Organic electroluminescent materials and their elements

Abstract

To provide an organic electroluminescent material and a device thereof.SOLUTION: The organic electroluminescent material is a metal complex containing an La ligand La having a structure represented by formula 1. These novel compounds, when used in an electroluminescent device, obtain sufficiently excellent device performance, such as, for example, decreased device voltage, improved current efficiency, power efficiency and external quantum efficiency and can entirely improve various device performances and finally can extremely significantly improve overall device performance. There are further disclosed an organic electroluminescent device comprising the metal complex and a composition comprising the metal complex.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to compounds used in organic electronic devices such as organic light-emitting devices. More particularly, to compounds having the 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 electromotive cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect elements (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting elements.

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

[0004] OLEDs are divided into three different types according to their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. The triplet emission generated in the device is wasted through a non-radiative decay path, and this limitation, which limits the internal quantum efficiency (IQE) of fluorescent OLEDs to only 25%, has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs that use triplet emission from complex-containing heavy metals as the emitter. Therefore, it is possible to harvest singlet and triplet emission and achieve 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contribute to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency with thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, which allows for a transition of excitons back from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons through the penetration of triplet excitons between reverse systems (reverse intersystem crossing).

[0005] OLEDs may be further classified into small molecule OLEDs and polymer OLEDs, depending on the form of the material required. Small molecule refers to an organic or organometallic material that is not a polymer, and may have a large molecular weight as long as it has a precise structure. Dendrimers with a clear structure are recognized as small molecules. Polymer OLEDs include conjugated polymers and unconjugated polymers having luminescent groups in the side chains. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can become polymer OLEDs.

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

[0007] The emission color of an OLED can be achieved through the structural design of the light-emitting material. An OLED may contain one or more light-emitting layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized for green, yellow, and red OLEDs, blue phosphorescent elements still have problems such as insufficient blue saturation, short lifespan, and high operating voltage. Commercially available full-color OLED displays generally employ a mixed strategy, using blue fluorescence and yellow, red, or green phosphorescence. Currently, there is a problem in that the efficiency of phosphorescent OLEDs rapidly decreases at high brightness. Furthermore, there is a desire for a more saturated emission spectrum, higher efficiency, and a longer device lifespan.

[0008] US2013119354A1 discloses a metal complex having the following general formula structure. [ka] (However, R1 to R4 are selected from hydrogen, deuterium, alkyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, and combinations thereof.) While the aforementioned application only discloses the use of aryl substituents of a phenyl group in metal complexes and devices, it does not disclose or teach the effect on the performance of metal complexes and devices having the specific substituents described in the present application.

[0009] CN107236006A discloses a red photometallic complex having the following general formula structure. [ka]

[0010] The application discloses the use of arylamine-substituted fluorene ligands in metal complexes and devices. The application also discloses the use of polyarylamine-substituted fluorene groups in metal complexes, but does not disclose or teach the effect on the performance of metal complexes and devices containing ligands with specific skeletal structures having the specific substituents of the present application.

[0011] CN101108964A discloses a red photometallic complex having the following general formula structure. [ka]

[0012] The application discloses a red photometal complex containing a diketone-containing ligand having a carbazole substituent, and its use in organic electroluminescent devices. The application discloses the presence of a carbazole substituent in phenylquinoline and a metal complex coordinating with a diketone ligand, but it does not disclose or teach the metal complex containing a ligand with a specific skeleton structure having the specific substituents relating to the present application, or its effect on the performance of the device. [Prior art documents] [Patent Documents]

[0013] [Patent Document 1] US2013119354A1 [Patent Document 2] CN107236006A [Patent Document 3] CN101108964A [Non-patent literature]

[0014] [Non-Patent Document 1] Applied Physics Letters, 1987, 5 1(12):913~915 [Overview of the Initiative] [Problems that the invention aims to solve]

[0015] To solve at least some of the above-mentioned problems, the present invention provides L having the structure of formula 1. a The objective is to provide a series of metal complexes including ligands. When these novel compounds are used in electroluminescent devices, they can achieve sufficiently superior device performance, such as a decrease in device voltage and improved current efficiency, power efficiency, and external quantum efficiency, as well as comprehensively improve various aspects of the device's performance, ultimately significantly enhancing the overall performance of the device. [Means for solving the problem]

[0016] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal M. a A metal complex containing L a A metal complex having the structure represented by formula 1 is disclosed. [ka] (In Equation 1, metal M is selected from metals with a relative atomic mass greater than 40.) The ring Cy is selected from aromatic rings with 6 to 24 substituted or unsubstituted ring atoms, heteroaromatic rings with 5 to 24 substituted or unsubstituted ring atoms, or combinations thereof, and the ring Cy contains at least 3 carbon atoms. The ring Cy is bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond. X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and each instance is either the same or different. If two R's exist simultaneously, the two R's are either the same or different. X1~X8 are either the same or different each time they appear, C, CR x CR x1 Or selected from N, at least one of X1 to X4 is C, bonded to the ring Cy, X1, X2, X3, or X4 are bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond, At least one of X1 to X8 is CR x1 selected from, and R x1 has a structure represented by Formula 2,

Chemical Formula

[0017] Further embodiments of the present invention disclose an electroluminescent element comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex described in the above embodiments.

[0018] Further embodiments of the present invention disclose compositions comprising the metal complex described in the above embodiments.

[0019] The present invention has an L having a structure represented by formula 1. a A series of metal complexes including ligands are disclosed. When these novel compounds are used in electroluminescent devices, they can achieve sufficiently excellent device performance, such as a decrease in device voltage and improved current efficiency, power efficiency, and external quantum efficiency, as well as comprehensively improve various aspects of the device performance, ultimately significantly improving the overall performance of the device. [Brief explanation of the drawing]

[0020] [Figure 1] This is a schematic diagram of an organic light-emitting device which may include a metal complex according to the present invention and a composition containing the metal complex. [Figure 2] This is a schematic diagram of another organic light-emitting device which may include a metal complex according to the present invention and a composition containing the metal complex. [Modes for carrying out the invention]

[0021] OLEDs can be manufactured on a variety of substrates, including glass, plastic, and metal. Figure 1 shows an organic light-emitting apparatus 100 as an example without limitation. The apparatus is not necessarily manufactured to scale, and some layer structures may be omitted in the figure as necessary. The apparatus 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The apparatus 100 may be manufactured by sequentially depositing the described layers. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Patent US7279704B2, all of which are incorporated herein by reference.

[0022] There are many more examples for each of these layers. Exemplarily, a flexible, transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, incorporated entirely by reference. For example, in U.S. Patent Application Publication No. 2003 / 0230980, incorporated entirely by reference, an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 by Thompson et al., incorporated entirely by reference. For example, in U.S. Patent Application Publication No. 2003 / 0230980, incorporated entirely by reference, an example of an n-type doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio. Examples of cathodes, including composite cathodes having a thin metal layer such as Mg:Ag and a sputter-deposited transparent conductive ITO layer coated thereon, are disclosed in U.S. Patents 5,703,436 and 5,707,745, which are incorporated by full text. The principle and use of blocking layers are described in more detail in U.S. Patents 6,097,147 and U.S. Patent Publication 2003 / 0230980, which are incorporated by full text. Examples of injection layers are provided in U.S. Patent Publication 2004 / 0174116, which is incorporated by full text. Protective layers are described in U.S. Patent Publication 2004 / 0174116, which is incorporated by full text.

[0023] The layered structures described above are provided by non-limiting embodiments. The functions of an OLED can be realized 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 various materials can be used to achieve optimal performance. Any functional layer may include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0024] In one embodiment, the OLED may be described as having an "organic layer" provided between the cathode and the anode. The organic layer may consist of one or more layers.

[0025] An encapsulation layer is also required for OLEDs, and an organic light-emitting device 200 is shown exemplarily and without limitation as shown in Figure 2. The difference from Figure 1 is that an encapsulation layer 102 may be included on the cathode 190 to prevent harmful substances from the outside, such as moisture and oxygen. Any material capable of providing encapsulation functionality, such as glass or an organic-inorganic mixed layer, may be used as the encapsulation layer. The encapsulation layer should be located directly or indirectly outside the OLED element. Multilayer thin-film encapsulation is described in U.S. Patent US7968146B2, the entirety of which is incorporated herein by reference.

[0026] The elements manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the elements. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting lamps and / or signal lamps, head-up displays, all or part transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable elements, smartwatches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and taillights.

[0027] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0028] "Top" refers to the point furthest from the substrate, and "bottom" refers to the point closest to the substrate. When it is stated that the first layer is located "on" the second layer, the first layer is located relatively far from the substrate. Unless it is specified that the first layer "is in contact" with the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, it can still be stated that the cathode is located "on" the anode.

[0029] "A solution is processable" means that it is dissolvable, dispersed, or transportable in a liquid medium in the form of a solution or suspension, and / or can be deposited from a liquid medium.

[0030] It is believed that a ligand that directly enhances the photosensitivity of the propellant material may be called "photosensitive." If a ligand does not enhance the photosensitivity of the propellant material, it may be called "auxiliary." However, it is believed that auxiliary ligands can alter the properties of photosensitive ligands.

[0031] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin statistical limit due to the presence of delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet annihilation (TTA).

[0032] On the other hand, E-type delayed fluorescence relies on the conversion of excited states between triplet and singlet states, rather than on the collision of two triplet states. Compounds capable of producing E-type delayed fluorescence must have an extremely small singlet-triplet gap to facilitate 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 penetration rate between reverse systems (RISCs) is sufficiently fast, non-radiative decay from the triplet state can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlet states may even be 100%, far exceeding the 25% exciton spin statistics due to electro.

[0033] The characteristic of E-type delayed fluorescence is that it can be observed from an excited complex system or a single compound. Not limited to theory, E-type delayed fluorescence is observed when the luminescent material has a small singlet-triplet energy gap (ΔE S-T ) must be present. Organic nonmetal-containing donor-receptor luminescent materials can achieve this. The emission of these materials is typically characterized as donor-receptor charge transition (CT) emission. In these donor-receptor compounds, the spatial separation of HOMO and LUMO is generally small ΔE S-T This will generate the following states. These states may include the CT state. Typically, donor-acceptor luminescent materials are constructed by bonding an electron-donor moiety (e.g., an amine group or carbazole derivative) to an electron-acceptor moiety (e.g., a nitrogen-containing six-membered aromatic ring).

[0034] Definitions of technical terms related to substituents

[0035] Halogens or halides include fluorine, chlorine, bromine, and iodine, as used herein.

[0036] Alkyl groups include linear and branched alkyl groups as used herein. Alkyl groups may have 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms. 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. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexane are preferred. The alkyl group may also be substituted.

[0037] A cycloalkyl group includes a cyclic alkyl group as used herein. The cycloalkyl group may be a cycloalkyl group having 3 to 20 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 group, and 2-norbornyl group. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may also be substituted.

[0038] A heteroalkyl group, as used herein, is defined as an alkyl chain in which one or more carbon atoms are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may have 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl group, ethoxymethyl group, ethoxyethyl group, methylthiomethyl group, ethylthiomethyl group, ethylthioethyl group, methoxymethoxymethyl group, ethoxymethoxymethyl group, ethoxyethoxyethyl group, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, mercaptomethyl group, mercaptoethyl group, mercaptopropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermanium methyl group, trimethylgermanium ethyl group, trimethylgermanium isopropyl group, dimethylethylgermanium methyl group, dimethylisopropylgermanium methyl group, tert-butyldimethylgermanium methyl group, triethylgermanium methyl group, triethylgermanium ethyl group, triisopropylgermanium methyl group, triisopropylgermanium ethyl group, trimethylsilylmethyl group, trimethylsilylethyl group, trimethylsilylisopropyl group, trimethylsilylisopropyl group, triisopropylsilylmethyl group, and triisopropyloylsilylethyl group. Furthermore, the heteroalkyl group may be substituted.

[0039] As used herein, an 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 is 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 norbornyl alkenyl groups. Alkenyl groups may also be substituted.

[0040] The alkynyl group, as used herein, includes a linear alkynyl group. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, and is preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3,3-dimethyl-1-butynyl group, 3-ethyl-3-methyl-1-pentynyl group, 3,3-diisopropyl-1-pentynyl group, phenylethynyl group, and phenylpropynyl group. Of these, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, and phenylethynyl group are preferred. The alkynyl group may also be substituted.

[0041] As used herein, aryl groups or aromatic groups refer to non-condensed and condensed 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-condensed 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.

[0042] As used herein, a heterocyclic group or heterocycle refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups with 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups with 3 to 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. 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 oxyranil, oxetanil, tetrahydrofuranil, tetrahydropyranil, dioxopentyl, dioxanil, azilidinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinil, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Furthermore, the heterocyclic groups may be substituted.

[0043] A heteroaryl group, as used herein, may include non-condensed and condensed heteroaromatic groups having 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. An isoaryl group also refers to a heteroaryl group. A heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and more preferably a heteroaryl group having 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, oxathiaidine, oxadiazine, indole, benzimidazole, indazole, indenodine, benzoxazole, benzisoxazole, The formula preferably contains benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, frangipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and seleniumbenzopyridine, and preferably also contains dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and its aza-like compounds. Furthermore, the heteroaryl group may be substituted.

[0044] As used herein, an alkoxy group is represented by an -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group, or -O-heterocyclic group. Examples and preferred examples of alkyl groups, cycloalkyl groups, heteroalkyl groups, and heterocyclic groups are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may also be substituted.

[0045] An aryloxy group is represented as an -O-aryl group or an -O-heteroaryl group as used herein. Examples and preferred examples of aryl and heteroaryl groups 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 aryloxy groups include phenoxy and biphenoxy. The aryloxy group may also be substituted.

[0046] An aralkyl group, as used herein, 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 aralkyl groups are 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-methylbenzyl This includes lolobenzyl, 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. Of 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.

[0047] The alkylsilyl group, as used herein, includes a silyl group substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and 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.

[0048] The arylsilyl group, as used herein, includes 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 preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may also be substituted.

[0049] The alkylgermanium group, as used herein, includes germanium groups substituted with alkyl groups. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium group, triethylgermanium group, methyldiethylgermanium group, ethyldimethylgermanium group, tripropylgermanium group, tributylgermanium group, triisopropylgermanium group, methyldiisopropylgermanium group, dimethylisopropylgermanium group, tri-tert-butylgermanium group, triisobutylgermanium group, dimethyl-tert-butylgermanium group, and methyldi-tert-butylgermanium group. The alkylgermanium group may also be substituted.

[0050] An arylgermanium group, as used herein, includes a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group may be an aryl germanium group having 6 to 30 carbon atoms, and preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyl dibiphenylgermanium, diphenyl biphenylgermanium, phenyl diethylgermanium, diphenyl ethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyl diisopropylgermanium, diphenyl isopropylgermanium, diphenylbutylgermanium, diphenyl isobutylgermanium, and diphenyl-tert-butylgermanium. The arylgermanium group may also be substituted.

[0051] In azadibenzofuran, azadibenzothiophene, etc., "aza" refers to the substitution of one or more CH groups in the corresponding aromatic fragment with nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogues having two or more nitrogen atoms in the ring system. Those skilled in the art will readily conceive of other nitrogen analogues of the aza derivatives described above, and all of these analogues will be defined as being included in the terminology used herein.

[0052] In the present invention, unless otherwise specified, substituted alkyl groups, substituted cycloalkyl groups, substituted heteroalkyl groups, substituted heterocyclic groups, substituted aralkyl groups, substituted alkoxy groups, substituted aryloxy groups, substituted alkenyl groups, substituted alkynyl groups, substituted aryl groups, substituted heteroaryl groups, substituted alkylsilyl groups, substituted arylsilyl groups, substituted alkylgermanium groups, substituted arylgermanium groups, substituted amino groups, substituted acyl groups, substituted carbonyl groups, substituted carboxyl groups, substituted ester groups, substituted sulf groups Using any term from the group consisting of a sulfinyl group, a substituted sulfonyl group, or a substituted phosphino group, one of the following groups is used: 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, alkylgermanium group, arylgermanium group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group. The group consists of deuterium, halogens, unsubstituted alkyl groups with 1 to 20 carbon atoms, unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, unsubstituted heterocyclic groups with 3 to 20 carbon atoms, unsubstituted aralkyl groups with 7 to 30 carbon atoms, unsubstituted alkoxy groups with 1 to 20 carbon atoms, unsubstituted aryloxy groups with 6 to 30 carbon atoms, unsubstituted alkenyl groups with 2 to 20 carbon atoms, unsubstituted alkynyl groups with 2 to 20 carbon atoms, unsubstituted aryl groups with 6 to 30 carbon atoms, and unsubstituted helical groups with 3 to 30 carbon atoms. This means that the group may be substituted with one or more of the following: teloaryl groups, unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, unsubstituted arylsilyl groups with 6 to 20 carbon atoms, unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, unsubstituted arylgermanium groups with 6 to 20 carbon atoms, unsubstituted amino groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

[0053] When describing molecular fragments that are bonded to other parts by substituents or other forms, it should be understood that the name can be determined by whether it is a fragment (e.g., a phenyl group, a phenylene group, a naphthyl group, a dibenzofuranyl group) or a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designation of substituents or different forms of fragment bonding are considered equivalent.

[0054] In the compounds referred to herein, hydrogen atoms may be partially or completely substituted with deuterium. Other atoms, such as carbon and nitrogen, may also be substituted with other stable isotopes of those atoms. Substitution of other stable isotopes in the compounds may be preferable to improve the efficiency and stability of the device.

[0055] In the compounds referred to herein, multiple substitution means a range up to the number of available substitutions, including double substitutions. When a substituent in a compound referred to herein is multiple-substituted (including double, triple, quadruple substitutions, etc.), it means that the substituent may be present at multiple available substitutional positions on its bond structure, and the substituent present at all of the multiple available substitutional positions may have the same structure or different structures.

[0056] Unless otherwise specifically limited to the fact that adjacent substituents may bond to form a ring in the compounds referred to herein, adjacent substituents in such compounds cannot bond to form a ring. The phrase "adjacent substituents may bond to form a ring in the compounds referred to herein" includes not only the case where adjacent substituents may bond to form a ring, but also the case where adjacent substituents do not bond to form a ring. If adjacent substituents may bond to form a ring, the resulting ring may be monocyclic or polycyclic, and may be alicyclic, heteroalicyclic, aryl, or heteroaryl. 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.

[0057] The statement that adjacent substituents may bond to form a ring is understood to mean that two substituents bonded to the same carbon atom are chemically bonded to each other to form a ring, and this can be illustrated by the following formula. [ka]

[0058] The statement that adjacent substituents may bond to form a ring can also be interpreted as meaning that two substituents bonded to carbon atoms directly bonded to each other chemically form a ring, and this can be illustrated by the following formula. [ka]

[0059] The statement that adjacent substituents may bond to form a ring can also be interpreted as meaning that two substituents bonded to a further distant carbon atom may chemically bond to each other to form a ring, and this can be illustrated by the following formula. [ka]

[0060] Furthermore, the statement that adjacent substituents may bond to form a ring is understood to mean 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 where the hydrogen atom is bonded, thereby forming a ring. This is illustrated in the following formula. [ka]

[0061] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal M. a A metal complex containing L a A metal complex having the structure represented by formula 1 is disclosed. [ka] (In Equation 1, metal M is selected from metals with a relative atomic mass greater than 40.) The ring Cy is selected from aromatic rings with 6 to 24 substituted or unsubstituted ring atoms, heteroaromatic rings with 5 to 24 substituted or unsubstituted ring atoms, or combinations thereof, and the ring Cy contains at least 3 carbon atoms. The ring Cy is bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond. X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and each instance is either the same or different. If two R's exist simultaneously, the two R's are either the same or different. X1~X8 are either the same or different each time they appear, C, CR x CR x1 Or selected from N, at least one of X1 to X4 is C, bonded to the ring Cy, X1, X2, X3, or X4 are bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond, When X1, X2, X3, or X4 are bonded to the metal M by a metal-carbon bond, X1, X2, X3, or X4 are selected from C. At least one of X1 to X8 is CR x1 Selected from and R x1 It has the structure represented by Equation 2, [ka] In formula 2, R A and R B Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Rings A and B are selected from identical or different carbon rings with 3 to 30 ring atoms, heterorings with 3 to 30 ring atoms, or combinations thereof. n is either 0 or 1. A1, A2, B1, B2, and E are selected from C, N, B, P, CR''', SiR''', or GeR''', either identically or differently each time they appear. L is selected from single bonds, O, S, SO2, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups with 1 to 20 carbon atoms, cycloalkylene groups with 3 to 20 carbon atoms, heterocyclylene groups with 3 to 20 ring atoms, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 3 to 30 carbon atoms, and combinations thereof. R', R'', R''', R x , R A , R BEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted carbon atoms. Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, "*" represents the joining point in equation 2 above, Adjacent R', R x They may be joined together to form a ring. Adjacent R'', R''', R A , R B They may be joined together to form a ring.

[0062] In this specification, "R', R x The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R' together, or two substituents R' together. x Both, substituents R' and R x This means that one or more of these substituents may bond together to form a ring. Clearly, none of these substituents have to bond together to form a ring.

[0063] In this specification, "R'', R''', R A , R B The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R'' together, or two substituents R'' together. A The two substituents R B Mutual, substituent R A and R'' together, substituent R B and R'' together, substituent R A and R''' with each other, substituent R B This means that one or more of the R''' substituents, or the R'' and R''' substituents, may bond to each other to form a ring. Clearly, none of these substituents have to bond to each other to form a ring.

[0064] In the embodiment, L has a structure represented by formula 1. a The ligand is a dilocate ligand. That is, L a It coordinates with the metal only through the dotted line bonds shown in Equation 1. In Equation 1, there are no forms or sites that coordinate with other metals, for example, R x1 It does not coordinate with metal M.

[0065] In this specification, "carbocyclic ring" refers to a ring group in which the ring atoms constituting the cyclic group consist only of carbon atoms and no heteroatoms. The cyclic group includes monocyclic rings and polycyclic rings (such as spirocyclic rings, bridged rings, and fused rings). "Carbocyclic ring" includes saturated or unsaturated carbocyclic rings, and for example, alicyclic rings (such as cycloalkyl groups, cycloalkenyl groups, and cycloalkynyl groups) and aromatic rings are both carbocyclic rings.

[0066] In this specification, “heterocycle” means that the ring atoms constituting the cyclic group have one or more heteroatoms. The heteroatoms may be selected from nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The cyclic group may be monocycle or polycycle (e.g., spirocycle, bridging ring, fused ring). “Heterocycle” includes saturated carbon rings or unsaturated carbon rings, and for example, both heteroalicycles and heteroaromatic rings are heterocycles.

[0067] In this specification, when n is 0, L does not exist in Equation 2, that is, Equation 2 has the following structure. [ka] When n is 1 and L is selected from single bonds, equation 2 has the following structure. [ka]

[0068] According to one embodiment of the present invention, the ring Cy is the same or different each time it appears. [ka] It is one of the structures selected from the group consisting of the following. (R represents one substitution, multiple substitutions, or no substitution, and if multiple Rs exist in any one type of structure, then R is either the same or different.) R is the same or different each time it appears, and can be hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted carbon atoms. Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, Adjacent substituents R may be bonded together to form a ring. The "#" symbol indicates the bonding point with metal M. [ka] This represents a connection point with X1, X2, X3, or X4.

[0069] In this specification, "adjacent substituents R may bond to form a ring" means that one or more of the groups of any two adjacent substituents R may bond to form a ring. Clearly, none of these substituents have to bond to form a ring.

[0070] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b )n (L c ) q It has the general formula, M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt, either identically or differently each time it appears, and preferably M is selected from Pt or Ir, either identically or differently each time it appears. L a , L b and L c These are the first, second, and third ligands that coordinate with metal M, and L c and L a or L b They are the same or different, L a , L b and L c These may be bound together to form a polydentate 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 metal M, and if m is 2 or greater, there are multiple L a They are identical or different, and if n is 2, then two L b They are either the same or different, and if q is 2, then two L c They are the same or different. L a Each occurrence may be the same or different [ka] [ka] [ka] [ka] [ka] [ka] Selected from the group consisting of, X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and if two R's exist simultaneously, the two R's are either identical or different. R, R x and R x1 Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. R x1 It has the structure represented by Equation 2, [ka] R A and R B Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Rings A and B are selected from identical or different carbon rings with 3 to 30 ring atoms, heterorings with 3 to 30 ring atoms, or combinations thereof. A1, A2, B1, B2, and E are selected from C, N, B, P, CR''', SiR''', or GeR''', either identically or differently each time they appear. n is either 0 or 1. L is selected from single bonds, O, S, SO2, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups with 1 to 20 carbon atoms, cycloalkylene groups with 3 to 20 carbon atoms, heterocyclylene groups with 3 to 20 ring atoms, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 3 to 30 carbon atoms, and combinations thereof. "*" represents the joining point in equation 2 above, Adjacent R', R x They may be joined together to form a ring. Adjacent R elements may be bonded together to form a ring. Adjacent R'', R''', R A , R B They may be joined together to form a ring. L b and L cis the same or different each time it appears [Chemical formula] and is represented by any one selected from the group consisting of X b is the same or different each time it appears and is O, S, Se, NR N1 , CR C1 R C2 selected from the group consisting of R a and R b are the same or different each time they appear and represent mono-substitution, multi-substitution or no substitution adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may combine to form a ring R’, R’’, R’’’, R, R x , R A , R B , R a , R b , R c , R N1 , R C1 and R C2Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted carbon atoms. Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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.

[0071] In this specification, "adjacent substituent R" a , R b , R c , R N1 , R C1 and R C2 The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a The two substituents R b Mutual, substituent R a and R b Mutual, substituent R a and R c Mutual, substituent R b and R c Mutual, substituent R a and R N1 Mutual, substituent R b and R N1 Mutual, substituent R a and RC1 Mutual, substituent R a and R C2 Mutual, substituent R b and R C1 Mutual, substituent R b and R C2 Allies, and R C1 and R C2 This means that one or more of these substituents may bond together to form a ring. Clearly, these substituents do not necessarily have to bond together to form a ring. For example, [ka] Adjacent substituents R a , R b They may be bonded together to form a ring. a If they may be joined to form a ring, [ka] teeth, [ka] It is possible to form such a structure.

[0072] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m It has the structure shown and is represented by equation 3. [ka] (m is chosen from 1, 2 or 3, and if m is chosen from 1, then two L b If the same or different, and m is selected from 2 or 3, then multiple L a They are the same or different. X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and if two R's exist simultaneously, the two R's are either identical or different. Y1-Y4 are selected from CR or N, either identically or differently each time they appear. X3~X8 are either the same or different each time they appear in CR x CR x1 Or selected from N, At least one of X3 to X8 is CR x1 Selected from and R x1 It has the structure represented by Equation 2, [ka] R A and R B Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Rings A and B are selected from identical or different carbon rings with 3 to 30 ring atoms, heterorings with 3 to 30 ring atoms, or combinations thereof. A1, A2, B1, B2, and E are selected from C, N, B, P, CR''', SiR''', or GeR''', either identically or differently each time they appear. n is either 0 or 1. L is selected from single bonds, O, S, SO2, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups with 1 to 20 carbon atoms, cycloalkylene groups with 3 to 20 carbon atoms, heterocyclylene groups with 3 to 20 ring atoms, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 3 to 30 carbon atoms, and combinations thereof. R', R'', R''', R, R x , R A , R BR1 to R8 are identical or different each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted carbon Selected from the group consisting of aryl groups with 6 to 30 primary atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, Adjacent R1 to R8 elements may be bonded together to form a ring. Adjacent R', R x They may be joined together to form a ring. Adjacent R elements may be bonded together to form a ring. Adjacent R'', R''', R A , R B They may be joined together to form a ring.

[0073] In this specification, "adjacent R1-R8 atoms may bond to each other to form a ring" means that any one or more groups of adjacent substituents from any two of R1-R8 atoms may bond to each other to form a ring. Clearly, none of these substituents are required to bond to each other to form a ring.

[0074] According to one embodiment of the present invention, X1 to X8 are the same or different each time they appear and are selected from CR x or CR x1 is selected.

[0075] According to one embodiment of the present invention, X1 to X8 are the same or different each time they appear and are selected from CR x or CR x1 is selected, and among X1 to X8, only one selected from CR x1 is selected.

[0076] According to one embodiment of the present invention, X3 to X8 are the same or different each time they appear and are selected from CR x or CR x1 is selected.

[0077] According to one embodiment of the present invention, X3 to X8 are the same or different each time they appear and are selected from CR x or CR x1 is selected, and among X3 to X8, only one selected from CR x1 is selected.

[0078] According to one embodiment of the present invention, Y1 to Y4 are the same or different each time they appear and are selected from CR.

[0079] According to one embodiment of the present invention, at least one of X3 to X8 is N. For example, one of X3 to X8 is selected from N, or two of X3 to X8 are selected from N.

[0080] According to one embodiment of the present invention, at least one of X1 to X8 is N. For example, one of X1 to X8 is selected from N, or two of X1 to X8 are selected from N.

[0081] According to one embodiment of the present invention, at least one of Y1 to Y4 is N. For example, one of Y1 to Y4 is selected from N, or two of Y1 to Y4 are selected from N.

[0082] According to one embodiment of the present invention, the metal complex has the structure of Ir(L a ) m (L b ) 3-m and is represented by Formula 3A. [Chemical formula] (m is selected from 1, 2, or 3. When m is selected from 1, two L b are the same or different. When m is selected from 2 or 3, multiple L a are the same or different. X is selected from the group consisting of O, S, Se, NR’, SiR’R’, and GeR’R’. When two R’ exist simultaneously, the two R’ are the same or different. R, R x and R x1 each represent monosubstitution, polysubstitution, or no substitution, being the same or different each time they appear. R x1 has the structure represented by Formula 2. [Chemical formula] R A and R B each represent monosubstitution, polysubstitution, or no substitution, being the same or different each time they appear. Ring A and Ring B are each independently selected from a carbocyclic ring having 3 to 30 ring atoms, a heterocyclic ring having 3 to 30 ring atoms, or a combination thereof. A1, A2, B1, B2, E are each independently selected from C, N, B, P, CR''', SiR''', or GeR''' each time they appear. n is 0 or 1. L is selected from a single bond, O, S, SO2, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', a heteroalkylene group having 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, a heterocyclylene group having 3 to 20 ring atoms, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 3 to 30 carbon atoms, and combinations thereof. R', R'', R''', R, R x , R A , R B R1 to R8 are identical or different each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted carbon Selected from the group consisting of aryl groups with 6 to 30 primary atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, Adjacent R1 to R8 elements may be bonded together to form a ring. Adjacent R', R x They may be joined together to form a ring. Adjacent R elements may be bonded together to form a ring. Adjacent R'', R''', R A , R B They may be joined together to form a ring.

[0083] According to one embodiment of the present invention, X is selected from O or S.

[0084] According to one embodiment of the present invention, X is selected from O.

[0085] According to one embodiment of the present invention, A1, A2, B1, and B2 are selected from C, either identically or differently each time they appear.

[0086] According to one embodiment of the present invention, E is selected from N, either identically or differently each time it appears.

[0087] According to one embodiment of the present invention, R x Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0088] According to one embodiment of the present invention, R x Each occurrence is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 6 carbon atoms, cyano groups, and combinations thereof.

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

[0090] According to one embodiment of the present invention, rings A and B are selected from carbon rings with 5 to 12 ring atoms, heterorings with 5 to 12 ring atoms, or combinations thereof, and are identical or different each time they appear.

[0091] According to one embodiment of the present invention, rings A and B are selected from carbon rings with 5 to 6 ring atoms, heterorings with 5 to 6 ring atoms, or combinations thereof, which may be identical or different each time they appear.

[0092] According to one embodiment of the present invention, R x1 It has the structure represented by Equation 4. [ka] (A3~A6 are the same or different each time they appear CR) A Or selected from N, B3-B6 are either the same or different each time they appear in CR B Or selected from N, n is either 0 or 1. L is selected from single bonds, O, S, SO2, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups with 1 to 20 carbon atoms, cycloalkylene groups with 3 to 20 carbon atoms, heterocyclylene groups with 3 to 20 ring atoms, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 3 to 30 carbon atoms, and combinations thereof. R A , RB and R’’ are each, independently at each occurrence, 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 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and are selected from the group consisting of: adjacent R’’, R A , R B may be bonded to each other to form a ring; “*” represents the bonding position of the formula 4.)

[0093] In this Example, when n is 0, L is not present in formula 4, that is, formula 4 has the following structure. [Chemical formula] When n is 1 and L is selected from a single bond, formula 4 has the following structure. [Chemical formula]

[0094] According to one embodiment of the present invention, A3 to A6 are each, independently at each occurrence, CRA They are selected from among them.

[0095] According to one embodiment of the present invention, B3 to B6 are identical or different each time they appear in CR B They are selected from among them.

[0096] According to one embodiment of the present invention, at least one of A3 to A6 is selected from N. For example, one of A3 to A6 is selected from N, or two of A3 to A6 are selected from N.

[0097] According to one embodiment of the present invention, at least one of B3 to B6 is selected from N. For example, one of B3 to B6 is selected from N, or two of B3 to B6 are selected from N.

[0098] According to one embodiment of the present invention, R A and R B Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0099] According to one embodiment of the present invention, R A and R B At least one of these is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C3-C6 alkylsilyl groups, substituted or unsubstituted C3-C6 alkylgermanium groups, cyano groups, and combinations thereof.

[0100] According to one embodiment of the present invention, R A and R B Each occurrence is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 6 carbon atoms, cyano groups, and combinations thereof.

[0101] According to one embodiment of the present invention, R A and R B Each occurrence is selected from the group consisting of hydrogen, deuterium, fluorine, cyano group, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated n-butyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group, deuterated cyclohexyl group, phenyl group, pyridine group, trimethylsilyl group, trimethylgermanium group, and combinations thereof, either identically or differently.

[0102] According to one embodiment of the present invention, L is selected from a single bond, O, S, Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', a heteroalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, a heterocyclylene group having 3 to 10 ring atoms, an arylene group having 6 to 10 carbon atoms, a heteroarylene group having 3 to 10 carbon atoms, and combinations thereof.

[0103] According to one embodiment of the present invention, L is selected from a single bond, O, S, NR'', R''C=CR'', and a phenylene group.

[0104] According to one embodiment of the present invention, L is selected from single bonds.

[0105] According to one embodiment of the present invention, R'' is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C3-C6 alkylsilyl groups, substituted or unsubstituted C3-C6 alkylgermanium groups, and combinations thereof, with each occurrence being the same or different.

[0106] According to one embodiment of the present invention, R'' is selected from the group consisting of hydrogen, deuterium, fluorine, cyano group, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated n-butyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group, deuterated cyclohexyl group, phenyl group, pyridine group, trimethylsilyl group, trimethylgermanium group, and combinations thereof, with each occurrence being the same or different.

[0107] According to one embodiment of the present invention, at least one of X3 to X8 is CR x1 They are selected from among them.

[0108] According to one embodiment of the present invention, at least one of X4 to X8 is CR x1 They are selected from among them.

[0109] According to one embodiment of the present invention, X4 is CR x1 They are selected from among them.

[0110] According to one embodiment of the present invention, at least one of X5 to X8 is CR x1 They are selected from among them.

[0111] According to one embodiment of the present invention, X7 or X8 is CR x1 They are selected from among them.

[0112] According to one embodiment of the present invention, X8 is CR x1 They are selected from among them.

[0113] According to one embodiment of the present invention, at least one of X1 to X8 is CR x Selected from and the R x The group is selected from cyano or fluorine, and at least one of X5 to X8 is CR. x1 They are selected from among them.

[0114] According to one embodiment of the present invention, at least one of X3 to X8 is CR x Selected from and the R x The group is selected from cyano or fluorine, and at least one of X5 to X8 is CR. x1 They are selected from among them.

[0115] According to one embodiment of the present invention, at least one of X5 to X8 is CR x Selected from and the R x The group is selected from cyano or fluorine, and at least one of X5 to X8 is CR. x1 They are selected from among them.

[0116] According to one embodiment of the present invention, X7 is CR x Selected from, the R x is a cyano group or fluorine, and X8 is CR x1 They are selected from among them.

[0117] According to one embodiment of the present invention, X8 is CR x Selected from, the R x is a cyano group or fluorine, and X7 is CR x1 They are selected from among them.

[0118] According to one embodiment of the present invention, R x1 Each occurrence may be the same or different [ka] [ka] [ka] [ka] It is selected from the group consisting of the following.

[0119] According to one embodiment of the present invention, An1 to An 118 The hydrogen in this may be partially or completely deuterated.

[0120] According to one embodiment of the present invention, An1 to An 135 The hydrogen in this may be partially or completely deuterated.

[0121] According to one embodiment of the present invention, R is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, substituted or unsubstituted C6-C20 amino groups, and combinations thereof, with each occurrence being the same or different.

[0122] According to one embodiment of the present invention, R is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof, with each occurrence being the same or different.

[0123] According to one embodiment of the present invention, at least one R is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, substituted or unsubstituted C6-C20 amino groups, and combinations thereof.

[0124] According to one embodiment of the present invention, at least one R is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0125] According to one embodiment of the present invention, at least one or at least two of R1 to R8 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the number of carbon atoms of all of R1 to R4 and / or R5 to R8 is at least 4.

[0126] According to one embodiment of the present invention, at least one or at least two of R1 to R4 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the total number of carbon atoms of all R1 to R4 is at least 4.

[0127] According to one embodiment of the present invention, at least one or at least two of R5 to R8 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the total number of carbon atoms of all R5 to R8 is at least 4.

[0128] 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 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0129] 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.

[0130] 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 a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a neopentyl group, a tert-pentyl group, any of the above groups that are partially or entirely deuterated, and deuterium.

[0131] According to one embodiment of the present invention, L a Each occurrence is either the same or different L a1 ~L a1832 It is selected from the group consisting of L. a1 ~L a1832 The specific structure is shown in claim 18.

[0132] According to one embodiment of the present invention, La1 ~L a1832 The hydrogen atoms in this may be partially or completely deuterated.

[0133] According to one embodiment of the present invention, L b Each occurrence is either the same or different L b1 ~L b334 It is selected from the group consisting of L. b1 ~L b334 The specific structure is shown in claim 19.

[0134] According to one embodiment of the present invention, L b1 ~L b334 The hydrogen atoms in this may be partially or completely deuterated.

[0135] According to one embodiment of the present invention, L c Each occurrence is either the same or different L c1 ~L c360 It is selected from the group consisting of L. c1 ~L c360 The specific structure is shown in claim 20.

[0136] According to one embodiment of the present invention, the metal complex is Ir(L a )3 or Ir(L a ) 2L b or IrL a (L b )2 or Ir(L a ) 2L c or IrL a (L c )2 or Ir(L a )(L b )(L c ) has the structure, L a Each occurrence is either the same or different L a1 ~L a1832 Selected from the group consisting of L b Each occurrence is either the same or different L b1 ~L b334 Selected from the group consisting of L c Each occurrence is either the same or different L c1 ~L c360It is selected from the group consisting of L. a1 ~L a1832 The specific structure is shown in claim 18, L b1 ~L b334 The specific structure is shown in claim 19, L c1 ~L c360 The specific structure is shown in claim 20.

[0137] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 1576. The specific structures of metal complex 1 to metal complex 1576 are shown in claim 21.

[0138] According to one embodiment of the present invention, the hydrogen in metal complexes 1 to 1576 may be partially or completely deuterated.

[0139] According to one embodiment of the present invention, L a Each occurrence is either the same or different L a1 ~L a1891 It is selected from the group consisting of L. a1 ~L a1891 The specific structure is shown in claim 18.

[0140] According to one embodiment of the present invention, L a1 ~L a1891 The hydrogen atoms in this may be partially or completely deuterated.

[0141] According to one embodiment of the present invention, L b Each occurrence is either the same or different L b1 ~L b341 It is selected from the group consisting of L. b1 ~L b341 The specific structure is shown in claim 19.

[0142] According to one embodiment of the present invention, L b1 ~L b341 The hydrogen atoms in this may be partially or completely deuterated.

[0143] According to one embodiment of the present invention, L c Each occurrence is either the same or different L c1 ~L c360 It is selected from the group consisting of L. c1 ~L c360 The specific structure is shown in claim 20.

[0144] According to one embodiment of the present invention, the metal complex is Ir(L a )3 or Ir(L a ) 2L b or IrL a (L b )2 or Ir(L a ) 2L c or IrL a (L c )2 or Ir(L a )(L b )(L c ) has the structure, L a Each occurrence is either the same or different L a1 ~L a1891 Selected from the group consisting of L b Each occurrence is either the same or different L b1 ~L b341 Selected from the group consisting of L c Each occurrence is either the same or different L c1 ~L c360 It is selected from the group consisting of L. a1 ~L a1891 The specific structure is shown in claim 18, L b1 ~L b341 The specific structure is shown in claim 19, L c1 ~L c360 The specific structure is shown in claim 20.

[0145] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 1646. The specific structures of metal complex 1 to metal complex 1646 are shown in claim 21.

[0146] According to one embodiment of the present invention, the hydrogen in metal complexes 1 to 1646 may be partially or completely deuterated.

[0147] According to one embodiment of the present invention, an electroluminescent element comprising an anode, a cathode, and an organic layer provided between the anode and the cathode is further disclosed, wherein at least one of the organic layers comprises a metal complex as described in any one of the embodiments described above.

[0148] According to one embodiment of the present invention, in the electroluminescent element, the organic layer containing the metal complex is a light-emitting layer.

[0149] According to one embodiment of the present invention, in the electroluminescent element, the light-emitting layer emits green light.

[0150] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element contains a host compound, and the host compound comprises one or more types. When the host compound is a combination of multiple types of compounds, it comprises at least one n-type host compound and at least one p-type host compound.

[0151] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element contains a first host compound.

[0152] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element includes a first host compound and a second host compound.

[0153] According to one embodiment of the present invention, in the electroluminescent element, 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, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0154] According to one embodiment of the present invention, in the electroluminescent element, the first host compound has a structure represented by formula X. [ka] (L x Each occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups with 3 to 20 carbon atoms, substituted or unsubstituted arylene groups with 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 20 carbon atoms, or combinations thereof. V is the same or different each time it appears, C, CR v Or selected from N, and at least one of V is C, L x Combine, T is the same or different each time it appears, C, CR t Or selected from N, and at least one of T is C, L x Combine, R v and R tEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted carbon atoms. Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, Ar1 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or combinations thereof, with each occurrence being identical or different. adjacent substituent R v and R t (They may be joined together to form a ring.)

[0155] In this embodiment, "adjacent substituent R v and R t The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v The two substituents R t Mutual, substituent R v and R tThis means that one or more of these substituents may be bonded together to form a ring. Clearly, none of these substituents are required to be bonded together to form a ring.

[0156] According to one embodiment of the present invention, in the electroluminescent element, the first host compound has a structure represented by one of formulas Xa to Xj. [ka] (L x Each occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups with 3 to 20 carbon atoms, substituted or unsubstituted arylene groups with 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 20 carbon atoms, or combinations thereof. V is the same or different each time it appears in CR v Or selected from N, T is the same or different each time it appears in CR t Or selected from N, R v and R tEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted carbon atoms. Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, Ar1 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or combinations thereof, with each occurrence being identical or different. adjacent substituent R v and R t (They may be joined together to form a ring.)

[0157] The second compound has the structure represented by formula 5. [ka] (E1~E6 are the same or different each time they appear, C, CR) e Or selected from N, and at least two of E1 to E6 are N, and at least one of E1 to E6 is C, and combined with formula A, [ka] Q is the same or different each time it appears, O, S, Se, N, NR Q CR Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q Selected from the group consisting of two R Q If both exist at the same time, then two R Q They may be the same or different. p is either 0 or 1, and r is either 0 or 1. If Q is chosen from N, then p is 0 and r is 1. Q is O, S, Se, NR Q CR 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. L is selected from the following, each time it appears, whether identical or different: 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-Q8 are either the same or different each time they appear, and are C, CR. q Or selected from N, R e , R Q and R qEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted carbon atoms Selected from the group consisting of aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, substituted or unsubstituted amino groups with 0 to 20 carbon atoms, 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, The asterisk (*) indicates the point where equation A and equation 5 are joined. adjacent substituent R e , R Q , R q (They may be joined together to form a ring.)

[0158] In this specification, "adjacent substituent R" e , R Q , R q The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R e The two substituents R Q The two substituents R q Mutual, substituent R Q and R q This means that one or more of these substituents may be bonded together to form a ring. Clearly, none of these substituents are required to be bonded together to form a ring.

[0159] According to one embodiment of the present invention, in the electroluminescent element, when a 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.

[0160] According to one embodiment of the present invention, in the electroluminescent element, when a metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 3% to 13% of the total weight of the light-emitting layer.

[0161] According to one embodiment of the present invention, the organic electroluminescent element 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 types of materials. The most commonly used multiple types of materials are a hole transport material doped with a certain proportion of p-type conductive doping material. Commonly seen p-type doping materials are as follows: [ka]

[0162] In other embodiments of the present invention, a composition comprising the metal complex described in any one of the embodiments described above is disclosed.

[0163] Combination with other materials

[0164] The materials of the specific layers used in the organic light-emitting devices described herein can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, and their contents are incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily identify other materials that can be used in combination by referring to the literature.

[0165] In this specification, the materials of specific layers used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. Exemplarily, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080-0101 of patent application US2015 / 0349273A1, and are incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily identify other materials that can be used in combination by referring to the literature.

[0166] In the examples of material synthesis, unless otherwise specified, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used in their commercially available form. The synthesized products were subjected to structural verification and characterization tests in a manner familiar to those skilled in the art, using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatograph, a liquid chromatograph / mass spectrometer, a gas chromatograph / mass spectrometer, a differential thermal scanning calorimetry system, a Shanghai Liangguang Technology fluorescence spectrophotometer, a Wuhan Cosite electrochemical workstation, an Anhui Beik sublimation apparatus, etc.). In the examples of devices, the characteristics of the devices were also tested in a manner familiar to those skilled in the art, using instruments commonly used in the art (including, but not limited to, an Angstrom Engineering vapor deposition machine, a Suzhou Fluorida optical test system, a service life test system, a Beijing Liangtuo ellipsometer, etc.). Those skilled in the art are familiar with the use of the equipment, test methods, and other related matters, and can reliably and unaffected obtain sample-specific data; therefore, these related matters will not be repeatedly described in this specification.

[0167] Examples of material synthesis

[0168] Synthesis Example 1: Synthesis of Metal Complex 765 [ka]

[0169] At room temperature and under nitrogen gas protection, intermediate 1 (2.0 g, 2.2 mmol) and intermediate 2 (1.2 g, 2.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 765 (1.0 g, 0.9 mmol, 40%), a yellow solid. This product was confirmed to be the target product with a molecular weight of 1047.3.

[0170] Synthesis Example 2: Synthesis of Metal Complex 785 [ka]

[0171] At room temperature and under nitrogen gas protection, intermediate 1 (2.0 g, 2.2 mmol) and intermediate 3 (1.3 g, 2.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 785 (1.0 g, 0.8 mmol, 36%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1159.5.

[0172] Synthesis Example 3: Synthesis of Metal Complex 773 [ka]

[0173] At room temperature and under nitrogen gas protection, intermediate 1 (2.1 g, 2.5 mmol) and intermediate 4 (1.3 g, 2.8 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 773 (0.5 g, 0.5 mmol, 20%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1075.4.

[0174] Synthesis Example 4: Synthesis of Metal Complex 697 [ka]

[0175] At room temperature and under nitrogen gas protection, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 5 (1.6 g, 4.0 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 697 (1.0 g, 1.0 mmol, 33%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1022.3.

[0176] Synthesis Example 5: Synthesis of Metal Complex 778 [ka]

[0177] At room temperature and under nitrogen gas protection, intermediate 1 (3.0 g, 3.7 mmol) and intermediate 6 (2.8 g, 5.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 778 (1.5 g, 1.4 mmol, 38%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1103.4.

[0178] Synthesis Example 6: Synthesis of Metal Complex 782 [ka]

[0179] At room temperature and under nitrogen gas protection, intermediate 1 (1.4 g, 1.7 mmol) and intermediate 7 (1.1 g, 2.0 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 782 (0.5 g, 0.4 mmol, 24%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1159.5.

[0180] Synthesis Example 7: Synthesis of Metal Complex 777 [ka]

[0181] At room temperature and under nitrogen gas protection, intermediate 1 (1.0 g, 1.2 mmol) and intermediate 8 (0.7 g, 1.5 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 777 (0.3 g, 0.3 mmol, 25%), a yellow solid. This product was confirmed to be the target product with a molecular weight of 1103.4.

[0182] Synthesis Example 8: Synthesis of Metal Complex 867 [ka]

[0183] At room temperature and under nitrogen gas protection, intermediate 1 (1.7 g, 2.1 mmol) and intermediate 9 (1.2 g, 2.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded yellow solid 867 (1.0 g, 0.9 mmol, 43%). This product was confirmed to be the target product with a molecular weight of 1049.4.

[0184] Synthesis Example 9: Synthesis of Metal Complex 799 [ka]

[0185] At room temperature and under nitrogen gas protection, intermediate 1 (1.9 g, 2.3 mmol) and intermediate 10 (1.5 g, 3.5 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 96 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 799 (1.55 g, 1.48 mmol, 64%), a yellow solid. This product was confirmed to be the target product with a molecular weight of 1047.3.

[0186] Synthesis Example 10: Synthesis of Metal Complex 839 [ka]

[0187] At room temperature and under nitrogen gas protection, intermediate 1 (1.9 g, 2.3 mmol) and intermediate 11 (1.3 g, 3.1 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 839 (1.3 g, 1.27 mmol, 55%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1040.3.

[0188] Synthesis Example 11: Synthesis of Metal Complex 1577 [ka]

[0189] At room temperature and under nitrogen gas protection, intermediate 25 (3.7 g, 5.1 mmol) and intermediate 13 (2.0 g, 7.6 mmol) were sequentially added to 290 mL of ethanol, and the reaction was carried out at a temperature of 80°C for 24 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. The solution was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain intermediate 14 (1.75 g, 2.3 mmol, 45%).

[0190] [ka]

[0191] At room temperature and under nitrogen gas protection, intermediate 14 (0.6 g, 0.7 mmol) and carbazole (0.33 g, 2.0 mmol) were sequentially added to 30 mL of DMF solvent, and the reaction was carried out at a temperature of 100°C for 24 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1577 (0.45 g, 0.42 mmol, 60%). This product was confirmed to be the target product with a molecular weight of 911.2.

[0192] Synthesis Example 12: Metal Complex 789 [ka]

[0193] At room temperature and under nitrogen gas protection, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 15 (1.6 g, 3.6 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 789 (1.66 g, 1.6 mmol, 52%). This product was confirmed to be the target product with a molecular weight of 1055.4.

[0194] Synthesis Example 13: Synthesis of Metal Complex 725 [ka]

[0195] At room temperature and under the protection of nitrogen gas, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 16 (1.7 g, 4.1 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (50.0 mL) and DMF (50.0 mL), and the reaction was carried out at a temperature of 100°C for 72 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 725 (0.9 g, 0.88 mmol, 29%), a yellow solid. The molecular weight of this product was confirmed to be 1022.4, which was the target product.

[0196] Synthesis Example 14: Synthesis of Metal Complex 797 [ka]

[0197] At room temperature and under nitrogen gas protection, intermediate 1 (0.88 g, 1.1 mmol) and intermediate 17 (0.6 g, 1.2 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 797 (0.36 g, 0.32 mmol, 29%), a yellow solid. This product was confirmed to be the target product with a molecular weight of 1123.4.

[0198] Synthesis Example 15: Synthesis of Metal Complex 1584 [ka]

[0199] At room temperature and under nitrogen gas protection, intermediate 1 (2.1 g, 2.5 mmol) and intermediate 18 (1.3 g, 2.8 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1584 (0.54 g, 0.50 mmol, 20%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1083.3.

[0200] Synthesis Example 16: Synthesis of Metal Complex 1606 [ka]

[0201] At room temperature and under nitrogen gas protection, intermediate 1 (2.0 g, 2.5 mmol) and intermediate 19 (1.8 g, 3.3 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1606 (1.0 g, 0.85 mmol, 34%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1163.4.

[0202] Synthesis Example 17: Synthesis of Metal Complex 1598 [ka]

[0203] At room temperature and under nitrogen gas protection, intermediate 1 (0.5 g, 0.6 mmol) and intermediate 20 (0.3 g, 0.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1598 (0.3 g, 0.28 mmol, 47%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1065.3.

[0204] Synthesis Example 18: Synthesis of Metal Complex 959 [ka]

[0205] At room temperature and under nitrogen gas protection, intermediate 21 (1.5 g, 1.61 mmol) and intermediate 22 (1.05 g, 1.93 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 959 (0.61 g, 0.54 mmol, 33%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1271.6.

[0206] Synthesis Example 19: Synthesis of Metal Complex 1612 [ka]

[0207] At room temperature and under nitrogen gas protection, intermediate 21 (2.0 g, 2.2 mmol) and intermediate 23 (1.3 g, 2.8 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1612 (0.47 g, 0.45 mmol, 20%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1184.5.

[0208] Synthesis Example 20: Synthesis of Metal Complex 1643 [ka]

[0209] At room temperature and under nitrogen gas protection, intermediate 24 (2.0 g, 2.2 mmol) and intermediate 26 (1.3 g, 2.6 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1643 (0.75 g, 0.4 mmol, 28%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1216.6.

[0210] Synthesis Example 21: Synthesis of Metal Complex 1645 [ka]

[0211] At room temperature and under nitrogen gas protection, intermediate 27 (2.0 g, 2.5 mmol) and intermediate 28 (1.6 g, 3.6 mmol) were successively added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the reaction was carried out at a temperature of 100°C for 120 hours. After the reaction cooled, the reaction solution was concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) yielded metal complex 1645 (0.75 g, 0.4 mmol, 28%), which was a yellow solid. This product was confirmed to be the target product with a molecular weight of 1013.3.

[0212] Examples of elements

[0213] Element Example 1 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. Then, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Subsequently, the specified organic layer was subjected to a vacuum of approximately 10°C. -8 In the case of Toll, deposition was carried out sequentially on the ITO anode by hot vacuum deposition at a speed of 0.2 to 2 angstroms / second. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound H1 was used as the electron blocking layer (EBL). Then, the metal complex 697 according to the present invention was co-deposited with compounds H1 and H2 as a dopant and used as the light-emitting layer (EML). On the EML, compound HB was used as the hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm was deposited as the electron injection layer, and 120 nm of aluminum was deposited as the cathode. Then, the device was transferred to a glove box and encapsulated using a glass cover to complete the device.

[0214] Comparative Example 1 of the Element The embodiment of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that the metal complex 697 in the present invention is replaced with compound GD1 in the light-emitting layer (EML).

[0215] The detailed layer structure and thickness of the element are shown in the table below. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0216] [Table 1]

[0217] The structure of the material used in the element is represented as follows: [ka]

[0218] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), device voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 2.

[0219] [Table 2]

[0220] As can be seen from the comparative data of Example 1 and Comparative Example 1 in Table 2, the difference between metal complex 697 in the present invention and compound GD1 in the comparative example is the ligand L a The only difference is that the carbazole substituent above is replaced with a phenyl group. When used in similar organic electroluminescent devices, the voltage of Example 1 decreased by 0.26V, CE improved by 8.4%, PE improved by 16.1%, and EQE improved by 9.7%. As a result, the R according to the present invention x1 L having substituents aIt has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0221] Element Example 2 Embodiment 2 of the device is the same as Embodiment 1 of the device, except that the metal complex 867 in the light-emitting layer (EML) is used to replace the metal complex 697 in the present invention.

[0222] Comparative Example 2 of the Element The embodiment of Comparative Example 2 of the device is the same as that of Example 1 of the device, except that the metal complex 697 in the present invention is replaced with compound GD2 in the light-emitting layer (EML).

[0223] The detailed layer structure and thickness of the element are shown in Table 3. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0224] [Table 3]

[0225] The structure of the new material used in the device is represented as follows: [ka]

[0226] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), element voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 4.

[0227] [Table 4]

[0228] As can be seen from the comparative data between Example 2 and Comparative Example 2 in Table 4, the difference between metal complex 867 in the present invention and compound GD2 in the comparative example is the ligand L a The only difference is that the diphenylamino substituent above is replaced with deuterium. When used in similar organic electroluminescent elements, the voltage of Example 2 decreased by 0.2V, CE improved by 6.7%, PE improved by 10.7%, and EQE improved by 8.2%. As a result, the R according to the present invention x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0229] Element Example 3 The embodiment of the third example of the device is the same as that of the first example of the device, except that the metal complex 765 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0230] Element Example 4 Embodiment 4 of the device is the same as Embodiment 1 of the device, except that the metal complex 785 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0231] Comparative Example 3 of the Element The embodiment of Comparative Example 3 of the device is the same as that of Example 1 of the device, except that the metal complex 697 in the present invention is replaced with compound GD3 in the light-emitting layer (EML).

[0232] The detailed layer structure and thickness of the element are shown in Table 5. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0233] [Table 5]

[0234] The structure of the material used in the element is represented as follows: [ka]

[0235] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), element voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 6.

[0236] [Table 6]

[0237] As can be seen from the comparative data of Examples 3 and 4 and Comparative Example 3 in Table 6, L a In addition to having a cyano substituent in the ligand, the difference between metal complex 765 and metal complex 785 in the present invention and compound GD3 in the comparative example is the ligand L a The only difference is that the substituted or unsubstituted carbazole substituents above are replaced with phenyl groups. When used in similar organic electroluminescent devices, Examples 3 and 4 showed a voltage decrease of 0.29V and 0.35V, respectively, an improvement in CE of 5.3% and 10.6%, respectively, an improvement in PE of 10.4% and 22.1%, respectively, and an improvement in EQE of 5.8% and 10.8%, respectively. At the same time, Examples 3 and 4 were shown to have a narrower full width at half maximum (FMAX) of 1.4nm and 0.5nm, respectively, compared to Comparative Example 3, when the maximum emission wavelength remained unchanged, resulting in more saturated green emission. As a result, the R according to the present invention x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0238] In short, the present invention R x1 L having substituents a Metal complexes containing ligands can, for example, lower the voltage of the device and improve CE, PE, and EQE, resulting in devices with superior performance. They can also comprehensively improve various aspects of the device's performance, ultimately leading to a significant overall improvement in the device's performance.

[0239] Element Example 5 Embodiment 5 of the device is the same as Embodiment 1 of the device, except that the metal complex 725 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0240] Comparative Example 4 of the Element The embodiment of Comparative Example 4 of the device is the same as that of Example 1 of the device, except that the metal complex 697 in the present invention is replaced with compound GD4 in the light-emitting layer (EML).

[0241] Element Example 6 Embodiment 6 of the device is the same as Embodiment 1 of the device, except that the metal complex 1577 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML). In this embodiment, the ratio of compound H1:compound H2:metal complex 1577 is 56:38:6.

[0242] Comparative Example 5 of the Element The embodiment of Comparative Example 5 of the device is the same as that of Example 6 of the device, except that the metal complex 1577 in the present invention is replaced with compound GD5 in the light-emitting layer (EML).

[0243] The detailed layer structure and thickness of the element are shown in Table 7. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0244] [Table 7]

[0245] The structure of the new material used in the device is represented as follows: [ka]

[0246] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), element voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 8.

[0247] [Table 8]

[0248] As can be seen from the data in Table 8, when comparing Example 5 and Comparative Example 4, the difference between the metal complex 725 in the present invention and compound GD4 in the comparative example is the ligand L a The only difference is that the carbazole substituent above is replaced with a biphenyl group. When used in similar organic electroluminescent devices, a comparison between Example 5 and Comparative Example 4 showed a decrease in voltage of 0.30V, an improvement in CE of 2.5%, an improvement in PE of 10.5%, and an improvement in EQE of 3.6%.

[0249] Comparing Example 6 with Comparative Example 5, the difference between the metal complex 1577 in the present invention and compound GD5 in the comparative example is the ligand L a The only difference is that the carbazole substituent above is replaced with a deuterated methyl group. When used in similar organic electroluminescent devices, a comparison between Example 6 and Comparative Example 5 showed a decrease in voltage of 0.15V, an improvement in CE of 13.0%, an improvement in PE of 17.5%, and an improvement in EQE of 11.8%.

[0250] As a result, R according to the present invention x1 L having substituents aIt has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0251] Element Example 7 Embodiment 7 of the device is the same as Embodiment 1 of the device, except that the metal complex 789 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0252] Element Example 8 Embodiment 8 of the device is the same as Embodiment 1 of the device, except that the metal complex 1584 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0253] Element Example 9 Embodiment 9 of the device is the same as Embodiment 1 of the device, except that the metal complex 797 in the present invention is replaced with the metal complex 697 in the light-emitting layer (EML).

[0254] Element Example 10 Embodiment 10 of the device is the same as Embodiment 1 of the device, except that the metal complex 1606 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0255] Element Example 11 Embodiment 11 of the device is the same as Embodiment 1 of the device, except that the metal complex 959 in the light-emitting layer (EML) is used to replace the metal complex 697 in the present invention.

[0256] Element Example 12 Embodiment 12 of the device is the same as Embodiment 1 of the device, except that the metal complex 1643 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML). In this embodiment, the ratio of compound H1:compound H2:metal complex 1643 is 71:23:6.

[0257] The detailed layer structure and thickness of the element are shown in Table 9. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0258] [Table 9]

[0259] The structure of the new material used in the device is represented as follows: [ka]

[0260] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), device voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 10.

[0261] [Table 10]

[0262] As can be seen from the data in Table 10, when comparing Examples 7 to 10 with Comparative Example 3, L a In addition to the presence of a cyano substituent in the ligand, the difference between metal complexes 789, 1584, 797, and 1606 in the present invention and compound GD3 in the comparative example is the ligand L aThe only difference is that the carbazole groups with different substitutions above are substituted with phenyl groups. When used in similar organic electroluminescent devices, the full width at half maximum of Examples 7 to 10 was narrowed by 0.5 nm, 2.1 nm, 1.0 nm, and 2.3 nm, respectively, the voltage decreased by 0.40 V, 0.46 V, 0.26 V, and 0.29 V, respectively, the CE improved by 4.3%, 7.4%, 4.3%, and 3.2%, respectively, the PE improved by 15.6%, 22.1%, 11.7%, and 11.7%, respectively, and the EQE improved by 3.7%, 6.5%, 5.0%, and 3.9%. As a result, the R according to the present invention x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0263] As can be seen from the data of Examples 11 and 12, metal complexes 959 and 1643 in the present invention are both R x1 L with substituents a If ligands are present, each L a Ligand and L b The ligands had different substituents. As can be seen from the device results, the EQE was 25% or higher in all cases, and the CE was approximately 100 cd / A in all cases, with the EQE of Example 11 reaching 26.55%. At the same time, their PE and voltage were also at high levels, demonstrating high overall device performance.

[0264] The above describes the R according to the present invention. x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0265] Element Example 13 Embodiment 13 of the device is the same as Embodiment 1 of the device, except that the metal complex 799 is used to replace the metal complex 697 in the present invention in the light-emitting layer (EML).

[0266] Comparative Example 6 of the Element The embodiment of Comparative Example 6 of the device is the same as that of Example 1 of the device, except that the metal complex 697 in the present invention is replaced with compound GD6 in the light-emitting layer (EML).

[0267] The detailed layer structure and thickness of the element are shown in Table 11. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0268] [Table 11]

[0269] The structure of the new material used in the device is represented as follows: [ka]

[0270] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), element voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 12.

[0271] [Table 12]

[0272] As can be seen from the comparison between Example 13 and Comparative Example 6, the difference between metal complex 799 in the present invention and compound GD6 in the comparative example is the ligand L aThe only difference is that the carbazole substituent above is replaced with a phenyl group. When used in similar organic electroluminescent devices, the full width at half maximum of Example 13 was reduced by 2.0 nm, the voltage decreased by 0.11 V, the CE improved by 5.8%, the PE improved by 9.5%, and the EQE improved by 6.5%.

[0273] The above describes the R according to the present invention. x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0274] Element Example 14 Embodiment 14 of the device is the same as Embodiment 1 of the device, except that the metal complex 839 in the light-emitting layer (EML) is used to replace the metal complex 697 in the present invention. In this embodiment, the ratio of compound H1:compound H2:metal complex 839 is 71:23:6.

[0275] Comparative Example 7 of the Element The embodiment of Comparative Example 7 of the device is the same as that of Example 14 of the device, except that the metal complex 839 in the present invention is replaced with compound GD7 in the light-emitting layer (EML).

[0276] The detailed layer structure and thickness of the element are shown in Table 13. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0277] [Table 13]

[0278] The structure of the new material used in the device is represented as follows: [ka]

[0279] The IVL characteristics of the element were measured. Current density: 15 mA / cm² 2 The CIE data for the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), element voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and shown in Table 14.

[0280] [Table 14]

[0281] As can be seen from the element data in Table 14, when comparing Example 14 and Comparative Example 7, L a In addition to the presence of a fluorine substituent in the ligand, the difference between metal complex 839 in the present invention and compound GD7 in the comparative example is the ligand L a The only difference is that the carbazole substituent above is replaced with a phenyl group. When used in similar organic electroluminescent devices, the voltage of Example 14 decreased by 0.66V, CE improved by 4.6%, PE improved by 23.3%, and EQE improved by 5.5%. The above describes the R according to the present invention. x1 L having substituents a It has been proven that by using metal complexes containing ligands, it is possible to obtain devices with superior performance, comprehensively improve various aspects of the device's performance, and ultimately significantly improve the overall performance of the device.

[0282] In short, the present invention R x1 L having substituents a By using a metal complex containing ligands, it is possible to obtain devices with superior performance, such as reduced voltage and improved CE, PE, and EQE, as well as comprehensively improve various aspects of the device's performance, ultimately resulting in a significant overall improvement in the device's performance.

[0283] It should be understood that the various embodiments described herein are illustrative only and not intended to limit the scope of the invention. Therefore, it will be obvious to those skilled in the art that the invention to be protected includes variations of the specific and preferred embodiments described herein. Without departing from the concept of the invention, many of the materials and structures described herein can be substituted with other materials and structures. It should be understood that the various theories regarding why the invention works are not limiting.

Claims

1. M (L) ａ ) ｍ (L ｂ ) ｎ It has a general formula, L ａ The organic layer has a structure represented by formula 1, and M is an organic layer containing a metal complex selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt, which is the same or different each time it appears. L ａ and L ｂ are a first ligand and a second ligand that coordinate with the metal M, respectively, and L ａ and L ｂ may combine to form a polydentate ligand m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m+n is equal to the oxidation state of the metal M, and if m is 2 or greater, multiple L ａ They are either the same or different, and if n is 2, then there are two L ｂ They are the same or different. 【Chemistry 1】 (In formula 1, The ring Cy is selected from aromatic rings with 6 to 24 substituted or unsubstituted ring atoms, heteroaromatic rings with 5 to 24 substituted or unsubstituted ring atoms, or combinations thereof, and the ring Cy contains at least three carbon atoms. The ring Cy is bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond. X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and if two R's exist simultaneously, the two R's are either identical or different. X １ ~X ８ Each appearance is either the same or different C, CR ｘ CR ｘ１ Or selected from N, X １ ~X ４ One of them is C, which is bonded to the ring Cy, X １ , X ２ , X ３ or X ４ It is bonded to the metal M by a metal-carbon bond or a metal-nitrogen bond, X １ ~X ８ At least one of them is CR ｘ１ Selected from and R ｘ１ It has the structure represented by formula 4, 【Chemistry 2】 In formula 4, A ３ ~A ６ Each appearance is either the same or different CR Ａ Or selected from N, B ３ ~B ６ Each appearance is either the same or different CR Ｂ Or selected from N, n is either 0 or 1, L represents a single bond, O, S, SO ２ , Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups having 1 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, heterocyclylene groups having 3 to 20 ring atoms, arylene groups having 6 to 30 carbon atoms, heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof selected from these, R', R'', R ｘ , R Ａ , R Ｂ Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 2 to 20 carbon atoms Selected from the group consisting of alkynyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, 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 having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof, "*" indicates the connection point in formula 4 above. Adjacent R', R ｘ They may be joined together to form a ring. Adjacent R'', R Ａ , R Ｂ They may be joined together to form a ring. L ｂ Each occurrence may be the same or different 【Transformation 3】 Selected from the group consisting of, R ａ and R ｂ Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Adjacent substituent R ａ , R ｂ , R ｃ They may be bonded together to form a ring. R ａ , R ｂ , R ｃ Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, or substituted or unsubstituted aryloxy groups having 2 to 20 carbon atoms. An organic layer selected from the group consisting of quinyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, 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 having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof.

2. The ring Cy is the same or different each time it appears, and is based on the following formula. 【Chemistry 4】 The organic layer according to claim 1, which is one structure selected from the group consisting of the following. (R represents one substitution, multiple substitutions, or no substitution, and if multiple Rs exist in any one type of structure, the Rs are either the same or different.) R is the same or different each time it appears, and is hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 2 to 20 carbon atoms Selected from the group consisting of alkynyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, 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 having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof, Adjacent substituents R may be bonded together to form a ring. The "#" symbol indicates the bonding point with metal M. The substructure shown below 【Transformation 5】 is, X １ , X ２ , X ３ or X ４ (This indicates the point of connection with [another element].)

3. L ａ Each occurrence may be the same or different 【Chemistry 6-1】 【Chemistry 6-2】 【Transformation 6-3】 【Chemistry 6-4】 【Transformation 6-5】 【Transformation 6-6】 Selected from the group consisting of, X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and if two R's exist simultaneously, the two R's are either identical or different. R, R ｘ and R ｘ１ Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. R ｘ１ It has the structure represented by formula 4, 【Transformation 7】 A ３ ~A ６ Each appearance is either the same or different CR Ａ Or selected from N, B ３ ~B ６ Each appearance is either the same or different CR Ｂ Or selected from N, n is either 0 or 1, L represents a single bond, O, S, SO ２ , Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups having 1 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, heterocyclylene groups having 3 to 20 ring atoms, arylene groups having 6 to 30 carbon atoms, heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof selected from these, "*" indicates the connection point in formula 4 above. Adjacent R', R ｘ They may be joined together to form a ring. Adjacent R elements may be bonded together to form a ring. Adjacent R'', R Ａ , R Ｂ They may be joined together to form a ring. L ｂ Each occurrence may be the same or different 【Transformation 8】 It is a structure that can be represented by any one selected from the group consisting of the following: R ａ and R ｂ Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Adjacent substituent R ａ and R ｂ They may be bonded together to form a ring. R', R'', R, R ｘ , R Ａ , R Ｂ , R ａ and R ｂ Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, or substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms. The organic layer according to claim 1, selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, 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 having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof.

4. The organic layer according to Claim 1, wherein M is selected from Pt or Ir, either identically or differently each time it appears.

5. Metal complexes are Ir(L ａ ) ｍ (L ｂ ) ３－ｍ The organic layer according to claim 1, having the structure and represented by formula 3. 【Chemistry 9】 (m is selected from 1, 2 or 3, and if m is selected from 1, two L ｂ If m is the same or different, and m is selected from 2 or 3, then multiple L ａ They are the same or different. X is selected from the group consisting of O, S, Se, NR', SiR'R', and GeR'R', and if two R's exist simultaneously, the two R's are either identical or different. Y １ ~Y ４ Each occurrence is selected from CR or N, either identically or differently. X ３ ~X ８ Each appearance is either the same or different CR ｘ CR ｘ１ Or selected from N, X ３ ~X ８ At least one of them is CR ｘ１ selected from, and R ｘ１ has a structure represented by Formula 4, 【Chemistry 10】 In formula 4, A3 to A6 are selected from CR A or N, either identically or differently each time they appear. B3 to B6 are selected from CR B or N, either identically or differently each time they appear. n is either 0 or 1, L represents a single bond, O, S, SO ２ , Se, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups having 1 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, heterocyclylene groups having 3 to 20 ring atoms, arylene groups having 6 to 30 carbon atoms, heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof selected from these, R', R'', R, R ｘ , R Ａ , R Ｂ , R １ ~R ８ are each independently selected, upon each occurrence, 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 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, 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, cyano group, isocyano group, hydroxy group, sulfanyl group, phosphino group, and combinations thereof. Adjacent R １ ~R ８ They may be joined together to form a ring. Adjacent R', R ｘ They may be joined together to form a ring. Adjacent R elements may be bonded together to form a ring. Adjacent R'', R Ａ , R Ｂ They may be joined together to form a ring.

6. X ３ ~X ８ Each appearance is either the same or different CR ｘ or CR ｘ１ Selected from and / or Y １ ~Y ４ The organic layer according to claim 5, wherein each instance is selected from CR, either identically or differently.

7. X ３ ~X ８ At least one of them is N and / or Y １ ~Y ４ The organic layer according to claim 5, wherein at least one of them is N.

8. X is selected from O or S, the organic layer according to any one of claims 1 to 7.

9. R ｘ The organic layer according to any one of claims 1 to 7, wherein each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C3-C20 alkylgermanium groups, cyano groups, and combinations thereof.

10. The organic layer according to any one of claims 1 to 7, wherein R x is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C3-C6 alkylsilyl groups, substituted or unsubstituted C3-C6 alkylgermanium groups, cyano groups, and combinations thereof, with each occurrence being the same or different.

11. The organic layer according to any one of claims 1 to 7, wherein R x is selected from the group consisting of hydrogen, deuterium, fluorine, cyano group, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated n-butyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group, deuterated cyclohexyl group, phenyl group, pyridine group, trimethylsilyl group, trimethylgermanium group, and combinations thereof, whether identical or different each time it appears.

12. R ｘ１ The organic layer according to any one of claims 1 to 7, having a structure represented by formula 4. 【Chemistry 11】 (A ３ ~A ６ Each appearance is either the same or different CR Ａ Or selected from N, B ３ ~B ６ Each appearance is either the same or different CR Ｂ Or selected from N, n is either 0 or 1, L is selected from single bonds, O, S, NR'', CR''R'', SiR''R'', GeR''R'', BR'', PR'', P(O)R'', R''C=CR'', heteroalkylene groups with 1 to 10 carbon atoms, cycloalkylene groups with 3 to 10 carbon atoms, heterocyclylene groups with 3 to 10 ring atoms, arylene groups with 6 to 10 carbon atoms, heteroarylene groups with 3 to 10 carbon atoms, and combinations thereof. R Ａ And RB is the same or different each time it appears, hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C2-C20 alkenyl group, substituted or Selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof, Adjacent R Ａ , R Ｂ They may be joined together to form a ring. The asterisk (*) indicates the connection point in equation 4.

13. A ３ ~A ６ Each appearance is either the same or different CR Ａ Selected from and / or B ３ ~B ６ Each appearance is either the same or different CR Ｂ Selected from, R Ａ and R Ｂ The organic layer according to claim 12, wherein each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C3-C20 alkylgermanium groups, cyano groups, and combinations thereof.

14. The organic layer according to claim 12, wherein R A and R B are selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C3-C6 alkylsilyl groups, substituted or unsubstituted C3-C6 alkylgermanium groups, cyano groups, and combinations thereof, with each occurrence being the same or different.

15. The organic layer according to claim 12, wherein at least one of R A and R B is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C3-C12 heteroaryl group, a substituted or unsubstituted C3-C6 alkylsilyl group, a substituted or unsubstituted C3-C6 alkylgermanium group, a cyano group, and combinations thereof.

16. The organic layer according to claim 12, wherein L is selected from a single bond, O, S, NR'', R''C=CR'', and a phenylene group.

17. The organic layer according to claim 12, wherein L is selected from single bonds.

18. X ５ ~X ８ At least one of them is CR ｘ１ An organic layer selected from, according to claim 1 or 5.

19. The organic layer according to claim 1 or 5, wherein at least one of X7 or X8 is selected from CR x1.

20. The organic layer according to claim 1 or 5, wherein X8 is selected from CR x1.

21. X ５ ~X ８ At least one of them is CR ｘ Selected from and the R ｘ X is selected from cyano group or fluorine, ５ ~X ８ At least one of them is CR ｘ１ An organic layer selected from, according to claim 1 or 5.

22. The organic layer according to claim 1 or 5, wherein X7 is selected from CRx, Rx is a cyano group or fluorine, X8 is selected from CRx1, and / or X8 is selected from CRx, Rx is a cyano group or fluorine, and X7 is selected from CRx1.

23. R ｘ１ An is the same or different each time it appears. １ ~An75, An81 ~An １３５ Selected from the group consisting of, 【Chemistry 12-1】 【Chemistry 12-2】 【Chemistry 12-3】 【Chemistry 12-4】 The aforementioned An １ ~An75, An81 ~An １３５ The organic layer according to claim 1 or 5, wherein the hydrogen in the organic layer may be partially or entirely deuterated.

24. The organic layer according to any one of claims 2 to 7, wherein R is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, substituted or unsubstituted C6-C20 amino groups, and combinations thereof, with each occurrence being the same or different.

25. The organic layer according to any one of claims 2 to 7, wherein at least one R is selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted ring C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and combinations thereof.

26. R １ ~R ８ At least one or at least two of these are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted ring cycloalkyl groups having 3 to 20 carbon atoms, or combinations thereof, and all of the R １ ~R ４ and / or R ５ ~R ８ The organic layer according to claim 5, wherein the sum of the number of carbon atoms is at least 4.

27. ​​The organic layer according to claim 5, wherein at least one or at least two of R1 to R4 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms in a ring, or a combination thereof, and the sum of the carbon atoms of all R1 to R4 is at least 4, and / or at least one or at least two of R5 to R8 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms in a ring, or a combination thereof, and the sum of the carbon atoms of all R5 to R8 is at least 4.

28. R ２ , R ３ , R ６ , R ７ The organic layer according to claim 5, wherein at least one, at least two, at least three, or all of the members are selected from the group consisting of deuterium, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted ring C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and combinations thereof.

29. The organic layer according to claim 5, wherein 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.

30. The organic layer according to claim 4, wherein at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a neopentyl group, a tert-pentyl group, any of the above groups that are partially or entirely deuterated, and deuterium.

31. L ａ Each appearance is either the same or different L ａ１ ~La75, La81 ~L a164, La170 ~ La253, La259 ~ La347, La353 ~ La684, La690 ~ La773, La779 ~ La862, La869 ~ La1094, L a1100 ~L a1183, L a1189 ~L ａ１８９１ Selected from the group consisting of L ａ１ ~L a75 , La81 ~L a164 , La170 ~L a253 , La259 ~L a347 , La353 ~L a684 , La690 ~L a773 , La779 ~L a862 , La869 ~L a1094 , L a1100 ~L a1183, L a1189 ~L ａ１８９１ The specific structure is as follows: L below ａ１ ~L a75 , La81 ~L a164 , La170 ~L a253 , La259 ~L a347 , La353 ~L a684 , La690 ~L a773 , La779 ~L a862 , La869 ~L a1094 , L a1100 ~L a1183, L a1189 ~L ａ１４４０ It has the following structure: 【Chemistry 13】 However, X, Cy, R Ｘ４ ~R Ｘ８ The atoms or groups are selected from the following table: Table 1-1 Table 1-2 Table 1-3 Table 1-4 Table 1-5 Table 1-6 Table 1-7 Table 1-8 Table 1-9 Table 1-10 Table 1-11 Table 1-12 Table 1-13 Table 1-14 Table 1-15 Table 1-16 Table 1-17 Table 1-18 Table 1-19 Table 1-20 Table 1-21 Table 1-22 Table 1-23 Table 1-24 Table 1-25 Table 1-26 Table 1-27 Table 1-28 Table 1-29 Table 1-30 Table 1-31 Table 1-32 Table 1-33 Table 1-34 Table 1-35 Table 1-36 Table 1-37 Table 1-38 Table 1-39 Table 1-40 Table 1-41 Table 1-42 Table 1-43 Table 1-44 Table 1-45 L below ａ１４４１ ~L ａ１５１４ It has the following structure: 【Chemistry 14】 However, X, Cy, R Ｘ４ ~R Ｘ８ The atoms or groups are selected from the following table: Table 2-1 Table 2-2 Table 2-3 L below ａ１５１５ ~L ａ１５８８ It has the following structure: 【Chemistry 15】 X, Cy, R Ｘ４ ~R Ｘ８ The atoms or groups are selected from the following table: Table 3-1 Table 3-2 Table 3-3 Table 3-4 L below ａ１５８９ ~L ａ１６６２ It has the following structure: 【Chemistry 16】 However, X, Cy, R Ｘ４ ~R Ｘ８ The atoms or groups are selected from the following table: Table 4-1 Table 4-2 Table 4-3 L below ａ１６６３ ~L ａ１７３６ It has the following structure: 【Chemistry 17】 However, X, Cy, R Ｘ４ ~R Ｘ８ The atoms or groups are selected from the following table: Table 5-1 Table 5-2 Table 5-3 L below ａ１７３７ ~L ａ１７６０ It has the following structure: [Chemistry 18] However, Cy, R Ｘ４ ~R Ｘ７ The atoms or groups are selected from the following table: Table 6-1 Table 6-2 L below ａ１７６１ ~L ａ１７８４ It has the following structure: 【Chemistry 19】 However, X, Cy, R Ｘ４ ~R Ｘ６ , R Ｘ８ The atoms or groups are selected from the following table: Table 7-1 Table 7-2 L below ａ１７８５ ~L ａ１８０８ It has the following structure: 【Chemistry 20】 However, Cy, R Ｘ４ ~R Ｘ５ , R Ｘ７ ~R Ｘ８ The atoms or groups are selected from the following table: Table 8-1 Table 8-2 L below ａ１８０９ ~L ａ１８３２ It has the following structure: 【Chemistry 21】 However, Cy, R Ｘ４ , R Ｘ６ ~R Ｘ８ The atoms or groups are selected from the following table: Table 9-1 Table 9-2 In the table above, Cy1 to Cy9 have the following structure: 【Chemistry 22】 In Cy1 to Cy9, "#" represents the bonding site with metal M, and the substructure is as shown in the following formula. 【Chemistry 23】 is, X １ , X ２ , X ３ or X ４ This represents the joining point, In the table above, TMS represents trimethylsilyl, and TMG represents trimethylgermanium group. 【Chemistry 24-1】 【Chemistry 24-2】 【Chemistry 24-3】 Said L ａ１ ~L a75 , La81 ~L a164 , La170 ~L a253 , La259 ~L a347 , La353 ~L a684 , La690 ~L a773 , La779 ~L a862 , La869 ~L a1094 , L a1100 ~L a1183, L a1189 ~L ａ１８９１ The organic layer according to claim 23, wherein some or all of the hydrogen atoms in the layer may be deuterated.

32. L ｂ Each occurrence may be the same or different, and the structure is as follows: 【Chemistry 25-1】 【Chemistry 25-2】 【Chemistry 25-3】 【Chemistry 25-4】 【Chemistry 25-5】 【Chemistry 25-6】 【Chemistry 25-7】 【Chemistry 25-8】 【Chemistry 25-9】 【Chemistry 25-10】 Selected from the group consisting of, Said L ｂ１ ~L ｂ３４１ The organic layer according to claim 31, wherein some or all of the hydrogen atoms in the layer may be deuterated.

33. The metal complex is selected from the group consisting of metal complex 1 to metal complex 1646. The aforementioned metal complexes 1 to 1364 are IrL ａ (L ｂ ) ２ It has a structure with two L ｂ They are the same or different, L ａ and L ｂ These correspond to the structures shown in the table below, Table 10-1 Table 10-2 Table 10-3 Table 10-4 Table 10-5 Table 10-6 Table 10-7 Table 10-8 Table 10-9 Table 10-10 Table 10-11 Table 10-12 Table 10-13 Table 10-14 Table 10-15 Table 10-16 Table 10-17 Table 10-18 Table 10-19 Table 10-20 Table 10-21 Metal complexes 1365 to 1382 are Ir(L ａ ) ２ L ｂ It has a structure with two L ａ They are the same or different, L ａ and L ｂ These correspond to the structures shown in the table below, Table 11 Metal complexes 1563 to 1568 are Ir(L ａ ) ３ It has a structure with three L ａ They are the same or different, three L's ａ These correspond to the structures shown in the table below, Table 12 Metal complexes 1577 to 1646 are IrL ａ (L ｂ ) ２ It has a structure with two L ｂ They are identical, L ａ and L ｂ These correspond to the structures shown in the table below, Table 13-1 Table 13-2 The organic layer according to claim 32, wherein the hydrogen in metal complexes 1 to 1382, 1563 to 1568, and 1577 to 1646 may be partially or completely deuterated.

34. An electronic component module including an electroluminescent element comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, An electronic component module wherein at least one of the organic layers includes the organic layer described in claim 1.

35. The electronic component module according to claim 34, wherein the organic layer containing the metal complex is a light-emitting layer.

36. The electronic component module according to claim 35, wherein the light-emitting layer further comprises a first host compound.

37. The electronic component module according to claim 36, wherein the light-emitting layer further contains a second host compound.

38. The electronic component module according to claim 37, wherein at least one of the host compounds 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, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

39. The electronic component module according to claim 37, wherein 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% of the total weight of the light-emitting layer.

40. A display comprising the organic layer described in claim 1.

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