An electroluminescent device
By using a new material combination of the first metal complex and the first compound in the electroluminescent device, the problems of reduced efficiency at high brightness and insufficient performance of the blue phosphorescent device are solved, and a more efficient and longer life electroluminescent effect is achieved.
Patent Information
- Application Number
- CN202011492494.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-12-17
- Publication Date
- 2025-02-28
- Estimated Expiration
- 2040-12-17
AI Technical Summary
The efficiency of existing phosphorescence OLEDs is rapidly reduced under high brightness, and blue phosphorescence devices have problems such as unsaturation, short life and high operating voltage, making it difficult to meet the industry's performance needs for electroluminescent devices.
A novel material combination consisting of a first metal complex and a first compound is used for the luminescent layer of the electroluminescent device to achieve a darker color, lower voltage, higher efficiency and longer lifetime.
The darker red color, lower driving voltage, higher luminous efficiency and longer life of electroluminescent devices are achieved, improving device performance.
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Figure CN114649495B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an electronic device, such as an electroluminescent device. More particularly, the electroluminescent device uses a novel material combination consisting of a first metal complex and a first compound. In addition, an electronic device and a compound combination are also disclosed. 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] In order to meet the industry's increasing demands for various aspects of electroluminescent device performance, such as luminescent color, luminescent color saturation, driving voltage, luminescent efficiency, device life, etc., research related to phosphorescent devices is still in urgent need of further study. In the research of phosphorescent devices, the combination of phosphorescent luminescent materials and host materials is very important. The selection of the combination of phosphorescent luminescent materials and host materials is directly related to the luminescent performance of the device. Therefore, the selection and optimization of the combination of phosphorescent luminescent materials and host materials is an important part of the industry's related research. Summary of the invention
[0009] The present invention aims to provide an electroluminescent device with a novel material combination to solve at least part of the above problems. The electroluminescent device uses a novel material combination consisting of a first metal complex and a first compound, and the novel material combination can be used in the light-emitting layer of the electroluminescent device. The novel material combination can enable the novel electroluminescent device to obtain a deeper red color, lower voltage, higher efficiency and longer life, and can provide better device performance.
[0010] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0011] anode,
[0012] cathode,
[0013] and an organic layer disposed between the anode and the cathode, the organic layer comprising a first metal complex and a first compound;
[0014] in,
[0015] The first metal complex comprises a ligand L coordinated to the metal a , and the metal is selected from metals with a relative atomic mass greater than 40; L a Having a structure represented by Formula 1:
[0016]
[0017] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N;
[0018] Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; said R y2 With-L1-SiR s1 R s2 R s3 structure;
[0019] R x , R y1 , R s1, R s2 , R s3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0020] Adjacent substituent R x , R y1 , R s1 , R s2 , R s3 can optionally be linked to form a ring;
[0021] Z is selected from O, S or Se;
[0022] L1 is selected 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;
[0023] in,
[0024] The first compound has a structure represented by Formula 2:
[0025]
[0026] Z1, Z8 are selected from CR in the same or different ways each time they appear z1 or N;
[0027] Each time Z2, Z3, Z6, and Z7 appear, they are selected from CR z2 or N;
[0028] Z4, Z5 are selected from CR in the same or different ways each time they appear z3 or N;
[0029] E has a structure represented by Formula 3-1 or Formula 3-2:
[0030]
[0031] In Formula 3-1 and Formula 3-2, each occurrence of E1-E8 is identically or differently selected from C, CR e or N; and in formula 3-1, at least two of E1-E6 are N, and in formula 3-2, at least two of E1-E8 are N;
[0032] * indicates the location where E and L are connected;
[0033] L is selected 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;
[0034] R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0035] R z2 , R z3 , R e 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0036] Adjacent substituent R z1 , R z2 , R z3 can optionally be linked to form a ring;
[0037] Adjacent substituent R e Can optionally be linked to form a ring.
[0038] According to another embodiment of the present invention, an electronic device is disclosed, which includes the above electroluminescent device.
[0039] According to another embodiment of the present invention, a compound combination is also disclosed, which includes the first metal complex and the first compound.
[0040] The present invention provides an electroluminescent device with a novel material combination, wherein a novel material combination consisting of a first metal complex and a first compound is used in the electroluminescent device, and the novel material combination can be used in the light-emitting layer of the electroluminescent device. The novel material combination can enable the novel electroluminescent device to obtain a deeper red color, lower voltage, higher efficiency and longer life, and can provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS
[0041] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the electroluminescent device disclosed herein.
[0042] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0043] 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.
[0044] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.
[0045] 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.
[0046] 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.
[0047] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0048] 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.
[0049] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0050] 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.
[0051] 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.
[0052] 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.
[0053] 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).
[0054] 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.
[0055] 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).
[0056] Definition of Substituent Terms
[0057] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0058] 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 6 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. In addition, the alkyl group may be optionally substituted. 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.
[0059] 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.
[0060] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.
[0061] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.
[0062] 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.
[0063] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl 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, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.
[0064] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.
[0065] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl or -O-heteroalkyl. Examples and preferred examples of alkyl, cycloalkyl and heteroalkyl 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, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy may be optionally substituted.
[0066] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.
[0067] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,
[0068] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.
[0069] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.
[0070] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0071] 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 aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino. The alkyl radical may be substituted with an alkyl radical having 3 to 20 ring carbon atoms, an unsubstituted cycloalkyl radical having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl radical having 1 to 20 carbon atoms, an unsubstituted aralkyl radical having 7 to 30 carbon atoms, an unsubstituted alkoxy radical having 1 to 20 carbon atoms, an unsubstituted aryloxy radical having 6 to 30 carbon atoms, an unsubstituted alkenyl radical having 2 to 20 carbon atoms, an unsubstituted alkynyl radical having 2 to 20 carbon atoms, an unsubstituted aryl radical having 6 to 30 carbon atoms, an unsubstituted heteroaryl radical having 3 to 30 carbon atoms, an unsubstituted alkylsilyl radical having 3 to 20 carbon atoms, an unsubstituted arylsilyl radical having 6 to 20 carbon atoms, an unsubstituted amino radical having 0 to 20 carbon atoms, an acyl radical, a carbonyl radical, a carboxylic acid radical, an ester radical, a cyano radical, an isocyano radical, a mercapto radical, a sulfinyl radical, a sulfonyl radical, a phosphino radical, and combinations thereof.
[0072] 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.
[0073] 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.
[0074] 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.
[0075] In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation that adjacent substituents can be connected to form a ring and the situation that 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, as well as an alicyclic ring, a heteroalicyclic ring, an aromatic ring or a 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.
[0076] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to 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:
[0077]
[0078] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to 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:
[0079]
[0080] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0081]
[0082] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0083] anode,
[0084] cathode,
[0085] and an organic layer disposed between the anode and the cathode, the organic layer comprising a first metal complex and a first compound;
[0086] in,
[0087] The first metal complex comprises a ligand L coordinated to the metal a , and the metal is selected from metals with a relative atomic mass greater than 40; L a Having a structure represented by Formula 1:
[0088]
[0089] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N;
[0090] Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; said R y2 With-L1-SiR s1 R s2 R s3 structure;
[0091] R x , R y1 , R s1 , R s2 , R s3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0092] Adjacent substituent R x , R y1 , R s1 , R s2 , R s3 can optionally be linked to form a ring;
[0093] Z is selected from O, S or Se;
[0094] L1 is selected 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;
[0095] Wherein, the first compound has a structure represented by Formula 2:
[0096]
[0097] Z1, Z8 are selected from CR in the same or different ways each time they appear z1 or N;
[0098] Each time Z2, Z3, Z6, and Z7 appear, they are selected from CR z2 or N;
[0099] Z4, Z5 are selected from CR in the same or different ways each time they appear z3 or N;
[0100] E has a structure represented by Formula 3-1 or Formula 3-2:
[0101]
[0102] In Formula 3-1 and Formula 3-2, each occurrence of E1-E8 is identically or differently selected from C, CR e or N; and in formula 3-1, at least two of E1-E6 are N, and in formula 3-2, at least two of E1-E8 are N;
[0103] * indicates the location where E and L are connected;
[0104] L is selected 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;
[0105] R z1each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0106] R z2 , R e 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0107] Adjacent substituent R z1 , R z2 , R z3 can optionally be linked to form a ring;
[0108] Adjacent substituent R e Can optionally be linked to form a ring.
[0109] In this embodiment, the adjacent substituent R x , R y1 , R s1 , R s2 , R s3 can be optionally linked to form a ring, which is intended to indicate that for adjacent groups of substituents, for example, two substituents R x Between the two substituents R y1 Between, the substituent R s1 and R s2 Between, the substituent R s1 and Rs3 Between, and the substituent R s2 and R s3 Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring. y2 Not connected to form a ring.
[0110] In this context, adjacent substituents R z1 , R z2 , R z3 can be optionally linked to form a ring, which is intended to indicate that when there are multiple R z1 , R z2 , R z3 When the adjacent substituent R z2 Between adjacent substituents R z1 With R z2 Between adjacent substituents R z2 With R z3 between the two substituents R z3 between them, can be optionally connected to form a ring. Obviously, when there are multiple substituents R z1 , R z2 , R z3 When the adjacent substituent R z1 , R z2 , R z3 They can also not be connected to form a ring.
[0111] In this context, adjacent substituents R e can be optionally connected to form a ring, which is intended to indicate that when there are multiple substituents R e When any adjacent substituent R e Obviously, when there are multiple substituents R e When any adjacent substituent R e They can also not be connected to form a ring.
[0112] According to one embodiment of the present invention, in Formula 1, Y1-Y6 each time appears, the same or different selected from CR y1 , CR y2 or N, and when there are multiple substituents R y1 When the adjacent substituent R y1 Not connected to form a ring.
[0113] According to one embodiment of the present invention, in Formula 1, Y1-Y6 each time appears, the same or different selected from CR y1 , CR y2 or N, at least one of Y1-Y6 is selected from CR y2 , and the Ry2 With-L1-SiR s1 R s2 R s3 structure;
[0114] R s1 , R s2 , R s3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0115] L1 is selected 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;
[0116] Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
[0117] In this context, adjacent substituents R s1 , R s2 , R s3 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, substituent R s1 and R s2 Between, the substituent R s1 and R s3 Between, and the substituent R s2 and R s3 Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring. y1 None of them connect to form a ring.
[0118] According to one embodiment of the present invention, in Formula 1, two adjacent X1-X4 are C, and one of the C forms a carbon-metal bond with the metal, and the one of X1-X4 that is adjacent to the carbon-metal bond is selected from CR x , and the R x is selected from 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 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 alkyl having 2 to 20 carbon atoms alkenyl, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0119] In this embodiment, two adjacent ones of X1-X4 are C, and one of the C is connected to the metal via a carbon-metal bond. In this case, the one of X1-X4 that is adjacent to the carbon-metal bond is selected from CR x , and the R x For example, when X1 is C, X2 is also C and forms a carbon-metal bond with the metal, then L a have In this case, the one of X1-X4 that is adjacent to the carbon-metal bond is X3, and X3 is selected from CR x , and the R x When, for example, in Formula 1, X2 is C, X1 is also C and forms a carbon-metal bond with the metal, then L a have If the structure is , then the ortho position of X1-X4 where no carbon-metal bond exists can be substituted, which is obviously not the case included in this embodiment.
[0120] According to one embodiment of the present invention, in Formula 1, at least one of X1-X8 and Y1-Y6 is selected from CR x or CR y1 ; and said R x , R y1Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0121] In this embodiment, at least one of X1-X8 and Y1-Y6 is selected from CR x or CR y1 , means that at least one of X1-X8 is selected from CR x Or at least one of Y1-Y6 is selected from CR y1 , and the R x , R y1 is selected identically or differently on each occurrence from the group of substituents which are not hydrogen.
[0122] According to one embodiment of the present invention, in Formula 1, at least two or three of X1-X8 and Y1-Y6 are selected from CR x and / or CR y1 ; and said R x , R y1 Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0123] In this embodiment, at least two or three of X1-X8 and Y1-Y6 are selected from CR x and / or CR y1 , means that X1-X8 and Y1-Y6 contain at least one or more of the following: (1) at least two of X1-X8 are selected from CR x ; (2) At least two of Y1-Y6 are selected from CR y1 ; (3) At least two of X1-X8 are selected from CR x , and at least one of Y1-Y6 is selected from CR y1 ; (4) At least one of X1-X8 is selected from CR x , and at least two of Y1-Y6 are selected from CR y1 ; (5) At least three of X1-X8 are selected from CR x ; (6) At least three of Y1-Y6 are selected from CR y1 ; (7) At least one of X1-X8 is selected from CR x , and at least one of Y1-Y6 is selected from CR y1 . And in any of the above cases, the R x , R y1 is selected identically or differently on each occurrence from the group of substituents which are not hydrogen.
[0124] According to one embodiment of the present invention, in Formula 1, X7 is selected from CR x or N, where R x 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 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 alkyl having 2 to 20 carbon atoms, The invention also includes but is not limited to alkenyl groups having 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 amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0125] According to one embodiment of the present invention, in the formula 3-1, each occurrence of E1-E6 is selected from C, CR eor N, at least two of E1-E6 are N, and the adjacent substituents R e None of them connect to form a ring.
[0126] According to one embodiment of the present invention, the first metal complex has M(L a ) m (L b ) n (L c ) q structure;
[0127] Wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
[0128] L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex respectively; 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 the metal M; when m is greater than 1, multiple L a can be the same or different; when n is 2, the two L b can be the same or different. When q is 2, the two L c Can be the same or different;
[0129] L a , L b and L c can optionally be linked to form a multidentate ligand;
[0130] L b and L c Each occurrence is identically or differently selected from the group consisting of:
[0131]
[0132] Among them, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0133] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0134] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0135] R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0136] Among them, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
[0137] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and RN1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0138] In this embodiment, L a , L b and L c can be optionally linked to form a multidentate ligand, and is intended to represent L a , L b and L c can be connected arbitrarily to form a tetradentate ligand or a hexadentate ligand. a , L b and L c They can also be unconnected to form a multidentate ligand.
[0139] According to one embodiment of the present invention, the first metal complex has M(L a ) m (L b ) n (L c ) q structure;
[0140] Wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
[0141] L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex respectively; 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 the metal M; when m is greater than 1, multiple L a can be the same or different; when n is 2, the two L b can be the same or different. When q is 2, the two L c Can be the same or different; L a , L b and L ccan optionally be linked to form a multidentate ligand;
[0142] L b Each occurrence is identically or differently selected from the following structures:
[0143]
[0144] Among them, X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0145] R a1 , R b1 , R c1 , R N2 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0146] Among them, the adjacent substituent R a1 , R b1 , R c1 can optionally be linked to form a ring;
[0147] L c Each occurrence is identically or differently selected from the group consisting of:
[0148]
[0149] Among them, R a , R b , R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0150] X e Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NRN3 ;
[0151] R a , R b , R c , R N3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0152] Among them, the adjacent substituent R b , R c Can optionally be linked to form a ring.
[0153] In this embodiment, the adjacent substituent R a1 , R b1 , R c1 can be optionally connected to form a ring, which is intended to represent the substituent R a1 With R c1 Between or substituent R b1 With R c1 can be connected to form a ring. Obviously, the substituent R a1 With R c1 Between or substituent R b1 With R c1 They can also not be connected to form a ring.
[0154] In this embodiment, the adjacent substituent R b , R c can be optionally connected to form a ring, which is intended to indicate that when there are multiple substituents R b , multiple substituents R c When the adjacent substituent R b Between or adjacent substituents R c Obviously, when there are multiple substituents R b , multiple substituents R cWhen the adjacent substituent R b Between or adjacent substituents R c They can also not be connected to form a ring.
[0155] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.
[0156] According to an embodiment of the present invention, the metal M is Ir.
[0157] According to one embodiment of the present invention, wherein the L a Having a structure represented by Formula 4:
[0158]
[0159] in,
[0160] Z is selected from O or S;
[0161] X3-X8 are selected from CR in the same or different way each time they appear x or N;
[0162] Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; wherein at least one of Y1-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure;
[0163] R x , R y1 , R s1 , R s2 , R s3Each 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0164] L1 is selected 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, and combinations thereof;
[0165] Adjacent substituent R x , R s1 , R s2 , R s3 Can optionally be linked to form a ring.
[0166] In this article, the adjacent substituent R x , R s1 , R s2 , R s3 can be optionally linked to form a ring, which is intended to indicate that for adjacent groups of substituents, for example, two substituents R x Between, the substituent R s1 and R s2 Between, the substituent R s1 and R s3 Between, and the substituent R s2 and R s3 Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring.
[0167] According to one embodiment of the present invention, wherein the first metal complex has a structure represented by Formula 5:
[0168]
[0169] in,
[0170] m is 1 or 2;
[0171] Z is selected from O or S at each occurrence, identically or differently; preferably, Z is O;
[0172] X3-X8 are selected from CR in the same or different way each time they appear x or N;
[0173] Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; wherein at least one of Y1-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure;
[0174] R x , R y1 , R s1 , R s2 , R s3 R1, R2, R3, R4, R5, R6, R7 are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0175] L1 is selected 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, and combinations thereof;
[0176] Adjacent substituent R x , R s1 , R s2 , R s3can optionally be linked to form a ring;
[0177] Adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally linked to form a ring.
[0178] In this embodiment, the adjacent substituent R x , R s1 , R s2 , R s3 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R x Between, the substituent R s1 With R s2 Between, the substituent R s1 With R s3 Between, and the substituent R s2 With R s3 Any one or more of these substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring.
[0179] In this embodiment, adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally connected to form a ring, which is intended to mean that adjacent substituent groups, for example, between substituents R1 and R2, between substituents R1 and R3, between substituents R2 and R3, between substituents R4 and R5, between substituents R5 and R6, between substituents R4 and R6, between substituents R1 and R7, between substituents R2 and R7, between substituents R3 and R7, between substituents R4 and R7, between substituents R5 and R7, and between substituents R6 and R7, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring.
[0180] According to one embodiment of the present invention, wherein the first metal complex has a structure represented by Formula 5, wherein R1-R7 each time appears, the same or different selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted alkyl with 6 -30 carbon atoms, aryloxy, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when each of R1-R7 is When independently selected from substituted alkyl having 1-20 carbon atoms, substituted cycloalkyl having 3-20 ring carbon atoms, substituted heteroalkyl having 1-20 carbon atoms, substituted aryl having 6-30 carbon atoms, or substituted heteroaryl having 3-30 carbon atoms, the substitution is selected from the group consisting of hydrogen, 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 aryl having 7-30 carbon atoms, Aralkyl, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0181] According to one embodiment of the present invention, the first metal complex has a structure represented by Formula 5, wherein Z is O.
[0182] According to one embodiment of the present invention, the first metal complex has a structure represented by Formula 5:
[0183]
[0184] in,
[0185] m is 1 or 2;
[0186] Z is selected, identically or differently, from O or S at each occurrence;
[0187] wherein R1-R7 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0188] According to one embodiment of the present invention, the first metal complex has a structure represented by Formula 5:
[0189]
[0190] in,
[0191] m is 1 or 2;
[0192] Z is selected, identically or differently, from O or S at each occurrence;
[0193] wherein at least one of R1-R3 is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof.
[0194] According to one embodiment of the present invention, the first metal complex has a structure represented by Formula 5:
[0195]
[0196] in,
[0197] m is 1 or 2;
[0198] Z is selected, identically or differently, from O or S at each occurrence;
[0199] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof.
[0200] According to one embodiment of the present invention, the first metal complex has a structure represented by Formula 5:
[0201]
[0202] in,
[0203] m is 1 or 2;
[0204] Z is selected, identically or differently, from O or S at each occurrence;
[0205] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof.
[0206] According to one embodiment of the present invention, each occurrence of Y1-Y2 is identically or differently selected from CR y1 or N; Y3-Y6 are selected from CR at each occurrence, the same or different y1 , CR y2 or N, and at least one of Y3-Y6 is selected from CR y2 , and the R y2 With-L-SiR s1 R s2 R s3 structure;
[0207] R y1each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0208] R s1 , R s2 , R s3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0209] L is selected 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;
[0210] Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
[0211] In this context, adjacent substituents R s1 , R s2 , R s3can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, substituent R s1 and R s2 Between, the substituent R s1 and R s3 Between, and the substituent R s2 and R s3 Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring. y1 None of them connect to form a ring.
[0212] According to one embodiment of the present invention, each occurrence of Y1-Y2 is identically or differently selected from CR y1 or N; R y1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when said R y1The term "alkyl" refers to a substituted alkyl, a substituted cycloalkyl, a substituted heteroalkyl, a substituted aralkyl, a substituted alkoxy, a substituted aryloxy, a substituted alkenyl, a substituted alkynyl, a substituted aryl, a substituted heteroaryl, a substituted amino, a substituted acyl, a substituted carbonyl, a substituted carboxyl, a substituted ester, a substituted sulfinyl, a substituted sulfonyl, and a substituted phosphino, and means that any one of the alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups may be replaced by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted The alkylene radicals are substituted with cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 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.
[0213] According to one embodiment of the present invention, R s1 , R s2 , R s3 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0214] Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
[0215] According to one embodiment of the present invention, each occurrence of Y1-Y2 is identically or differently selected from CR y1 or N; Y3-Y6 are selected from CR at each occurrence, the same or different y1 , CR y2 or N, and at least one of Y3-Y6 is selected from CR y2 , and the R y2 With-L-SiR s1 R s2 R s3 structure;
[0216] R y1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0217] R s1 , R s2 , R s3 each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof;
[0218] L is selected 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;
[0219] Adjacent substituent R s1 , Rs2 , R s3 Can optionally be linked to form a ring.
[0220] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y1-Y6 are each independently selected from CR y1 or CR y2 .
[0221] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, at least one of Y1-Y6 is selected from N.
[0222] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Z is selected from O.
[0223] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, at least one of X3-X8 is selected from N.
[0224] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, one of X3-X8 is selected from N
[0225] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X8 is N.
[0226] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3-X8 are each independently selected from CR x .
[0227] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3-X8 are each independently selected from CR x ; and said R x is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, or a combination thereof.
[0228] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3-X8 are each independently selected from CR x ; and said R x Selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, and combinations thereof.
[0229] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3 is selected from CR x , and the Rx is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, or a combination thereof.
[0230] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3 is selected from CR x , and the R x is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, cyano, or a combination thereof.
[0231] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, X3 is selected from CR x , and the R x Selected from methyl or deuterated methyl.
[0232] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y2 is selected from CR y1 or CR y2 ; said R y1 is selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof; said R y2 With-L1-SiR s1 R s2 R s3 The structure of R s1 , R s2 , R s3Each 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 3 to 30 carbon atoms, aryl, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; L1 is selected from a single bond, substituted or unsubstituted alkylene having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, substituted or unsubstituted arylene having 6-20 carbon atoms, substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or combinations thereof; the adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
[0233] According to one embodiment of the present invention, when R y1 When selected from substituted alkyl having 1 to 20 carbon atoms or substituted cycloalkyl having 3 to 20 ring carbon atoms, the substitution is preferably selected from deuterium, fluorine, cyano or a combination thereof.
[0234] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y1-Y6 are each independently selected from CR y1 or CR y2 , and at least one of Y1-Y6 is selected from CR y2 , the R y2 With-L1-SiR s1 R s2 R s3 The structure of, wherein L1 is selected from a single bond, R s1 , R s2 and R s3 Each is independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and combinations thereof.
[0235] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, at least one of Y2 and Y4 is selected from CR y2 ; and said R y2 With-L1-SiR s1 R s2 R s3 The structure of R s1 , R s2 and R s3 are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof; and R s1 , R s2 and R s3 At least one or two of the moieties are independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.
[0236] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y2 or Y4 is selected from CR y2 ; and said R y2 With-L1-SiR s1 R s2 R s3 The structure of R s1 , R s2 and R s3 are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof; and R s1 , R s2 and R s3 At least one or two of the moieties are independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.
[0237] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y2 is CR y2 ; and said R y2 With-L1-SiR s1 R s2 R s3 The structure of R s1 , R s2 and R s3are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof; and R s1 , R s2 and R s3 At least one or two of the moieties are independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.
[0238] According to one embodiment of the present invention, in Formula 4 and / or Formula 5, Y1-Y6 are each independently selected from CR y1 or CR y2 , and at least one of Y1-Y6 is selected from CR y2 ; and said R y2 With-L1-SiR s1 R s2 R s3 The structure of R s1 , R s2 and R s3 Each is independently selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trifluoromethyl, phenyl, and combinations thereof.
[0239] According to one embodiment of the present invention, in Formula 1, Y1-Y6 each time appears, the same or different selected from CR y or N; R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon 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 2 -20 carbon atoms, alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when said R yWhen the alkyl radical is selected from substituted alkyl radicals having 1 to 20 carbon atoms, substituted cycloalkyl radicals having 3 to 20 ring carbon atoms, or substituted heteroalkyl radicals having 1 to 20 carbon atoms, the substitution is selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted alkyl radicals having 1 to 20 carbon atoms, unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, unsubstituted aralkyl radicals having 7 to 30 carbon atoms, unsubstituted alkyl radicals having 1 to 20 carbon atoms, Oxy groups, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, 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 amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0240] According to one embodiment of the present invention, in Formula 1, X1-X8 are selected from C, CR x or N; R x 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 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 groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0241] 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 a323 The group consisting of L a1 To L a323 The specific structure is as follows:
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256] 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 b322 The group consisting of L b1 To L b322 The specific structure is as follows:
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264] 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 c231 The group consisting of: c1 To Lc231 The specific structure is as follows:
[0265]
[0266]
[0267]
[0268]
[0269]
[0270]
[0271]
[0272] According to one embodiment of the present invention, the first metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure;
[0273] Wherein, when the first 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 a323 Any one or two of the group consisting of L b Choose from L b1 To L b322 When the first 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 a323 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the first metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1 To L a323 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 -Lc231 Any one or any two of the group consisting of.
[0274] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of Compound 1 to Compound 612; Compound 1 to Compound 492 have Ir(L a )2(L b ) structure, where two L a Same, L a and L b The corresponding structures are selected from the following table:
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281] Among them, compounds 493 to 612 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b They correspond to the structures listed in the following table:
[0282]
[0283]
[0284]
[0285] According to one embodiment of the present invention, the first compound has a structure represented by Formula 6:
[0286]
[0287] in,
[0288] Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Z h2 , Z h3 , Z h6 , Z h7 Each occurrence is selected from C, CR, either identically or differentlyz2 or N; Z h4 -Z h5 Each occurrence is selected from C, CR, either identically or differently z3 or N; Z h9 -Z h16 Each occurrence is the same or different selection from CR zh or N;
[0289] R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0290] R z2 , R z3 , R zh 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0291] In Formula 6, the adjacent substituent R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ring zh can optionally be linked to form a ring;
[0292] The definitions of E and L are the same as those in Formula 2.
[0293] In this context, adjacent substituents R z2 , R z3 can be optionally linked to form a 6-10 membered ring, and is intended to indicate that when there are multiple R z2 , R z3 When the adjacent substituent R z2 Between and adjacent substituents R z2 and R z3 can be optionally connected to form a 6-membered ring, a 7-membered ring, an 8-membered ring, a 9-membered ring or a 10-membered ring. Obviously, when there are multiple substituents R z2 , R z3 When the adjacent substituent R z2 , R z3 They can also not be connected to form a ring.
[0294] In this context, adjacent substituents R on the same six-membered ring zh can be optionally connected to form a 6-10 membered ring, which is intended to indicate that when multiple substituents R are present on the same six-membered ring zh When any two adjacent substituents R zh can be connected to form a ring. For example, in Formula 6, Z h13 To Z h16 All selected from CR zh , these substituents R zh are all on the same six-membered ring. At this time, any adjacent R zh Can be connected to form a ring. For example, in Formula 6, Z h12 To Z h13 All selected from CR zh , the two substituents R zh are not on the same six-membered ring, then the two R zh Obviously, when there are multiple substituents R on the same six-membered ring zh When the adjacent substituent R zh They can also not be connected to form a ring.
[0295] According to one embodiment of the present invention, the first compound has a structure represented by Formula 7:
[0296]
[0297] in,
[0298] Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Z h2 , Z h3 , Z h6 , Z h7Each occurrence is selected from C, CR, either identically or differently z2 or N; Z h4 -Z h5 Each occurrence is selected from C, CR, either identically or differently z3 or N; Z h9 -Z h12 Each occurrence is selected from C, CR, either identically or differently zh or N; Z h13 -Z h21 Each occurrence is the same or different selection from CR zh or N;
[0299] R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0300] R z2 , R z3 , R zh 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0301] In Formula 7, the adjacent substituent R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ringzh can optionally be linked to form a ring;
[0302] The definitions of E and L are the same as those in Formula 2.
[0303] According to one embodiment of the present invention, the first compound has a structure represented by Formula 8:
[0304]
[0305] in,
[0306] Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Z h2 , Z h3 , Z h6 , Z h7 Each occurrence is selected from C, CR, either identically or differently z2 or N; Z h4 -Z h5 Each occurrence is selected from C, CR, either identically or differently z3 or N; Z h9 -Z h13 Each occurrence is selected from C, CR, either identically or differently zh or N; Z h14 -Z h23 Each occurrence is the same or different selection from CR zh or N;
[0307] R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0308] R z2 , R z3 , R zhEach 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0309] In Formula 8, the adjacent substituent R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ring zh can optionally be linked to form a ring;
[0310] The definitions of E and L are the same as those in Formula 2.
[0311] According to one embodiment of the present invention, the first compound has a structure represented by Formula 9:
[0312]
[0313] in,
[0314] Z1, Z8 are selected from CR in the same or different ways each time they appear z1 or N; Z2, Z3, Z6, Z7 are each independently selected from CR z2 or N; Z4, Z5 are selected from CR in the same or different manner each time they appear z3 , and the two substituents R in Z4 and Z5 z3 Connect to form a ring;
[0315] R z1each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0316] R z2 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0317] R z3 Each occurrence is identically or differently selected from the group consisting of: hydrogen, 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 cycloalkyl having 6 to 30 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0318] Adjacent substituent R z2 , R z3 can optionally form a ring;
[0319] The definitions of E and L are the same as those in Formula 2.
[0320] In this embodiment, the adjacent substituent R z2 , R z3 can be optionally connected to form a ring, which is intended to represent adjacent groups of substituents, for example, adjacent substituents R in Z2-Z3 z2 Between, adjacent substituents R in Z6-Z7 z2 The substituent R in Z3 z2 With the substituent R in Z4 z3 The substituent R in Z3 z2 With the substituent R in Z5 z3 The substituent R in Z6 z2 With the substituent R in Z4 z3 between, and the substituent R in Z6 z2 With the substituent R in Z5 z3 Any one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0321] In this context, adjacent substituents R e can be optionally connected to form a ring, which is intended to indicate that any adjacent substituents R e Obviously, any adjacent substituents R e They can also not be connected to form a ring.
[0322] According to one embodiment of the present invention, in Formula 9, the two substituents R in Z4 and Z5 are z3 The ring formed by the connection has at least 7 ring atoms.
[0323] According to one embodiment of the present invention, the first compound has a structure represented by any one of Formula 10, Formula 11, Formula 12, Formula 13, Formula 14 or Formula 15:
[0324]
[0325]
[0326] in,
[0327] In formula 10, Z1, Z8 are selected from CR z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different manner each time they appearz2 or N; Z h1 -Z h7 Each occurrence is the same or different selection from CR zh or N;
[0328] In formula 11, Z1, Z8 are selected from CR z1 or N; Z2, Z6, Z7 are selected from CR the same or different each time they appear z2 or N; Z h1 -Z h7 Each occurrence is the same or different selection from CR zh or N;
[0329] In formula 12, Z1, Z8 are selected from CR z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different manner each time they appear z2 or N; Z h1 -Z h6 Each occurrence is the same or different selection from CR zh or N;
[0330] In Formula 13, Z1, Z8 are selected from CR z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different manner each time they appear z2 or N; Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N;
[0331] In formula 14, Z1, Z8 are selected from CR z1 or N; Z2, Z6, Z7 are selected from CR the same or different each time they appear z2 or N; Z h1 -Z h8 Each occurrence is the same or different selection from CR zh or N;
[0332] In Formula 15, Z1, Z8 are selected from CR z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different manner each time they appear z2 or N; Z h1 -Z h8 Each occurrence is the same or different selection from CR zh or N;
[0333] R z1each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
[0334] R z2 , R zh 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0335] Adjacent substituent R z1 , R z2 , R zh can optionally be linked to form a ring;
[0336] The definitions of E and L are the same as those in Formula 2.
[0337] In this embodiment, the adjacent substituent R z1 , R z2 , R zh can be optionally linked to form a ring, which is intended to indicate adjacent groups of substituents, for example, adjacent substituents R z1 With R z2 Between adjacent substituents R z2 Between adjacent substituents R z2 With R zh Between, and adjacent substituents R zhAny one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0338] According to one embodiment of the present invention, in Formula 10, Formula 11, Formula 12, Formula 13, Formula 14 or Formula 15, R z2 , R zh each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
[0339] Adjacent substituent R z2 , R zh Can optionally be linked to form a ring.
[0340] In this embodiment, the adjacent substituent R z2 , R zh can be optionally linked to form a ring, which is intended to indicate adjacent groups of substituents, for example, adjacent substituents R z2 Between adjacent substituents R z2 With R zh Between, and adjacent substituents R zh Any one or more of these substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0341] According to one embodiment of the present invention, in Formula 6 to Formula 8, Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 In formula 9 to formula 15, Z1, Z8 are selected from CR z1 .
[0342] According to one embodiment of the present invention, in Formulae 6 to 15, E is selected from the group consisting of: substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted benzoquinazoline, and substituted or unsubstituted benzoquinoxaline; optionally, the hydrogen in the above groups can be partially or completely replaced by deuterium.
[0343] According to one embodiment of the present invention, in Formula 6 to Formula 15, E is selected from the group consisting of:
[0344]
[0345]
[0346] According to one embodiment of the present invention, in Formulae 6 to 15, L is selected from the group consisting of: a single bond, a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a triphenylene group, a pyridylene group, a furylene group, a thienylene group, a dibenzofuranyl group, a dibenzothienyl group, and a combination thereof; optionally, the hydrogen in the above groups can be partially or completely replaced by deuterium.
[0347] According to one embodiment of the present invention, in Formulae 6 to 15, L is selected from a single bond or a phenylene group.
[0348] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H1-1 to compound H1-40, and the specific structures of compound H1-1 to compound H1-40 are as follows:
[0349]
[0350]
[0351]
[0352] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H2-1 to compound H2-40, and the specific structures of the compounds H2-1 to compound H2-40 are as follows:
[0353]
[0354]
[0355]
[0356]
[0357]
[0358] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H3-1 to compound H3-40, and the specific structures of the compounds H3-1 to compound H3-40 are as follows:
[0359]
[0360]
[0361]
[0362]
[0363] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H4-1 to compound H4-34, and the specific structures of the compounds H4-1 to compound H4-34 are shown below:
[0364]
[0365]
[0366]
[0367] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H5-1 to compound H5-37, and the specific structures of the compounds H5-1 to compound H5-37 are shown below:
[0368]
[0369]
[0370]
[0371] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H6-1 to compound H6-33, and the specific structures of the compounds H6-1 to compound H6-33 are as follows:
[0372]
[0373]
[0374]
[0375] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H7-1 to compound H7-29, and the specific structures of the compounds H7-1 to compound H7-29 are shown below:
[0376]
[0377]
[0378]
[0379] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H8-1 to compound H8-32, and the specific structures of the compounds H8-1 to compound H8-32 are shown below:
[0380]
[0381]
[0382]
[0383] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H9-1 to compound H9-14, and the specific structures of the compounds H9-1 to compound H9-14 are shown below:
[0384]
[0385] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, the first metal complex is a light-emitting material, and the first compound is a host material.
[0386] According to an embodiment of the invention, the device emits red light.
[0387] According to an embodiment of the invention, the device emits white light.
[0388] According to another embodiment of the present invention, an electronic device is disclosed, which includes an electroluminescent device. The specific structure of the electroluminescent device is as shown in any of the above embodiments.
[0389] According to another embodiment of the present invention, a compound combination is also disclosed, which includes the first metal complex and the first compound.
[0390] In this embodiment, the first metal complex and the first compound can be further selected from the structures described in any of the above embodiments.
[0391] Combination with other materials
[0392] 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.
[0393] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of hosts, light-emitting dopants, 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.
[0394] 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 equipment conventional 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 method well known to those skilled in the art has been carried out to confirm the structure and test the characteristics. Because those skilled in the art are aware of the related contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned related contents are no longer expanded and repeated in this patent.
[0395] Material synthesis example:
[0396] 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:
[0397] Synthesis Example 1: Synthesis of Compound 198
[0398] Step 1: Synthesis of intermediate 1
[0399]
[0400] 2,6-dibromo-4-methylphenol (58.2g, 218.9mmol) was dissolved in 700mL dry DMF, and then the reaction solution was cooled to 0°C, and then NaH (10.6g, 281.5mmol) was added in batches. After the addition, the mixture was stirred at 0°C until no obvious gas was released from the solution. Then iodomethane (46.7g, 328.4mmol) was added, and then the reaction was heated to room temperature and stirred overnight. After TLC showed that the reaction was complete, water and ethyl acetate were added, extracted, and the organic phases were combined. The organic phases were washed several times with saturated brine, dried, and spin-dried to obtain a crude product. The target product, colorless oily liquid intermediate 1 (57.7g, 94.3%), was obtained by separation by silica gel column chromatography (eluent: petroleum ether).
[0401] Step 2: Synthesis of Intermediate 2
[0402]
[0403] Intermediate 1 (57.7 g, 206 mmol), 2-fluorophenylboronic acid (28.8 g, 206 mmol), tetrakistriphenylphosphine palladium (4.76 g, 4.1 mmol) and sodium carbonate (42.7 g, 309 mmol) were placed in a 1L reaction bottle, and 300 mL of toluene, 100 mL of ethanol and 100 mL of water were added. The system was evacuated to replace nitrogen and refluxed overnight. After TLC detection to complete the reaction, it was cooled to room temperature, diluted with water, extracted with dichloromethane, the organic phases were combined, dried, rotary evaporated, and separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:100, v / v) to obtain colorless oily liquid intermediate 2 (39 g, 64.1%).
[0404] Step 3: Synthesis of Intermediate 3
[0405]
[0406] Intermediate 2 (39 g, 132.1 mmol) was dissolved in 500 mL of dichloromethane, and then the reaction solution was cooled to 0°C, and then boron tribromide (49.7 g, 198.2 mmol) was slowly added thereto, and then the reaction was placed at this temperature and continued to react for 2 hours. After TLC showed that the reaction was complete, water was carefully added thereto to quench the reaction, and dichloromethane was added to extract, the organic phases were combined, dried, rotary evaporated, and separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v / v), to obtain white solid intermediate 3 (31.8 g, 85.5%).
[0407] Step 4: Synthesis of intermediate 4
[0408]
[0409] In a 500mL three-necked flask, intermediate 3 (31.8g, 113mmol), potassium carbonate (31.3g, 226mmol), and DMF (300mL) were added respectively, and then the resulting reaction mixture was heated to 100°C under nitrogen protection for overnight reaction. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added thereto, extracted, and the organic phases were combined, washed several times with saturated brine, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent: petroleum ether) to obtain the target product, white solid intermediate 4 (16.4g, 55.6%).
[0410] Step 5: Synthesis of Intermediate 5
[0411]
[0412] In a 250mL three-necked flask, intermediate 4 (16.4g, 62.8mmol), pinacol borate (20.7g, 81.6mmol), Pd(dppf)Cl2 (1.4g, 1.9mmol), potassium acetate (9.2g, 94.2mmol) and 1,4-dioxane (300mL) were added respectively, and then the resulting reaction mixture was heated to reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added thereto, extracted, and the organic phases were combined, washed several times with saturated brine, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent ethyl acetate: petroleum ether = 1:50, v / v) to obtain the target product white solid intermediate 5 (13.5g, 69.8%).
[0413] Step 6: Synthesis of Intermediate 6
[0414]
[0415] 2,4-dibromoquinoline (6.15 g, 21.4 mmol), intermediate 5 (6.6 g, 21.4 mmol), tetrakistriphenylphosphine palladium (1.2 g, 1.1 mmol), sodium carbonate (3.4 g, 32.1 mmol), 1,4-dioxane (90 mL) and water (20 mL) were added to a 250 mL three-necked flask, and then the resulting reaction mixture was heated to reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, it was filtered, and the resulting solid was washed with hydrated petroleum ether several times and dried to obtain a crude product, which was separated by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v / v) to obtain the target product white solid intermediate 6 (5.2 g, 62.6%).
[0416] Step 7: Synthesis of Intermediate 7
[0417]
[0418] The intermediate 6 (5.2 g, 13.4 mmol) was dissolved in 134 mL of ultra-dry tetrahydrofuran, and then the reaction solution was cooled to -72 ° C, and then n-butyl lithium solution (6.4 mL, 12.0 mmol) was added dropwise under nitrogen protection, and the temperature was maintained for 30 min after the addition was completed, and then trimethylsilyl trifluoromethanesulfonate (TMSOTf) (4.2 g, 18.8 mmol) was added thereto, and after the addition was completed, the reaction was heated to room temperature for 2 h, and then a saturated sodium bicarbonate solution was added thereto to quench the reaction. Then ethyl acetate was added to the reaction, the liquids were separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:2, v / v) to obtain the target product white solid intermediate 7 (3.2 g, 62.7%).
[0419] Step 8: Synthesis of Iridium Dimer:
[0420]
[0421] A mixture of intermediate 7 (3 g, 7.9 mmol), iridium trichloride trihydrate (693 mg, 2.0 mmol), 2-ethoxyethanol (21 mL) and water (7 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which could be used in the next step without further purification.
[0422] Step 9: Synthesis of compound 198
[0423]
[0424] The ethoxyethanol solution of the iridium dimer obtained in step 8, 3.7-diethyl-1,1,1-trifluoromethylnonane-4,6-dione (798 mg, 3.0 mmol) and potassium carbonate (1.38 g, 10.0 mL) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 1.2 g of product compound 198 (49.2% yield) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS to be the target product with a molecular weight of 1218.4.
[0425] Synthesis Example 2: Synthesis of Compound 268
[0426] Step 1: Synthesis of iridium dimer:
[0427]
[0428] A mixture of intermediate 8 (0.3 g, 0.69 mmol), iridium trichloride trihydrate (60 mg, 0.17 mmol), 2-ethoxyethanol (6 mL) and water (2 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which was used in the next step without further purification.
[0429] Step 2: Synthesis of compound 268
[0430]
[0431] The ethoxyethanol solution of the iridium dimer obtained in step 4, 3.7-diethyl-3-methylnonane-4,6-dione (77 mg, 0.34 mmol) and potassium carbonate (117 mg, 0.85 mmol) were added to a 50 mL round-bottom flask and reacted at room temperature for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 80 mg of product compound 268 (36.5% yield) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS to be the target product with a molecular weight of 1290.6.
[0432] Synthesis Example 3: Synthesis of Compound 490
[0433] Step 1: Synthesis of iridium dimer:
[0434]
[0435] A mixture of intermediate 9 (2.4 g, 5.52 mmol), iridium trichloride trihydrate (480 mg, 1.36 mmol), 2-ethoxyethanol (30 mL) and water (10 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which could be used in the next step without further purification.
[0436] Step 2: Synthesis of compound 490
[0437]
[0438] The ethoxyethanol solution of the iridium dimer obtained in step 1, 3.7-diethyl-3-methylnonane-4,6-dione (462 mg, 2.04 mmol) and potassium carbonate (936 mg, 5.8 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 640 mg of product compound 490 (72.6% yield) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS to be the target product with a molecular weight of 1296.6.
[0439] Those skilled in the art should know that the above preparation method is only an illustrative example, and those skilled in the art can improve it to obtain the structure of other first metal complexes of the present invention. The first metal complex and the first compound used in the present invention can also be purchased or obtained by referring to the preparation method in the prior art, or can also be obtained by referring to the Chinese application with application number CN2020102702502 and CN2020102850167, which will not be repeated here.
[0440] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiment is only an example and should not be understood as limiting. Those skilled in the art can reasonably improve the preparation method of the following embodiment based on the prior art. For example, the ratio of various materials in the light-emitting layer is not particularly limited. Those skilled in the art can reasonably choose within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer material, the main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 90%-99%, and the light-emitting material can account for 1%-10%; or the main material can account for 95%-99%, and the light-emitting material can account for 1%-5%. In addition, the main material can be one or two materials, and the ratio of the two main materials to the main material can be 100:0 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60. In the embodiments of the device, the characteristics of the device are also tested using conventional equipment in the field (including but not limited to the vapor deposition machine produced by Angstrom Engineering, the optical testing system and life testing system produced by Suzhou Fusida, the ellipsometer produced by Beijing Liangtuo, etc.) using methods familiar to those skilled in the art.
[0441] Device Example 1
[0442] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 In the case of 1000 Å / s, the ITO anode is 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 EB1 is used as an electron blocking layer (EBL). Then, compound 198 is doped in the host compound H2-4 as an emitting layer (EML). Compound HB is used as a hole blocking layer (HBL). On the HBL, a mixture of compound ET and 8-hydroxyquinoline-lithium (Liq) is deposited as an electron transport layer (ETL). Finally, a 1nm thick Liq is deposited as an electron injection layer, and 120nm of Al is deposited as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
[0443] Device Example 2
[0444] The preparation method of Device Example 2 is the same as that of Device Example 1, except that Compound H4-17 is used instead of Compound H2-4 in the emission layer (EML).
[0445] Device Example 3
[0446] The preparation method of Device Example 3 is the same as that of Device Example 1, except that Compound H5-1 is used instead of Compound H2-4 in the emission layer (EML).
[0447] Device Example 4
[0448] The preparation method of device example 4 is the same as that of device example 1, except that compound 268 is used instead of compound 198 in the emission layer (EML) (the weight ratio of compound 268 to compound H2-4 is 2.5:97.5).
[0449] Device Example 5
[0450] Device Example 5 was prepared in the same manner as Device Example 2, except that Compound 268 was used instead of Compound 198 in the emissive layer (EML).
[0451] Device Example 6
[0452] Device Example 6 was prepared in the same manner as Device Example 4, except that Compound 490 was used instead of Compound 268 in the emissive layer (EML).
[0453] Device Example 7
[0454] Device Example 7 was prepared in the same manner as Device Example 2, except that Compound 490 was used instead of Compound 198 in the emissive layer (EML).
[0455] Device Comparison Example 1
[0456] The preparation method of device comparative example 1 is the same as that of device example 1, except that the comparative compound CBP is used instead of compound H2-4 in the emission layer (EML).
[0457] The device layer structure and thickness are shown in the table below. Where more than one material is used, different compounds are doped in the weight ratios recorded.
[0458] Table 1 Device structure of device examples
[0459]
[0460]
[0461] The material structure used in the device is shown below:
[0462]
[0463] The IVL and lifetime data of the devices were measured. Table 2 shows the IVL and lifetime data of the devices at 15 mA / cm 2 Data of CIE, voltage (Voltage), external quantum efficiency (EQE), luminous efficiency (CE), energy efficiency (PE) and lifetime LT97 measured at current density.
[0464] Table 2 Device data
[0465]
[0466]
[0467] Discussion: It can be seen from Table 2 that Examples 1-7, which contain a specific combination of the first compound and the first metal complex selected by the present invention in the device, have a redder color, lower voltage, higher efficiency and longer life relative to Comparative Example 1. In the prior art, the compound CBP is usually selected as the main material for use in conjunction with quinolyl dibenzofuran-Ir type luminescent materials. Obviously, the performance of this material combination in terms of device performance is far from the performance of the new material combination disclosed in the present invention in the device. The special combination of the specific main body and quinolyl dibenzofuran-Ir type luminescent material disclosed in the present invention has very good performance in key parameters such as color, voltage, efficiency and life. The relevant device data far exceeds the performance of the luminescent layer material combination used in the prior art, providing the industry with a luminescent layer material combination with excellent performance and deep red color emission.
[0468] 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. An electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a first metal complex and a first compound, the organic layer being a light-emitting layer, the first metal complex being a light-emitting material, and the first compound being a host material; in, The first metal complex comprises a ligand L coordinated to the metal a , and the metal is selected from metals with a relative atomic mass greater than 40; L a Having a structure represented by Formula 1: X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; Y1-Y6 are selected from CR y1 , CR y2 or N; said R y2 With-L1-SiR s1 R s2 R s3 structure; R x , R y1 , R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; Adjacent substituent R x , R y1 , R s1 , R s2 , R s3 can optionally be linked to form a ring; Z is selected from O, S or Se; L1 is selected 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; The first compound has a structure represented by any one of Formula 7, Formula 8, and Formula 10 to Formula 15: Z1, Z8, Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different ways each time they appear. z2 or N; In formula 7 to formula 8, Z h2 , Z h3 , Z h6 , Z h7 Each occurrence is selected from C, CR, either identically or differently z2 or N; Z h4 , Z h5 Each occurrence is the same or different selection from CR z3 or N; Z h9 -Z h23 Each occurrence is selected from C, CR, either identically or differently zh or N; In equations 10 to 15, Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N; E has a structure represented by Formula 3-1 or Formula 3-2: In Formula 3-1 and Formula 3-2, each occurrence of E1-E8 is identically or differently selected from C, CR e or N; and in formula 3-1, at least two of E1-E6 are N, and in formula 3-2, at least two of E1-E8 are N; * indicates the location where E and L are connected; L is selected 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; R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; R z2 , R z3 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; R e , R zh 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; In Formula 7 to Formula 8, the adjacent substituents R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ring zh Can be optionally connected to form a ring; in Formula 10 to Formula 15, adjacent substituents R z1 , R z2 , R zh can optionally be linked to form a ring; Adjacent substituent R e Can optionally be linked to form a ring.
2. The electroluminescent device according to claim 1, wherein in Formula 1, Y1-Y6 are selected from CR y1 , CR y2 or N, and when there are multiple substituents R y1 When the adjacent substituent R y1 Not connected to form a ring.
3. The electroluminescent device according to claim 1 or 2, wherein in the formula 1, Y1-Y6 each time appears, is selected from CR y1 , CR y2 or N, at least one of Y1-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure; R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; L1 is selected 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; Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
4. The electroluminescent device according to claim 1, wherein two adjacent ones of X1-X4 are C, and one of the Cs is connected to the metal via a carbon-metal bond, and the one of X1-X4 that is adjacent to the carbon-metal bond is selected from CR x , and R X The invention is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof.
5. The electroluminescent device according to claim 1, wherein at least one of X1-X8 and Y1-Y6 is selected from CR x or CR y1 ; and said R x , R y1 Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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 2-20 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 amino having 0-20 carbon atoms, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof.
6. The electroluminescent device according to claim 5, wherein at least two or three of X1-X8 and Y1-Y6 are selected from CR x and / or CR y1 ; and said R x , R y1 Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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 2-20 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 amino having 0-20 carbon atoms, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof.
7. The electroluminescent device of claim 1, wherein the first metal complex has M(L a ) m (L b ) n (L c ) q structure; in, The metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex, respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; When m is greater than 1, multiple L a can be the same or different; when n is 2, the two L b can be the same or different. When q is 2, the two L c Can be the same or different; L a , L b and L c can optionally be linked to form a multidentate ligand; L b and L c Each occurrence is identically or differently selected from the group consisting of: Among them, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; Among them, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
8. The electroluminescent device of claim 1, wherein the first metal complex has M(L a ) m (L b ) n (L c ) q structure; in, The metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; When m is greater than 1, multiple L a can be the same or different; when n is 2, the two L b can be the same or different. When q is 2, the two L c Can be the same or different; L a , L b and L c can optionally be linked to form a multidentate ligand; Among them, L b Each occurrence is identically or differently selected from the following structures: Among them, X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a1 , R b1 , R c1 , R N2 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; Among them, the adjacent substituent R a1 , R b1 , R c1 can optionally be linked to form a ring; L c Each occurrence is identically or differently selected from the group consisting of: Among them, R a , R b , R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X e Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N3 ; R a , R b , R c , R N3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; Among them, the adjacent substituent R b , R c Can optionally be linked to form a ring.
9. The electroluminescent device according to claim 1, wherein said L a Having a structure represented by Formula 4: in, Z is selected from O or S; X3-X8 are selected from CR in the same or different way each time they appear x or N; Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; wherein at least one of Y1-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure; R x , R y1 , R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; L1 is selected 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, and combinations thereof; Adjacent substituent R x , R s1 , R s2 , R s3 Can optionally be linked to form a ring.
10. The electroluminescent device of claim 8, wherein the first metal complex has a structure represented by Formula 5: in, m is 1 or 2; Z is selected, identically or differently, from O or S at each occurrence; X3-X8 are selected from CR in the same or different way each time they appear x or N; Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; wherein at least one of Y1-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure; R x , R y1 , R s1 , R s2 , R s3 R1, R2, R3, R4, R5, R6, R7 are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 3 carbon atoms, 0 carbon atoms, aryloxy groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkylsilyl groups, substituted or unsubstituted arylsilyl groups, substituted or unsubstituted amino groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; L1 is selected 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, and combinations thereof; Adjacent substituent R x , R s1 , R s2 , R s3 can optionally be linked to form a ring; Adjacent substituents R1, R2, R3, R4, R5, R6, R7 can be optionally linked to form a ring.
11. An electroluminescent device as claimed in claim 10, wherein at least one or two of R1-R3 is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof.
12. The electroluminescent device according to claim 9, wherein: Y1-Y2 are selected from CR y1 or N; Y3-Y6 are selected from CR at each occurrence, the same or different y1 , CR y2 or N, and at least one of Y3-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure; R y1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; L1 is selected 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; Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
13. The electroluminescent device according to claim 12, wherein: At least one of Y3-Y6 is selected from CR y2 , and the R y2 With-L1-SiR s1 R s2 R s3 structure; R s1 , R s2 , R s3 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
14. The electroluminescent device of claim 9, wherein Y1-Y6 are each independently selected from CR y1 or CR y2 .
15. The electroluminescent device of claim 9, wherein at least one of Y1-Y6 is selected from N.
16. The electroluminescent device of claim 9, wherein Z is O.
17. The electroluminescent device of claim 9, wherein at least one of X3-X8 is selected from N.
18. The electroluminescent device of claim 9, wherein X3-X8 are each independently selected from CR x .
19. The electroluminescent device according to claim 18, wherein R x is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, or a combination thereof.
20. The electroluminescent device of claim 18, wherein: X3 Selected from CR x , and the R x is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, or a combination thereof.
21. The electroluminescent device according to claim 20, wherein said R x is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, cyano, or a combination thereof.
22. The electroluminescent device of claim 9, wherein: Y2 is selected from CR y1 or CR y2 ; said R y1 is selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof; said R y2 With-L1-SiR s1 R s2 R s3 structure; R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; L1 is selected 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; Adjacent substituent R s1 , R s2 , R s3 Can optionally be linked to form a ring.
23. The electroluminescent device of claim 22, wherein Y1-Y6 are each independently selected from CR y1 or CR y2 , and at least one of Y1-Y6 is selected from CR y2 , the R y2 With-L1-SiR s1 R s2 R s3 The structure of, wherein L1 is selected from a single bond, R s1 , R s2 and R s3 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and combinations thereof; and R s1 , R s2 and R s3 At least one or two of the moieties are independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.
24. The electroluminescent device of claim 22, wherein at least one of Y2 and Y4 is selected from CR y2 .
25. The electroluminescent device of claim 23, wherein: R s1 , R s2 and R s3 Each is independently selected from the group consisting of methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trifluoromethyl, phenyl, and combinations thereof.
26. The electroluminescent device of claim 7, wherein L a Each occurrence is identically or differently selected from the group consisting of:
27. The electroluminescent device of claim 26, wherein L b Each occurrence is identically or differently selected from the group consisting of: in, L c Each occurrence is identically or differently selected from the group consisting of:
28. The electroluminescent device of claim 27, wherein: The first metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure; Wherein, when the first 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 a319 Any one or two of the group consisting of L b Choose from L b1 To L b322 When the first 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 a319 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the first metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1 To L a319 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 To L c231 Any one or any two of the group consisting of.
29. The electroluminescent device of claim 28, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 612; wherein compounds 1 to 492 have Ir(L a )2(L b ) structure, where two L a Same, L a and L b The corresponding structures are selected from the following table: in, Compounds 493 to 612 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b They correspond to the structures listed in the following table:
30. The electroluminescent device of claim 1, wherein the first compound has a structure represented by any one of Formula 7 or Formula 8: in, Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Z h2 , Z h3 , Z h6 , Z h7 Each occurrence is selected from C, CR, either identically or differently z2 or N; Z h4 , Z h5 Each occurrence is the same or different selection from CR z3 or N; Z h9 -Z h23 Each occurrence is selected from C, CR, either identically or differently zh or N; R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; R z2 , R z3 , R zh each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; In Formula 7 or Formula 8, the adjacent substituent R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ring zh can optionally be linked to form a ring; The definitions of E and L are the same as those in claim 1.
31. The electroluminescent device of claim 1, wherein: The first compound has a structure represented by any one of Formula 10 to Formula 15: in, Z1, Z8 are selected from CR in the same or different ways each time they appear z1 or N; Z2, Z3, Z6, Z7 are selected from CR in the same or different manner each time they appear z2 or N; Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N; R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; R z2 , R zh each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; Adjacent substituent R z1 , R z2 , R zh can optionally be linked to form a ring; The definitions of E and L are the same as those in claim 1.
32. The electroluminescent device of claim 31, wherein Z h1 , Z h8 , Z1, Z8 are selected from CR each time they appear, either identically or differently z1 .
33. An electroluminescent device as described in claim 31, wherein the E is selected from the group consisting of: substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazoline, and substituted or unsubstituted benzoquinoxalinyl; optionally, the hydrogen in the above groups can be partially or completely replaced by deuterium.
34. The electroluminescent device of claim 33, wherein said E is selected from the group consisting of:
35. The electroluminescent device of claim 31, wherein: The L is selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a triphenylene group, a pyridylene group, a furylene group, a thienylene group, a dibenzofuranyl group, a dibenzothienyl group, and a combination thereof; optionally, the hydrogen in the above groups can be partially or completely replaced by deuterium.
36. The electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:
37. The electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:
38. The electroluminescent device of claim 37, which emits red light or white light.
39. An electronic device comprising the electroluminescent device according to any one of claims 1 to 38.
40. A compound combination comprising a first metal complex and a first compound; in, The first metal complex comprises a ligand L coordinated to the metal a , and the metal is selected from metals with a relative atomic mass greater than 40; L a Having a structure represented by Formula 1: X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; Each occurrence of Y1-Y6 is selected from CR y1 , CR y2 or N; said R y2 With-L1-SiR s1 R s2 R s3 structure; R x , R y1 , R s1 , R s2 , R s3 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; Adjacent substituent R x , R y1 , R s1 , R s2 , R s3 can optionally be linked to form a ring; Z is selected from O, S or Se; L1 is selected 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; The first compound has a structure represented by any one of Formula 7, Formula 8, and Formula 10 to Formula 15: Z1, Z8, Z h1 , Z h8 Each occurrence is the same or different selection from CR z1 or N; Each time Z2, Z3, Z6, and Z7 appear, they are selected from CR z2 or N; In formula 7 to formula 8, Z h2 , Z h3 , Z h6 , Z h7 Each occurrence is selected from C, CR, either identically or differently z2 or N; Z h4 , Z h5 Each occurrence is the same or different selection from CR z3 or N; Z h9 -Z h23 Each occurrence is selected from C, CR, either identically or differently zh or N; In equations 10 to 15, Z h1 -Z h9 Each occurrence is the same or different selection from CR zh or N; E has a structure represented by Formula 3-1 or Formula 3-2: In Formula 3-1 and Formula 3-2, each occurrence of E1-E8 is identically or differently selected from C, CR e or N; and in formula 3-1, at least two of E1-E6 are N, and in formula 3-2, at least two of E1-E8 are N; * indicates the location where E and L are connected; L is selected 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; R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; R z2 , R z3 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; R e , R zh 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 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 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 amino groups having 0 to 20 carbon atoms, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, phosphino groups, and combinations thereof; In Formula 7 to Formula 8, the adjacent substituents R z2 , R z3 can be optionally linked to form a 6-10 membered ring; adjacent substituents R on the same six-membered ring zh can optionally be linked to form a ring; In Formulae 10 to 15, the adjacent substituents R z1 , R z2 , R zh can optionally be linked to form a ring; Adjacent substituent R e Can optionally be linked to form a ring.
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