Organic electroluminescent material and device thereof

Abstract

The present invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a series of metal complexes comprising a La ligand having the structure of Formula 1, wherein the La ligand has a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure, and also has a fluorine substituent at a specific position of the 6-membered aza ring, and also has a specific Ar substituent and a fluorine or cyano substituent in the 6-membered-5-membered-6-membered fused ring structure. The metal complex can be used as a light-emitting material for an electroluminescent device. Such novel compounds can be applied to electroluminescent devices to improve the luminescence performance, driving voltage, and efficiency (CE, PE, and EQE) of the device, thereby exhibiting more saturated luminescence and significantly improving the overall performance of the device. The present invention further discloses an organic electroluminescent device comprising the metal complex and a compound composition comprising the metal complex.

Description

Technology Field

[0001] The present invention relates to a compound used in an organic electronic device, for example, an organic light-emitting diode. More specifically, L having the structure of Formula 1 a The invention relates to a metal complex containing a ligand, and to an electroluminescent device and a compound composition containing said metal complex. Background Technology

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic 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 CN111875640A, the following structure A metal complex comprising [unclear text] was disclosed, and additionally an iridium complex having the following structure The application disclosed a metal complex in which a fluorine atom is connected to the 5-position of pyridine in a pyridine-DBX backbone ligand, but the application did not disclose or teach a metal complex in which a specific fluorine substituent is connected to a specific position of pyridine in a pyridine-(6-membered-5-membered-6-membered fused ring) backbone ligand and a specific substituent is attached to a 6-membered-5-membered-6-membered ((6-membered)-(5-membered)-(6-membered)) fused ring structure, and the effect thereof on device performance.

[0009] In US20210054010A1, the following ligand structure: A metal complex comprising is disclosed, wherein rings A and D are independent pentagonal or hexagonal carbon rings or heterorings, and at least one R D is a carbon ring or a heteroring. Additionally, iridium complexes having the following structure: Although disclosed, the application did not disclose or teach that a specific fluorine substituent is connected to a specific position of the six-membered aza ring in a six-membered aza ring-(six-membered-five-six-membered fusion ring) backbone ligand, a metal complex having a specific substituent in a six-membered-five-six-membered fusion ring structure, and the effect thereof on device performance.

[0010] In US20200251666A1, the following ligand structure: A metal complex having [ ] is disclosed, wherein at least one of X1-X8 is selected from C-CN, and additionally, the metal complex has the following structure It was disclosed that it comprises [the element]. When applied to organic electroluminescent devices, the performance and color saturation of the device can be improved, and although it has already reached a relatively high level in the industry, there is still room for improvement. Furthermore, the application did not disclose or teach that a specific fluorine substituent is connected to a specific position of the 6-membered aza-ring in a 6-membered aza-ring (6-membered-5-membered-6-membered fused ring) backbone ligand, a metal complex having a specific substituent in a 6-membered-5-membered-6-membered fused ring structure, and the effect thereof on device performance. The problem to be solved

[0011] To solve at least partially the above problem, the present invention has an L having the structure of Formula 1 a The purpose is to provide a series of metal complexes containing a ligand. The above L a The ligand has a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure, and also has a fluorine substituent at a specific position of the 6-membered aza ring, and has a specific Ar substituent and a fluorine or cyano substituent in the 6-membered-5-membered-6-membered fused ring structure. The metal complex can be used as a light-emitting material for electroluminescent devices. This novel compound can be applied to electroluminescent devices to improve the device's light emission performance, driving voltage, and efficiency (CE, PE, and EQE), thereby exhibiting more saturated light emission and significantly improving the device's overall performance. means of solving the problem

[0012] According to one embodiment of the present invention, a metal M, and a ligand L coordinated with the metal M a A metal complex comprising was disclosed, and L a It has a structure represented by Equation 1,

[0013] ,

[0014] Here,

[0015] Metal M is selected from metals with a relative atomic mass greater than 40, and

[0016] Z is selected from the group consisting of O, S, Se, NR, CRR, SiRR, and GeRR; if two Rs exist simultaneously, the two Rs are identical or different;

[0017] Y1-Y4 are the same or different CR whenever they appear y or selected from N;

[0018] At least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine;

[0019] X1-X8 appear the same or different C, CR whenever they appear x Selected from , CAr or N;

[0020] At least two of X1-X4 are C, one of which is connected to a nitrogen-containing six-membered ring as shown in Formula 1, and the other is connected to a metal through a metal-carbon bond;

[0021] At least one of X1-X8 is CR x Selected from, and the above R x It is a cyano group or fluorine;

[0022] At least one of X1-X8 is selected from CAr;

[0023] Ar has a structure represented by Equation 2, and

[0024] ,

[0025] a is selected from 0, 1, 2, 3, 4, or 5;

[0026] R a1 and R a2 Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0027] Rings Ar1 and Ar2 are selected from aromatic rings having 6 to 30 cyclic atoms, aromatic rings having 5 to 30 cyclic atoms, or combinations thereof, whenever they appear, either identically or differently; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8;

[0028] R, R x , R y , R a1 and R a2 Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0029] "*" indicates the connection position of Equation 2;

[0030] Adjacent substituents R, R x , R y , R a1 and R a2 It can be arbitrarily connected to form a ring;

[0031] In Equation 1 " " indicates a connection with metal M.

[0032] According to another embodiment of the present invention, an electroluminescent device is further disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises a metal complex according to the aforementioned embodiment.

[0033] According to another embodiment of the present invention, a compound composition comprising a metal complex according to the above-described embodiment is further disclosed. Effects of the invention

[0034] The present invention relates to L having the structure of Formula 1 a A series of metal complexes containing ligands were disclosed. The above L a The ligand has a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure, and also has a fluorine substituent at a specific position of the 6-membered aza ring, and also has a specific Ar substituent and a fluorine or cyano substituent in the 6-membered-5-membered-6-membered fused ring structure. The metal complex can be used as a light-emitting material for electroluminescent devices. This novel compound can be applied to electroluminescent devices to improve the device's light emission performance, driving voltage, and efficiency (CE, PE, and EQE), thereby exhibiting more saturated light emission and significantly improving the device's overall performance. Brief explanation of the drawing

[0035] FIG. 1 is a schematic diagram of an organic light-emitting device that may contain the metal complex and compound composition disclosed herein. FIG. 2 is a schematic diagram of another organic light-emitting device that may contain the metal complex and compound composition disclosed herein. Specific details for implementing the invention

[0036] 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 column 6-10 of U.S. Patent US7,279,704B2, the entire contents of which are incorporated by reference into this application.

[0037] Each layer in these layers has more examples. An example is the flexible and transparent substrate-anode combination disclosed in U.S. Patent No. 5,844,363, 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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, 3-D displays, vehicle displays, and taillights.

[0042] The materials and structures described in the text may also be used in other organic electronic devices listed above.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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).

[0047] 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.

[0048] 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 energy gap (ΔES-T) between the singlet and triplet states. Organic co-receptor emitting materials containing nonmetals have the potential to realize these characteristics. The emission from such materials is generally characterized as co-receptor charge transfer (CT) type emission. In these co-receptor type compounds, the spatial separation of the HOMO and LUMO generally generates a small ΔES-T. This state may include the CT state. Generally, co-receptor emitting materials are constructed by linking an electron co-receptor part (e.g., an amino group or a carbazole derivative) with an electron acceptor part (e.g., a six-membered aromatic ring containing N).

[0049] Regarding the definition of substituent terms,

[0050] Halogens or halides—as used in the text—include fluorine, chlorine, bromine, and iodine.

[0051] The alkyl group includes straight-chain alkyl groups and branched alkyl groups as used in the text. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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-diisopropyl1-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.

[0056] 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, naphthyl 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 group, biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-(2-phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4''-tertbutyl group-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, mesityl group, and m-quaterphenyl group. In addition, aryl groups can be arbitrarily substituted.

[0057] As used herein, a heterocyclic or heterocyclile group is considered a non-aromatic cyclic group. A non-aromatic heterocyclic group comprises a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group 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 a preferred non-aromatic heterocyclic group comprises 3 to 7 ring atoms and comprises at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include the oxiranyl group, oxetanyl group, tetrahydrofuran group, tetrahydropyran group, dioxolane group, dioxane group, aziridinyl group, dihydropyrrole group, tetrahydropyrrole group, piperidine group, oxazolidinyl group, morpholino group, piperazinyl group, oxepine group, thiepine group, azepine group, and tetrahydrosilole group. Additionally, heterocyclic groups may be optionally substituted.

[0058] 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 a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. 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 are dibenzothienyl, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothienyl, 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, benzothiazole, quinoline, isoquinoline, cinnoline group, quinazoline, quinoxaline, naphthiridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine group,It comprises a furanodipyridine group, a benzothienopyridine group, a thienodipyridine group, a benzoselenophenopyridine group, and a selenophenodipyridine group, and preferably comprises a dibenzothienyl group, a dibenzofuran group, a dibenzoselenophen group, a carbazole group, an indolocarbazole group, an imidazole group, a pyridine group, a triazine group, a benzimidazole group, a 1,2-azaborane group, a 1,3-azaborane group, a 1,4-azaborane group, a borazine group, and aza analogs thereof. Additionally, a heteroaryl group may be optionally substituted.

[0059] 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 a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a tetrahydrofuranyloxy group, a tetrahydropyranyloxy group, a methoxypropyloxy group, an ethoxyethyloxy group, a methoxymethyloxy group, and an ethoxymethyloxy group. In addition, the alkoxy group can be arbitrarily substituted.

[0060] The aryloxy group is represented as an -O-aryl group or a -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.

[0061] An arylkyl group includes 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 an o-bromobenzyl group, a p-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, a p-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzyl group, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzyl group, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzyl group, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, and a 1-chloro-2-phenylisopropyl group. In the above, a benzyl group, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, and a 2-phenylisopropyl group are preferred. In addition, Aralkilgi can be arbitrarily substituted.

[0062] 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.

[0063] 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, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyl-t-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0064] 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.

[0065] The arylgermanyl group comprises a germanyl group substituted with at least one aryl group or heteroaryl group 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.

[0066] 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.

[0067] 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, and substituted sulfinyl group is used, this refers to alkyl group, cycloalkyl group, heteroalkyl group, heterocyclic group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, Any one group among 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 to 20 carbon atoms, unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl group having 1 to 20 carbon atoms, unsubstituted heterocyclic group having 3 to 20 ring carbon atoms, unsubstituted aralkyl group having 7 to 30 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted alkynyl group having 2 to 20 carbon atoms, An unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, an unsubstituted arylgermanyl group having 6 to 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, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof.

[0068] It must 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, naphthyl group, dibenzofuran group). As used in the text, these different ways of specifying substituents or fragment connections are considered to be the same.

[0069] 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.

[0070] 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.

[0071] 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 condensed 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.

[0072] 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:

[0073]

[0074] 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:

[0075]

[0076] 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 a more distant carbon atom are connected to each other by chemical bonds to form a ring, which is exemplified by the following equation:

[0077]

[0078] 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 adjacent substituents 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:

[0079]

[0080] According to one embodiment of the present invention, a metal M, and a ligand L coordinated with the metal M a A metal complex comprising was disclosed, and L a It has a structure represented by Equation 1,

[0081] ,

[0082] Here,

[0083] Metal M is selected from metals with a relative atomic mass greater than 40, and

[0084] Z is selected from the group consisting of O, S, Se, NR, CRR, SiRR, and GeRR; if two Rs exist simultaneously, the two Rs are identical or different;

[0085] Y1-Y4 are the same or different CR whenever they appear y or selected from N;

[0086] At least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine;

[0087] X1-X8 appear the same or different C, CR whenever they appearx Selected from , CAr or N;

[0088] At least two of X1-X4 are C, and one of the C is connected to a nitrogen-containing six-membered ring as shown in Equation 1 (i.e. (connected via the "#"), another C is connected to the metal via a metal-carbon bond;

[0089] At least one of X1-X8 is CR x Selected from, and the above R x It is a cyano group or fluorine;

[0090] At least one of X1-X8 is selected from CAr;

[0091] Ar has a structure represented by Equation 2, and

[0092] ,

[0093] a is selected from 0, 1, 2, 3, 4, or 5;

[0094] R a1 and R a2 Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0095] Rings Ar1 and Ar2 are selected from aromatic rings having 6 to 30 cyclic atoms, aromatic rings having 5 to 30 cyclic atoms, or combinations thereof, whenever they appear, either identically or differently; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8;

[0096] R, R x , R y , R a1 and R a2Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0097] "*" indicates the connection position of Equation 2;

[0098] Adjacent substituents R, R x , R y , R a1 and R a2 It can be arbitrarily connected to form a ring;

[0099] In Equation 1 " " indicates a connection with metal M.

[0100] In the text, "adjacent substituents R, R x , Ry , R a1 and R a2 "Can be arbitrarily connected to form a ring" means that, among adjacent groups of substituents, for example, between two substituents R, two substituents R x Between, two substituents R y Between, two substituents R a1 Between, two substituents R a2 Between, substituents R and R x Between, substituent R a1 and R a2 Between, substituent R a1 and R x Between, substituent R a2 and R x "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.

[0101] According to one embodiment of the present invention, L a It has a structure represented by one of equations 1a-1f,

[0102]

[0103] Here,

[0104] Z is selected from the group consisting of O, S, Se, NR, CRR, SiRR, and GeRR; if two Rs exist simultaneously, the two Rs are identical or different;

[0105] Y1-Y4 are the same or different CR whenever they appear y or selected from N;

[0106] At least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine;

[0107] In Equations 1a and 1c, X3-X8 are the same or different CR whenever they appear xSelected from , CAr or N;

[0108] In Equations 1b and 1f, X1 and X4-X8 are identical or different whenever they appear CR x Selected from , CAr or N;

[0109] In Equations 1d and 1e, X1-X2 and X5-X8 are identical or different whenever they appear CR x Selected from , CAr or N;

[0110] At least one of X1-X8 is CR x Selected from, and the above R x It is a cyano group or fluorine;

[0111] At least one of X1-X8 is selected from CAr;

[0112] Ar has a structure represented by Equation 2, and

[0113] ,

[0114] a is selected from 0, 1, 2, 3, 4, or 5;

[0115] R a1 and R a2 Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0116] Rings Ar1 and Ar2 are selected from aromatic rings having 6 to 30 cyclic atoms, aromatic rings having 5 to 30 cyclic atoms, or combinations thereof, whenever they appear, either identically or differently; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8;

[0117] R, R x , R y , R a1 and R a2Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0118] "*" indicates the connection position of Equation 2;

[0119] Adjacent substituents R, R x , R y , R a1 and R a2 It can be arbitrarily connected to form a ring;

[0120] In Equations 1a through 1f, " " indicates a connection with metal M.

[0121] In this text, "ring atoms" in aromatic and heteroaromatic rings refer to atoms that constitute the ring itself in a structure in which valence is bonded to a cyclic structure in which the atoms possess aromaticity (e.g., monocyclic (hetero)aromatic rings, fused (hetero)aromatic rings). In the ring, carbon atoms and heteroatoms (including, but not limited to, O, S, N, Se, or Si, etc.) are all counted as ring atoms. If the ring is substituted by a substituent, the atoms contained in the substituent are not included in the number of ring atoms. For example, the number of ring atoms for the phenyl, pyridine, and triazinyl groups is 6, each; the number of ring atoms for fused dithiophene and fused difuran is 8; the number of ring atoms for the benzothienyl and benzofuran groups is 9, each; and the number of ring atoms for the naphthyl, quinoline, isoquinoline, quinazolin, and quinoxaline groups is 10, each; The number of ring atoms in the dibenzothienyl group, dibenzofuran group, fluorene group, azadibenzothienyl group, azadibenzofuran group, and azafluorene group is 13, respectively; the various examples described herein are merely illustrative, and the same inference is made for other cases. In Equation 2, when a is 0, i.e., Ar is It means having a structure represented by, where "the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8" indicates that ring Ar1 has an aromatic or heteroaromatic ring with a total number of ring atoms greater than or equal to 8; and in Equation 2, when a is 1, i.e., Ar is It means having a structure represented by, for example, where ring Ar1 and ring Ar2 are both phenyl groups, and R a1 and R a2 When all are hydrogen, the total number of ring atoms in rings Ar1 and Ar2 is 12; also, for example, rings Ar1 and Ar2 are both phenyl groups, and R a1 All of it is hydrogen, and R a2In the case where is a single substituted phenyl group, the total number of ring atoms in rings Ar1 and Ar2 is 12. In Equation 2, when a is 2, that is, Ar is It means having a structure represented by . In other cases, the same analogy is applied.

[0122] According to one embodiment of the present invention, the metal complex described herein is M(L a ) m (L b ) n (L c ) q Equipped with the general formula of;

[0123] Here,

[0124] Metal M is selected from metals with a relative atomic mass greater than 40, preferably M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt, either identically or differently whenever appearing; more preferably M is selected from Pt or Ir, either identically or differently whenever appearing;

[0125] L a , L b and L c are the first ligand, second ligand, and third ligand, respectively, coordinating with metal M, and L a , L b and L c is identical or different; here, L a , L b and L c can be randomly connected to form multidentate ligands; for example, L a , L b and L c can be randomly connected to form a tetradentate ligand, or L a , L b and L c ... connects to form a six-digit ligand, or L a , L b and L cThe spaces are not all connected and do not form multidentate ligands;

[0126] m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, q is selected from 0, 1, or 2, and the sum of m+n+q is equal to the oxidation state of metal M; if m is greater than or equal to 2, multiple L a are identical or different, and when n is 2, two L b is identical or different; if q is 2, two L c is identical or different;

[0127] L b and L c Whenever it appears, it is selected from a structure represented as any one of the groups consisting of the structures below, identical or different, and

[0128]

[0129] Here,

[0130] R a and R b Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0131] X b O, S, Se, NR that is the same or different whenever it appears N1 , CR C1 R C2 Selected from a group consisting of;

[0132] R a , R b , R c , R N1 , R C1 and R C2Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0133] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 It can be arbitrarily connected to form a ring;

[0134] The above L b and L c to " " indicates a connection with metal M.

[0135] In this text, "adjacent substituent R a , Rb , R c , R N1 , R C1 and R C2 "The statement that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, two substituents R a Between, two substituents R b Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, and substituent R C1 and R C2 Between, it means that any one or more of these substituent groups can be connected to form a ring. It is self-evident that not all of these substituents may be connected to form a ring. For example, the formula For example, two substituents R a The spaces are connected to form a loop, resulting in the following structure: or It can form.

[0136] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m It is equipped with a structure represented by Equation 3, and

[0137]

[0138] Here,

[0139] m is selected from 1, 2, or 3, and if m is 1, two L b is identical or different; if m is 2 or 3, multiple L a is identical or different;

[0140] Z is selected from the group consisting of O, S, Se, NR, CRR, SiRR, and GeRR; if two Rs exist simultaneously, the two Rs are identical or different;

[0141] Y1-Y4 are the same or different CR whenever they appear y or selected from N;

[0142] At least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine;

[0143] X3-X8 CR is the same or different whenever it appears x, CAr or selected from N;

[0144] At least one of X3-X8 is CR x Selected from, and the above R x It is a cyano group or fluorine;

[0145] At least one of X3-X8 is selected from CAr;

[0146] Ar has a structure represented by Equation 2, and

[0147] ,

[0148] a is selected from 0, 1, 2, 3, 4, or 5;

[0149] R a1 and R a2 Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0150] Rings Ar1 and Ar2 are selected from aromatic rings having 6 to 30 cyclic atoms, aromatic rings having 5 to 30 cyclic atoms, or combinations thereof, whenever they appear, either identically or differently; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8;

[0151] R, R x , R y , R a1 , R a2 and R1-R8, whenever they appear, are identical or different 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 to 20 carbon atoms Selected from the group consisting of alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0152] Adjacent substituents R, R x , R y , R a1 and R a2 It can be arbitrarily connected to form a ring;

[0153] Adjacent substituents R1-R8 can be arbitrarily connected to form a ring.

[0154] In this text, "adjacent R1-R8 can be arbitrarily connected to form a ring" means that any one or more groups of any two adjacent substituents among R1-R8 can be connected to form a ring. It is obvious that none of these substituents may be connected and thus not form a ring.

[0155] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m It has a structure represented by formula 3a or 3b, and

[0156]

[0157] Here,

[0158] m is selected from 1, 2, or 3, and if m is 1, two L b is identical or different; if m is 2 or 3, multiple L a is identical or different;

[0159] R x , R y and Ar represent a single substitution, multiple substitution, or no substitution, either identically or differently, whenever they appear;

[0160] Ar has a structure represented by Equation 2, and

[0161] ,

[0162] a is selected from 0, 1, 2, 3, 4, or 5;

[0163] R a1 and R a2 Whenever it appears, it represents a single permutation, multiple permutation, or no permutation, either identically or differently;

[0164] Rings Ar1 and Ar2 are selected from aromatic rings having 6 to 30 cyclic atoms, aromatic rings having 5 to 30 cyclic atoms, or combinations thereof, whenever they appear, either identically or differently; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8;

[0165] R x , R y , R a1 , R a2 and R1-R8, whenever they appear, are identical or different 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 to 20 carbon atoms Selected from the group consisting of alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0166] Adjacent substituent R x , R y , R a1 and R a2 It can be arbitrarily connected to form a ring;

[0167] Adjacent substituents R1-R8 can be arbitrarily connected to form a ring.

[0168] In this text, "adjacent substituent R x , R y , R a1 and R a2 "The statement that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, two substituents R x Between, two substituents R y Between, two substituents R a1 Between, two substituents R a2 Between, substituent R a1 and R a2 Between, substituent R a1 and R x Between, substituent R a2 and R x "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.

[0169] According to one embodiment of the present invention, where Z is selected from the group consisting of O and S.

[0170] According to one embodiment of the present invention, where Z is selected from O.

[0171] According to one embodiment of the present invention, where a is selected from 0, 1, 2 or 3.

[0172] According to one embodiment of the present invention, here, a is 1.

[0173] According to one embodiment of the present invention, where Y1-Y4 are CR that are the same or different each time they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; the remainder is R yWhenever they appear, they are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 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, either identically or differently.

[0174] In this text, "remainder R y "is Y2 and / or Y3 in Y1-Y4 CR y Selected from and R y go Fluorine R y In addition, the rest in Y1-Y4 are also CR y R when selected in y It means. The following case: 1) Y2 is CR y Selected from and R y If α is fluorine, "the remaining R y "is at least one of Y1, Y3, and Y4 CR y The above R when selected from y Meaning of; 2) Y3 is CR y Selected from and R y If α is fluorine, "the remaining R y "is at least one of Y1, Y2, and Y4 CR y The above R when selected from y Meaning of; 3) Y2 and Y3 are CR y Selected from and R y If it is fluorine, "the remaining R y "is at least one of Y1 and Y4 CR y The above R when selected from y Meaning of; includes.

[0175] According to one embodiment of the present invention, where Y1-Y4 are CR that are the same or different each time they appear y Selected from; at least one of Y2 and Y3 is CR ySelected from, and the above R y go It is fluorine; the remainder is R y Whenever it appears, it is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, and combinations thereof, either identically or differently.

[0176] According to one embodiment of the present invention, where Y1-Y4 are CR that are the same or different each time they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y go It is fluorine; the remainder is R y The group is selected from hydrogen, deuterium, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, t-amyl group, or a combination thereof; optionally, the hydrogen in the group is partially or wholly substituted by deuterium.

[0177] According to one embodiment of the present invention, where at least one of Y2 and Y3 is CR y Selected from, and the above R y go It is fluorine; at least one of Y1-Y4 is CR y Selected from, R y It is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0178] According to one embodiment of the present invention, where Y2 and Y3 are CR y Selected from, and one of the above R y silver It is fluorine; and the above R of the other one among them y It is selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof.

[0179] According to one embodiment of the present invention, where Y2 and Y3 are CR y Selected from, and one of the above R y silver It is fluorine; and the above R of the other one among them y It is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, and combinations thereof.

[0180] According to one embodiment of the present invention, where Y2 and Y3 are CR y Selected from, and one of the above R y silver It is fluorine; and the above R of the other one among them y It is selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, neopentyl group, cyclopentyl group, cyclohexyl group, deuterized methyl group, deuterized ethyl group, deuterized propyl group, deuterized isopropyl group, deuterized n-butyl group, deuterized isobutyl group, deuterized t-butyl group, deuterized neopentyl group, deuterized cyclopentyl group, deuterized cyclohexyl group, and trimethylsilyl group.

[0181] According to one embodiment of the present invention, where Y1-Y4 are CR that are the same or different each time they appear yOr selected from N; at least one of Y1-Y4 is selected from N; for example, one of Y1-Y4 is selected from N or two are selected from N.

[0182] According to one embodiment of the present invention, where X1-X8 are C, CR, which are the same or different each time they appear x , CAr Or selected from N; at least one of X1-X8 is selected from N; for example, one of X1-X8 is selected from N or two are selected from N.

[0183] According to one embodiment of the present invention, where X3-X8 are CR identical or different each time they appear x , CAr Or selected from N; at least one of X3-X8 is selected from N; for example, one of X3-X8 is selected from N or two are selected from N.

[0184] According to one embodiment of the present invention, where X3-X8 are CR identical or different each time they appear x or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R x Whenever they appear, they are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and combinations thereof, either identically or differently.

[0185] According to one embodiment of the present invention, where X3-X8 are CR identical or different each time they appearx or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R x Whenever they appear, they are selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof, either identically or differently.

[0186] In this text, "remainder R x "is selected from CAr at least one of X3-X8, and plural is CR x If selected from, at least one of R x is a cyano group or fluorine, and R is selected from cyano groups or fluorine. x Other R x that is, "the remainder R x It is called ". For example, X7 is CR x Selected from and the above R x A is a cyano group or fluorine, X8 is selected from CAr, and at least one of X3-X6 is CR x If selected from, CR among X3-X6 x The above R selected from x that is, "the remainder R x It is called.

[0187] According to one embodiment of the present invention, where X3-X8 are CR identical or different each time they appear x or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R xWhenever it appears, it is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, and combinations thereof, either identically or differently.

[0188] According to one embodiment of the present invention, wherein at least one of X3-X8 is CR x Selected from; the above R x It is a cyano group or fluorine, and at least one of X3-X8 is selected from CAr.

[0189] According to one embodiment of the present invention, wherein at least one of X5-X8 is CR x Selected from; the above R x It is a cyano group or fluorine, and at least one of X5-X8 is selected from CAr.

[0190] According to one embodiment of the present invention, where one of X7 and X8 is CR x Selected from; the above R x It is a cyano group or fluorine, and the other one of X7 and X8 is selected from CAr.

[0191] According to one embodiment of the present invention, where X7 is CR x Selected from; the above R x It is selected from cyano groups or fluorine; X8 is selected from CAr.

[0192] According to one embodiment of the present invention, where, R a1 and R a2Whenever they appear, they are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof, either identically or differently.

[0193] According to one embodiment of the present invention, where, R a1 and R a2 Whenever they appear, they are selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 15 carbon atoms, and combinations thereof, either identically or differently.

[0194] According to one embodiment of the present invention, where, R a1 and R a2 Whenever it appears, it is selected from the group consisting of hydrogen, deuterium, fluorine, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, neopentyl group, cyclopentyl group, cyclohexyl group, phenyl group, pyridine group, trimethylsilyl group, and combinations thereof, either identically or differently; optionally, hydrogen in the group may be partially or wholly substituted by deuterium.

[0195] According to one embodiment of the present invention, the ring Ar1 and the ring Ar2 are selected from a benzene ring, a heteroaromatic ring having five or six ring atoms, or a combination thereof, whichever appears identically or differently.

[0196] According to one embodiment of the present invention, the ring Ar1 and the ring Ar2 are selected from a benzene ring or a heteroaromatic ring having six ring atoms, whichever appears differently.

[0197] According to one embodiment of the present invention, ring Ar1 and ring Ar2 are selected from the benzene ring, either identically or differently, whenever they appear.

[0198] According to one embodiment of the present invention, the ring Ar1 and ring Ar2 are selected from an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof, which may appear identically or differently; and the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.

[0199] According to one embodiment of the present invention, ring Ar1 and ring Ar2 are selected from the group consisting of a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, a phenanthrene ring, anthracene ring, a fluorene ring, a silafluorene ring, a quinoline ring, an isoquinoline ring, a fused dithiophene ring, a fused difuran ring, a benzofuran ring, a benzothiophen ring, a dibenzofuran ring, a dibenzothiophen ring, a triphenylene ring, a carbazole ring, an azacarbazole ring, an azafluorene ring, an azasilafluorene ring, an azadibenzofuran ring, an azadibenzothiophen ring, and combinations thereof, in which case they appear identically or differently; the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30; optionally, hydrogen in the group may be partially or wholly substituted with deuterium.

[0200] According to one embodiment of the present invention, in Ar, the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 24.

[0201] According to one embodiment of the present invention, in Ar, the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 18.

[0202] According to one embodiment of the present invention, Ar appears the same or different each time.

[0203]

[0204]

[0205]

[0206]

[0207] and selected from a group consisting of combinations thereof;

[0208] Optionally, hydrogen in the above group may be partially or wholly substituted by deuterium; where "*" indicates the connection position of the Ar.

[0209] According to one embodiment of the present invention, at least one or at least two of R1-R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total sum of the number of carbon atoms of all R1-R4 and / or R5-R8 is at least 4.

[0210] According to one embodiment of the present invention, at least one or at least two of R1-R4 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total number of carbon atoms of all R1-R4 is at least 4.

[0211] According to one embodiment of the present invention, at least one or at least two of R5-R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total number of carbon atoms of all R5-R8 is at least 4.

[0212] According to one embodiment of the present invention, wherein at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, 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.

[0213] According to one embodiment of the present invention, wherein at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, 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.

[0214] According to one embodiment of the present invention, wherein at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group, neopentyl group, t-amyl group, and combinations thereof; optionally, hydrogen in said group may be partially or wholly substituted by deuterium.

[0215] According to one embodiment of the present invention, here, L a L is the same or different whenever it appearsa1 to L a879 It is selected from a group consisting of, where L a1 to L a879 Refer to Claim 17 for the specific structure of.

[0216] According to one embodiment of the present invention, here, L a1 to L a879 Hydrogen atoms in it can be partially or wholly replaced by deuterium.

[0217] According to one embodiment of the present invention, here, L b L is the same or different whenever it appears b1 to L b334 It is selected from a group consisting of, where L b1 to L b334 Refer to claim 18 for the specific structure of.

[0218] According to one embodiment of the present invention, here, L b1 to L b334 Hydrogen atoms in it can be partially or wholly replaced by deuterium.

[0219] According to one embodiment of the present invention, here, L c Whenever it appears, it is selected from a group consisting of the following structures, either identically or differently.

[0220]

[0221]

[0222]

[0223] According to one embodiment of the present invention, the metal complex is Ir(L a )3, IrL a (L b )2, Ir(L a )2L b , Ir(L a )2L c , IrL a (L c )2 or IrL a L bL c It has the structure of, where ligand L a L is the same or different whenever it appears a1 to L a879 Selected from any one, any two, or any three of the group consisting of, and ligand L b L is the same or different whenever it appears b1 to L b334 Selected from any one or any two of the group consisting of, and ligand L c L is the same or different whenever it appears c1 to L c50 It is selected from any one or any two of the groups consisting of.

[0224] According to one embodiment of the present invention, the metal complex is IrL a (L b It has the structure of )2, and two L b is identical or different, and ligand L a L is the same or different whenever it appears a1 to L a879 Selected from any one of the group consisting of, and ligand L b L is the same or different whenever it appears b1 to L b334 It is selected from any one or any two of the groups consisting of.

[0225] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 396, wherein the specific structure of metal complex 1 to metal complex 396 is referenced in claim 19.

[0226] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises a metal complex according to any of the aforementioned embodiments.

[0227] According to one embodiment of the present invention, the organic layer comprising the metal complex is a light-emitting layer.

[0228] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound.

[0229] According to one embodiment of the present invention, the light-emitting layer additionally comprises a second host compound.

[0230] According to one embodiment of the present invention, at least one of the host compounds 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 indolocarbazole group, a dibenzothienyl group, an azadibenzothienyl 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.

[0231] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 4, and

[0232] ,

[0233] Here,

[0234] E1-E6 are C, CR, identical or different whenever they appear e Or selected from N, at least two of E1-E6 are N, at least one of E1-E6 is C, and connected to Equation 5;

[0235] ,

[0236] Here,

[0237] Q is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR", either identically or differently whenever it appears; if two R"s exist simultaneously, the two R"s may be identical or different;

[0238] P is 0 or 1, and r is 0 or 1;

[0239] If Q is selected from N, p is 0 and r is 1;

[0240] If Q is selected from the group consisting of O, S, Se, NR", CR"R", SiR"R", GeR"R" and R"C=CR", then p is 1 and r is 0;

[0241] L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, which may appear identically or differently;

[0242] Q1-Q8 are C, CR, identical or different whenever they appear q or selected from N;

[0243] "*" indicates the connection location between Equation 5 and Equation 4;

[0244] R e , R" and R qWhenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0245] Adjacent substituent R e , R" and R q It can be connected arbitrarily to form a ring.

[0246] In this text, "adjacent substituent R e , R" and R q "The statement that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, two substituents R e Between, two substituents R" Between, two substituents R q Between, substituents R" and Rq "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.

[0247] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 4a or 4b,

[0248]

[0249] Here, in Equation 4a or Equation 4b,

[0250] Q is selected from the group consisting of O, S, Se, NR", CR"R" and SiR"R", GeR"R" and R"C=CR", either identically or differently whenever it appears; if two R"s exist simultaneously, the two R"s may be identical or different;

[0251] L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, which may appear identically or differently;

[0252] Q1-Q8 are C, CR, identical or different whenever they appear q or selected from N;

[0253] R" and R qWhenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, 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;

[0254] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof, which may appear identically or differently;

[0255] Preferably, Ar3 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazole group, or a combination thereof;

[0256] Adjacent substituents R", R q It can be connected arbitrarily to form a ring.

[0257] In this text, "adjacent substituent R", R q "Can be arbitrarily connected to form a ring" means that, among adjacent substituent groups, for example, between two substituents R", two substituents R q Between, substituents R" and R q "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.

[0258] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 6 or Formula 7,

[0259]

[0260] Here,

[0261] G appears the same or differently whenever C(R g )2, NR g Selected from , O or S;

[0262] L TWhenever it appears, it is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, either identically or differently;

[0263] T appears the same or differently C, CR whenever it appears t or selected from N;

[0264] R t , R g Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, Selected from the group consisting of a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0265] Ar4 is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof, which may appear identically or differently;

[0266] In Equation 6, adjacent substituent R t , R g It can be arbitrarily connected to form a loop;

[0267] In Equation 7, adjacent substituent R t It can be connected arbitrarily to form a ring.

[0268] According to one embodiment of the present invention, the second host compound has a structure represented by one of Formulas 6-a to 6-f and Formulas 7-a to 7-j, and

[0269]

[0270]

[0271] Here, in Equations 6-a to 6-f, T, G, L T , Ar4 has the same definition as in Equation 6;

[0272] Here, in Equations 7-a to 7-j, T, L T , Ar4 has the same definition as in Equation 7.

[0273] In this text, "adjacent substituent R t "Can be arbitrarily connected to form a ring" means that any two adjacent substituents R among them t "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.

[0274] In this text, "adjacent substituent R t , R g"The statement that they can be arbitrarily connected to form a ring means that, among adjacent substituent groups, for example, two substituents R t Between, two substituents R g Between, substituent R t and R g "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.

[0275] According to one embodiment of the present invention, the metal complex in the electroluminescent device is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0276] According to one embodiment of the present invention, the metal complex in the electroluminescent device is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.

[0277] According to another embodiment of the present invention, a compound composition comprising a metal complex according to any one of the aforementioned embodiments is disclosed.

[0278] Combination with other materials

[0279] 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 paragraphs 0132–0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. Whereby the materials described or mentioned 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.

[0280] In the text, materials that can be used in specific layers of an organic light-emitting diode are described as being usable in combination with various other materials present in the device. For example, the compounds disclosed in the text may be used in combination with various hosts, dopants, 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 can readily refer to the literature to identify other materials that may be combined and used.

[0281] In the examples of material synthesis, all reactions are carried out under nitrogen gas 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.

[0282] Material Synthesis Example:

[0283] The method for preparing the compound of the present invention is not limited to the following, but is a typical example, and is not limited thereto, and its synthesis route and method of preparation are as follows.

[0284] Synthesis Example 1: Synthesis of Metal Complex 134

[0285] Step 1:

[0286]

[0287] Intermediate 1 (15g, 60.7mmol), B2pin2 (16.9g, 66.8mmol), Pd(OAc)2 (0.41g, 1.8mmol), Xphos (1.7g, 3.6mmol), KOAc (8.9g, 91mmol), and dioxane (300mL) were added sequentially to a dry round-bottom flask of 1000mL, and the reaction was carried out for 12 hours under N2 protection while heating until reflux was reached, and the reaction mixture was cooled to obtain the crude product of intermediate 2, and the subsequent reaction was carried out directly.

[0288] Step 2:

[0289]

[0290] 2-chloro-4-fluoro-5-methylpicoline (9.9 g, 67.9 mmol), Pd(dppf)Cl2 (1.78 g, 2.4 mmol), K2CO3 (12.6 g, 91 mmol), and water (100 mL) are added to the crude product of Step 1. The reaction is carried out for 12 hours under N2 protection while heating until reflux occurs. After cooling, the mixture is extracted with DCM, the organic phase is collected, the solvent is removed by vacuum rotation, and the mixture is purified by column chromatography to obtain intermediate 3 (15.7 g, 85.8% yield).

[0291] Step 3:

[0292]

[0293] In a 250 mL dry round-bottom flask, intermediate 3 (15.7 g, 51 mmol), potassium tert-butoxide (0.58 g, 5.2 mmol), and DMSO- d6 (90 mL) is added, and the reaction is carried out overnight by heating to 100°C under N2 protection. After the reaction mixture has completely cooled, DCM and saturated saline solution are added for extraction, the organic phase is collected, the solvent is removed by vacuum rotation, and the product is purified by column chromatography to obtain intermediate 4 (8.2 g, yield 52.6%).

[0294] Step 4:

[0295]

[0296] Intermediate 4 (4.4 g, 14.4 mmol) is sequentially added to a 500 mL dry round-bottom flask, dissolved by adding 150 mL of THF, the temperature is lowered to -78 °C, LDA (8.7 mL, 17.3 mmol) is added and reacted for 1.5 h, ZnCl2 (10.8 mL, 10.8 mmol) is added and reacted for 0.5 h. Additionally, Pd(OAc)2 (0.13 g, 0.58 mmol), Sphos (0.47 g, 1.1 mmol), and 4-iodo-1,1'-biphenyl (3.82 g, 18.7 mmol) are added. The reaction mixture is heated to room temperature and reacted overnight. After the reaction is complete, a saturated aqueous ammonium chloride solution is added and quenched, and the organic phase is collected by extraction with EA, the solvent is removed by vacuum rotation, and the product is purified by column chromatography to obtain intermediate 5 (3.0 g, yield 45.6%).

[0297] Step 5:

[0298]

[0299] Intermediate 5 (2.2 g, 4.8 mmol), iridium complex (3.0 g, 3.7 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 95 °C under N2 protection and reacted for 144 h. After the reaction mixture was cooled, it was filtered through Celite. The yellow solid on the Celite was washed twice each with methanol and n-hexane, dissolved in dichloromethane to collect the organic phase, the solvent was removed by vacuum rotation, and purified by column chromatography to obtain the yellow solid metal complex 134 (0.64 g, yield 16.2%). The structure of the product was confirmed to be the target product with a molecular weight of 1069.4.

[0300] Synthesis Example 2: Synthesis of Metal Complex 150

[0301] Step 1:

[0302]

[0303] 2-chloro-4-deuteromethyl-5-fluoropyridine (2.6 g, 17.8 mmol), Pd(dppf)Cl2 (0.47 g, 0.6 mmol), K2CO3 (3.4 g, 24.3 mmol), and water (20 ml) are added to the crude product of intermediate 2. The reaction is carried out for 12 hours under N2 protection while heating until reflux occurs. After cooling, the mixture is extracted with DCM, the organic phase is collected, the solvent is removed by vacuum rotation, and the product is purified by column chromatography to obtain intermediate 6 (3.44 g, yield 69.6%).

[0304] Step 2:

[0305]

[0306] Intermediate 6 (3.44 g, 11.3 mmol) is sequentially added to a 500 mL dry round-bottom flask, dissolved by adding 200 mL of THF, the temperature is lowered to -78 °C, LDA (8.5 mL, 8.5 mmol) is added and reacted for 1.5 h, ZnCl2 (6.8 mL, 13.5 mmol) is added and reacted for 0.5 h. Additionally, Pd(OAc)2 (0.10 g, 0.45 mmol), Sphos (0.37 g, 0.90 mmol), and 4-iodo-1,1'-biphenyl (4.1 g, 14.7 mmol) are added. The reaction mixture is heated to room temperature and reacted overnight. After the reaction is complete, a saturated aqueous ammonium chloride solution is added and quenched, and the organic phase is collected by extraction with EA, the solvent is removed by vacuum rotation, and the product is purified by column chromatography to obtain intermediate 7 (2.1 g, yield 41.1%).

[0307] Step 3:

[0308]

[0309] Intermediate 7 (1.2 g, 2.6 mmol), iridium complex (2.0 g, 2.4 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 95 °C under N2 protection and reacted for 144 h. After the reaction mixture was cooled, it was filtered through Celite. The yellow solid on the Celite was washed twice each with methanol and n-hexane, dissolved in dichloromethane to collect the organic phase, the solvent was removed by vacuum rotation, and purified by column chromatography to obtain the yellow solid metal complex 150 (0.21 g, yield 8.2%). The structure of the product was confirmed to be the target product with a molecular weight of 1069.4.

[0310] 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 modifying it.

[0311] Device Example 1

[0312] 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 -8 The materials are sequentially deposited onto an ITO anode via thermal vacuum deposition at a rate of 0.2–2 angstroms / second under a vacuum of Torr. Compound HI is used as the hole injection layer (HIL). Compound HT is used as the hole transport layer (HTL). Compound H1 is used as the electron blocking layer (EBL). Then, the metal complex 134 of the present invention is doped into Compound H1 and Compound H2 and co-deposited to be used as the emissive layer (EML). Compound H3 is deposited on the EML as the hole blocking layer (HBL). Next, Compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited to be used as the electron transport layer (ETL). Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) is deposited to serve as the electron injection layer, and 120 nm of aluminum is deposited to serve as the cathode. Next, the component is transferred back to the glove box, and the component is completed by encapsulating it using a glass lid.

[0313] Device Example 2

[0314] Except for using metal complex 150 instead of metal complex 134 of the present invention in the light-emitting layer (EML), the method of implementation of device Example 2 is the same as that of device Example 1.

[0315] Device Comparison Example 1

[0316] Except for using compound GD1 instead of the metal complex 134 of the present invention in the light-emitting layer (EML), the method of implementation of device Comparative Example 1 is the same as device Example 1.

[0317] Device Comparison Example 2

[0318] Except for using compound GD2 instead of the metal complex 134 of the present invention in the light-emitting layer (EML), the method of implementation of device Comparative Example 2 is the same as device Example 1.

[0319] Device Comparison Example 3

[0320] Except for using compound GD3 instead of the metal complex 134 of the present invention in the light-emitting layer (EML), the method of implementation of device Comparative Example 3 is the same as device Example 1.

[0321] The detailed device layer structure and thickness are as shown in the table below. Layers in which two or more materials are used are obtained by doping different compounds in the weight ratios mentioned therein.

[0322] [Table 1] Device structures of Device Examples 1 to 2 and Comparative Examples 1 to 3

[0323]

[0324] The material structure used in the device is as follows:

[0325]

[0326]

[0327] The IVL characteristics of the device were measured. 1000 cd / m² 2 CIE data of the device under these conditions, maximum emission wavelength λ max Full Width at Half (FWHM), Voltage (V), Current Efficiency (CE), Power Efficiency (PE), and External Quantum Efficiency (EQE) were measured. These data are recorded and displayed in Table 2.

[0328] [Table 2] Device data of Device Examples 1 to 2 and Comparative Examples 1 to 3

[0329]

[0330] discussion:

[0331] Table 2 displays the device performance of the metal complex of the present invention and the comparative metal complex. When comparing Example 1 and Example 2 with Comparative Example 1, the light-emitting materials used in the device are the metal complex 134 and metal complex 150 of the present invention, and the metal complex GD1 that is not a metal complex of the present invention, respectively, and the main difference is L a The difference lies in the substituents on the pyridine group of the ligand and whether there are cyano substituents on the dibenzofuran group. Compared to Comparative Example 1, the full width at half maximum (FWHM) of Example 1 and Example 2 narrowed by 28.3 nm and 27.1 nm, respectively; the driving voltage decreased by 0.5 V and 0.48 V, respectively; CE improved by 10.2% and 11.2%, respectively; PE improved by 31.6% and 32.6%, respectively; EQE improved by 9.7% and 10.1%, respectively; and the maximum emission wavelength was blue-shifted by 4 nm. As can be seen from this, the L having a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure of the present invention a In the ligand, if a metal complex having a fluorine substituent at a specific position of the 6-membered aza ring and a cyano group substituted in the 6-membered-5-membered-6-membered fused ring structure is applied to the device, the individual performance of the device can be significantly improved, for example, by lowering the driving voltage and improving the device efficiency (CE, PE, and EQE), and also by significantly improving the luminescence saturation of the device, the overall performance of the device can be significantly improved.

[0332] Comparing Example 1 and Comparative Example 2, the light-emitting materials used in the device are the metal complex 134 of the present invention and the metal complex GD2, which is not a metal complex of the present invention, respectively, and the difference is L aThe Ar substituent on the dibenzofuran group in the ligand is different. Compared to Comparative Example 2, the CE and full width at half maximum of Example 1 are similar, the driving voltage decreased by 0.17 V, and PE and EQE improved by 11.2% and 5.2%, respectively. As can be seen from this, the L having a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure of the present invention a In the ligand, if a metal complex having the Ar substitution of the present invention in the above 6-membered-5-membered-6-membered fused ring structure is applied to a device, the driving voltage of the device can be lowered, the device efficiency (PE and EQE) can be greatly improved, and the overall performance of the device can be significantly improved.

[0333] When comparing Examples 1 and 2 with Comparative Example 3, the light-emitting materials used in the device are the metal complex 134 and metal complex 150 of the present invention, and the metal complex GD3 that is not a metal complex of the present invention, respectively, and the difference is L a In the ligand, one substituent on the pyridine group is changed from F to CD3, and the Ar substituent on the benzofuran group is different. Compared to Comparative Example 3, the full width at half maximum of Example 1 and Example 2 increased by 2.1 nm and 3.3 nm, respectively, but the driving voltage decreased by 0.17 V and 0.15 V, respectively; CE improved by 16.1% and 17.2%, respectively; PE improved by 24% and 25%, respectively; and EQE improved by 16.8% and 17.2%, respectively. As can be seen from this, the L having a 6-membered aza ring-(6-membered-5-membered-6-membered fused ring) skeletal structure of the present invention a In the ligand, a fluorine substituent is provided at a specific position of the 6-membered aza ring, and when a metal complex having the Ar substituent of the present invention in the 6-membered-5-membered-6-membered fused ring structure is applied to a device, the individual performance of the device can be significantly improved, for example, by lowering the driving voltage and improving device efficiency (CE, PE, and EQE), and significantly improving the overall performance of the device.

[0334] As can be seen from this, L having a 6-atom aza ring-(6-membered-5-membered-6-membered fusion ring) skeletal structure of the present invention a In the ligand, a fluorine substituent is provided at a specific position of the 6-membered aza ring, and when a metal complex having a specific substitution with the Ar of the present invention is applied to the 6-membered-5-membered-6-membered fused ring structure, the individual performance of the device can be significantly improved, for example, by lowering the driving voltage and improving device efficiency (CE, PE, and EQE), and significantly improving the overall performance of the device.

[0335] Using Gaussian 09 software, computation method: geometric optimization calculations were performed using the CEP-31G base set including the B3LYP hybrid functionals method and effective nuclear potential to calculate the HOMO and LUMO energy levels of metal complex 133, metal complex 149, and the non-metal complexes of the present invention, GD4 and GD5, and the difference between their HOMO and LUMO energy levels E g was calculated, and their difference is, only L a The only difference is the position of the F substitution in the pyridine group of the ligand.

[0336] The DFT calculation results are recorded and displayed in Table 3.

[0337] [Table 3] DFT results of metal complexes 133, 149 and GD4, GD5

[0338]

[0339] The metal complex structure calculated by DFT is as follows.

[0340]

[0341] discussion:

[0342] Table 3 shows the DFT calculation results of the metal complex of the present invention and the comparative metal complex. The HOMO-LUMO energy level differences of metal complex 133 and metal complex 149 of the present invention are 3.20 eV and 3.18 eV, respectively. The HOMO-LUMO energy level differences of metal complexes GD4 and GD5, which are not metal complexes of the present invention, are merely 3.11 eV and 3.04 eV, respectively. A higher energy level difference indicates that excitons generated in the electroluminescent device can return to the ground state in a higher energy form; therefore, it is advantageous for realizing a more blue-shifted emission spectrum to achieve more saturated green emission, which is of great help in realizing the BT2020 wide color gamut. The above results [regarding] the L of the present invention a It is indicated that metal complexes having ligands can be used as light-emitting materials in the light-emitting layer of an electroluminescent device, and by using the metal complex of the present invention, higher light-emitting efficiency, a narrower full width at half maximum, and a more saturated green light spectrum can be provided, thereby significantly improving the overall performance of the device.

[0343] 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, the metal complex is Ir(L a ) m (L b ) 3-m Represented as;L a and L b are the first and second ligands coordinating with the metal Ir, respectively; m is selected from 1, 2, or 3, and if m is 1, the two L b is identical or different; if m is 2 or 3, multiple L a is identical or different;L a is represented by Equation 1a, and ,where Z is selected from the group consisting of O, S, and Se; Y1-Y4 are the same or different CR whenever they appear y Or selected from N; Y2 and / or Y3 is CR y Selected from, and the above R y silver It is fluorine; X3-X8 are the same or different CR whenever they appear x Selected from , CAr or N; at least one of X3-X8 is CR x Selected from, and the above R x is a cyano group or fluorine; at least one of X3-X8 is selected from CAr; Ar is represented by Formula 2, and ,a is selected from 0, 1 or 2;R a1 and R a2 appears identically or differently as single substitution, multiple substitution, or non-substitution; rings Ar1 and Ar2 appear identically or differently as selected from aromatic rings having 6 to 30 cyclic atoms, heteroaromatic rings having 5 to 30 cyclic atoms, or combinations thereof; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8; and R a1 and R a2 Whenever appearing, 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, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, a phosphino group, and combinations thereof, in the same or different ways; R x and R y Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon group having 0 to 20 carbon atoms Selected from the group consisting of amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, phosphino groups, and combinations thereof; "*" indicates the linkage position of Formula 2; and adjacent substituent R x , R y , R a1 and R a2 can be arbitrarily connected to form a loop; in Equation 1a " " indicates a connection with the metal Ir; L b Whenever it appears, it is selected from a structure represented as any one of the groups formed below that are identical or different, and , , , ; Here, R a and R b represents a single permutation, multiple permutation, or no permutation, either identically or differently, whenever it appears;R a and R b Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a phosphino group, and combinations thereof; and an adjacent substituent R a and R b The can be arbitrarily connected to form a ring; and the above L b to " "Ir represents a connection with metal Ir; where, a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanyl group, a substituted arylgermanyl group, a substituted amino group is any one of the alkyl group, cycloalkyl group, heteroalkyl group, heterocyclic group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanyl group, arylgermanyl group, amino group having 1 to 20 carbon atoms Alkyl group, unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, unsubstituted heteroalkyl group having 1 to 20 carbon atoms, unsubstituted heterocyclic group having 3 to 20 cyclic carbon atoms, unsubstituted aralkyl group having 7 to 30 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted alkynyl group having 2 to 20 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, unsubstituted heteroaryl group having 3 to 30 carbon atoms, unsubstituted alkylsilyl group having 3 to 20 carbon atoms, unsubstituted arylsilyl group having 6 to 20 carbon atoms, unsubstituted having 3 to 20 carbon atoms A metal complex meaning that it can be substituted by one or at least two selected from an alkyl germanyl group, an unsubstituted aryl germanyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, a carboxylic acid group, a cyano group, an isocyano group, a sulfanyl group, a phosphino group, and combinations thereof. Claim 2 In claim 1, L a is represented by Equation 1a, and ;Z is selected from the group consisting of O, S, and Se; Y1-Y4 are CR that are the same or different whenever they appear y or selected from N; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; X3-X8 are the same or different CR whenever they appear x Selected from , CAr or N; at least one of X3-X8 is CR x Selected from, and the above R x is a cyano group or fluorine; at least one of X3-X8 is selected from CAr; Ar is represented by Formula 2, and ,a is selected from 0 or 1;R a1 and R a2 appears identically or differently as single substitution, multiple substitution, or non-substitution; rings Ar1 and Ar2 appear identically or differently as selected from aromatic rings having 6 to 30 cyclic atoms, heteroaromatic rings having 5 to 30 cyclic atoms, or combinations thereof; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8; and R x , R y , R a1 and R a2 Whenever it appears, 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, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and combinations thereof, either identically or differently; "*" indicates the linkage position in Formula 2; and in Formula 1a, " A metal complex representing a connection with the metal Ir. Claim 3 In claim 1, where, L b It is selected from the structure below, and ;Here, R a and R b represents a single permutation, multiple permutation, or no permutation, either identically or differently, whenever it appears;R a and R b Whenever appearing, 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 cyclic atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxylic acid group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a phosphino group, and combinations thereof; and an adjacent substituent R a , R b The can be arbitrarily connected to form a ring; and the above L b to " A metal complex representing a connection with the metal Ir. Claim 4 In claim 1, the metal complex is Ir(L a ) m (L b ) 3-m It is represented by Equation 3, and Here, m is selected from 1, 2, or 3, and if m is 1, two L b is identical or different; if m is 2 or 3, multiple L a is the same or different; Z is selected from the group consisting of O and S; Y1-Y4 are the same or different CR whenever they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; X3-X8 are the same or different CR whenever they appear x, Selected from CAr; at least one of X3-X8 is CR x Selected from, and the above R x is a cyano group or fluorine; at least one of X3-X8 is selected from CAr; Ar is represented by Formula 2, and ,a is selected from 0, 1, or 2;R a1 and R a2 appears identically or differently as single substitution, multiple substitution, or non-substitution; rings Ar1 and Ar2 appear identically or differently as selected from aromatic rings having 6 to 30 cyclic atoms, heteroaromatic rings having 5 to 30 cyclic atoms, or combinations thereof; the total number of cyclic atoms in rings Ar1 and Ar2 is greater than or equal to 8; and R a1 and R a2 Whenever it appears, 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, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and combinations thereof, either identically or differently; R x , R y , and R1-R8 are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a phosphino group, and combinations thereof, wherein adjacent substituents R1-R8 can optionally be connected to form a ring. Claim 5 A metal complex in which Z is O, in any one of claims 1 to 4. Claim 6 In any one of claims 1 to 4, a is a metal complex of 1. Claim 7 In any one of claims 1 to 4, Y1-Y4 are identical or different CR whenever they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; the remainder is R y A metal complex selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 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, which appear identically or differently each time. Claim 8 In any one of claims 1 to 4, Y1-Y4 are identical or different CR whenever they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; the remainder is R y A metal complex selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 9 In any one of claims 1 to 4, Y1-Y4 are identical or different CR whenever they appear y Selected from; at least one of Y2 and Y3 is CR y Selected from, and the above R y silver It is fluorine; the remainder is R y A metal complex selected from hydrogen, deuterium, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, t-amyl group, or combinations thereof; optionally, hydrogen in the said group is partially or wholly substituted by deuterium. Claim 10 In any one of claims 1 to 4, at least one of Y2 and Y3 is CR y Selected from, and the above R y go It is fluorine; at least one of Y1-Y4 is CR y Selected from, R y A metal complex selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof. Claim 11 In any one of claims 1 to 4, Y2 and Y3 are CR y Selected from, and one of the above R y silver It is fluorine; and the above R of the other one among them y A metal complex selected from the group consisting of silver deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and combinations thereof. Claim 12 In any one of claims 1 to 4, at least one of X5-X8 is CR x Selected from; the above R x The silver is a cyano group or fluorine, and at least one of X5-X8 is a metal complex selected from CAr. Claim 13 In any one of claims 1 to 4, one of X7 and X8 is CR x Selected from; the above R x It is a cyano group or fluorine, and the other one of X7 and X8 is a metal complex selected from CAr. Claim 14 In any one of claims 1 through 4, X3-X8 are identical or different CR whenever they appear x or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R x A metal complex 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, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and combinations thereof, which appear identically or differently each time. Claim 15 In any one of claims 1 through 4, X3-X8 are identical or different CR whenever they appear x or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R x A metal complex selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof, which appear identically or differently each time. Claim 16 In any one of claims 1 through 4, X3-X8 are identical or different CR whenever they appear x or selected from CAr; at least one of X3-X8 is selected from CAr; and the above R x At least one of them is selected from cyano groups or fluorine, and the remainder R x A metal complex selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 cyclic carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 17 In any one of claims 1 to 4, R a1 and R a2 A metal complex selected from the group consisting of hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 15 carbon atoms, and combinations thereof, which appear identically or differently each time. Claim 18 In any one of claims 1 to 4, R a1 and R a2 A metal complex that is selected from the group consisting of hydrogen, deuterium, fluorine, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, neopentyl group, cyclopentyl group, cyclohexyl group, phenyl group, pyridine group, trimethylsilyl group, and combinations thereof, which appear identically or differently each time; optionally, hydrogen in said group may be partially or wholly substituted by deuterium. Claim 19 In any one of claims 1 to 4, ring Ar1 and ring Ar2 are selected from aromatic rings having 6 to 18 ring atoms, heteroaromatic rings having 5 to 18 ring atoms, or combinations thereof, which appear identically or differently; and a metal complex in which the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30. Claim 20 In any one of claims 1 to 4, ring Ar1 and ring Ar2 are, whenever they appear, identically or differently selected from the group consisting of a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, a phenanthrene ring, anthracene ring, a fluorene ring, a silafluorene ring, a quinoline ring, an isoquinoline ring, a fused dithiophene ring, a fused difuran ring, a benzofuran ring, a benzothiophen ring, a dibenzofuran ring, a dibenzothiophen ring, a triphenylene ring, a carbazole ring, an azacarbazole ring, an azafluorene ring, an azasilafluorene ring, an azadibenzofuran ring, an azadibenzothiophen ring, and combinations thereof; and the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 24; Optionally, a metal complex in which hydrogen in the above group can be partially or wholly substituted by deuterium. Claim 21 In any one of claims 1 to 4, ring Ar1 and ring Ar2 are metal complexes selected from benzene rings, heteroaromatic rings having 5 or 6 ring atoms, or combinations thereof, which appear identically or differently. Claim 22 In any one of claims 1 to 4, ring Ar1 and ring Ar2 are metal complexes selected from benzene rings or heteroaromatic rings having six ring atoms, which are identical or different whenever they appear. Claim 23 In any one of claims 1 to 4, ring Ar1 and ring Ar2 are metal complexes selected from benzene rings, which are identical or different whenever they appear. Claim 24 In any one of claims 1 to 4, Ar is the same or different each time it appears Selected from a group consisting of combinations thereof; optionally, hydrogen in said group may be partially or wholly substituted by deuterium; where "*" indicates a metal complex with a linkage position of said Ar. Claim 25 A metal complex according to claim 4, wherein at least one or at least two of R1-R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total sum of the number of carbon atoms of all R1-R4 and / or R5-R8 is at least 4. Claim 26 A metal complex according to claim 4, wherein at least one or at least two of R1-R4 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total number of carbon atoms of all R1-R4 is at least 4; and / or at least one or at least two of R5-R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 cyclic carbon atoms, or a combination thereof, and the total number of carbon atoms of all R5-R8 is at least 4. Claim 27 In claim 4, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are metal complexes selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 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. Claim 28 In claim 4, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are metal complexes selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof. Claim 29 In claim 4, at least one, at least two, at least three, or all of R2, R3, R6, R7 are selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group, neopentyl group, t-amyl group, and combinations thereof; optionally, hydrogen in said group may be partially or wholly substituted by deuterium, forming a metal complex. Claim 30 In claim 1, L a is selected from a group consisting of structures that make it identical or different whenever it appears: Optionally, the above L a1 to L a544 , L a553 to L a560 , L a569 to L a576 , L a585 to L a596 , L a621 to L a805 , L a822 to L a879 Hydrogen atoms in it can be partially or wholly replaced by deuterium. Claim 31 In Article 30, L b Metal complexes selected from a group consisting of structures that are identical or different whenever they appear: Optionally, the above L b1 to L b333 Hydrogen atoms in it can be partially or wholly replaced by deuterium. Claim 32 In claim 31, the metal complex is IrL a (L b It is represented as )2, and two L b is the same or different, and L a y L a1 to L a544 , L a553 to L a560 , L a569 to L a576 , L a585 to L a596 , L a621 to L a805 , L a822 to L a879 It is any one selected from the group consisting of, and L b y L b1 to L b333 Any one or two selected from the group consisting of; the metal complex is selected from the group consisting of metal complexes 1 to 396, wherein metal complexes 1 to 396 are IrL a (L b It is represented as )2, and two L b is identical, and L a and L b Metal complexes corresponding to the structures shown in the table below, respectively: . Claim 33 An electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex according to claim 1. Claim 34 In claim 33, the organic layer containing the metal complex is an electroluminescent element that is a light-emitting layer. Claim 35 In claim 34, the light-emitting layer additionally comprises a first host compound, an electroluminescent device. Claim 36 The electroluminescent device according to claim 35, wherein the light-emitting layer additionally comprises a second host compound; and at least one of the first host compound and the second host compound 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 indolocarbazole group, a dibenzothienyl group, an azadibenzothienyl group, a dibenzofuran group, an azadibenzofuran group, a dibenzoselenopene group, a triphenylene group, an azatriphenylene group, a fluorene group, a silaflorene 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. Claim 37 In claim 36, the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer, in an electroluminescent device. Claim 38 A compound composition comprising a metal complex according to claim 1.

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