filtered and concentrated. The crude solid was purified on silica gel using DCM to 90 / 10 DCM / ethyl acetate solvent system to give 3.3 g of a red-brown solid. 3.3 g of the solid was purified using a C18 cartridge using a solvent system of 80 / 20 to 85 / 15 acetonitrile / water. The combined fractions were concentrated and dried in a vacuum oven overnight to give 2.36 g of a white solid in 71% yield.

[0092] Synthesis of Ir(III) dimer [ka] 4-(4-Fluoro-3,5-dimethylphenyl)-7-(3,3,3-trifluoropropyl)quinazoline (2.56 g, 7.34 mmol) was placed in a RBF and dissolved in ethoxyethanol (23 mL) and water (8 mL). The mixture was degassed with nitrogen gas for 15 minutes, then iridium chloride (0.68 g, 1.84 mmol) was charged and the reaction was heated at 105° C. for 24 hours. The reaction was cooled to room temperature, diluted with 10 mL of MeOH, and washed with MeOH. The Ir(III) dimer was obtained as an orange powder (1.50 g, 89% yield).

[0093] Synthesis of compound 681 [ka] The dimer (1.50 g, 0.81 mmol), 3,7-diethylnonane-4,6-dione (1.73 g, 8.13 mmol), and 2-ethoxyethanol (50 ml) were combined in a round bottom flask. Nitrogen was bubbled directly through the suspension for 15 minutes. Potassium carbonate (1.12 g, 8.13 mmol) was added and the reaction was allowed to proceed at room temperature overnight. Upon completion, the reaction was filtered through Celite with DCM until a red color appeared. The solution was concentrated to give a dark red oily solid, which was dissolved in DCM and adsorbed onto Celite. The sample was purified on silica gel to give 0.24 g of a dark red solid in 13% yield.

[0094] Synthesis of compound 22

[0095] Synthesis of (4,4,4-trifluoro-3-(trifluoromethyl)butyl)zinc(II) iodide [ka] Lithium chloride (1.87 g, 44.1 mmol) was charged to the reaction flask. The flask was evacuated and heated with a heat gun for 10 minutes. The flask was cooled to room temperature and zinc (2.88 g, 44.1 mmol) was added to the flask. The flask was again evacuated and heated with a heat gun for 10 minutes. The flask was cooled to room temperature and THF (80 mL) was poured into the reaction and 1,2-dibromoethane (0.42 mL, 4.90 mmol) was added. This mixture was stirred for 30 minutes in an oil bath set at 60° C. Diiodine (0.25 g, 0.98 mmol) and chlorotrimethylsilane (0.12 ml, 0.98 mmol) dissolved in 4 mL of THF were added and the mixture was cooled to room temperature. The mixture was again stirred for 30 minutes in an oil bath set at 60° C. The mixture was again cooled to room temperature. 1,1,1-trifluoro-4-iodo-2-(trifluoromethyl)butane (7.50 g, 24.5 mmol) was then injected into the reaction mixture via syringe. The heterogeneous reaction mixture was stirred and heated overnight in an oil bath set at 50° C. The reaction mixture was cooled to room temperature and stirring was stopped. The product was used as is.

[0096] Synthesis of 2-(3,5-dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline [ka] 8-(5-Chloroquinolin-2-yl)-2,6-dimethylbenzofuro[2,3-b]pyridine (3.40 g, 9.48 mmol), 2'-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine (CPhos) (0.33 g, 0.76 mmol), and diacetoxypalladium (0.09 g, 0.38 mmol) were diluted in THF (190 mL). The mixture was degassed by bubbling nitrogen gas for 15 minutes, and (3,3,3-trifluoropropyl)zinc(II) iodide (35 mL, 10.4 mmol) was added via syringe. The mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was quenched with aqueous ammonium chloride and extracted twice with 200 mL of ethyl acetate. These extracts were dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified via column chromatography using a solvent system of heptane / EA (95 / 5 to 90 / 10). The product was triturated with methanol and recrystallized from heptane to give 2-(3,5-dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline as a white solid (2.5 g, 51% yield).

[0097] Synthesis of Ir(III) dimer [ka] 2-(3,5-Dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline (2.48 g, 6.02 mmol) was placed in a round bottom flask and dissolved in ethoxyethanol (24 mL) and water (8 mL). The mixture was degassed by bubbling nitrogen gas for 15 minutes, then iridium chloride (0.72 g, 1.94 mmol) was charged and the reaction was heated at 105° C. for 24 hours. The reaction was cooled to room temperature, diluted with 10 mL of MeOH, filtered, and washed with MeOH to give the Ir(III) dimer (1.2 g, 59% yield).

[0098] Synthesis of compound 22 [ka] Ir(III) dimer (0.50 g, 0.24 mmol) was dissolved in ethoxyethanol (8 mL) and pentane-2,4-dione (0.25 mL, 2.39 mmol) was added. The mixture was degassed by bubbling nitrogen gas for 15 min, after which K2CO3 (0.33 g, 2.39 mmol) was added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the mixture was diluted with DCM, filtered through Celite and washed with DCM. The crude product was applied to Celite and purified via column chromatography (pretreated with TEA) using a solvent system of heptane / DCM (95 / 5). The product was recrystallized several times (5 times) from MeOH / DCM, EtOH / DCM, and THF / i-PrOH to give 0.18 g of the desired compound (34% yield).

[0099] Synthesis of compound 473 [ka] Ir(III) dimer (0.70 g, 0.33 mmol) was dissolved in ethoxyethanol (15 mL) and 3,7-diethylnonane-4,6-dione (0.71 g, 3.34 mmol) was added. The mixture was degassed by bubbling nitrogen gas for 15 min, after which K2CO3 (0.46 g, 3.34 mmol) was added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the mixture was diluted with DCM, filtered through Celite and washed with DCM. The crude product was applied to Celite and purified via column chromatography (pretreated with TEA) using a solvent system of heptane / DCM (95 / 5 to 90 / 10). The product was triturated from methanol to give 0.21 g of dopant (26% yield). Combination with other materials

[0100] The materials described herein as useful for a particular layer in an organic light-emitting device can be used in combination with a wide variety of other materials present in the device.For example, the emissive dopants disclosed herein can 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 referenced below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that may be useful in combination. HIL / HTL:

[0101] The hole injection / transport material used in the embodiments of the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injection / transport material. Examples of materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorocarbons; polymers with conductive dopants; conductive polymers such as PEDOT / PSS; self-assembly monomers derived from compounds such as phosphonic acid and silane derivatives; MoO xp-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds.

[0102] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structure: [ka]

[0103] Ar 1 From Ar 9each of which is a group consisting of aromatic hydrocarbon ring compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indole, and aromatic heterocyclic compounds such as xazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and aromatic hydrocarbon ring groups and aromatic heterocyclic groups having 2 to 10 cyclic structural units of the same or different types, which are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic cyclic group. wherein each Ar is further substituted with substituents 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0104] In one embodiment, Ar 1 From Ar 9 teeth, [ka] are independently selected from the group consisting of: where k is an integer from 1 to 20; 101 From X 108 is C (including CH) or N; Z 101 is NAr 1 , O, or S; Ar 1 has the same radical as defined above.

[0105] Examples of metal complexes used in the HIL or HTL include, but are not limited to, those of the general formula: [ka] where Met is a metal that may have an atomic weight greater than 40; 101 -Y 102 ) is a bidentate ligand, and Y 101 and Y 102 is 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.

[0106] In one embodiment, (Y 101 -Y 102 In another embodiment, (Y 101 -Y 102 In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex is + For the / Fc couple, it has a minimum oxidation potential of less than about 0.6 V in solution. host:

[0107] The light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may contain a host material that uses the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is higher than that of the dopant. In the table below, host materials preferred for devices emitting each color are classified, but any host material may be used with any dopant as long as the triplet criteria are met.

[0108] Examples of metal complexes used as host materials preferably have the general formula: [ka] where Met is a metal; 103 -Y 104 ) is a bidentate ligand, and Y 103 and Y 104 is independently selected from C, N, O, P, and S; 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; and k'+k'' is the maximum number of ligands that may be attached to the metal.

[0109] In one embodiment, the metal complex is a complex: [ka] where (ON) is a bidentate ligand with the metal coordinated to atoms O and N.

[0110] In another embodiment, Met is selected from Ir and Pt. 103 -Y 104 ) is a carbene ligand.

[0111] Examples of the organic compound used as the host material include a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indole, benzimidazole, and aromatic heterocyclic compounds such as benzofuropyridine, 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 aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which may be of the same or different types and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Each group is further substituted with substituents 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0112] In one embodiment, the host compound contains at least one of the following groups in the molecule: [ka] In the formula, R 101 From 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. k is an integer from 0 to 20 or 1 to 20; k''' is an integer from 0 to 20. X 101 From X 108 is selected from C (including CH) or N. 101 and Z 102 is NR 101 , O, or S. HBL:

[0113] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons that leave the light emitting layer. The presence of such a blocking layer in a device can result in significantly higher efficiency compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine light emission to desired areas of an OLED.

[0114] In one embodiment, the compounds used in the HBL contain the same molecules as those used as hosts described above.

[0115] In another embodiment, the compound used in the HBL contains at least one of the following groups in the molecule: [ka] where k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3. ETL:

[0116] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound may be used as long as it is typically used to transport electrons.

[0117] In one embodiment, the compound used in the ETL contains at least one of the following groups in the molecule: [ka] In the formula, 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. 1 From Ar 3 has the same definition as that of Ar mentioned above. k is an integer from 1 to 20. X 101 From X 108 is selected from C (including CH) or N.

[0118] In another embodiment, the metal complex used in the ETL comprises, but is not limited to, the following general formula: [ka] In the formula, (ON) or (NN) is a bidentate ligand having a metal coordinated to the atoms O, N or N, N; 101 is another ligand; and k' is an integer value between 1 and the maximum number of ligands that can be attached to the metal.

[0119] In any of the above-mentioned compounds used in each layer of an OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically mentioned substituent, such as but not limited to methyl, phenyl, pyridyl, etc., includes the non-deuterated, partially deuterated, and fully deuterated versions thereof. Similarly, the classes of substituents, such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc., also include the non-deuterated, partially deuterated, and fully deuterated versions thereof.

[0120] In addition to and / or in combination with the materials disclosed herein, many hole injection materials, hole transport materials, host materials, dopant materials, exciton / hole blocking layer materials, electron transport and electron injection materials can be used in OLED.Non-limiting examples of materials that can be used in combination with the materials disclosed herein in OLED are listed in Table A below.Table A lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials. [Table A-1] [Table A-2] [Table A-3] [Table A-4] [Table A-5] [Table A-6] [Table A-7] [Table A-8] [Table A-9] [Table A-10] [Table A-11] [Table A-12] [Table A-13] [Table A-14] [Table A-15] [Table A-16] [Table A-17] [Table A-18] [Table A-19] [Table A-20] [Table A-21] [Table A-22] EXAMPLES

[0121] Device Example

[0122] All of the devices in the examples were fabricated under high vacuum (<10 -7 The devices were fabricated by thermal evaporation at 1000 Å (350 Å) Torr. The anode electrode was 1200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of LiF and 1,000 Å of Al. All devices were encapsulated immediately after fabrication in a nitrogen glove box (H2O and O2 <1 ppm) with a glass lid sealed with epoxy resin, and a moisture getter was included in the package. The organic stack of the device examples consisted of, from the ITO surface, 100 Å of LG101 (purchased from LG chem) as a hole injection layer (HIL); 400 Å of 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD) as a hole transport layer (HTL); 300 Å of an emissive layer (EML) containing Compound H (79%) as a host, a stable dopant (SD) (18%), and Compound 453, Compound 781, or Compound 699 as an emitter; 100 Å of Compound H as a blocking layer; and 450 Å of Alq3 (tris-8-hydroxyquinoline aluminum) as an ETL. The emitters were chosen to provide the desired color, and the stable dopant (SD) mixed with the electron transport host and emitter to help transport positive charges in the emissive layer. The comparative device was fabricated similarly to the device examples, except that Comparative Compound 1 was used as the emitter in the EML. Table 1 shows the composition of the EML in the devices, and the device results and data are summarized in Table 2. As used herein, NPD, compound H, SD, and AlQ3 are represented by the following structures: [ka]

[0123] Comparative Example Comparative compound 1 used in the experiments is represented by the following structure: [ka]

[0124] Invention compound: Representative invention compounds used in the experiments, Compound 453, Compound 781, Compound 699, Compound 22, and Compound 473, are represented by the following structures. [ka]

[0125] Table 1 below lists the compounds that were used as emissive dopants in the EML layer in the experimental devices. [Table 1]

[0126] Table 2 below provides device performance data for invention device examples 1, 2, 3, 4, and 5, and comparative device example 1. [Table 2]

[0127] Table 2 summarizes the performance of the experimental devices. 1931 CIE values ​​are expressed as 10 mA / cm 2 The luminous efficiency was measured at 1000cd / m 2 The EQE and LT of Comparative Example 1 were measured. 95% was assigned a value of 1.00. Values ​​obtained from the inventive examples are relative to those obtained from the comparative examples. All of the inventive device examples show higher external quantum efficiency (EQE) than Comparative Example 1 (1.74, 1.74, 1.82, 1.64, and 1.80 vs. 1.00). The LT at 1,000 nits for the inventive compounds Compounds 453, 781, 699, 22, and 473 (Inventive Device Examples 1, 2, 3, 4, and 5) was 95% The lifetimes, expressed as ##EQU1## were also more stable than those of Comparative Compound 1 (Comparative Example 1) (8.55, 9.09, 5.73, 1.53, and 1.54 vs. 1.00).

[0128] It is understood that the various embodiments described herein are merely exemplary and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. Thus, the invention as claimed may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It is understood that the various theories of why the invention works are not intended to be limiting. [Prior art documents] [Patent documents]

[0129] [Patent Document 1] U.S. Pat. No. 5,844,363 [Patent Document 2] U.S. Patent No. 6,303,238 [Patent Document 3] U.S. Patent No. 5,707,745 [Patent Document 4] U.S. Patent No. 7,279,704 [Explanation of symbols]

[0130] 100 Organic Light Emitting Device 110 Substrate 115 Anode 120 Hole injection layer 125 Hole transport layer 130 Electron Blocking Layer 135 Light-emitting layer 140 Hole Blocking Layer 145 Electron transport layer 150 Electron injection layer 155 Protective layer 160 Cathode 162 First conductive layer 164 Second Conductive Layer 200 Inverted OLED, device 210 Substrate 215 Cathode 220 Light-emitting layer 225 Hole transport layer 230 Anode

Claims

1. Formula M(L １ ) ｘ (L ２ ) ｙ (L ３ ) ｚ A compound represented by the formula: The compound can function as a phosphorescent emitter in an organic light emitting device at room temperature; having at least one aromatic ring and at least one substituent R; each of said at least one substituent R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of said at least one substituent R is directly bonded to one of said aromatic rings; In each of said at least one substituent R, the C having F bonded thereto is separated from said aromatic ring by at least one carbon atom, said M being selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; 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; L １ , L ２ , and L ３ When each of the following is present, L １ , L ２ , and L ３ At least one is different from the others; L １ has the following structure: 【Chemistry 1】 X １ From X ８ each independently contains carbon or nitrogen; R ａ , and R ｃ represents the maximum number of substitutions possible from monosubstitution or represents no substitution; R ａ , and R ｃ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , and R ｃ two adjacent substituents may be linked to form a ring or a multidentate ligand; R ａ , and R ｃ at least one of the groups contains at least one substituent R; L ２ , and L ３ are each independently selected from the group consisting of: 【Chemistry 2】 X １ From X １３ each independently contains carbon or nitrogen; X is BR', NR', PR', O, S, Se, C=O, S=O, SO ２ , CR′R″, SiR′R″, and GeR′R″; R′ and R″ are optionally fused or joined to form a ring; R ａ , R ｂ , R ｃ and R ｄ represents the maximum number of substitutions possible, from monosubstitution to no substitution; R', R", R ａ , R ｂ , R ｃ and R ｄ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , R ｂ , R ｃ and R ｄ wherein two adjacent substituents of may be linked to form a ring or a polydentate ligand.

2. 2. The compound of claim 1, wherein at least one X is present and X is selected from the group consisting of NR', O, S, Se, CR'R'', and SiR'R''.

3. R', R", R ａ , R ａ ', R ｂ , R ｃ , R ｃ ' and R ｄ is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

4. Formula Ir(L １ ) ２ (L ２ 2. The compound according to claim 1, wherein

5. At least one pair of adjacent substituents R ａ ' or R ｃ 2. The compound of claim 1, wherein:

6. At least one pair of adjacent substituents R ａ ' or R ｃ 6. The compound of claim 5, wherein:

7. At least one pair of substituents R ａ ' or R ｃ 2. The compound of claim 1, wherein:

8. X １ , X ２ , X ３ , or X ４ The compound of claim 1 , wherein at least one of is nitrogen.

9. L １ has the following structure: 【Chemistry 3】 X ９’ From X １２’ are each independently carbon or nitrogen X' is selected from the group consisting of BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R", SiR'R", and GeR'R", R' and R" are each 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; The compound of claim 1 , wherein R′ and R″ are optionally fused or joined to form a ring.

10. L １ has the following structure: 【Chemistry 4】 L ２ 2. The compound of claim 1 having the structure: 【Chemistry 5】

11. 1. A consumer product including an organic light emitting device, comprising: an anode; A cathode; an organic layer disposed between the anode and the cathode, the organic layer comprising a compound capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature; having at least one aromatic ring and at least one substituent R; each of said at least one substituent R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of said at least one substituent R is directly bonded to one of said aromatic rings; In each of said at least one substituent R, the C having F bonded thereto is separated from said aromatic ring by at least one carbon atom, said M being selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; 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; L １ , L ２ , and L ３ When each of the following is present, L １ , L ２ , and L ３ At least one is different from the others; L １ has the following structure: 【Chemistry 6】 X １ From X ８ each independently contains carbon or nitrogen; R ａ , and R ｃ represents the maximum number of substitutions possible, from monosubstitution to no substitution; R ａ , and R ｃ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , and R ｃ two adjacent substituents may be linked to form a ring or a multidentate ligand; R ａ , and R ｃ at least one of the groups contains at least one substituent R; L ２ , and L ３ are each independently selected from the group consisting of: 【Chemistry 7】 X １ From X １３ each independently contains carbon or nitrogen; X is BR', NR', PR', O, S, Se, C=O, S=O, SO ２ , CR′R″, SiR′R″, and GeR′R″; R′ and R″ are optionally fused or joined to form a ring; R ａ , R ｂ , R ｃ and R ｄ represents the maximum number of substitutions possible, from monosubstitution to no substitution; R', R", R ａ , R ｂ , R ｃ and R ｄ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , R ｂ , R ｃ and R ｄ wherein two adjacent substituents of may be linked to form a ring or a polydentate ligand.

12. 1. An organic light emitting device, comprising: an anode; A cathode; an organic layer disposed between the anode and the cathode, the organic layer comprising a compound capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature; having at least one aromatic ring and at least one substituent R; each of said at least one substituent R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof; each of said at least one substituent R is directly bonded to one of said aromatic rings; In each of said at least one substituent R, the C having F bonded thereto is separated from said aromatic ring by at least one carbon atom, said M being selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; 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; L １ , L ２ , and L ３ When each of the following is present, L １ , L ２ , and L ３ At least one is different from the others; L １ has the following structure: 【Chemistry 8】 X １ From X ８ each independently contains carbon or nitrogen; R ａ , and R ｃ represents the maximum number of substitutions possible, from monosubstitution to no substitution; R ａ , and R ｃ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , and R ｃ two adjacent substituents may be linked to form a ring or a multidentate ligand; R ａ , and R ｃ at least one of the groups contains at least one substituent R; L ２ , and L ３ are each independently selected from the group consisting of: 【Chemistry 9】 X １ From X １３ each independently contains carbon or nitrogen; X is BR', NR', PR', O, S, Se, C=O, S=O, SO ２ , CR′R″, SiR′R″, and GeR′R″; R′ and R″ are optionally fused or joined to form a ring; R ａ , R ｂ , R ｃ and R ｄ represents the maximum number of substitutions possible, from monosubstitution to no substitution; R', R", R ａ , R ｂ , R ｃ and R ｄ 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R ａ , R ｂ , R ｃ and R ｄ wherein two adjacent substituents of may be linked to form a ring or a polydentate ligand.

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