Organic electroluminescent material and device thereof

Abstract

Organic electroluminescent materials and devices thereof are disclosed. The organic electroluminescent material is a metal complex containing a La ligand with a structure as shown in a formula 1. When the novel metal complexes are applied to an electroluminescent device, the half-peak width and the capacitance of the device can be reduced, the response time and the refresh frequency of an OLED display device at a low gray scale can be improved by the organic electroluminescent device, excellent device performance can be kept, the comprehensive performance of the device can be improved, and the application prospect is wide. The method has huge advantages and wide prospects in industrial application. Also disclosed are an organic electroluminescent device comprising the metal complex and a composition comprising the metal complex.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound L comprising a structure of formula 1 a The invention relates to a metal complex of a ligand, an organic electroluminescent device comprising the metal complex and a compound composition comprising 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 Ebx van Slyke is a fluorescent OLED. It uses only singlet states to emit light. The triplet states 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 used triplet emission from heavy metals containing complexes as emitters. Therefore, singlets 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 states to singlet states. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs 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] From the perspective of electronics, the display principle of OLED is that under the action of an external electric field greater than a certain threshold, holes and electrons are injected from the anode and cathode in the form of current into the organic thin film light-emitting layer sandwiched between the anode and cathode, and the two combine to form excitons, which undergo radiation recombination and cause light emission. Since the organic light-emitting film has a very obvious capacitance characteristic, the capacitance of the organic light-emitting film layer is a key factor affecting the response time and refresh rate of OLED display devices at low grayscales.

[0009] CN111655705A discloses a metal complex having the structure shown below: Where R 5 is selected from halogen, nitrile, nitro, etc., substituted or unsubstituted alkyl having 3 to 30 carbon atoms, etc., R 4 Selected from hydrogen, deuterium, halogen and many other groups, and further discloses the following specific structure: This application does not disclose or teach that R 5 is a substituent having a total number of carbon atoms greater than or equal to 2, and R at a specific position 4 The invention discloses a metal complex when the metal complex is an aromatic group or a heteroaromatic group and the influence of the metal complex on the device performance.

[0010] US20210403496A1 discloses a phosphorescent metal complex having the structure shown below: wherein Ar is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof; X 4 Selected from CR x or N, R x Selected from hydrogen, deuterium, halogen and many other groups, and further discloses the following specific structure: This application does not disclose or teach that X in the metal complex 4 Selected from CR x , and R x A metal complex when the substituent has a total carbon atom count greater than or equal to 2 and the influence of the metal complex on device performance. Summary of the invention

[0011] The present invention aims to provide a series of L comprising the structure of formula 1 a The metal complexes of ligands can solve at least part of the above problems. These new metal complexes can be used in electroluminescent devices to significantly reduce the half-peak width and capacitance of the device, which is beneficial to improving the overall performance of the device.

[0012] According to one embodiment of the present invention, a metal complex comprises a metal M and a ligand L coordinated with the metal M. a , La Having a structure represented by Formula 1:

[0013]

[0014] in,

[0015] Cy is selected from the group consisting of Y 1 , Y 2 An aromatic ring having 6 to 24 ring atoms, comprising Y 1 , Y 2 A heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0016] G 1 and G 2 is selected identically or differently at each occurrence from a single bond, O or S;

[0017] X 1 -X 3 Each occurrence is selected from C, CR, either identically or differently x or N;X 1 -X 3 One of them is selected from C and is matched with Y 2 connected;

[0018] G 2 Selected from single bonds, X 1 , X 2 or X 3 When selected from N, the X 1 , X 2 or X 3 By G 2 Forming a metal-nitrogen bond to the metal; or G 2 is selected from a single bond, O or S, X 1 , X 2 or X 3 When selected from C, the X 1 , X 2 or X 3 By G 2 Connected to metal;

[0019] Y 1 and Y 2 is selected identically or differently at each occurrence from C or N;

[0020] Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;

[0021] R y indicates single substitution, multiple substitution, or no substitution; when there are multiple R y When the R ySame or different;

[0022] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0023] R n It has a structure represented by formula 2:

[0024]

[0025] R n The number of carbon atoms is greater than or equal to 2;

[0026] “*” indicates the connection position between Formula 2 and Formula 1;

[0027] R x , R y , R', R 1 , R 2 and R 3 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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;

[0028] Adjacent substituent R y can optionally be linked to form a ring;

[0029] Adjacent substituent R x and R' can be optionally linked to form a ring;

[0030] Adjacent substituent R 1 , R 2 and R 3 Can optionally be linked to form a ring.

[0031] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers includes the metal complex described in the above embodiment.

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

[0033] The present invention aims to provide a series of L comprising the structure of formula 1 a The metal complexes of the ligands can solve at least part of the above problems. These new metal complexes can be applied to electroluminescent devices to reduce the half-peak width and capacitance of the device. The organic electroluminescent device can improve the response time and refresh rate of the OLED display device at low gray scales, and can maintain excellent device performance, which is conducive to improving the comprehensive performance of the device. The metal complexes have great advantages and broad prospects in industrial applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 Schematic diagram of an organic light-emitting device that may contain the metal complex disclosed herein and the compound composition containing the metal complex.

[0035] Figure 2 is another schematic diagram of an organic light-emitting device that may contain the metal complex disclosed herein and the compound composition comprising the metal complex. DETAILED DESCRIPTION

[0036] 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 can 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.

[0037] 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 one doped with F at a molar ratio of 50:1. 4

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] 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 a metal such as Mg:Ag and 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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).

[0047] 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.

[0048] 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).

[0049] Definition of Substituent Terms

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

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] Aryl or aromatic group - As used herein, 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, phenanthrene, indene, 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.

[0057] Heterocyclic group - as used herein, non-aromatic cyclic groups are considered. Non-aromatic heterocyclic groups include saturated heterocyclic groups with 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups with 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 with 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 oxirane, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azacycloheptinyl and tetrahydrothioxyl. In addition, the heterocyclic group may be optionally substituted.

[0058] 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.

[0059] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. 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.

[0060] 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.

[0061] 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,

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or at least two CH 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 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.

[0067] 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 carboxyl, The acid group, substituted ester group, substituted sulfinyl group, refers to any one of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, an alkylgermanyl group, an arylgermanyl group, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a sulfinyl group, a sulfonyl group and a phosphino group, which may be substituted by one or at least two of the following: deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted alkyl group having 3 to 20 carbon atoms. unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 carbon 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 3-30 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.

[0068] 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.

[0069] 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.

[0070] In the compounds mentioned in the present disclosure, multiple substitution 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 multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0071] 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.

[0072] 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:

[0073]

[0074] 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:

[0075]

[0076] 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:

[0077]

[0078] 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:

[0079]

[0080] According to one embodiment of the present invention, a metal complex comprises a metal M and a ligand L coordinated with the metal M. a , L a Having a structure represented by Formula 1:

[0081]

[0082] in,

[0083] Cy is selected from the group consisting of Y 1 , Y 2 An aromatic ring having 6 to 24 ring atoms, comprising Y 1 , Y 2 A heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0084] G 1 and G 2 is selected identically or differently at each occurrence from a single bond, O or S;

[0085] X 1 -X 3 Each occurrence is selected from C, CR, either identically or differently x or N;X 1 -X 3 One of them is selected from C and is matched with Y 2 connected;

[0086] G 2 Selected from single bonds, X 1 , X 2 or X 3 When selected from N, the X 1 , X 2 or X 3 By G 2 Forming a metal-nitrogen bond to the metal; or G 2 is selected from a single bond, O or S, X 1 , X 2 or X 3 When selected from C, the X 1 , X 2 or X 3 By G 2 Connected to metal;

[0087] Y 1 and Y 2 is selected identically or differently at each occurrence from C or N;

[0088] Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;

[0089] R y indicates single substitution, multiple substitution, or no substitution; when there are multiple R y When the R y Same or different;

[0090] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0091] R n It has a structure represented by formula 2:

[0092]

[0093] R n The number of carbon atoms is greater than or equal to 2;

[0094] “*” indicates the connection position between Formula 2 and Formula 1;

[0095] R x , R y , R', R 1 , R 2 and R 3 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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;

[0096] Adjacent substituent R y can optionally be linked to form a ring;

[0097] Adjacent substituent R x and R' can be optionally linked to form a ring;

[0098] Adjacent substituent R 1 , R 2 and R 3 Can optionally be linked to form a ring.

[0099] In this paper, when G 1 When selected from a single bond, it means Y 1 Directly connected to metal M; when G 2 When selected from a single bond, it means that X 1 , X 2 or X 3 Directly connected to metal M.

[0100] In this context, “the adjacent substituent R y "can optionally be linked to form a ring" is intended to mean that the adjacent substituents R y Any one or more of the groups can be optionally connected to form a ring. Obviously, none of these substituents can be connected to form a ring.

[0101] In this context, “the adjacent substituent R x and R' can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example two substituents R x Between two substituents R', between substituents R x Between R and R', any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring.

[0102] In this context, “the adjacent substituent R 1 , R 2 and R 3 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, such as substituents R 1 and R 2 Between, the substituent R 1 and R 3 Between, the substituent R 3 and R 2 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.

[0103] According to one embodiment of the present invention, wherein Cy appears each time in the same or different manner and is selected from any structure in the group consisting of:

[0104]

[0105] in,

[0106] R yEach occurrence of the same or different represents mono-, poly-, or unsubstituted; when multiple R y When the R y Same or different;

[0107] R y 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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;

[0108] Adjacent substituent R y can optionally be linked to form a ring;

[0109] Wherein, “#” indicates the position connected to the metal M. Indicates that X 1 , X 2 or X 3 The location of the connection.

[0110] According to one embodiment of the present invention, the metal complex has M(L a ) m (L b ) n (L c ) q The general formula of

[0111] M is selected from metals with a relative atomic mass greater than 40; preferably, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, either identically or differently;

[0112] L a , L b and Lc are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand;

[0113] m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a The same or different; when n is equal to 2, the two L b The same or different; when q is equal to 2, the two L c Same or different;

[0114] L b and L c Each occurrence is identically or differently selected from any one of the following groups:

[0115]

[0116]

[0117] in,

[0118] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;

[0119] R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0120] R a , R b , R c , R N1 , R C1 and R C2The 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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;

[0121] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0122] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b 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 C2Between, the substituent R b and R C1 Between, the substituent R b and R C2 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. For example, The adjacent substituent R a , R b can be optionally linked to form a ring, when R a When optionally linked to form a ring, Can be formed structure.

[0123] According to one embodiment of the present invention, G 1 and G 2 is selected identically or differently on each occurrence from a single bond or O.

[0124] According to one embodiment of the present invention, G 1 and G 2 It is a single bond.

[0125] According to one embodiment of the present invention, the metal complex has Ir(L a ) m (L b ) 3-m The general structure of the formula 3 is:

[0126]

[0127] in,

[0128] m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different;

[0129] Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;

[0130] U 1 -U 8 Each occurrence is selected from CR u or N;

[0131] X 3 -X 6 Each occurrence is selected from CR x or N;

[0132] Y 3 -Y 6 Each occurrence is selected from CR y or N;

[0133] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0134] R n It has a structure represented by formula 2:

[0135]

[0136] R n The number of carbon atoms is greater than or equal to 2;

[0137] “*” indicates the connection position between Formula 2 and Formula 3;

[0138] R'、R u , R x , R y , R 1 , R 2 and R 3 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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;

[0139] Adjacent substituent R y can optionally be linked to form a ring;

[0140] Adjacent substituent R x and R' can be optionally linked to form a ring;

[0141] Adjacent substituent R u can optionally be linked to form a ring;

[0142] Adjacent substituent R 1 , R 2 and R 3 Can optionally be linked to form a ring.

[0143] In this context, “the adjacent substituent R u "can optionally be linked to form a ring" is intended to mean that the adjacent substituents R u Any one or more of the groups can be optionally connected to form a ring. Obviously, none of these substituents can be connected to form a ring.

[0144] According to one embodiment of the present invention, m is selected from 1 or 2.

[0145] According to one embodiment of the present invention, m is selected from 1.

[0146] According to one embodiment of the present invention, R 1 , R 2 and R 3 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 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, cyano, and combinations thereof; and R 1 , R 2 and R 3 The sum of carbon atoms is greater than or equal to 1.

[0147] According to one embodiment of the present invention, R 1 , R 2 and R 3 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 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, cyano, and combinations thereof; and R 1 , R 2 and R 3 At least one of them is 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, and combinations thereof.

[0148] According to one embodiment of the present invention, R 1 , R 2 and R 3 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations thereof; and R 1 , R 2 and R 3 The sum of carbon atoms is greater than or equal to 1.

[0149] According to one embodiment of the present invention, R 1 , R 2 and R 3 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations thereof; and R 1 , R 2 and R 3 At least one of them is selected from substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, and combinations thereof.

[0150] According to one embodiment of the present invention, R 1 , R 2 and R 3 Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, and combinations thereof; and R 1 , R 2 and R 3 At least one of them is selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0151] According to one embodiment of the present invention, R 1 , R 2 and R 3 is selected, at each occurrence, identically or differently, from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms; and R 1 , R 2 and R 3 Not connected to form a ring or R 1 , R 2 and R 3 There are two connections in the loop. For example, R 1 , R 2 and R 3 Two of them are connected to form a substituted or unsubstituted cycloalkyl group.

[0152] According to one embodiment of the present invention, R 1 , R 2 and R 3 At least one of them is selected from hydrogen or deuterium.

[0153] According to one embodiment of the present invention, R 1 , R 2 and R 3 One of them is selected from hydrogen or deuterium.

[0154] According to one embodiment of the present invention, R 1 , R 2 and R 3 Two of them are selected from hydrogen or deuterium.

[0155] According to one embodiment of the present invention, R n Each occurrence is identically or differently selected from the group consisting of:

[0156]

[0157]

[0158] Optionally, the above R n The hydrogen in the ion can be partially or completely replaced by deuterium.

[0159] According to one embodiment of the present invention, X 3 -X 6 Each occurrence is selected from CR x .

[0160] According to one embodiment of the present invention, X 3 -X 6 Each occurrence is selected from CR x or N, and X 3 -X 6 At least one of them is N, for example, X 3 -X 6 One of N or X 3 -X 6 Two of them are selected from N.

[0161] According to one embodiment of the present invention, Y 3 -Y 6 Each occurrence is selected from CR y .

[0162] According to one embodiment of the present invention, Y 3 -Y 6 Each occurrence is selected from CR yor N, and Y 3 -Y 6 At least one of them is N, for example, Y 3 -Y 6 One of N or Y 3 -Y 6 Two of them are selected from N.

[0163] According to one embodiment of the present invention, U 1 -U 8 Each occurrence is selected from CR u .

[0164] According to one embodiment of the present invention, U 1 -U 8 Each occurrence is selected from CR u or N, and U 1 -U 8 At least one of them is N, for example, U 1 -U 8 One of N or U 1 -U 8 Two of them are selected from N, or U 1 -U 4 One of N, or U 5 -U 8 One of them is selected from N.

[0165] According to one embodiment of the present invention, R x 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 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 alkylgermanyl having 3-20 carbon atoms, cyano, and combinations thereof.

[0166] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, cyano, and combinations thereof.

[0167] According to one embodiment of the present invention, Rx Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

[0168] According to one embodiment of the present invention, R y 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 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 alkylgermanyl having 3-20 carbon atoms, cyano, and combinations thereof.

[0169] According to one embodiment of the present invention, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, cyano, and combinations thereof.

[0170] According to one embodiment of the present invention, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

[0171] According to one embodiment of the present invention, R uEach 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 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 alkylgermanyl having 3-20 carbon atoms, cyano, and combinations thereof.

[0172] According to one embodiment of the present invention, R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, cyano, and combinations thereof.

[0173] According to one embodiment of the present invention, R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

[0174] According to one embodiment of the present invention, X 3 -X 6 At least one of the following is selected from CR x , the R x is cyano or fluorine; and the substituent R n All carbon atoms in the carbon are selected from primary carbon, secondary carbon or tertiary carbon.

[0175] According to one embodiment of the present invention, X 4 -X 6 At least one of the following is selected from CR x , the R x is cyano or fluorine; and the substituent R n All carbon atoms in the carbon are selected from primary carbon, secondary carbon or tertiary carbon.

[0176] According to one embodiment of the present invention, X 6 Yes CR x , the R x is cyano or fluorine; and the substituent Rn All carbon atoms in the carbon are selected from primary carbon, secondary carbon or tertiary carbon.

[0177] According to one embodiment of the present invention, X 3 -X 6 Each occurrence is selected from CR x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, 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 alkylgermanyl having 3 to 20 carbon atoms, and combinations thereof; and the substituent R n At least one of the carbon atoms in a molecule is a quaternary carbon.

[0178] According to one embodiment of the present invention, X 4 -X 6 Each occurrence is selected from CR x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, and combinations thereof; and the substituent R n At least one of the carbon atoms in a molecule is a quaternary carbon.

[0179] According to one embodiment of the present invention, X 6 Yes CR x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof; and the substituent R n At least one of the carbon atoms in a molecule is a quaternary carbon.

[0180] According to one embodiment of the present invention, Y 3 -Y 6 At least one selected from CRy , and the R y 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.

[0181] According to one embodiment of the present invention, Y 3 -Y 6 At least one selected from CR y , and the R y Selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, and combinations thereof.

[0182] According to one embodiment of the present invention, Y 3 -Y 6 At least one selected from CR y , and the R y Selected from the group consisting of deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

[0183] According to one embodiment of the present invention, U 1 -U 8 At least one or at least two selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof; and all of said R u The sum of the number of carbon atoms is at least 4.

[0184] According to one embodiment of the present invention, U 1 -U 4 At least one or at least two selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4.

[0185] According to one embodiment of the present invention, U 5 -U 8 At least one or at least two selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4.

[0186] According to one embodiment of the present invention, Ar is selected from the group consisting of Ar1 to Ar147 each time it appears, the same or different, and the specific structures of Ar1 to Ar147 are shown in claim 15.

[0187] According to one embodiment of the present invention, the hydrogen in Ar1-Ar114, Ar116-Ar126, Ar129, Ar131-Ar136, Ar142-Ar143 and Ar146-Ar147 can be partially or completely replaced by deuterium.

[0188] According to one embodiment of the present invention, L a Each occurrence is selected from L a1 To L a6954 The group consisting of L a1 To L a6954 The specific structure is shown in claim 16.

[0189] According to one embodiment of the present invention, wherein the L a1 To L a6954 The hydrogen in the ion can be partially or completely replaced by deuterium.

[0190] According to one embodiment of the present invention, L b Each occurrence is selected from L b1 To L b158 The group consisting of L b1 To L b158 The specific structure is shown in claim 17.

[0191] According to one embodiment of the present invention, wherein the L b1 To L b18 , L b20 To L b26 and L b31 To L b158 The hydrogen in the ion can be partially or completely replaced by deuterium.

[0192] According to one embodiment of the present invention, the metal complex has Ir(L a ) 3or Ir(L a )(L b ) 2 or Ir(L a ) 2 (L b ) structure, L a Each occurrence is selected from L a1 To L a6954 One, two or three of the group, L b Each occurrence is selected from L b1 To L b158 One or two of the group.

[0193] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 6728, and the specific structures of the metal complex 1 to metal complex 6728 are described in claim 18.

[0194] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex described in any of the above embodiments.

[0195] According to one embodiment of the present invention, the organic layer containing the metal complex is a light-emitting layer.

[0196] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound.

[0197] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound and a second host compound.

[0198] According to one embodiment of the present invention, the first main compound and / or the second main compound contains 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, silylate, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0199] According to one embodiment of the present invention, the first host compound has a structure represented by formula X-1 or X-2:

[0200]

[0201] in,

[0202] L xis selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0203] G is selected, identically or differently, from C(R g ) 2 NR g , O or S;

[0204] Each occurrence of V is selected from C, CR v or N;

[0205] In formula X-1, each occurrence of T is identical or different and is selected from C, CR t or N;

[0206] In formula X-2, each occurrence of T is identically or differently selected from CR t or N;

[0207] R g , R v and R t 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;

[0208] Ar 1 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0209] Adjacent substituent Rg , R v and R t Can optionally be linked to form a ring.

[0210] In this embodiment, "the adjacent substituent R g , R v and R t "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R v Between the two substituents R t Between the two substituents R g Between, the substituent R v and R t Between, the substituent R v and R g Between, the substituent R g and R t 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.

[0211] According to one embodiment of the present invention, the first host compound has a structure represented by one of Formula Xa to Formula Xp:

[0212]

[0213] in,

[0214] L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0215] G is selected, identically or differently, from C(R g ) 2 NR g , O or S;

[0216] Each time V appears, it is selected from CR in the same or different way. v or N;

[0217] Each occurrence of T is selected from CR t or N;

[0218] R g , R v and R tThe 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;

[0219] Ar 1 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0220] Adjacent substituent R g , R v and R t Can optionally be linked to form a ring.

[0221] According to one embodiment of the present invention, the first host compound is selected from the group consisting of the following compounds:

[0222]

[0223]

[0224]

[0225] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 4:

[0226]

[0227] in,

[0228] E 1 -E 6 Each occurrence is selected from C, CR, either identically or differently e or N, and E 1 -E6 At least two of them are N, E 1 -E 6 At least one of them is C and is connected to formula A;

[0229]

[0230] in,

[0231] Q is the same or different each time it appears and is selected from O, S, Se, N, NR Q , CR Q R Q ,SiR Q R Q ,GeR Q R Q and R Q C=CR Q When there are two R Q When two R Q Can be the same or different;

[0232] p is 0 or 1; r is 0 or 1;

[0233] When Q is selected from N, p is 0 and r is 1;

[0234] When Q is selected from O, S, Se, NR Q , CR Q R Q ,SiR Q R Q ,GeR Q R Q and R Q C=CR Q When the group is composed, p is 1 and r is 0;

[0235] L q is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0236] Q 1 -Q 8 Each occurrence is selected from C, CR, either identically or differently q or N;

[0237] R e , R Q and R qEach 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0238] “*” represents the connection position between Formula A and Formula 4;

[0239] Adjacent substituent R e , R Q , R q Can optionally be linked to form a ring.

[0240] In this context, “the adjacent substituent R e , R Q , R q "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R e Between the two substituents R Q Between the two substituents R q Between the two substituents R Q and R q 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.

[0241] According to one embodiment of the present invention, the second host compound is selected from the group consisting of the following compounds:

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248] According to one embodiment of the present invention, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0249] According to one embodiment of the present invention, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

[0250] According to an embodiment of the present invention, the organic electroluminescent device further comprises a hole injection layer, which can be a single material functional layer or a functional layer comprising multiple materials, wherein the multiple materials comprised are most commonly hole transport materials doped with a certain proportion of p-type conductive doping materials. Common p-type doping materials include:

[0251] According to one embodiment of the present invention, a compound composition is also disclosed, which comprises the metal complex described in any of the aforementioned embodiments.

[0252] Combination with other materials

[0253] 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.

[0254] 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 light-emitting dopants disclosed herein can be used in combination with a variety of 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.

[0255] 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.

[0256] Material Synthesis Example

[0257] Synthesis Example 1: Synthesis of Metal Complex 5343

[0258] Step 1: Synthesis of Intermediate 3

[0259]

[0260] In a dry 250 mL round-bottom flask, intermediate 1 (7.7 g, 25.1 mmol), intermediate 2 (5.7 mL, 30.1 mmol), tetrakis(triphenylphosphine)palladium (1.4 g, 1.2 mmol), potassium carbonate (6.9 g, 50.2 mmol), toluene / ethanol / water (5 / 1 / 1, 70.0 mL), N 2Under protection, the reaction was carried out overnight at 110° C. After the reaction was completed, the mixture was extracted with ethyl acetate and purified by column chromatography to obtain a white solid intermediate 3 (6.0 g, 22.4 mmol, 89% yield).

[0261] Step 2: Synthesis of intermediate 4

[0262]

[0263] In a dry 250 mL round-bottom flask, intermediate 3 (10.0 g, 37.4 mmol), bis-pinacol borate (10.4 g, 41.1 mmol), potassium acetate (7.3 g, 74.8 mmol), palladium acetate (0.4 g, 1.9 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.8 g, 3.7 mmol) and 1,4-dioxane (100.0 ml) were added in sequence. 2 Under protection, the reaction was carried out at 100°C overnight. After the reaction was complete, the mixture was filtered through celite and concentrated under reduced pressure to obtain intermediate 4, which was directly used in the next step.

[0264] Step 3: Synthesis of Intermediate 5

[0265]

[0266] In a dry 250 mL round-bottom flask, the intermediate 4,2-bromopyridine (5.9 g, 37.4 mmol), potassium carbonate (10.3 g, 74.8 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.4 g, 1.9 mmol), 1,4-dioxane / water (90 mL / 30 mL) mixed solvent, N 2 Under protection, the reaction was carried out at 100° C. overnight. After the reaction was completed, the mixture was extracted with dichloromethane and purified by column chromatography to obtain a white solid intermediate 5 (8.8 g, 28.4 mmol, 76% yield (two steps)).

[0267] Step 4: Synthesis of intermediate 6

[0268]

[0269] A dry 250 mL round-bottom flask was charged with intermediate 5 (7.0 g, 22.5 mmol), ethyl acetate (70 mL), ammonium formate (7.1 g, 112.9 mmol), Pd / C (10%, 1.2 g), N 2 Under protection, the reaction was carried out at room temperature overnight. After the reaction was completed, the mixture was filtered through celite, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate 6 (2.4 g, 7.6 mmol, 34%).

[0270] Step 5: Synthesis of Intermediate 7

[0271]

[0272] In a dry 250 mL three-necked round-bottom flask, intermediate 6 (2.4 g, 7.6 mmol) and tetrahydrofuran (30 mL) were added. 2 Under protection, cooled to -70°C, 2.0M lithium diisopropylamide tetrahydrofuran solution (6 mL) was slowly added dropwise to the reaction system, reacted at -70°C for 1.5 hours, N-fluorobisbenzenesulfonamide (4.8 g, 15.3 mmol) was added, and reacted at room temperature until the reaction was complete. The reaction solution was quenched with a small amount of water, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate 7 (2.2 g, 6.6 mmol, 87% yield).

[0273] Step 6: Synthesis of Intermediate 8

[0274]

[0275] In a dry 100 mL round-bottom flask, intermediate 7 (2.2 g, 6.6 mmol), deuterated carbazole (1.4 g, 8.0 mmol), potassium tert-butoxide (1.0 g, 9.3 mmol), DMF (30 mL), N 2 Under protection, the reaction was carried out at 100°C overnight. After the reaction was completed, the reaction was concentrated under reduced pressure and purified by column chromatography to obtain a white solid intermediate 8 (2.3 g, 4.7 mmol, 72% yield).

[0276] Step 7: Synthesis of Metal Complex 5343

[0277]

[0278] In a dry 250 mL round-bottom flask, intermediate 9 (1.1 g, 1.2 mmol), intermediate 8 (0.7 g, 1.5 mmol), 2-ethoxyethanol (20 mL) and DMF (20 mL) were added in sequence. 2 Under protection, the reaction was heated at 100°C for 5 days. After the reaction was cooled, it was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 5343 (0.63 g, 0.52 mmol, 43% yield). The product was determined to be the target product with a molecular weight of 1209.6.

[0279] Synthesis Example 2: Synthesis of Metal Complex 3525

[0280]

[0281] In a dry 250 mL round-bottom flask, intermediate 3 (2.0 g, 2.4 mmol), intermediate 2 (1.4 g, 2.9 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence. 2 Under protection, the reaction was heated at 100°C for 5 days. After the reaction was cooled, it was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 3525 (1.2 g, 1.09 mmol, 46% yield). The product was determined to be the target product with a molecular weight of 1097.4.

[0282] Synthesis Example 3: Synthesis of Metal Complex 5291

[0283] Step 1: Synthesis of intermediate 11

[0284]

[0285] A 1.3 M cyclohexylmagnesium chloride tetrahydrofuran solution (9 mL) was added to a dry 100 mL three-necked round-bottom flask. 2 After 1 hour of reaction, add 2.0M zinc chloride tetrahydrofuran solution (3mL) to the system, add intermediate 1 (2.0g, 6.5mmol), palladium acetate (0.07g, 0.3mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.27g, 0.6mmol) to the system, and react overnight at room temperature. After the reaction is complete, extract with ethyl acetate and purify by column chromatography to obtain white solid intermediate 11 (1.3g, 4.2mmol, 65% yield).

[0286] Step 2: Synthesis of intermediate 12

[0287]

[0288] In a dry 100 mL round-bottom flask, intermediate 11 (1.3 g, 4.2 mmol), bis-pinacol borate (1.2 g, 4.6 mmol), potassium acetate (0.8 g, 8.4 mmol), palladium acetate (0.05 g, 0.2 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.2 g, 0.4 mmol) and 1,4-dioxane (30.0 mL) were added in sequence. Under nitrogen protection, the reaction was carried out at 100 ° C overnight. After the reaction was complete, the mixture was filtered through celite and concentrated under reduced pressure to obtain intermediate 12, which was directly used in the next step.

[0289] Step 3: Synthesis of intermediate 13

[0290]

[0291] In a dry 100 mL round-bottom flask, intermediate 12, 2-bromopyridine (0.7 g, 4.2 mmol), potassium carbonate (1.2 g, 8.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (0.15 g, 0.2 mmol), 1,4-dioxane / water (30 mL / 10 mL) mixed solvent were added in sequence, and reacted at 100 ° C overnight under nitrogen protection. After the reaction was complete, dichloromethane was extracted and purified by column chromatography to obtain a white solid intermediate 13 (1.0 g, 2.8 mmol, 67% yield (two steps)).

[0292] Step 4: Synthesis of intermediate 14

[0293]

[0294] Add intermediate 13 (1.0 g, 2.8 mmol) and tetrahydrofuran (30 mL) to a dry 100 mL three-necked round-bottom flask, cool to -70 ° C under nitrogen protection, slowly add 2.0 M lithium diisopropylamide tetrahydrofuran solution (2 mL) to the reaction system, react at -70 ° C for 1.5 hours, add 2.0 M zinc chloride tetrahydrofuran solution (1 mL), warm to room temperature, continue to react for 0.5 hours, add deuterated iodobenzene (1.2 g, 5.7 mmol), palladium acetate (0.03 g, 0.14 mmol), 2-dicyclohexylphosphine-2', 6'-dimethoxy-biphenyl (0.12 g, 0.28 mmol), and react at room temperature overnight. After the reaction is complete, the reaction solution is quenched with a small amount of water, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate 7 (0.7 g, 1.6 mmol, 58% yield).

[0295] Step 5: Synthesis of Metal Complex 5291

[0296]

[0297] In a dry 250 mL round-bottom flask, intermediate 1 (1.0 g, 1.1 mmol), intermediate 14 (0.6 g, 1.4 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence. 2 Under protection, the reaction was heated at 100°C for 5 days. After the reaction was cooled, it was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 5291 (0.6 g, 0.52 mmol, 48% yield). The product was determined to be the target product with a molecular weight of 1157.6.

[0298] 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.

[0299] Device Example 1

[0300] First, a glass substrate was cleaned with an 80 nm thick indium tin oxide (ITO) anode (with a sheet resistance of 14-20 Ω / sq and a light emitting area of ​​0.04 cm 2 ), 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 by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HT and compound PD are used as hole injection layer (HIL). Compound HT is used as hole transport layer (HTL). Compound PH-23 is used as electron blocking layer (EBL). Then the metal complex 5343 of the present invention is doped in compound PH-23 and compound H-40 and co-deposited as light-emitting layer (EML). On EML, compound HB is used as hole blocking layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as electron injection layer, and 120 nm of aluminum is evaporated 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.

[0301] Device Example 2

[0302] Device Example 2 was carried out in the same manner as Device Example 1, except that the metal complex 3525 was used in place of the inventive metal complex 5343 in the light emitting layer (EML).

[0303] Device Example 3

[0304] Device Example 3 was carried out in the same manner as Device Example 1, except that the metal complex 5291 was used in place of the metal complex 5343 of the present invention in the light emitting layer (EML).

[0305] Device Comparison Example 1

[0306] The implementation of Comparative Device Example 1 is the same as that of Example 1, except that the metal complex 5343 of the present invention is replaced by Compound GD1 in the light emitting layer (EML).

[0307] Device Comparison Example 2

[0308] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that the metal complex 5343 of the present invention is replaced by Compound GD2 in the light emitting layer (EML).

[0309] Device Comparison Example 3

[0310] The implementation of Comparative Device Example 3 is the same as that of Device Example 1, except that the metal complex 5343 of the present invention is replaced by compound GD3 in the light emitting layer (EML).

[0311] Device Comparison Example 4

[0312] The implementation of Comparative Device Example 4 is the same as that of Example 1, except that the metal complex 5343 of the present invention is replaced by compound GD4 in the light emitting layer (EML).

[0313] 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.

[0314] Table 1 Device structures of Examples 1-3 and Comparative Examples 1-4

[0315]

[0316] The material structure used in the device is shown below:

[0317]

[0318]

[0319] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured under max ), full width at half maximum (FWHM). The device was tested for capacitance using an impedance analyzer (Keysight E4990A): a DC bias of -4V to 5V was applied to the electrodes at both ends of the device, and a 100mV sinusoidal AC voltage signal was superimposed, and the device was tested under an AC voltage with a frequency of 500Hz. The CV curve of the device was measured, and the maximum capacitance of the device (C max ), these data are recorded and shown in Table 2.

[0320] Table 2 Device data of Examples 1-3 and Comparative Examples 1-4

[0321]

[0322] discuss:

[0323] Example 1 has the same L as Comparative Example 1. b ligands, which differ only in L a Ligand R n The substituents are isopropyl and deuterated methyl with carbon atoms greater than 2. From the data in Table 2, it can be seen that at 15 mA / cm 2The half-peak width of Example 1 is narrower by 7.8 nm compared with that of Comparative Example 1; at a frequency of 500 Hz, the maximum capacitance C max 0.69nF lower.

[0324] Example 2 has the same L as Comparative Example 2. b ligands, which differ only in L a Ligand R n The substituents are isopropyl and hydrogen with carbon atoms greater than 2. From the data in Table 2, it can be seen that at 15 mA / cm 2 The half-peak width of Example 2 is 4.5 nm narrower than that of Comparative Example 2; at a frequency of 500 Hz, the maximum capacitance C max 0.54nF lower.

[0325] Example 2 has the same L as Comparative Example 3. b ligand, which differs from L a Ligand R n The substituents are isopropyl and hydrogen with carbon atoms greater than 2, and L a The Ar substituents in the ligand are deuterated carbazole substituents and deuterium. n When both Ar and Ar do not meet the requirements of this application, at 15 mA / cm 2 The half-peak width of Example 2 is narrower by 17.2 nm than that of Comparative Example 3; at a frequency of 500 Hz, the maximum capacitance C max 0.46nF lower.

[0326] Example 3 has the same L as Comparative Example 4. b ligands, which differ only in L a Ligand R n The substituents are cyclohexyl and deuterated methyl groups with carbon atoms greater than 2. 2 The half-peak width of Example 3 is narrower by 10.5 nm than that of Comparative Example 4; at a frequency of 500 Hz, the maximum capacitance C max 0.46nF lower.

[0327] The above data show that the present invention provides a n Compared with the metal complex of La ligand with Ar substituent, the comparative example without the characteristics of the present invention can obtain a narrower half-peak width and a lower maximum capacitance. The organic electroluminescent device can improve the response time and refresh rate of the OLED display device at low gray scales and maintain excellent device performance.

[0328] 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 comprising a metal M and a ligand L coordinated to the metal M a , L a Having a structure represented by Formula 1: in, Cy is selected from an aromatic ring containing Y1 and Y2 having 6 to 24 ring atoms, a heteroaromatic ring containing Y1 and Y2 having 5 to 24 ring atoms, or a combination thereof; G1 and G2 are identically or differently selected at each occurrence from a single bond, O or S; X1-X3 are selected from C, CR in the same or different manner at each occurrence x or N; one of X1-X3 is selected from C and is connected to Y2; When G2 is selected from a single bond, and X1, X2 or X3 is selected from N, the X1, X2 or X3 is connected to the metal through G2 to form a metal-nitrogen bond; or when G2 is selected from a single bond, O or S, and X1, X2 or X3 is selected from C, the X1, X2 or X3 is connected to the metal through G2; X4-X6 are selected from CR in the same or different way each time they appear x or N; Y1 and Y2 are selected, at each occurrence, identically or differently, from C or N; Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different; R y indicates single substitution, multiple substitution, or no substitution; when there are multiple R y When the R y Same or different; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R n It has a structure represented by formula 2: R n The number of carbon atoms is greater than or equal to 2; "*" indicates the connection position between Formula 2 and Formula 1; R x , R y , R', R1, R2 and R3 are each 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituent R y can optionally be linked to form a ring; Adjacent substituent R x and R' can be optionally linked to form a ring; Adjacent substituents R1, R2 and R3 can optionally be linked to form a ring.

2. The metal complex according to claim 1, wherein Each occurrence of Cy is identically or differently selected from any structure in the group consisting of: in, R y Each occurrence of the same or different represents mono-, poly-, or unsubstituted; when multiple R y When the R y Same or different; R y 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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; Adjacent substituent R y can optionally be linked to form a ring; Wherein, "#" indicates the position connected to the metal M, Indicates the location connected to X1, X2, or X3.

3. The metal complex according to claim 1, wherein Metal complexes have M(L a ) m (L b ) n (L c ) q The general formula of M is selected from metals with a relative atomic mass greater than 40; preferably, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, either identically or differently; L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a The same or different; when n is equal to 2, the two L b The same or different; when q is equal to 2, the two L c Same or different; L b and L c Each occurrence is identically or differently selected from any one of the following groups: in, X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ; R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R a , R b , R c , R N1 , R C1 and R C2 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group 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; Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

4. The metal complex according to any one of claims 1 to 3, wherein G1 and G2 are identically or differently selected at each occurrence from a single bond or O; preferably, G1 and G2 are a single bond.

5. The metal complex according to claim 1, wherein The metal complex has Ir(L a ) m (L b ) 3-m The general structure of the formula 3 is: in, m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different; Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different; U1-U8 are selected from CR in the same or different way each time they appear. u or N; X3-X6 are selected from CR in the same or different way each time they appear x or N; Each occurrence of Y3-Y6 is identical or different and is selected from CR y or N; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R n It has a structure represented by formula 2: R n The number of carbon atoms is greater than or equal to 2; "*" indicates the connection position between Formula 2 and Formula 3; R'、R u , R x , R y , R1, R2 and R3 are each 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R y can optionally be linked to form a ring; Adjacent substituent R x and R' can be optionally linked to form a ring; Adjacent substituent R u can optionally be linked to form a ring; Adjacent substituents R1, R2 and R3 can optionally be linked to form a ring.

6. The metal complex according to claim 5, wherein m is selected from 1 or 2; preferably, m is selected from 1.

7. The metal complex according to any one of claims 1 to 6, wherein Z is selected from O or S; preferably, Z is selected from O.

8. The metal complex according to claim 1, wherein R1, R2 and R3 are each 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 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, cyano, and combinations thereof; and the sum of the carbon atoms of R1, R2 and R3 is greater than or equal to 1; Preferably, R1, R2 and R3 are selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations thereof at each occurrence; and the sum of carbon atoms of R1, R2 and R3 is greater than or equal to 1; More preferably, R1, R2 and R3 are selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and combinations thereof at each occurrence, the same or different; and at least one of R1, R2 and R3 is selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

9. The metal complex according to any one of claims 1 to 5, wherein R n Each time it occurs, choose the same or different one from R n1 To R n85 Groups composed of: Optionally, the R n1 To R n85 The hydrogen in the ion can be partially or completely replaced by deuterium.

10. The metal complex according to claim 5, wherein X3-X6 are selected from CR in the same or different way each time they appear x , and / or Y3-Y6 are selected from CR y , and / or U1-U8 are selected from CR in the same or different manner each time they appear u ; R x , R y and R u 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 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 alkylgermanyl having 3 to 20 carbon atoms, cyano, and combinations thereof; Preferably, R x , R y and R u each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, cyano, and combinations thereof; More preferably, R x , R y and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

11. The metal complex according to any one of claims 1 to 5, wherein At least one of X3-X6 is selected from CR x , the R x is cyano or fluorine; and the substituent R n All carbon atoms in are selected from primary carbon, secondary carbon or tertiary carbon; Preferably, at least one of X4-X6 is selected from CR x , the R x is cyano or fluorine; and the substituent R n All carbon atoms in are selected from primary carbon, secondary carbon or tertiary carbon; More preferably, X6 is CR x , the R x is cyano or fluorine; and the substituent R n All carbon atoms in the carbon are selected from primary carbon, secondary carbon or tertiary carbon.

12. The metal complex according to any one of claims 1 to 5, wherein X3-X6 are selected from CR in the same or different way each time they appear x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, 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 alkylgermanyl having 3 to 20 carbon atoms, and combinations thereof; and the substituent R n At least one of the carbon atoms in the molecule is a quaternary carbon. Preferably, X4-X6 are selected from CR x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 12 carbon atoms, and combinations thereof; and the substituent R n At least one of the carbon atoms in the molecule is a quaternary carbon. More preferably, X6 is CR x , the R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof; and the substituent R n At least one of the carbon atoms in a molecule is a quaternary carbon.

13. The metal complex according to claim 5, wherein Each occurrence of Y3-Y6 is CR y or N, and at least one of Y3-Y6 is selected from CR y , and the R y 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; Preferably, at least one of Y3-Y6 is selected from CR y , and the R y Selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, and combinations thereof.

14. The metal complex according to claim 5, wherein At least one or at least two of U1-U8 are selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof; and all of said R u The sum of the number of carbon atoms is at least 4; Preferably, at least one or at least two of U1-U4 and / or U5-U8 are selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4.

15. The metal complex according to any one of claims 1 to 5, wherein Ar is selected, at each occurrence, identically or differently, from the group consisting of Ar1 to Ar147: Optionally, the "*" in Ar1 to Ar147 represents the connection position of Formula 1 or Formula 3; the hydrogen in Ar1-Ar114, Ar116-Ar126, Ar129, Ar131-Ar136, Ar142-Ar143 and Ar146-Ar147 can be partially or completely replaced by deuterium.

16. The metal complex according to claim 1, wherein L a Each occurrence is selected from L a1 -L a6954 Groups composed of: in, L a1 -L a6954 It has the following structure: Where R n , R x4 , R x5 , R x6 ,Ar,R y3 -R y6 An atom or group selected from the following table: Optionally, the ligand L a1 To L a6954 The hydrogen in can optionally be partially or completely replaced by deuterium.

17. The metal complex according to claim 5 or 16, wherein L b Each occurrence is identically or differently selected from the group consisting of: Optionally, the L b1 To L b18 , L b20 To L b26 and L b31 To L b158 The hydrogen in the ion can be partially or completely replaced by deuterium.

18. The metal complex according to claim 17, wherein The metal complex has Ir(L a )(L b )2 structure, where two L b Same or different; L a Each occurrence is selected from L a1 To L a6954 In the group composed of b Each occurrence is selected from L b1 To L b158 One or two of the groups that make up the group; Preferably, the metal complex is selected from the group consisting of metal complex 1 to metal complex 6728, wherein metal complex 1 to metal complex 6728 have Ir(L a )(L b )2 structure, where two L b Same; L a and L b They correspond to the structures in the following table: Optionally, hydrogen in the metal complexes 1 to 6728 can be partially or completely replaced by deuterium.

19. An organic electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex according to any one of claims 1 to 18.

20. The organic electroluminescent device according to claim 19, wherein: The organic layer including the metal complex is a light-emitting layer.

21. The organic electroluminescent device according to claim 20, wherein: The light-emitting layer further comprises a first host compound or further comprises a first host compound and a second host compound; Preferably, the first host compound and / or the second 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, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

22. The organic electroluminescent device according to claim 21, wherein: The metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer; Preferably, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

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

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