Organic layer containing a metal complex

Abstract

To disclose an electroluminescent material and device.SOLUTION: An electroluminescent material is a metal complex containing a metal M and a ligand La coordinated with the M, wherein La has a structure represented by Formula 1. The metal complexes can be used as light-emitting materials in electroluminescent devices. These novel metal complexes allow better tuning of the emission color of the device while maintaining an extremely narrow full width at half maximum, resulting in a deeper red emission, and lower a driving voltage or maintain a lower operating voltage of the device and greatly improve the efficiency of the device. These novel metal complexes can provide better device performance. The present invention further discloses electroluminescent devices and compound compositions.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound used in an organic electronic device such as an organic light-emitting device, and more particularly to a metal complex containing a ligand having a structure represented by Formula 1, an electroluminescent device containing the metal complex, and a compound composition. [Background technology]

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device containing an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and emissive layers (Applied Physics Letters, 1987, 51(12):913-915). Once a bias was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may contain multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer tremendous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them highly suitable for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs are divided into three different types depending on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. Triplets generated in the device are wasted through nonradiative decay pathways, resulting in an internal quantum efficiency (IQE) of only 25%, hindering the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs, which use triplet emission from heavy metal-containing complexes as the emitter. Therefore, singlet and triplet emissions can be harvested, achieving an IQE of 100%. Due to their high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, allowing excitons to transition from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons by triplet excitons threading between reverse systems (reverse intersystem crossing).

[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material used. Small molecules refer to non-polymeric organic or organometallic materials, and as long as they have a precise structure, the molecular weight of the small molecule can be large. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Post-polymerization during the manufacturing process can turn small molecule OLEDs into polymer OLEDs.

[0006] Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of an OLED can be achieved by the structural design of the emissive material. An OLED may contain one or more emissive layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still suffer from problems such as unsaturated blue, short lifetime, and high operating voltage. Commercially available full-color OLED displays generally use a mixed strategy, employing blue fluorescence and yellow, red, or green phosphorescence. Currently, phosphorescent OLEDs suffer from a rapid decrease in efficiency at high brightness. Furthermore, there is a demand for more saturated emission spectra, higher efficiency, and longer device lifetimes.

[0008] Phosphorescent metal complexes can be used as phosphorescent doping materials in the emissive layer in the fields of organic electroluminescence lighting and display. Currently developed metal complexes still have various shortcomings in their performance in electroluminescent devices. To meet the ever-increasing needs of the industry, such as lower voltages, higher device efficiency, specific wavelength ranges of luminescent color, more saturated luminescent color, and longer device life, further research and development of metal complexes is still needed. Summary of the Invention [Problem to be solved by the invention]

[0009] In order to solve at least some of the problems described above, the present invention provides a metal complex containing a ligand having a structure represented by Formula 1. The metal complex can be used as an emitting material in an organic electroluminescent device. These novel metal complexes can better control the emission color of the device while maintaining an extremely narrow full width at half maximum, achieving a deeper red emission, and reducing the device's driving voltage or maintaining a low voltage level, thereby significantly improving the device's efficiency. These novel metal complexes can provide better device performance. [Means for solving the problem]

[0010] According to one embodiment of the present invention, a metal M and a ligand L coordinated with M are a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a discloses a metal complex having a structure represented by formula 1:

[0011] [ka] (Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Ring C is selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 ring atoms; R i , R ii are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R iii represents, identically or differently, one or more substitutions at each occurrence; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iiiare the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or selected from the group consisting of unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring.

[0012] According to another embodiment of the present invention, there is provided an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex, the metal complex comprising a metal M and a ligand L coordinated to M. a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a Further disclosed is an electroluminescent device having a structure represented by Formula 1:

[0013] [ka] (Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Ring C is selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 ring atoms; R i , R ii are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R iii represents, identically or differently, one or more substitutions at each occurrence; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iiiare the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or selected from the group consisting of unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring.

[0014] According to other embodiments of the present invention, there is further disclosed a compound composition comprising the metal complex described in the above embodiments. [Effects of the Invention]

[0015] The novel metal complexes having polycyclic ligands according to the present invention can be used as light-emitting materials in electroluminescent devices. These novel metal complexes can better adjust the emission color of the device while maintaining a very narrow full width at half maximum, achieving deeper red light emission, and reducing the device's driving voltage or maintaining a low voltage level, thereby significantly improving device efficiency. These novel metal complexes can provide better device performance. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a schematic diagram of an organic light-emitting device that may include metal complex and compound compositions according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light-emitting device that may include the metal complex and compound compositions according to the present invention. [Figure 3] FIG. 1 is a structural schematic diagram of a typical top-emitting OLED device that may include the metal complex and compound compositions according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0017] OLEDs can be fabricated on a variety of substrates, including glass, plastic, and metal. FIG. 1 illustrates, by way of example and not limitation, an organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted from the drawings, if necessary. 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 emissive layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. Device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0018] There are many examples of each of these layers. Illustratively, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., incorporated herein by reference in its entirety. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin metal layer, such as Mg:Ag, coated thereon with a sputter-deposited transparent conductive ITO layer. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties, describe the principles and use of blocking layers in more detail. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, provides examples of injection layers. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, describes protective layers.

[0019] The structure of a typical top-emitting OLED device is shown in Figure 3. OLED device 300 includes an anode layer 301, a hole-injection layer (HIL) 302, a first hole-transport layer (HTL1) 303, a second hole-transport layer (HTL2) 304 (also called a prime layer), an emissive layer (EML) 305, a hole-blocking layer (HBL) 306 (the hole-blocking layer 306 is optional), an electron-transport layer (ETL) 307, an electron-injection layer (EIL) 308, a cathode layer 309, and a capping layer 310. The anode layer 301 is made of a highly reflective material or a combination of materials, including, but not limited to, Ag, Al, Ti, Cr, Pt, Ni, TiN, and combinations of the above materials with ITO and / or MoOx (molybdenum oxide). Typically, the reflectance of the anode is greater than 50%, preferably greater than 70%, and more preferably greater than 80%. The cathode layer 309 is a semi-transparent or transparent conductive material, including, but not limited to, MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or a combination thereof. The average transmittance of light having a wavelength in the visible light region is greater than 15%, preferably greater than 20%, and more preferably greater than 25%.

[0020] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0021] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0022] An OLED also requires an encapsulation layer. As shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 to protect against harmful substances, such as moisture and oxygen, from the outside. Any material capable of providing an encapsulation function, such as glass or an organic-inorganic hybrid layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the exterior of the OLED device. Multilayer thin-film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0023] Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lamps, head-up displays, fully or partially transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and tail lights.

[0024] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0025] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is relatively far from the substrate. Other layers may be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if various organic layers are present between the cathode and anode.

[0026] "Solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0027] It is believed that if a ligand directly enhances the photosensitizing properties of the emitting material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emitting material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand can modify the properties of the photosensitizing ligand.

[0028] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistics limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0029] On the other hand, E-type delayed fluorescence relies on the conversion of triplet and singlet excited states rather than the collision of two triplets. Compounds capable of generating E-type delayed fluorescence must have an extremely small singlet-triplet gap to allow for the energy state conversion. Thermal energy can activate the triplet-to-singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading between reverse intersystems (RISC) is sufficiently fast, the non-radiative decay from the triplet can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlets can be 100%, far exceeding the 25% spin statistics of the exciton due to electrochemical reactions.

[0030] The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T) is required. Organic non-metal-containing donor-acceptor emissive materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, ΔE S-T These states may include CT states. Donor-acceptor emissive materials are typically constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0031] Definitions of Substituent Terminology Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0032] As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. Illustrative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. The alkyl group may be substituted.

[0033] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may be substituted.

[0034] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropylsilylethyl. Heteroalkyl groups may also be substituted.

[0035] As used herein, the term "alkenyl group" includes linear, branched, and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 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 norbornylalkenyl groups. The alkenyl groups may be substituted.

[0036] As used herein, the term "alkynyl group" includes straight-chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group 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, and phenylpropynyl groups. Of these, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. The alkynyl group may be substituted.

[0037] As used herein, the term "aryl group" or "aromatic group" refers to both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group 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, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-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'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-dimethylphenyl, mesitylene, and m-tetraphenyl. The aryl group may also be substituted.

[0038] As used herein, the term "heterocyclic group" or "heterocycle" refers to a non-aromatic cyclic group. 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, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Heterocyclic groups may also be substituted.

[0039] As used herein, the term "heteroaryl group" refers to both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. The term "isoaryl group" also refers to heteroaryl groups. The heteroaryl group may be a heteroaryl group containing 3 to 30 carbon atoms, preferably a heteroaryl group containing 3 to 20 carbon atoms, and more preferably a heteroaryl group containing 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Heteroaryl groups may also be substituted.

[0040] As used herein, the alkoxy group refers to an -O-alkyl group, an -O-cycloalkyl group, an -O-heteroalkyl group, or an -O-heterocyclic group. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group, and the heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may be substituted.

[0041] As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.

[0042] As used herein, the term "aralkyl group" includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, 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, and 1-chloro-2-phenylisopropyl. Among these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.

[0043] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. The alkylsilyl group may also be substituted.

[0044] As used herein, the term "arylsilyl group" refers to a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.

[0045] As used herein, the term "alkylgermanium group" includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and is preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of the alkylgermanium group include a trimethylgermanium group, a triethylgermanium group, a methyldiethylgermanium group, an ethyldimethylgermanium group, a tripropylgermanium group, a tributylgermanium group, a triisopropylgermanium group, a methyldiisopropylgermanium group, a dimethylisopropylgermanium group, a tri-tert-butylgermanium group, a triisobutylgermanium group, a dimethyl-tert-butylgermanium group, and a methyldi-tert-butylgermanium group. The alkylgermanium group may also be substituted.

[0046] As used herein, the term "arylgermanium group" refers to a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, and is preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenyldibiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. The arylgermanium group may also be substituted.

[0047] The "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the replacement of one or more C—H groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.

[0048] In the present invention, unless otherwise specified, the following groups are included: a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted The use of any of the terms from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups means that any one of the groups is substituted with deuterium, halogen, non- Substituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, and unsubstituted heteroaryl groups having 3 to 30 carbon atoms. , an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanium group having 3 to 20 carbon atoms, an unsubstituted arylgermanium group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0049] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.

[0050] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.

[0051] In the compounds referred to herein, multiple substitution refers to a range up to the most available substitution, including double substitution. When a substituent in a compound referred to herein is referred to as multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on the bond structure, and the substituents present at all available substitution positions may be the same structure or different structures.

[0052] Unless specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, and adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents are not bonded to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such descriptions, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0053] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0054] [ka]

[0055] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0056] [ka]

[0057] The statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that two substituents bonded to carbon atoms further apart are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0058] [ka]

[0059] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. An example is shown in the following formula.

[0060] [ka]

[0061] According to one embodiment of the present invention, a metal M and a ligand L coordinated with M are a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a discloses a metal complex having a structure represented by formula 1:

[0062] [ka] (Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Ring C is selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 ring atoms; R i , R ii are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R iii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeRy R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R y are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iiiare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring.

[0063] In this specification, adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R i two substituents R ii two substituents R iii two substituents R y two substituents R x R i and R x R i and R iiiBetween the substituents R and R y and the substituent R iii and R may be bonded to each other to form a ring. Obviously, these substituents do not have to be bonded to each other to form a ring.

[0064] According to one embodiment of the present invention, R iii represents, identically or differently, one or more substitutions at each occurrence; R iii are the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted the alkyl group is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having 0 to 20 carbon atoms.

[0065] According to one embodiment of the present invention, the metal complex may contain other ligands. a may be combined with the ligand to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

[0066] According to one embodiment of the present invention, ring A and / or ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms, and ring C is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 6 to 18 ring atoms.

[0067] According to one embodiment of the present invention, ring A and / or ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms, and ring C is selected from an aromatic ring having 6 to 10 carbon atoms or a heteroaromatic ring having 6 to 10 ring atoms.

[0068] According to one embodiment of the present invention, the L a is selected from the structures represented by any one of formulas 2 to 17.

[0069] [ka] (In formulas 2 to 17, X1 to X2 are the same or different for each occurrence.) x or N, and X3 is CR i or N, and A1 to A6 are the same or different at each occurrence and are selected from CR ii or N, and X4 to X7 may be the same or different at each occurrence and are selected from CH, CR iii or N, and at least one of X4 to X7 is CR iii Selected from Z may be the same or different for each occurrence. iv R iv , SiR iv R iv , PR iv , O, S or NR iv Selected from two R iv When two R iv are the same or different, for example, Z is CR iv R iv If selected from two R iv may be the same or different, and may be, for example, SiR iv Riv If selected from two R iv may be the same or different, Y is SiR y R y , N.R. y , PR y , O, S or Se, and two R y When two R y may be the same or different, for example, Y is SiR y R y If selected from two R y may be the same or different, R, R x , R y , R i , R ii and R iv are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iiiare the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or selected from the group consisting of unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R i , R x , R y , R, R ii , R iii and R iv may be bonded to form a ring.

[0070] According to one embodiment of the present invention, L a is selected from the structures represented by formula 2 or formula 3.

[0071] According to one embodiment of the present invention, L a is selected from the structure represented by formula 3.

[0072] According to one embodiment of the present invention, in Formulas 2 to 17, X1 to X n and / or A1-A m At least one of the X is selected from N, ncorresponds to the largest number present in any one of the formulas 2 to 17 of X1 to X7, and A m corresponds to the largest number present in any one of the formulas 2 to 17 of A1 to A6. For example, in formula 3, the X n corresponds to X7, which is the largest number present in formula 3 of X1 to X7, and m corresponds to A4, which is the largest number present in formula 3 among A1 to A6, that is, in formula 3, at least one of X1 to X7 and / or A1 to A4 is selected from N.

[0073] According to one embodiment of the present invention, in Formulas 2 to 17, X1 to X n At least one of the X is selected from N, n corresponds to the largest number present in any one of formulas 2 to 17 of X1 to X7.

[0074] According to one embodiment of the present invention, in formulas 2 to 17, X2 is N.

[0075] According to one embodiment of the present invention, in Formulas 2 to 17, X1 and X2 are each independently CR x X3 is selected from CR i A1 to A6 are each independently selected from CR ii X4 to X7 are selected from the group consisting of CH and CR, and each occurrence may be the same or different. iii and at least one of X4 to X7 is CR iii and adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring.

[0076] In this specification, adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R ii two substituents Riii two substituents R x R i and R iii and the substituent R i and R x This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0077] According to one embodiment of the present invention, in Formulas 2 to 17, X1 and X2 are each independently CR x Selected from X3, CR i A1 to A6 are each independently selected from CR ii X4 to X7 are selected from the group consisting of CH and CR, and each occurrence may be the same or different. iii and at least one of X4 to X7 is CR iii wherein R x , R i , R ii are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; R iii are the same or different at each occurrence and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; Adjacent substituents R x , R i , R ii , Riii may be bonded to form a ring.

[0078] According to one embodiment of the present invention, in Formulas 2 to 17, X1 and X2 are each independently CR x Selected from X3, CR i A1 to A6 are each independently selected from CR ii X4 to X7 are selected from the group consisting of CH and CR, and each occurrence may be the same or different. iii and at least one of X4 to X7 is CR iii wherein R x , R i , R ii at least one or two of, each occurrence, are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; R iii is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof, and each occurrence may be the same or different; Adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring.

[0079] In this embodiment, the R x , R i , R iiare the same or different at each occurrence and are selected from the group of substituents. x Substituents, all R i Substituents and all R ii It means that at least one or two substituents of a group of substituents, at each occurrence, may be the same or different and are selected from the group of substituents.

[0080] According to one embodiment of the present invention, in Formulas 2 to 17, at least one or two of A1 to A6 are CR ii Selected from X3, CR i Selected from.

[0081] According to one embodiment of the present invention, in Formulas 2 to 17, at least one or two of A1 to A6 are CR ii wherein R ii are the same or different at each occurrence and are selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof; X3 is CR i wherein R i are the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

[0082] According to one embodiment of the present invention, in Formulas 2 to 17, at least one or two of A1 to A6 are CR iiwherein R ii is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof, and each occurrence may be the same or different; X3 is CR i wherein R i is, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0083] According to one embodiment of the present invention, in Formulas 2 to 17, R is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0084] According to an embodiment of the present invention, in Formulas 2 to 17, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, trimethylsilyl, or a combination thereof.

[0085] According to one embodiment of the present invention, in formulas 2 to 17, Y is selected from O or S.

[0086] According to one embodiment of the present invention, in formulas 2 to 17, Y is selected from O.

[0087] According to one embodiment of the present invention, in Formulas 2 to 17, X1 and X2 are each independently CR x Selected from.

[0088] According to one embodiment of the present invention, in Formulas 2 to 17, X1 is CR x X2 is selected from CR x Or selected from N.

[0089] According to one embodiment of the present invention, in Formulas 2 to 17, X1 is CR x X2 is selected from CR x or N, wherein R x are the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0090] According to one embodiment of the present invention, the ligand L a has the structure represented by formula 18.

[0091] [ka] (In formula 18, Y is selected from O or S; R x1 , R x2 , R i , R ii1 , R ii2 , Rii3 , R ii4 , R, R iii1 , R iii2 , R iii3 , R iii4 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iii1 , R iii2 , R iii3 , R iii4at least one of which may be the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, The alkyl group is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, all of which have 0 to 20 carbon atoms.

[0092] According to one embodiment of the present invention, the ligand L a has the structure represented by formula 18.

[0093] [ka] (In formula 18, Y is selected from O or S; R x1 , R x2 One or two of the following and / or R ii1 , R ii2 , R ii3 , R ii4at least one or two of, each occurrence, may be the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; R is selected from halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or combinations thereof; R iii1 , R iii2 , R iii3 , R iii4 and at least one or two of the groups, which may be the same or different at each occurrence, are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0094] According to one embodiment of the present invention, the ligand L a has the structure represented by formula 18.

[0095] [ka] (In formula 18, Y is selected from O or S; R x1 , R x2 One or two of the following and / or R ii1 , Rii2 , R ii3 and R ii4 at least one or two of, each occurrence, may be the same or different and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or combinations thereof; R iii1 , R iii2 , R iii3 , R iii4 and at least one or two of, each occurrence, may be the same or different and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0096] According to one embodiment of the present invention, in Equation 18: Y is selected from O or S; R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following are true: ii1 , R ii2 , R ii3 , R ii4at least one or two of, each occurrence, are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; R is selected from the group consisting of halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0097] According to one embodiment of the present invention, in Equation 18: Y is selected from O or S; R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following are true: ii1 , R ii2 , R ii3 , R ii4 at least one or two of, each occurrence, are the same or different and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; R is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

[0098] According to one embodiment of the present invention, in Formula 18, R ii1 , R ii2 , R ii3 One of the following (e.g., R ii1 or R ii2 or R ii3 ) or two (e.g., R ii1 and R ii2 , or R ii2 and R ii3 , or R ii1 and R ii3 ) are the same or different at each occurrence and are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

[0099] According to one embodiment of the present invention, in Formula 18, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.

[0100] In this example, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 and at least one of R is selected from the group of substituents, which may be the same or different at each occurrence, means that R x1 , R x2 at least one of R is selected from the group of substituents, whether identical or different at each occurrence, and / or R iii1 , R iii2 , R iii3 , R iii4 at least one of R is selected from the group of substituents, whether identical or different at each occurrence, and / or R ii1 , R ii2 , R ii3 , R ii4 is selected from the group of substituents, and / or R is selected from the group of substituents.

[0101] According to one embodiment of the present invention, in Formula 18, R iii2 , R iii3 , R ii1 , R ii2 , R ii3 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.

[0102] In this example, R iii2 , R iii3 , R ii1 , R ii2 , R ii3 and at least one of R is selected from the group of substituents, which may be the same or different at each occurrence, means that R iii2 , R iii3at least one of R is selected from the group of substituents, whether identical or different at each occurrence, and / or R ii1 , R ii2 , R ii3 is selected from the group of substituents, and / or R is selected from the group of substituents.

[0103] According to one embodiment of the present invention, in Formula 18, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.

[0104] In this example, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 and at least one of R is selected from the group of substituents, which may be the same or different at each occurrence, means that R x1 , R x2 at least one of R is selected from the group of substituents, whether identical or different at each occurrence, and / or R iii1 , R iii2 , R iii3 , R iii4 at least one of R is selected from the group of substituents, whether identical or different at each occurrence, and / or R ii1 , R ii2 , R ii3 , R ii4is selected from the group of substituents, and / or R is selected from the group of substituents.

[0105] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1904 The L is selected from the group consisting of a1 ~L a1904 The specific structure is shown in claim 12.

[0106] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1906 The L is selected from the group consisting of a1 ~L a1904 A specific structure of L is shown in claim 12. a1905 ~L a1906 is as follows:

[0107] [ka]

[0108] According to one embodiment of the present invention, the L a1 ~L a1904 The hydrogen atoms in the structure may be partially or completely replaced with deuterium atoms.

[0109] According to one embodiment of the present invention, the L a1 ~L a1906 The hydrogen atoms in the structure may be partially or completely replaced with deuterium atoms.

[0110] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b ) n (L c ) q It has the following structure. (Metal M is selected from metals with a relative atomic mass greater than 40, L a , L band L c are the first, second and third ligands of the complex, respectively; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; m+n+q equals the oxidation state of the metal M; and when m is greater than 1, multiple L a are the same or different, and if n is 2, the two L b are the same or different, and if q is 2, the two L c are the same or different, L a , L b and L c may be linked to form multidentate ligands, e.g., L a , L b and L c may be linked to form a tetradentate or hexadentate ligand, and L a , L b and L c may not be bonded to form a multidentate ligand, L b and L c may be the same or different for each occurrence [ka] selected from the group consisting of R a , R b and R c are the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 and CR C1 R C2 selected from the group consisting of X c and X d are O, S, Se and NR, which may be the same or different for each occurrence. N2 selected from the group consisting of R a , R b , R c , R N1 , R N2 , R C1 and R C2are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring.

[0111] In this example, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R a two substituents R b two substituents R c R a and R b R a and Rc R b and R c R a and R N1 R b and R N1 R c and R N1 R a and R C1 R a and R C2 R b and R C1 R b and R C2 R c and R C1 R c and R C2 R a and R N2 R b and R N2 Comrades and R C1 and R C2 This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0112] In this example, L a , L b and L c may be bonded to form a multidentate ligand means that L a , L b and L c It means that any two or three of L may combine to form a tetradentate or hexadentate ligand. a , L b and L c may not be bonded to form a multidentate ligand.

[0113] According to one embodiment of the invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0114] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0115] According to one embodiment of the present invention, the metal M is Ir.

[0116] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures:

[0117] [ka] (R1 to R7 each may be the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. , a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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.

[0118] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures:

[0119] [ka] (at least one of R1 to R3, at each occurrence, is the same or different and is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least one of R4 to R6, at each occurrence, is the same or different and is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.)

[0120] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures:

[0121] [ka] (at least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.)

[0122] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures:

[0123] [ka] (at least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof, and / or at least two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof)

[0124] According to one embodiment of the present invention, the metal complex has the formula Ir(L a ) m (L b ) 3-m and has a structure represented by formula 1-1 or 1-2.

[0125] [ka] (m is 1 or 2, X1~X2 are the same or different for each occurrence. x or N, and X3 may be the same or different for each occurrence and may be selected from CR i or N, and A1 to A4 are the same or different for each occurrence and are selected from CR ii or N, and X4 to X7 may be the same or different at each occurrence and are selected from CH, CR iii or N, and at least one of X4 to X7 is CR iii Selected from Y is SiR y R y , N.R. y , PR y , O, S or Se, and two R y When two R y are the same or different, R, R x , R y , R i , R iiR1, R2, R3, R4, R5, R6, and R7 each may be the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms. a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl 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; R iiiare the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or selected from the group consisting of unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R and R x , R y , R i , R ii and R iii may be bonded to form a ring, Adjacent substituents R1, R2, R3, R4, R5, R6, and R7 may be bonded to form a ring.

[0126] According to one embodiment of the present invention, at least one or two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and / or at least one or two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0127] According to one embodiment of the present invention, at least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof; and / or at least two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

[0128] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b322 and L c may be the same or different for each occurrence of L c1 ~L c231 wherein said L b1 ~L b322 and L c1 ~L c231 The specific structure is shown in claim 17.

[0129] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )2(Lc ) or Ir(L a )(L c )2 or Ir(L a )(L b )(L c ) structure.

[0130] Among them, the metal complex is Ir(L a )2(L b ), L a may be the same or different for each occurrence of L a1 ~L a1904 and L b L b1 ~L b322 and the metal complex is Ir(L a )2(L c ), L a may be the same or different for each occurrence of L a1 ~L a1904 and L c L c1 ~L c231 and the metal complex is Ir(L a )(L c )2, L a L a1 ~L a1904 and L c may be the same or different for each occurrence of L c1 ~L c231 and the metal complex is Ir(L a )(L b )(L c ), L a L a1 ~L a1904 and L b L b1 ~L b322 and L c L c1 ~Lc231 It is any one selected from the group consisting of:

[0131] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compounds 1 to 1010, and specific structures of Compounds 1 to 1010 are set forth in claim 18.

[0132] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 or Ir(L a )(L b )(L c ) structure.

[0133] Among them, the metal complex is Ir(L a )2(L b ), L a may be the same or different for each occurrence of L a1 ~L a1906 and L b L b1 ~L b322 and the metal complex is Ir(L a )2(L c ), L a may be the same or different for each occurrence of L a1 ~L a1906 and L c L c1 ~L c231 and the metal complex is Ir(L a )(L c )2, L a L a1 ~L a1906 and L c may be the same or different for each occurrence of L c1 ~Lc231 and the metal complex is Ir(L a )(L b )(L c ), L a L a1 ~L a1906 and L b L b1 ~L b322 and L c L c1 ~L c231 It is any one selected from the group consisting of:

[0134] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 1028, The compounds 1 to 800 and compounds 1011 to 1028 are Ir(L a )2(L b ) structure, of which two L a are identical, and L a and L b are selected from the structures shown in the table below,

[0135] [Table 1]

[0136] [Table 2]

[0137] [Table 3]

[0138] [Table 4]

[0139] [Table 5]

[0140] [Table 6]

[0141] [Table 7]

[0142] [Table 8]

[0143] [Table 9]

[0144] [Table 10]

[0145] Compounds 801 to 1010 are Ir(L a )2(L b ) structure, of which two L a is different, L a and L b are selected from the structures shown in the table below.

[0146] [Table 11]

[0147] [Table 12]

[0148] [Table 13]

[0149] According to one embodiment of the present invention, an anode; A cathode; Further disclosed is an electroluminescent device comprising: an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex, and a specific structure of the metal complex is shown in any one of the above examples.

[0150] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

[0151] According to one embodiment of the present invention, the electroluminescent element emits red light.

[0152] According to one embodiment of the present invention, the electroluminescent element emits white light.

[0153] According to an embodiment of the present invention, in the electroluminescent device, the organic layer is an emitting layer, and the emitting layer further comprises at least one host material.

[0154] According to one embodiment of the present invention, in the electroluminescent device, at least one of the host materials comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0155] According to another embodiment of the present invention, there is further disclosed a compound composition comprising a metal complex, the specific structure of which is shown in any one of the above embodiments.

[0156] Combination with other materials The materials of the specific layers used in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132 to 0161 of U.S. Patent Application No. US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. The materials described or referenced are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0157] It is noted herein that specific layer materials used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0158] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, a differential scanning calorimeter, a Shanghai Lingguang Technology fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system, a service life test system from Suzhou Fusida, an ellipsometer from Beijing Liangtuo, and the like) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification. [Example]

[0159] Examples of material synthesis: The preparation method of the compound according to the present invention is not limited. Taking the following compound as a typical but non-limiting example, its synthetic route and preparation method are as follows:

[0160] Synthetic Example 1: Synthesis of Compound 341 Step 1: Synthesis of intermediate 3: [ka]

[0161] Intermediate 1 (2.1 g, 5.2 mmol), Intermediate 2 (2.43 g, 5.2 mmol), tetrakis(triphenylphosphine)palladium (0.295 g, 0.26 mmol), sodium carbonate (0.818 g, 7.7 mmol), 1,4-dioxane (20 mL), and water (5 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:3, v / v) afforded Intermediate 3 (2.9 g, 78.5% yield) as a white solid.

[0162] Step 2: Synthesis of intermediate 4: [ka]

[0163] Intermediate 3 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol. 10 mL of 2 M HCl was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then dried to give Intermediate 4 (2.6 g, 97.2% yield) as a yellow solid.

[0164] Step 3: Synthesis of intermediate 5: [ka]

[0165] Intermediate 4 (2.6 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol), and DMF (40 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give intermediate 5 (2 g, 99.9% yield) as a yellow solid.

[0166] Step 4: Synthesis of intermediate 6: [ka]

[0167] Intermediate 5 (2 g, 4 mmol), neopentylboronic acid (935 mg, 8 mmol), palladium acetate (90 mg, 0.4 mmol), Sphos (328 mg, 0.8 mmol), potassium phosphate trihydrate (3.2 g, 12 mmol), and toluene (30 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) gave intermediate 6 (2 g, 94.4% yield) as a yellow solid.

[0168] Step 5: Synthesis of Iridium Dimer: [ka]

[0169] A mixture of intermediate 6 (1.1 g, 2.08 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0170] Step 6: Synthesis of Compound 341 [ka]

[0171] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3-methylnonane-4,6-dione (271 mg, 1.2 mmol), and potassium carbonate (0.57 g, 4.15 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.27 g of compound 341 (22% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1474.8.

[0172] Synthetic Example 2: Synthesis of Compound 441 Step 1: Synthesis of compound 441 [ka]

[0173] The ethoxyethanol solution of the iridium dimer obtained in Step 5 of Synthesis Example 1, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (58 mg, 0.24 mmol), and potassium carbonate (0.11 g, 0.8 mmol) were added to a 50 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.05 g of the product, Compound 441, was obtained (yield 21%). LC-MS confirmed the structure of the target product with a molecular weight of 1488.8.

[0174] Synthetic Example 3: Synthesis of Compound 442 Step 1: Synthesis of intermediate 8: [ka]

[0175] Intermediate 7 (1.6 g, 4.1 mmol), Intermediate 2 (1.93 g, 4.1 mmol), tetrakis(triphenylphosphine)palladium (0.237 g, 0.2 mmol), sodium carbonate (0.652 g, 6.2 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:3, v / v) afforded Intermediate 8 (2.46 g, 86.5% yield) as a white solid.

[0176] Step 2: Synthesis of intermediate 9: [ka]

[0177] Intermediate 8 (2.46 g, 3.5 mmol) was dissolved in 10 mL of ethanol. 10 mL of 2 M HCl was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then dried to give Intermediate 9 (2.32 g, 99.9% yield) as a yellow solid.

[0178] Step 3: Synthesis of intermediate 10: [ka]

[0179] Intermediate 9 (2.32 g, 3.65 mmol), cesium carbonate (3.56 g, 10.9 mmol), and DMF (35 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give Intermediate 10 (1.4 g, 80.3% yield) as a yellow solid.

[0180] Step 4: Synthesis of iridium dimer: [ka]

[0181] A mixture of intermediate 10 (1.4 g, 2.93 mmol), iridium trichloride trihydrate (344 mg, 0.98 mmol), 2-ethoxyethanol (21 mL), and water (7 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0182] Step 5: Synthesis of Compound 442 [ka]

[0183] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (353 mg, 1.47 mmol), and potassium carbonate (0.67 g, 4.9 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.88 g of compound 442 (64.8% yield) was obtained. The product was further purified by silica gel column chromatography. LC-MS confirmed the structure of the target product with a molecular weight of 1384.6.

[0184] Synthetic Example 4: Synthesis of Compound 438 Step 1: Synthesis of intermediate 12: [ka]

[0185] Intermediate 1 (1.45 g, 3.59 mmol), Intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction mixture was heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Ethyl acetate was added to the reaction mixture, the solution was separated, and the liquid phase was extracted with ethyl acetate. The organic phases were combined, dried, and then rotary evaporated to completely remove the solvent. The crude product was obtained by silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:2, v / v) to give Intermediate 12 (2.2 g, 95.7% yield) as a white solid.

[0186] Step 2: Synthesis of intermediate 13: [ka]

[0187] Intermediate 12 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol. 2 M HCl (10 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then dried to give Intermediate 13 (1.8 g, 99.8% yield) as a yellow solid.

[0188] Step 3: Synthesis of intermediate 14: [ka]

[0189] Intermediate 13 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (30 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give intermediate 14 (1.2 g, 83.2% yield) as a yellow solid.

[0190] Step 4: Synthesis of intermediate 15: [ka]

[0191] Intermediate 14 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) gave intermediate 15 (0.88 g, 67.5% yield) as a yellow solid.

[0192] Step 5: Synthesis of Iridium Dimer: [ka]

[0193] A mixture of intermediate 15 (0.88 g, 1.91 mmol), iridium trichloride trihydrate (193 mg, 0.55 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0194] Step 6: Synthesis of Compound 438 [ka]

[0195] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (200 mg, 0.83 mmol), and potassium carbonate (0.38 g, 2.75 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.41 g of compound 438 was obtained, yielding 55.3%. LC-MS confirmed the structure of the compound, which was the target product with a molecular weight of 1348.7.

[0196] Synthetic Example 5: Synthesis of Compound 446 Step 1: Synthesis of intermediate 17: [ka]

[0197] Intermediate 16 (1.45 g, 3.59 mmol), Intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:2, v / v) afforded Intermediate 17 (2.0 g, 90% yield) as a white solid.

[0198] Step 2: Synthesis of intermediate 18: [ka]

[0199] Intermediate 17 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol. 2 M HCl (10 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then pumped to dryness to give Intermediate 18 (1.8 g, 99.8% yield) as a yellow solid.

[0200] Step 3: Synthesis of intermediate 19: [ka]

[0201] Intermediate 18 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (35 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give intermediate 19 (1.2 g, 83.2% yield) as a yellow solid.

[0202] Step 4: Synthesis of intermediate 20: [ka]

[0203] Intermediate 19 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:50, v / v) gave intermediate 20 (0.88 g, 67.5% yield) as a yellow solid.

[0204] Step 5: Synthesis of Iridium Dimer: [ka]

[0205] A mixture of intermediate 20 (0.51 g, 1.1 mmol), iridium trichloride trihydrate (130 mg, 0.37 mmol), 2-ethoxyethanol (27 mL), and water (9 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0206] Step 6: Synthesis of Compound 446 [ka]

[0207] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (130 mg, 0.55 mmol), and potassium carbonate (0.26 g, 1.85 mmol) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.24 g of compound 446 (48% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1348.7.

[0208] Synthetic Example 6: Synthesis of Compound 1021 Step 1: Synthesis of intermediate 21: [ka]

[0209] Intermediate 16 (1.89 g, 4.68 mmol), Intermediate 2 (2.18 g, 4.67 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), sodium carbonate (0.74 g, 7 mmol), 1,4-dioxane (28 mL), and water (7 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:2, v / v) afforded Intermediate 21 (2.3 g, 70% yield) as a white solid.

[0210] Step 2: Synthesis of intermediate 22: [ka]

[0211] Intermediate 21 (4.5 g, 6.34 mmol) was dissolved in 30 mL of ethanol. 2 M HCl (30 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then pumped to dryness to give Intermediate 22 (3.1 g, 99.8% yield) as a yellow solid.

[0212] Step 3: Synthesis of intermediate 23: [ka]

[0213] Intermediate 22 (3.1 g, 6.34 mmol), cesium carbonate (5.16 g, 15.8 mmol), and DMF (50 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and then dried to give Intermediate 23 (5.5 g, 88% yield) as a yellow solid.

[0214] Step 4: Synthesis of intermediate 24: [ka]

[0215] Intermediate 23 (3.13 g, 6.3 mmol), neopentylboronic acid (2.21 g, 19 mmol), palladium acetate (144 mg, 0.64 mmol), Sphos (525 mg, 1.28 mmol), potassium phosphate trihydrate (5.1 g, 19.02 mmol), and toluene (30 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) gave intermediate 24 (2.6 g, 75% yield) as a yellow solid.

[0216] Step 5: Synthesis of Iridium Dimer: [ka]

[0217] A mixture of intermediate 24 (1.6 g, 3 mmol), iridium trichloride trihydrate (356 mg, 1 mmol), 2-ethoxyethanol (36 mL), and water (12 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the mixture was filtered, the solid was washed with methanol, and dried under vacuum to give the iridium dimer, which was used in the next step without further purification.

[0218] Step 6: Synthesis of Compound 1021 [ka]

[0219] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (360 mg, 1.5 mmol), potassium carbonate (0.69 g, 5 mmol), and 2-ethoxyethanol (35 mL) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.1 g of compound 1021 (6% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1488.8.

[0220] Synthetic Example 7: Synthesis of Compound 405 Step 1: Synthesis of intermediate 26: [ka]

[0221] Intermediate 25 (1.45 g, 3.59 mmol), Intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:2, v / v) afforded Intermediate 26 (2.2 g, 95.7% yield) as a white solid.

[0222] Step 2: Synthesis of intermediate 27: [ka]

[0223] Intermediate 26 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol. 2 M HCl (10 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then dried to give Intermediate 27 (1.8 g, 99.8% yield) as a yellow solid.

[0224] Step 3: Synthesis of intermediate 28: [ka]

[0225] Intermediate 27 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (35 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give intermediate 28 (1.2 g, 83.2% yield) as a yellow solid.

[0226] Step 4: Synthesis of intermediate 29: [ka]

[0227] Intermediate 28 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a separatory funnel containing diatomaceous earth, and the filtrate was collected. The solvent was then completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:50, v / v) afforded intermediate 29 (0.88 g, 67.5% yield) as a yellow solid.

[0228] Step 5: Synthesis of Iridium Dimer: [ka]

[0229] A mixture of intermediate 29 (0.88 g, 1.91 mmol), iridium trichloride trihydrate (193 mg, 0.55 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the mixture was filtered to give 210 mg of the iridium dimer, which was used in the next step without further purification.

[0230] Step 6: Synthesis of Compound 405 [ka]

[0231] The iridium dimer (210 mg, 0.114 mmol) obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (165 mg, 0.69 mmol), potassium carbonate (0.1 g, 1.35 mmol), and ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.1 g of compound 405 (yield 13.5%) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1348.7.

[0232] Synthetic Example 8: Synthesis of Compound 205 Step 1: Synthesis of Compound 205 [ka]

[0233] The iridium dimer (210 mg, 0.114 mmol) obtained in Step 5 of Synthesis Example 7, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (184 mg, 0.69 mmol), potassium carbonate (0.1 g, 1.35 mmol), and ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed, to obtain 0.1 g of compound 205 (yield 13.2%). LC-MS confirmed the structure of the target product with a molecular weight of 1374.6.

[0234] Synthetic Example 9: Synthesis of Compound 1019 Step 1: Synthesis of intermediate 31: [ka]

[0235] Intermediate 30 (2.2 g, 5.2 mmol), Intermediate 11 (2.43 g, 5.2 mmol), tetrakis(triphenylphosphine)palladium (0.295 g, 0.26 mmol), sodium carbonate (0.818 g, 7.7 mmol), 1,4-dioxane (20 mL), and water (5 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:3, v / v) afforded Intermediate 31 (2.9 g, 76.5% yield) as a white solid.

[0236] Step 2: Synthesis of intermediate 32: [ka]

[0237] Intermediate 31 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol. 2 M HCl (10 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then pumped to dryness to give Intermediate 32 (2.7 g, 97.2% yield) as a yellow solid.

[0238] Step 3: Synthesis of intermediate 33: [ka]

[0239] Intermediate 32 (2.7 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol), and DMF (40 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and dried to give intermediate 33 (2 g, 98.4% yield) as a yellow solid.

[0240] Step 4: Synthesis of intermediate 34: [ka]

[0241] Intermediate 33 (2 g, 3.94 mmol), neopentylboronic acid (914 mg, 7.88 mmol), palladium acetate (90 mg, 0.4 mmol), Sphos (328 mg, 0.8 mmol), potassium phosphate trihydrate (3.2 g, 12 mmol), and toluene (30 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) gave intermediate 34 (1.1 g, 50.6% yield) as a yellow solid.

[0242] Step 5: Synthesis of Iridium Dimer: [ka]

[0243] A mixture of intermediate 34 (1.1 g, 2.02 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0244] Step 6: Synthesis of Compound 1019 [ka]

[0245] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (271 mg, 1.2 mmol), and potassium carbonate (0.57 g, 4.15 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.22 g of compound 1019 (yield 17.5%) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1376.7.

[0246] Synthetic Example 10: Synthesis of Compound 447 Step 1: Synthesis of intermediate 36: [ka]

[0247] Intermediate 16 (2.61 g, 6.47 mmol), Intermediate 35 (2.67 g, 6.47 mmol), tetrakis(triphenylphosphine)palladium (0.37 g, 0.32 mmol), sodium carbonate (1.03 g, 9.7 mmol), 1,4-dioxane (52 mL), and water (13 mL) were added to a round-bottom flask. Under nitrogen gas protection, the reaction was heated to 90 °C and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and spun to completely remove the solvent by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:2, v / v) afforded the desired product, Intermediate 36 (3.1 g, 72%), as a white solid.

[0248] Step 2: Synthesis of intermediate 37: [ka]

[0249] Intermediate 36 (3.12 g, 4.77 mmol) was dissolved in 20 mL of ethanol. 2N HCl (20 mL) was added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed multiple times with water and then dried to give the desired product, Intermediate 37 (2.74 g, 96%) as a yellow solid.

[0250] Step 3: Synthesis of intermediate 38: [ka]

[0251] Intermediate 37 (2.74 g, 4.6 mmol), cesium carbonate (3.89 g, 11.93 mmol), and DMF (40 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Water was added until a large amount of yellow solid precipitated from the solution, which was then filtered. The solid was washed several times with water and then dried to give the desired product, Intermediate 38 (1.84 g, 91%), as a yellow solid.

[0252] Step 4: Synthesis of intermediate 39: [ka]

[0253] Intermediate 38 (0.56 g, 1.27 mmol), neopentylboronic acid (0.42 g, 3.81 mmol), Pd2(dba)3 (0.058 g, 0.06 mmol), Sphos (0.052 g, 0.127 mmol), potassium phosphate trihydrate (1.02 g, 3.81 mmol), and toluene (15 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The mixture was filtered through a diatomaceous earth funnel and the filtrate was collected. The solvent was completely removed by rotary evaporation to give the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:100, v / v) afforded the desired product, intermediate 39 (0.58 g, 95%), as a yellow solid.

[0254] Step 5: Synthesis of Iridium Dimer: [ka]

[0255] A mixture of intermediate 39 (0.58 g, 1.23 mmol), iridium trichloride trihydrate (0.12 g, 0.35 mmol), 2-ethoxyethanol (36 mL), and water (12 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0256] Step 6: Synthesis of Compound 447 [ka]

[0257] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.13 g, 0.53 mmol), potassium carbonate (0.69 g, 5 mmol), and 2-ethoxyethanol (35 mL) were added to a round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.18 g of the product, Compound 447, was obtained (37% yield). LC-MS confirmed the structure of the target product with a molecular weight of 1376.7.

[0258] Synthetic Example 11: Synthesis of Compound 1020 Step 1: Synthesis of iridium dimer: [ka]

[0259] A mixture of intermediate 40 (1 g, 2.17 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0260] Step 2: Synthesis of Compound 1020 [ka]

[0261] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (271 mg, 1.2 mmol), and potassium carbonate (0.57 g, 4.15 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.45 g of compound 1020 (40.1% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1350.7.

[0262] Synthetic Example 12: Synthesis of Compound 1018 Step 1: Synthesis of intermediate 41: [ka]

[0263] Intermediate 19 (344 mg, 0.81 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium dichloride (28 mg, 0.04 mmol) were dissolved in THF (5 mL). Under nitrogen gas protection, a 2 mol / L THF solution of 3,3,3-trifluoro-2,2-dimethylpropylmagnesium bromide (4 mL) was added and the reaction was carried out at 45 °C. After LC-MS showed the disappearance of intermediate 19, the reaction was stopped and quenched by adding aqueous ammonium chloride solution. The mixture was extracted with EA, and the organic phase was collected, dried, and rotary evaporated to remove the solvent. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:100, v / v) gave intermediate 41 (248 mg, 60% yield).

[0264] Step 2: Synthesis of iridium dimer: [ka]

[0265] A mixture of Intermediate 41 (0.28 g, 0.54 mmol), iridium trichloride trihydrate (50 mg, 0.14 mmol), 2-ethoxyethanol (15 mL), and water (5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solid was collected by filtration, washed three times with methanol, and the solvent was removed under vacuum. The iridium dimer was collected as a red solid and used in the next step without further purification.

[0266] Step 3: Synthesis of Compound 1018 [ka]

[0267] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (51 mg, 0.21 mmol), potassium carbonate (98 mg, 0.71 mmol), and 15 mL of ethoxyethanol were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.1 g of the product, compound 1018, was obtained (49% yield). LC-MS confirmed the compound's structure as the target product with a molecular weight of 1456.6.

[0268] Synthetic Example 13: Synthesis of Compound 452 Step 1: Synthesis of intermediate 44: [ka]

[0269] Intermediate 42 (418 mg, 0.95 mmol), Intermediate 43 (370 mg, 1 mmol), tetrakis(triphenylphosphine)palladium (55 mg, 0.048 mmol), sodium carbonate (151 mg, 1.43 mmol), 1,4-dioxane (8 mL), and water (2 mL) were added to a 100 mL round-bottom flask. The reaction mixture was heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, the liquid phase was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:3, v / v) afforded Intermediate 44 (500 mg, 81.3% yield) as a white solid.

[0270] Step 2: Synthesis of intermediate 45: [ka]

[0271] Intermediate 44 (500 mg, 0.77 mmol) and diphenyl ether (4 mL) were heated to 180 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The crude product was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) to give intermediate 45 (110 mg, 30% yield) as a yellow solid.

[0272] Step 3: Synthesis of iridium dimer: [ka]

[0273] A mixture of intermediate 45 (110 mg, 0.23 mmol), iridium trichloride trihydrate (25 mg, 0.077 mmol), 2-ethoxyethanol (6 mL), and water (2 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0274] Step 4: Synthesis of Compound 452 [ka]

[0275] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (111 mg, 0.46 mmol), and potassium carbonate (159 mg, 1.15 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.04 g of compound 452 (37.6% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1380.6.

[0276] Synthetic Example 14: Synthesis of Compound 1017 Step 1: Synthesis of intermediate 47: [ka]

[0277] Intermediate 19 (0.5 g, 1.18 mmol), Intermediate 46 (346 mg, 2.36 mmol), Pd2(dba)3 (12 mg, 0.012 mmol), tBuDavephos (21 mg, 0.06 mmol), lithium acetate (0.39 g, 5.9 mmol), water (43 mg, 2.36 mmol), and DMF (30 mL) were added to a reaction tube. The mixture was sealed under nitrogen gas and heated to 150 °C overnight. After completion of the reaction, the mixture was cooled to room temperature. The solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography afforded Intermediate 47 (0.4 g, 73.5%) as a yellow solid.

[0278] Step 2: Synthesis of iridium dimer: [ka]

[0279] A mixture of intermediate 47 (0.7 g, 1.52 mmol), iridium trichloride trihydrate (0.18 g, 0.5 mmol), 2-ethoxyethanol (27 mL), and water (9 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was filtered, the solid was washed with methanol, and dried to give the iridium dimer, which was used in the next step without further purification.

[0280] Step 3: Synthesis of compound 1017 [ka]

[0281] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.18 g, 0.76 mmol), potassium carbonate (0.35 g, 2.53 mmol), and 2-ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.37 g of the product, compound 1017, was obtained (54% yield). LC-MS confirmed the structure of the target product with a molecular weight of 1352.6.

[0282] Synthetic Example 15: Synthesis of Compound 1022 Step 1: Synthesis of intermediate 49: [ka]

[0283] Intermediate 42 (600 mg, 1.37 mmol), Intermediate 48 (546 mg, 1.43 mmol), tetrakis(triphenylphosphine)palladium (79 mg, 0.069 mmol), sodium carbonate (218 mg, 2.06 mmol), 1,4-dioxane (8 mL), and water (2 mL) were added to a 100 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, the liquid was separated, the liquid phase was extracted with ethyl acetate, the organic phases were combined, dried, and the solvent was completely removed by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:3, v / v) afforded Intermediate 49 (620 mg, 68.4% yield) as a white solid.

[0284] Step 2: Synthesis of intermediate 50: [ka]

[0285] Intermediate 49 (620 mg, 0.94 mmol) and diphenyl ether (5 mL) were heated to 140 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. The crude product was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:20, v / v) to give intermediate 50 (260 mg, 56.5% yield) as a yellow solid.

[0286] Step 3: Synthesis of iridium dimer: [ka]

[0287] A mixture of intermediate 50 (260 mg, 0.53 mmol), iridium trichloride trihydrate (62 mg, 0.18 mmol), 2-ethoxyethanol (9 mL), and water (3 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solution was carefully spun on a rotary evaporator to remove the water, yielding a solution of the iridium dimer in ethoxyethanol, which was used in the next step without further purification.

[0288] Step 4: Synthesis of Compound 1022 [ka]

[0289] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (86 mg, 0.36 mmol), and potassium carbonate (124 mg, 0.9 mmol) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. The mixture was then filtered through a diatomaceous earth funnel and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely removed. After filtration, 0.08 g of compound 1022 (31.5% yield) was obtained. LC-MS confirmed the structure of the target product with a molecular weight of 1408.6.

[0290] Those skilled in the art should know that the above preparation methods are merely exemplary and can be modified to obtain the structures of other compounds of the present invention.

[0291] By designing a special ligand structure, the metal complex of the present invention realizes a deeper red emission, and the following photoluminescence spectrum (PL) data proves that such a deeper red emission is an unexpected and excellent effect.

[0292] Spectral data The photoluminescence spectrum (PL) data of the compounds of the present invention and the comparative compounds were measured using a fluorescence spectrophotometer, model number Ryokou F98, manufactured by Shanghai Ryokou Technology Co., Ltd. Samples of the compounds of the present invention and the comparative compounds were each diluted with HPLC-grade toluene at a concentration of 3 × 10 -5 After preparing a solution of 100 mol / L, it was excited with light of 500 nm wavelength at room temperature (298 K) and its emission spectrum was measured. The measurement results are shown in Table 1.

[0293] [Table 14]

[0294] The structures of the compounds according to the present invention and the comparative compounds are shown below.

[0295] [ka]

[0296] summary Phenylisoquinoline ligands are a ligand structure that has been widely studied and used in the prior art, particularly in the field of red phosphorescent metal complexes. Studies have revealed that the introduction of a fused ring structure in addition to the isoquinoline ring of such ligands results in a significant blue shift in emission wavelength. For example, as can be seen from the data in Table 1, compound RD-B, which has a phenylbenzylisoquinoline ligand, exhibits a 4 nm blue shift in maximum emission wavelength compared to compound RD-A. In the present invention, compounds 442, 341, and 441 of the present invention also have fused ring structures at the same position on the isoquinoline ring, but their maximum emission wavelengths are significantly red shifted compared to compound RD. This red shift effect is contrary to the trend observed in the prior art. These comparisons demonstrate the unique structure of the metal complexes of the present invention, which can provide metal complexes with novel structures that produce unexpectedly deeper red emission colors.

[0297] Example of the element Element Example 1 First, a glass substrate with a 120 nm thick indium tin oxide (ITO) anode 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 then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8 In the case of a 100-nm-thick ITO anode, the layers were deposited sequentially by hot vacuum evaporation at a rate of 0.2 to 2 Å / s. Compound HI was doped into compound HT to form a hole injection layer (HIL, 3:97) with a thickness of 100 Å. Compound HT was used as a hole transport layer (HTL), with a thickness of 400 Å. Compound EB was used as an electron blocking layer (EBL), with a thickness of 50 Å. Compound 341 of the present invention was then doped into host compound RH to form an emitting layer (EML, 5:95), with a thickness of 400 Å. Compound HB was used as a hole blocking layer (HBL), with a thickness of 50 Å. Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL to form an electron transport layer (ETL), with a thickness of 350 Å. Finally, a 1-nm-thick Liq layer was deposited as an electron injection layer, and 120 nm of Al was deposited as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0298] Comparative Example 1 of the Element The preparation method of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that Compound RD is substituted for Compound 341 of the present invention in the light-emitting layer (EML).

[0299] Element Example 3 The preparation method of Device Example 3 is the same as Device Example 1, except that in the light-emitting layer (EML), Compound 438 of the present invention is used instead of Compound 341 of the present invention, and the weight ratio of Compound 438 of the present invention to Compound RH is adjusted to 3:97.

[0300] Element Example 4 The preparation method of Device Example 4 is the same as Device Example 3, except that Compound 446 of the present invention replaces Compound 438 of the present invention in the light-emitting layer (EML).

[0301] Element Example 5 The preparation method of Device Example 5 is the same as Device Example 3, except that Compound 1021 of the present invention replaces Compound 438 of the present invention in the light-emitting layer (EML).

[0302] Element Example 6 The preparation method of Device Example 6 is the same as Device Example 3, except that Compound 405 of the present invention is substituted for Compound 438 of the present invention in the light-emitting layer (EML).

[0303] Device Example 7 The preparation method of Device Example 7 is the same as Device Example 3, except that Compound 1019 of the present invention is substituted for Compound 438 of the present invention in the light-emitting layer (EML).

[0304] Device Example 8 The preparation method of Device Example 8 is the same as Device Example 3, except that Compound 447 of the present invention replaces Compound 438 of the present invention in the light-emitting layer (EML).

[0305] Device Example 9 The preparation method of Device Example 9 is the same as Device Example 3, except that Compound 1020 of the present invention replaces Compound 438 of the present invention in the light-emitting layer (EML).

[0306] Device Example 10 The preparation method of Device Example 10 is the same as Device Example 3, except that Compound 1018 of the present invention replaces Compound 438 of the present invention in the light-emitting layer (EML).

[0307] Device Example 11 The preparation method of Device Example 11 is the same as Device Example 3, except that Compound 1017 of the present invention is substituted for Compound 438 of the present invention in the light-emitting layer (EML).

[0308] Comparative Example 3 of the Element The preparation method of Comparative Example 3 of the device is the same as that of Example 3 of the device, except that the compound RD1 is substituted for the compound 438 of the present invention in the light-emitting layer (EML).

[0309] The layer structure and thickness of some of the elements are shown in the table below: When more than one material is used, it is obtained by doping with different compounds in the weight ratios given above.

[0310] [Table 15]

[0311] The structure of the material used in the element is represented as follows:

[0312] [ka]

[0313] [ka]

[0314] The IVL characteristics of the device were measured. Table 3 shows the IVL characteristics at 15 mA / cm 2 The CIE data, driving voltage, maximum emission wavelength (λ) of the example and comparative example of the element measured under a constant current of max ), full width at half maximum (FWHM) and external quantum efficiency (EQE) are shown.

[0315] [Table 16]

[0316] summary As can be seen from the data shown in Table 3, Example 1 exhibited an extremely low FWHM close to that of Comparative Example 1, and when a low voltage was maintained at approximately the same level, the complexion was obviously red-shifted and the CIE x The ρ changed from 0.684 in Comparative Example 1 to 0.688, and the maximum emission wavelength was red-shifted from 621 nm in Comparative Example 1 to 625 nm, achieving a deeper red emission. Furthermore, the external quantum efficiency of Example 1 was also significantly improved by about 7.3%, further improving the extremely high efficiency level of 24.11% in Comparative Example 1. It has been demonstrated that the present invention can provide a deep red phosphorescent material with a narrow full width at half maximum, low voltage, and high efficiency, demonstrating the broad application potential of the compounds of the present invention.

[0317] Compared to Comparative Example 3, Examples 3 to 11 maintained an extremely narrow FWHM and low voltage level roughly equivalent to Comparative Example 3, but all of the maximum emission wavelengths of Examples 3 to 11 were red-shifted, achieving deeper red light emission. The device efficiencies of Examples 3 to 11 were also significantly improved over the extremely high efficiency level of 24.24% of Comparative Example 3. In particular, Examples 3, 4, 8, and 9 achieved extremely high device efficiencies of over 26%. This once again proves that the present invention can provide deep red phosphorescent light-emitting materials with narrow FWHM, low voltage, and high efficiency, demonstrating the broad application potential of the compounds of the present invention.

[0318] Furthermore, since the top-emitting device structure is a device structure that is widely used in commercial devices, the present specification further verifies the excellent effects of the metal complex according to the present invention in top-emitting devices.

[0319] Element Example 2 First, a 0.7 mm thick glass substrate with a pre-patterned indium tin oxide (ITO) 75 Å / Ag 1500 Å / ITO 150 Å anode was used. The substrate was then dried in a glove box to remove moisture, attached to a holder, and placed in a vacuum chamber. Hereinafter, for the specified organic layer, a vacuum of approximately 10 -6In the case of a 1000-kV TTL, the anode was sequentially deposited by hot vacuum evaporation at a rate of 0.01 to 10 Å / s. First, compound HT1 and compound HI were co-evaporated to form a hole-injection layer (HIL, 97:3, 100 Å). Compound HT1 was evaporated on the HIL to form a hole-transport layer (HTL, 2200 Å). The HTL also served as a microcavity control layer. Next, compound EB1 was evaporated on the hole-transport layer to form an electron-blocking layer (EBL, 50 Å). Compound 341 and compound RH were co-evaporated to form an emitting layer (EML, 3:97, 400 Å). Compound ET1 and Liq were co-evaporated on the EML to form an electron-transport layer (ETL, 40:60, 350 Å). 10 Å of metallic Yb was evaporated to form an electron-injection layer (EIL), and 140 Å of metallic Ag and Mg were co-evaporated in a 9:1 ratio to form a cathode. Finally, compound CPL54 was vapor-deposited to form a cathode cover layer (CPL, 650 Å), which was purchased from Jiangsu Marchue Technology Co., Ltd. The device was then transferred to a glove box and encapsulated with a glass cover and a moisture absorbent under a nitrogen gas atmosphere to complete the device.

[0320] Comparative example 2 of the element The preparation method of Comparative Example 2 of the device is the same as that of Example 2 of the device, except that Compound RD is substituted for Compound 341 of the present invention in the light-emitting layer (EML).

[0321] Device Example 12 The preparation method of Device Example 12 is the same as Device Example 2, except that Compound 447 of the present invention replaces Compound 341 of the present invention in the light-emitting layer (EML).

[0322] The layer structure and thickness of some of the elements are shown in the table below: When more than one material is used, it is obtained by doping with different compounds in the weight ratios given above.

[0323] [Table 17]

[0324] The structure of the new material used in the device is represented as follows:

[0325] [ka]

[0326] The IVL characteristics of the device were measured. 2 The CIE data of the element, the maximum radiation wavelength λ max The voltage (V), full width at half maximum (FWHM), and external quantum efficiency (EQE) were measured, and these data are recorded and shown in Table 5.

[0327] [Table 18]

[0328] summary As can be seen from Table 5, the top-emitting device of Example 2, in which the compound of the present invention was used in the emissive layer, also exhibited excellent performance. Example 2 maintained a very narrow full width at half maximum (FWHM) similar to that of Comparative Example 2, and maintained a low voltage level with nearly the same level. Furthermore, the emission color of Example 2 was significantly red-shifted compared to Comparative Example 2. The CIEx changed from 0.680 to 0.690, and the maximum emission wavelength red-shifted from 618 nm to 623 nm. At the same time, Example 2 achieved a significant improvement in EQE, improving by approximately 17%, when the voltage was maintained at a level comparable to that of Comparative Example 2. Example 12 exhibited a very narrow FWHM level almost identical to that of Comparative Example 2, and maintained a low voltage level with nearly the same level as that of Comparative Example 2. More importantly, Example 12 achieved a very significant improvement in EQE, improving by approximately 13%, while significantly red-shifting the maximum emission wavelength. Thus, the device performance of Example 12 was similar to that of Example 2. The excellent properties of the metal complexes according to the invention and their enormous application potential in top-emitting devices are once again demonstrated.

[0329] It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Therefore, it will be apparent to those skilled in the art that the invention sought to be protected includes variations on the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting. [Explanation of symbols]

[0330] 100 Organic light-emitting device 101 Substrate 102 Encapsulation Layer 110 Anode 120 Hole injection layer 130 Hole transport layer 140 Electron Blocking Layer 150 luminescent layer 160 Hole Blocking Layer 170 Electron transport layer 180 Electron injection layer 190 Cathode 300 OLED elements 301 Anode layer 302 Hole injection layer 303 First hole transport layer 304 Second hole transport layer 305 Light-emitting layer 306 Hole Blocking Layer 307 Electron transport layer 308 Electron injection layer 309 Cathode Layer 310 Capping Layer

Claims

Claim 1: An organic layer comprising a metal complex having the general formula M(L a ) m (L b ) n , the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu, L a and L b are a first ligand and a second ligand of the complex, respectively, m is 1 or 2, n is 1 or 2, m+n is equal to the oxidation state of the metal M, when m is greater than 1, a plurality of L a s may be the same or different, when n is greater than 1, two L b s may be the same or different, and L a and L b may be bonded to form a multidentate ligand; Said L ａ has a structure represented by Formula 1, 【Chemistry 1】 (Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Ring C is selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 ring atoms; R ｉ , R ｉｉ are the same or different and represent mono-, multi- or no substitution at each occurrence; R ｉｉｉ represents, identically or differently, one or more substitutions at each occurrence; Y is SiR ｙ R ｙ , GeR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se; Two R's ｙ When two R ｙ may be the same or different, X １ ~X ２ is the same or different for each occurrence ｘ or N, R, R ｉ , R ｉｉ , R ｘ and R ｙ are the same or different at each occurrence and each represents hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R ｉｉｉ are the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon selected from the group consisting of aryl groups having 6 to 30 atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R ｉ , R ｘ , R ｙ , R, R ｉｉ and R ｉｉｉ may be bonded to form a ring.) The L b is an organic layer selected from the following structures: 【Chemistry 2】 (R a , R b and R c are the same or different and each occurrence represents mono-, multi- or unsubstituted; X c and X d are selected from O; R a , R b , and R c each appearing the same or different are hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R a , R b , and R c may be bonded to form a ring.

2. Ring A and / or ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms, and ring C is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 6 to 18 ring atoms; The organic layer according to claim 1 .

3. Said L ａ is selected from the structures represented by any one of formulas 2 to 17, The organic layer according to claim 1 . 【Transformation 3】 (In formulas 2 to 17, X １ ~X ２ is the same or different for each occurrence ｘ or N, and X ３ is CR ｉ or N, and A １ ~A ６ is the same or different for each occurrence ｉｉ or N, and X ４ ~X ７ may be the same or different for each occurrence, and may be CH, CR ｉｉｉ or N, and X ４ ~X ７ At least one of the following is CR ｉｉｉ Selected from Z may be the same or different for each occurrence. ｉｖ R ｉｖ , SiR ｉｖ R ｉｖ , P.R. ｉｖ , O, S or NR ｉｖ Selected from two R ｉｖ When two R ｉｖ are the same or different, Y is SiR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se, and two R ｙ When two R ｙ are the same or different, R, R ｘ , R ｙ , R ｉ , R ｉｉ and R ｉｖ are the same or different at each occurrence and each represents hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R ｉｉｉ are the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon selected from the group consisting of aryl groups having 6 to 30 atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R ｉ , R ｘ , R ｙ , R, R ｉｉ , R ｉｉｉ and R ｉｖ may be bonded to form a ring.)

4. The L a is selected from the structures represented by formula 2 or formula 3: The organic layer according to claim 3 .

5. In formulas 2 to 17, X １ ~X ｎ and / or A １ ~A ｍ At least one of the X is selected from N, ｎ is the X １ ~X ７ corresponds to the largest number present in any one of formulas 2 to 17, ｍ is the above-mentioned A １ ~A ６ The number corresponding to the largest number present in any one of the formulas 2 to 17. The organic layer according to claim 3 .

6. In formulas 2 to 17, at least one of X 1 to X n is selected from N, and said X n corresponds to said X 1 to X 7 that has the largest number present in any one of formulas 2 to 17. The organic layer according to claim 3 .

7. In formulas 2 to 17, X １ ~X ２ are each independently CR ｘ Selected from X ３ is CR ｉ Selected from A １ ~A ６ are each independently CR ｉｉ Selected from X ４ ~X ７ may be the same or different for each occurrence, and may be CH or CR. ｉｉｉ and X ４ ~X ７ At least one of the following is CR ｉｉｉ and adjacent substituents R ｘ , R ｉ , R ｉｉ , R ｉｉｉ may be bonded to form a ring, The R ｘ , R ｉ , R ｉｉ are, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; The R ｉｉｉ are the same or different at each occurrence and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; The organic layer according to claim 3 .

8. at least one or two of R x , R i , and R ii each appearing may be the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; R iii , each occurrence, may be the same or different and is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof; The organic layer according to claim 3 .

9. In formulas 2 to 17, A １ ~A ６ At least one or two of the following are CR ｉｉ and wherein R ｉｉ are the same or different at each occurrence and are selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof; X ３ is CR ｉ and wherein R ｉ are the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof; The organic layer according to claim 3 .

10. R i , each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof; R ii , each occurrence, may be the same or different and is selected from the group consisting of deuterium, fluorine, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a neopentyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, a trimethylsilyl group, an isopropyldimethylsilyl group, a phenyldimethylsilyl group, a trifluoromethyl group, a cyano group, a phenyl group, and combinations thereof; The organic layer according to claim 3 .

11. In formulas 2 to 17, R is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; The organic layer according to claim 3 .

12. R is selected from hydrogen, deuterium, fluorine, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a neopentyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated isobutyl group, a deuterated tert-butyl group, a deuterated cyclopentyl group, a deuterated cyclopentylmethyl group, a deuterated cyclohexyl group, a deuterated neopentyl group, a trimethylsilyl group, or a combination thereof. The organic layer according to claim 3 .

13. In formulas 2 to 17, Y is selected from O or S. The organic layer according to claim 3 .

14. In formulas 2 to 17, X １ is CR ｘ Selected from X ２ is CR ｘ or N, The R ｘ is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; The organic layer according to claim 3 .

15. The ligand L ａ has a structure represented by formula 18: The organic layer according to claim 1 . 【Chemistry 4】 (In formula 18, Y is selected from O or S, R ｘ１ , R ｘ２ , R ｉ , R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ , R, R ｉｉｉ１ , R ｉｉｉ２ , R ｉｉｉ３ , R ｉｉｉ４ are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon R is selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, carboxyl group, cyano group, isocyano group, hydroxy group, sulfanyl group, phosphino group, and combinations thereof, each of which has 0 to 20 carbon atoms; ｉｉｉ１ , R ｉｉｉ２ , R ｉｉｉ３ , R ｉｉｉ４ at least one of at each occurrence is the same or different and is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or Selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms. 。）

16. One or two of R x1 and R x2 and / or R ii1 , R ii2 , R ii3 , and R ii4 and at least one or two of R iii1 , R iii2 , R iii3 are, each occurrence, the same or different, selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R is selected from halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; at least one or two of R iii3 and R iii4 , each occurrence being the same or different, are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; The organic layer of claim 15.

17. In formula 18, R ｘ１ , R ｘ２ , R ｉｉｉ１ , R ｉｉｉ２ , R ｉｉｉ３ , R ｉｉｉ４ , R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof. Ru, The organic layer of claim 15.

18. L ａ is selected from the group consisting of the following structures, which may be the same or different at each occurrence: The organic layer according to claim 1 . 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Chemistry 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Transformation 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 (In the above structure, TMS is trimethylsilyl, Said L ａ１ ~L ａ１９０４ The hydrogen atoms in the structure may be partially or completely replaced with deuterium atoms.

19. The metal M is Ir. The organic layer according to claim 1 .

20. L ｂ is the same or different at each occurrence and is selected from the following structures: The organic layer according to claim 1 . 【Chemical 86】 (R １ ~R ７ are the same or different at each occurrence and each represents hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; (It is.)

21. At least one or two of R 1 to R 3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least one or two of R 4 to R 6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; The organic layer of claim 20.

22. The metal complex has the formula Ir(L ａ ) ｍ (L ｂ ) ３－ｍ and having a structure represented by formula 1-1 or 1-2, The organic layer of claim 20. 【Transformation 87】 (m is 1 or 2, X １ ~X ２ is the same or different for each occurrence ｘ or N, and X ３ is the same or different for each occurrence ｉ or N, and A １ ~A ４ is the same or different for each occurrence ｉｉ or N, and X ４ ~X ７ may be the same or different for each occurrence, and may be CH, CR ｉｉｉ or N, and X ４ ~X ７ At least one of the following is CR ｉｉｉ Selected from Y is SiR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se, and two R ｙ When two R ｙ are the same or different, R, R ｘ , R ｙ , R ｉ , R ｉｉ , R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ are the same or different at each occurrence and each represents hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R ｉｉｉ are the same or different at each occurrence and represent deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon selected from the group consisting of aryl groups having 6 to 30 atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, carboxyl groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R and R ｘ , R ｙ , R ｉ , R ｉｉ and R ｉｉｉ may be bonded to form a ring, Adjacent substituents R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ may be bonded to form a ring 。）

23. L ｂ may be the same or different for each occurrence. 【Chemical 88】 【Chemistry 89】 【Chemistry 90】 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 Selected from the group consisting of:

20. The organic layer of claim 1 or 18.

24. The metal complex is Ir(L ａ ) ２ (L b ) The metal complex is Ir(L ａ ) ２ (L ｂ ) structure, L ａ may be the same or different for each occurrence of L ａ１ ~L ａ１９０４ and L ｂ Is, L ｂ１ ~L ｂ３２２ Any one selected from the group consisting of: The organic layer of claim 23.

25. The metal complex is selected from the group consisting of Compound 1 to Compound 1010, The compounds 1 to 800 have a structure of Ir(L a ) 2 (L b ), in which two L a s are the same, and L a and L b s are selected from the structures shown in the following table, respectively: Table 1 Table 2 Table 3 Table 4 Table 5 Table 6 Table 7 Table 8 Compounds 801 to 1010 have a structure of Ir(L a ) 2 (L b ), in which two L a s are different, and L a s and L b s are each selected from the structures shown in the following table:

25. The organic layer of claim 24. Table 9 Table 10 Table 11 Table 12

Images