Electroluminescent material and device thereof

Abstract

The invention discloses an electroluminescent material and a device thereof. The electroluminescent material is a metal complex comprising a metal M and a ligand La coordinated with the M, and the La has a structure represented by formula 1. The metal complex can be used as a luminescent material in an electroluminescent device. The novel metal complexes can better adjust the light emitting color of a device and realize dark red light emission while maintaining very narrow half-peak width, and can reduce the driving voltage of the device or maintain a low voltage level, thereby greatly improving the efficiency of the device. The novel metal complex can provide better device performance. An electroluminescent device and a compound composition are also disclosed.

Description

[0001] This patent application is a divisional application of Chinese Invention Patent Application No. 202211093543.3, which has a priority date of October 29, 2021 and is entitled "An Electroluminescent Material and Device Thereof".

[0002] This application claims priority to Chinese Patent Application No. 202111270497.5, filed on October 29, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a metal complex comprising a ligand of formula 1, and an electroluminescent device and compound composition comprising the metal complex. Background Technology

[0004] Organic electronic devices include, but are not limited to, the following types: 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 photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0005] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0006] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0007] OLEDs can also be classified 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. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0008] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0009] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0010] Phosphorescent metal complexes can be used as phosphorescent dopant materials in the emitting layer for applications in organic electroluminescent lighting or displays. However, the performance of currently developed metal complexes in electroluminescent devices still has several shortcomings. To meet the industry's ever-increasing demands, such as lower voltage, higher device efficiency, emission colors within specific wavelength ranges, more saturated emission colors, and longer device lifetimes, further research and development of metal complexes is urgently needed. Summary of the Invention

[0011] This invention aims to provide a series of metal complexes with ligands having the structure of Formula 1 to solve at least some of the aforementioned problems. These metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes, while maintaining a very narrow full width at half maximum (FWHM), can better regulate the emission color of the device, achieving a deeper red emission, and can reduce or maintain a low driving voltage, significantly improving device efficiency. These novel metal complexes provide better device performance.

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

[0013]

[0014] Among them, ring A and ring B are each independently selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms; ring C is selected from aromatic rings with 6-30 carbon atoms or heteroaromatic rings with 6-30 ring atoms.

[0015] R i R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R iii The same or different occurrences each time indicate single or multiple substitution;

[0016] Y is selected from SiR y R y GeR y R y NR y PR y , O, S or Se;

[0017] When two R exist simultaneously y At that time, two R y They can be the same or different;

[0018] X1-X2 are selected from CR each time they appear, either the same or different. x Or N;

[0019] R, R i R ii R x and R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0020] R iii Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0021] Adjacent substituent Ri R x R y , R, R ii and R iii They can be arbitrarily connected to form a ring.

[0022] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex comprising a metal M and a ligand L coordinated to M. a The metal M is selected from metals with a relative atomic mass greater than 40, and the L a It has a structure represented by Equation 1:

[0023]

[0024] Among them, ring A and ring B are each independently selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms; ring C is selected from aromatic rings with 6-30 carbon atoms or heteroaromatic rings with 6-30 ring atoms.

[0025] R i R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R iii The same or different occurrences each time indicate single or multiple substitution;

[0026] Y is selected from SiR y R y GeR y R y NR y PR y , O, S or Se;

[0027] When two R exist simultaneously y At that time, two R y They can be the same or different;

[0028] X1-X2 are selected from CR each time they appear, either the same or different. x Or N;

[0029] R, R i R ii R x and R yEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0030] R iii Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0031] Adjacent substituent R i R x R y , R, R ii and R iii They can be arbitrarily connected to form a ring.

[0032] According to another embodiment of the present invention, a compound composition comprising the metal complex described in the above embodiments is also disclosed.

[0033] The novel metal complexes with polycyclic ligands disclosed in this invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes, while maintaining a very narrow full width at half maximum (FWHM), can better regulate the emission color of the device, achieving a deeper red emission, and can reduce or maintain a low driving voltage, significantly improving device efficiency. These novel metal complexes provide better device performance. Attached Figure Description

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

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

[0036] Figure 3 This is a schematic diagram of a typical top-emitting OLED device that may contain the metal complexes and compound compositions disclosed herein. Detailed Implementation

[0037] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. 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. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0038] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein 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 herein 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 herein 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 herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a 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 also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0039] A typical top-emitting OLED device structure is as follows: Figure 3As shown in the diagram. The OLED device 300 includes: an anode layer 301, a hole injection layer (HIL) 302, a first hole transport layer (HTL1) 303, a second hole transport layer (HTL2) 304 (also called a prime layer), an emissive layer (EML) 305, a hole blocking layer (HBL) 306 (the hole blocking layer 306 is optional), an electron transport layer (ETL) 307, an electron injection layer (EIL) 308, a cathode layer 309, and a capping layer 310. The anode layer 101 is a material or combination of materials with high reflectivity, including but not limited to Ag, Al, Ti, Cr, Pt, Ni, TiN, and combinations of the above materials with ITO and / or MoOx (molybdenum oxide). Typically, the anode has a reflectivity greater than 50%; preferably, the anode has a reflectivity greater than 70%; more preferably, the anode has a reflectivity greater than 80%. The cathode layer 109 should be a translucent or transparent conductive material, including but not limited to MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or combinations thereof, with an average transmittance of greater than 15% for light in the visible light region; preferably, the average transmittance of greater than 20% for light in the visible light region; more preferably, the average transmittance of greater than 25% for light in the visible light region.

[0040] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0041] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0042] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0043] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0044] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0045] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0046] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0047] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0048] 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: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0049] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0050] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0051] Definition of the term "substituent group"

[0052] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0053] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0054] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0055] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0056] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups 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, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0057] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 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, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0058] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 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-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0059] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0060] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 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. Isoaryl also refers to heteroaryl. Heteroaryl can 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, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0061] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0062] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0063] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0064] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0065] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0066] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0067] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0068] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0069] In this disclosure, unless otherwise defined, when using any term from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, etc. The substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl group. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having 3 carbon atoms. Cycloalkyl groups with 20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, unsubstituted aryl groups with 6-30 carbon atoms, and so on. The substituted heteroaryl group having 3-30 carbon atoms, the unsubstituted alkylsilyl group having 3-20 carbon atoms, the unsubstituted arylsilyl group having 6-20 carbon atoms, the unsubstituted alkylgermanium group having 3-20 carbon atoms, the unsubstituted arylgermanium group having 6-20 carbon atoms, and the unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0070] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (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 substituents or attaching segments are considered equivalent.

[0071] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0072] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0073] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0074] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0075]

[0076] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0077]

[0078] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0079]

[0080] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0081]

[0082] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand L coordinated to M. a The metal M is selected from metals with a relative atomic mass greater than 40, and the L a It has a structure represented by Equation 1:

[0083]

[0084] Among them, ring A and ring B are each independently selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms; ring C is selected from aromatic rings with 6-30 carbon atoms or heteroaromatic rings with 6-30 ring atoms.

[0085] R i R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R iii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0086] Y is selected from SiR y R y GeR y R y NR y PR y , O, S or Se;

[0087] When two R exist simultaneously y At that time, two R y They can be the same or different;

[0088] X1-X2 are selected from CR each time they appear, either the same or different. x Or N;

[0089] R, R i R ii R x and R yEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0090] R iii Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0091] Adjacent substituent R i R x R y , R, R ii and R iii They can be arbitrarily connected to form a ring.

[0092] In this paper, adjacent substituents Ri R x R y , R, R ii and R iii They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R i Between the two substituents R ii Between the two substituents R iii Between the two substituents R y Between the two substituents R x Between, substituent R i With R x Between, substituent R i With R iii Between, substituents R and R y Between, and substituent R iii Between R, any one or more of these substituents can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0093] According to one embodiment of the present invention, R iii The same or different occurrences each time indicate single or multiple substitution;

[0094] R iii Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0095] According to one embodiment of the invention, the metal complex optionally includes other ligands that can interact with the L a They can be optionally linked to form tridentate, tetradentate, pentadentate, or hexadentate ligands.

[0096] According to one embodiment of the present invention, ring A and / or ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms; ring C is selected from an aromatic ring having 6-18 carbon atoms or a heteroaromatic ring having 6-18 ring atoms.

[0097] According to one embodiment of the present invention, ring A and / or ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6-10 carbon atoms, or a heteroaromatic ring having 3-10 carbon atoms; ring C is selected from an aromatic ring having 6-10 carbon atoms or a heteroaromatic ring having 6-10 ring atoms.

[0098] According to one embodiment of the present invention, wherein the L a Choose any one of the structures from Equation 2 to Equation 17:

[0099]

[0100] in,

[0101] In Equations 2-17, X1-X2 are selected from CR each time they appear, either identically or differently. x Or N; X3 is selected from CR i Or N; A1-A6 are selected from CR each time they appear, either identically or differently. ii Or N; X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii Or N, and at least one of X4 to X7 is selected from CR iii ;

[0102] Z is selected from CR each time it appears, either identically or differently. iv R iv SiR iv R iv PR iv O, S or NR iv When two R exist simultaneously iv At that time, two R iv Same or different; for example, when Z is selected from CR iv R iv At that time, two R iv They can be the same or different; for example, when Z is selected from SiR iv R iv At that time, two R iv They can be the same or different;

[0103] Y is selected from SiR y R y NR y PR y O, S, or Se; when two Rs exist simultaneouslyy At that time, two R y They can be the same or different; for example, when Y is selected from SiR y R y At that time, two R y They can be the same or different;

[0104] R, R x R y R i R ii and R iv Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0105] R iiiEach time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0106] Adjacent substituent R i R x R y , R, R ii and R iii They can be arbitrarily connected to form a ring.

[0107] According to one embodiment of the present invention, L a Choose the structure represented by free form 2 or form 3.

[0108] According to one embodiment of the present invention, L a Choose the structure represented by free form 3.

[0109] According to one embodiment of the present invention, in formulas 2-17, X1-X n and / or A1-A m At least one of them is selected from N, and the X n The A corresponds to the largest of the sequence numbers of X1-X7 in any one of Equations 2-17. m The largest of the sequence numbers corresponding to A1-A6 in any one of Equations 2-17; for example, for Equation 3, X n The A corresponds to X7, which has the largest index among X1-X7 in Equation 3. m The largest of the A1-A6 in Equation 3 is A4, meaning that in Equation 3, at least one of X1-X7 and / or A1-A4 is selected from N.

[0110] According to one embodiment of the present invention, in formulas 2-17, X1-X n At least one of them is selected from N, and the X n The largest of the sequence numbers that exists in any one of Equations 2-17, corresponding to X1-X7.

[0111] According to one embodiment of the present invention, in formulas 2-17, X2 is N.

[0112] According to one embodiment of the present invention, in formulas 2-17, X1-X2 are each independently selected from CR. x X3 is selected from CR i A1-A6 are each independently selected from CR ii X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii And at least one of X4 to X7 is selected from CR iii ; adjacent substituent R x R i R ii R iii They can be arbitrarily connected to form a ring.

[0113] In this paper, adjacent substituents R x R i R ii R iii They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R ii Between the two substituents R iii Between the two substituents R x Between, substituent R i With R iii Between, and substituent R i With R x Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0114] According to one embodiment of the present invention, in formulas 2-17, X1-X2 are each independently selected from CR. x X3 is selected from CR i A1-A6 are each independently selected from CR ii X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii And at least one of X4 to X7 is selected from CR iii ; and the R x R i R iiEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, cyano groups, and combinations thereof;

[0115] R iii Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, cyano groups, and combinations thereof;

[0116] Adjacent substituent R x R i R ii R iii They can be arbitrarily connected to form a ring.

[0117] According to one embodiment of the present invention, in formulas 2-17, X1-X2 are each independently selected from CR. x X3 is selected from CR i A1-A4 are each independently selected from CR ii X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii And at least one of X4 to X7 is selected from CR iii ; and the R x R i R ii At least one or two of them, each time appearing in the same or different manner, are selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, 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 alksilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof;

[0118] R iiiEach time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0119] Adjacent substituent R x R i R ii R iii They can be arbitrarily connected to form a ring.

[0120] In this embodiment, the R x R i R ii At least one or two of them, each time they appear, are selected from the said substituent set, either identically or differently, intended to indicate that in the case of two R... x Substituents, all R i Substituents and all R ii At least one or two of the substituents in the group consisting of substituents are selected from the group of substituents in the same or different ways each time they appear.

[0121] According to one embodiment of the present invention, in formulas 2-17, at least one or two of A1-A6 are selected from CR. ii X3 is selected from CR i .

[0122] According to one embodiment of the present invention, in formulas 2-17, at least one or two of A1-A6 are selected from CR. ii And the R ii Each time it appears, it is selected from the same or different groups of deuterium, halogen, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alksilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, cyano group, or combinations thereof;

[0123] X3 is selected from CR i ; and the R iEach time it appears, it is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, cyano groups, or combinations thereof.

[0124] According to one embodiment of the present invention, in formulas 2-17, at least one or two of A1-A6 are selected from CR. ii And the R ii Each time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0125] X3 is selected from CR i ; wherein R i Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0126] According to one embodiment of the present invention, in formulas 2-17, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, or combinations thereof.

[0127] According to one embodiment of the present invention, in Formulas 2-17, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, trimethylsilyl, or combinations thereof.

[0128] According to one embodiment of the present invention, in formulas 2-17, Y is selected from O or S.

[0129] According to one embodiment of the present invention, in formulas 2-17, Y is selected from O.

[0130] According to one embodiment of the present invention, in formulas 2-17, X1 and X2 are each independently selected from CR. x .

[0131] According to one embodiment of the present invention, in formulas 2-17, X1 is selected from CR x X2 is selected from CR x Or N.

[0132] According to one embodiment of the present invention, in formulas 2-17, X1 is selected from CR x X2 is selected from CR x Or N; and the R x Each time it appears, it is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, or combinations thereof.

[0133] According to one embodiment of the present invention, wherein the ligand L a It has the structure represented by Equation 18:

[0134]

[0135] In Equation 18,

[0136] Y is selected from O or S;

[0137] R x1 R x2 R i R ii1 R ii2 R ii3 R ii4 , R, R iii1 R iii2 R iii3 R iii4Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0138] R iii1 R iii2 R iii3 R iii4 At least one of the following, each time appearing identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0139] According to one embodiment of the present invention, wherein the ligand L a It has the structure represented by Equation 18:

[0140]

[0141] In Equation 18,

[0142] Y is selected from O or S;

[0143] R x1 R x2 One or two and / or R ii1 R ii2 R ii3 R ii4 At least one or two of them, each time appearing identically or differently, are selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alkylsilyl groups having 6-20 carbon atoms, etc. Arylsilyl groups with carbon atoms, or combinations thereof; R is selected from halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof;

[0144] R iii1 R iii2 R iii3 R iii4 At least one or two of them, each time appearing identically or differently, are selected from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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, and combinations thereof.

[0145] According to one embodiment of the present invention, wherein the ligand L a It has the structure represented by Equation 18:

[0146]

[0147] In Equation 18,

[0148] Y is selected from O or S;

[0149] R x1 R x2One or two and / or R ii1 R ii2 R ii3 and R ii4 At least one or two of them, each time appearing identically or differently, are selected from the group consisting of: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof; R is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof;

[0150] R iii1 R iii2 R iii3 R iii4 At least one or two of them, when appearing in the same or different manner each time, are selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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, and combinations thereof.

[0151] According to one embodiment of the present invention, wherein, in formula 18,

[0152] Y is selected from O or S;

[0153] R iii1 R iii2 R iii3 R iii4 At least one or two of them and R ii1 R ii2 R ii3 R ii4At least one or two of them, when appearing in the same or different manner each time, are selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alksilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or combinations thereof;

[0154] R is selected from the group consisting of: halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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, or combinations thereof.

[0155] According to one embodiment of the present invention, wherein, in formula 18,

[0156] Y is selected from O or S;

[0157] R iii1 R iii2 R iii3 R iii4 At least one or two of them and R ii1 R ii2 R ii3 R ii4 At least one or two of them, when appearing in the same or different manner each time, are selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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 alksilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof;

[0158] R is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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, or combinations thereof.

[0159] According to one embodiment of the present invention, wherein, in formula 18, R ii1 Rii2 R ii3 One of them (e.g., R) ii1 Or R ii2 Or R ii3 ) or two (e.g., R) ii1 and R ii2 、or R ii2 and R ii3 、or R ii1 and R ii3 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, or combinations thereof.

[0160] According to one embodiment of the present invention, wherein, in formula 18, R x1 R x2 R iii1 R iii2 R iii3 R iii4 R ii1 R ii2 R ii3 R ii4 At least one of R is selected, in the same or different manner each time it appears, from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof.

[0161] In this embodiment, R x1 R x2 R iii1 R iii2 R iii3 R iii4 R ii1 R ii2 R ii3 R ii4 At least one of R is selected from the substituent group each time it appears, either identically or differently, to indicate that: R x1 R x2 At least one of them, when appearing each time, is selected from the same or different substituent group, and / or R iii1 R iii2 R iii3 R iii4 At least one of them, when appearing each time, is selected from the same or different substituent group, and / or Rii1 R ii2 R ii3 R ii4 At least one of them is selected from the group of substituents each time it appears, either identically or differently, and / or R is selected from the group of substituents.

[0162] According to one embodiment of the present invention, wherein, in formula 18, R iii2 R iii3 R ii1 R ii2 R ii3 At least one of R is selected, in the same or different manner each time it appears, from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof.

[0163] In this embodiment, R iii2 R iii3 R ii1 R ii2 R ii3 At least one of R is selected from the substituent group each time it appears, either identically or differently, to indicate that: R iii2 R iii3 At least one of them, when appearing each time, is selected from the same or different substituent group, and / or R ii1 R ii2 R ii3 At least one of them is selected from the group of substituents each time it appears, either identically or differently, and / or R is selected from the group of substituents.

[0164] According to one embodiment of the present invention, wherein, in formula 18, R x1 R x2 R iii1 R iii2 R iii3 R iii4 R ii1 R ii2 R ii3 R ii4 At least one of R is selected from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 cyclic carbon atoms, and combinations thereof, each time it appears in the same or different manner.

[0165] In this embodiment, R x1 R x2 R iii1 R iii2 R iii3 R iii4 Rii1 R ii2 R ii3 R ii4 At least one of R is selected from the substituent group each time it appears, either identically or differently, to indicate that: R x1 R x2 At least one of them, when appearing each time, is selected from the same or different substituent group, and / or R iii1 R iii2 R iii3 R iii4 At least one of them, when appearing each time, is selected from the same or different substituent group, and / or R ii1 R ii2 R ii3 R ii4 At least one of them is selected from the group of substituents each time it appears, either identically or differently, and / or R is selected from the group of substituents.

[0166] According to one embodiment of the present invention, L a Choose L each time it appears, either the same or different. a1 To L a1904 The group consisting of L a1 To L a1904 The specific structure is described in claim 12.

[0167] According to one embodiment of the present invention, L a Choose L each time it appears, either the same or different. a1 To L a1906 The group consisting of L a1 To L a1904 The specific structure is described in claim 12, wherein the L a1905 To L a1906 for:

[0168]

[0169] According to one embodiment of the present invention, wherein the L a1 To L a1904 In the structure, hydrogen can be partially or completely replaced by deuterium.

[0170] According to one embodiment of the present invention, wherein the L a1 To L a1906 In the structure, hydrogen can be partially or completely replaced by deuterium.

[0171] According to one embodiment of the present invention, the metal complex has M(L) a ) m (L b ) n (Lc ) q The structure;

[0172] Among them, metal M is selected from metals with a relative atomic mass greater than 40; L a L b and L c These are the first, second, and third ligands of the complex, respectively; m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m + n + q equals the oxidation state of metal M; when m is greater than 1, multiple L... a Same or different; when n is 2, the two L b Same or different; when q is 2, the two L c Same or different;

[0173] L a L b and L c They can be optionally linked to form multidentate ligands; for example, L... a L b and L c They can be selectively linked to form tetradentate or hexadentate ligands; L a L b and L c Alternatively, they can all be left unconnected, thus preventing the formation of multidentate ligands;

[0174] L b and L c Each time the same or different occurrences appear, select the group consisting of the following structures:

[0175]

[0176] Among them, R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0177] X b Each time it appears, select the group consisting of the following, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0178] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0179] R a R b R c R N1 RN2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0180] Wherein, the adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0181] In this embodiment, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, 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, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1Between, substituent R c and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R c and R C1 Between, substituent R c and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0182] In this embodiment, L a L b and L c They can be optionally linked to form polydentate ligands, intended to represent L a L b and L c Any two or three of them can connect to form a tetradentate or hexadentate ligand. It is obvious that L... a L b and L c Alternatively, they can all be left unconnected, thus preventing the formation of polydentate ligands.

[0183] According to one embodiment of the present invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0184] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0185] According to one embodiment of the present invention, the metal M is Ir.

[0186] According to one embodiment of the present invention, L b Each occurrence, whether identical or different, is selected from the following structure:

[0187]

[0188] R1–R7 are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1–20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3–20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1–20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3–20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7–30 carbon atoms, substituted or unsubstituted alkoxy groups having 1–20 carbon atoms, substituted or unsubstituted aroxy groups having 6–30 carbon atoms, and substituted or unsubstituted groups having 2–20 carbon atoms. Alkenyl groups, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0189] According to one embodiment of the present invention, L b Each occurrence, whether identical or different, is selected from the following structure:

[0190]

[0191] Wherein, at least one of R1-R3 is selected, in the same or different manner each time it appears, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is selected, in the same or different manner each time it appears, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0192] According to one embodiment of the present invention, L b Each occurrence, whether identical or different, is selected from the following structure:

[0193]

[0194] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0195] According to one embodiment of the present invention, L b Each occurrence, whether identical or different, is selected from the following structure:

[0196]

[0197] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0198] According to one embodiment of the present invention, the metal complex has the formula Ir(L a ) m (L b ) 3-m The general formula, and has a structure represented by formula 1-1 or formula 1-2:

[0199]

[0200] in,

[0201] m is 1 or 2;

[0202] X1-X2 are selected from CR each time they appear, either the same or different. x Or N; X3 is selected from CR each time it appears, either the same or different. i Or N; A1-A4 are selected from CR each time they appear, either identically or differently. ii Or N; X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii Or N, and at least one of X4 to X7 is selected from CR iii ;

[0203] Y is selected from SiRy R y NR y PR y O, S, or Se; when two Rs exist simultaneously y At that time, two R y Same or different;

[0204] R, R x R y R i R ii R1, R2, R3, R4, R5, R6, and R7, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0205] R iiiEach time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0206] Adjacent substituents R, R x R y R i R ii and R iii They can be arbitrarily connected to form a loop;

[0207] Adjacent substituents R1, R2, R3, R4, R5, R6, and R7 can optionally be linked to form a ring.

[0208] According to one embodiment of the present invention, wherein at least one or two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one or two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0209] According to one embodiment of the present invention, wherein at least two of R1-R3 are selected, each time appearing identically or differently, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, each time appearing identically or differently, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0210] According to one embodiment of the present invention, L b Choose L each time it appears, either the same or different. b1 To L b322 The group formed, L c Choose L each time it appears, either the same or different. c1 To L c231 The group consisting of; the L b1 To L b322 and L c1 To L c231 The specific structure is described in claim 17.

[0211] According to one embodiment of the present invention, the metal complex has Ir(L) a )2(L b ) or Ir(L a )2(L c ) or Ir(L a (L) c )2 or Ir(L a (L) b (L) c The structure of );

[0212] Wherein, when the metal complex has Ir(L a )2(L b When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1904 Any one or any two of the groups formed, L b Choose freely L b1 To L b322 Any one of the groups; when the metal complex has Ir(L a )2(L c When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1904 Any one or any two of the groups formed, L cChoose freely L c1 To L c231 Any one of the groups; when the metal complex has Ir(L a (L) c When L is in the structure of )2 a Choose freely L a1 To L a1904 Any of the groups formed, L c Choose L each time it appears, either the same or different. c1 -L c231 Any one or two of the group consisting of; when the metal complex has Ir(L a (L) b (L) c When L is in the structure of ) a Choose freely L a1 To L a1904 Any of the groups formed, L b Choose freely L b1 To L b322 Any of the groups formed, L c Choose freely L c1 To L c231 Any one of the groups formed.

[0213] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compound 1 to compound 1010; the specific structures of compound 1 to compound 1010 are given in claim 18.

[0214] According to one embodiment of the present invention, the metal complex has Ir(L) a )2(L b ) or Ir(L a )2(L c ) or Ir(L a (L) c )2 or Ir(L a (L) b (L) c The structure of );

[0215] Wherein, when the metal complex has Ir(L a )2(L b When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1906 Any one or any two of the groups formed, L b Choose freely L b1 To L b322 Any one of the groups; when the metal complex has Ir(L a )2(Lc When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1906 Any one or any two of the groups formed, L c Choose freely L c1 To L c231 Any one of the groups; when the metal complex has Ir(L a (L) c When L is in the structure of )2 a Choose freely L a1 To L a1906 Any of the groups formed, L c Choose L each time it appears, either the same or different. c1 -L c231 Any one or two of the group consisting of; when the metal complex has Ir(L a (L) b (L) c When L is in the structure of ) a Choose freely L a1 To L a1906 Any of the groups formed, L b Choose freely L b1 To L b322 Any of the groups formed, L c Choose freely L c1 To L c231 Any one of the groups formed.

[0216] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compound 1 to compound 1028;

[0217] The compounds 1 to 800 and 1011 to 1028 described herein have Ir(L a )2(L b The structure of ) in which two L a Same, L a and L b These correspond to the structures listed in the table below:

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] Among them, compounds 801 to 1010 have Ir(L a )2(L b The structure of ) in which two L a Different, L a and L b These correspond to the structures listed in the table below:

[0230]

[0231]

[0232]

[0233] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0234] anode,

[0235] cathode,

[0236] And an organic layer disposed between the anode and the cathode, the organic layer containing a metal complex, the specific structure of which is shown in any of the foregoing embodiments.

[0237] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

[0238] According to one embodiment of the present invention, the electroluminescent device emits red light.

[0239] According to one embodiment of the present invention, the electroluminescent device emits white light.

[0240] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further includes at least one host material.

[0241] According to one embodiment of the present invention, in the electroluminescent device, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0242] According to another embodiment of the present invention, a compound composition comprising a metal complex is also disclosed, wherein the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0243] Combination with other materials

[0244] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0245] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of host layers, transport layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are 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 herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0246] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0247] Material synthesis examples:

[0248] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0249] Synthesis Example 1: Synthesis of Compound 341

[0250] Step 1: Synthesis of intermediate 3:

[0251]

[0252] Intermediate 1 (2.1 g, 5.2 mmol), intermediate 2 (2.43 g, 5.2 mmol), tetrakis(triphenylphosphine)palladium (0.295 g, 0.26 mmol), sodium carbonate (0.818 g, 7.7 mmol), 1,4-dioxane (20 mL), and water (5 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:3, v / v) to obtain a white solid intermediate 3 (2.9 g, yield 78.5%).

[0253] Step 2: Synthesis of intermediate 4:

[0254]

[0255] Intermediate 3 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 4 (2.6 g, yield 97.2%).

[0256] Step 3: Synthesis of intermediate 5:

[0257]

[0258] Intermediate 4 (2.6 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol), and DMF (40 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated in the solution. The solution was filtered, washed several times with water, and dried to obtain yellow solid intermediate 15 (2 g, yield 99.9%).

[0259] Step 4: Synthesis of Intermediate 6:

[0260]

[0261] Intermediate 5 (2 g, 4 mmol), neopentylboronic acid (935 mg, 8 mmol), palladium acetate (90 mg, 0.4 mmol), Sphos (328 mg, 0.8 mmol), potassium phosphate trihydrate (3.2 g, 12 mmol), and toluene (30 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting solvent: ethyl acetate: petroleum ether = 1:20, v / v) to obtain a yellow solid intermediate 6 (2 g, yield 94.4%).

[0262] Step 5: Synthesis of iridium dimer:

[0263]

[0264] A mixture of intermediate 6 (1.1 g, 2.08 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain a solution of the dimer ethoxyethanol, which could be used in the next reaction without further purification.

[0265] Step 6: Synthesis of Compound 341

[0266]

[0267] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 271 mg (1.2 mmol) of 3,7-diethyl-3-methylnonane-4,6-dione, and 0.57 g (4.15 mmol) of potassium carbonate were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The solution was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.27 g of compound 341 was obtained, with a yield of 22%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1474.8.

[0268] Synthesis Example 2: Synthesis of Compound 441

[0269] Step 1: Synthesis of Compound 441

[0270]

[0271] An ethoxylated ethanol solution of the iridium dimer obtained in step 5 of Example 1, along with 3,7-diethyl-3,7-dimethylnonane-4,6-dione (58 mg, 0.24 mmol) and potassium carbonate (0.11 g, 0.8 mmol), was added to a 50 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.05 g of product compound 441 was obtained, with a yield of 21%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1488.8.

[0272] Synthesis Example 3: Synthesis of Compound 442

[0273] Step 1: Synthesis of Intermediate 8:

[0274]

[0275] Intermediate 7 (1.6 g, 4.1 mmol), intermediate 2 (1.93 g, 4.1 mmol), tetrakis(triphenylphosphine)palladium (0.237 g, 0.2 mmol), sodium carbonate (0.652 g, 6.2 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:3, v / v) to obtain a white solid intermediate 8 (2.46 g, yield 86.5%).

[0276] Step 2: Synthesis of Intermediate 9:

[0277]

[0278] Intermediate 8 (2.46 g, 3.5 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 9 (2.32 g, 99.9% yield).

[0279] Step 3: Synthesis of Intermediate 10:

[0280]

[0281] Intermediate 9 (2.32 g, 3.65 mmol), cesium carbonate (3.56 g, 10.9 mmol), and DMF (35 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated in the solution. The solution was filtered, washed several times with water, and dried to obtain yellow solid intermediate 10 (1.4 g, yield 80.3%).

[0282] Step 4: Synthesis of iridium dimer:

[0283]

[0284] A mixture of intermediate 10 (1.4 g, 2.93 mmol), iridium trichloride trihydrate (344 mg, 0.98 mmol), 2-ethoxyethanol (21 mL), and water (7 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0285] Step 5: Synthesis of Compound 442

[0286]

[0287] An ethoxylated ethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (353 mg, 1.47 mmol), and potassium carbonate (0.67 g, 4.9 mmol) were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then poured into a funnel containing diatomaceous earth, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.88 g of compound 442 was obtained, with a yield of 64.8%. The product was further purified by column chromatography. The structure of the compound was confirmed by LC-MS as the target product, with a molecular weight of 1384.6.

[0288] Synthesis Example 4: Synthesis of Compound 438

[0289] Step 1: Synthesis of Intermediate 12:

[0290]

[0291] Intermediate 1 (1.45 g, 3.59 mmol), intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:2, v / v) to obtain a white solid intermediate 12 (2.2 g, yield 95.7%).

[0292] Step 2: Synthesis of intermediate 13:

[0293]

[0294] Intermediate 12 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried under vacuum to obtain yellow solid intermediate 13 (1.8 g, 99.8% yield).

[0295] Step 3: Synthesis of intermediate 14:

[0296]

[0297] Intermediate 13 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (30 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution. The mixture was filtered, washed several times with water, and dried to obtain yellow solid intermediate 14 (1.2 g, yield 83.2%).

[0298] Step 4: Synthesis of Intermediate 15:

[0299]

[0300] Intermediate 14 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness to obtain the crude product, and separated by silica gel column chromatography (eluting with ethyl acetate:petroleum ether = 1:20, v / v) to obtain a yellow solid intermediate 15 (0.88 g, yield 67.5%).

[0301] Step 5: Synthesis of iridium dimer:

[0302]

[0303] A mixture of intermediate 15 (0.88 g, 1.91 mmol), iridium trichloride trihydrate (193 mg, 0.55 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0304] Step 6: Synthesis of Compound 438

[0305]

[0306] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 200 mg (0.83 mmol) of 3,7-diethyl-3,7-dimethylnonane-4,6-dione, and 0.38 g (2.75 mmol) of potassium carbonate were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.41 g of compound 438 was obtained, with a yield of 55.3%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1348.7.

[0307] Synthesis Example 5: Synthesis of Compound 446

[0308] Step 1: Synthesis of Intermediate 17:

[0309]

[0310] Intermediate 16 (1.45 g, 3.59 mmol), intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:2, v / v) to obtain a white solid intermediate 17 (2.0 g, 90% yield).

[0311] Step 2: Synthesis of intermediate 18:

[0312]

[0313] Intermediate 17 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 18 (1.8 g, 99.8% yield).

[0314] Step 3: Synthesis of Intermediate 19:

[0315]

[0316] Intermediate 18 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (35 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution. The mixture was filtered, washed several times with water, and dried to obtain yellow solid intermediate 19 (1.2 g, yield 83.2%).

[0317] Step 4: Synthesis of Intermediate 20:

[0318]

[0319] Intermediate 19 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:50, v / v) to obtain a yellow solid intermediate 20 (0.88 g, yield 67.5%).

[0320] Step 5: Synthesis of iridium dimer:

[0321]

[0322] A mixture of intermediate 20 (0.51 g, 1.1 mmol), iridium trichloride trihydrate (130 mg, 0.37 mmol), 2-ethoxyethanol (27 mL), and water (9 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0323] Step 6: Synthesis of Compound 446

[0324]

[0325] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 130 mg (0.55 mmol) of 3,7-diethyl-3,7-dimethylnonane-4,6-dione, and 0.26 g (1.85 mmol) of potassium carbonate were added to a 100 mL round-bottom flask, and the mixture was reacted at 50 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.24 g of compound 446 was obtained, with a yield of 48%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1348.7.

[0326] Synthesis Example 6: Synthesis of Compound 1021

[0327] Step 1: Synthesis of Intermediate 17:

[0328]

[0329] Intermediate 16 (1.89 g, 4.68 mmol), intermediate 2 (2.18 g, 4.67 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), sodium carbonate (0.74 g, 7 mmol), 1,4-dioxane (28 mL), and water (7 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:2, v / v) to obtain a white solid intermediate 21 (2.3 g, 70% yield).

[0330] Step 2: Synthesis of intermediate 22:

[0331]

[0332] Intermediate 21 (4.5 g, 6.34 mmol) was dissolved in 30 mL of ethanol, followed by the addition of 2 M HCl (30 mL). The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 22 (3.1 g, 99.8% yield).

[0333] Step 3: Synthesis of intermediate 23:

[0334]

[0335] Intermediate 22 (3.1 g, 6.34 mmol), cesium carbonate (5.16 g, 15.8 mmol), and DMF (50 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution. The mixture was filtered, washed several times with water, and dried to obtain yellow solid intermediate 23 (5.5 g, 88% yield).

[0336] Step 4: Synthesis of intermediate 24:

[0337]

[0338] Intermediate 23 (3.13 g, 6.3 mmol), neopentylboronic acid (2.21 g, 19 mmol), palladium acetate (144 mg, 0.64 mmol), Sphos (525 mg, 1.28 mmol), potassium phosphate trihydrate (5.1 g, 19.02 mmol), and toluene (30 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:20, v / v) to obtain a yellow solid intermediate 24 (2.6 g, 75% yield).

[0339] Step 5: Synthesis of iridium dimer:

[0340]

[0341] A mixture of intermediate 24 (1.6 g, 3 mmol), iridium trichloride trihydrate (356 mg, 1 mmol), 2-ethoxyethanol (36 mL), and water (12 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was filtered, the solid was washed with methanol, and dried under vacuum to give the iridium dimer, which could be used in the next reaction without further purification.

[0342] Step 6: Synthesis of Compound 1021

[0343]

[0344] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (360 mg, 1.5 mmol), potassium carbonate (0.69 g, 5 mmol), and 2-ethoxyethanol (35 mL) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.1 g of compound 1021 was obtained, in a yield of 6%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1488.8.

[0345] Synthesis Example 7: Synthesis of Compound 405

[0346] Step 1: Synthesis of intermediate 26:

[0347]

[0348] Intermediate 25 (1.45 g, 3.59 mmol), intermediate 11 (1.43 g, 3.59 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.18 mmol), sodium carbonate (0.57 g, 5.4 mmol), 1,4-dioxane (16 mL), and water (4 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture. The mixture was separated into aqueous and organic phases, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:2, v / v) to obtain a white solid intermediate 26 (2.2 g, yield 95.7%).

[0349] Step 2: Synthesis of intermediate 27:

[0350]

[0351] Intermediate 26 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 27 (1.8 g, 99.8% yield).

[0352] Step 3: Synthesis of intermediate 28:

[0353]

[0354] Intermediate 27 (1.8 g, 3.4 mmol), cesium carbonate (2.2 g, 6.8 mmol), and DMF (35 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated in the solution. The solution was filtered, washed several times with water, and dried to obtain yellow solid intermediate 28 (1.2 g, yield 83.2%).

[0355] Step 4: Synthesis of intermediate 29:

[0356]

[0357] Intermediate 28 (1.2 g, 2.83 mmol), neopentylboronic acid (656 mg, 5.66 mmol), palladium acetate (32 mg, 0.14 mmol), Sphos (116 mg, 0.28 mmol), potassium phosphate trihydrate (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:50, v / v) to obtain a yellow solid intermediate 29 (0.88 g, yield 67.5%).

[0358] Step 5: Synthesis of iridium dimer:

[0359]

[0360] A mixture of intermediate 29 (0.88 g, 1.91 mmol), iridium trichloride trihydrate (193 mg, 0.55 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was filtered to give 210 mg of iridium dimer, which could be used in the next reaction without further purification.

[0361] Step 6: Synthesis of Compound 405

[0362]

[0363] The iridium dimer (210 mg, 0.114 mmol) obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (165 mg, 0.69 mmol), potassium carbonate (0.1 g, 1.35 mmol), and ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.1 g of compound 405 was obtained, with a yield of 13.5%. The structure of this compound was confirmed as the target product by LC-MS, with a molecular weight of 1348.7.

[0364] Synthesis Example 8: Synthesis of Compound 205

[0365] Step 1: Synthesis of Compound 205

[0366]

[0367] The iridium dimer (210 mg, 0.114 mmol) obtained in step 5 of Synthetic Example 7, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (184 mg, 0.69 mmol), potassium carbonate (0.1 g, 1.35 mmol), and ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.1 g of compound 205 was obtained, with a yield of 13.2%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1374.6.

[0368] Synthesis Example 9: Synthesis of Compound 1019

[0369] Step 1: Synthesis of intermediate 31:

[0370]

[0371] Intermediate 30 (2.2 g, 5.2 mmol), intermediate 2 (2.43 g, 5.2 mmol), tetrakis(triphenylphosphine)palladium (0.295 g, 0.26 mmol), sodium carbonate (0.818 g, 7.7 mmol), 1,4-dioxane (20 mL), and water (5 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture. The mixture was separated into aqueous and organic phases, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:3, v / v) to obtain a white solid intermediate 31 (2.9 g, yield 76.5%).

[0372] Step 2: Synthesis of intermediate 32:

[0373]

[0374] Intermediate 31 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2 M HCl. The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain yellow solid intermediate 32 (2.7 g, yield 97.2%).

[0375] Step 3: Synthesis of intermediate 33:

[0376]

[0377] Intermediate 32 (2.7 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol), and DMF (40 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated in the solution. The solution was filtered, washed several times with water, and dried to obtain yellow solid intermediate 33 (2 g, yield 98.4%).

[0378] Step 4: Synthesis of intermediate 34:

[0379]

[0380] Intermediate 33 (2 g, 3.94 mmol), neopentylboronic acid (914 mg, 7.88 mmol), palladium acetate (90 mg, 0.4 mmol), Sphos (328 mg, 0.8 mmol), potassium phosphate trihydrate (3.2 g, 12 mmol), and toluene (30 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting solvent: ethyl acetate: petroleum ether = 1:20, v / v) to obtain a yellow solid intermediate 34 (1.1 g, yield 50.6%).

[0381] Step 5: Synthesis of iridium dimer:

[0382]

[0383] A mixture of intermediate 34 (1.1 g, 2.02 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0384] Step 6: Synthesis of Compound 1019

[0385]

[0386] An ethoxylated ethanol solution of the iridium dimer obtained in the previous step, 271 mg (1.2 mmol) of 3,7-diethyl-3,7-dimethylnonane-4,6-dione, and 0.57 g (4.15 mmol) of potassium carbonate were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The solution was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.22 g of compound 1019 was obtained, with a yield of 17.5%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1376.7.

[0387] Synthesis Example 10: Synthesis of Compound 447

[0388] Step 1: Synthesis of intermediate 36:

[0389]

[0390] Intermediate 16 (2.61 g, 6.47 mmol), intermediate 35 (2.67 g, 6.47 mmol), tetrakis(triphenylphosphine)palladium (0.37 g, 0.32 mmol), sodium carbonate (1.03 g, 9.7 mmol), 1,4-dioxane (52 mL), and water (13 mL) were added to a round-bottom flask. The reaction mixture was then heated to 90 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:2, v / v) to obtain the target product, white solid intermediate 36 (3.1 g, 72%).

[0391] Step 2: Synthesis of intermediate 37:

[0392]

[0393] Intermediate 36 (3.12 g, 4.77 mmol) was dissolved in 20 mL of ethanol, followed by the addition of 2N HCl (20 mL). The reaction was then heated to reflux and stirred overnight. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. The solid was filtered, washed several times with water, and dried to obtain the target product, yellow solid intermediate 37 (2.74 g, 96%).

[0394] Step 3: Synthesis of intermediate 38:

[0395]

[0396] Intermediate 37 (2.74 g, 4.6 mmol), cesium carbonate (3.89 g, 11.93 mmol), and DMF (40 mL) were heated to 135 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. Water was added until a large amount of yellow solid precipitated in the solution. The mixture was filtered, and the solid was washed several times with water and then dried to obtain the target product, yellow solid intermediate 38 (1.84 g, 91%).

[0397] Step 4: Synthesis of intermediate 39:

[0398]

[0399] Intermediate 38 (0.56 g, 1.27 mmol), neopentylboronic acid (0.42 g, 3.81 mmol), Pd2(dba)3 (0.58 g, 0.06 mmol), Sphos (0.53 g, 0.127 mmol), potassium phosphate trihydrate (1.02 g, 3.81 mmol), and toluene (15 mL) were heated to reflux overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The mixture was then filtered through a funnel containing diatomaceous earth. The filtrate was collected, evaporated to dryness, and the crude product was separated by silica gel column chromatography (eluting solvent: ethyl acetate: petroleum ether = 1:100, v / v) to obtain the target product, yellow solid intermediate 39 (0.58 g, 95%).

[0400] Step 5: Synthesis of iridium dimer:

[0401]

[0402] A mixture of intermediate 39 (0.58 g, 1.23 mmol), iridium trichloride trihydrate (0.12 g, 0.35 mmol), 2-ethoxyethanol (36 mL), and water (12 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0403] Step 6: Synthesis of Compound 447

[0404]

[0405] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 0.13 g (0.53 mmol) of 3,7-diethyl-3,7-dimethylnonane-4,6-dione, 0.69 g (5 mmol) of potassium carbonate, and 35 mL of 2-ethoxyethanol were added to a round-bottom flask and reacted at 50 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. Filtration yielded 0.18 g of product compound 447, in 37% yield. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product, with a molecular weight of 1376.7.

[0406] Synthesis Example 11: Synthesis of Compound 1020

[0407] Step 1: Synthesis of iridium dimer:

[0408]

[0409] A mixture of intermediate 40 (1 g, 2.17 mmol), iridium trichloride trihydrate (293 mg, 0.83 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0410] Step 2: Synthesis of Compound 1020

[0411]

[0412] An ethoxylated ethanol solution of the iridium dimer obtained in the previous step, 271 mg (1.2 mmol) of 3,7-diethyl-3,7-dimethylnonane-4,6-dione, and 0.57 g (4.15 mmol) of potassium carbonate were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The solution was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.45 g of compound 341 was obtained, with a yield of 40.1%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1350.7.

[0413] Synthesis Example 12: Synthesis of Compound 1018

[0414] Step 1: Synthesis of intermediate 41:

[0415]

[0416] Intermediate 19 (344 mg, 0.81 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ide](3-chloropyridine)palladium dichloride (28 mg, 0.04 mmol) were dissolved in THF (5 mL). Under nitrogen protection, a 2 mol / L THF solution of 3,3,3-trifluoro-2,2-dimethylpropylmagnesium bromide (4 mL) was added and the reaction was carried out at 45 °C. The reaction was stopped when intermediate 19 disappeared as monitored by LC-MS. The reaction was quenched by adding ammonium chloride aqueous solution, extracted with EA, and the organic phase was collected, dried, and the solvent was removed by rotary evaporation. The mixture was separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:100, v / v) to give intermediate 41 (248 mg, yield 60%).

[0417] Step 2: Synthesis of iridium dimer:

[0418]

[0419] A mixture of intermediate 41 (0.28 g, 0.54 mmol), iridium trichloride trihydrate (50 mg, 0.14 mmol), 2-ethoxyethanol (15 mL), and water (5 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was filtered and the solid was collected. The solid was washed three times with methanol, and the solvent was removed under vacuum. The resulting red solid iridium dimer was collected and could be used in the next reaction without further purification.

[0420] Step 3: Synthesis of Compound 1018

[0421]

[0422] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (51 mg, 0.21 mmol), potassium carbonate (98 mg, 0.71 mmol), and 15 mL of ethoxyethanol were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.1 g of product compound 1018 was obtained, in 49% yield. The structure of the compound was confirmed by LC-MS as the target product, with a molecular weight of 1456.6.

[0423] Synthesis Example 13: Synthesis of Compound 452

[0424] Step 1: Synthesis of intermediate 44:

[0425]

[0426] Intermediate 42 (418 mg, 0.95 mmol), intermediate 43 (370 g, 1 mmol), tetrakis(triphenylphosphine)palladium (55 mg, 0.048 mmol), sodium carbonate (151 mg, 1.43 mmol), 1,4-dioxane (8 mL), and water (2 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was then separated by silica gel column chromatography (eluting agent: ethyl acetate: petroleum ether = 1:3, v / v) to obtain a white solid intermediate 44 (500 mg, yield 81.3%).

[0427] Step 2: Synthesis of intermediate 45:

[0428]

[0429] Intermediate 44 (500 mg, 0.77 mmol) and diphenyl ether (4 mL) were heated to 180 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The crude product was separated by silica gel column chromatography (eluting ethyl acetate: petroleum ether = 1:20, v / v) to obtain a yellow solid intermediate 45 (110 mg, yield 30%).

[0430] Step 3: Synthesis of iridium dimer:

[0431]

[0432] A mixture of intermediate 45 (110 mg, 0.23 mmol), iridium trichloride trihydrate (25 mg, 0.077 mmol), 2-ethoxyethanol (6 mL), and water (2 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0433] Step 4: Synthesis of Compound 452

[0434]

[0435] An ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (111 mg, 0.46 mmol), and potassium carbonate (159 mg, 1.15 mmol) were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.04 g of compound 341 was obtained, with a yield of 37.6%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1380.6.

[0436] Synthesis Example 14: Synthesis of Compound 1017

[0437] Step 1: Synthesis of intermediate 47:

[0438]

[0439] Intermediate 19 (0.5 g, 1.18 mmol), intermediate 46 (346 mg, 2.36 mmol), Pd2(dba)3 (12 mg, 0.012 mmol), tBuDavephos (21 mg, 0.06 mmol), lithium acetate (0.39 g, 5.9 mmol), water (43 mg, 2.36 mmol), and DMF (30 mL) were added to a reaction tube. The tube was sealed under nitrogen protection and heated to 150 °C overnight. After the reaction was completed, the tube was cooled to room temperature and evaporated to dryness to obtain a crude product. The crude product was separated by silica gel column chromatography to obtain a yellow solid intermediate 47 (0.4 g, 73.5%).

[0440] Step 2: Synthesis of iridium dimer:

[0441]

[0442] A mixture of intermediate 47 (0.7 g, 1.52 mmol), iridium trichloride trihydrate (0.18 g, 0.5 mmol), 2-ethoxyethanol (27 mL), and water (9 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was filtered, the solid was washed with methanol, and dried to obtain the iridium dimer, which could be used in the next reaction without further purification.

[0443] Step 3: Synthesis of Compound 1017

[0444]

[0445] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.18 g, 0.76 mmol), potassium carbonate (0.35 g, 2.53 mmol), and 2-ethoxyethanol (10 mL) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen protection. The mixture was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.37 g of product compound 1017 was obtained, with a yield of 54%. The structure of this compound was confirmed by LC-MS as the target product, with a molecular weight of 1352.6.

[0446] Synthesis Example 15: Synthesis of Compound 1022

[0447] Step 1: Synthesis of intermediate 49:

[0448]

[0449] Intermediate 42 (600 mg, 1.37 mmol), intermediate 48 (546 mg, 1.43 mmol), tetrakis(triphenylphosphine)palladium (79 mg, 0.069 mmol), sodium carbonate (218 mg, 2.06 mmol), 1,4-dioxane (8 mL), and water (2 mL) were added to a 100 mL round-bottom flask. The reaction mixture was then heated to 80 °C and stirred overnight under nitrogen protection. After TLC showed that the reaction was complete, the mixture was cooled to room temperature. Ethyl acetate was then added to the reaction mixture, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and evaporated to dryness to obtain the crude product. The crude product was separated by silica gel column chromatography (eluting agent: ethyl acetate:petroleum ether = 1:3, v / v) to obtain a white solid intermediate 49 (620 mg, yield 68.4%).

[0450] Step 2: Synthesis of Intermediate 50:

[0451]

[0452] Intermediate 49 (620 mg, 0.94 mmol) and diphenyl ether (5 mL) were heated to 140 °C overnight under nitrogen protection. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The crude product was separated by silica gel column chromatography (eluting ethyl acetate: petroleum ether = 1:20, v / v) to give intermediate 50 (260 mg, yield 56.5%) as a yellow solid.

[0453] Step 3: Synthesis of iridium dimer:

[0454]

[0455] A mixture of intermediate 50 (260 mg, 0.53 mmol), iridium trichloride trihydrate (62 mg, 0.18 mmol), 2-ethoxyethanol (9 mL), and water (3 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully evaporated by rotary evaporation to obtain an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0456] Step 4: Synthesis of Compound 1022

[0457]

[0458] An ethoxylated ethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (86 mg, 0.36 mmol), and potassium carbonate (124 mg, 0.9 mmol) were added to a 100 mL round-bottom flask, and the mixture was reacted at 60 °C for 24 hours under nitrogen protection. The solution was then filtered through a funnel containing diatomaceous earth and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not to dryness. After filtration, 0.08 g of compound 1022 was obtained, with a yield of 31.5%. The structure of this compound was confirmed as the target product by LC-MS, with a molecular weight of 1408.6.

[0459] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0460] Through a special ligand structure design, the metal complex of the present invention achieves a deeper red luminescence. The following photoluminescence spectral (PL) data further demonstrates that this deeper red luminescence is an unexpected and excellent effect.

[0461] Spectral data

[0462] The photoluminescence (PL) spectra of the compound of the present invention and the comparative compound were determined using a Prism F98 fluorescence spectrophotometer manufactured by Shanghai Prism Technology Co., Ltd. The compound sample of the present invention or the comparative compound sample were prepared with HPLC-grade toluene to a concentration of 3 × 10⁻⁶. -5 A solution of mol / L was prepared, and then excited with light at a wavelength of 500 nm at room temperature (298 K) and its emission spectrum was measured. The measurement results are shown in Table 1.

[0463] Table 1 Spectral Data

[0464] Serial Number Sample number <![CDATA[Maximum emission wavelength λ max (nm)]]> 1 Compound RD-A 623 2 Compound RD-B 619 3 Compound RD 619 4 Compound 442 631 5 Compound 341 622 6 Compound 441 622

[0465] The structures of the related compounds of this invention and the comparative compounds are shown below:

[0466]

[0467]

[0468] discuss:

[0469] Phenylisoquinoline ligands are a widely studied and applied class of ligand structures in the prior art, especially in the field of red phosphorescent metal complexes. Studies have found that introducing an additional fused-ring structure onto the isoquinoline ring of such ligands leads to a significant blue shift in emission wavelength. For example, as shown in Table 1, the maximum emission wavelength of compound RD-B, which contains a phenylbenzoisoquinoline ligand, is 4 nm blue-shifted compared to compound RD-A. In this invention, compounds 442, 341, and 441 also introduce fused-ring structures at the same positions on the isoquinoline ring, but their maximum emission wavelengths all exhibit a significant red shift compared to compound RD. This red shift effect is diametrically opposed to the trends observed in the prior art. These comparisons demonstrate the uniqueness of the metal complex structure of this invention, providing a novel metal complex structure with an unexpectedly deeper red emission color.

[0470] Device Examples

[0471] Device Example 1

[0472] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, the ITO anode was sequentially deposited at a rate of 0.2–2 Å / s via thermal vacuum evaporation. Compound HI was doped into compound HT as a hole injection layer (HIL, 3:97), with a thickness of… The compound HT is used as a hole transport layer (HTL), with a thickness of Compound EB is used as an electron blocking layer (EBL), with a thickness of Then, compound 341 of the present invention is doped into the host compound RH as a light-emitting layer (EML, 5:95), with a thickness of Compound HB is used as a hole blocking layer (HBL), with a thickness of On the HBL, a mixture of the deposited compound ET and 8-hydroxyquinoline-lithium (Liq) serves as an electron transport layer (ETL), with a thickness of [missing information]. Finally, a 1 nm thick Liq layer was deposited as the electron injection layer, and a 120 nm thick Al layer was deposited as the cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and desiccant to complete the device.

[0473] Device Comparison Example 1

[0474] The device comparative example 1 was prepared in the same manner as device example 1, except that compound RD was used instead of compound 341 of the present invention in the light-emitting layer (EML).

[0475] Device Example 3

[0476] The preparation method of Device Example 3 is the same as that of Device Example 1, except that Compound 438 of the present invention is used instead of Compound 341 of the present invention in the light-emitting layer (EML) and the weight ratio of Compound 438 and Compound RH of the present invention is adjusted to 3:97.

[0477] Device Example 4

[0478] The preparation method of device example 4 is the same as that of device example 3, except that compound 446 of the present invention is used instead of compound 438 of the present invention in the light-emitting layer (EML).

[0479] Device Example 5

[0480] The preparation method of device example 5 is the same as that of device example 3, except that compound 1021 of the present invention is used instead of compound 438 of the present invention in the light-emitting layer (EML).

[0481] Device Example 6

[0482] The preparation method of Device Example 6 is the same as that of Device Example 3, except that Compound 405 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0483] Device Example 7

[0484] The preparation method of Device Example 7 is the same as that of Device Example 3, except that Compound 1019 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0485] Device Example 8

[0486] The preparation method of Device Example 8 is the same as that of Device Example 3, except that Compound 447 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0487] Device Example 9

[0488] The preparation method of Device Example 9 is the same as that of Device Example 3, except that Compound 1020 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0489] Device Example 10

[0490] The preparation method of Device Example 10 is the same as that of Device Example 3, except that Compound 1018 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0491] Device Example 11

[0492] The preparation method of Device Example 11 is the same as that of Device Example 3, except that Compound 1017 of the present invention is used instead of Compound 438 of the present invention in the light-emitting layer (EML).

[0493] Device Comparison Example 3

[0494] The device comparative example 3 was prepared in the same manner as device example 3, except that compound RD1 was used instead of compound 438 of the present invention in the light-emitting layer (EML).

[0495] The partial layer structure and thickness of the device are shown in the table below. The device uses more than one material; it is obtained by doping different compounds in the stated weight ratios.

[0496] Table 2 Partial device structures of device embodiments and comparative examples.

[0497]

[0498]

[0499]

[0500] The structure of the materials used in the device is shown below:

[0501]

[0502]

[0503] The IVL characteristics of the device were measured. Table 3 shows the results at 15 mA / cm². 2 CIE data, drive voltage, and maximum emission wavelength (λ) of the device embodiment and device comparison example measured under constant current. max ), half-maximum width at half maximum (FWHM), and external quantum efficiency (EQE).

[0504] Table 3 Device Data

[0505]

[0506]

[0507] discuss:

[0508] As shown in Table 3, Example 1, while maintaining a very narrow half-peak width and a substantially flat lower voltage similar to Comparative Example 1, exhibits a significant red shift in color, according to CIE. xThe maximum emission wavelength shifted from 0.684 in Comparative Example 1 to 0.688, and the maximum emission wavelength shifted from 621 nm in Comparative Example 1 to 625 nm, achieving a deeper red emission. Moreover, the external quantum efficiency of Example 1 was significantly improved from the extremely high efficiency level of 24.11% in Comparative Example 1, with an improvement of nearly 7.5%. This confirms that the present invention provides a deep red phosphorescent material with narrow peak width, low voltage, and high efficiency, fully demonstrating the broad application prospects of the compound of the present invention.

[0509] Compared to Comparative Example 3, Examples 3-11, while maintaining a very narrow full width at half maximum (FWHM) and low voltage level essentially equivalent to Comparative Example 3, exhibited a red shift in the maximum emission wavelength, achieving a deeper red emission. Furthermore, the device efficiency of Examples 3-11 was significantly improved beyond the extremely high efficiency of 24.24% achieved in Comparative Example 3, with Examples 3, 4, 8, and 9 achieving ultra-high device efficiencies exceeding 26%. This further confirms that the present invention provides a narrow-peak-width, low-voltage, and highly efficient deep red phosphorescent material, and fully demonstrates the broad application prospects of the compounds of this invention.

[0510] Furthermore, since top-emitting device structures are widely used in commercial devices, this paper further verifies the excellent performance of the metal complex of the present invention in top-emitting devices.

[0511] Device Example 2

[0512] First, a 0.7mm thick glass substrate is used, on which a pre-patterned indium tin oxide (ITO) substrate is formed. / Ag / ITO As the anode, the substrate was then dried in a glove box to remove moisture and mounted on a support before being transferred into the vacuum chamber. The organic layer specified below was applied at a vacuum degree of approximately 10... -6 Under Torr conditions The deposition rate was achieved sequentially on the anode via vacuum thermal evaporation. First, compounds HT1 and HI were simultaneously deposited as a hole injection layer (HIL, 97:3). Compound HT1 was deposited on HIL as a hole transport layer (HTL). HTL also serves as a microcavity conditioning layer. Next, compound EB1 is deposited on the hole transport layer as an electron blocking layer (EBL). Then, compound 341 and compound RH of the present invention were co-deposited as the luminescent layer (EML, 3:97). On the EML, compound ET1 and Liq were co-deposited as an electron transport layer (ETL, 40:60). Evaporation Metallic Yb was used as the electron injection layer (EIL), and metallic Ag and Mg were co-deposited in a 9:1 ratio. As the cathode, the evaporated compound CPL54 was used as the cathode capping layer (CPL, The compound CPL54 was purchased from Jiangsu Sanyue Technology Co., Ltd. The device was then transferred back to the glove box and sealed with a glass cap and desiccant in a nitrogen atmosphere to complete the device.

[0513] Device Comparison Example 2

[0514] The device comparative example 2 was prepared in the same manner as device example 2, except that compound RD was used instead of compound 341 of the present invention in the light-emitting layer (EML).

[0515] Device Example 12

[0516] The preparation method of device example 12 is the same as that of device example 2, except that compound 447 of the present invention is used instead of compound 341 of the present invention in the light-emitting layer (EML).

[0517] The partial layer structure and thickness of the device are shown in the table below. The device uses more than one material; it is obtained by doping different compounds in the stated weight ratios.

[0518] Table 4. Partial device structures of Examples 2, 12 and Comparative Example 2

[0519]

[0520]

[0521] The structure of the new material used in the device is shown below:

[0522]

[0523] The IVL characteristics of the device were measured at 10 mA / cm. 2 The CIE data and maximum emission wavelength λ of the device were measured. max Voltage (V), full width at half maximum (FWHM), and external quantum efficiency (EQE) were recorded and are shown in Table 5.

[0524] Table 5 Device data for Examples 2, 12 and Comparative Example 2

[0525]

[0526] discuss:

[0527] As can be seen from Table 5, the top-emitting device of Example 2, which uses the compound of the present invention in the light-emitting layer, also exhibits excellent performance. Example 2 maintains a very narrow half-width at half-maximum (HWHM) and a substantially similar low voltage level to Comparative Example 2. Furthermore, the emission color of Example 2 shows a significant redshift compared to Comparative Example 2: CIEx shifts from 0.680 to 0.690, and the maximum emission wavelength redshifts from 618 nm to 623 nm. Simultaneously, Example 2 achieves a significant improvement in EQE, approaching 17%, while maintaining a voltage comparable to Comparative Example 2. Example 12 exhibits an extremely narrow HWHM almost identical to Comparative Example 2, maintains a substantially similar low voltage level, and, more importantly, shows a significant redshift in the maximum emission wavelength, while also achieving a significant improvement in EQE, approaching 13%, demonstrating similar excellent device performance to Example 2. This further demonstrates the superior properties of the metal complexes of the present invention and their great application potential in top-emitting devices.

[0528] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A metal complex comprising a metal M and a ligand L coordinated to M. a The metal M is selected from metals with a relative atomic mass greater than 40, and the L a It has a structure represented by Equation 1: in, Ring A and ring B are each independently selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms; ring C is selected from aromatic rings with 6-30 carbon atoms or heteroaromatic rings with 6-30 ring atoms. R i R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R iii The same or different occurrences each time indicate single or multiple substitution; Y is selected from SiR y R y GeR y R y NR y PR y , O, S or Se; When two R exist simultaneously y At that time, two R y They can be the same or different; X1-X2 are selected from CR each time they appear, either the same or different. x Or N; R, R i R ii R x and R y Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; R iii Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Adjacent substituent R i R x R y , R, R ii and R iii They can be arbitrarily connected to form a ring.

2. The metal complex as described in claim 1, wherein, Ring A and / or ring B are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms; ring C is selected from aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 6-18 ring atoms. Preferably, ring A and / or ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6-10 carbon atoms, or a heteroaromatic ring having 3-10 carbon atoms; ring C is selected from an aromatic ring having 6-10 carbon atoms or a heteroaromatic ring having 6-10 ring atoms.

3. The metal complex as described in claim 1 or 2, wherein the L a Choose any one of the structures from Equation 2 to Equation 17: in, In Equations 2-17, X1-X2 are selected from CR each time they appear, either identically or differently. x Or N; X3 is selected from CR i Or N; A1-A6 are selected from CR each time they appear, either identically or differently. ii Or N; X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii Or N, and at least one of X4 to X7 is selected from CR iii ; Z is selected from CR each time it appears, either identically or differently. iv R iv SiR iv R iv PR iv O, S or NR iv When two R exist simultaneously iv At that time, two R iv Same or different; Y is selected from SiR y R y NR y PR y O, S, or Se; when two Rs exist simultaneously y At that time, two R y Same or different; R, R x R y R i R ii and R iv Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; R iii Each time it appears, it is selected from the group consisting of the following, either identically or differently: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Adjacent substituent R i R x R y , R, R ii R iii and R iv They can be arbitrarily connected to form a loop; Preferably, L a Choose the structure represented by free form 2 or form 3; More preferably, L a Choose the structure represented by free form 3.

4. The metal complex as described in claim 3, wherein, In equations 2-17, X1-X n and / or A1-A m At least one of them is selected from N, and the X n The A corresponds to the largest of the sequence numbers of X1-X7 in any one of Equations 2-17. m The one with the largest sequence number among any one of Equations 2-17 corresponding to A1-A6; Preferably, in equations 2-17, X1-X n At least one of them is selected from N, and the X n The largest of the sequence numbers that exists in any one of Equations 2-17 for X1-X7; More preferably, X2 is N.

5. The metal complex as described in claim 3, wherein, In Equations 2-17, X1-X2 are each independently selected from CR. x X3 is selected from CR i A1-A6 are each independently selected from CR ii X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii And at least one of X4 to X7 is selected from CR iii ; adjacent substituent R x R i R ii R iii They can be arbitrarily connected to form a loop; Preferably, the R x R i R ii Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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, cyano groups, and combinations thereof; The R iii Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, cyano groups, and combinations thereof; More preferably, the R x R i R ii At least one or two of them, each time appearing in the same or different manner, are selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, 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 alksilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof; R iii Each time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

6. The metal complex according to any one of claims 3-5, wherein, In Equations 2-17, at least one or two of A1-A6 are selected from CR. ii And the R ii Each time it appears, it is selected from the same or different groups of deuterium, halogen, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alksilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, cyano group, or combinations thereof; X3 is selected from CR i And the R i Each time it appears, it is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alksilyl with 3-20 carbon atoms, substituted or unsubstituted arylsilyl with 6-20 carbon atoms, cyano, or combinations thereof; Preferably, the R i Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof. The R ii Each time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyl dimethylsilyl, phenyl dimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

7. The metal complex according to any one of claims 3-6, wherein, In Formulas 2-17, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof. Preferably, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, trimethylsilyl, or combinations thereof.

8. The metal complex according to any one of claims 3-7, wherein, In Equations 2-17, Y is selected from O or S.

9. The metal complex according to any one of claims 3-8, wherein, In Equations 2-17, X1 is selected from CR. x X2 is selected from CR x Or N; Preferably, the R x It is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alkoxyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof.

10. The metal complex according to any one of claims 1-9, wherein, The ligand L a It has the structure represented by Equation 18: In Equation 18, Y is selected from O or S; R x1 R x2 R i R ii1 R ii2 R ii3 R ii4 , R, R iii1 R iii2 R iii3 R iii4 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; R iii1 R iii2 R iii3 R iii4 At least one of the following, each time appearing identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Substituted 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Preferably, R x1 R x2 One or two and / or R ii1 R ii2 R ii3 R ii4 At least one or two of the following are selected, in the same or different manner each time they appear, from deuterium, halogen, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alksilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, or combinations thereof; R is selected from halogen, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alksilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, or combinations thereof; R iii1 R iii2 R iii3 R iii4 At least one or two of them, when appearing in the same or different manner, are selected from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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 alksilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof; More preferably, R x1 R x2 One or two and / or R ii1 R ii2 R ii3 R ii4 At least one or two of them, each time appearing identically or differently, are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof; R is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic 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 alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, or combinations thereof; R iii1 R iii2 R iii3 R iii4 At least one or two of them, when appearing in the same or different manner each time, are selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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, and combinations thereof.

11. The metal complex of claim 10, wherein, In Equation 18, R x1 R x2 R iii1 R iii2 R iii3 R iii4 R ii1 R ii2 R ii3 R ii4 At least one of R is selected from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof. Preferably, R x1 R x2 R iii1 R iii2 R iii3 R iii4 R ii1 R ii2 R ii3 R ii4 At least one of R is selected from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 cyclic carbon atoms, and combinations thereof, each time it appears in the same or different manner.

12. The metal complex according to any one of claims 1-11, wherein, L a Each occurrence is either identical or different from the group consisting of the following structures: In the above structure, TMS is trimethylsilyl; Optionally, the L a1 To L a1904 In the structure, hydrogen can be partially or completely replaced by deuterium.

13. The metal complex according to any one of claims 1-12, wherein, The metal complex has M(L) a ) m (L b ) n (L c ) q The structure; Among them, metal M is selected from metals with a relative atomic mass greater than 40; L a L b and L c These are the first, second, and third ligands of the complex, respectively; m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m + n + q equals the oxidation state of metal M; when m is greater than 1, multiple L... a Same or different; when n is 2, the two L b Same or different; when q is 2, the two L c Same or different; L a L b and L c They can be selectively linked to form multidentate ligands; L b and L c Each time the same or different occurrences appear, select the group consisting of the following structures: Among them, R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; X b Each time it appears, select the group consisting of the following, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ; R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Wherein, the adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

14. The metal complex of claim 13, wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; Preferably, the metal M is selected from Ir, Pt or Os; more preferably, the metal M is Ir.

15. The metal complex of claim 13 or 14, wherein L b Each occurrence, whether identical or different, is selected from the following structure: R1–R7 are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1–20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3–20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1–20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3–20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7–30 carbon atoms, substituted or unsubstituted alkoxy groups having 1–20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Preferably, at least one or two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one or two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; More preferably, wherein at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

16. The metal complex of claim 15, wherein the metal complex has the formula Ir(L a ) m (L b ) 3-m The general formula, and has a structure represented by formula 1-1 or formula 1-2: in, m is 1 or 2; X1-X2 are selected from CR each time they appear, either the same or different. x Or N; X3 is selected from CR each time it appears, either the same or different. i Or N; A1-A4 are selected from CR each time they appear, either identically or differently. ii Or N; X4-X7 are selected from CH or CR each time they appear, either identically or differently. iii Or N, and at least one of X4 to X7 is selected from CR iii ; Y is selected from SiR y R y NR y PR y O, S, or Se; when two Rs exist simultaneously y At that time, two R y Same or different; R, R x R y R i R ii R1, R2, R3, R4, R5, R6, and R7, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted groups having 6-30 carbon atoms. Aryloxy groups, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; R iii Each time it appears, it is selected from the group consisting of the following, either identically or differently: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto groups having 0-20 carbon atoms, and combinations thereof; Adjacent substituents R, R x R y R i R ii and R iii They can be arbitrarily connected to form a loop; Adjacent substituents R1, R2, R3, R4, R5, R6, and R7 can optionally be linked to form a ring; Preferably, at least one or two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one or two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; More preferably, wherein at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

17. The metal complex according to any one of claims 13-15, wherein L b Each occurrence is either identical or different from the group consisting of the following structures: in, L c Each occurrence is either identical or different from the group consisting of the following structures:

18. The metal complex of claim 17, wherein, The metal complex has Ir(L) a )2(L b ) or Ir(L a )2(L c ) or Ir(L a (L) c )2 or Ir(L a (L) b (L) c The structure of ); Wherein, when the metal complex has Ir(L a )2(L b When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1904 Any one or any two of the groups formed, L b Choose freely L b1 To L b322 Any one of the groups; when the metal complex has Ir(L a )2(L c When L is in the structure of ) a Choose L each time it appears, either the same or different. a1 To L a1904 Any one or any two of the groups formed, L c Choose freely L c1 To L c231 Any one of the groups; when the metal complex has Ir(L a (L) c When L is in the structure of )2 a Choose freely L a1 To L a1904 Any of the groups formed, L c Choose L each time it appears, either the same or different. c1 To L c231 Any one or two of the group consisting of; when the metal complex has Ir(L a (L) b (L) c When L is in the structure of ) a Choose freely L a1 To L a1904 Any of the groups formed, L b Choose freely L b1 To L b322 Any of the groups formed, L c Choose freely L c1 To L c231 Any one of the groups formed; Preferably, the metal complex is selected from the group consisting of compound 1 to compound 1010; The compounds 1 to 800 described herein have Ir(L a )2(L b The structure of ) in which two L a Same, L a and L b These correspond to the structures listed in the table below: Among them, compounds 801 to 1010 have Ir(L a )2(L b The structure of ) in which two L a Different, L a and L b These correspond to the structures listed in the table below:

19. An electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex according to any one of claims 1-18.

20. The electroluminescent device of claim 19, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

21. The electroluminescent device of claim 19 or 20, wherein the electroluminescent device emits red or white light.

22. The electroluminescent device of claim 21, wherein the light-emitting layer further comprises at least one host material; preferably, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

23. A compound composition comprising the metal complex according to any one of claims 1-18.

24. The use of the metal complex as described in any one of claims 1-18 in electroluminescent devices.

25. An organic layer comprising the metal complex according to any one of claims 1-18.

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