An electroluminescent device
By using La ligand metal complexes, first compounds and second compounds of specific structures in organic electroluminescent devices, the problems of reduced efficiency and short device life in the prior art are solved, and more efficient and longer life electroluminescent effects are achieved.
Patent Information
- Application Number
- CN202110338405.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-03-30
- Publication Date
- 2025-02-25
- Estimated Expiration
- 2041-03-30
AI Technical Summary
The efficiency of existing organic electroluminescent devices is rapidly reduced under high brightness, and blue phosphorescent devices have problems such as blue unsaturation, short device life and high operating voltage, making it difficult to achieve a more saturated luminescence spectrum, higher efficiency and longer device life.
The electroluminescent device comprising a first metal complex having a specific La ligand structure, a first compound having a specific structure and a second compound having a specific structure, is significantly improved by combinations of these compounds, especially device life.
By selecting specific compound combinations, the performance of organic electroluminescent devices is significantly improved, especially device life, and achieve higher comprehensive performance effects.
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Figure CN115148914B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an electroluminescent device. More particularly, it relates to an electroluminescent device comprising L having a structure of Formula 1 a An electroluminescent device comprising a first metal complex of a ligand, a first compound having a structure of Formula 2 and a second compound having a structure of Formula 3, and an electronic device comprising the electroluminescent device and a compound combination comprising the first metal complex, the first compound and the second compound. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic 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] US20200203631A1 discloses an organic electroluminescent device comprising a first host compound having a structure of formula 1 The second host compound having the structure of formula 2 And a metal complex having a structure of formula 3 The second main compound of interest in this application is a compound comprising a dibenzo five-membered heterocyclic group connected to a substituted or unsubstituted carbazole group. This application does not disclose that the second compound of the present application and a metal complex comprising a specific fluorine / cyano substituted ligand can be used in a device to obtain better device performance.
[0009] US2020091442A1 discloses a metal complex containing a fluorine-substituted ligand, wherein the fluorine-substituted ligand has the following structure Wherein X1-X7 is selected from C, CR or N. The application only discloses such metal complexes with fluorine-substituted ligands in As devices in host materials, the device performance of such metal complexes with fluorine-substituted ligands in other host materials has not been studied.
[0010] US2020251666A1 discloses a metal complex comprising a cyano-substituted ligand, wherein the cyano-substituted ligand has the following structure Where X1-X4 is selected from C, CR x1 or N, X5-X8 selected from CR x2 or N, R x1 and R x2 At least one of them is a cyano group. The application only discloses that such metal complexes with cyano-substituted ligands are As devices in host materials, the device performance of such metal complexes with cyano-substituted ligands in other host materials has not been studied.
[0011] US2019363261A1 discloses a method having The following metal complexes are disclosed in the examples: and in Application in host materials: This application does not focus on the fact that when metal complexes containing specific fluorine / cyano substituted ligands are used in such host materials, devices can obtain better performance. Summary of the invention
[0012] The present invention aims to provide a series of L having a structure of Formula 1 a An electroluminescent device comprising a first metal complex of a ligand, a first compound having a structure of Formula 2, and a second compound having a structure of Formula 3 solves at least part of the above problems.
[0013] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0014] anode,
[0015] cathode,
[0016] and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex, a first compound, and a second compound;
[0017] The first metal complex comprises a metal M and a ligand L coordinated with the metal M. a , ligand L a Having a structure represented by Formula 1:
[0018]
[0019] in,
[0020] The metal M is selected from metals with a relative atomic mass greater than 40;
[0021] Cy is selected from substituted or unsubstituted aryl having 5 to 24 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 24 ring atoms at each occurrence, the same or different; the Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0022] X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R' at each occurrence; when two R' are present at the same time, the two R' are the same or different;
[0023] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N, and at least one of X1-X4 is C and connected to the Cy;
[0024] X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0025] At least one of X1-X8 is CR x , and the R x is cyano or fluorine;
[0026] The adjacent substituents R', R x can optionally be linked to form a ring;
[0027] Wherein, the first compound has a structure represented by Formula 2:
[0028]
[0029] in,
[0030] Each time U appears, it is selected from C, CR u or N;
[0031] Each time V appears, it is selected from CR in the same or different way. v or N;
[0032] L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0033] Adjacent substituent R u and R v can optionally be linked to form a ring;
[0034] Wherein, the second compound has a structure represented by Formula 3:
[0035]
[0036] in,
[0037] Ar1 has a structure represented by Formula A:
[0038]
[0039] in,
[0040] Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se;
[0041] L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0042] Each occurrence of Z1-Z8 is selected from C, CR z or N, and at least one of Z1-Z8 is C and connected to L3;
[0043] At least one CR in Z1-Z8 z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
[0044] Ar2 is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence, the same or different;
[0045] “*” represents the connection position between Ar1 and L3;
[0046] Adjacent substituent Rz can optionally be linked into a ring;
[0047] R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0048] R'、R x , R u , R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0049] According to one embodiment of the present invention, an electronic device is disclosed, which includes the electroluminescent device described in the above embodiment.
[0050] According to another embodiment of the present invention, a compound combination is disclosed, which comprises the first metal complex, the first compound and the second compound described in the above embodiment.
[0051] The present invention aims to provide a series of L having a structure of Formula 1 a An electroluminescent device comprising a first metal complex of a ligand, a first compound having a structure of Formula 2, and a second compound having a structure of Formula 3. By selecting such a combination of compounds, the performance of the organic electroluminescent device can be significantly improved compared with the prior art, especially the life of the device can be significantly improved, and ultimately the beneficial effect of significantly improving the overall performance of the device can be achieved. BRIEF DESCRIPTION OF THE DRAWINGS
[0052] Figure 1 is a schematic diagram of an electroluminescent device that may contain combinations of metal complexes and compounds disclosed herein.
[0053] Figure 2 is a schematic diagram of another electroluminescent device that may contain the metal complexes and compound combinations disclosed herein. DETAILED DESCRIPTION
[0054] 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.
[0055] 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.
[0056] 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.
[0057] 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.
[0058] 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.
[0059] 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.
[0060] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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).
[0065] 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.
[0066] 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).
[0067] Definition of Substituent Terms
[0068] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0069] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
[0070] 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.
[0071] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.
[0072] 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.
[0073] 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.
[0074] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.
[0075] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.
[0076] 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.
[0077] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.
[0078] 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.
[0079] 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,
[0080] 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.
[0081] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.
[0082] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.
[0083] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.
[0084] 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.
[0085] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted The carboxylic acid group, substituted ester group, substituted sulfinyl group, refers to any one of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, an alkylgermanyl group, an arylgermanyl group, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a sulfinyl group, a sulfonyl group and a phosphino group, which may be substituted by one or more deuterium, a halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted alkyl group having 3 to 20 carbon atoms. cycloalkyl having ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0086] 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.
[0087] 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.
[0088] 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.
[0089] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0090] 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:
[0091]
[0092] 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:
[0093]
[0094] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0095]
[0096] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0097]
[0098] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0099] anode,
[0100] cathode,
[0101] and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex, a first compound, and a second compound;
[0102] The first metal complex comprises a metal M and a ligand L coordinated with the metal M. a , ligand L a Having a structure represented by Formula 1:
[0103]
[0104] in,
[0105] The metal M is selected from metals with a relative atomic mass greater than 40;
[0106] Cy is selected from substituted or unsubstituted aryl having 5 to 24 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 24 ring atoms at each occurrence, the same or different; the Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0107] X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R' at each occurrence; when two R' are present at the same time, the two R' are the same or different;
[0108] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N, and at least one of X1-X4 is C and connected to the Cy;
[0109] X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0110] At least one of X1-X8 is CR x , and the R x is cyano or fluorine;
[0111] The adjacent substituents R', R x can optionally be linked to form a ring;
[0112] Wherein, the first compound has a structure represented by Formula 2:
[0113]
[0114] in,
[0115] Each time U appears, it is selected from C, CR u or N;
[0116] Each time V appears, it is selected from CR in the same or different way. v or N;
[0117] L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0118] Adjacent substituent R u and R v can optionally be linked to form a ring;
[0119] Wherein, the second compound has a structure represented by Formula 3:
[0120]
[0121] in,
[0122] Ar1 has a structure represented by Formula A:
[0123]
[0124] in,
[0125] Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se;
[0126] L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0127] Each occurrence of Z1-Z8 is selected from C, CR z or N, and at least one of Z1-Z8 is C and connected to L3;
[0128] At least one CR in Z1-Z8 z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
[0129] Ar2 is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence, the same or different;
[0130] “*” represents the connection position between Ar1 and L3;
[0131] Adjacent substituent R z can optionally be linked into a ring;
[0132] R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0133] R'、R x , R u , R vEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0134] In this application, "adjacent substituents R', R x "can be optionally connected to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R x Between the two substituents R' and R x 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.
[0135] In this application, “adjacent substituents R u , R v "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R u Between the two substituents R v Between the two substituents R u and R v 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.
[0136] In this application, “adjacent substituents R z "can be optionally linked to form a ring" is intended to mean that adjacent groups of substituents, for example, any two adjacent substituents R z 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.
[0137] According to an embodiment of the present invention, Ar1 does not contain substituted or unsubstituted carbazole groups.
[0138] According to one embodiment of the present invention, Cy is selected from any structure in the group consisting of:
[0139]
[0140] in,
[0141] Each occurrence of R is the same or different, indicating mono-substitution, poly-substitution, or no substitution; when multiple R are present in any structure, the R may be the same or different;
[0142] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0143] Two adjacent substituents R can optionally be linked to form a ring;
[0144] Wherein, “#” indicates the position connected to the metal M. Indicates a location connected to X1, X2, X3, or X4.
[0145] In this embodiment, "adjacent substituents R can be optionally connected to form a ring" is intended to mean that adjacent substituent groups, for example, between any two adjacent substituents R, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may not be connected to form a ring.
[0146] According to one embodiment of the present invention, the first metal complex has M(L a ) m (L b ) n (L c ) q The general formula of
[0147] in,
[0148] M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt;
[0149] L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand;
[0150] m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a The same or different; when n is equal to 2, the two L b The same or different; when q is equal to 2, the two L c Same or different;
[0151] L a Each occurrence is identically or differently selected from the group consisting of:
[0152]
[0153]
[0154]
[0155]
[0156]
[0157] X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R'; when two R's are present at the same time, the two R's are the same or different;
[0158] R and R x Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0159] At least one R x is selected from cyano or fluorine;
[0160] Adjacent substituents R, R', R x can optionally be linked to form a ring;
[0161] L b and L c Each occurrence is identically or differently selected from any one of the following groups:
[0162]
[0163] in,
[0164] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;
[0165] R a , R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0166] Adjacent substituent R a , R b , R c , R N1 , R C1 , R C2 can optionally be linked to form a ring;
[0167] R, R', R x , R a , R b , R c , R N1 , R C1 and R C2The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0168] In this application, "adjacent substituents R, R', R x "can be optionally linked to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R, between two substituents R x Between the two substituents R' and R x Between the two substituents R and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0169] In this embodiment, "the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and RN1 Between, the substituent R b and R N1 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, 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.
[0170] According to one embodiment of the present invention, the metal M is selected from Pt or Ir, the same or different each time it occurs.
[0171] According to one embodiment of the present invention, the first metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 5:
[0172]
[0173] in,
[0174] m is 1, 2 or 3; when m is 2 or 3, multiple L a The same or different; when m is 1, the two L b Same or different;
[0175] X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R'; when two R's are present at the same time, the two R's are the same or different;
[0176] Each occurrence of X3-X8 is the same or different selection from CR x or N;
[0177] At least one of X3-X8 is CR x , and the R x is cyano or fluorine;
[0178] R, when present at each occurrence, is identical or different and represents mono-substitution, poly-substitution, or no substitution;
[0179] R1-R8, R', R xand R, at each occurrence, is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0180] Adjacent substituents R1-R8 can be optionally linked to form a ring;
[0181] Adjacent substituents R', R and R x Can optionally be linked to form a ring.
[0182] In this embodiment, "adjacent substituents R1-R8 can be optionally connected to form a ring" is intended to mean that adjacent substituent groups, for example, between any two adjacent substituents in R1-R8, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may not be connected to form a ring.
[0183] According to one embodiment of the present invention, X is selected from O or S.
[0184] According to one embodiment of the present invention, X is selected from O.
[0185] According to one embodiment of the present invention, at least one of X3-X8 is selected from N, for example, one of X3-X8 is selected from N, or two of X3-X8 are selected from N.
[0186] According to one embodiment of the present invention, X3-X8 is selected from CR x , and at least one of them is R x It is cyano or fluorine.
[0187] According to one embodiment of the present invention, at least one of X5-X8 is selected from CRx , and the R x is cyano or fluorine; preferably, X7 or X8 is CR x , and the R x It is cyano or fluorine.
[0188] According to one embodiment of the present invention, at least one of X5-X8 is selected from CR x , and the R x is cyano or fluorine; at least one of X5-X8 is selected from CR x , and the R x is 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 substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0189] According to one embodiment of the present invention, X7 is selected from CR x , and the R x is cyano or fluorine; and X8 is also selected from CR x , and the R x is 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 substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0190] According to one embodiment of the present invention, X8 is selected from CR x , and the R x is cyano; at the same time X7 is also selected from CR x , and the R x is 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 substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0191] According to one embodiment of the present invention, at least one or at least two or at least three or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
[0192] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof;
[0193] According to one embodiment of the present invention, at least one, at least two, at least three or all of R2, R3, R6 and R7 are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; optionally, the hydrogen in the above groups can be partially or completely deuterated.
[0194] According to one embodiment of the present invention, at least one or more of R5-R8 is selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, or a combination thereof; and the total number of carbon atoms of R5-R8 is at least 4.
[0195] According to one embodiment of the present invention, at least two of X3-X8 are selected from CR x , and one of the R x is selected from fluorine or cyano, at least one other R x Selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, cyano, and combinations thereof.
[0196] According to one embodiment of the present invention, at least two of X3-X8 are selected from CR x , and one of the R x is selected from fluorine or cyano, at least one other R x Selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, cyano, and combinations thereof.
[0197] According to one embodiment of the present invention, wherein R appears each time and is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.
[0198] According to one embodiment of the present invention, at least one R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0199] According to one embodiment of the present invention, R' is selected from the group consisting of: a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, and combinations thereof.
[0200] According to one embodiment of the present invention, R' is selected from methyl or deuterated methyl.
[0201] 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 a188 The group consisting of L a1 To L a188 The specific structure is described in claim 10.
[0202] 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 b128 The group consisting of L b1 To L b128 The specific structure is described in claim 11.
[0203] According to one embodiment of the present invention, L c Each time it appears, choose the same or different one from L c1 To L c360 The group consisting of L c1 To L c360 The specific structure is described in claim 12.
[0204] According to one embodiment of the present invention, the first metal complex has Ir(L a )(L b )(L c ) or Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )3, where L a Each time it appears, choose the same or different one from L a1 To L a188 The group composed of L b Each time it appears, choose the same or different one from L b1 To L b128 The group composed of L c Each time it appears, choose the same or different one from L c1 To L c360 The group consisting of L a1 To L a188 The specific structure is described in claim 10, L b1 To L b128 The specific structure is described in claim 11, wherein L c1 To L c360 The specific structure is described in claim 12.
[0205] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of GD1 to GD178, wherein the specific structures of GD1 to GD178 are described in claim 13.
[0206] According to one embodiment of the present invention, the first compound has a structure represented by Formula 2a:
[0207]
[0208] Wherein, in Formula 2a,
[0209] Each time U appears, it is selected from C, CR u or N;
[0210] Each time V appears, it is selected from CR in the same or different way. v or N;
[0211] Ar4 is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence;
[0212] L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0213] R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0214] Adjacent substituents Ar4, R u and R v Can optionally be linked to form a ring.
[0215] In this application, "adjacent substituents Ar4, R u and R v "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R u Between the two substituents R v Between, the substituent R v Any one or more of these substituent groups may be connected to form a ring between Ar4 and Ar4. Obviously, none of these substituent groups may be connected to form a ring.
[0216] According to one embodiment of the present invention, the first compound has a structure represented by Formula 2b:
[0217]
[0218] Wherein, in Formula 2b,
[0219] Each time U appears, it is selected from CR in the same or different way. u or N;
[0220] Each time V appears, it is selected from CR in the same or different way. v or N;
[0221] Ar4 is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence;
[0222] L1 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0223] R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0224] Adjacent substituents Ar4, R u and R v Can optionally be linked to form a ring.
[0225] According to one embodiment of the present invention, each time U appears, it is selected from C or CR in the same or different manner. u .
[0226] According to one embodiment of the present invention, each time V appears, it is selected from CR v .
[0227] According to one embodiment of the present invention, at least one of U is selected from N, for example, at least one of U is N, or at least two of U are N.
[0228] According to one embodiment of the present invention, at least one of V is selected from N, for example, at least one of V is N, or at least two of V are N.
[0229] According to one embodiment of the present invention, R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
[0230] According to one embodiment of the present invention, R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof.
[0231] According to one embodiment of the present invention, R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
[0232] According to one embodiment of the present invention, Z1-Z8 are selected from C or CR each time they appear, either identically or differently. z .
[0233] According to one embodiment of the present invention, at least one of Z1-Z8 is selected from N, for example, one of Z1-Z8 is selected from N, or two of Z1-Z8 are selected from N.
[0234] According to one embodiment of the present invention, at least two of Z1-Z8 are CR z, and the at least one R z is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; at least one other R z is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a combination thereof.
[0235] According to one embodiment of the present invention, at least one, at least two, or at least three of Z1-Z8 are selected from CR z , and the R z is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
[0236] According to one embodiment of the present invention, at least one, at least two, or at least three of Z1-Z8 are selected from CR z , and the R z Any of the following groups selected from unsubstituted or substituted by one or more of deuterium, halogen, and cyano: phenyl, naphthyl, biphenyl, and terphenyl.
[0237] According to one embodiment of the present invention, at least one of Z1-Z4 is selected from C and connected to L3; Z5 and / or Z8 is selected from R z , and the R z It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0238] According to one embodiment of the present invention, at least one of Z1-Z4 is selected from C and connected to L3; at the same time, at least one of Z1-Z4 is selected from CR z , and the R z It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0239] According to one embodiment of the present invention, the second compound has a structure represented by one of Formula 3-1 to Formula 3-4:
[0240] in,
[0241] Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se;
[0242] L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0243] Each occurrence of Z1-Z8 is selected from C, CR z or N;
[0244] In Formula 3-1 and Formula 3-2, at least one of Z1-Z8 is C and connected to L3, and at least one of Z1-Z8 is selected from CR z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
[0245] W1-W8 are selected from C, CR in the same or different manner at each occurrence w or N;
[0246] Ar2 and Ar3 are identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof at each occurrence;
[0247] R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0248] R w and R nEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0249] Adjacent substituent R z , R w , R n Can optionally be linked to form a ring.
[0250] In this embodiment, "the adjacent substituent R z , R w , R n "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R z Between the two substituents R w Between the two substituents R n Between the two substituents R w and R n 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.
[0251] According to one embodiment of the present invention, L1 to L3 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, the same or different when each occurs.
[0252] According to one embodiment of the present invention, each occurrence of L1 to L2 is identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
[0253] According to one embodiment of the present invention, each occurrence of L1 to L2 is identically or differently selected from a single bond, a phenylene group or a biphenylene group.
[0254] According to one embodiment of the present invention, each occurrence of L1 to L2 is identically or differently selected from a single bond.
[0255] According to one embodiment of the present invention, L3 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a combination thereof, the same or different each time it occurs.
[0256] According to one embodiment of the present invention, L3 is selected from a single bond, a phenylene group or a biphenylene group, the same or different each time it occurs.
[0257] According to one embodiment of the present invention, wherein L3 is selected from a single bond the same or differently each time it occurs.
[0258] According to one embodiment of the present invention, each occurrence of Ar2 to Ar3 is identically or differently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.
[0259] According to one embodiment of the present invention, wherein Ar2 to Ar3 each time appear the same or differently selected from any of the following groups which are unsubstituted or substituted by one or more of deuterium, halogen, cyano: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidine, pyrazinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, diazadibenzothiophenyl, and combinations thereof.
[0260] According to one embodiment of the present invention, wherein Ar2 to Ar3 each time appear the same or differently selected from any of the following groups which are unsubstituted or substituted by one or more of deuterium, halogen, cyano: phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
[0261] According to one embodiment of the present invention, wherein Ar4 is identically or differently selected each time from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.
[0262] According to one embodiment of the present invention, wherein Ar4 appears the same or differently each time and is selected from any of the following groups which are unsubstituted or substituted by one or more of deuterium, halogen, and cyano: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, diazadibenzothiophenyl, and combinations thereof.
[0263] According to one embodiment of the present invention, wherein Ar4 appears the same or differently each time and is selected from any of the following groups which are unsubstituted or substituted by one or more of deuterium, halogen, and cyano: phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
[0264] According to one embodiment of the present invention, the first compound is selected from the group consisting of compounds 2-1 to 2-241, wherein the specific structures of compounds 2-1 to 2-241 are described in claim 26.
[0265] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds H-1 to H-178, wherein the specific structures of compounds H-1 to H-178 are described in claim 27.
[0266] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the first metal complex is doped in the first compound and the second compound, and the weight of the first metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
[0267] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the first metal complex is doped in the first compound and the second compound, and the weight of the first metal complex accounts for 3%-13% of the total weight of the light-emitting layer.
[0268] According to one embodiment of the present invention, an electronic device is also disclosed, which includes the electroluminescent device described in any of the above embodiments.
[0269] According to one embodiment of the present invention, a compound combination is further disclosed, which comprises the first metal complex, the first compound and the second compound described in any of the aforementioned embodiments.
[0270] Combination with other materials
[0271] 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.
[0272] 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, 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.
[0273] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.
[0274] Device Embodiment
[0275] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiment is only an example and should not be construed as limiting. 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 select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer material, the main material can account for 70%-99%, and the light-emitting material can account for 1%-30%; or the main material can account for 90%-98%, and the light-emitting material can account for 2%-10%, or the main material can account for 87%-98%, and the light-emitting material can account for 2%-13%. In addition, the main material can be one or two materials, wherein the ratio of the two main materials to the main material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60. The characteristics of the light-emitting device prepared in the embodiment are tested using conventional equipment in the art and methods well known to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, and can obtain the inherent data of the sample with certainty and without influence, the above-mentioned related contents will not be elaborated in this patent. The first metal complex, the first compound, the second compound and other compounds used in the present invention are easily obtained by those skilled in the art, for example, they can be obtained by commercial sales, or by reference to the preparation methods in the prior art, or by reference to the preparation methods in the U.S. patent applications with publication numbers US20200251666A1 and US2019363261A1, which will not be described here.
[0276] Device Example 1a
[0277] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8In the case of 1000 Å / s, the ITO anode is sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound C-1 is used as an electron blocking layer (EBL). Then compound GD121 is doped in compound 2-1 and compound H-1, and co-evaporation is used as an emitting layer (EML). Compound C-3 is used as a hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-evaporated as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover to complete the device.
[0278] Device Example 1b
[0279] Device Example 1b was prepared the same as Example 1a, except that Compound 2-171 was used instead of Compound 2-1 in the emissive layer (EML).
[0280] Device Example 1c
[0281] Device Example 1c was prepared the same as Example 1a, except that Compound 2-167 was used instead of Compound 2-1 in the emissive layer (EML).
[0282] Device Example 1d
[0283] Device Example 1d was prepared the same as Example 1a, except that Compound 2-170 was used instead of Compound 2-1 in the emissive layer (EML).
[0284] Device Comparative Example 1a
[0285] The device of Comparative Example 1a was prepared in the same manner as Example 1a, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0286] Device Comparative Example 1b
[0287] The device of Comparative Example 1b was prepared in the same manner as Example 1a, except that Compound C-2 was used instead of Compound H-1 in the emission layer (EML).
[0288] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0289] Table 1 Device structures of device embodiments 1a to 1d and comparative examples 1a-1b
[0290]
[0291] The material structure used in the device is shown below:
[0292]
[0293]
[0294] Table 2 shows that at 15 mA / cm 2 CIE data and current efficiency measured at constant current density; and at 80mA / cm 2 Device lifetime (LT95) measured at constant current density.
[0295] Table 2 Device data of device examples 1a to 1d and comparative examples 1a-1b
[0296]
[0297] discuss:
[0298] In Examples 1a to 1d and Comparative Example 1a, the metal complex GD121 of the present invention and the second compound H-1 of the present invention are used in the organic light-emitting layer, and in addition, the first compounds 2-1, 2-171, 2-167 and 2-170 of the present invention and the non-compound C-1 of the present invention are used respectively. From the test results in Table 2, it can be seen that the current efficiencies of Examples 1a to 1d and Comparative Example 1a are equivalent, but compared with Comparative Example 1a, the device lifespans of Examples 1a to 1d are increased by 111.3%, 58.9%, 44.7% and 77.5%, respectively.
[0299] In Example 1a and Comparative Example 1b, the metal complex GD121 of the present invention and the first compound 2-1 of the present invention are used in the organic light-emitting layer. In addition, the second compound H-1 of the present invention and the non-compound C-2 of the present invention are also used. Compared with Example 1a and Comparative Example 1b, the current efficiency is equivalent, and the device life is improved by 93.4%. It should be pointed out that compound C-2 is a commercial main material. When the electroluminescent device comprising the first metal complex and the first compound of the present invention further comprises the second compound of the present application, its performance is significantly better than that comprising the commercial compound C-2, especially the substantial improvement of the device life, which shows the superiority of the electroluminescent device performance of the present invention.
[0300] From the above discussion, it can be seen that the electroluminescent device comprising the first compound, the second compound and the first metal complex of the present invention has a significantly improved device life compared to the electroluminescent device not of the present invention.
[0301] Device Example 2
[0302] Device Example 2 was prepared the same as Example 1a, except that Compound H-82 was used instead of Compound H-1 in the emissive layer (EML).
[0303] Device Comparison Example 2
[0304] The device of Comparative Example 2 was prepared in the same manner as in Example 2, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0305] Device Example 3
[0306] Device Example 3 was prepared the same as Example 1a, except that Compound H-96 was used instead of Compound H-1 in the emissive layer (EML).
[0307] Device Comparison Example 3
[0308] The device of Comparative Example 3 was prepared in the same manner as in Example 3, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0309] Device Example 4
[0310] Device Example 4 was prepared the same as Example 1a, except that compound GD120 was used instead of compound GD121 in the emissive layer (EML).
[0311] Device Comparative Example 4a
[0312] The device of Comparative Example 4a was prepared in the same manner as in Example 4, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0313] Device Comparative Example 4b
[0314] The device of Comparative Example 4b was prepared in the same manner as Example 4, except that Compound C-2 was used instead of Compound H-1 in the emission layer (EML).
[0315] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0316] Table 3 Device structures of device embodiments 2-4 and comparative examples 2-3 and 4a-4b
[0317]
[0318]
[0319] The material structure used in the device is shown below:
[0320]
[0321] Table 4 shows that at 15 mA / cm 2 CIE data and current efficiency measured at constant current density; and at 80mA / cm 2 Device lifetime (LT95) measured at constant current density.
[0322] Table 4 Device data of device examples 2-4 and comparative examples 2-3 and 4a-4b
[0323]
[0324] discuss:
[0325] In Example 2 and Comparative Example 2, the metal complex GD121 of the present invention and the second host compound H-82 of the present invention are used in the organic light-emitting layer, and in addition, the compound 2-1 of the present invention and the non-compound C-1 of the present invention are used respectively. Compared with Example 2 and Comparative Example 2, the current efficiency is equivalent, and the device life is improved by 20.7%.
[0326] In Example 3 and Comparative Example 3, the metal complex GD121 of the present invention and the second host compound H-96 of the present invention are used in the organic light-emitting layer, and in addition, the compound 2-1 of the present invention and the non-compound C-1 of the present invention are used respectively. Compared with Comparative Example 3, the current efficiency of Example 3 is equivalent, and the device life is improved by 24.4%.
[0327] In Example 4 and Comparative Example 4a, the metal complex GD120 of the present invention and the second compound H-1 of the present invention are used in the organic light-emitting layer, and in addition, the first compound 2-1 of the present invention and the non-compound C-1 of the present invention are used respectively. Compared with Comparative Example 4a, the current efficiency of Example 4 is slightly improved, and the device life is improved by 43.1%.
[0328] In Example 4 and Comparative Example 4b, the metal complex GD120 of the present invention and the first compound 2-1 of the present invention are used in the organic light-emitting layer. In addition, the second compound H-1 of the present invention and the non-compound C-2 of the present invention are also used. Compared with Comparative Example 4b, the current efficiency of Example 4 is equivalent, and the device life is improved by 64.9%. It should be pointed out that compound C-2 is a commercial main material. When the electroluminescent device comprising the first metal complex and the first compound of the present invention further comprises the second compound of the present application, its performance is significantly better than that comprising the commercial compound C-2, especially the substantial improvement of the device life, which shows the superiority of the electroluminescent device performance of the present invention.
[0329] It can be seen from the above that the electroluminescent device comprising the first compound, the second compound and the first metal complex of the present invention can achieve a significant improvement in device life compared with the electroluminescent device not of the present invention.
[0330] Device Example 5
[0331] The preparation of device Example 5 was the same as Example 1a, except that compound H-107 was used instead of compound H-1 in the emission layer (EML), and 2-1:H-107:GD121=69:23:8.
[0332] Device Comparative Example 5a
[0333] The device of Comparative Example 5a was prepared in the same manner as in Example 5, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0334] Device Comparative Example 5b
[0335] The device of Comparative Example 5b was prepared in the same manner as Example 5, except that Compound C-3 was used instead of Compound H-107 in the emission layer (EML).
[0336] Device Example 6
[0337] Device Example 6 was prepared the same as Example 5, except that Compound H-119 was used instead of Compound H-107 in the emissive layer (EML).
[0338] Device Comparative Example 6a
[0339] The device of Comparative Example 6a was prepared in the same manner as in Example 6, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0340] Device Comparative Example 6b
[0341] The device of Comparative Example 6b was prepared in the same manner as in Example 6, except that Compound C-4 was used in place of Compound GD121 in the emission layer (EML).
[0342] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0343] Table 5 Device structures of device embodiments 5-6 and comparative examples 5a-5b and 6a-6b
[0344]
[0345] The new material structure used in the device is shown below:
[0346]
[0347] Table 6 shows that at 15 mA / cm 2 CIE data and current efficiency measured at constant current density; and at 80mA / cm 2Device lifetime (LT95) measured at constant current density.
[0348] Table 6 Device data of device examples 5-6 and comparative examples 5a-5b and 6a-6b
[0349]
[0350] discuss:
[0351] In Example 5 and Comparative Example 5a, the metal complex GD121 of the present invention and the second compound H-107 of the present invention are used in the organic light-emitting layer. In addition, the first compound 2-1 of the present invention and the non-compound C-1 of the present invention are also used. Compared with Comparative Example 5a, the current efficiency of Example 5 is equivalent, and the device life is improved by 24.6%.
[0352] Similarly, in Example 6 and Comparative Example 6a, the metal complex GD121 of the present invention and the second compound H-119 of the present invention are used in the organic light-emitting layer, and the first compound 2-1 of the present invention and the non-compound C-1 of the present invention are also used. Compared with Comparative Example 6a, Example 6 has the same current efficiency and the device life is improved by 12.1%.
[0353] In Example 5 and Comparative Example 5b, the metal complex GD121 of the present invention and the first compound 2-1 of the present invention are used in the organic light-emitting layer, and the second compound H-107 of the present invention and the non-inventive compound C-3 are also used. Compared with Comparative Example 5b, the current efficiency of Example 5 is slightly improved, and the device life is improved by 65.6%.
[0354] In Example 6 and Comparative Example 6b, the first compound 2-1 of the present invention and the main compound H-119 of the present invention are used in the organic light-emitting layer. In addition, the metal complex GD121 of the present invention and the metal complex C-4 not of the present invention are used respectively. Compared with Comparative Example 6b, the current efficiency and device life of Example 6 are significantly improved by 23.8% and 58.3% respectively.
[0355] It can be seen from the above results that the electroluminescent device comprising the first compound, the second compound and the first metal complex of the present invention has greatly improved device performance, especially improved device life, compared with electroluminescent devices not of the present invention.
[0356] Device Example 7
[0357] The preparation of device Example 7 was the same as Example 1a, except that compound GD30 was used instead of compound GD121 in the emission layer (EML), and 2-1:H-1:GD30=47:47:6.
[0358] Device Comparative Example 7a
[0359] The device of Comparative Example 7a was prepared in the same manner as in Example 7, except that Compound C-1 was used instead of Compound 2-1 in the emission layer (EML).
[0360] Device Comparative Example 7b
[0361] The device of Comparative Example 7b was prepared in the same manner as in Example 7, except that Compound C-2 was used instead of Compound H-1 in the emission layer (EML).
[0362] Device Example 8
[0363] Device Example 8 was prepared the same as Example 7, except that compound GD43 was used instead of compound GD30 in the emissive layer (EML).
[0364] Device Comparative Example 8a
[0365] The device of Comparative Example 8a was prepared in the same manner as in Example 8, except that Compound C-2 was used instead of Compound H-1 in the emission layer (EML).
[0366] Device Comparative Example 8b
[0367] The device of Comparative Example 8b was prepared in the same manner as in Example 8, except that Compound C-5 was used in place of Compound GD43 in the emission layer (EML).
[0368] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0369] Table 7 Device structures of device embodiments 7-8 and comparative examples 7a-7b and 8a-8b
[0370]
[0371] The new material structure used in the device is shown below:
[0372]
[0373] Table 8 shows that at 15 mA / cm 2 CIE data and current efficiency measured at constant current density; and at 80mA / cm 2 Device lifetime (LT95) measured at constant current density.
[0374] Table 8 Device data of device examples 7-8 and comparative examples 7a-7b and 8a-8b
[0375]
[0376]
[0377] discuss:
[0378] In Example 7 and Comparative Example 7a, the metal complex GD30 of the present invention and the second compound H-1 of the present invention are used in the organic light-emitting layer. In addition, the first compound 2-1 of the present invention and the non-compound C-1 of the present invention are used respectively. Compared with Comparative Example 7a, the current efficiency of Example 7 is improved, and the device life is improved by 20.1%. Similarly, when the metal complex GD43 of the present invention is used, the current efficiency of Example 8 is also improved compared with Comparative Example 8a, and the device life is improved by 65.1%.
[0379] In Example 7 and Comparative Example 7b, the metal complex GD30 of the present invention and the first compound 2-1 of the present invention are used in the organic light-emitting layer, and the second compound H-1 of the present invention and the non-compound C-2 of the present invention are also used. Compared with Comparative Example 7b, the current efficiency of Example 7 is improved, and the device life is improved by 84.3%.
[0380] In Examples 7 and 8 and Comparative Example 8b, the first compound 2-1 of the present invention and the second compound H-1 of the present invention are used in the organic light-emitting layer, and in addition, metal complexes GD30 and GD43 of the present invention and metal complex C-5 not of the present invention are used respectively. Compared with Comparative Example 8b, the current efficiency of Examples 7 and 8 is increased by 19.7% and 11.8%, respectively, and the device life is increased by 80.9% and 19.5%, respectively.
[0381] In summary, the electroluminescent device comprising the first compound, the second compound and the first metal complex of the present invention has greatly improved device performance, especially significantly improved device life, compared with electroluminescent devices not of the present invention. This provides the industry with an excellent combination of light-emitting layer materials.
[0382] 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 at least a first metal complex, a first compound, and a second compound; in, The first metal complex comprises a metal M and a ligand L coordinated to the metal M. a , ligand L a Having a structure represented by Formula 1: in, The metal M is selected from metals with a relative atomic mass greater than 40; Cy is selected from substituted or unsubstituted aryl having 5 to 24 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 24 ring atoms at each occurrence, the same or different; the Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R' at each occurrence; when two R' are present at the same time, the two R' are the same or different; X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N, and at least one of X1-X4 is C and connected to the Cy; X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; At least one of X1-X8 is CR x , and the R x is cyano or fluorine; The adjacent substituents R', R x can optionally be linked to form a ring; Wherein, the first compound has a structure represented by Formula 2: in, Each time U appears, it is selected from C, CR u or N; Each time V appears, it is selected from CR in the same or different way. v or N; L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R u and R v can optionally be linked to form a ring; Wherein, the second compound has a structure represented by Formula 3: in, Ar1 has a structure represented by Formula A: in, Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se; L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Each occurrence of Z1-Z8 is selected from C, CR z or N, and at least one of Z1-Z8 is C and connected to L3; At least one CR in Z1-Z8 z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Ar2 is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence, the same or different; "*" represents the connection position between Ar1 and L3; Adjacent substituent R z can be optionally linked into a ring; R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; When R z The substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino group refers to any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl and amino groups, which may be substituted by one or more deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted 3 to 20 ring carbon atoms The present invention is substituted with an unsubstituted heterocyclic group, an unsubstituted aralkyl group having 7-30 carbon atoms, an unsubstituted alkoxy group having 1-20 carbon atoms, an unsubstituted aryloxy group having 6-30 carbon atoms, an unsubstituted alkenyl group having 2-20 carbon atoms, an unsubstituted alkynyl group having 2-20 carbon atoms, an unsubstituted aryl group having 6-30 carbon atoms, an unsubstituted alkylsilyl group having 3-20 carbon atoms, an unsubstituted arylsilyl group having 6-20 carbon atoms, an unsubstituted alkylgermanyl group having 3-20 carbon atoms, an unsubstituted arylgermanyl group having 6-20 carbon atoms, an unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof; R'、R x , R u , R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted 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.
2. The electroluminescent device according to claim 1, wherein Cy is selected from any one of the following groups: in, Each occurrence of R is the same or different, indicating mono-substitution, poly-substitution, or no substitution; when multiple R are present in any structure, the R may be the same or different; R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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; Two adjacent substituents R can optionally be linked to form a ring; Wherein, "#" indicates the position connected to the metal M, Indicates a location connected to X1, X2, X3, or X4.
3. The electroluminescent device according to claim 1, wherein The first metal complex has M(L a ) m (L b ) n (L c ) q The general formula of ; where M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a The same or different; when n is equal to 2, the two L b The same or different; when q is equal to 2, the two L c Same or different; L a Each occurrence is identically or differently selected from the group consisting of: X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R'; when two R's are present at the same time, the two R's are the same or different; R and R x Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; At least one R x is selected from cyano or fluorine; Adjacent substituents R, R', R x can optionally be linked to form a ring; L b and L c Each occurrence is identically or differently selected from any one of the following groups: in, X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ; R a , R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; Adjacent substituent R a , R b , R c , R N1 , R C1 , R C2 can optionally be linked to form a ring; R, R', R x , R a , R b , R c , R N1 , R C1 and R C2 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
4. The electroluminescent device according to claim 1, wherein M is selected, identically or differently on each occurrence, from Pt or Ir.
5. The electroluminescent device according to claim 1, wherein The first metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 5: in, m is 1, 2 or 3; when m is 2 or 3, multiple L a The same or different; when m is 1, the two L b Same or different; X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R'; when two R's are present at the same time, the two R's are the same or different; Each occurrence of X3-X8 is the same or different selection from CR x or N; At least one of X3-X8 is CR x , and the R x is cyano or fluorine; R, when present at each occurrence, is identical or different and represents mono-substitution, poly-substitution, or no substitution; R1-R8, R', R x and R, at each occurrence, is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R1-R8 can be optionally linked to form a ring; Adjacent substituents R', R and R x Can optionally be linked to form a ring.
6. The electroluminescent device according to claim 1, wherein X is selected from O or S.
7. The electroluminescent device according to claim 1, wherein: At least one of X5-X8 is selected from CR x , and the R x It is cyano or fluorine.
8. The electroluminescent device according to claim 1, wherein: X7 or X8 is CR x , and the R x It is cyano or fluorine.
9. The electroluminescent device according to claim 5, wherein: At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
10. The electroluminescent device according to claim 5, wherein: At least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; optionally, the hydrogen in the above groups can be partially or completely deuterated.
11. The electroluminescent device according to claim 1, wherein At least two of X3-X8 are selected from CR x , and one of the R x is selected from fluorine or cyano, at least one other R x Selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, cyano, and combinations thereof.
12. The electroluminescent device according to claim 1, wherein: At least two of X3-X8 are selected from CR x , and one of the R x is selected from fluorine or cyano, at least one other R x Selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, cyano, and combinations thereof.
13. The electroluminescent device according to claim 2, wherein: R is 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.
14. The electroluminescent device according to claim 13, wherein: At least one R is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
15. The electroluminescent device according to claim 1, wherein: L a Each occurrence is identically or differently selected from the group consisting of:
16. The electroluminescent device according to claim 3, wherein: L b Each occurrence is identically or differently selected from the group consisting of:
17. The electroluminescent device according to claim 3, wherein: L c Each occurrence is identically or differently selected from the group consisting of:
18. The electroluminescent device of claim 1, wherein: The first metal complex is selected from the group consisting of:
19. The electroluminescent device of claim 1, wherein: The first compound has a structure represented by Formula 2a: Wherein, in Formula 2a, Each time U appears, it is selected from C, CR u or N; Each time V appears, it is selected from CR in the same or different way. v or N; Ar4 is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence; L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted 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; Adjacent substituents Ar4, R u and R v Can optionally be linked to form a ring.
20. The electroluminescent device of claim 1, wherein: The first compound has a structure represented by Formula 2b: Wherein, in Formula 2b, Each time U appears, it is selected from CR in the same or different way. u or N; Each time V appears, it is selected from CR in the same or different way. v or N; Ar4 is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence; L1 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted 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; Adjacent substituents Ar4, R u and R v Can optionally be linked to form a ring.
21. The electroluminescent device of claim 1, wherein: Each occurrence of U is selected from C or CR, either identically or differently. u , and / or V is selected from CR v .
22. The electroluminescent device of claim 1, wherein: R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
23. The electroluminescent device according to claim 1, wherein R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
24. The electroluminescent device of claim 1, wherein: Each occurrence of Z1-Z8 is selected from C or CR, either identically or differently. z .
25. The electroluminescent device of claim 1, wherein: At least two of Z1-Z8 are CR z , and the at least one R z is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; at least one other R z is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a combination thereof.
26. The electroluminescent device of claim 1, wherein: At least one, at least two, or at least three of Z1-Z8 are selected from CR z , and the R z is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
27. The electroluminescent device of claim 1, wherein: At least one, at least two, or at least three of Z1-Z8 are selected from CR z , and the R z Any of the following groups selected from unsubstituted or substituted by one or more of deuterium, halogen, and cyano: phenyl, naphthyl, biphenyl, and terphenyl.
28. The electroluminescent device of claim 1, wherein: At least one of Z1-Z4 is selected from C and is connected to L3; Z5 and / or Z8 is selected from R z , and the R z It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
29. The electroluminescent device of claim 1, wherein: At least one of Z1-Z4 is selected from C and connected to L3; at the same time, at least one of Z1-Z4 is selected from CR z , and the R z It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
30. The electroluminescent device of claim 1, wherein: The second compound has a structure represented by one of Formula 3-1 to Formula 3-4: in, Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se; L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Each occurrence of Z1-Z8 is selected from C, CR z or N; In Formula 3-1 and Formula 3-2, at least one of Z1-Z8 is C and connected to L3, and at least one of Z1-Z8 is selected from CR z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; W1-W8 are selected from C, CR in the same or different manner at each occurrence w or N; Ar2 and Ar3 are identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof at each occurrence; R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R w and R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted 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; Adjacent substituent R z , R w , R n Can optionally be linked to form a ring.
31. The electroluminescent device of claim 1, wherein: L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.
32. The electroluminescent device of claim 1, wherein: L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
33. The electroluminescent device of claim 1, wherein L1 to L3 are selected from single bonds at each occurrence, the same or different.
34. The electroluminescent device of claim 20, wherein: Ar2 to Ar4 are identically or differently selected at each occurrence from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.
35. An electroluminescent device as claimed in claim 34, wherein Ar2 to Ar4 are selected from the following groups which are unsubstituted or substituted by one or more of deuterium, halogen, and cyano groups, the same or different at each occurrence: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, diazadibenzothiophenyl, and combinations thereof.
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 second compound is selected from the group consisting of:
38. The electroluminescent device of claim 1, wherein the organic layer is a light-emitting layer, the first metal complex is doped in the first compound and the second compound, and the weight of the first metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
39. The electroluminescent device of claim 38, wherein the weight of the first metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
40. An electronic device comprising the electroluminescent device according to any one of claims 1 to 39.
41. A compound combination comprising a first metal complex, a first compound, and a second compound; in, The first metal complex comprises a metal M and a ligand L coordinated to the metal M. a , ligand L a Having a structure represented by Formula 1: in, The metal M is selected from metals with a relative atomic mass greater than 40; Cy is selected from substituted or unsubstituted aryl having 5 to 24 ring atoms, or substituted or unsubstituted heteroaryl having 5 to 24 ring atoms at each occurrence, the same or different; the Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R' at each occurrence; when two R' are present at the same time, the two R' are the same or different; X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N, and at least one of X1-X4 is C and connected to the Cy; X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; At least one of X1-X8 is CR x , and the R x is cyano or fluorine; The adjacent substituents R', R x can optionally be linked to form a ring; Wherein, the first compound has a structure represented by Formula 2: in, Each time U appears, it is selected from C, CR u or N; Each time V appears, it is selected from CR in the same or different way. v or N; L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R u and R v can optionally be linked to form a ring; Wherein, the second compound has a structure represented by Formula 3: in, Ar1 has a structure represented by Formula A: in, Each occurrence of Z is identically or differently selected from the group consisting of O, S and Se; L3 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Each occurrence of Z1-Z8 is selected from C, CR z or N, and at least one of Z1-Z8 is C and connected to L3; At least one CR in Z1-Z8 z , and the R z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Ar2 is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof at each occurrence, the same or different; "*" represents the connection position between Ar1 and L3; Adjacent substituent R z can be optionally linked into a ring; R z The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; When R z The substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino group refers to any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl and amino groups, which may be substituted by one or more deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted 3 to 20 ring carbon atoms The present invention is substituted with an unsubstituted heterocyclic group, an unsubstituted aralkyl group having 7-30 carbon atoms, an unsubstituted alkoxy group having 1-20 carbon atoms, an unsubstituted aryloxy group having 6-30 carbon atoms, an unsubstituted alkenyl group having 2-20 carbon atoms, an unsubstituted alkynyl group having 2-20 carbon atoms, an unsubstituted aryl group having 6-30 carbon atoms, an unsubstituted alkylsilyl group having 3-20 carbon atoms, an unsubstituted arylsilyl group having 6-20 carbon atoms, an unsubstituted alkylgermanyl group having 3-20 carbon atoms, an unsubstituted arylgermanyl group having 6-20 carbon atoms, an unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof; R'、R x , R u , R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted 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.
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