Organic electroluminescent materials and devices

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a material comprising L having a structure of Formula 1 a The present invention discloses a metal complex of a ligand, wherein the metal complex can be used as a luminescent material in an electroluminescent device. These novel compounds can be applied to electroluminescent devices to exhibit more excellent performance, can reduce the driving voltage, improve the device efficiency, especially improve the EQE, and ultimately significantly improve the overall performance of the device. Also disclosed is an electroluminescent device comprising the metal complex and a compound combination comprising the metal complex.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound comprising L having a structure of Formula 1 a The invention relates to a metal complex of a ligand, and an electroluminescent device and a compound combination comprising the metal complex. Background Art

[0002] Organic electronic devices include, but are not limited to, the following categories: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaics (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 plasmonic light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be categorized based on the form of the materials used, into small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

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

[0007] The luminescent color of OLEDs can be achieved through the structural design of luminescent materials. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life, and high operating voltage. Commercial full-color OLED displays generally adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which remains a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency, and longer device life.

[0008] The applicant disclosed in the previous US20200251666A1 a ligand having the following structure: wherein at least one of X1-X8 is selected from C-CN, further disclosed is an iridium complex having the following structure Its application in organic electroluminescent devices can improve device performance and color saturation. Although it has reached a high level in the industry, there is still room for improvement. This application only discloses metal complexes in which R4 is an aryl substituent of a phenyl group and their use in devices. It does not disclose or teach the effect of introducing a (hetero)aryl group, as specified in this application, at a specific position in the metal complex on device performance.

[0009] In the previous US20200091442A1, the applicant disclosed a ligand having the following structure Further disclosed is an iridium complex having the structure In this application, fluorine at specific positions in the ligand can improve material performance, including increasing device lifespan and thermal stability, but there is still room for improvement. This application only discloses metal complexes in which R4 is an aryl substituent of a phenyl group and their applications in devices. It does not disclose or teach the impact of introducing a (hetero)aryl group, as specified in this application, at a specific position in the metal complex on device performance.

[0010] US2013119354A1 discloses a metal complex having the following general structure: , wherein R1-R4 are selected from hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. This application only discloses metal complexes in which R1 is an aryl substituent of a phenyl group and their applications in devices. It does not disclose or teach the effects of introducing a (hetero)aryl group, as specified in this application, at a specific position in the metal complex on device performance.

[0011] US20200287144A1 discloses a metal complex comprising a ligand structure shown in the following structure: wherein X1 is selected from silicon and germanium, and further disclosed is an iridium complex having the following general structure: This application mainly focuses on the effect of introducing silicon or germanium groups into metal complexes on device performance, and does not disclose or teach the effect of introducing (hetero) aromatic groups as specified in this application at specific positions in metal complexes on device performance. Summary of the Invention

[0012] The present invention aims to provide a series of L having a structure of formula 1 a Ligand-metal complexes are proposed to solve at least some of the above problems.

[0013] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a metal M and a ligand L coordinated with the metal M. a , where L aHaving a structure represented by Formula 1:

[0014]

[0015] In formula 1,

[0016] The metal M is selected from metals with a relative atomic mass greater than 40;

[0017] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0018] X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R' are present at the same time, the two R's are the same or different;

[0019] X1-X5 are selected from CR in the same or different ways each time they appear. x or N;

[0020] Ar has a structure represented by Formula 2:

[0021]

[0022] a is selected from 0, 1, 2, 3, 4 or 5;

[0023] R a1 and R a2 Each occurrence of the same or different means mono-, poly- or no-substitution;

[0024] Ring Ar1 and Ring Ar2 are identical or different at each occurrence and are selected from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof; and the total number of ring atoms in Ring Ar1 and Ring Ar2 is greater than or equal to 8;

[0025] R', R x , R a1 and R a2Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0026] “*” indicates the connection position of formula 2;

[0027] Adjacent substituents R', R x , R a1 , R a2 Can optionally be linked to form a ring.

[0028] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0029] anode,

[0030] cathode,

[0031] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex described in the above embodiment.

[0032] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises the metal complex described in the above embodiment.

[0033] The present invention discloses a series of L having a structure of formula 1 a The metal complexes of the ligands can be used as luminescent materials in electroluminescent devices. These novel compounds can be applied to electroluminescent devices to exhibit superior performance, such as lowering the driving voltage, improving device efficiency, and particularly improving the EQE, ultimately significantly enhancing the overall performance of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound combinations disclosed herein.

[0035] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the metal complexes and compound combinations disclosed herein. DETAILED DESCRIPTION

[0036] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. 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 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0037] There are many more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0038] The above layered structures are provided by way of non-limiting examples. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.

[0039] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0040] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1 The difference is that an encapsulation layer 102 can also be included above cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0041] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0042] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0043] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.

[0044] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0045] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.

[0046] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0047] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap so as to convert between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.

[0048] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0049] Definition of Substituent Terms

[0050] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0051] Alkyl - as used herein, includes straight chain and branched chain alkyl groups. 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, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0052] Cycloalkyl - as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0053] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbon atoms in the alkyl chain substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl can be optionally substituted.

[0054] Alkenyl - as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, alkenyl groups can be optionally substituted.

[0055] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl groups can be optionally substituted.

[0056] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

[0057] Heterocyclic group or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothiol. Additionally, heterocyclyl groups may be optionally substituted.

[0058] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain from 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group may have from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, and more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0059] Alkoxy - as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

[0060] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenyloxy. In addition, the aryloxy group may be optionally substituted.

[0061] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,

[0062] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0063] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0064] Alkylgermanyl - As used herein, alkyl-substituted germanium groups are encompassed. The alkylgermanyl group can 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, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyl-tert-butylgermanyl, and methyldi-tert-butylgermanyl. Additionally, the alkylgermanyl group can be optionally substituted.

[0065] Arylgermanyl - As used herein, encompasses germanium groups substituted with at least one aryl or heteroaryl group. The arylgermanyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyltert-butylgermanyl. 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 moiety are replaced by a nitrogen atom. 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. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.

[0067] In the present disclosure, unless otherwise defined, when using any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted Carboxylic acid group, substituted ester group, substituted sulfinyl group, refers to any one of alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl, sulfonyl and phosphino groups, which may be one or more selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted alkyl group having 3 to 20 carbon atoms, cycloalkyl groups having ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclyl groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups and combinations thereof.

[0068] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.

[0069] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in compounds may be preferred because it enhances device efficiency and stability.

[0070] In the compounds described herein, multiple substitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0071] In the compounds mentioned in the present disclosure, unless clearly defined, such as adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including the situation where adjacent substituents can be connected to form a ring, and also including the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can 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 away. 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 statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0073]

[0074] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other via a chemical bond to form a ring, as can be exemplified by the following formula:

[0075]

[0076] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to further distant carbon atoms are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0077]

[0078] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0079]

[0080] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a metal M and a ligand L coordinated with the metal M. a , where L a Having a structure represented by Formula 1:

[0081]

[0082] In formula 1,

[0083] The metal M is selected from metals with a relative atomic mass greater than 40;

[0084] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0085] X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R' are present at the same time, the two R's are the same or different;

[0086] X1-X5 are selected from CR in the same or different ways each time they appear. x or N;

[0087] Ar has a structure represented by Formula 2:

[0088]

[0089] a is selected from 0, 1, 2, 3, 4 or 5;

[0090] R a1 and R a2 Each occurrence of the same or different means mono-, poly- or no-substitution;

[0091] Ring Ar1 and Ring Ar2 are identical or different at each occurrence and are selected from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof; and the total number of ring atoms in Ring Ar1 and Ring Ar2 is greater than or equal to 8;

[0092] R', R x , R a1 and R a2Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0093] “*” indicates the connection position of formula 2;

[0094] Adjacent substituents R', R x , R a1 , R a2 Can optionally be linked to form a ring.

[0095] In this context, "adjacent substituents R', R x , R a1 , R a2 "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R', two substituents R x Between the two substituents R a1 Between the two substituents R a2 Between the two substituents R a1 and R a2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0096] In this article, the "ring atoms" in aromatic rings and heteroaromatic rings refer to the atoms that form the ring itself in a ring structure with aromaticity (for example, a monocyclic (hetero)aromatic ring, a condensed (hetero)aromatic ring). The carbon atoms and heteroatoms (including but not including O, S, N, Se or Si, etc.) in the ring are all counted in the number of ring atoms. When 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 of phenyl, pyridyl, and triazinyl is 6; the number of ring atoms of dithiophene and difuran is 8; the number of ring atoms of benzothienyl and benzofuranyl is 9; the number of ring atoms of naphthyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl is 10; the number of ring atoms of dibenzothiophene, dibenzofuran, fluorene, azadibenzothiophene, azadibenzofuran and azafluorene is 13; the various examples described here are only for illustration, and other cases are similar. When a is 0 in formula 2, it means that Ar has In the structure represented by, "the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8" means that ring Ar1 is an aromatic ring or heteroaromatic ring with a total number of ring atoms greater than or equal to 8; when a in formula 2 is 1, it means that Ar has For example, when both ring Ar1 and ring Ar2 are phenyl, R a1 and R a2 When both are hydrogen, the total number of ring atoms of ring Ar1 and ring Ar2 is 12; for example, when both ring Ar1 and ring Ar2 are phenyl, R a1 are all hydrogen, R a2 When the ring Ar1 and the ring Ar2 are monosubstituted and are phenyl, the total number of ring atoms in the ring Ar1 and the ring Ar2 is equal to 12. The same applies to other cases.

[0097] According to one embodiment of the present invention, Cy is selected from any one of the following groups:

[0098]

[0099] in,

[0100] Each occurrence of R is the same or different, indicating monosubstitution, polysubstitution, or no substitution; when multiple R are present in any structure, the R are the same or different;

[0101] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0102] Adjacent substituents R can optionally be linked to form a ring;

[0103] Among them, '#' indicates the position connected to the metal M, Indicates the location connected to X1, X2, X3, or X4.

[0104] In this document, "adjacent substituents R can optionally be linked to form a ring" is intended to mean that any one or more of the substituents formed between any two adjacent substituents R can be linked to form a ring. Obviously, these substituents may not be linked to form a ring.

[0105] According to one embodiment of the present invention, wherein L a Each occurrence is identically or differently selected from the group consisting of:

[0106]

[0107]

[0108] X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R' are present at the same time, the two R's are the same or different;

[0109] Ar has a structure represented by Formula 2:

[0110]

[0111] a is selected from 0, 1, 2, 3, 4 or 5;

[0112] Ring Ar1 and Ring Ar2 are identical or different at each occurrence and are selected from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof; and the total number of ring atoms in Ring Ar1 and Ring Ar2 is greater than or equal to 8;

[0113] R, R x , R a1 and R a2 Each occurrence is identical or different and represents mono-, poly-, or unsubstituted;

[0114] R, R', R x , R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0115] Adjacent substituents R, R', R x , R a1 and R a2 can optionally be linked to form a ring;

[0116] “*” indicates the connection position of Formula 2.

[0117] In this context, "adjacent substituents R, R', R x , R a1 and R a2 "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R, between two substituents R', between two substituents R xBetween the two substituents R a1 Between the two substituents R a2 Between the two substituents R a1 and R a2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0118] According to one embodiment of the present invention, the metal complex has M(L a ) m (L b ) n (L c ) q The general formula of

[0119] in,

[0120] M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, the same or different; preferably, M is selected from Pt or Ir at each occurrence, the same or different;

[0121] L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; among them, L a , L b and L c can optionally be linked to form multidentate ligands;

[0122] m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, multiple L a Same or different; when n is equal to 2, the two L b Same or different; when q is equal to 2, the two L c Same or different;

[0123] L b and L c Each occurrence is identically or differently selected from the structure shown in any one of the group consisting of:

[0124]

[0125]

[0126] in,

[0127] R a , Rb Each occurrence is identical or different and represents mono-, poly-, or unsubstituted;

[0128] X b Each occurrence is identical or different and is selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;

[0129] R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0130] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0131] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R aBetween the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0132] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, the same or different each time it appears.

[0133] According to one embodiment of the present invention, the metal M is selected from Pt or Ir, the same or different each time it occurs.

[0134] According to one embodiment of the present invention, the metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 3:

[0135]

[0136] in,

[0137] X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R' are present at the same time, the two R's are the same or different;

[0138] m is selected from 1, 2 or 3; when m is selected from 1, two L b Same or different; when m is selected from 2 or 3, multiple L a Same or different;

[0139] Each occurrence of Y1-Y4 is the same or different and is selected from CRy or N;

[0140] X1-X5 are selected from CR in the same or different ways each time they appear. x or N;

[0141] Ar has a structure represented by Formula 2:

[0142]

[0143] a is selected from 0, 1, 2, 3, 4 or 5;

[0144] R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no substitution;

[0145] Ring Ar1 and Ring Ar2 are identical or different at each occurrence and are selected from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof; and the total number of ring atoms in Ring Ar1 and Ring Ar2 is greater than or equal to 8;

[0146] “*” indicates the connection position of formula 2;

[0147] R', R x , R y , R1-R8, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0148] Adjacent substituents R', R x , R y , Ra1 , R a2 can optionally be linked to form a ring;

[0149] Adjacent substituents R1 to R8 can optionally be linked to form a ring.

[0150] In this context, “adjacent substituents R′, R x , R y , R a1 , R a2 "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R', two substituents R x Between the two substituents R y Between the two substituents R a1 Between the two substituents R a2 Between the two substituents R a1 and R a2 Between the two substituents R' and R x Between, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring. "Adjacent substituents R1-R8 can optionally be connected to form a ring" is intended to mean that adjacent substituent groups, for example, between adjacent substituents R1 and R2, between adjacent substituents R3 and R2, between adjacent substituents R3 and R4, between adjacent substituents R5 and R4, between adjacent substituents R5 and R6, between adjacent substituents R7 and R6, between adjacent substituents R7 and R8, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0151] According to one embodiment of the present invention, the metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 3A:

[0152]

[0153] X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R' are present at the same time, the two R's are the same or different;

[0154] m is selected from 1, 2 or 3; when m is selected from 1, two L b Same or different; when m is selected from 2 or 3, multiple L a Same or different;

[0155] R x and R yThe same or different at each occurrence indicates mono-, poly- or no substitution;

[0156] Ar has a structure represented by Formula 2:

[0157]

[0158] a is selected from 0, 1, 2, 3, 4 or 5;

[0159] R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no substitution;

[0160] Ring Ar1 and Ring Ar2 are identical or different at each occurrence and are selected from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof; and the total number of ring atoms in Ring Ar1 and Ring Ar2 is greater than or equal to 8;

[0161] *” indicates the connection position of formula 2;

[0162] R', R x , R y , R1-R8, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0163] Adjacent substituents R', R x , R y , R a1 , R a2 can optionally be linked to form a ring;

[0164] Adjacent substituents R1 to R8 can optionally be linked to form a ring.

[0165] According to one embodiment of the present invention, each occurrence of X1-X5 is the same or different and is selected from CR x .

[0166] According to one embodiment of the present invention, each occurrence of Y1-Y4 is the same or different and is selected from CR y .

[0167] According to an embodiment of the present invention, at least one of X1-X5 is N, for example, one or two of X1-X8 are N.

[0168] According to an embodiment of the present invention, at least one of Y1-Y4 is N, for example, one or two of Y1-Y4 are N.

[0169] According to one embodiment of the present invention, X is selected from O or S.

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

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

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

[0173] According to one embodiment of the present invention, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.

[0174] According to one embodiment of the present invention, R a1 and R a2Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 15 carbon atoms, and combinations thereof.

[0175] According to one embodiment of the present invention, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, and combinations thereof.

[0176] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-18 ring atoms, heteroaromatic rings having 5-18 ring atoms, or a combination thereof each time they appear; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.

[0177] According to one embodiment of the present invention, in Ar, the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 24.

[0178] According to one embodiment of the present invention, in Ar, the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 18.

[0179] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are identically or differently selected each time from an aromatic ring having 6 ring atoms, or a heteroaromatic ring having 5 or 6 ring atoms, or a combination thereof.

[0180] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings or heteroaromatic rings having 6 ring atoms each time they occur.

[0181] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected, identically or differently, from aromatic rings having 6 ring atoms each time they occur.

[0182] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from the group consisting of the following each time they appear, the same or different: a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a triazine ring, a phenanthrene ring, an anthracene ring, a silanol ring, a quinoline ring, an isoquinoline ring, a benzofuran ring, a dithiophene ring, a difuran ring, a benzothiophene ring, an indene ring, a dibenzofuran ring, a dibenzothiophene ring, a triphenylene ring, a carbazole ring, an azacarbazole ring, an azadibenzofuran ring, an azadibenzothiophene ring, an azasilanol 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 30.

[0183] According to one embodiment of the present invention, wherein Ar is selected from the group consisting of the following each time it occurs, the same or different:

[0184]

[0185] and combinations thereof;

[0186] Optionally, the above groups may be partially or fully deuterated; wherein "*" indicates the attachment position of the Ar.

[0187] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, and combinations thereof.

[0188] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 11 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.

[0189] According to one embodiment of the present invention, wherein the R xAt least one of the following is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, and combinations thereof.

[0190] According to one embodiment of the present invention, R x At least one of the following is selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.

[0191] According to one embodiment of the present invention, R x At least one of them is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a cyano group, and combinations thereof.

[0192] According to one embodiment of the present invention, at least one of X1-X5 is selected from CR x , and the R x It is cyano or fluorine.

[0193] According to one embodiment of the present invention, at least one of X3-X5 is selected from CR x , and the R x It is cyano or fluorine.

[0194] According to one embodiment of the present invention, X5 is CR x , and the R x It is cyano or fluorine.

[0195] According to one embodiment of the present invention, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof.

[0196] According to one embodiment of the present invention, R yEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 15 carbon atoms, and combinations thereof.

[0197] According to one embodiment of the present invention, at least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0198] According to one embodiment of the present invention, at least one or at least two or at least three or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, 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.

[0199] According to one embodiment of the present invention, at least one or at least two or at least three or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

[0200] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; optionally, the hydrogen in the above groups is partially or completely deuterated.

[0201] According to one embodiment of the present invention, R' is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0202] According to one embodiment of the present invention, R' is a methyl group or a deuterated methyl group.

[0203] According to one embodiment of the present invention, each occurrence of R7 is identical or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted an 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 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0204] According to one embodiment of the present invention, L a Each time it appears, the same or different selection is made from L a1 To L a1177 The group consisting of L a1 To L a1177 The specific structure is as follows:

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] According to one embodiment of the present invention, L b Each time it appears, the same or different selection is made from L b1 To L b128 The group consisting of L b1 To L b128 The specific structure is as follows:

[0261]

[0262]

[0263]

[0264] According to one embodiment of the present invention, L c Each time it appears, the same or different selection is made from L c1 To L c360 The group consisting of L c1To L c360 The specific structure is as follows:

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, the same or different selection is made from L a1 To L a1177 Any one or two of the group consisting of L b Choose from L b1 To L b128 Any of the groups consisting of.

[0273] According to one embodiment of the present invention, the metal complex has Ir(L a )(L b )2 structure, L a Each time it appears, the same or different selection is made from L a1 To L a1177 Any one of the group consisting of L b Choose from L b1 To L b128 Any one or any two of the group consisting of.

[0274] According to one embodiment of the present invention, the metal complex has Ir(L a )3 structure, L a Each time it appears, the same or different selection is made from L a1 To L a1177 Any one, any two, or any three of the group consisting of.

[0275] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, the same or different selection is made from L a1To L a1177 Any one or two of the group consisting of L c Choose from L c1 To L c360 Any of the groups consisting of.

[0276] According to one embodiment of the present invention, the metal complex has Ir(L a )(L c )2 structure, L a Each time it appears, the same or different selection is made from L a1 To L a1177 Any one of the group consisting of L c Choose from L c1 To L c360 Any one or any two of the group consisting of.

[0277] According to one embodiment of the present invention, the metal complex has Ir(L a )(L b )(L c ) structure, where L a Each time it appears, the same or different selection is made from L a1 To L a1177 Any one of the groups consisting of L b Choose from L b1 To L b128 Any one of the group consisting of L c Choose from L c1 To L c360 Any of the groups consisting of.

[0278] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complexes 1 to 1008, wherein the metal complexes 1 to 1008 have IrL a (L b )2 structure, where two L b Same, where L a and L b They correspond to the structures shown in the following table:

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:

[0294] anode,

[0295] cathode,

[0296] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex described in any one of the preceding embodiments.

[0297] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

[0298] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device emits green light.

[0299] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device emits white light.

[0300] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device comprises a first host compound.

[0301] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device comprises a first host compound and a second host compound.

[0302] According to one embodiment of the present invention, at least one of the host compounds in the electroluminescent device contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0303] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 4:

[0304]

[0305] in,

[0306] Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and they are connected to formula A;

[0307]

[0308] in,

[0309] Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" may be the same or different;

[0310] p is 0 or 1; r is 0 or 1;

[0311] When Q is selected from N, p is 0 and r is 1;

[0312] When Q is selected from the group consisting of O, S, Se, NR", CR"R", SiR"R", GeR"R" and R"C=CR", p is 1 and r is 0;

[0313] L is identical or different at each occurrence and is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0314] Q1-Q8 are each identically or differently selected from C, CRq or N;

[0315] R e , R" and R qEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0316] “*” represents the connection position between Formula A and Formula 4;

[0317] Adjacent substituent R e , R”, R q Can optionally be linked to form a ring.

[0318] In this context, “the adjacent substituent R e , R”, R q "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R e Between two substituents R", between two substituents R q Between the two substituents R" and R q Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0319] According to one embodiment of the present invention, each occurrence of E1-E6 is selected from C, CR e or N, and three of E1-E6 are N, and at least one of E1-E6 is CR e , and the R e Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0320] According to one embodiment of the present invention, each occurrence of E1-E6 is selected from C, CR e or N, and three of E1-E6 are N, and at least one of E1-E6 is CR e , and the R e Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, and combinations thereof.

[0321] According to one embodiment of the present invention, each occurrence of Q is identically or differently selected from O, S, N or NR.

[0322] According to one embodiment of the present invention, at least one or at least two of Q1-Q8 are selected from CR q , and the R q is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof.

[0323] According to one embodiment of the present invention, at least one or at least two of Q1-Q8 are selected from CR q , and the R q is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, or a combination thereof.

[0324] According to one embodiment of the present invention, L is selected from a single bond, 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, the same or different each time it occurs.

[0325] According to one embodiment of the present invention, wherein L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted fluorenyl group at each occurrence.

[0326] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted biphenylene group, the same or different each time it occurs.

[0327] According to one embodiment of the present invention, the first host compound is selected from the group consisting of H-1 to H-243, wherein the specific structures of H-1 to H-243 are as follows:

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347] According to one embodiment of the present invention, the second host compound in the electroluminescent device has a structure represented by Formula 5:

[0348]

[0349] in,

[0350] L xis identically or differently selected at each occurrence 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;

[0351] Each occurrence of V is selected from C, CR, or the like v or N, and at least one of V is C, and L x connect;

[0352] Each occurrence of U is selected from C, CR, or the like. u or N, and at least one of U is C, and with L x connect;

[0353] R v and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0354] Ar6 is selected, at each occurrence, identically or differently, 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;

[0355] Adjacent substituent R v and R u can optionally be linked to form a ring;

[0356] In this embodiment, "the adjacent substituent R v and R u"can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R v Between the two substituents R u Between the two substituents R v and R u Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0357] According to one embodiment of the present invention, the second host compound in the electroluminescent device has a structure represented by one of Formula 5-a to Formula 5-j:

[0358]

[0359]

[0360] in,

[0361] L x is identically or differently selected at each occurrence 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;

[0362] Each occurrence of V is selected from C, CR, or the like v or N, and at least one of V is C, and L x connect;

[0363] Each occurrence of U is selected from C, CR, or the like. u or N, and at least one of U is C, and with L x connect;

[0364] R v and R uEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0365] Ar6 is selected, at each occurrence, identically or differently, 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;

[0366] Adjacent substituent R v and R u can optionally be linked to form a ring;

[0367] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compounds X-1 to X-128, wherein the specific structures of compounds X-1 to X-128 are as follows:

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379] According to one embodiment of the present invention, in the electroluminescent device, 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.

[0380] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

[0381] According to another embodiment of the present invention, a compound combination is disclosed, which comprises the metal complex described in any one of the aforementioned embodiments.

[0382] Combination with other materials

[0383] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0384] The materials described herein as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0385] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kosite's electrochemical workstation, Anhui Beiyi Ke's sublimator, etc.), and is tested for structure confirmation and characteristics using methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical testing system, life test system, Beijing Liangtuo's ellipsometer, etc.), and are tested using methods well known to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, testing methods and other related content, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related content is no longer expanded in this patent.

[0386] Material synthesis example:

[0387] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0388] Synthesis Example 1: Synthesis of Metal Complex 127

[0389] Step 1:

[0390]

[0391] A dry 500 mL round-bottom flask was charged sequentially with 5-methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated with stirring at 130°C for 24 h. After cooling, the mixture was filtered, rinsed three times with methanol and n-hexane, and drained to yield 7.5 g of intermediate 1 (97% yield) as a yellow solid.

[0392] Step 2:

[0393]

[0394] To a dry 500 mL round-bottom flask, intermediate 1 (7.5 g, 6.8 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (3.8 g, 14.8 mmol) were added in sequence. The atmosphere was purged with nitrogen three times and protected with nitrogen. The mixture was stirred at room temperature overnight. The mixture was filtered through celite, rinsed twice with dichloromethane, and the organic phase below was collected and concentrated under reduced pressure to give 9.2 g of intermediate 2 (93% yield).

[0395] Step 3:

[0396]

[0397] To a dry 500 mL round-bottom flask were added intermediate 2 (1.3 g, 1.7 mmol), intermediate 3 (0.9 g, 2.3 mmol), and 250 mL of ethanol. The atmosphere was replaced with nitrogen three times and then protected with nitrogen. The reaction was heated at 100°C for 18 h. After the reaction was cooled, it was filtered through celite. The mixture was washed twice with methanol and n-hexane, respectively. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid product, metal complex 127 (0.75 g, 47.7% yield). The product was confirmed to be the target product with a molecular weight of 925.3.

[0398] Synthesis Example 2: Synthesis of Metal Complex 505

[0399] Step 1:

[0400]

[0401] A dry 500 mL round-bottom flask was charged sequentially with 5-tert-butyl-2-phenylpyridine (13.2 g, 62.9 mmol), iridium trichloride trihydrate (5.5 g, 15.7 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated with stirring at 130°C for 24 h. After cooling, the mixture was filtered, rinsed three times with methanol and n-hexane, and drained to yield 9.7 g of intermediate 4 (97% yield).

[0402] Step 2:

[0403]

[0404] To a dry 500 mL round-bottom flask were added intermediate 4 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (4.3 g, 16.7 mmol). The atmosphere was replaced with nitrogen three times under a nitrogen blanket and stirred overnight at room temperature. Filtered through celite, rinsed twice with dichloromethane, the organic phase below was collected and concentrated under reduced pressure to yield 13.2 g of intermediate 5 as a yellow solid (93% yield).

[0405] Step 3:

[0406]

[0407] To a dry 500 mL round-bottom flask were added intermediate 5 (1.4 g, 1.8 mmol), intermediate 3 (0.9 g, 2.2 mmol), and 300 mL of ethanol. The atmosphere was replaced with nitrogen three times and then protected with nitrogen. The reaction was heated at 100°C for 24 h. After the reaction cooled, it was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid product, metal complex 505 (0.75 g, 41.3% yield). The product was confirmed to be the target product with a molecular weight of 1009.4.

[0408] Synthesis Example 3: Synthesis of Metal Complex 520

[0409] Step 1:

[0410]

[0411] To a dry 250 mL round-bottom flask were added intermediate 6 (2.0 g, 4.9 mmol), intermediate 5 (2.7 g, 3.3 mmol), 2-ethoxyethanol, and 50 mL each of N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated at 100°C for 96 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid product, metal complex 520 (1.74 g, 51.5% yield). The product was confirmed to be the target product with a molecular weight of 1023.4.

[0412] Synthesis Example 4: Synthesis of Metal Complex 532

[0413] Step 1:

[0414]

[0415] To a dry 500 mL round-bottom flask were added intermediate 7 (1.8 g, 4.5 mmol), intermediate 5 (2.5 g, 3.0 mmol), and 300 mL of ethanol. The atmosphere was replaced with nitrogen three times and then protected with nitrogen. The reaction was heated at 100°C for 24 h. After the reaction cooled, it was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid product, metal complex 532 (0.55 g, 18.2% yield). The product was confirmed to be the target product with a molecular weight of 1009.4.

[0416] Synthesis Example 5: Synthesis of Metal Complex 181

[0417] Step 1:

[0418]

[0419] To a dry 500 mL round-bottom flask were added intermediate 2 (2.6 g, 3.5 mmol), intermediate 8 (2.2 g, 5.3 mmol), and 250 mL of ethanol. The atmosphere was replaced with nitrogen three times and then protected with nitrogen. The reaction was heated at 100°C for 18 h. After the reaction was cooled, it was filtered through celite. The mixture was washed twice with methanol and n-hexane, respectively. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid product, metal complex 181 (1.1 g, 33.3% yield). The product was confirmed to be the target product with a molecular weight of 943.2.

[0420] Synthesis Example 6: Synthesis of Metal Complex 559

[0421] Step 1:

[0422]

[0423] To a dry 500 mL round-bottom flask were added intermediate 5 (2.1 g, 2.6 mmol), intermediate 8 (1.5 g, 3.6 mmol), and 300 mL of ethanol. The atmosphere was replaced with nitrogen three times and then protected with nitrogen. The reaction was heated at 100°C for 24 h. After the reaction cooled, it was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid product, metal complex 559 (1.30 g, 48.7% yield). The product was confirmed to be the target product with a molecular weight of 1027.3.

[0424] Synthesis Example 7: Synthesis of Metal Complex 197

[0425] Step 1:

[0426]

[0427] To a dry 250 mL round-bottom flask were added Intermediate 2 (2.0 g, 2.8 mmol), Intermediate 9 (1.8 g, 3.9 mmol), 50 mL each of 2-ethoxyethanol and N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated at 100°C for 72 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on top of the celite was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to yield the metal complex 197 (1.2 g, 43.4% yield) as a yellow solid. This product was confirmed to be the target product with a molecular weight of 1006.3.

[0428] Synthesis Example 8: Synthesis of Metal Complex 460

[0429] Step 1:

[0430]

[0431] A dry 250 mL round-bottom flask was charged with 4-(methyl-d3)-2-phenylpyridine-5-d (5.0 g, 28.9 mmol), iridium trichloride (2.6 g, 7.4 mmol), 2-ethoxyethanol (60 mL), and water (20 mL). The mixture was heated to reflux under nitrogen and stirred for 24 h. After cooling, the mixture was filtered under reduced pressure and washed three times with methanol and then n-hexane to obtain 4.0 g of intermediate 10 as a yellow solid (94.8% yield).

[0432] Step 2:

[0433]

[0434] To a dry 500 mL round-bottom flask were added intermediate 10 (4.0 g, 3.5 mmol), anhydrous dichloromethane (250 mL), methanol (10 mL), and silver trifluoromethanesulfonate (1.9 g, 7.6 mmol). The atmosphere was replaced with nitrogen three times under a nitrogen blanket and stirred overnight at room temperature. The mixture was filtered through celite and washed twice with dichloromethane. The organic phase below was collected and concentrated under reduced pressure to afford 5.1 g of intermediate 11 (97.4% yield).

[0435] Step 3:

[0436]

[0437] To a dry 250 mL round-bottom flask were added intermediate 12 (1.5 g, 3.7 mmol), intermediate 11 (2.1 g, 2.2 mmol), 50 mL of N,N-dimethylformamide, and 50 mL of 2-ethoxyethanol. The mixture was heated to reflux under N2 protection and allowed to react for 96 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid product, metal complex 460 (0.82 g, 40.0% yield). This product was confirmed to be the target product with a molecular weight of 932.3.

[0438] Synthesis Example 9: Synthesis of Metal Complex 571

[0439] Step 1:

[0440]

[0441] To a dry 250 mL round-bottom flask were added intermediate 13 (1.4 g, 1.7 mmol), intermediate 5 (1.0 g, 2.4 mmol), 50 mL each of 2-ethoxyethanol and N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated at 100°C for 72 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to yield the metal complex 571 as a yellow solid (0.5 g, 28.4% yield). This product was confirmed to be the target product with a molecular weight of 1034.3.

[0442] Synthesis Example 10: Synthesis of Metal Complex 572

[0443] Step 1:

[0444]

[0445] To a dry 250 mL round-bottom flask were added intermediate 5 (2.4 g, 2.9 mmol), intermediate 14 (1.5 g, 3.4 mmol), 50 mL each of 2-ethoxyethanol and N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated at 100°C for 72 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to yield the yellow solid metal complex 572 (0.7 g, 23.0% yield). The product was confirmed to be the target product with a molecular weight of 1048.4.

[0446] Synthesis Example 11: Synthesis of Metal Complex 579

[0447] Step 1:

[0448]

[0449] To a dry 250 mL round-bottom flask were added Intermediate 5 (2.2 g, 2.7 mmol), Intermediate 15 (1.5 g, 3.6 mmol), 50 mL each of 2-ethoxyethanol and N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated at 100°C for 72 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid product, metal complex 579 (0.8 g, 30.7% yield). The product was confirmed to be the target product with a molecular weight of 1034.3.

[0450] Synthesis Example 12: Synthesis of Metal Complex 697

[0451] Step 1:

[0452]

[0453] A dry 500 mL round-bottom flask was charged sequentially with 5-neopentyl-2-phenylpyridine (13.4 g, 59.1 mmol), iridium trichloride trihydrate (5.2 g, 14.8 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water. The atmosphere was replaced with nitrogen three times under a nitrogen blanket and heated with stirring at 130°C for 24 h. After cooling, the mixture was filtered, rinsed three times with methanol and n-hexane, and drained to yield 8.5 g of intermediate 16 (88% yield).

[0454] Step 2:

[0455]

[0456] To a dry 500 mL round-bottom flask were added intermediate 16 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (4.3 g, 16.7 mmol). The atmosphere was replaced with nitrogen three times under a nitrogen blanket and stirred overnight at room temperature. Filtered through celite, rinsed twice with dichloromethane, and the organic phase below was collected and concentrated under reduced pressure to yield 11.8 g of intermediate 17 as a yellow solid (100% yield).

[0457] Step 3:

[0458]

[0459] To a dry 250 mL round-bottom flask were added intermediate 17 (2.0 g, 2.3 mmol), intermediate 13 (1.4 g, 3.2 mmol), 50 mL each of 2-ethoxyethanol and N,N-dimethylformamide. The atmosphere was replaced with nitrogen three times under nitrogen protection and heated at 100°C for 72 h. After cooling, the reaction mixture was filtered through celite. The mixture was washed twice with methanol and then with n-hexane. The yellow solid on the celite was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid product, metal complex 697 (0.8 g, 32.7% yield). The product was confirmed to be the target product with a molecular weight of 1062.4.

[0460] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0461] Device Example 1-1

[0462] First, a glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were deposited under a vacuum of approximately 10 -8 In the case of 100 nm, the ITO anode is sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound X-4 is used as an electron blocking layer (EBL). Then the metal complex 127 of the present invention is doped in compound X-4 and compound H-91 and co-deposited as a light-emitting layer (EML). On the EML, compound H-1 is used as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0463] Device Example 2-1

[0464] The implementation of Device Example 2-1 is the same as that of Device Example 1-1, except that the present metal complex 505 is used instead of the present metal complex 127 in the light-emitting layer.

[0465] Device Example 2-2

[0466] The implementation of Device Example 2-2 is the same as that of Device Example 1-1, except that the present metal complex 520 is used instead of the present metal complex 127 in the light-emitting layer.

[0467] Device Examples 2-3

[0468] The implementation of Device Example 2-3 is the same as that of Device Example 1-1, except that the present metal complex 532 is used instead of the present metal complex 127 in the light-emitting layer.

[0469] Device Comparison Example 1-1

[0470] The device of Comparative Example 1-1 was implemented in the same manner as that of Example 1-1, except that the metal complex 127 of the present invention was replaced with Compound GD1 in the emission layer (EML).

[0471] Device Comparison Example 2-1

[0472] The device of Comparative Example 2-1 was implemented in the same manner as that of Device Example 1-1, except that the metal complex 127 of the present invention was replaced with Compound GD2 in the emission layer (EML).

[0473] Device Comparison Example 2-2

[0474] The device of Comparative Example 2-2 was implemented in the same manner as that of Device Example 1-1, except that the metal complex 127 of the present invention was replaced with Compound GD3 in the emission layer (EML).

[0475] Device Comparison Examples 2-3

[0476] The device of Comparative Example 2-3 was carried out in the same manner as that of Device Example 1-1, except that the metal complex 127 of the present invention was replaced with Compound GD4 in the emission layer (EML).

[0477] Device Comparison Examples 2-4

[0478] The device of Comparative Example 2-4 was carried out in the same manner as that of Device Example 1-1, except that Compound GD5 was used in place of the metal complex 127 of the present invention in the emission layer (EML).

[0479] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.

[0480] Table 1 Device structures of Examples 1-1, 2-1 to 2-3 and Comparative Examples 1-1, 2-1 to 2-4

[0481]

[0482]

[0483] The material structure used in the device is shown below:

[0484]

[0485]

[0486] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE). External quantum efficiency (EQE) data is at 15mA / cm 2 The test was carried out under constant current. These data are recorded and shown in Table 2.

[0487] Table 2 Device data of Examples 1-1, 2-1 to 2-3 and Comparative Examples 1-1, 2-1 to 2-4

[0488]

[0489]

[0490] discuss:

[0491] Table 2 shows the device performance of the embodiments and comparative examples. The difference between Example 1-1 and Comparative Example 1-1, and between Examples 2-1 to 2-3 and Comparative Example 2-1, is that the specific Ar substituent of the metal complex is replaced by a phenyl group. When the half-width and maximum emission wavelength are equivalent and the driving voltage is slightly reduced, the CE, PE and EQE of the device are significantly improved. Compared with Comparative Example 1-1, Example 1-1 improves EQE by about 8.3%, PE by about 8.6%, and CE by about 7.4%. Compared with Comparative Example 2-1, Examples 2-1 to 2-3 improve EQE by about 10.2%, 8.2%, and 6.7%, respectively, PE by 14.7%, 16.8% and 10.5%, respectively, and CE by 9.6%, 7.4% and 5.3%, respectively. This shows that the metal complex of the present invention having a specific Ar substituent replacing the phenyl group is superior to the comparative example in many performance aspects of the device, and can significantly improve the overall performance of the device.

[0492] Metal complexes GD3, GD4 and GD5 with specific Ar substitution at other positions were synthesized for comparison, namely Comparative Examples 2-2 to 2-4. aThe biphenyl group of the ligand is substituted at different positions. Under the condition of the same driving voltage, the CE, PE and EQE of the device are greatly improved. Compared with Comparative Examples 2-2 to 2-4, Example 2-1 shows that the EQE is increased by 12.5%, 29.7% and 21.7% respectively; the PE is increased by 10.1%, 37.9% and 23.8% respectively; and the CE is increased by 7.2%, 32% and 22.6% respectively. This shows that the L-type ligand of the present invention with a specific Ar substituent at a specific position is a good choice for the device. a The metal complexes of the ligands outperformed the complexes of the comparative examples in multiple aspects of device performance, significantly improving the overall performance of the device. The observed advantages of introducing specific substituents at specific positions in the compounds of the present invention were completely unexpected and would have been impossible to predict, even for those skilled in the art.

[0493] Device Example 3-1

[0494] The method of Device Example 3-1 is the same as that of Device Example 1-1, except that the present metal complex 181 is used instead of the present metal complex 127 in the light-emitting layer.

[0495] Device Example 3-2

[0496] The method of device example 3-2 is the same as that of device example 1-1, except that the metal complex 559 of the present invention is used instead of the metal complex 127 of the present invention in the light-emitting layer.

[0497] Device Example 4-1

[0498] Device Example 4-1 was carried out in the same manner as Device Example 1-1, except that the present metal complex 197 was used in place of the present metal complex 127 in the light-emitting layer.

[0499] Device Example 4-2

[0500] The implementation of Device Example 4-2 is the same as that of Device Example 1-1, except that the present metal complex 460 is used instead of the present metal complex 127 in the light-emitting layer.

[0501] Device Example 4-3

[0502] The method of device example 4-3 is the same as that of device example 1-1, except that the metal complex 571 of the present invention is used instead of the metal complex 127 of the present invention in the light-emitting layer.

[0503] Device Example 4-4

[0504] The method of device example 4-4 is the same as that of device example 1-1, except that the metal complex 572 of the present invention is used instead of the metal complex 127 of the present invention in the light-emitting layer.

[0505] Device Examples 4-5

[0506] The method of device example 4-5 is the same as that of device example 1-1, except that the metal complex 579 of the present invention is used instead of the metal complex 127 of the present invention in the light-emitting layer.

[0507] Device Examples 4-6

[0508] Device Example 4-6 was carried out in the same manner as Device Example 1-1, except that the present metal complex 697 was used in place of the present metal complex 127 in the light-emitting layer.

[0509] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.

[0510] Table 3 Device structures of Examples 3-1 to 3-2 and 4-1 to 4-6

[0511]

[0512] The new material structure used in the device is shown below:

[0513]

[0514] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE). External quantum efficiency (EQE) data is at 15mA / cm 2 The test was carried out under constant current. These data are recorded and shown in Table 4.

[0515] Table 4 Device data of Examples 3-1 to 3-2 and 4-1 to 4-6

[0516]

[0517]

[0518] discuss:

[0519] Table 4 shows the device performance of Examples 3-1 to 3-2 and 4-1 to 4-6 of the present invention. a In addition to having specific Ar substituents at specific positions of the ligand, the ligand further has fluorine substitutions. Compared with Examples 1-1 and 2-1 without fluorine substitutions, EQE, CE and PE are slightly improved.

[0520] Meanwhile, the metal complexes of Examples 4-1 to 4-6 except for L a In addition to having a specific Ar substituent at a specific position of the ligand, it further includes a cyano substitution. Compared with Examples 1-1, 2-1 to 2-3 without cyano substitution, all of them show further significant improvements, such as a significant reduction in driving voltage, a narrowing of the half-peak width between 21.7nm and 26.9nm, and a reduction in the maximum emission wavelength λ. max Under similar circumstances, narrowing the half-peak width is conducive to obtaining more saturated luminescence. The EQE can reach a level greater than 24%, especially Example 4-1 reaches 26.35%.

[0521] The above results show that the L containing specific Ar substituted at a specific position of the present invention a The metal complex of the ligand is further a The ligand has at least one substituent, such as fluorine or cyanide, which is superior to the complex of the comparative example in many performance aspects of the device, can significantly improve the overall performance of the device, and the device performance can be further improved compared to the metal complex containing only specific Ar substitution.

[0522] At the same time, the metal complex 505 of the present invention was used as a luminescent dopant and was combined with first host compounds of different structures to be applied to the light-emitting layer of an organic electroluminescent device to prepare device embodiments 5-1 to 5-5, and their performance was characterized.

[0523] Device Example 5-1

[0524] Device Example 5-1 was implemented in the same manner as Device Example 2-1, except that the ratio of Compound X-4, Compound H-91, and Metal Complex 505 in the light-emitting layer was 66:28:6.

[0525] Device Example 5-2

[0526] Device Example 5-2 was carried out in the same manner as Device Example 5-1, except that Compound H-1 was used instead of H-91 in the light-emitting layer.

[0527] Device Example 5-3

[0528] Device Example 5-3 was carried out in the same manner as Device Example 5-1, except that Compound H-141 was used instead of H-91 in the light-emitting layer.

[0529] Device Example 5-4

[0530] Device Example 5-4 was carried out in the same manner as Device Example 5-1, except that Compound H-171 was used instead of Compound H-91 in the light-emitting layer.

[0531] Device Example 5-5

[0532] Device Example 5-5 was carried out in the same manner as Device Example 5-1, except that Compound H-172 was used instead of Compound H-91 in the light-emitting layer.

[0533] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.

[0534] Table 5 Device structures of device examples 5-1 to 5-5

[0535]

[0536]

[0537] The new material structure used in the device is shown below:

[0538]

[0539] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE). External quantum efficiency (EQE) data is at 15mA / cm 2 The test was conducted at a constant current. These data are recorded and shown in Table 6.

[0540] Table 6 Device data of device examples 5-1 to 5-5

[0541]

[0542] From the above data, it can be seen that the performance of Examples 5-1 to 5-5 is comparable to that of Example 2-1, wherein the EQE is also around 24%, and in particular, the EQE of Example 5-2 reaches 25.03%. a The metal complex of the ligand can be used as a luminescent material in the luminescent layer of an electroluminescent device. When it is used in combination with a host material of different structures, excellent device performance can be achieved.

[0543] In summary, the present invention comprises L having a specific Ar substitution at a specific position aIn devices, the metal complexes of the present invention exhibit superior performance compared to existing metal complexes with Ar substituents at other positions within the La ligand, reducing driving voltage and improving device efficiency, particularly EQE, ultimately significantly enhancing overall device performance. The observed advantages of the compounds of the present invention are completely unexpected and would have been impossible to predict, even for those skilled in the art.

[0544] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. A metal complex, wherein: The metal complex has Ir(L a ) m (L b ) 3-m The general formula, wherein m is selected from 1, two L b the same or different; wherein La has a structure represented by Formula 1: In formula 1, Cy is selected from the same or different Each occurrence of R is the same or different, indicating mono-substitution, poly-substitution, or no substitution; when multiple R are present in any structure, the R are the same or different; Among them, '#' indicates the position connected to the metal Ir, represents the position connected to Formula 1; X is selected from the group consisting of O, S and Se; X1-X5 are selected from CR in the same or different way each time they appear. x ; Ar has a structure represented by Formula 2: a is selected from 0 or 1; R a1 and R a2 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; Ring Ar1 and ring Ar2 are identically or differently selected from benzene rings, naphthalene rings, biphenyl rings, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; "*" indicates the attachment position of Formula 2; R, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, cyano, isocyano, and Its combination; L b Each occurrence is identically or differently selected from any one of the following groups: in, R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R a , R b Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; The metal complex is not the following compound:

2. The metal complex according to claim 1, wherein R, at each occurrence, is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

3. The metal complex according to claim 1 or 2, wherein L a Each occurrence is identically or differently selected from the group consisting of: wherein X is selected from the group consisting of O, S and Se; Ar has a structure represented by Formula 2: a is selected from 0 or 1; Ring Ar1 and ring Ar2 are identically or differently selected from benzene rings, naphthalene rings, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; "*" indicates the connection position of formula 2; R, R x , R a1 and R a2 Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; L b Each occurrence is identically or differently selected from any one of the following groups: in, R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cyano, and combinations thereof; R a , R b Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, and combinations thereof.

4. The metal complex according to claim 1, wherein Metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 3: in, X is selected from the group consisting of O, S and Se; m is selected from 1; two L b Same or different; Y1-Y4 are selected from CR y ; X1-X5 are selected from CR in the same or different way each time they appear. x ; Ar has a structure represented by Formula 2: a is selected from 0 or 1; R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no-substitution; Ring Ar1 and ring Ar2 are identically or differently selected from benzene rings, naphthalene rings, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cyano, and combinations thereof; R1-R8 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, cyano, and combinations thereof; "*" indicates the connection position of formula 2.

5. The metal complex according to claim 1 or 4, wherein X is selected from O or S, and a is selected from 1.

6. The metal complex according to claim 1 or 4, wherein R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

7. The metal complex according to claim 1 or 4, wherein R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, and combinations thereof.

8. The metal complex according to claim 1 or 4, wherein Ra1 and Ra2 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, and combinations thereof.

9. The metal complex as claimed in claim 1 or 4, wherein in Ar, ring Ar1 and ring Ar2 are identically or differently selected from the group consisting of a benzene ring, a naphthalene ring, and a combination thereof each time they appear; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.

10. The metal complex according to claim 1 or 4, wherein Ar at each occurrence is identically or differently selected from the group consisting of: and combinations thereof; Optionally, the above groups may be partially or fully deuterated; wherein "*" indicates the attachment position of the Ar.

11. The metal complex according to claim 1 or 4, wherein R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cyano, and combinations thereof.

12. The metal complex according to claim 1 or 4, wherein R x At least one of them is selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, cyano, and combinations thereof.

13. The metal complex according to claim 1 or 4, wherein R x At least one of them is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a cyano group, and combinations thereof.

14. The metal complex according to claim 1 or 4, wherein At least one of X1-X5 is selected from CR x , and the R x It is cyano or fluorine.

15. The metal complex according to claim 1 or 4, wherein At least one of X3-X5 is selected from CR x , and the R x It is cyano or fluorine.

16. The metal complex according to claim 1 or 4, wherein X5 is CR x , and the R x It is cyano or fluorine.

17. The metal complex according to claim 4, wherein R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

18. The metal complex according to claim 4, wherein At least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

19. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

20. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.

21. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; optionally, the hydrogen in the above groups can be partially or completely deuterated.

22. The metal complex according to claim 1, wherein L a Each occurrence is identically or differently selected from the group consisting of:

23. The metal complex according to claim 22, wherein L b Each occurrence is identically or differently selected from the group consisting of:

24. The metal complex according to claim 23, wherein The metal complex has IrL a (L b )2 structure, where two L b Same, where L a and L b They correspond to the structures shown in the following table: 。 25. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 24.

26. The electroluminescent device of claim 25, wherein: The organic layer including the metal complex is a light-emitting layer.

27. The electroluminescent device of claim 25, wherein: The electroluminescent device emits green light or white light.

28. The electroluminescent device of claim 26, wherein: The light-emitting layer includes a first host compound.

29. The electroluminescent device of claim 28, wherein the light-emitting layer further comprises a second host compound.

30. The electroluminescent device of claim 29, wherein the first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

31. The electroluminescent device of claim 28, wherein: The first host compound has a structure represented by Formula 4: in, Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, and at least one of E1-E6 is C, and is connected to formula A; in, Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" can be the same or different; p is 0 or 1; r is 0 or 1; When Q is selected from N, p is 0 and r is 1; When Q is selected from the group consisting of O, S, Se, NR", CR"R", SiR"R", GeR"R" and R"C=CR", p is 1 and r is 0; L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N; R e , R' and R q each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; "*" represents the connection position between Formula A and Formula 4; Adjacent substituent R e , R”, R q Can optionally be linked to form a ring.

32. The electroluminescent device of claim 31, wherein each occurrence of E1-E6 is identically or differently selected from C, CR e or N, and three of E1-E6 are N, and at least one of E1-E6 is CR e , and the R e Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; and / or Q is selected, identically or differently, at each occurrence, from O, S, N or NR"; and / or at least one or at least two of Q1-Q8 are selected from CR q , and the R q is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof; and / or L is identically or differently selected at each occurrence from a single bond, 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.

33. The electroluminescent device of claim 28, wherein: The first host compound is selected from the group consisting of:

34. The electroluminescent device of claim 29, wherein: The second host compound has a structure represented by Formula 5: in, L x is selected, at each occurrence, identically or differently, 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; Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect; Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and L x connect; R v and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Ar6 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R v and R u Can optionally be linked to form a ring.

35. The electroluminescent device of claim 34, wherein: The second host compound has a structure represented by one of Formula 5-a to Formula 5-j:

36. The electroluminescent device of claim 29, wherein: The second host compound is selected from the group consisting of:

37. The electroluminescent device as claimed in claim 29, wherein a 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.

38. The electroluminescent device according to claim 29, wherein the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.

39. A compound combination comprising the metal complex according to any one of claims 1-24.

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