Organic Light Emitting Materials and Devices

Abstract

To provide a compound including ligands improving device performance.SOLUTION: For example, provided herein is an Ir complex compound with 2-phenylpyridine ligands with specific substituents on the pyridine rings, which is prepared as the formula in the figure.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] This application is a non-provisional application of U.S. Patent Application No. 62 / 320,915, filed April 11, 2016, and U.S. Patent Application No. 62 / 368,518, filed July 29, 2016, the disclosures of which are incorporated by reference in their entireties.

[0002] The present invention relates to compounds for use as light emitters, and to devices, such as organic light emitting diodes, which include said compounds. [Background technology]

[0003] Optoelectronic devices that utilize 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 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 diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over traditional 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. Alternatively, OLEDs can be designed to emit white light. Conventional liquid crystal display emission from a white backlight is filtered with absorbing filters to produce red, green, and blue emission. Similar techniques can be used with OLEDs. White OLEDs can be either single EML devices or stacked structures. 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] Ir(ppy) 3 The compound is tris(2-phenyl)iridium, which is represented as

[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] According to an embodiment, there is provided a compound comprising a ligand L represented by the formula: [ka] In the structure of formula I, R 1 and R 6 represent mono-, di-, tri-, or tetra-substitution, or unsubstituted; R 2 represents mono-, di-, or tri-substitution, or unsubstituted; R 1 , R 2 , R 3 , R 4 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 any adjacent substituents of may be bonded or fused to form a ring; R 3 , R 4 , and R 5 at least one of is not hydrogen; a is an integer from 0 to 10; (i) When a is 0, at least one of R 7 , R 8 , and R adjacent to ring B 2 is not hydrogen, (ii) When a is 1 - 10, at least one of R adjacent to ring A 2 and R adjacent to ring C 6 is not hydrogen; The ligand L coordinates with a metal M having an atomic weight greater than 40; The ligand L may be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands.

[0016] According to another embodiment, an organic light emitting diode / device (OLED) is also provided. The OLED can include an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer can include a compound including a ligand L represented by the formula: [ka] According to yet other embodiments, the organic light emitting device is incorporated into one or more devices selected from a consumer product, an electronic component module, and / or a lighting panel.

[0017] According to yet another embodiment, there is provided a composition comprising a compound comprising a ligand L represented by the formula: [ka] [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 of each of these layers are available. 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 a 50:1 molar ratio of m-MTDATA to F, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. 4-TCNQ doped. 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 1:1 molar ratio 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), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, cars, video walls including multiple displays aligned together, theater or stadium screens, and signage. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices made according to the present 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 may 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 term "halo," "halogen," or "halide" includes fluorine, chlorine, bromine, and iodine.

[0033] As used herein, the term "alkyl" refers to both straight and branched chain alkyl groups. Preferred alkyl groups contain from 1 to 15 carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, and 2,2-dimethylpropyl. Additionally, the alkyl groups may be substituted.

[0034] As used herein, the term "cycloalkyl" refers to a cyclic alkyl group. Preferred cycloalkyl groups contain 3 to 10 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, and the like. Additionally, 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 to 7 ring atoms, including 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] In this specification, the term "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, for example, the other rings being cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups contain 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. An aryl group having 6 carbons, an aryl group having 10 carbons, or an aryl group having 12 carbons is particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene being preferred. Additionally, the aryl group may be substituted.

[0040] As used herein, the term "heteroaryl" refers to a monocyclic heteroaromatic group that may contain 1-5 heteroatoms. 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 being "fused"), at least one of the rings being heteroaryl, and the other rings may be, for example, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred heteroaryl groups are those containing 3-30 carbon atoms, preferably those containing 3-20 carbon atoms, and more preferably those containing 3-12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziso ... Examples of heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, with dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza analogs thereof being preferred. Furthermore, the heteroaryl group may be optionally substituted.

[0041] The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocycle, aryl, and heteroaryl may be unsubstituted or substituted with one or more substituents selected from 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 one embodiment, compounds are described that include a ligand L represented by the formula: [ka] In the structure of formula I: R 1 and R 6 represents mono-, di-, tri-, or tetra-substitution, or represents no substitution; R 2 represents mono-, di-, or tri-substitution, or represents unsubstitution; R 1 , R 2 , R 3 , R 4 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 any adjacent substituents of may be joined or fused to form a ring; R3 , R 4 , and R 5 At least one of is not hydrogen; a is an integer from 0 to 10; (i) If a is 0, then R 7 , R 8 and R adjacent to ring B 2 (ii) when a is 1 to 10, at least one of R 2 and R adjacent to ring C 6 At least one of is not hydrogen; said ligand L coordinates with a metal M of atomic weight greater than 40; The ligand L may be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands.

[0046] In some embodiments, ring A is bonded to ring C at a para position relative to the N of ring C. In some embodiments, ring A is bonded to ring C meta position relative to the N of ring C. In some embodiments, ring B is bonded to ring C at a para position relative to the N of ring C, or ring B is bonded to adjacent ring A or adjacent ring A para position relative to ring C. In some embodiments, ring B is bonded to ring C at a meta position relative to the N of ring C, or ring B is bonded to adjacent ring A or adjacent ring A meta position relative to ring C.

[0047] In some embodiments, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu, hi some embodiments, M is Ir or Pt.

[0048] In some embodiments, the compound is homoleptic. In other embodiments, the compound is heteroleptic.

[0049] In some embodiments, (i) when a is 0, R 7 , R 8 and R adjacent to ring B 2is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof; and (ii) when a is 1 to 10, R adjacent to ring A is 2 and R adjacent to ring C 6 At least one of is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof.

[0050] In some embodiments, R 3 , R 4 , and R 5 At least one of is selected from the group consisting of alkyl, cycloalkyl, fluorine, partially or fully deuterated variants thereof, and combinations thereof.

[0051] In some embodiments, R 1 is hydrogen.

[0052] In some embodiments, (i) when a is 0, R adjacent to at least one ring B is 2 is not hydrogen, and R 7 and R 8 at least one of R is not hydrogen, and (ii) when a is 1 to 10, R adjacent to at least one ring A is 2 is not hydrogen, and at least one R adjacent to ring C 6 is not hydrogen.

[0053] In some embodiments, when a is 1 to 10, R 7 and R 8 is hydrogen. In some embodiments, a is 2-10.

[0054] In some embodiments, the ligand L is selected from the group consisting of: [ka]

[0055] In some embodiments, the ligand L is defined in the table below based on the structure: A1 ~L A1432 , L B1 ~L B1432 , L C1 ~L C1432 , L D1 ~L D1432 is selected from the group consisting of: [ka] [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

Table A-23

Table A-24

Table A-25

Table A-26

Table A-27

Table A-28

Table A-29

Table A-30

Table A-31

Table A-32

Table A-33

Table A-34

Table A-35

Table A-36

Table A-37

Table A-38

Table A-39

Table A-40

Table A-41

Table A-42

Table A-43

Table A-44

Table A-45

Table A-46

Table A-47

Table A-48

Table A-49

Table A-50

Table A-51

Table A-52

Table A-53

Table A-54

Table A-55

Table A-56

Table A-57

Table A-58

Table A-59

Table A-60

Table A-61

Table A-62

Table A-63

Table A-64

Table A-65

Table A-66

Table A-67

Table A-68

[0056] In some embodiments, the compound is ML n (L B ) m-n wherein M is Ir or Pt; B is a bidentate ligand; when M is Ir, m is 3 and n is 1, 2, or 3; when M is Pt, m is 2 and n is 1 or 2.

[0057] In some such embodiments, the compound is an IrL 3 In some such embodiments, the compound is represented by the formula: B ) 2 It is expressed by the formula: L B is different from L.

[0058] In some embodiments, the compound is Ir(L) 2 (L B ) is expressed by the formula L B is different from L.

[0059] In some embodiments, the compound is Pt(L)(L B ) and L and L B In some such embodiments, L and L can be the same or different. B In some embodiments, L and L are linked to form a tetradentate ligand. B is bonded at two sites to form a macrocyclic tetradentate ligand.

[0060] The compound is ML n(L B ) m-n In some embodiments of the formula: (i) M is Ir, m is 3, and n is 1 or 2, or (ii) M is Pt, m is 2, and n is 1; B is selected from the group consisting of: [ka] [ka] In the formula, X 1 ~X 13 are each independently selected from the group consisting of carbon and 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'' may be fused or joined to form a ring; R a , R b , R c , and R d may each represent monosubstitution to the maximum number of substitutions possible, or no substitution; R', R'', R a , R b , R c , and R d are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R a , R b , R c , and R d Any two adjacent substituents of may be fused or linked to form a ring or to form a multidentate ligand.

[0061] The compound is ML n (L B ) m-n In some embodiments of the formula: (i) M is Ir, m is 3, and n is 1 or 2, or (ii) M is Pt, m is 2, and n is 1; B is the L shown below. B1 ~L B300 is selected from the group consisting of: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0062] In organometallic complexes, the ligand L is L A1 ~L A1432 , L B1 ~L B1432 , L C1 ~L C1432 , and L D1 ~L D1432 L B can be other ligands. Thus, the ligand L B1 ~L B1432 , L B1 ~L B300 It is easy to see that they are different and distinct.

[0063] In some embodiments, the compound is selected from the group consisting of Compound A-1 through Compound A-429,600, Compound B-1 through Compound B-429,600, Compound C-1 through Compound C-429,600, and Compound D-1 through Compound D-429,600; The compound kx has the formula Ir(L ki )(L Bj ) 2 Represented by; where x=300i+j-300; k is A, B, C, or D; i is an integer from 1 to 1430, and j is an integer from 1 to 300; L B1 ~L B300 is represented by the structure provided herein.

[0064] In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, or TADF (also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0065] In other embodiments, an organic light emitting device (OLED) is described, comprising: an anode; a cathode; and an organic layer disposed between the anode and the cathode. In some embodiments, a consumer product is described that comprises the OLED described herein. The organic layer comprises a compound having a ligand L represented by the formula: [ka]

[0066] According to another aspect of the present disclosure, there is provided a composition comprising a compound having a ligand L represented by the formula: [ka]

[0067] The OLEDs disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer, and in some embodiments, the compound can be an emissive dopant, and in other embodiments, the compound can be a non-emissive dopant.

[0068] The organic layer may also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the host used may be a) a bipolar material, b) an electron transport material, c) a hole transport material, or d) a wide band gap material with little charge transport role. In some embodiments, the host may include a metal complex. The host may be a triphenylene, including a benzo-fused thiophene or a benzo-fused furan. Any substituent in the host may independently be C n H 2n+1 , O.C. n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2, N(Ar 1 )(Ar 2 ), CH=CH-C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n -Ar 1 In the above substituents, 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 an inorganic compound, such as a Zn-containing inorganic material, such as ZnS.

[0069] The host may be a compound containing 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. The host may include a metal complex. The host may be a specific compound selected from the group consisting of, but is not limited to, the following: [ka] [ka] More information on possible hosts is provided below.

[0070] According to another aspect of the present invention, there is disclosed a composition comprising a compound represented by formula I. The composition can comprise 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 as disclosed herein. Combination with other materials

[0071] 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.

[0072] Conductive dopants: The charge transport layer is doped with a conductive dopant to significantly change the density of charge carriers and therefore its conductivity. The conductivity can be increased by creating charge carriers in the matrix material or, depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant and an n-type conductive dopant is used in the electron transport layer.

[0073] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials. EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO 06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US2012146012 [ka] HIL / HTL:

[0074] 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 x p-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes, and crosslinkable compounds.

[0075] Examples of aromatic amine derivatives used in the HIL or HTL include, but are not limited to, the following general structure: [ka]

[0076] 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. Each Ar can be unsubstituted or substituted with a substituent selected from the group consisting of 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.

[0077] In one embodiment, Ar 1 From Ar9 is selected independently from the group consisting of [Chem.] . In the formula, 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 as defined above.

[0078] Examples of metal complexes used in HIL or HTL include, but are not limited to, the following general formula. [Chem.] In the formula, Met is a metal that can have an atomic weight greater than 40; (Y 101 -Y 102 ) is a bidentate ligand, and Y 101 and Y 102 are independently selected from C, N, O, P, and S; L 101 is a co-ligand; k' is an integer value from 1 to the maximum number of ligands that can attach to the metal; and k'+k'' is the maximum number of ligands that can attach to the metal.

[0079] In one embodiment, (Y 101 -Y 102 ) is a 2-phenylpyridine derivative. In another embodiment, (Y 101 -Y 102 ) is a carbene ligand. In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex has a minimum oxidation potential of less than about 0.6 V in solution with respect to the Fc + / Fc couple.

[0080] Non-limiting examples of HIL materials and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the documents disclosing these materials. CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07-073529、JP2005112765、JP2007091719、JP2008021687、JP2014-009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018 [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] EBL:

[0081] Electron blocking layers (EBLs) can be used to reduce the number of electrons and / or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Blocking layers can also be used to confine emission to desired regions of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group as one of the hosts described below. host:

[0082] 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. The host material is not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is greater than that of the dopant. Any host material may be used with any dopant as long as the triplet criterion is met.

[0083] 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.

[0084] 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.

[0085] In another embodiment, Met is selected from Ir and Pt. 103 -Y 104 ) is a carbene ligand.

[0086] Examples of other organic compounds used as the host material include the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, 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, and benzimidazoline. and aromatic heterocyclic compounds such as benzofuropyridine, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and 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 option in each group can be unsubstituted or substituted with a substituent selected from the group consisting of 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.

[0087] 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. Z 101 and Z 102 is NR 101 , O, or S.

[0088] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials. EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR201301 15564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090 167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US201 2075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US201402 25088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO20 09066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO201212 8298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472

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[0089] One or more additional emitter dopants can be used together with the compounds of the present disclosure.The example of additional emitter dopant is not particularly limited, and any compound can be used as long as the compound is typically used as an emitter material.Suitable emitter materials include, but are not limited to, compounds that can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e. TADF (also called E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

[0090] Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials. CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US 2014103305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US73 32232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586 , US8871361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO200201 5645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842 , WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO20 11044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO201317 4471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450,

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[0091] A hole blocking layer (HBL) can 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 can result in significantly higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and / or a higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and / or a higher triplet energy than one or more of the hosts closest to the HBL interface.

[0092] In one embodiment, the compounds used in the HBL contain the same molecules as those used as hosts described above.

[0093] 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:

[0094] 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.

[0095] In one embodiment, the compound used in the ETL contains at least one of the following groups in the molecule: [ka] JPEG0007681648000123.jpg23154In 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.

[0096] 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.

[0097] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials. CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2 005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, U S20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US20 11210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO20 09148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO 2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535. [ka] [ka] [ka] Charge Generation Layer (CGL)

[0098] In tandem or stacked OLEDs, the CGL plays an important role in performance and consists of n-doped and p-doped layers for the injection of electrons and holes, respectively. The electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively, after which the bipolar current gradually reaches a steady state. Typical CGL materials contain n-type and p-type conductive dopants used in the transport layers.

[0099] 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 of the specifically mentioned substituents, such as but not limited to methyl, phenyl, pyridyl, etc., can be their non-deuterated, partially deuterated, and fully deuterated versions. Similarly, the classes of substituents, such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc., can be their non-deuterated, partially deuterated, and fully deuterated versions. EXAMPLES

[0100] Compound IrL A1431 (L B91 ) 2 Synthesis of [ka]

[0101] Process 1 [ka]

[0102] A 250 mL two-necked round bottom flask was flushed with nitrogen and then charged under nitrogen with 2-bromo-4-chloro-5-methylpyridine (9.88 g, 47.9 mmol), phenylboronic acid (6.42 g, 52.6 mmol), diacetoxypalladium (0.537 g, 2.393 mmol), triphenylphosphane (2.51 g, 9.57 mmol), potassium hydroxide (5.37 g, 96 mmol), and acetonitrile (150 ml) / ethanol (75 ml) mixture to give a red suspension. The reaction mixture was heated to 60° C. under nitrogen for 16 hours. The reaction mixture was then cooled to room temperature (ca. 22° C.), filtered through a pad of silica gel, and evaporated to dryness. The residue was purified by column chromatography (silica gel, heptane / EtOAc=2 / 1 (v:v)) and crystallized from heptane as colorless crystals (6.5 g, 67% yield).

[0103] Process 2 [ka]

[0104] Under nitrogen, 4-chloro-5-methyl-2-phenylpyridine (5 g, 24.55 mmol), (4-cyclohexylphenyl)boronic acid (5.01 g, 24.55 mmol), potassium phosphate tribasic acid monohydrate (11.31 g, 49.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (2 mol%) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (4 mol%) were dissolved in a dimethoxyethane (DME) (70 ml) / water (5 ml) mixture to give a red suspension. The reaction mixture was degassed and heated to reflux for 16 h.

[0105] The reaction mixture was then cooled to room temperature (about 22° C.) The organic phase was then separated, filtered, evaporated, and purified by silica gel column chromatography eluted with heptane / tetrahydrofuran (THF) 9 / 1 (v / v) to give a clear solidified colorless oil (6.8 g, 85% yield).

[0106] Process 3 [ka]

[0107] Under nitrogen, 4-(4-cyclohexylphenyl)-5-methyl-2-phenylpyridine (6.8 g, 20.77 mmol), ((methyl-d 3 )Sulfinyl)methane-d 3 (61.2 g, 727 mmol) and sodium 2-methylpropan-2-olate (0.998 g, 10.38 mmol) were suspended together in a flask. The flask was immersed in an oil bath at 71° C. for 18 hours. The reaction mixture was then cooled to room temperature (approximately 22° C.) and 3 equivalents of D 2 It was quenched with O, diluted with brine and extracted with EtOAc. The organic phase was separated, filtered, evaporated and purified on a silica gel column eluted with heptane / THF 95 / 5 (v / v) to give colorless crystals (6.0 g, 87% yield).

[0108] Process 4 [ka]

[0109] Under nitrogen, methanol solvated iridium triflate salt (4 g, 5.12 mmol) and 4-(4-(cyclohexyl-1-d)phenyl)-5-(methyl-d 3 )-2-Phenylpyridine (5.94 g, 17.90 mmol) was suspended in an ethanol (30 ml) / methanol (30.0 ml) mixture. The reaction mixture was degassed and then the flask was immersed in an oil bath at 70 °C for 3 days. The reaction mixture was then cooled to room temperature (approximately 22 °C), filtered and the solid material was dried. The mixture was purified by silica gel column chromatography eluted with a gradient heptane / toluene 4 / 1 to 1 / 4 (v / v) mixture. The pure fractions were evaporated and crystallized from DCM / ethanol to give 1.8 g of a light yellow solid (39% yield).

[0110] IrL A1432 (L B91 ) 2 Synthesis of [ka]

[0111] Process 1 [ka]

[0112] Under nitrogen, 4-chloro-5-methyl-2-phenylpyridine (6 g, 29.5 mmol), (3,4-dimethylphenyl)boronic acid (4.86 g, 32.4 mmol), and potassium phosphate tribasic acid hydrate (13.57 g, 58.9 mmol) were dissolved in a mixture of DME (60 ml) / water (2 mL) to give a colorless suspension. 2 (dba) 3 (0.405 g, 0.442 mmol) and SPhos (0.410 g, 0.884 mmol) were added in one portion and the reaction mixture was degassed and heated to 100° C. under nitrogen for 16 h. Afterwards, the reaction mixture was cooled to room temperature (about 22° C.). The organic phase was separated, evaporated and purified by silica gel column chromatography eluted with heptane / THF 95 / 5 (v / v) and then crystallized from heptane to give white crystals (7.0 g, 85% yield).

[0113] Process 2 [ka]

[0114] Under nitrogen, 4-(3,4-dimethylphenyl)-5-methyl-2-phenylpyridine (7 g, 25.6 mmol), ((methyl-d3)sulfinyl)methane-d3 (86 g, 1,024 mmol), and sodium 2-methylpropan-2-olate (1.723 g, 17.92 mmol) were dissolved in a flask to give a brown solution. The flask was immersed in an oil bath at 71 °C for 14 hours, cooled to room temperature (approximately 22 °C), and 3 equivalents of D 2 The mixture was quenched with O and then diluted with brine. The resulting solution was extracted with EtOAc, and the organic extracts were combined, filtered, and evaporated. The crude material was purified by column chromatography using a silica gel column eluted with heptane / THF 95 / 5 (v / v) to give 4-(3,4-bis(methyl-d3)phenyl)-5-(methyl-d3)-2-phenylpyridine (6.0 g, 83% yield) as a white solid.

[0115] Process 3 [ka]

[0116] Methanol solvated iridium triflate salt (2.8 g, 3.58 mmol) and 4-(3,4-bis(methyl-d3)phenyl)-5-(methyl-d3)-2-phenylpyridine (3.03 g, 10.74 mmol) were suspended in a flask under nitrogen in a mixture of EtOH (30 ml) / MeOH (30.0 ml) to give a yellow suspension. The flask was immersed in an oil bath at 71° C. and stirred under nitrogen for 3 days. The mixture was cooled to room temperature (about 22° C.) and the yellow solid was filtered and purified by column chromatography using a silica gel column eluted with toluene / heptane 85 / 15 (v / v), followed by crystallization from toluene / ethanol and toluene / heptane to give a yellow solid (1.8 g, 59% yield). Device Example

[0117] All of the devices in the examples were fabricated under high vacuum (<10 -7The devices were fabricated by thermal evaporation at 4000 Å / cm² / cm² / cm² / cm² / s at 1000 Å / s. The anode electrode was 800 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (lithium 8-hydroxyquinoline) and 1,000 Å of Al. All devices were stored in a nitrogen glove box (H 2 O and O 2 The device was encapsulated with a glass lid sealed with epoxy resin in a 1 ppm (<1 ppm) and a moisture getter was packaged. The organic stack of the device example consisted of, from the ITO surface, 100 Å of HAT-CN as hole injection layer (HIL); 450 Å of HTM as hole transport layer (HTL); and 400 Å thick light emitting layer (EML). The light emitting layer included H-host (H1):E-host (H2) in a ratio of 6:4 and 12 wt % of green emitter. As ETL, 350 Å of Liq (8-hydroxyquinoline lithium) doped with 40% ETM. Table 1 shows the schematic device structure. The chemical structures of the device materials are shown below. [ka] [ka]

[0118] The fabricated device was subjected to DC 80 mA / cm 2 The EL, JVL, and lifetime were evaluated at 1000 nits. The acceleration factor was assumed to be 1.8, and the LT97 was calculated at 9,000 nits from the 80 mA / cm2 LT data. The device performance is shown in Table 2. Table 1: Schematic device structures [Table 1] Table 2: Device performance [Table 2]

[0119] Example IrL A1431 (L B91 ) 2 and IrL A1432 (L B91) 2 The efficiency of compound IrL is higher than that of the comparative example, probably because the alkyl substitution of the peripheral rings has a better alignment with the transition dipole moment of the molecule. The concept is shown in the diagram below. Furthermore, compound IrL A1431 (L B91 ) 2 and IrL A1432 (L B91 ) 2 are all blue-shifted relative to the comparative example, which has a lower device lifetime. [ka]

[0120] 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]

[0121] [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]

[0122] 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 170 Barrier Layer 200 Inverted OLED, device 210 Substrate 215 Cathode 220 Light-emitting layer 225 Hole transport layer 230 Anode

Claims

1. A compound represented by the formula M(L A ) n (L B ) mn , The L A is different from the L B , The L A comprises the following formula I: 【Chemistry 1】 (In formula I, m is 2 or 3, n is 1 or 2, when m is 3, n is 1 or 2; when m is 2, n is 1; R ２ represents mono-, di-, or tri-substitution; R 2 is selected from the group consisting of alkyl, cycloalkyl, and partially or fully deuterated variants thereof; R3, R ４ , R ５ , R7, and R ８ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R2, R ３ , R ４ , R ５ , R7, and R ８ any adjacent substituents of may be joined or fused to form a ring; R ３ , R ４ , and R ５ at least one of is selected from the group consisting of alkyl, cycloalkyl, fluorine, partially or fully deuterated variants thereof, and combinations thereof; The L A is coordinated with a metal M; The metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu, or the metal M is Ir or Pt. The compound, wherein L B is selected from the group consisting of the following: 【Chemistry 2】 (In the formula, X 1 -X 10 are each independently selected from the group consisting of carbon and 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″ may be fused or joined to form a ring; R a and R b may each represent monosubstitution to the maximum number of substitutions possible, or no substitution; R', R'', R a , and R b are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; At least one of R a and R b is not hydrogen; Any two adjacent substituents of R a and R b may be fused or bonded to form a ring.

2. The compound of claim 1, wherein at least one of R 7 and R 8 is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof.

3. R7 and R ８ The compound of claim 1 , wherein at least one of is not hydrogen.

4. The compound of claim 1, wherein L A is selected from L A1 to L A1432 as defined in the following table based on the structure below. 【Chemistry 3】 【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】 【Table A-23】 【Table A-24】 【Table A-25】 【Table A-26】 【Table A-27】 【Table A-28】 【Table A-29】 【Table A-30】 【Table A-31】 【Table A-32】 【Table A-33】 【Table A-34】 【Table A-35】 【Table A-36】 【Table A-37】 【Table A-38】 【Table A-39】 【Table A-40】 【Table A-41】 【Table A-42】 【Table A-43】 【Table A-44】 【Table A-45】 【Table A-46】 【Table A-47】 【Table A-48】 【Table A-49】 【Table A-50】 【Table A-51】 【Table A-52】 【Table A-53】 【Table A-54】 【Table A-55】 【Table A-56】 【Table A-57】 【Table A-58】 【Table A-59】 【Table A-60】 【Table A-61】 【Table A-62】 【Table A-63】 【Table A-64】 【Table A-65】 【Table A-66】 【Table A-67】 5. The metal M is Ir or Pt; When the metal M is Ir, m is 3 and n is 1 or 2; 2. The compound of claim 1, wherein when the metal M is Pt, m is 2 and n is 1.

6. The L B is any one of L B2 to L B1 shown below. Ｂ３００ 2. The compound of claim 1 selected from the group consisting of: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】

7. an anode; A cathode; an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of the formula M(L A ) n (L B ) mn , The L A is different from the L B , The L A comprises the following formula I: 【Chemistry 15】 (In formula I, m is 2 or 3, n is 1 or 2, when m is 3, n is 1 or 2; when m is 2, n is 1; R ２ represents mono-, di-, or tri-substitution; R 2 is selected from the group consisting of alkyl, cycloalkyl, and partially or fully deuterated variants thereof; R3, R ４ , R ５ , R7, and R ８ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R2, R ３ , R ４ , R ５ , R7, and R ８ any adjacent substituents of may be joined or fused to form a ring; R ３ , R ４ , and R ５ at least one of is selected from the group consisting of alkyl, cycloalkyl, fluorine, partially or fully deuterated variants thereof, and combinations thereof; The L A is coordinated with a metal M; The metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu, or the metal M is Ir or Pt. An organic light emitting device (OLED) characterized in that L B is selected from the group consisting of: 【Chemical 16】 (In the formula, X 1 -X 10 are each independently selected from the group consisting of carbon and 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″ may be fused or joined to form a ring; R a and R b may each represent monosubstitution to the maximum number of substitutions possible, or no substitution; R', R'', R a , and R b are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; At least one of R a and R b is not hydrogen; Any two adjacent substituents of R a and R b may be fused or bonded to form a ring.

8. The organic layer further comprises a host; 8. The organic light emitting device (OLED) of claim 7, wherein the host comprises 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.

9. 1. A consumer product comprising an organic light emitting device, the 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 represented by the formula M(L A ) n (L B ) mn ; The L A is different from the L B , The L A comprises the following formula I: 【Chemistry 17】 (In formula I, m is 2 or 3, n is 1 or 2, when m is 3, n is 1 or 2; when m is 2, n is 1; R ２ represents mono-, di-, or tri-substitution; R 2 is selected from the group consisting of alkyl, cycloalkyl, and partially or fully deuterated variants thereof; R3, R ４ , R ５ , R7, and R ８ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R2, R ３ , R ４ , R ５ , R7, and R ８ any adjacent substituents of may be joined or fused to form a ring; R ３ , R ４ , and R ５ at least one of is selected from the group consisting of alkyl, cycloalkyl, fluorine, partially or fully deuterated variants thereof, and combinations thereof; The L A is coordinated with a metal M; The metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu, or the metal M is Ir or Pt. A consumer product, wherein L B is selected from the group consisting of: 【Chemistry 18】 (In the formula, X 1 -X 10 are each independently selected from the group consisting of carbon and 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″ may be fused or joined to form a ring; R a and R b may each represent monosubstitution to the maximum number of substitutions possible, or no substitution; R', R'', R a , and R b are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; At least one of R a and R b is not hydrogen; Any two adjacent substituents of R a and R b may be fused or bonded to form a ring.

10. 10. The consumer product of claim 9, wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor illumination and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3-D display, a virtual reality or augmented reality display, a car, a large area wall, a theater or stadium screen, and a sign.

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