A luminescent material with a polycyclic ligand

Abstract

A luminescent material with a polycyclic ligand is disclosed. The luminescent material is a metal complex of a novel polycyclic ligand having the structure of Formula 1 and can be used as a luminescent material in an electroluminescent device. These novel metal complexes can cause a significant red shift in the maximum emission wavelength of the device in the electroluminescent device, can significantly adjust the emission color, and at the same time have a very narrow emission spectrum, can greatly improve the saturation of the device luminescence, and can provide better device performance. An electroluminescent device and a compound combination are also disclosed.

Description

Technical Field

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

[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 photoreceptors, organic field-effect quantum dots (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent 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 tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The 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 a cathode and an anode. Since OLEDs are a self-emitting solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be classified into three different types according to their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlets and triplets, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from 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 and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.

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

[0007] The emission color of OLEDs can be achieved through the structural design of the emitting materials. OLEDs can include one or more emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue color unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.

[0008] In the two articles Inorg. Chem. 2005, 44, 5677 (DOI: 10.1021 / ic050385s) and Synthetic Metals. 2005, 155, 539 (DOI: 10.1016 / j.synthmet.2005.08.034), metal complexes with structures were respectively disclosed. These two articles focused on the performance study of metal complexes with ligands containing quinoline. Neither of them disclosed or taught the performance changes brought about by introducing a fused ring structure between the aryl and heteroaryl groups in a specific aryl - heteroaryl ligand structure.

[0009] In CN108148577A, metal complexes with the following structure were disclosed: One of the many disclosed structures is: The inventor focused on the performance changes brought about by introducing a specific 5 - membered fused ring at a specific position on the phenanthroline ring in the ligand of the metal complex, but this application did not disclose or teach the performance changes brought about by introducing a fused ring structure between the aryl and heteroaryl groups in a specific aryl - heteroaryl ligand structure.

[0010] In US20080214818A1, metal complexes with the following structure were disclosed: One of the many disclosed structures is: The inventor focused on the application of ligands with phenanthroline and phenanthrenone structures in metal complex luminescent materials. However, this application did not disclose or teach the performance changes brought about by introducing a fused ring structure between the aryl and heteroaryl groups in a specific aryl - heteroaryl ligand structure.

[0011] Although various phosphorescent metal complexes have been reported in the prior art, they still cannot meet the increasing industry requirements for device performance, such as more saturated luminescence, higher luminescence efficiency, lower operating voltage, and longer device lifetime, etc. Therefore, further development is still needed in the field of phosphorescent metal complexes. Summary of the Invention

[0012] The present invention aims to provide a series of metal complexes with polycyclic ligands to solve at least part of the above problems. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can cause a significant red - shift in the maximum emission wavelength of the device in the electroluminescent device, can significantly adjust the emission color, and at the same time have a very narrow emission spectrum, can greatly improve the saturation of device luminescence, and can provide better device performance.

[0013] According to an embodiment of the present invention, a metal complex is disclosed, which comprises a ligand L aand a metal M, wherein M is selected from metals having an atomic mass greater than 40, and L a has a structure represented by Formula 1:

[0014]

[0015] wherein ring A and ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 30 carbon atoms, or a heteroaromatic ring having 3 - 30 carbon atoms; ring C is selected from a heteroaromatic ring having 3 - 30 carbon atoms;

[0016] R x each occurrence is the same or different and represents mono-substitution, multi-substitution, or no substitution;

[0017] Y is selected from CR y R y , SiR y R y , GeR y R y , NR y , PR y , O, S, or Se;

[0018] R x and R y each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, a substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, a substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0019] Adjacent substituents R x and R y can optionally be linked to form a ring.

[0020] According to another embodiment of the present invention, there is also disclosed an electroluminescent device, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the metal complex as shown in the above embodiments.

[0021] According to another embodiment of the present invention, there is also disclosed a compound combination, which contains the metal complex as shown in the above embodiments.

[0022] The novel metal complexes with polycyclic ligands disclosed by the present invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes can cause a significant red shift in the maximum emission wavelength of the device in the electroluminescent device, can significantly adjust the emission color, and at the same time can obtain a very narrow emission spectrum, can greatly improve the saturation of the device emission, and can provide better device performance. Description of the Drawings

[0023] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the metal complexes and compound combinations disclosed herein.

[0024] Figure 2 is a schematic diagram of another organic light-emitting device that can contain the metal complexes and compound combinations disclosed herein. Detailed Description of the Invention

[0025] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 Schematically and non-limitingly shows an organic light-emitting device 100. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.

[0026] Each of these layers has more instances. For example, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. 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, incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated 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, incorporated herein by reference in its entirety. U.S. Patents Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of the barrier layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties. Examples of the injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety.

[0027] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve a desired emission spectrum.

[0028] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0029] The OLED also requires a encapsulation layer, as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0030] 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) incorporating the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0031] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0032] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed 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 there are various organic layers between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

[0033] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0034] When it is believed that a ligand directly contributes to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When it is believed that a ligand does not contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0035] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0036] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay of the triplet state, the fraction of the singlet excited state refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.

[0037] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0038] Definition of substituent terms

[0039] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0040] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.

[0041] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl, 1 - adamantyl, 2 - adamantyl, 1 - norbornyl, 2 - norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, and 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0042] Heteroalkyl - as used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0043] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - methylvinyl, styryl, 2,2 - diphenylethylene, 1,2 - diphenylethylene, 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, cycloheptatrieneyl, cyclooctenyl, cyclooctatetraeneyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0044] Alkynyl - As used herein, linear alkynyl is encompassed. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropargyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0045] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0046] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.

[0047] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups having 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and their nitrogen - containing analogs. Additionally, the heteroaryl can be optionally substituted.

[0048] Alkoxy - As used herein, it is represented by - O - alkyl, - O - cycloalkyl, - O - heteroalkyl, or - O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocycloalkyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0049] Aryloxy - As used herein, it is represented by - O - aryl or - O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0050] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0051] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0052] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0053] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0054] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0055] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0056] In the present disclosure, unless otherwise defined, when any one of the following terms is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocycloalkyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermyl having 3 to 20 carbon atoms, unsubstituted arylgermyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0057] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attachment fragment are considered equivalent.

[0058] In the compounds mentioned in the present disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0059] Among the compounds mentioned in the present disclosure, polysubstituted refers to the range including disubstituted up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.

[0060] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally be connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), as well as an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, 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.

[0061] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0062]

[0063] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0064]

[0065] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0066]

[0067] In addition, the expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to, in the case where one of the adjacent two substituents represents hydrogen, the second substituent being bonded at the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0068]

[0069] According to an embodiment of the present invention, a metal complex is disclosed, which comprises a ligand L a and a metal M, wherein the M is selected from metals with a relative atomic mass greater than 40, and the L a has a structure represented by Formula 1:

[0070]

[0071] wherein, ring A and ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 30 carbon atoms, or a heteroaromatic ring having 3 - 30 carbon atoms; ring C is selected from a heteroaromatic ring having 3 - 30 carbon atoms;

[0072] R x represents, each time it appears, the same or different, a mono-substituted, multi-substituted or unsubstituted group;

[0073] Y is selected from CR y R y , SiR y R y , GeR y R y , NR y , PR y , O, S or Se; when two R y are present simultaneously, the two R y can be the same or different;

[0074] R x and R y are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 carbon atoms in the ring, a substituted or unsubstituted heteroalkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 - 20 carbon atoms, a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 - 20 carbon atoms, a substituted or unsubstituted amino group having 0 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0075] Adjacent substituents R x and R y can optionally be linked to form a ring.

[0076] In this embodiment, adjacent substituents R x and R y can optionally be linked to form a ring, which is intended to represent adjacent substituent groups among them. For example, adjacent substituents R x , adjacent substituents R y , and adjacent substituents R x and R y . Any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring.

[0077] According to an embodiment of the present invention, wherein ring A and ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 18 carbon atoms, or a heteroaromatic ring having 3 - 18 carbon atoms; and / or ring C is selected from a heteroaromatic ring having 3 - 18 carbon atoms.

[0078] According to an embodiment of the present invention, wherein ring A and ring B are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 10 carbon atoms, or a heteroaromatic ring having 3 - 10 carbon atoms; and / or ring C is selected from a heteroaromatic ring having 3 - 10 carbon atoms.

[0079] According to an embodiment of the present invention, wherein ring A and ring B are each independently selected from a benzene ring, a naphthalene ring, an indene ring, a pyridine ring, a furan ring, a thiophene ring, a pyrrole ring, a cyclopentadiene ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a naphthyridine ring, a benzofuran ring, a benzothiophene ring, or an indole ring; and / or ring C is selected from an imidazole ring, a pyridine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a naphthyridine ring, an azabenzofuran ring, an azabenzothiophene ring, or an azaindole ring.

[0080] According to an embodiment of the present invention, wherein L a has a structure represented by any one of the group consisting of Formula 2 to Formula 15:

[0081]

[0082]

[0083] X1 - X 10 is the same or different each time it appears and is selected from CR x or N;

[0084] Z1 and Z2 are the same or different each time they appear and are selected from O, S, or NR z ;

[0085] Y is selected from CRy R y ,SiR y R y ,GeR y R y ,NR y ,PR y ,O, S or Se; when two Rs are present simultaneously, y the two Rs y are the same or different;

[0086] R x 、R z 、R y is each independently selected, each time it appears, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0087] adjacent substituents R x 、R z 、R y can optionally be joined to form a ring.

[0088] In this context, adjacent substituents R x 、R z 、R y can optionally be joined to form a ring, which is intended to mean any adjacent group of substituents, for example adjacent substituents R x , adjacent substituents R y , and adjacent substituents R z , and any one or more of these adjacent groups of substituents can be joined to form a ring. Obviously, none of these adjacent groups of substituents may also be joined to form a ring.

[0089] According to one embodiment of the present invention, wherein, L aHas a structure represented by Formula 2, Formula 3, Formula 5, Formula 7, Formula 10, Formula 12, or Formula 14.

[0090] According to one embodiment of the present invention, wherein L a Has a structure represented by Formula 2, Formula 5, or Formula 10.

[0091] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, the substituent R x , R z , R y At least two adjacent substituents are connected to form a ring. For example, in the structure represented by any one of Formulas 2 to 15, at least two adjacent substituents R x Are connected to form a ring, and / or adjacent substituents R x And R z Are connected to form a ring, and / or two adjacent substituents R y Are connected to form a ring, and / or adjacent substituents R x And R y Are connected to form a ring.

[0092] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, at least two adjacent substituents R x Are connected to form a ring.

[0093] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, at least one of X1 - X n Is selected from N, and the X n Corresponds to the largest serial number among those where X1 - X 10 Exists in any one of Formulas 2 - 15.

[0094] In this embodiment, in Formulas 2 to 15, at least one of X1 - X n Is selected from N, and the X n Corresponds to the largest serial number among those where X1 - X 10 Exists in any one of Formulas 2 to 15; for example, for Formula 2, the X n Corresponds to the largest serial number among those where X1 - X 10 Exists in Formula 2, which is X8, that is, in Formula 2, at least one of X1 - X8 is selected from N. Another example, for Formula 3, the X n Corresponds to the largest serial number among those where X1 - X 10 Exists in Formula 3, which is X6, that is, in Formula 3, at least one of X1 - X6 is selected from N.

[0095] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, X3 is N.

[0096] According to one embodiment of the present invention, in Formula 2 to Formula 15, X1-X 10 is the same or different each time it appears and is selected from CR x .

[0097] According to one embodiment of the present invention, in Formula 2 to Formula 15, R x , R z , R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.

[0098] According to one embodiment of the present invention, in Formula 2 to Formula 15, R x , R z , R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, and combinations thereof.

[0099] According to one embodiment of the present invention, in Formula 2 to Formula 15, R x , R z , R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, trimethylpyrimidinyl, di-tert-butyltriazinyl, and combinations thereof.

[0100] According to an embodiment of the present invention, in Formulae 2 to 15, X1 to X n are at least one or two or three, each occurrence being the same or different, and are selected from CR x , and the X n corresponds to the largest serial number among X1 - X 10 present in any one of Formulae 2 to 15; and the R x is, each occurrence being the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, cyano, and combinations thereof.

[0101] In this embodiment, in Formulae 2 to 15, X1 - X n are at least one or two or three, each occurrence being the same or different, and are selected from CR x , and the X n corresponds to the largest serial number among X1 - X 10 present in any one of Formulae 2 to 15; for example, for Formula 2, the X n corresponds to the largest serial number X8 among X1 - X 10 present in Formula 2, that is, in Formula 2, at least one or two or three of X1 - X8 are, each occurrence being the same or different, selected from CR x . Again, for example, for Formula 3, the X n corresponds to the largest serial number X6 among X1 - X 10 present in Formula 3, that is, in Formula 3, at least one or two or three of X1 - X6 are, each occurrence being the same or different, selected from CR x .

[0102] According to an embodiment of the present invention, in Formulae 2 to 15, X3 to X5 are, each occurrence being the same or different, selected from CR x , and the R x is, each occurrence being the same or different, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, cyano, and combinations thereof.

[0103] According to one embodiment of the present invention, in Formulas 2 - 15, X3 to X5 are each independently selected from CR x , and said R x is each independently selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, trimethylpyrimidinyl, di-tert-butyltriazinyl, and combinations thereof.

[0104] According to one embodiment of the present invention, in Formulas 2 to 15, X1 - X 10 is each independently selected from CR x or N; wherein at least one of X1 - X n is selected from CR x , and said X n corresponds to the X1 - X 10 with the largest serial number among those present in any one of Formulas 2 to 15; and said R x is each independently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0105] In the present context, in Formulas 2 to 15, at least one of X1 - X n is selected from CR x , and said X n corresponds to the X1 - X 10 with the largest serial number among those present in any one of Formulas 2 to 15; for example, for Formula 2, said X n corresponds to the X1 - X 10The largest numbered one X8 among those present in Formula 2, that is, in Formula 2, at least one of X1 - X8 is selected from CR x . Also, for example, for Formula 3, the X n corresponds to the X1 - X 10 The largest numbered one X6 among those present in Formula 3, that is, in Formula 3, at least one of X1 - X6 is selected from CR x .

[0106] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, X1 - X 10 is the same or different each time it appears and is selected from CR x or N; wherein at least one of X1 - X n is selected from CR x , the X n corresponds to the X1 - X 10 the largest numbered one among those present in any one of Formulas 2 to 15; and the R x is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, cyano, and combinations thereof.

[0107] According to one embodiment of the present invention, wherein, in Formulas 2 to 15, X1 - X 10 is the same or different each time it appears and is selected from CR x or N; wherein at least one of X1 - X n is selected from CR x , the X n corresponds to the X1 - X 10 the largest numbered one among those present in any one of Formulas 2 to 15; and the R x is the same or different each time it appears and is selected from the group consisting of: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert - butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, trimethylpyrimidinyl, di - tert - butyltriazinyl, and combinations thereof.

[0108] According to one embodiment of the present invention, wherein, in Formulas 2 to 4, Formulas 7 to 9, Formulas 12 to 15, at least one of X1 - X3 is selected from CR x ; in Formulas 5, 10, X1 - X3, X9, X 10at least one selected from CR x ; in Formula 6 and Formula 11, at least one of X1-X3, X7, X8 is selected from CR x ; and said R x is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0109] According to one embodiment of the present invention, in Formulas 2 to 15, at least one of X1-X3 is the same or different each time it appears and is selected from CR x ; said R x is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0110] According to one embodiment of the present invention, in Formulas 2 to 15, X3 is selected from CR x ; said R x is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0111] According to one embodiment of the present invention, in Formulas 2, 5, 7, 8, 10, 12, 14, at least one or two of X4 - X8 are the same or different each time they appear and are selected from CR x ; in Formulas 3, 4, 6, 9, 11, 13, 15, at least one or two of X4 - X6 are the same or different each time they appear and are selected from CR x ; and said R xEach occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0112] According to one embodiment of the present invention, in Formulas 2 to 15, at least one or two of X4-X6 are the same or different and are selected from CR each occurrence x ; said R x Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0113] According to one embodiment of the present invention, in Formulas 2 to 15, X5 is selected from CR x ; said R xEach occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0114] According to one embodiment of the present invention, in Formulas 2 to 15, at least 1 or 2 or 3 of X1-X5 are the same or different and are each selected from CR x ; said R x Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, and combinations thereof.

[0115] According to one embodiment of the present invention, in Formulas 2 to 15, at least 1 or 2 or 3 of X1-X5 are the same or different and are each selected from CR x ; said R x Each occurrence is the same or different and is selected from the group consisting of: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, trimethylpyrimidinyl, di-tert-butyltriazinyl, and combinations thereof.

[0116] According to one embodiment of the present invention, Y is selected from O, S or Se.

[0117] According to one embodiment of the present invention, Y is selected from O or S.

[0118] According to an embodiment of the present invention, wherein said L a is the same or different each time it appears and is selected from the group consisting of L a1 to L a1492 :

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] In the above structure, TMS represents trimethylsilyl.

[0161] According to one embodiment of the present invention, wherein the metal complex has the structure of M(L a ) m (L b ) n (L c ) q ;

[0162] The metal M is selected from metals with a relative atomic mass greater than 40;

[0163] L a 、L b and L care the first ligand, the second ligand, and the third ligand of the complex, respectively; L a , L b and L c can optionally be linked to form a polydentate ligand;

[0164] m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m + n + q is equal to the oxidation state of metal M;

[0165] When m is greater than 1, multiple L a can be the same or different; when n is 2, two L b can be the same or different; when q is 2, two L c can be the same or different;

[0166] L b and L c are each independently selected from the group consisting of the following structures, either the same or different each time they appear:

[0167]

[0168] R a 、R b and R c represent mono-substitution, multi-substitution, or no substitution;

[0169] X b is each independently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0170] X c and X d are each independently selected from the group consisting of: O, S, Se, and NR N2 ;

[0171] R a 、R b 、R c 、R N1 、R N2 、R C1 and R C2Each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0172] Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring.

[0173] In this example, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring, which is intended to represent adjacent substituent groups therein. For example, between two substituents R a , between two substituents R b , between two substituents R c , between substituent R a and R b , between substituent R a and R c , between substituent R b and R c , between substituent R a and R N1 , between substituent R b and R N1 , between substituent R a and R C1 , between substituent R a and RC2 between, substituent R b and R C1 between, substituent R b and R C2 between, substituent R a and R N2 between, substituent R b and R N2 between, and R C1 and R C2 between. Any one or more of these substituent groups may be connected to form a ring. Obviously, these substituents may also not be connected to form a ring.

[0174] In this embodiment, L a , L b and L c can optionally be connected to form a polydentate ligand, which is intended to mean that any two or three of L a , L b and L c can be connected to form a tetradentate ligand or a hexadentate ligand. Obviously, L a , L b and L c may also not be connected and thus do not form a polydentate ligand.

[0175] According to an embodiment of the present invention, wherein the metal complex has the structure of M(L a ) m (L b ) n ;

[0176] Metal M is selected from metals with a relative atomic mass greater than 40;

[0177] L a , L b are the first ligand and the second ligand of the complex respectively; L a , L b can optionally be connected to form a polydentate ligand;

[0178] m is 1, 2 or 3, n is 0, 1 or 2, and m + n is equal to the oxidation state of metal M;

[0179] When m is greater than 1, multiple L a can be the same or different; when n is 2, two L b can be the same or different;

[0180] L b is the same or different each time it appears and is selected from the following structures:

[0181]

[0182] Each occurrence of R1–R7 is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0183] In this example, L a and L b can optionally be connected to form a multidentate ligand, which is intended to represent any two or all of the ligands in L a and L b , for example, two L a , two L b , one L a and one L b or all of the L a and L b can be connected to form a tetradentate ligand or a hexadentate ligand. Obviously, L a and L b can also not be connected to each other so as not to form a multidentate ligand.

[0184] According to one embodiment of the present invention, wherein each occurrence of L b is the same as or different from each other and is independently selected from the following structures:

[0185]

[0186] wherein at least one of R1-R3 is independently selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is independently selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof.

[0187] According to one embodiment of the present invention, wherein L bIdentically or differently selected from the following structures each time it appears:

[0188]

[0189] Wherein at least two of R1 - R3 are selected from 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, or combinations thereof; and / or at least two of R4 - R6 are 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, or combinations thereof.

[0190] According to one embodiment of the present invention, wherein L b Identically or differently selected from the following structures each time it appears:

[0191]

[0192] Wherein at least two of R1 - R3 are selected from substituted or unsubstituted alkyl groups having 2 - 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 - 20 carbon atoms, or combinations thereof; and / or at least two of R4 - R6 are selected from substituted or unsubstituted alkyl groups having 2 - 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 - 20 carbon atoms, or combinations thereof.

[0193] According to one embodiment of the present invention, wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au, or Cu.

[0194] According to one embodiment of the present invention, wherein the metal M is selected from Ir, Pt, or Os.

[0195] According to one embodiment of the present invention, wherein the metal M is Ir.

[0196] According to one embodiment of the present invention, wherein L b Identically or differently selected from the group consisting of L b1 to L b322 :

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] L c Each occurrence is the same or different and is selected from the group consisting of L c1 to L c231 :

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] According to one embodiment of the present invention, wherein the metal complex has the structure of Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2; when the metal complex has the structure of Ir(L a )2(L b ), L a Each occurrence is the same or different and is selected from any one or any two of the group consisting of L a1 to L a1492 , and L b is selected from any one of the group consisting of L b1 to L b322 ; when the metal complex has the structure of Ir(L a )2(L c ), L a Each occurrence is the same or different and is selected from any one or any two of the group consisting of L a1 to L a1492 , and L c is selected from any one of the group consisting of L c1 to L c231Any one of the groups formed; when the metal complex has Ir(L a )(L c )2 structure, L a is selected from any one of the group consisting of L a1 to L a1492 , and L c , each occurrence being the same or different, is selected from any one or any two of the group consisting of L c1 to L c231 .

[0213] According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 200, wherein Compound 1 to Compound 150 have the structure of Ir(L a )2(L b ), wherein two L a are the same, and L a and L b correspond to the structures listed in the following table respectively:

[0214]

[0215]

[0216]

[0217] Among them, Compound 151 to Compound 200 have the structure of Ir(L a )2(L b ), wherein two L a are different, and L a and L b correspond to the structures listed in the following table respectively:

[0218]

[0219]

[0220] According to an embodiment of the present invention, an electroluminescent device is also disclosed, which includes:

[0221] An anode,

[0222] A cathode,

[0223] And an organic layer disposed between the anode and the cathode, the organic layer contains a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0224] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0225] According to an embodiment of the present invention, the device emits red light or white light.

[0226] According to an embodiment of the present invention, in the device, the light-emitting layer further comprises at least one host material.

[0227] According to an embodiment of the present invention, in the device, the at least one host material contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0228] According to an embodiment of the present invention, in the device, the host material may be a conventional host material in the prior art. For example, it may typically but non - restrictively include the following host materials:

[0229]

[0230]

[0231] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0232] Combined with other materials

[0233] The materials for specific layers in the organic light - emitting devices described in the present invention can be used in combination with various other materials present in the device. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non - restrictive examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0234] The materials described herein as being specific layers useful in organic light emitting devices can be used in combination with a variety of other materials present in the devices. For example, the light emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of U.S. Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non - limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0235] 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 received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art (including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatographs, liquid chromatography - mass spectrometers, gas chromatography - mass spectrometers, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc.) by methods well - known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art (including but not limited to evaporation coaters produced by Angstrom Engineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc.) by methods well - known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above - mentioned devices and testing methods and can obtain the inherent data of the samples determinately and without influence, the above - mentioned relevant content will not be elaborated further in this patent.

[0236] Examples of material synthesis:

[0237] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0238] Synthesis Example 1: Synthesis of Compound 99

[0239] Step 1: Synthesis of Intermediate 3

[0240]

[0241] Intermediate 1 (9.10 g, 62.69 mmol), Intermediate 2 (23.30 g, 81.50 mmol), copper(I) iodide (0.60 g, 3.13 mmol), N,N - dimethylglycine hydrochloride (DMG .HCl (0.44 g, 3.13 mmol), potassium carbonate (21.66 g, 156.73 mmol) were dissolved in N,N-dimethylformamide (100 mL). Then, under nitrogen protection, the reaction was heated to 100 °C and stirred for 20 hours, and then cooled to room temperature. Then, ethyl acetate was added to the reaction system, and the layers were separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and the solvent was removed in vacuo to obtain the crude product. The crude product was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:10, v / v) to obtain Intermediate 3 (16.00 g, yield 73%).

[0242] Step 2: Synthesis of Intermediate 4

[0243]

[0244] Intermediate 3 (4.00 g, 11.42 mmol) was dissolved in 40 mL of ultra-dry tetrahydrofuran. Under a nitrogen atmosphere, a solution of n-butyllithium (12.56 mmol, 2 M / L, 6.3 mL) was slowly added dropwise at -76 °C, and the mixture was stirred for 2.5 hours. After the raw materials reacted completely, water was added to quench the reaction, and the temperature was raised to 0 °C. Then, iodine (3.50 g, 13.7 mmol) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 4.35 g, 28.55 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The crude product was obtained by filtration. Column chromatography separation (PE:EA = 50:1) gave the yellow liquid Intermediate 4 (2.77 g, yield 90%).

[0245] Step 3: Synthesis of Iridium Dimer

[0246]

[0247] A mixture of Intermediate 4 (3.97 g, 14.75 mmol), iridium(III) chloride trihydrate (1.30 g, 3.69 mmol), 2-ethoxyethanol (48 mL) and water (16 mL) was refluxed under a nitrogen atmosphere for 40 hours. After cooling to room temperature, 3.10 g of iridium dimer was obtained by filtration and could be directly used in the next reaction without further purification.

[0248] Step 4: Synthesis of Compound 99

[0249]

[0250] The iridium dimer obtained in Step 3, intermediate 5 (2.09 g, 9.23 mmol), and potassium carbonate (2.55 g, 18.45 mmol) were added to a reaction tube containing 20 mL of dichloromethane, and the mixture was heated to 60 °C under nitrogen protection and reacted for 24 hours. Subsequently, it was poured into a funnel filled with diatomaceous earth for filtration, and the filter cake was washed with ethanol. Dichloromethane was added to the filter cake and the filtrate was collected. Then ethanol was added and the resulting solution was concentrated, but not to dryness. After filtration, 1.35 g of product compound 99 was obtained, and the overall yield of the two steps was 38.3%. The structure of this product was confirmed to be the target product by LC-MS, with a molecular weight of 954.3.

[0251] Synthesis Example 2: Synthesis of Compound 91

[0252] Step 1: Synthesis of Iridium Dimer

[0253]

[0254] A mixture of intermediate 6 (1.5 g, 6.80 mmol), iridium(III) chloride trihydrate (0.60 g, 1.70 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under a nitrogen atmosphere for 40 hours. After cooling to room temperature, 0.80 g of iridium dimer was obtained by filtration and could be directly used in the next step without further purification.

[0255] Step 2: Synthesis of Compound 91

[0256]

[0257] The iridium dimer obtained in Step 1, intermediate 5 (0.36 g, 1.50 mmol), and potassium carbonate (0.83 g, 6.00 mmol) were added to a reaction tube containing 20 mL of dichloromethane, and the mixture was heated to 60 °C under nitrogen protection and reacted for 40 hours. Subsequently, it was poured into a funnel filled with diatomaceous earth for filtration and washed with ethanol. Dichloromethane was added to the filter cake and the filtrate was collected. Then ethanol was added and the resulting solution was concentrated, but not to dryness. After filtration, 0.36 g of product compound 91 was obtained, and the overall yield of the two steps was 25.0%. The structure of this product was confirmed to be the target product by LC-MS, with a molecular weight of 854.3.

[0258] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0259] Device Example

[0260] Device Example 1

[0261] First, clean the glass substrate, which has an indium tin oxide (ITO) anode with a thickness of 120 nm, and then treat it with oxygen plasma and UV ozone. After treatment, dry the substrate in a glove box to remove moisture. Then mount the substrate on a substrate holder and load it into a vacuum chamber. The following specified organic layers are deposited sequentially on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / second under a vacuum of about 10 -8 Torr. Compound HI is used as the hole injection layer (HIL). Compound HT is used as the hole transport layer (HTL). Compound EB is used as the electron blocking layer (EBL). Then, the compound 99 of the present invention is doped in the host compound RH2 as the emitting layer (EML). Compound HB is used as the hole blocking layer (HBL). On the HBL, compounds ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as the electron transport layer (ETL). Finally, deposit 1 nm thick Liq as the electron injection layer, and deposit 120 nm of Al as the cathode. Then transfer the device back to the glove box and encapsulate it with a glass cover and a moisture absorbent to complete the device.

[0262] Device Example 2

[0263] The device of Device Example 2 is prepared in the same manner as that of Device Example 1, except that compound 91 of the present invention is used instead of compound 99 in the emitting layer (EML), and compound RH1 is used instead of compound RH2 as the host material.

[0264] Device Comparative Example 1

[0265] The device of Device Comparative Example 1 is prepared in the same manner as that of Device Example 1, except that compound RD-1 is used instead of compound 99 in the emitting layer (EML).

[0266] Device Comparative Example 2

[0267] The device of Device Comparative Example 2 is prepared in the same manner as that of Device Example 2, except that compound RD-2 is used instead of compound 91 in the emitting layer (EML).

[0268] The device layer structure and thickness are shown in the following table. For those where more than one material is used, different compounds are doped in the recorded weight ratios.

[0269] Table 1 Device Structure of Device Examples

[0270]

[0271] The material structures used in the device are shown as follows:

[0272]

[0273]

[0274] The IVL characteristics of the device were measured. Table 2 shows the maximum emission wavelength (λ 2 ) and full width at half maximum (FWHM) data measured at a current density of 15 mA / cm max .

[0275] Table 2 Device Data

[0276]

[0277] Discussion:

[0278] By comparing the data between Example 1 and Comparative Example 1, it can be found that the maximum emission wavelength of Example 1 reached 690 nm, which was significantly redshifted by as much as 53 nm compared with Comparative Example 1, and the amplitude was unexpectedly large; the full width at half maximum of Example 1 was 36.4 nm, and compared with the already very narrow full width at half maximum of 44.3 nm of Comparative Example 1, it was further significantly narrowed by nearly 8 nm. It is proved that the compound of the present invention can significantly redshift the emission spectrum of the device, can significantly adjust the emission color of the device, achieve deep red emission, and can significantly narrow the full width at half maximum, achieving very saturated emission.

[0279] By comparing the data between Example 2 and Comparative Example 2, it can be found that the maximum emission wavelength of Example 2 reached 643 nm, which was significantly redshifted by as much as 48 nm compared with Comparative Example 2; the full width at half maximum of Example 2 reached an astonishing 28.3 nm, which was very rare, and compared with Comparative Example 2, it was extremely narrowed by 51.3 nm, and the amplitude was unexpectedly large, achieving very saturated emission. It is proved again that the compound of the present invention can significantly redshift the emission spectrum of the device, can significantly adjust the emission color of the device, achieve deep red emission, and at the same time can significantly narrow the full width at half maximum, achieving very saturated emission.

[0280] In summary, the compound of the present invention can significantly adjust the emission color of the device, and at the same time has a very narrow full width at half maximum, can greatly improve the saturation of the device emission, and has excellent application prospects.

[0281] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be obvious to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced by other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A metal complex having the structure of Ir(L a )2(L b ), wherein, The L a has a structure represented by Formula 1: Among them, ring A and ring B are selected from benzene rings; ring C is selected from pyridine rings or quinoline rings; R x each occurrence independently represents mono-substitution, poly-substitution or no substitution, which may be the same or different; Y is selected from O or S; R x each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof; Among them, the L b is selected from the following structures: R a , R b and R c represent mono-substitution, multi-substitution or no substitution; X c and X d selected from O; R a 、R b 、R c each occurrence of which is the same as or different from one another and is independently selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a cyano group, and combinations thereof; The substituted alkyl group having 1-20 carbon atoms, the substituted cycloalkyl group having 3-20 ring carbon atoms, the substituted aryl group having 6-30 carbon atoms, and the substituted heteroaryl group having 3-30 carbon atoms mean that any one of the alkyl group, cycloalkyl group, aryl group, and heteroaryl group can be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl group having 1-20 carbon atoms, unsubstituted cycloalkyl group having 3-20 ring carbon atoms, unsubstituted aryl group having 6-30 carbon atoms, unsubstituted heteroaryl group having 3-30 carbon atoms, and combinations thereof; The metal complex is not the following compound:

2. The metal complex according to claim 1, wherein, L a having a structure represented by Formula 2 or Formula 5: X1-X 10 each occurrence being the same as or different from each other and independently selected from CR x ; Y is selected from O; R x each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

3. The metal complex according to claim 2, wherein L a has a structure represented by Formula 5.

4. The metal complex according to claim 2, wherein, R x Each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof.

5. The metal complex according to claim 2, wherein R x Each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

6. The metal complex according to claim 2, wherein, R x Each occurrence is independently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trifluoromethyl, phenyl, trimethylpyrimidinyl, di-tert-butyltriazinyl, and combinations thereof.

7. The metal complex according to claim 2, wherein, In Formulas 2 and 5, X1-X 10 is the same as or different from each other each time it appears and is selected from CR x ; where at least one of X1-X n is selected from CR x , and the X n corresponds to the one with the largest serial number among X1-X 10 present in any one of Formulas 2 and 5; and the R x is the same as or different from each other each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

8. The metal complex according to claim 7, wherein Said R x Each occurrence is the same as or different from and is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.

9. The metal complex according to claim 7, wherein Said R x Each occurrence is the same or different and is selected from the group consisting of: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, trifluoromethyl, phenyl, trimethylpyrimidinyl, di-tert-butyltriazinyl, and combinations thereof.

10. The metal complex according to claim 2, wherein, In Formula 2, at least one of X1 - X3 is selected from CR x ; in Formula 5, at least one of X1 - X3, X9, X 10 is selected from CR x ; and each occurrence of said R x is the same or different and is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof.

11. The metal complex according to claim 10, wherein in Formula 2 and Formula 5, each occurrence of X1-X3 is the same or different and at least one is independently selected from CR x .

12. The metal complex according to claim 10, wherein in Formula 2 and Formula 5, X3 is selected from CR x .

13. The metal complex according to claim 2, wherein In Formula 2 and Formula 5, at least one or two of X4-X8 are the same or different each time they appear and are independently selected from CR x ; and said R x is the same or different each time it appears and is independently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

14. The metal complex according to claim 13, wherein, In Formula 2 and Formula 5, at least one or two of X4 - X6 are each independently selected from CR, either the same or different, each time they appear x .

15. The metal complex according to claim 13, wherein in Formula 2 and Formula 5, X5 is selected from CR x .

16. The metal complex according to claim 1, wherein, Said L a is the same as or different from each occurrence and is selected from the group consisting of the following structures:

17. The metal complex according to claim 1, wherein L b is the same as or different from each other and is selected from the following structures each time it appears: Each occurrence of R1-R7 is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, cyano group, and combinations thereof.

18. The metal complex according to claim 17, wherein at least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, or combinations thereof; and / or at least one of R4-R6 is a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, or a combination thereof.

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

20. The metal complex according to claim 16, wherein L b is the same or different each time it appears and is selected from the group consisting of the following structures:

21. The metal complex according to claim 20, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 6, Compound 8 to Compound 14, Compound 16, Compound 17, Compound 19, Compound 22 to Compound 24, Compound 26 to Compound 30, Compound 39, Compound 40, Compound 42 to Compound 44, Compound 46 to Compound 51, Compound 53 to Compound 59, Compound 61, Compound 62, Compound 64, Compound 67 to Compound 69, Compound 71 to Compound 75, Compound 84 to Compound 85, Compound 87 to Compound 89, Compound 91 to Compound 96, Compound 98 to Compound 104, Compound 106, Compound 107, Compound 109, Compound 112 to Compound 114, Compound 116 to Compound 120, Compound 129 to Compound 130, Compound 132 to Compound 134, Compound 136 to Compound 141, Compound 144 to Compound 145, Compound 148 to 149, Compound 151 to Compound 155, Compound 158, Compound 160 to Compound 167, Compound 170, Compound 172 to Compound 179, Compound 182, Compound 184 to Compound 191, Compound 194, Compound 196 to Compound 200; Among the compounds 1 to 6, compounds 8 to 14, compound 16, compound 17, compound 19, compounds 22 to 24, compounds 26 to 30, compound 39, compound 40, compounds 42 to 44, compounds 46 to 51, compounds 53 to 59, compound 61, compound 62, compound 64, compounds 67 to 69, compounds 71 to 75, compounds 84 to 85, compounds 87 to 89, compounds 91 to 96, compounds 98 to 104, compound 106, compound 107, compound 109, compounds 112 to 114, compounds 116 to 120, compounds 129 to 130, compounds 132 to 134, compounds 136 to 141, compounds 144 to 145, compounds 148 to 149 have the structure of Ir(L a )2(L b ), where the two L a are the same, and L a and L b are respectively selected from the structures listed in the following table: Among them, Compounds 151 to 155, compound 158, compounds 160 to 167, compound 170, compounds 172 to 179, compound 182, compounds 184 to 191, compound 194, compounds 196 to 200 have the structure of Ir(L a )2(L b ), where the two L a are different, and L a and L b correspond to the structures listed in the following table respectively:

22. An electroluminescent device, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex according to any one of claims 1-21.

23. The electroluminescent device according to claim 22, wherein, The organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

24. The electroluminescent device according to claim 23, wherein, The device emits red light or white light.

25. The electroluminescent device according to claim 23, wherein, The light-emitting layer further comprises at least one host material.

26. The electroluminescent device according to claim 25, wherein, The at least one host material contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicofluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

27. A compound combination, comprising the metal complex according to any one of claims 1-21.

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