Electroluminescent material and device thereof

Abstract

An electroluminescent material and device thereof are disclosed. The electroluminescent material is a metal complex comprising a ligand represented by Formula 1, and can be used as a luminescent material in an electroluminescent device. These novel metal complexes can effectively modulate the emission wavelength, reduce the driving voltage of the electroluminescent device, significantly improve the current efficiency, power efficiency, and EQE of the electroluminescent device, and extend the device lifetime, providing better device performance. An electroluminescent device and a compound composition are also disclosed.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a metal complex comprising a ligand represented by Formula 1, and organic electroluminescent devices and compound compositions comprising the compound. Background Technology

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. 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. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as fabrication on flexible substrates.

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

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

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

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] US20070034863A1 discloses metal complexes comprising the following structures: Its ligands connect two ring systems via a Y-axis. Among its many disclosed structures are, for example... Complexes in which B, N, or P atoms are substituted with alkyl or phenyl groups as bridging atoms. The significant effects of further introducing fused ring structures at specific positions are not disclosed or taught.

[0009] CN110698518A discloses a phosphorescent material with the following general structural formula: Where X is N or P. Specific examples include: They failed to notice the significant impact of further introducing fused ring structures at specific locations.

[0010] While existing technologies have reported on phosphorescent materials, further research and development are needed to meet the industry's increasing demands for device performance, such as device emission color, emission saturation, voltage, device efficiency, and device lifetime. Summary of the Invention

[0011] The present invention aims to provide a series of metal complexes comprising ligands represented by Formula 1 to solve at least some of the aforementioned problems. These metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can reduce the driving voltage of electroluminescent devices, significantly improve the current efficiency, power efficiency, and EQE of electroluminescent devices, and extend device lifetime, thus providing better device performance.

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

[0013]

[0014] in,

[0015] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0016] W is selected from B, N, or P each time it appears, either the same or different.

[0017] Rings A, C, and D are selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms each time they appear;

[0018] Ring B is selected from heterocycles having 5-30 ring atoms;

[0019] R a Rb R c and R d Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0020] R a R b R c and R d Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0021] Adjacent substituent R a R b R c and R d They can be arbitrarily connected to form a ring.

[0022] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode; wherein the organic layer comprises a metal complex as shown in the above embodiments.

[0023] According to another embodiment of the present invention, a compound composition comprising the metal complex as shown in the above embodiments is also disclosed.

[0024] The novel metal complexes disclosed in this invention, comprising ligands represented by Formula 1, can be used as luminescent materials in electroluminescent devices. These novel metal complexes can effectively control the emission wavelength, reduce the driving voltage of electroluminescent devices, significantly improve the current efficiency, power efficiency, and EQE of electroluminescent devices, and extend device lifespan, thus providing better device performance. Attached Figure Description

[0025] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound compositions disclosed herein.

[0026] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the metal complexes and compound compositions disclosed herein. Detailed Implementation

[0027] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0028] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0029] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0030] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0031] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0032] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0033] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0034] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0035] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0036] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0037] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0038] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0039] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0040] Definition of the term "substituent group"

[0041] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0042] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0043] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0044] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0045] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0050] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0051] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0052] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0053] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0054] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0055] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0056] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0057] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0058] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0059] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0060] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0061] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0062] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0063] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0064]

[0065] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0066]

[0067] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0068]

[0069] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0070]

[0071] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand L coordinated to the metal. a The metal M is selected from metals with a relative atomic mass greater than 40, and the ligand L... a It has the structure represented by Equation 1:

[0072]

[0073] in,

[0074] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0075] W is selected from B, N, or P each time it appears, either the same or different.

[0076] Rings A, C, and D are selected from five-membered unsaturated carbon rings, aromatic rings with 6-30 carbon atoms, or heteroaromatic rings with 3-30 carbon atoms each time they appear;

[0077] Ring B is selected from heterocycles having 5-30 ring atoms;

[0078] R a R b R c and R d Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0079] R a R b R c and R dEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0080] Adjacent substituent R a R b R c and R d They can be arbitrarily connected to form a ring.

[0081] In this paper, adjacent substituents R a R b R c and R d They can be optionally linked to form a ring, intended to represent any adjacent set of substituents, for example, adjacent substituents R a Adjacent substituent R b Adjacent substituent R c Adjacent substituent R d Adjacent substituent R a With R b Adjacent substituent R a With R d Any one or more of these adjacent substituent groups can connect to form a ring. It is also obvious that these adjacent substituent groups can remain unconnected to form a ring.

[0082] According to one embodiment of the invention, the metal complex optionally includes other ligands that can interact with the L a They can be optionally linked to form tridentate, tetradentate, pentadentate, or hexadentate ligands.

[0083] According to one embodiment of the present invention, wherein the L a In the rings, rings A, C, and D are either identical or different aromatic rings with 6-18 carbon atoms or heteroaromatic rings with 3-18 carbon atoms each time they appear; ring B is selected from heteroaromatic rings with 5-18 ring atoms.

[0084] According to one embodiment of the present invention, wherein the L a In this context, rings A, C, and D are selected from aromatic rings having 6-10 carbon atoms or heteroaromatic rings having 3-10 carbon atoms each time they appear; ring B is selected from fused heteroaromatic rings having 8-18 ring atoms.

[0085] In this embodiment, ring B is selected from a fused heteroaromatic ring having 8-18 ring atoms, meaning that ring B is selected from a fused heteroaromatic ring and the fused heteroaromatic ring has 8-18 ring atoms. For example, when ring B is selected from an indole ring, it is a fused heteroaromatic ring and has 9 ring atoms. As another example, when ring B is selected from an azidoindole ring, it is a fused heteroaromatic ring and also has 9 ring atoms.

[0086] According to one embodiment of the present invention, wherein the L a In this ring, rings A, C, and D are each independently selected from benzene rings, pyridine rings, pyrimidine rings, furan rings, thiophene rings, pyrrole rings, imidazole rings, thiazole rings, oxazole rings, pyrazole rings, isothiazole rings, isoxazole rings, naphthylene rings, quinoline rings, isoquinoline rings, naphthidine rings, benzofuran rings, benzothiophene rings, benzoimidazolium rings, benzothiazole rings, benzoxazole rings, pyridofuran rings, or pyridothiophene rings; ring B is selected from pyrrole rings, indole rings, imidazole rings, pyrazole rings, or azidoindole rings.

[0087] According to one embodiment of the present invention, wherein the L a In this ring, rings A, C, and D are each independently selected from benzene rings, naphthalene rings, pyridine rings, or pyrimidine rings; ring B is selected from pyrrole rings, indole rings, or azidoindole rings.

[0088] According to one embodiment of the present invention, wherein the L a Choose any one of the structures represented by Equations 2 to 19:

[0089]

[0090]

[0091] in,

[0092] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0093] W is selected from B, N, or P each time it appears, either the same or different.

[0094] A1-A4 are selected from N or CR each time they appear, either identically or differently. a ;

[0095] B1-B4 are selected from N or CR each time they appear, either identically or differently. b ;

[0096] C1-C5 are selected from N or CR each time they appear, either identically or differently. c ;

[0097] D1-D4 are selected from N or CR each time they appear, either identically or differently. d ;

[0098] Z3 is selected from O, S, Se, NR each time it appears, either identically or differently. z CR z R z SiR z R z or PR z When two R exist simultaneously z At that time, two R z Same or different;

[0099] R a R b R c R d and R z Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0100] Adjacent substituent R a R b Rc R d and R z They can be arbitrarily connected to form a ring.

[0101] According to one embodiment of the present invention, L a Choose the structure represented by free formula 2, formula 4, formula 7, formula 10, formula 16 or formula 17.

[0102] According to one embodiment of the present invention, L a Choose the structure represented by free form 2, form 4, form 10 or form 16.

[0103] According to one embodiment of the present invention, in Equations 2 to 19, Z1 is N and Z2 is C.

[0104] According to one embodiment of the present invention, in Equations 2 to 19, Z2 is N and Z1 is C.

[0105] According to one embodiment of the present invention, in Equations 2 to 19, W is N.

[0106] According to one embodiment of the present invention, in Equations 2 to 19, Z1 is N, and D1 and / or D2 is N; or in Equations 2 to 19, Z2 is N, and C1 and / or C2 is N.

[0107] According to one embodiment of the present invention, in Equations 2 to 19, Z1 is N and D2 is N; or in Equations 2 to 19, Z2 is N and C2 is N.

[0108] According to one embodiment of the present invention, A1-A4 are each independently selected from CR a B1-B4 are each independently selected from CR b C1-C5 are each independently selected from CR c D1-D4 are each independently selected from CR d The R a R b R c and R dEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0109] Adjacent substituent R a R b R c and R d They can be arbitrarily connected to form a ring.

[0110] According to one embodiment of the present invention, A1-A4 are each independently selected from CR a B1-B4 are each independently selected from CR b C1-C5 are each independently selected from CR c D1-D4 are each independently selected from CR d The R a R b R c and R dEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 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 groups having 0-20 carbon atoms, cyano groups, and combinations thereof.

[0111] Adjacent substituent R a R b R c and R d They can be arbitrarily connected to form a ring.

[0112] According to one embodiment of the present invention, A1-A4 are each independently selected from CR a B1-B4 are each independently selected from CR b C1-C5 are each independently selected from CR c D1-D4 are each independently selected from CR d The R a R b R c and R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, cyano groups, and combinations thereof;

[0113] Adjacent substituent R a R b R c and R d They can be arbitrarily connected to form a ring.

[0114] According to an embodiment of the present invention, in formulas 2, 4 to 18, A1-A nAt least one of them is selected from CR each time it appears, either identically or differently. a The A n The one with the largest sequence number corresponding to A1-A4 in Equations 2, 4 to 18;

[0115] Or in equations 2 to 19, B1-B n At least one of them is selected from CR each time it appears, either the same or different. b The B n The one with the largest sequence number among any one of Equations 2-19 corresponding to B1-B4;

[0116] Or in equations 2 to 19, C1-C n At least one of them is selected from CR each time it appears, either identically or differently. c The C n The one with the largest sequence number among any one of Equations 2-19 corresponding to C1-C5;

[0117] Or in equations 2 to 19, D1-D n At least one of them is selected from CR each time it appears, either the same or different. d The D n The one with the largest sequence number among any one of Equations 2-19 corresponding to D1-D4;

[0118] And the R a R b R c and R d Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof;

[0119] Adjacent substituent R a R b R cand R d They can be arbitrarily connected to form a ring.

[0120] In this document, in Equations 2, 4 to 18, A1-A n At least one of them is selected from CR each time it appears, either the same or different. a The A n The largest of the sequence numbers corresponding to A1-A4 in any one of Equations 2, 4 to 18. For example, for Equation 2, the A... n A2 corresponds to the largest of the A1-A4 in Equation 2, meaning that in Equation 2, at least one of A1-A2 is selected from CR each time it appears, either identically or differently. a For example, regarding equation 4, the A... n The largest of A1-A4 in Equation 4 corresponds to A4, meaning that in Equation 4, at least one of A1-A4 is selected from CR each time it appears, either identically or differently. a Similarly, in equations 2 to 19, B1-B n At least one of them is selected from CR each time it appears, either the same or different. b The B n The largest of the sequence numbers of B1-B4 in any one of Equations 2-19, for example, for Equation 2, the B... n The largest of B1-B4 in Equation 2 corresponds to B4, meaning that in Equation 2, at least one of B1-B4 is selected from CR each time it appears, either identically or differently. b For example, regarding equation 18, the B... n The largest of the B1-B4 in Equation 18 is B2, meaning that in Equation 18, at least one of B1-B2 is selected from CR each time it appears, either identically or differently. b Similarly, in equations 2 to 19, C1-C n At least one of them is selected from CR each time it appears, either identically or differently. c The C n The largest of the C1-C5 sequences in any one of Equations 2-19, for example, for Equation 2, the C... n C3 is the largest of the C1-C5 in Equation 2, meaning that in Equation 2, at least one of C1-C3 is selected from CR each time it appears, either identically or differently. c For example, regarding equation 11, the C... n C5 is the largest of the C1-C5 in Equation 11, meaning that at least one of C1-C5 is selected from CR each time it appears, either identically or differently. cSimilarly, in equations 2 to 19, D1-D n At least one of them is selected from CR each time it appears, either identically or differently. d The D n The largest of the sequence numbers corresponding to D1-D4 in any one of Equations 2-19, for example, for Equation 2, the D... n The largest index D2 among D1-D4 in Equation 2 means that at least one of D1-D2 is selected from CR each time it appears, either identically or differently. d For example, regarding equation 7, the D... n The largest of the D1-D4 in Equation 7 corresponds to D4, meaning that in Equation 7, at least one of D1-D4 is selected from CR each time it appears, either identically or differently. d .

[0121] According to one embodiment of the present invention, in formulas 2, 4 to 18, A1 and / or A2 are selected from CR each time they appear, either identically or differently. a ; or in Equations 2 to 17, at least one of B2 to B4 is selected from CR each time it appears, either identically or differently. b ; or in Equations 18 to 19, B1 and / or B2 are selected from CR b ; or in Equations 2 to 19, at least one of C1 to C3 is selected from CR each time it appears, either identically or differently. c ; or in Equations 2 to 19, D1 and / or D2 are selected from CR d ; and the R a R b R c and R d Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0122] According to one embodiment of the present invention, in formulas 2, 4 to 18, A1 and / or A2 are selected from CR each time they appear, either identically or differently. a; or in Equations 2 to 17, at least one of B2 to B4 is selected from CR each time it appears, either identically or differently. b ; or in Equations 18 to 19, B1 and / or B2 are selected from CR b ; or in Equations 2 to 19, at least one of C1 to C3 is selected from CR each time it appears, either identically or differently. c ; or in Equations 2 to 19, D1 and / or D2 are selected from CR d ; and the R a R b R c and R d Each time it appears, it is selected from the group consisting of the following, either identically or differently: deuterium, fluorine, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, trimethylgermanyl, phenyl, pyridyl, triazine, trifluoromethyl, methoxy, dimethylamino, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.

[0123] According to one embodiment of the present invention, in formulas 18 to 19, B1 or B2 is selected from CR. b ;R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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, and combinations thereof.

[0124] According to one embodiment of the present invention, L a Choose L each time it appears, either the same or different. a1 To L a1241 The group consisting of; the L a1 To L a1241 For the specific structure, please refer to claim 9.

[0125] According to one embodiment of the present invention, wherein the L a1 To L a1241 In the structure, hydrogen can be partially or completely replaced by deuterium.

[0126] According to one embodiment of the present invention, L a Choose L each time it appears, either the same or different. a1 To L a1287 The group consisting of; the L a1 To L a1241 For the specific structure, please refer to claim 9, wherein the La1242 To L a1287 The structure is as follows:

[0127]

[0128]

[0129]

[0130] According to one embodiment of the present invention, wherein the L a1 To L a1287 In the structure, hydrogen can be partially or completely replaced by deuterium.

[0131] According to one embodiment of the present invention, the metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0132] Among them, metal M is selected from Ir, Rh, Re, Os, Pt, Au, or Cu; L a L b and L c These are the first, second, and third ligands coordinated with the metal M, respectively; m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, q is selected from 0, 1, or 2, and m+n+q equals the oxidation state of metal M; when m equals 2 or 3, multiple L... a They can be the same or different; when n equals 2, 2 L b They can be the same or different; when q equals 2, there are 2 Ls. c They can be the same or different;

[0133] L a L b and L c They can be selectively linked to form multidentate ligands;

[0134] L b and L c Each time the same or different occurrences appear, select the group consisting of the following structures:

[0135]

[0136]

[0137] in,

[0138] R i R ii and R iiiEach occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0139] X a Each time it appears, select the group consisting of the following, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0140] X b and X c Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0141] R i R ii R iii R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0142] Adjacent substituent R i R ii R iii R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0143] In this embodiment, adjacent substituents R i Rii R iii R N1 R N2 R C1 and R C2 They can be optionally connected to form a loop, intended to represent the L b L c Adjacent substituent groups in the structure, for example, adjacent substituent R i Between, adjacent substituents R ii Between, adjacent substituents R iii Between, adjacent substituents R i With R ii Between, adjacent substituents R ii With R iii Between, adjacent substituents R i With R iii Between, adjacent substituents R i With R N1 Between, adjacent substituents R i With R C1 Between, adjacent substituents R i With R C2 Between, adjacent substituents R ii With R N1 Between, adjacent substituents R iii With R N1 Between, adjacent substituents R ii With R C1 Between, adjacent substituents R ii With R C2 Between, adjacent substituents R iii With R C1 Between, adjacent substituents R iii With R C2 Between, adjacent substituents R i With R N2 Between, adjacent substituents R ii With R N2 Between, and adjacent substituents R C1 With R C2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0144] In this embodiment, L a L b and L c They can be optionally linked to form polydentate ligands, for example, L a L b and L cAny two or three of them can connect to form a tetradentate or hexadentate ligand. It is obvious that L... a L b and L c Alternatively, they can all be left unconnected, thus preventing the formation of polydentate ligands.

[0145] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0146] According to one embodiment of the present invention, the metal M is Ir.

[0147] According to one embodiment of the present invention, L b Each occurrence is selected from the following structure, either identically or differently:

[0148]

[0149] R1–R7 are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1–20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3–20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1–20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3–20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7–30 carbon atoms, substituted or unsubstituted alkoxy groups having 1–20 carbon atoms, substituted or unsubstituted aroxy groups having 6–30 carbon atoms, substituted or unsubstituted alkenyl groups having 2–20 carbon atoms, substituted or unsubstituted alkenyl groups, and so on. Alkyne groups having 2-20 carbon atoms, 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, phosphin, and combinations thereof having 0-20 carbon atoms.

[0150] According to one embodiment of the present invention, L b Each occurrence is selected from the following structure, either identically or differently:

[0151]

[0152] Wherein, at least one or two of R1-R3, when appearing in the same or different manner, are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one or two of R4-R6, when appearing in the same or different manner, are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0153] According to one embodiment of the present invention, L b Each occurrence is selected from the following structure, either identically or differently:

[0154]

[0155] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0156] According to one embodiment of the present invention, L c Each occurrence, whether identical or different, is selected from the following structure:

[0157]

[0158] Among them, R8-R 15Each 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;

[0159] Adjacent substituents R8-R 15 They can be arbitrarily connected to form a ring.

[0160] In this embodiment, the adjacent substituents R8-R 15 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, substituents R8 and R9, substituents R9 and R... 10 , substituent R 10 and R 11 , substituent R 11 and R 12 , substituent R 12 and R 13 , substituent R 13 and R 14 and substituent R 14 and R 15 Any one or more of these substituents can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.

[0161] According to one embodiment of the present invention, wherein the L b Choose L each time it appears, either the same or different. b1 To L b322 The group consisting of; the L b1 To L b322 For the specific structure, please refer to claim 13.

[0162] According to one embodiment of the present invention, wherein the L cChoose L each time it appears, either the same or different. c1 To L c321 The group consisting of; the L c1 To L c321 For the specific structure, please refer to claim 13.

[0163] According to one embodiment of the present invention, wherein the L c Choose L each time it appears, either the same or different. c1 To L c331 The group consisting of; the L c1 To L c321 For the specific structure, please refer to claim 13, wherein the L c322 To L c331 The structure is as follows:

[0164] According to one embodiment of the present invention, the metal complex is an Ir complex and has the following properties: Ir(L a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a (L) c Any of the structures shown in )2; when the metal complex has Ir(L a (L) b (L) c When the structure of ) is used, the L a Choose freely L a1 To L a1241 Any of the groups formed, the L b Choose freely L b1 To L b322 Any one of the groups, the L c Choose freely L c321 Any one of the groups; when the metal complex has Ir(L a )2(L b When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a1 To L a1241 The L is any one or any two of the groups formed. 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 the structure of ) is used, the L aChoose L each time it appears, either the same or different. a1 To L a1241 The L is any one or any two of the groups formed. c Choose freely L c321 Any one of the groups; when the metal complex has Ir(L a (L) c When the structure of )2 is used, the L a Choose freely L a1 To L a1241 Any of the groups formed, the L c Choose L each time it appears, either the same or different. c321 Any one or two of the group consisting of; optionally, the hydrogen in the structure of the metal complex can be partially or completely replaced by deuterium.

[0165] According to one embodiment of the present invention, the metal complex is an Ir complex and has the following properties: Ir(L a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a (L) c Any of the structures shown in )2; when the metal complex has Ir(L a (L) b (L) c When the structure of ) is used, the L a Choose freely L a1 To L a1287 Any of the groups formed, the L b Choose freely L b1 To L b322 Any one of the groups, the L c Choose freely L c331 Any one of the groups; when the metal complex has Ir(L a )2(L b When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a1 To L a1287 The L is any one or any two of the groups formed. 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 the structure of ) is used, the L aChoose L each time it appears, either the same or different. a1 To L a1287 The L is any one or any two of the groups formed. c Choose freely L c331 Any one of the groups; when the metal complex has Ir(L a (L) c When the structure of )2 is used, the L a Choose freely L a1 To L a1287 Any of the groups formed, the L c Choose L each time it appears, either the same or different. c331 Any one or two of the group consisting of; optionally, the hydrogen in the structure of the metal complex can be partially or completely replaced by deuterium.

[0166] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compound 1 to compound 690;

[0167] Among them, compounds 1 to 538 and compounds 669 to 688 have Ir(L a )2(L b The general formula for ), where the two L's a Same, L a and L b These correspond to the structures listed in the table below:

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] Compounds 539 to 668, 689 and 690 have Ir(L a (L) c The general formula for )2, where the two L c Same, L a and L c These correspond to the structures listed in the table below:

[0177]

[0178]

[0179]

[0180] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0181] anode,

[0182] cathode,

[0183] And an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex, the specific structure of which is shown in any of the foregoing embodiments.

[0184] According to one embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0185] According to one embodiment of the present invention, the electroluminescent device emits red light.

[0186] According to one embodiment of the present invention, the electroluminescent device emits yellow light.

[0187] According to one embodiment of the present invention, the electroluminescent device emits green light.

[0188] According to one embodiment of the present invention, the electroluminescent device emits white light.

[0189] According to one embodiment of the present invention, in the device, the light-emitting layer further includes at least one host material.

[0190] According to one embodiment of the present invention, the light-emitting layer in the device further includes at least two host materials.

[0191] According to one embodiment of the present invention, in the device, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0192] According to one embodiment of the present invention, in the device, the body material can be a conventional body material in the prior art, for example, it can typically, but not be limited to, the following body materials:

[0193]

[0194]

[0195]

[0196] According to another embodiment of the present invention, a compound composition comprising a metal complex, wherein the specific structure of the metal complex is as shown in any of the foregoing embodiments is also disclosed.

[0197] Combination with other materials

[0198] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0199] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0200] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0201] Material synthesis examples:

[0202] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0203] Synthesis Example 1: Synthesis of Compound 5

[0204] Step 1: Synthesis of Intermediate 3

[0205]

[0206] Intermediate 1 (2.16 g, 10.9 mmol), intermediate 2 (3.9 g, 10.9 mmol), Pd(PPh3)4 (624 mg, 0.54 mmol), and Na2CO3 (1.74 g, 16.35 mmol) were placed in a 250 mL three-necked flask. Then, 1,4-dioxane / H2O (44 mL / 11 mL) was added, and nitrogen was purged. The mixture was reacted overnight at 80 °C. After TLC analysis to confirm complete reaction, the mixture was cooled to room temperature, diluted with EA, extracted with water, and the organic phase was collected. After concentration, the organic phase was purified by column chromatography to obtain intermediate 3 (3.94 g, yield 91.9%).

[0207] Step 2: Synthesis of Intermediate 4

[0208]

[0209] Intermediate 3 (3.94 g, 10 mmol) and Cs2CO3 (8.1 g, 25 mmol) were mixed in DMF (100 mL), and after purging with nitrogen, the mixture was reacted at 135 °C for 1 hour. After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature, water was added, and the product precipitated. The product was filtered, and the filter cake was washed with an appropriate amount of water and PE. After drying, intermediate 4 (2.6 g, yield 72.9%) was obtained.

[0210] Step 3: Synthesis of Intermediate 5

[0211]

[0212] Intermediate 4 (2.3 g, 6.5 mmol), Pd(OAc)2 (72 mg, 0.32 mmol), PCy3·HBF4 (tricyclohexylphosphine tetrafluoroborate, 236 mg, 0.64 mmol) and K2CO3 (1.8 g, 13 mmol) were mixed in DMAc (32 mL), purged with nitrogen, and reacted at 135 °C for 24 hours. After cooling to room temperature, water was added, and the mixture was extracted with dichloromethane. After concentration, intermediate 5 (720 mg, yield 34.6%) was obtained by column chromatography.

[0213] Step 4: Synthesis of Iridium Dimer 6

[0214]

[0215] Intermediate 5 (720 mg, 2.2 mmol) and IrCl3·3H2O (282 mg, 0.8 mmol) were mixed in ethoxyethanol (12 mL) and water (4 mL), purged with nitrogen, and refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the crude product of iridium dimer 6 was obtained by concentration and used directly in the next step without further purification.

[0216] Step 5: Synthesis of Compound 5

[0217]

[0218] The iridium dimer 6 obtained in step 4 was mixed with 3,7-diethyl-3-methyl-4,6-nonanedione (270 mg, 1.2 mmol), K₂CO₃ (552 mg, 4 mmol), and ethoxyethanol (12 mL) in a 100 mL single-necked flask. After purging with nitrogen, the mixture was reacted overnight at 45 °C. After the reaction was complete as monitored by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed with DCM into a 250 mL flask, and EtOH (approximately 10 mL) was added. The DCM was removed by rotary evaporation at room temperature, and a solid precipitated out. This solid was filtered off and washed with an appropriate amount of EtOH. The crude product was purified by column chromatography to obtain product compound 5 (240 mg, overall yield of 28.4%). The product was identified as the target product with a molecular weight of 1056.4.

[0219] Synthesis Example 2: Synthesis of Compound 26

[0220] Step 1: Synthesis of Iridium Dimer 8

[0221]

[0222] Intermediate 7 (45 mg, 0.13 mmol) and IrCl3·3H2O (18 mg, 0.052 mmol) were mixed in ethoxyethanol (3.9 mL) and water (1.3 mL), purged with nitrogen, and refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the crude product of iridium dimer 8 was obtained by concentration and used directly in the next step without further purification.

[0223] Step 2: Synthesis of Compound 26

[0224]

[0225] The prepared iridium dimer 8 was mixed with 3,7-diethyl-3-methyl-4,6-nonanedione (18 mg, 0.08 mmol), K₂CO₃ (36 mg, 0.26 mmol), and ethoxyethanol (4 mL) in a 100 mL single-necked flask. After purging with nitrogen, the mixture was reacted overnight at 45 °C. The reaction was monitored by TLC until complete, and then cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed with DCM into a 250 mL flask and subjected to column chromatography to give product compound 26 (20 mg, overall yield of 35.0%). The product was identified as the target product with a molecular weight of 1100.4.

[0226] Synthesis Example 3: Synthesis of Compound 559

[0227]

[0228] Intermediate 9 (2.6 g, 3.2 mmol), intermediate 10 (1.4 g, 4.8 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 120 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth. The solution was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give compound 559 (1.3 g, yield 44.9%). This product was identified as the target product with a molecular weight of 904.3.

[0229] Synthesis Example 4: Synthesis of Compound 689

[0230]

[0231] Intermediate 11 (2.2 g, 2.3 mmol), intermediate 12 (1.1 g, 3.2 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 120 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth. The solution was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give compound 689 (0.4 g, 16% yield). This product was identified as the target product with a molecular weight of 1072.5.

[0232] Synthesis Example 5: Synthesis of Compound 690

[0233]

[0234] Intermediate 9 (1.8 g, 2.2 mmol), intermediate 13 (0.9 g, 2.6 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 120 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth. The solution was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give compound 690 (0.9 g, 43% yield). This product was identified as the target product with a molecular weight of 960.4.

[0235] Synthesis Example 6: Synthesis of Compound 35

[0236] Step 1: Synthesis of Iridium Dimer 15

[0237]

[0238] Intermediate 14 (1.22 g, 3.42 mmol) and IrCl3·3H2O (402 mg, 1.14 mmol) were mixed in ethoxyethanol (30 mL) and water (10 mL), and after purging with nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, it was filtered to obtain iridium dimer 15, which could be used directly in the next step without further purification.

[0239] Step 2: Synthesis of Compound 35

[0240]

[0241] The prepared iridium dimer 15 was mixed with 3,7-diethyl-3-methyl-4,6-nonanedione (387 mg, 1.71 mmol), K₂CO₃ (788 mg, 5.7 mmol), and ethoxyethanol (30 mL) in a 100 mL single-necked flask. After purging with nitrogen, the mixture was reacted overnight at 60 °C. The reaction was monitored by TLC until complete, and then cooled to room temperature. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, and the crude product was dissolved in DCM. After concentration, the mixture was filtered and recrystallized with DCM / MeOH to give product compound 35 (360 mg, overall yield of 28%). The product was confirmed as the target product with a molecular weight of 1128.4.

[0242] Synthesis Example 7: Synthesis of Compound 671

[0243] Step 1: Synthesis of Iridium Dimer 17

[0244]

[0245] Intermediate 16 (74 mg, 0.18 mmol) and IrCl3·3H2O (24 mg, 0.07 mmol) were mixed in ethoxyethanol (6 mL) and water (2 mL), and after purging with nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the crude product of iridium dimer 17 was obtained by filtration and used directly in the next step without further purification.

[0246] Step 2: Synthesis of Compound 671

[0247]

[0248] The prepared iridium dimer 17 was mixed with 3,7-diethyl-3-methyl-4,6-nonanedione (25 mg, 0.11 mmol), K₂CO₃ (49 mg, 0.35 mmol), and ethoxyethanol (6 mL) in a 100 mL single-necked flask. After purging with nitrogen, the mixture was reacted overnight at 60 °C. The reaction was monitored by TLC until complete, and then cooled to room temperature. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, the crude product was dissolved in DCM, concentrated, filtered, and the filter cake was washed with MeOH. After drying, product compound 671 was obtained (20 mg, overall yield of 23%). The product was confirmed as the target product with a molecular weight of 1240.5.

[0249] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0250] Through a special ligand structure design, the metal complexes of the present invention can effectively control the emission wavelength. The following photoluminescence (PL) spectral data demonstrate this excellent effect of the metal complexes of the present invention.

[0251] Spectral data

[0252] The photoluminescence (PL) spectra of the compound of the present invention and the comparative compound were determined using a Prism F98 fluorescence spectrophotometer manufactured by Shanghai Prism Technology Co., Ltd. Samples of compound 35 of the present invention or comparative compound RD-A were prepared with HPLC-grade toluene to a concentration of 3 × 10⁻⁶. -5 A solution of mol / L was prepared, and then excited with light at a wavelength of 500 nm at room temperature (298 K) and its emission spectrum was measured.

[0253] The structures of compound 35 of this invention and comparative compound RD-A are as follows:

[0254]

[0255] The maximum emission wavelength of compound RD-A in the PL spectrum is 575 nm, while the maximum emission wavelength of compound 35 of this invention is 625 nm, achieving red light emission. It can be seen that the compounds of this invention can effectively control the emission wavelength due to their special ligand structure design, demonstrating the superior performance of the metal complexes of this invention.

[0256] In addition, the compounds of the present invention also have excellent device performance. The following device examples further verify the excellent performance of the compounds of the present invention in devices.

[0257] Device Example 1.1

[0258] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, the ITO anode was sequentially evaporated at a rate of 0.2-2 Å / s via thermal vacuum evaporation. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transport layer (HTL). Compound X-4 was used as an electron blocking layer (EBL). Then, compound 5 of the present invention was co-deposited on compound H-1 and compound SD as an emissive layer (EML, the weight ratio of compound H-1, compound SD and compound 5 of the present invention is 80:17:3). On the EML, compound H-1 served as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as an electron injection layer, and a 120 nm thick layer of aluminum was deposited as a cathode. The device was then transferred back to a glove box and sealed with a glass cover and desiccant to complete the device.

[0259] Device Example 1.2

[0260] The preparation method of device example 1.2 is the same as that of device example 1.1, except that compound X-4 and compound H-12 are used instead of compound H-1 and compound SD in the light-emitting layer (EML), and the weight ratio of compound X-4, compound H-12 and compound 5 of the present invention is adjusted to 47:47:6.

[0261] Device Comparison Example 1.1

[0262] The device comparative example 1.1 was prepared in the same manner as device example 1.1, except that compound RD-A was used instead of compound 5 of the present invention in the light-emitting layer (EML).

[0263] Device Comparison Example 1.2

[0264] The device comparative example 1.2 was prepared in the same manner as the device example 1.2, except that compound RD-A was used instead of compound 5 of the present invention in the light-emitting layer (EML).

[0265] The partial layer structure and thickness of the device are shown in the table below. The device uses more than one material; it is obtained by doping different compounds in the stated weight ratios.

[0266] Table 1. Partial device structures of device embodiments and comparative examples.

[0267]

[0268] The structure of the materials used in the device is shown below:

[0269]

[0270] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured, including the maximum emission wavelength (λ). max The data include voltage efficiency, current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE). These data are recorded and presented in Table 2.

[0271] Table 2 Device Data

[0272]

[0273] discuss:

[0274] As shown in Table 2, the compound containing multi-ring ligands in this invention exhibits significant advantages over the comparative compounds in terms of device performance, particularly in driving voltage and efficiency. Furthermore, it demonstrates superior device performance across various light-emitting substrates: Example 1.1 shows significant improvements in CE, PE, and EQE compared to Comparative Example 1.1, with increases of 36%, 44%, and 6%, respectively, and a nearly 6% decrease in driving voltage. Compared to Comparative Example 1.2, Example 1.2 shows even better device performance, with more significant improvements in CE, PE, and EQE, reaching 64%, 86%, and 20%, respectively, and a 12% decrease in driving voltage. These data comparisons demonstrate that the metal complex of this invention, due to its L... a The special fused ring structure design of the ligands gives it the excellent property of comprehensively and significantly improving device performance, fully demonstrating the superior performance and excellent application prospects of the metal complex of the present invention.

[0275] Device Example 2.1

[0276] The preparation method of device example 2.1 is the same as that of device example 1.1, except that compound 5 of the present invention is replaced by compound 559 of the present invention in the light-emitting layer (EML).

[0277] Device Example 2.2

[0278] The preparation method of device embodiment 2.2 is the same as that of device embodiment 1.2, except that compound 5 of the present invention is replaced by compound 559 of the present invention in the light-emitting layer (EML).

[0279] Device Example 2.3

[0280] The preparation method of device example 2.3 is the same as that of device example 1.2, except that compound 689 of the present invention is used instead of compound 5 of the present invention in the light-emitting layer (EML).

[0281] Device Example 2.4

[0282] The preparation method of device example 2.4 is the same as that of device example 1.2, except that compound 690 of the present invention is used instead of compound 5 of the present invention in the light-emitting layer (EML).

[0283] The partial layer structure and thickness of the device are shown in the table below. The device uses more than one material; it is obtained by doping different compounds in the stated weight ratios.

[0284] Table 3 Partial device structures of device embodiments and comparative examples.

[0285]

[0286]

[0287] The structure of the new material used in the device is shown below:

[0288]

[0289] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured, including the maximum emission wavelength (λ). max The data include voltage efficiency, current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE). These data are recorded and presented in Table 4.

[0290] Table 4 Device Data

[0291]

[0292] discuss:

[0293] The device data from Examples 2.1, 2.2, 2.3, and 2.4 show that using different types of auxiliary ligands in the compounds of this invention can successfully adjust the emission wavelength of the device to the yellow-green emission region, while also exhibiting good device performance: the EQE of Examples 2.1, 2.2, 2.3, and 2.4 can reach 21.25%, 24.03%, 23.71%, and 23.12%, respectively, demonstrating high device efficiency. Furthermore, Examples 2.1 to 2.4 all achieve low voltage, especially Examples 2.1, 2.2, and 2.4, where the driving voltage is very low (less than or equal to 2.78V). More notably, at 80mA / cm... 2At the specified current density, the lifetimes (LT97) of Examples 2.1, 2.2, and 2.4 reached 112.5h, 257h, and 154h, respectively, indicating that the metal complex of the present invention is a yellow and green light material with excellent performance.

[0294] In summary, the metal complex of the present invention, due to L a The special fused ring structure design of the ligands has comprehensively improved the device performance, and the metal complex of the present invention can also effectively control the emission wavelength, which can meet the needs of OLED devices for various emission bands from green light to red light, fully demonstrating the excellent application prospects of the metal complex of the present invention.

[0295] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A metal complex having Ir(L a )2(L b ) or Ir(L a (L) c The general formula of )2; the ligand L a It has a structure represented by Equation 2: ； in, Z1 is N, Z2 is C; W is selected from N; A1-A2 are selected from CR each time they appear, either identically or differently. a ; B1-B4 are selected from CR each time they appear, either identically or differently. b ; C1-C3 are selected from CR each time they appear, either the same or different. c ; D1-D2 are selected from CR each time they appear, either the same or different. d ; R a R b R c and R d Each time it appears, it is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, and combinations thereof; L b Each occurrence, whether identical or different, is selected from the following structure: Among them, X b and X c Selected from O; R i R ii and R iii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R i R ii and R iii 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, and combinations thereof; L c Each occurrence of the same or different selections is governed by the following structure: R i and R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R i and R ii 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, and combinations thereof; The substituted alkyl means that the alkyl can be replaced by one or more alkyl groups selected from deuterium, halogens, unsubstituted alkyl groups having 1-12 carbon atoms, and combinations thereof.

2. The metal complex of claim 1, wherein the L a In the middle, R a R b R c and R d Each time it appears, it is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, and combinations thereof.

3. The metal complex as described in claim 1, in, R a Each time it appears, it is selected from either hydrogen or deuterium, either in the same or different ways.

4. The metal complex of claim 1, wherein A1-A2 are each independently selected from C1. a B1-B4 are each independently selected from CR b C1-C3 are each independently selected from CR c D1-D2 are each independently selected from CR d The R a Each time it appears, it is selected from the group consisting of: hydrogen or deuterium, either identically or differently; R b R c and R d 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.

5. The metal complex as described in claim 4, wherein, The R b R c and R d Each time it appears, it is selected from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, and combinations thereof.

6. The metal complex of claim 1, wherein in formula 2, A1 and / or A2 are selected from CR each time they appear, either identically or differently. a ; or at least one of B2 to B4 is selected from CR each time it appears, either identically or differently. b ; or at least one of C1 to C3 is selected from CR each time it appears, either identically or differently. c ; or D1 and / or D2 are selected from CR d ; and the R a R b R c and R d Each time it appears, it is selected from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, and combinations thereof.

7. The metal complex of claim 1, wherein R a R b R c and R d 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, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, and combinations thereof.

8. The metal complex as described in claim 1, wherein, L a Each occurrence is either identical or different from the group consisting of the following structures: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Where TMS represents trimethylsilyl and Ph represents phenyl; Optionally, the L a1 To L a6 L a15 L a17 L a19 L a29 To L a34 L a42 To L a43 L a45 L a47 L a54 To L a59 L a67 To L a68 L a70 L a72 L a79 To L a84 L a92 To L a93 L a95 L a97 L a104 To L a109 L a116 To L a117 L a119 L a121 L a128 To L a133 L a140 To L a141 L a143 L a145 L a152 To L a157 L a164 To L a165 L a167 L a169 L a176 To L a181 L a188 To L a189 L a191 L a193 L a200 To L a205 L a212 To L a213 L a215 L a217 L a224 To L a226 L a231 To L a243 L a245 L a1151 To L a1166 L a1238 L a1240 L a1242 To L a1243 L a1245 L a1247 To L a1248 L a1252 To L a1253 L a1257 To L a1258 L a1262 To L a1263 L a1267 To L a1268 L a1272 To L a1273 L a1277 To L a1278 and L a1287 In the structure, hydrogen can be partially or completely replaced by deuterium.

9. The metal complex as claimed in claim 1, wherein, L c Each time the same or different occurrences appear, select the group consisting of the following structures: ； R i and R ii Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R i and R ii Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, and combinations thereof.

10. The metal complex of claim 1, wherein, The metal complex has Ir(L) a )2(L b The general formula of the ligand L; a It has a structure represented by Equation 2: ； in, Z1 is N, Z2 is C; W is selected from N; A1-A2 are selected from CR each time they appear, either identically or differently. a ; B1-B4 are selected from CR each time they appear, either identically or differently. b ; C1-C3 are selected from CR each time they appear, either the same or different. c ; D1-D2 are selected from CR each time they appear, either the same or different. d ; R a R b R c and R d Each time it appears, it is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, and combinations thereof; L b Each occurrence, whether identical or different, is selected from the following structure: R1–R7 are selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1–20 carbon atoms, and combinations thereof, each time they appear in the same or different manner.

11. The metal complex of claim 10, wherein, At least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms each time they appear; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms each time they appear.

12. The metal complex of claim 1, wherein, L c Each occurrence, whether identical or different, is selected from the following structure: Among them, R8-R 15 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, and combinations thereof.

13. The metal complex of claim 8, wherein, L b Each occurrence is either identical or different from the group consisting of the following structures: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Among them, L c Each occurrence is either identical or different from the group consisting of the following structures: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， 。 14. The metal complex of claim 13, wherein, Having Ir(L) a )2(L b ) and Ir(L a (L) c Any of the structures shown in )2; when the metal complex has Ir(L a )2(L b When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a1 To L a6 L a15 L a17 L a19 L a29 To L a34 L a42 To L a43 L a45 L a47 L a54 To L a59 L a67 To L a68 L a70 L a72 L a79 To L a84 L a92 To L a93 L a95 L a97 L a104 To L a109 L a116 To L a117 L a119 L a121 L a128 To L a133 L a140 To L a141 L a143 L a145 L a152 To L a157 L a164 To L a165 L a167 L a169 L a176 To L a181 L a188 To L a189 L a191 L a193 L a200 To L a205 L a212 To L a213 L a215 L a217 L a224 To L a226 L a231 To L a243 L a245 L a1151 To L a1166 L a1238 L a1240 L a1242 To L a1243 L a1245 L a1247 To L a1248 L a1252 To L a1253 L a1257 To L a1258 L a1262 To L a1263 L a1267 To L a1268 L a1272 To L a1273 L a1277 To L a1278 and L a1287 The L is any one or any two of the groups formed. b Choose freely L b1 To L b42 L b63 To L b90 L b95 To L b109 L b112 To L b115 L b118 To L b122 L b125 To L b127 L b130 To L b135 L b138 To L b142 L b152 To L b167 L b172 To L b194 L b199 To L b214 L b219 To L b225 L b229 To L b235 Any one of the groups; when the metal complex has Ir(L a (L) c When the structure of )2 is used, the L a Choose freely L a1 To L a6 L a15 L a17 L a19 L a29 To L a34 L a42 To L a43 L a45 L a47 L a54 To L a59 L a67 To L a68 L a70 L a72 L a79 To L a84 L a92 To L a93 L a95 L a97 L a104 To L a109 L a116 To L a117 L a119 L a121 L a128 To L a133 L a140 To L a141 L a143 L a145 L a152 To L a157 L a164 To L a165 L a167 L a169 L a176 To L a181 L a188 To L a189 L a191 L a193 L a200 To L a205 L a212 To L a213 L a215 L a217 L a224 To L a226 L a231 To L a243 L a245 L a1151 To L a1166 L a1238 L a1240 L a1242 To L a1243 L a1245 L a1247 To L a1248 L a1252 To L a1253 L a1257 To L a1258 L a1262 To L a1263 L a1267 To L a1268 L a1272 To L a1273 L a1277 To L a1278 and L a1287 Any of the groups formed, the L c Choose L each time it appears, either the same or different. c1 To L c35 L c232 To L c303 L c322 To L c331 Any one or two of the group consisting of; optionally, the hydrogen in the structure of the metal complex can be partially or completely replaced by deuterium.

15. The metal complex of claim 14, wherein the metal complex is selected from the group consisting of compounds 1 to 21, 23, 25, 27, 29, 539 to 553, 559 to 570, 603 to 617, 623 to 649, 603 to 617, 623 to 649, 655 to 666, 673 to 680, 682, 684, 686, and 688 to 690. in, Compounds 1 to 21, 23, 25, 27, 29, 673 to 680, 682, 684, 686, and 688 possess Ir(L a )2(L b The general formula for ), where the two L's a Same, L a and L b These correspond to the structures listed in the table below: Compounds 539 to 550, 559 to 564, 603 to 614, 623 to 628, 635 to 660, and 689 to 690 have Ir(L a (L) c The general formula for )2, where the two L c Same, L a and L c These correspond to the structures listed in the table below: 。 16. An electroluminescent device, comprising: anode, cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex as described in any one of claims 1-15.

17. The electroluminescent device of claim 16, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

18. The electroluminescent device of claim 16 or 17, wherein the electroluminescent device emits red, yellow, green or white light.

19. The electroluminescent device of claim 17, wherein the light-emitting layer further comprises at least one host material.

20. The electroluminescent device of claim 19, wherein the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

21. A compound composition comprising the metal complex as described in any one of claims 1-15.

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