Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure as shown in a formula 1. The novel compounds can be used as luminescent materials in organic electroluminescent devices and can provide better device performance, such as low voltage, high current efficiency and high external quantum efficiency. The invention further discloses an organic electroluminescent device containing the compound with the structure shown in the formula 1 and a compound composition.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a compound having a specific structure of formula 1, and an organic electroluminescent device and a compound composition comprising the compound. 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 electroluminescent devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

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

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

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

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

[0008] Right 1 of US20210305520A1 discloses an organic electroluminescent device, wherein the light-emitting layer comprises a first host material and a light-emitting material, wherein the light-emitting material is a phosphorescent metal complex, which defines the energy level relationship between the first host material and the phosphorescent metal complex. It can be seen that the research is about the effect of the energy level matching between the first host material and the phosphorescent metal complex on the device performance. In addition, it is also disclosed that the phosphorescent metal complex has the following general formula: Where R A A wide range of selected groups selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, etc., and any two R B Can be optionally connected to form a ring; the application discloses some platinum metal complexes such as The specific platinum complex disclosed in the application has unsubstituted or deuterated positions on the benzene ring directly connected to the imidazole carbene N, and does not disclose metal complexes having other substituents on the benzene ring directly connected to the imidazole N, and does not disclose or teach the excellent effects of using such metal complexes in devices.

[0009] The prior art discloses some blue phosphorescent materials for use in the research of blue phosphorescent devices. However, in the research of blue phosphorescent devices, there are still certain limitations in voltage, device efficiency, etc. Therefore, the application potential of such materials deserves further in-depth research and development. Summary of the invention

[0010] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the above problems. The compounds can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide excellent device performance, such as low voltage, high current efficiency and high external quantum efficiency. These advantages are of great help in improving the level of blue phosphorescent devices.

[0011] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0012]

[0013] In formula 1,

[0014] The metal M is selected from metals with a relative atomic mass greater than 40;

[0015] Ring A, Ring B, Ring D are identically or differently selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or a combination thereof,

[0016] L 1 , L 2is selected, at each occurrence, identically or differently, from a single bond, O, S, Se, (CR'R') y , (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4 or 5;

[0017] K 1 -K 4 is selected identically or differently at each occurrence from a single bond, O or S;

[0018] Z 1 -Z 3 is selected identically or differently at each occurrence from C or N;

[0019] X 1 -X 4 Each occurrence is selected from CR xx , CR x or N, and X 1 -X 4 At least one of the following is selected from CR xx ;

[0020] The R xx Having a structure represented by Formula 2:

[0021]

[0022] In formula 2,

[0023] "*" indicates the connection position of Formula 2;

[0024] Ring E 1 and Ring E 2 is selected, identically or differently at each occurrence, from a carbocycle having 3 to 30 carbon atoms, a heterocycle having 3 to 30 carbon atoms, or a combination thereof;

[0025] J is selected, identically or differently, at each occurrence, from N, P, CR", SiR" or GeR";

[0026] L is selected from a single bond, O, S, SO 2, Se, NR"', CR"'R"', SiR"'R"', GeR"'R"', BR"', PR"', P(O)R"', substituted or unsubstituted alkylene having 2-20 carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0027] R in Formula 1 has a structure represented by Formula 3:

[0028]

[0029] In formula 3,

[0030] "#" indicates the connection position of Formula 3;

[0031] Ring F, Ring G and Ring N are identically or differently selected at each occurrence from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof;

[0032] Z 4 -Z 7 is selected identically or differently at each occurrence from C or N;

[0033] R a , R b , R d , R e , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted;

[0034] R n1 Each occurrence is identical or different, indicating mono- or poly-substitution, and the R n1selected from the group consisting of halogen, substituted or unsubstituted alkyl having 2-20 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 having 2-20 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;

[0035] R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n 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 substituent R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n Can optionally be linked to form a ring.

[0037] According to one embodiment of the present invention, an electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compound having the structure of Formula 1.

[0038] According to one embodiment of the present invention, a compound composition is disclosed, which comprises the compound having the structure of Formula 1.

[0039] The present invention discloses a series of compounds having the structure of Formula 1. The compounds can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide excellent device performance, such as low voltage, high current efficiency and high external quantum efficiency. These advantages are of great help in improving the level of blue phosphorescent devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0041] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0042] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0043] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is one doped with F at a molar ratio of 50:1. 4

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

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

[0013] U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0044] 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.

[0045] 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.

[0046] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The 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.

[0047] 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.

[0048] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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).

[0053] 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.

[0054] 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).

[0055] Definition of Substituent Terms

[0056] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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,

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0073] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, Substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups refer to any one of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylgermanyl groups, arylgermanyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups and phosphino groups, which may be substituted by one or more of deuterium, halogen groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, Cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms , unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0074] 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.

[0075] 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.

[0076] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0077] 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.

[0078] 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:

[0079]

[0080] 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:

[0081]

[0082] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other 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:

[0083]

[0084] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0085]

[0086] In formula 1,

[0087] The metal M is selected from metals with a relative atomic mass greater than 40;

[0088] Ring A, Ring B, Ring D are identically or differently selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or a combination thereof,

[0089] L 1 , L 2 is selected, at each occurrence, identically or differently, from a single bond, O, S, Se, (CR'R') y , (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4 or 5;

[0090] K 1 -K 4 is selected identically or differently at each occurrence from a single bond, O or S;

[0091] Z 1 -Z 3 is selected identically or differently at each occurrence from C or N;

[0092] X 1 -X 4 Each occurrence is selected from CR xx , CR x or N, and X 1 -X 4 At least one of the following is selected from CR xx ;

[0093] The R xx Having a structure represented by Formula 2:

[0094]

[0095] In formula 2,

[0096] "*" indicates the connection position of Formula 2;

[0097] Ring E 1 and Ring E 2 is selected, identically or differently at each occurrence, from a carbocycle having 3 to 30 carbon atoms, a heterocycle having 3 to 30 carbon atoms, or a combination thereof;

[0098] J is selected, identically or differently, at each occurrence, from N, P, CR", SiR" or GeR";

[0099] L is selected from a single bond, O, S, SO 2 , Se, NR"', CR"'R"', SiR"'R"', GeR"'R"', BR"', PR"', P(O)R"', substituted or unsubstituted alkylene having 2-20 carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0100] R in Formula 1 has a structure represented by Formula 3:

[0101]

[0102] In formula 3,

[0103] "#" indicates the connection position of Formula 3;

[0104] Ring F, Ring G and Ring N are identically or differently selected at each occurrence from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof;

[0105] Z 4 -Z 7 is selected identically or differently at each occurrence from C or N;

[0106] R a , R b , R d , R e , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted;

[0107] R n1 Each occurrence is identical or different, indicating mono- or poly-substitution, and the R n1selected from the group consisting of halogen, substituted or unsubstituted alkyl having 2-20 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 having 2-20 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;

[0108] R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n 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;

[0109] Adjacent substituent R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n Can optionally be linked to form a ring.

[0110] In this document, "carbocycle" includes saturated carbocycle and unsaturated carbocycle; "unsaturated carbocycle" includes aromatic unsaturated carbocycle (aromatic ring) and non-aromatic unsaturated carbocycle; "heterocycle" includes saturated heterocycle and unsaturated heterocycle; "unsaturated heterocycle" includes aromatic unsaturated heterocycle (heteroaromatic ring) and non-aromatic unsaturated heterocycle.

[0111] In this context, “the adjacent substituent R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R x between two substituents R', between two substituents R"', between two substituents R a Between the two substituents R b Between the two substituents R d Between the two substituents R e Between the two substituents R f Between the two substituents R g Between the two substituents R n Between, the substituent R a Between R', the substituent R b Between R', the substituent R d and R', the substituent R e and R", the substituent R e Between R'' and R'', the substituent R f and R n Between, and the substituent R g and R n Any one or more of these substituent groups may be connected to form a ring. Obviously, these adjacent substituents may not be connected to form a ring.

[0112] According to one embodiment of the present invention, the M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt.

[0113] According to one embodiment of the present invention, the M is selected from Pt or Pd.

[0114] According to one embodiment of the present invention, wherein the M is selected from Pt.

[0115] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G, and ring N are selected from a five-membered unsaturated carbocyclic ring, an aromatic ring with 6 to 30 carbon atoms, or a heteroaromatic ring with 3 to 30 carbon atoms when they appear each time; the ring E 1 、Ring E 2 Each occurrence is identically or differently selected from a saturated carbocyclic ring having 3 to 30 carbon atoms, an unsaturated carbocyclic ring having 5 to 30 carbon atoms, or an unsaturated heterocyclic ring having 3 to 30 carbon atoms.

[0116] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G, and ring N are selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms, the ring E is the same or different when it appears each time. 1 、Ring E 2 Each occurrence is identically or differently selected from a saturated carbocyclic ring having 5 to 18 carbon atoms, an aromatic ring having 6 to 18 carbon atoms, a heteroaromatic ring having 3 to 18 carbon atoms, or a combination thereof.

[0117] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G, and ring N are selected from benzene ring, pyridine ring, indene ring, fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzosilole ring, dibenzosilole ring, benzothiophene ring, dibenzothiophene ring, dibenzoselenophene ring, cyclopentadiene ring, furan ring, thiophene ring, silole ring, or a combination thereof when they appear each time; the ring E 1 、Ring E 2 Each occurrence is identically or differently selected from a cyclopentane ring, a cyclohexane ring, a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a benzosilole ring, a benzothiophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.

[0118] According to one embodiment of the present invention, wherein said L 1 Selected from single bond, O, S, (CR'R') y , (SiR'R') y , NR', or a combination thereof; said y is 1 or 2.

[0119] According to one embodiment of the present invention, wherein said L 1 is selected from a single bond, O or S.

[0120] According to one embodiment of the present invention, wherein said L 1 Select from single bonds.

[0121] According to one embodiment of the present invention, wherein the K 1 -K 4 Select from single bonds.

[0122] According to one embodiment of the present invention, wherein said Z 1 Selected from N, Z 2 and Z 3 Selected from C.

[0123] According to one embodiment of the present invention, the compound has a structure represented by one of Formula 1-1 to Formula 1-7:

[0124]

[0125] In Formula 1-1 to Formula 1-7,

[0126] L 2 is selected, at each occurrence, identically or differently, from a single bond, O, S, Se, (CR'R') y , (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; y is selected from 1, 2, 3, 4 or 5 at each occurrence, the same or different;

[0127] W 1 -W 16 Each occurrence is selected from CR w or N;

[0128] X 1 -X 4 Each occurrence is selected from CR xx , CR x or N, and X 1 -X 4 At least one of the following is selected from CR xx , and the R xx Having a structure represented by Formula 2-1:

[0129]

[0130] "*" indicates the connection position of Formula 2;

[0131] E 3 -E 10 Each occurrence is selected from CR e or N;

[0132] L is selected from a single bond, O, S, SO 2 , Se, NR"', CR"'R"', SiR"'R"', GeR"'R"', BR"', PR"', P(O)R"', substituted or unsubstituted alkylene having 2-20 carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0133] R has a structure represented by Formula 3-1:

[0134]

[0135] In formula 3-1,

[0136] “#” indicates the connection position of the formula 3-1;

[0137] F 1 To F 5 Each independently selected from CR f or N;

[0138] G 1 To G 5 Each independently selected from CR g or N;

[0139] N 1 To N 3 Each independently selected from CR n , CR n1 or N, and N 1 To N 3 At least one is CR n1 ;

[0140] The R n1selected from the group consisting of halogen, substituted or unsubstituted alkyl having 2-20 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 having 2-20 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;

[0141] R', R'', R w , R x , R e , R f , R g , R n 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;

[0142] The adjacent substituents R', R'', Rw , R x , R e , R f , R g , R n Can optionally be linked to form a ring.

[0143] As used herein, “adjacent substituents R′, R″′, R w , R x , R e , R f , R g , R n "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R"', between two substituents R w Between the two substituents R x Between the two substituents R e Between the two substituents R f Between the two substituents R g Between the two substituents R n Between, the substituent R w and R', the substituent R e Between R'' and R'', the substituent R f and R n Between, and the substituent R g and R n Any one or more of these substituent groups may be connected to form a ring. Obviously, these adjacent substituents may not be connected to form a ring.

[0144] According to one embodiment of the present invention, the compound has a structure represented by Formula 1-1.

[0145] According to one embodiment of the present invention, wherein the L is selected from a single bond, O, S, Se, NR"', CR"'R"', SiR"'R"', GeR"'R"', PR"' or P(O)R"'; the R"' is the same or different each time it appears and is selected from the group consisting of: hydrogen, 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.

[0146] According to one embodiment of the present invention, wherein said L is selected from a single bond.

[0147] According to one embodiment of the present invention, wherein said E 3 -E 10 Each occurrence is selected from CR e, the R e 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 alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof.

[0148] According to one embodiment of the present invention, wherein the R e Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 ring carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-24 carbon atoms, and combinations thereof.

[0149] According to one embodiment of the present invention, wherein the R e Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, phenyl, partially or fully deuterated phenyl, pyridyl, partially or fully deuterated pyridyl, and combinations thereof.

[0150] According to one embodiment of the present invention, wherein the X 1 -X 4 Each occurrence is selected from CR xx or CR x , and X 1 -X 4 At least one of the following is selected from CR xx .

[0151] According to one embodiment of the present invention, wherein the X 2 Selected from CR xx .

[0152] According to one embodiment of the present invention, wherein the X 3 Selected from CR xx .

[0153] According to one embodiment of the present invention, wherein the R xx Each occurrence is identically or differently selected from the group consisting of Rx-1 to Rx-86, and the specific structures of Rx-1 to Rx-86 are shown in claim 10.

[0154] According to one embodiment of the present invention, wherein the N 1 and N 3 Each independently selected from CR n , N 2 Selected from CR n1 , and the R n1 Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 2 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; said R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, and combinations thereof.

[0155] According to one embodiment of the present invention, wherein the R n1 Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 3 to 10 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 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano, and combinations thereof; said R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 3-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, cyano, and combinations thereof.

[0156] According to one embodiment of the present invention, wherein the Rn1 each occurrence is identically or differently selected from the group consisting of: ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, neopentyl, partially or fully deuterated neopentyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, 4,4-dimethylcyclohexyl, partially or fully deuterated 4,4-dimethylcyclohexyl, and combinations thereof; said R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, trimethylsilyl, cyano, and combinations thereof.

[0157] According to one embodiment of the present invention, wherein the F 1 To F 5 Each independently selected from CR f ; G 1 To G 5 Each independently selected from CR g ; said R f , R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted 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 arylsilanyl 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.

[0158] According to one embodiment of the present invention, wherein the R f , R g 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano, and combinations thereof.

[0159] According to one embodiment of the present invention, wherein the R f , R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, trimethylsilyl, partially or fully deuterated trimethylsilyl, and combinations thereof.

[0160] According to one embodiment of the present invention, wherein the R f , R g At least one of the following is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, and combinations thereof.

[0161] According to one embodiment of the present invention, wherein the R f , R g At least one of them is selected from deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0162] According to one embodiment of the present invention, wherein the F 1 To F 5 and / or G 1 To G 5 Selected from CH or CD.

[0163] According to one embodiment of the present invention, wherein the F 1 To F 5 and / or G 1 To G 5 From CD.

[0164] According to one embodiment of the present invention, wherein said L 2 Selected from single bond, O, S, (SiR'R') y ,NR',(CR'R') y, or a combination thereof; said y is 1 or 2; said R', at each occurrence, is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and a combination thereof.

[0165] According to one embodiment of the present invention, wherein said L 2 is selected from a single bond, O or S.

[0166] According to one embodiment of the present invention, wherein said L 2 Selected from O.

[0167] According to one embodiment of the present invention, wherein R', R'', R w , R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0168] According to one embodiment of the present invention, wherein R', R'', R w , R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.

[0169] According to one embodiment of the present invention, the substituent R is selected from the group consisting of An-1 to An-77 the same or differently each time it appears, and the specific structures of An-1 to An-77 are shown in claim 15.

[0170] According to one embodiment of the present invention, the hydrogen in the structures of An-1 to An-77 can be partially or completely replaced by deuterium.

[0171] According to one embodiment of the present invention, the compound is selected from Pt(La )(L b ) or Pd(L a )(L b ) structure, where L a and L b are the first ligand and the second ligand coordinated with the metal Pt or Pd, respectively, the L a Choose from L a 1-1 to L a 1-75, L a 2-1 to L a 2-50, and L a 3-1 to L a 3-24 groups, the L b Choose from L b 1-1 to L b 1-28, L b 2-1 to L b 2-45, and L b 3-1 to L b 3-40 groups, the L a 1-1 to L a 1-75, L a 2-1 to L a 2-50, L a 3-1 to L a 3-24, L b 1-1 to L b 1-28, L b 2-1 to L b 2-45, and L b 3-1 to L b The specific structure of 3-40 is shown in claim 16.

[0172] According to one embodiment of the present invention, the compound is selected from the group consisting of compound Pt1 to compound Pt584 and compound Pd1 to compound P24, and the specific structures of compound Pt1 to compound Pt584 and compound Pd1 to compound P24 are shown in claim 16.

[0173] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:

[0174] anode,

[0175] cathode,

[0176] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula 1, and the compound having a structure of Formula 1 is any one of the above embodiments.

[0177] According to an embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0178] According to an embodiment of the present invention, the device emits blue light.

[0179] According to an embodiment of the present invention, the device emits white light.

[0180] According to an embodiment of the present invention, the light-emitting layer comprises at least one host material.

[0181] According to an embodiment of the present invention, the light-emitting layer comprises at least two host materials.

[0182] According to one embodiment of the present invention, the main material 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, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0183] According to another embodiment of the present invention, a compound composition is disclosed, which comprises a compound having a structure of Formula 1, wherein the compound having a structure of Formula 1 is shown in any of the above embodiments.

[0184] Combination with other materials

[0185] 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.

[0186] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0187] In the embodiment of material synthesis, unless otherwise specified, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. All reagents not otherwise specified are 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 elaborated in this patent.

[0188] Material synthesis example:

[0189] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0190] Synthesis Example 1: Synthesis of Compound Pt3

[0191] Step 1: Synthesis of Intermediate 1

[0192]

[0193] Under nitrogen conditions, 2,6-dibromo-4-tert-butylaniline (15.3 g, 50 mmol), phenyl-D5-boronic acid (14.1 g, 111 mmol), Pd(PPh 3 ) 4 (2.9 g, 2.5 mmol) and potassium carbonate (10.4 g, 75 mmol) were dissolved in toluene (150 mL) and water (50 mL), and the reaction temperature was raised to reflux and the reaction was allowed to react overnight. After the reaction was complete, the mixture was extracted with ethyl acetate and water, and the organic layer was washed twice with sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Finally, intermediate 1 (17.3 g, 55.5 mmol) was purified by column chromatography.

[0194] Step 2: Synthesis of Intermediate 2

[0195]

[0196] Under nitrogen protection, carbazole (8.3 g, 50 mmol), 2-bromo-1-chloro-4-fluorobenzene (10.4 g, 50 mmol), and cesium carbonate (32.5 g, 100 mmol) were added to a 500 mL flask, and 300 mL of N,N-dimethylformamide was added. The reaction system was heated to 100 ° C and stirred overnight. After the reaction was completed, intermediate 2 (14.2 g, 39.8 mmol) was purified by column chromatography.

[0197] Step 3: Synthesis of Intermediate 3

[0198]

[0199] Under nitrogen conditions, intermediate 1 (4.0 g, 12.8 mmol), intermediate 2 (4.8 g, 13.5 mmol), Pd(OAc) 2 (0.11 g, 0.5 mmol), 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (BINAP, 0.62 g, 1.0 mmol), NaOt-Bu (2.5 g, 25.8 mmol), and toluene (130 mL) were added to a flask. The reaction was heated to reflux and stirred overnight. After the reaction was completed, it was cooled to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain intermediate 3 (6.0 g, 10.2 mmol).

[0200] Step 4: Synthesis of Intermediate 5

[0201]

[0202] Under nitrogen conditions, intermediate 3 (3.0 g, 5.2 mmol), intermediate 4 (2.0 g, 5.0 mmol), Pd(OAc) 2 (0.045 g, 0.2 mmol), SPhos (0.16 g, 0.4 mmol), NaOt-Bu (0.96 g, 10 mmol) and xylene (50 mL) were added into a flask. The reaction temperature was raised to 130 °C and stirred overnight. After the reaction was completed, the reaction was detected by TLC. The mixture was cooled to room temperature, concentrated under reduced pressure and purified by column chromatography to obtain intermediate 5 (3.6 g, 3.7 mmol).

[0203] Step 5: Synthesis of Intermediate 6

[0204]

[0205] Under nitrogen conditions, intermediate 5 (3.6 g, 3.7 mmol), triethyl orthoformate (13.7 g, 92.5 mmol) and concentrated hydrochloric acid (0.5 mL) were added to a flask. The reaction was heated to 100 °C and stirred overnight. After the reaction was completed, it was detected by TLC. The reaction was cooled to room temperature, the reaction solution was concentrated and purified by column chromatography to obtain intermediate 6 (2.6 g, 2.6 mmol).

[0206] Step 6: Synthesis of compound Pt3

[0207]

[0208] Under nitrogen conditions, intermediate 6 (2.6 g, 2.6 mmol), Ag 2 O (0.33g, 1.42mmol), 1,2-dichloroethane (DCE, 30mL) were added to the flask, and the reaction was carried out at room temperature for 12h. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and then (1,5-cyclooctadiene) platinum dichloride (0.93g, 2.5mmol) was added. After adding o-dichlorobenzene (30mL), the reaction temperature was raised to 185°C and stirred for 72h. After the reaction was cooled to room temperature, the compound Pt3 (0.56g, 0.48mmol) was purified by column chromatography. The product was identified as the target product with a molecular weight of 1160.5.

[0209] Synthesis Example 2: Synthesis of Compound Pt8

[0210] Step 1: Synthesis of intermediate 7

[0211]

[0212] Under nitrogen protection, 3,6-di-tert-butyl-9H-carbazole (8.8 g, 31.5 mmol), 2-bromo-1-chloro-4-fluorobenzene (6.3 g, 30 mmol), and cesium carbonate (19.5 g, 60 mmol) were added to a 500 mL flask, and N,N-dimethylformamide (150 mL) was added. The reaction system was heated to 100°C and stirred overnight. After the reaction was completed, intermediate 7 (7.9 g, 16.8 mmol) was purified by column chromatography.

[0213] Step 2: Synthesis of intermediate 8

[0214]

[0215] Under nitrogen conditions, intermediate 1 (3.1 g, 10 mmol), intermediate 7 (4.9 g, 10.5 mmol), Pd(OAc) 2(0.09 g, 0.4 mmol), 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (BINAP, 0.5 g, 0.8 mmol), NaOt-Bu (1.9 g, 20 mmol), and toluene (100 mL) were added to a flask, the reaction was heated to reflux and stirred overnight, cooled to room temperature, and the reaction solution was concentrated and purified by column chromatography to obtain intermediate 8 (5.0 g, 7.1 mmol).

[0216] Step 3: Synthesis of intermediate 9

[0217]

[0218] Under nitrogen conditions, intermediate 8 (5.0 g, 7.1 mmol), intermediate 4 (2.7 g, 6.6 mmol), Pd(OAc) 2 (0.06 g, 0.26 mmol), SPhos (0.21 g, 0.52 mmol), NaOt-Bu (1.27 g, 13.2 mmol) and xylene (50 mL) were added into a flask. The reaction temperature was raised to 130 °C and stirred overnight. After the reaction was completed, the reaction was detected by TLC. The mixture was cooled to room temperature, concentrated under reduced pressure and purified by column chromatography to obtain intermediate 9 (3.6 g, 3.3 mmol).

[0219] Step 4: Synthesis of intermediate 10

[0220]

[0221] Under nitrogen conditions, intermediate 9 (3.6 g, 3.3 mmol), triethyl orthoformate (13.7 g, 92.5 mmol) and concentrated hydrochloric acid (0.5 mL) were added to a flask. The reaction was heated to 100 °C and stirred overnight. After the reaction was completed by TLC detection, it was cooled to room temperature, the reaction solution was concentrated and purified by column chromatography to obtain intermediate 10 (3.3 g, 2.9 mmol).

[0222] Step 5: Synthesis of compound Pt8

[0223]

[0224] Under nitrogen conditions, intermediate 10 (3.3 g, 2.9 mmol), Ag 2O (0.38g, 1.62mmol), 1,2-dichloroethane (DCE) (30mL) were added to the flask, and the reaction was carried out at room temperature for 12h. After the reaction was complete, the solvent was removed by concentration under reduced pressure, (1,5-cyclooctadiene) platinum dichloride (1.1g, 2.9mmol) was added, and o-dichlorobenzene (30mL) was added. The reaction temperature was raised to 185°C and stirred for 24h. After the reaction was cooled to room temperature, the compound Pt8 (0.99g, 0.78mmol) was purified by column chromatography. The product was identified as the target product with a molecular weight of 1272.6.

[0225] Synthesis Example 3: Synthesis of Compound Pt30

[0226] Step 1: Synthesis of intermediate 11

[0227]

[0228] Under nitrogen protection, carbazole (4.1 g, 25 mmol), 1-bromo-2-chloro-4-fluorobenzene (5.2 g, 25 mmol), and cesium carbonate (16.2 g, 50 mmol) were added to a 500 mL flask, and N,N-dimethylformamide (250 mL) was added. The reaction system was heated to 100°C and stirred overnight. After the reaction was completed, intermediate 11 (7.1 g, 19.9 mmol) was purified by column chromatography.

[0229] Step 2: Synthesis of intermediate 12

[0230]

[0231] Under nitrogen conditions, intermediate 1 (3.1 g, 10 mmol), intermediate 11 (3.7 g, 10.5 mmol), Pd(OAc) 2 (0.09 mg, 0.4 mmol), 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (BINAP, 0.50 g, 0.8 mmol), NaOt-Bu (2.0 g, 20 mmol), and toluene (100 mL) were added to a flask, the reaction was heated to reflux and stirred overnight, cooled to room temperature, and the reaction solution was concentrated and purified by column chromatography to obtain intermediate 12 (2.8 g, 4.7 mmol).

[0232] Step 3: Synthesis of intermediate 13

[0233]

[0234] Under nitrogen conditions, intermediate 12 (2.8 g, 4.7 mmol), intermediate 4 (1.9 g, 4.6 mmol), Pd(OAc) 2(0.04 g, 0.2 mmol), SPhos (0.16 g, 0.4 mmol), NaOt-Bu (0.9 g, 9.2 mmol) and xylene (50 mL) were added into a flask. The reaction temperature was raised to 130 °C and stirred overnight. After the reaction was completed, the reaction was detected by TLC. The mixture was cooled to room temperature, concentrated under reduced pressure and purified by column chromatography to obtain intermediate 13 (3.3 g, 3.4 mmol).

[0235] Step 4: Synthesis of intermediate 14

[0236]

[0237] Under nitrogen conditions, intermediate 13 (3.3 g, 3.4 mmol), triethyl orthoformate (25.1 g, 170 mmol) and concentrated hydrochloric acid (0.5 mL) were added to a flask. The reaction was heated to 100°C and stirred overnight. After the reaction was completed, it was detected by TLC. The reaction was cooled to room temperature, the reaction solution was concentrated and purified by column chromatography to obtain intermediate 14 (3.3 g, 3.3 mmol).

[0238] Step 5: Synthesis of compound Pt30

[0239]

[0240] Under nitrogen conditions, intermediate 14 (3.3 g, 3.3 mmol), Ag 2 O (0.42g, 1.8mmol), 1,2-dichloroethane (DCE) (30mL) were added to the flask, and the reaction was carried out at room temperature for 12h. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and then (1,5-cyclooctadiene) platinum dichloride (1.16g, 3.1mmol) was added. After adding o-dichlorobenzene (30mL), the reaction temperature was raised to 185°C and stirred for 24h. After the reaction was cooled to room temperature, the compound Pt30 (1.43g, 1.23mmol) was obtained by purification by column chromatography. The product was identified as the target product with a molecular weight of 1160.5.

[0241] 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.

[0242] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiment is only an example and should not be construed as limiting. A person skilled in the art can reasonably improve the preparation method of the following embodiment based on the prior art. For example, the ratio of various materials in the light-emitting layer is not particularly limited. A person skilled in the art can reasonably select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer material, the main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 85%-99%, and the light-emitting material can account for 1%-15%. In addition, the main material can be one or two materials, and the ratio of the two main materials to the main material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60.

[0243] Device Embodiment

[0244] Device Example 1

[0245] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -7 Compound HT and compound HI were co-deposited (weight ratio of 97:3) as a hole injection layer (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, the compound N-1 as the first host, the compound P-1 as the second host, and the compound Pt3 of the present invention as the dopant were co-evaporated (the weight ratio was 35.1:52.9:12) to serve as the light-emitting layer (EML) with a thickness of Compound N-1 was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated (weight ratio of 40:60) as an electron transport layer (ETL) with a thickness of Finally, evaporation LiF with a thickness of 1000 nm was used as an electron injection layer, and the The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture getter to complete the device.

[0246] Device Example 2

[0247] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound Pt8 is used instead of the present compound Pt3 in the light emitting layer (EML).

[0248] Device Example 3

[0249] The implementation of Device Example 3 is the same as that of Device Example 1, except that the present compound Pt30 is used instead of the present compound Pt3 in the light emitting layer (EML).

[0250] Device Comparison Example 1

[0251] The implementation of the device comparative example 1 is the same as that of the device example 1, except that the compound Pt-A ​​is used in the light emitting layer (EML) instead of the compound Pt3 of the present invention.

[0252] Comparative Example 2

[0253] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that the compound Pt-B is used in the light emitting layer (EML) instead of the compound Pt3 of the present invention.

[0254] 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.

[0255] Table 1 Partial device structures of device embodiments and comparative examples

[0256]

[0257]

[0258] The material structure used in the device is shown below:

[0259]

[0260]

[0261] At 1000cd / m 2 The CIE values, voltage, external quantum efficiency (EQE) and current efficiency (CE) of Examples 1-3 and Comparative Examples 1-2 were measured. The relevant data are shown in Table 2.

[0262] Table 2 Device data

[0263]

[0264] discuss:

[0265] In Comparative Example 1, a material not having the specific R xx Substituents and Specific R n1As the luminescent material, the comparative compound Pt-A ​​with the substituent group is used. Compared with Comparative Example 1, Examples 1-3 all have lower voltages. More importantly, EQE and CE are greatly improved. EQE is greatly improved by 29.8%, 32.2% and 27.4%, respectively, and CE is greatly improved by 37.1%, 43.4% and 28.4%, respectively. The above data comparison proves that the luminescent material with specific R xx Substituents and Specific R n1 Advantages of the compounds of formula 1 with substituents.

[0266] Comparative Example 2 used a xx Substituents but not having a specific R n1 The comparative compound Pt-B with the substituent is used as the luminescent material. From the data in Table 2, it can be seen that its device performance is already at a very high level in the blue phosphorescent device, with low voltage, high EQE and high CE. Compared with Comparative Example 2, Example 1 has a voltage that is basically equivalent to that of Comparative Example 2, which is at a low voltage level. More importantly, the EQE is further greatly improved by 12.3%, and the CE is further greatly improved by 7.0%. This set of data comparison once again proves that the invention has a specific R xx Substituents and Specific R n1 Advantages of the compounds of formula 1 with substituents.

[0267] The above results show that the use of the invention has a specific R n1 Substituents and having specific R xx The substituted compound of formula 1 is used as a luminescent material in a blue phosphorescent electroluminescent device to obtain low voltage, high external quantum efficiency and high current efficiency, thereby improving the overall performance of the device. These advantages are of great help in improving the level of blue light devices.

[0268] 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 compound having a structure of Formula 1: In formula 1, The metal M is selected from metals with a relative atomic mass greater than 40; Ring A, Ring B, Ring D are identically or differently selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or a combination thereof, L1, L2 each time appearing are identically or differently selected from a single bond, O, S, Se, (CR'R') y , (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4 or 5; K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S; Z1-Z3 are selected from C or N at each occurrence, identically or differently; X1-X4 are selected from CR in the same or different ways each time they appear xx , CR x or N, and at least one of X1-X4 is selected from CR xx ; The R xx Having a structure represented by Formula 2: In formula 2, "*" indicates the connection position of Formula 2; Ring E1 and Ring E2 are identically or differently selected at each occurrence from a carbocycle having 3 to 30 carbon atoms, a heterocycle having 3 to 30 carbon atoms, or a combination thereof; J is selected, identically or differently, at each occurrence, from N, P, CR", SiR" or GeR"; L is selected from a single bond, O, S, SO2, Se, NR', CR', R', SiR', R', GeR', R', BR', PR', P(O)R', substituted or unsubstituted alkylene having 2-20 carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof; R in Formula 1 has a structure represented by Formula 3: In formula 3, "#" indicates the connection position of Formula 3; Ring F, Ring G and Ring N are identically or differently selected at each occurrence from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; Z4-Z7 are selected, at each occurrence, identically or differently, from C or N; R a , R b , R d , R e , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted; R n1 Each occurrence is identical or different, indicating mono- or poly-substitution, and the R n1 selected from the group consisting of halogen, substituted or unsubstituted alkyl having 2-20 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 having 2-20 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; R x , R', R", R"', R a , R b , R d , R e , R f , R g , R n 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 x , R', R", R"', R a , R b , R d , R e , R f , R g , R n Can optionally be linked to form a ring.

2. The compound of claim 1, wherein the M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt; preferably, the M is selected from Pt or Pd; more preferably, the M is selected from Pt.

3. The compound according to claim 1 or 2, wherein the ring A, ring B, ring D, ring F, ring G, and ring N are selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms, the same or different when each occurs; the ring E1 and ring E2 are selected from a saturated carbocyclic ring having 3 to 30 carbon atoms, an unsaturated carbocyclic ring having 5 to 30 carbon atoms, or an unsaturated heterocyclic ring having 3 to 30 carbon atoms, the same or different when each occurs; Preferably, each occurrence of Ring A, Ring B, Ring D, Ring F, Ring G, Ring N is identical or different and is selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms; each occurrence of Ring E1 and Ring E2 is identical or different and is selected from a saturated carbocyclic ring having 5-18 carbon atoms, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms; More preferably, the ring A, ring B, ring D, ring F, ring G, and ring N are selected from benzene rings, pyridine rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, dibenzofuran rings, benzosilole rings, dibenzosilole rings, benzothiophene rings, dibenzothiophene rings, dibenzoselenophene rings, cyclopentadiene rings, furan rings, thiophene rings, silole rings, or combinations thereof at each occurrence; the ring E1 and ring E2 are selected from cyclopentane rings, cyclohexane rings, benzene rings, pyridine rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, benzosilole rings, benzothiophene rings, cyclopentadiene rings, furan rings, thiophene rings, silole rings, or combinations thereof at each occurrence.

4. The compound according to claim 1 or 2, wherein said L1 is selected from a single bond, O, S, (CR'R') y , (SiR'R') y , NR', or a combination thereof; said y is 1 or 2; Preferably, wherein said L1 is selected from a single bond, O or S; More preferably, wherein said L1 is selected from a single bond.

5. The compound of claim 1 or 2, wherein said K1-K4 is selected from a single bond.

6. The compound of claim 1 or 2, wherein Z1 is selected from N, and Z2 and Z3 are selected from C.

7. The compound according to claim 1, wherein the compound has a structure represented by one of Formula 1-1 to Formula 1-7: In Formula 1-1 to Formula 1-7, L2 is selected, at each occurrence, identically or differently, from a single bond, O, S, Se, (CR'R') y , (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; y is selected from 1, 2, 3, 4 or 5 at each occurrence, the same or different; W1-W 16 Each occurrence is the same or different selection from CR w or N; X1-X4 are selected from CR in the same or different way each time they appear. xx , CR x or N, and at least one of X1-X4 is selected from CR xx , and the R xx Having a structure represented by Formula 2-1: "*" indicates the connection position of Formula 2; E3-E 10 Each occurrence is the same or different selection from CR e or N; L is selected from a single bond, O, S, SO2, Se, NR', CR', R', SiR', R', GeR', R', BR', PR', P(O)R', substituted or unsubstituted alkylene having 2-20 carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof; R has a structure represented by Formula 3-1: In formula 3-1, "#" indicates the connection position of the formula 3-1; F1 to F5 are each independently selected from CR f or N; G1 to G5 are each independently selected from CR g or N; N1 to N3 are each independently selected from CR n , CR n1 or N, and at least one of N1 to N3 is CR n1 ; The R n1 selected from the group consisting of halogen, substituted or unsubstituted alkyl having 2-20 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 having 2-20 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; R', R'', R w , R x , R e , R f , R g , R n 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; The adjacent substituents R', R'', R w , R x , R e , R f , R g , R n can optionally be linked to form a ring; Preferably, the compound has a structure represented by Formula 1-1.

8. The compound of claim 1 or 7, wherein the L is selected from a single bond, O, S, Se, NR', CR'R', SiR'R', GeR'R', PR' or P(O)R'; the R' is selected from the group consisting of hydrogen, 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; Preferably, said L is selected from a single bond.

9. The compound of claim 7, wherein the E3-E 10 Each occurrence is the same or different selection from CR e , the R e 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 alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof; Preferably, the R e each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 24 carbon atoms, and combinations thereof; More preferably, the R e Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, phenyl, partially or fully deuterated phenyl, pyridyl, partially or fully deuterated pyridyl, and combinations thereof.

10. The compound of claim 1 or 7, wherein each occurrence of X1-X4 is identically or differently selected from CR xx or CR x , and at least one of X1-X4 is selected from CR xx ; Preferably, X2 or X3 is selected from CR xx ; More preferably, the R xx Each occurrence is identically or differently selected from the group consisting of Rx-1 to Rx-86:

11. The compound of claim 7, wherein N1 and N3 are each independently selected from CR n , N2 is selected from CR n1 , and the R n1 Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 2 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; said R n each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, and combinations thereof; Preferably, the R n1 each occurrence is identically or differently selected from the group consisting of: ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, neopentyl, partially or fully deuterated neopentyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, 4,4-dimethylcyclohexyl, partially or fully deuterated 4,4-dimethylcyclohexyl, and combinations thereof; said R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, trimethylsilyl, cyano, and combinations thereof.

12. The compound according to claim 7 or 11, wherein each of F1 to F5 is independently selected from CR f ; G1 to G5 are each independently selected from CR g ; said R f , R g each occurrence being 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 arylsilanyl 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, the R f , R g 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano, and combinations thereof; More preferably, the R f , R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, trimethylsilyl, partially or fully deuterated trimethylsilyl, and combinations thereof.

13. The compound of claim 1 or 7, wherein said L2 is selected from a single bond, O, S, (SiR'R') y ,NR',(CR'R') y , or a combination thereof; y is 1 or 2; R' is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and a combination thereof at each occurrence; Preferably, said L2 is selected from a single bond, O or S; More preferably, L2 is selected from O.

14. The compound of claim 7, wherein R', R'', R w , R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; Preferably, the R', R'', R w , R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.

15. The compound of claim 1 or 7, wherein the substituent R is selected from the group consisting of An-1 to An-77, the same or different at each occurrence: in, Optionally, hydrogen in the structures An-1 to An-77 can be partially or fully replaced by deuterium.

16. The compound of claim 1, wherein the compound is selected from the group consisting of a )(L b ) or Pd(L a )(L b ) structure, where L a and L b are the first ligand and the second ligand coordinated with the metal Pt or Pd, respectively, the L a Choose from L a 1-1 to L a 1-75, L a 2-1 to L a 2-50, and L a 3-1 to L a Groups consisting of 3-24 people: The L a The "#" in the structure indicates that the L a Structure and L b The location of the connection; Among them, ligand L b Choose from L b 1-1 to L b 1-28, L b 2-1 to L b 2-45, and L b 3-1 to L b Groups of 3-40: The L b In the structure Indicates the L b Structure and L a The position of the "#" connection in the Preferably, the compound is selected from the group consisting of Compound Pt1 to Compound Pt584 and Compound Pd1 to Compound P24; Wherein, the compounds Pt1 to Pt584 have Pt(L a )(L b ) represents a structure, wherein L a and the L b The corresponding structures are selected from the following table: The compounds Pd1 to Pd24 have Pd(L a )(L b ) represents a structure, wherein L a and the L b The corresponding structures are selected from the following table: 。 17. An organic electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to any one of claims 1 to 16.

18. The organic electroluminescent device according to claim 17, wherein the organic layer is a light-emitting layer, and the compound is a light-emitting material.

19. The organic electroluminescent device of claim 18, wherein the device emits blue light or white light.

20. The organic electroluminescent device of claim 18, wherein the light-emitting layer comprises at least one host material; preferably, the light-emitting layer comprises at least two host materials; more preferably, the host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

21. A compound composition comprising the compound of any one of claims 1-16.

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