Organic light-emitting device and display device thereof
By introducing a combination of metal complexes and terminal luminescent materials with specific wavelengths and half-width at half maximum into the light-emitting layer of OLEDs, the performance problems of blue phosphorescent devices were solved, high-efficiency and long-life OLEDs were achieved, and the industry's demand for higher performance was met.
Patent Information
- Application Number
- CN202410369542.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-03-28
- Publication Date
- 2025-09-30
AI Technical Summary
Existing organic electroluminescent devices (OLEDs) have problems such as blue unsaturation, short device life and high operating voltage in blue phosphorescent devices. In addition, the impact of the combination of different luminescent materials on device performance has not been fully studied, making it difficult to meet the requirements of high efficiency and long life.
The light-emitting layer contains both a metal complex (Pt complex, Pd complex or Au complex) and a terminal light-emitting material to ensure that the maximum emission wavelength is 500nm<λmax1≤580nm, 500nm≤λmax2≤600nm, and the full width at half maximum FWHM2≤60nm, so as to achieve high efficiency and long life.
While maintaining a low driving voltage, the device efficiency (CE, PE and EQE) and life are significantly improved, with excellent overall performance.
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Figure CN120718641A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic electronic device, such as an organic electroluminescent device, and more particularly to an organic electroluminescent device comprising a metal complex and a terminal luminescent material in a light-emitting layer, and a display device comprising the organic electroluminescent device. 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 photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, 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 that included an arylamine hole transport layer and a tris-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 was applied to the device, green light was 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 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 categorized into three different types based on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, 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 use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be categorized based on the form of the materials used, into small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, 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] Various OLED manufacturing methods exist. Small molecule OLEDs are typically produced by vacuum thermal evaporation. Polymer OLEDs are produced using solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be produced using solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The luminescent color of OLEDs can be achieved through the structural design of luminescent materials. OLEDs can include one or more 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 generally adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which remains a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency, and longer device life.
[0008] CN116437679A discloses an organic electroluminescent device, wherein the light-emitting layer comprises a host material, a first luminescent material, and a second luminescent material, wherein the second luminescent material is a phosphorescent metal complex. The device disclosed in the application controls the first excited triplet energy level between the host material and the luminescent material to satisfy the following conditions: T1(Host)>T1(Emt1)>T1(Emt2), and the peak emission wavelengths of the first and second luminescent materials satisfy the following conditions: λ max (Emt1)<λ max (Emt2), enabling multicolor luminescence using a single-light-emitting-layer device structure. However, the application does not disclose or teach a device comprising a light-emitting layer containing both a metal complex and another light-emitting material having a maximum wavelength and full width at half maximum within a specific range, nor the related device performance.
[0009] In addition to new luminescent materials, the combination of different materials, especially the combination of different luminescent materials, is also particularly important in affecting device performance. To meet the industry's increasing demands, especially for higher device efficiency and longer lifespan, further research and development is needed to apply the combination of different luminescent materials in devices. Summary of the Invention
[0010] The present invention aims to provide a novel organic electroluminescent device to solve at least part of the above problems. The light-emitting layer of the organic electroluminescent device contains a maximum emission wavelength of the photoluminescence spectrum of λ max1 Metal complexes (Pt complexes, Pd complexes or Au complexes) with a maximum emission wavelength of λ max2 , terminal luminescent material with full width at half maximum of FWHM2, especially, 500nm<λ max1 ≤580nm, 500nm≤λ max2 The novel organic electroluminescent device of the present invention can achieve a significant improvement in device efficiency (CE, PE and EQE) and lifespan while maintaining a low driving voltage and a narrow half-maximum width, and has excellent comprehensive performance.
[0011] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0012] anode,
[0013] cathode,
[0014] and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising at least a metal complex and a terminal light-emitting material;
[0015] The metal complex is selected from: a Pt complex, a Pd complex or an Au complex;
[0016] The maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 ;
[0017] The maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , the full width at half maximum in the photoluminescence spectrum of the terminal luminescent material is FWHM2;
[0018] Among them, 500nm<λ max1 ≤580nm, 500nm≤λ max2 ≤600nm, and FWHM2≤60nm.
[0019] According to another embodiment of the present invention, a display device is disclosed, which includes the organic electroluminescent device as described above.
[0020] According to another embodiment of the present invention, there is also disclosed an application of the organic electroluminescent device described above in a display device. BRIEF DESCRIPTION OF THE DRAWINGS
[0021] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent device disclosed herein.
[0022] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0023] 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.
[0024] There are many 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, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a 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, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.
[0025] The above layered structures are provided by way of non-limiting examples. The functionality 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 emission spectrum.
[0026] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.
[0027] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1The difference is that an encapsulation layer 102 can also be included above 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 the 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.
[0028] 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, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
[0029] The materials and structures described herein can also be used in other organic electronic devices listed above.
[0030] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When 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, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.
[0031] 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.
[0032] As used herein, "terminal luminescent material" refers to the material that serves as the final luminescent source of the organic electroluminescent device described herein (a device whose luminescent layer comprises at least two luminescent materials) when the device is lit. For example, if the luminescent layer of the organic electroluminescent device comprises a metal complex (phosphorescent luminescent material) and a fluorescent luminescent material, if when the device is lit, the two materials do not emit light / almost no light due to energy transfer, and the device uses the fluorescent luminescent material as the main luminescent source, then the fluorescent luminescent material is the terminal luminescent material of the electroluminescent device, including but not limited to device embodiments 1 to 3 of the present invention. Of course, the terminal luminescent material in the organic electroluminescent device of the present invention can be a single material or a variety of different materials.
[0033] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.
[0034] 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).
[0035] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies 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 so as to convert 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 the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.
[0036] 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-metallic 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 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 (such as an amino group or a carbazole derivative) to an electron acceptor moiety (such as a six-membered aromatic ring containing N).
[0037] Definition of Substituent Terms
[0038] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.
[0039] Alkyl - as used herein, includes straight chain and branched chain 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.
[0040] Cycloalkyl - as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.
[0041] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbon atoms in the alkyl chain substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. 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. The example of heteroalkyl includes 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 can be optionally substituted.
[0042] Alkenyl - as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, alkenyl groups can be optionally substituted.
[0043] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups 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 groups can be optionally substituted.
[0044] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group can 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, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused 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-quaterphenyl. In addition, the aryl group may be optionally substituted.
[0045] Heterocyclic group - 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 oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxyl. In addition, the heterocyclic group may be optionally substituted.
[0046] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain from 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group may have from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, and more preferably from 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, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...
[0047] Alkoxy - as used herein, is 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 those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.
[0048] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenyloxy. In addition, the aryloxy group may be optionally substituted.
[0049] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group 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.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,
[0050] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may be an alkylsilyl group having 3 to 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, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.
[0051] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.
[0052] Alkylgermanyl - As used herein, alkyl-substituted germanium groups are encompassed. The alkylgermanyl group can be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyl-tert-butylgermanyl, and methyldi-tert-butylgermanyl. Additionally, the alkylgermanyl group can be optionally substituted.
[0053] Arylgermanyl - As used herein, encompasses germanium groups substituted with at least one aryl or heteroaryl group. The arylgermanyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyltert-butylgermanyl. Additionally, the arylgermanyl group may be optionally substituted.
[0054] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., means that one or more CH groups in the corresponding aromatic moiety 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 nitrogen atoms in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.
[0055] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphino group, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl, sulfonyl and phosphino group, any one of which may be selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted alkyl having 6-30 carbon atoms aryl, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0056] 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 an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.
[0057] In the compounds described herein, 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 compounds may be preferred because it enhances device efficiency and stability.
[0058] In the compounds described herein, polysubstitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.
[0059] In the compounds mentioned in the present disclosure, unless clearly defined, such as 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 the situation where adjacent substituents can be connected to form a ring, and also including 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.
[0060] The statement that adjacent substituents can optionally be 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, as can be exemplified by the following formula:
[0061]
[0062] The statement that adjacent substituents can optionally be 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 via a chemical bond to form a ring, as can be exemplified by the following formula:
[0063]
[0064] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to further distant carbon atoms are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:
[0065]
[0066] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0067]
[0068] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0069] anode,
[0070] cathode,
[0071] and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising at least a metal complex and a terminal light-emitting material;
[0072] The metal complex is selected from: a Pt complex, a Pd complex or an Au complex;
[0073] The maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 ;
[0074] The maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , the full width at half maximum in the photoluminescence spectrum of the terminal luminescent material is FWHM2;
[0075] Among them, 500nm<λ max1 ≤580nm, 500nm≤λ max2 ≤600nm, and FWHM2≤60nm.
[0076] According to an embodiment of the present invention, the terminal light-emitting material is an organic material.
[0077] According to one embodiment of the present invention, the terminal luminescent material is a fluorescent luminescent material.
[0078] According to one embodiment of the present invention, the terminal luminescent material is a delayed fluorescent material.
[0079] According to one embodiment of the present invention, the delayed fluorescent material is a thermally activated delayed fluorescent (TADF) material.
[0080] According to an embodiment of the present invention, the terminal luminescent material is one material or a plurality of different materials.
[0081] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 1:
[0082]
[0083] in,
[0084] The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence;
[0085] Ring A1 to Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
[0086] L'1 to L'4 are each identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are identical or different;
[0087] a1 to a4 are selected from 0 or 1 the same or differently at each occurrence, and at least two of a1 to a4 are selected from 1;
[0088] E1 to E4 are each identically or differently selected from C or N;
[0089] G1 to G4 are each identically or differently selected from a single bond, O, S or NR";
[0090] R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted;
[0091] R1 to R4, R' and R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0092] Adjacent substituents R1 to R4, R' and R" can optionally be linked to form a ring.
[0093] As used herein, “adjacent substituents R1 to R4, R′ and R″ can optionally be linked to form a ring” is intended to mean that adjacent groups of substituents, for example, between two substituents R1, between two substituents R2, between two substituents R3, between two substituents R4, between two substituents R′, between two substituents R″, between substituents R1 and R2, between substituents R1 and R4, between substituents R2 and R3, between substituents R3 and R4, between substituents R′ and R1, between substituents R′ and R2, between substituents R′ and R3, between substituents R′ and R4, between substituents R″ and R1, between substituents R″ and R2, between substituents R″ and R3, between substituents R″ and R4, any one or more of these substituent groups can be linked to form a ring. Obviously, none of these substituents can be linked to form a ring.
[0094] Herein, each occurrence of a1 to a4 is identically or differently selected from 0 or 1 and is intended to indicate the following: when a1 is selected from 0, it indicates that ring A1 and ring A2 are not connected; when a2 is selected from 0, it indicates that ring A2 and ring A3 are not connected; when a3 is selected from 0, ring A3 and ring A4 are not connected; when a4 is selected from 0, ring A1 and ring A4 are not connected; when a1, a2, a3 or a4 is selected from 1, it indicates that L'1, L'2, L'3 or L'4 is present and is selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, and combinations thereof.
[0095] Herein, when L'1, L'2, L'3, or L'4 is selected from a single bond, it indicates that Ring A1 and Ring A2, Ring A2 and Ring A3, Ring A3 and Ring A4, or Ring A4 and Ring A1 are directly connected via a single bond. When G1, G2, G3, or G4 is selected from a single bond, it indicates that Ring A1, Ring A2, Ring A3, or Ring A4 is directly connected to the metal M via a single bond.
[0096] Herein, in Formula 1, the connection manner of L'1 to L'4 and rings A1 to A4 is intended to indicate that: L'1 in Formula 1 can be connected to any ring atom in ring A1 or ring A2, and does not only include the case where L'1 is connected to the atom adjacent to E1 in ring A1 or the atom adjacent to E2 in ring A2; similarly, L'2 in Formula 1 can be connected to any atom in ring A2 or ring A3, and does not only include the case where L'2 is connected to the atom adjacent to E2 in ring A2 or the atom adjacent to E3 in ring A3; and the same applies to L'3 and L'4.
[0097] According to an embodiment of the present invention, a1 to a4 are selected from 0 or 1 the same or differently each time they appear, and at least three of a1 to a4 are selected from 1.
[0098] According to one embodiment of the present invention, a4 is selected from 0, and a1 to a3 are selected from 1.
[0099] According to one embodiment of the present invention, L'1 to L'4 are selected from a single bond, NR', O, and S, the same or different each time they occur.
[0100] According to one embodiment of the present invention, each occurrence of G1 to G4 is identically or differently selected from a single bond, O, S or NR", and at least two of G1-G4 are selected from a single bond.
[0101] According to one embodiment of the present invention, each occurrence of G1 to G4 is identically or differently selected from a single bond, O, S or NR", and at least three of G1-G4 are selected from a single bond.
[0102] According to one embodiment of the present invention, wherein G1 is selected from a single bond, O, S or NR", and G2 to G4 are selected from a single bond.
[0103] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 2:
[0104]
[0105] in,
[0106] The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence;
[0107] Ring A1 to Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
[0108] L'1 to L'3 are each identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are identical or different;
[0109] E1 to E4 are each identically or differently selected from C or N;
[0110] G1 is selected, identically or differently at each occurrence, from a single bond, O, S or NR";
[0111] R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted;
[0112] R1 to R4, R' and R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0113] Adjacent substituents R1 to R4, R' and R" can optionally be linked to form a ring.
[0114] According to one embodiment of the present invention, wherein Ring A1 to Ring A4 are identically or differently selected each time from an aromatic ring having 6-18 ring atoms, a heteroaromatic ring having 5-18 ring atoms, or a combination thereof.
[0115] According to one embodiment of the present invention, one or two of Rings A1 to A4 are selected from heteroaromatic rings containing at least 5 ring atoms, and the rest of Rings A1 to A4 are selected from aromatic rings having 6 ring atoms, or heteroaromatic rings having 6 ring atoms.
[0116] According to one embodiment of the present invention, one or two of Rings A1 to A4 comprise a 5-membered heteroaromatic ring structure, and the rest of Rings A1 to A4 are selected from an aromatic ring having 6 ring atoms, or a heteroaromatic ring having 6 ring atoms.
[0117] According to one embodiment of the present invention, ring A1 and ring A3 are selected from aromatic rings having 6 ring atoms, ring A2 is selected from heteroaromatic rings having 9 ring atoms, and ring A4 is selected from heteroaromatic rings having 6 ring atoms.
[0118] According to one embodiment of the present invention, each time Ring A1 to Ring A4 appears, they are selected identically or differently from the following group: pyrrole ring, furan ring, thiophene ring, selenophene ring, imidazole ring, imidazole carbene ring, oxazole ring, thiazole ring, selenazole ring, benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, benzopyrrole ring, benzofuran ring, benzothiophene ring, benzoselenophene ring, benzimidazole ring, benzimidazole carbene ring, benzoxazole ring, benzothiazole ring, benzoselenazole ring, fluorene ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzoselenophene ring, azafluorene ring, azacarbazole ring, azadibenzofuran ring, azadibenzothiophene ring, azadibenzoselenophene ring, and combinations thereof.
[0119] According to one embodiment of the present invention, wherein each occurrence of ring A2 is selected from imidazole ring, imidazole carbene ring, oxazole ring, thiazole ring, benzimidazole ring, benzimidazole carbene ring, benzoxazole ring, or benzothiazole ring.
[0120] According to one embodiment of the present invention, at least one of G1 to G4 is selected from O or S.
[0121] According to one embodiment of the present invention, in Formula 2, L'1, L'2 and L'3 are each selected from a single bond, NR', O, S, the same or different when they appear; G1 is each selected from a single bond, O or NR".
[0122] According to one embodiment of the present invention, in Formula 2, L'1, L'2 and L'3 are each selected from a single bond; and G1 is each selected from O.
[0123] According to one embodiment of the present invention, in Formula 2, L'2 is selected from NR', O, S, the same or different each time it occurs; G1 is selected from a single bond, O or NR" the same or different each time it occurs.
[0124] According to one embodiment of the present invention, in Formula 2, L'2 is selected from O each time it occurs; and G1 is selected from a single bond each time it occurs.
[0125] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:
[0126]
[0127] in,
[0128] The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence;
[0129] Ring A1, Ring A 22, Ring A3, Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
[0130] Ring A 21 is selected from heteroaromatic rings having 5 ring atoms;
[0131] E1 to E4 are each identically or differently selected from C or N;
[0132] G1 is selected from O or S in the same or different manner at each occurrence;
[0133] Y1, Y4, Y 11 Each occurrence is identically or differently selected from CR'', N, NR'', O or S;
[0134] Y2, Y3, Y5 to Y 10 Each occurrence is identically or differently selected from C or N;
[0135] R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted;
[0136] R1 to R4, R'' are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0137] Adjacent substituents R1 to R4, R'' can be optionally linked to form a ring.
[0138] In this embodiment, “adjacent substituents R1 to R4, R'' can optionally be linked to form a ring” is intended to mean that adjacent substituent groups, for example, between two substituents R1, between two substituents R2, between two substituents R3, between two substituents R4, between two substituents R'', between substituents R1 and R2, between substituents R1 and R4, between substituents R2 and R3, between substituents R3 and R4, between substituents R'' and R1, between substituents R'' and R2, between substituents R'' and R3, between substituents R'' and R4, any one or more of these substituent groups can be linked to form a ring. Obviously, none of these substituents can be linked to form a ring.
[0139] According to one embodiment of the present invention, the metal M is selected from Pt or Pd, the same or different each time it occurs.
[0140] According to one embodiment of the present invention, the metal M is selected from Pt.
[0141] According to one embodiment of the present invention, G1 is selected from O; E1 and E3 are selected from C; E2 and E4 are selected from N.
[0142] According to one embodiment of the present invention, in Formula 3, Ring A1, Ring A 22 , Ring A3, Ring A4 are each identically or differently selected from an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof; Ring A 21 On each occurrence, is identically or differently selected from heteroaromatic rings having 5 ring atoms.
[0143] According to one embodiment of the present invention, in Formula 3, Ring A1, Ring A 22 , Ring A3 is selected from a benzene ring in the same or different manner each time it occurs, Ring A4 is selected from a pyridine ring in the same or different manner each time it occurs, Ring A 21 Each occurrence is identically or differently selected from imidazole rings.
[0144] According to one embodiment of the present invention, in Formula 3, Ring A1, Ring A 22 Each occurrence is the same or different and is selected from a benzene ring, each occurrence of Ring A3 is the same or different and is selected from a dibenzofuran ring, each occurrence of Ring A4 is the same or different and is selected from a pyridine ring, 21 Each occurrence is identically or differently selected from imidazole rings.
[0145] According to one embodiment of the present invention, in Formula 3, Y2, Y3, Y5 to Y 10 Each occurrence is identically or differently selected from C; Y1, Y 11Each occurrence of R' is identical or different and is selected from CR', said R'' being identical or different and is 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, cyano, and combinations thereof.
[0146] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3-1:
[0147]
[0148] Among them, in formula 3-1,
[0149] Y4 is identically or differently selected at each occurrence from NR"', O or S;
[0150] R1 to R4, R'' are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0151] According to one embodiment of the present invention, in Formula 3 and Formula 3-1, Y4 is selected from NR', O or S the same or differently each time it appears; the R' is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0152] According to one embodiment of the present invention, in Formula 3 and Formula 3-1, Y4 is selected from NR'' the same or differently each time it appears, and R'' is selected 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 the same or differently each time it appears.
[0153] According to one embodiment of the present invention, wherein R1 to R4 are selected from the group consisting of the following at each occurrence, the same or different: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, hydroxyl, thiol, and combinations thereof.
[0154] According to one embodiment of the present invention, at least one of R1, at least one of R2, at least one of R3, or at least one of R4, each occurrence of which is the same or different, is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, or a combination thereof.
[0155] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 127, and the specific structures of the metal complex 1 to metal complex 127 are shown in claim 15.
[0156] According to one embodiment of the present invention, hydrogen in the metal complexes 1 to 127 can be partially or completely replaced by deuterium.
[0157] According to one embodiment of the present invention, the terminal light-emitting material comprises at least one boron-nitrogen heterocyclic structure.
[0158] According to one embodiment of the present invention, the terminal light-emitting material comprises at least one substituted or unsubstituted carbazole structure.
[0159] According to one embodiment of the present invention, the terminal light-emitting material comprises at least two substituted or unsubstituted carbazole structures.
[0160] According to one embodiment of the present invention, the terminal light-emitting material comprises at least one substituted or unsubstituted diarylamino structure.
[0161] According to one embodiment of the present invention, the terminal light-emitting material comprises at least two substituted or unsubstituted diarylamino structures.
[0162] According to one embodiment of the present invention, the terminal light-emitting material comprises at least one substituted or unsubstituted carbazole group and at least one substituted or unsubstituted diarylamino structure.
[0163] According to one embodiment of the present invention, the terminal light-emitting material structure has a structure represented by Formula 4:
[0164]
[0165] in,
[0166] Ring A, Ring B, Ring C, Ring D, and Ring E are each independently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 30 carbon atoms;
[0167] Z1, X1 and X2 are each independently selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR Si1 or GeR Ge1 ;
[0168] T1 to T8 are each independently selected from C, CR t or N;
[0169] a, b, c, d are each independently selected from 0 or 1;
[0170] L1, L2, L3, L4 are each selected from the group consisting of a single bond, O, S, Se, BR L or NR L ;
[0171] Each occurrence of R is the same or different and represents mono-, poly- or no substitution;
[0172] R, R t , R L , R Si1 and R Ge1Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, -BR B R B , and combinations thereof;
[0173] R B Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0174] Adjacent substituents R, R t , R L , R Si1 , RGe1 and R B Can optionally be linked to form a ring.
[0175] In this embodiment, "a, b, c, and d are each independently selected from 0 or 1" is intended to indicate that T1 and T2, T3 and T4, T5 and T6, and T7 and T8, corresponding to a, b, c, and d, are connected or disconnected. For example, when a is 0, T1 and T2 are disconnected (i.e., T1 and T2 are not connected); the same is true when one or more of a, b, c, and d is 0.
[0176] In this context, adjacent substituents R, R t , R L , R Si1 , R Ge1 and R B can be optionally linked to form a ring, which is intended to indicate adjacent substituent groups, for example, between two substituents R, between two substituents R B Between the substituent R and the substituent R Si1 Between the substituent R and the substituent R Ge1 Between the substituent R and the substituent R L between, and between substituent R and substituent R B In between, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0177] As used herein, "carbocycle" includes saturated carbocycle and unsaturated carbocycle, "unsaturated carbocycle" includes aromatic unsaturated carbocycle and non-aromatic unsaturated carbocycle, "heterocycle" includes saturated heterocycle and unsaturated heterocycle, and "unsaturated heterocycle" includes aromatic unsaturated heterocycle and non-aromatic unsaturated heterocycle.
[0178] According to one embodiment of the present invention, the terminal light emitting material structure has a structure represented by Formula 5:
[0179]
[0180] in,
[0181] Ring A, Ring B, Ring C, Ring D, and Ring E are each independently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 30 carbon atoms;
[0182] Z1, X1 and X2 are each independently selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR Si1 or GeR Ge1 ;
[0183] T7 and T8 are each independently selected from C, CR tor N;
[0184] d is selected from 0 and 1;
[0185] L4 is selected from the group consisting of a single bond, O, S, Se, BR, etc. L or NR L ;
[0186] Each occurrence of R is the same or different and represents mono-, poly- or no substitution;
[0187] R, R t , R L , R Si1 and R Ge1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, -BR B R B , and combinations thereof;
[0188] R BEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0189] Adjacent substituents R, R t , R L , R Si1 , R Ge1 and R B Can optionally be linked to form a ring.
[0190] According to one embodiment of the present invention, wherein the ring A, ring B, ring C, ring D and ring E are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms;
[0191] According to one embodiment of the present invention, wherein the ring A, ring B, ring C, ring D and ring E are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;
[0192] According to one embodiment of the present invention, wherein, the ring A, ring B, ring C, ring D and ring E are each independently selected from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.
[0193] According to one embodiment of the present invention, the ring A, ring B, ring C, ring D and ring E are selected from benzene rings.
[0194] According to one embodiment of the present invention, wherein said Z1 is selected from B, P=O or P=S, and said X1 and X2 are each independently selected from N or P;
[0195] According to one embodiment of the present invention, Z1 is selected from B, and X1 and X2 are selected from N.
[0196] According to one embodiment of the present invention, wherein said Z1 is selected from N or P, X1 and X2 are each independently selected from B, P=O or P=S;
[0197] According to one embodiment of the present invention, Z1 is selected from N, and X1 and X2 are selected from B.
[0198] According to one embodiment of the present invention, wherein, each occurrence of L1, L2, L3, L4 is the same or different and is selected from single bond, O, BR L or NR L .
[0199] According to one embodiment of the present invention, a+b+c+d is greater than or equal to 1.
[0200] According to one embodiment of the present invention, a+d is greater than or equal to 1.
[0201] According to one embodiment of the present invention, a is 0 and d is 1.
[0202] According to one embodiment of the present invention, a is 1 and d is 1.
[0203] According to one embodiment of the present invention, the terminal light-emitting material has a structure represented by one of Formulas 4-1 to 4-7:
[0204]
[0205] in,
[0206] Each occurrence of R is the same or different and represents mono-, poly- or no substitution;
[0207] 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, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, -BR B R B , and combinations thereof;
[0208] R B Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0209] Adjacent substituents R and R B Can optionally be linked to form a ring.
[0210] In this embodiment, adjacent substituents R and R B can be optionally linked to form a ring, which means that two adjacent substituents R on the same ring can be linked to form a ring, and adjacent substituents R and R B Obviously, two adjacent substituents R on the same ring may not be connected to form a ring. B They may not be connected to form a ring.
[0211] According to one embodiment of the present invention, the terminal material has a structure represented by Formula 4-1 or Formula 4-2.
[0212] According to one embodiment of the present invention, wherein, each occurrence of R 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, and combinations thereof.
[0213] According to one embodiment of the present invention, wherein, each occurrence of R is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, and combinations thereof.
[0214] According to one embodiment of the present invention, there are multiple Rs in Formula 4-1 to Formula 4-7, and at least one (for example, one, two, three or four) of the multiple Rs is selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, or a combination thereof.
[0215] According to one embodiment of the present invention, the terminal light-emitting material is selected from the group consisting of compound DF-1 to compound DF-102, and the specific structures of compound DF-1 to compound DF-102 are shown in claim 24.
[0216] According to one embodiment of the present invention, the hydrogen in the compounds DF-1 to DF-102 can be partially or completely replaced by deuterium.
[0217] According to one embodiment of the present invention, the maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 , 505nm≤λ max1 ≤560nm.
[0218] According to one embodiment of the present invention, the maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 , 510nm≤λ max1 ≤550nm.
[0219] According to one embodiment of the present invention, the maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , 510nm≤λ max2 ≤580nm.
[0220] According to one embodiment of the present invention, the maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , 510nm≤λ max2 ≤560nm.
[0221] According to one embodiment of the present invention, 505 nm ≤ λ max1 ≤560nm, 510nm≤λ max2 ≤580nm.
[0222] According to one embodiment of the present invention, 510 nm ≤ λ max1 ≤550nm; 510nm≤λ max2 ≤560nm.
[0223] According to one embodiment of the present invention, the maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 The maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , where λ max1 ≤λ max2 , or 0<λ max1 -λ max2 ≤30nm.
[0224] According to one embodiment of the present invention, 0≤λ max2 -λ max1 ≤40nm, or 0<λ max1 -λ max2 ≤20nm.
[0225] According to one embodiment of the present invention, wherein the 10nm≤λ max2 -λ max1 ≤30nm, or 0<λ max1 -λ max2 ≤10nm.
[0226] According to one embodiment of the present invention, the organic electroluminescent device emits green light or yellow light.
[0227] According to one embodiment of the present invention, the maximum emission wavelength of the electroluminescence spectrum of the organic electroluminescent device is λ max ; Among them, 500nm<λ max ≤600nm.
[0228] According to one embodiment of the present invention, the maximum emission wavelength of the electroluminescence spectrum of the organic electroluminescent device is λ max ; Among them, 510nm≤λ max ≤580nm.
[0229] According to one embodiment of the present invention, the weight of the terminal light-emitting material in the light-emitting layer of the organic electroluminescent device accounts for 0.01%-5% of the total weight of the light-emitting layer.
[0230] According to one embodiment of the present invention, the weight of the terminal light-emitting material in the light-emitting layer of the organic electroluminescent device accounts for 0.05%-3% of the total weight of the light-emitting layer.
[0231] According to one embodiment of the present invention, the weight of the terminal light-emitting material in the light-emitting layer of the organic electroluminescent device accounts for 0.1%-1% of the total weight of the light-emitting layer.
[0232] According to one embodiment of the present invention, the full width at half maximum (FWHM2) of the terminal light-emitting material in the organic electroluminescent device is ≤60 nm.
[0233] According to one embodiment of the present invention, the full width at half maximum (FWHM2) of the terminal light-emitting material in the organic electroluminescent device is ≤50 nm.
[0234] According to one embodiment of the present invention, the full width at half maximum (FWHM2) of the terminal light-emitting material in the organic electroluminescent device is ≤40 nm.
[0235] According to one embodiment of the present invention, the full width at half maximum (FWHM2) of the terminal light-emitting material in the organic electroluminescent device is ≤35 nm.
[0236] According to one embodiment of the present invention, the triplet energy level of the metal complex is T 1(Emt1), the triplet energy level of the fluorescent material is T 1(Emt2) , where T 1(Emt1) >T 1(Emt2) .
[0237] According to one embodiment of the present invention, the triplet energy level of the first host material is T 1(host1) , where T 1(host1) >T 1(Emt1) , T 1(host1) >T 1(Emt2) .
[0238] According to one embodiment of the present invention, T 1(host1) >T 1(Emt1) >T 1(Emt2) .
[0239] According to one embodiment of the present invention, the light-emitting layer further comprises a second host material, and the triplet energy level of the second host material is T 1(host2) , T 1(host2) >T 1(Emt1) , T 1(host2) >T 1(Emt2) .
[0240] According to one embodiment of the present invention, T 1(host2) >T 1(Emt1) >T 1(Emt2) .
[0241] According to one embodiment of the present invention, T 1(host1) >T 1(host2) >T 1(Emt1) >T 1(Emt2) .
[0242] According to one embodiment of the present invention, the organic electroluminescent device uses a terminal luminescent material as a main light source.
[0243] According to one embodiment of the present invention, the organic electroluminescent device emits fluorescent light.
[0244] According to one embodiment of the present invention, the organic electroluminescent device emits delayed fluorescence.
[0245] According to one embodiment of the present invention, the light-emitting layer comprises a host material.
[0246] According to one embodiment of the present invention, the host material is a host material.
[0247] According to one embodiment of the present invention, the host material includes a first host material and a second host material.
[0248] According to one embodiment of the present invention, the first host material has a structure represented by Formula X-1 or Formula X-2:
[0249]
[0250] in,
[0251] L x 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;
[0252] G is selected from C(R g )2、NR g , O or S;
[0253] Each occurrence of V is selected from C, CR, or the like v or N;
[0254] In formula X-1, each occurrence of T is identical or different and is selected from C, CR T or N;
[0255] In formula X-2, each occurrence of T is identical or different and is selected from CR T or N;
[0256] R g , R v and R TEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0257] Ar1 is identical or different at each occurrence and is selected 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;
[0258] Adjacent substituent R g , R v and R T Can optionally be linked to form a ring.
[0259] In this embodiment, "the adjacent substituent R g , R v and R T "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R v Between the two substituents R T Between the two substituents R g Between, the substituent R v and R T Between, the substituent R v and R g Between, the substituent R g and R T 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.
[0260] According to one embodiment of the present invention, the first host material has a structure represented by one of Formulas Xa to Xp:
[0261]
[0262]
[0263] in,
[0264] L x 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;
[0265] G is selected from C(R g )2、NR g , O or S;
[0266] Each occurrence of V is selected from CR v or N;
[0267] Each occurrence of T is selected from CR T or N;
[0268] R g , R v and R T Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0269] Ar1 is identical or different at each occurrence and is selected 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;
[0270] Adjacent substituent R g , R v and R T Can optionally be linked to form a ring.
[0271] According to one embodiment of the present invention, the first host material is selected from the group consisting of the following compounds:
[0272]
[0273]
[0274]
[0275]
[0276]
[0277] According to one embodiment of the present invention, the second host material has a structure represented by Formula Y:
[0278]
[0279] in,
[0280] H1-H6 are selected from C, CR, or the like at each occurrence. h or N, and at least two of H1-H6 are N, at least one of H1-H6 is C, and they are connected to formula A;
[0281]
[0282] in,
[0283] Q is the same or different each time and is selected from O, S, Se, N, NR Q , CR Q R Q , SiR Q R Q ,GeR Q R Q and R Q C=CR Q When there are two R Q When two R Q Can be the same or different;
[0284] p is 0 or 1; r is 0 or 1;
[0285] When Q is selected from N, p is 0 and r is 1;
[0286] When Q is selected from O, S, Se, NR Q , CR Q R Q , SiR Q R Q ,GeR Q R Q and R Q C=CR Q When the group is composed of , p is 1 and r is 0;
[0287] L Q The second occurrences are identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0288] Each occurrence of Q1-Q8 is selected from C, CR q or N;
[0289] R h , R Q 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 an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0290] “*” represents the connection position between formula A and formula Y;
[0291] Adjacent substituent Rh , R Q , R q Can optionally be linked to form a ring.
[0292] In this context, “the adjacent substituent R h , R Q , R q "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R h Between the two substituents R Q Between the two substituents R q Between the two substituents R Q 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.
[0293] According to one embodiment of the present invention, the second host material is selected from the group consisting of the following compounds:
[0294]
[0295]
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302]
[0303] According to another embodiment of the present invention, a display device is disclosed, which includes the organic electroluminescent device according to any of the above embodiments.
[0304] According to another embodiment of the present invention, there is also disclosed an application of the organic electroluminescent device described in any of the above embodiments in a display device.
[0305] Combination with other materials
[0306] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, 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 readily consult the literature to identify other materials that can be used in combination.
[0307] The materials described herein as being useful in specific layers of an organic light-emitting device 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.
[0308] The terminal luminescent material used in the present invention can be prepared by referring to documents such as Angew.Chem.Int.Ed.2023,62,e202304104 (DOI: 10.1002 / anie.202304104), and its preparation method is not described here. The above-mentioned documents are only exemplary, and those skilled in the art can easily obtain other documents.
[0309] Material synthesis example:
[0310] The preparation method of the metal complex of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthesis routes and preparation methods are as follows:
[0311] Synthesis Example 1: Synthesis of Metal Complex 69
[0312] Step 1: Synthesis of intermediate 3:
[0313]
[0314] Under nitrogen, Intermediate 1 (4.7 g, 16.9 mmol), Intermediate 2 (5.5 g, 18.6 mmol), Pd(PPh3)4 (0.78 g, 0.67 mmol), and potassium carbonate (3.5 g, 25.3 mmol) were dissolved in 1,4-dioxane (90 mL) and water (30 mL). The reaction was heated to reflux and allowed to react overnight. After completion of the reaction, the mixture was extracted with ethyl acetate (EA) and water. The organic layer was washed twice with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. Column chromatography afforded Intermediate 3 (6.2 g, 15.1 mmol).
[0315] Step 2: Synthesis of intermediate 4:
[0316]
[0317] Under nitrogen, intermediate 3 (3.0 g, 7.3 mmol), pinacol diboronate (2.1 g, 8.1 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos, 0.21 g, 0.44 mmol), and potassium acetate (1.08 g, 11.0 mmol) were dissolved in 1,4-dioxane (90 mL). The reaction mixture was heated to reflux and allowed to react overnight. After completion of the reaction, the mixture was extracted with EA and water. The organic layer was washed twice with aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to afford intermediate 4 (3.5 g, 7.0 mmol).
[0318] Step 3: Synthesis of Intermediate 6:
[0319]
[0320] Under nitrogen, Intermediate 4 (3.5 g, 7.0 mmol), Intermediate 5 (4.5 g, 8.0 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.19 g, 0.44 mmol), and potassium carbonate (1.52 g, 11.0 mmol) were dissolved in 1,4-dioxane (90 mL) and water (30 mL). The reaction was heated to reflux and allowed to react overnight. After completion of the reaction, the mixture was extracted with EA and water. The organic layer was washed twice with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. Column chromatography afforded Intermediate 6 (5.2 g, 5.7 mmol).
[0321] Step 4: Synthesis of metal complex 69:
[0322]
[0323] To a dry 250 mL round-bottom flask were added intermediate 6 (2.98 g, 3.3 mmol), potassium chloroplatinate (1.24 g, 3.0 mmol), and acetic acid (50 mL). Under nitrogen, the mixture was heated to reflux for 48 h. After the reaction cooled, water was added and the mixture was filtered. The filter cake was washed twice with methanol and n-hexane, respectively, and then dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 69 (1.68 g, 51.0% yield). The product structure was confirmed to be the target product with a molecular weight of 1097.4.
[0324] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other metal complex structures of the present invention by improving it.
[0325] 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 existing technology. For example, the ratio of the 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 existing technology. For example, based on the total weight of the light-emitting layer materials, the host material can account for 75%-98%, the metal complex can account for 1%-20%, and the terminal light-emitting material can account for 0.01%-5%; or the host material can account for 88%-98%, the metal complex can account for 0.05%-3%, and the terminal light-emitting material can account for 0.1%-1%. In addition, the host material is two materials, and the ratio of the two host materials to the host material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 70:30 to 30:70. In the embodiments of the device, the characteristics of the device are also tested using conventional equipment in the field (including but not limited to the vapor deposition machine produced by Angstrom Engineering, the optical testing system and life testing system produced by Suzhou Fushida, the ellipsometer produced by Beijing Liangtuo, etc.) using methods familiar to those skilled in the art.
[0326] In the present invention, the maximum emission wavelength λ of the photoluminescence spectrum of the compound max The test methods for full width at half maximum (FWHM) are as follows:
[0327] The photoluminescence spectrum (PL) data of the test compound was measured using a Lingguang F98 fluorescence spectrophotometer produced by Shanghai Lingguang Technology Co., Ltd. The test compound was dissolved in toluene solvent to prepare 1×10 -6mol / L concentration of the solution, nitrogen was passed through the prepared test solution to remove oxygen for 5 minutes, the test solution was placed in a quartz sample tube and excited with 400nm wavelength light at room temperature (298K) and its emission spectrum was measured. The emission spectrum has a maximum emission wavelength λ max And the full width at half maximum FWHM (also known as the full width at half maximum or half peak width, that is, the peak width at half the peak height, the distance between the two points where a straight line parallel to the bottom of the peak passes through the midpoint of the peak height and intersects the two sides of the peak).
[0328] As an example, the maximum emission wavelength λ of the photoluminescence spectra of the following metal complexes and terminal luminescent materials was determined by the above method: max And the full width at half maximum (FWHM) in the photoluminescence spectrum. The specific results are shown in Table 1:
[0329] Table 1 Maximum emission wavelength and full width at half maximum of photoluminescence spectra of compounds
[0330]
[0331] Device Examples
[0332] Device Example 1
[0333] First, a 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 deposited under a vacuum of approximately 10 -8 In the case of torr, it is evaporated on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second. Compound HT and compound HT1 are co-evaporated to serve as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound PH-23 is used as an electron blocking layer (EBL). Then the metal complex 69 of the present invention is doped as a phosphorescent sensitizer and the terminal luminescent material compound DF-70 with the first host material compound PH-1 and the second host material compound H-40 and co-evaporated to serve as an emitting layer (EML). On the EML, compound HB serves as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-evaporated as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a desiccant to complete the device.
[0334] Device Example 2
[0335] The implementation method of device example 2 is the same as that of device example 1, except that the metal complex 1 of the present invention is used to replace the metal complex 69 in the light-emitting layer (EML), and the weight ratio of the first host material compound PH-1, the second host material compound H-40, the metal complex 1 of the present invention, and the terminal light-emitting material DF-70 of the present invention is 55:36:8:1.
[0336] Device Comparative Example 1
[0337] The implementation method of device comparison example 1 is the same as that of device example 1, except that the first host material compound PH-1 is used in the light-emitting layer (EML), the second host material compound H-40 and the terminal light-emitting material DF-70 of the present invention are co-evaporated to form the light-emitting layer (EML), and the weight ratio is 49.5:49.5:1.
[0338] Device Comparative Example 2
[0339] The implementation method of device comparison example 2 is the same as that of device example 1, except that the first host material compound PH-1, the second host material compound H-40 and the metal complex 69 of the present invention are co-evaporated to form the light-emitting layer (EML), and the weight ratio is 46:46:8.
[0340] Device Comparative Example 3
[0341] The implementation method of device comparison example 3 is the same as that of device example 2, except that the first host material compound PH-1 is used in the light-emitting layer (EML), the second host material compound H-40 and the terminal light-emitting material DF-70 of the present invention are co-evaporated to form the light-emitting layer (EML), and the weight ratio is 59:40:1.
[0342] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.
[0343] Table 2 Partial device structures of Examples 1-2 and Comparative Examples 1-3
[0344]
[0345] The material structure used in the device is shown below:
[0346]
[0347]
[0348] At 15 mA / cm 2 The CIE data of the device were measured at a constant current of max), full width at half maximum (FWHM), driving voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE), at 10000 cd / cm 2 The device lifetime LT97 was measured at the initial brightness and these data are recorded and shown in Table 3.
[0349] Table 3 Device data of Examples 1-2 and Comparative Examples 1-3
[0350]
[0351] The only difference between Example 1 and Comparative Example 1 is that a metal complex with a maximum emission wavelength within a specific range is used as a phosphorescence sensitizer in the light-emitting layer of Example 1, and another light-emitting material with a maximum emission wavelength within the same specific range and a narrow half-width is sensitized to serve as a terminal light-emitting material, while Comparative Example 1 does not use a metal complex as a phosphorescence sensitizer.
[0352] As can be seen from the data in Table 3, the maximum emission wavelengths of Example 1 and Comparative Example 1 are nearly identical, indicating that the light emitted by the device in Example 1 originates from the terminal luminescent material. Furthermore, compared to the conventional fluorescent light-emitting device of Comparative Example 1, the device in Example 1 of the present invention achieves unexpectedly significant improvements in device efficiency and lifetime, while maintaining a narrow half-width (FWHM) and low voltage comparable to those of Comparative Example 1. Specifically, CE, PE, and EQE significantly increase by 58.1%, 56.5%, and 57.9%, respectively, and lifetime is significantly increased by 14.5 times.
[0353] The only difference between Example 1 and Comparative Example 2 is that Example 1 utilizes both the metal complex of the present invention and a terminal luminescent material, resulting in a device that emits fluorescence, while Comparative Example 2 utilizes only the metal complex in the luminescent layer without a terminal luminescent material, resulting in a device that emits phosphorescence. Compared to the phosphorescent device of Comparative Example 2, the sensitized fluorescent device of Example 1 unexpectedly exhibits superior performance in all aspects: higher CE, PE, and EQE, a narrower half-width (FWHM), and a lower voltage. In particular, the lifetime of the sensitized fluorescent device of Example 1 is 4.1 times that of the phosphorescent device of Comparative Example 2.
[0354] The only difference between Example 2 and Comparative Example 3 is that, in addition to the terminal luminescent material, the light-emitting layer of Example 2 further uses the metal complex 1 of the present invention as a phosphorescence sensitizer.
[0355] Similarly, the device data in Table 3 shows that the maximum emission wavelengths of Example 2 and Comparative Example 3 are consistent, indicating that the light emitted by the device in Example 2 also originates from the terminal luminescent material. Compared to Comparative Example 3, Example 2, while maintaining a narrow half-width and low voltage similar to those of Comparative Example 3, further achieves significant improvements in device efficiency and lifetime. Specifically, CE, PE, and EQE are significantly increased by 80.9%, 82.7%, and 79.5%, respectively, and lifetime is increased by 19.4 times.
[0356] The above results show that, whether compared with ordinary fluorescent light-emitting devices that do not contain phosphorescence sensitizers or ordinary phosphorescent light-emitting devices that do not contain terminal light-emitting materials, the device of the present invention uses a metal complex with a maximum emission wavelength within a specific range as a phosphorescence sensitizer in the light-emitting layer, and sensitizes a terminal light-emitting material with a maximum emission wavelength within a specific range and a narrow half-width, has better overall performance. It can not only maintain a low driving voltage level and a narrow half-width, but also achieve a significant improvement in device efficiency and life, showing unique advantages.
[0357] Device Example 3
[0358] The implementation of Device Example 3 is the same as that of Device Example 1, except that the terminal emitting material compound DF-81 of the present invention is used in the emitting layer (EML) instead of the compound DF-70.
[0359] Device Comparative Example 4
[0360] The implementation method of device comparison example 4 is the same as that of device example 3, except that the first host material compound PH-1, the second host material compound H-40 and the terminal light-emitting material DF-81 of the present invention are co-evaporated to form the light-emitting layer (EML) in the light-emitting layer, and the weight ratio is 49.5:49.5:1.
[0361] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.
[0362] Table 4 Partial device structures of Example 3 and Comparative Example 4
[0363]
[0364] The new material structure used in the device is shown below:
[0365]
[0366] At 1000cd / cm 2 The CIE data of the device was measured at a constant brightness of max), full width at half maximum (FWHM), driving voltage (V), current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE), at 10000 cd / cm 2 The device lifetime LT95 was measured at the initial brightness and these data are recorded and shown in Table 5.
[0367] Table 5 Device data of Example 3 and Comparative Example 4
[0368]
[0369] Similarly, the difference between Example 3 and Comparative Example 4 is that the light-emitting layer of Example 3 uses a metal complex with a maximum emission wavelength within a specific range as a phosphorescence sensitizer, and sensitizes a terminal light-emitting material with a maximum emission wavelength within the same specific range and a half-peak width that meets specific conditions (≤60nm), while Comparative Example 4 does not use a metal complex as a phosphorescence sensitizer.
[0370] Similarly, the device data in Table 5 show that the maximum emission wavelengths of Example 3 and Comparative Example 4 are consistent, indicating that the light emitted by the device in Example 2 also originates from the terminal luminescent material. Compared to Comparative Example 4, Example 3, while maintaining a narrow half-width and low voltage similar to those of Comparative Example 4, further achieves significant improvements in device efficiency and lifetime. Specifically, CE, PE, and EQE are significantly increased by 94.9%, 110.4%, and 90.2%, respectively, and lifetime is increased by 6.2 times.
[0371] The above data show that compared with ordinary fluorescent light-emitting devices that do not contain phosphorescence sensitizers, the device of the present invention uses a metal complex with a maximum emission wavelength within a specific range as a phosphorescence sensitizer in the light-emitting layer to sensitize the terminal light-emitting material with a maximum emission wavelength within a specific range and a narrow half-width. It has very excellent comprehensive performance, not only maintaining a low driving voltage level and a narrow half-width, but also achieving a significant improvement in device efficiency and life, which makes up for the shortcomings of ordinary fluorescent light-emitting devices in efficiency and life, and exhibits more excellent comprehensive performance.
[0372] In summary, the device of the present invention can efficiently sensitize the terminal luminescent material in the luminescent layer by using a metal complex whose maximum emission wavelength meets specific conditions in the luminescent layer, thereby obtaining a device with excellent performance, such as low driving voltage, high device efficiency (CE, PE and EQE) and very excellent device life, and has broad application prospects.
[0373] It should be understood that the various embodiments described herein are merely 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 can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.
Claims
1. An organic electroluminescent device comprising: anode, cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising at least a metal complex and a terminal light-emitting material; The metal complex is selected from: a Pt complex, a Pd complex or an Au complex; The maximum emission wavelength in the photoluminescence spectrum of the metal complex is λ max1 ; The maximum emission wavelength in the photoluminescence spectrum of the terminal luminescent material is λ max2 , the full width at half maximum in the photoluminescence spectrum of the terminal luminescent material is FWHM2; in, 500nm<λ max1 ≤580nm, 500nm≤λ max2 ≤600nm, and FWHM2≤60nm.
2. The organic electroluminescent device according to claim 1, wherein The terminal luminescent material is an organic material; preferably, the terminal luminescent material is a fluorescent luminescent material, and more preferably, the terminal luminescent material is a delayed fluorescent material.
3. The organic electroluminescent device according to claim 1 or 2, wherein: The metal complex has a structure represented by Formula 1: in, The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence; Ring A1 to Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; L'1 to L'4 are each identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are identical or different; a1 to a4 are selected from 0 or 1 the same or differently at each occurrence, and at least two of a1 to a4 are selected from 1; E1 to E4 are each identically or differently selected from C or N; G1 to G4 are each identically or differently selected from a single bond, O, S or NR"; R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted; R1 to R4, R' and R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R1 to R4, R' and R" can optionally be linked to form a ring.
4. The organic electroluminescent device according to any one of claims 1 to 3, wherein: The metal complex has a structure represented by Formula 2: in, The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence; Ring A1 to Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; L'1 to L'3 are each identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are identical or different; E1 to E4 are each identically or differently selected from C or N; G1 is selected, identically or differently at each occurrence, from a single bond, O, S or NR"; R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted; R1 to R4, R' and R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R1 to R4, R' and R" can optionally be linked to form a ring.
5. The organic electroluminescent device according to claim 3 or 4, wherein: Ring A1 to Ring A4 are each identically or differently selected from an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof; Preferably, one or two of Rings A1 to A4 are selected from heteroaromatic rings containing at least 5 ring atoms, and the rest of Rings A1 to A4 are selected from aromatic rings having 6 ring atoms, or heteroaromatic rings having 6 ring atoms.
6. The organic electroluminescent device according to claim 3 or 4, wherein: Each occurrence of Ring A1 to Ring A4 is identically or differently selected from the group consisting of a pyrrole ring, a furan ring, a thiophene ring, a selenophene ring, an imidazole ring, an imidazole carbene ring, an oxazole ring, a thiazole ring, a selenazole ring, a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a benzopyrrole ring, a benzofuran ring, a benzothiophene ring, a benzoselenophene ring, a benzimidazole ring, a benzimidazole carbene ring, a benzoxazole ring, a benzothiazole ring, a benzoselenazole ring, a fluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzoselenophene ring, an azafluorene ring, an azacarbazole ring, an azadibenzofuran ring, an azadibenzothiophene ring, an azadibenzoselenophene ring, and combinations thereof.
7. The organic electroluminescent device according to claim 4, wherein: In Formula 2, L'1, L'2 and L'3 are each selected from a single bond, NR', O, S, the same or different when they appear; G1 is each selected from a single bond, O or NR"; Preferably, in Formula 2, L'1, L'2 and L'3 are selected from single bonds; and G1 is selected from O.
8. The organic electroluminescent device according to any one of claims 1 to 4, wherein: The metal complex has a structure represented by Formula 3: in, The metal M is selected, identically or differently, from Pt, Pd or Au on each occurrence; Ring A1, Ring A 22 , Ring A3, Ring A4 are identically or differently selected at each occurrence from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; Ring A 21 is selected from heteroaromatic rings having 5 ring atoms; E1 to E4 are each identically or differently selected from C or N; G1 is selected from O or S in the same or different manner at each occurrence; Y1, Y4, Y 11 Each occurrence is identically or differently selected from CR'', N, NR'', O or S; Y2, Y3, Y5 to Y 10 Each occurrence is identically or differently selected from C or N; R1 to R4 each time appear, the same or different, represent mono-, poly- or unsubstituted; R1 to R4, R'' are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R1 to R4, R'' can be optionally linked to form a ring.
9. The organic electroluminescent device according to any one of claims 3 to 8, wherein: The metal M is selected, identically or differently, from Pt or Pd on each occurrence; Preferably, the metal M is selected from Pt.
10. The organic electroluminescent device according to any one of claims 3 to 8, wherein: G1 is selected from O; E1 and E3 are selected from C; E2 and E4 are selected from N.
11. The organic electroluminescent device according to claim 8, wherein: In Formula 3, Ring A1, Ring A 22 , Ring A3, Ring A4 are each identically or differently selected from an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof; Ring A 21 are selected, identically or differently on each occurrence, from a heteroaromatic ring having 5 ring atoms; Preferably, in Formula 3, Ring A1, Ring A 22 , Ring A3 is selected from a benzene ring in the same or different manner each time it occurs, Ring A4 is selected from a pyridine ring in the same or different manner each time it occurs, Ring A 21 Each occurrence is identically or differently selected from imidazole rings.
12. The organic electroluminescent device according to any one of claims 8 to 11, wherein: In Formula 3, Y4 is selected from NR', O or S at each occurrence, the same or different; R' is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; Preferably, Y4 is selected from NR'' at each occurrence, the same or different, and R'' is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
13. The organic electroluminescent device according to claim 12, wherein: In Formula 3, Y2, Y3, Y5 to Y 10 Each occurrence is identically or differently selected from C; Y1, Y 11 Each occurrence of R' is identical or different and is selected from CR', said R'' being identical or different and is 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, cyano, and combinations thereof.
14. The organic electroluminescent device according to any one of claims 3 to 13, wherein: R1 to R4 are, at each occurrence, 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 alkenyl having 2 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof; Preferably, at least one of R1, at least one of R2, at least one of R3, or at least one of R4, which are the same or different at each occurrence, are selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, cyano, or a combination thereof.
15. The organic electroluminescent device according to claim 1, wherein the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 127, and the specific structures of Metal Complex 1 to Metal Complex 127 are as follows: Optionally, hydrogen in Metal Complexes 1 to 127 can be partially or fully replaced by deuterium.
16. The organic electroluminescent device according to claim 1, wherein: The terminal luminescent material has a structure represented by Formula 4: in, Ring A, Ring B, Ring C, Ring D, and Ring E are each independently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 30 carbon atoms; Z1, X1 and X2 are each independently selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR Si1 or GeR Ge1 ; T1 to T8 are each independently selected from C, CR t or N; a, b, c, d are each independently selected from 0 or 1; L1, L2, L3, L4 are each selected from the group consisting of a single bond, O, S, Se, BR L or NR L ; Each occurrence of R is the same or different and represents mono-, poly- or no substitution; R, R t , R L , R Si1 and R Ge1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, -BR B R B , and combinations thereof; R B Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R, R t , R L , R Si1 , R Ge1 and R B Can optionally be linked to form a ring.
17. The organic electroluminescent device according to claim 16, wherein the ring A, ring B, ring C, ring D and ring E are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Preferably, the ring A, ring B, ring C, ring D and ring E are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms; More preferably, the ring A, ring B, ring C, ring D and ring E are each independently selected from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof; Most preferably, the ring A, ring B, ring C, ring D and ring E are selected from benzene rings.
18. The organic electroluminescent device according to claim 16 or 17, wherein the Z1 is selected from B, P=O or P=S, and the X1 and X2 are each independently selected from N or P; Preferably, wherein said Z1 is selected from B, X1 and X2 are selected from N.
19. The organic electroluminescent device according to claim 16 or 17, wherein each of L1, L2, L3, and L4 is the same or different and is selected from a single bond, O, BR L or NR L .
20. The organic electroluminescent device according to claim 16 or 17, wherein a+b+c+d is greater than or equal to 1; Preferably, a+d is greater than or equal to 1; More preferably, wherein said a is 0 and d is 1; or wherein said a is 1 and d is 1.
21. The organic electroluminescent device according to claim 1, wherein the terminal light-emitting material has a structure represented by one of Formulas 4-1 to 4-7: in, Each occurrence of R is the same or different and represents mono-, poly- or no substitution; 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, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, -BR B R B , and combinations thereof; R B Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R and R B can optionally be linked to form a ring; Preferably, the terminal material has a structure represented by Formula 4-1 or Formula 4-2.
22. The organic electroluminescent device according to claim 16 or 21, wherein each occurrence of R 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, and combinations thereof; Preferably, each occurrence of R is identical or different and is 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 amino having 0 to 20 carbon atoms, and combinations thereof.
23. The organic electroluminescent device according to claim 21, wherein there are multiple R groups in Formulas 4-1 to 4-7, and at least one of the multiple R groups 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, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, or a combination thereof.
24. The organic electroluminescent device according to claim 1, wherein the terminal light-emitting material is selected from the group consisting of compound DF-1 to compound DF-102: Optionally, hydrogen in Compound DF-1 to Compound DF-102 can be partially or fully substituted with deuterium.
25. The organic electroluminescent device according to claim 1 or 2, wherein: 505nm≤λ max1 ≤560nm,510nm≤λ max2 ≤580nm; Preferably, 510 nm ≤ λ max1 ≤550nm; 510nm≤λ max2 ≤560nm.
26. The organic electroluminescent device according to claim 1 or 2, wherein: l max1 ≤λ max2 ,or0<min max1 -l max2 ≤30nm; Preferably, 0≤λ max2 -λ max1 ≤40nm, or 0<λ max1 -λ max2 ≤20nm; More preferably, 10≤λ max2 -λ max1 ≤30nm, or 0<λ max1 -λ max2 ≤10nm.
27. The organic electroluminescent device according to claim 1 or 2, wherein: FWHM2≤50nm; preferably, FWHM2≤40nm.
28. A display device comprising the organic electroluminescent device according to any one of claims 1 to 27.
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