Electroluminescent material and device thereof

Abstract

The present invention discloses an electroluminescent material and a device thereof. The electroluminescent material comprises a metal complex containing a ligand represented by Formula 1 and can be used as a light-emitting material in an electroluminescent device. Such novel metal complexes can effectively control the emission wavelength, reduce the driving voltage of the electroluminescent device, significantly improve the current efficiency, power efficiency, and EQE of the electroluminescent device, improve the device lifespan, and provide even superior device performance. The present invention further discloses an electroluminescent device and a compound composition.

Description

Technology Field

[0001] The present invention relates to a compound used in an organic electronic device, for example, an organic light-emitting device. In particular, it relates to a metal complex comprising a ligand represented by Formula 1, and an organic electroluminescent device and a compound composition comprising said compound. 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 devices (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photoreceptors, 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 two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline aluminum layer as the electron transport layer and emissive layer (Applied Physics Letters, 1987, 51(12): 913-915). When 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 include multiple layers, such as a charge injection and transport layer, a charge and exciton blocking layer, and one or more emissive layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer tremendous potential for display and lighting applications. In addition, the inherent properties of organic materials (e.g., their flexibility) make them suitable for special applications (e.g., manufacturing on flexible substrates).

[0004] OLEDs can be classified into three different types based on their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It utilizes only singlet-state emission. Triplet states generated in the device are wasted through non-radiative decay channels. Consequently, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported a phosphorescent OLED that uses triplet-state emission from complex-containing heavy metals as the emitter. Thus, since both singlet and triplet states can be obtained, an IQE of 100% can be achieved. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have made a direct contribution to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters are provided with a small singlet-triplet state gap so that excitons can return from the triplet state to the singlet state. In TADF devices, triplet state excitons can generate singlet state excitons through reverse intersystem crossing, thereby achieving high IQE.

[0005] OLEDs can also be classified into low-molecular-weight and high-molecular-weight OLEDs depending on the form of the materials used. Low-molecular-weight materials refer to any organic or organometallic materials that are not polymers. If they possess a precise structure, the molecular weight of low-molecular-weight materials can be very large. Dendritic polymers with a clear structure are considered small molecules. High-molecular-weight OLEDs include conjugated polymers and non-conjugated polymers equipped with pendant emitting groups. If post-polymerization occurs during the manufacturing process, low-molecular-weight OLEDs can be transformed into high-molecular-weight OLEDs.

[0006] Various OLED manufacturing methods already exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. If the material can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution processes.

[0007] The emission color of an OLED can be realized through the structural design of the light-emitting material. OLEDs may include a single or multiple light-emitting layers to realize a desired spectrum. In green, yellow, and red OLEDs, phosphorescent materials have already been successfully commercialized. However, blue phosphorescent devices still face issues such as blue desaturation, short device lifespan, and high operating voltage. Commercial full-color OLED displays typically employ a mixed strategy using blue fluorescence and phosphorescent yellow or red and green. Currently, the problem of phosphorescent OLED efficiency rapidly decreasing at high brightness levels still persists. Furthermore, there is a desire to achieve a more saturated emission spectrum, higher efficiency, and a longer device lifespan.

[0008] In US20070034863A1 A metal complex containing a structure was disclosed, and in its ligand, two ring systems are connected via Y. Among the numerous structures disclosed, It includes ligands having B, N, or P atoms substituted with alkyl or phenyl groups as crosslinking atoms. This did not disclose or teach about the massive effects brought about by introducing a fusion structure at a specific additional position.

[0009] CN110698518A disclosed a phosphorescent material, and its general structural formula ..., where X is N or P. Specific examples include and There is. Additionally, it did not pay attention to the massive effect brought about by introducing a fusion structure at a specific location.

[0010] Regarding phosphorescent materials, although existing technologies have reported on them, in-depth research and development are still required to meet the industry's ever-improving demands for device performance, such as device emission color, emission saturation, voltage, device efficiency, and device lifespan. The problem to be solved

[0011] The present invention aims to provide a series of metal complexes comprising a ligand represented by Formula 1 to solve at least a part of the above problem. The metal complexes can be used as light-emitting materials in organic electroluminescent devices. These novel metal complexes can reduce the driving voltage of the electroluminescent device, significantly improve the current efficiency, power efficiency, and EQE of the electroluminescent device, improve the device lifespan, and provide even better device performance. means of solving the problem

[0012] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal aA metal complex comprising is disclosed, wherein the metal M is selected from metals with a relative atomic mass greater than 40; and the ligand L a It has a structure represented by Equation 1, and

[0013]

[0014] Here,

[0015] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0016] W is selected from B, N, or P, either identically or differently, whenever it appears;

[0017] Rings A, C, and D are selected from pentagonal unsaturated carbon rings, aromatic rings having 6-30 carbon atoms, or heteroaromatic rings having 3-30 carbon atoms, respectively, whenever they appear, either identically or differently;

[0018] Ring B is selected from a hetero ring having 5-30 ring atoms;

[0019] R a , R b , R c and R d Each time it appears, it represents a single substitution, multiple substitution, or non-substitution, either identically or differently;

[0020] R a , R b , R c and R dWhenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0021] Adjacent substituent R a , R b , R c and R d It can be connected arbitrarily to form a ring.

[0022] According to another embodiment of the present invention, an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode is further disclosed, wherein the organic layer comprises a metal complex according to the embodiment.

[0023] According to another embodiment of the present invention, a compound composition comprising a metal complex according to the above embodiment is further disclosed. Effects of the invention

[0024] A novel metal complex comprising a ligand represented by Formula 1 disclosed in the present invention can be used as a light-emitting material in an electroluminescent device. Such a novel metal complex can effectively control the emission wavelength, reduce the driving voltage of the electroluminescent device, significantly improve the current efficiency, power efficiency, and EQE of the electroluminescent device, improve the device lifespan, and provide even better device performance. Brief explanation of the drawing

[0025] FIG. 1 is a schematic diagram of an organic light-emitting device that may include the metal complex and compound composition disclosed in the text. FIG. 2 is a schematic diagram of another organic light-emitting device that may include the metal complex and compound composition disclosed in the text. Specific details for implementing the invention

[0026] OLEDs can be manufactured on various types of substrates (e.g., glass, plastic, and metal). FIG. 1 schematically and non-limitingly illustrates an organic light-emitting device (100). The drawings are not necessarily drawn in proportion, and some layer structures in the drawings may be omitted 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), a light-emitting layer (150), a hole blocking layer (160), an electron transport layer (170), an electron injection layer (180), and a cathode (190). The device (100) may be manufactured by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent US7279704B2, the entire contents of which are incorporated by reference into this application.

[0027] Each layer in these layers has more examples. An example is the flexible and transparent substrate-anode combination disclosed in U.S. Patent No. 5844363, combined by quoting the full text. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, combined by quoting the full text. An example of a host material is disclosed in U.S. Patent No. 6303238 (granted to Thompson et al.), combined by quoting the full text. An example of an n-doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, combined by quoting the full text. U.S. Patents No. 5703436 and No. 5707745, combined by quoting the full text, disclose examples of cathodes, which include composite cathodes having a metal thin layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. U.S. Patent No. 6097147 and U.S. Patent Application Publication No. 2003 / 0230980, combined by quoting the full text, describe in more detail the principles and uses of a blocking layer. U.S. Patent Application Publication No. 2004 / 0174116, combined by quoting the full text, provides examples of an injection layer. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, combined by quoting the full text.

[0028] The above-described hierarchical structure is provided through non-limiting embodiments. The function of the OLED can be implemented by combining the various types of layers described above, or some layers may be completely omitted. It may further include other layers not explicitly described. Optimal performance can be achieved by using a single material or a mixture of various materials within each layer. Any functional layer may include multiple sub-layers. For example, the light-emitting layer may have two layers of different light-emitting materials to achieve a desired light emission spectrum.

[0029] In one embodiment, the 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.

[0030] OLEDs also require an encapsulation layer, and in FIG. 2, an organic light-emitting device (200) is schematically and indefinitely illustrated. The difference from FIG. 1 is that an encapsulation layer (102) is further included on the cathode (190) to prevent harmful substances (e.g., moisture and oxygen) from the environment. Any material capable of providing encapsulation function can be used as the encapsulation layer (e.g., glass or an organic-inorganic mixed layer). The encapsulation layer must be placed directly or indirectly on the outside of the OLED device. Multi-thin film encapsulation is described in U.S. Patent US7968146B2, the entire contents of which are incorporated by reference in this application.

[0031] A device manufactured according to an embodiment of the present invention may be integrated into various types of consumer goods having one or more electronic component modules (or units) of said device. Some examples of such consumer goods include flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal emitters, head-up displays, displays that are entirely transparent or partially transparent, flexible displays, smartphones, tablets, tablet phones, wearable devices, smartwatches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3D displays, vehicle displays, and taillights.

[0032] The materials and structures described in the text may also be used in other organic electronic devices listed above.

[0033] As used in the text, "top" means the position furthest from the substrate, and "bottom" means the position closest to the substrate. When it is described that the first layer is "placed" on the second layer, the first layer is placed so as to be relatively far from the substrate. Unless it is specified that the first layer "and" the second layer are "in contact," other layers may exist between the first layer and the second layer. For example, even if various types of organic layers exist between the cathode and the anode, it can still be described that the cathode is "placed" on the anode.

[0034] As used in the text, "solution treatable" means that it can be dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension, and / or can be precipitated from a liquid medium.

[0035] If a ligand is considered to act directly on the photosensitivity of a luminescent material, the ligand can be referred to as a "photosensitive ligand." If a ligand is considered not to act on the photosensitivity of a luminescent material, the ligand can be referred to as an "auxiliary ligand," which can modify the properties of the photosensitive ligand.

[0036] The internal quantum efficiency (IQE) of fluorescent OLEDs is believed to be able to exceed the 25% spin statistics limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0037] In another aspect, E-type delayed fluorescence does not rely on collisions between two triplet states but rather on transitions between the triplet state and the singlet-excited state. Compounds capable of generating E-type delayed fluorescence must possess a very small singlet-triplet gap to facilitate transitions between energy states. Thermal energy can activate the transition from the triplet state to the singlet state. This type of delayed fluorescence is also referred to as thermally activated delayed fluorescence (TADF). A notable characteristic of TADF is that the delay factor increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is sufficiently fast to minimize non-radiative decay caused by the triplet state, the proportion of back-filled singlet-excited states can reach 75%. The total proportion of singlet states can be 100%, which far exceeds 25% of the spin statistics of excitons generated by the electric field.

[0038] The characteristics of E-type delayed fluorescence can be found in exciplex systems or single compounds. Unbound by theory, E-type delayed fluorescence is believed to require that the emitting material possess a small singlet-triplet energy gap (△ES-T). Organic donor-acceptor emitting materials containing nonmetals have the potential to realize these characteristics. The emission of such materials is generally characterized as donor-acceptor charge transfer (CT) type emission. In these donor-acceptor compounds, the spatial separation of HOMO and LUMO is generally small △E S-T It generates. This state may include a CT state. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor portion (e.g., an amino group or a carbazole derivative) and an electron acceptor portion (e.g., a six-membered aromatic ring containing N).

[0039] Regarding the definition of substituent terms,

[0040] Halogens or halides—as used in the text—include fluorine, chlorine, bromine, and iodine.

[0041] As used herein, the alkyl group includes straight-chain alkyl groups and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 12 carbon atoms is preferred, and an alkyl group having 1 to 6 carbon atoms is more preferred. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-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 groups. In the above, methyl, ethyl, propyl, isopropyl, n-butyl, secondary butyl, isobutyl, t-butyl, n-pentyl, neopentyl, and n-hexyl groups are preferred. Additionally, alkyl groups may be optionally substituted.

[0042] The cycloalkyl group comprises a cyclic alkyl group as used herein. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and a cycloalkyl group having 4 to 10 carbon atoms is preferred. Examples of cycloalkyl groups include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, etc. Among the above, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 4,4-dimethylcyclohexyl group are preferred. Additionally, the cycloalkyl group may be optionally substituted.

[0043] The heteroalkyl group is as used herein, and the heteroalkyl group comprises a group formed by substituting one or more carbons in the alkyl group chain 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, a heteroalkyl group having 1 to 10 carbon atoms is preferred, and a heteroalkyl group having 1 to 6 carbon atoms is more preferred. Examples of heteroalkyl groups include methoxymethyl group, ethoxymethyl group, ethoxyethyl group, methylthiomethyl group, ethylthiomethyl group, ethylthioethyl group, methoxymethoxymethyl group, ethoxymethoxymethyl group, ethoxyethoxyethyl group, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, sulfanylmethyl group, sulfanylethyl group, sulfanylpropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermanylmethyl group, trimethylgermanylethyl group, trimethylgermanylisopropyl group, dimethylethylgermanylmethyl group, dimethylisopropylgermanylmethyl group, tert-butyldimethylgermanylmethyl group, triethylgermanylmethyl group, triethylgermanylethyl group, triisopropylgermanylmethyl group, It includes triisopropylgermanylethyl group, trimethylsilylmethyl group, trimethylsilylethyl group, trimethylsilylisopropyl group, triisopropylsilylmethyl group, and triisopropylsilylethyl group. Additionally, heteroalkyl groups may be optionally substituted.

[0044] As used in the text, alkenyl groups include straight-chain olefin groups, branched olefin groups, and cyclic olefin groups. The 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 group, propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group, cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, cycloheptenyl group, cycloheptatrienyl group, cyclooctenyl group. It includes a cyclooctatetraenyl group and a norbornenyl group. Additionally, the alkenyl group may be optionally substituted.

[0045] The alkynyl group includes a straight-chain alkynyl group as used in the text. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, and preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include an ethynyl group, a propynyl group, a propagyl 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, a phenylpropynyl group, etc. In the above, an ethynyl group, a propynyl group, a propagyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, and a phenylethynyl group are preferred. Additionally, an alkynyl group may be optionally substituted.

[0046] Aryl groups or aromatic groups are considered as condensed systems and non-condensed systems as used in the text. An 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 groups, biphenyl groups, terphenyl groups, triphenylene groups, tetraphenylene groups, naphthalene groups, anthracene groups, phenalene groups, phenanthrene groups, fluorene groups, pyrene groups, chrysene groups, perylene groups, and azulene groups, and preferably include phenyl groups, biphenyl groups, terphenyl groups, triphenylene groups, fluorene groups, and naphthalene groups. Examples of non-fusion aryl groups include phenyl group, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl group, m-tolyl group, p-tolyl group, p-(2-phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4''-tertbutyl-p-terphenyl-4-yl, o-cumenyl group, m-coumenyl group, p-coumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, mesitylenyl group, and It contains an m-quaterphenyl group. Additionally, the aryl group may be optionally substituted.

[0047] Heterocyclic groups or heterocyclils, as used herein, consider non-aromatic cyclic groups. 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, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms, and preferred non-aromatic heterocyclic groups having 3 to 7 ring atoms and including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetanyl, tetrahydrofuran, tetrahydropyranyl, dioxolane, dioxane, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholino, piperazinyl, oxecycloheptatriene, thiocycloheptatriene, azacycloheptatriene, and tetrahydrosilol. Additionally, heterocyclic groups may be optionally substituted.

[0048] As used herein, a heteroaryl group comprises a non-fused and fused heteroaromatic group that may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. An isoaryl group also refers to a heteroaryl group. A heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazol, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, Oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazol, quinoline, isoquinoline, synolin, quinazolin, quinoxaline, naphthiridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothienopyridine,It comprises thienodipyridine, benzofuranopyridine, furanodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and preferably comprises dibenzothiophen, dibenzofuran, dibenzoselenophenophen, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine, and aza analogs thereof. Additionally, heteroaryl groups may be optionally substituted.

[0049] The alkoxy group is represented as an -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group, or -O-heterocyclic group as used in the text. Examples and preferred examples of alkyl groups, cycloalkyl groups, heteroalkyl groups, and heterocyclic groups are as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, hexyloxy groups, cyclopropyloxy groups, cyclobutyloxy groups, cyclopentyloxy groups, cyclohexyloxy groups, tetrahydrofuranyloxy groups, tetrahydropyranyloxy groups, methoxypropyloxy groups, ethoxyethyloxy groups, methoxymethyloxy groups, and ethoxymethyloxy groups. Additionally, the alkoxy group may be optionally substituted.

[0050] The aryloxy group is represented as an -O-aryl group or an -O-heteroaryl group as used in the text. Examples and preferred examples of aryl groups and heteroaryl groups are as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy groups and biphenyloxy groups. Additionally, the aryloxy group may be optionally substituted.

[0051] An arylkyl group comprises an alkyl group substituted with an aryl group as used herein. The arylkyl group may be an arylkyl group having 7 to 30 carbon atoms, preferably an arylkyl group having 7 to 20 carbon atoms, and more preferably an arylkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl t-butyl group, α-naphthylmethyl group, 1-α-naphthyl-ethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthyl-ethyl group, 2-β-naphthyl-ethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, It includes o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group. In the above, benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl group are preferred. In addition, Aralkilgi can be arbitrarily substituted.

[0052] The alkylsilyl group comprises a silyl group substituted with an alkyl group as used in the text. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tribubutylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, and methyl-di-t-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0053] The arylsilyl group comprises a silyl group substituted with at least one aryl group as used herein. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl group, phenyldibiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, and diphenyl-t-butylsilyl group. Additionally, the arylsilyl group may be optionally substituted.

[0054] The alkylgermanyl group comprises a germanyl group substituted with an alkyl group as used in the text. The alkylgermanyl group may be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tribubutylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, trit-butylgermanyl, triisobutylgermanyl, dimethylt-butylgermanyl, and methyldi-t-butylgermanyl. Additionally, the alkylgermanyl group may be optionally substituted.

[0055] The arylgermanyl group comprises a germanyl group substituted with at least one aryl or heteroaryl as used in the text. The arylgermanyl group may be an arylgermanyl group having 6 to 30 carbon atoms, preferably an arylgermanyl group having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl group, phenyldibiphenylgermanyl group, diphenylbiphenylgermanyl group, phenyldiethylgermanyl group, diphenylethylgermanyl group, phenyldimethylgermanyl group, diphenylmethylgermanyl group, phenyldiisopropylgermanyl group, diphenylisopropylgermanyl group, diphenylbutylgermanyl group, diphenylisobutylgermanyl group, and diphenyl t-butylgermanyl group. Additionally, the arylgermanyl group may be optionally substituted.

[0056] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f, h]quinoxaline, dibenzo[f, h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Those skilled in the art can easily conceive of other nitrogen analogs of the aza derivatives described above, and all such analogs are determined to be included in the terms described herein.

[0057] In the present invention, unless otherwise defined, where any term from the group consisting of substituted alkyl group, substituted cycloalkyl group, substituted heteroalkyl group, substituted heterocyclic group, substituted aralkyl group, substituted alkoxy group, substituted aryloxy group, substituted alkenyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted alkylgermanyl group, substituted arylgermanyl group, substituted amino group, substituted acyl group, substituted carbonyl group, substituted carboxylic acid group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphino group is used, this refers to an alkyl group, cycloalkyl group, heteroalkyl group, heterocyclic group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, Any one group among heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanyl group, arylgermanyl group, amino group, acyl group, carbonyl group, carboxylic acid group, ester group, sulfinyl group, sulfonyl group and phosphino group, deuterium, halogen, unsubstituted alkyl group having 1-20 carbon atoms, unsubstituted cycloalkyl group having 3-20 ring carbon atoms, unsubstituted heteroalkyl group having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring carbon atoms, unsubstituted aralkyl group having 7-30 carbon atoms, unsubstituted alkoxy group having 1-20 carbon atoms, unsubstituted aryloxy group having 6-30 carbon atoms, unsubstituted alkenyl group having 2-20 carbon atoms, An unsubstituted alkynyl group having 2-20 carbon atoms, an unsubstituted aryl group having 6-30 carbon atoms, an unsubstituted heteroaryl group having 3-30 carbon atoms, an unsubstituted alkylsilyl group having 3-20 carbon atoms, an unsubstituted arylsilyl group having 6-20 carbon atoms, an unsubstituted alkylgermanyl group having 3-20 carbon atoms, an unsubstituted arylgermanyl group having 6-20 carbon atoms,This means that it can be substituted by one or more selected from unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof.

[0058] It should be understood that when a molecular fragment is described as a substituent or connected to another part in other forms, it is named according to whether it is a fragment (e.g., phenyl group, phenylene group, naphthyl group, dibenzofuran group) or the whole molecule (e.g., benzene, naphthalene group, dibenzofuran group). As used in the text, these different ways of specifying substituents or fragment connections are considered the same.

[0059] In the compounds described in this application, hydrogen atoms may be partially or wholly replaced with deuterium. Other elements, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof. Since this improves the efficiency and stability of the device, replacing other stable isotopes in the compounds may be desirable.

[0060] In the compounds mentioned in this application, multiple substitutions represent a range up to the maximum available substitutions, including double substitutions. In the compounds mentioned in this application, if a substituent represents multiple substitutions (including disubstitutions, trisubstitutions, tetrasubstitutions, etc.), it indicates that the substituent may exist at multiple available substitution positions in the linked structure, and the substituents existing at multiple available substitution positions may have the same structure or different structures.

[0061] In the compounds mentioned in the present invention, adjacent substituents in the compounds may not be arbitrarily connected to form a ring unless explicitly limited, for example, that adjacent substituents may be arbitrarily connected to form a ring. In the compounds mentioned in the present invention, the statement that adjacent substituents may be arbitrarily connected to form a ring includes cases where adjacent substituents are connected to form a ring, and also includes cases where adjacent substituents are not connected to form a ring. In cases where adjacent substituents may be arbitrarily connected to form a ring, the formed ring may be a monocyclic ring, a polycyclic ring (including spiro rings, cross-linked rings, and fused rings), an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a heteroaromatic ring. In these expressions, 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.

[0062] The intent of the expression that adjacent substituents can be arbitrarily connected to form a ring is also to consider that two substituents bonded to the same carbon atom are connected to each other by chemical bonds to form a ring, which is exemplified by the following equation:

[0063]

[0064] The intent of the expression that adjacent substituents can be arbitrarily connected to form a ring is also to consider that two substituents bonded to carbon atoms directly connected to each other are connected by chemical bonds to form a ring, which is exemplified by the following equation:

[0065]

[0066] The intention of the expression that adjacent substituents can be arbitrarily connected to form a ring is to consider that two substituents bonded to a more distant carbon atom are connected to each other by chemical bonds to form a ring, which is exemplified by the following equation:

[0067]

[0068] Furthermore, the intent of the expression that adjacent substituents can be arbitrarily connected to form a ring is also to consider that if one of two substituents bonded to carbon atoms directly connected to each other represents hydrogen, the second substituent is bonded to the side where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:

[0069]

[0070] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal a A metal complex comprising is disclosed, wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the ligand L a It has a structure represented by Equation 1, and

[0071]

[0072] Here,

[0073] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0074] W is selected from B, N, or P, either identically or differently, whenever it appears;

[0075] Rings A, C, and D are selected from pentagonal unsaturated carbon rings, aromatic rings having 6-30 carbon atoms, or heteroaromatic rings having 3-30 carbon atoms, respectively, whenever they appear, either identically or differently;

[0076] Ring B is selected from a hetero ring having 5-30 ring atoms;

[0077] R a , R b , R c and R d Each time it appears, it represents a single substitution, multiple substitution, or non-substitution, either identically or differently;

[0078] R a , R b , R c and R d Whenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0079] Adjacent substituent R a , R b , R c and R dIt can be connected arbitrarily to form a ring.

[0080] In this text, R a , R b , R c and R d The fact that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, adjacent substituent R a Between, adjacent substituent R b Between, adjacent substituent R c Between, adjacent substituent R d Between, adjacent substituent R a and R b Between, adjacent substituent R a and R d Between, it means that any one or more of these adjacent substituent groups can be connected to form a ring. It is obvious that these adjacent substituent groups may not all be connected and thus may not form a ring.

[0081] According to one embodiment of the present invention, the metal complex optionally includes other ligands, and the other ligands are the L a It can be arbitrarily connected to form a 3-bed ligand, a 4-bed ligand, a 5-bed ligand, or a 6-bed ligand.

[0082] According to one embodiment of the present invention, the L a In this, ring A, ring C and ring D are selected from aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 3-18 carbon atoms, either identically or differently, whenever they appear; ring B is selected from heteroaromatic rings having 5-18 ring atoms.

[0083] According to one embodiment of the present invention, the L aIn this case, ring A, ring C and ring D are selected from aromatic rings having 6-10 carbon atoms or heteroaromatic rings having 3-10 carbon atoms, which are identical or different whenever they appear; ring B is selected from fused heteroaromatic rings having 8-18 ring atoms.

[0084] In this embodiment, the statement that ring B is selected from a fused heteroaromatic ring having 8 to 18 ring atoms means that ring B is selected from a fused heteroaromatic ring and the fused heteroaromatic ring has 8 to 18 ring atoms. For example, if ring B is selected from an indole ring, it is a fused heteroaromatic ring and has 9 ring atoms. Also, for example, if ring B is selected from an azaindole ring, it is a fused heteroaromatic ring and also has 9 ring atoms.

[0085] According to one embodiment of the present invention, the L a In this case, ring A, ring C and ring D are each independently selected from a benzene ring, pyridine ring, pyrimidine ring, furan ring, thiophene ring, pyrrole ring, imidazole ring, thiazole ring, oxazole ring, pyrazol ring, isothiazol ring, isooxazole ring, naphthalene ring, quinoline ring, isoquinoline ring, naphthalidine ring, benzofuran ring, benzothiophene ring, benzimidazole ring, benzothiazol ring, benzoxazole ring, pyridofuran ring, or pyridothiophene ring; ring B is selected from a pyrrole ring, indole ring, imidazole ring, pyrazol ring, or azaindole ring.

[0086] According to one embodiment of the present invention, the L a In this case, ring A, ring C and ring D are each independently selected from a benzene ring, a naphthalene ring, a pyridine ring, or a pyrimidine ring; ring B is selected from a pyrrole ring, an indole ring, or an azaindole ring.

[0087] According to one embodiment of the present invention, the L a is selected from a structure represented by any one of Equations 2 to 19, and

[0088]

[0089]

[0090] Here,

[0091] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0092] W is selected from B, N, or P, either identically or differently, whenever it appears;

[0093] A1-A4 are N or CR, identical or different, whenever they appear a Selected from;

[0094] B1-B4 are N or CR, identical or different whenever they appear b Selected from;

[0095] C1-C5 appear the same or different N or CR whenever they appear c Selected from;

[0096] D1-D4 are N or CR, identical or different, whenever they appear d Selected from;

[0097] Z3 appears the same or differently as O, S, Se, NR whenever it appears z , CR z R z , SiR z R z or PR z Selected from; two R z If they exist simultaneously, two R's z is identical or different;

[0098] R a , R b , R c , R d and R zWhenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0099] Adjacent substituent R a , R b , R c , R d and R z It can be connected arbitrarily to form a ring.

[0100] According to one embodiment of the present invention, L a is selected from the structure represented by Equation 2, Equation 4, Equation 7, Equation 10, Equation 16, or Equation 17.

[0101] According to one embodiment of the present invention, L ais selected from the structure represented by Equation 2, Equation 4, Equation 10, or Equation 16.

[0102] According to one embodiment of the present invention, in Equations 2 to 19, Z1 is N and Z2 is C.

[0103] According to one embodiment of the present invention, in Equations 2 to 19, Z2 is N and Z1 is C.

[0104] According to one embodiment of the present invention, in Equations 2 to 19, W is N.

[0105] According to one embodiment of the present invention, in the formulas 2 to 19, Z1 is N and D1 and / or D2 is N; or in the formulas 2 to 19, Z2 is N and C1 and / or C2 is N.

[0106] According to one embodiment of the present invention, in the above formulas 2 to 19, Z1 is N and D2 is N; or in the above formulas 2 to 19, Z2 is N and C2 is N.

[0107] According to one embodiment of the present invention, A1-A4 are each independently CR a Selected from, and B1-B4 are each independently CR b Selected from, and C1-C5 are each independently CR c Selected from, and D1-D4 each independently CR d Selected from; R a , R b , R c and R dWhenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0108] Adjacent substituent R a , R b , R c and R d It can be connected arbitrarily to form a ring.

[0109] According to one embodiment of the present invention, A1-A4 are each independently CR a Selected from, and B1-B4 are each independently CR b Selected from, and C1-C5 are each independently CR c Selected from, and D1-D4 each independently CRd Selected from; R a , R b , R c and R d Whenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted 0-20 carbon atoms Selected from the group consisting of amino groups, cyano groups, and combinations thereof;

[0110] Adjacent substituent R a , R b , R c and R d It can be connected arbitrarily to form a ring.

[0111] According to one embodiment of the present invention, A1-A4 are each independently CR a Selected from, and B1-B4 are each independently CR b Selected from, and C1-C5 are each independently CR c Selected from, and D1-D4 each independently CR d Selected from; R a , R b , R c and R dWhenever appearing, is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a cyano group, and combinations thereof, in the same or different ways;

[0112] Adjacent substituent R a , R b , R c and R d It can be connected arbitrarily to form a ring.

[0113] According to one embodiment of the present invention, in Equations 2, 4 to 18, A1-A n At least one of them appears the same or different CR a Selected from, and the above A n ... corresponds to the one with the largest number among the above A1-A4, existing in Equations 2, 4 to 18;

[0114] Or, in Equations 2 to 19, B1-B n At least one of them appears the same or different CR b Selected from; the above B n ... corresponds to the one with the largest number existing in any one of Equations 2 to 19 among the above B1-B4;

[0115] Or, in Equations 2 to 19, C1-C n At least one of them appears the same or different CR c Selected from; the above C n... corresponds to the one with the largest number existing in any one of Equations 2 to 19 among the above C1-C5;

[0116] Or, in Equations 2 to 19, D1-D n At least one of them appears the same or different CR d Selected from; the above D n corresponds to the largest number existing in any one of Equations 2 to 19 among the above D1-D4;

[0117] In addition, the above R a , R b , R c and R d Whenever appearing, deuterium, halogen, cyano group, hydroxyl group, sulfanyl group, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, having 6-20 carbon atoms Selected from the group consisting of a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, and combinations thereof;

[0118] Adjacent substituent R a , R b , R c and R dIt can be connected arbitrarily to form a ring.

[0119] In the text, in the above Equations 2, 4 through 18, A1-A n At least one of them appears the same or different CR a Selected from, and the above A n corresponds to the one with the largest number among A1-A4 above, existing in any one of Equations 2, 4 to 18; for example, in the case of Equation 2, the above A n ... corresponds to A2, which has the largest number among A1-A4 present in Equation 2; that is, in Equation 2, whenever at least one of A1-A2 appears, CR is identical or different a Selected from; also, for example, in the case of Equation 4, the above A n ... corresponds to the largest number A4 among the above A1-A4 existing in Equation 4, that is, in Equation 4, whenever at least one of A1-A4 appears, CR is the same or different a Selected from. Likewise, in the above Equations 2 to 19, B1-B n At least one of them appears the same or different CR b Selected from, and the above B n corresponds to the largest number existing in any one of Equations 2 to 19 among the above B1-B4; for example, in the case of Equation 2, the above B n ... corresponds to the largest number B4 among the above B1-B4 existing in Equation 2, that is, in Equation 2, whenever at least one of B1-B4 appears, CR is the same or different b Selected from; also, for example, in the case of Equation 18, the above B n ... corresponds to B2, the number with the largest value among B1-B4 present in Equation 18; that is, in Equation 18, whenever at least one of B1-B2 appears, CR is identical or different bSelected from. Likewise, in the above Equations 2 to 19, C1-C n At least one of them appears the same or different CR c Selected from, and the above C n corresponds to the largest number existing in any one of Equations 2 to 19 among the above C1-C5; for example, in the case of Equation 2, the above C n ... corresponds to C3, the number with the largest number present in Equation 2 among the above C1-C5; that is, in Equation 2, whenever at least one of C1-C3 appears, CR is identical or different c Selected from; also, for example, in the case of Equation 11, the above C n ... corresponds to the largest numbered C5 among the above C1-C5 present in Equation 11, that is, in Equation 11, whenever at least one of C1-C5 appears, CR is the same or different c Selected from. Likewise, in the above Equations 2 to 19, D1-D n At least one of them appears the same or different CR d Selected from, and the above D n corresponds to the largest number among any one of Equations 2 to 19 among the above D1-D4; for example, in the case of Equation 2, the above D n corresponds to D2, the number with the largest value among D1-D4 present in Equation 2; that is, in Equation 2, whenever at least one of D1-D2 appears, CR is the same or different d Selected from; also, for example, in the case of Equation 7, the above D n corresponds to the largest number D4 among the above D1-D4 present in Equation 7, that is, in Equation 7, CR is identical or different whenever at least one of D1-D4 appears. d It is selected from.

[0120] According to one embodiment of the present invention, in Equations 2, 4 to 18, A1 and / or A2 are the same or different CR whenever they appear a Selected from; or in Equations 2 to 17, whenever at least one of B2 to B4 appears, CR is the same or different b Selected from; or in Equations 18 to 19, B1 and / or B2 is CR b Selected from; or CR identically or differently whenever at least one of C1 to C3 appears in Equations 2 to 19. c Selected from; or in the above Equations 2 to 19, D1 and / or D2 is CR d Selected from; R a , R b , R c and R d Whenever they appear, they are selected from the group consisting of deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, substituted or unsubstituted amino group having 0-20 carbon atoms, and combinations thereof, either identically or differently.

[0121] According to one embodiment of the present invention, in Equations 2, 4 to 18, A1 and / or A2 are the same or different CR whenever they appear aSelected from; or in Equations 2 to 17, whenever at least one of B2 to B4 appears, CR is the same or different b Selected from; or in Equations 18 to 19, B1 and / or B2 is CR b Selected from; or CR identically or differently whenever at least one of C1 to C3 appears in Equations 2 to 19. c Selected from; or in the above Equations 2 to 19, D1 and / or D2 is CR d Selected from; R a , R b , R c and R d Whenever they appear, they are selected from the group consisting of deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, norbornyl group, adamantyl group, trimethylsilyl group, triethylsilyl group, trimethylgermanyl group, phenyl group, pyridine group, triazine group, trifluoromethyl group, methoxy group, dimethylamino group, deuterized methyl group, deuterized ethyl group, deuterized isopropyl group, deuterized isobutyl group, deuterized t-butyl group, deuterized cyclopentyl group, deuterized cyclopentylmethyl group, deuterized cyclohexyl group, deuterized neopentyl group, and combinations thereof, either identically or differently.

[0122] According to one embodiment of the present invention, in Equations 18 to 19, B1 or B2 is CR b Selected from; R b Whenever they appear, they are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic 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, L a L that is the same or different whenever it appears a1 to L a1241 Selected from a group consisting of; the above L a1 to L a1241 Refer to Claim 9 for the specific structure of.

[0124] According to one embodiment of the present invention, the L a1 to L a1241 Hydrogen in the structure can be partially or wholly replaced by deuterium.

[0125] According to one embodiment of the present invention, L a L that is the same or different whenever it appears a1 to L a1287 Selected from a group consisting of; and the above L a1 to L a1241 The specific structure of refers to claim 9, and said L a1242 to L a1287 The structure of is as follows:

[0126]

[0127]

[0128]

[0129] According to one embodiment of the present invention, the L a1 to L a1287 Hydrogen in the structure can be partially or wholly replaced by deuterium.

[0130] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b ) n (L c ) q Equipped with the general formula of;

[0131] Here, the metal M is selected from Ir, Rh, Re, Os, Pt, Au, or Cu; L a , L band L c are respectively a first ligand, a second ligand, and a third ligand coordinating with the metal M; m is selected from 1, 2, or 3; n is selected from 0, 1, or 2; q is selected from 0, 1, or 2; the sum of m+n+q is equal to the oxidation state of the metal M; and when m is equal to 2 or 3, a plurality of L a may be the same or different; if n is equal to 2, two L b may be the same or different; if q is equal to 2, two L c It may be the same or different;

[0132] L a , L b and L c can be arbitrarily connected to form multidentate ligands;

[0133] L b and L c Whenever it appears, it is selected from a group consisting of the following structures, either identically or differently, and

[0134]

[0135] Here,

[0136] R i , R ii and R iii represents a single permutation, multiple permutation, or no permutation, either identically or differently, whenever it appears;

[0137] X a O, S, Se, NR that is the same or different whenever it appears N1 and CR C1 R C2 Selected from a group consisting of;

[0138] X b and X c O, S, Se, and NR appearing identically or differently whenever N2 Selected from a group consisting of;

[0139] R i , Rii , R iii , R N1 , R N2 , R C1 and R C2 Whenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0140] Adjacent substituent R i , R ii , R iii , R N1 , R N2 , R C1 and R C2 It can be connected arbitrarily to form a ring.

[0141] In this embodiment, adjacent substituent Ri , R ii , R iii , R N1 , R N2 , R C1 and R C2 The fact that it can be arbitrarily connected to form a ring is that the above L b , L c In an adjacent group of substituents in the structure, for example, adjacent substituent R i Between, adjacent substituent R ii Between, adjacent substituent R iii Between, adjacent substituent R i and R ii Between, adjacent substituent R ii and R iii Between, adjacent substituent R i and R iii Between, adjacent substituent R i and R N1 Between, adjacent substituent R i and R C1 Between, adjacent substituent R i and R C2 Between, adjacent substituent R ii and R N1 Between, adjacent substituent R iii and R N1 Between, adjacent substituent R ii and R C1 Between, adjacent substituent R ii and R C2 Between, adjacent substituent R iii and R C1 Between, adjacent substituent R iii and R C2 Between, adjacent substituent R i and R N2 Between, adjacent substituent R ii and R N2 Between, and adjacent substituent R C1 and R C2"Between" signifies that any one or more of these substituents can be connected to form a ring. It is self-evident that not all of these substituents may be connected to form a ring.

[0142] In this embodiment, L a , L b and L c can be arbitrarily connected to form multidentate ligands, for example, L a , L b and L c Any two or three of them can be connected to form a tetradentate or hexadentate ligand. It is self-evident that L a , L b and L c They may not all be connected and may not form multidentate ligands.

[0143] According to one embodiment of the present invention, the metal M is selected from Ir, Pt, or Os.

[0144] According to one embodiment of the present invention, the metal M is Ir.

[0145] According to one embodiment of the present invention, L b Whenever it appears, it is selected from the structure below, either identically or differently, and

[0146]

[0147] Here, R1-R7, whenever they appear, are identical or different hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic carbon atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted 3-30 carbon atoms It is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0148] According to one embodiment of the present invention, L b Whenever it appears, it is selected from the structure below, either identically or differently, and

[0149]

[0150] Herein, at least one or two of R1-R3 are selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, or a combination thereof, which appear identically or differently; and / or at least one or two of R4-R6 are selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, or a combination thereof, which appear identically or differently.

[0151] According to one embodiment of the present invention, L b Whenever it appears, it is selected from the structure below, either identically or differently, and

[0152]

[0153] Herein, at least two of R1-R3 are selected from a substituted or unsubstituted alkyl group having 2-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 2-20 carbon atoms, or a combination thereof, whenever they appear, either identically or differently; and / or at least two of R4-R6 are selected from a substituted or unsubstituted alkyl group having 2-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 2-20 carbon atoms, or a combination thereof, whenever they appear, either identically or differently.

[0154] According to one embodiment of the present invention, L c Whenever it appears, it is selected from the structure below, either identically or differently, and

[0155]

[0156] Here, R8-R15 Whenever appearing, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, Selected from the group consisting of a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0157] Adjacent substituent R8-R 15 It can be connected arbitrarily to form a ring.

[0158] In this embodiment, adjacent substituents R8-R 15 The fact that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, substituents R8 and R9, and substituents R9 and R 10 , substituent R 10 and R 11 , substituent R 11 and R 12 , substituent R 12 and R13 , substituent R 13 and R 14 , and substituent R 14 and R 15 , this means that any one or more of these substituents can be connected to form a ring. It is obvious that these substituents may not all be connected to form a ring.

[0159] According to one embodiment of the present invention, L b L that is the same or different whenever it appears b1 to L b322 Selected from a group consisting of; the above L b1 to L b322 Refer to Claim 13 for the specific structure of.

[0160] According to one embodiment of the present invention, the L c L that is the same or different whenever it appears c1 to L c321 Selected from a group consisting of; the above L c1 to L c321 Refer to Claim 13 for the specific structure of.

[0161] According to one embodiment of the present invention, the L c L that is the same or different whenever it appears c1 to L c331 Selected from a group consisting of; and the above L c1 to L c321 The specific structure of refers to Claim 13, and said L c322 to L c331 The structure of is as follows:

[0162]

[0163] According to one embodiment of the present invention, the metal complex is an Ir complex, and Ir(L a )(L b )(L c ), Ir(L a )2(L b ), Ir(La )2(L c ) and Ir(L a )(L c )2 having a structure represented as any one of the two types; and the metal complex is Ir(L a )(L b )(L c If the structure of ) is provided, the above L a is L a1 to L a1241 Selected from any one of the groups consisting of, and the above L b is L b1 to L b322 Selected from any one of the groups consisting of, and the above L c is L c1 to L c321 Any one of the group consisting of is selected from; and said metal complex is Ir(L a )2(L b If the structure of ) is provided, the above L a L that is the same or different whenever it appears a1 to L a1241 Selected from any one or any two types among the group consisting of, and the above L b is L b1 to L b322 Any one of the group consisting of is selected from; and said metal complex is Ir(L a )2(L c If the structure of ) is provided, the above L a L that is the same or different whenever it appears a1 to L a1241 Selected from any one or any two types among the group consisting of, and the above L c is L c1 to L c321 Any one of the group consisting of is selected from; and said metal complex is Ir(L a )(L c If the structure of )2 is provided, the above L a is L a1 to L a1241Selected from any one of the groups consisting of, and the above L c L that is the same or different whenever it appears c1 to L c321 Any one or any two of the group consisting of; optionally, hydrogen in the metal complex structure may be partially or wholly substituted with deuterium.

[0164] According to one embodiment of the present invention, the metal complex is an Ir complex, and Ir(L a )(L b )(L c ), Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a )(L c )2 having a structure represented as any one of the two types; and the metal complex is Ir(L a )(L b )(L c If the structure of ) is provided, the above L a is L a1 to L a1287 Selected from any one of the groups consisting of, and the above L b is L b1 to L b322 Selected from any one of the groups consisting of, and the above L c is L c1 to L c331 Any one of the group consisting of is selected from; and said metal complex is Ir(L a )2(L b If the structure of ) is provided, the above L a L that is the same or different whenever it appears a1 to L a1287 Selected from any one or any two types among the group consisting of, and the above L b is L b1 to L b322 Any one of the group consisting of is selected from; and said metal complex is Ir(La )2(L c If the structure of ) is provided, the above L a L that is the same or different whenever it appears a1 to L a1287 Selected from any one or any two types among the group consisting of, and the above L c is L c1 to L c331 Any one of the group consisting of is selected from; and said metal complex is Ir(L a )(L c If the structure of )2 is provided, the above L a is L a1 to L a1287 Selected from any one of the groups consisting of, and the above L c L that is the same or different whenever it appears c1 to L c331 Any one or any two of the group consisting of; optionally, hydrogen in the metal complex structure may be partially or wholly substituted with deuterium.

[0165] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds 1 to 690, and

[0166] Here, compounds 1 to 538 and compounds 669 to 688 are Ir(L a )2(L b Equipped with the general formula of ), where two L a is identical, and L a and L b Each corresponds to the structures listed in the table below, and

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] Compounds 539 to 668, Compound 689 and Compound 690 are Ir(L a )(L c It has the general formula of )2, where two L c is identical, and L a and L c Each corresponds to the structures listed in the table below.

[0178]

[0179]

[0180]

[0181] According to one embodiment of the present invention, an electroluminescent element is further disclosed, and this

[0182] anode,

[0183] cathode, and

[0184] It includes an organic layer disposed between the anode and the cathode, wherein the organic layer includes one type of metal complex, and the specific structure of the metal complex is as shown in the arbitrary embodiment above.

[0185] According to one embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0186] According to one embodiment of the present invention, the electroluminescent element emits red light.

[0187] According to one embodiment of the present invention, the electroluminescent element emits yellow light.

[0188] According to one embodiment of the present invention, the electroluminescent element emits green light.

[0189] According to one embodiment of the present invention, the electroluminescent element emits white light.

[0190] According to one embodiment of the present invention, in the device, the light-emitting layer further comprises at least one type of host material.

[0191] According to one embodiment of the present invention, in the device, the light-emitting layer further comprises at least two types of host materials.

[0192] According to one embodiment of the present invention, in the element, the at least one host material comprises at least one chemical group selected from the group consisting of a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, a dibenzothiophen group, an azadibenzothiophen group, a dibenzofuran group, an azadibenzofuran group, a dibenzoselenophene group, a triphenylene group, an azatriphenylene group, a fluorene group, a silafluorene group, a naphthyl group, a quinoline group, an isoquinoline group, a quinazolin group, a quinoxaline group, a phenanthrene group, an azaphenanthrene group, and combinations thereof.

[0193] According to one embodiment of the present invention, in the device, the host material may be a standard host material of the prior art, and, for example, may typically include a host material such as the following, but is not limited thereto:

[0194]

[0195]

[0196]

[0197] According to another embodiment of the present invention, a compound composition comprising one type of metal complex is further disclosed, and the specific structure of the metal complex is as shown in the above optional embodiment.

[0198] Combination with other materials

[0199] The material used in a specific layer of the organic light-emitting device described in the present invention may be used in combination with various other materials present in the device. Such combinations of materials are described in detail in paragraph 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and those skilled in the art may readily refer to the literature to identify other materials that may be combined and used.

[0200] In the text, materials that can be used in specific layers of an organic light-emitting device are described as being usable in combination with various other materials present in said device. For example, the light-emitting dopant disclosed in the text may be used in combination with various types of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. Such combinations of materials are described in detail in paragraph 0080-0101 of patent application US2015 / 0349273A1, the entire contents of which are incorporated by reference in the text. Whereby the materials described or mentioned are non-limiting examples of materials that may be used in combination with the compounds disclosed in the text, and those skilled in the art may readily refer to the literature to identify other materials that may be combined and used.

[0201] In the examples of material synthesis, all reactions are carried out under nitrogen protection unless otherwise noted. All reaction solvents are anhydrous and are used as received from commercial sources. The structure of the synthesized product is confirmed and its properties are tested by methods well known to those skilled in the art using one or more types of equipment standard in the art (including, but not limited to, BRUKER’s nuclear magnetic resonance spectrometer, SHIMADZU’s liquid chromatography, liquid chromatograph-mass spectrometry, gas chromatograph-mass spectrometry, differential scanning calorimeter, Shanghai LENGGUANG TECH.’s fluorescence spectrophotometer, Wuhan CORRTEST’s electrochemical workstation, and Anhui BEQ’s sublimation apparatus). In the embodiment of the device, the characteristics of the device are also tested using equipment standard in the field (including, but not limited to, a deposition machine produced by ANGSTROM ENGINEERING, an optical test system and a life test system produced by Suzhou FATAR, an ellipsometer produced by Beijing ELLITOP, etc.) and by methods well known to those skilled in the art. Those skilled in the art are well aware of the use of the equipment, test methods, and other related matters, and can obtain the intrinsic data of the sample reliably and without influence; therefore, the above-mentioned related matters are not further explained herein.

[0202] Material Synthesis Example:

[0203] The method for preparing the compounds of the present invention is not limited, and typical examples include but are not limited to the following compounds, and the synthesis route and method of preparation are as follows:

[0204] Synthesis Example 1: Synthesis of Compound 5

[0205] Step 1: Synthesis of Intermediate 3

[0206]

[0207] Intermediate 1 (2.16 g, 10.9 mmol), Intermediate 2 (3.9 g, 10.9 mmol), Pd(PPh3)4 (624 mg, 0.54 mmol), and Na2CO3 (1.74 g, 16.35 mmol) were added to a 250 mL three-necked flask, followed by the addition of 1,4-dioxane / H2O (44 mL / 11 mL), the mixture was replaced with nitrogen gas, and the reaction was carried out overnight at 80 °C. After confirming that the reaction was complete by TLC, the mixture was cooled to room temperature, diluted with EA, and extracted by adding water. The organic phase was collected, concentrated, and purified by column chromatography to obtain Intermediate 3 (3.94 g, yield 91.9%).

[0208] Step 2: Synthesis of Intermediate 4

[0209]

[0210] Intermediate 3 (3.94 g, 10 mmol) and Cs2CO3 (8.1 g, 25 mmol) are mixed in DMF (100 mL), the mixture is replaced with nitrogen gas, and the reaction is carried out at 135°C for 1 hour. After confirming that the reaction is complete by TLC, the mixture is cooled to room temperature. Water is added to the mixture to precipitate the product, which is then filtered. The filter cake is washed with an appropriate amount of water and PE, and then dried to obtain intermediate 4 (2.6 g, yield 72.9%).

[0211] Step 3: Synthesis of Intermediate 5

[0212]

[0213] Intermediate 4 (2.3g, 6.5mmol), Pd(OAc)2 (72mg, 0.32mmol), PCy 3·HBF4 (tricyclohexylphosphonium tetrafluoroborate, 236 mg, 0.64 mmol) and K2CO3 (1.8 g, 13 mmol) were mixed in DMAc (32 mL), the mixture was replaced with nitrogen gas, and the reaction was carried out at 135°C for 24 hours. After cooling to room temperature, water was added, the mixture was extracted with dichloromethane, concentrated, and then separated by column chromatography to obtain intermediate 5 (720 mg, yield 34.6%).

[0214] Step 4: Synthesis of Iridium Dimer 6

[0215]

[0216] Intermediate 5 (720 mg, 2.2 mmol) and IrCl3*3H2O (282 mg, 0.8 mmol) are mixed with ethoxyethanol (12 mL) and water (4 mL), and after being replaced with nitrogen gas, the mixture is refluxed at 130°C for 24 hours. After the reaction is cooled to room temperature, it is concentrated to obtain a crude product of iridium dimer 6, which is used directly in the next step without the need for further purification.

[0217] Step 5: Synthesis of Compound 5

[0218]

[0219] The iridium dimer 6 obtained in step 4, 3,7-diethyl-3-methyl-4,6-nonandione (270 mg, 1.2 mmol), K2CO3 (552 mg, 4 mmol), and ethoxyethanol (12 mL) were mixed in a 100 mL single-neck flask, the mixture was replaced with nitrogen gas, and the reaction was carried out overnight at 45°C. After checking that the reaction was complete by TLC, the mixture was cooled to room temperature. The reaction mixture was filtered through Celite, and the filter cake was washed with an appropriate amount of EtOH. Then, the crude product was washed with DCM in a 250 mL branched flask, EtOH (about 10 mL) was added to it, and the DCM was removed by rotating at room temperature. When a solid precipitate was observed, it was filtered, the crude product was washed again with an appropriate amount of EtOH, and the crude product was purified by column chromatography to obtain product compound 5 (240 mg, total yield of two steps 28.4%). The product was confirmed to be the target product with a molecular weight of 1056.4.

[0220] Synthesis Example 2: Synthesis of Compound 26

[0221] Step 1: Synthesis of Iridium Dimer 8

[0222]

[0223] Intermediate 7 (45 mg, 0.13 mmol) and IrCl3*3H2O (18 mg, 0.052 mmol) are mixed in ethoxyethanol (3.9 mL) and water (1.3 mL), and after being replaced with nitrogen gas, the mixture is refluxed at 130°C for 24 hours. After the reaction is cooled to room temperature, it is concentrated to obtain a crude product of iridium dimer 8, which is used directly in the next step without the need for further purification.

[0224] Step 2: Synthesis of Compound 26

[0225]

[0226] The iridium dimer 8 obtained by preparation, 3,7-diethyl-3-methyl-4,6-nonandione (18 mg, 0.08 mmol), K2CO3 (36 mg, 0.26 mmol), and ethoxyethanol (4 mL) were mixed in a 100 mL single-neck flask, the mixture was replaced with nitrogen gas, and the reaction was carried out overnight at 45 °C. After confirming that the reaction was complete by TLC, the mixture was cooled to room temperature. The reaction mixture was filtered through Celite, and the filter cake was washed with an appropriate amount of EtOH. The crude product was then washed with DCM in a 250 mL branched flask, and the crude product was subjected to column chromatography to obtain product compound 26 (20 mg, total yield of two steps 35.0%). The product was confirmed to be the target product with a molecular weight of 1100.4.

[0227] Synthesis Example 3: Synthesis of Compound 559

[0228]

[0229] Intermediate 9 (2.6 g, 3.2 mmol), intermediate 10 (1.4 g, 4.8 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were sequentially added to a 250 mL dry round-bottom flask, and the mixture was heated to 100 °C under N2 protection conditions and reacted for 120 h. After the reaction cooled, the mixture was filtered through Celite. The mixture was washed twice with methanol and n-hexane, respectively, and the yellow solid on top of the Celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain compound 559 (1.3 g, yield 44.9%). The product was identified as the target product with a molecular weight of 904.3.

[0230] Synthesis Example 4: Synthesis of Compound 689

[0231]

[0232] Intermediate 11 (2.2 g, 2.3 mmol), intermediate 12 (1.1 g, 3.2 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were sequentially added to a 250 mL dry round-bottom flask and reacted for 120 h at 100 °C under N2 protection conditions. After the reaction cooled, the mixture was filtered through Celite. The mixture was washed twice with methanol and n-hexane, respectively, the yellow solid on top of the Celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain compound 689 (0.4 g, yield 16%). The product was identified as the target product with a molecular weight of 1072.5.

[0233] Synthesis Example 5: Synthesis of Compound 690

[0234]

[0235] Intermediate 9 (1.8 g, 2.2 mmol), intermediate 13 (0.9 g, 2.6 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were sequentially added to a 250 mL dry round-bottom flask and reacted for 120 h at 100 °C under N2 protection conditions. After the reaction cooled, the mixture was filtered through Celite. The mixture was washed twice with methanol and n-hexane, respectively, the yellow solid on top of the Celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain compound 690 (0.9 g, yield 43%). The product was identified as the target product with a molecular weight of 960.4.

[0236] Synthesis Example 6: Synthesis of Compound 35

[0237] Step 1: Synthesis of Iridium Dimer 15

[0238]

[0239] Intermediate 14 (1.22 g, 3.42 mmol) and IrCl3*3H2O (402 mg, 1.14 mmol) are mixed with ethoxyethanol (30 mL) and water (10 mL), and after being replaced with nitrogen gas, the mixture is refluxed at 130°C for 24 hours. After the reaction is cooled to room temperature, it is filtered to obtain iridium dimer 15, which is used directly in the next step without the need for further purification.

[0240] Step 2: Synthesis of Compound 35

[0241]

[0242] The iridium dimer 15 obtained by preparation, 3,7-diethyl-3-methyl-4,6-nonandione (387 mg, 1.71 mmol), K2CO3 (788 mg, 5.7 mmol), and ethoxyethanol (30 mL) were mixed in a 100 mL single-neck flask, the mixture was replaced with nitrogen gas, and the reaction was carried out overnight at 60 °C. After confirming that the reaction was complete by TLC, the mixture was cooled to room temperature. The reaction mixture was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, the crude product was dissolved in DCM, concentrated, filtered, and recrystallized with DCM / MeOH to obtain product compound 35 (360 mg, total yield of 28% in two steps). The product was confirmed to be the target product with a molecular weight of 1128.4.

[0243] Synthesis Example 7: Synthesis of Compound 671

[0244] Step 1: Synthesis of Iridium Dimer 17

[0245]

[0246] Intermediate 16 (74 mg, 0.18 mol) and IrCl3*3H2O (24 mg, 0.07 mmol) are mixed in ethoxyethanol (6 mL) and water (2 mL), and after being replaced with nitrogen gas, the mixture is refluxed at 130°C for 24 hours. After the reaction is cooled to room temperature, it is filtered to obtain iridium dimer 17, which is used directly in the next step without the need for further purification.

[0247] Step 2: Synthesis of Compound 671

[0248]

[0249] The iridium dimer 17 obtained by preparation, 3,7-diethyl-3-methyl-4,6-nonandione (25 mg, 0.11 mmol), K2CO3 (49 mg, 0.35 mmol), and ethoxyethanol (6 mL) were mixed in a 100 mL single-neck flask, the mixture was replaced with nitrogen gas, and the reaction was carried out overnight at 60 °C. After confirming that the reaction was complete by TLC, the mixture was cooled to room temperature. The reaction mixture was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, the crude product was dissolved in DCM, concentrated, filtered, and the filter cake was washed with MeOH. After drying, the product compound 671 (20 mg, total yield of two steps 23%) was obtained. The product was confirmed to be the target product with a molecular weight of 1240.5.

[0250] As will be known to those skilled in the art, the above manufacturing method is merely one exemplary example, and those skilled in the art can obtain the structure of other compounds of the present invention by developing it.

[0251] Through the design of a special ligand structure, the metal complex of the present invention can effectively control the emission wavelength, and the following photoluminescence (PL) data demonstrates this excellent effect of the metal complex of the present invention.

[0252] Spectrum data

[0253] Photoluminescence (PL) spectral data of the compound of the present invention and the comparative compound were measured using a fluorescence spectrophotometer with model number LENGGUANG F98 manufactured by Shanghai LENGGUANG Technology Co., Ltd. Samples of Compound 35 of the present invention and Comparative Compound RD-A were each prepared at a concentration of 3×10 using HPLC-level toluene. -5 After preparing a solution with mol / L, it is excited with light of 500 nm wavelength at room temperature (298 K) and its emission spectrum is measured.

[0254] The structures of compound 35 of the present invention and comparative compound RD-A are as follows:

[0255]

[0256] In the PL spectrum, the maximum emission wavelength of the comparative compound RD-A is 575 nm, but in the PL spectrum, the maximum emission wavelength of the compound 35 of the present invention is 625 nm, thereby realizing red light emission. As can be seen from this, the compounds of the present invention can effectively control the emission wavelength by having a special ligand structure design, and the excellent properties of the metal complex of the present invention have been proven.

[0257] In addition, the compound of the present invention further possesses excellent device performance; therefore, the excellent characteristics of the compound of the present invention in a device are further verified below through device examples.

[0258] Device Example 1.1

[0259] First, a glass substrate equipped with an 80 nm thick indium tin oxide (ITO) anode is cleaned and then treated using oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. Next, the substrate is mounted in a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied approximately 10 -8The layers are sequentially deposited on an ITO anode via thermal vacuum deposition at a rate of 0.02–2 angstroms / second at a vacuum level of Torr. Compound HI is used as the hole injection layer (HIL). Compound HT is used as the hole transport layer (HTL). Compound X-4 is used as the electron blocking layer (EBL). Then, Compound 5 of the present invention is doped into Compound H-1 and Compound SD and co-deposited to be used as an emissive layer (EML, with a weight ratio of Compound H-1, Compound SD, and Compound 5 of the present invention of 80:17:3). Compound H-1 is deposited on the EML to be used as the hole blocking layer (HBL). Compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited on the HBL to be used as the electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is deposited as the electron injection layer, and 120 nm of aluminum is deposited as the cathode. Next, the device is transferred back to a glove box and encapsulated using a glass lid and a desiccant to complete the device.

[0260] Device Example 1.2

[0261] Except for using compounds X-4 and H-12 instead of compounds H-1 and SD in the light-emitting layer (EML) and adjusting the weight ratio of compounds X-4, H-12 and compounds 5 of the present invention to 47:47:6, the method of manufacturing device Example 1.2 is the same as device Example 1.1.

[0262] Device Comparative Example 1.1

[0263] In the light-emitting layer (EML), instead of compound 5 of the present invention, compound RD-A Except for using, the manufacturing method of device Comparative Example 1.1 is the same as that of device Example 1.1.

[0264] Device Comparative Example 1.2

[0265] In the light-emitting layer (EML), instead of compound 5 of the present invention, compound RD-A Except for using, the manufacturing method of device Comparative Example 1.2 is the same as that of device Example 1.2.

[0266] The layer structure and thickness of the device portion are as shown in the table below. Here, layers in which two or more materials are used are obtained by doping different compounds in the weight ratios mentioned therein.

[0267] [Table 1] Structures of some devices in the device examples and comparative examples

[0268]

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

[0270]

[0271] The IVL characteristics of the device were measured. 1000 cd / m² 2 CIE data of the device under the conditions, maximum emission wavelength (λ max Voltage, current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and displayed in Table 2.

[0272] [Table 2] Device Data

[0273]

[0274] discussion:

[0275] As can be seen in Table 2, the device performance of the compound containing multiple fused ring ligands in the present invention exhibits a significant advantage over the device performance of the comparative compound in terms of driving voltage and efficiency, and possesses superior device characteristics in various types of luminescent hosts: Example 1.1 showed significant improvements in CE, PE, and EQE compared to Comparative Example 1.1, with improvements reaching 36%, 44%, and 6%, respectively, and the driving voltage decreased by nearly 6% compared to Comparative Example 1.1; the device performance of Example 1.2 was even better than that of Comparative Example 1.2, with more distinct improvements in CE, PE, and EQE, reaching 64%, 86%, and 20%, respectively, and the driving voltage of Example 1.2 decreased by 12% compared to Comparative Example 1.2. This data comparison indicates that the metal complex of the present invention L a It has been proven that the device possesses excellent characteristics that comprehensively and significantly improve device performance due to the design of a special fusion ring structure of the ligand, and the excellent performance and excellent application prospects of the metal complex of the present invention have been fully realized.

[0276] Device Example 2.1

[0277] Except for using Compound 559 of the present invention instead of Compound 5 of the present invention in the light-emitting layer (EML), the method of manufacturing device Example 2.1 is the same as device Example 1.1.

[0278] Device Example 2.2

[0279] Except for using Compound 559 of the present invention instead of Compound 5 of the present invention in the light-emitting layer (EML), the method of manufacturing device Example 2.2 is the same as device Example 1.2.

[0280] Device Example 2.3

[0281] Except for using compound 689 of the present invention instead of compound 5 of the present invention in the light-emitting layer (EML), the method of manufacturing device Example 2.3 is the same as device Example 1.2.

[0282] Device Example 2.4

[0283] Except for using compound 690 of the present invention instead of compound 5 of the present invention in the light-emitting layer (EML), the method of manufacturing device Example 2.4 is the same as device Example 1.2.

[0284] The layer structure and thickness of the device portion are as shown in the table below. Here, a layer in which two or more materials are used is obtained by doping different compounds in the weight ratios listed therein.

[0285] [Table 3] Partial device structure of the device example

[0286]

[0287] The structure of the new material used in the device is as follows:

[0288]

[0289] The IVL characteristics of the device were measured. 1000 cd / m² 2 CIE data of the device under the conditions, maximum emission wavelength (λ max ), voltage, current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured. These data are recorded and displayed in Table 4.

[0290] [Table 4] Device Data

[0291]

[0292] discussion:

[0293] As can be seen from the device data of Examples 2.1, 2.2, 2.3, and 2.4, by incorporating different types of auxiliary ligands into the compounds of the present invention, the emission wavelength of the device can be successfully controlled to be in the yellow-green emission region, and further, good device performance is provided: the EQE of Examples 2.1, 2.2, 2.3, and 2.4 can reach 21.25%, 24.03%, 23.71%, and 23.12%, respectively, and possesses high device efficiency; furthermore, Examples 2.1 to 2.4 can all achieve low voltage, and in particular, the driving voltage of Examples 2.1, 2.2, and 2.4 is all very low (less than or equal to 2.78 V). It is also worth mentioning that 80 mA / cm² 2 Under current density conditions, the lifetimes (LT97) of Examples 2.1, 2.2, and 2.4 reached long lifetime levels of 112.5h, 257h, and 154h, respectively, which indicates that the metal complex of the present invention is a yellow light and green light material having excellent characteristics.

[0294] In summary, the metal complex of the present invention is L a Excellent device performance has been comprehensively enhanced due to the design of a special fused ring structure of the ligand. Furthermore, the metal complex of the present invention can effectively control the emission wavelength, thereby satisfying the demand for various emission wavelength ranges from green light to red light in OLED devices and fully realizing the excellent application prospects of the metal complex of the present invention.

[0295] It should be understood that the various embodiments described in the text are merely illustrative and are not intended to limit the scope of the invention. Accordingly, it is obvious to those skilled in the art that the claimed invention may include modifications of the specific and preferred embodiments described in the text. Many of the materials and structures described in the text may be replaced with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding the reasons for the operation of the invention are not limiting.

Claims

Claim 1 In metal complexes, Ir(L a )2(L b ) or Ir(L a )(L c Expressed as the general formula of )2, where, L a , L b and L c are each a first ligand, a second ligand, and a third ligand coordinated with the metal M; and a plurality of L a may be the same or different; two L c It may be the same or different; and the above ligand L a is represented by the structure of Equation 1, and Here, Z1 is N and Z2 is C; W is selected from N; ring A is selected from a benzene ring, ring C is selected from a benzene ring or a naphthalene ring; ring B is an indole ring; ring D is a pyridine ring; R a , R b , R c and R d represents a single substitution, multiple substitution, or non-substitution, identical or different whenever it appears;R a , R b , R c and R d Whenever it appears, is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof, either identically or differently; L b Whenever it appears, it is selected from the structure below, either identically or differently: ;Here, X b and X c is selected from O;R i , R ii and R iii represents a single substitution, multiple substitution, or non-substitution, identical or different whenever it appears;R i , R ii and R iii is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof, which appear identically or differently; L c Whenever it appears, it is selected from the structure below, either identically or differently: ;R i and R ii represents a single permutation, multiple permutation, or no permutation, identically or differently, whenever it appears;R i and R ii A metal complex in which, whenever it appears, either identically or differently, it 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 cyclic carbon atoms, and combinations thereof; wherein the substituted alkyl group, the substituted cycloalkyl group, means that any one group among the alkyl group and the cycloalkyl group is substituted by one or more substituents selected from deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, and combinations thereof. Claim 2 In claim 1, the above L a is selected from a structure represented by any one of Equations 2 and 10, and , Here, Z1 is N and Z2 is C; W is selected from N; A1-A2 are identical or different CR whenever they appear a Selected from; B1-B4 are the same or different CR whenever they appear b Selected from; C1-C5 are the same or different whenever they appear CR c Selected from; D1-D2 are the same or different CR whenever they appear d Selected from;R a , R b , R c and R d A metal complex selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 3 In Article 2, L a A metal complex selected from the structure represented by Equation 2. Claim 4 In claim 2, in the above Equations 2 and 10, A1-A2 are each independently CR a Selected from, and B1-B4 are each independently CR b Selected from, and C1-C5 are each independently CR c Selected from, and D1-D2 each independently CR d Selected from; R a , R b , R c and R d A metal complex selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 12 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 5 In claim 2, in the above Equations 2 and 10, A1-A n At least one of them appears the same or different CR a Selected from, and the above A n corresponds to the largest number among the above A1-A2 existing in Equations 2 and 10; or, in Equations 2 and 10, B1-B n At least one of them appears the same or different CR b Selected from; the above B n corresponds to the largest number among B1-B4 above, existing in any one of Equations 2 and 10; or, in Equations 2 and 10, C1-C n At least one of them appears the same or different CR c Selected from; the above C n corresponds to the largest number existing in any one of Equations 2 and 10 among the above C1-C5; or, in Equations 2 and 10, D1-D n At least one of them appears the same or different CR d Selected from; the above D n corresponds to the largest number existing in any one of Equations 2 and 10 among the above D1-D2; and the above R a , R b , R c and R d A metal complex selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 6 In claim 5, in the above Equations 2 and 10, A1 and / or A2 are the same or different whenever they appear CR a Selected from; or in Equations 2 and 10, whenever at least one of B2 to B4 appears, CR is the same or different b Selected from; or in Equations 2 and 10, CR is identical or different whenever at least one of C1 to C3 appears. c Selected from; or in Equation 2, Equation 10, D1 and / or D2 is CR d Selected from; the above R a , R b , R c and R d A metal complex selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 7 In claim 1, the above R a , R b , R c and R d A metal complex selected from the group consisting of deuterium, fluorine, methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, norbornyl group, adamantyl group, trifluoromethyl group, deuterolytic methyl group, deuterolytic ethyl group, deuterolytic isopropyl group, deuterolytic isobutyl group, deuterolytic t-butyl group, deuterolytic cyclopentyl group, deuterolytic cyclopentylmethyl group, deuterolytic cyclohexyl group, deuterolytic neopentyl group, and combinations thereof, appearing identically or differently each time. Claim 8 In Article 1, L a A group consisting of the following structures, identical or different whenever it appears (where L a437 , L a641 and L a642 Metal complexes selected from (excluding): Here, TMS represents a trimethylsilyl group and Ph represents a phenyl group; here, optionally, the L a1 to L a10 , L a15 , L a17 , L a19 , L a24 to L a25 , L a29 to L a38 , L a42 to L a43 , L a45 , L a47 , L a52 to L a63 , L a67 to L a68 , L a70 , L a72 , L a77 to L a88 , L a92 to L a93 , L a95 , L a97 , L a102 to L a113 , L a116 to L a117 , L a119 , L a121 , L a126 to L a137 , L a140 to L a141 , L a143 , L a145 , L a150 to L a161 , L a164 to L a165 , L a167 , L a169 , L a174 to L a185 , L a188 to L a189 , L a191 , L a193 , L a200 to L a209 , L a212 to L a213 , L a215 , L a217 , L a222 to L a226 , L a231 to L a243 , L a245 , L a255 , L a279 , L a295 to L a303 , L a306 , L a308 to L a309 , L a314 , L a318 to L a322 , L a328 to L a336 , L a345 to L a347 , L a354 to L a357 , L a364 to L a371 , L a374 , L a376 to L a391 , L a394 , L a396 to L a405 , L a408 , L a410 to L a419 , L a422 , L a424 to L a433 , L a436 to L a447 , L a450 , L a452 to L a453 , L a473 to L a475 , L a496 to L a503 , L a506 , L a508 to L a519 , L a522 , L a524 to L a533 , L a536 , L a538 to L a539 , L a542 to L a549 , L a552 , L a554 to L a562 , L a565 , L a567 to L a578 , L a581 , L a583 to L a584 , L a587 to L a592 , L a595 , L a598 to L a604 , L a607 , L a610 to L a614 , L a617 , L a620 to L a624 , L a627 , L a630 , L a633 to L a637 , L a640 , L a643 to L a648 , L a651 , L a654 to L a659 , L a662 , L a665 to L a670 , L a673 to L a674 , L a677 to L a681 , L a684 to L a685 , L a688 to L a692 , L a695 to L a696 , L a699 to L a703 , L a707 to L a708 , L a711 to L a715 , L a718 to L a719 , L a722 to L a726 , L a729 to L a735 , L a738 to L a739 , L a742 to L a746 , L a749 to L a750 , L a753 to L a757 , L a760 to L a761 , L a764 to L a768 , L a771 to L a772 , L a775 to L a779 , L a782 to L a783 , L a786 to L a790 , L a793 to L a794 , L a797 to L a801 , L a804 to L a805 , L a810 to L a814 , L a817 , L a820 to L a824 , L a827 to L a828 , L a830 to L a834 , L a837 to L a838 , L a841 to L a845 , L a848 to L a849 , L a852 to L a856 , L a859 to L a860 , L a863 to L a867 , L a870 to L a871 , L a874 to L a877 , L a881 to L a884 , L a888 to L a891 , L a895 to L a896 , L a902 to L a903 , L a909 , L a911 to L a917 , L a1095 , L a1151 to L a1172 , L a1174 to L a1178 , L a1181 to L a1183 , L a1186 to L a1188 , L a1191 to L a1193 , L a1196 , L a1238 , L a1240 , L a1242 to L a1243 , L a1247 to L a1248 , L a1252 to L a1253 , L a1255 , L a1257 to L a1258 , L a1260 , L a1262 to L a1263 , L a1267 to L a1268 , L a1272 to L a1273 , L a1277 to L a1278 and L a1287 In the structure, hydrogen can be partially or wholly replaced by deuterium. Claim 9 In claim 1, R i and R ii A metal complex selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 12 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 10 In Article 1, L b Whenever it appears, it is selected from the structure below, either identically or differently, and Herein, R1-R7 are metal complexes selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, and combinations thereof, which appear identically or differently. Claim 11 A metal complex according to claim 10, wherein at least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, which are the same or different whenever they appear; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, which are the same or different whenever they appear. Claim 12 In Article 1, L c Whenever it appears, it is selected from the structure below, either identically or differently, and Here, R8-R 15 A metal complex selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 13 In Article 8, L b A metal complex selected from the group consisting of the following structures, which are identical or different whenever they appear: Here, L c Whenever it appears, it is selected from a group consisting of the following structures, either identically or differently: Claim 14 In claim 13, optionally, the hydrogen in the metal complex structure may be partially or wholly substituted with deuterium, in a metal complex. Claim 15 In claim 14, the metal complex is compounds 1 to 40, compounds 42, compounds 44, compounds 46, compounds 48, compounds 50 to 51, compounds 53, compounds 55, compounds 57, compounds 59, compounds 61, compounds 63, compounds 65, compounds 67 to 83, compounds 85, compounds 87, compounds 89, compounds 91, compounds 93, compounds 95, compounds 97, compounds 100, compounds 102, compounds 104, compounds 106, compounds 108, compounds 110, compounds 112, compounds 114, compounds 116, compounds 118, compounds 120, compounds 122, compounds 124, compounds 126, compounds 128, compounds 130, compounds 132, compounds 134, compounds 136, compounds 138, Compound 140, Compound 142, Compound 144, Compound 146, Compound 148, Compound 150, Compound 152, Compound 154, Compound 156, Compound 158, Compound 160, Compound 162 to Compound 195, Compound 197, Compound 199, Compound 201, Compound 203, Compound 205, Compound 207, Compound 209, Compounds 211 to 227, Compound 229, Compound 231, Compound 233, Compound 235, Compound 237, Compound 239, Compound 241, Compound 244, Compound 246, Compound 248, Compound 250, Compound 252, Compound 254, Compound 256, Compounds 258 to 322, Compound 324, Compound 326, Compound 328, Compound 330, Compound 332, Compound 334, Compound 336, Compound 338, Compounds 355 to 370, Compound 387, Compound 389, Compound 391, Compound 393, Compound 395, Compound 397, Compound 399, Compound 401, Compounds 403 to 435, Compound 437, Compound 439, Compound 441, Compound 443, Compound 445, Compound 447, Compound 449,Compound 452, Compound 454, Compound 456, Compound 458, Compound 460, Compound 462, Compound 464, Compounds 466 to 483, Compound 485, Compound 487, Compound 489, Compound 491, Compound 493, Compound 495, Compound 497, Compound 500, Compound 502, Compound 504, Compound 506, Compound 508, Compound 510, Compound 512, Compound 514, Compounds 515 to 530, Compounds 539 to 550, Compounds 559 to 564, Compounds 603 to 614, Compounds 623 to 628, Compounds 635 to 646, Compounds 655 to 660, Compounds 671 to 680 and Compounds 689 to A metal complex selected from the group consisting of compound 690: wherein compounds 1 to 40, compounds 42, compounds 44, compounds 46, compounds 48, compounds 50 to 51, compounds 53, compounds 55, compounds 57, compounds 59, compounds 61, compounds 63, compounds 65, compounds 67 to 83, compounds 85, compounds 87, compounds 89, compounds 91, compounds 93, compounds 95, compounds 97, compounds 100, compounds 102, compounds 104, compounds 106, compounds 108, compounds 110, compounds 112, compounds 114, compounds 116, compounds 118, compounds 120, compounds 122, compounds 124, compounds 126, compounds 128, compounds 130, compounds 132, compounds 134, compounds 136, Compound 138, Compound 140, Compound 142, Compound 144, Compound 146, Compound 148, Compound 150, Compound 152, Compound 154, Compound 156, Compound 158, Compound 160, Compound 162 to Compound 195, Compound 197, Compound 199, Compound 201, Compound 203, Compound 205, Compound 207, Compound 209,Compounds 211 to 227, Compound 229, Compound 231, Compound 233, Compound 235, Compound 237, Compound 239, Compound 241, Compound 244, Compound 246, Compound 248, Compound 250, Compound 252, Compound 254, Compound 256, Compounds 258 to 322, Compound 324, Compound 326, Compound 328, Compound 330, Compound 332, Compound 334, Compound 336, Compound 338, Compounds 355 to 370, Compound 387, Compound 389, Compound 391, Compound 393, Compound 395, Compound 397, Compound 399, Compound 401, Compound 403 to 435, Compound 437, Compound 439, Compound 441, Compounds 443, 445, 447, 449, 452, 454, 456, 458, 460, 462, 464, 466 to 483, 485, 487, 489, 491, 493, 495, 497, 500, 502, 504, 506, 508, 510, 512, 514, 515 to 530, and 671 to 680 are Ir(L, a )2(L b It is expressed as a general formula of ), where two L a is identical, and L a and L b Each corresponds to the structures listed in the table below, and Compounds 539 to 550, compounds 559 to 564, compounds 603 to 614, compounds 623 to 628, compounds 635 to 646, compounds 655 to 660 and compounds 689 to 690 are Ir(L a )(L c It is expressed as a general formula of )2, where two L c is identical, and L a and L c Each corresponds to the structures listed in the table below. Claim 16 An electroluminescent device comprising, wherein the device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode, and wherein the organic layer comprises a metal complex according to any one of claims 1 to 15. Claim 17 In claim 16, the organic layer is a light-emitting layer and the metal complex is a light-emitting material in an electroluminescent device. Claim 18 In claim 17, the electroluminescent element is an electroluminescent element that emits red light, yellow light, green light, or white light. Claim 19 In claim 17, the light-emitting layer further comprises at least one type of host material, forming an electroluminescent device. Claim 20 In claim 19, the electroluminescent device comprises at least one chemical group selected from the group consisting of at least one host material, which is a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an indolocarbazole group, a dibenzothiophen group, an azadibenzothiophen group, a dibenzofuran group, an azadibenzofuran group, a dibenzoselenopene group, a triphenylene group, an azatriphenylene group, a fluorene group, a silafluorene group, a naphthalene group, a quinoline group, an isoquinoline group, a quinazolin group, a quinoxaline group, a phenanthrene group, an azaphenanthrene group, and combinations thereof. Claim 21 A compound composition comprising a metal complex according to any one of claims 1 to 15. Claim 22 delete

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