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 shown in a formula 1 and an Lb ligand with a structure shown in a formula 2. When the novel metal complexes are applied to electroluminescent devices, more saturated green light emission and lower efficiency roll-off can be obtained, more choices are provided for application of phosphorescent OLED materials and devices in high-brightness scenes, meanwhile, the metal complexes have lower device capacitance in the devices, and the application range of the metal complexes is widened. And the response rate of the OLED display device at a low gray scale can be improved, and the refresh frequency of the device can be improved. The metal complex 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 use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound comprising a structure of formula 1 a The ligand and L of the structure of formula 2 b 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] CN105980519A discloses a compound M(L) n (L') m , where M(L) n The section has the following structure: CyD and / or CyC contain two adjacent carbon atoms which are substituted by a group R which forms a ring with the carbon atoms: The following specific structure is further disclosed: This application does not teach that the ligand L' is a compound having a polyvalent condensed aromatic ring structure with specific substituents and the effect of the compound on the device performance. Summary of the invention

[0010] The present invention aims to provide a series of L comprising the structure of formula 1 a The ligand and L of the structure of formula 2 b The metal complexes of ligands can solve at least some of the above problems. These new metal complexes can be used in electroluminescent devices to obtain more saturated green light emission, lower efficiency roll-off at high brightness, and response rate at low grayscale. Improving the refresh rate of the device is beneficial to improving the overall performance of the device.

[0011] According to one embodiment of the present invention, a metal complex is disclosed, which has M(L a ) m (L b ) n (L c ) q The general structure of

[0012] Wherein, the metal M is selected from metals with a relative atomic mass greater than 40;

[0013] 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 Is it the same or different? c and the L b are the same or different; where La , L b and L c can optionally be linked to form a multidentate ligand;

[0014] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, m+n+q is equal to the oxidation state of metal M; when m is 2, the two L a The same or different; when n is 2, the two L b Same or different;

[0015] L c is selected from monoanionic bidentate ligands;

[0016] L a Having a structure represented by Formula 1, L b Having a structure represented by Formula 2:

[0017]

[0018] in,

[0019] Ring C y 、Ring C u and Ring C w is selected, identically or differently at each occurrence, from an aromatic ring having 6 to 24 ring atoms, a heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0020] G1, G2, G3 and G4 are selected, at each occurrence, identically or differently, from a single bond, O or S;

[0021] Each occurrence of Z is identical or different and is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' are present at the same time, the two R' are identical or different;

[0022] X1-X4 are selected from C, CR in the same or different manner at each occurrence x1 , CR n or N;

[0023] One of X1-X4 is selected from C and is connected to the ring C y Connected; at least one of X1-X4 is selected from CR n ;

[0024] X5-X8 are selected from CR in the same or different way each time they appear. x2 or N;

[0025] At least one of X5-X8 is selected from CR x2 , and the R x2 is cyano or fluorine;

[0026] When G2 is selected from a single bond, and X1, X2, X3 or X4 is selected from N, the X1, X2, X3 or X4 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, X3 or X4 is selected from C, the X1, X2, X3 or X4 is connected to the metal through G2;

[0027] R y , R u and R w Each occurrence of the same or different represents mono-, poly-, or unsubstituted; when multiple R y When the R y Same or different; when there are multiple R u When the R u Same or different; when there are multiple R w When the R w Same or different;

[0028] R n The group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0029] Ring C u contains two adjacent C atoms, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or ring C w There are two adjacent C atoms in the compound, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring:

[0030]

[0031] In formula 3, "*" representsu and / or ring C w The connection position of the two adjacent C atoms in ;

[0032] p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1;

[0033] When p1 or p2 is selected from 0, A1 and A2 are selected from CRR at each occurrence, the same or different; when p1 and p2 are selected from 1, 2, 3, 4 or 5 at each occurrence, A1 and A2 are selected from CR at each occurrence, the same or different;

[0034] A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O);

[0035] R x1 , R x2 , R y , R u , R w , R', R and R 1 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;

[0036] Adjacent substituents R, R 1 can optionally be linked to form a ring;

[0037] Adjacent substituent R u , R w can optionally be linked to form a ring;

[0038] Adjacent substituent R y can optionally be linked to form a ring;

[0039] The adjacent substituents R', R x2 Can optionally be linked to form a ring.

[0040] 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.

[0041] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the metal complex described in the above embodiment.

[0042] The present invention aims to provide a series of L comprising the structure of formula 1 a The ligand and L of the structure of formula 2 b 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 obtain more saturated green light emission and lower efficiency roll-off, providing more options for phosphorescent OLED materials and devices in high-brightness scene applications. At the same time, the metal complexes of the present invention have lower device capacitance in the device, which is more helpful to improve the response rate of OLED display devices at low grayscales and increase the refresh rate of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] 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.

[0044] 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.

[0045] Figure 3 It is a schematic diagram of the capacitance-voltage (CV) characteristic curve of an electroluminescent device. DETAILED DESCRIPTION

[0046] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0047] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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).

[0057] 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.

[0058] 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).

[0059] As used herein, unless otherwise specified, "maximum capacitance" refers to the peak value that the device capacitance can reach at a specific frequency as the test voltage increases, such as Figure 3 Generally, the display industry pays more attention to the capacitance of OLED devices in the range of 100-1000 Hz, and the capacitance data under 500 Hz is the most commonly used. Therefore, the device capacitance measured in the device embodiments of this article is the capacitance under 500 Hz.

[0060] Definition of Substituent Terms

[0061] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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,

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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:

[0084]

[0085] 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:

[0086]

[0087] 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:

[0088]

[0089] 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:

[0090]

[0091] According to one embodiment of the present invention, a metal complex is disclosed, having M(L a ) m (L b ) n (L c ) q The general structure of

[0092] The metal M is selected from metals with a relative atomic mass greater than 40;

[0093] 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 Is it the same or different? c and the L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand;

[0094] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, m+n+q is equal to the oxidation state of metal M; when m is 2, the two L a The same or different; when n is 2, the two L b Same or different;

[0095] L c is selected from monoanionic bidentate ligands;

[0096] L a Having a structure represented by Formula 1, L b Having a structure represented by Formula 2:

[0097]

[0098] in,

[0099] Ring C y 、Ring C u and Ring C w is selected, identically or differently at each occurrence, from an aromatic ring having 6 to 24 ring atoms, a heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0100] G1, G2, G3 and G4 are selected, at each occurrence, identically or differently, from a single bond, O or S;

[0101] Each occurrence of Z is identical or different and is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' are present at the same time, the two R' are identical or different;

[0102] X1-X4 are selected from C, CR in the same or different manner at each occurrence x1 , CR n or N;

[0103] One of X1-X4 is selected from C and is connected to the ring C y Connected; at least one of X1-X4 is selected from CR n ;

[0104] X5-X8 are selected from CR in the same or different way each time they appear. x2 or N;

[0105] At least one of X5-X8 is selected from CR x2 , and the R x2 is cyano or fluorine;

[0106] When G2 is selected from a single bond, and X1, X2, X3 or X4 is selected from N, the X1, X2, X3 or X4 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, X3 or X4 is selected from C, the X1, X2, X3 or X4 is connected to the metal through G2;

[0107] R y , R u and R w Each occurrence of the same or different represents mono-, poly-, or unsubstituted; when multiple R y When the R y Same or different; when there are multiple R u When the R u Same or different; when there are multiple R w When the R w Same or different;

[0108] R nThe group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0109] Ring C u contains two adjacent C atoms, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or ring C w There are two adjacent C atoms in the compound, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring:

[0110]

[0111] In formula 3, "*" represents u and / or ring C w The connection position of the two adjacent C atoms in ;

[0112] p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1;

[0113] When p1 or p2 is selected from 0, A1 and A2 are selected from CRR at each occurrence, the same or different; when p1 and p2 are selected from 1, 2, 3, 4 or 5 at each occurrence, A1 and A2 are selected from CR at each occurrence, the same or different;

[0114] A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O);

[0115] R x1 , Rx2 , R y , R u , R w , R', R and R 1 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;

[0116] Adjacent substituents R, R 1 can optionally be linked to form a ring;

[0117] Adjacent substituent R u , R w can optionally be linked to form a ring;

[0118] Adjacent substituent R y can optionally be linked to form a ring;

[0119] The adjacent substituents R', R x2 Can optionally be linked to form a ring.

[0120] In this context, when G1 is selected from a single bond, it means that ring C y directly connected to the metal M; when G2 is selected from a single bond, it means that X1, X2, X3 or X4 is directly connected to the metal M.

[0121] In this context, when G3 is selected from a single bond, it means that ring C u Directly connected to the metal M; when G4 is selected from a single bond, it means that the ring C w Directly connected to metal M.

[0122] As used herein, “adjacent substituents R, R 1"can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R 1 Between the substituents R and R 1 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.

[0123] In this context, “the adjacent substituent R u , R w "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example two substituents R u Between the two substituents R w Between, the substituent R u and R w 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.

[0124] 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.

[0125] As used herein, “adjacent substituents R′, R x2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example two substituents R x2 Between two substituents R', between substituents R x2 Between R and R', 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.

[0126] According to one embodiment of the present invention, wherein ring C y Each occurrence is identically or differently selected from any one of the following groups:

[0127]

[0128] in,

[0129] 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;

[0130] R y and R y1The 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;

[0131] Adjacent substituent R y can optionally be linked to form a ring;

[0132] Wherein, “#” indicates the position connected to the metal M. Indicates a location connected to X1, X2, X3, or X4.

[0133] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from any one of the following groups:

[0134]

[0135]

[0136] in,

[0137] R u and R w Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0138] Ring C u and / or ring C w There are at least two adjacent C atoms in the compound, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring;

[0139]

[0140] In formula 3, "*" represents ring Cu and / or ring C w The connection position of the two adjacent C atoms in ;

[0141] p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1;

[0142] When p1 or p2 is selected from 0, A1 and A2 are selected from CRR the same or differently each time they appear; when p1 and p2 are selected from 1, 2, 3, 4 or 5 the same or differently each time they appear, A1 and A2 are selected from CR the same or differently each time they appear; when two Rs are present at the same time, the two Rs are the same or different;

[0143] A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O);

[0144] R u , R ux , R w , R and R 1 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;

[0145] Adjacent substituents R, R 1 can optionally be linked to form a ring;

[0146] Adjacent substituent R u , R w Can optionally be linked to form a ring.

[0147] In this embodiment, the substituent R u The ring is ring C u , substituent R w The ring is ring C w .

[0148] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears, the same or different.

[0149] According to one embodiment of the present invention, the metal M is selected from Pt or Ir, the same or different each time it occurs.

[0150] According to one embodiment of the present invention, the metal M is selected from Ir the same or differently each time it occurs.

[0151] According to one embodiment of the present invention, G1 and G2 are selected from a single bond or O the same or differently each time they appear.

[0152] According to one embodiment of the present invention, G1 and G2 are single bonds.

[0153] According to one embodiment of the present invention, G3 and G4 are single bonds.

[0154] According to one embodiment of the present invention, L c Each occurrence is identically or differently selected from any one of the following groups:

[0155]

[0156] in,

[0157] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;

[0158] R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0159] 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;

[0160] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0161] 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.

[0162] According to one embodiment of the present invention, L c It has the following structure:

[0163] in,

[0164] R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0165] R a and R b 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 an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group 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;

[0166] Adjacent substituent R a and R b Can optionally be linked to form a ring.

[0167] According to one embodiment of the present invention, R a and R b 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 alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0168] 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 4 is:

[0169]

[0170] in,

[0171] m is selected from 1 or 2; when m is selected from 1, the two L b The same or different; when m is selected from 2, the two L a Same or different;

[0172] 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;

[0173] Each occurrence of Y3-Y6 is identical or different and is selected from CR y or N;

[0174] X3 is selected from CR in the same or different way each time it appears x1 or N;

[0175] X5-X8 are selected from CR in the same or different way each time they appear. x2 or N; at least one of X5-X8 is CR x2 , and the R x2 is cyano or fluorine;

[0176] U3-U6 are selected from CR in the same or different order each time they appear. u or N;

[0177] W3-W6 are selected from CR in the same or different manner each time they appear. w or N;

[0178] There are at least two adjacent C atoms in U3-U6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring;

[0179]

[0180] In Formula 3, "*" indicates the connection position with two adjacent C atoms in U3-U6 and / or W3-W6;

[0181] p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1;

[0182] When p1 or p2 is selected from 0, A1 and A2 are selected from CRR the same or differently each time they appear; when p1 and p2 are selected from 1, 2, 3, 4 or 5 the same or differently each time they appear, A1 and A2 are selected from CR the same or differently each time they appear; when two Rs are present at the same time, the two Rs are the same or different;

[0183] A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O);

[0184] R n The group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0185] R x1 , R x2 , R y , R u , R w , R', R and R 1The 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;

[0186] Adjacent substituents R, R 1 can optionally be linked to form a ring;

[0187] Adjacent substituent R y can optionally be linked to form a ring;

[0188] The adjacent substituents R', R x2 Can optionally be linked to form a ring.

[0189] According to one embodiment of the present invention, m is selected from 1.

[0190] According to one embodiment of the present invention, Z is selected from O or S the same or differently each time it occurs.

[0191] According to one embodiment of the present invention, Z is selected from O.

[0192] According to one embodiment of the present invention, R n Each occurrence is identically or differently selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0193] According to one embodiment of the present invention, R nEach occurrence is identically or differently selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.

[0194] According to one embodiment of the present invention, R n On each occurrence it is identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0195] According to one embodiment of the present invention, R n Each occurrence is identically or differently selected from the group consisting of:

[0196]

[0197] Optionally, the above R n The hydrogen in can be partially or completely replaced by deuterium;

[0198] The above R n The "*" in " represents the connection position with X1, X2, X3 or X4.

[0199] According to one embodiment of the present invention, each occurrence of Y3-Y6 is identically or differently selected from CR y .

[0200] According to one embodiment of the present invention, each occurrence of Y3-Y6 is identically or differently selected from CR y Or N, and at least one of Y3-Y6 is N, for example, one of Y3-Y6 is selected from N or two of Y3-Y6 are selected from N.

[0201] According to one embodiment of the present invention, each occurrence of Y3-Y6 is the same or different 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 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, and combinations thereof.

[0202] According to one embodiment of the present invention, 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 ySelected 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, and combinations thereof.

[0203] According to one embodiment of the present invention, each occurrence of Y3-Y6 is the same or different CR y or N, and at least one of Y3-Y6 is selected from CR y , and the R y Each occurrence is identically or differently selected from the group consisting of hydrogen, 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.

[0204] According to one embodiment of the present invention, X3 is selected from CR x1 , and the R x1 Each occurrence is identically or differently selected from 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, or a combination thereof.

[0205] According to one embodiment of the present invention, X3 is selected from CR x1 , and the R x1 Each occurrence is identically or differently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cyano, or a combination thereof.

[0206] According to one embodiment of the present invention, X5-X8 are selected from CR x2 .

[0207] According to one embodiment of the present invention, X5-X8 are selected from CR x2 Or N, and at least one of X5-X8 is N, for example, one of X5-X8 is selected from N or two of X5-X8 are selected from N.

[0208] According to one embodiment of the present invention, at least two of X5-X8 are selected from CR x2 , and one of the R x2 is cyano or fluorine; the other R x2selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl ... atom, an alkynyl group having 6 to 30 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, 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 a combination thereof having 0 to 20 carbon atoms.

[0209] According to one embodiment of the present invention, at least two of X5-X8 are selected from CR x2 , and one of the R x2 is cyano or fluorine; the other R x2 Selected from the group consisting of deuterium, 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.

[0210] According to one embodiment of the present invention, X7 or X8 is CR x2 , and the R x2 It is cyano or fluorine.

[0211] According to one embodiment of the present invention, X7 is CR x2 , and the R x2 It is cyano or fluorine.

[0212] According to one embodiment of the present invention, X7 is CR x2 , and the R x2 It's cyano.

[0213] According to one embodiment of the present invention, X7 is selected from CR x2 , and the R x2 is cyano or fluorine, X8 is selected from CR x2 , and the R x2is selected from deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.

[0214] According to one embodiment of the present invention, X7 is selected from CR x2 , and the R x2 is cyano or fluorine, X8 is selected from CR x2 , and the R x2 is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.

[0215] According to one embodiment of the present invention, there are at least two adjacent C atoms in U3-U6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring.

[0216] According to one embodiment of the present invention, there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring.

[0217] According to one embodiment of the present invention, W4 and W5 are selected from C atoms, and the C atoms are fused with Formula 3 to form a non-aromatic ring.

[0218] According to one embodiment of the present invention, in Formula 3, p1 is selected from 1, 2 or 3, p2 is selected from 0; A1 and A2 are selected from CRR the same or differently each time they appear; A3 is selected from CR the same or differently each time they appear 1 R 1 , O, S, NR 1 Or C(=O).

[0219] According to one embodiment of the present invention, in Formula 3, p1 is selected from 1, 2 or 3, p2 is selected from 0; A1 and A2 are selected from CRR the same or differently each time they appear; A3 is selected from CR the same or differently each time they appear 1 R 1 .

[0220] According to one embodiment of the present invention, Formula 3 has a structure represented by the following Formula 5:

[0221]

[0222] in,

[0223] In formula 5, "*" represents uand / or ring C w The connection position of the two adjacent C atoms in ;

[0224] p1 is selected from 1, 2 or 3;

[0225] A3 is selected from CR in the same or different way each time it appears 1 R 1 , O, S, NR 1 or C(=O);

[0226] R and R 1 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;

[0227] Adjacent substituents R, R 1 Can optionally be linked to form a ring.

[0228] According to one embodiment of the present invention, R and R 1The following are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, 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 arylsilanyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, and combinations thereof.

[0229] According to one embodiment of the present invention, R and R 1 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.

[0230] According to one embodiment of the present invention, R and R 1 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, and combinations thereof.

[0231] According to one embodiment of the present invention, R y1 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0232] According to one embodiment of the present invention, R ux 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0233] According to one embodiment of the present invention, R x1 and R x2 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.

[0234] According to one embodiment of the present invention, R x1 and R x2 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.

[0235] According to one embodiment of the present invention, R x1 and R x2 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, biphenyl, naphthyl, carbazolyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

[0236] 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.

[0237] According to one embodiment of the present invention, R yEach 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.

[0238] 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.

[0239] According to one embodiment of the present invention, 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.

[0240] According to one embodiment of the present invention, 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.

[0241] According to one embodiment of the present invention, at least one of Y3-Y6 is 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.

[0242] According to one embodiment of the present invention, L aEach occurrence is selected from L a1 To L a3526 The group consisting of L a1 To L a3526 The specific structure is shown in claim 16.

[0243] According to one embodiment of the present invention, wherein the L a1 To L a3526 The hydrogen in the ion can be partially or completely replaced by deuterium.

[0244] According to one embodiment of the present invention, L b Each occurrence is selected from L b1 To L b294 The group consisting of L b1 To L b294 The specific structure is shown in claim 17.

[0245] According to one embodiment of the present invention, wherein the L b1 To L b294 The hydrogen in the ion can be partially or completely replaced by deuterium.

[0246] According to one embodiment of the present invention, L c Each occurrence is selected from L c1 To L c142 The group consisting of L c1 To L c142 The specific structure is shown in claim 18.

[0247] According to one embodiment of the present invention, L c1 To L c18 , L c20 To L c26 and L c31 To L c142 The hydrogen in the ion can be partially or completely replaced by deuterium.

[0248] According to one embodiment of the present invention, the metal complex has 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 a3526 One or two of the group consisting of L b Each occurrence is selected from L b1 To L b294 One or two of the group.

[0249] According to one embodiment of the present invention, the metal complex has Ir(L a )(L b )(L c ) structure, L a Each occurrence is selected from L a1 To L a3526 One of the groups, L b Each occurrence is selected from L b1 To L b294 One of the groups, L c Each occurrence is selected from L c1 To L c142 One of the groups.

[0250] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 5544, and the specific structures of the metal complex 1 to metal complex 5544 are described in claim 19.

[0251] 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.

[0252] According to one embodiment of the present invention, the organic layer containing the metal complex is a light-emitting layer.

[0253] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound.

[0254] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound and a second host compound.

[0255] 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.

[0256] According to one embodiment of the present invention, the first host compound has a structure represented by formula X-1 or X-2:

[0257]

[0258] in,

[0259] 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;

[0260] G is selected, identically or differently, from C(R g )2. NR g , O or S;

[0261] Each occurrence of V is selected from C, CR v or N;

[0262] In formula X-1, each occurrence of T is identical or different and is selected from C, CR t or N;

[0263] In formula X-2, each occurrence of T is identically or differently selected from CR t or N;

[0264] 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;

[0265] Ar1 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;

[0266] Adjacent substituent Rg , R v and R t Can optionally be linked to form a ring.

[0267] 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.

[0268] According to one embodiment of the present invention, the first host compound has a structure represented by one of Formula Xa to Formula Xp:

[0269]

[0270] in,

[0271] 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;

[0272] G is selected, identically or differently, from C(R g )2. NR g , O or S;

[0273] Each time V appears, it is selected from CR in the same or different way. v or N;

[0274] Each occurrence of T is selected from CR t or N;

[0275] 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;

[0276] Ar1 is identically or differently selected at each occurrence 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;

[0277] Adjacent substituent R g , R v and R t Can optionally be linked to form a ring.

[0278] According to one embodiment of the present invention, the first host compound is selected from the group consisting of the following compounds:

[0279]

[0280]

[0281]

[0282] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 6:

[0283]

[0284] in,

[0285] Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, and at least one of E1-E6 is C, and they are connected to formula A;

[0286]

[0287] in,

[0288] 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;

[0289] p is 0 or 1; r is 0 or 1;

[0290] When Q is selected from N, p is 0 and r is 1;

[0291] 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;

[0292] 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;

[0293] Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N;

[0294] 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;

[0295] “*” represents the connection position between Formula A and Formula 6;

[0296] Adjacent substituent R e , R Q , R q Can optionally be linked to form a ring.

[0297] 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.

[0298] According to one embodiment of the present invention, the second host compound is selected from the group consisting of the following compounds:

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305] 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.

[0306] 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.

[0307] 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:

[0308] 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.

[0309] Combination with other materials

[0310] 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.

[0311] 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.

[0312] 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.

[0313] Material Synthesis Example

[0314] Synthesis Example 1: Synthesis of Metal Complex 2810

[0315] Step 1: Synthesis of intermediate 1

[0316]

[0317] Under nitrogen protection, 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (15.0 g, 56.1 mmol), biboric acid pinacol ester (18.5 g, 72.3 mmol), Pd(dppf)Cl2 (1.4 g, 1.9 mmol), potassium acetate (13.8 g, 140.3 mmol), N,N-dimethylformamide (DMF, 100 mL) were added to a dry 250 mL round-bottom flask in sequence, and the mixture was reacted overnight at 100 ° C. After the reaction was complete, the mixture was washed with a large amount of water, extracted with ethyl acetate, and the organic phase was concentrated to obtain a crude intermediate 1, which was directly used in the next step.

[0318] Step 2: Synthesis of Intermediate 2

[0319]

[0320] Under nitrogen protection, the intermediate 1,2-chloro-5-tert-butylpyridine (9.5 g, 56.1 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), sodium carbonate (14.9 g, 140.3 mmol), 1,4-dioxane / water (3 / 1, 160 mL) from the previous step were added to a dry 250 mL round-bottom flask in sequence, and reacted at 100°C overnight. After the reaction was complete, the product was extracted with ethyl acetate and purified by column chromatography to obtain intermediate 2 (8.1 g, 25.2 mmol, 45% yield).

[0321] Step 3: Synthesis of Intermediate 3

[0322]

[0323] Under nitrogen protection, intermediate 2 (8.1 g, 25.2 mmol), iridium trichloride trihydrate (3.0 g, 8.5 mmol), 2-ethoxyethanol (2-Eyhoxyethanol, 30 mL) and water (10 mL) were added to a dry 250 mL round-bottom flask in sequence. After reacting at 130 ° C for 24 h, the solid was collected by filtration. After the solid was dried, it was dissolved in dichloromethane (100 mL), and silver trifluoromethanesulfonate (1.8 g, 7.0 mmol) and methanol (5 ml) were added. Stir overnight at room temperature. After the reaction was complete, it was filtered and the filtrate was concentrated under reduced pressure to obtain a yellow solid intermediate 3 (6.0 g, 5.7 mmol, 67% yield).

[0324] Step 4: Synthesis of Metal Complex 2810

[0325]

[0326] In a dry 100 mL round-bottom flask, intermediate 3 (1.3 g, 1.25 mmol), intermediate 4 (0.55 g, 1.35 mmol), 2-ethoxyethanol (15 mL) and DMF (15 mL) were added in sequence, and the reaction was heated at 100 ° C for 5 days under N2 protection. After the reaction was cooled, it was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 2810 (0.8 g, 52% yield). The product was determined to be the target product with a molecular weight of 1239.6.

[0327] Synthesis Example 2: Synthesis of Metal Complex 2832

[0328]

[0329] In a dry 100 mL round-bottom flask, intermediate 3 (1.0 g, 0.96 mmol), intermediate 4 (0.6 g, 1.0 mmol), 2-ethoxyethanol (15 mL) and DMF (15 mL) were added in sequence, and the reaction was heated at 100 ° C for 5 days under N2 protection. After the reaction was cooled, it was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 2832 (0.5 g, 36% yield). The product was determined to be the target product with a molecular weight of 1435.8.

[0330] Synthesis Example 3: Synthesis of Metal Complex 1640:

[0331]

[0332] In a dry 250 mL round-bottom flask, intermediate 6 (2.5 g, 2.7 mmol), intermediate 7 (1.5 g, 3.0 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence, and the mixture was heated at 100 ° C for 5 days under N2 protection. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain a yellow solid metal complex 1640 (1.8 g, 55% yield). The product was determined to be the target product with a molecular weight of 1219.6.

[0333] 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.

[0334] Device Example 1

[0335] 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 sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound PD is doped in compound HT as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound PH-1 is used as an electron blocking layer (EBL). Then the metal complex 2810 of the present invention is doped in compound PH-1 and compound H-40 and co-deposited as a light-emitting layer (EML). On EML, compound H-2 is used as a hole blocking layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a 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.

[0336] Device Comparison Example 1

[0337] The implementation of Comparative Device Example 1 is the same as that of Example 1, except that the metal complex 2810 is replaced with Compound GD1 in the light emitting layer (EML).

[0338] 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.

[0339] Table 1 Device structures of Example 1 and Comparative Example 1

[0340]

[0341] The material structure used in the device is shown below:

[0342]

[0343]

[0344] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM) of maximum emission wavelength, current efficiency (CE), external quantum efficiency (EQE) and at 11500cd / m 2The current efficiency (CE) and external quantum efficiency (EQE) of the device were measured under 100 Hz. The capacitance of the device was tested 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. The device was tested under an AC voltage with a frequency of 500Hz. The CV curve of the device was measured to obtain the maximum capacitance (C max ). These data are recorded and shown in Table 2.

[0345] Table 2 Device data of Example 1 and Comparative Example 1

[0346]

[0347] From the data in Table 2, it can be seen that the spectrum of Example 1 is blue-shifted by 9nm compared with Comparative Example 1. 2 Under the condition of high brightness 11500cd / m 2 Under the condition of 1 / 200 ℃, the current efficiency (CE) and external quantum efficiency (EQE) of Example 1 are higher than those of Comparative Example 1. At the same time, the maximum capacitance of Example 1 is 0.31nF lower than that of Comparative Example 1. The above data show that the embodiment with the characteristics of the present invention has more saturated green light emission and lower efficiency roll-off than Comparative Example 1, which provides more choices for the application of phosphorescent OLED materials and devices in high-brightness scenes. At the same time, the embodiment with the characteristics of the present invention has lower device capacitance than the comparative example, which is more helpful to improve the response rate of OLED display devices at low grayscales and increase the refresh rate of the device.

[0348] Device Example 2

[0349] The implementation method of Device Example 2 is the same as that of Device Example 1, except that the metal complex 2832 of the present invention is used instead of the metal complex 2810 in the light emitting layer (EML), wherein compound PH-1:compound H-40:metal complex 2832=47:47:6.

[0350] Device Comparison Example 2

[0351] The implementation of Comparative Device Example 2 is the same as that of Example 2, except that the metal complex 2832 is replaced with Compound GD2 in the light emitting layer (EML).

[0352] 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.

[0353] Table 3 Device structures of Example 2 and Comparative Example 2

[0354]

[0355] The new material structure used in the device is shown below:

[0356]

[0357] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM) of maximum emission wavelength, current efficiency (CE), external quantum efficiency (EQE) and at 11500cd / m 2 The current efficiency (CE) and external quantum efficiency (EQE) of the device were measured under 100 Hz. The capacitance of the device was tested 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. The device was tested under an AC voltage with a frequency of 500Hz. The CV curve of the device was measured to obtain the maximum capacitance (C max ). These data are recorded and shown in Table 4.

[0358] Table 4 Device data of Example 2 and Comparative Example 2

[0359]

[0360] From the data in Table 4, it can be seen that the spectrum of Example 2 is blue-shifted by 1 nm compared with Comparative Example 2. 2 Under the condition of high brightness 11500cd / m 2 Under the condition of , the current efficiency (CE) of Example 2 is consistent with that of Comparative Example 2, while the external quantum efficiency (EQE) is slightly higher than that of Comparative Example 1. At the same time, the maximum capacitance of Example 2 is 1.57nF lower than that of Comparative Example 2. The above data show that the embodiment with the characteristics of the present invention has a more saturated green light emission and a lower efficiency roll-off than Comparative Example 1, which provides more choices for the application of phosphorescent OLED materials and devices in high-brightness scenes. At the same time, the embodiment with the characteristics of the present invention has a lower device capacitance than the comparative example, which is more helpful to improve the response rate of the OLED display device at low grayscale and increase the refresh frequency of the device.

[0361] The above results show that L having the structure of Formula 1 of the present invention a The ligand and L of the structure of formula 2 bThe metal complex of the ligand can obtain more saturated green luminescence, lower efficiency roll-off and lower device capacitance. It is more conducive to the application of OLED materials and devices in high-brightness scenes, and improves the response rate of OLED display devices at low grayscale and increases the refresh frequency of the device. The metal complex of the present invention is conducive to improving the comprehensive performance of the device and has great advantages and broad prospects in industrial applications.

[0362] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A metal complex having M(L a ) m (L b ) n (L c ) q The general structure of The metal M is selected from metals with a relative atomic mass greater than 40; 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 Is it the same or different? c and the L b are the same or different; L a , L b and L c can optionally be linked to form a multidentate ligand; m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, m+n+q is equal to the oxidation state of metal M; when m is 2, the two L a The same or different; when n is 2, the two L b Same or different; L c is selected from monoanionic bidentate ligands; L a Having a structure represented by Formula 1, L b Having a structure represented by Formula 2: in, Ring C y 、Ring C u and Ring C w is selected, identically or differently at each occurrence, from an aromatic ring having 6 to 24 ring atoms, a heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; G1, G2, G3 and G4 are selected, at each occurrence, identically or differently, from a single bond, O or S; Each occurrence of Z is identical or different and is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' are present at the same time, the two R' are identical or different; X1-X4 are selected from C, CR in the same or different manner at each occurrence x1 , CR n or N; One of X1-X4 is selected from C and is connected to the ring C y Connected; at least one of X1-X4 is selected from CR n ; X5-X8 are selected from CR in the same or different way each time they appear. x2 or N; At least one of X5-X8 is selected from CR x2 , and the R x2 is cyano or fluorine; When G2 is selected from a single bond, and X1, X2, X3 or X4 is selected from N, the X1, X2, X3 or X4 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, X3 or X4 is selected from C, the X1, X2, X3 or X4 is connected to the metal through G2; R y , R u and R w Each occurrence of the same or different represents mono-, poly-, or unsubstituted; when multiple R y When the R y Same or different; when there are multiple R u When the R u Same or different; when there are multiple R w When the R w Same or different; R n The group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ring C u contains two adjacent C atoms, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or ring C w There are two adjacent C atoms in the compound, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring: In formula 3, "*" represents u and / or ring C w The connection position of the two adjacent C atoms in ; p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1; When p1 or p2 is selected from 0, A1 and A2 are selected from CRR at each occurrence, the same or different; when p1 and p2 are selected from 1, 2, 3, 4 or 5 at each occurrence, A1 and A2 are selected from CR at each occurrence, the same or different; A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O); R x1 , R x2 , R y , R u , R w , R', R and R 1 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 substituents R, R 1 can optionally be linked to form a ring; Adjacent substituent R u , R w can optionally be linked to form a ring; Adjacent substituent R y can optionally be linked to form a ring; The adjacent substituents R', R x2 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 and R y1 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 a location connected to X1, X2, X3, or X4.

3. The metal complex according to claim 1, wherein L b Each occurrence is identically or differently selected from any one of the following groups: in, R u and R w Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; Ring C u and / or ring C w There are at least two adjacent C atoms in the compound, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; In formula 3, "*" represents u and / or ring C w The connection position of the two adjacent C atoms in ; p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1; When p1 or p2 is selected from 0, A1 and A2 are selected from CRR the same or differently each time they appear; when p1 and p2 are selected from 1, 2, 3, 4 or 5 the same or differently each time they appear, A1 and A2 are selected from CR the same or differently each time they appear; when two Rs are present at the same time, the two Rs are the same or different; A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O); R u , R ux , R w , R and R 1 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 substituents R, R 1 can optionally be linked to form a ring; Adjacent substituent R u , R w Can optionally be linked to form a ring.

4. The metal complex according to claim 1, wherein The metal M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; Preferably, the metal M is chosen, identically or differently on each occurrence, from Pt or Ir.

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 4 is: in, m is selected from 1 or 2; when m is selected from 1, the two L b The same or different; when m is selected from 2, the two 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; Each occurrence of Y3-Y6 is identical or different and is selected from CR y or N; X3 is selected from CR in the same or different way each time it appears x1 or N; X5-X8 are selected from CR in the same or different way each time they appear. x2 or N; at least one of X5-X8 is CR x2 , and the R x2 is cyano or fluorine; Each occurrence of U3-U6 is selected from CR u or N; W3-W6 are selected from CR in the same or different manner each time they appear. w or N; There are at least two adjacent C atoms in U3-U6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; In Formula 3, "*" indicates the connection position with two adjacent C atoms in U3-U6 and / or W3-W6; p1 and p2 are selected from 0, 1, 2, 3, 4 or 5 each time they appear, the same or different, and the sum of p1 and p2 is greater than or equal to 1; When p1 or p2 is selected from 0, A1 and A2 are selected from CRR the same or differently each time they appear; when p1 and p2 are selected from 1, 2, 3, 4 or 5 the same or differently each time they appear, A1 and A2 are selected from CR the same or differently each time they appear; when two Rs are present at the same time, the two Rs are the same or different; A3 and A4 are selected from CR 1 R 1 , O, S, NR 1 or C(=O); R n The group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R x1 , R x2 , R y , R u , R w , R', R and R 1 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkyne 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 substituents R, R 1 can optionally be linked to form a ring; Adjacent substituent R y can optionally be linked to form a ring; The adjacent substituents R', R x2 Can optionally be linked to form a ring.

6. The metal complex according to any one of claims 1 to 5, wherein Z is selected, identically or differently, at each occurrence from O or S; preferably, Z is selected from O.

7. The metal complex according to any one of claims 1 to 5, wherein R n Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; Preferably, R n Each occurrence is identically or differently selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms; More preferably, R n Each occurrence is identically or differently selected from substituted or unsubstituted alkyl radicals having 1 to 6 carbon atoms.

8. The metal complex according to claim 5, wherein Each occurrence of Y3-Y6 is CR, either identically or differently y or N, and at least one of Y3-Y6 is selected from CR y , and the 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, and combinations thereof; Preferably, each occurrence of Y3-Y6 is identical or different CR y or N, and at least one of Y3-Y6 is selected from CR y , and the R y Each occurrence is identically or differently 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.

9. The metal complex according to claim 1 or 5, wherein X3 Selected from CR x1 , and the R x1 is selected, at each occurrence, identically or differently, from 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, the R x1 Each occurrence is identically or differently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cyano, or a combination thereof.

10. The metal complex according to claim 1 or 5, wherein X7 or X8 is CR x2 , and the R x2 is cyano or fluorine; Preferably, X7 is CR x2 , and the R x2 is cyano or fluorine; More preferably, X7 is CR x2 , and the R x2 It's cyano.

11. The metal complex according to claim 1 or 5, wherein At least two of X5-X8 are selected from CR x2 , and one of the R x2 is cyano or fluorine; the other R x2 selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl ... atom, an alkynyl group having 6 to 30 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; Preferably, at least two of X5-X8 are selected from CR x2 , and one of the R x2 is cyano or fluorine; the other R x2 Selected from the group consisting of deuterium, 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; More preferably, X7 is selected from CR x2 , and the R x2 is cyano or fluorine, X8 is selected from CR x2 , and the R x2 is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.

12. The metal complex according to claim 5, wherein Each occurrence of Y3-Y6 is identical or different and is selected from CR y ; R y 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 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.

13. The metal complex according to claim 5, wherein There are at least two adjacent C atoms in U3-U6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; and / or there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; Preferably, there are at least two adjacent C atoms in W3-W6, and the two adjacent C atoms are fused with Formula 3 to form a non-aromatic ring; More preferably, W4 and W5 are selected from C atoms, and the C atoms are fused with Formula 3 to form a non-aromatic ring.

14. The metal complex according to any one of claims 1 to 5 and 13, wherein In formula 3, p1 is selected from 1, 2 or 3, and p2 is selected from 0; A1 and A2 are selected from CRR identically or differently at each occurrence; A3 is selected from CR in the same or different way each time it appears 1 R 1 ; R and R 1 The following are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 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, cyano, and combinations thereof; Preferably, R and R 1 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; More preferably, R and R 1 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, and combinations thereof; Adjacent substituents R, R 1 Can optionally be linked to form a ring.

15. The metal complex according to claim 1 or 5, wherein R n Each occurrence is identically or differently selected from the group consisting of: Optionally, the above R n The hydrogen in can be partially or completely replaced by deuterium; The above R n The "*" in represents the connection position with X1, X2, X3 or X4.

16. The metal complex according to claim 1, wherein L a Each occurrence is selected from L a1 To L a3526 Groups composed of: in, L a1 To L a3526 It has the following structure: Where R y3 -R y6 , R x3 , R x5 -R x8 , R n , Z is selected from atoms or groups in the following table: Optionally, the ligand L a1 To L a3526 The hydrogen in can be optionally partially or completely replaced by deuterium; the P1-P90 is selected from the group consisting of the following structures: Among them, "*" in P1-P90 indicates the interaction with ligand L a connection location.

17. The metal complex according to claim 1 or 16, wherein L b Each occurrence is selected from L b1 To L b294 Groups composed of: Optionally, the L b1 To L b294 The hydrogen in the ion can be partially or completely replaced by deuterium.

18. The metal complex according to claim 1 or 17, wherein L c The ligand is selected, identically or differently, from the following structures on each occurrence: Optionally, the above L c1 To L c18 , L c20 To L c26 and L c31 To L c142 The hydrogen in the ion can be partially or completely replaced by deuterium.

19. The metal complex according to claim 18, wherein The metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 5544; Among them, metal complexes 1 to 5544 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 5544 can be partially or completely replaced by deuterium.

20. 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 19.

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

22. The organic electroluminescent device according to claim 21, 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.

23. The organic electroluminescent device according to claim 22, 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.

24. A compound composition comprising the metal complex according to any one of claims 1 to 19.

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