An organic luminescent material containing germanium-substituted quinoline ligand

Abstract

Disclosed is an organic luminescent material containing a germanium-substituted quinoline ligand. The organic luminescent material is a metal complex comprising a metal M and a ligand L coordinated with the M. a , the ligand L a The novel metal complex has a structure represented by Formula 1. The novel metal complex can be used as a luminescent material in an electroluminescent device. These novel metal complexes can effectively adjust the maximum emission wavelength of the device to achieve deep red luminescence, while improving the external quantum efficiency of the device and providing better device performance. An electroluminescent device and a compound combination are also disclosed.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a metal complex containing a ligand of formula 1, and an organic electroluminescent device and a compound combination containing the metal complex. Background Art

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-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 is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, 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 on flexible substrates.

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

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

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

[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.

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

[0009] US20210115077A1 discloses a method comprising A metal complex of a ligand, wherein G represents a silicon atom or a germanium atom, and wherein CY2 is a carbon ring or a heterocycle. etc. contain metal complexes with germanium-substituted quinoline ligands; this application focuses on the changes in device performance brought about by the simultaneous introduction of specific cyclic substituents and silicon / germanium groups into phenylquinoline ligands; in addition, in the structures disclosed therein, the germanium groups are all at the 6-position of quinoline, and it does not note the changes in device performance brought about by the germanium groups at other positions of quinoline.

[0010] Although the introduction of germanium groups into metal complexes has been reported, the relevant metal complexes still have problems such as insufficient luminescence saturation, insufficient voltage, insufficient luminescence efficiency or emission wavelength not meeting the requirements. Therefore, phosphorescent metal complexes containing germanium groups still need further development. Summary of the invention

[0011] The present invention aims to provide a series of metal complexes containing germanium-substituted quinoline 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 effectively adjust the maximum emission wavelength of the device to achieve deep red luminescence, while improving the external quantum efficiency of the device and providing better device performance.

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

[0013]

[0014] Wherein, X1-X5 are selected from CRR in the same or different manner each time they appear x or N;

[0015] Ring A represents a fused ring system formed by at least two structures selected from a five-membered carbocyclic ring, a five-membered heterocyclic ring, a six-membered carbocyclic ring or a six-membered heterocyclic ring;

[0016] R y Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0017] R x , R y , R g The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0018] Adjacent substituent R y , R g Can optionally be linked to form a ring.

[0019] According to another embodiment of the present invention, an electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer arranged between the anode and the cathode; the organic layer contains a metal complex, and the specific structure of the metal complex is shown in any of the above embodiments.

[0020] According to another embodiment of the present invention, a compound combination is also disclosed, which includes a metal complex, and the specific structure of the metal complex is shown in any of the above embodiments.

[0021] The novel metal complex containing germanium-substituted quinoline ligand disclosed in the present invention can be used as a luminescent material in an electroluminescent device. These novel metal complexes can effectively adjust the maximum emission wavelength of the device to achieve deep red luminescence, and at the same time can improve the external quantum efficiency of the device and provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound combinations disclosed herein.

[0023] Figure 2is a schematic diagram of another organic light-emitting device that may contain the metal complex and compound combination disclosed herein. DETAILED DESCRIPTION

[0024] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0025] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0026] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0027] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0028] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0029] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0030] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0031] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0032] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0033] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0034] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0035] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0036] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0037] Definition of Substituent Terms

[0038] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0039] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-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. In addition, the alkyl group may be optionally substituted.

[0040] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0041] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.

[0042] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0043] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.

[0044] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.

[0045] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0046] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0047] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0048] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0049] 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,

[0050] 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.

[0051] 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.

[0052] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.

[0053] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.

[0054] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0055] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any one of which may be selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted cycloalkyl having 6-30 carbon atoms, unsubstituted cycloalkyl having 2-2 ... Aryl, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0056] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0057] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0058] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0059] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0060] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0061]

[0062] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0063]

[0064] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0065]

[0066] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0067]

[0068] According to another embodiment of the present invention, a metal complex is also disclosed, which comprises a metal M and a ligand L coordinated with the M. a , the metal M is selected from metals with a relative atomic mass greater than 40, and the L a Having a structure represented by Formula 1:

[0069]

[0070] Wherein, X1-X5 are selected from CR in the same or different manner each time they appear. x or N;

[0071] Ring A represents a fused ring system formed by at least two structures selected from a five-membered carbocyclic ring, a five-membered heterocyclic ring, a six-membered carbocyclic ring or a six-membered heterocyclic ring;

[0072] R y Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0073] R x , R y , R g The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0074] Adjacent substituent R y , R g Can optionally be linked to form a ring.

[0075] In this context, adjacent substituents R y , R g can be optionally connected to form a ring, which is intended to indicate adjacent groups of substituents, such as adjacent substituents R y , the adjacent substituent R g , any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.

[0076] According to one embodiment of the present invention, in Formula 1, X1-X5 are selected from CR x .

[0077] According to one embodiment of the present invention, in Formula 1, at least one of X1-X5 is selected from N.

[0078] According to one embodiment of the present invention, the metal complex has M(L a ) m (L b ) n (L c ) q structure;

[0079] L a , L b and L c are the first ligand, the second ligand and the third ligand of the metal complex respectively; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than 1, multiple L a The same or different; when n is 2, the two L b The same or different; when q is 2, the two L c Same or different;

[0080] L a , L b and L c can optionally be linked to form a multidentate ligand;

[0081] L b and L c Each occurrence is identically or differently selected from the group consisting of:

[0082]

[0083] Among them, R a , R band R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0084] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0085] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0086] R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring 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 cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0087] Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

[0088] In this embodiment, the adjacent substituent R a , R b , Rc , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0089] In this embodiment, L a , L b and L c can optionally be linked to form a multidentate ligand, such as L a , L b and L c Any two of them can be connected to form a tetradentate ligand. For example, L a , L b and L c They can also be linked to form hexadentate ligands. Obviously, L a , L b and L c It is also possible that none of them are connected so as not to form a multidentate ligand.

[0090] According to one embodiment of the present invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0091] According to one embodiment of the present invention, M is selected from Ir or Pt.

[0092] According to one embodiment of the present invention, M is Ir.

[0093] According to one embodiment of the present invention, in Formula 1, the ring A represents a condensed ring system having 8 to 30 ring atoms.

[0094] According to one embodiment of the present invention, in Formula 1, Ring A is selected from any one of the following CA-1 to CA-22:

[0095] Y1-Y8 are selected from CR y or N;

[0096] Each time Z appears, it is selected from CR y R y , NR y ,O,SiR y R y , P.R. y , S, S(O), S(O)2, Se, Se(O) or Se(O)2;

[0097] R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0098] Adjacent substituent R y can optionally be linked to form a ring;

[0099] In the structures of CA-1 to CA-22, indicates the position of the bond with the carbon atom, Indicates the location of bonding with metal atoms.

[0100] In this embodiment, the adjacent substituent R y can be optionally connected to form a ring, which is intended to indicate that any adjacent substituents R y Obviously, any adjacent substituents R y They can also not be connected to form a ring.

[0101] According to one embodiment of the present invention, in Formula 1, the ring A is selected from CA-1, CA-10, CA-14, CA-15, CA-18 or CA-19.

[0102] According to one embodiment of the present invention, in Formula 1, the ring A is selected from CA-1, CA-10 or CA-18.

[0103] According to one embodiment of the present invention, in CA-1 to CA-22, Z is selected from CR y R y , NR y ,O,SiR y R y , S or Se.

[0104] According to one embodiment of the present invention, in CA-1 to CA-22, Z is selected from NR y , O or S.

[0105] According to one embodiment of the present invention, in CA-1 to CA-22, at least one of Y1-Y8 is selected from N.

[0106] According to one embodiment of the present invention, in CA-1 to CA-22, Y1 is N.

[0107] According to one embodiment of the present invention, in CA-1 to CA-22, Y1-Y8 are selected from CR y .

[0108] According to one embodiment of the present invention, in Formula 1, X1-X5 are selected from CR x In CA-1 to CA-22, Y1-Y8 are selected from CR y .

[0109] According to one embodiment of the present invention, in CA-1 to CA-22, at least one of Y1-Y8 is selected from CRy ; and said R y each occurrence is identically or differently 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 heterocyclyl having 3 to 20 ring 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 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0110] According to one embodiment of the present invention, in CA-1 to CA-22, at least one of Y1-Y8 is selected from CR y ; and said R y Each occurrence is identically or differently 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, hydroxyl, mercapto, and combinations thereof.

[0111] According to one embodiment of the present invention, in CA-1 to CA-22, at least one of Y1-Y8 is selected from CR y ; and said R y Each occurrence is identically or differently selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, phenyl, pyridyl, triazine, cyano, and combinations thereof.

[0112] According to one embodiment of the present invention, wherein the L a Having a structure represented by Formula 2:

[0113]

[0114] Wherein, X1-X5 are selected from CR in the same or different manner each time they appear. x or N;

[0115] Y1-Y6 are selected from CR y or N;

[0116] Z is selected from NR y , O or S;

[0117] R x , R y , R g The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0118] Adjacent substituent R y , R g Can optionally be linked to form a ring.

[0119] According to one embodiment of the present invention, in Formula 2, at least one of X1-X5 and / or Y1-Y6 is selected from N.

[0120] According to one embodiment of the present invention, in Formula 2, X1 and / or Y1 are selected from N.

[0121] According to one embodiment of the present invention, in Formula 2, Y1 is selected from N.

[0122] According to one embodiment of the present invention, in Formula 2, X1-X5 is selected from CR x , Y1-Y6 are selected from CRy .

[0123] According to one embodiment of the present invention, in Formula 1 or Formula 2, R x The second occurrence is selected, identically or differently, 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 heterocyclyl having 3 to 20 ring 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 a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof having 0 to 20 carbon atoms.

[0124] According to one embodiment of the present invention, in Formula 1 or Formula 2, R x The first occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 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 alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0125] According to one embodiment of the present invention, in Formula 1 or Formula 2, at least one of X1-X5 is selected from CR x , and / or at least one of Y1-Y6 is selected from CR y ; and said R x1 , R yeach occurrence is identically or differently 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 heterocyclyl having 3 to 20 ring 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 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0126] According to one embodiment of the present invention, in Formula 1 or Formula 2, X3 and / or X4 are selected from CR x , and / or Y2 and / or Y6 are each selected from CR y ; and said R x1 , R y Each occurrence is identically or differently 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 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, cyano, and combinations thereof.

[0127] According to one embodiment of the present invention, in Formula 1 or Formula 2, X3 and / or X4 are selected from CR x , and / or Y2 and / or Y6 are each selected from CR y ; and said R x , R y Each occurrence is identically or differently selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, phenyl, pyridyl, triazine, cyano, and combinations thereof.

[0128] According to one embodiment of the present invention, in Formula 1 or Formula 2, the R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0129] According to one embodiment of the present invention, in Formula 1 or Formula 2, the R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0130] According to one embodiment of the present invention, in Formula 1 or Formula 2, the R g Each occurrence is identically or differently selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trifluoromethyl, phenyl, pyridyl, and combinations thereof.

[0131] According to one embodiment of the present invention, wherein the L b It has the following structure:

[0132]

[0133] R 11 To R 17each occurrence is the same or different 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 heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted cycloalkyl having 2-20 carbon atoms alkenyl, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0134] According to one embodiment of the present invention, R 11 -R 13 At least one or two of them are 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 a combination thereof at each occurrence; and / or R 14 -R 16 At least one or two of the above are selected, at each occurrence, identically or differently, from 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 heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0135] According to one embodiment of the present invention, R 11 -R 13 At least one or two of them are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms, or a combination thereof at each occurrence; and / or R 14 -R 16 At least one or two of the above are selected, at each occurrence, identically or differently, from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

[0136] According to one embodiment of the present invention, the metal complex has M(L a )2(L b ) has the general structure.

[0137] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) has the general structure.

[0138] According to one embodiment of the present invention, wherein the L a Each occurrence is identically or differently selected from the group consisting of the following structures, wherein L a1 To L a575 For the specific structure, please refer to claim 17.

[0139] According to one embodiment of the present invention, wherein the L a1 To L a575 The hydrogen in the structure can be partially or completely replaced by deuterium.

[0140] According to one embodiment of the present invention, wherein the L b Each time it appears, choose the same or different one from L b1 To L b322 The group consisting of L c Each time it appears, choose the same or different one from L c1 To L c231 The group consisting of: b1 To L b322 and L c1 To L c231 For the specific structure, please refer to claim 18.

[0141] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure; wherein, when the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1 To L a575 Any one or two of the group consisting of L b Choose from L b1 To L b322 When the metal complex has Ir(L a )2(L c) structure, L a Each time it appears, choose the same or different one from L a1 To L a575 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1 To L a575 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 To L c231 Any one or any two of the group consisting of.

[0142] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 260, and the specific structures of Compound 1 to Compound 260 are shown in Claim 19.

[0143] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0144] anode,

[0145] cathode,

[0146] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex, and the specific structure of the metal complex is as shown in any of the aforementioned embodiments.

[0147] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0148] According to an embodiment of the invention, the device emits red light.

[0149] According to an embodiment of the invention, the device emits white light.

[0150] According to one embodiment of the present invention, in the device, the light-emitting layer further includes at least one host material.

[0151] According to one embodiment of the present invention, in the device, the at least one host compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof

[0152] According to one 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 not limitatively include the following host materials:

[0153]

[0154] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises a metal complex. The specific structure of the metal complex is shown in any of the above embodiments.

[0155] Combination with other materials

[0156] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0157] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0158] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0159] Material synthesis example:

[0160] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0161] Synthesis Example 1: Synthesis of Compound 101

[0162] Step 1: Synthesis of intermediate 3

[0163]

[0164] Intermediate 1 (2.74 g, 8.44 mmol), intermediate 2 (2.60 g, 8.44 mmol), tetrakistriphenylphosphine palladium (0.49 g, 0.42 mmol), sodium carbonate (1.79 g, 16.88 mmol), 1,4-dioxane (20 mL) and water (7 mL) were added to a 100 mL round-bottom flask, and then the reaction was heated to 100 ° C under nitrogen protection and stirred overnight, and cooled to room temperature after TLC showed that the reaction was complete. Then ethyl acetate was added to the reaction system, the liquid was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent ethyl acetate: petroleum ether = 1:10, v / v) to obtain a white solid intermediate 3 (0.79 g, yield 77%).

[0165] Step 2: Synthesis of iridium dimer

[0166]

[0167] A mixture of intermediate 3 (2.28 g, 5.35 mmol), iridium trichloride trihydrate (0.47 g, 1.34 mmol), 2-ethoxyethanol (45 mL) and water (15 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the solid was filtered and washed several times with methanol and dried to give an iridium dimer (0.95 g, 65.7% yield), which was used directly in the next step without further purification.

[0168] Step 3: Synthesis of compound 101

[0169]

[0170] A mixture of iridium dimer (0.95 g, 0.44 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.42 g, 1.76 mmol), potassium carbonate (0.60 g, 4.4 mmol) and 2-ethoxyethanol (30 mL) obtained in the previous step was stirred at 50 ° C for 24 hours. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the precipitate was filtered through diatomaceous earth and washed with methanol. Dichloromethane was added to the obtained filter cake and the filtrate was collected. Methanol was then added and the obtained solution was concentrated until solid precipitation occurred. After filtration, a red product compound 101 (0.23 g, 0.18 mmol) was obtained. The structure of the compound was confirmed as the target product by LC-MS, and the molecular weight was 1284.35.

[0171] Synthesis Example 2: Synthesis of Compound 61

[0172]

[0173] A mixture of iridium dimer (0.19 g, 0.087 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.092 g, 0.35 mmol), potassium carbonate (0.12 g, 0.87 mmol) and 2-ethoxyethanol (5 mL) obtained in step 2 of Synthesis Example 1 was stirred at room temperature for 24 hours. After the reaction was complete, the precipitate was filtered through diatomaceous earth and washed with methanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Methanol was then added and the obtained solution was concentrated until a solid precipitated. After filtration, a red product compound 61 (0.07 g, 0.05 mmol) was obtained. The structure of the compound was confirmed as the target product by LC-MS, and the molecular weight was 1310.29.

[0174] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0175] Device Example 1

[0176] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 In the case of 1000 Å / s, the ITO anode is deposited sequentially by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as hole injection layer (HIL). Compound HT is used as hole transport layer (HTL). Compound EB is used as electron blocking layer (EBL). Then, compound 101 of the present invention is doped in host compound RH as light-emitting layer (EML). Compound HB is used as hole blocking layer (HBL). On HBL, co-deposition compound ET and 8-hydroxyquinoline-lithium (Liq) are used as electron transport layer (ETL). Finally, 1 nm thick Liq is deposited as electron injection layer, and 120 nm Al is deposited as cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0177] Device Example 2

[0178] Device Example 2 was prepared in the same manner as Device Example 1, except that Compound 61 was used instead of the present compound 101 in the emissive layer (EML).

[0179] Device Comparison Example 1

[0180] Device Comparative Example 1 was prepared in the same manner as Device Example 1, except that Compound RD-1 was used instead of Compound 101 of the present invention in the emission layer (EML).

[0181] Device Comparison Example 2

[0182] Device Comparative Example 2 was prepared in the same manner as Device Example 1, except that Compound RD-2 was used instead of Compound 101 of the present invention in the emission layer (EML).

[0183] Device Comparison Example 3

[0184] Device Comparative Example 3 was prepared in the same manner as Device Example 1, except that Compound RD-3 was used instead of Compound 101 of the present invention in the emission layer (EML).

[0185] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0186] Table 1 Device structure of device examples

[0187]

[0188] The material structure used in the device is shown below:

[0189]

[0190] The IVL characteristics of the device were measured. Table 2 shows the IVL characteristics of the device at 15 mA / cm 2 CIE data of device embodiments and comparative examples measured at current density, maximum emission wavelength λ max , voltage (V), external quantum efficiency (EQE) and full width at half maximum (FWHM) data.

[0191] Table 2 Device data

[0192]

[0193] discuss:

[0194] From the data in Table 2, it can be seen that Examples 1 and 2 have low voltages and narrow half-peak widths comparable to those of Comparative Examples 1-3, indicating that Examples 1 and 2 can achieve saturated red light emission under low voltage driving, demonstrating the excellent performance of the compounds of the present invention in the device.

[0195] By comparing Examples 1 and 2 with Comparative Examples 1 and 2, it can be seen that the metal complex of the present application can effectively adjust the luminescence spectrum of such compounds due to the introduction of germanium groups at specific positions on the ligand skeleton. In addition, the EQE of Comparative Examples 1 and 2 are 21.07% and 24.33%, respectively, which are already very high external quantum efficiencies, but by introducing germanium groups, we further improve the external quantum efficiency of the device to 25.91% and 25.43%, which is very rare and highlights the uniqueness and importance of the present invention.

[0196] By comparing Examples 1 and 2 with Comparative Example 3, it can be seen that in the metal complex of the present application, by fixing the germanium group at a specific position, the EQE of the device can be further greatly improved on the basis of the already high EQE of Comparative Example 3 (the EQE of Examples 1 and 2 are increased by 14.8% and 12.7% respectively relative to Comparative Example 3), which is very rare. In addition, Example 1 and Comparative Example 3 only change the position of the germanium group substitution in the metal complex structure as a luminescent dopant, but the maximum emission wavelength of the device is significantly red-shifted by as much as 4nm, achieving a deeper red luminescence, reflecting the unique advantages brought by the introduction of the germanium group substitution at a specific position on the quinoline ring in the ligand of the present invention, and fully reflecting the uniqueness and importance of the present invention.

[0197] 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 apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A metal complex having M(L a )2(L b ) structure, where M is selected from Ir, L a The same or different, the L a Having a structure represented by Formula 2: Wherein, X1-X5 are selected from CR in the same or different manner each time they appear. x ; Each occurrence of Y1-Y6 is selected from CR y ; Z is selected, identically or differently, from O or S at each occurrence; R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; R g Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; and substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 ring carbon atoms, means that any one of the alkyl and cycloalkyl groups is substituted by one or more deuterium groups; The L b It has the following structure: Among them, X c and X d Selected from O; R a , R b , R c Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; The substituted alkyl group having 1 to 20 carbon atoms and the substituted cycloalkyl group having 3 to 20 ring carbon atoms refer to any one of the alkyl group and the cycloalkyl group being substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms and unsubstituted alkoxy group having 1 to 20 carbon atoms.

2. The metal complex according to claim 1, wherein Z is selected from O.

3. The metal complex according to claim 1, wherein In Formula 2, at least one of X1-X5 is selected from CR x , and / or at least one of Y1-Y6 is selected from CR y ; and said R x , R y Each occurrence is identically or differently selected from the group consisting of deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

4. The metal complex according to claim 3, wherein In Formula 2, X3 and / or X4 are selected from CR x , and / or Y2 and / or Y6 are each selected from CR y ; and said R x , R y Each occurrence is identically or differently selected from the group consisting of deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

5. The metal complex according to claim 3, wherein The R x , R y Each occurrence is identically or differently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, isobutyl, neopentyl, and combinations thereof.

6. The metal complex according to claim 1, wherein The R g Each occurrence is identically or differently selected from substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms.

7. The metal complex according to claim 6, wherein The R g Each occurrence is identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 12 carbon atoms.

8. The metal complex according to claim 6, wherein The R g Each occurrence is identically or differently selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl.

9. The metal complex according to claim 1, wherein The L b It has the following structure: R 11 To R 17 Each occurrence of is the same or different 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, and combinations thereof.

10. The metal complex according to claim 9, wherein R 11 -R 13 At least one or two of them are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof at each occurrence; and / or R 14 -R 16 At least one or two of them are selected, at each occurrence, identically or differently, from 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, or a combination thereof.

11. The metal complex according to claim 9, wherein R 11 -R 13 At least one or two of them are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof at each occurrence; and / or R 14 -R 16 At least one or two of them are selected, at each occurrence, identically or differently, from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.

12. The metal complex according to claim 1, wherein L a Each occurrence is identically or differently selected from the group consisting of: In the above structure, Et represents an ethyl group; Optionally, the L a1 , L a2 , L a8 , L a29 , L a30 , L a36 , L a114 , L a115 , L a121 , L a141 , L a142 , L a148 , L a179 , L a180 , L a189 , L a190 , L a199 , L a200 , L a209 , L a210 , L a219 , L a220 , L a229 , L a230 , L a239 , L a240 , L a249 , L a250 , L a259 , L a260 , L a269 , L a270 , L a279 , L a288 , L a297 , L a306 , L a492 , L a493 , L a501 , L a502 , L a545 The hydrogen atoms in the structure can be partially or completely replaced by deuterium.

13. The metal complex according to claim 12, wherein L b Each occurrence is identically or differently selected from the group consisting of:

14. The metal complex according to claim 13, wherein The metal complex has Ir(L a )2(L b ) structure; Among them, L a Each time it appears, choose the same or different one from L a1 , L a2 , L a8 , L a29 , L a30 , L a36 , L a114 , L a115 , L a121 , L a141 , L a142 , L a148 , L a179 , L a180 , L a189 , L a190 , L a199 , L a200 , L a209 , L a210 , L a219 , L a220 , L a229 , L a230 , L a239 , L a240 , L a249 , L a250 , L a259 , L a260 , L a269 , L a270 , L a279 , L a288 , L a297 , L a306 , L a492 , L a493 , L a501 , L a502 , L a545 Any one or two of the group consisting of L b Choose from L b1 To L b235 , L b268 To L b322 Any of the groups consisting of.

15. The metal complex of claim 14, wherein the metal complex is selected from the group consisting of Compound 1, Compound 4, Compound 9, Compound 11, Compound 13, Compound 14, Compound 20, Compound 21, Compound 24, Compound 29, Compound 31, Compound 33, Compound 34, Compound 40, Compound 41, Compound 44, Compound 49, Compound 51, Compound 53, Compound 54, Compound 60, Compound 61, Compound 64, Compound 69, Compound 71, Compound 73, Compound 74, Compound 80, Compound 81, Compound 84, Compound 89, Compound 91, Compound 93, Compound 94, Compound 100, Compound 101, Compound 104, Compound 109, Compound 111, Compound 112 3. Compound 114, compound 120, compound 121, compound 124, compound 129, compound 131, compound 133, compound 134, compound 140, compound 161, compound 164, compound 169, compound 171, compound 173, compound 174, compound 180, compound 181, compound 184, compound 189, compound 191, compound 193, compound 194, compound 200, compound 201, compound 205, compound 208, compound 213, compound 217, compound 220, compound 225, compound 229, compound 232, compound 237, compound 241, compound 244, compound 249, compound 253, and compound 256; wherein compound 1, compound 4, compound 9, compound 11, compound 13, compound 14, compound 20, compound 21, compound 24, compound 29, compound 31, compound 33, compound 34, compound 40, compound 41, compound 44, compound 49, compound 51, compound 53, compound 54, compound 60, compound 61, compound 64, compound 69, compound 71, compound 73, compound 74, compound 80, compound 81, compound 84, compound 89, compound 91, compound 93, compound 94, Compound 100, Compound 101, Compound 104, Compound 109, Compound 111, Compound 113, Compound 114, Compound 120, Compound 121, Compound 124, Compound 129, Compound 131, Compound 133, Compound 134, Compound 140, Compound 161, Compound 164, Compound 169, Compound 171, Compound 173, Compound 174, Compound 180, Compound 181, Compound 184, Compound 189, Compound 191, Compound 193, Compound 194 and Compound 200 have Ir(L a )2(L b ) structure, where two L a Same, L a and L b The corresponding structures are selected from the following table: in, Compound 201, Compound 205, Compound 208, Compound 213, Compound 217, Compound 220, Compound 225, Compound 229, Compound 232, Compound 237, Compound 241, Compound 244, Compound 249, Compound 253, Compound 256 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b The corresponding structures are selected from the following table:

16. An electroluminescent device comprising: anode, cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex according to any one of claims 1 to 15.

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

18. The electroluminescent device of claim 16, wherein: The device emits red light or white light.

19. The electroluminescent device of claim 17, wherein: The light-emitting layer also includes at least one host material.

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

21. A compound combination comprising the metal complex according to any one of claims 1 to 15.

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