Organic electroluminescent material and device thereof

Abstract

To provide an organic electroluminescent material and a device thereof.SOLUTION: The organic electroluminescent material is a metal complex containing 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 a compound for use in an organic electronic device, such as an organic light-emitting device. More particularly, the present invention relates to a compound having a structure represented by formula 1: a The present invention relates to a metal complex containing the ligand, an organic electroluminescence device containing the metal complex, and a composition containing the metal complex. [Background technology]

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

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

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

[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material required. Small molecules refer to materials that are not polymeric, either organic or organometallic, and the molecular weight of small molecules can be large as long as they have a precise structure. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Small molecule OLEDs can become polymer OLEDs when post-polymerization occurs during the manufacturing process.

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

[0007] The emission color of an OLED can be achieved by the structural design of the emitting material. An OLED may include one or more emitting layers to achieve a desired spectrum. In green, yellow, and red OLEDs, phosphorescent materials have already been successfully commercialized, but blue phosphorescent elements still have problems such as blue not being saturated, short service life, and high operating voltage. Commercial full-color OLED displays generally use a mixed strategy, using blue fluorescence and yellow, red, or green phosphorescence. Currently, there is a problem that the efficiency of phosphorescent OLEDs drops rapidly at high brightness. It is also desirable to have a more saturated emission spectrum, higher efficiency, and longer device service life.

[0008] US2013119354A1 discloses metal complexes having the following general structure: [ka] (wherein R1 to R4 are selected from hydrogen, deuterium, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and combinations thereof.) The application only discloses the use of aryl substituents in which R1 is a phenyl group in metal complexes and devices, but does not disclose or teach the effect on the performance of metal complexes and devices having specific substituents according to the present application.

[0009] CN107236006A discloses red light metal complexes having the following general structure: [ka]

[0010] In this application, metal complexes having fluorene-based ligands substituted with arylamines and their use in devices are disclosed.In this application, the use of fluorene groups substituted with polyarylamines in metal complexes is disclosed, but the metal complexes containing ligands of specific framework structures having specific substituents according to the present application and their effects on the performance of devices are not disclosed or taught.

[0011] CN101108964A discloses red light metal complexes having the following general structure: [ka]

[0012] The application discloses red light metal complexes containing diketone-containing ligands with carbazole substituents and their use in organic electroluminescence devices. The application discloses the presence of carbazole substituents in phenylquinolines and metal complexes that coordinate with diketone ligands, but does not disclose or teach the metal complexes containing ligands with specific framework structures having specific substituents according to the present application, and the effects on the performance of the devices. [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 Summary of the Invention [Problem to be solved by the invention]

[0015] In order to solve at least some of the above problems, the present invention provides a compound having the structure of formula 1, a The present invention provides a series of metal complexes containing ligands. These novel compounds can be used in electroluminescence devices to obtain sufficiently excellent device performance, such as lowering the device voltage, improving current efficiency, power efficiency and external quantum efficiency, and can comprehensively improve various device performances, ultimately significantly improving the overall device performance. [Means for solving the problem]

[0016] According to one embodiment of the present invention, a metal M and a ligand L coordinated to the metal M are a A metal complex comprising L a Disclosed is a metal complex having a structure represented by formula 1: [ka] (In formula 1, the metal M is selected from metals having a relative atomic mass greater than 40; ring Cy is, at each occurrence, the same or different, selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof, and said ring Cy contains at least 3 carbon atoms; the ring Cy is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; X is, at each occurrence, the same or different, selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R' are present simultaneously, the two R' are the same or different; X1 to X8 are the same or different for each occurrence, and are C, CR x , C.R. x1 or N, and at least one of X1 to X4 is C and is bonded to the ring Cy; X1, X2, X3 or X4 is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; At least one of X1 to X8 is CR. x1 and R x1 has a structure represented by formula 2: [ka] In formula 2, R A and R B represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are selected from a carbocyclic ring having 3 to 30 ring atoms, a heterocyclic ring having 3 to 30 ring atoms, or a combination thereof; n is 0 or 1, A1, A2, B1, B2, and E are each identically or differently selected from C, N, B, P, CR''', SiR''', or GeR'''' at each occurrence; 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 x , R A , R Bare each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, "*" represents the bonding point in formula 2; Adjacent R' and R x may be bonded to each other to form a ring, Adjacent R'', R''', R A , R B may be bonded to each other to form a ring.)

[0017] According to another embodiment of the present invention, there is further disclosed an electroluminescent device comprising an anode, a cathode, and organic layers disposed between the anode and the cathode, wherein at least one of the organic layers comprises a metal complex as described in the above embodiment.

[0018] According to other embodiments of the present invention, there is further disclosed a composition comprising a metal complex as described in the above embodiments.

[0019] The present invention relates to a compound having a structure represented by formula 1. a A series of metal complexes containing ligands are disclosed. These novel compounds can be used in electroluminescence devices to obtain sufficiently excellent device performance, such as lowering the device voltage, improving current efficiency, power efficiency and external quantum efficiency, and can comprehensively improve various device performances, ultimately significantly improving the overall device performance. [Brief description of the drawings]

[0020] [Figure 1] 1 is a schematic diagram of an organic light emitting device that may include a metal complex according to the present invention and a composition including the metal complex. [Diagram 2] 1 is a schematic diagram of another organic light emitting device that may include a metal complex according to the present invention and a composition including the metal complex. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0021] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. FIG. 1 shows an organic light-emitting device 100 by way of example and without limitation. The drawings are not necessarily drawn to scale, and some layer structures may be omitted in the drawings, as necessary. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of US Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

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

[0023] The above-mentioned split-layer structure is provided by way of non-limiting examples. The functions of the 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 multiple materials can be used to achieve optimal performance. Any of the functional layers may include multiple sub-layers, for example, an emitting layer may have two layers of different emitting materials to achieve a desired emission spectrum.

[0024] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0025] An OLED also requires an encapsulation layer, and as shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not by way of limitation. The difference from FIG. 1 is that it may include an encapsulation layer 102 on the cathode 190 to prevent harmful substances from the outside, such as moisture and oxygen. Any material that can provide an encapsulation function, such as glass or an organic-inorganic mixed layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the outside of the OLED element. Multilayer thin-film encapsulation is described in U.S. Pat. No. US7968146B2, the entire contents of which are incorporated herein by reference.

[0026] Devices manufactured according to embodiments of the invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signaling lamps, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, handheld video cameras, viewfinders, microdisplays, 3-D displays, in-vehicle displays, and tail lights.

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

[0028] "Top" means furthest from the substrate and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is described as being relatively far from the substrate. There may be other layers between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if there are various organic layers between the cathode and anode.

[0029] "Solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0030] It is believed that if a ligand directly enhances the photosensitizing properties of the emissive material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emissive material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand may modify the properties of the photosensitizing ligand.

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

[0032] On the other hand, E-type delayed fluorescence depends on the conversion of excited states between triplet and singlet, not on the collision of two triplets. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap to allow the conversion of energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of penetration (reverse intersystem crossing) between reverse systems (RISC) is fast enough, the proportion of backfilled singlet excited states can reach 75%, minimizing non-radiative decay from triplets. The total proportion of singlets can be 100%, far exceeding the 25% of exciton spin statistics due to electrochemical.

[0033] The characteristic of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited to theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T ) for the luminescent devices. Organic non-metal-containing donor-acceptor luminescent materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) type emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, with a ΔE S-T These states may include CT states. Typically, donor-acceptor emissive materials are constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0034] Definitions of Substituent Terminology

[0035] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0036] As used herein, alkyl groups include straight and branched chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. 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 be optionally substituted.

[0037] As used herein, the cycloalkyl group includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of the cycloalkyl group 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 be substituted.

[0038] As used herein, a heteroalkyl group is one in which one or more carbons in an alkyl chain are replaced with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Illustrative examples of heteroalkyl groups are methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermaniummethyl, trimethylgermaniumethyl, trimethylgermaniumisopropyl, dimethylethylgermaniummethyl, dimethylisopropylgermaniummethyl, tert-butyldimethylgermaniummethyl, triethylgermaniummethyl, triethylgermaniumethyl, triisopropylgermaniummethyl, triisopropylgermaniumethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropyloylsilylethyl. Heteroalkyl groups may also be substituted.

[0039] As used herein, alkenyl groups include linear, branched and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornylalkenyl groups. The alkenyl group may be substituted.

[0040] As used herein, the term "alkynyl group" includes linear alkynyl groups. 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 the alkynyl group include an ethynyl group, a propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3,3-dimethyl-1-butynyl group, a 3-ethyl-3-methyl-1-pentynyl group, a 3,3-diisopropyl-1-pentynyl group, a phenylethynyl group, and a phenylpropynyl group. Among these, an ethynyl group, a propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, and a phenylethynyl group are preferred. The alkynyl group may be substituted.

[0041] As used herein, aryl or aromatic groups contemplate 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, and are preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-dimethylphenyl, mesitylene and m-tetraphenyl. The aryl group may also be substituted.

[0042] Heterocyclic group or heterocycle, as used herein, refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Heterocyclic groups may also be substituted.

[0043] Heteroaryl groups, as used herein, may include non-fused and fused 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. Isoaryl groups also refer to heteroaryl groups. Heteroaryl groups may be heteroaryl groups having 3 to 30 carbon atoms, preferably heteroaryl groups having 3 to 20 carbon atoms, and more preferably heteroaryl groups having 3 to 12 carbon atoms. Suitable heteroaryl groups are dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, frangipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogues. Heteroaryl groups may also be substituted.

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

[0045] As used herein, the aryloxy group is represented by -O-aryl group or -O-heteroaryl group. Examples and preferred examples of the aryl group and the heteroaryl group are the same as those mentioned above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and is preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.

[0046] As used herein, the term "aralkyl group" includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among them, 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] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group 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] As used herein, the term "arylsilyl group" 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 is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.

[0049] As used herein, the term "alkyl germanium group" includes a germanium group substituted with an alkyl group. The alkyl germanium group may be an alkyl germanium group having 3 to 20 carbon atoms, and is preferably an alkyl germanium group having 3 to 10 carbon atoms. Examples of the alkyl germanium group include a trimethyl germanium group, a triethyl germanium group, a methyldiethyl germanium group, an ethyldimethyl germanium group, a tripropyl germanium group, a tributyl germanium group, a triisopropyl germanium group, a methyldiisopropyl germanium group, a dimethylisopropyl germanium group, a tri-tert-butyl germanium group, a triisobutyl germanium group, a dimethyl-tert-butyl germanium group, and a methyldi-tert-butyl germanium group. The alkyl germanium group may be substituted.

[0050] As used herein, the term "arylgermanium group" includes a germanium group substituted with at least one aryl group or heteroaryl group. The arylgermanium group may be an aryl group germanium group having 6 to 30 carbon atoms, and is preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenyldibiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. The arylgermanium group may also be substituted.

[0051] The "aza" in azadibenzofuran, azadibenzothiophene, etc. refers to the replacement of one or more CH groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can easily imagine other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.

[0052] In the present invention, unless otherwise specified, the following groups are included: a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted sulfur group, a substituted aryl ... When any of the terms from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups is used, any one of the following groups is included: alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino. The group is selected from the group consisting of deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heptyl group having 3 to 30 carbon atoms, an unsubstituted aryl ... It means that the aryl group may be substituted with one or more selected from a heteroaryl group, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanium group having 3 to 20 carbon atoms, an unsubstituted arylgermanium group having 6 to 20 carbon atoms, an unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

[0053] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as to whether it is a fragment (e.g., a phenyl group, a phenylene group, a naphthyl group, a dibenzofuranyl group) or an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are recognized as equivalents.

[0054] In the compounds mentioned herein, hydrogen atoms may be partially or completely replaced by deuterium.Other atoms, such as carbon and nitrogen, may also be replaced by their other stable isotopes.In order to improve the efficiency and stability of the device, the replacement of other stable isotopes in the compounds may be preferred.

[0055] In the compounds referred to herein, multiple substitution refers to the range up to the most available substitution, including double substitution.When a substituent in a compound referred to herein means multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent can be present at multiple available substitution positions on the bond structure, and the substituents present at multiple available substitution positions can be the same structure or different structures.

[0056] Unless otherwise specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents do not bond to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be a monocyclic or polycyclic ring, and an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such a description, 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 be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0058] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0059] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms further apart are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0060] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. The following formula is an example. [ka]

[0061] According to one embodiment of the present invention, a metal M and a ligand L coordinated to the metal M are a A metal complex comprising L a Disclosed is a metal complex having a structure represented by formula 1: [ka] (In formula 1, the metal M is selected from metals having a relative atomic mass greater than 40; ring Cy is, at each occurrence, the same or different, selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof, and said ring Cy contains at least 3 carbon atoms; the ring Cy is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; X is, at each occurrence, the same or different, selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R' are present simultaneously, the two R' are the same or different; X1 to X8 are the same or different for each occurrence, and are C, CR x , C.R. x1 or N, and at least one of X1 to X4 is C and is bonded to the ring Cy; X1, X2, X3 or X4 is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; When X1, X2, X3 or X4 is bonded to the metal M by a metal-carbon bond, X1, X2, X3 or X4 is selected from C; At least one of X1 to X8 is CR. x1 and R x1 has a structure represented by formula 2: [ka] In formula 2, R A and R B represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are selected from a carbocyclic ring having 3 to 30 ring atoms, a heterocyclic ring having 3 to 30 ring atoms, or a combination thereof; n is 0 or 1, A1, A2, B1, B2, and E are each identically or differently selected from C, N, B, P, CR''', SiR''', or GeR'''' at each occurrence; 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 x , R A , R Bare each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, "*" represents the bonding point in formula 2; Adjacent R' and R x may be bonded to each other to form a ring, Adjacent R'', R''', R A , R B may be bonded to each other to form a ring.)

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

[0063] As used herein, "R", "R" and "R A , R B may be bonded to form a ring" refers to adjacent substituent groups, for example, two substituents R" and two substituents R A Two substituents R B R A and R″, the substituent R B and R″, the substituent R A and R''', the substituent R B and R''', and any one or more of the substituents R'' and R''' may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0064] In this embodiment, L having a structure represented by formula 1 a The ligand is a bidentate ligand, i.e., L a coordinates to the metal only through the dotted bond shown in formula 1. In formula 1, there are no other metal coordination forms or sites, e.g., R x1 does not coordinate with metal M.

[0065] In this specification, the term "carbocycle" refers to a ring atom constituting the cyclic group that is composed of only carbon atoms and has no heteroatoms. The cyclic group includes a monocycle and a polycycle (such as a spirocycle, a bridged ring, or a condensed ring). The term "carbocycle" includes a saturated or unsaturated carbocycle, and for example, an alicycle (such as a cycloalkyl group, a cycloalkenyl group, or a cycloalkynyl group) and an aromatic ring are both carbocycles.

[0066] In this specification, the term "heterocycle" refers to a ring atom that constitutes the cyclic group having one or more heteroatoms. The heteroatoms may be selected from nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The cyclic group includes monocyclic and polycyclic rings (spirocyclic, bridged, condensed, etc.). The term "heterocycle" includes saturated or unsaturated carbocyclic rings, and for example, both heteroalicyclic and heteroaromatic rings are heterocyclic rings.

[0067] As used herein, when n is 0, L is absent in formula 2, ie, formula 2 has the following structure: [ka] When n is 1 and L is selected from a single bond, formula 2 has the following structure: [ka]

[0068] According to one embodiment of the invention, the rings Cy may be identical or different at each occurrence. [ka] It is any one structure selected from the group consisting of: (R may be the same or different at each occurrence and represent mono-, poly- or unsubstituted, and when multiple R are present in any one structure, said R may be the same or different, R each occurrence may be the same or different and is hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Adjacent substituents R may be bonded to form a ring; "#" represents the bond site with metal M, [ka] represents the bonding site with X1, X2, X3 or X4.

[0069] In this specification, "adjacent substituents R may be bonded to form a ring" means that any one or more of the group consisting of any two adjacent substituents R may be bonded to form a ring. Obviously, these substituents do not have to be bonded to form a ring.

[0070] According to one embodiment of the present invention, the metal complex is a ) m (L b )n (L c ) q having the general formula M at each occurrence is identically or differently selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, preferably M at each occurrence is identically or differently selected from Pt or Ir; L a , L b and L c are the first, second and third ligands coordinated to the metal M, respectively, and L c and the above L a or L b are the same or different, L a , L b and L c may be linked to form a multidentate ligand, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M. When m is 2 or more, multiple L a are the same or different, and if n is 2, the two L b are the same or different, and if q is 2, the two L c are the same or different, L a may be the same or different for each occurrence. [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 when two R' are simultaneously present, the two R' are the same or different; R, R x and R x1 represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; R x1 has a structure represented by formula 2: [ka] R A and R B represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are 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, and E are each identically or differently selected from C, N, B, P, CR''', SiR''', or GeR'''' at each occurrence; 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; "*" represents the bonding point in formula 2; Adjacent R' and R x may be bonded to each other to form a ring, Adjacent R's may be bonded to each other to form a ring, Adjacent R'', R''', R A , R B may be bonded to each other to form a ring, L b and L cmay be the same or different for each occurrence. [ka] A structure represented by any one selected from the group consisting of: X b Each occurrence may be the same or different and may be O, S, Se, or NR N1 , C.R. C1 R C2 Selected from the group consisting of R a and R b represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; Adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may be bonded 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 C2are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon the alkyl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each of which is a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

[0071] In the present specification, "adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a Two substituents R b R a and R b R a and R c R b and R c R a and R N1 R b and R N1 R a and RC1 R a and R C2 R b and R C1 R b and R C2 R C1 and R C2 This means that any one or more of the substituents may be bonded to each other to form a ring. Obviously, none of these substituents may be bonded to each other to form a ring. For example, [ka] Adjacent substituents R in a , R b may be bonded to form a ring. a may be bonded to form a ring, [ka] teeth, [ka] The structure can be formed as follows.

[0072] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m and is represented by formula 3. [ka] (m is selected from 1, 2, or 3, and when m is selected from 1, two L b are the same or different, and when m is selected from 2 or 3, 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', and when two R' are simultaneously present, the two R' are the same or different; Y1 to Y4 are the same or different and selected from CR or N at each occurrence; X3~X8 are the same or different CRs each time they appear. x , C.R. x1 or N, At least one of X3 to X8 is CR x1 and R x1 has a structure represented by formula 2: [ka] R A and R B represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are 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, and E are each identically or differently selected from C, N, B, P, CR''', SiR''', or GeR'''' at each occurrence; 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 BR1 to R8 each occurrence may be the same or different and each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Adjacent R1 to R8 may be bonded to form a ring, Adjacent R' and R x may be bonded to each other to form a ring, Adjacent R's may be bonded to each other to form a ring, Adjacent R'', R''', R A , R B may be bonded to each other to form a ring.)

[0073] In this specification, "adjacent R1 to R8 may be bonded together to form a ring" means that any one or more groups among a group consisting of any two adjacent substituents among R1 to R8 may be bonded together to form a ring. Obviously, none of these substituents may be bonded together to form a ring.

[0074] According to one embodiment of the present invention, X1 to X8 are the same or different CRs each time they occur. x or CR x1 Selected from.

[0075] According to one embodiment of the present invention, X1 to X8 are the same or different CRs each time they occur. x or CR x1 Selected from X1 to X8 and CR x1 Only one may be chosen.

[0076] According to one embodiment of the present invention, X3 to X8 are CRs that are the same or different for each occurrence. x or CR x1 Selected from.

[0077] According to one embodiment of the present invention, X3 to X8 are CRs that are the same or different for each occurrence. x or CR x1 Selected from X3 to X8 and CR x1 Only one may be chosen.

[0078] According to one embodiment of the present invention, Y1 to Y4 are identically or differently selected from CR for each occurrence.

[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 an 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 is Ir(L a ) m (L b ) 3-m and is represented by Formula 3A. [ka] (m is selected from 1, 2, or 3, and when m is selected from 1, two L b are the same or different, and when m is selected from 2 or 3, 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', and when two R' are simultaneously present, the two R' are the same or different; R, R x and R x1 represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; R x1 has a structure represented by formula 2: [ka] R A and R B represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are 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, and E are each identically or differently selected from C, N, B, P, CR''', SiR''', or GeR'''' at each occurrence; 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 each occurrence may be the same or different and each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Adjacent R1 to R8 may be bonded to form a ring, Adjacent R' and R x may be bonded to each other to form a ring, Adjacent R's may be bonded to each other to form a ring, Adjacent R'', R''', R A , R B may be bonded to each other 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 invention, A1, A2, B1 and B2 are identically or differently selected from C at each occurrence.

[0086] According to one embodiment of the invention, E is selected from N, identically or differently at each occurrence.

[0087] According to one embodiment of the present invention, R x are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof.

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

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

[0090] According to one embodiment of the present invention, ring A and ring B, each occurrence being the same or different, are selected from a carbocyclic ring having 5 to 12 ring atoms, a heterocyclic ring having 5 to 12 ring atoms, or a combination thereof.

[0091] According to one embodiment of the present invention, ring A and ring B, each occurrence being the same or different, are selected from a carbocyclic ring having 5-6 ring atoms, a heterocyclic ring having 5-6 ring atoms, or a combination thereof.

[0092] According to one embodiment of the present invention, R x1 has a structure represented by formula 4. [ka] (A3 to A6 are the same or different CRs for each occurrence. A or N, B3 to B6 are the same or different CRs for each occurrence. B or N, 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 A , RB and R'' each occurrence may be the same or different and is hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Adjacent R'', R A , R B may be bonded to each other to form a ring, "*" represents the bonding point in formula 4.)

[0093] In this embodiment, when n is 0, L is absent in formula 4, ie, formula 4 has the following structure: [ka] When n is 1 and L is selected from a single bond, formula 4 has the following structure: [ka]

[0094] According to one embodiment of the present invention, A3 to A6 are CRs that are the same or different for each occurrence.A Selected from.

[0095] According to one embodiment of the present invention, B3 to B6 are the same or different CRs for each occurrence. B Selected from.

[0096] According to an 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 an 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 are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof.

[0099] According to one embodiment of the present invention, R A and R B At least one of is selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, a cyano group, and combinations thereof.

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

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

[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 a single bond.

[0105] According to one embodiment of the present invention, R″ at each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, and combinations thereof.

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

[0107] According to one embodiment of the present invention, at least one of X3 to X8 is CR x1 Selected from.

[0108] According to one embodiment of the present invention, at least one of X4 to X8 is CR x1 Selected from.

[0109] According to one embodiment of the present invention, X4 is a CR x1 Selected from.

[0110] According to one embodiment of the present invention, at least one of X5 to X8 is CR x1 Selected from.

[0111] According to one embodiment of the present invention, X7 or X8 is CR x1 Selected from.

[0112] According to one embodiment of the present invention, X8 is a CR x1 Selected from.

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

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

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

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

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

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

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

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

[0121] According to one embodiment of the present invention, R, at each occurrence, is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 6 to 20 carbon atoms, and combinations thereof.

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

[0123] According to one embodiment of the present invention, at least one R is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 6 to 20 carbon atoms, and combinations thereof.

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

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

[0128] According to one embodiment of the present invention, at least one or at least two or at least three or all of R2, R3, R6 and R7 are selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0129] According to one embodiment of the present invention, at least one or at least two or 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 or at least two or at least three or all of R2, R3, R6 and R7 are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, any of the above groups partially or fully deuterated, and deuterium.

[0131] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1832 Among them, L a1 ~L a1832 A specific structure of the above is shown in claim 18.

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

[0133] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b334 Among them, L b1 ~L b334 A specific structure of the above is shown in claim 19.

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

[0135] According to one embodiment of the present invention, L c may be the same or different for each occurrence of L c1 ~L c360 Among them, L c1 ~L c360 A specific structure of the above 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 ) structure, L a may be the same or different for each occurrence of L a1 ~L a1832 L b may be the same or different for each occurrence of L b1 ~L b334 L c may be the same or different for each occurrence of L c1 ~L c360Among them, L a1 ~L a1832 The specific structure of is shown in claim 18, b1 ~L b334 The specific structure of is shown in claim 19, c1 ~L c360 A specific structure of the above 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, hydrogen atoms in metal complex 1 to metal complex 1576 may be partially or completely deuterated.

[0139] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1891 Among them, L a1 ~L a1891 A specific structure of the above is shown in claim 18.

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

[0141] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b341 Among them, L b1 ~L b341 A specific structure of the above is shown in claim 19.

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

[0143] According to one embodiment of the present invention, L c may be the same or different for each occurrence of L c1 ~L c360 Among them, L c1 ~L c360 A specific structure of the above 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 ) structure, L a may be the same or different for each occurrence of L a1 ~L a1891 L b may be the same or different for each occurrence of L b1 ~L b341 L c may be the same or different for each occurrence of L c1 ~L c360 Among them, L a1 ~L a1891 The specific structure of is shown in claim 18, b1 ~L b341 The specific structure of is shown in claim 19, c1 ~L c360 A specific structure of the above 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, hydrogen atoms in metal complex 1 to metal complex 1646 may be partially or completely deuterated.

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

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

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

[0150] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent device comprises a host compound, which comprises one or more host compounds, and when the host compound is a combination of multiple compounds, the host compound 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 device includes a first host compound.

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

[0153] According to one embodiment of the present invention, in the electroluminescent device, the first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0154] According to an embodiment of the present invention, in the electroluminescent device, the first host compound has a structure represented by Formula X: [ka] (L x each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; V may be the same or different for each occurrence, C, CR v or N, and at least one of V is C; L x Binds to T may be the same or different for each occurrence, C, CR t or N, and at least one of T is C; L x Binds to R v and R tare each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Ar1 is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R v and R t may be bonded to form a ring.

[0155] In the examples, "adjacent substituents R v and R t may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v Two substituents R t R v and R tThis means that any one or more of these substituents may be bonded to each other to form a ring. Obviously, none of these substituents may be bonded to each other to form a ring.

[0156] According to one embodiment of the present invention, in the electroluminescent device, the first host compound has a structure represented by one of Formulae Xa to Xj. [ka] (L x each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; V may be the same or different for each occurrence. v or N, T may be the same or different for each occurrence. t or N, R v and R tare each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, Ar1 is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R v and R t may be bonded to form a ring.

[0157] The second compound has a structure represented by Formula 5. [ka] (E1 to E6 are C, CR, or the same or different for each occurrence. e or N, and at least two of E1 to E6 are N, and at least one of E1 to E6 is C; and bonded to formula A; [ka] Q is, identically or differently, O, S, Se, N, NR Q , C.R. Q R Q , SiR Q R Q , G.E.R. Q R Q and R Q C=CR Q Two R Q When two R Q may be the same or different, p is 0 or 1; r is 0 or 1; When Q is selected from N, p is 0 and r is 1; Q is O, S, Se, or NR Q , C.R. Q R Q , SiR Q R Q , G.E.R. 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, each occurrence, the same or different, selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1 to Q8 are the same or different for each occurrence, C, CR q or N, R e , R Q and R qeach occurrence may be the same or different and may be hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, "*" represents the bond between Formula A and Formula 5, Adjacent substituents R e , R Q , R q may be bonded to form a ring.

[0158] In the present specification, "adjacent substituents R e , R Q , R q may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R e Two substituents R Q Two substituents R q R Q and R q This means that any one or more of these substituents may be bonded to each other to form a ring. Obviously, none of these substituents may be bonded to each other to form a ring.

[0159] According to one embodiment of the present invention, in the electroluminescent device, 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% based on the total weight of the light emitting layer.

[0160] According to an embodiment of the present invention, in the electroluminescent device, 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% based on the total weight of the light-emitting layer.

[0161] According to an embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer. The hole injection layer may be a functional layer of a single material or a functional layer containing multiple materials. The multiple materials most often used are hole transport materials doped with a certain percentage of p-type conductive doping materials. Common p-type doping materials are as follows: [ka]

[0162] According to another embodiment of the present invention, a composition is disclosed comprising a metal complex as described in any one of the above embodiments.

[0163] Combination with other materials

[0164] The materials of the specific layers used in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of US Patent Application US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. 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 easily refer to the literature to identify other materials that can be used in combination.

[0165] It is stated herein that the materials of specific layers used in the organic light-emitting device can be used in combination with a variety of other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0166] In the examples of material synthesis, all reactions are carried out under nitrogen protection unless otherwise stated. All reaction solvents are anhydrous and used as obtained from commercial sources. The synthesized products were subjected to structural confirmation and property testing using one or more instruments (including but not limited to Bruker nuclear magnetic resonance, Shimadzu liquid chromatography, liquid chromatography / mass spectrometer, gas chromatography / mass spectrometer, differential scanning calorimeter, Shanghai Liangguang Technology fluorescence spectrophotometer, Wuhan Science & Technology electrochemical work station, Anhui Beiqi sublimation equipment, etc.) in a manner familiar to those skilled in the art. In the examples of devices, the properties of the devices were also tested using instruments (including but not limited to Angstrom Engineering deposition machine, Suzhou Fusida optical test system, service life test system, Beijing Liangtuo ellipsometer, etc.) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment, testing methods, etc., and can reliably and unaffectedly obtain the specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification.

[0167] Examples of material synthesis

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

[0169] At room temperature under nitrogen gas protection, intermediate 1 (2.0 g, 2.2 mmol) and intermediate 2 (1.2 g, 2.7 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in that order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 765 (1.0 g, 0.9 mmol, 40%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (2.0 g, 2.2 mmol) and intermediate 3 (1.3 g, 2.7 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 785 (1.0 g, 0.8 mmol, 36%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (2.1 g, 2.5 mmol) and intermediate 4 (1.3 g, 2.8 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 773 (0.5 g, 0.5 mmol, 20%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 5 (1.6 g, 4.0 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in that order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 697 (1.0 g, 1.0 mmol, 33%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (3.0 g, 3.7 mmol) and intermediate 6 (2.8 g, 5.7 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in that order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 778 (1.5 g, 1.4 mmol, 38%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (1.4 g, 1.7 mmol) and intermediate 7 (1.1 g, 2.0 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in that order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 782 (0.5 g, 0.4 mmol, 24%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (1.0 g, 1.2 mmol) and intermediate 8 (0.7 g, 1.5 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the mixture was heated to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 777 (0.3 g, 0.3 mmol, 25%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (1.7 g, 2.1 mmol) and intermediate 9 (1.2 g, 2.7 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain a yellow solid 867 (1.0 g, 0.9 mmol, 43%). The 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 under nitrogen gas protection, intermediate 1 (1.9 g, 2.3 mmol) and intermediate 10 (1.5 g, 3.5 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in that order, and the temperature was raised to 100°C and reacted for 96 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 799 (1.55 g, 1.48 mmol, 64%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (1.9 g, 2.3 mmol) and intermediate 11 (1.3 g, 3.1 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the temperature was raised to 100°C and reacted for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 839 (1.3 g, 1.27 mmol, 55%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 25 (3.7 g, 5.1 mmol) and intermediate 13 (2.0 g, 7.6 mmol) were added to 290 mL of ethanol, heated to 80° C., and reacted for 24 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The mixture 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 under nitrogen gas protection, intermediate 14 (0.6 g, 0.7 mmol) and carbazole (0.33 g, 2.0 mmol) were added to 30 mL of DMF solvent, and the temperature was raised to 100° C. and reacted for 24 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether=1 / 1) to obtain metal complex 1577 (0.45 g, 0.42 mmol, 60%). The 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 under nitrogen gas protection, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 15 (1.6 g, 3.6 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in that order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 789 (1.66 g, 1.6 mmol, 52%). The 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 under nitrogen gas protection, intermediate 1 (2.5 g, 3.0 mmol) and intermediate 16 (1.7 g, 4.1 mmol) were added to a mixed solvent of 2-ethoxyethanol (50.0 mL) and DMF (50.0 mL) in order, and the temperature was raised to 100°C and reacted for 72 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 725 (0.9 g, 0.88 mmol, 29%) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1022.4.

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

[0197] At room temperature under nitrogen gas protection, intermediate 1 (0.88 g, 1.1 mmol) and intermediate 17 (0.6 g, 1.2 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the mixture was heated to 100°C and reacted for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 797 (0.36 g, 0.32 mmol, 29%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (2.1 g, 2.5 mmol) and intermediate 18 (1.3 g, 2.8 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in order, and the temperature was raised to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 1584 (0.54 g, 0.50 mmol, 20%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (2.0 g, 2.5 mmol) and intermediate 19 (1.8 g, 3.3 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the mixture was heated to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 1606 (1.0 g, 0.85 mmol, 34%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 1 (0.5 g, 0.6 mmol) and intermediate 20 (0.3 g, 0.7 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the mixture was heated to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain a yellow solid metal complex 1598 (0.3 g, 0.28 mmol, 47%). The 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 under nitrogen gas protection, intermediate 21 (1.5 g, 1.61 mmol) and intermediate 22 (1.05 g, 1.93 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and the temperature was raised to 100°C and reacted for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 959 (0.61 g, 0.54 mmol, 33%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 21 (2.0 g, 2.2 mmol) and intermediate 23 (1.3 g, 2.8 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the mixture was heated to 100°C and reacted for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 1612 (0.47 g, 0.45 mmol, 20%) as a yellow solid. The 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 under nitrogen gas protection, intermediate 24 (2.0 g, 2.2 mmol) and intermediate 26 (1.3 g, 2.6 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the mixture was heated to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain a yellow solid metal complex 1643 (0.75 g, 0.4 mmol, 28%). The 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 under nitrogen gas protection, intermediate 27 (2.0 g, 2.5 mmol) and intermediate 28 (1.6 g, 3.6 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the mixture was heated to 100°C and reacted for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure. The product was purified by silica gel column chromatography (dichloromethane / petroleum ether = 1 / 1) to obtain metal complex 1645 (0.75 g, 0.4 mmol, 28%) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 1013.3.

[0212] Example of the element

[0213] Element Example 1 First, a glass substrate with an indium tin oxide (ITO) anode with a thickness of 80 nm was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, the vacuum level was set to about 10 for the specified organic layers. -8 In the case of 3000 Hz, the layers were deposited on the ITO anode by hot vacuum deposition at a rate of 0.2-2 angstroms / second. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transport layer (HTL). Compound H1 was used as an electron blocking layer (EBL). Metal complex 697 according to the present invention was co-deposited with compounds H1 and H2 as a dopant to be used as an emissive layer (EML). Compound HB was used as a hole blocking layer (HBL) on the EML. Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL) on the HBL. Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm was deposited as an electron injection layer, and aluminum with a thickness of 120 nm was deposited as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

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

[0215] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the 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 the metal complex 697 of the present invention and the compound GD1 of the comparative example is the ligand L a The only difference is that the carbazole substituent above is replaced with a phenyl group. When they are used in a similar organic electroluminescence device, the voltage of Example 1 is reduced by 0.26 V, the CE is improved by 8.4%, the PE is improved by 16.1%, and the EQE is improved by 9.7%. As a result, the R x1 L having a substituent aIt has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0221] Element Example 2 The embodiment of Device Example 2 is similar to Device Example 1, except that Metal Complex 867 replaces Metal Complex 697 of the present invention in the light-emitting layer (EML).

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

[0223] The detailed layer structure and thickness of the device are shown in Table 3. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the data are recorded and shown in Table 4.

[0227] [Table 4]

[0228] As can be seen from the comparative data of Example 2 and Comparative Example 2 in Table 4, the difference between the metal complex 867 of the present invention and the compound GD2 of the comparative example is the ligand L a The only difference is that the diphenylamino substituent in the above is replaced by deuterium. When used in a similar organic electroluminescence device, the voltage of Example 2 was reduced by 0.2 V, the CE was improved by 6.7%, the PE was improved by 10.7%, and the EQE was improved by 8.2%. As a result, the R x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0229] Element Example 3 The embodiment of device example 3 is similar to device example 1, except that metal complex 765 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

[0230] Element Example 4 The embodiment of device example 4 is similar to device example 1, except that metal complex 785 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

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

[0232] The detailed layer structure and thickness of the device are shown in Table 5. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the data are recorded and shown in Table 6.

[0236] [Table 6]

[0237] As can be seen from the comparative data of Example 3, Example 4 and Comparative Example 3 in Table 6, L a In addition to the presence of cyano substituents on the ligand, the difference between the metal complexes 765 and 785 of the present invention and the compound GD3 of the comparative example is the ligand L a The substituted or unsubstituted carbazole substituents in the above are simply replaced with phenyl groups. By being used in similar organic electroluminescence devices, Examples 3 and 4 have a voltage drop of 0.29V and 0.35V, respectively, a CE improvement of 5.3% and 10.6%, a PE improvement of 10.4% and 22.1%, and an EQE improvement of 5.8% and 10.8%. At the same time, Examples 3 and 4 have a full width at half maximum narrower by 1.4nm and 0.5nm, respectively, than Comparative Example 3 when the maximum emission wavelength remains unchanged, and a more saturated green emission is obtained. As a result, the R x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0238] In short, the R x1 L having a substituent a The metal complex containing the ligand can obtain a device with better performance, for example, lower device voltage and improved CE, PE and EQE, and can also comprehensively improve various performances of the device, ultimately greatly improving the overall performance of the device.

[0239] Element Example 5 The embodiment of device example 5 is similar to device example 1, except that metal complex 725 replaces metal complex 697 of 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 similar to that of Example 1 of the device, except that the compound GD4 replaces the metal complex 697 of the present invention in the light-emitting layer (EML).

[0241] Element Example 6 The embodiment of the device of Example 6 is the same as that of the device of Example 1, except that in the light-emitting layer (EML), the metal complex 1577 is substituted for the metal complex 697 of the present invention, in which 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 similar to that of Example 6 of the device, except that the compound GD5 replaces the metal complex 1577 of the present invention in the light-emitting layer (EML).

[0243] The detailed layer structure and thickness of the device are shown in Table 7. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the 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 of the present invention and the compound GD4 of the comparative example is the ligand L a The only difference is that the carbazole substituent in the above is replaced with a biphenyl group. When they are used in a similar organic electroluminescence device, the voltage is reduced by 0.30 V, the CE is improved by 2.5%, the PE is improved by 10.5%, and the EQE is improved by 3.6%, when compared between Example 5 and Comparative Example 4.

[0249] Comparing Example 6 and Comparative Example 5, the difference between the metal complex 1577 of the present invention and the compound GD5 of the comparative example is the ligand L a The only difference is that the carbazole substituent in the above is replaced with a deuterated methyl group. When they are used in a similar organic electroluminescence device, the voltage is reduced by 0.15 V, the CE is improved by 13.0%, the PE is improved by 17.5%, and the EQE is improved by 11.8%, when compared between Example 6 and Comparative Example 5.

[0250] As a result, the present invention x1 L having a substituent aIt has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0251] Element Example 7 The embodiment of device example 7 is similar to device example 1, except that metal complex 789 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

[0252] Element Example 8 The embodiment of device example 8 is similar to device example 1, except that metal complex 1584 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

[0253] Element Example 9 The embodiment of Device Example 9 is similar to Device Example 1, except that Metal Complex 797 replaces Metal Complex 697 of the present invention in the light-emitting layer (EML).

[0254] Element Example 10 The embodiment of device example 10 is similar to device example 1, except that metal complex 1606 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

[0255] Element Example 11 The embodiment of device example 11 is similar to device example 1, except that metal complex 959 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

[0256] Element Example 12 The embodiment of the device of Example 12 is the same as that of the device of Example 1, except that in the light-emitting layer (EML), the metal complex 697 of the present invention is replaced by the metal complex 1643. Among them, the ratio of compound H1: compound H2: metal complex 1643 is 71:23:6.

[0257] The detailed layer structure and thickness of the device are shown in Table 9. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the 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 cyano substituents on the ligand, the difference between the metal complexes 789, 1584, 797, and 1606 of the present invention and the comparative compound GD3 is the presence of ligand L aThe only difference is that the carbazole groups having different substitutions on the above are substituted with phenyl groups. By using them in similar organic electroluminescence 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 was reduced by 0.40 V, 0.46 V, 0.26 V, and 0.29 V, respectively, the CE was improved by 4.3%, 7.4%, 4.3%, and 3.2%, respectively, the PE was improved by 15.6%, 22.1%, 11.7%, and 11.7%, respectively, and the EQE was improved by 3.7%, 6.5%, 5.0%, and 3.9%. As a result, the R x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0263] As can be seen from the data in Examples 11 and 12, the metal complexes 959 and 1643 of the present invention are both R x1 Substituent L a When the ligand is present, each L a Ligand and L b There were different substituents on the ligand. As can be seen from the device results, the EQE was all above 25%, and the CE was all about 100 cd / A, among which the EQE of Example 11 reached 26.55%. At the same time, their PE and voltage were also at a high level, indicating the high overall performance of the device.

[0264] As described above, R according to the present invention x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0265] Element Example 13 The embodiment of device example 13 is similar to device example 1, except that metal complex 799 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

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

[0267] The detailed layer structure and thickness of the device are shown in Table 11. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the 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 the metal complex 799 of the present invention and the compound GD6 of the comparative example is the ligand L aThe only difference is that the carbazole substituent in the above is replaced with a phenyl group. When used in a similar organic electroluminescence device, the full width at half maximum of Example 13 was narrowed by 2.0 nm, the voltage was reduced by 0.11 V, the CE was improved by 5.8%, the PE was improved by 9.5%, and the EQE was improved by 6.5%.

[0273] As described above, R according to the present invention x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0274] Element Example 14 The embodiment of the device of Example 14 is the same as that of the device of Example 1, except that in the light-emitting layer (EML), the metal complex 697 of the present invention is replaced by the metal complex 839. Among them, 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 similar to that of Example 14 of the device, except that compound GD7 replaces metal complex 839 of the present invention in the light-emitting layer (EML).

[0276] The detailed layer structure and thickness of the device are shown in Table 13. Layers using more than one material can be obtained by doping different compounds in the weight ratios mentioned above.

[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 was 15 mA / cm 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the device were measured and the data are recorded and shown in Table 14.

[0280] [Table 14]

[0281] As can be seen from the element data in Table 14, comparing Example 14 with Comparative Example 7, L a In addition to the presence of fluorine substituents on the ligand, the difference between the metal complex 839 of the present invention and the comparative compound GD7 is the presence of ligand L a The only difference is that the carbazole substituent in the above is replaced with a phenyl group. When they are used in a similar organic electroluminescence device, the voltage of Example 14 is reduced by 0.66 V, the CE is improved by 4.6%, the PE is improved by 23.3%, and the EQE is improved by 5.5%. x1 L having a substituent a It has been proven that the use of metal complexes containing ligands can lead to devices with superior performance, comprehensive improvements in various performance aspects of the device, and ultimately a significant improvement in the overall performance of the device.

[0282] In short, the R x1 L having a substituent a By using a metal complex containing a ligand, it is possible to obtain a device with better performance, for example, lower device voltage and improved CE, PE and EQE, and also to comprehensively improve various performances of the device, ultimately greatly improving the overall performance of the device.

[0283] It should be understood that the various embodiments described herein are merely illustrative and are not intended to limit the scope of the present invention. Thus, it will be apparent to those skilled in the art that the invention sought to be protected includes variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the concept of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims

1. Metal M and ligand L coordinated with metal M ａ A metal complex comprising: ａ A metal complex having a structure represented by formula 1. 【Chemistry 1】 (In formula 1, the metal M is selected from metals having a relative atomic mass greater than 40; Ring Cy, at each occurrence, is the same or different and is selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof, and said ring Cy contains at least 3 carbon atoms; the ring Cy is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; X, at each occurrence, is the same or different and is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R' are present simultaneously, the two R' are the same or different; X １ ~X ８ Each occurrence may be the same or different, C, CR ｘ , C.R. ｘ１ or N, １ ~X ４ At least one of is C and is bonded to the ring Cy; X １ , X ２ , X ３ or X ４ is bonded to the metal M via a metal-carbon bond or a metal-nitrogen bond; X １ ~X ８ At least one of the following is CR ｘ１ and R ｘ１ has a structure represented by formula 2: 【Chemistry 2】 In formula 2, R Ａ and R Ｂ represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are selected from a carbocycle having 3 to 30 ring atoms, a heterocycle having 3 to 30 ring atoms, or a combination thereof; n is 0 or 1; A １ , A ２ , B １ , B ２ , E is, at each occurrence, the same or different, selected from C, N, B, P, CR'', SiR'''', or GeR''''; L is a single bond, O, S, SO ２ , 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 ｘ , R Ａ , R Ｂ are the same or different at each occurrence and each represents hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl ... a substituted or unsubstituted alkynyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a phosphino group, and combinations thereof; "*" represents the bonding point in formula 2; Adjacent R' and R ｘ may be bonded to each other to form a ring, Adjacent R'', R'', R Ａ , R Ｂ may be bonded to each other to form a ring.)

2. Ring Cy may be the same or different in each occurrence. 【Chemistry 3】 The metal complex according to claim 1, which has any one structure selected from the group consisting of: (R is the same or different at each occurrence and represents mono-substitution, polysubstitution, or no substitution. When multiple R are present in any one structure, said R are the same or different, R each occurrence may be the same or different and is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aryloxy ... a substituted or unsubstituted alkynyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring, "#" represents the bond site with the metal M, 【Chemistry 4】 , X １ , X ２ , X ３ or X ４ It represents the bonding point with

3. The metal complex is M(L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ having the general formula M at each occurrence is the same or different and is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, preferably M at each occurrence is the same or different and is selected from Pt or Ir; L ａ , L ｂ and L ｃ are the first, second and third ligands coordinated to the metal M, respectively, and L ｃ and the L ａ Or L ｂ are the same or different, L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M, and when m is 2 or more, multiple L ａ are the same or different, and when n is 2, two L ｂ are the same or different, and when q is 2, two L ｃ are the same or different, L ａ may be the same or different for each occurrence. 【Chemistry 5-1】 【Chemistry 5-2】 【Chemistry 5-3】 【Chemistry 5-4】 【Chemistry 5-5】 【Chemistry 5-6】 Selected from the group consisting of: X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R' are simultaneously present, the two R' are the same or different; R, R ｘ and R ｘ１ represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; R ｘ１ has a structure represented by formula 2: 【Chemistry 6】 R Ａ and R Ｂ represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are selected from a carbocycle having 3 to 30 ring atoms, a heterocycle having 3 to 30 ring atoms, or a combination thereof; A １ , A ２ , B １ , B ２ , E is, at each occurrence, the same or different, selected from C, N, B, P, CR'', SiR'''', or GeR''''; n is 0 or 1; L is a single bond, O, S, SO ２ , 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; "*" represents the bonding point in formula 2; Adjacent R' and R ｘ may be bonded to each other to form a ring, Adjacent R's may be bonded to each other to form a ring, Adjacent R'', R'', R Ａ , R Ｂ may be bonded to each other to form a ring, L ｂ and L ｃ may be the same or different for each occurrence. 【Chemistry 7】 A structure represented by any one selected from the group consisting of: X ｂ Each occurrence may be the same or different and may be O, S, Se, NR Ｎ１ , C.R. Ｃ１ R Ｃ２ Selected from the group consisting of: R ａ and R ｂ represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; Adjacent Substituents R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｃ１ and R Ｃ２ may be bonded 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 Ｃ２ each occurrence is the same or different and represents hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or 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, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a phosphino group, and combinations thereof.

4. The metal complex is Ir(L ａ ) ｍ (L ｂ ) ３－ｍ The metal complex of claim 1 having the structure and represented by formula 3: 【Chemistry 8】 (m is selected from 1, 2, or 3, and when m is selected from 1, two L ｂ are the same or different, and when m is selected from 2 or 3, a plurality of L ａ are the same or different, X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R' are simultaneously present, the two R' are the same or different; Y １ ~Y ４ is selected from CR or N, X ３ ~X ８ CR may be the same or different for each occurrence. ｘ , C.R. ｘ１ or N, X ３ ~X ８ At least one of the following is CR ｘ１ and R ｘ１ has a structure represented by formula 2: 【Chemistry 9】 R Ａ and R Ｂ represents, identically or differently, a single substitution, a multiple substitution, or no substitution at each occurrence; ring A and ring B are the same or different and are selected from a carbocycle having 3 to 30 ring atoms, a heterocycle having 3 to 30 ring atoms, or a combination thereof; A １ , A ２ , B １ , B ２ , E is, at each occurrence, the same or different, selected from C, N, B, P, CR'', SiR'''', or GeR''''; n is 0 or 1; L is a single bond, O, S, SO ２ , 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 , R １ ~R ８ are the same or different at each occurrence and each represents hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl ... a substituted or unsubstituted alkynyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a phosphino group, and combinations thereof; Adjacent R １ ~R ８ may be bonded to each other to form a ring, Adjacent R' and R ｘ may be bonded to each other to form a ring, Adjacent R's may be bonded to each other to form a ring, Adjacent R'', R'', R Ａ , R Ｂ may be bonded to each other to form a ring.)

5. X ３ ~X ８ CR may be the same or different for each occurrence. ｘ or CR ｘ１ and / or Y １ ~Y ４ 5. The metal complex of claim 4, wherein each occurrence is the same or different and is selected from CR.

6. X ３ ~X ８ At least one of is N, and / or Y １ ~Y ４ The metal complex of claim 4, wherein at least one of is N.

7. 7. The metal complex according to claim 1, wherein X is selected from O or S.

8. R ｘ are, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof; Preferably, R ｘ are, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, a cyano group, and combinations thereof; More preferably, R ｘ are each independently selected from the group consisting of hydrogen, deuterium, fluorine, a cyano group, 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 deuterated methyl group, a deuterated ethyl group, a deuterated propyl group, a deuterated isopropyl group, a deuterated n-butyl group, a deuterated isobutyl group, a deuterated tert-butyl group, a deuterated cyclopentyl group, a deuterated cyclohexyl group, a phenyl group, a pyridine group, a trimethylsilyl group, a trimethylgermanium group, and combinations thereof.

9. R ｘ１ The metal complex according to any one of claims 1 to 6, having a structure represented by formula 4: 【Chemistry 10】 (A ３ ~A ６ CR may be the same or different for each occurrence. Ａ or N, B ３ ~B ６ CR may be the same or different for each occurrence. Ｂ or N, n is 0 or 1; L is a single bond, O, S, SO ２ , 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 Ａ , R Ｂ and R″ at each occurrence may be the same or different and is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or selected from the group consisting of an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a phosphino group, and combinations thereof; Adjacent R'', R Ａ , R Ｂ may be bonded to each other to form a ring, "*" represents the bonding point in formula 4.

10. A ３ ~A ６ CR may be the same or different for each occurrence. Ａ and / or B ３ ~B ６ CR may be the same or different for each occurrence. Ｂ Selected from R Ａ and R Ｂ are, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a cyano group, and combinations thereof; Preferably, R Ａ and R Ｂ are, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, a cyano group, and combinations thereof; More preferably, R Ａ and R Ｂ 10. The metal complex according to claim 9, wherein at least one of is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, a cyano group, and combinations thereof.

11. 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; Preferably, L is selected from a single bond, O, S, NR'', R''C=CR'', a phenylene group, More preferably, L is selected from a single bond.

12. X ５ ~X ８ At least one of the following is CR ｘ１ Selected from Preferably, X ７ or X ８ At least one of the following is CR ｘ１ Selected from More preferably, X ８ is CR ｘ１ The metal complex according to claim 1 or 4, which is selected from

13. X ５ ~X ８ At least one of the following is CR ｘ and R ｘ is selected from a cyano group and fluorine; X ５ ~X ８ At least one of the following is CR ｘ１ Selected from Preferably, X ７ is CR ｘ wherein R ｘ is a cyano group or fluorine; X ８ is CR ｘ１ and / or X ８ is CR ｘ , wherein R ｘ is a cyano group or fluorine; X ７ is CR ｘ１ The metal complex according to claim 1 or 4, which is selected from

14. R ｘ１ An may be the same or different for each occurrence. １ ~An １３５ Selected from the group consisting of: 【Chemistry 11-1】 【Chemistry 11-2】 【Chemistry 11-3】 【Chemistry 11-4】 Preferably, the An １ ~An １３５ The metal complex according to claim 1 , wherein the hydrogen atoms in

15. R, each occurrence being the same or different, is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 6 to 20 carbon atoms, and combinations thereof; 7. The metal complex according to any one of claims 1 to 6, wherein at least one R is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

16. R １ ~R ８ At least one or at least two of the R are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R １ ~R ４ and / or R ５ ~R ８ is at least 4, R １ ~R ４ At least one or at least two of the R are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R １ ~R ４ and / or the sum of the carbon atoms of R ５ ~R ８ At least one or at least two of the R are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R ５ ~R ８ The metal complex according to claim 4 , wherein the sum of the numbers of carbon atoms of is at least 4.

17. R ２ , R ３ , R ６ , R ７ at least one or at least two or at least three or all of are selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof; Preferably, R ２ , R ３ , R ６ , R ７ at least one, or at least two, or at least three, or all, of 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; More preferably, R ２ , R ３ , R ６ , R ７ 5. The metal complex according to claim 4, wherein at least one, at least two, or at least three, or all of the above 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 which are partially or fully deuterated, and deuterium.

18. L ａ Each occurrence may be the same or different. ａ１ ~L ａ１８９１ and L is selected from the group consisting of ａ１ ~L ａ１８９１ The specific structure of is as follows: The following L ａ１ ~L ａ１４４０ has the following structure: 【Chemistry 12】 where X, Cy, R Ｘ４ ~R Ｘ８ is selected from the atoms or groups in the table below, 【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】 The following L ａ１４４１ ~L ａ１５１４ has the following structure: 【Chemistry 13】 where X, Cy, R Ｘ４ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-45】 【Table 1-46】 【Table 1-47】 The following L ａ１５１５ ~L ａ１５８８ has the following structure: 【Chemistry 14】 X, Cy, R Ｘ４ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-48】 【Table 1-49】 【Table 1-50】 The following L ａ１５８９ ~L ａ１６６２ has the following structure: 【Chemistry 15】 where X, Cy, R Ｘ４ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-51】 【Table 1-52】 【Table 1-53】 The following L ａ１６６３ ~L ａ１７３６ has the following structure: 【Chemistry 16】 where X, Cy, R Ｘ４ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-54】 【Table 1-55】 【Table 1-56】 The following L ａ１７３７ ~L ａ１７６０ has the following structure: 【Chemistry 17】 Where Cy, R Ｘ４ ~R Ｘ７ is selected from the atoms or groups in the table below, 【Table 1-57】 The following L ａ１７６１ ~L ａ１７８４ has the following structure: 【Chemistry 18】 where X, Cy, R Ｘ４ ~R Ｘ６ , R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-58】 The following L ａ１７８５ ~L ａ１８０８ has the following structure: 【Chemistry 19】 Where Cy, R Ｘ４ ~R Ｘ５ , R Ｘ７ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-59】 The following L ａ１８０９ ~L ａ１８３２ has the following structure: 【Chemistry 20】 Where Cy, R Ｘ４ , R Ｘ６ ~R Ｘ８ is selected from the atoms or groups in the table below, 【Table 1-60】 In the above table, Cy1 to Cy9 have the following structures: 【Chemistry 21】 In Cy1 to Cy9, "#" represents a bonding site with the metal M, 【Chemical 22】 , X １ , X ２ , X ３ or X ４ represents the bonding site of In the above table, TMS stands for trimethylsilyl, TMG stands for trimethylgermanium group, 【Chemistry 23-1】 【Chemistry 23-2】 【Chemistry 23-3】 Preferably, the L ａ１ ~L ａ１８９１ The metal complex according to claim 14 , wherein the hydrogen atoms in

19. L ｂ may be the same or different for each occurrence. 【Chemistry 24-1】 【Chemistry 24-2】 【Chemistry 24-3】 【Chemistry 24-4】 【Chemistry 24-5】 【Chemistry 24-6】 【Chemistry 24-7】 【Chemistry 24-8】 【Chemistry 24-9】 【Chemistry 24-10】 Selected from the group consisting of: Preferably, the L ｂ１ ~L ｂ３４１ The metal complex according to claim 3, 4 or 18, wherein the hydrogen atoms in

20. L ｃ may be the same or different for each occurrence. 【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】 20. The metal complex of claim 19, selected from the group consisting of:

21. The metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 1646; Metal complex 1 to metal complex 1364 are IrL ａ (L ｂ ) ２ and two L ｂ are the same or different, L ａ and L ｂ correspond to the structures shown in the table below, 【Table 2-1】 【Table 2-2】 【Table 2-3】 【Table 2-4】 【Table 2-5】 【Table 2-6】 【Table 2-7】 【Table 2-8】 【Table 2-9】 【Table 2-10】 【Table 2-11】 【Table 2-12】 【Table 2-13】 【Table 2-14】 【Table 2-15】 【Table 2-16】 【Table 2-17】 【Table 2-18】 【Table 2-19】 【Table 2-20】 Metal complexes 1365 to 1382 are Ir(L ａ ) ２ L ｂ and two L ａ are the same or different, L ａ and L ｂ correspond to the structures shown in the table below, 【Table 2-21】 Metal complexes 1383 to 1562 are Ir(L ａ ) ２ L ｃ and two L ａ are the same or different, L ａ and L ｃ correspond to the structures shown in the table below, 【Table 2-22】 【Table 2-23】 【Table 2-24】 Metal complexes 1563 to 1568 are Ir(L ａ ) ３ and has three L ａ are the same or different, and the three L ａ correspond to the structures shown in the table below, 【Table 2-25】 Metal complexes 1569 to 1576 are Ir(L ａ ) (L ｂ ) (L ｃ ) structure, L ａ , L ｂ and L ｃ correspond to the structures shown in the table below, 【Table 2-26】 Metal complexes 1577 to 1646 are IrL ａ (L ｂ ) ２ and two L ｂ are identical, and L ａ and L ｂ correspond to the structures shown in the table below, 【Table 2-27】 【Table 2-28】 Preferably, the hydrogen atoms in the metal complexes 1 to 1646 may be partially or completely deuterated.

22. An electroluminescent device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, An electroluminescence device, wherein at least one of the organic layers comprises the metal complex according to any one of claims 1 to 21.

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

24. The light-emitting layer further includes a first host compound, Preferably, the light-emitting layer further comprises a second host compound, More preferably, 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, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

25. the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex is 1% to 30% based on the total weight of the light-emitting layer; The electroluminescent device according to claim 24, wherein the weight of the metal complex is preferably 3% to 13% based on the total weight of the light-emitting layer.

26. A composition comprising the metal complex according to any one of claims 1 to 21.

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