Organic electroluminescent material and device thereof

Abstract

To provide an organic electroluminescent material and an element thereof.SOLUTION: The organic electroluminescent material is a metal complex containing an La ligand having a structure represented by formula 1, and in which the La ligand has a multi-membered fused ring structural unit of 6-membered ring-5-membered ring-6-membered ring, and includes particular R1 substituent and Rn substituent. When applied to electroluminescent element, the novel compound can further reduce the half value-width of the emission spectrum while maintaining the high performance of the element, improve the luminescence saturation degree of the element, and have high efficiency under conditions that more closely approach the commercial luminescence requirements of BT.2020.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound for use in an organic light-emitting device such as an organic electronic device. In particular, the compound has a structure represented by Formula 1. a The present invention relates to a metal complex containing a ligand, an organic electroluminescent device containing the metal complex, and a composition containing the metal complex. [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 service life, 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 service life.

[0008] Full-color displays are now widely used in our work and daily lives, such as mobile phone displays, computer monitors, and shopping mall advertising displays. They are primarily used to display information such as text, graphics, animations, videos, and recordings. Display and image formation are performed by pixels. Each pixel unit controls RGB subpixels to display different full-color images, and each pixel unit consists of one or more RGB subpixels. Color reproduction generally refers to the colors that can be displayed by the RGB subpixels of a display. BT.2020 is currently the highest color gamut requirement for color reproduction, and the higher the BT.2020 coverage of a full-color display, the better its color reproduction. However, while BT.2020's color gamut specification is higher, the color saturation of the three primary colors in BT.2020 makes it difficult for ordinary devices to achieve this. BT.2020 requires the color coordinates of the three primary colors red, green, and blue to be (0.708, 0.292), (0.131, 0.046), and (0.170, 0.797), respectively. In currently commonly used display panels, the red and blue light elements can both almost meet the color gamut requirements, but the performance of the green light element is limited mainly by its inability to meet the color gamut requirements. Therefore, the color coordinates of the green light element must be adjusted to approach the BT.2020 requirements.

[0009] CN111655705A discloses a metal complex having a structure represented by the following formula: [ka] (wherein R5 is selected from groups such as halogen, nitrile group, nitro group, and substituted or unsubstituted alkyl group having 3 to 30 carbon atoms.) Additionally, the following specific structures are disclosed: [ka] The application does not disclose or teach that, while a quaternary carbon atom is present at the R5 position of a metal complex, other specific substituents are also present at specific positions, and the effect of said metal complexes on the performance of devices. [Prior art documents] [Patent documents]

[0010] [Patent Document 1] Chinese Patent Application Publication No. 111655705 [Non-patent literature]

[0011] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]

[0012] In order to solve at least some of the above-mentioned problems, the present invention provides a series of L-type compounds having a structure represented by Formula 1. a The present invention aims to provide a metal complex containing a ligand, L a The ligand has a 6-membered ring-5-membered ring-6-membered ring multi-membered fused ring structure unit, and specific R and R nThese novel metal complexes, when applied to electroluminescent devices, can achieve excellent device performance, significantly improve the device's luminescence performance, and achieve more saturated luminescence that meets the commercial BT.2020 requirements. [Means for solving the problem]

[0013] According to one embodiment of the present invention, a metal M and a ligand L coordinated with the metal M are a A metal complex comprising L a discloses a metal complex having a structure represented by formula 1: [ka] (In formula 1, ring Cy, which may be the same or different at each occurrence, is selected from an aromatic ring containing Y1 and Y2 and having 6 to 24 ring atoms, a heteroaromatic ring containing Y1 and Y2 and having 5 to 24 ring atoms, or a combination thereof; G1 and G2, each occurrence, are the same or different and are selected from a single bond, O, or S; X1 to X6 are the same or different for each occurrence. x or N, one of X1 to X3 is selected from C and is bonded to Y1; one of X1, X2 and X3 is selected from N and is bonded to the metal by a metal-nitrogen bond, or one of X1, X2 and X3 is selected from C and is bonded to the metal by G2; Y1 and Y2, at each occurrence, are the same or different and are selected from C or N; Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R' are present at the same time, the two R' are the same or different; R represents mono-, poly- or unsubstituted, and when multiple R are present, the multiple R are the same or different; R, R xand R' each occurrence may be the same or different 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, an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R1 is selected from a cyano group or fluorine; R n has a structure represented by formula 2, [ka] In Formula 2, "*" represents the bonding point between Formula 2 and Formula 1, L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; R2, R3 and R4 each may be the same or different and each represent a 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring; Adjacent substituents R' and R x may be bonded to form a ring, Adjacent substituents R2, R3 and R4 may be bonded to form a ring.

[0014] According to another embodiment of the present invention, there is further disclosed an organic electroluminescence device including an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein at least one of the organic layers contains the metal complex described in the above embodiment.

[0015] According to other embodiments of the present invention, there are further disclosed compositions comprising the metal complexes described in the above embodiments.

[0016] In order to solve at least some of the above-mentioned problems, the present invention provides a series of L-type compounds having a structure represented by Formula 1. a The present invention provides a metal complex containing a ligand, L a The ligand has a 6-membered ring-5-membered ring-6-membered ring fused multi-membered ring structural unit, and specific R and R n These novel compounds, when applied to electroluminescent devices, can achieve excellent device performance, further reduce the half-width of the emission spectrum while maintaining high device performance, improve the device's luminescence saturation, and achieve high efficiency under conditions closer to the commercial luminescence requirements of BT.2020. [Brief explanation of the drawings]

[0017] [Figure 1] 1 is a schematic diagram of an organic light-emitting device that may include a metal complex according to the present invention and a composition including the metal complex. [Figure 2] 1 is a schematic diagram of another organic light-emitting device that may include a metal complex according to the present invention and a composition including the metal complex. [Figure 3] 1 is a schematic diagram of the structure of a typical top-emission OLED device. DETAILED DESCRIPTION OF THE INVENTION

[0018] 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.

[0019] 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.

[0020] As used herein, the term "color coordinates" refers to the corresponding coordinates in the CIE 1931 color space.

[0021] The structure of a typical top-emission OLED device is shown in Figure 3. OLED device 300 includes an anode 110, a hole-injection layer (HIL) 120, a hole-transport layer (HTL) 130, an electron-blocking layer (EBL) 140 (also called a prime layer), an emissive layer (EML) 150, a hole-blocking layer (HBL) 160 (the hole-blocking layer 160 is an optional layer), an electron-transport layer (ETL) 170, an electron-injection layer (EIL) 180, a cathode 190, a capping layer 191, and an encapsulation layer 102. The anode 110 is made of a material or a combination of materials with high reflectivity, 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 reflectivity of the anode is greater than 50%, preferably greater than 70%, and more preferably greater than 80%. The cathode 190 is a semi-transparent or transparent conductive material, including, but not limited to, MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or a combination thereof, and has an average transmittance of greater than 15% for light in the visible light wavelength range, preferably greater than 20%, and more preferably greater than 25% for light in the visible light wavelength range. The hole injection layer 120 may be a single-material layer, such as the commonly used HATCN. The hole injection layer 120 may also be a hole transport material doped with a certain percentage of a p-type conductive dopant; the doping ratio is usually no more than 5%, and commonly between 1% and 3%. The electron blocking layer (EBL) 140 is an optional layer, but because it closely matches the energy level of the host material, a device structure that includes an EBL is typically used. The thickness of the hole transport layer is typically 100 nm to 200 nm, and because a microcavity effect exists in top-emission devices, the thickness of the hole transport layer or electron blocking layer can be adjusted to tune the microcavity of the device.For example, to optimize the microcavity effect of one top-emitting OLED device, i.e., to achieve the highest current efficiency, the microcavity can be adjusted by adjusting the thickness of the HTL after keeping the thickness of the EBL constant. Those skilled in the art should understand that the difference between two top-emitting devices is only the material used in one of the organic layers of the device. For example, if a different organic material is used only in the EML (while other functional layers are similar), the refractive indexes of the different organic materials in the EML may be slightly different, so the optimal microcavity lengths of the two top-emitting devices may be slightly different. That is, for different top-emitting devices, under the same setting conditions (e.g., CE). max , CIEx coordinates or EQE max , etc.), the optimal microcavity length may be slightly different.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0027] "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.

[0028] "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.

[0029] 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.

[0030] 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).

[0031] 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.

[0032] 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).

[0033] Definitions of Substituent Terminology

[0034] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0035] 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.

[0036] 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.

[0037] 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. Illustrative examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermaniummethyl, trimethylgermaniumethyl, trimethylgermaniumisopropyl, dimethylethylgermaniummethyl, dimethylisopropylgermaniummethyl, tert-butyldimethylgermaniummethyl, triethylgermaniummethyl, triethylgermaniumethyl, triisopropylgermaniummethyl, triisopropylgermaniumethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropyloylsilylethyl. Heteroalkyl groups may also be substituted.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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 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.

[0050] 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.

[0051] 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 sulfonyl group, a substituted hydroxyl group, a ... When any of the terms from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups is used. The group is selected from the group consisting of deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroxy group having 3 to 30 carbon atoms, an unsubstituted aryl ... This means that the aryl group may be substituted with one or more groups selected from the group consisting of 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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: [ka]

[0057] 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: [ka]

[0058] 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: [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. [ka]

[0060] According to one embodiment of the present invention, a metal M and a ligand L coordinated with the metal M are a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and L a discloses a metal complex having a structure represented by formula 1: [ka] (In formula 1, ring Cy, which may be the same or different at each occurrence, is selected from an aromatic ring containing Y1 and Y2 and having 6 to 24 ring atoms, a heteroaromatic ring containing Y1 and Y2 and having 5 to 24 ring atoms, or a combination thereof; G1 and G2, each occurrence, are the same or different and are selected from a single bond, O, or S; X1 to X6 are the same or different for each occurrence. x or N, one of X1 to X3 is selected from C and is bonded to Y1; one of X1, X2 and X3 is selected from N and is bonded to the metal by a metal-nitrogen bond, or one of X1, X2 and X3 is selected from C and is bonded to the metal by G2; Y1 and Y2, at each occurrence, are the same or different and are selected from C or N; Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R' are present at the same time, the two R' are the same or different; R represents mono-, poly- or unsubstituted, and when multiple R are present, the multiple R are the same or different; R, R x and R' each occurrence may be the same or different 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, an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R1 is selected from a cyano group or fluorine; R n has a structure represented by formula 2, [ka] In Formula 2, "*" represents the bonding point between Formula 2 and Formula 1, L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; R2, R3 and R4 each may be the same or different and each represent a 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring; Adjacent substituents R' and R x may be bonded to form a ring, Adjacent substituents R2, R3 and R4 may be bonded to form a ring.

[0061] In this specification, the phrase "adjacent substituents R may be bonded to form a ring" means that adjacent substituent groups, for example, any one or more of two substituents R, may be bonded to form a ring. Obviously, these substituents do not have to be bonded to form a ring.

[0062] As used herein, "adjacent substituents R' and R xmay be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R', two substituents R x Between the substituents R' and R x This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0063] In this specification, the phrase "adjacent substituents R2, R3, and R4 may be bonded to form a ring" means that adjacent substituent groups, for example, any one or more of the substituents R2 and R3, the substituents R2 and R4, and the substituents R4 and R3, may be bonded to form a ring. Obviously, these substituents do not have to be bonded to form a ring.

[0064] According to one embodiment of the present invention, in Formula 1: [ka] is selected from any one of the following structures, which may be the same or different at each occurrence: [ka] (R may be the same or different at each occurrence and represent mono-, poly- or unsubstituted, and when multiple R are present in any one structure, said R may be the same or different, R may be the same or different at each occurrence and is 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring; "#" indicates the binding site with G1, [ka] represents the bonding site to X1, X2 or X3.

[0065] According to one embodiment of the present invention, the metal complex is a ) m (L b ) n (L c ) q having the general formula L a , L b and L c are the first, second and third ligands coordinated to the metal M, respectively, and L c and the aforementioned L a or Lb are the same or different, L a , L b and L c may be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M, and when m is 2 or more, 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 each occurrence may be the same or different and have a structure represented by any one of formulas 1-1 to 1-14, [ka] [ka] Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R' are present at the same time, the two R' are the same or different; X3 to X6 are the same or different CRs for each occurrence. x or selected from N, R represents mono-, poly- or unsubstituted, and when multiple R are present, the R are the same or different; R1 is selected from a cyano group or fluorine; L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; R, R xR' may be the same or different at each occurrence and is 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R2, R3 and R4 each appearing may be the same or different and each represent fluorine, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring; Adjacent substituents R' and R x may be bonded to form a ring, Adjacent substituents R2, R3, and R4 may be bonded to form a ring; L b and L c is the same or different at each occurrence and is selected from monoanionic bidentate ligands.

[0066] According to one embodiment of the present invention, L b and L c may be the same or different for each occurrence. [ka] The structure is selected from any one of the groups consisting of: (X b are O, S, Se, NR, or the same or different for each occurrence.N1 , C.R. C1 R C2 selected from the group consisting of R a and R b are the same or different at each occurrence and represent mono-, multi- or no substitution; R a , R b , R c , R N1 , R C1 and R C2 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom 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 hydroxyl 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 C1 and R C2 may be bonded to form a ring.

[0067] In the present specification, "adjacent substituents R a , Rb , R c , R N1 , 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 R a and R b R a and R c R b and R c R a and R N1 R b and R N1 R a and R C1 R a and R C2 R b and R C1 R b and R C2 Comrades and R C1 and R C2 This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring. For example, [ka] Adjacent substituents R a , R b may be bonded to form a ring. a may be bonded to form a ring, [ka] teeth, [ka] The following structure may be formed.

[0068] According to one embodiment of the invention, the metals M, identically or differently at each occurrence, are selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.

[0069] According to one embodiment of the invention, the metals M, identically or differently at each occurrence, are selected from Pt or Ir.

[0070] According to one embodiment of the present invention, G1 and G2 are selected from single bonds.

[0071] According to an embodiment of the present invention, Y1 is selected from C.

[0072] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m It has a general structure of the formula: and has a structure represented by formula 3. [ka] (m is selected from 1, 2, or 3, and when m is selected from 1, two L b are the same or different, and when m is selected from 2 or 3, there are multiple L a are the same or different, Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R' are present at the same time, the two R' are the same or different; U1 to U8 are the same or different CRs for each occurrence. u or selected from N, X3 to X6 are the same or different CRs for each occurrence. x or selected from N, Y3 to Y6 are the same or different and selected from CR or N at each occurrence; R1 is selected from a cyano group or fluorine; L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; R', R u , R x and R, each occurrence, may be the same or different 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, an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R2, R3, and R4 each may be the same or different and each represent a 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 C alkylsilyl group, a substituted or unsubstituted C arylsilyl group, a substituted or unsubstituted C arylsilyl group, a substituted or unsubstituted C arylsilyl group, a substituted or unsubstituted C alkylgermanium group, a substituted or unsubstituted C amino group, 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; Adjacent substituents R u may be bonded to form a ring, Adjacent substituents R may be bonded to form a ring; Adjacent substituents R' and R x may be bonded to form a ring, Adjacent substituents R2, R3, and R4 may be bonded to form a ring.

[0073] In the present specification, "adjacent substituents R u may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R u This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0074] According to one embodiment of the present invention, Z is selected from O or S.

[0075] According to one embodiment of the present invention, Z is selected from O.

[0076] According to one embodiment of the present invention, L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkylene group having 4 to 10 carbon atoms, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and combinations thereof.

[0077] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted methylene group.

[0078] According to one embodiment of the present invention, R2, R3 and R4, each occurrence of which may be the same or different, are 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 cyano group, and combinations thereof.

[0079] According to one embodiment of the present invention, R2, R3 and R4, each occurrence, are the same or different and are selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a cyano group, and combinations thereof.

[0080] According to one embodiment of the present invention, R2, R3 and R4, each occurrence of which may be the same or different, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

[0081] According to one embodiment of the present invention, R2, R3 and R4, at each occurrence, are the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0082] According to one embodiment of the present invention, X3 to X6 are the same or different CRs for each occurrence.x Selected from.

[0083] According to one embodiment of the present invention, X3 to X6 are the same or different CRs for each occurrence. x or N, at least one of which is N. For example, one of X3 to X6 is selected from N, or two of X3 to X6 are selected from N.

[0084] According to an embodiment of the present invention, X6 is selected from N.

[0085] According to one embodiment of the present invention, Y3 to Y6 are selected from CR, identically or differently for each occurrence.

[0086] According to one embodiment of the present invention, Y3 to Y6 are identically or differently selected from CR or N for each occurrence, and at least one of them is N. For example, one of Y3 to Y6 is selected from N, or two of Y3 to Y6 are selected from N.

[0087] According to one embodiment of the present invention, R x and R, at each occurrence, are the same or different 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 alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof.

[0088] According to one embodiment of the present invention, R xand R, at each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 12 carbon atoms, a cyano group, and combinations thereof.

[0089] According to one embodiment of the present invention, R x and R, each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridine, trimethylsilyl, trimethylgermanium, and combinations thereof.

[0090] According to one embodiment of the present invention, at least one R 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0091] According to one embodiment of the present invention, at least one R 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0092] According to one embodiment of the present invention, Y3 to Y6 at each occurrence may be the same or different and are selected from CR, and R at each occurrence may be the same or different 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 alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof.

[0093] According to one embodiment of the present invention, Y3 to Y6 at each occurrence are the same or different and are selected from CR, and R at each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, and combinations thereof.

[0094] According to one embodiment of the present invention, at least one of X3 to X6 is CR x wherein R xis 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 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 alkynyl 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, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having 0 to 20 carbon atoms.

[0095] According to one embodiment of the present invention, at least one of X3 to X6 is CR x wherein R x 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 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 cyano group, and combinations thereof.

[0096] According to one embodiment of the present invention, at least one of X3 to X6 is CR x wherein R x is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

[0097] According to one embodiment of the present invention, the X6 x wherein R x is selected from deuterium, 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, or a combination thereof.

[0098] According to one embodiment of the present invention, the X6 x wherein R x is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

[0099] According to one embodiment of the present invention, the X6 x wherein R x is selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

[0100] According to one embodiment of the present invention, the X6 x wherein R x is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, or a combination thereof.

[0101] According to one embodiment of the present invention, at least one R is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and combinations thereof.

[0102] According to one embodiment of the present invention, at least one R is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and combinations thereof.

[0103] According to one embodiment of the present invention, R n may be the same or different for each occurrence. [ka] and R n The hydrogen atoms in may be partially or completely deuterated.

[0104] According to one embodiment of the present invention, U1 to U8 may be the same or different for each occurrence. u Selected from.

[0105] According to one embodiment of the present invention, U1 to U8 may be the same or different for each occurrence. u Or, at least one of U1 to U8 is selected from N. For example, one of U1 to U8 is selected from N, or two of U1 to U8 are selected from N.

[0106] According to one embodiment of the present invention, R u 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 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 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, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.

[0107] According to one embodiment of the present invention, R u 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, and combinations thereof.

[0108] According to one embodiment of the present invention, R u and each occurrence may be the same or different and are selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and combinations thereof.

[0109] According to one embodiment of the present invention, R u are each the same or different and are selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridine, trimethylsilyl, trimethylgermanium, and combinations thereof.

[0110] According to one embodiment of the present invention, at least one or at least two of U1 to U8 are CR u wherein R u 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, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0111] According to one embodiment of the present invention, at least one or at least two of U5 to U8 are CR u wherein R u 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, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0112] According to one embodiment of the present invention, at least one or at least two of U1 to U4 are CR u wherein R u 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, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0113] According to one embodiment of the present invention, U6 or U7 is u wherein R u 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, or a combination thereof.

[0114] According to one embodiment of the present invention, U6 or U7 is u wherein R u is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 ring carbon atoms, or a combination thereof.

[0115] According to one embodiment of the present invention, at least one of U1 to U4 is a CR u At least one of Y3 to Y6 is selected from CR, and the R u 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, or a combination thereof, and uThe sum of the numbers of carbon atoms in R is 2 or more.

[0116] According to one embodiment of the present invention, at least one of U5 to U8 is a CR u At least one of Y3 to Y6 is selected from CR, and the R u 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, or a combination thereof, and u The sum of the numbers of carbon atoms in R is 2 or more.

[0117] According to one embodiment of the present invention, at least one of U1 to U4 is a CR u At least one of U5 to U8 is selected from CR u wherein R u 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, or a combination thereof, and said R u The sum of the numbers of carbon atoms is 2 or more.

[0118] According to one embodiment of the present invention, R' at each occurrence is the same or different and is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

[0119] According to one embodiment of the present invention, R' is a methyl group or a deuterated methyl group.

[0120] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a3530 The L is selected from the group consisting of a1 ~L a3530 The specific structure is shown in claim 15.

[0121] According to one embodiment of the present invention, L a1 ~L a3530 The hydrogen atoms in may be partially or completely deuterated.

[0122] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b151 The L is selected from the group consisting of b1 ~L b151 The specific structure is shown in claim 16.

[0123] According to one embodiment of the present invention, L b1 ~L b18 , L b20 ~L b26 and L b31 ~L b151 The hydrogen atoms in may be partially or completely deuterated.

[0124] According to one embodiment of the present invention, L c is the same or different at each occurrence and is selected from the group consisting of the following structures: [ka]

[0125] According to one embodiment of the present invention, the metal complex is Ir(L a )3, IrL a (L b )2, Ir(L a )2L b , Ir(L a )2L c , IrL a (L c )2 or IrL a L b L c and the ligand L a may be the same or different for each occurrence of L a1 ~L a3530 and the ligand L is selected from any one, any two, or any three of the group consisting of b may be the same or different for each occurrence of L b1 ~L b151 and the ligand L is selected from any one or any two of the group consisting of c may be the same or different for each occurrence of Lc1 ~L c50 It is selected from any one or any two of the group consisting of:

[0126] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 3806. Specific structures of Metal Complex 1 to Metal Complex 3806 are set forth in claim 17.

[0127] According to one embodiment of the present invention, there is further disclosed an organic electroluminescent device including an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein at least one of the organic layers contains the metal complex described in any one of the above-mentioned embodiments.

[0128] According to one embodiment of the present invention, in the organic electroluminescence device, the organic layer containing the metal complex is a light-emitting layer.

[0129] According to one embodiment of the present invention, the organic electroluminescent element emits green light.

[0130] According to one embodiment of the present invention, the organic electroluminescent element emits white light.

[0131] According to an embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further contains a first host compound.

[0132] According to an embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further contains a first host compound and a second host compound.

[0133] According to one embodiment of the present invention, in the electroluminescent device, the first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0134] According to one embodiment of the present invention, the first host compound has a structure represented by formula X-1 or X-2. [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; G may be identical or different for each occurrence of C(R g )2, NR g , O or S; V may be the same or different for each occurrence. v or selected from N, In formula X-1, T may be the same or different at each occurrence and may be C, CR t or selected from N, In formula X-2, T may be the same or different for each occurrence. t or selected from N, R g , R v and R tare 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R g , R v and R t may be bonded to form a ring.

[0135] In the examples, "adjacent substituents R g , R v and R t may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v two substituents R t two substituents R g R v and R t Rv and R g R g and R t This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0136] According to one embodiment of the present invention, the first host compound has a structure represented by one of Formulas Xa to Xp. [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; G may be identical or different for each occurrence of C(R g )2, NR g , O or S; V may be the same or different for each occurrence. v or selected from N, T may be the same or different for each occurrence. t or selected from N, R g , R v and R tare 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R g , R v and R t may be bonded to form a ring.

[0137] According to one embodiment of the present invention, the first host compound is selected from the group consisting of the following compounds: [ka] [ka] [ka]

[0138] The second compound has a structure represented by Formula 5: [ka] E1 to E6 are the same or different for each occurrence, and are C, CR e or N, and at least two of E1 to E6 are N, and at least one of E1 to E6 is C, and bonded to formula A; [ka] Q may be the same or different at each occurrence and may be O, S, Se, N, NR Q , C.R. Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q and two R Q When two R Q may be the same or different, p is 0 or 1, r is 0 or 1, When Q is selected from N, p is 0 and r is 1; Q is O, S, Se, or NR Q , C.R. Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q When selected from the group consisting of: p is 1 and r is 0; L1 in each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1 to Q8 are the same or different for each occurrence. q or selected from N, R e , R Q and R q 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom 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 amine 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; "*" represents the bond between Formula A and Formula 5, Adjacent substituents R e , R Q , R q may be bonded to form a ring.

[0139] In the present specification, "adjacent substituents R e , R Q , R q may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R e two substituents R Q two substituents R q two substituents RQ and R q This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0140] According to one embodiment of the present invention, the second host compound is selected from the group consisting of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka]

[0141] According to one embodiment of the present invention, the metal complex in the electroluminescent device is doped into the first host compound and the second host compound, and the weight of the metal complex is 1% to 30% based on the total weight of the light-emitting layer.

[0142] According to one embodiment of the present invention, the metal complex in the electroluminescent device is doped into the first host compound and the second host compound, and the weight of the metal complex is 3% to 13% based on the total weight of the light-emitting layer.

[0143] According to one embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer. The hole injection layer may be a functional layer of a single material or a functional layer containing multiple materials. The multiple materials most commonly used are hole transport materials doped with a certain percentage of p-type conductive doping materials. Common p-type doping materials are as follows: [ka]

[0144] According to another embodiment of the present invention, a composition is disclosed comprising the metal complex described in any one of the above embodiments.

[0145] According to another embodiment of the present invention, a combination of compounds is disclosed that includes a metal complex described in any one of the above embodiments.

[0146] Combination with other materials

[0147] 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.

[0148] It is stated herein that the materials of specific layers used in organic light-emitting devices can be used in combination with various other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with various 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.

[0149] 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, and a differential scanning calorimeter, a Shanghai Liang Optoelectronics 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 and a service life test system from Suzhou Fusida, and an ellipsometer from Beijing Liangtuo) 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.

[0150] Material Synthesis Examples

[0151] Synthesis Example 1: Synthesis of Metal Complex 1345 [ka] To a dry 250 mL round-bottom flask were added, in order, intermediate 1 (1.8 g, 2.2 mmol), intermediate 2 (1.0 g, 2.4 mmol), 2-ethoxyethanol (30 mL), and dimethylformamide (DMF, 30 mL). The reaction was heated at 100 °C for 144 h under N2 protection. After the reaction cooled, it was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 1345 (1.3 g, 1.2 mmol, 55% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1019.4 and a melting point of 407 °C.

[0152] Synthesis Example 2: Synthesis of Metal Complex 2252 [ka] A dry 250 mL round-bottom flask was charged with intermediate 3 (0.7 g, 0.8 mmol), intermediate 4 (0.4 g, 1.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 2252 (0.4 g, 0.3 mmol, 38% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1131.5.

[0153] Synthesis Example 3: Synthesis of Metal Complex 1583 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 1 (2.8 g, 3.4 mmol), Intermediate 5 (2.0 g, 4.7 mmol), 2-ethoxyethanol (40 mL), and DMF (40 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 1583 (1.6 g, 1.6 mmol, 47% yield). The product was confirmed to be the target product with a molecular weight of 1033.4 and a melting point of 354 °C.

[0154] Synthesis Example 4: Synthesis of Metal Complex 1493 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 1 (1.2 g, 1.5 mmol), Intermediate 6 (0.9 g, 1.8 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 1493 (0.72 g, 0.65 mmol, 43% yield). The product was confirmed to be the target product with a molecular weight of 1106.4 and a melting point of 363 °C.

[0155] Synthesis Example 5: Synthesis of Metal Complex 2262 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (2.6 g, 2.8 mmol), Intermediate 2 (1.7 g, 4.2 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), and the mixture was heated to 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 2262 (2.0 g, 1.8 mmol, 63% yield). The product was confirmed to be the target product with a molecular weight of 1131.5 and a melting point of 388 °C.

[0156] Synthesis Example 6: Synthesis of Metal Complex 2164 [ka] A dry 250 mL round-bottom flask was charged with intermediate 8 (1.4 g, 1.8 mmol), intermediate 2 (1.0 g, 2.5 mmol), 2-ethoxyethanol (25 mL), and DMF (25 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 2164 (0.6 g, 0.6 mmol, 34% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 975.4 and a melting point of 451 °C.

[0157] Synthesis Example 7: Synthesis of Metal Complex 2394 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (1.2 g, 1.3 mmol), Intermediate 9 (1.0 g, 2.0 mmol), 2-ethoxyethanol (20 mL), and DMF (20 mL), and the mixture was heated to 100 °C for 144 h under N2 protection. The mixture was concentrated under reduced pressure and filtered through diatomaceous earth. The mixture was washed twice with methanol and twice with n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected. Purification by column chromatography afforded a yellow solid, metal complex 2394 (1.1 g, 0.9 mmol, 70% yield). The product was confirmed to be the target product with a molecular weight of 1215.5 and a melting point of 426 °C.

[0158] Synthesis Example 8: Synthesis of Metal Complex 2955 [ka] A dry 250 mL round-bottom flask was charged with intermediate 8 (1.3 g, 1.7 mmol), intermediate 10 (1.0 g, 2.0 mmol), 2-ethoxyethanol (20 mL), and DMF (20 mL), and the mixture was heated at 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 2955 (0.6 g, 0.6 mmol, 33% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1083.5 and a melting point of 379 °C.

[0159] Synthesis Example 9: Synthesis of Metal Complex 982 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 11 (3.0 g, 3.6 mmol), Intermediate 12 (2.5 g, 5.0 mmol), 2-ethoxyethanol (50 mL), and DMF (50 mL), and the mixture was heated to 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give Metal Complex 982 (2.0 g, 1.8 mmol, 49% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1139.5 and a melting point of 364 °C.

[0160] Synthesis Example 10: Synthesis of Metal Complex 3671 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (2.7 g, 3.3 mmol), Intermediate 13 (2.5 g, 4.9 mmol), 2-ethoxyethanol (50 mL), and DMF (50 mL), and the mixture was heated at 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 3671 (1.6 g, 1.3 mmol, 39% yield). The product was confirmed to be the target product with a molecular weight of 1279.6 and a melting point of 385 °C.

[0161] Synthesis Example 11: Synthesis of Metal Complex 2526 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (4.8 g, 5.1 mmol), Intermediate 14 (4.0 g, 6.6 mmol), 2-ethoxyethanol (80 mL), and DMF (80 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 2526 (5.2 g, 3.9 mmol, 76% yield). The product was confirmed to be the target product with a molecular weight of 1327.7 and a melting point of 383 °C.

[0162] Synthesis Example 12: Synthesis of Metal Complex 2657 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (5.1 g, 5.4 mmol), Intermediate 15 (3.6 g, 6.0 mmol), 2-ethoxyethanol (50 mL), and DMF (50 mL), and the mixture was heated to 100 °C for 96 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 2657 (6.0 g, 4.7 mmol, 87% yield). The product was confirmed to be the target product with a molecular weight of 1327.7 and a melting point of 422 °C.

[0163] Synthesis Example 13: Synthesis of Metal Complex 1371 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 1 (0.7 g, 0.8 mmol), Intermediate 16 (0.5 g, 1.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), and the mixture was heated at 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 1371 (0.28 g, 0.25 mmol, 31% yield). The product was confirmed to be the target product with a molecular weight of 1090.4 and a melting point of 421 °C.

[0164] Synthesis Example 14: Synthesis of Metal Complex 2393 [ka] A dry 250 mL round-bottom flask was charged with Intermediate 7 (1.8 g, 1.9 mmol), Intermediate 16 (1.3 g, 2.7 mmol), 2-ethoxyethanol (40 mL), and DMF (40 mL), and the mixture was heated to 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid, metal complex 2393 (1.4 g, 1.2 mmol, 63% yield). The product was confirmed to be the target product with a molecular weight of 1202.5 and a melting point of 350 °C.

[0165] Synthesis Example 15: Synthesis of Metal Complex 2921 [ka] A dry 250 mL round-bottom flask was charged with intermediate 7 (1.5 g, 1.6 mmol), intermediate 6 (1.1 g, 2.2 mmol), 2-ethoxyethanol (40 mL), and DMF (40 mL), and heated to 100 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 2921 (1.3 g, 1.1 mmol, 69% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1218.6 and a melting point of 387 °C.

[0166] Synthesis Example 16: Synthesis of Metal Complex 2249 [ka] A dry 250 mL round-bottom flask was charged with intermediate 18 (1.7 g, 1.8 mmol), intermediate 19 (1.0 g, 2.4 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), and the mixture was heated to 100 °C for 144 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 2249 (0.9 g, 0.8 mmol, 44% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1156.5 and a melting point of 439 °C.

[0167] 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.

[0168] Element Example 1

[0169] First, a glass substrate with an 80 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. -6 In the case of a 1000-kV OLED, the layers were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.2 to 2 Å / s. Compound HI was used as a hole-injection layer (HIL). Compound HT was used as a hole-transport layer (HTL). Compound PH-23 was used as an electron-blocking layer (EBL). Compounds PH-23 and H-40 were doped with the metal complex 1345 of the present invention and co-deposited to form an emitting layer (EML). Compound H-2 was used as a hole-blocking layer (HBL) on the EML. Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL to form an electron-transport layer (ETL). Finally, a 1-nm-thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited to form an electron-injection layer, and 120 nm of aluminum was deposited to form 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.

[0170] Element Example 2

[0171] The embodiment of Device Example 2 is similar to Device Example 1, except that Metal Complex 1583 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0172] Comparative Example 1 of the Element

[0173] The embodiment of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that the compound GD1 replaces the metal complex 1345 of the present invention in the light-emitting layer (EML).

[0174] Comparative example 2 of the element

[0175] The embodiment of Comparative Example 2 of the device is similar to that of Example 1 of the device, except that the compound GD2 replaces the metal complex 1345 of the present invention in the light-emitting layer (EML).

[0176] Comparative Example 3 of the Element

[0177] The embodiment of Comparative Example 3 of the device is the same as that of Example 1 of the device, except that the compound GD3 replaces the metal complex 1345 of the present invention in the light-emitting layer (EML).

[0178] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0179] [Table 1]

[0180] The structure of the material used in the device is shown below. [ka]

[0181] The IVL characteristics of the device were measured. 2 CIE data of the element under constant current, maximum emission wavelength (λ max The wavelength, full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) were measured, and the data are recorded and shown in Table 2.

[0182] [Table 2]

[0183] The difference between Example 1 and Example 2 and Comparative Example 1 and Comparative Example 2, respectively, is the luminescent material R nThe only difference is whether the structure of Formula 2 in the present invention is true. As can be seen from the data in Table 2, Example 1 and Example 2 had comparable or slightly lower driving voltages than Comparative Examples 1 and 2, respectively, and comparable or slightly improved current efficiency and external quantum efficiency. However, surprisingly, the half-widths of Examples 1 and 2 were even narrower than the narrow half-widths of Comparative Examples 1 and 2. The half-widths of Examples 1 and 2 were 5.5 nm and 3.2 nm narrower than Comparative Example 1, respectively, and 4.4 nm and 2.1 nm narrower than Comparative Example 2, respectively. It should be emphasized that the half-widths of Comparative Examples 1 and 2 have already reached a high level in the industry, and it would be very difficult to further reduce the half-widths while maintaining the device efficiency and voltage. This result was unexpected. The narrower half-widths enable higher color purity and are closer to the industry's requirements for the luminescent performance of green light-emitting materials. Therefore, it has been shown that the metal complex according to the present invention can provide a device with superior performance.

[0184] The metal complex GD3 used in Comparative Example 3 was R n The data in Table 2 show that, compared to Comparative Example 3, Examples 1 and 2 have narrower half-widths of 28.2 nm and 25.9 nm, improved EQE by 20.5% and 19.7%, and improved CE by 24.2% and 23.3%, respectively.

[0185] At the same time, as can be seen from the data in Table 2, Examples 1 and 2 exhibited a 9 nm blue shift relative to Comparative Example 1 and a 2 nm red shift relative to Comparative Example 2. Such results are completely opposite to the results disclosed in CN111655705A and would be unexpected by those skilled in the art.

[0186] As can be seen from the above, R1 and R nThe metal complexes according to the present application which also contain substituents can reduce the half-width while maintaining excellent device efficiency, and are therefore advantageous in providing high-performance devices with more saturated emission.

[0187] Element Example 3

[0188] The embodiment of Device Example 3 is similar to Device Example 1, except that Metal Complex 2252 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0189] Comparative Example 4 of the Element

[0190] The embodiment of Comparative Example 4 of the device is the same as that of Example 1 of the device, except that the compound GD4 replaces the metal complex 1345 of the present invention in the light-emitting layer (EML).

[0191] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0192] [Table 3]

[0193] The structure of the metal complex newly used in the device is shown below. [ka]

[0194] The IVL characteristics of the device were measured. 2 Under the conditions, the CIE data of the element, the maximum radiation wavelength (λ max The wavelength, full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) were measured, and the data are recorded and shown in Table 4.

[0195] [Table 4]

[0196] The difference between the light-emitting materials used in Example 3 and Comparative Example 4 is that R n The only difference is whether the structure of Formula 2 in the present invention is the same. As can be seen from the data in Table 4, the device voltage increased by 0.2 V and the efficiency decreased by 5.3%, but Example 3 still achieved a high level of over 23%. More importantly, Example 3 exhibited a 10 nm blue shift in emission wavelength and a 6.1 nm narrower half-width than Comparative Example 4. The bluer emission wavelength and narrower half-width of Example 3 than Comparative Example 4 allow the device to have a wider color gamut and higher color purity. This is closer to the industry's requirements for the luminescent performance of green light materials. Therefore, it has been demonstrated that the metal complex of the present invention can produce devices with superior performance.

[0197] Element Example 4

[0198] The embodiment of Device Example 4 is similar to Device Example 1, except that Metal Complex 1493 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0199] Comparative Example 5 of the Element

[0200] The embodiment of Comparative Example 5 of the device is the same as that of Example 1 of the device, except that the compound GD5 replaces the metal complex 1345 of the present invention in the light-emitting layer (EML).

[0201] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0202] [Table 5]

[0203] The structure of the metal complex newly used in the device is shown below. [ka]

[0204] The IVL characteristics of the device were measured. 2 CIE data of the element under constant current, maximum emission wavelength (λ max The wavelength, full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) were measured, and the data are recorded and shown in Table 6.

[0205] [Table 6]

[0206] The difference between the light-emitting material used in Example 4 and that used in Comparative Example 5 is R n The only difference is whether the structure of Formula 2 in the present invention is the same as that of Example 4. As can be seen from the data in Table 6, compared to Comparative Example 5, Example 4 had a driving voltage lower by 0.12 V, a slight decrease in current efficiency, and a slight increase in external quantum efficiency, while the emission wavelength was blue-shifted by 10 nm and the half-width was narrowed by 3.4 nm. This reaffirms that the metal complex of the present invention can achieve a wider color gamut and higher color purity while maintaining excellent device performance. This comes closer to the industry's requirements for the luminescent performance of green light-emitting materials. This demonstrates that the metal complex of the present invention can achieve devices with better performance.

[0207] Example of top-emission device: To study the device performance when the metal complex most closely meets the BT.2020 light-emitting requirements, the microcavities of the following top-emission devices were adjusted until the CIEx of the device reached 0.170, and the device performance was recorded. As described above for the top-emission devices, because different metal complexes have different refractive indices, the lengths of the microcavities of top-emission devices containing these different metal complexes may be slightly different, i.e., the thickness of the HTL may be slightly different.

[0208] Element Example 5

[0209] First, a 0.7 mm thick glass substrate with a pre-patterned indium tin oxide (ITO) 75 Å / Ag 1500 Å / ITO 150 Å was used as the anode, where the 150 Å ITO deposited on the Ag served as the hole injection function. 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 layers, a vacuum of approximately 10 -6 At Torr, the layers were deposited sequentially on the anode by hot vacuum evaporation at rates of 0.01–10 Å / s. First, compounds HT and PD were co-evaporated to form a hole injection layer (HIL, 97:3, 100 Å). Compound HT was then deposited on the HIL to form a hole transport layer (HTL, which simultaneously served as a microcavity control layer, controlling the microcavity to within 1000–1500 Å). Compound PH-23 was then deposited on the hole transport layer to form an electron blocking layer (EBL, 50 Å). Metal complex 1493, compound PH-1, and compound H-40 were co-evaporated to form an emissive layer (EML, 4:48:48, 400 Å), compound H-2 was co-evaporated to form a hole-blocking layer (HBL, 50 Å), compounds ET and Liq were co-evaporated to form an electron-transporting layer (ETL, 40:60, 350 Å), 10 Å of metal Yb was co-evaporated to form an electron-injecting layer (EIL), and metals Ag and Mg were co-evaporated in a 9:1 ratio to form a cathode (140 Å), and compound CP (compound CP has a refractive index of approximately 2.01 at 530 nm) was co-evaporated to a thickness of 800 Å to form a capping layer. The device was then transferred to a glove box and encapsulated in a nitrogen gas atmosphere with a glass cover to complete the device. In this example, the CIEx of the device obtained by adjusting the microcavity to about 1340 Å was 0.170, and the CE 0.170 obtained.

[0210] Device Example 6

[0211] The embodiment of the device in Example 6 is the same as that of the device in Example 5, except that the metal complex 1345 of the present invention is used instead of the metal complex 1493 of the present invention in the light-emitting layer. In this example, the microcavity was adjusted to about 1370 Å, and the CIEx of the device obtained was 0.170. 0.170 obtained.

[0212] Comparative Example 6 of the Element

[0213] The embodiment of Comparative Example 6 of the device is the same as that of Example 5 of the device, except that the metal complex GD5 of the present invention is used instead of the metal complex 1493 of the present invention in the light-emitting layer. In this example, the CIEx of the device obtained by adjusting the microcavity to about 1410 Å was 0.170, and the CE 0.170 obtained.

[0214] Comparative Example 7 of the Element

[0215] The embodiment of Comparative Example 7 of the device is the same as that of Example 5 of the device, except that the metal complex GD2 of the present invention is used instead of the metal complex 1493 of the present invention in the light-emitting layer. In this example, the microcavity of the device obtained by adjusting the diameter to about 1370 Å was 0.170, and the CE 0.170 obtained.

[0216] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0217] [Table 7]

[0218] The structure of the new material used in the device is as follows: [ka]

[0219] 10mA / cm2 The IVL characteristics of the device were measured under a constant current of 1000 kJ / s. The color coordinates of the device corresponding to x = 0.170 in the color coordinates CIE (x, y), the current efficiency (CE 0.170 ), external quantum efficiency (EQE 0.170 ) were recorded. The data were recorded and shown in Table 8.

[0220] [Table 8]

[0221] As can be seen from the data in Table 8, when the color coordinates CIE(x,y) of Example 5 and Comparative Example 6 are CIEx=0.170, the color coordinates of Example 5 and Comparative Example 6 are both close to the green color coordinates CIE (0.170, 0.797) of BT.2020, i.e., Example 5 and Comparative Example 6 both have relatively saturated green emission. However, the current efficiency and external quantum efficiency of Example 5 are improved by 16.3% and 16.4%, respectively, compared to Comparative Example 6, both of which are significant improvements. Therefore, it is shown that the use of the technical solution of the present invention can provide a device with better performance that approaches the emission requirements of BT.2020, and can maintain excellent device performance under these emission requirements.

[0222] Similarly, when the color coordinates CIE(x,y) of Example 6 and Comparative Example 7 are CIEx=0.170, the color coordinates of Example 6 and Comparative Example 7 are both close to the green color coordinates CIE(0.170,0.797) of BT.2020, i.e., Example 6 and Comparative Example 7 both have relatively saturated green emission. However, the current efficiency and external quantum efficiency of Example 6 are each improved by about 5% compared to Comparative Example 7. This shows that the use of the technical solution of the present invention can provide a device with better performance that approaches the emission requirements of BT.2020, and can maintain excellent device performance under these emission requirements.

[0223] Device Example 7

[0224] The embodiment of Device Example 7 is similar to Device Example 1, except that Metal Complex 2262 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0225] Device Example 8

[0226] The embodiment of Device Example 8 is similar to Device Example 1, except that Metal Complex 2164 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0227] Device Example 9

[0228] The embodiment of Device Example 9 is similar to Device Example 1, except that Metal Complex 2394 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0229] Device Example 10

[0230] The embodiment of Device Example 10 is similar to Device Example 1, except that Metal Complex 2955 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0231] Device Example 11

[0232] The embodiment of Device Example 11 is similar to Device Example 1, except that Metal Complex 982 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0233] Device Example 12

[0234] The embodiment of Device Example 12 is similar to Device Example 1, except that Metal Complex 3671 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0235] Device Example 13

[0236] The embodiment of Device Example 13 is the same as Device Example 1, except that in the light-emitting layer (EML), metal complex 2526 replaces metal complex 1345 of the present invention, and in the HIL, compound HT:compound PD=97:3 replaces compound HI.

[0237] Device Example 14

[0238] The embodiment of Device Example 14 is similar to Device Example 13, except that metal complex 2657 replaces metal complex 2526 of the present invention in the light-emitting layer (EML).

[0239] Device Example 15

[0240] The embodiment of Device Example 15 is similar to Device Example 1, except that Metal Complex 1371 replaces Metal Complex 1345 of the present invention in the light-emitting layer (EML).

[0241] Device Example 16

[0242] The embodiment of Device Example 16 is similar to Device Example 13, except that Metal Complex 2393 replaces Metal Complex 2526 of the present invention in the light-emitting layer (EML).

[0243] Device Example 17

[0244] The embodiment of Device Example 17 is similar to Device Example 13, except that metal complex 2921 replaces metal complex 2526 of the present invention in the light-emitting layer (EML).

[0245] Device Example 18

[0246] The embodiment of Device Example 18 is similar to Device Example 13, except that Metal Complex 2249 replaces Metal Complex 2526 of the present invention in the light-emitting layer (EML).

[0247] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0248] [Table 9] TIFF0007762972000066.tif104168

[0249] The structure of the new material used in the device is as follows: [ka] [ka]

[0250] The IVL characteristics of the device were measured. 2 CIE data of the element under constant current, maximum emission wavelength (λ max The wavelength, full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) were measured, and the data are recorded and shown in Table 10.

[0251] [Table 10]

[0252] As can be seen from the data in Table 10, the light-emitting materials used in Examples 7 to 18 were all L having the structure of Formula 1 according to the present application. a The devices in Examples 7 to 18, which contained the ligand, all had deep green emission, narrow half-widths, and external quantum efficiencies (EQEs) of 24% or more at the deep green emission wavelength, reaching a high level in the field. Among them, Examples 10, 12 to 14, and 17 all had external quantum efficiencies (EQEs) of 25.5% or more, and in particular, Examples 13 and 14 had surprising external quantum efficiencies (EQEs) of 27.02% and 27.25%. Therefore, the present invention is based on the L-type fluorine-containing compound having different substituents and a structure represented by Formula 1.a It has been shown that metal complexes containing the ligand can achieve excellent device performance. At the same time, in this application, L having a structure represented by Formula 1 a Ligands and different L b By combining with ligands, superior device performance can also be obtained.

[0253] As can be seen from the above results, the specific R and R n L having a structure represented by formula 1, substituted with a By applying the metal complex containing the ligand to an organic electroluminescence device, the half-width of the emission spectrum can be further reduced while maintaining the high performance of the device, and the luminescence saturation of the device can be improved, resulting in high efficiency under conditions that are closer to the commercial luminescence requirements of BT.2020. n L having a structure represented by formula 1, substituted with a Metal complexes containing the ligands are high performance luminescent materials with promising commercial applications.

[0254] 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.

Claims

1. Metal M and ligand L coordinated with metal M ａ A metal complex comprising: L ａ has a structure represented by Formula 1, 【Chemistry 1】 In Formula 1, the metal M is selected from Ir; In formula 1, 【Chemistry 2】 is selected from the following structures, which may be the same or different for each occurrence: 【Transformation 3】 "#" represents the bonding site with G 1 ; 【Chemistry 4】 represents the bonding site to X 1 ; G １ and G ２ is chosen from single bonds at each occurrence, X3 to X ６ is the same or different for each occurrence ｘ or N, X 1 is selected from C, and Y １ Combined with X2 is selected from C, G ２ and bonded to the metal M by Y 1 is selected from C and Y 2 is selected from N; Z is selected from the group consisting of O, S, and Se; R represents a mono-substituted, poly-substituted, or unsubstituted group, and when a plurality of Rs are present, the plurality of Rs are the same or different; R, R ｘ 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 2 to 20 ring ... a substituted or unsubstituted alkynyl group having 6 to 20 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 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, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; R １ is selected from a cyano group, R ｎ has a structure represented by formula 2: 【Transformation 5】 In Formula 2, "*" represents the bonding point between Formula 2 and Formula 1, L is selected from a single bond and a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, the substituted alkylene group meaning that the alkylene group is substituted with deuterium; R ２ , R ３ and R ４ are the same or different at each occurrence and are selected from unsubstituted alkyl groups having 1 to 20 carbon atoms; Adjacent substituents R may be bonded to form a ring, Adjacent substituents R ｘ may be bonded to form a ring, Adjacent substituents R ２ , R ３ and R ４ may be bonded to form a ring, Metal complexes.

2. In formula 1, 【Transformation 6】 is selected from the following structures: 【Transformation 7】 (R may be the same or different at each occurrence and represent mono-, poly- or unsubstituted, and when multiple R are present in any one structure, said R may be the same or different, R, at each occurrence, may be the same or different and is 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 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 alkenyl group having 2 to 20 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 alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, and combinations thereof; Adjacent substituents R may be bonded to form a ring, "#" is G １ represents the point of attachment to 【Transformation 8】 represents the bonding site to X1.

3. The metal complex is M(L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ having the general formula L ａ , L ｂ and L ｃ are the first, second and third ligands coordinated to the metal M, respectively, and L ｃ and the above L ａ or L ｂ are the same or different, and L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M, and when m is 2 or more, multiple L ａ are the same or different, and when n is 2, two L ｂ are the same or different, and when q is 2, two L ｃ are the same or different, L ｂ and L ｃ may be the same or different for each occurrence. 【Chemistry 9】 2. The metal complex according to claim 1, wherein the metal complex is selected from the group consisting of: (X ｂ are the same or different for each occurrence and are O, S, Se, NR Ｎ１ , C.R. Ｃ１ R Ｃ２ selected from the group consisting of R ａ and R ｂ are the same or different at each occurrence and represent mono-, multi- or no substitution; R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｃ１ and R Ｃ２ 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 2 to 20 ring ... a substituted or unsubstituted alkynyl group having 6 to 20 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 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, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; Adjacent substituents R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｃ１ and R Ｃ２ may be bonded to form a ring.)

4. Z is selected from O or S; The metal complex of claim 1.

5. The metal complex is Ir(L ａ ) ｍ (L ｂ ) ３－ｍ 4. The metal complex of claim 3, having a general structure of the formula: and having a structure represented by formula 3. 【Chemistry 10】 (m is selected from 1, 2, or 3, and when m is selected from 1, two L ｂ are the same or different, and when m is selected from 2 or 3, a plurality of L ａ are the same or different, Z is selected from the group consisting of O, S, and Se; U １ ~U ８ are selected from CRu, identically or differently at each occurrence; X ３ ~X ６ is selected from CRx, which may be the same or different at each occurrence; Y ３ ~Y ６ are selected from CR, identically or differently for each occurrence, R １ is selected from a cyano group, R ｕ , R ｘ and R, at each occurrence, is the same or different and is 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 alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; L is selected from a single bond and an unsubstituted alkylene group having 1 to 20 carbon atoms; R ２ , R ３ and R ４ are the same or different at each occurrence and are selected from unsubstituted alkyl groups having 1 to 20 carbon atoms; Adjacent substituents R ｕ may be bonded to form a ring, Adjacent substituents R may be bonded to form a ring, Adjacent substituents R ｘ may be bonded to form a ring, Adjacent substituents R ２ , R ３ , R ４ may be bonded to form a ring.)

6. 2. The metal complex according to claim 1, wherein L is selected from the group consisting of a single bond and an unsubstituted alkylene group having 1 to 6 carbon atoms.

7. L is selected from a single bond, a deuterated methylene group, or an unsubstituted methylene group; The metal complex of claim 1.

8. R ２ , R ３ and R ４ are the same or different at each occurrence and are selected from unsubstituted alkyl groups having 1 to 12 carbon atoms; The metal complex of claim 1.

9. R ２ , R ３ and R ４ are the same or different at each occurrence and are selected from unsubstituted alkyl groups having 1 to 6 carbon atoms; The metal complex of claim 1.

10. X ３ ~X ６ is the same or different for each occurrence ｘ and Y ３ ~Y ６ are selected from CR, which may be the same or different for each occurrence, and U １ ~U ８ is the same or different for each occurrence ｕ Selected from R ｘ , R and R ｕ 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 alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof; The metal complex according to claim 5.

11. R ｘ , R and R ｕ are each the same or different and are selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridine, trimethylsilyl, trimethylgermanium, and combinations thereof; The metal complex according to claim 5.

12. Y ３ ~Y ６ is CR, which may be the same or different for each occurrence, and Y ３ ~Y ６ at least one of the groups is selected from CR, wherein R 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof; The metal complex according to claim 5.

13. X ３ ~X ６ At least one of the following is CR ｘ wherein R ｘ 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 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 alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof; The metal complex of claim 1.

14. X ６ is CR ｘ wherein R ｘ is selected from the group consisting of deuterium, 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, and combinations thereof; The metal complex of claim 1.

15. R ｎ may be the same or different for each occurrence. 【Chemistry 11】 selected from the group consisting of The above R ｎ wherein the hydrogen atoms in the formula (I) may be partially deuterated. The metal complex of claim 1.

16. U １ ~U ８ At least one or at least two of ｕ wherein R ｕ 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, or a combination thereof, and all of the R ｕ the sum of the carbon atoms in The metal complex according to claim 5.

17. U １ ~U ４ At least one of the following is CR ｕ Selected from Y ３ ~Y ６ At least one of the R ｕ 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, or a combination thereof, ｕ the sum of the numbers of carbon atoms in R is 2 or more; Or U ５ ~U ８ At least one of the following is CR ｕ Selected from Y ３ ~Y ６ At least one of the R ｕ 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, or a combination thereof, ｕ the sum of the numbers of carbon atoms in R is 2 or more; Or U １ ~U ４ At least one of the following is CR ｕ Selected from U ５ ~U ８ At least one of the following is CR ｕ wherein R ｕ 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, or a combination thereof, and ｕ The sum of the numbers of carbon atoms in The metal complex according to claim 5.

18. L ａ may be the same or different for each occurrence of L ａ１ ~ L a1690 , L a3367 ~ L a3387 , L a3398 ~ L a3402 , L a3413 ~ L a3417 , L a3428 ~ L a3432 , L a3443 ~ L a3447 , L a3458 , L a3462 ~ L selected from the group consisting of a3476, L a3487 to L a3502, L a3505, L ａ１ ~L a1690 、L a3367 ~L a3387 、L a3398 ~L a3402 、L a3413 ~L a3417 、L a3428 ~L a3432 、L a3443 ~L a3447は、 【Chemistry 12】 wherein R １ , R ｎ , R ｘ４ , R ｘ５ , R ｘ６ , R １ ~R ４ is selected from the atoms or groups in the table below, 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 However, the structures of P1 to P156 are as follows: 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 However, L ａ３４５８ , L ａ３４６２ to L a3476 , L a3487 to L a3502 , and L a3505 are as follows: [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 The above L ａ１ Hydrogen in L a1690 to L a3367 to L a3387 , L a3398 to L a3402 , L a3413 to L a3417 , L a3428 to L a3432 , L a3443 to L a3447 , L a3458 , L a3462 to L a3476 , L a3487 to L a3502 , and L a3505 may be partially deuterated. The metal complex according to claim 3.

19. L ｂ may be the same or different for each occurrence. 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 selected from the group consisting of The above L ｂ１ ~L ｂ１８ , L ｂ２０ ~L ｂ２６ and L ｂ３１ ~L ｂ１５１ wherein the hydrogen atoms in the formula (I) may be partially or completely deuterated.

19. The metal complex of claim 18.

20. The metal complex is Ir(L ａ ) (L ｂ ) ２ The structure of which two L ｂ are identical, The metal complex is selected from the group consisting of metal complexes in the table below, and the metal complex is Ir(L ａ ) (L ｂ ) ２ The structure of which two L ｂ are identical, and L ａ and L ｂ and each correspond to a structure in the table below.

21. An organic electroluminescent device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, At least one of the organic layers contains the metal complex according to claim 1. Organic electroluminescent element.

22. 22. The organic electroluminescence device according to claim 21, wherein the organic layer containing the metal complex is a light-emitting layer.

23. The light-emitting layer further contains a first host compound.

23. The organic electroluminescence device according to claim 22.

24. The light-emitting layer further contains a second host compound.

24. The organic electroluminescence device according to claim 23.

25. the first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof; 25. The organic electroluminescence device according to claim 24.

26. the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex is 1% to 30% based on the total weight of the light-emitting layer; 25. The organic electroluminescence device according to claim 24.

27. A composition comprising the metal complex of claim 1.

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