Organic electroluminescent materials and devices
By using metal complexes containing specific La ligand structures as luminescent materials in OLEDs, the problems of reduced efficiency in high brightness and insufficient performance of blue phosphorescent devices are solved, and more efficient and lasting OLED performance is achieved.
Patent Information
- Application Number
- CN202110423792.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-04-21
- Publication Date
- 2025-03-14
- Estimated Expiration
- 2041-04-21
AI Technical Summary
The efficiency of existing organic light emitting diodes (OLEDs) rapidly decrease under high brightness conditions, and blue phosphorescent devices have problems such as unsaturation, short life and high operating voltage, which affects the performance of full-color OLED displays.
Metal complexes containing specific La ligand structures are used as the luminescent material in electroluminescent devices, which can improve the efficiency of the device and improve the overall performance.
By using these new metal complexes, the efficiency and comprehensive performance of OLED devices can be significantly improved, device life can be extended, and operating voltage can be reduced.
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Figure CN115215906B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound comprising L having a structure of Formula 1 a The invention relates to a metal complex of a ligand, and an electroluminescent device and a compound combination comprising the metal complex. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.
[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and 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] US2013119354A1 discloses a method having the following Iridium complexes with the structure R1 -R 4 is selected from hydrogen, deuterium, alkyl, cyclic alkyl, aryl, heteroaryl, and R is not disclosed or taught. 1 Contains the effects of cyanide.
[0009] US20200287144A1 discloses a metal complex comprising a ligand structure having the following structure: Where X 1 Selected from silicon and germanium, further disclosed is an iridium complex having the following general structure: The specific structures disclosed are: This application focuses on the effect of introducing silicon or germanium groups into metal complexes on device performance, and does not disclose or teach the effect of introducing CN-containing substituents at specific positions in metal complexes on device performance. Summary of the invention
[0010] The present invention aims to provide a series of L having a structure of Formula 1 a Ligand-metal complexes are proposed to solve at least some of the above problems.
[0011] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a metal M and a ligand L coordinated with the metal M. a , wherein the metal M is selected from metals with a relative atomic mass greater than 40, L a Having a structure represented by Formula 1:
[0012]
[0013] In formula 1,
[0014] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;
[0015] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0016] X 1 -X 4 Each occurrence is selected from C, CR, either identically or differently x or N, X 1 -X 4 At least one of them is C and is connected to the Cy;
[0017] X 5 -X 7 Each occurrence is selected from CR x or N;
[0018] X 8 Selected from C;
[0019] X 1 , X 2 , X 3 or X 4 Connected to the metal M via a metal-carbon bond or a metal-nitrogen bond;
[0020] R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted 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 amine 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 thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0021] R xeach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 -20 carbon atoms, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted arylgermanyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0022] R w The group consisting of the following is selected, at each occurrence, identically or differently: substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted aralkylene having 7 to 30 carbon atoms, substituted or unsubstituted alkyleneoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylenethio having 1 to 20 carbon atoms, substituted or unsubstituted substituted arylenethio groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene groups having 2 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylenesilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenesilanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylenegermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenegermanyl groups having 6 to 20 carbon atoms, and combinations thereof;
[0023] The adjacent substituents R', R w , R x Can optionally be linked to form a ring.
[0024] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising:
[0025] anode,
[0026] cathode,
[0027] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex described in the above embodiment.
[0028] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises the metal complex described in the above embodiment.
[0029] The present invention discloses a series of L having a structure of Formula 1 a The metal complex of the ligand can be used as a luminescent material in an electroluminescent device. These novel metal complexes can be applied to electroluminescent devices to improve the efficiency of the device, and ultimately achieve the beneficial effect of significantly improving the overall performance of the device. BRIEF DESCRIPTION OF THE DRAWINGS
[0030] Figure 1 is a schematic diagram of an electroluminescent device that may contain combinations of metal complexes and compounds disclosed herein.
[0031] Figure 2 is a schematic diagram of another electroluminescent device that may contain the metal complexes and compound combinations disclosed herein. DETAILED DESCRIPTION
[0032] 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.
[0033] 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.
[0034] 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.
[0035] 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.
[0036] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0037] 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.
[0038] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0039] 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.
[0040] 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.
[0041] 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.
[0042] 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).
[0043] 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.
[0044] 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).
[0045] Definition of Substituent Terms
[0046] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0047] 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.
[0048] 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.
[0049] 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.
[0050] Alkenyl - as used herein, encompasses straight chain, branched, and cyclic olefin groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, 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, +
[0051] 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.
[0052] Aryl or aromatic group or aromatic ring - As used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, 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.
[0053] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.
[0054] Heteroaryl or heteroaromatic ring - 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.
[0055] 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.
[0056] 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.
[0057] Alkylthio-as used herein, represented by -S-alkyl, -S-cycloalkyl, -S-heteroalkyl or -S-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as above. Alkylthio can be an alkylthio with 1 to 20 carbon atoms, preferably an alkylthio with 1 to 6 carbon atoms. Examples of alkylthio include methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, tetrahydrofuranylthio, tetrahydropyranylthio, methylthiopropylthio, ethylthioethylthio, methylthiomethylthio and ethylthiomethylthio. In addition, alkylthio can be optionally substituted.
[0058] Arylthio-As used herein, represented by -S-aryl or -S-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Arylthio may be an arylthio having 6 to 30 carbon atoms, preferably an arylthio having 6 to 20 carbon atoms. Examples of arylthio include phenylthio, biphenylthio, naphthylthio. In addition, arylthio may be optionally substituted.
[0059] 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,
[0060] 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or at least two CH groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0065] 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 alkylthio, substituted arylthio, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilanyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl The substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl means that any one of an alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino group may be replaced by one or at least two groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted cycloalkyl having 3-20 carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 carbon 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 aralkyl having 6-30 carbon atoms The invention also includes but is not limited to aryl groups, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups and combinations thereof.
[0066] 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.
[0067] 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.
[0068] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.
[0069] 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, heterocyclic, 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.
[0070] 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:
[0071]
[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to 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:
[0073]
[0074] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0075]
[0076] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0077]
[0078] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a metal M and a ligand L coordinated with the metal M. a , wherein the metal M is selected from metals with a relative atomic mass greater than 40, L a Having a structure represented by Formula 1:
[0079]
[0080] In formula 1,
[0081] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;
[0082] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0083] X 1 -X 4 Each occurrence is selected from C, CR, either identically or differently x or N, X 1 -X 4 At least one of them is C and is connected to the Cy;
[0084] X 5 -X 7 Each occurrence is selected from CR x or N;
[0085] X 8 Selected from C;
[0086] X 1 , X 2 , X 3 or X 4 Connected to the metal M via a metal-carbon bond or a metal-nitrogen bond;
[0087] R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted 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 amine 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 thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0088] R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 -20 carbon atoms, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted arylgermanyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0089] R wThe group consisting of the following is selected, at each occurrence, identically or differently: substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted aralkylene having 7 to 30 carbon atoms, substituted or unsubstituted alkyleneoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylenethio having 1 to 20 carbon atoms, substituted or unsubstituted substituted arylenethio groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene groups having 2 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylenesilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenesilanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylenegermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenegermanyl groups having 6 to 20 carbon atoms, and combinations thereof;
[0090] The adjacent substituents R', R w , R x Can optionally be linked to form a ring.
[0091] As used herein, “adjacent substituents R′, R w and R x "can be optionally connected to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R x Between the two substituents R' and R x Between the two substituents R w and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0092] According to one embodiment of the present invention, wherein Cy is selected from any structure in the group consisting of:
[0093]
[0094] in,
[0095] Each occurrence of R is the same or different, indicating mono-substitution, poly-substitution, or no substitution; when multiple R are present in any structure, the R are the same or different;
[0096] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted 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 amine 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;
[0097] Two adjacent substituents R can optionally be linked to form a ring;
[0098] Wherein, “#” indicates the position connected to the metal M. Indicates that X 1 , X 2 , X 3 or X 4 The location of the connection.
[0099] Herein, "two adjacent substituents R can be optionally connected to form a ring" is intended to mean that any one or more of the substituent groups formed between any two adjacent substituents R can be connected to form a ring. Obviously, these substituents may not be connected to form a ring.
[0100] According to one embodiment of the present invention, L a Each occurrence is identically or differently selected from the group consisting of:
[0101]
[0102]
[0103] in,
[0104] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0105] R and R x Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0106] R, R' are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0107] R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 -20 carbon atoms, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted arylgermanyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0108] Rw The group consisting of the following is selected, at each occurrence, identically or differently: substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted aralkylene having 7 to 30 carbon atoms, substituted or unsubstituted alkyleneoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylenethio having 1 to 20 carbon atoms, substituted or unsubstituted substituted arylenethio groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene groups having 2 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylenesilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenesilanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylenegermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenegermanyl groups having 6 to 20 carbon atoms, and combinations thereof;
[0109] Adjacent substituents R, R', R w and R x Can optionally be linked to form a ring.
[0110] As used herein, “adjacent substituents R, R′, R w and R x "can be optionally connected 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 x Between the two substituents R' and R x Between the two substituents R w and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0111] According to one embodiment of the present invention, the metal complex has M(L a ) m (L b ) n (L c ) q The general formula of
[0112] in,
[0113] M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt;
[0114] L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand; for example, L a , L b and L c Any two of can be connected to form a tetradentate ligand; for example, L a , L b and L c can be connected to each other to form a hexadentate ligand; or for example, L a , L b , L c None of them are connected so as not to form a multidentate ligand;
[0115] m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a The same or different; when n is equal to 2, the two L b The same or different; when q is equal to 2, the two L c Same or different;
[0116] L b and L c Each occurrence is identically or differently selected from any one of the following groups:
[0117]
[0118] in,
[0119] R a , R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0120] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;
[0121] R a , R b , R c , R N1 , R C1and R C2 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine 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;
[0122] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.
[0123] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0124] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears, the same or different.
[0125] According to one embodiment of the present invention, the metal M is selected from Pt or Ir, the same or different each time it occurs.
[0126] According to one embodiment of the present invention, the metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 3:
[0127]
[0128] in,
[0129] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0130] m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different;
[0131] Y 1 -Y 4 Each occurrence is selected from CR y or N;
[0132] X 3 -X 7 Each occurrence is selected from CR x or N;
[0133] X 8 Selected from C;
[0134] R', R y , R 1 -R 8The 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 amine 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;
[0135] R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 -20 carbon atoms, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted arylgermanyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0136] R wThe group consisting of the following is selected, at each occurrence, identically or differently: substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted aralkylene having 7 to 30 carbon atoms, substituted or unsubstituted alkyleneoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylenethio having 1 to 20 carbon atoms, substituted or unsubstituted substituted arylenethio groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene groups having 2 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylenesilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenesilanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylenegermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenegermanyl groups having 6 to 20 carbon atoms, and combinations thereof;
[0137] The adjacent substituents R', R w , R x and R y can optionally be linked to form a ring;
[0138] Adjacent substituent R 1 -R 8 Can optionally be linked to form a ring.
[0139] As used herein, “adjacent substituents R′, R w , R x and R y "can be optionally connected to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R x Between the two substituents R y Between the two substituents R w and R x Any one or at least two of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0140] In this context, “the adjacent substituent R 1 -R 8 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, adjacent substituents R 1 and R 2 Between adjacent substituents R 3 and R 2Between adjacent substituents R 3 and R 4 Between adjacent substituents R 5 and R 4 Between adjacent substituents R 5 and R 6 Between adjacent substituents R 7 and R 6 Between adjacent substituents R 7 and R 8 Any one or at least two of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0141] According to one embodiment of the present invention, the metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 3A:
[0142]
[0143] in,
[0144] m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different;
[0145] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0146] R x and R y The same or different at each occurrence indicates mono-, poly- or no-substitution;
[0147] R', R y , R 1 -R 8The 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 amine 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;
[0148] R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 -20 carbon atoms, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted alkylgermanyl, substituted or unsubstituted arylgermanyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0149] R wThe group consisting of the following is selected, at each occurrence, identically or differently: substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted aralkylene having 7 to 30 carbon atoms, substituted or unsubstituted alkyleneoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylenethio having 1 to 20 carbon atoms, substituted or unsubstituted substituted arylenethio groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene groups having 2 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylenesilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenesilanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylenegermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylenegermanyl groups having 6 to 20 carbon atoms, and combinations thereof;
[0150] The adjacent substituents R', R w , R x and R y can optionally be linked to form a ring;
[0151] Adjacent substituent R 1 -R 8 Can optionally be linked to form a ring.
[0152] According to one embodiment of the present invention, X is selected from O or S.
[0153] According to one embodiment of the present invention, wherein X is O.
[0154] According to one embodiment of the present invention, X 1 -X 7 Each occurrence is selected from C or CR, either identically or differently x .
[0155] According to one embodiment of the present invention, X 1 -X 7 At least one of them is N, for example, X 1 -X 7 One of them is N or X 1 -X 7 There are two N in it.
[0156] According to one embodiment of the present invention, in Formula 3, X 3 -X 7Each occurrence is selected from CR x .
[0157] According to one embodiment of the present invention, in Formula 3, X 3 -X 7 At least one of them is N, for example, X 3 -X 7 One of them is N or X 3 -X 7 There are two N in it.
[0158] According to one embodiment of the present invention, Y 1 -Y 4 Each occurrence is selected from CR y .
[0159] According to one embodiment of the present invention, Y 1 -Y 4 At least one of them is N, for example, Y 1 -Y 4 One of them is N or Y 1 -Y 4 There are two N in it.
[0160] According to one embodiment of the present invention, X 3 -X 7 At least one selected from CR x , and the R x It's cyano.
[0161] According to one embodiment of the present invention, X 5 -X 7 At least one selected from CR x , and the R x It's cyano.
[0162] According to one embodiment of the present invention, X 7 Yes CR x , and the R x It's cyano.
[0163] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, and combinations thereof.
[0164] According to one embodiment of the present invention, Rx Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
[0165] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, cyano, and combinations thereof.
[0166] According to one embodiment of the present invention, R x At least one of the following is selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
[0167] According to one embodiment of the present invention, R x At least one of the following is selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, cyano, and combinations thereof.
[0168] According to one embodiment of the present invention, R w Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkylene having 1-20 carbon atoms, substituted or unsubstituted heterocyclylene having 3-20 ring atoms, substituted or unsubstituted aralkylene having 7-30 carbon atoms, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, and combinations thereof.
[0169] According to one embodiment of the present invention, R wEach occurrence is identically or differently selected from the group consisting of 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, and combinations thereof.
[0170] According to one embodiment of the present invention, R w On each occurrence it is identically or differently selected from arylene groups having 6 to 30 carbon atoms.
[0171] According to one embodiment of the present invention, R w Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted arylene having 6 to 12 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 12 carbon atoms.
[0172] According to one embodiment of the present invention, R w Each occurrence is identically or differently selected from the group consisting of: cyclopentylene, cyclohexylene, phenylene, pyridylene, pyrimidylene, triazinylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, silylene, quinolylene, isoquinolylene, dithienylene, difuranylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, triphenylene, carbazolylene, azacarbazolylene, azafluorenylene, azasilylene, azadibenzofuranylene, azadibenzothienylene, and combinations thereof; optionally, the hydrogen in the above groups is partially or fully deuterated.
[0173] According to one embodiment of the present invention, R w Each occurrence is identically or differently selected from the group consisting of A-1 to A-194, the specific structures of A-1 to A-194 are shown below:
[0174]
[0175]
[0176]
[0177] and combinations thereof.
[0178] According to one embodiment of the present invention, the hydrogen in A-1 to A-194 can be partially or completely replaced by deuterium.
[0179] According to one embodiment of the present invention, in Formula 3 and 3A, R yEach 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 aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.
[0180] According to one embodiment of the present invention, in Formula 3 and 3A, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 11 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
[0181] According to one embodiment of the present invention, in Formula 3, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms.
[0182] According to one embodiment of the present invention, in Formula 3 and 3A, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, and combinations thereof.
[0183] According to one embodiment of the present invention, in Formula 3 and 3A, at least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0184] According to one embodiment of the present invention, in Formula 3 and 3A, R 5 -R 8At least one or at least two of them are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R 5 -R 8 The sum of the number of carbon atoms is at least 4.
[0185] According to one embodiment of the present invention, in Formula 3 and 3A, R 6 and R 7 At least one or at least two of them are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R 6 and R 7 The sum of the number of carbon atoms is at least 4.
[0186] According to one embodiment of the present invention, in Formula 3 and 3A, R 7 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 a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amine 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 thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0187] According to one embodiment of the present invention, in Formula 3 and 3A, R 7 The group is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 ring carbon atoms, or a combination thereof.
[0188] According to one embodiment of the present invention, in Formula 3 and 3A, R 2 , R 3 , R 6 , R 7At least one or at least two or at least three or all of them are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0189] According to one embodiment of the present invention, in Formula 3 and 3A, R 2 , R 3 , R 6 , R 7 At least one, at least two, at least three, or all of them are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.
[0190] According to one embodiment of the present invention, in Formula 3 and 3A, R 2 , R 3 , R 6 , R 7 At least one or at least two or at least three or all of them are selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof.
[0191] According to one embodiment of the present invention, R' is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
[0192] According to one embodiment of the present invention, R' is selected from methyl or deuterated methyl.
[0193] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 To L a770 The group, where L a1 To L a770 The specific structure is as follows:
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224] According to one embodiment of the present invention, L a1To L a770 The hydrogen in the structure can be partially or completely replaced by deuterium.
[0225] According to one embodiment of the present invention, L b Each time it appears, choose the same or different one from L b1 To L b329 The group consisting of L b1 To L b329 The specific structure is as follows:
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233]
[0234]
[0235] According to one embodiment of the present invention, L b1 To L b329 The hydrogen in the structure can be partially or completely replaced by deuterium.
[0236] According to one embodiment of the present invention, L c Each time it appears, choose the same or different one from L c1 To L c360 The group consisting of L c1 To L c360 The specific structure is as follows:
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245] According to one embodiment of the present invention, the metal complex has Ir(L a ) 2 (L b ) structure, L a Each time it appears, choose the same or different one from L a1 To L a770 Any one or two of the group consisting of L b Choose from L b1 To L b329 Any of the groups consisting of.
[0246] According to one embodiment of the present invention, the metal complex has Ir(L a )(L b ) 2 The structure of L a Each time it appears, choose the same or different one from L a1 To L a770 Any of the groups consisting of L b Choose from L b1 To L b329 Any one or any two of the group consisting of.
[0247] According to one embodiment of the present invention, the metal complex has Ir(L a ) 3 The structure of L a Each time it appears, choose the same or different one from L a1 To L a770 Any one, any two, or any three of the group consisting of.
[0248] According to one embodiment of the present invention, the metal complex has Ir(L a ) 2 (L c ) structure, L a Each time it appears, choose the same or different one from L a1 To L a770 Any one or two of the group consisting of L c Choose from L c1 To L c360 Any of the groups consisting of.
[0249] According to one embodiment of the present invention, the metal complex has Ir(L a )(L c )2 The structure of L a Each time it appears, choose the same or different one from L a1 To L a770 Any of the groups consisting of L c Choose from L c1 To L c360 Any one or any two of the group consisting of.
[0250] According to one embodiment of the present invention, the metal complex has Ir(L a )(L b )(L c ) structure, where L a Each time it appears, choose the same or different one from L a1 To L a770 Any of the groups consisting of L b Choose from L b1 To L b329 Any of the groups consisting of L c Choose from L c1 To L c360 Any of the groups consisting of.
[0251] According to one embodiment of the present invention, the metal complex is selected from metal complex 1 to metal complex 1578, and the specific structures of metal complex 1 to metal complex 1578 are as follows:
[0252] Among them, metal complexes 1 to 1488 have IrL a (L b ) 2 The structure of two L b The structures of L are the same or different. a and two L b They correspond to the structures shown in the following table:
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268]
[0269]
[0270]
[0271]
[0272]
[0273]
[0274] Among them, metal complexes 1489 to 1530 have Ir(L a ) 2 L c The structure of two L a Same or different, two L a and L c They correspond to the structures shown in the following table:
[0275]
[0276] Among them, metal complexes 1531 to 1554 have Ir(L a )(L b )(L c ) structure, where L a , L b , L c They correspond to the structures shown in the following table:
[0277] Metal Complexes <![CDATA[L a ]]> <![CDATA[L b ]]> <![CDATA[L c ]]> Metal Complexes <![CDATA[L a ]]> <![CDATA[L b ]]> <![CDATA[L c <!-- 91 -->]]> 1531 <![CDATA[L a1 ]]> <![CDATA[L b1 ]]> <![CDATA[L c31 ]]> 1532 <![CDATA[L a1 ]]> <![CDATA[L b3 ]]> <![CDATA[L c31 ]]> 1533 <![CDATA[L a1 ]]> <![CDATA[L b12 ]]> <![CDATA[L c31 ]]> 1534 <![CDATA[L a1 ]]> <![CDATA[L b15 ]]> <![CDATA[L c31 ]]> 1535 <![CDATA[L a1 ]]> <![CDATA[L b17 ]]> <![CDATA[L c31 ]]> 1536 <![CDATA[L a1 ]]> <![CDATA[L b81 ]]> <![CDATA[L c31 ]]> 1537 <![CDATA[L a1 ]]> <![CDATA[L b85 ]]> <![CDATA[L c31 ]]> 1538 <![CDATA[L a1 ]]> <![CDATA[L b90 ]]> <![CDATA[L c31 ]]> 1539 <![CDATA[L a218 ]]> <![CDATA[L b1 ]]> <![CDATA[L c31 ]]> 1540 <![CDATA[L a218 ]]> <![CDATA[L b3 ]]> <![CDATA[L c31 ]]> 1541 <![CDATA[L a218 ]]> <![CDATA[L b12 ]]> <![CDATA[L c31 ]]> 1542 <![CDATA[L a218 ]]> <![CDATA[L b15 ]]> <![CDATA[L c31 ]]> 1543 <![CDATA[L a218 ]]> <![CDATA[L b17 ]]> <![CDATA[L c31 ]]> 1544 <![CDATA[L a218 ]]> <![CDATA[L b81 ]]> <![CDATA[L c31 ]]> 1545 <![CDATA[L a218 ]]> <![CDATA[L b85 ]]> <![CDATA[L c31 ]]> 1546 <![CDATA[L a218 ]]> <![CDATA[L b90 ]]> <![CDATA[L c31 ]]> 1547 <![CDATA[L a463 ]]> <![CDATA[L b1 ]]> <![CDATA[L c31 ]]> 1548 <![CDATA[L a463 ]]> <![CDATA[L b3 ]]> <![CDATA[L c31 ]]> 1549 <![CDATA[L a463 ]]> <![CDATA[L b12 ]]> <![CDATA[L c31 ]]> 1550 <![CDATA[L a463 ]]> <![CDATA[L b15 ]]> <![CDATA[L c31 ]]> 1551 <![CDATA[L a463 ]]> <![CDATA[L b17 ]]> <![CDATA[L c31 ]]> 1552 <![CDATA[L a463 ]]> <![CDATA[L b81 ]]> <![CDATA[L c31 ]]> 1553 <![CDATA[L a463 ]]> <![CDATA[L b85 ]]> <![CDATA[L c31 ]]> 1554 <![CDATA[L a463 ]]> <![CDATA[L b90 ]]> <![CDATA[L c31 ]]> ;
[0278] Among them, metal complexes 1555 to 1578 have Ir(L a )3 The structure of which 3 L a Same or different, 3 Ls a They correspond to the structures shown in the following table:
[0279] Metal Complexes <![CDATA[L a ]]> <![CDATA[L a ]]> <![CDATA[L a ]]> Metal Complexes <![CDATA[L a ]]> <![CDATA[L a ]]> <![CDATA[L a ]]> 1555 <![CDATA[L a1 ]]> <![CDATA[L a1 ]]> <![CDATA[L a1 ]]> 1556 <![CDATA[L a54 ]]> <![CDATA[L a54 ]]> <![CDATA[L a54 ]]> 1557 <![CDATA[L a218 ]]> <![CDATA[L a218 ]]> <![CDATA[L a218 ]]> 1558 <![CDATA[L a230 ]]> <![CDATA[L a230 ]]> <![CDATA[L a230 ]]> 1559 <![CDATA[L a243 ]]> <![CDATA[L a243 ]]> <![CDATA[L a243 ]]> 1560 <![CDATA[L a155 ]]> <![CDATA[L a155 ]]> <![CDATA[L a155 ]]> 1561 <![CDATA[L a313 ]]> <![CDATA[L a313 ]]> <![CDATA[L a313 ]]> 1562 <![CDATA[L a254 ]]> <![CDATA[L a254 ]]> <![CDATA[L a254 ]]> 1563 <![CDATA[L a171 ]]> <![CDATA[L a171 ]]> <![CDATA[L a171 ]]> 1564 <![CDATA[L a465 ]]> <![CDATA[L a465 ]]> <![CDATA[L a465 ]]> 1565 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a4 ]]> 1566 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a6 ]]> 1567 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a10 ]]> 1568 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a13 ]]> 1569 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a25 ]]> 1570 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a28 ]]> 1571 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a35 ]]> 1572 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a37 ]]> 1573 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a40 ]]> 1574 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a42 ]]> 1575 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a45 ]]> 1576 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a65 ]]> 1577 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a80 ]]> 1578 <![CDATA[L a1 ]]> <![CDATA[L a3 ]]> <![CDATA[L a88 ]]> .
[0280] According to one embodiment of the present invention, hydrogen in the structures of metal complexes 1 to 1578 can be partially or completely replaced by deuterium.
[0281] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0282] anode,
[0283] cathode,
[0284] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex described in any one of the above embodiments.
[0285] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.
[0286] According to an embodiment of the present invention, the electroluminescent device emits green light.
[0287] According to an embodiment of the present invention, the electroluminescent device emits white light.
[0288] According to an embodiment of the present invention, the light-emitting layer of the electroluminescent device comprises a first host compound.
[0289] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device comprises a first host compound and a second host compound.
[0290] According to one embodiment of the present invention, the first host compound and / or the second host compound in the electroluminescent device contain 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.
[0291] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 4:
[0292]
[0293] in,
[0294] E 1 -E 6 Each occurrence is selected from C, CR, either identically or differently e or N, and E 1 -E 6 At least two of them are N, E 1 -E 6 At least one of them is C and is connected to formula A;
[0295]
[0296] in,
[0297] Q is selected from the group consisting of O, S, Se, N, NR"', CR"'R"', SiR"'R"', GeR"'R"' and R"'C=CR"' at each occurrence; when two R"' exist at the same time, the two R"' may be the same or different;
[0298] p is 0 or 1; r is 0 or 1;
[0299] When Q is selected from N, p is 0 and r is 1;
[0300] When Q is selected from the group consisting of O, S, Se, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', p is 1 and r is 0;
[0301] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0302] Q 1 -Q 8 Each occurrence is selected from C, CR, either identically or differently q or N;
[0303] R e , R'' and R qEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine 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;
[0304] “*” represents the connection position between Formula A and Formula 4;
[0305] Adjacent substituent R e , R”', R q Can optionally be linked to form a ring.
[0306] In this context, “the adjacent substituent R e , R”, R q "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R e Between two substituents R", between two substituents R q Between the two substituents R" and R q Any one or at least two of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0307] According to one embodiment of the present invention, each occurrence of Q is identically or differently selected from O, S, N or NR".
[0308] According to one embodiment of the present invention, E 1 -E 6 Each occurrence is selected from C, CR, either identically or differently e or N, and E 1 -E 6 There are three N, E 1- E 6At least one is CR e , and the R e Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
[0309] According to one embodiment of the present invention, E 1 -E 6 Each occurrence is selected from C, CR, either identically or differently e or N, and E 1 -E 6 There are three N, E 1 -E 6 At least one is CR e , and the R e Each occurrence is identically or differently selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof.
[0310] According to one embodiment of the present invention, R e Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
[0311] According to one embodiment of the present invention, R e Each occurrence is identically or differently selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof.
[0312] According to one embodiment of the present invention, Q 1 -Q 8 At least one or at least two selected from CR q , and the R q is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof.
[0313] According to one embodiment of the present invention, Q 1 -Q 8At least one or at least two selected from CR q , and the R q is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, or a combination thereof.
[0314] According to one embodiment of the present invention, each occurrence of R'' is identically or differently selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a combination thereof.
[0315] According to one embodiment of the present invention, R'' is selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, or a combination thereof, at each occurrence.
[0316] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, the same or different each time it occurs.
[0317] According to one embodiment of the present invention, wherein L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted fluorenylene the same or differently each time it appears.
[0318] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted biphenylene group, the same or different when it appears each time.
[0319] According to one embodiment of the present invention, the first host compound is selected from the group consisting of H-1 to H-243, wherein the specific structures of H-1 to H-243 are as follows:
[0320]
[0321]
[0322]
[0323]
[0324]
[0325]
[0326]
[0327]
[0328]
[0329]
[0330]
[0331]
[0332]
[0333]
[0334]
[0335]
[0336]
[0337]
[0338]
[0339] According to one embodiment of the present invention, the second host compound in the electroluminescent device has a structure represented by Formula 5:
[0340]
[0341] in,
[0342] L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0343] Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect;
[0344] Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and Lx connect;
[0345] R v and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine 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;
[0346] Ar 6 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0347] Adjacent substituent R v and R u Can optionally be linked to form a ring.
[0348] In this embodiment, "the adjacent substituent R v and R u "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R v Between the two substituents R u Between the two substituents R v and R u Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0349] According to one embodiment of the present invention, the second host compound in the electroluminescent device has a compound having a formula of 5-a to
[0350] The structure represented by one of formula 5-j:
[0351]
[0352]
[0353] in,
[0354] L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0355] Each time V appears, it is selected from CR in the same or different way. v or N;
[0356] Each time U appears, it is selected from CR in the same or different way. u or N;
[0357] R v and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine 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;
[0358] Ar 6 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0359] Adjacent substituent R v and R uCan optionally be linked to form a ring.
[0360] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compounds X-1 to X-150, wherein the specific structures of compounds X-1 to X-150 are as follows:
[0361]
[0362]
[0363]
[0364]
[0365]
[0366]
[0367]
[0368]
[0369]
[0370]
[0371]
[0372]
[0373]
[0374] According to an embodiment of the present invention, in the electroluminescent device, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
[0375] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.
[0376] According to another embodiment of the present invention, a compound combination is disclosed. The compound combination comprises the metal complex described in any of the aforementioned embodiments.
[0377] Combination with other materials
[0378] 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.
[0379] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0380] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.
[0381] Material synthesis example:
[0382] 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:
[0383] Synthesis Example 1: Synthesis of Metal Complex 493
[0384] Step 1:
[0385]
[0386] 5-Methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were added to a dry 500 mL round-bottom flask in sequence, and the nitrogen atmosphere was replaced three times and protected by nitrogen atmosphere, and heated and stirred at 130°C for 24 h. After cooling, the mixture was filtered, rinsed three times with methanol and n-hexane respectively, and dried to obtain 7.5 g of yellow solid intermediate 1 (97% yield).
[0387] Step 2:
[0388]
[0389] In a dry 500 mL round-bottom flask, add intermediate 1 (7.5 g, 6.8 mmol), anhydrous dichloromethane 250 mL, methanol 10 mL, silver trifluoromethanesulfonate (3.8 g, 14.8 mmol), replace with nitrogen three times and protect with nitrogen, stir at room temperature overnight. Filter through diatomaceous earth, rinse with dichloromethane twice, collect the organic phase below and concentrate under reduced pressure to obtain 9.2 g of intermediate 2 (93% yield).
[0390] Step 3:
[0391]
[0392] In a dry 250mL round-bottom flask, add intermediate 3 (3.0g, 8.6mmol), intermediate 2 (3.7g, 5.8mmol), 2-ethoxyethanol and N,N-dimethylformamide 50mL each, replace with nitrogen three times and protect with nitrogen, heat at 100℃ for 96h. After the reaction is cooled, filter with diatomaceous earth. Wash with methanol and n-hexane twice respectively, dissolve the yellow solid on the diatomaceous earth with dichloromethane, collect the organic phase, concentrate under reduced pressure, and purify by column chromatography to obtain a yellow solid product metal complex 493 (2.20g, 43.4% yield). The product is determined to be the target product with a molecular weight of 874.2.
[0393] Synthesis Example 2: Synthesis of Metal Complex 735
[0394] Step 1:
[0395]
[0396] In a dry 250mL round-bottom flask, add intermediate 4 (1.5g, 4.0mmol), intermediate 2 (2.1g, 2.9mmol), 2-ethoxyethanol and N,N-dimethylformamide 50mL each, replace with nitrogen three times and protect with nitrogen, heat at 100℃ for 96h. After the reaction is cooled, filter with diatomaceous earth. Wash with methanol and n-hexane twice respectively, dissolve the yellow solid on the diatomaceous earth with dichloromethane, collect the organic phase, concentrate under reduced pressure, and purify by column chromatography to obtain a yellow solid product metal complex 735 (1.1g, 42.6% yield). The product is determined to be the target product with a molecular weight of 899.2.
[0397] Synthesis Example 3: Synthesis of Metal Complex 975
[0398] Step 1:
[0399]
[0400] 5-tert-butyl-2-phenylpyridine (13.2 g, 62.9 mmol), iridium trichloride trihydrate (5.5 g, 15.7 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were added to a dry 500 mL round-bottom flask in sequence, and the nitrogen atmosphere was replaced three times and protected by nitrogen atmosphere, and heated and stirred at 130°C for 24 h. After cooling, the mixture was filtered, rinsed three times with methanol and n-hexane respectively, and dried to obtain 9.7 g of intermediate 5 (97% yield).
[0401] Step 2:
[0402]
[0403] In a dry 500 mL round-bottom flask, intermediate 5 (9.7 g, 7.7 mmol), anhydrous dichloromethane 250 mL, methanol 10 mL, silver trifluoromethanesulfonate (4.3 g, 16.7 mmol) were added in sequence, nitrogen was replaced three times and nitrogen was protected, and stirred at room temperature overnight. Celite was filtered, and dichloromethane was rinsed twice, and the organic phase below was collected and concentrated under reduced pressure to obtain 13.2 g of yellow solid intermediate 6 (93% yield).
[0404] Step 3:
[0405]
[0406] Add intermediate 3 (1.2 g, 3.5 mmol), intermediate 6 (2.0 g, 2.5 mmol), 2-ethoxyethanol and N, N-dimethylformamide 50 mL each into a dry 250 mL round-bottom flask, replace with nitrogen three times and protect with nitrogen, heat at 100 ° C for 96 h. After the reaction is cooled, filter with diatomaceous earth. Wash with methanol and n-hexane twice respectively, dissolve the yellow solid on the diatomaceous earth with dichloromethane, collect the organic phase, concentrate under reduced pressure, and purify by column chromatography to obtain a yellow solid product metal complex 975 (1.3 g, 54.3% yield). The product is determined to be the target product with a molecular weight of 958.3.
[0407] Synthesis Example 4: Synthesis of Metal Complex 1192
[0408] Step 1:
[0409]
[0410] In a dry 250mL round-bottom flask, add intermediate 7 (1.5g, 4.0mmol), intermediate 6 (2.2g, 2.7mmol), 2-ethoxyethanol and N,N-dimethylformamide 50mL each, replace with nitrogen three times and protect with nitrogen, heat at 100℃ for 96h. After the reaction is cooled, filter with diatomaceous earth. Wash with methanol and n-hexane twice respectively, dissolve the yellow solid on the diatomaceous earth with dichloromethane, collect the organic phase, concentrate under reduced pressure, and purify by column chromatography to obtain a yellow solid product metal complex 1192 (1.3g, 50.0% yield). The product is determined to be the target product with a molecular weight of 983.3.
[0411] 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.
[0412] Device Example 1-1
[0413] 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 -8In the case of 1000 Å / s, the ITO anode is sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound H1 is used as an electron blocking layer (EBL). Then the metal complex 493 of the present invention is co-deposited with compound H1 and compound H2 as a dopant as a light-emitting layer (EML). On the EML, compound HB is used as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover to complete the device.
[0414] Device Comparison Example 1-1
[0415] The device comparative example 1-1 is implemented in the same manner as the device example 1-1, except that the metal complex 493 of the present invention is replaced with compound GD1 in the light emitting layer (EML).
[0416] Device Comparison Example 1-2
[0417] The implementation of Comparative Device Example 1-2 is the same as that of Example 1-1, except that the metal complex 493 of the present invention is replaced with Compound GD2 in the light emitting layer (EML).
[0418] 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.
[0419] Table 1 Device structures of Example 1-1 and Comparative Examples 1-1 to 1-2
[0420]
[0421] The material structure used in the device is shown below:
[0422]
[0423]
[0424] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , voltage (V), current efficiency (CE), power efficiency (PE). External quantum efficiency (EQE) data is at 15mA / cm 2 The tests were performed at a constant current and these data are recorded and shown in Table 2.
[0425] Table 2 Device structure and device data of Examples 1-1 to 1-2 and Comparative Examples 1-1 to 1-2
[0426]
[0427] Table 2 shows the device performance of the compounds of the present invention and the comparative compounds. The only difference between Example 1-1 and Comparative Example 1-1 is that the L a The substitution position of the cyano substituent on the ligand is different. The driving voltage of the device is slightly reduced, the PE is slightly increased, and the EQE is significantly increased by 10.1%. The difference between Example 1-1 and Comparative Example 1-2 is only that the L of the metal complex a Ligand X 8 The device voltage was reduced by 0.17 V, and CE, PE and EQE were increased by 9.5%, 17.1% and 11.0%, respectively, depending on whether the substituent at the position contained a cyano group.
[0428] The above data show that in the present invention, a The metal complex substituted with a cyano-containing substituent at a specific position is significantly better than the metal complex of the comparative example in terms of device efficiency performance, and can significantly improve the overall performance of the device.
[0429] Device Example 2-1
[0430] The implementation of Device Example 2-1 is the same as that of Device Example 1-1, except that the present metal complex 975 is used instead of the present metal complex 493 in the light-emitting layer.
[0431] Device Example 2-2
[0432] The implementation of Device Example 2-2 is the same as that of Device Example 1-1, except that the present metal complex 1192 is used instead of the present metal complex 493 in the light-emitting layer.
[0433] Device Comparison Example 2-1
[0434] The device comparative example 2-1 is implemented in the same manner as the device example 1-1, except that the compound GD3 is used instead of the metal complex 493 of the present invention in the light emitting layer (EML).
[0435] Device Comparison Example 2-2
[0436] The device comparative example 2-2 is implemented in the same manner as the device example 1-1, except that the compound GD4 is used instead of the metal complex 493 of the present invention in the light emitting layer (EML).
[0437] 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.
[0438] Table 3 Device structures of Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-2
[0439]
[0440] The new material structure used in the device is shown below:
[0441]
[0442] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE). These data are recorded and shown in Table 4.
[0443] Table 4 Device structure and device data of Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-2
[0444]
[0445] Table 4 shows the device performance of the compounds of the present invention and the comparative compounds. The difference between Example 2-1 and Comparative Example 2-1, and between Example 2-2 and Comparative Example 2-2, is that the L a Ligand X 8 Whether the substituent at the position contains a cyano group. Compared with Comparative Example 2-1, the driving voltage of the device in Example 2-1 is reduced by 0.42V, and CE, PE and EQE are significantly improved by 15.9%, 33.7% and 15.4%, respectively; compared with Comparative Example 2-2, the driving voltage of the device in Example 2-2 is reduced by 0.11V, CE and PE are improved by about 5%, and EQE is improved by 8.1%.
[0446] The above data show that in the present invention, a The metal complex substituted with a cyano substituent at a specific position is significantly better than the metal complex of the comparative example in terms of device efficiency performance, and can significantly improve the overall performance of the device.
[0447] From the above discussed embodiments and comparative examples, it can be seen that the present invention contains L a Ligand X 8 The metal complexes with substituents containing cyano groups at the positions of the metal complexes can significantly improve device performance compared to the comparative metal complexes. The advantages observed for the compounds of the present invention are completely unexpected. Even for those skilled in the art, it is impossible to predict this situation.
[0448] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.
Claims
1. A metal complex, the metal complex is Ir(L a ) m (L b ) 3-m And has a structure represented by Formula 3: in, X is selected from the group consisting of O, S, Se; m is selected from 1; two L b Same or different; Each occurrence of Y1-Y4 is identical or different and is selected from CR y ; X3-X7 are selected from CR in the same or different way each time they appear. x ; X8 is selected from C; R y , R1-R8 are each 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 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-10 carbon atoms, cyano, isocyano, and combinations thereof; R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 10 carbon atoms, cyano, isocyano, and combinations thereof; R w Each occurrence is identically or differently selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, and combinations thereof; Wherein, the substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, and substituted alkylsilyl refer to any one of the alkyl, cycloalkyl, aryl, heteroaryl, and alkylsilyl groups which may be substituted by one or at least two groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted aryl having 6 to 12 carbon atoms, unsubstituted heteroaryl having 3 to 12 carbon atoms, unsubstituted alkylsilyl having 3 to 10 carbon atoms, cyano, isocyano, and combinations thereof.
2. The metal complex according to claim 1, wherein R x , R y , R1-R8 are selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, cyano, and combinations thereof at each occurrence; R w Each occurrence is identically or differently selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 12 carbon atoms, and combinations thereof.
3. The metal complex according to any one of claims 1 to 2, wherein X is selected from O or S.
4. The metal complex according to claim 3, wherein R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 4-10 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3-10 carbon atoms, cyano, and combinations thereof.
5. The metal complex according to claim 1, wherein R x At least one of the following is selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
6. The metal complex according to claim 1, wherein R x At least one of the following is selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, cyano, and combinations thereof.
7. The metal complex according to claim 1, wherein R w On each occurrence it is identically or differently selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.
8. The metal complex according to claim 1, wherein R w Each occurrence is identically or differently selected from the group consisting of: phenylene, pyridinylene, pyrimidinylene, triazinylene, naphthylene, quinolylene, isoquinolylene, dithienylene, difuranylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, carbazolylene, azacarbazolylene, azadibenzofuranyl, azadibenzothienylene, and combinations thereof; optionally, the hydrogen in the above groups is partially or fully deuterated.
9. The metal complex according to claim 1, wherein R w Each time it occurs, it is selected from and combinations thereof; Optionally, the hydrogen in the above groups can be partially or completely replaced by deuterium; wherein "*" indicates the connection position with X8, and "#" indicates the connection position with "CN".
10. The metal complex according to claim 1, wherein R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 4-10 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 3-12 carbon atoms, and combinations thereof.
11. The metal complex according to claim 4, wherein At least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 4-10 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, and combinations thereof.
12. The metal complex according to claim 4, wherein At least one or at least two of R5-R8 are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and the total number of carbon atoms of all R5-R8 is at least 4.
13. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and combinations thereof.
14. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.
15. The metal complex according to claim 4, wherein At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; optionally, the hydrogen in the above groups can be partially or completely deuterated.
16. The metal complex according to claim 1, wherein L a Each occurrence is identically or differently selected from the group consisting of: Wherein, optionally, the hydrogen in the La structure can be partially or completely replaced by deuterium.
17. The metal complex according to claim 16, wherein L b Each occurrence is identically or differently selected from the group consisting of: Wherein, optionally, the L b The hydrogen in the structure can be partially or completely replaced by deuterium.
18. The metal complex according to claim 17, wherein Metal complexes with IrL a (L b )2 structure, where two L b The structures of L are the same or different. a and two L b They correspond to the structures shown in the following table:
19. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between an anode and a cathode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 18.
20. The electroluminescent device of claim 19, wherein: The organic layer including the metal complex is a light-emitting layer.
21. The electroluminescent device of claim 19, wherein: The electroluminescent device emits green light or white light.
22. The electroluminescent device of claim 20, wherein: The light-emitting layer includes a first host compound.
23. The electroluminescent device of claim 22, wherein: The light-emitting layer further includes a second host compound.
24. The electroluminescent device of claim 23, wherein: The first host compound and / or the second host compound contain 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.
25. The electroluminescent device of claim 23, wherein: The first host compound has a structure represented by Formula 4: in, Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, and at least one of E1-E6 is C, and they are connected to formula A; in, Q is selected from the group consisting of O, S, Se, N, NR"', CR"'R"', SiR"'R"', GeR"'R"' and R"'C=CR"' at each occurrence; when two R"' exist at the same time, the two R"' may be the same or different; p is 0 or 1; r is 0 or 1; When Q is selected from N, p is 0 and r is 1; When Q is selected from the group consisting of O, S, Se, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', p is 1 and r is 0; L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N; R e , R'' and R q each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, and combinations thereof; "*" represents the connection position between Formula A and Formula 4; Adjacent substituent R e , R'', R q can be optionally linked into a ring; The 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 means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino may be replaced by one or at least two of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group, unsubstituted aralkyl group having 7 to 30 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted alkynyl group having 2 to 20 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, unsubstituted heteroaryl group having 3 to 30 carbon atoms, unsubstituted alkylsilyl group having 3 to 20 carbon atoms, unsubstituted arylsilanyl group having 6 to 20 carbon atoms, unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, unsubstituted arylgermanyl group having 6 to 20 carbon atoms, unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group and combinations thereof.
26. The electroluminescent device of claim 25, wherein: The first host compound is selected from the group consisting of:
27. The electroluminescent device of claim 23, wherein: The second host compound has a structure represented by Formula 5: in, L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect; Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and L x connect; R v and R u each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, and combinations thereof; Ar6 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R v and R u can optionally be linked to form a ring; The 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 means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino may be replaced by one or at least two of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group, unsubstituted aralkyl group having 7 to 30 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted alkynyl group having 2 to 20 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, unsubstituted heteroaryl group having 3 to 30 carbon atoms, unsubstituted alkylsilyl group having 3 to 20 carbon atoms, unsubstituted arylsilanyl group having 6 to 20 carbon atoms, unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, unsubstituted arylgermanyl group having 6 to 20 carbon atoms, unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group and combinations thereof.
28. The electroluminescent device of claim 23, wherein the second host compound has a structure represented by one of Formula 5-a to Formula 5-j:
29. The electroluminescent device of claim 27, wherein: The second host compound is selected from the group consisting of:
30. The electroluminescent device according to claim 23, wherein a metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
31. The electroluminescent device according to claim 23, wherein the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
32. A compound combination comprising the metal complex according to any one of claims 1-18.
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