Phosphorescent organic metal complex and its use

Abstract

Metal complex having a general formula Ir(L a ) m (L b ) n exhibits, whereby it is L a and L b about the first ligand and the second ligand, each coordinated to the metal Ir; and L a and L b optionally, they can be connected in such a way that they form a multidentate ligand; m is equal to 1, 2 or 3, n is equal to 0, 1 or 2, and m+n corresponds to the oxidation state of the metal Ir; where, if m is greater than or equal to 2, the multiple L a are the same or different; if n equals 2, the two L b are the same or different; where L a a structure represented by formula 1a: where Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different from CR in every occurrence x or N can be selected; Y1 to Y4 are the same or different in each occurrence from CR y or N can be selected; X7 is a CR x it is about and the R x it is cyano; At least one of Y1 to Y4 is a CR y deals and the R y selected from the group consisting of: halogen, a substituted or unsubstituted alkyl with 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl with 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl with 2 to 10 carbon atoms, a substituted or unsubstituted aryl with 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms and combinations of these; R x and R yThe following are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl with 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl with 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl with 2 to 10 carbon atoms, a substituted or unsubstituted aryl with 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms and combinations thereof; Ar is selected from the group consisting of: a substituted or unsubstituted aryl with 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R yand Ar can optionally be connected in such a way that they form a ring; it is L b In each instance, whether the same or different, it is an arbitrary one selected from the group consisting of the following structures: where R a and R b Whether each occurrence is the same or different, they represent a monosubstitution, a multiple substitution or a non-substitution; R a and R bThe following are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group with 3 to 20 ring atoms, a substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, a substituted or unsubstituted aryl with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms,a substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, a substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof; and , in structures of L b neighboring substituents R a and R b They can optionally be connected in such a way that they form a ring.

Description

Reference to related application(s)

[0001] This application claims priority to Chinese Patent Application No. CN 1 13 816 996 A, filed on June 20, 2020. Technical area

[0002] The present disclosure relates to compounds for organic electronic devices, for example, organic light-emitting devices. More specifically, the present disclosure relates to a metal complex comprising a ligand having a structure represented by Formula 1, and to an organic electroluminescent device and compound formulation comprising the metal complex. background

[0003] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmon-emitting devices.

[0004] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole-transport layer and a tris-8-hydroxyquinolato aluminum layer as the electron and emitting layers (Applied Physics Letters, 1987, 51 (12): 913 to 915). When a bias voltage was applied to the device, green light was emitted from the device. This device laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emitting layers between the cathode and anode. Because the OLED is a self-emitting solid-state device, it offers tremendous potential for display and lighting applications.Furthermore, the inherent properties of organic materials, such as their flexibility, make them well suited for certain applications such as manufacturing on flexible substrates.

[0005] OLEDs can be divided into three different types according to their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported a phosphorescent OLED that uses triplet emission from heavy metal-containing complexes as emitters. This allows both singlets and triplets to be harvested, achieving an IQE of 100%. The discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs) due to their high efficiency.Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters exhibit a small singlet-triplet gap, allowing the triplet-to-singlet transition. In the TADF device, the triplet excitons can undergo reverse intersystem crossing to generate singlet excitons, resulting in a high IQE.

[0006] OLEDs can also be classified as small-molecule and polymer OLEDs depending on the shape of the materials used. A small molecule refers to any organic or organometallic material that is not a polymer. The molecular mass of a small molecule can be large as long as it has a clearly defined structure. Dendrimers with clearly defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with emissive side groups. A small-molecule OLED can become a polymer OLED if post-polymerization occurs during the manufacturing process.

[0007] There are various methods for OLED manufacturing. Small-molecule OLEDs are generally manufactured by thermal vacuum evaporation. Polymer OLEDs are manufactured using a solution process such as spin-coating, inkjet printing, and slot printing. If the material can be dissolved or dispersed in a solvent, the small-molecule OLED can also be manufactured using a solution process.

[0008] The emission color of an OLED can be achieved through the structural design of the emitter. An OLED can have one emitting layer or multiple emitting layers to achieve the desired spectrum. Phosphorescent emitters have successfully achieved commercialization in green, yellow, and red OLEDs. Blue phosphorescent devices still suffer from a non-saturated blue color, a short device lifetime, and a high operating voltage. Commercial color OLED displays typically employ a hybrid strategy, using fluorescent blue and phosphorescent yellow, or red and green. Currently, the efficiency decline of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission color, higher efficiency, and a longer device lifetime are desired.

[0009] Cyano substituents are not often introduced into phosphorescent metal complexes such as iridium complexes. US 2014 / 0 252 333 A1 disclosed a series of cyanophenyl-substituted iridium complexes that showed no clear effect of cyano groups. Since cyano is a substituent with excellent electron-withdrawing ability, cyano is also used to blue-shift the emission spectrum of phosphorescent metal complexes, such as the one disclosed in US 2004 / 0 121 184 A1.

[0010] DE 10 2020 101 561 A1 and EP 1 238 981 A2, both of which describe the metal complexes with the specific L a -structures not disclosed in the present application are also considered to be prior art. Overview

[0011] The present disclosure aims to provide a series of metal complexes containing a ligand having a structure represented by Formula 1 to solve at least some of the above-mentioned problems. The metal complexes can be used as light-emitting materials in organic electroluminescent devices. These novel compounds can not only maintain high device efficiency and low voltage in organic electroluminescent devices, but also enable these devices to have a narrower half-width and significantly improve the color saturation of light emitted by these devices, thereby providing better device performance.

[0012] According to one embodiment of the present disclosure, a metal complex is disclosed having a general formula Ir(L a ) m (Lb ) n where L is a and L b the first ligand and the second ligand, each coordinated to the metal Ir; and L a and L b can optionally be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2 and m+n is the oxidation state of the metal Ir; where, if m is greater than or equal to 2, the plurality of L a are the same or different; if n is 2, the two L b are the same or different; where L a has a structure represented by a formula 1a:where Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different at each occurrence from CR x or N can be selected; Y1 to Y4 at each occurrence the same or different from CR yor N can be selected; X7 is CR x and the R x it is cyano; at least one of Y1 to Y4 is CR y and the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these; R x and R yare selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these; Ar is selected at each occurrence, identically or differently, from the group consisting of: a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R yand Ar can optionally be connected to form a ring; L is b at each occurrence, the same or different, is any one selected from the group consisting of the following structures:where R a and R b represent, identically or differently at each occurrence, a monosubstitution, a multiple substitution or a non-substitution; R a and R bat each occurrence, identically or differently, are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms,a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations of these; and, in structures of L b neighboring substituents R a and R b can optionally be connected to form a ring

[0013] According to another embodiment of the present disclosure, an electroluminescent device is further disclosed including an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex described above.

[0014] According to another embodiment of the present disclosure, a compound formulation comprising the metal complex described above is further disclosed.

[0015] The novel metal complex comprising a ligand having a structure represented by Formula 1a, as disclosed by the present disclosure, can be used as a light-emitting material in an electroluminescent device. These novel compounds can not only maintain high device efficiency and low voltage in organic electroluminescent devices, but also enable these devices to have a narrower half-width and significantly improve the color saturation of light emitted by these devices, thereby providing better device performance. The present disclosure discloses a series of novel metal complexes containing a ligand having a structure represented by Formula 1a.By constructing the ligand with the structure represented by Formula 1a, the metal complexes can unexpectedly exhibit numerous properties, such as high efficiency, low voltage, and finely tunable emission within a narrow range. The least expected property is a very narrow peak width of the emitted light. These advantages are of great help in improving the levels and color saturation of green / white light-emitting devices. Short description of the drawings Fig. Figure 1 is a schematic view of an organic light-emitting device that may include a metal complex and a compound formulation disclosed herein. Fig. Figure 2 is a schematic view of another organic light-emitting device that may include a compound and compound formulation disclosed herein. Detailed description

[0016] OLEDs can be manufactured on various types of substrates such as glass, plastic and metal foil. Fig.1 schematically illustrates an organic light-emitting device 100 without limitation. The figures are not necessarily drawn to scale. Some of the layers in the figures may be omitted if desired. The device 100 may include a substrate 101, an anode 110, a hole-injection layer 120, a hole-transport layer 130, an electron-blocking layer 140, an emitting layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. The device 100 may be fabricated by depositing the described layers in this order. The properties and functions of these various layers, as well as exemplary materials, are described in more detail in US 2005 / 0 260 449 A1, columns 6 to 10.

[0017] Further examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in US Pat. No. 5,844,363. 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 US Pat. No. 2003 / 0230980. Examples of host materials are disclosed in US Pat. No. 6,303,238 to Thompson et al. An example of an n-doped electron-transport layer is BPhen doped with Li in a molar ratio of 1:1, as disclosed in US Pat. No. 2003 / 0230980. US 5,703,436 A and US 5,707,745 A disclose examples of cathodes, including composite cathodes comprising a thin metal layer such as Mg:Ag, with an overlying transparent, electrically conductive ITO layer deposited by sputtering. The theory and use of blocking layers are described in more detail in US 6,068,147 A and US 2003 / 0 230 980 A1.Examples of injection layers are provided in US 2004 / 0 174 116 A1. A description of protective layers can be found in US 2004 / 0 174 116 A1.

[0018] The layered structure described above is provided by way of non-limiting examples. Functional OLEDs can be achieved by combining the various described layers in different ways, or layers can be omitted entirely. They can also include other layers not specifically described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Each functional layer can include multiple sublayers. For example, the emissive layer can comprise two layers of different emissive materials to achieve the desired emission spectrum.

[0019] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer can comprise a single layer or multiple layers.

[0020] An OLED can be encapsulated by a barrier layer. Fig. 2 schematically illustrates an organic light emitting device 200 without limitation. Fig. 2 differs from Fig.1 is that the organic light-emitting device includes a barrier layer 102 located above the cathode 190 to protect it from harmful environmental species such as moisture and oxygen. Any material capable of providing the barrier function can be used as the barrier layer, for example, glass or organic-inorganic hybrid layers. The barrier layer should be placed directly or indirectly outside the OLED device. A multilayer thin-film encapsulation was described in US 2008 / 0237 181 A1.

[0021] Devices fabricated according to embodiments of the present disclosure can be integrated into a wide variety of consumer products incorporating one or more modules (or units) of electronic components. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signaling fixtures, point-of-view displays, fully or partially transparent displays, flexible displays, smartphones, tablets, phablets, wearable devices, smartwatches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and vehicle taillights.

[0022] The materials and structures described herein can be used in other organic electronic devices listed above.

[0023] As used herein, "top" means farthest from the substrate, whereas "bottom" means closest to the substrate. When a first layer is described as being "disposed above" a second layer, the first layer is disposed farther from the substrate. Other layers may be located between the first and second layers unless it is stated that the first layer is "in contact with" the second layer. For example, a cathode may be described as being "disposed above" an anode even though various organic layers are located therebetween.

[0024] As used herein, “solution processable” means the ability to be dissolved, dispersed, transported, and / or separated from a liquid medium, either in solution or suspension form.

[0025] A ligand can be described as "photoactive" if it is assumed that the ligand directly contributes to the photoactive properties of an emitting material. A ligand can be described as "auxiliary" if it is assumed that the ligand does not contribute to the photoactive properties of an emitting material, although an auxiliary ligand can alter the properties of a photoactive ligand.

[0026] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the spin-statistics limit of 25% through delayed fluorescence. As used herein, two types of delayed fluorescence exist: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0027] In contrast, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the transition between the triplet states and the excited singlet states. Compounds capable of generating E-type delayed fluorescence must have very small singlet-triplet gaps to convert between energy levels. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A special feature of TADF is that the delayed component increases with increasing temperature.If the rate of reverse intersystem crossing (RISC) is high enough to minimize non-radiative decay from the triplet state, the fraction of repopulated excited singlet states can potentially reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin-statistics limit for electrically generated excitons.

[0028] Delayed E-type fluorescence properties can be found in an exciplex system or in a single compound. Without being bound by theory, it is believed that delayed E-type fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔES-T). Organic, non-metal-containing, luminescent donor-acceptor materials may be able to achieve this. The emission in these materials is generally referred to as donor-acceptor charge transfer (CT) emission. The spatial separation of the HOMO and LUMO in these donor-acceptor compounds generally results in a small ΔES-T. These states can be accompanied by CT states.In general, luminescent donor-acceptor materials are prepared by connecting an electron donor moiety such as amino or carbazole derivatives and an electron acceptor moiety such as N-containing six-membered aromatic rings. Definition of terms of substituents

[0029] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0030] Alkyl - as used herein, includes both straight- and branched-chain alkyl groups. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, and more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group and a 3-methylpentyl group.Of the above, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, a neopentyl group, and an n-hexyl group are preferred. Furthermore, the alkyl group may be optionally substituted.

[0031] Cycloalkyl, as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be those having 3 to 20 ring carbon atoms, preferably those having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may be optionally substituted.

[0032] Heteroalkyl - as used herein, includes a group formed by replacing one or more carbons in an alkyl chain with one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. Heteroalkyl may be those having 1 to 20 carbon atoms, preferably those having 1 to 10 carbon atoms, and more preferably those having 1 to 6 carbon atoms.Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, t-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisopropyl. Furthermore, the heteroalkyl group can be optionally substituted.

[0033] Alkenyl, as used herein, includes straight-chain, branched-chain, and cyclic alkene groups. Alkenyl can be those with 2 to 20 carbon atoms, preferably those with 2 to 10 carbon atoms. Examples of alkenyl include vinyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butandienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Furthermore, the alkenyl group may be optionally substituted.

[0034] Alkynyl - as used herein includes straight-chain alkynyl groups. Alkynyl can be those having 2 to 20 carbon atoms, preferably those having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Of the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. In addition, the alkynyl group can be optionally substituted.

[0035] Aryl or an aromatic group—as used herein—includes unfused and fused systems. The aryl can be those having 6 to 30 carbon atoms, preferably those having 6 to 20 carbon atoms, and more preferably those having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of unfused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-Phenylpropyl)phenyl, 4'-methylbiphenylyl, 4"-t-butyl-p-terphenyl-4-yl, o-cumenyl, m-cumenyl, p-cumenyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quarterphenyl.Furthermore, the aryl group can be optionally substituted.

[0036] Heterocyclic groups, or heterocycles, as used herein include non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, each containing at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur.Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. Furthermore, the heterocyclic group can be optionally substituted.

[0037] Heteroaryl - as used herein, includes unfused and fused heteroaromatic groups having 1 to 5 heteroaromatics, wherein at least one heteroatom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. A heteroaromatic group is also referred to as heteroaryl. The heteroaryl can be those having 3 to 30 carbon atoms, preferably those having 3 to 20 carbon atoms, and more preferably those having 3 to 12 carbon atoms.Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, Pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furodipyridine, Benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza analogues thereof. Furthermore, the heteroaryl group can be optionally substituted.

[0038] Alkoxy—as used herein—is represented by an -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic group. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as those described above. Alkoxy groups may be those having 1 to 20 carbon atoms, preferably those having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy groups. Furthermore, the alkoxy group may be optionally substituted.

[0039] Aryloxy—as used herein—is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. Aryloxy groups can be those having 6 to 30 carbon atoms, preferably those having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. Furthermore, the aryloxy group can be optionally substituted.

[0040] Arylalkyl - as used herein, refers to an alkyl substituted with an aryl group. The arylalkyl can be those having 7 to 30 carbon atoms, preferably those having 7 to 20 carbon atoms, and more preferably those having 7 to 13 carbon atoms.Zu Beispielen für Arylalkylgruppen zählen Benzyl, 1-Phenylethyl, 2-Phenylethyl, 1-Phenylisopropyl, 2-Phenylisopropyl, Phenyl-t-butyl, alpha-Naphthylmethyl, 1-alpha-Naphthylethyl, 2-alpha-Naphthylethyl, 1-alpha-Naphthylisopropyl, 2-alpha-Naphthylisopropyl, beta-Naphthylmethyl, 1-beta-Naphthylethyl, 2-beta-Naphthylethyl, 1-beta-Naphthylisopropyl, 2-beta-Naphthylisopropyl, p-Methylbenzyl, m-Methylbenzyl, o-Methylbenzyl, p-Chlorbenzyl, m-Chlorbenzyl, o-Chlorbenzyl, p-Brombenzyl, m-Brombenzyl, o-Brombenzyl, p-Jodbenzyl, m-Jodbenzyl, o-Jodbenzyl, p-Hydroxybenzyl, m-Hydroxybenzyl, o-Hydroxybenzyl, p-Aminobenzyl, m-Aminobenzyl, o-Aminobenzyl, p-Nitrobenzyl, m-Nitrobenzyl, o-Nitrobenzyl, p-Cyanobenzyl, m-Cyanobenzyl, o-Cyanobenzyl, 1-Hydroxy-2-phenylisopropyl und 1-Chlor-2-phenylisopropyl. Von den Obigen werden Benzyl, p-Cyanobenzyl, m-Cyanobenzyl, o-Cyanobenzyl, 1-Phenylethyl, 2-Phenylethyl, 1-Phenylisopropyl und 2-Phenylisopropyl bevorzugt.Furthermore, the arylalkyl group can be optionally substituted.

[0041] Alkylsilyl - as used herein, refers to a silyl group substituted with an alkyl group. Alkylsilyl groups can be those having 3 to 20 carbon atoms, preferably those having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, and methyldi-t-butylsilyl. Furthermore, the alkylsilyl group can be optionally substituted.

[0042] Arylsilyl - as used herein, refers to a silyl group substituted with an aryl group. Arylsilyl groups can be those having 6 to 30 carbon atoms, preferably those having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyl-t-butylsilyl. Furthermore, the arylsilyl group can be optionally substituted.

[0043] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., means that one or more CH groups in the respective aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogues with two or more nitrogens in the ring system. One of ordinary skill in the art can readily envision other nitrogen analogues of the aza derivatives described above, and all such analogues are intended to be encompassed within the terms set forth herein.

[0044] In the present disclosure, unless otherwise defined, when any term of the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, a substituted heterocyclic group, substituted arylalkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, a substituted carboxylic acid group, a substituted ester group, substituted sulfinyl, substituted sulfonyl, and substituted phosphino is used, it means any group consisting of alkyl, cycloalkyl, heteroalkyl, a heterocyclic group, arylalkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, Alkylsilyl, arylsilyl, amino, acyl, carbonyl, a carboxylic acid group, an ester group, sulfinyl,Sulfonyl and phosphino may be substituted with one or more units selected from the group consisting of deuterium, halogen, an unsubstituted alkyl having 1 to 20 carbon atoms, an unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted arylalkyl having 7 to 30 carbon atoms, an unsubstituted alkoxy having 1 to 20 carbon atoms, an unsubstituted aryloxy having 6 to 30 carbon atoms, an unsubstituted alkenyl having 2 to 20 carbon atoms, an unsubstituted alkynyl having 2 to 20 carbon atoms, an unsubstituted aryl having 6 to 30 carbon atoms, an unsubstituted Heteroaryl having 3 to 30 carbon atoms, an unsubstituted alkylsilyl having 3 to 20 carbon atoms, an unsubstituted arylsilyl having 6 to 20 carbon atoms,an unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations of these.

[0045] It is understood that when a molecular fragment is described as a substituent or otherwise bonded to another moiety, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these various ways of referring to a substituent or bonded fragment are considered equivalent.

[0046] In the compounds mentioned in the present disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms, such as carbon and nitrogen, may also be replaced by their other stable isotopes. Replacement by other stable isotopes in the compounds may be preferred due to their improvements in device efficiency and stability.

[0047] In the compounds mentioned in the present disclosure, multiple substitution refers to a range that includes di-substitution up to the maximum available substitution. When a substitution in the compounds mentioned in the present disclosure represents multiple substitution (including di-, tri-, tetra-substitutions, etc.), this means that the substituent can be present at a plurality of available substitution positions on its linking structure, where the substituents present at a plurality of available substitution positions can have the same structure or different structures.

[0048] In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be connected to form a ring unless expressly defined otherwise, for example, that adjacent substituents can optionally be connected to form a ring. In the compounds mentioned in the present disclosure, the expression that adjacent substituents can optionally be connected to form a ring includes a case where adjacent substituents can be connected to form a ring and a case where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the formed ring may be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic, or heteroaromatic.In such an expression, adjacent substituents may refer to substituents bonded to the same atom, to substituents bonded to carbon atoms directly bonded to one another, or to substituents bonded to carbon atoms that are further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and to substituents bonded to carbon atoms directly bonded to one another.

[0049] Furthermore, the expression that adjacent substituents can optionally be joined to form a ring is intended to mean that two substituents attached to the same carbon atom are joined together via a chemical bond to form a ring, which can be exemplified by the following formula:

[0050] The expression that adjacent substituents can optionally be connected to form a ring is intended to mean, moreover, that two substituents bound to directly bonded carbon atoms are connected to each other via a chemical bond to form a ring, which can be exemplified by the following formula:

[0051] Furthermore, the expression that adjacent substituents may optionally be joined to form a ring is intended to further mean that, in the case where one of the two substituents bonded to carbon atoms directly bonded to each other is hydrogen, the second substituent is bonded at a position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0052] According to one embodiment of the present disclosure, a metal complex is disclosed having a general formula Ir(L a ) m (L b ) n where L is a and L b the first ligand and the second ligand, each coordinated to the metal Ir; and L a and L b can optionally be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2 and m+n is the oxidation state of the metal Ir; where, if m is greater than or equal to 2, the plurality of L a are the same or different; if n is 2, the two L b are the same or different; where L a has a structure represented by a formula 1a: where Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different at each occurrence from CR x or N can be selected; Y1 to Y4 at each occurrence the same or different from CR y or N can be selected; X7 is CR x and the R x it is cyano; at least one of Y1 to Y4 is CR y and the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these; R x and R yare selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these; Ar is selected at each occurrence, identically or differently, from the group consisting of: a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R yand Ar can optionally be connected to form a ring; L is b at each occurrence, the same or different, is any one selected from the group consisting of the following structures:where R a and R b represent, identically or differently at each occurrence, a monosubstitution, a multiple substitution or a non-substitution; R a and R bat each occurrence, identically or differently, are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms,a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations of these; and, in structures of L b neighboring substituents R a and R b can optionally be connected to form a ring.

[0053] According to one embodiment of the present disclosure, L b in the metal complex, at each occurrence, identically or differently, is any one selected from the following structures:

[0054] According to another embodiment of the present disclosure, R a and R b in the metal complex at each occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these.

[0055] According to a further embodiment of the present disclosure, the metal complex has a general formula Ir(L a ) m (L b ) 3-m and a structure represented by a formula 2: where m is selected from 1 or 2; where, if m is 2, the two L a are equal or different; if m is 1, the two L b are the same or different; Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different at each occurrence from CR x or N can be selected; Y1 to Y4 at each occurrence the same or different from CR y or N can be selected; X7 is CR x and the R x it is cyano; at least one of Y1 to Y4 is CR y and the R yis selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations thereof; where R x and R y are selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations of these; R1 to R8 are selected, identically or differently at each occurrence, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations of these; Ar is selected at each occurrence, identically or differently, from the group consisting of: a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R y , Ar and R1 to R8 can optionally be connected to form a ring.

[0056] According to one embodiment of the present disclosure, Z in the metal complex is selected from O and S.

[0057] According to one embodiment of the present disclosure, X3 to X7 in the metal complex are, at each occurrence, identically or differently selected from CR x selected.

[0058] According to one embodiment of the present disclosure, X3 to X7 in the metal complex are, at each occurrence, identically or differently selected from CR x or N is selected and at least one of X1 to X7 is N.

[0059] According to one embodiment of the present disclosure, at least two of X3 to X7 in the metal complex are CR x selected and where R x from X7 to Cyano and at least one of the Rx is selected at each occurrence, the same or different, from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations of these.

[0060] According to one embodiment of the present disclosure, at least two of X3 to X7 in the metal complex are CR x selected, and R x from X7 to Cyano and at least one of the R xis selected at each occurrence, the same or different, from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations of these.

[0061] According to one embodiment of the present disclosure, at least one of R x in the metal complex are selected at each occurrence, identically or differently, from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms.

[0062] According to one embodiment of the present disclosure, Y1 to Y4 in the metal complex are selected, identically or differently, at each occurrence from CR y selected.

[0063] According to one embodiment of the present disclosure, Y1 to Y4 in the metal complex are selected, identically or differently, at each occurrence from CR y or N is selected and at least one of Y1 to Y4 is N.

[0064] According to one embodiment of the present disclosure, at least one of Y1 to Y4 in the metal complex is CR y selected and the R y is selected at each occurrence, the same or different, from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these.

[0065] According to one embodiment of the present disclosure, Y2 and / or Y3 in the metal complex are selected from CR y selected and the R y is selected at each occurrence, identically or differently, from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, and combinations of these.

[0066] According to one embodiment of the present invention, Y2 and / or Y3 in the metal complex are CR y selected and the R yis selected at each occurrence, identically or differently, from a substituted alkyl having 1 to 12 carbon atoms, a substituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted aryl having 6 to 20 carbon atoms, or combinations thereof; and the substitution in the above substituted groups comprises at least one deuterium atom.

[0067] According to one embodiment of the present disclosure, the R y at each occurrence, identically or differently, are selected from the group consisting of: a partially or fully deuterated alkyl having 1 to 12 carbon atoms, a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

[0068] According to one embodiment of the present disclosure, in the metal complex, when a carbon atom is at a benzylic position in the R yis a primary carbon atom, a secondary carbon atom or a tertiary carbon atom, at least one deuterium atom in the R y at the benzylic position.

[0069] According to one embodiment of the present disclosure, Y2 and / or Y3 in the metal complex are selected from CR y selected and the R y is selected, identically or differently at each occurrence, from the group consisting of: a partially or fully deuterated alkyl having 1 to 12 carbon atoms, a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof; wherein, when a carbon atom at a benzylic position in the R y is a primary carbon atom, a secondary carbon atom or a tertiary carbon atom, hydrogen at the benzylic position in the R y is completely substituted by deuterium.

[0070] According to one embodiment of the present disclosure, the R y in the metal complex at each occurrence, identically or differently, are selected from the group consisting of: CD3, CD2CH3, CD2CD3, CD(CH3)2, CD(CD3)2, CD2CH(CH3)2, CD2C(CH3)3, and combinations of these.

[0071] According to one embodiment of the present disclosure, at least two of Y1 to Y4 in the metal complex are selected, identically or differently, at each occurrence from CR y selected and at least one of the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and at least one of Ry selected from deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or combinations thereof.

[0072] According to one embodiment of the present disclosure, at least two of Y1 to Y4 in the metal complex are selected, identically or differently, at each occurrence from CR y selected and at least one of the R y is selected from the group consisting of: a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof; wherein at least one of R y is deuterium.

[0073] According to one embodiment of the present invention, Y2 and / or Y3 in the metal complex are CR y selected and the R y is selected at each occurrence, identically or differently, from a partially or fully deuterated alkyl having 1 to 12 carbon atoms or a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms; and Y1 and / or Y4 are selected from CD.

[0074] According to one embodiment of the present disclosure, Ar in the metal complex is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, or combinations thereof; wherein hydrogen in Ar is optionally partially or fully substituted by deuterium.

[0075] According to one embodiment of the present disclosure, in Formula 2, at least one or two of R1 to R8, at each occurrence, are selected, identically or differently, from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof.

[0076] According to one embodiment of the present disclosure, at least one of R1 to R8 in the metal complex is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof.

[0077] According to one embodiment of the present disclosure, in Formula 2, at least one, two, three, or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, fluorine, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations thereof.

[0078] According to one embodiment of the present disclosure, Z in the metal complex is O.

[0079] According to one embodiment of the present disclosure, Y3 in the metal complex is N.

[0080] According to one embodiment of the present disclosure, at least one of Y1 to Y4 in the metal complex is CR y selected and the R yis selected at each occurrence, the same or different, from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, and combinations of these.

[0081] According to one embodiment of the present disclosure, at least two of Y1 to Y4 in the metal complex are selected, identically or differently, at each occurrence from CR y selected wherein at least one of the R yis selected from the group consisting of: a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and at least one of R y selected from deuterium, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or combinations thereof.

[0082] According to one embodiment of the present disclosure, Ar in the metal complex is selected from substituted or unsubstituted phenyl and hydrogen in Ar is optionally partially or fully substituted by deuterium.

[0083] According to one embodiment of the present disclosure, one, two, three or all of R2, R3, R6 and R7 in the metal complex are selected from the group consisting of: deuterium, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms and a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms and combinations thereof.

[0084] According to one embodiment of the present disclosure, one, two, three, or all of R2, R3, R6, and R7 in the metal complex are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the above groups may be partially or fully deuterated.

[0085] According to one embodiment of the present disclosure, the ligand L a defined according to claim 28.

[0086] According to one embodiment of the present disclosure, the ligand L b defined according to claim 29.

[0087] According to one embodiment of the present disclosure, the metal complex is defined according to claim 30.

[0088] According to one embodiment of the present disclosure, the metal complex is defined according to claim 31.

[0089] According to one embodiment of the present disclosure, an electroluminescent device is disclosed comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex according to any one of the embodiments described above.

[0090] According to one embodiment of the present disclosure, the organic layer in the electroluminescent device is a light-emitting layer and the metal complex is a light-emitting material.

[0091] According to one embodiment of the present disclosure, the light-emitting layer of the electroluminescent device further comprises at least one host compound.

[0092] According to one embodiment of the present disclosure, the light-emitting layer of the electroluminescent device further comprises at least two host compounds.

[0093] According to one embodiment of the present disclosure, the at least one of the host compounds of the electroluminescent device has at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, aza-dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0094] According to one embodiment of the present disclosure, the electroluminescent device emits green or white light.

[0095] According to another embodiment of the present disclosure, a compound formulation is further disclosed which includes a metal complex whose specific structure is as in any of the embodiments described above. Combination with other materials

[0096] The materials described in the present disclosure for a particular layer in an organic light-emitting device can be used in combination with various other materials present in the device. The combinations of these materials are described in more detail in US 2016 / 0359 122 A1, paragraphs 132 to 161. The materials described or mentioned in the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of ordinary skill in the art can readily consult the literature to identify other materials that may be useful in combination.

[0097] The materials described herein as useful for a particular layer in an organic light-emitting device may be used in combination with a variety of other materials present in the device. For example, dopants disclosed herein may be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080 to 0101 of US 2015 / 0 349 273 A1. The materials described or mentioned in the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of ordinary skill in the art can readily consult the literature to identify other materials that may be useful in combination.

[0098] In the material synthesis embodiments, all reactions were carried out under nitrogen protection unless otherwise stated. All reaction solvents were anhydrous and used as obtained from commercial sources. Synthetic products were structurally confirmed and their properties were tested using one or more conventional state-of-the-art equipment (including, but not limited to, a nuclear magnetic resonance apparatus manufactured by Bruker, a liquid chromatography-mass spectrometer manufactured by Shimadzu, a liquid chromatography-mass spectrometer manufactured by Shimadzu, a gas chromatography-mass spectrometer manufactured by Shimadzu, a differential scanning calorimeter manufactured by Shimadzu, a fluorescence spectrophotometer manufactured by Shanghai Lengguang Tech., an electrochemical workstation manufactured by Wuhan Corrtest, and a sublimation device manufactured by ANHUI BEQ, etc.).) by methods well known to those skilled in the art. In the embodiments of the device, the characteristics of the device were also tested using conventional prior art equipment (including, but not limited to, an evaporator manufactured by ANGSTROM ENGI-NEERING, an optical inspection system manufactured by SUZHOU FATAR, a lifetime test system manufactured by SUZHOU FATAR, and an ellipsometer manufactured by BEIJING ELLITOP, etc.) by methods well known to those skilled in the art. Since the above-mentioned uses of the equipment, test methods, and other related contents are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without influence, so the above related contents are not further described in this patent. Example of material synthesis

[0099] The method for producing a compound in the present disclosure is not limited herein. Typically, the following compounds are used as examples without limitation, and their synthesis routes and production methods are described below. Synthesis Example 1: Synthesis of a Metal Complex 55Step 1:

[0100] 2-Phenylpyridine (6.5 g, 41.9 mmol), iridium trichloride trihydrate (3.6 g, 10.2 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were added sequentially to a dry 500 mL round-bottom flask, purged three times with nitrogen, placed in a 130 °C heating mantle, and heated and stirred under nitrogen for 24 h. The reaction product was cooled, filtered, washed three times with methanol and n-hexane, respectively, and pumped to dryness to afford 5.4 g of intermediate 1 (yield: 99%). Step 2:

[0101] Intermediate 1 (5.4 g, 5.0 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (2.6 g, 10.1 mmol) were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and stirred overnight under nitrogen protection at room temperature. The reaction product was filtered through Celite and washed twice with dichloromethane. The organic phase was then collected and concentrated under reduced pressure to afford 7.1 g of intermediate 2 (yield: 99%). Step 3:

[0102] Intermediate 3 (1.8 g, 4.5 mmol), intermediate 2 (2.2 g, 3.0 mmol), 50 mL of 2-ethoxyethanol, and 50 mL of N,N-dimethylformamide were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and heated at 100 °C for 96 h under nitrogen protection. The reaction was cooled, filtered through Celite, and washed twice with methanol and n-hexane, respectively. Yellow solids on the Celite were dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to afford 1.5 g of metal complex 55 (yield: 56%). The product structure was confirmed as the target product with a molecular mass of 895. Synthesis Example 2: Synthesis of a metal complex 97

[0103] Intermediate 4 (1.8 g, 4.4 mmol), intermediate 2 (2.1 g, 3.0 mmol), 50 mL of 2-ethoxyethanol, and 50 mL of N,N-dimethylformamide were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and heated at 100 °C for 96 h under nitrogen protection. The reaction was cooled, filtered through Celite, and washed twice with methanol and n-hexane, respectively. Yellow solids on the Celite were dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to afford 1.5 g of metal complex 97 (yield: 55%). The product structure was confirmed as the target product with a molecular mass of 905. Synthesis Example 3: Synthesis of a metal complex 261Step 1:

[0104] 4-Methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were added sequentially to a dry 500 mL round-bottom flask, purged three times with nitrogen, placed in a 130 °C heating mantle, and heated and stirred under nitrogen for 24 h. The reaction product was cooled, filtered, washed three times with methanol and n-hexane, respectively, and pumped to dryness to afford 7.9 g of intermediate 5 (yield: 99%). Step 2:

[0105] Intermediate 5 (7.9 g, 7.0 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (3.8 g, 14.8 mmol) were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and stirred overnight under nitrogen protection at room temperature. The reaction product was filtered through Celite and washed twice with dichloromethane. The organic phase was then collected and concentrated under reduced pressure to afford 10.0 g of intermediate 6 (yield: 96%). Step 3:

[0106] Intermediate 7 (2.2 g, 6.1 mmol), intermediate 6 (3.0 g, 4.0 mmol), 50 mL of 2-ethoxyethanol, and 50 mL of N,N-dimethylformamide were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and heated at 100 °C for 96 h under nitrogen protection. The reaction was cooled, filtered through Celite, and washed twice with methanol and n-hexane, respectively. Yellow solids on the Celite were dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to afford metal complex 261 as a yellow solid (2.1 g, yield: 59%). The product structure was confirmed as the target product with a molecular mass of 888. Synthesis Example 4: Synthesis of a metal complex 131Step 1:

[0107] 5-Methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were added sequentially to a dry 500 mL round-bottom flask, purged three times with nitrogen, placed in a 130 °C heating mantle, and heated and stirred under nitrogen for 24 h. The reaction product was cooled, filtered, washed three times with methanol and n-hexane, respectively, and pumped to dryness to afford 7.5 g of intermediate 8 as a yellow solid (yield: 97%). Step 2:

[0108] Intermediate 8 (7.5 g, 6.8 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (3.8 g, 14.8 mmol) were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and stirred overnight under nitrogen protection at room temperature. The reaction product was filtered through Celite and washed twice with dichloromethane. The organic phase was then collected and concentrated under reduced pressure to afford 9.2 g of intermediate 9 (yield: 93%). Step 3:

[0109] Intermediate 7 (2.2 g, 6.1 mmol), intermediate 9 (3.0 g, 4.0 mmol), 50 mL of 2-ethoxyethanol, and 50 mL of N,N-dimethylformamide were sequentially added to a dry 500 mL round-bottom flask, purged three times with nitrogen, and heated at 100 °C for 96 h under nitrogen protection. The reaction was cooled, filtered through Celite, and washed twice with methanol and n-hexane, respectively. Yellow solids on the Celite were dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to afford metal complex 131 as a yellow solid (1.5 g, yield: 42%). The product structure was confirmed as the target product with a molecular mass of 888.

[0110] Those skilled in the art will appreciate that the above manufacturing method is merely an illustrative example. Those skilled in the art can obtain other interconnect structures of the present disclosure by modifying the manufacturing method. Device example 1

[0111] First, a glass substrate with an indium tin oxide (ITO) anode with a thickness of 80 nm was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was mounted on a substrate carrier and placed in a vacuum chamber. The following organic layers were sequentially deposited by thermal vacuum evaporation on the ITO anode at a rate of 0.2 to 2 angstroms per second at a vacuum level of approximately 10 -8torr. A compound HI was used as the hole injection layer (HIL). A compound HT was used as the hole transporting layer (HTL). A compound EB was used as the electron blocking layer (EBL). The metal complex 55 of the present disclosure was doped into the compound EB and the compound HB, and the resulting mixture was co-deposited for use as an emissive layer (EML). On the EML, the compound HB was used for use as the hole blocking layer (HBL). On the HBL, a compound ET and 8-hydroxyquinolinolato lithium (Liq) were deposited for use as the electron transporting layer (ETL).Finally, 8-hydroxyquinolinolato lithium (Liq) was deposited at a thickness of 1 nm for use as the electron injection layer, and Al was deposited at a thickness of 120 nm for use as the cathode. The device was transferred back to the glove box and encapsulated with a glass lid and a moisture getter to complete the device. Device example 2

[0112] The reaction procedure in Device Example 2 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with the metal complex 97 of the present disclosure. Device example 3

[0113] The reaction procedure in Device Example 3 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with the metal complex 261 of the present disclosure. Device example 4

[0114] The reaction procedure in Device Example 4 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with the metal complex 131 of the present disclosure. Device comparison example 1

[0115] The reaction procedure in Comparative Device Example 1 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure in the EML was replaced by a comparative compound GD1. Device comparison example 2

[0116] The reaction procedure in Comparative Device Example 2 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure in the EML was replaced by a comparative compound GD2. Device comparison example 3

[0117] The reaction procedure in Comparative Device Example 3 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure in the EML was replaced by a comparative compound GD3. Device comparison example 4

[0118] The reaction procedure in Comparative Device Example 4 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with a comparative compound GD4. Device comparison example 5

[0119] The reaction procedure in Comparative Device Example 5 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with a comparative compound GD5. Device comparison example 6

[0120] The reaction procedure in Comparative Device Example 6 was the same as that in Device Example 1 except that the metal complex 55 of the present disclosure was replaced in the EML with a comparative compound GD7.

[0121] The exact structures and thicknesses of the device layers are shown in the following table. A layer using more than one material is obtained by doping different compounds in their weight ratio, as described. Table 1 Device structures in device examples Device ID HIL HTL EBL EML HBL ETL Example 1 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Metal complex 55 (46: 46: 8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40: 60) (350 Å) Example 2 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Metal complex 97 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Example 3 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Metal complex 261 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Example 4 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Metal complex 131 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Comparison example 1 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Compound GD1 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Comparison example 2 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Compound GD2 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Comparison example 3 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Compound GD3 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Comparison example 4 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Compound GD4 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å) Comparison example 5 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Connection EB: Connection HB: Compound HB (100 Å) Connection ET: Compound GD5 (46:46:8) (400 Å) Liq (40:60) (350 Å) Comparison example 6 Compound HI (100 Å) Compound HT (350 Å) Compound EB (50 Å) Compound EB: Compound HB: Compound GD7 (46:46:8) (400 Å) Compound HB (100 Å) Compound ET: Liq (40:60) (350 Å)

[0122] Structures of the materials used in the devices are shown as follows:

[0123] The current-voltage-luminance (IVL) characteristics of the devices were measured under a condition of 1,000 cd / m 2 CIE data, λ max , a full width at half maximum (FWHM), a drive voltage (V), a current efficiency (CE), a power efficiency (PE), and an external quantum efficiency (EQE) of the devices were measured. The data were collected and presented in Table 2. Table 2 Device data Device ID CIE (x, y) l max (nm) FWHM (nm) Voltage (V) CE (cd / A) PE (In / Out) EQE (%) Connection ET Example 1 (0,314, 0,649) 525 36,5 2,74 97 111 25,1 Example 2 (0,313, 0,649) 523 35,1 2,75 94 108 24,5 Example 3 (0,335, 0,649) 528 36,8 2,75 100 114 25,7 Example 4 (0,328, 0,642) 528 36,8 2,73 98 113 25,1 Comparison example 1 (0,335, 0,638) 528 42,7 2,76 103 117 26,0 Comparison example 2 (0,354, 0,626) 532 42,9 2,72 103 119 26,1 Comparison example 3 (0,331, 0,639) 527 51,3 2,73 91 105 23,3 Comparison example 4 (0,341, 0,630) 528 59,3 2,98 87 92 22,5 Comparison example 5 (0,329, 0,639) 526 51,2 2,72 93 108 24,1 Comparison example 6 (0,335, 0,629) 523 62,3 3,45 82 75 21,9 Discussion:

[0124] From the data presented in Table 2, although the EQE of Device Examples 1 to 3 is slightly lower than that of Comparative Device Examples 1 and 2, these EQE levels are still very high in the industry. However, the half-width of Device Example 1, which is 6.2 nm narrower than that of Comparative Device Example 1, the half-width of Device Example 2, which is 7.6 nm narrower than that of Comparative Device Example 1, and the half-width of Device Example 3, which is 6.1 nm narrower than that of Comparative Device Example 2, reach 36.5 nm, 35.1 nm, and 36.8 nm, respectively, which are very narrow. This indicates that the emitted light has very high color saturation, which is very rare.Furthermore, with regard to current efficiency and efficiency, it is apparent from the comparison of relevant data in Examples 1, 2, 3, and 4 and Comparative Examples 1, 2, and 3 that the introduction of deuterium, alkyl, deuterated alkyl, and other substituents into a pyridine ring of the ligand in the metal complex disclosed by the present disclosure can still enable maintaining high-level performance of related devices in the industry. Furthermore, the introduction of a substitution of the dibenzofuran pyridine ligand into the pyridine ring of the metal complex disclosed by the present disclosure enables a successful blue-shift of the emission wavelength of the device, thereby effectively adjusting the color of the light emitted by the device.

[0125] The EQE of Device Example 1 and the EQE of Device Example 2 are 7.7% and 5.2% higher, respectively, than that of Comparative Device Example 3, indicating that aryl substitution at a specific position in the metal complex disclosed by the present disclosure can improve the EQE of the material. Meanwhile, the half-width of Device Example 1 and the half-width of Device Example 2 are 14.8 nm and 16.2 nm, respectively, narrower than that of Comparative Device Example 3, indicating more significant advantages.

[0126] Compared with Comparative Device Example 5, Device Example 4 improves the EQE by 4%, significantly improves the current efficiency and efficiency, and, more importantly, significantly narrows the half-width by 14.4 nm, indicating very significant advantages. This further demonstrates that aryl substitution at a specific position in the metal complex disclosed by the present disclosure leads to excellent effects.

[0127] Compared with Comparative Device Example 6, Device Example 4 significantly improves the EQE by 14.6%, significantly improves the current efficiency and efficiency, significantly lowers the drive voltage, and, more importantly, significantly narrows the half-width by 25.5 nm, indicating very significant advantages. This further demonstrates that cyano substitution at a specific position in the metal complex disclosed by the present disclosure leads to excellent effects.

[0128] Furthermore, compared with the prior art (Comparative Example 4), Device Example 1, Device Example 2, Device Example 3, and Device Example 4 all exhibit significant advantages in various aspects of device performance. Compared with Comparative Device Example 4, Device Example 1, Device Example 2, Device Example 3, and Device Example 4 exhibit half-widths narrowed by 22.8 nm, 24.2 nm, 22.5 nm, and 22.5 nm, respectively; drive voltages lowered by 0.24 V, 0.23 V, 0.23 V, and 0.25 V, respectively; and EQE improved by 11.6%, 8.9%, 14.2%, and 11.6%, respectively.The results show that the present disclosure has significantly improved the device performance by various effects of cyano, aryl, and alkyl substitution at different positions of the dibenzofuran-pyridine ligand in the metal complex disclosed herein, compared with the prior art (Comparative Example 4).

[0129] In summary, compared with the prior art, the metal complex of the present disclosure exhibits remarkable effects of significantly narrowed half-width, greatly improved color saturation of the light emitted by the device, and, at the same time, significantly improved high efficiency and low voltage due to the structural design by introducing a specific aromatic ring and a cyano substituent into one specific ring of the ligand and, at the same time, introducing a substituent into another specific ring of the ligand. The metal complex disclosed by the present disclosure exhibits significant advantages and broad prospects in industrial applications. Spectroscopy data

[0130] The photoluminescence (PL) spectroscopy data of the metal complex of the present disclosure and the comparative compounds were measured using a fluorescence spectrophotometer F98 manufactured by SHANGHAI LENGGUANG TECHNOLOGY CO., LTD. The metal complex 131 of the present disclosure and the comparative compounds GD5, GD6, GD7, GD8, and GD9 were prepared using HPLC-grade toluene to form solutions each with a concentration of 3 × 10 -5 mol / l and then excited at room temperature (298 K) using light with a wavelength of 500 nm, and their emission spectra were measured.

[0131] The metal complex 131 of the present disclosure and the comparative compounds GD5, GD6, GD7, GD8 and GD9 have the following structures:

[0132] The maximum emission wavelength (λ max ) and the full width at half maximum (FWHM) of each of these compounds in PL spectroscopy are presented in Table 3. Table 3 Spectroscopy data Connection No. l max (nm) FWHM (nm) Metal complex 131 524 33,9 GD5 523 46,1 GD6 528 38,8 GD7 522 56,3 GD8 528 55,3 GD9 527 49,1

[0133] From the data in Table 3, it can be seen that, compared with those of comparative compounds GD5 and GD9, the half-width of the metal complex 131 disclosed by the present disclosure is significantly narrowed by 12.2 nm and 15.2 nm, respectively, indicating that the introduction of phenyl (aromatic ring) and methyl (substituent) into the ligand structure of the metal complex disclosed by the present disclosure can bring about the advantageous effect of greatly narrowing the half-width of the PL emission maximum for the metal complex. Compared with those of comparative compounds GD7 and GD8, the half-width of the metal complex 131 is significantly narrowed by 22.4 nm and 15.2 nm, respectively.21.4 nm, indicating that the introduction of cyano substitution and methyl (substituent) into the ligand structure of the metal complex disclosed by the present disclosure can bring about the advantageous effect of a greatly narrowed half-width of the PL emission maximum for the metal complex.

[0134] Furthermore, from the comparison of data between compounds GD7 and GD8, it can be found that GD7 introduces a methyl group (substituent) into the pyridine ring of the ligand, while the half-width of GD7 is 1 nm wider. However, the metal complex 131 disclosed by the present disclosure also introduces a methyl group (substituent) into the pyridine ring of the ligand. Surprisingly, its half-width was unexpectedly further narrowed by 4.9 nm based on the very narrow half-width (38.8 nm) of the comparative compound GD6. This result indicates that the introduction of methyl substitution into the pyridine ring in the pyridine-dibenzofuran ligand structure of the metal complex disclosed by the present disclosure brings about the unexpected excellent effect of greatly narrowing the half-width of the PL emission maximum for the metal complex.

[0135] Metal complex 131 of the present disclosure differs in structure from compound GD6 by an alkyl substituent, and compound GD5 similarly differs in structure from compound GD9 by an alkyl substituent at the same substitution position. However, the half-width of metal complex 131 of the present disclosure was 4.9 nm narrower than that of GD6, and the half-width of compound GD5 was 3 nm narrower than that of GD9. This result further demonstrates that the metal complex of the present disclosure can achieve significant and unexpected excellent effects through structural engineering, that is, the structural modification involving the introduction of a substituent into the pyridine ring of the ligand structure in combination with the introduction of cyano and aromatic ring substitution into the dibenzofuran structure.

[0136] The above data show that the PL emission wavelength of the metal complex of the present disclosure can be finely tuned and the metal complex can achieve an unexpected excellent effect of greatly narrowing the half-width of PL emission by a structural design by introducing a specific aromatic ring and a cyano substituent into a specific ring of the ligand and meanwhile introducing a substituent into another specific ring of the ligand.

Claims

[1] Metal complex having a general formula Ir(L a ) m (L b ) n where L is a and L b the first ligand and the second ligand, each coordinated to the metal Ir; and L a and L b can optionally be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2 and m+n is the oxidation state of the metal Ir; where, if m is greater than or equal to 2, the plurality of L a are the same or different; if n is 2, the two L b are the same or different; where L a has a structure represented by formula 1a: where Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different at each occurrence from CR x or N can be selected; Y1 to Y4 at each occurrence the same or different from CR y or N can be selected; X7 is CR x and the R x it is cyano; at least one of Y1 to Y4 is CR y and the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; R x and R yare selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these; Ar is selected at each occurrence, identically or differently, from the group consisting of: a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R yand Ar can optionally be connected to form a ring; L is b at each occurrence, the same or different, is any one selected from the group consisting of the following structures: where R a and R b represent, identically or differently at each occurrence, a monosubstitution, a multiple substitution or a non-substitution; R a and R bat each occurrence, identically or differently, are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms,a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations of these; and, in structures of L b neighboring substituents R a and R b can optionally be connected to form a ring. [2] Metal complex according to claim 1, wherein L is b at each occurrence, the same or different, is any one selected from the following structures: [3] Metal complex according to claim 1 or 2, wherein R a and R bat each occurrence, identically or differently, are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these. [4] A metal complex according to claim 3, which has a general formula Ir(L a ) m (L b ) 3-m and has a structure represented by a formula 2: where m is selected from 1 or 2; where, if m is 2, the two L a are equal or different; if m is 1, the two L b are the same or different; Z is selected from the group consisting of O, S, Se; X3 to X7 the same or different at each occurrence from CR x or N can be selected; Y1 to Y4 at each occurrence the same or different from CR y or N can be selected; X7 is CR x and the R x it is cyano; at least one of Y1 to Y4 is CR y and the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations thereof; where R x and R yare selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations of these; R1 to R8 are selected, identically or differently at each occurrence, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations of these; Ar is selected at each occurrence, identically or differently, from the group consisting of: a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and neighboring substituents R x , R y , Ar and R1 to R8 can optionally be connected to form a ring. [5] A metal complex according to any one of claims 1 to 3, wherein Z is selected from O and S. [6] Metal complex according to one of claims 1 to 5, wherein X3 to X7 on each occurrence are identical or different from CR x be selected. [7] Metal complex according to one of claims 1 to 5, wherein X3 to X7 on each occurrence are identical or different from CR x or N and at least one of X1 to X7 is N. [8] A metal complex according to any one of claims 1 to 7, wherein at least two of X3 to X7 are selected from CR x selected and where R x of X7 is Cyano and at least one of the R xat each occurrence, the same or different, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations of these. [9] The metal complex according to claim 8, wherein at least two of X3 to X7 are CR x selected, and where R x of X7 is Cyano and at least one of the R xat each occurrence, the same or different, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations thereof. [10] A metal complex according to claim 9, wherein at least one of R x at each occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 6 carbon atoms. [11] Metal complex according to one of claims 1 to 10, wherein Y1 to Y4 on each occurrence are identical or different from CR y be selected. [12] Metal complex according to one of claims 1 to 10, wherein Y1 to Y4 on each occurrence are identical or different from CR y or N is selected and at least one of Y1 to Y4 is N. [13] A metal complex according to any one of claims 1 to 11, wherein at least one of Y1 to Y4 is CR y is selected and the R y at each occurrence, the same or different, is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations of these. [14] The metal complex according to any one of claims 1 to 13, wherein Y2 and / or Y3 is CR y will be selected and the R yat each occurrence, the same or different, is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, and combinations thereof. [15] Metal complex according to claim 13, wherein Y2 and / or Y3 are CR y will be selected and the R y at each occurrence, identically or differently, is selected from a substituted alkyl having 1 to 12 carbon atoms, a substituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted aryl having 6 to 20 carbon atoms, or combinations thereof; and the substitution in the above substituted groups comprises at least one deuterium atom. [16] The metal complex according to claim 15, wherein R yat each occurrence, is selected, identically or differently, from the group consisting of: a partially or fully deuterated alkyl having 1 to 12 carbon atoms, a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof. [17] The metal complex according to claims 15 or 16, wherein when a carbon atom at a benzylic position in the R y is a primary carbon atom, a secondary carbon atom or a tertiary carbon atom, at least one deuterium atom is present in the R y is located at the benzylic position. [18] Metal complex according to any one of claims 15 to 17, wherein Y2 and / or Y3 is CR y will be selected and the R yis selected at each occurrence, identically or differently, from the group consisting of: a partially or fully deuterated alkyl having 1 to 12 carbon atoms, a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof; wherein, when a carbon atom at a benzylic position in the R y is a primary carbon atom, a secondary carbon atom or a tertiary carbon atom, hydrogen at the benzylic position in the R y is completely substituted by deuterium. [19] The metal complex according to any one of claims 15 to 18, wherein R y at each occurrence, the same or different, is selected from the group consisting of: CD3, CD2CH3, CD2CD3, CD(CH3)2, CD(CD3)2, CD2CH(CH3)2, CD2C(CH3)3, and combinations of these. [20] A metal complex according to any one of claims 1 to 12, wherein at least two of Y1 to Y4 on each occurrence are, identically or differently, selected from CR y selected and wherein at least one of the R y is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and at least one of R yselected from deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or combinations thereof. [21] The metal complex according to claim 20, wherein at least two of Y1 to Y4 at each occurrence are, identically or differently, selected from CR y selected and wherein at least one of the R y is selected from the group consisting of: a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof; and at least one of R y is deuterium. [22] Metal complex according to claim 20 or 21, wherein Y2 and / or Y3 are CR y will be selected and the R y at each occurrence, identically or differently, is selected from a partially or fully deuterated alkyl having 1 to 12 carbon atoms or a partially or fully deuterated cycloalkyl having 3 to 10 ring carbon atoms; and Y1 and / or Y4 are selected from CD. [23] A metal complex according to any one of claims 1 to 22, wherein Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, or combinations thereof; hydrogen in Ar is optionally partially or fully substituted by deuterium. [24] A metal complex according to any one of claims 4 to 23, wherein in formula 2 at least one or two of R1 to R8, the same or different at each occurrence, is (are) selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof. [25] The metal complex of claim 24, wherein at least one of R1 to R8 is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof. [26] A metal complex according to any one of claims 4 to 25, wherein in formula 2 at least one, two, three or all of R2, R3, R6 and R7 is (are) selected from the group consisting of: deuterium, fluorine, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms and combinations thereof. [27] The metal complex according to any one of claims 4 to 26, wherein one, two, three or all of R2, R3, R6 and R7 is (are) selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl and combinations thereof; optionally, the above groups may be partially or fully deuterated. [28] Metal complex according to claim 1, wherein the ligand L a at each occurrence, the same or different, is any one selected from the group consisting of: [29] Metal complex according to claim 28, wherein the ligand L b at each occurrence, the same or different, is any one selected from the group consisting of: [30] A metal complex according to claim 29, which has a structure represented by any one of Ir(L a )2(L b ) or Ir(L a )(L b )2; where, if the metal complex has the structure of Ir(L a )2(L b ), L a at each occurrence, is selected, identically or differently, from any one or any two of the group consisting of L a1 to L a32 , L a39 to L a76 , L a83 to L a114 , L a121 to La157 , L a164 to L a195 , L 202 to L a233 , L a240 to L a271 , L a276 to L a292 , L a541 to L a734 , L a795 to L a808 , and L a830 to L a839 exists and L b selected from any of the group consisting of L b1 to L b78 consists; if the metal complex has the structure of Ir(L a )(L b )2, L a selected from any of the group consisting of L a1 to L a32 , L a39 to L a76 , L a83 to L a114 , L a121 to L a157 , L a164 to L a195 , L 202 to L a233 , L a240 to L a271 , L a276 to L a292 , L a541 to L a734 , L a795 to L a808 , and L a830 to L a839 exists and L bat each occurrence, is selected, identically or differently, from any one or any two of the group consisting of L b1 to L b78 consists. [31] The metal complex of claim 30, wherein the metal complex is selected from the group listed in the table below; where the metal complex has the structure of Ir(L a )(L b )2, where the two L b are equal and L a and L b separately correspond to the structures listed in the following table: metal complex L a L b metal complex L a L b 1 L a2 L b1 2 L a3 L b1 3 L a6 L b1 4 L a8 L b1 5 L a9 L b1 6 L a10 L b1 7 L a11 L b1 8 L a12 L b1 9 L a13 L b1 10 L a14 L b1 11 L a15 L b1 12 L a16 L b1 13 L a17 L b1 14 L a18 L b1 15 L a19 L b1 16 L a20 L b1 17 L a21 L b1 18 L a23 L b1 19 L a25 L b1 20 L a27 L b1 21 L a29 L b1 22 L a31 L b1 25 L a39 L b1 26 L a41 L b1 27 L a46 L b1 28 L a50 L b1 29 L a53 L b1 30 L a59 L b1 31 L a60 L b1 32 L a84 L b1 33 L a88 L b1 34 L a91 L b1 36 L a123 L b1 37 L a124 L b1 38 L a127 L b1 39 L a134 L b1 40 L a136 L b1 41 L a146 L b1 42 L a166 L b1 43 L a172 L b1 44 L a203 L b1 45 L a204 L b1 46 L a207 L b1 47 L a241 L b1 48 L a242 L b1 49 L a245 L b1 50 L a248 L b1 51 L a250 L b1 52 L a254 L b1 53 L a255 L b1 54 L a256 L b1 55 L a276 L b1 56 L a277 L b1 92 L a541 L b1 93 L a549 L b1 94 L a593 L b1 95 L a560 L b1 96 L a562 L b1 97 L a563 L b1 98 L a567 L b1 99 L a581 L b1 100 L a588 L b1 101 L a590 L b1 102 L a591 L b1 103 L a595 L b1 104 L a596 L b1 105 L a597 L b1 106 L a603 L b1 107 L a616 L b1 108 L a617 L b1 109 L a618 L b1 110 L a619 L b1 111 L a620 L b1 112 L a644 L b1 113 L a645 L b1 114 L a647 L b1 125 L a795 L b1 126 L a802 L b1 131 L a2 L b3 132 L a3 L b3 133 L a6 L b3 134 L a6 L b3 135 L a9 L b3 136 L a10 L b3 137 L a11 L b3 138 L a12 L b3 139 L a13 L b3 140 L a14 L b3 141 L a15 L b3 142 L a16 L b3 143 L a17 L b3 144 L a18 L b3 145 L a19 L b3 146 L a20 L b3 147 L a21 L b3 148 L a23 L b3 149 L a25 L b3 150 L a27 L b3 151 L a29 L b3 152 L a31 L b3 155 L a39 L b3 156 L a41 L b3 157 L a46 L b3 158 L a50 L b3 159 L a53 L b3 160 L a59 L b3 161 L a60 L b3 162 L a84 L b3 163 L a83 L b3 164 L a91 L b3 166 L a123 L b3 167 L a124 L b3 168 L a127 L b3 169 L a134 L b3 170 L a136 L b3 171 L a146 L b3 172 L a166 L b3 173 L a172 L b3 174 L a203 L b3 175 L a204 L b3 176 L a207 L b3 177 L a241 L b3 178 L a242 L b3 179 L a245 L b3 180 L a248 L b3 181 L a250 L b3 182 L a254 L b3 183 L a255 L b3 184 L a256 L b3 185 L a276 L b3 186 L a277 L b3 223 L a549 L b3 224 L a593 L b3 225 L a560 L b3 226 L a562 L b3 227 L a563 L b3 228 L a567 L b3 229 L a581 L b3 230 L a588 L b3 231 L a590 L b3 232 L a591 L b3 233 L a595 L b3 234 L a596 L b3 235 L a597 L b3 236 L a603 L b3 237 L a616 L b3 238 L a617 L b3 239 L a618 L b3 240 L a619 L b3 241 L a620 L b3 242 L a644 L b3 243 L a645 L b3 244 L a647 L b3 255 L a795 L b3 256 L a802 L b3 261 L a2 L b4 262 L a3 L b4 263 L a6 L b4 264 L a6 L b4 265 L a9 L b4 266 L a10 L b4 267 L a11 L b4 268 L a12 L b4 269 L a13 L b4 270 L a14 L b4 271 L a15 L b4 272 L a16 L b4 273 L a17 L b4 274 L a18 L b4 275 L a19 L b4 276 L a20 L b4 277 L a21 L b4 278 L a23 L b4 279 L a25 L b4 280 L a27 L b4 281 L a29 L b4 282 L a31 L b4 285 L a39 L b4 286 L a41 L b4 287 L a46 L b4 288 L a50 L b4 289 L a53 L b4 290 L a59 L b4 291 L a60 L b4 292 L a84 L b4 293 L a88 L b4 294 L a91 L b4 296 L a123 L b4 297 L a124 L b4 298 L a127 L b4 299 L a134 L b4 300 L a136 L b4 301 L a146 L b4 302 L a166 L b4 303 L a172 L b4 304 L a203 L b4 305 L a204 L b4 306 L a207 L b4 307 L a241 L b4 308 L a242 L b4 309 L a245 L b4 310 L a248 L b4 311 L a250 L b4 312 L a254 L b4 313 L a255 L b4 314 L a256 L b4 315 L a276 L b4 316 L a277 L b4 352 L a541 L b4 353 L a549 L b4 354 L a593 L b4 355 L a560 L b4 356 L a562 L b4 357 L a563 L b4 358 L a567 L b4 359 L a581 L b4 360 L a588 L b4 361 L a590 L b4 362 L a591 L b4 363 L a595 L b4 364 L a596 L b4 365 L a597 L b4 366 L a603 L b4 367 L a616 L b4 368 L a617 L b4 369 L a618 L b4 370 L a619 L b4 371 L a620 L b4 372 L a644 L b4 373 L a645 L b4 374 L a647 L b4 385 L a795 L b4 386 L a802 L b4 391 L a2 L b8 392 L a3 L b8 393 L a6 L b8 394 L a6 L b8 395 L a9 L b8 396 L a10 L b8 397 L a11 L b8 398 L a12 L b8 399 L a13 L b8 400 L a14 L b8 401 L a15 L b8 402 L a16 L b8 403 L a17 L b8 404 L a18 L b8 405 L a19 L b8 406 L a20 L b8 407 L a21 L b8 408 L a23 L b8 409 L a25 L b8 410 L a27 L b8 411 L a29 L b8 412 L a31 L b8 415 L a39 L b8 416 L a41 L b8 417 L a46 L b8 418 L a50 L b8 419 L a53 L b8 420 L a59 L b8 421 L a60 L b8 422 L a84 L b8 423 L a88 L b8 424 L a91 L b8 426 L a123 L b8 427 L a124 L b8 428 L a127 L b8 429 L a134 L b8 430 L a136 L b8 431 L a146 L b8 432 L a166 L b8 433 L a172 L b8 434 L a203 L b8 435 L a204 L b8 436 L a207 L b8 437 L a241 L b8 438 L a242 L b8 439 L a245 L b8 440 L a248 L b8 441 L a250 L b8 442 L a254 L b8 443 L a255 L b8 444 L a256 L b8 445 L a276 L b8 446 L a277 L b8 482 L a541 L b8 483 L a549 L b8 484 L a593 L b8 485 L a560 L b8 486 L a562 L b8 487 L a563 L b8 488 L a567 L b8 489 L a581 L b8 490 L a588 L b8 491 L a590 L b8 492 L a591 L b8 493 L a595 L b8 494 L a596 L b8 495 L a597 L b8 496 L a603 L b8 497 L a616 L b8 498 L a617 L b8 499 L a618 L b8 500 L a619 L b8 501 L a620 L b8 502 L a644 L b8 503 L a645 L b8 504 L a647 L b8 515 L a795 L b8 516 L a802 L b8 521 L a2 L b30 522 L a3 L b30 523 L a6 L b30 524 L a6 L b30 525 L a9 L b30 526 L a10 L b30 527 L a11 L b30 528 L a12 L b30 529 L a13 L b30 530 L a14 L b30 531 L a15 L b30 532 L a16 L b30 533 L a17 L b30 534 L a18 L b30 535 L a19 L b30 536 L a20 L b30 537 L a21 L b30 538 L a23 L b30 539 L a25 L b30 540 L a27 L b30 541 L a29 L b30 542 L a31 L b30 545 L a39 L b30 546 L a41 L b30 547 L a46 L b30 548 L a50 L b30 549 L a53 L b30 550 L a59 L b30 551 L a60 L b30 552 L a84 L b30 553 L a88 L b30 554 L a91 L b30 556 L a123 L b30 557 L a124 L b30 558 L a127 L b30 559 L a134 L b30 560 L a136 L b30 561 L a146 L b30 562 L a166 L b30 563 L a172 L b30 564 L a203 L b30 565 L a204 L b30 566 L a207 L b30 567 L a241 L b30 568 L a242 L b30 569 L a245 L b30 570 L a248 L b30 571 L a250 L b30 572 L a254 L b30 573 L a255 L b30 574 L a256 L b30 575 L a276 L b30 576 L a277 L b30 612 L a541 L b30 613 L a549 L b30 614 L a593 L b30 615 L a560 L b30 616 L a562 L b30 617 L a563 L b30 618 L a567 L b30 619 L a581 L b30 620 L a588 L b30 621 L a590 L b30 622 L a591 L b30 623 L a595 L b30 624 L a596 L b30 625 L a597 L b30 626 L a603 L b30 627 L a616 L b30 628 L a617 L b30 629 L a618 L b30 630 L a619 L b30 631 L a620 L b30 632 L a644 L b30 633 L a645 L b30 634 L a647 L b30 635 L a740 L b30 636 L a741 L b30 645 L a795 L b30 646 L a802 L b30 [32] The metal complex of claim 5, wherein Z is 0. [33] The metal complex of claim 12, wherein Y3 is N. [34] The metal complex according to claim 13, wherein at least one of Y1 to Y4 is CR y is selected and the R yat each occurrence, the same or different, is selected from the group consisting of: halogen, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, and combinations thereof. [35] The metal complex according to claim 20, wherein at least two of Y1 to Y4 at each occurrence are, identically or differently, selected from CR y selected and wherein at least one of the R yis selected from the group consisting of: a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; and at least one of R y selected from deuterium, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or combinations thereof. [36] The metal complex of claim 23, wherein Ar is selected from substituted or unsubstituted phenyl; hydrogen in Ar is optionally partially or fully substituted by deuterium. [37] The metal complex of claim 26, wherein one, two, three or all of R2, R3, R6 and R7 is (are) selected from the group consisting of: deuterium, a substituted or unsubstituted alkyl having 1 to 12 carbon atoms and a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms and combinations thereof. [38] An electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 37. [39] An electroluminescent device according to claim 38, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material. [40] The electroluminescent device of claim 39, wherein the light-emitting layer further comprises at least one host compound; [41] The electroluminescent device of claim 40, wherein the light-emitting layer further comprises at least two host compounds. [42] The electroluminescent device of claim 40 or 41, wherein the at least one of the host compounds has at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, aza-dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof. [43] The electroluminescent device of claim 39, wherein the electroluminescent device emits green or white light. [44] A compound formulation comprising the metal complex according to any one of claims 1 to 37.

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