Metal complex, electroluminescent device and application thereof

Abstract

The present invention provides a metal complex, an electroluminescent device and application thereof. The metal in the metal complex is selected from metals with a relative atomic mass greater than 40, and contains a ligand L a , the L a The structure shown in Formula I is as follows, and a substituent containing a saturated heterocycle is introduced at a specific site, and the luminescent properties of the metal complex are optimized through the mutual synergy between multiple substituents. The metal complex is used as a phosphorescent luminescent material of an electroluminescent device, which can significantly improve the saturation of the luminescent color, and at the same time obtain higher luminous efficiency, luminous power efficiency and external quantum efficiency.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a metal complex, an electroluminescent device and applications thereof. 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 photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices, etc.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included a hole transport layer of arylamine, and an electron transport layer and a light-emitting layer of tri-8-hydroxyquinoline-aluminum; 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 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 OLED is a self-luminous solid-state device, it offers 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 divided into three different types based on their light emission mechanism. The OLED invented by Tang and Van Slyke is a fluorescent OLED, which uses only singlet light emission, and the triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%, which limits the commercialization of fluorescent OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters, thereby being able to harvest singlet and triplet states and achieve 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds; these emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be divided into small molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer; as long as they have a precise structure, the molecular weight of a small molecule can be large; in addition, dendrimers with a well-defined structure are also considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-group luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] There are various methods for making OLEDs. Small molecule OLEDs are usually made by vacuum thermal evaporation. Polymer OLEDs are made by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be made by solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one or more luminescent layers to achieve the desired spectrum. Green, yellow and red phosphorescent OLEDs 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 usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, the field of OLED devices also expects to have a more saturated emission spectrum, higher efficiency and longer device life.

[0008] Phosphorescent iridium complexes can be used as phosphorescent doping materials for light-emitting layers and applied in the field of organic electroluminescence or display. In order to meet the needs of different situations, by adjusting the structural type of the material ligand, the color of the material can be adjusted on a certain basis to obtain phosphorescent iridium complexes with different emission wavelengths.

[0009] WO2019221481A1 discloses an organic phosphorescent material, the general structural formula of which is Among them, R1 and R2 can be alkyl, cycloalkyl, heterocyclic, cyclic ketone, heteroaryl, etc., and a large number of structures disclosed thereof are mentioned. This application focuses on the application of two substituents at specific positions on the isoquinoline ring of the phenylisoquinoline ligand, and does not notice that different effects can be achieved by introducing specific substituents on the phenyl group of the phenylisoquinoline ligand.

[0010] Although metal complex structures containing heteroatom substituents have been reported in the literature, the types of materials are relatively few, and the existing phosphorescent materials still have shortcomings such as low luminescent color saturation and low luminous efficiency. Therefore, the development of more types and higher performance electroluminescent materials and devices remains the research focus in this field. Summary of the invention

[0011] In order to develop more types of electroluminescent materials with higher performance, one of the objects of the present invention is to provide a metal complex, wherein the metal in the metal complex is selected from metals with a relative atomic mass greater than 40, and comprises a ligand L a , the L a Having the structure shown in Formula I:

[0012]

[0013] In Formula I, the dotted line represents the binding site between the ligand and the metal atom;

[0014] In Formula I, R is selected from the group consisting of 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 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 2- 20 carbon atoms alkenyl, 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0015] In Formula I, X1, X2, X3, and X4 are each independently selected from CR x or N, the adjacent substituent R x can optionally be linked to form a ring;

[0016] In Formula I, Y1, Y2, and Y3 are each independently selected from CR y1 , CR y2 or N, and at least one of Y1, Y2, and Y3 is CR y2 ;

[0017] R y2 It has a structure as shown in Formula II:

[0018]

[0019] In formula II, * represents the attachment site of the group;

[0020] In formula II, C1 is carbon;

[0021] In formula II, ring A is selected from a substituted or unsubstituted saturated heterocycle having 3 to 10 ring carbon atoms and at least one heteroatom X;

[0022] Each occurrence of X is identically or differently selected from the group consisting of: NR n , O, S and Se;

[0023] R n selected from the group consisting of hydrogen, deuterium, 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 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 alkenyl 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;

[0024] In Formula II, L is selected, at each occurrence, identically or differently, from the group consisting of 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 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;

[0025] In Formula II, R Aa represents mono-, poly- or unsubstituted;

[0026] In Formula I and Formula II, R x , R y1 , R Aa , R AcEach 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 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 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof;

[0027] Adjacent substituent R Aa , R Ac , R n Can optionally be linked to form a ring.

[0028] In the metal complex provided by the present invention, saturated heterocyclic substitution is performed on the metal complex structure, which not only improves the luminous efficiency of the material, but also greatly improves the saturation of the luminescent color of the material.

[0029] A second object of the present invention is to provide an electroluminescent device, comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex as described above.

[0030] A third object of the present invention is to provide an application of the electroluminescent device as described above in an electronic device, an electronic component module, a display device or a lighting device.

[0031] A fourth object of the present invention is to provide a compound formulation comprising the metal complex as described above.

[0032] Compared with the prior art, the present invention has the following beneficial effects:

[0033] The present invention provides a kind of comprising specific ligand L a The metal complex, the ligand L a Substituents containing saturated heterocycles are introduced at specific sites, and the luminescent properties of the metal complex are optimized through the mutual synergy between multiple substituents. As a phosphorescent luminescent material of an electroluminescent device, the metal complex can significantly improve the saturation of the luminescent color, while obtaining higher luminous efficiency, luminous power efficiency and external quantum efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 A schematic diagram of an organic light-emitting device containing the metal complex and compound formula provided by the present invention;

[0035] Figure 2 A schematic diagram of another organic light-emitting device containing the metal complex and compound formula provided by the present invention. DETAILED DESCRIPTION

[0036] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0037] OLEDs can be manufactured on a variety of substrates, such as glass, plastic or 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 US7279704B2, the entire contents of which are incorporated herein by reference.

[0038] There are 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, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of 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, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0039] The above layered structure is provided by way of non-limiting example. The functions 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 light-emitting spectrum.

[0040] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0041] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the 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 an 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.

[0042] 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, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays, vehicle displays, and taillights.

[0043] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0044] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where 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, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0045] 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.

[0046] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0047] 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).

[0048] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but 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 for the conversion 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 (IRISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0049] 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-metal-containing 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. Generally, 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).

[0050] Definition of Substituent Terms

[0051] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0052] Alkyl - as used herein, includes straight chain and branched alkyl. Alkyl can be an alkyl with 1 to 20 carbon atoms, preferably an alkyl with 1 to 6 carbon atoms, more preferably an alkyl with 1 to 6 carbon atoms. Examples of alkyl 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. In addition, alkyl can be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, alkyl can be optionally substituted.

[0053] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0054] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0055] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, 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 may be optionally substituted.

[0056] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl 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 may be optionally substituted.

[0057] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl 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, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0058] Heterocyclic or heterocyclic - 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 atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl.

[0059] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 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, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0060] Alkoxy-as used herein, 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 described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0061] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0062] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups 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, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0063] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 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, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0064] Arylsilyl - as used herein, encompasses at least one aryl-substituted silyl. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0065] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment 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 nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0066] In the present disclosure, unless otherwise defined, when 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 aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino. The present invention relates to an alkyl radical having 3-20 carbon atoms, an unsubstituted cycloalkyl radical having 3-20 ring carbon atoms, an unsubstituted heteroalkyl radical having 1-20 carbon atoms, an unsubstituted heterocyclyl radical having 3-20 ring atoms, an unsubstituted aralkyl radical having 7-30 carbon atoms, an unsubstituted alkoxy radical having 1-20 carbon atoms, an unsubstituted aryloxy radical having 6-30 carbon atoms, an unsubstituted alkenyl radical having 2-20 carbon atoms, an unsubstituted aryl radical having 6-30 carbon atoms, an unsubstituted heteroaryl radical having 3-30 carbon atoms, an unsubstituted alkylsilyl radical having 3-20 carbon atoms, an unsubstituted arylsilyl radical having 6-20 carbon atoms, an unsubstituted amino radical having 0-20 carbon atoms, an acyl radical, a carbonyl radical, a carboxylic acid radical, an ester radical, a cyano radical, an isocyano radical, a mercapto radical, a sulfinyl radical, a sulfonyl radical, a phosphino radical, and a combination thereof.

[0067] 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 a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0068] In the compounds mentioned in this disclosure, 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 the compounds may be preferred because it enhances the efficiency and stability of the device.

[0069] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0070] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, 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 both the situation where adjacent substituents can be connected to form a ring and 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, 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.

[0071] The expression that adjacent substituents can be optionally 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, which can be exemplified by the following formula:

[0072]

[0073] The expression that adjacent substituents can be optionally 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 by a chemical bond to form a ring, which can be exemplified by the following formula:

[0074]

[0075] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0076]

[0077] In a specific embodiment, the present invention provides a metal complex, wherein the metal in the metal complex is selected from metals with a relative atomic mass greater than 40, and comprises a ligand L a , the L a Having the structure shown in Formula I:

[0078]

[0079] In Formula I, the dotted line represents the binding site between the ligand and the metal atom;

[0080] In Formula I, R is selected from the group consisting of 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 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 2- 20 carbon atoms alkenyl, 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0081] In Formula I, X1, X2, X3, and X4 are each independently selected from CR x or N, the adjacent substituent R x can optionally be linked to form a ring;

[0082] In Formula I, Y1, Y2, and Y3 are each independently selected from CR y1 , CR y2 or N, and at least one of Y1, Y2, and Y3 is CR y2 ;

[0083] R y2 It has a structure as shown in Formula II:

[0084]

[0085] In formula II, * represents the attachment site of the group;

[0086] In formula II, C1 is carbon;

[0087] In formula II, ring A is selected from a substituted or unsubstituted saturated heterocycle having 3 to 10 ring carbon atoms and at least one heteroatom X;

[0088] Each occurrence of X is identically or differently selected from the group consisting of: NR n , O, S and Se;

[0089] R n selected from the group consisting of hydrogen, deuterium, 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 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 alkenyl 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;

[0090] In Formula II, L is selected, at each occurrence, identically or differently, from the group consisting of 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 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;

[0091] In Formula II, R Aa represents mono-, poly- or unsubstituted;

[0092] In Formula I and Formula II, R x , R y1 , R Aa , R AcEach 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 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 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof;

[0093] Adjacent substituent R Aa , R Ac , R n Can optionally be linked to form a ring.

[0094] In this embodiment, the adjacent substituent R x can be optionally connected to form a ring, which is intended to indicate that when there are multiple substituents R x When any adjacent substituent R x Obviously, when there are multiple substituents R x When any adjacent substituent R x They can also not be connected to form a ring.

[0095] In this embodiment, the adjacent substituent R Aa , R Ac , R n can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R Aa When adjacent substituent groups, for example, adjacent substituent groups R Aa Between, substituent R Aa With R Ac , Substituent R Aa With R n Between and substituent R Ac With R n Any one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.

[0096] In one embodiment, the metal complex has the structural formula M(L a ) m (Lb ) n (L c ) q ;

[0097] Wherein, M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt; L a , L b , L c are the first ligand, the second ligand, and the third ligand coordinated with the M respectively; L a , L b , L c can optionally be linked to form a multidentate ligand; for example, L a , L b and L c Any two of can be connected to form a tetradentate ligand; for example, L a , L b and L c They can be linked to each other to form hexadentate ligands;

[0098] m and n are each independently selected from 1 or 2; q is selected from 0 or 1; the sum of m, n, q is equal to the oxidation state of M;

[0099] When m is 2, 2 L a Can be the same or different;

[0100] When n is 2, 2 L b Can be the same or different;

[0101] The L b , L c Each is independently selected from any one of the following structures:

[0102]

[0103] Among them, the dotted lines represent the binding sites between the ligand and the metal atom;

[0104] R a , R b , R c Each independently represents mono-, poly- or unsubstituted;

[0105] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0106] X c , X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NRN2 ;

[0107] R a , R b , R c , R N1 , R N2 , R C1 , 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 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 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof;

[0108] Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 , R C2 Can optionally be linked to form a ring.

[0109] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between 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 Rb 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, the substituent R a and R N2 Between, the substituent R b and R N2 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.

[0110] In a preferred embodiment, the M is selected from Pt or Ir.

[0111] In a preferred embodiment, the M is Ir.

[0112] In one embodiment, Y1 and Y3 in Formula I are each independently selected from CR y1 or CR y2 , or Y2 is CR y2 .

[0113] In a preferred embodiment, Y2 is CR y2 , said Y1, Y3 are each independently selected from CR y1 .

[0114] In a preferred embodiment, the R y1 Selected from hydrogen or deuterium.

[0115] In one embodiment, X1, X2, X3, and X4 are each independently selected from CR x or N, at least one of which is N; the adjacent substituent R x Can optionally be linked to form a ring.

[0116] In a preferred embodiment, any one of X1, X2, X3, and X4 is N.

[0117] In a preferred embodiment, X1, X2 and X4 are CR x , X3 is N.

[0118] In one embodiment, X1, X2, X3, and X4 are each independently selected from CR x, or X1, X2 and X4 are each independently selected from CR x , X3 is N; and there are 2 adjacent substituents R x Connect to form an unsaturated ring.

[0119] In a preferred embodiment, the unsaturated ring is selected from unsaturated rings having 5 to 10 ring atoms.

[0120] In a preferred embodiment, the unsaturated ring is selected from a five-membered unsaturated carbon ring, a five-membered heteroaromatic ring, a six-membered heteroaromatic ring or a benzene ring.

[0121] In a specific embodiment, the L a Select any one of the following structures:

[0122]

[0123]

[0124] Among them, the dotted lines represent the binding sites between the ligand and the metal atom;

[0125] R xx Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0126] R, R y1 , R y2 , R x Each independently has the same definition as in Formula I;

[0127] Z is selected, at each occurrence, identically or differently, from the group consisting of: O, S and CR w R w ; When two substituents R are present at the same time w When two R w can be the same or different; for example, in CR w R w In the two R w Can be the same or different;

[0128] R xx , R weach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted aryl having 7-30 carbon atoms, substituted or unsubstituted heteroaryl having 7-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, hydroxyl, thiol, and combinations thereof;

[0129] Adjacent substituent R xx , R w Can optionally be linked to form a ring.

[0130] In this embodiment, the adjacent substituent R xx , R w can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R xx When adjacent substituent groups, such as adjacent substituents R xx Between the two substituents R w Between, the substituent R xx With R w Any one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.

[0131] In a specific embodiment, the R x , R xx , R y1 At least one of the following is independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted aryl having 7-30 carbon atoms, substituted or unsubstituted heteroaryl having 7-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, hydroxyl, thiol, and combinations thereof.

[0132] In a preferred embodiment, the R x , R xx , R y1At least two of the above are independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, cyano, hydroxyl, thiol, and combinations thereof.

[0133] In a preferred embodiment, the R x , R xx , R y1 At least three of the above are independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, cyano, hydroxyl, thiol, and combinations thereof.

[0134] In one embodiment, the metal complex is an iridium complex and has a structure as shown in Formula III, Formula IV or Formula V:

[0135]

[0136] In Formula III, Formula IV, and Formula V, m is 1 or 2;

[0137] R1, R2, R3, R4, R5, R6, R7 are each independently 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 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 alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0-20 carbon atoms, and combinations thereof;

[0138] Adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally linked to form a ring.

[0139] In this embodiment, adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally connected to form a ring, which is intended to mean that adjacent substituent groups, for example, between substituents R1 and R2, between substituents R1 and R3, between substituents R2 and R3, between substituents R4 and R5, between substituents R5 and R6, between substituents R4 and R6, between substituents R1 and R7, between substituents R2 and R7, between substituents R3 and R7, between substituents R4 and R7, between substituents R5 and R7, and between substituents R6 and R7, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring.

[0140] In a preferred embodiment, in Formula III to Formula V, at least one of R1, R2, and R3 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, and combinations thereof; and / or at least one of R4, R5, and R6 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, and combinations thereof.

[0141] In a preferred embodiment, in Formula III to Formula V, at least two of R1, R2, and R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, and combinations thereof; and / or at least two of R4, R5, and R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, and combinations thereof.

[0142] In a specific embodiment, the L a It has a structure as shown in Formula VI:

[0143]

[0144] In Formula VI, the dotted line represents the binding site between the ligand and the metal atom;

[0145] In Formula VI, R, R y2 Each independently has the same definition as in Formula I;

[0146] In Formula VI, R x1 , R x2 , R x3 Each is independently 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0147] In a preferred embodiment, the R x1 , R x2 are each independently selected from hydrogen or deuterium; said R x3 The group is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms.

[0148] In a preferred embodiment, the R x3 Selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, 4,4-dimethylcyclohexyl, 4,4-diethylcyclohexyl, 4-oxacyclohexyl, trimethylsilyl, dimethylisopropylsilyl, and partially or completely deuterated versions of the above groups.

[0149] In a preferred embodiment, each occurrence of X is identical or different and is selected from NR n , O or S.

[0150] In a preferred embodiment, X is O.

[0151] In a preferred embodiment, when the number of X in the ring A is ≥2, any two X are separated by at least one ring carbon atom.

[0152] In one embodiment, the ring A is selected from a saturated heterocyclic ring having 4-7 ring atoms.

[0153] In a preferred embodiment, the ring A is selected from a saturated heterocyclic ring having 5-6 ring atoms.

[0154] In a preferred embodiment, there is at least one ring carbon atom between X and C1 in the ring A.

[0155] In a specific embodiment, R is selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0156] In a preferred embodiment, R is selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, phenyl, and partially or completely deuterated groups thereof.

[0157] In a specific embodiment, each occurrence of L is identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, and a substituted or unsubstituted cycloalkylene group having 3 to 10 ring carbon atoms.

[0158] In a preferred embodiment, the L is selected from a single bond or a methylene group.

[0159] In a preferred embodiment, said L is a single bond.

[0160] In a specific embodiment, the R Aa , R Ac Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms.

[0161] In a preferred embodiment, the R Aa , R Ac is selected, identically or differently on each occurrence, from hydrogen, deuterium, methyl, ethyl, isopropyl or isobutyl.

[0162] In a specific embodiment, the L a Each time it appears, choose the same or different one from L a1-1 ~L a1-844 , L a2-1 ~L a2-520 , L a3-1 ~L a3-170 , L a4-1 ~L a4-380 , L a5-1 ~L a5-320 , L a6-1 ~L a6-80 and L a7-1 ~L a7-224 Groups composed of:

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] The dotted lines represent the binding sites between the ligand and the metal atom.

[0226] In a specific embodiment, the L b Each time it appears, choose the same or different one from L b1 ~L b322 Groups composed of:

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] The dotted lines represent the binding sites between the ligand and the metal atom.

[0235] In a specific embodiment, the L c Each time it appears, choose the same or different one from L c1 ~L c231 Groups composed of:

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242] The dotted lines represent the binding sites between the ligand and the metal atom.

[0243] In one embodiment, the metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure; wherein, when the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1-1 ~L a1-844 , L a2-1 ~L a2-520 , L a3-1 ~L a3-170 , L a4-1 ~L a4-380 , L a5-1 ~La5-320 , L a6-1 ~L a6-80 and L a7-1 ~L a7-224 Any one or any two of the group consisting of L b Choose from L b1 To L b322 Any one of the group consisting of; when the metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, choose the same or different one from L a1-1 ~L a1-844 , L a2-1 ~L a2-520 , L a3-1 ~L a3-170 , L a4-1 ~L a4-380 , L a5-1 ~L a5-320 , L a6-1 ~L a6-80 and L a7-1 ~L a7-224 Any one or any two of the group consisting of L c Choose from L c1 To L c231 Any one of the group consisting of; when the metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1-1 ~L a1-844 , L a2-1 ~L a2-520 , L a3-1 ~L a3-170 , L a4-1 ~L a4-380 , L a5-1 ~L a5-320 , L a6-1 ~L a6-80 and L a7-1 ~L a7-224 Any one of the group consisting of L c Each time it appears, choose the same or different one from L c1 -L c231 Any one or any two of the group consisting of.

[0244] In one embodiment, the metal complex is selected from the group consisting of Compound 1 to Compound 430; wherein Compound 1 to Compound 400 have Ir(L a )2(L b ) structure, where two La Same, L a and L b They correspond to the structures selected from the following table:

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251] Compounds 401 to 420 have Ir(L a )(L b )(L c ) structure, where L a , L b and L c They correspond to the structures selected from the following table:

[0252] Compound <![CDATA[L a ]]> <![CDATA[L b ]]> Lc 401 <![CDATA[L a1-12 ]]> <![CDATA[L b3 ]]> <![CDATA[L c1 ]]> 402 <![CDATA[L a1-68 ]]> <![CDATA[L b7 ]]> <![CDATA[L c3 ]]> 403 <![CDATA[L a1-322 ]]> <![CDATA[L b31 ]]> <![CDATA[L c3 ]]> 404 <![CDATA[L a1-346 ]]> <![CDATA[L b80 ]]> <![CDATA[L c9 ]]> 405 <![CDATA[L a1-354 ]]> <![CDATA[L b88 ]]> <![CDATA[L c1 ]]> 406 <![CDATA[L a1-362 ]]> <![CDATA[L b122 ]]> <![CDATA[L c3 ]]> 407 <![CDATA[L a1-385 ]]> <![CDATA[L b126 ]]> <![CDATA[L c9 ]]> 408 <![CDATA[L a1-386 ]]> <![CDATA[L b157 ]]> <![CDATA[L c17 ]]> 409 <![CDATA[L a1-676 ]]> <![CDATA[L b182 ]]> <![CDATA[L c31 ]]> 410 <![CDATA[L a1-729 ]]> <![CDATA[L b209 ]]> <![CDATA[L c1 ]]> 411 <![CDATA[L a2-4 ]]> <![CDATA[L b3 ]]> <![CDATA[L c3 ]]> 412 <![CDATA[L a2-24 ]]> <![CDATA[L b7 ]]> <![CDATA[L c9 ]]> 413 <![CDATA[L a2-64 ]]> <![CDATA[L b31 ]]> <![CDATA[L c17 ]]> 414 <![CDATA[L a2-90 ]]> <![CDATA[L b80 ]]> <![CDATA[L c31 ]]> 415 <![CDATA[L a3-55 ]]> <![CDATA[L b88 ]]> <![CDATA[L c68 ]]> 416 <![CDATA[L a3-157 ]]> <![CDATA[L b122 ]]> <![CDATA[L c1 ]]> 417 <![CDATA[L a5-52 ]]> <![CDATA[L b126 ]]> <![CDATA[L c9 ]]> 418 <![CDATA[L a6-15 ]]> <![CDATA[L b157 ]]> <![CDATA[L c1 ]]> 419 <![CDATA[L a7-57 ]]> <![CDATA[L b182 ]]> <![CDATA[L c68 ]]> 420 <![CDATA[L a7-161 ]]> <![CDATA[L b209 ]]> <![CDATA[L c31 ]]>

[0253] Compounds 421 to 430 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b They correspond to the structures selected from the following table:

[0254]

[0255]

[0256] The metal complex provided by the present invention can be prepared by a synthesis method disclosed in the prior art, and for the sake of simplicity, the present invention will not list them one by one. Exemplarily, the synthesis route of the metal complex is as follows: after synthesizing and preparing the ligand of the corresponding compound, the ligand reacts with iridium trichloride to obtain the corresponding iridium dimer, and then the iridium dimer reacts with the corresponding diketone to obtain the metal complex.

[0257] In a specific embodiment, the present invention provides an electroluminescent device, comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex as described above.

[0258] In a specific embodiment, the organic layer includes a light-emitting layer, and the light-emitting material of the light-emitting layer includes the metal complex as described above.

[0259] In a preferred embodiment, the electroluminescent device emits red light or white light.

[0260] In a preferred embodiment, the light-emitting layer further comprises at least one host material.

[0261] In a preferred embodiment, the light-emitting layer further comprises at least two host materials.

[0262] In a preferred embodiment, at least one of the host materials 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.

[0263] In a specific embodiment, the present invention provides a use of the electroluminescent device as described above in an electronic device, an electronic component module, a display device or a lighting device.

[0264] In one embodiment, the present invention provides a compound formulation comprising the metal complex as described above.

[0265] Combination with other materials

[0266] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, 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.

[0267] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the materials disclosed herein can be used in combination with a variety of light-emitting dopants, 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.

[0268] 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 conventional equipment 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 Cost's electrochemical workstation and Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Angstrom Engineering, the optical test system produced by Suzhou Fushida, the life test system or the ellipsometer produced by Beijing Liangtuo, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents are no longer expanded in this patent.

[0269] Material synthesis example:

[0270] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0271] Synthesis Example 1

[0272] This embodiment provides a metal complex Ir(L a1-322 )2(L b122 )(Compound 214), the specific structure is as follows:

[0273]

[0274] The preparation method comprises the following steps:

[0275] (1) Synthesis of intermediate 1

[0276]

[0277] Dissolve m-bromotoluene (58.4mmol, 10g) in 240mL tetrahydrofuran (THF), evacuate the reaction system and replace nitrogen three times, place the reaction bottle in a dry ice-ethanol system and cool to -72°C, slowly drop n-butyllithium (n-BuLi, 2.5M, 71mmol, 28mL) into the system, react for 30min after the addition is complete, then dissolve tetrahydropyrone (76mmol, 7.6g) and slowly drop it. After the addition is complete, slowly return to room temperature and react overnight. Thin layer chromatography (TLC) is used to detect the reaction until it is complete. Add water to quench the reaction, separate the THF layer, extract the aqueous phase with ethyl acetate (EA) three times, combine the organic phases, dry, rotary evaporate, and purify by column chromatography to obtain the product intermediate 1 (10.58g, yield 94.2%).

[0278] (2) Synthesis of Intermediate 2

[0279]

[0280] The intermediate 1 (53.8mmol, 10.34g) obtained in step (1) was dissolved in 270mL of dichloromethane (DCM), the reaction system was evacuated and replaced with nitrogen three times, the reaction bottle was placed in a dry ice-ethanol system and cooled to -72°C, titanium tetrachloride (107.6mmol, 11.8mL) was slowly added dropwise to the system, and the reaction was continued for 30min after the addition was completed, and then dimethyl zinc (215mmol, 215mL) was slowly added dropwise. After the addition was completed, the temperature was slowly restored to room temperature and the reaction was allowed to proceed overnight. TLC was used to detect the reaction until it was complete; water was slowly added to quench the reaction, the organic layer was separated, the aqueous phase was extracted with DCM three times, the organic phases were combined, dried, rotary evaporated, and purified by column chromatography to obtain the product intermediate 2 (6.35g, with a yield of 62%).

[0281] (3) Synthesis of Intermediate 3

[0282]

[0283] Dicyclooctadiene dimethoxyiridium ([Ir(cod)(OMe)]2, 110.7 mg, 0.117 mmol), 4,4-di-tert-butylbipyridine (dtbpy, 897 mg, 3.3 mmol) were dissolved in 15 mL of cyclohexane, the system was evacuated and replaced with nitrogen three times, pinacol borane (HBpin, 855 mg, 6.68 mmol) was added to the system, and stirred for 30 min; in another bottle, the intermediate 2 (6.35 g, 33.4 mmol) obtained in step (2), biboric acid pinacol ester (8.5 g, 33.4 mmol) and 20 mL of cyclohexane were added, the system was evacuated and replaced with nitrogen three times, the catalyst was transferred in, the reaction was heated to reflux for 24 h, cooled to room temperature, methanol was slowly added to quench the reaction, the reaction was spin-dried, and purified by column chromatography to obtain the product intermediate 3 (8.8 g, 27.8 mmol, yield 83%).

[0284] (4) Synthesis of intermediate 4

[0285]

[0286] 1,6-Dichloroisoquinoline (2.36 g, 11.9 mmol), intermediate 3 (4.33 g, 13.7 mmol) obtained in step (3), tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (0.69 g, 0.59 mmol), Na2CO3 (1.89 g, 17.86 mmol), 45 mL of 1,4-dioxane and 15 mL of water were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. TLC was used to detect the completion of the reaction, and the mixture was diluted with water. The organic phase was separated, the aqueous phase was extracted with EA, the organic phases were combined, and the product intermediate 4 (4.07 g, 11.56 mmol, yield 97%) was purified by column chromatography.

[0287] (5) Synthesis of Intermediate 5

[0288]

[0289] The intermediate 4 obtained in step (4) (4.07 g, 11.56 mmol), isobutylboric acid (2.4 g, 23.13 mmol), palladium acetate Pd(OAc)2 (0.13 g, 0.58 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.47 g, 1.16 mmol), K3PO4·3H2O (9.24 g, 34.68 mmol), and toluene (PhMe) 58 mL were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. The reaction was detected by TLC until the reaction was complete. The solvent was dried and purified by column chromatography to obtain the product intermediate 5 (4.2 g, 11.24 mmol, with a yield of 97%).

[0290] (6) Synthesis of iridium dimer

[0291]

[0292] A mixture of intermediate 5 (3.3 g, 8.8 mmol) obtained in step (5), iridium trichloride trihydrate (0.89 g, 2.5 mmol), 2-ethoxyethanol (18 mL) and water (18 mL) was refluxed under a nitrogen atmosphere for 24 h. After cooling to room temperature, the mixture was filtered, and the solid was washed with methanol and dried to obtain an iridium dimer.

[0293] (7) Synthesis of Compound 214

[0294]

[0295] A mixture of iridium dimer obtained in step (6), 3,7-diethyl-3-methylnonane-4,6-dione (1.13 g, 5 mmol), K2CO3 (1.73 g, 12.5 mmol) and 2-ethoxyethanol (30 mL) was stirred at room temperature under nitrogen atmosphere for 24 h. After the reaction was complete, the precipitate was filtered through diatomaceous earth and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, the target product was obtained, and further purified by hot filtration with acetonitrile to obtain a total of 1.8 g of the target product compound 214 with a yield of 48.1%. The structure of the compound was confirmed to be correct by mass spectrometry, and the molecular weight was 1162.6.

[0296] Synthesis Example 2

[0297] This embodiment provides a metal complex Ir(L a1-68 )2(L b122 ) (Compound 203), the specific structure is as follows:

[0298]

[0299] The preparation method comprises the following steps:

[0300] (1) Synthesis of intermediate 6

[0301]

[0302] Dissolve m-bromotoluene (58.4mmol, 10g) in 195mL THF, evacuate the reaction system and replace nitrogen three times, place the reaction bottle in a dry ice-ethanol system and cool to -72°C, slowly drop n-BuLi (2.5M, 64.4mmol, 26mL) into the system, react for 30min after the addition is complete, then dissolve dihydro-3(2H)-furanone (70.2mmol, 6.04g) and slowly drop it therein. After the addition is complete, slowly return to room temperature and react overnight. TLC detection until the reaction is complete. Add water to quench the reaction, separate the THF layer, extract the aqueous phase with EA three times, combine the organic phases, dry, rotary evaporate, and purify by column chromatography to obtain the product intermediate 6 (9.18g, yield 88%).

[0303] (2) Synthesis of intermediate 7

[0304]

[0305] The intermediate 6 (51.6 mmol, 9.18 g) obtained in step (1) was dissolved in 170 mL of DCM, the reaction system was evacuated and replaced with nitrogen three times, the reaction bottle was placed in a dry ice-ethanol system and cooled to -72°C, titanium tetrachloride (103.1 mmol, 11.3 mL) was slowly added dropwise to the system, and the reaction was continued for 30 min after the addition was completed, and then dimethyl zinc (206 mmol, 206 mL) was slowly added dropwise. After the addition was completed, the temperature was slowly restored to room temperature and the reaction was allowed to proceed overnight. TLC was used to detect the reaction until it was complete; water was slowly added to quench the reaction, the organic layer was separated, the aqueous phase was extracted with DCM three times, the organic phases were combined, dried, rotary evaporated, and purified by column chromatography to obtain the product intermediate 7 (8.72 g, with a yield of 96%).

[0306] (3) Synthesis of Intermediate 8

[0307]

[0308] [Ir(cod)(OMe)]2 (164 mg, 0.25 mmol) and 4,4-di-tert-butylbipyridine (dtbpy, 1.33 g, 4.96 mmol) were dissolved in 20 mL of cyclohexane, the system was evacuated and replaced with nitrogen three times, pinacol borane (HBpin, 1.27 g, 9.91 mmol) was added to the system, and stirred for 30 min; in another bottle, the intermediate 7 (8.72 g, 49.5 mmol) obtained in step (2), pinacol borate (12.58 g, 49.5 mmol) and 40 mL of cyclohexane were added, the system was evacuated and replaced with nitrogen three times, the catalyst was transferred in, the reaction was heated to reflux for 24 h, cooled to room temperature, methanol was slowly added to quench the reaction, the mixture was spin-dried, and purified by column chromatography to obtain the product intermediate 8 (7.96 g, 26.34 mmol, yield 53%).

[0309] (4) Synthesis of Intermediate 9

[0310]

[0311] 1,6-Dichloroisoquinoline (2.17 g, 10.98 mmol), intermediate 8 obtained in step (3) (3.65 g, 12.1 mmol), Pd(PPh3)4 (0.64 g, 0.55 mmol), Na2CO3 (1.75 g, 16.47 mmol), 42 mL of 1,4-dioxane and 14 mL of water were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. TLC was used to detect when the reaction was complete, and the mixture was diluted with water. The organic phase was separated, the aqueous phase was extracted with EA, the organic phases were combined, and the product intermediate 9 (3.32 g, 9.85 mmol, yield 89.7%) was purified by column chromatography.

[0312] (5) Synthesis of Intermediate 10

[0313]

[0314] The intermediate 9 obtained in step (4) (2.38 g, 7.04 mmol), isobutylboric acid (1.44 g, 14.1 mmol), Pd(OAc)2 (80 mg, 0.35 mmol), Sphos (290 mg, 0.7 mmol), K3PO4·3H2O (5.63 g, 21.13 mmol), and PhMe 35 mL were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. The reaction was detected by TLC until the reaction was complete. The solvent was dried and purified by column chromatography to obtain the product intermediate 10 (2.5 g, 6.95 mmol, yield 98.7%).

[0315] (6) Synthesis of iridium dimer

[0316]

[0317] A mixture of intermediate 10 (1.75 g, 4.87 mmol) obtained in step (5), iridium trichloride trihydrate (0.49 g, 1.39 mmol), 2-ethoxyethanol (10 mL) and water (10 mL) was refluxed under a nitrogen atmosphere for 24 h. After cooling to room temperature, the mixture was filtered, and the solid was washed with methanol and dried to obtain an iridium dimer.

[0318] (7) Synthesis of Compound 203

[0319]

[0320] A mixture of iridium dimer obtained in step (6), 3,7-diethyl-3-methylnonane-4,6-dione (0.47 g, 2.08 mmol), K2CO3 (0.96 g, 6.95 mmol) and 2-ethoxyethanol (20 mL) was stirred at room temperature under nitrogen atmosphere for 24 h. After the reaction was complete, the precipitate was filtered through diatomaceous earth and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, the target product was obtained, which was further purified by hot filtration with acetonitrile to obtain a total of 1.3 g of the target product compound 203 with a yield of 84.5%. The structure of the compound was confirmed to be correct by mass spectrometry, and the molecular weight was 1134.6.

[0321] Synthesis Comparative Example 1

[0322] This comparative example provides a comparative compound 2, the specific structure of which is as follows:

[0323]

[0324] The preparation method comprises the following steps:

[0325] (1) Synthesis of intermediate 11

[0326]

[0327] 1,3-Dibromotoluene (42.4mmol, 10g) was dissolved in 170mL THF, the reaction system was evacuated and replaced with nitrogen three times, the reaction bottle was placed in a dry ice-ethanol system and cooled to -72°C, n-BuLi (2.5M, 48.7mmol, 19.5mL) was slowly added dropwise to the system, and the reaction was continued for 30min after the addition was completed, and then tetrahydropyrone (50.88mmol, 5.1g) was added dropwise thereto, and the temperature was slowly restored to room temperature after the addition was completed, and the reaction was continued overnight. TLC was detected until the reaction was complete. Water was added to quench the reaction, the THF layer was separated, the aqueous phase was extracted with EA three times, the organic phases were combined, dried, rotary evaporated, and purified by column chromatography to obtain the product intermediate 11 (9.24g, 36.1mmol, yield 85.1%).

[0328] (2) Synthesis of intermediate 12

[0329]

[0330] The intermediate 11 (36.1mmol, 9.24g) obtained in step (1) was dissolved in 180mL DCM, the reaction system was evacuated and replaced with nitrogen three times, the reaction bottle was placed in a dry ice-ethanol system and cooled to -72°C, titanium tetrachloride (72.8mmol, 8mL) was slowly added dropwise to the system, and the reaction was continued for 30min after the addition was completed, and then dimethyl zinc (144.4mmol, 145mL) was slowly added dropwise. After the addition was completed, the temperature was slowly restored to room temperature and the reaction was allowed to proceed overnight. TLC was used to detect the reaction until it was complete. Water was slowly added to quench the reaction, the organic layer was separated, the aqueous phase was extracted three times with DCM, the organic phases were combined, dried, rotary evaporated, and purified by column chromatography to obtain the product intermediate 12 (4.07g, 33.42mmol, yield 62%).

[0331] (3) Synthesis of intermediate 13

[0332]

[0333] The intermediate 12 (4.07 g, 15.7 mmol) obtained in step (2), pinacol diboron (4.4 g, 17.32 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride Pd(dppf)Cl2 (576 mg, 0.79 mmol), and potassium acetate (KOAc, 2.32 g, 23.6 mmol) were dissolved in 80 mL of 1,4-dioxane, and the system was evacuated and replaced with nitrogen three times, and refluxed to react. The reaction was detected by TLC until the reaction was complete, and the product was dried by spin drying and purified by column chromatography to obtain the product intermediate 13 (3.3 g, 11 mmol, yield 70%).

[0334] (4) Synthesis of intermediate 14

[0335]

[0336] 1,6-Dichloroisoquinoline (1.89 g, 9.53 mmol), intermediate 13 (3.79 g, 12.6 mmol) obtained in step (3), Pd(PPh3)4 (0.26 g, 0.48 mmol), Na2CO3 (1.52 g, 14.2 mmol), 36 mL of 1,4-dioxane and 12 mL of water were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. TLC was used to detect when the reaction was complete, and the mixture was diluted with water. The organic phase was separated, the aqueous phase was extracted with EA, the organic phases were combined, and the product intermediate 14 (1.92 g, 5.68 mmol, yield 60%) was purified by column chromatography.

[0337] (5) Synthesis of Intermediate 15

[0338]

[0339] The intermediate 14 obtained in step (4) (1.92 g, 5.68 mmol), isobutylboric acid (1.16 g, 11.36 mmol), Pd(OAc)2 (64 mg, 0.28 mmol), Sphos (0.23 g, 0.57 mmol), K3PO4·3H2O (4.54 g, 17.0 mmol), and PhMe 28 mL were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. The reaction was detected by TLC until the reaction was complete. The solvent was dried and purified by column chromatography to obtain the product intermediate 15 (1.86 g, 5.18 mmol, yield 91.3%).

[0340] (6) Synthesis of iridium dimer

[0341]

[0342] A mixture of intermediate 15 (1.54 g, 4.28 mmol) obtained in step (5), iridium trichloride trihydrate (0.43 g, 1.22 mmol), 2-ethoxyethanol (9 mL) and water (9 mL) was refluxed under a nitrogen atmosphere for 24 h. After cooling to room temperature, the mixture was filtered, and the solid was washed with methanol and dried to obtain an iridium dimer.

[0343] (7) Synthesis of Comparative Compound 2

[0344]

[0345] A mixture of iridium dimer obtained in step (6), 3,7-diethyl-3-methylnonane-4,6-dione (416 mg, 1.84 mmol), K2CO3 (846 mg, 6.12 mmol) and 2-ethoxyethanol (18 mL) was stirred at room temperature under nitrogen atmosphere for 24 h. After the reaction was complete, the precipitate was filtered through diatomaceous earth and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, the target product was obtained, which was further purified by hot filtration with acetonitrile to obtain the target product comparative compound 2, a total of 1.1 g, 1.01 mmol, with a yield of 82.5%. The structure of the compound was confirmed to be correct by mass spectrometry, and the molecular weight was 1134.6.

[0346] Synthesis Comparative Example 2

[0347] This comparative example provides a comparative compound 1, the specific structure of which is as follows:

[0348]

[0349] The preparation method comprises the following steps:

[0350] (1) Synthesis of intermediate 16

[0351]

[0352] 6-Bromo-1-(3,5-dimethylphenyl)isoquinoline (3.57 g, 11.44 mmol), isobutylboric acid (2.33 g, 22.88 mmol), Pd(OAc)2 (128 mg, 0.57 mmol), Sphos (0.47 g, 1.14 mmol), K3PO4·3H2O (9.14 g, 34.32 mmol), and 57 mL of toluene were added to the reaction flask. The system was evacuated and replaced with nitrogen three times, and heated to reflux. The reaction was allowed to proceed overnight. The reaction was detected by TLC until completion. The solvent was dried and purified by column chromatography to obtain the product intermediate 16 (2.72 g, 9.4 mmol, with a yield of 82%).

[0353] (2) Synthesis of iridium dimer:

[0354]

[0355] A mixture of intermediate 16 (2.72 g, 9.4 mmol) obtained in step (1), iridium trichloride trihydrate (0.95 g, 2.69 mmol), 2-ethoxyethanol (30 mL) and water (10 mL) was refluxed under a nitrogen atmosphere for 24 h. After cooling to room temperature, the mixture was filtered, and the solid was washed several times with methanol and dried to obtain an iridium dimer.

[0356] (3) Synthesis of Comparative Compound 1

[0357]

[0358] A mixture of iridium dimer (0.36 g, 0.22 mmol) obtained in step (2), 3,7-diethyl-3-methylnonane-4,6-dione (127 mg, 0.56 mmol), K2CO3 (309 mg, 2.24 mmol) and 2-ethoxyethanol (6 mL) was stirred at room temperature under nitrogen atmosphere for 24 h. After the reaction was complete, the precipitate was filtered through diatomaceous earth and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, the target product was obtained, which was further purified by hot filtration with acetonitrile to obtain the target product comparative compound 1, a total of 0.41 g, 0.41 mmol, with a yield of 92%. The structure of the compound was confirmed to be correct by mass spectrometry, and the molecular weight was 994.5.

[0359] 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.

[0360] Device Example 1

[0361] The present device embodiment provides an electroluminescent device, which comprises: a substrate, an ITO anode 120 nm, a hole injection layer Hole transport layer Electron blocking layer Luminescent layer Hole blocking layer Electron transport layer The electron injection layer is 1nm and the cathode (aluminum) is 120nm. The preparation method is as follows:

[0362] (1) A glass substrate having a 120 nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture and mounted on a substrate holder and placed in a vacuum chamber. The organic layers specified below were then deposited at a vacuum of approximately 10 -8 In the case of trust The rate of evaporation is carried out on the ITO anode by thermal vacuum evaporation in sequence:

[0363] (2) Compound HI is used as a hole injection layer (HIL);

[0364] (3) evaporating compound HT on the hole injection layer to serve as a hole transport layer (HTL);

[0365] (4) evaporating compound EB1 on the hole transport layer to serve as an electron blocking layer (EBL);

[0366] (5) depositing a light-emitting layer on the electron blocking layer, and doping the compound 214 provided in Synthesis Example 1 of the present invention in a ratio of 3% into the host compound RH to serve as a light-emitting layer (EML);

[0367] (6) evaporating compound HB on the light-emitting layer to serve as a hole blocking layer (HBL);

[0368] (7) Co-evaporating compound ET and 8-hydroxyquinoline-lithium (Liq) on the HBL as an electron transport layer (ETL);

[0369] (8) 1 nm of Liq was deposited on the electron transport layer as an electron injection layer (EIL), and 120 nm of Al was deposited as a cathode;

[0370] The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture getter to complete the device.

[0371] Device Example 2

[0372] Device Example 2 differs from Device Example 1 only in that Compound EB1 in step (4) is replaced by Compound EB2.

[0373] Device Example 3

[0374] The only difference between Device Example 3 and Device Example 2 is that Compound 214 in step (5) is replaced by Compound 203 provided in Synthesis Example 2.

[0375] Device Comparison Example 1

[0376] The difference between device example 1 and device example 1 is that compound 214 in step (5) is replaced by comparative compound 1.

[0377] Device Comparison Example 2

[0378] The only difference between device Example 2 and device Example 2 is that compound 214 in step (5) is replaced by comparative compound 2.

[0379] The detailed device layer structure and thickness are shown in Table 1. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0380] Table 1 Device structures of device embodiments and comparative examples

[0381]

[0382] The material structure used in the device is shown below:

[0383] Compound HI is Compound HT is Compound EB1 is Compound EB2 is Compound RH is Compound HB is Compound ET is Comparative compound 1 is Comparative compound 2 is The compound 214 provided by the present invention is Compound 203 is

[0384] Device performance test and discussion:

[0385] The JVL characteristics of the device were measured. Table 2 shows the CIE color coordinates (x, y), maximum emission wavelength (λ max ), half maximum width (FWHM), voltage (V), luminous efficiency (CE), luminous power efficiency (PE) and external quantum efficiency (EQE) data.

[0386] Table 2 Device data

[0387]

[0388]

[0389] By comparing the data of Comparative Example 1 and Examples 1 and 3, it can be seen that the metal complex provided by the present invention, which introduces a saturated heterocyclic substituent on a specific ring of the ligand, further narrows the half-peak width of the device luminescence. In addition, the driving voltage of device Examples 1 and 3 is significantly reduced relative to that of Comparative Example 1, and the external quantum efficiency (EQE) of device Examples 1 and 3 is further improved on the basis of the already high EQE level of Comparative Example 1, while the luminous efficiency (CE) and luminous power efficiency (PE) of device Examples 1 and 3 are significantly improved relative to that of Comparative Example 1. This illustrates that the metal complex provided by the present invention, which introduces a saturated heterocyclic substituent on a specific ring of the ligand, can provide better performance. By comparing the data of Comparative Example 2 and Examples 1 to 3, it can be seen that in the metal complex structure provided by the present invention, after introducing a specific substituent (such as a methyl group) at a specific position of the ligand, the half-width of the device luminescence is greatly narrowed, and the luminescent color saturation is greatly improved; in addition, the maximum emission wavelength of Examples 1 to 3 is blue-shifted by 6 to 7 nm, the driving voltage is also reduced, and the luminescent current efficiency (CE), luminescent power efficiency (PE) and external quantum efficiency (EQE) are greatly improved, thereby obtaining better luminescence performance.

[0390] In summary, the metal complex provided by the present invention can significantly improve the half-peak width of the device luminescence and significantly improve the saturation of the luminescent color. In addition, the luminescent color can be finely controlled by changing the substituents in the ligand to obtain higher device efficiency and lower voltage, which fully proves the uniqueness and importance of the present invention.

[0391] The applicant declares that the present invention illustrates a metal complex, an electroluminescent device and its application through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned process steps, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. It should be clear to those skilled in the art that any improvement to the present invention, the equivalent replacement of the raw materials selected by the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the scope of protection and disclosure of the present invention. Many of the materials and structures described herein can be replaced by other materials and structures without departing from the spirit of the present invention. It should be understood that various theories about why the present invention works are not intended to be limiting.

Claims

1. A metal complex, characterized in that The structural formula of the metal complex is Ir(L a )2(L b ); 2 L a The same or different, the L a for Among them, the dotted lines represent the binding sites between the ligand and the metal atom; R is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; R y2 It has a structure as shown in Formula II: Wherein, * represents the attachment site of the group; C1 is carbon; Ring A is selected from a substituted or unsubstituted saturated heterocyclic ring having 5-6 ring atoms, wherein the saturated heterocyclic ring contains 1 heteroatom X; X is selected from O; There is at least one ring carbon atom between X and C1 in ring A; L is selected from a single bond; R Aa represents mono-, poly- or unsubstituted; R xx Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; R Ac Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; R xx , R x , R y1 , R Aa 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, and combinations thereof; The L b Selected from the following structures: Among them, the dotted lines represent the binding sites between the ligand and the metal atom; X c , X d Selected from O; R a , R b , R c 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, cyano, and combinations thereof; The substituted alkyl group having 1 to 20 carbon atoms and the substituted cycloalkyl group having 3 to 20 ring carbon atoms refer to that any one of the alkyl group and the cycloalkyl group may be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof.

2. The metal complex according to claim 1, characterized in that The R y1 Selected from hydrogen or deuterium.

3. The metal complex according to claim 1, characterized in that The R x , R xx , R y1 At least one, two or three of the above are independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, and combinations thereof.

4. The metal complex according to claim 1, characterized in that The metal complex is an iridium complex and has a structure as shown in Formula III: In formula III, m is 2; R1, R2, R3, R4, R5, R6, and R7 are each independently 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, and combinations thereof.

5. The metal complex according to claim 4, characterized in that At least one of R1, R2, and R3 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof; and / or at least one of R4, R5, and R6 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

6. The metal complex according to claim 5, characterized in that At least two of the R1, R2, and R3 are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof; and / or at least two of the R4, R5, and R6 are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

7. The metal complex according to claim 1, characterized in that The L a It has a structure as shown in Formula VI: Among them, the dotted lines represent the binding sites between the ligand and the metal atom; R, R y2 Each independently has the same definition as in claim 1; R x1 , R x2 , R x3 Each is independently 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, and combinations thereof.

8. The metal complex according to claim 7, characterized in that The R x1 , R x2 are each independently selected from hydrogen or deuterium; said R x3 It is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

9. The metal complex according to claim 8, characterized in that The R x3 Selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, and partially or fully deuterated versions of the above groups.

10. The metal complex according to claim 1, characterized in that The R is selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

11. The metal complex according to claim 10, characterized in that The R is selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, and partially or completely deuterated groups thereof.

12. The metal complex according to claim 1, characterized in that The R Aa , R Ac Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms.

13. The metal complex according to claim 12, characterized in that The R Aa , R Ac is selected, identically or differently on each occurrence, from hydrogen, deuterium, methyl, ethyl, isopropyl or isobutyl.

14. The metal complex according to claim 1, characterized in that The L a Each occurrence is identically or differently selected from the group consisting of: The dotted lines represent the binding sites between the ligand and the metal atom.

15. The metal complex according to claim 14, characterized in that The L b Each occurrence is identically or differently selected from the group consisting of: The dotted lines represent the binding sites between the ligand and the metal atom.

16. The metal complex according to claim 15, characterized in that The metal complex has Ir(L a )2(L b ) structure; Among them, L a Each time it appears, choose the same or different one from L a1-1 ~L a1-11 , L a1-16 ~L a1-19 , L a1-23 ~L a1-43 , L a1-48 ~L a1-51 , L a1-55 ~L a1-75 , L a1-80 ~L a1-83 , L a1-87 ~L a1-96 , L a1-223 ~L a1-233 , L a1-238 ~L a1-241 , L a1-246 ~L a1-265 , L a1-270 ~L a1-273 , L a1-277 ~L a1-297 , L a1-302 ~L a1-305 , L a1-309 ~L a1-329 , L a1-334 ~L a1-337 , L a1-3341 ~L a1-350 , L a2-1 ~L a2-9 , L a2-14 ~L a2-17 , L a2-14 ~L a2-29 , L a2-34 ~L a2-37 , L a2-121 ~L a2-129 , L a2-134 ~L a2-137 , L a2-134 ~L a2-149 , L a2-154 ~L a2-157 , L a2-161 ~L a2-169 , L a2-174 ~L a2-177 , L a2-181 ~L a2-189 , L a2-194 ~L a2-197 , and L a7-1 ~L a7-8 , L a7-11 ~L a7-15 , L a7-19 ~L a7-26 , L a7-30 ~L a7-33 , L a7-37 ~L a7-44 , L a7-48 ~L a7-51 , L a7-48 ~L a7-62 , L a7-66 ~L a7-69 Any one or any two of the group consisting of L b Choose from L b1 To L b322 Any one of the groups consisting of.

17. The metal complex according to claim 15, characterized in that The metal complex is selected from Compound 1, Compound 3 to Compound 4, Compound 7 to Compound 15, Compound 30 to Compound 31, Compound 39, Compound 41, Compound 43 to Compound 44, Compound 47 to Compound 55, Compound 70 to Compound 71, Compound 79, Compound 81, Compound 83 to Compound 84, Compound 87 to Compound 95, Compound 110 to Compound 111, Compound 119, Compound 121, Compound 123 to Compound 124, Compound 127 to Compound 135, Compound 150 to Compound 151, Compound 159, Compound 161, Compound 163 to Compound 164, Compound 167 to Compound 175, Compound 190 to Compound 191, Compound 199, Compound 201, Compound 202 Compound 203 to Compound 205, Compound 207 to Compound 215, Compound 230 to Compound 232, Compound 239, Compound 241, Compound 243 to Compound 245, Compound 247 to Compound 255, Compound 270 to Compound 272, Compound 279, Compound 281, Compound 283 to Compound 285, Compound 287 to Compound 295, Compound 310 to Compound 312, Compound 319, Compound 321, Compound 323 to Compound 325, Compound 327 to Compound 335, Compound 350 to Compound 352, Compound 359, Compound 361, Compound 363 to Compound 365, Compound 367 to Compound 375, Compound 390 to Compound 392, and Compound 399; Compound 1, compound 3 to compound 4, compound 7 to compound 15, compound 30 to compound 31, compound 39, compound 41, compound 43 to compound 44, compound 47 to compound 55, compound 70 to compound 71, compound 79, compound 81, compound 83 to compound 84, compound 87 to compound 95, compound 110 to compound 111, compound 119, compound 121, compound 123 to compound 124, compound 127 to compound 135, compound 150 to compound 151, compound 159, compound 161, compound 163 to compound 164, compound 167 to compound 175, compound 190 to compound 191, compound 199, compound 201, compound 203 to compound 1 Compound 205, Compound 207 to Compound 215, Compound 230 to Compound 232, Compound 239, Compound 241, Compound 243 to Compound 245, Compound 247 to Compound 255, Compound 270 to Compound 272, Compound 279, Compound 281, Compound 283 to Compound 285, Compound 287 to Compound 295, Compound 310 to Compound 312, Compound 319, Compound 321, Compound 323 to Compound 325, Compound 327 to Compound 335, Compound 350 to Compound 352, Compound 359, Compound 361, Compound 363 to Compound 365, Compound 367 to Compound 375, Compound 390 to Compound 392, Compound 399 has Ir(L a )2(L b ) structure, where two L a Same, L a and L b They correspond to the structures selected from the following table: The compounds 421, 423 and 429 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b They correspond to the structures selected from the following table: 。 18. An electroluminescent device, characterized in that: The electroluminescent device comprises a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 17.

19. The electroluminescent device according to claim 18, characterized in that The organic layer includes a light-emitting layer, and the light-emitting material of the light-emitting layer includes the metal complex according to any one of claims 1 to 17.

20. The electroluminescent device according to claim 19, characterized in that The electroluminescent device emits red light or white light.

21. The electroluminescent device according to claim 19, characterized in that The light-emitting layer also contains at least one or at least two main materials; at least one of the main materials 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.

22. Use of the electroluminescent device according to claim 18 in electronic equipment, electronic component modules, display devices or lighting devices.

23. A compound formulation, characterized in that: The compound formula comprises the metal complex as claimed in any one of claims 1 to 17.

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