An electroluminescent device
By using the first metal complex and the first compound of La ligand with a specific structure in OLEDs, the problems of reduced efficiency at high brightness and insufficient performance of blue phosphorescent devices are solved, and higher efficiency and longer device life are achieved.
Patent Information
- Application Number
- CN202110165136.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-02-06
- Publication Date
- 2025-03-28
- Estimated Expiration
- 2041-02-06
AI Technical Summary
Existing organic electroluminescent devices (OLEDs) have reduced efficiency under high brightness conditions. Blue phosphorescent devices have problems such as unsaturation, short life and high operating voltage, making it difficult to achieve a more saturated luminescence spectrum, higher efficiency and longer device life.
An electroluminescent device is employed that comprises a first metal complex with a La ligand with a specific structure and a first compound with a specific structure, which are combined in an organic layer to improve the efficiency and performance of the device.
Through this combination, the efficiency of OLEDs is significantly improved, especially the improvement of external quantum efficiency (EQE), or the driving voltage and half-maximum width are reduced, achieving better comprehensive performance.
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Figure CN114914381B_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 and a first compound having a structure of Formula 3, and an electronic device comprising the electroluminescent device and a compound combination comprising the first metal complex and the first 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] CN111808142A discloses a metal complex having the following general structure: And its application in organic electroluminescent devices, further discloses the following specific compounds: The light-emitting layer in the organic electroluminescent device comprises the metal complex and a host material, and the host material is one or a mixture of 4,4'-N,N'-biphenyldicarbazole (CBP), octahydroxyquinoline, metal phenoxybenzothiazole compounds, polyfluorene, aromatic fused rings, and zinc complexes. The device embodiment only discloses the device structure of CBP as the host material, and does not focus on the combined use of a host compound other than CBP and the metal complex in the device.
[0009] US20200251666A1 discloses a metal complex comprising a ligand having the following structure: And the use of the metal complex in an organic electroluminescent device, further discloses a metal complex having the following general structure: And further discloses the following metal complex: And the complex and Application in host materials. The application does not disclose the metal complexes substituted with the specific (hetero)aryl groups in the present application and their applications in organic electroluminescent devices, nor does it teach that the metal complexes substituted with the specific (hetero)aryl groups in the present application have better performance in host materials having a triazine skeleton.
[0010] US20200287144A1 discloses a metal complex comprising the following ligands: And the use of the metal complex in an organic electroluminescent device, wherein X1 is selected from silicon and germanium, and further discloses the following structure: etc., which also discloses limited host materials, and only discloses the device structure of CBP as the host material in the examples. This application focuses on the effect of silane and germanium groups in the ligand on the device performance, and does not focus on the improvement of device performance by metal complexes with specific (hetero)aryl substitutions on dibenzofuran, nor on the improvement of device performance by different host materials.
[0011] US2010187977A1 discloses a compound having the following general structure: Ring A consists of The invention discloses some phosphorescent dopants, but the invention does not disclose or teach the use of metal complexes containing the specific (hetero)aryl substituted ligands in the invention as phosphorescent dopants, and the effects on device performance when used in such host materials.
[0012] US20170186965A1 discloses a The invention discloses a structured compound and an electroluminescent device comprising the compound. However, the application only involves phenylpyridine Ir and Pt complexes as phosphorescent dopants in the examples. The application does not focus on the metal complexes containing the specific (hetero)aryl substituted ligands in the present application as phosphorescent dopants, and the device can obtain better performance when used in such host materials.
[0013] US20200127213A1 discloses an organic photoelectric device, wherein the light-emitting layer comprises The first subject represented by Although the application lists some phosphorescent dopants, it does not focus on the metal complex containing the specific (hetero)aryl substituted ligand in the present application as a phosphorescent dopant, and when used in such a host material, the device can obtain better performance.
[0014] US2019363261A1 discloses a method having and The invention discloses a compound formed by bonding, and an electroluminescent device comprising the compound. However, the application only involves phenylpyridine Ir complexes as luminescent dopants in the examples. The application does not focus on metal complexes containing specific (hetero)aryl substituted ligands in the present application as phosphorescent dopants, and the device can obtain better performance when used in such host materials.
[0015] JP2017107992A discloses an organic compound having the following general structural formula and an organic light-emitting device comprising the compound: Wherein, X is oxygen or sulfur, and R1 to R5 are independently hydrogen, alkyl, cyano or fluorine. However, the application only involves phenylpyridine Ir complexes as phosphorescent dopants in the embodiments. The application does not pay attention to the metal complexes containing specific (hetero)aryl substituted ligands in the present application as phosphorescent dopants, and the device can obtain better performance when used in such host materials. Summary of the invention
[0016] The present invention aims to provide a series of L having a structure of Formula 1 a The first metal complex of the ligand and the electroluminescent device having the first compound having the structure of Formula 3 solve at least part of the above problems.
[0017] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0018] anode,
[0019] cathode,
[0020] and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first compound;
[0021] 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:
[0022]
[0023] In formula 1,
[0024] The metal M is selected from metals with a relative atomic mass greater than 40;
[0025] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;
[0026] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0027] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; at least one of X1-X4 is C and is connected to the Cy;
[0028] X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0029] At least one of X1-X8 is CR x , and the R x Ar has a structure represented by Formula 2:
[0030]
[0031] a is selected from 0, 1, 2, 3, 4 or 5;
[0032] R a1 and R a2 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;
[0033] Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8;
[0034] “*” indicates the connection position of formula 2;
[0035] Wherein, the first compound has a structure represented by Formula 3:
[0036]
[0037] in,
[0038] Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and they are connected to formula 4;
[0039]
[0040] in,
[0041] Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" can be the same or different;
[0042] p is 0 or 1; r is 0 or 1;
[0043] When Q is selected from N, p is 0 and r is 1;
[0044] When Q is selected from the group consisting of O, S, Se, NR", CR"R", SiR"R", GeR"R" and R"C=CR", p is 1 and r is 0;
[0045] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0046] Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N;
[0047] “*” represents the connection position between Formula 4 and Formula 3;
[0048] R', R x , R a1 , R a2 , R e , R' and R qEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0049] The adjacent substituents R', R x , R a1 , R a2 can optionally be linked to form a ring;
[0050] Adjacent substituent R e , R”, R q Can optionally be linked to form a ring.
[0051] According to one embodiment of the present invention, an electronic device is disclosed, which includes the electroluminescent device described in the above embodiment.
[0052] According to another embodiment of the present invention, a compound combination is disclosed, which comprises the first metal complex and the first compound described in the above embodiment.
[0053] 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 and a first compound having a structure of Formula 3. By selecting a combination of the two compounds, the performance of the organic electroluminescent device can be significantly improved compared with the prior art, such as improving the device efficiency, especially improving the EQE, or reducing the driving voltage and the half-peak width, and ultimately achieving the beneficial effect of significantly improving the overall performance of the device. BRIEF DESCRIPTION OF THE DRAWINGS
[0054] Figure 1 is a schematic diagram of an electroluminescent device that may contain combinations of metal complexes and compounds disclosed herein.
[0055] Figure 2 is a schematic diagram of another electroluminescent device that may contain the metal complexes and compound combinations disclosed herein. DETAILED DESCRIPTION
[0056] 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.
[0057] 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.
[0058] 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.
[0059] 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.
[0060] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0061] 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.
[0062] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0063] 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.
[0064] 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.
[0065] 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.
[0066] 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).
[0067] 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.
[0068] 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).
[0069] Definition of Substituent Terms
[0070] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0071] 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.
[0072] 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.
[0073] 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.
[0074] 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.
[0075] 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.
[0076] 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.
[0077] 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.
[0078] 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.
[0079] 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.
[0080] 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.
[0081] 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,
[0082] 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.
[0083] 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.
[0084] 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.
[0085] 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.
[0086] 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.
[0087] 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.
[0088] 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.
[0089] 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.
[0090] 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.
[0091] 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.
[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 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:
[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 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:
[0095]
[0096] 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:
[0097]
[0098] 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:
[0099]
[0100] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0101] anode,
[0102] cathode,
[0103] and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first compound;
[0104] 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:
[0105]
[0106] In formula 1,
[0107] The metal M is selected from metals with a relative atomic mass greater than 40;
[0108] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;
[0109] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0110] X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; at least one of X1-X4 is C and is connected to the Cy;
[0111] X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
[0112] At least one of X1-X8 is CR x , and the R x Ar has a structure represented by Formula 2:
[0113]
[0114] a is selected from 0, 1, 2, 3, 4 or 5;
[0115] R a1 and R a2 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;
[0116] Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8;
[0117] “*” indicates the connection position of formula 2;
[0118] Wherein, the first compound has a structure represented by Formula 3:
[0119]
[0120] in,
[0121] Each occurrence of E1-E6 is selected from C, CR e or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and they are connected to formula 4;
[0122]
[0123] in,
[0124] Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" can be the same or different;
[0125] p is 0 or 1; r is 0 or 1;
[0126] When Q is selected from N, p is 0 and r is 1;
[0127] When Q is selected from the group consisting of O, S, Se, NR", CR"R", SiR"R", GeR"R" and R"C=CR", p is 1 and r is 0;
[0128] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0129] Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N;
[0130] “*” represents the connection position between Formula 4 and Formula 3;
[0131] R', R x (refers to the existence of X1-X8 and excluding the above specific R X The remaining R X ), R a1 , R a2 , R e , R' and R q Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted 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;
[0132] The adjacent substituents R', R x , R a1 , R a2 can optionally be linked to form a ring;
[0133] Adjacent substituent R e , R”, R q Can optionally be linked to form a ring.
[0134] As used herein, “adjacent substituents R′, R x , R a1 , R a2 "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 a1 Between the two substituents R a2 Between the two substituents R' and R xBetween the two substituents R a1 and R a2 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 context, “the adjacent substituent R e , R”, R q "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R e Between two substituents R", between two substituents R q Between the two substituents R" and R q Any one or 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 article, "ring atoms" in aromatic rings and heteroaromatic rings refer to atoms that are bonded to form a cyclic structure with aromaticity (for example: a monocyclic (hetero) aromatic ring, a condensed (hetero) aromatic ring) that constitutes the ring itself. Carbon atoms and heteroatoms (including but not including O, S, N, Se or Si, etc.) in the ring are all counted in the number of ring atoms. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the number of ring atoms. For example, the number of ring atoms of phenyl, pyridyl, and triazine is 6; the number of ring atoms of dithiophene and difuran is 8; the number of ring atoms of benzothienyl and benzofuranyl is 9; the number of ring atoms of naphthyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl is 10; the number of ring atoms of dibenzothiophene, dibenzofuran, fluorene, azadibenzothiophene, azadibenzofuran and azafluorene is 13; the various examples described here are only for illustration, and other cases are similar. When a in Formula 2 is 0, it means that Ar has In this case, "the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8" means that ring Ar1 is an aromatic ring or heteroaromatic ring with a total number of ring atoms greater than or equal to 8; when a in formula 2 is 1, it means that Ar has For example, in this case, both ring Ar1 and ring Ar2 are phenyl, R a1 and R a2 When both are hydrogen, the total number of ring atoms of ring Ar1 and ring Ar2 is 12; for example, when both ring Ar1 and ring Ar2 are phenyl, R a1 All are hydrogen, R a2 When it is monosubstituted and is phenyl, the total number of ring atoms in the ring Ar1 and the ring Ar2 is equal to 12. The same applies to other cases.
[0137] According to one embodiment of the present invention, in the first metal complex, Cy is selected from any structure in the group consisting of:
[0138] in,
[0139] 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;
[0140] 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;
[0141] Two adjacent substituents R can optionally be linked to form a ring;
[0142] Among them, '#' indicates the position connected to the metal M, Indicates a location connected to X1, X2, X3, or X4.
[0143] Herein, "two adjacent substituents R can be optionally connected to form a ring" is intended to mean that any one or more of the substituent groups formed between any two adjacent substituents R can be connected to form a ring. Obviously, these substituents may not be connected to form a ring.
[0144] According to one embodiment of the present invention, L a Each occurrence is identically or differently selected from the group consisting of:
[0145]
[0146]
[0147]
[0148]
[0149]
[0150] wherein X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0151] R and R x Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0152] R x At least one of them is Ar, and the Ar has a structure represented by Formula 2:
[0153]
[0154] a is selected from 0, 1, 2, 3, 4 or 5;
[0155] Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8;
[0156] R a1 and R a2 Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0157] R, R', R x , R a1 and R a2The 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;
[0158] Adjacent substituents R, R', R x , R a1 and R a2 can optionally be linked to form a ring;
[0159] “*” indicates the connection position of Formula 2.
[0160] As used herein, “adjacent substituents R, R′, R x , R a1 and R a2 "can be optionally connected to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R, between two substituents R', between two substituents R x Between the two substituents R a1 Between the two substituents R a2 Between the two substituents R' and R x Between the two substituents R a1 and R a2 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.
[0161] According to one embodiment of the present invention, the first metal complex has M(L a ) m (L b ) n (L c ) qThe general formula of
[0162] in,
[0163] M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, the same or different; preferably, M is selected from Pt or Ir at each occurrence, the same or different;
[0164] 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;
[0165] 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;
[0166] L b and L c Each occurrence is identically or differently selected from any one of the following groups:
[0167]
[0168] in,
[0169] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;
[0170] R a , R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0171] 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;
[0172] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.
[0173] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0174] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears, the same or different.
[0175] 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.
[0176] 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:
[0177]
[0178] in,
[0179] m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different;
[0180] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0181] Each occurrence of Y1-Y4 is identical or different and is selected from CR y or N;
[0182] X3-X8 are selected from CR in the same or different way each time they appear x or N;
[0183] X3-X8 are selected from CR in the same or different way each time they appear x or N;
[0184] At least one of X3-X8 is CR x , and R x Ar has a structure represented by Formula 2:
[0185]
[0186] a is selected from 0, 1, 2, 3, 4 or 5;
[0187] R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no-substitution;
[0188] Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8;
[0189] R', R x , R y , R1-R8, R a1 and R a2 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;
[0190] “*” indicates the connection position of formula 2;
[0191] The adjacent substituents R', R x , R y , R a1 , R a2 can optionally be linked to form a ring;
[0192] Adjacent substituents R1 to R8 can optionally be linked to form a ring.
[0193] As used herein, “adjacent substituents R′, R x , R y , R a1, R a2 "can be optionally connected to form a ring" is intended to mean that adjacent groups of substituents, for example, between two substituents R', between two substituents R x Between the two substituents R y Between the two substituents R a1 Between the two substituents R a2 Between the two substituents R a1 and R a2 Between the two substituents R' and R x Between, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring. "Adjacent substituents R1-R8 can optionally be connected to form a ring" is intended to mean that adjacent substituent groups, for example, between adjacent substituents R1 and R2, between adjacent substituents R3 and R2, between adjacent substituents R3 and R4, between adjacent substituents R5 and R4, between adjacent substituents R5 and R6, between adjacent substituents R7 and R6, between adjacent substituents R7 and R8, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.
[0194] 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 5A:
[0195]
[0196] in,
[0197] m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different;
[0198] X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R'; when two R' exist at the same time, the two R' are the same or different;
[0199] R x and R y The same or different at each occurrence indicates mono-, poly- or no-substitution;
[0200] R x At least one of them is Ar, and the Ar has a structure represented by Formula 2:
[0201]
[0202] a is selected from 0, 1, 2, 3, 4 or 5;
[0203] Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8;
[0204] R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no-substitution;
[0205] R', R x , R y , R1-R8, R a1 and R a2 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;
[0206] “*” indicates the connection position of formula 2;
[0207] The adjacent substituents R', R x , R y , R a1 , R a2 can optionally be linked to form a ring;
[0208] Adjacent substituents R1 to R8 can optionally be linked to form a ring.
[0209] According to one embodiment of the present invention, in the first metal complex, X1-X8 are selected from C and CR x, and R x At least one of them is Ar.
[0210] According to one embodiment of the present invention, in Formula 5, X3-X8 are selected from CR x .
[0211] According to one embodiment of the present invention, in Formula 5, Y1-Y4 are selected from CR y .
[0212] According to one embodiment of the present invention, in the first metal complex, at least one of X1-X8 is N, for example, one of X1-X8 is N or two of them are N.
[0213] According to an embodiment of the present invention, in Formula 5, at least one of X3-X8 is N, for example, one of X3-X8 is N or two of them are N.
[0214] According to an embodiment of the present invention, in Formula 5, at least one of Y1-Y4 is N, for example, one of Y1-Y4 is N or two of them are N.
[0215] According to one embodiment of the present invention, in the first metal complex, at least one of X5-X8 is selected from CR x , and the R x It's Ar.
[0216] According to one embodiment of the present invention, in the first metal complex, at least one of X7 or X8 is selected from CR x , and the R x It's Ar.
[0217] According to one embodiment of the present invention, in the first metal complex, X8 is selected from CR x , and the R x It's Ar.
[0218] According to one embodiment of the present invention, in the first metal complex, at least two of X5-X8 are selected from CR x , and at least one of them is R x is Ar, at least another R x Selected from fluorine or cyano.
[0219] According to one embodiment of the present invention, in the first metal complex, X7 and X8 are selected from CR x , one of which is selected from CR x , and the R x It is Ar, another R x Selected from fluorine or cyano.
[0220] According to one embodiment of the present invention, in the first metal complex, X8 is selected from CR x , and the R x is Ar, X7 is selected from CR x , and the R x Selected from fluorine or cyano.
[0221] According to one embodiment of the present invention, in the first metal complex, X7 is selected from CR x , and the R x is Ar, X8 is selected from CR x , and the R x Selected from fluorine or cyano.
[0222] According to one embodiment of the present invention, in the first metal complex, a is selected from 0, 1, 2 or 3.
[0223] According to one embodiment of the present invention, in the first metal complex, a is selected from 1.
[0224] According to one embodiment of the present invention, in the first metal complex, X is selected from O or S.
[0225] According to one embodiment of the present invention, in the first metal complex, X is selected from O.
[0226] According to one embodiment of the present invention, in the first metal complex, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
[0227] According to one embodiment of the present invention, in the first metal complex, R a1 and R a2Each 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, and combinations thereof.
[0228] According to one embodiment of the present invention, in the first metal complex, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 15 carbon atoms, and combinations thereof.
[0229] According to one embodiment of the present invention, in the first metal complex, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, and combinations thereof.
[0230] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-18 ring atoms, heteroaromatic rings having 5-18 ring atoms, or combinations thereof each time they appear; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.
[0231] According to one embodiment of the present invention, in Ar, the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 24.
[0232] According to one embodiment of the present invention, in Ar, the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 18.
[0233] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings having 5 or 6 ring atoms, or heteroaromatic rings having 5 or 6 ring atoms, or a combination thereof, in each occurrence, the same or different.
[0234] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings or heteroaromatic rings having 6 ring atoms, the same or different at each occurrence.
[0235] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings having 6 ring atoms, the same or different at each occurrence.
[0236] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from the group consisting of: benzene ring, pyridine ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, silylfluorene ring, quinoline ring, isoquinoline ring, benzofuran ring, benzothiophene ring, indene ring, dibenzofuran ring, dibenzothiophene ring, triazine ring, triphenylene ring, carbazole ring, azacarbazole ring, azafluorene ring, azadibenzofuran ring, azadibenzothiophene ring, and combinations thereof each time they appear; and the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.
[0237] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings having 6 ring atoms, heteroaromatic rings having 5 or 6 ring atoms, or a combination thereof, in each occurrence, either identically or differently.
[0238] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings or heteroaromatic rings having 6 ring atoms, the same or different at each occurrence.
[0239] According to one embodiment of the present invention, in Ar, ring Ar1 and ring Ar2 are selected from aromatic rings having 6 ring atoms, the same or different at each occurrence.
[0240] According to one embodiment of the present invention, in the first metal complex, Ar is selected from the following group consisting of the same or different each time it appears:
[0241]
[0242] and combinations thereof;
[0243] Optionally, the hydrogen in the above groups may be partially or fully deuterated; wherein "*" indicates the attachment position of the substituent.
[0244] According to one embodiment of the present invention, in the first metal complex, R xEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.
[0245] According to one embodiment of the present invention, in the first metal complex, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 11 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
[0246] According to one embodiment of the present invention, in the first metal complex, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, cyano, and combinations thereof.
[0247] According to one embodiment of the present invention, in the first metal complex, at least two of X3-X8 are selected from CR x , where at least one R x is Ar, and 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.
[0248] According to one embodiment of the present invention, in the first metal complex, at least two of X3-X8 are selected from CR x , where at least one R x is Ar, and at least one other R xSelected 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 3-11 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, cyano, and combinations thereof.
[0249] According to one embodiment of the present invention, in the first metal complex, at least two of X3-X8 are selected from CR x , where at least one R x is Ar, and at least one other R x Selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, cyano, and combinations thereof.
[0250] According to one embodiment of the present invention, in the first metal complex, at least three of X3-X8 are selected from CR x , where at least one R x is Ar, at least one R x is selected from fluorine or cyano, and at least one R x Selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, and combinations thereof.
[0251] According to one embodiment of the present invention, in the first metal complex, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.
[0252] According to one embodiment of the present invention, in the first metal complex, R yEach 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, and combinations thereof.
[0253] According to one embodiment of the present invention, in the first metal complex, R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 15 carbon atoms, and combinations thereof.
[0254] According to one embodiment of the present invention, in the first metal complex, at least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0255] According to one embodiment of the present invention, in the first metal complex, 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.
[0256] According to one embodiment of the present invention, in the first metal complex, 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, and combinations thereof.
[0257] According to one embodiment of the present invention, in the first metal complex, 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, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the hydrogen in the above groups is partially or completely deuterated.
[0258] According to one embodiment of the present invention, in the first metal complex, R' is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
[0259] According to one embodiment of the present invention, in the first metal complex, R' is a methyl group or a deuterated methyl group.
[0260] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The group consisting of L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17.
[0261] 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 18.
[0262] According to one embodiment of the present invention, L c Each time it appears, choose the same or different one from L c1 -L c360 The group consisting of L c1 -L c360 The specific structure is described in claim 19.
[0263] According to one embodiment of the present invention, the first metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , La2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any one or two of the group consisting of L b Choose from L b1 To L b128 Any of the group consisting of a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17, L b1 To L b128 The specific structure is described in claim 18.
[0264] According to one embodiment of the present invention, the first metal complex has Ir(L a )(L b )2 structure, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any of the groups consisting of L b Choose from L b1 To L b128 Any one or any two of the group consisting of a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17, L b1 To L b128 The specific structure is described in claim 18.
[0265] According to one embodiment of the present invention, the first metal complex has Ir(La )3 structure, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any one, any two, or any three of the group consisting of a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17.
[0266] According to one embodiment of the present invention, the first metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any one or two of the group consisting of L c Choose from L c1 To L c360 Any of the group consisting of a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17, L c1 To L c360 The specific structure is described in claim 19.
[0267] According to one embodiment of the present invention, the first metal complex has Ir(L a )(Lc )2 structure, L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any of the groups consisting of L c Choose from L c1 To L c360 Any one or any two of the group consisting of a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 The specific structure is described in claim 17, L c1 To L c360 The specific structure is described in claim 19.
[0268] According to one embodiment of the present invention, the first metal complex has Ir(L a )(L b )(L c ) structure, where L a Each time it appears, choose the same or different one from L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244 and L a5-1 To L a5-111 Any of the groups consisting of L b Choose from L b1 To L b128 Any of the groups consisting of L c Choose from L c1 To L c360 Any one of the group consisting of; wherein L a1-1 To L a1-509 , L a2-1 To L a2-538 , L a3-1 To L a3-249 , L a4-1 To L a4-244and L a5-1 To L a5-111 The specific structure is described in claim 17, L b1 To L b128 The specific structure is described in claim 18, L c1 To L c360 The specific structure is described in claim 19.
[0269] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of metal complex 1 to metal complex 1280, wherein the specific structures of metal complex 1 to metal complex 1280 are as described in claim 20.
[0270] According to one embodiment of the present invention, in the first compound, each occurrence of E1-E6 is identically or differently selected from C, CR e Or N, and at least two of E1-E6 are N, at least two of E1-E6 are C, and both Cs are connected to Formula 4.
[0271] According to one embodiment of the present invention, in the first compound, each occurrence of E1-E6 is identically or differently selected from C, CR e Or N, and at least two of E1-E6 are N, at least two of E1-E6 are C, and both Cs are connected to Formula 4, in one of the Formulas 4, p is 0 and r is 1; in the other Formula 4, p is 1 and r is 0.
[0272] According to one embodiment of the present invention, in the first compound, each occurrence of E1-E6 is identically or differently selected from C, CR e or N, and three of E1-E6 are N, and at least one of E1-E6 is CR e , and the R e Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
[0273] According to one embodiment of the present invention, in the first compound, each occurrence of E1-E6 is identically or differently selected from C, CR e or N, and three of E1-E6 are N, and at least one of E1-E6 is CR e , and the R eEach occurrence is identically or differently selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof.
[0274] According to one embodiment of the present invention, the first compound has a structure represented by Formula 3a or Formula 3b:
[0275]
[0276] Wherein, in Formula 3a or Formula 3b,
[0277] Q is selected from the group consisting of O, S, Se, NR", CR"R" and SiR"R", GeR"R" and R"C=CR" when it appears the same or different each time; when two R" are present at the same time, the two R" may be the same or different;
[0278] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0279] Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N;
[0280] R" and R qEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0281] Ar3 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0282] The adjacent substituent R", R q Can optionally be linked to form a ring.
[0283] In this embodiment, the "adjacent substituent R", R q "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R", q Between the two substituents R" and R q Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0284] According to one embodiment of the present invention, in Formula 3a and Formula 3b, Ar3 is selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, or a combination thereof.
[0285] According to one embodiment of the present invention, in the first compound, Q1-Q8 each time appears, the same or different is selected from C or CR q , R q Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, and combinations thereof.
[0286] According to one embodiment of the present invention, in the first compound, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof, the same or different each time it appears.
[0287] According to one embodiment of the present invention, in the first compound, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted fluorenylene.
[0288] According to one embodiment of the present invention, in the first compound, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted biphenylene group, the same or different each time it occurs.
[0289] According to one embodiment of the present invention, in the first metal complex, R" 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 combination thereof, at each occurrence.
[0290] According to one embodiment of the present invention, in the first metal complex, R" is selected from methyl, deuterated methyl or phenyl the same or differently each time it appears.
[0291] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound H-1 to compound H-243, wherein the specific structures of compound H-1 to compound H-243 are described in claim 26.
[0292] According to one embodiment of the present invention, the organic layer containing the first metal complex and the first compound in the electroluminescent device is a light-emitting layer.
[0293] According to an embodiment of the present invention, the light-emitting layer of the electroluminescent device emits green light.
[0294] According to an embodiment of the present invention, the light-emitting layer of the electroluminescent device emits white light.
[0295] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device further comprises a second compound.
[0296] According to one embodiment of the present invention, the second compound contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0297] According to one embodiment of the present invention, the second compound has a structure represented by Formula 6:
[0298]
[0299] in,
[0300] L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0301] Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect;
[0302] Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and L x connect;
[0303] R v and R uEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0304] Ar4 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0305] Adjacent substituent R v and R u Can optionally be linked to form a ring.
[0306] In this context, “the adjacent substituent R v and R u "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R v Between the two substituents R u Between the two substituents R v and R u Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0307] According to one embodiment of the present invention, the second compound has a structure represented by one of Formula 6-a to Formula 6-j:
[0308]
[0309]
[0310] in,
[0311] L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0312] Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect;
[0313] Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and L x connect;
[0314] R v and R u Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0315] Ar4 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0316] Adjacent substituent R v and R u Can optionally be linked to form a ring.
[0317] According to one embodiment of the present invention, the second main compound is selected from the group consisting of compounds X-1 to X-128, wherein the specific structures of compounds X-1 to X-128 are described in claim 28.
[0318] According to one embodiment of the present invention, in the electroluminescent device, 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.
[0319] According to one embodiment of the present invention, in the electroluminescent device, 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.
[0320] According to another embodiment of the present invention, an electronic device is disclosed, which includes the electroluminescent device described in any of the above embodiments.
[0321] According to another embodiment of the present invention, a compound combination is disclosed, which includes a first metal complex and a first compound, wherein the specific structures of the first metal complex and the first compound are shown in any of the aforementioned embodiments.
[0322] Combination with other materials
[0323] 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.
[0324] 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.
[0325] 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.
[0326] Device Embodiment
[0327] 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 100:0 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60. 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 referring to the preparation methods in the prior art, or by referring to the preparation methods in the U.S. patent applications with publication numbers US20200251666A1, US2019363261A1, and US2010187977A1, which will not be described here.
[0328] Device Example 1-1
[0329] 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 X-4 is used as an electron blocking layer (EBL). Then the metal complex 641 of the present invention is doped in compound X-4 and compound H-1 and co-deposited as a light-emitting layer (EML). On EML, compound H-1 is used as a hole blocking layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
[0330] Device Examples 1-2
[0331] The implementation of Device Example 1-2 is the same as that of Device Example 1-1, except that the present invention compound H-91 is used in place of the present invention compound H-1 in the light-emitting layer.
[0332] Device Examples 1-3
[0333] The implementation of Device Example 1-3 is the same as that of Device Example 1-1, except that the present invention compound H-141 is used in place of the present invention compound H-1 in the light-emitting layer.
[0334] Device Examples 1-4
[0335] Device Example 1-4 was carried out in the same manner as Device Example 1-1, except that the present invention compound H-171 was used in place of the present invention compound H-1 in the light-emitting layer.
[0336] Device Examples 1-5
[0337] The implementation of Device Example 1-5 is the same as that of Device Example 1-1, except that the present invention compound H-172 is used in place of the present invention compound H-1 in the light-emitting layer.
[0338] Device Comparison Example 1-1
[0339] The implementation of the device comparative example 1-1 is the same as that of the device example 1-1, except that the compound CBP is used in the light-emitting layer instead of the compounds H-1 and X-4 of the present invention.
[0340] Device Comparison Example 1-2
[0341] The implementation of device comparative example 1-2 is the same as that of device example 1-1, except that the metal complex GD1 is used in the light-emitting layer instead of the metal complex 641 of the present invention.
[0342] Device Comparison Examples 1-3
[0343] The implementation of device comparative example 1-3 is the same as that of device example 1-2, except that the metal complex GD1 is used in the light-emitting layer instead of the metal complex 641 of the present invention.
[0344] Device Comparison Examples 1-4
[0345] The implementation of device comparative example 1-4 is the same as that of device example 1-3, except that the metal complex GD1 is used in the light-emitting layer instead of the metal complex 641 of the present invention.
[0346] Device Comparison Examples 1-5
[0347] The implementation of device comparative examples 1-5 is the same as that of device examples 1-5, except that the metal complex GD1 is used in the light-emitting layer instead of the metal complex 641 of the present invention.
[0348] Device Example 2-1
[0349] The implementation of Device Example 2-1 is the same as that of Device Example 1-1, except that the present metal complex 745 is used instead of the present compound 641 in the light-emitting layer.
[0350] Device Example 2-2
[0351] The device example 2-2 is implemented in the same manner as the device example 2-1, except that the present invention compound H-91 is used in place of the present invention compound H-1 in the light-emitting layer.
[0352] Device Examples 2-3
[0353] Device Example 2-3 was carried out in the same manner as Device Example 2-1, except that the present invention compound H-141 was used in place of the present invention compound H-1 in the light-emitting layer.
[0354] Device Examples 2-4
[0355] Device Example 2-4 was carried out in the same manner as Device Example 2-1, except that the present invention compound H-172 was used in place of the present invention compound H-1 in the light-emitting layer.
[0356] Device Comparison Example 2-1
[0357] The implementation of the device comparative example 2-1 is the same as that of the device example 2-1, except that the compound CBP is used in the light-emitting layer instead of the compounds H-1 and X-4 of the present invention.
[0358] 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.
[0359] Table 1 Device structures of Examples 1-1 to 1-5, 2-1 to 2-4 and Comparative Examples 1-1 to 1-5, 2-1
[0360]
[0361]
[0362]
[0363] The material structure used in the device is shown below:
[0364]
[0365]
[0366] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE). These data are recorded and shown in Table 2.
[0367] Table 2 Device data of Examples 1-1 to 1-5, 2-1 to 2-4 and Comparative Examples 1-1 to 1-5, 2-1
[0368]
[0369]
[0370] discuss:
[0371] Table 2 shows the device performance of the embodiments and comparative examples. It can be seen from embodiments 1-1 to 1-5 and comparative example 1-1 that in the devices of the metal complex 641 containing specific Ar-substituted ligands in the present invention with the first compounds H-1, H-91, H-141, H-171 and H-172 of the present invention as the main material, compared with the use of CBP as the main material in the prior art, when the brightness and color coordinates are basically the same, the CE is 2.32 times, 2.19 times, 2.21 times, 2.23 times and 2.21 times that of the comparative example, respectively, and the EQE is 2.35 times, 2.22 times, 2.25 times, 2.26 times and 2.25 times that of the comparative example, respectively. At the same time, the driving voltage is reduced by 4.3V to 4.4V, and the PE is 5.8 times, 5.15 times, 5.3 times, 5.5 times and 5.5 times that of the comparative example, respectively, showing excellent performance that greatly exceeds the main body of the prior art.
[0372] Similarly, compared with Comparative Example 2-1, in the devices using the first compound H-1, H-91, H-141 and H-172 of the present invention as the main material, the metal complex 745 containing a specific Ar-substituted ligand in the present invention has a CE of 2.32 times, 2.25 times, 2.23 times and 2.24 times that of the comparative example, respectively, and an EQE of 2.34 times, 2.28 times, 2.27 times and 2.28 times that of the comparative example, respectively. At the same time, the driving voltage is reduced by 3.6V to 3.8V, and the PE is 5.24 times, 4.89 times, 5.11 times and 4.90 times that of the comparative example, respectively, which is also greatly improved. It is worth noting that Examples 2-1 to 2-5 and Comparative Example 2-1 use metal complex 745 with specific Ar in other substitution positions, which reflects that the metal complex containing specific Ar substitution in the present invention has universality and, in combination with the first compound of the present invention, has a huge improvement over the prior art.
[0373] When the same first compound of the present invention is used as the main material, Example 1-1 is compared with Comparative Example 1-2, Example 1-2 is compared with Comparative Example 1-3, Example 1-3 is compared with Comparative Example 1-4, and Example 1-5 is compared with Comparative Example 1-5. When the main materials are the first compound of the present invention H-1, H-91, H-141, and H-172, respectively, the metal complex 641 containing a specific Ar-substituted ligand of the present invention is compared with GD1 containing a phenyl-substituted ligand. When the emission wavelength and driving voltage are equivalent, the CE is increased by 11.2%, 9.6%, 9.5%, and 11.8%, respectively. The EQE is increased by 11.5%, 9.9%, 9.8%, and 12.0%, respectively, and the PE is increased by 14.9%, 12.0%, 12.8%, and 18.3%, respectively, showing excellent performance that greatly exceeds the metal complexes of the prior art.
[0374] The above results show that the combination of the metal complex with specific Ar substitution of the present invention and the first compound of the present invention is applied to the electroluminescent device, and shows obvious advantages over the combination of the metal complex of the present invention and the main material of the prior art, and the combination of the metal complex of the comparative example and the first compound of the present invention, and the CE, PE and EQE of the device are greatly improved, and the comprehensive performance of the device is greatly optimized. Therefore, the combination of the metal complex of the present invention and the first compound has great advantages.
[0375] Device Example 3-1
[0376] The implementation of Device Example 3-1 is the same as that of Device Example 1-1, except that the present metal complex 660 is used instead of the present compound 641 in the light-emitting layer.
[0377] Device Example 3-2
[0378] Device Example 3-2 is implemented in the same manner as Device Example 3-1, except that the present invention compound H-91 is used in place of the present invention compound H-1 in the light-emitting layer.
[0379] Device Example 3-3
[0380] The implementation of device example 3-3 is the same as that of device example 3-1, except that the present invention compound H-141 is used in place of the present invention compound H-1 in the light-emitting layer.
[0381] Device Examples 3-4
[0382] Device Example 3-4 was carried out in the same manner as Device Example 3-1, except that the present invention compound H-171 was used in place of the present invention compound H-1 in the light-emitting layer.
[0383] Device Examples 3-5
[0384] Device Example 3-5 was implemented in the same manner as Device Example 3-1, except that the present invention compound H-172 was used in place of the present invention compound H-1 in the light-emitting layer.
[0385] Device Examples 3-6
[0386] The implementation method of device example 3-6 is the same as that of device example 3-2, except that the metal complex 678 of the present invention is used instead of the compound 660 of the present invention in the light-emitting layer, and the ratio of compound X-4:compound H-91:metal complex 678 is 63:31:6.
[0387] Device Examples 3-7
[0388] The implementation method of device example 3-7 is the same as that of device example 3-2, except that the metal complex 520 of the present invention is used in place of the compound 660 of the present invention in the light-emitting layer, and the ratio of compound X-4:compound H-91:metal complex 520 is 63:31:6. .
[0389] Device Comparison Example 3-1
[0390] The device comparative example 3-1 is implemented in the same manner as the device example 3-1, except that the compound CBP is used in the light-emitting layer instead of the compounds H-1 and X-4 of the present invention.
[0391] Device Comparison Example 3-2
[0392] The implementation of the device comparative example 3-2 is the same as that of the device example 3-1, except that the metal complex GD2 is used in the light-emitting layer instead of the metal complex 660 of the present invention.
[0393] Device Comparison Example 3-3
[0394] The implementation method of device comparative example 3-3 is the same as that of device example 3-2, except that the metal complex GD2 is used in the light-emitting layer instead of the metal complex 660 of the present invention.
[0395] Device Comparison Example 3-4
[0396] The implementation of device comparative example 3-4 is the same as that of device example 3-3, except that the metal complex GD2 is used in the light-emitting layer instead of the metal complex 660 of the present invention.
[0397] Device Comparison Examples 3-5
[0398] The implementation of device comparative example 3-5 is the same as that of device example 3-6, except that the metal complex GD2 is used in the light-emitting layer instead of the metal complex 678 of the present invention.
[0399] Device Comparison Examples 3-6
[0400] The implementation of device comparative example 3-6 is the same as that of device example 3-7, except that the metal complex GD3 is used in the light-emitting layer instead of the metal complex 520 of the present invention.
[0401] 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.
[0402] Table 3 Device structures of Examples 3-1 to 3-5 and Comparative Examples 3-1 to 3-5
[0403]
[0404]
[0405] The new material structure used in the device is shown below:
[0406]
[0407]
[0408] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max, full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE). These data are recorded and shown in Table 4.
[0409] Table 4 Device data of Examples 3-1 to 3-7 and Comparative Examples 3-1 to 3-6
[0410]
[0411] discuss:
[0412] Table 4 shows the device performance of the embodiments and comparative examples. It can be seen from Examples 3-1 to 3-5 and Comparative Example 3-1 that in the devices containing the metal complexes substituted with specific Ar in the present invention and using the first compounds H-1, H-91, H-141, H-171 and H-172 of the present invention as the main material, compared with the use of CBP as the main material in the prior art, when the brightness and color coordinates are basically the same, the CE is 1.76 times, 1.73 times, 1.76 times, 1.77 times and 1.84 times that of the comparative example, respectively, and the EQE is 1.75 times, 1.72 times, 1.76 times, 1.79 times and 1.85 times that of the comparative example, respectively, the driving voltage is reduced by 3.3V to 3.48V, and the PE is 3.84 times, 3.78 times, 3.88 times, 4.03 times and 4.16 times that of the comparative example, respectively, showing excellent performance that greatly exceeds the main body of the prior art. The above results show that the metal complex containing a specific Ar-substituted ligand in the present invention, when further containing a cyano substitution, has a significant improvement over the prior art when combined with the first compound of the present invention.
[0413] When the same first compound of the present invention is used as the main material, Example 3-1 is compared with Comparative Example 3-2, Example 3-2 is compared with Comparative Example 3-3, and Example 3-3 is compared with Comparative Example 3-4. When the main materials are the first compound of the present invention H-1, H-91, and H-141, respectively, the metal complex 660 containing a specific Ar substitution in the present invention is compared with GD2 containing a phenyl substituted ligand, showing a more superior performance. When the metal complex GD2 is used as a light-emitting dopant, its half-peak width is in the range of 35.5nm to 36.6nm, and the EQE is in the range of 24.1% to 25.6%, which is already a relatively high level in the industry. Nevertheless, the metal complex 660 with specific Ar-substituted ligands of the present invention still achieved further improvement in performance. Compared with Comparative Example 3-2, the half-width of Example 3-1 was narrowed by 1 nm, and the EQE was improved by 13.2%; compared with Comparative Example 3-3, the half-width of Example 3-2 was narrowed by 1.7 nm, and the EQE was improved by 6.7%; compared with Comparative Example 3-4, the half-width of Example 3-3 was narrowed by 1.6 nm, and the EQE was improved by 7%.
[0414] What is more noteworthy is that when the half-peak widths of Examples 3-1 to 3-5 are all less than 35.0nm, the EQEs all reach a relatively high level (higher than 26.9%), especially Example 3-5, whose EQE reaches 28.9%, which is a very high level in the industry. This shows that the combination of the luminescent material of the present invention and the first compound has an important significance in improving the color purity and efficiency of the device.
[0415] Compared with Comparative Example 3-5, and Example 3-7 with Comparative Example 3-6, the metal complex containing a specific Ar substituted ligand in the present invention is compared with the metal complex containing a phenyl substituted ligand in the comparative example, showing superior performance. Compared with Comparative Example 3-5, the half-peak width of Example 3-6 is narrowed by 1.4nm, and the CE, PE and EQE are improved by 10.6%, 12.4% and 10.2%, respectively. Compared with Comparative Example 3-6, the half-peak width of Example 3-7 is narrowed by 3.6nm, and the CE, PE and EQE are improved by 5.8%, 7.4% and 5.9%, respectively. The metal complexes with multiple Ar structure substitutions of the present invention, in combination with the first compound of the present invention, have a significant improvement over the prior art.
[0416] The metal complex with specific Ar substitution of the present invention, and further with cyano substitution, is used in combination with the first compound of the present invention in an electroluminescent device, and shows obvious advantages over the combination of the metal complex of the present invention with the main material of the prior art, and the combination of the metal complex of the comparative example with the first compound of the present invention, and the CE, PE and EQE of the device are greatly improved, and the comprehensive performance of the device is greatly optimized. Therefore, the combination of the metal complex of the present invention and the first compound has great advantages.
[0417] Device Example 4-1
[0418] The implementation of Device Example 4-1 is the same as that of Device Example 1-1, except that the present metal complex 221 is used instead of the present compound 641 in the light-emitting layer.
[0419] Device Example 4-2
[0420] Device Example 4-2 is implemented in the same manner as Device Example 4-1, except that the present invention compound H-91 is used in place of the present invention compound H-1 in the light-emitting layer.
[0421] Device Example 4-3
[0422] Device Example 4-3 was implemented in the same manner as Device Example 4-1, except that the present invention compound H-141 was used in place of the present invention compound H-1 in the light-emitting layer.
[0423] Device Example 4-4
[0424] Device Example 4-4 was implemented in the same manner as Device Example 4-1, except that the present invention compound H-172 was used in place of the present invention compound H-1 in the light-emitting layer.
[0425] Device Comparison Example 4-1
[0426] The device comparative example 4-1 is implemented in the same manner as the device example 4-1, except that the compound CBP is used in the light-emitting layer instead of the compounds H-1 and X-4 of the present invention.
[0427] Device Comparison Example 4-2
[0428] The implementation of the device comparative example 4-2 is the same as that of the device example 4-1, except that the metal complex GD4 is used in the light-emitting layer instead of the metal complex 221 of the present invention.
[0429] Device Comparison Example 4-3
[0430] The implementation of device comparative example 4-3 is the same as that of device example 4-2, except that the metal complex GD4 is used in the light-emitting layer instead of the metal complex 221 of the present invention.
[0431] Device Comparison Example 4-4
[0432] The implementation of device comparative example 4-4 is the same as that of device example 4-3, except that the metal complex GD4 is used in the light-emitting layer instead of the metal complex 221 of the present invention.
[0433] Device Comparison Examples 4-5
[0434] The implementation of device comparison example 4-5 is the same as that of device comparison example 4-4, except that the metal complex GD4 is used in the light-emitting layer instead of the metal complex 221 of the present invention.
[0435] 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.
[0436] Table 5 Device structures of Examples 4-1 to 4-4 and Comparative Examples 4-1 to 4-6
[0437]
[0438] The new material structure used in the device is shown below:
[0439]
[0440] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max, full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE). These data are recorded and shown in Table 6.
[0441] Table 6 Device data of Examples 4-1 to 3-4 and Comparative Examples 4-1 to 4-6
[0442]
[0443] Table 6 shows the device performance of the embodiments and comparative examples. It can be seen from the comparison between Examples 4-1 to 4-4 and Comparative 4-1 that the metal complex 221 containing a specific Ar-substituted ligand in the present invention is used as the main material in the device of the first compound H-1, H-91, H-141 and H-172 of the present invention. Compared with the use of CBP as the main material in the prior art, the CE is 1.98 times, 1.92 times, 1.94 times and 1.89 times that of the comparative example when the brightness and color coordinates are basically the same. EQE is 1.99 times, 1.94 times, 1.96 times and 1.91 times that of the comparative example. The driving voltage is reduced by 4.0V to 4.1V, and the PE is 4.75 times, 4.63 times, 4.83 times and 4.71 times that of the comparative example, respectively, showing excellent performance that greatly exceeds the main body of the prior art. The above results show that the metal complex containing a specific Ar-substituted ligand in the present invention, and further containing fluorine substitution, has a significant improvement beyond the prior art under the cooperation of the first compound of the present invention.
[0444] When the same first compound of the present invention is used as the main material, Example 4-1 is compared with Comparative Example 4-2, Example 4-2 is compared with Comparative Example 4-3, Example 4-3 is compared with Comparative Example 4-4, and Example 4-4 is compared with Comparative Example 4-5. When the main bodies are the first compounds of the present invention H-1, H-91, H-141 and H-172, respectively, the metal complex 221 containing a specific Ar-substituted ligand in the present invention is compared with GD4 containing a phenyl-substituted ligand, showing a superior performance. When the metal complex GD4 is used as a light-emitting dopant, its EQE is in the range of 23.8% to 24.9%, which is already a high level in the industry. Despite this, the metal complex 221 with a specific Ar-substituted ligand of the present invention has achieved further performance improvements, with EQE increased by 14.7%, 10.8%, 8.0% and 7.4%, respectively. From the above, it can be seen that the metal complex containing a specific Ar-substituted ligand in the invention, when further containing a fluorine substitution, can significantly improve the overall performance of the device when combined with the first compound compared to the metal complex containing a fluorine and phenyl-substituted ligand.
[0445] In summary, the present invention comprises L having specific Ar substitution aThe electroluminescent device of the metal complex of the ligand and the first main compound shows obvious advantages over the combination of the metal complex of the present invention and the main material of the prior art, and the combination of the metal complex of the comparative example and the first compound of the present invention, and can improve the device efficiency, especially the improvement of EQE, or the reduction of the driving voltage and the reduction of the half-peak width, and ultimately achieve the beneficial effect of significantly improving the overall performance of the device.
[0446] 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 and a first 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 formula 1, The metal M is selected from metals with a relative atomic mass greater than 40; Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; X is selected from the group consisting of O, S, Se; X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; at least one of X1-X4 is C and is 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 X7-X8 is CR x , and the R x Ar has a structure represented by Formula 2: a is selected from 0, 1, 2, 3, 4 or 5; R a1 and R a2 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; "*" indicates the connection position of formula 2; Wherein, the first compound has a structure represented by Formula 3a or Formula 3b: Wherein, in Formula 3a or Formula 3b, Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" can be the same or different; L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1-Q8 are selected from CR in the same or different way each time they appear. q or N; Ar3 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; R', R x , R a1 , R a2 , R' and R q each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituent R x , R a1 , R a2 can optionally be linked to form a ring; The adjacent substituent R", R q Can optionally be linked to form a ring.
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 cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Two adjacent substituents R can optionally be linked to form a ring; Among them, '#' 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 or 2, wherein: The first metal complex has M(L a ) m (L b ) n (L c ) q The general formula of in, 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 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 and R b2 Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R, R', R x , R a1 , R a2 , R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms alkenyl, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 can optionally be linked to form a ring; "*" indicates the connection position of formula 2.
4. The electroluminescent device according to claim 1 or 2, wherein: M is selected, identically or differently on each occurrence, from Pt or Ir.
5. The electroluminescent device according to claim 1 or 2, wherein: The first metal complex Ir(L a ) m (L b ) 3-m Having a structure represented by Formula 5: in, m is selected from 1, 2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, multiple L a Same or different; X is selected from the group consisting of O, S, Se; Each occurrence of Y1-Y4 is identical or different and is selected from CR y or N; X3-X8 are selected from CR in the same or different way each time they appear x or N; At least one of X7-X8 is CR x , and R x Ar has a structure represented by Formula 2: a is selected from 0, 1, 2, 3, 4 or 5; R a1 and R a2 The same or different at each occurrence indicates mono-, poly- or no substitution; Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; R x , R y , R1-R8, R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms alkenyl, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; "*" indicates the connection position of formula 2; Adjacent substituent R x , R y , R a1 , R a2 can optionally be linked to form a ring; Adjacent substituents R1 to R8 can optionally be linked to form a ring.
6. The electroluminescent device according to claim 1, wherein X is selected from O or S, and a is selected from 0, 1, 2 or 3.
7. The electroluminescent device according to claim 1, wherein: a is selected from 1.
8. The electroluminescent device according to claim 5, wherein: X3-X8 are the same or different selected from CR each time they appear x ; and / or Y1-Y4 are identical or different when they appear each time and are selected from CR y .
9. The electroluminescent device according to claim 5, wherein: At least one of X3-X8 is N, and / or at least one of Y1-Y4 is N.
10. The electroluminescent device according to claim 1, wherein X8 from CR x , and the R x It's Ar.
11. The electroluminescent device according to claim 1, wherein R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
12. The electroluminescent device according to claim 1, wherein: R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 15 carbon atoms, and combinations thereof.
13. The electroluminescent device according to claim 1, wherein: R a1 and R a2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, and combinations thereof.
14. The electroluminescent device as claimed in claim 1, wherein in Ar, ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-18 ring atoms, heteroaromatic rings having 5-18 ring atoms, or a combination thereof each time they appear; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.
15. The electroluminescent device as claimed in claim 1, wherein in Ar, ring Ar1 and ring Ar2 are selected from the group consisting of: a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluorene ring, a silylfluorene ring, a quinoline ring, an isoquinoline ring, a dithiophene ring, a difuran ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a triphenylene ring, a carbazole ring, an azacarbazole ring, an azafluorene ring, an azasilylfluorene ring, an azadibenzofuran ring, an azadibenzothiophene ring, and combinations thereof, and the total number of ring atoms of ring Ar1 and ring Ar2 is greater than or equal to 8 and less than or equal to 30.
16. The electroluminescent device of claim 1, wherein in Ar, ring Ar1 and ring Ar2 are each identically or differently selected from an aromatic ring having 6 ring atoms, a heteroaromatic ring having 5 or 6 ring atoms, or a combination thereof.
17. The electroluminescent device of claim 1, wherein each occurrence of ring Ar1 and ring Ar2 is identically or differently selected from aromatic or heteroaromatic rings having 6 ring atoms.
18. The electroluminescent device of claim 1, wherein each occurrence of ring Ar1 and ring Ar2 is identically or differently selected from aromatic rings having 6 ring atoms.
19. The electroluminescent device of claim 1, wherein: Ar at each occurrence is identically or differently selected from the group consisting of: and combinations thereof; Optionally, the hydrogen in the above groups may be partially or fully deuterated; wherein "*" indicates the attachment position of the substituent.
20. The electroluminescent device of 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.
21. The electroluminescent device of 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, and combinations thereof.
22. The electroluminescent device of 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, and combinations thereof; optionally, the hydrogen in the above groups can be partially or completely deuterated.
23. The electroluminescent device of claim 1, wherein: R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.
24. The electroluminescent device of claim 1, wherein: R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 11 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, cyano, and combinations thereof.
25. The electroluminescent device of claim 1, wherein: At least two of X3-X8 are selected from CR x , where at least one R x is Ar, and 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.
26. The electroluminescent device of claim 1, wherein: At least two of X3-X8 are selected from CR x , where at least one R x is Ar, and at least one other R x Selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, cyano, and combinations thereof.
27. The electroluminescent device of claim 5, wherein: R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof.
28. The electroluminescent device of claim 5, wherein: At least one R y Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 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.
29. The electroluminescent device of claim 3, wherein: L a Each occurrence is identically or differently selected from the group consisting of: In the above structure, "TMS" stands for "trimethylsilyl".
30. The electroluminescent device of claim 29, wherein: L b Each occurrence is identically or differently selected from the group consisting of:
31. The electroluminescent device of claim 30, wherein: L c Each occurrence is identically or differently selected from the group consisting of:
32. The electroluminescent device of claim 31, wherein: The first metal complex has Ir(L a )2(L b ) or Ir(L a )(L b )2 or Ir(L a )3 structure, where L a Each time it appears, choose the same or different one from L a1-1 To L a1-494 , L a1-499 , L a1-504 To L a1-505 , L a2-1 To L a2-524 , L a2-529 , L a2-534 and L a5-1 To L a5-6 , L a5-10 To L a5-15、 L a5-19 To L a5-24 , L a5-28 To L a5-111 Any one, any two, or any three of the group consisting of L b Choose from L b1 To L b128 Any one or two of the groups consisting of; Or the first metal complex has Ir(L a )2(L c ) or Ir(L a )(L c )2 structure, where L a Each time it appears, choose the same or different one from L a1-1 To L a1-494 , L a1-499 , L a1-504 To L a1-505 , L a2-1 To L a2-524 , L a2-529 , L a2-534 and L a5-1 To L a5-6 , L a5-10 To L a5-15、 L a5-19 To L a5-24 , L a5-28 To L a5-111 Any one or two of the group consisting of L c Choose from L c1 To L c360 Any one or two of the groups consisting of; Or the first metal complex has Ir(L a )(L b )(L c ) structure, where L a Each time it appears, choose the same or different one from L a1-1 To L a1-494 , L a1-499 , L a1-504 To L a1-505 , L a2-1 To L a2-524 , L a2-529 , L a2-534 and L a5-1 To L a5-6 , L a5-10 To L a5-15、 L a5-19 To L a5-24 , L a5-28 To L a5-111 Any of the groups consisting of L b Choose from L b1 To L b128 Any of the groups consisting of L c Choose from L c1 To L c360 Any of the groups consisting of.
33. The electroluminescent device of claim 31, wherein: The first metal complex is selected from the group consisting of metal complex 1 to metal complex 1280, wherein metal complex 1 to metal complex 1280 have IrL a (L b )2 structure, where two L b Same, where L a and L b They correspond to the structures shown in the following table:
34. The electroluminescent device of claim 1, wherein: The first compound has a structure represented by Formula 3b: Wherein, in Formula 3b, Q is the same or different when it appears each time and is selected from the group consisting of O, S, Se, NR"; when two R" are present at the same time, the two R" may be the same or different; L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N; R" and R q 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, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; Ar3 each occurrence is identical or different selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof; The adjacent substituent R", R q Can optionally be linked to form a ring.
35. The electroluminescent device of claim 1, wherein: Ar3 is selected from substituted or unsubstituted phenyl, substituted or substituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, or a combination thereof.
36. The electroluminescent device of claim 34, wherein: Q1-Q8 are selected from C or CR at each occurrence, either identically or differently q , R q Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, and combinations thereof.
37. The electroluminescent device of claim 34, wherein: L is 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.
38. The electroluminescent device of claim 34, wherein: L is selected, at each occurrence, identically or differently, from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted fluorenylene.
39. The electroluminescent device of claim 34, wherein: L is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted biphenylene group.
40. The electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:
41. The electroluminescent device of claim 1, wherein: The organic layer is a light-emitting layer, and the light-emitting layer further comprises a second compound; the second compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
42. The electroluminescent device of claim 41, wherein: The second compound has a structure represented by Formula 6: in, L x is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect; Each occurrence of U is selected from C, CR, or u or N, and at least one of U is C, and L x connect; R v and R u 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, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; Ar4 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R v and R u Can optionally be linked to form a ring.
43. The electroluminescent device of claim 42, wherein: The second compound has a structure represented by one of Formula 6-a to Formula 6-j:
44. The electroluminescent device of claim 43, wherein: The second compound is selected from the group consisting of:
45. The electroluminescent device as claimed in claim 41, wherein a 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.
46. The electroluminescent device of claim 41, wherein the weight of the first metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
47. An electronic device comprising the electroluminescent device according to any one of claims 1 to 46.
48. A compound combination comprising a first metal complex and a first compound, wherein: 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 formula 1, The metal M is selected from metals with a relative atomic mass greater than 40; Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; X is selected from the group consisting of O, S, Se; X1-X8 are selected from C, CR in the same or different manner at each occurrence x or N; at least one of X1-X4 is C and is 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 X7-X8 is CR x , and the R x Ar has a structure represented by Formula 2: a is selected from 0, 1, 2, 3, 4 or 5; R a1 and R a2 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; Ring Ar1 and ring Ar2 are identically or differently selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof at each occurrence; and the total number of ring atoms in ring Ar1 and ring Ar2 is greater than or equal to 8; "*" indicates the connection position of formula 2; Wherein, the first compound has a structure represented by Formula 3a or Formula 3b: in, Q is the same or different each time it appears and is selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; when two R" are present at the same time, the two R" can be the same or different; L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1-Q8 are selected from C, CR in the same or different manner at each occurrence q or N; Ar3 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; "*" represents the connection position between Formula 4 and Formula 3; R', R x , R a1 , R a2 , R' and R q 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, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, phosphino, and combinations thereof; Adjacent substituent R x , R a1 , R a2 can optionally be linked to form a ring; The adjacent substituent R", R q Can optionally be linked to form a ring.
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