Organic electroluminescent material and device thereof

Abstract

To provide an organic electroluminescent material and a device thereof.SOLUTION: The organic electroluminescent material is a metal complex containing a ligand La having a structure of Formula 1. Such new compounds with a fluorine substituent introduced at a particular position of the ligand La are applicable to electroluminescent devices and can provide more saturated luminescence and better device performance such as improved device efficiency and reduced device voltage. Further provided are an electroluminescent device containing the metal complex and a compound composition containing the metal complex.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound for use in an organic electronic device such as an organic light-emitting device. More particularly, the present invention relates to a compound having a structure represented by Formula 1, a The present invention relates to a metal complex containing the ligand, an organic electroluminescent device containing the metal complex, and a combination of compounds. [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] Cyano group substitution is not always introduced into phosphorescent metal complexes, such as iridium complexes. The applicant's basic application US20200251666A1 discloses metal complexes having cyano group-substituted ligands, which can be used in organic electroluminescent devices to improve the performance and color saturation of the devices, which has reached a high level in the industry, but there is still room for improvement. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] U.S. Patent Application Publication No. 20200251666A1 [Non-patent literature]

[0010] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]

[0011] In order to solve at least part of the above-mentioned problems, the present invention provides a compound represented by formula 1, a The present invention provides a series of metal complexes containing the ligands. The metal complexes can be used as light-emitting materials in electroluminescent devices. These novel compounds can be applied to electroluminescent devices and can provide better device performance, such as more saturated light emission, improved device efficiency, and reduced device voltage. [Means for solving the problem]

[0012] 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:

[0013] [ka] (wherein in formula 1, the metal M is selected from metals having a relative atomic mass greater than 40; Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X1 to X8 may be the same or different for each occurrence. x or selected from N, Y1 to Y4 may be the same or different for each occurrence. y or selected from N, R, R x , R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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 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; At least one of X1 to X8 is CR x and the R x is a cyano group, At least one of Y2 and Y3 is CR y and the R y is F, Adjacent substituents R and R x and R y may be bonded to form a ring.

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

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

[0016] L having a structure represented by formula 1 according to the present invention a A series of metal complexes containing the ligand L a By introducing fluorine substituents at specific positions of the ligands, these novel compounds can be applied to electroluminescent devices and provide better device performance, such as more saturated emission, improved device efficiency, and reduced device voltage. [Brief explanation of the drawings]

[0017] [Figure 1] 1 is a schematic diagram of an organic light emitting device that may include a combination of metal complexes and compounds according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light emitting device that may include a combination of metal complexes and compounds according to the present invention. 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] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

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

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

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

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

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

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

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

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

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

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

[0031] Definitions of Substituent Terminology

[0032] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0033] 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.

[0034] 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.

[0035] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisopropyl. Heteroalkyl groups may also be substituted.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] In the present invention, unless otherwise specified, when any term from the group consisting of substituted alkyl group, substituted cycloalkyl group, substituted heteroalkyl group, substituted heterocyclic group, substituted aralkyl group, substituted alkoxy group, substituted aryloxy group, substituted alkenyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted amino group, substituted acyl group, substituted carbonyl group, substituted carboxyl group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, and substituted phosphino group is used, any one group from the group consisting of alkyl group, cycloalkyl group, heteroalkyl group, heterocyclyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is included. , deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted 6 carbon atoms This means that the aryl group may be substituted with one or more groups selected from an aryl group having from 3 to 30 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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:

[0053] [ka]

[0054] 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:

[0055] [ka]

[0056] 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.

[0057] [ka]

[0058] 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:

[0059] [ka] (wherein in formula 1, the metal M is selected from metals having a relative atomic mass greater than 40; Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X1 to X8 may be the same or different for each occurrence. x or selected from N, Y1 to Y4 may be the same or different for each occurrence. y or selected from N, R, R x , R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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 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; At least one of X1 to X8 is CR x and the R x is a cyano group, At least one of Y2 and Y3 is CR y and the R y is F, Adjacent substituents R and R x and R y may be bonded to form a ring.

[0060] In the present specification, "adjacent substituents R, R x , R y may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R, two substituents R x two substituents R y two substituents R y and R x two substituents R and R xThis means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0061] According to one embodiment of the present invention, L a has a structure represented by one of formulas 1a-1e.

[0062] [ka] (Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and two R When present simultaneously, two R's may be the same or different. In Formula 1a and Formula 1c, X3 to X8 may be the same or different at each occurrence and may be CR x or selected from N, In formula 1b, X1 and X4 to X8 each appear the same or different and are CR x or selected from N, In Formula 1d and Formula 1e, X1 to X2 and X5 to X8 may be the same or different at each occurrence and may represent CR x or selected from N, Y1 to Y4 may be the same or different for each occurrence. y or selected from N, R, R x , R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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 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; In Formula 1a and Formula 1c, at least one of X3 to X8 is CR x and the R x is a cyano group, In formula 1b, at least one of X1 and X4 to X8 is CR x and the R x is a cyano group, In Formula 1d and Formula 1e, at least one of X1 to X2 and X5 to X8 is CR x and the R x is a cyano group, At least one of Y2 and Y3 is CR y and the R y is F, Adjacent substituents R and R x , R y may be bonded to form a ring.

[0063] According to one embodiment of the present invention, the metal complex is a ) m (L b )n (L c ) q having the general formula the metal M is selected from metals with a relative atomic mass greater than 40, preferably M is selected, identically or differently at each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, more preferably M is selected, identically or differently at each occurrence, from Pt or Ir; L a , L b and L c are the primary, secondary, and tertiary ligands that coordinate with the metal M, respectively, and L c and the aforementioned L a or L b and L a , L b and L c may be linked to form multidentate ligands, for example, L a , L b and L c Any two of may be linked to form a tetradentate ligand, and for example, L a , L b and L c may be linked together to form a hexadentate ligand, and for example, L a , L b , L c may not all be linked to form a multidentate ligand, m=1, 2 or 3, n=0, 1 or 2, q=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 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 b and L c may be the same or different for each occurrence. [ka] and is selected from structures represented by any one of the groups consisting of: R a , Rb and R c are the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 , C.R. C1 R C2 selected from the group consisting of 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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 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.

[0064] In the present specification, "adjacent substituents R a , R b , R c , R N1 , R C1and R C2 may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a two substituents R b two substituents R c R a and R b R a and 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 these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0065] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 2:

[0066] [ka] (m is selected from 1, 2, or 3. When m=1, two L b are the same or different, and when m=2 or 3, multiple L a are the same or different, Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X3 to X8 are the same or different CRs for each occurrence. x or selected from N, Y1 to Y4 may be the same or different for each occurrence.y or selected from N, R, R x , R y R1 to R8 each appearing may be the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted ... a substituted or unsubstituted alkenyl group having 6 to 30 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 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; At least one of X3 to X8 is CR x and the R x is a cyano group, At least one of Y2 and Y3 is CR y and the R y is F, Adjacent substituents R and R x , R y R1 to R8 may be bonded to form a ring.)

[0067] In the examples, "adjacent substituents R, R x , R y The phrase "R1 to R8 may be bonded to form a ring" refers to adjacent substituent groups, for example, two substituents R, two substituents R x two substituents R yThis means that any one or more of two substituents among R1 to R8 may be bonded to each other to form a ring. Obviously, these substituents do not have to be bonded to each other to form a ring.

[0068] According to one embodiment of the present invention, Z is selected from O and S.

[0069] According to one embodiment of the present invention, Z is O.

[0070] According to one embodiment of the present invention, Y1 to Y4 may be the same or different for each occurrence. y and at least one of Y2 and Y3 is selected from CR y and the R y is F.

[0071] According to one embodiment of the present invention, Y1 to Y4 may be the same or different for each occurrence. y or N, and at least one of Y2 and Y3 is CR y and the R y is F.

[0072] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y is F, and the others of Y1 to Y4 are CR y If selected from y are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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.

[0073] In this specification, "other than Y1 to Y4" refers to the following situation: Y2 is CR y and the R yWhen Y3 is CR, "others of Y1 to Y4" refers to Y1 and Y3 to Y4. y and the R y When Y2 and Y3 are both CR, "others of Y1 to Y4" refers to Y4 and Y1 to Y2. y and the R y When is F, "others of Y1 to Y4" refers to Y1 and Y4.

[0074] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y is F, and the others of Y1 to Y4 are CR y If selected from y and each occurrence may be the same or different and is selected from the group consisting of hydrogen, 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, and combinations thereof.

[0075] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y is F, and the others of Y1 to Y4 are CR y If selected from y is selected from hydrogen, deuterium, a methyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, or a combination thereof, and the hydrogen atoms in the above groups may be partially or completely deuterated.

[0076] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y is F, and at least one of Y1 to Y4 is CR y and at least one R yis selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0077] According to one embodiment of the present invention, Y2 is y and the R y is fluorine, and Y3 is CR y and R y is selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0078] According to one embodiment of the present invention, Y3 is y and the R y is fluorine and Y2 is CR y and R y is selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0079] According to one embodiment of the present invention, X1 to X8 may be the same or different for each occurrence and may be C or CR. x Selected from.

[0080] According to one embodiment of the present invention, at least two of X1 to X8 are CR x and the one R x is a cyano group, and at least one other 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 is selected from the group consisting of an 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 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.

[0081] According to one embodiment of the present invention, at least two of X1 to X8 are CR x and the one R x is a cyano group, and at least one other 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 arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.

[0082] According to one embodiment of the present invention, at least two of X1 to X8 are CR x and the one R x is a cyano group, and at least one other R xis selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0083] According to one embodiment of the present invention, X7 and X8 are both CR x and wherein one of R x is a cyano group, and another one of the R x is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0084] According to one embodiment of the present invention, at least one of X5 to X8 is CR x and the R x is a cyano group.

[0085] According to one embodiment of the present invention, the X7 x and the R x is a cyano group.

[0086] According to one embodiment of the present invention, the X8 x and the R x is a cyano group.

[0087] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are 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.

[0088] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

[0089] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, and combinations thereof, and the hydrogen atoms in the above groups may be partially or completely deuterated.

[0090] According to one embodiment of the present invention, R 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.

[0091] According to one embodiment of the present invention, R is a methyl group or a deuterated methyl group.

[0092] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~La 766 L a1 ~La 766 The specific structure is shown in claim 14.

[0093] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b78 L b1 ~L b78 The specific structure is shown in claim 15.

[0094] According to one embodiment of the present invention, L b may be the same or different for each occurrence of Lb1 ~L b80 L b1 ~L b80 The specific structure is shown in claim 15.

[0095] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) structure, and L a may be the same or different for each occurrence of L a1 ~L a766 and L b L b1 ~L b78 It is any one selected from the group consisting of: a1 ~La 766 The specific structure of is shown in claim 14, b1 ~L b78 The specific structure is shown in claim 15.

[0096] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) structure, and L a may be the same or different for each occurrence of L a1 ~L a766 and L b L b1 ~L b80 It is any one selected from the group consisting of: a1 ~La 766 The specific structure of is shown in claim 14, b1 ~L b80 The specific structure is shown in claim 15.

[0097] According to one embodiment of the present invention, the metal complex is Ir(L a )(L b )2 structure, and L a L a1 ~L a766 and L b may be the same or different for each occurrence of L b1~L b78 Any one or two selected from the group consisting of: a1 ~La 766 The specific structure of is shown in claim 14, b1 ~L b78 The specific structure is shown in claim 15.

[0098] According to one embodiment of the present invention, the metal complex is Ir(L a )(L b )2 structure, and L a L a1 ~L a766 and L b may be the same or different for each occurrence of L b1 ~L b80 Any one or two selected from the group consisting of: a1 ~La 766 The specific structure of is shown in claim 14, b1 ~L b80 The specific structure is shown in claim 15.

[0099] According to one embodiment of the present invention, the metal complex is Ir(L a )3 structure, and L a may be the same or different for each occurrence of L a1 ~L a766 Any one, any two, or any three selected from the group consisting of: L a1 ~La 766 The specific structure is shown in claim 14.

[0100] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 360. Specific structures of metal complex 1 to metal complex 360 are set forth in claim 16.

[0101] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 390. Specific structures of metal complex 1 to metal complex 390 are set forth in claim 16.

[0102] According to one embodiment of the present invention, there is disclosed an electroluminescent device including an anode, a cathode, and organic layers disposed 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-described embodiments.

[0103] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

[0104] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element emits green light.

[0105] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent device comprises at least one first host compound.

[0106] According to an embodiment of the present invention, the light-emitting layer in the electroluminescent device further comprises at least two host compounds.

[0107] According to one embodiment of the present invention, the at least one host compound in the electroluminescent device comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0108] According to an embodiment of the present invention, the first host compound in the electroluminescent device has a structure represented by Formula 3:

[0109] [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; V may be the same or different for each occurrence. v or N, and at least one of V is C, and L x is combined with U may be the same or different for each occurrence. u or N, and at least one of U is C, and L x is combined with R v and R u 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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 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 Rv and R u may be bonded to form a ring.

[0110] In the examples, "adjacent substituents R v and R u may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v two substituents R u two substituents R v and R u This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0111] According to one embodiment of the present invention, the first host compound in the electroluminescent device has a structure represented by one of Formulas 3-a to 3-j.

[0112] [ka]

[0113] According to one embodiment of the present invention, in the electroluminescent device, when the metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 1% to 30% of the total weight of the light-emitting layer.

[0114] According to one embodiment of the present invention, in the electroluminescent device, when the metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 3% to 13% relative to the total weight of the light-emitting layer.

[0115] According to another embodiment of the present invention, a combination of compounds comprising a metal complex as described in any one of the above embodiments is disclosed.

[0116] Combination with other materials

[0117] 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.

[0118] 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.

[0119] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, a differential scanning calorimeter, a Shanghai Lingguang Technology fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system, a service life test system from Suzhou Fusida, an ellipsometer from Beijing Liangtuo, and the like) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification. [Example]

[0120] Examples of material synthesis

[0121] The preparation method of the compound according to the present invention is not limited. Taking the following compound as a typical but non-limiting example, its synthetic route and preparation method are as follows:

[0122] Synthesis Example 1: Synthesis of Metal Complex 4 [ka]

[0123] Intermediate 1 (2.2 g, 7.2 mmol), iridium complex 1 (3.5 g, 5.2 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added to a dry 250 mL round-bottom flask in this order. The reaction was heated at 110 °C for 120 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 obtain metal complex 4 (0.94 g, 22.4% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 805.2.

[0124] Synthetic Example 2: Synthesis of Metal Complex 14 [ka]

[0125] A 250 mL dry round-bottom flask was charged with intermediate 2 (1.5 g, 4.9 mmol), iridium complex 1 (2.9 g, 4.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), in that order. The reaction was heated at 90 °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 14 (0.70 g, 21.8% yield) as a yellow solid. The structure of the product was confirmed as the target product with a molecular weight of 805.2.

[0126] Synthetic Example 3: Synthesis of Metal Complex 44 [ka]

[0127] Intermediate 2 (1.6 g, 5.2 mmol), iridium complex 2 (3.1 g, 4.0 mmol), 2-ethoxyethanol (25 mL), and DMF (25 mL) were added to a dry 250 mL round-bottom flask in this order. The reaction was carried out at 90 °C under N2 protection for 144 h. 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 44 (0.58 g, 17.5% yield) as a yellow solid. The structure of the product was confirmed as the target product with a molecular weight of 833.2.

[0128] Synthesis Example 4: Synthesis of Metal Complex 103 [ka]

[0129] A 250 mL dry round-bottom flask was charged with intermediate 3 (1.2 g, 3.9 mmol), iridium complex 3 (2.5 g, 3.2 mmol), 2-ethoxyethanol (20 mL), and DMF (20 mL), in that order. The reaction was heated at 90 °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 103 (0.85 g, 30.9% yield) as a yellow solid. The structure of the product was confirmed as the target product with a molecular weight of 861.2.

[0130] Synthesis Example 5: Synthesis of Metal Complex 389 [ka]

[0131] A 250 mL dry round-bottom flask was charged with intermediate 4 (1.6 g, 4.2 mmol), iridium complex 4 (2.6 g, 3.2 mmol), 2-ethoxyethanol (25 mL), and DMF (25 mL), in that order. The reaction was heated at 90 °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 389 (0.48 g, 15.1% yield) as a yellow solid. The structure of the product was confirmed as the target product with a molecular weight of 993.3.

[0132] 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.

[0133] Element Example 1

[0134] 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. -8In the case of a 1000-kV TFT, the following materials 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 H1 was used as an electron blocking layer (EBL). Then, metal complex 4 of the present invention was doped into compounds H1 and H2 to form an emitting layer (EML). Compound H3 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 as an electron injection layer, and 120 nm of aluminum was deposited as a cathode. The device was then transferred to a glove box and encapsulated using a glass cover and a moisture absorbent to complete the device.

[0135] Element Example 2

[0136] The embodiment of device example 2 is similar to device example 1, except that metal complex 14 of the present invention replaces metal complex 4 of the present invention in the light-emitting layer (EML).

[0137] Element Example 3

[0138] The embodiment of device example 3 is similar to device example 1, except that metal complex 44 of the present invention replaces metal complex 4 of the present invention in the light-emitting layer (EML).

[0139] Element Example 4

[0140] The embodiment of Device Example 4 is similar to Device Example 1, except that Metal Complex 389 of the present invention replaces Metal Complex 4 of the present invention in the light-emitting layer (EML).

[0141] Comparative Example 1 of the Element

[0142] The embodiment of Comparative Example 1 of the device is similar to that of Example 1 of the device, except that the compound GD1 replaces the metal complex 4 according to the present invention in the light-emitting layer (EML).

[0143] Comparative example 2 of the element

[0144] 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 4 according to the present invention in the light-emitting layer (EML).

[0145] Comparative Example 3 of the Element

[0146] The embodiment of Comparative Example 3 of the device is similar to that of Example 1 of the device, except that the compound GD3 replaces the metal complex 4 according to the present invention in the light-emitting layer (EML).

[0147] The detailed layer structure and thickness of the device are shown in Table 1 below. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0148] [Table 1]

[0149] The structure of the material used in the element is represented as follows:

[0150] [ka] [ka]

[0151] The IVL characteristics of the element were measured. 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), and external quantum efficiency (EQE) were measured. These data are recorded and displayed in Table 2.

[0152] [Table 2]

[0153] summary

[0154] Table 2 shows the performance of the devices of the example and comparative examples. As can be seen from the data in Table 2, L a Compared to Comparative Example 1, which has no ligand substitution, Examples 1 and 2 exhibited a 4-5 nm blue-shift in emission wavelength and more saturated green emission. Furthermore, Examples 1 and 2 achieved device EQEs of 24.37% and 24.65%, respectively, both of which were higher than the 23.39% of Comparative Example 1, further improving on the already high level of Comparative Example 1. Furthermore, the device voltages of Examples 1 and 2 were both approximately 0.35 V lower than those of Comparative Example 1.

[0155] L a The spectrum of Comparative Example 3, which has deuterated methyl groups substituted at the Y2 and Y3 positions of the ligand, respectively, is similar to that of Examples 1 and 2, but the EQE of Comparative Example 3 is reduced to a different extent compared to Examples 1 and 2, and the device voltage is also higher than that of Examples 1 and 2.

[0156] L a In Comparative Example 2, which has a fluorine substitution at the Y1 position of the ligand, the maximum emission wavelength is red-shifted by about 20 nm and the full width at half maximum is wider by 18.5 nm and 23.9 nm, respectively, compared to Examples 1 and 2. Therefore, the emission color of Comparative Example 2 is unsaturated. In addition, Comparative Example 2 has a somewhat lower EQE than Examples 1 and 2, and the device voltage is also slightly higher than Examples 1 and 2.

[0157] As can be seen from the above results, the metal complexes according to the present invention having F-substituted ligands at specific positions are a Compared to metal complexes with no substitution or substitution by other alkyl groups at the same position of the ligand, or with fluorine substitution at other positions, the device performance improved, particularly the device voltage decreased, the EQE improved, and the saturation of the emission complexion improved.

[0158] Examples 3 and 4 both showed significant improvements over Comparative Examples 1 to 3, exhibiting higher EQEs and lower drive voltages. The drive voltage of Example 3 was 0.5 V, 0.22 V, and 0.21 V lower than Comparative Examples 1 to 3, respectively. Example 4, which used the metal complex of the present invention, achieved an EQE of 26.52%, which was improved by approximately 13.4%, 15.2%, and 14.6% over Comparative Examples 1 to 3, respectively. At the same time, the full width at half maximum of Example 4 was very narrow, at only 32.3 nm, which was at a very high level in the industry.

[0159] As can be seen from the above results, the metal complexes according to the present invention having F-substituted ligands at specific positions have improved device performance compared to metal complexes having fluorine substitutions at other positions on the ligand, in particular, improved emission color saturation, narrower full width at half maximum, improved EQE, and reduced voltage.

[0160] 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. The metal complex has an IrL a (L b ) 2 structure represented by formula 2. 【Chemistry 1】 (Two L ｂ are the same or different, Z is selected from O; X ３ ~X ８ is the same or different for each occurrence ｘ Selected from Y １ ~Y ４ is the same or different for each occurrence ｙ Selected from R １ ~R ８ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups of 1 to 6 carbon atoms, and combinations thereof; R ｘ are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a cyano group, and combinations thereof; X ７ is CR ｘ and the R ｘ is a cyano group, or X ８ is CR ｘ and the R ｘ is a cyano group, Y ２ and Y ３ At least one of the following is CR ｙ and the R ｙ is F, Y １ ~Y ４ Of these, the ones other than CF are CR ｙ and wherein R ｙ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and combinations thereof.

2. Y ２ and Y ３ At least one of the following is CR ｙ and the R ｙ is F and Y １ ~Y ４ Of these, the ones other than CF are CR ｙ and R ｙ 2. The metal complex according to claim 1, wherein each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

3. Y ２ and Y ３ At least one of the following is CR ｙ and the R ｙ is F and Y １ ~Y ４ Of these, the ones other than CF are CR ｙ and R ｙ is selected from hydrogen, deuterium, a methyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, or a combination thereof, and the hydrogen atoms in the group may be partially or completely deuterated.

4. Y ２ and Y ３ At least one of the following is CR ｙ and the R ｙ is F and Y １ ~Y ４ At least one of the following is CR ｙ and at least one R ｙ 2. The metal complex according to claim 1, wherein is selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and combinations thereof.

5. Y ２ is CR ｙ and the R ｙ is fluorine, and Y ３ is CR ｙ and the R ｙ is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and combinations thereof; Or, Y ３ is CR ｙ and the R ｙ is fluorine, and Y ２ is CR ｙ , and the R ｙ 2. The metal complex according to claim 1, wherein is selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and combinations thereof.

6. X ７ or X ８ is CR ｘ and the R ｘ is a cyano group, and at least one other R ｘ 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 aryl group having 6 to 12 carbon atoms, and combinations thereof.

7. X ７ is CR ｘ and the R ｘ The metal complex according to claim 1 , wherein is a cyano group.

8. R ２ , R ３ , R ６ , R ７ wherein at least one, at least two, at least three, or all of the above are selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and combinations thereof.

9. R ２ , R ３ , R ６ , R ７ wherein at least one, at least two, at least three, or all of the groups are selected from the group consisting of deuterium, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, and combinations thereof, and the hydrogen atoms in the groups may be partially or completely deuterated.

10. L ａ may be the same or different for each occurrence. 【Chemistry 2】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 The metal complex according to claim 1, which is any one selected from the group consisting of:

11. L ｂ may be the same or different for each occurrence. 【Transformation 3】 【change】 【change】 11. The metal complex of claim 10, selected from the group consisting of:

12. The metal complex is Ir(L ａ )(L ｂ ). ２ It has a structure of L ａ , and L ａ１ to L ａ２ , L ａ５ to L ａ６ , L ａ９ to L ａ１０ , L ａ１３ to L ａ１４ , L ａ１７ to L ａ１８ , L ａ２１ to L ａ２２ , L ａ２５ to L ａ２６ , L ａ２９ to L ａ３０ , L ａ３３ to L ａ３４ , L ａ３７ to L ａ３８ , L ａ４１ to L ａ４２ , L ａ４５ to L ａ４６ , L ａ４９ to L ａ５０ , L ａ５３ to L ａ５４ , L ａ５７ to L ａ５８ , L ａ６１ to L ａ６２ , L ａ６５ to L ａ６６ , L ａ６９ to L ａ７０ , L ａ７３ to L ａ７４ , L ａ８１ to L ａ８２ , L ａ８５ to L ａ８６ , L ａ８９ to L ａ９０ , L ａ９３ to L ａ９４ , L ａ９７ to L ａ９８ , L ａ１０１ to L ａ１０２ , L ａ１０５ to L ａ１０６ , L ａ１０９ to L ａ１１０ , L ａ１１３ to L ａ２８８ , L ａ３８１ to L ａ５５６ , L ａ７１１ to L ａ７１２ , L ａ７１５ ~L ａ７１６ , L ａ７１９ ~L ａ７２０ , L ａ７２３ ~L ａ７２４ , L ａ７２７ ~L ａ７２８ , L ａ７３１ ~L ａ７３２ , L ａ７３５ ~L ａ７３６ , L ａ７３９ ~L ａ７４０ , L ａ７４３ ~L ａ７４４ , L ａ７４７ ~L ａ７４８ and L is any one selected from the group consisting of ｂ Is, L ｂ１ ~L ｂ８０ The metal complex according to claim 11, wherein the metal complex is any one or two selected from the group consisting of:

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

14. an anode; A cathode; an organic layer provided between an anode and a cathode, An electroluminescence device, wherein at least one of the organic layers contains the metal complex according to any one of claims 1 to 13.

15. The electroluminescent device according to claim 14 , wherein the organic layer containing the metal complex is a light-emitting layer.

16. 16. The electroluminescent device according to claim 15, wherein the light-emitting layer emits green light.

17. 16. The electroluminescent device of claim 15, wherein the light-emitting layer comprises at least one first host compound.

18. 16. The electroluminescent device according to claim 15, wherein the light-emitting layer further comprises at least two host compounds.

19. 19. The electroluminescent device of claim 18, wherein the at least one host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

20. The first host compound has a structure represented by Formula 3, 【Chemistry 4】 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; V may be the same or different for each occurrence, and may be C, CR ｖ or N, and at least one of V is C; ｘ is combined with U may be the same or different for each occurrence, and may be C, CR ｕ or N, and at least one of U is C; L ｘ is combined with R ｖ and R ｕ 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 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 2 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 3 ... 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 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; Ar １ are the same or different at each occurrence and are 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 ｖ and R ｕ The electroluminescent device according to claim 17 , wherein may be bonded to form a ring.

21. 18. The electroluminescent device according to claim 17, wherein the metal complex is doped into at least one host compound, and the weight of the metal complex is 1% to 30% based on the total weight of the light-emitting layer.

22. 18. The electroluminescent device according to claim 17, wherein the metal complex is doped into at least one host compound, and the weight of the metal complex is 3% to 13% relative to the total weight of the light-emitting layer.

23. A combination of compounds comprising the metal complex according to any one of claims 1 to 13.

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