Electroluminescent material and device thereof

Abstract

Disclosed are electroluminescent materials and devices thereof. The electroluminescent material is a metal complex comprising a metal M and a ligand L coordinated to M a , the L a having a structure represented by Formula 1. The metal complex can be used as a light-emitting material in an electroluminescent device. These novel metal complexes can better tune the light-emitting color of the device while maintaining a very narrow full width at half maximum, achieve a deeper red emission, and enable a lower driving voltage or maintain a low voltage level and substantially improve the device efficiency. Such novel metal complexes can provide better device performance. Also disclosed are electroluminescent devices and compositions of compounds.

Description

TECHNICAL FIELD

[0001] The present application 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 structure 1, and electroluminescent devices and compound compositions comprising the same. BACKGROUND

[0002] Organic electronic devices include, but are not limited to, the following kinds: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke at Kodak reported a two-layer organic electroluminescent device that included an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). Upon biasing the device, green light emitted from the device. 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 light emitting layers between the cathode and anode. Since OLEDs are self-emissive solid state devices, they offer the potential for large area, flexible, bright, and energy efficient flat panel displays and lighting applications. In addition, the intrinsic properties of organic materials, such as their flexibility, can make them well suited for special applications, such as on flexible substrates.

[0004] OLEDs can be categorized into three different types according to their light emission mechanism. OLED invented by Tang and van Slyke is fluorescent OLED. It only uses singlet emission. The triplet states generated in the device are wasted through a nonradiative decay channel. Therefore, the internal quantum efficiency (IQE) of fluorescent OLED is only 25%. This limitation hinders the commercialization of OLED. In 1997, Forrest and Thompson reported phosphorescent OLED, which uses triplet emission from heavy metals containing complexes as emitters. 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). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gaps, making it possible for excitons to return from triplet to singlet states. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be quite large as long as it has a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods, such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the materials can be dissolved or dispersed in solvents.

[0007] The emission color of OLEDs can be achieved by the design of light-emitting material structure. OLEDs can include one or multiple light-emitting layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime and high operating voltage. Commercial full-color OLED displays usually employ a hybrid strategy, using blue fluorescent and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have more saturated emission spectrum, higher efficiency and longer device lifetime.

[0008] Phosphorescent metal complexes can be used as phosphorescent dopants in light-emitting layers for organic electroluminescent lighting or display applications. The metal complexes developed so far still have various shortcomings in electroluminescent devices. In order to meet the increasing demands of the industry, such as lower voltage, higher device efficiency, specific wavelength range of light-emitting color, more saturated light-emitting color, and longer device lifetime, the research and development of metal complexes still need to be further improved. SUMMARY

[0009] The present application aims to provide a series of metal complexes of ligands with structure of formula 1 to solve at least part of the above problems. The metal complexes can be used as light-emitting materials in organic electroluminescent devices. These new metal complexes can better adjust the light-emitting color of the device while maintaining a very narrow half-peak width, achieve deeper red light-emitting, and reduce the driving voltage of the device or maintain a low voltage level, greatly improve the device efficiency. These new metal complexes can provide better device performance.

[0010] According to one embodiment of the present application, 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 relative atomic mass greater than 40, and the L a has a structure represented by formula 1:

[0011]

[0012] wherein each of ring A and ring B is independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms; ring C is selected from an aromatic ring having 6-30 carbon atoms or a heteroaromatic ring having 6-30 ring atoms;

[0013] R i , R ii each occurrence, the same or different, represents single substitution, multiple substitution, or no substitution; R iii each occurrence, the same or different, represents single substitution or multiple substitution;

[0014] Y is selected from SiR y R y , GeR y R y , NR y , PR y , O, S or Se;

[0015] When two R y are present simultaneously, the two R y may be the same or different;

[0016] X1-X2is, on each occurrence, the same or different, selected from CR x or N;

[0017] R, R i , R ii , R x and R y is, on each occurrence, the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having from 7-30 carbon atoms, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilane having from 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having from 3-20 carbon atoms, substituted or unsubstituted aryl germanium having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphine, and combinations thereof;

[0018] R iii is, on each occurrence, the same or different, selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having from 7-30 carbon atoms, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilane having from 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having from 3-20 carbon atoms, substituted or unsubstituted aryl germanium having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphine, and combinations thereof;

[0019] adjacent substituents Ri , R x , R y , R, R ii and R iii may optionally be linked to form a ring.

[0020] According to another embodiment of the present application, 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, the metal complex comprising a metal M and a ligand L coordinated to M a , the metal M being selected from metals having a relative atomic mass greater than 40, the L a having a structure represented by Formula 1:

[0021]

[0022] wherein each of ring A, ring B is independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms; ring C is selected from an aromatic ring having 6-30 carbon atoms or a heteroaromatic ring having 6-30 ring atoms;

[0023] R i , R ii are the same or different at each occurrence and represent mono-substitution, poly-substitution, or no substitution; R iii are the same or different at each occurrence and represent mono-substitution or poly-substitution;

[0024] Y is selected from SiR y R y , GeR y R y , NR y , PR y , O, S or Se;

[0025] when two R y are present simultaneously, the two R y may be the same or different;

[0026] X1-X2are the same or different at each occurrence and are selected from CR x or N;

[0027] R, R i , R ii , R x and R yeach occurrence is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0028] R iii each occurrence is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0029] adjacent substituents R i , R x , R y , R, R ii , and R iii may optionally be linked to form a ring.

[0030] According to another embodiment of the present application, a compound composition comprising the metal complex described in the above embodiments is also disclosed.

[0031] The novel metal complexes with polycyclic ligands disclosed in the present application can be used as light emitting materials in electroluminescent devices. These novel metal complexes can better tune the light emitting color of the devices while maintaining very narrow full width at half maximum, achieve deeper red light emission, and can lower the driving voltage of the devices or maintain low voltage level, greatly improve the device efficiency. These novel metal complexes can provide better device performance. BRIEF DESCRIPTION OF DRAWINGS

[0032] Figure 1 is a schematic diagram of an organic light emitting device that can contain the metal complexes and compound compositions disclosed herein.

[0033] Figure 2 is a schematic diagram of another organic light emitting device that can contain the metal complexes and compound compositions disclosed herein.

[0034] Figure 3 is a schematic diagram of a typical top emitting OLED device that can contain the metal complexes and compound compositions disclosed herein. DETAILED DESCRIPTION

[0035] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light emitting device 100 is schematically, non-limitingly illustrated. The figures are not necessarily drawn to scale, and some layer structures in the figures can be omitted as desired. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of the layers, as well as exemplary materials, are described in more detail in U.S. Patent No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated herein by reference.

[0036] Each of these layers has more examples. For example, flexible and transparent substrate-anode combinations are disclosed in U.S. Patent No. 5,844,363, incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entirety, disclose examples of cathodes, including composite cathodes with a thin layer of metal such as Mg:Ag overlying a transparent, conductive, sputter-deposited ITO layer. The principles and use of a blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of a protection layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0037] A typical top-emitting OLED device structure is as follows Figure 3The 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 referred to as a prime layer), an emission layer (EML) 305, a hole blocking layer (HBL) 306, which is an optional layer, 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 with reflectivity greater than 50%; preferably, the reflectivity of the anode is greater than 70%; more preferably, the reflectivity of the anode is greater than 80%; while the cathode layer 109 should be a semi-transparent or transparent conductive material, including but not limited to MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or combinations thereof, with average transmittance greater than 15% for light with wavelength in the visible region; preferably, the average transmittance is greater than 20%; more preferably, the average transmittance is greater than 25%.

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

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

[0040] The OLED also requires a capping layer, such as Figure 2 An organic light emitting device 200 is shown schematically and non-limitingly, which is similar to the OLED device 100 described above Figure 1 Differently, the cathode 190 can also include a capping layer 102 on top to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing a capping function can be used as a capping layer, such as glass or an organic-inorganic hybrid layer. The capping layer should be placed directly or indirectly outside the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0041] Devices fabricated in accordance with embodiments of the application can be incorporated into a variety of consumer products, including electronic equipment, such as desktop and laptop computers, tablet computers, cell phones, digital media players and many other kinds of electronic equipment. Some examples of these products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor signage and / or signals, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays and tail lights.

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

[0043] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as "disposed on" a second layer, the first layer is disposed farther from the substrate than the second layer. Unless specified, there can be intervening layers between the first and second layers. For example, a cathode can be described as "disposed on" an anode even though various organic layers are between the cathode and the anode.

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

[0045] A ligand can be referred to as "photosensitive" when it is believed to directly contribute to the photoactive properties of an emissive material. A ligand can be referred to as "auxiliary" when it is believed not to contribute to the photoactive properties of an emissive material, although an auxiliary ligand can change the properties of a photosensitive ligand.

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

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

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

[0049] Definitions of terms regarding substituents

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

[0051] Alkyl - as used herein, includes straight-chain and branched-chain alkyl groups. Alkyl groups can be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Of the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, alkyl groups can be optionally substituted.

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

[0053] Heteroalkyl - As used herein, heteroalkyl includes groups in which one or more carbons of an alkyl group are replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. Heteroalkyl groups can be heteroalkyl groups having 1 to 20 carbon atoms, preferably heteroalkyl groups having 1 to 10 carbon atoms, more preferably heteroalkyl groups having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxy methyl, ethoxymethoxy methyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethygermylmethyl, triethygermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group can be optionally substituted.

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

[0055] 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.

[0056] 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.

[0057] 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.

[0058] Heteroaryl - As used herein, a non-fused and fused heteroaromatic group that can contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group can be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoseleophene, carbazole, indolocarbazole, pyridinoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazol, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, benzofuro[3,2-d]pyridine, furo[3,2-d]dipyridine, benzothieno[3,2-d]pyridine, thieno[3,2-d]dipyridine, benzoseleto[3,2-d]pyridine, seleto[3,2-d]dipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole, and nitrogen analogs thereof. Additionally, the heteroaryl group can be optionally substituted.

[0059] Alkoxy - As used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as described above. The 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, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group can be optionally substituted.

[0060] Aryloxy - As used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl 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. Additionally, the aryloxy group can be optionally substituted.

[0061] Arylalkyl - as used herein, encompasses an aryl group substituted with an alkyl group. The arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, 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-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, 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. Of the foregoing, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred. Additionally, the arylalkyl group can be optionally substituted.

[0062] Alkylsilyl - as used herein, encompasses an alkyl group substituted with a silyl group. 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, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, methyldi-t-butylsilyl. Additionally, the alkylsilyl group can be optionally substituted.

[0063] Arylsilyl - as used herein, encompasses a silyl group substituted with at least one aryl group. The arylsilyl group can be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-t-butylsilyl. Additionally, the arylsilyl group can be optionally substituted.

[0064] Alkylgermyl - as used herein, encompasses an alkyl-substituted germyl group. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of alkylgermyl groups include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tri-t-butylgermyl, triisobutylgermyl, dimethyl-t-butylgermyl, methyldi-t-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0065] Arylgermyl - as used herein, encompasses a germyl group substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of arylgermyl groups include triphenylgermyl, phenyldiphenylgermyl, diphenylphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyl-t-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0066] The term "aza" in azadibenzofurans, azadibenzothiophenes, and the like, refers to one or more C-H groups in the corresponding aromatic fragment being replaced with a nitrogen atom. For example, azatriphenylenes include dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above aza derivatives can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as described herein.

[0067] In the present disclosure, when any of the terms from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, and substituted phosphine, is used, unless otherwise defined, it means that any of the alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine groups can be substituted with one or more of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, hydroxyl, thiol, sulfinyl, sulfonyl, phosphine, and combinations thereof.

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

[0069] In the compounds mentioned in the present 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. The replacement of other stable isotopes in the compounds can be preferred due to its enhanced efficiency and stability of the device.

[0070] In the compounds mentioned in the present disclosure, poly-substitution means including di-substitution, up to the range of the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure represents poly-substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent can exist at multiple available substitution positions on the structure to which it is connected, and the substituent that exists at multiple available substitution positions can be the same structure or different structures.

[0071] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the formed ring can be a single ring or a multiple ring (including a spiro ring, a bridged ring, a fused ring, etc.), and an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms that are directly bonded to each other, or substituents bonded to carbon atoms that are further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms that are directly bonded to each other.

[0072] The expression that adjacent substituents can optionally be connected to form a ring is also intended to mean that two substituents bonded to the same carbon atom are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

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

[0075]

[0076] The expression that adjacent substituents can optionally be connected to form a ring is also intended to mean that two substituents bonded to carbon atoms that are further apart are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0077]

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

[0079]

[0080] According to one embodiment of the present application, a metal complex comprising a metal M selected from metals having a relative atomic mass greater than 40 and a ligand L coordinated to M is disclosed a , said L a having a structure represented by Formula 1:

[0081]

[0082] wherein each of ring A, ring B is independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms; ring C is selected from an aromatic ring having 6-30 carbon atoms or a heteroaromatic ring having 6-30 ring atoms;

[0083] R i , R ii each occurrence, identically or differently, represents mono-, poly-, or no substitution; R iii each occurrence, identically or differently, represents mono-, poly-, or no substitution;

[0084] Y is selected from SiR y R y , GeR y R y , NR y , PR y , O, S, or Se;

[0085] when two R y are present simultaneously, the two R y may be the same or different;

[0086] X1-X2, each occurrence, is selected from CR x or N;

[0087] R, R i , R ii , R x , and R yat each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0088] R iii at each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0089] adjacent substituents R i , R x , R y , R, R ii and R iii may optionally be linked to form a ring.

[0090] In this context, adjacent substituents Ri , R x , R y , R, R ii and R iii may optionally be joined to form a ring, is intended to mean that any one or more of these groups of substituents, for example, two substituents R i , two substituents R ii , two substituents R iii , two substituents R y , two substituents R x , a substituent R i and a substituent R x , a substituent R i and a substituent R iii , a substituent R and a substituent R y , and a substituent R iii and a substituent R, can be joined to form a ring. Obviously, none of these substituents can also be joined to form a ring.

[0091] According to one embodiment of the present application, wherein R iii each occurrence is the same or different, represents a mono- or poly-substituted;

[0092] R iii each occurrence is the same or different, is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilane having 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having 3-20 carbon atoms, substituted or unsubstituted aryl germanium having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0093] According to one embodiment of the present application, wherein the metal complex optionally comprises additional ligands, the additional ligands can be joined, optionally with the L a , to form a tridentate ligand, a tetradentate ligand, a pentadentate ligand, or a hexadentate ligand.

[0094] According to one embodiment of the present application, wherein each of ring A and / or ring B is independently selected from a five-membered unsaturated carbocyclic 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 of 6-18 carbon atoms, or a heteroaromatic ring having 6-18 ring atoms.

[0095] According to one embodiment of the present application, wherein each of ring A and / or ring B is independently selected from a five-membered unsaturated carbocyclic 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 of 6-10 carbon atoms, or a heteroaromatic ring having 6-10 ring atoms.

[0096] According to one embodiment of the present application, wherein the L a is selected from the structure represented by any one of Formula 2 to Formula 17:

[0097]

[0098]

[0099] wherein,

[0100] In Formula 2-Formula 17, X1-X2is the same or different at each occurrence and is selected from CR x or N; X3is selected from CR i or N; A1-A6is the same or different at each occurrence and is selected from CR ii or N; X4-X7is the same or different at each occurrence and is selected from CH, CR iii or N, and at least one of X4to X7is selected from CR iii ;

[0101] Z is the same or different at each occurrence and is selected from CR iv R iv , SiR iv R iv , PR iv , O, S or NR iv ; when two R iv are present simultaneously, the two R iv are the same or different; for example when Z is selected from CR iv R iv , the two R iv may be the same or different; further for example when Z is selected from SiR iv R iv , the two R iv may be the same or different;

[0102] Y is selected from SiR y R y , NRy PR y O, S, or Se; when two Rs exist simultaneously y 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;

[0103] 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;

[0104] R iiieach occurrence is the same or different selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having 3-20 carbon atoms, substituted or unsubstituted aryl germanium having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0105] adjacent substituents R i , R x , R y , R, R ii , and R iii may optionally be linked to form a ring.

[0106] According to one embodiment of the present application, wherein L a is selected from the structure represented by Formula 2 or Formula 3.

[0107] According to one embodiment of the present application, wherein L a is selected from the structure represented by Formula 3.

[0108] According to one embodiment of the present application, wherein in Formula 2- Formula 17, X1-X n and / or A1-A m is selected from N, said X n corresponding to the largest number of said X1-X7 present in any one of Formula 2- Formula 17, said A m corresponding to the largest number of said A1-A6 present in any one of Formula 2- Formula 17; for example, for Formula 3, said X n corresponding to the largest number of said X1-X7 present in Formula 3, X7, said A m corresponding to the largest number of said A1-A6 present in Formula 3, A4, i.e., in Formula 3, at least one of X1-X7 and / or A1-A4 is selected from N.

[0109] According to one embodiment of the present application, wherein in any one of Formulas 2-17, at least one of X1-X7 is selected from N. n n corresponding to the highest number of the X1-X7 present in any one of Formulas 2-17.

[0110] According to one embodiment of the present application, wherein in any one of Formulas 2-17, X2 is N.

[0111] According to one embodiment of the present application, wherein in any one of 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 the same or different at each occurrence and are selected from CH or CR iii , and at least one of X4 through X7 is selected from CR iii ; and adjacent substituents R x , R i , R ii , R iii may optionally be joined to form a ring.

[0112] Herein, adjacent substituents R x , R i , R ii , R iii may optionally be joined to form a ring is intended to mean that any one or more of the groups of adjacent substituents, for example, between two substituents R ii , between two substituents R iii , between two substituents R x , between substituent R i and R iii , and between substituent R i and R x , can be joined to form a ring. Obviously, none of these substituents can also be joined to form a ring.

[0113] According to one embodiment of the present application, wherein in any one of 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 the same or different at each occurrence and are selected from CH or CR iii , and at least one of X4 through X7 is selected from CR iii ; and the R x , R i , R ii ​each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilicon having from 6-20 carbon atoms, cyano, and combinations thereof;

[0114] R iii each occurrence is the same or different selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilicon having from 6-20 carbon atoms, cyano, and combinations thereof;

[0115] adjacent substituents R x , R i , R ii , R iii may optionally be linked to form a ring.

[0116] According to one embodiment of the present application, wherein in formula 2 - formula 17, X1-X2are each independently selected from CR x ; X3is selected from CR i ; A1-A4are each independently selected from CR ii ; X4-X7are each occurrence the same or different selected from CH or CR iii , and at least one of X4to X7is selected from CR iii ; and at least one or two of the R x , R i , R ii each occurrence is the same or different selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilicon having from 6-20 carbon atoms, cyano, and combinations thereof;

[0117] R iiiare the same or different at each occurrence selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof;

[0118] adjacent substituents R x , R i , R ii , R iii may optionally be joined to form a ring.

[0119] In the present embodiment, at least one or two of the R x , R i , R ii at each occurrence are the same or different selected from the group of substituents, is intended to mean that at least one or two substituents at each occurrence are the same or different selected from the group consisting of two R x substituents, all R i substituents, and all R ii substituents.

[0120] According to one embodiment of the present application, wherein in Formulae 2-17, at least one or two of A1-A6 are selected from CR ii ; and X3is selected from CR i .

[0121] According to one embodiment of the present application, wherein in Formulae 2-17, at least one or two of A1-A6 are selected from CR ii , and the R ii at each occurrence are the same or different selected from deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilane having 6-20 carbon atoms, cyano, or combinations thereof;

[0122] X3is selected from CR i ; and the R ieach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, cyano, or combinations thereof.

[0123] According to one embodiment of the present application, wherein in Formula 2- Formula 17, at least one or two of A1-A6 is selected from CR ii , and said R ii each occurrence is the same or different selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof;

[0124] X3is selected from CR i ; wherein said R i each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0125] According to one embodiment of the present application, wherein in Formula 2- Formula 17, wherein R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, or combinations thereof.

[0126] According to one embodiment of the present application, wherein in Formula 2- Formula 17, wherein R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated t-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, trimethylsilyl, or combinations thereof.

[0127] According to one embodiment of the present application, wherein in Formula 2- Formula 17, Y is selected from O or S.

[0128] According to one embodiment of the present application, wherein in Formula 2- Formula 17, Y is selected from O.

[0129] According to one embodiment of the present application, wherein in Formula 2- Formula 17, X1and X2are each independently selected from CR x .

[0130] According to one embodiment of the present application, wherein in Formula 2- Formula 17, X1is selected from CR x , X2is selected from CR x or N.

[0131] According to one embodiment of the present application, wherein in Formula 2- Formula 17, X1is selected from CR x , X2is selected from CR x or N; and said R x is, on each occurrence, the same or different, selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having from 6 to 20 carbon atoms, or a combination thereof.

[0132] According to one embodiment of the present application, wherein said ligand L a has a structure represented by Formula 18:

[0133]

[0134] wherein in Formula 18,

[0135] Y is selected from O or S;

[0136] R x1 , R x2 , R i , R ii1 , R ii2 , R ii3 , R ii4 , R, R iii1 , R iii2 , R iii3 , R iii4each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0137] R iii1 , R iii2 , R iii3 , R iii4 each occurrence is the same or different selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilane with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0138] According to one embodiment of the present application, wherein the ligand L a has a structure represented by Formula 18:

[0139]

[0140] wherein, in formula 18,

[0141] Y is selected from O or S;

[0142] R x1 , R x2 , R ii1 , R ii2 , R ii3 , R ii4 at least one or two of each occurrence is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having from 6 to 20 carbon atoms, or combinations thereof; R is selected from halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having from 6 to 20 carbon atoms, or combinations thereof;

[0143] R iii1 , R iii2 , R iii3 , R iii4 at least one or two of each occurrence is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having from 6 to 20 carbon atoms, and combinations thereof.

[0144] According to one embodiment of the present application, wherein the ligand L a has a structure represented by formula 18:

[0145]

[0146] wherein, in formula 18,

[0147] Y is selected from O or S;

[0148] R x1 , R x2one or both of R ii1 one or both of R ii2 one or both of R ii3 one or both of R ii4 are each, identically or differently on each occurrence, selected from the group consisting of a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, or a combination thereof; R is selected from a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, or a combination thereof;

[0149] one or both of R iii1 one or both of R iii2 one or both of R iii3 one or both of R iii4 are each, identically or differently on each occurrence, selected from the group consisting of a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, and combinations thereof.

[0150] According to one embodiment of the present application, in formula 18,

[0151] Y is selected from O or S;

[0152] one or both of R iii1 one or both of R iii2 one or both of R iii3 one or both of R iii4 one or both of R ii1 one or both of R ii2 one or both of R ii3 one or both of 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;

[0153] 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.

[0154] According to one embodiment of the present invention, wherein, in formula 18,

[0155] Y is selected from O or S;

[0156] 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;

[0157] 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.

[0158] According to one embodiment of the present invention, wherein, in formula 18, R ii1 Rii2 one of R ii3 one of R ii1 one of R ii2 one of R ii3 or two (e.g., R ii1 and R ii2 , or R ii2 and R ii3 , or R ii1 and R ii3 ) at each occurrence are the same or different selected from the group consisting of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, or a combination thereof.

[0159] According to one embodiment of the present application, wherein, in Formula 18, at least one of R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 at each occurrence is the same or different selected from the group consisting of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, and a combination thereof.

[0160] In the present embodiment, at least one of R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 at each occurrence is the same or different selected from the group of substituents, intended to mean that at least one of R x1 , R x2 at each occurrence is the same or different selected from the group of substituents, and / or at least one of R iii1 , R iii2 , R iii3 , R iii4 at each occurrence is the same or different selected from the group of substituents, and / or at least one of 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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 x1 , R x2 , at least one of R iii1 , R iii2 , R iii3 , R iii4 , at least one of R ii1 , R ii2 , R ii3 , R ii4 , at least one of R

[0165] According to one embodiment of the present application, wherein L a is, at each occurrence, identical or different, selected from the group consisting of L a1 to L a1904 , wherein the specific structures of L a1 to L a1904 are given in claim 12.

[0166] According to one embodiment of the present application, wherein L a is, at each occurrence, identical or different, selected from the group consisting of L a1 to L a1906 , wherein the specific structures of L a1 to L a1904 are given in claim 12, and L a1905 to L a1906 are:

[0167]

[0168] According to one embodiment of the present application, wherein the structure of L a1 to L a1904 is partially or completely substituted with deuterium.

[0169] According to one embodiment of the present application, wherein the structure of L a1 to L a1906 is partially or completely substituted with deuterium.

[0170] According to one embodiment of the present application, wherein the metal complex has the structure of M(L a ) m (L b ) n (Lc ) q the structure of

[0171] wherein the metal M is selected from metals having an atomic mass greater than 40; L a , L b and L c are respectively a first ligand, a second ligand and a third ligand of said complex; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than 1, the plurality of L a are identical or different; when n is 2, the two L b are identical or different; when q is 2, the two L c are identical or different;

[0172] L a , L b and L c may optionally be linked to form polydentate ligands; for example L a , L b and L c may optionally be linked to form tetradentate or hexadentate ligands; L a , L b and L c may also all be unlinked so as not to form polydentate ligands;

[0173] L b and L c are each, on each occurrence identically or differently, selected from the group consisting of the following structures:

[0174]

[0175] wherein R a , R b and R c , on each occurrence, identically or differently, represent mono-, poly- or no substitution;

[0176] X b , on each occurrence, is selected from the group consisting of O, S, Se, NR N1 and CR C1 R C2 ;

[0177] X c and X d , on each occurrence, are selected from the group consisting of O, S, Se and NR N2 ;

[0178] R a , R b , R c , R N1 , RN2 , R C1 , and R C2 are each, the same or different at each occurrence, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms in length, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilicon with 3-20 carbon atoms, substituted or unsubstituted arylsilicon with 6-20 carbon atoms, substituted or unsubstituted alkyl germanium with 3-20 carbon atoms, substituted or unsubstituted aryl germanium with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0179] wherein adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 , and R C2 may optionally be linked to form a ring.

[0180] In this embodiment, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 , and R C2 may optionally be linked to form a ring, is intended to mean that where adjacent groups of substituents, for example, between two substituents R a , between two substituents R b , between two substituents R c , between substituents R a and R b , between substituents R a and R c , between substituents R b and R c , between substituents R a and R N1 , between substituents R b and R N1 are linked to form a ring.between R and R, the substituents R c and R N1 between R and R, the substituents R a and R C1 between R and R, the substituents R a and R C2 between R and R, the substituents R b and R C1 between R and R, the substituents R b and R C2 between R and R, the substituents R c and R C1 between R and R, the substituents R c and R C2 between R and R, the substituents R a and R N2 between R and R, the substituents R b and R N2 between R and R, and R C1 and R C2 between R and R, any one or more of these groups of substituents can be linked to form a ring. It is obvious that none of these substituents can also be linked to form a ring.

[0181] In the present embodiment, L a , L b and L c may optionally be linked to form a polydentate ligand, which is intended to mean that any two or three of L a , L b and L c may be linked to form a tetradentate ligand or a hexadentate ligand. It is obvious that none of L a , L b and L c may also be linked so as not to form a polydentate ligand.

[0182] According to one embodiment of the application, wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0183] According to one embodiment of the application, wherein the metal M is selected from Ir, Pt or Os.

[0184] According to one embodiment of the application, wherein the metal M is Ir.

[0185] According to one embodiment of the application, wherein L b is, at each occurrence, identically or differently selected from the following structures:

[0186]

[0187] wherein R1-R7 are the same or different at each occurrence selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3-20 ring atoms, substituted or unsubstituted aralkyl having a number of carbon atoms from 7-30, substituted or unsubstituted alkoxy having from 1-20 carbon atoms, substituted or unsubstituted aryloxy having from 6-30 carbon atoms, substituted or unsubstituted alkenyl having from 2-20 carbon atoms, substituted or unsubstituted aryl having from 6-30 carbon atoms, substituted or unsubstituted heteroaryl having from 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having from 3-20 carbon atoms, substituted or unsubstituted arylsilicon having from 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having from 3-20 carbon atoms, substituted or unsubstituted aryl germanium having from 6-20 carbon atoms, substituted or unsubstituted amino having from 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0188] According to one embodiment of the present application, wherein L b is selected at each occurrence from the following structures:

[0189]

[0190] wherein at least one of R1-R3 is selected at each occurrence from substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is selected at each occurrence from substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1-20 carbon atoms, or combinations thereof.

[0191] According to one embodiment of the present application, wherein L b is selected at each occurrence from the following structures:

[0192]

[0193] wherein at least two of R1-R3 are each occurrence the same or different selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are each occurrence the same or different selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or combinations thereof.

[0194] According to one embodiment of the present application, wherein L b each occurrence is the same or different selected from the following structures:

[0195]

[0196] wherein at least two of R1-R3 are each occurrence the same or different selected from substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are each occurrence the same or different selected from substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2-20 carbon atoms, or combinations thereof.

[0197] According to one embodiment of the present application, wherein the metal complex has the formula Ir(L a ) m (L b ) 3-m of the general formula and has a structure represented by Formula 1-1 or Formula 1-2:

[0198]

[0199] wherein,

[0200] m is 1 or 2;

[0201] X1-X2 are each occurrence the same or different selected from CR x or N; X3 is each occurrence the same or different selected from CR i or N; A1-A4 are each occurrence the same or different selected from CR ii or N; X4-X7 are each occurrence the same or different selected from CH, CR iii or N, and at least one of X4-X7 is selected from CR iii ;

[0202] Y is selected from SiRy R y , NR y , PR y , O, S or Se; when two R y are present simultaneously, the two R y are the same or different;

[0203] R, R x , R y , R i , R ii , R1, R2, R3, R4, R5, R6, R7are the same or different at each occurrence selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0204] R iiieach occurrence is the same or different selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having 3-20 carbon atoms, substituted or unsubstituted aryl germanium having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0205] adjacent substituents R, R x , R y , R i , R ii and R iii may optionally be linked to form a ring;

[0206] adjacent substituents R1, R2, R3, R4, R5, R6, R7may optionally be linked to form a ring.

[0207] According to one embodiment of the present application, wherein at least one or two of R1-R3are each occurrence the same or different selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or combinations thereof; and / or at least one or two of R4-R6are each occurrence the same or different selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or combinations thereof.

[0208] 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.

[0209] 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.

[0210] 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 );

[0211] 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 cis selected from any one of the group consisting of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )(L c )2, L a is selected from any one of the group consisting of L a1 to L a1904 , L c is selected from any one of the group consisting of L c1 -L c231 ; when the metal complex has the structure of Ir(L a )(L b )(L c ), L a is selected from any one of the group consisting of L a1 to L a1904 , L b is selected from any one of the group consisting of L b1 to L b322 , L c is selected from any one of the group consisting of L c1 to L c231 .

[0212] According to an embodiment of the present application, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 1010; the specific structures of the Compound 1 to Compound 1010 are shown in claim 18.

[0213] According to an embodiment of the present application, wherein the metal complex has the structure of 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 ).

[0214] wherein, when the metal complex has the structure of Ir(L a )2(L b ), L a is selected from any one of the group consisting of L a1 to L a1906 , L b is selected from any one of the group consisting of L b1 to L b322 ; when the metal complex has the structure of Ir(L a )2(Lc ) of the metal complex is L a each occurrence is the same or different and is selected from any one or both of L a1 to L a1906 ; when the metal complex has the structure of Ir(L c each occurrence is the same or different and is selected from any one or both of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )(L c )2, L a is selected from any one of L a1 to L a1906 ; when the metal complex has the structure of Ir(L c each occurrence is the same or different and is selected from any one or both of L c1 -L c231 ; when the metal complex has the structure of Ir(L a )(L b )(L c ), L a is selected from any one of L a1 to L a1906 ; when the metal complex has the structure of Ir(L b each occurrence is the same or different and is selected from any one or both of L b1 to L b322 ; when the metal complex has the structure of Ir(L c each occurrence is the same or different and is selected from any one or both of L c1 to L c231 .

[0215] According to one embodiment of the present application, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 1028;

[0216] wherein the Compound 1 to Compound 800 and Compound 1011 to Compound 1028 have the structure of Ir(L a )2(L b ), wherein the two L a are the same, L a and L b correspond to the structures selected from the following table, respectively:

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] wherein compounds 801 to 1010 have the structure of Ir(L a )2(L b ), wherein the two L a are different, L a and L b correspond to the structures selected from the following table:

[0229]

[0230]

[0231]

[0232] According to one embodiment of the present application, there is also disclosed an electroluminescent device comprising:

[0233] an anode,

[0234] a cathode,

[0235] and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex, the metal complex having the specific structure as shown in any of the preceding embodiments.

[0236] According to one embodiment of the present application, in the electroluminescent device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0237] According to one embodiment of the present application, the electroluminescent device emits red light.

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

[0239] According to one embodiment of the present application, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one host material.

[0240] According to one embodiment of the present application, 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, indolocarbazole, dithiophene, azadithiophene, difuran, azadifuran, dioxaborine, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0241] According to another embodiment of the present application, a compound composition is also disclosed, which comprises a metal complex, the specific structure of which is shown in any of the aforementioned embodiments.

[0242] Combination with other materials

[0243] The materials described herein for specific layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. The combinations of these materials are described in detail in US Patent Application US2016 / 0359122A1 at paragraphs 0132-0161, which is incorporated by reference herein in its entirety. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that can be used in combination.

[0244] The materials described herein as being useful for specific layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein can be used in conjunction with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that can be present. The combinations of these materials are described in detail in US Patent Application US2015 / 0349273A1 at paragraphs 0080-0101, which is incorporated by reference herein in its entirety. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that can be used in combination.

[0245] In the examples of material synthesis, unless otherwise specified, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structure confirmation and property testing using one or more devices (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai Rayleigh Technology's fluorescence spectrophotometer, Wuhan Kosit's electrochemical workstation, Anhui Bei Yike's sublimation instrument, etc.) that are conventional in the art, in a manner well known to those skilled in the art. In the examples of devices, the properties of the devices were also tested using devices (including but not limited to evaporation machines produced by Angstrom Engineering, optical test systems and life test systems produced by Suzhou Fushida, ellipsometers produced by Beijing Liangtuo, etc.) that are conventional in the art, in a manner well known to those skilled in the art. Since those skilled in the art are all aware of the above-mentioned device usage, testing methods, etc. related content, the inherent data of the sample can be obtained definitely and unaffectedly, therefore the above-mentioned related content will not be expanded and described in this patent.

[0246] Examples of material synthesis:

[0247] The preparation method of the compounds of the present application is not limited, and the following compounds are typically but not limitedly exemplified, the synthetic routes and preparation methods of which are as follows:

[0248] Example 1 of synthesis: synthesis of compound 341

[0249] Step 1: synthesis of intermediate 3:

[0250]

[0251] 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, then the reaction was heated to 80°C under nitrogen protection and stirred overnight, and then cooled to room temperature after TLC showed that the reaction was complete. Then ethyl acetate was added to the reaction, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried, and rotary evaporated to obtain a crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:3, v / v) to obtain white solid intermediate 3 (2.9 g, yield 78.5%).

[0252] Step 2: synthesis of intermediate 4:

[0253]

[0254] Intermediate 3 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 10 mL of 2M HC1, and the reaction was heated to reflux with stirring overnight. After TLC showed that the reaction was complete, it was cooled to room temperature. The pH was then adjusted to neutral by the addition of saturated sodium carbonate solution, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 4 (2.6 g, yield 97.2%).

[0255] Step 3: Synthesis of intermediate 5:

[0256]

[0257] Intermediate 4 (2.6 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol), and DMF (40 mL) were heated to 135 °C under nitrogen protection overnight. After TLC showed that the reaction was complete, it was cooled to room temperature. 100 mL of water was added, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 15 (2 g, yield 99.9%).

[0258] Step 4: Synthesis of intermediate 6:

[0259]

[0260] A mixture of 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 tribasic (3.2 g, 12 mmol), and toluene (30 mL) was heated to reflux under nitrogen protection overnight. After TLC showed that the reaction was complete, it was cooled to room temperature. It was poured into a funnel containing diatomite and filtered to collect the filtrate, which was rotary-evaporated to give a crude product. The product was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:20, v / v) to give yellow solid intermediate 6 (2 g, yield 94.4%).

[0261] Step 5: Synthesis of iridium dimer:

[0262]

[0263] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully rotary-evaporated to give a dimer ethoxyethanol solution, which was used in the next reaction without further purification.

[0264] Step 6: Synthesis of compound 341

[0265]

[0266] To a 100 mL round bottom flask was added the ethoxyethanol solution of the iridium dimer from the previous step, 3,7-diethyl-3-methylnonane-4,6-dione (271 mg, 1.2 mmol) and potassium carbonate (0.57 g, 4.15 mmol) and heated to 60 °C under a nitrogen atmosphere for 24 hours. It was then poured into a funnel containing celite and washed with ethanol. To the resulting solid was added dichloromethane and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. Filtration resulted in 0.27 g of compound 341 in 22% yield. The structure of this compound was confirmed as the desired product by LC-MS with a molecular weight of 1474.8.

[0267] Synthesis Example 2: Synthesis of compound 441

[0268] Step 1: Synthesis of compound 441

[0269]

[0270] To a 100 mL round bottom flask was added the ethoxyethanol solution of the iridium dimer from the previous step, 3,7-diethyl-3-methylnonane-4,6-dione (271 mg, 1.2 mmol) and potassium carbonate (0.57 g, 4.15 mmol) and heated to 60 °C under a nitrogen atmosphere for 24 hours. It was then poured into a funnel containing celite and washed with ethanol. To the resulting solid was added dichloromethane and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. Filtration resulted in 0.27 g of compound 341 in 22% yield. The structure of this compound was confirmed as the desired product by LC-MS with a molecular weight of 1474.8.

[0271] Synthesis Example 3: Synthesis of compound 442

[0272] Step 1: Synthesis of intermediate 8:

[0273]

[0274] 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, then the reaction was heated to 80 °C under nitrogen protection overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Then add ethyl acetate to the reaction, separate, the aqueous phase is extracted with ethyl acetate, the combined organic phase is dried, rotary evaporated to give the crude product, which is separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:3, v / v) to give white solid intermediate 8 (2.46 g, yield 86.5%).

[0275] Step 2: Synthesis of intermediate 9:

[0276]

[0277] Intermediate 8 (2.46 g, 3.5 mmol) was dissolved in 10 mL of ethanol, then 2M HCl 10 mL was added, and then the reaction was heated to reflux and stirred overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Then add saturated sodium carbonate solution to adjust the pH to neutral, a large amount of yellow solid precipitated from the solution, filter, wash the solid with water several times and dry to give yellow solid intermediate 9 (2.32 g, yield 99.9%).

[0278] Step 3: Synthesis of intermediate 10:

[0279]

[0280] 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 under nitrogen protection overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Add 100 mL of water to the solution, a large amount of yellow solid precipitated, filter, wash the solid with water several times and dry to give yellow solid intermediate 10 (1.4 g, yield 80.3%).

[0281] Step 4: Synthesis of iridium dimer:

[0282]

[0283] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off on a rotary evaporator to give an ethoxyethanol solution of iridium dimer which was used in the next step without further purification.

[0284] Step 5: Synthesis of compound 442

[0285]

[0286] The ethoxyethanol solution of iridium dimer from 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 reacted at 60 °C for 24 hours under nitrogen protection. It was then filtered through a funnel containing celite 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 concentrated to dryness. Filtration gave 0.88 g of compound 442 in 64.8% yield. The product was further purified by column chromatography. The structure of the compound was confirmed as the target product by LC-MS with a molecular weight of 1384.6.

[0287] Synthesis Example 4: Synthesis of compound 438

[0288] Step 1: Synthesis of intermediate 12:

[0289]

[0290] A mixture of 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) was added to a 100 mL round bottom flask, which was then heated to 80 °C with stirring overnight under nitrogen protection. After the reaction was completed as indicated by TLC, it was cooled to room temperature. Ethyl acetate was then added to the reaction, which was partitioned, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried, and spun dry to give the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:2, v / v) to give white solid intermediate 12 (2.2 g, yield 95.7%).

[0291] Step 2: Synthesis of intermediate 13:

[0292]

[0293] Intermediate 12 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 2 M HC1 (10 mL) to it, and then the reaction was heated to reflux with stirring overnight, and it was cooled to room temperature after TLC showed that the reaction was complete. A saturated sodium carbonate solution was added to it to adjust the pH to neutral, and a large amount of yellow solid precipitated from the solution, which was filtered, washed with water several times, and then dried to obtain yellow solid intermediate 13 (1.8 g, yield 99.8%).

[0294] Step 3: Synthesis of intermediate 14:

[0295]

[0296] 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 under nitrogen protection overnight, and it was cooled to room temperature after TLC showed that the reaction was complete. 100 mL of water was added to it, and a large amount of yellow solid precipitated from the solution, which was filtered, washed with water several times, and then dried to obtain yellow solid intermediate 14 (1.2 g, yield 83.2%).

[0297] Step 4: Synthesis of intermediate 15:

[0298]

[0299] 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 tribasic (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen protection overnight, and it was cooled to room temperature after TLC showed that the reaction was complete. It was filtered into a funnel containing diatomite, and the filtrate was collected and rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:20, v / v) to obtain yellow solid intermediate 15 (0.88 g, yield 67.5%).

[0300] Step 5: Synthesis of iridium dimer:

[0301]

[0302] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off on a rotary evaporator to give an ethoxyethanol solution of iridium dimer which was used in the next step without further purification.

[0303] Step 6: Synthesis of compound 438

[0304]

[0305] The ethoxyethanol solution of iridium dimer from the previous step, 3,7-diethyl-3,7- dimethylnonane-4,6-dione (200 mg, 0.83 mmol) and potassium carbonate (0.38 g, 2.75 mmol) were added to a 100 mL round bottom flask and reacted at 60 °C for 24 hours under nitrogen protection. It was then filtered through a funnel containing celite 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 concentrated to dryness. Filtration gave 0.41 g of compound 438 in 55.3% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1348.7.

[0306] Synthesis Example 5: Synthesis of compound 446

[0307] Step 1: Synthesis of intermediate 17:

[0308]

[0309] A mixture of 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) was added to a 100 mL round bottom flask, which was then heated to 80 °C with stirring overnight under nitrogen protection. After the reaction was completed as indicated by TLC, it was cooled to room temperature. Ethyl acetate was then added to the reaction, which was partitioned, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried, and spun dry to give a crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:2, v / v) to give white solid intermediate 17 (2.0 g, yield 90%).

[0310] Step 2: Synthesis of intermediate 18:

[0311]

[0312] Intermediate 17 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 2 M HC1 (10 mL) to it, and then the reaction was heated to reflux with stirring overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. The pH was then adjusted to neutral by the addition of saturated Na2C03 solution, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and then dried to give yellow solid of intermediate 18 (1.8 g, yield 99.8%).

[0313] Step 3: Synthesis of intermediate 19:

[0314]

[0315] 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 under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. 100 mL of water was added to it, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and then dried to give yellow solid of intermediate 19 (1.2 g, yield 83.2%).

[0316] Step 4: Synthesis of intermediate 20:

[0317]

[0318] 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 tribasic (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. It was filtered through a funnel containing celite, and the filtrate was collected and rotary evaporated to give the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v / v) to give yellow solid of intermediate 20 (0.88 g, yield 67.5%).

[0319] Step 5: Synthesis of iridium dimer:

[0320]

[0321] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully rotary evaporated to give an ethoxyethanol solution of iridium dimer, which was used in the next reaction without further purification.

[0322] Step 6: Synthesis of compound 446

[0323]

[0324] The ethoxyethanol solution of the iridium dimer from the previous step, 3,7- diethyl-3,7-dimethylnonane-4,6-dione (130 mg, 0.55 mmol) and potassium carbonate (0.26 g, 1.85 mmol) were added to a 100 mL round bottom flask and reacted at 50 °C for 24 hours under nitrogen protection. It was then poured into a funnel containing celite 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 concentrated to dryness. Filtration resulted in 0.24 g of compound 446 with a yield of 48%. The structure of the compound was confirmed as the target product by LC-MS with a molecular weight of 1348.7.

[0325] Synthesis Example 6: Synthesis of compound 1021

[0326] Step 1: Synthesis of intermediate 17:

[0327]

[0328] 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, which was then heated to 80 °C with stirring overnight under nitrogen protection. After the reaction was completed as shown by TLC, it was cooled to room temperature. Ethyl acetate was then added to the reaction, which was separated into two phases. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:2, v / v) to obtain white solid intermediate 21 (2.3 g, yield 70%).

[0329] Step 2: Synthesis of intermediate 22:

[0330]

[0331] Intermediate 21 (4.5 g, 6.34 mmol) was dissolved in 30 mL of ethanol, followed by the addition of 2 M HC1 (30 mL) to it, which was then heated to reflux with stirring overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. The pH was then adjusted to neutral by the addition of saturated Na2C03 solution, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 22 (3.1 g, yield 99.8%).

[0332] Step 3: Synthesis of intermediate 23:

[0333]

[0334] 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 under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. 100 mL of water was added to it, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 23 (5.5 g, yield 88%).

[0335] Step 4: Synthesis of intermediate 24:

[0336]

[0337] A mixture of 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 tribasic (5.1 g, 19.02 mmol), and toluene (30 mL) was heated to reflux under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. It was filtered into a funnel containing celite, and the filtrate was collected and dried to give the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:20, v / v) to give yellow solid intermediate 24 (2.6 g, yield 75%).

[0338] Step 5: Synthesis of iridium dimer:

[0339]

[0340] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the solid was filtered, washed with methanol, and dried under vacuum to give the iridium dimer, which was used in the next reaction without further purification.

[0341] Step 6: Synthesis of compound 1021

[0342]

[0343] The ethoxyethanol solution of the iridium dimer from the previous step, 3,7- diethyl-3,7-dimethylnonane-4,6-dione (360 mg, 1.5 mmol) and 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. Then it was poured into a funnel containing celite and washed with ethanol. To the resulting solid, dichloromethane was added and the filtrate was collected. Then ethanol was added and the resulting solution was concentrated but not concentrated to dryness. After filtration, 0.1 g of compound 1021 was obtained with a yield of 6%. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1488.8.

[0344] Synthesis Example 7: Synthesis of compound 405

[0345] Step 1: Synthesis of intermediate 26:

[0346]

[0347] 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, then the reaction was heated to 80 °C with stirring overnight under nitrogen protection, and after TLC showed that the reaction was complete, it was cooled to room temperature. Then ethyl acetate was added to the reaction, separated, the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried, rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:2, v / v) to obtain white solid intermediate 26 (2.2 g, yield 95.7%).

[0348] Step 2: Synthesis of intermediate 27:

[0349]

[0350] Intermediate 26 (2.2 g, 3.4 mmol) was dissolved in 10 mL of ethanol, followed by the addition of 2 M HC1 (10 mL) to it, which was then heated to reflux with stirring overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. The pH was then adjusted to neutral by the addition of saturated Na2C03 solution, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 27 (1.8 g, yield 99.8%).

[0351] Step 3: Synthesis of intermediate 28:

[0352]

[0353] 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 under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. 100 mL of water was added to it, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to give yellow solid intermediate 28 (1.2 g, yield 83.2%).

[0354] Step 4: Synthesis of intermediate 29:

[0355]

[0356] 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 tribasic (2.26 g, 8.49 mmol), and toluene (20 mL) were heated to reflux under nitrogen protection overnight. After the reaction was completed as indicated by TLC, it was cooled to room temperature. It was filtered into a funnel containing diatomite, and the filtrate was collected and rotary evaporated to give the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v / v) to give yellow solid intermediate 29 (0.88 g, yield 67.5%).

[0357] Step 5: Synthesis of iridium dimer:

[0358]

[0359] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, it was filtered to give iridium dimer 210 mg, which was used in the next reaction without further purification.

[0360] Step 6: Synthesis of compound 405

[0361]

[0362] The iridium dimer from the previous step (210 mg, 0.114 mmol), 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. It was then poured into a funnel containing celite 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 concentrated to dryness. Filtration resulted in 0.1 g of compound 405 in 13.5% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1348.7.

[0363] Synthesis Example 8: Synthesis of compound 205

[0364] Step 1: Synthesis of compound 205

[0365]

[0366] The iridium dimer from the previous step (210 mg, 0.114 mmol), 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. It was then poured into a funnel containing celite 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 concentrated to dryness. Filtration resulted in 0.1 g of compound 405 in 13.5% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1348.7.

[0367] Synthesis Example 9: Synthesis of compound 1019

[0368] Step 1: Synthesis of intermediate 31:

[0369]

[0370] 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 into a 100 mL round bottom flask, then the reaction was heated to 80 °C under nitrogen protection and stirred overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Then ethyl acetate was added to the reaction, separated, the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried, rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:3, v / v) to obtain white solid intermediate 31 (2.9 g, yield 76.5%).

[0371] Step 2: Synthesis of intermediate 32:

[0372]

[0373] Intermediate 31 (2.9 g, 4.1 mmol) was dissolved in 10 mL of ethanol, then 2M HCl (10 mL) was added, and then the reaction was heated to reflux and stirred overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Then a saturated sodium carbonate solution was added to adjust the pH to neutral, a large amount of yellow solid precipitated from the solution, which was filtered, washed with water several times and dried to obtain yellow solid intermediate 32 (2.7 g, yield 97.2%).

[0374] Step 3: Synthesis of intermediate 33:

[0375]

[0376] Intermediate 32 (2.7 g, 4.0 mmol), cesium carbonate (2.6 g, 8 mmol) and DMF (40 mL) were heated to 135 °C under nitrogen protection overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. 100 mL of water was added, a large amount of yellow solid precipitated from the solution, which was filtered, washed with water several times and dried to obtain yellow solid intermediate 33 (2 g, yield 98.4%).

[0377] Step 4: Synthesis of intermediate 34:

[0378]

[0379] A mixture of 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 tribasic (3.2 g, 12 mmol) and toluene (30 mL) was heated to reflux under nitrogen overnight. After TLC showed the reaction was complete, it was cooled to room temperature. It was poured into a funnel containing celite and the filtrate was collected and concentrated to dryness. The crude product was separated by column chromatography on silica gel (eluent: ethyl acetate: petroleum ether = 1 :20, v / v) to give intermediate 34 as a yellow solid (1.1 g, 50.6% yield).

[0380] Step 5: Synthesis of iridium dimer:

[0381]

[0382] 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 nitrogen for 24 hours. After cooling to room temperature, the water was carefully spun off the solution on a rotary evaporator to give an ethoxyethanol solution of the iridium dimer which was used in the next step without further purification.

[0383] Step 6: Synthesis of compound 1019

[0384]

[0385] The ethoxyethanol solution of the iridium dimer from the previous step, 3,7- diethyl-3,7-dimethylnonane-4,6-dione (271 mg, 1.2 mmol) and potassium carbonate (0.57 g, 4.15 mmol) were added to a 100 mL round bottom flask and reacted at 60 °C under nitrogen for 24 hours. It was then poured into a funnel containing celite and filtered and washed with ethanol. To the resulting solid was added dichloromethane 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 in 17.5% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1376.7.

[0386] Synthesis Example 10: Synthesis of compound 447

[0387] Step 1: Synthesis of intermediate 36:

[0388]

[0389] 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, which was then heated to 90 °C under nitrogen protection overnight. After the reaction was completed as shown by TLC, it was cooled to room temperature. Ethyl acetate was then added to the reaction, which was separated into two layers. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was dried and rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:2, v / v) to obtain the target product, intermediate 36 (3.1 g, 72%), as a white solid.

[0390] Step 2: Synthesis of intermediate 37:

[0391]

[0392] Intermediate 36 (3.12 g, 4.77 mmol) was dissolved in 20 mL of ethanol, to which 2N HCl (20 mL) was added. The reaction was then heated to reflux and stirred overnight. After the reaction was completed as shown by TLC, it was cooled to room temperature. A saturated sodium carbonate solution was then added to adjust the pH to neutral, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to obtain the target product, intermediate 37 (2.74 g, 96%), as a yellow solid.

[0393] Step 3: Synthesis of intermediate 38:

[0394]

[0395] 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 under nitrogen protection overnight. After the reaction was completed as shown by TLC, it was cooled to room temperature. Water was then added to the solution, and a large amount of yellow solid precipitated from the solution. The solid was filtered, washed with water several times, and dried to obtain the target product, intermediate 38 (1.84 g, 91%), as a yellow solid.

[0396] Step 4: Synthesis of intermediate 39:

[0397]

[0398] A mixture of 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 tribasic (1.02 g, 3.81 mmol) and toluene (15 mL) was heated to reflux under nitrogen overnight. After TLC showed the reaction was complete, it was cooled to room temperature. It was poured into a funnel containing celite and the filtrate was collected and concentrated to dryness. The crude product was separated by column chromatography on silica gel (eluent: ethyl acetate: petroleum ether = 1 : 100, v / v) to give the target product, intermediate 39 (0.58 g, 95%) as a yellow solid.

[0399] Step 5: Synthesis of iridium dimer:

[0400]

[0401] 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 nitrogen for 24 hours. After cooling to room temperature, the water was carefully spun off the solution on a rotary evaporator to give an ethoxyethanol solution of the iridium dimer which was used in the next step without further purification.

[0402] Step 6: Synthesis of compound 447

[0403]

[0404] The ethoxyethanol solution of the iridium dimer from the previous step, 3,7- diethyl-3,7-dimethylnonane-4,6-dione (0.13 g, 0.53 mmol) and potassium carbonate (0.69 g, 5 mmol) and 2-ethoxyethanol (35 mL) were added to a round bottom flask and reacted at 50 °C under nitrogen for 24 hours. It was then poured into a funnel containing celite and filtered and washed with ethanol. To the resulting solid was added dichloromethane and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated but not to dryness. After filtration, 0.18 g of product, compound 447, was obtained 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.

[0405] Synthesis Example 11: Synthesis of compound 1020

[0406] Step 1: Synthesis of iridium dimer:

[0407]

[0408] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off on a rotary evaporator to give an ethoxyethanol solution of iridium dimer which was used in the next step without further purification.

[0409] Step 2: Synthesis of compound 1020

[0410]

[0411] The ethoxyethanol solution of iridium dimer from the previous step, 3,7-diethyl-3,7- dimethylnonane-4,6-dione (271 mg, 1.2 mmol) and potassium carbonate (0.57 g, 4.15 mmol) were added into a 100 mL round bottom flask and reacted at 60 °C for 24 hours under nitrogen protection. Then it was filtered through a funnel containing celite and washed with ethanol. Dichloromethane was added to the resulting solid and the filtrate was collected. Then ethanol was added and the resulting solution was concentrated but not concentrated 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 as the target product by LC-MS with a molecular weight of 1350.7.

[0412] Synthesis Example 12: Synthesis of compound 1018

[0413] Step 1: Synthesis of intermediate 41:

[0414]

[0415] Intermediate 19 (344 mg, 0.81 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene](3-chloropyridine)palladium dichloride (28 mg, 0.04 mmol) were dissolved in THF (5 mL), and 2 mol / L of 3,3,3-trifluoro-2,2-dimethylpropyl magnesium bromide in THF (4 mL) was added under nitrogen protection and reacted at 45 °C, and LC-MS was monitored until intermediate 19 disappeared, the reaction was stopped, quenched with aqueous ammonium chloride solution, extracted with EA, the organic phase was collected, dried, and the solvent was removed by rotary evaporation, and separation was performed by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:100, v / v) to obtain intermediate 41 (248 mg, yield 60%).

[0416] Step 2: Synthesis of iridium dimer:

[0417]

[0418] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the solid was filtered and washed with methanol for 3 times, and the solvent was removed under vacuum to collect the red solid iridium dimer, which was used in the next step without further purification.

[0419] Step 3: Synthesis of compound 1018

[0420]

[0421] The iridium dimer from the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (51 mg, 0.21 mmol) and 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. It was then filtered into a funnel containing celite 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 concentrated to dryness. Filtration resulted in 0.1 g of product compound 1018 with a yield of 49%. The structure of the compound was confirmed as the target product by LC-MS with a molecular weight of 1456.6.

[0422] Synthesis Example 13: Synthesis of compound 452

[0423] Step 1: Synthesis of intermediate 44:

[0424]

[0425] A mixture of 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) was added to a 100 mL round bottom flask, which was then heated to 80 °C with stirring overnight under nitrogen protection. After the reaction was completed as shown by TLC, it was cooled to room temperature. Ethyl acetate was then added to the reaction, which was separated into two layers. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and rotary evaporated to obtain the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:3, v / v) to obtain white solid intermediate 44 (500 mg, yield 81.3%).

[0426] Step 2: Synthesis of intermediate 45:

[0427]

[0428] Intermediate 44 (500 mg, 0.77 mmol), and diphenyl ether (4 mL) were heated to 180 °C under nitrogen overnight, and allowed to cool to room temperature after TLC showed the reaction was complete. The crude product was isolated by column chromatography on silica gel (eluent ethyl acetate: petroleum ether = 1 :20, v / v) to give intermediate 45 as a yellow solid (110 mg, 30% yield).

[0429] Step 3: Synthesis of iridium dimer:

[0430]

[0431] 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 nitrogen for 24 hours. After cooling to room temperature, the water was carefully spun off the solution on a rotary evaporator to give an ethoxyethanol solution of the iridium dimer which was used in the next step without further purification.

[0432] Step 4: Synthesis of compound 452

[0433]

[0434] The ethoxyethanol solution of the iridium dimer from 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 allowed to react at 60 °C under nitrogen for 24 hours. It was then poured into a funnel containing celite 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 concentrated to dryness. Filtration gave 0.04 g of compound 341 in 37.6% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1380.6.

[0435] Synthesis Example 14: Synthesis of compound 1017

[0436] Step 1: Synthesis of intermediate 47:

[0437]

[0438] To a reaction tube was added 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), sealed under nitrogen and heated to 150 °C overnight. After the reaction was complete, it was allowed to cool to room temperature and was spun dry to give a crude product which was separated by column chromatography on silica gel to give intermediate 47 as a yellow solid (0.4 g, 73.5%).

[0439] Step 2: Synthesis of iridium dimer:

[0440]

[0441] 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 nitrogen for 24 hours. After cooling to room temperature, the solid was filtered and washed with methanol and dried to give the iridium dimer which was used in the next step without further purification.

[0442] Step 3: Synthesis of compound 1017

[0443]

[0444] The iridium dimer from 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 heated to 50 °C under nitrogen for 24 hours. It was then poured into a funnel containing celite and filtered with ethanol. To the resulting solid was added dichloromethane and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated but not concentrated dry. After filtration, 0.37 g of product compound 1017 was obtained in 54% yield. The structure of this compound was confirmed as the target product by LC-MS with a molecular weight of 1352.6.

[0445] Synthesis Example 15: Synthesis of compound 1022

[0446] Step 1: Synthesis of intermediate 49:

[0447]

[0448] 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, then the reaction was heated to 80 °C under nitrogen protection overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. Then add ethyl acetate to the reaction, separate, the aqueous phase is extracted with ethyl acetate, the combined organic phase is dried, rotary evaporated to give the crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:3, v / v) to give intermediate 49 (620 mg, yield 68.4%) as a white solid.

[0449] Step 2: Synthesis of intermediate 50:

[0450]

[0451] Intermediate 49 (620 mg, 0.94 mmol) and diphenyl ether (5 mL) were heated to 140 °C under nitrogen protection overnight, after TLC showed that the reaction was completed, it was cooled to room temperature. The crude product was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:20, v / v) to give intermediate 50 (260 mg, yield 56.5%) as a yellow solid.

[0452] Step 3: Synthesis of iridium dimer:

[0453]

[0454] 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 nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to give an ethoxyethanol solution of iridium dimer, which was used in the next reaction without further purification.

[0455] Step 4: Synthesis of compound 1022

[0456]

[0457] The ethoxyethanol solution of the iridium dimer from 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 reacted at 60 °C for 24 hours under nitrogen protection. Then it was poured into a funnel containing diatomite and washed with ethanol. To the obtained solid, dichloromethane was added and the filtrate was collected. Then ethanol was added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.08 g of compound 1022 was obtained with a yield of 31.5%. The structure of the compound was confirmed as the target product by LC-MS with a molecular weight of 1408.6.

[0458] Those skilled in the art should know that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present application by improving it.

[0459] Through special ligand structure design, the metal complex of the present application realizes a more deep red luminescence, and the following photoluminescence spectrum (PL) data further proves that this more deep red luminescence is an unexpected excellent effect.

[0460] Spectrum data

[0461] The photoluminescence spectrum (PL) data of the compounds of the present application and the comparative compounds were measured using a fluorescence spectrophotometer produced by Shanghai Linxiang Technology Co., Ltd. with a model of Linxiang F98: the sample of the compound of the present application or the sample of the comparative compound was respectively prepared into a solution with a concentration of 3 x 10 -5 mol / L using toluene of HPLC grade, then excited at room temperature (298 K) using light with a wavelength of 500 nm and measured the emission spectrum. The measurement results are shown in Table 1.

[0462] Table 1 Spectrum data

[0463] Serial number Sample number 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

[0464] The structures of the related compounds of the present application and the comparative compounds are as follows:

[0465]

[0466] Discussion:

[0467] Phenylisoquinoline ligands are a class of ligand structures that have been extensively studied and applied in the prior art, especially in the field of red phosphorescent metal complexes. It has been found that introducing an additional fused ring structure to the isoquinoline ring of such ligands will cause a significant blue shift in the emission wavelength. For example, as can be seen from the data in Table 1, the maximum emission wavelength of compound RD-B having a phenylbenzoisoquinoline ligand is blue-shifted by 4 nm compared to compound RD-A. In the present application, however, the ligand structures of compound 442, compound 341, and compound 441 all have an additional fused ring structure introduced to the same position on the isoquinoline ring, but their maximum emission wavelengths are all significantly red-shifted compared to compound RD. This red-shift effect is in direct contrast to the trend that has been found in the prior art. These comparisons demonstrate the uniqueness of the metal complex structure of the present application, providing a brand new structure of metal complex with an unexpectedly deeper red color of light emission.

[0468] Device Example

[0469] Device Example 1

[0470] First, a glass substrate having a 120 nm thick indium tin oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were sequentially evaporated on the ITO anode at a rate of 0.2-2 Angstroms / second by thermal vacuum evaporation under a vacuum of about 10 -8 Compound HI was doped in compound HT and used as a hole injection layer (HIL, 3:97), thickness Compound HT was used as a hole transport layer (HTL), thickness Compound EB was used as an electron blocking layer (EBL), thickness Then, compound 341 of the present application was doped in host compound RH and used as an emission layer (EML, 5:95), thickness Compound HB was used as a hole blocking layer (HBL), thickness On the HBL, a mixture of compound ET and 8-hydroxyquinoline-lithium (Liq) was deposited as an electron transport layer (ETL), thickness Finally, 1 nm thick Liq was deposited as an electron injection layer, and 120 nm of Al was deposited as a cathode. The device was then transferred back to the glove box, and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0471] Device Comparative Example 1

[0472] 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 application in the emission layer (EML).

[0473] Device Example 3

[0474] Device Example 3 was prepared in the same manner as Device Example 1 except that Compound 438 of the Invention was used in place of Compound 341 of the Invention in the light-emitting layer (EML) and the weight ratio of Compound 438 of the Invention and Compound RH was adjusted to 3:97.

[0475] Device Example 4

[0476] Device Example 4 was prepared in the same manner as Device Example 3 except that Compound 446 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0477] Device Example 5

[0478] Device Example 5 was prepared in the same manner as Device Example 3 except that Compound 1021 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0479] Device Example 6

[0480] Device Example 6 was prepared in the same manner as Device Example 3 except that Compound 405 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0481] Device Example 7

[0482] Device Example 7 was prepared in the same manner as Device Example 3 except that Compound 1019 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0483] Device Example 8

[0484] Device Example 8 was prepared in the same manner as Device Example 3 except that Compound 447 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0485] Device Example 9

[0486] Device Example 9 was prepared in the same manner as Device Example 3 except that Compound 1020 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0487] Device Example 10

[0488] Device Example 10 was prepared in the same manner as Device Example 3 except that Compound 1018 of the Invention was used in place of Compound 438 of the Invention in the light-emitting layer (EML).

[0489] Device Example 11

[0490] Device Example 11 was prepared in the same manner as Device Example 3, except that Compound 1017 of the present application was used in place of Compound 438 of the present application in the light-emitting layer (EML).

[0491] Device Comparative Example 3

[0492] Device Comparative Example 3 was prepared in the same manner as Device Example 3, except that Compound RD1 was used in place of Compound 438 of the present application in the light-emitting layer (EML).

[0493] The partial layer structure and thickness of the devices are shown in the following table. Where more than one material is used, the different compounds are doped in the proportions by weight indicated.

[0494] Table 2. Partial Device Structure for Device Examples and Comparative Examples

[0495]

[0496]

[0497]

[0498] The structures of the materials used in the devices are shown below:

[0499]

[0500]

[0501] The IVL characteristics of the devices were measured. Table 3 shows the CIE data, Voltage, maximum emission wavelength (λ 2 CIE data, Voltage, maximum emission wavelength (λ max ), full width at half maximum (FWHM), and external quantum efficiency (EQE) for the Device Examples and Device Comparative Examples measured at constant current.

[0502] Table 3. Device Data

[0503]

[0504] Discussion:

[0505] As can be seen from the data shown in Table 3, Example 1 has a clear red shift in color with a CIE xThe maximum emission wavelength is red-shifted from 621 nm of Comparative Example 1 to 625 nm of Example 1, realizing a more deep red light emission. Moreover, the external quantum efficiency of Example 1 is further significantly improved from the extremely high efficiency level of 24.11% of Comparative Example 1, with an improvement of nearly 7.5%, which confirms that the present application provides a deep red phosphorescent light emitting material with narrow peak width, low voltage and high efficiency, and fully demonstrates the broad application prospect of the compound of the present application.

[0506] Comparative Example 3, the maximum emission wavelengths of Examples 3-11 are all red-shifted, realizing a more deep red light emission, while the device efficiencies of Examples 3-11 are all further significantly improved from the extremely high efficiency level of 24.24% of Comparative Example 3, especially Examples 3, 4, 8 and 9 all realize an ultra-high device efficiency of more than 26%. Again, it is confirmed that the present application provides a deep red phosphorescent light emitting material with narrow peak width, low voltage and high efficiency, and fully demonstrates the broad application prospect of the compound of the present application.

[0507] In addition, since the top-emitting device structure is a device structure widely used in commercial devices, the excellent effect of the metal complex of the present application in the top-emitting device is further verified herein.

[0508] Device Example 2

[0509] First, a 0.7 mm thick glass substrate with a pre-patterned indium tin oxide (ITO) anode was used. The substrate was then baked in a glove box to remove moisture and loaded on a holder into a vacuum chamber. The organic layers specified below were sequentially evaporated on the anode by vacuum thermal evaporation at a rate of 0.1 A / s under a vacuum degree of about 10 -6 Torr. First, compound HT1 and compound HI were simultaneously evaporated as a hole injection layer (HIL, 97:3, Compound HT1 was evaporated on the HIL as a hole transport layer (HTL, 100%). The HTL simultaneously served as a microcavity adjustment layer. Next, compound EB1 was evaporated on the hole transport layer as an electron blocking layer (EBL, 100%). Then, compound 341 of the present application and compound RH were co-evaporated as a light emitting layer (EML, 3:97, On the EML, compound ET1 and Liq were co-evaporated as an electron transport layer (ETL, 40:60, Evaporated Yb as electron injection layer (EIL), and co-evaporating metals Ag and Mg in a ratio of 9:1 as cathode. Finally, compound CPL54 was evaporated as cathode capping layer (CPL, ) was purchased from San-Mar Science and Technology Co. Ltd. Jiangsu. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorbent in a nitrogen atmosphere to complete the device.

[0510] Device Comparative Example 2

[0511] Device Comparative Example 2 was prepared in the same manner as Device Example 2, except that compound RD was used in place of compound 341 of the present application in the light-emitting layer (EML).

[0512] Device Example 12

[0513] Device Example 12 was prepared in the same manner as Device Example 2, except that compound 447 of the present application was used in place of compound 341 of the present application in the light-emitting layer (EML).

[0514] The partial layer structure and thickness of the devices are shown in the following table. Where more than one material is used, the different compounds are doped in the weight proportions indicated.

[0515] Table 4. Partial device structure for Example 2, Example 12, and Comparative Example 2

[0516]

[0517] The structures of the new materials used in the devices are shown below:

[0518]

[0519] The IVL characteristics of the devices were measured. The CIE data, maximum emission wavelength λ 2 , voltage (V), full width at half maximum (FWHM), and external quantum efficiency (EQE) of the devices were measured at 10 mA / cm max . These data are reported and shown in Table 5.

[0520] Table 5. Device data for Example 2, Example 12, and Comparative Example 2

[0521]

[0522] Discussion:

[0523] As can be seen from Table 5, the top-emitting device of Example 2 using the compound of the present application in the light-emitting layer also has very excellent performance. Example 2 maintains a very narrow half-peak width and a substantially flat lower voltage level similar to Comparative Example 2. In addition, the light-emitting color of Example 2 also has a significant red shift compared to Comparative Example 2: CIEx moves from 0.680 to 0.690, and the maximum emission wavelength red shifts from 618 nm to 623 nm. At the same time, Example 2 achieves a significant increase in EQE, with an increase of nearly 17%, while maintaining a voltage comparable to Comparative Example 2. Example 12 exhibits almost the same very narrow half-peak width level as Comparative Example 2, maintains a lower voltage level substantially flat with Comparative Example 2, and more importantly, the maximum emission wavelength of Example 12 has a significant red shift, while also achieving a significant increase in EQE, with an increase of nearly 13%, having very excellent device performance similar to Example 2. Again, it is proved that the metal complex of the present application has excellent characteristics, and has great application potential in top-emitting devices.

[0524] It should be understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the application. Accordingly, the claimed application can encompass modifications and equivalents of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted for one another without departing from the spirit of the application. It is intended that the application not be limited to the specific embodiments described, but that it include all embodiments falling within the scope of the application. It is further intended that the application not be limited by the various theories of operation of its various embodiments.

Claims

1. A metal complex having Ir(L a )2(L b The structure of L a L b These are the first and second ligands of the complex, respectively; two L... a Same or different; the L a It has a structure represented by Equation 3: in, X1-X2 are selected from CR each time they appear, either the same or different. x X3 is selected from CR i A1-A4 are selected from CR each time they appear, either identically or differently. ii X4-X7 are selected from CH and CR, either identically or differently, each time they appear. iii And at least one of X4 to X7 is selected from CR iii ; Y is selected from O or S; R, R i R ii R x Each time it appears, it is 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 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, and combinations thereof. R iii Each time it appears, it is selected from the group consisting of: deuterium, 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 alkylsilyl groups having 3-20 carbon atoms, and combinations thereof. The L b Selected from the following structures: in, X c and X d Selected from O; R a R b R c Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, cyano, and combinations thereof. The substituted alkyl, substituted cycloalkyl, substituted alkylsilyl means that any one of the alkyl, cycloalkyl, and alkylsilyl groups can be replaced by one or more groups selected from deuterium, halogens, unsubstituted alkyl groups having 1-20 carbon atoms, unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and combinations thereof.

2. The metal complex as claimed in claim 1, wherein R, 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 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 carbon atoms, and combinations thereof. R iii Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 carbon atoms, and combinations thereof.

3. The metal complex as described in claim 1, wherein, The R x R i R ii Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, 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, halogens, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 10 carbon atoms, and combinations thereof.

4. The metal complex as described in claim 1, wherein, 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, 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 alkylsilyl groups having 3 to 20 carbon atoms, 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, isopropyldimethylsilyl, trifluoromethyl, and combinations thereof.

5. The metal complex as described in claim 1, wherein, At least one or two of A1-A4 are selected from CR ii And the R ii Each time it appears, it is selected 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 alkylsilyl group having 3-20 carbon atoms, 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 groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, or combinations thereof.

6. The metal complex as described in claim 5, wherein, 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, isopropyldimethylsilyl, trifluoromethyl, 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, isopropyldimethylsilyl, trifluoromethyl, and combinations thereof.

7. The metal complex as described in claim 1, wherein, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, or combinations thereof.

8. The metal complex of claim 7, wherein, The R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, or combinations thereof.

9. The metal complex as claimed in claim 1, wherein, Y is selected from O.

10. The metal complex of claim 1, wherein, X1 is selected from CR x X2 is selected from CR x ; The R x It is selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, or combinations thereof.

11. The metal complex of claim 1, 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 same or different groups of: hydrogen, deuterium, 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 alkylsilyl groups having 3-20 carbon atoms, and combinations thereof; R iii1 R iii2 R iii3 R iii4 At least one of them, each time appearing, is 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 alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof. The substituted alkyl, substituted cycloalkyl, substituted alkylsilyl means that any one of the alkyl, cycloalkyl, and alkylsilyl groups can be replaced by one or more groups selected from deuterium, halogens, unsubstituted alkyl groups having 1-12 carbon atoms, unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, and combinations thereof.

12. The metal complex of claim 11, wherein, 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 deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 carbon atoms, or combinations thereof; R is selected from halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 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 12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4 to 10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 10 carbon atoms, and combinations thereof.

13. The metal complex of claim 11, wherein, 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 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 carbon atoms, or combinations thereof; R is selected from substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-10 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: substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4 to 10 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 10 carbon atoms, and combinations thereof.

14. The metal complex of claim 11, 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, 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.

15. The metal complex of claim 14, wherein, 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.

16. The metal complex of claim 1, 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 a11 L a14 L a18 To L a25 L a28 L a31 To L a41 L a44 L a48 To L a58 L a61 L a65 To L a75 L a78 L a82 To L a88 L a91 To L a99 L a102 L a104 To L a112 L a115 L a118 To L a125 L a128 L a131 To L a138 L a141 To L a150 L a153 L a156 To L a165 L a168 L a172 To L a180 L a183 L a186 To L a196 L a199 L a203 To L a213 L a216 L a220 To L a229 L a251 To L a260 L a263 L a267 To L a276 L a279 L a283 To L a292 L a295 L a299 To L a308 L a311 L a315 To L a324 L a327 L a331 To L a340 L a343 L a347 To L a356 L a359 L a363 To L a372 L a375 L a379 To L a388 L a391 L a395 To L a404 L a407 L a411 To L a420 L a434 To L a443 L a446 L a450 To L a459 L a462 L a466 To L a472 L a475 L a478 To L a487 L a490 L a494 To L a503 L a506 L a510 To L a519 L a522 L a526 To L a535 L a538 L a542 To L a547 L a550 L a553 To L a559 L a562 L a566 To L a575 L a578 L a582 To L a591 L a594 L a598 To L a607 L a610 L a614 To L a619 L a633 To L a642 L a645 L a648 To L a656 L a659 L a662 To L a668 L a671 To L a680 L a683 L a686 To L a692 L a695 To L a704 L a707 L a710 To L a716 L a719 To L a726 L a729 To L a737 L a740 To L a747 L a750 To L a756 L a770 To L a779 L a782 L a785 To L a795 L a800 L a803 To L a812 L a815 L a818 To L a828 L a831 L a834 To L a844 L a847 L a850 To L a859 L a861 L a864 To L a874 L a876 L a879 To L a889 L a891 L a894 To L a904 L a906 L a909 To L a919 L a921 L a924 To L a932 L a934 L a937 To L a945 L a947 L a950 To L a958 L a960 L a963 To L a971 L a973 L a976 To L a984 L a986 L a989 L a1008 To L a1017 L a1020 L a1023 To L a1033 L a1036 L a1039 To L a1049 L a1052 L a1055 To L a1065 L a1068 L a1071 To L a1081 L a1084 L a1087 To L a1095 L a1097 L a1100 To L a1109 L a1111 L a1114 To L a1123 L a1125 L a1128 To L a1137 L a1139 L a1142 To L a1151 L a1153 L a1156 To L a1165 L a1167 L a1170 To L a1179 L a1181 L a1184 To L a1193 L a1195 L a1198 To L a1207 L a1209 L a1212 L a1231 To L a1237 L a1239 L a1241 To L a1248 L a1250 L a1252 To L a1257 L a1259 L a1262 To L a1267 L a1269 L a1271 To L a1277 L a1279 L a1281 To L a1286 L a1288 To L a1293 L a1295 To L a1300 L a1302 To L a1307 L a1309 To L a1314 L a1316 To L a1321 L a1323 To L a1325 L a1327 To L a1330 L a1332 To L a1337 L a1339 L a1341 L a1360 To L a1365 L a1367 To L a1373 L a1375 To L a1381 L a1383 To L a1388 L a1390 To L a1396 L a1398 L a1400 To L a1405 L a1407 To L a1412 L a1414 To L a1438 L a1440 To L a1443 L a1445 To L a1448 L a1450 To L a1455 L a1458 L a1477 To L a1527 L a1795 To L a1889 L a1898 To L a1900 L a1905 L a1906 In the structure, hydrogen can be partially or completely replaced by deuterium.

17. The metal complex of claim 1, wherein L b Selected from the following structures: 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, and combinations thereof.

18. The metal complex of claim 17, wherein at least one or two of R1-R3, each occurrence being identical or different, are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and / or at least one or two of R4-R6, each occurrence being identical or different, are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.

19. The metal complex of claim 17, wherein at least two of R1-R3, each time appearing identically or differently, are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and / or at least two of R4-R6, each time appearing identically or differently, are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.

20. The metal complex of claim 17, wherein the metal complex has the formula Ir(L a ) m (L b ) 3-m The general formula, and has the structure represented by Equation 1-2: in, m is 2; X1-X2 are selected from CR each time they appear, either the same or different. x X3 is selected from CR each time it appears, either the same or different. i A1-A4 are selected from CR each time they appear, either identically or differently. 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 ; Y is selected from O; R, R x R i R ii Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-6 carbon atoms; R iii Each time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, halogen, substituted or unsubstituted alkyl with 1-6 carbon atoms, substituted or unsubstituted alkylsilyl with 3-10 carbon atoms; R1, R2, R3, R4, R5, R6, and R7 are selected from the group consisting of the following, either identically or differently, each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms; The substituted alkyl group, or substituted alkylsilyl group, refers to any one of the alkyl or alkylsilyl groups that can be replaced by one or more groups selected from deuterium or halogens.

21. The metal complex of claim 16, wherein L b Each occurrence is either identical or different from the group consisting of the following structures:

22. The metal complex of claim 21, wherein, The metal complex has Ir(L) a )2(L b The structure of ); Among them, two L a Similarly, the L a Choose freely L a1 To L a11 L a14 L a18 To L a25 L a28 L a31 To L a41 L a44 L a48 To L a58 L a61 L a65 To L a75 L a78 L a82 To L a88 L a91 To L a99 L a102 L a104 To L a112 L a115 L a118 To L a125 L a128 L a131 To L a138 L a141 To L a150 L a153 L a156 To L a165 L a168 L a172 To L a180 L a183 L a186 To L a196 L a199 L a203 To L a213 L a216 L a220 To L a229 L a251 To L a260 L a263 L a267 To L a276 L a279 L a283 To L a292 L a295 L a299 To L a308 L a311 L a315 To L a324 L a327 L a331 To L a340 L a343 L a347 To L a356 L a359 L a363 To L a372 L a375 L a379 To L a388 L a391 L a395 To L a404 L a407 L a411 To L a420 L a434 To L a443 L a446 L a450 To L a459 L a462 L a466 To L a472 L a475 L a478 To L a487 L a490 L a494 To L a503 L a506 L a510 To L a519 L a522 L a526 To L a535 L a538 L a542 To L a547 L a550 L a553 To L a559 L a562 L a566 To L a575 L a578 L a582 To L a591 L a594 L a598 To L a607 L a610 L a614 To L a619 L a633 To L a642 L a645 L a648 To L a656 L a659 L a662 To L a668 L a671 To L a680 L a683 L a686 To L a692 L a695 To L a704 L a707 L a710 To L a716 L a719 To L a726 L a729 To L a737 L a740 To L a747 L a750 To L a756 L a770 To L a779 L a782 L a785 To L a795 L a800 L a803 To L a812 L a815 L a818 To L a828 L a831 L a834 To L a844 L a847 L a850 To L a859 L a861 L a864 To L a874 L a876 L a879 To L a889 L a891 L a894 To L a904 L a906 L a909 To L a919 L a921 L a924 To L a932 L a934 L a937 To L a945 L a947 L a950 To L a958 L a960 L a963 To L a971 L a973 L a976 To L a984 L a986 L a989 L a1008 To L a1017 L a1020 L a1023 To L a1033 L a1036 L a1039 To L a1049 L a1052 L a1055 To L a1065 L a1068 L a1071 To L a1081 L a1084 L a1087 To L a1095 L a1097 L a1100 To L a1109 L a1111 L a1114 To L a1123 L a1125 L a1128 To L a1137 L a1139 L a1142 To L a1151 L a1153 L a1156 To L a1165 L a1167 L a1170 To L a1179 L a1181 L a1184 To L a1193 L a1195 L a1198 To L a1207 L a1209 L a1212 L a1231 To L a1237 L a1239 L a1241 To L a1248 L a1250 L a1252 To L a1257 L a1259 L a1262 To L a1267 L a1269 L a1271 To L a1277 L a1279 L a1281 To L a1286 L a1288 To L a1293 L a1295 To L a1300 L a1302 To L a1307 L a1309 To L a1314 L a1316 To L a1321 L a1323 To L a1325 L a1327 To L a1330 L a1332 To L a1337 L a1339 L a1341 L a1360 To L a1365 L a1367 To L a1373 L a1375 To L a1381 L a1383 To L a1388 L a1390 To L a1396 L a1398 L a1400 To L a1405 L a1407 To L a1412 L a1414 To L a1438 L a1440 To L a1443 L a1445 To L a1448 L a1450 To L a1455 L a1458 L a1477 To L a1527 L a1795 To L a1889 L a1898 To L a1900 L a1905 L a1906 Any of the groups formed, L b Choose freely L b1 To L b322 Any one of the groups formed.

23. The metal complex of claim 22, wherein the metal complex is selected from compounds 1 to 12, 14 to 65, 80 to 112, 114 to 165, 180 to 212, 214 to 265, 280 to 312, 314 to 365, 380 to 412, 414 to 465, 480 to 512, 514 to 565, 580 to 612, 614 to 665, 680 to 712, 714 to 765, 780 to 806, 809 to 816, 819, and 820. The group consisting of compounds 822 to 836, 839 to 846, 849, 850, 852 to 866, 869 to 876, 879, 880, 882 to 896, 899 to 906, 909, 910, 912 to 926, 929 to 936, 939, 940, 942 to 956, 959 to 966, 969, 970, 972 to 986, 989 to 996, 999, 1000, 1002 to 1010, and 1011 to 1028; The compounds 1 to 12, 14 to 65, 80 to 112, 114 to 165, 180 to 212, 214 to 265, 280 to 312, 314 to 365, 380 to 412, 414 to 465, 480 to 512, 514 to 565, 580 to 612, 614 to 665, 680 to 712, 714 to 765, 780 to 800, and 1011 to 1028 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: in, Compounds 801 to 806, 809 to 816, 819, 820, 822 to 836, 839 to 846, 849, 850, 852 to 866, 869 to 876, 879, 880, 882 to 896, 899 to 906, 909, 910, 912 to 926, 929 to 936, 939, 940, 942 to 956, 959 to 966, 969, 970, 972 to 986, 989 to 996, 999, 1000, 1002 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:

24. 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 1-23.

25. The electroluminescent device of claim 24, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

26. The electroluminescent device of claim 25, wherein the electroluminescent device emits red light or white light.

27. The electroluminescent device of claim 25, wherein the light-emitting layer further comprises at least one host material; said 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.

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

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