Organic electroluminescent device and electronic apparatus thereof

Abstract

An organic electroluminescent device and its electronic device are disclosed. The organic electroluminescent device includes an anode, a cathode, and a light-emitting layer disposed between the anode and cathode. The light-emitting layer includes a host material and a light-emitting material. The host material includes at least a first compound, a second compound, and a third compound. The first and second compounds have the same carrier transport performance, and the absolute value of the HOMO energy level difference between the first and second compounds is greater than or equal to 0.05 eV. The third compound has different carrier transport performance from the first compound. The light-emitting material includes at least one phosphorescent material. This organic electroluminescent device can provide better device performance, such as improved device power efficiency. An electronic device incorporating this organic electroluminescent device is also disclosed.

Description

Technical Field

[0001] This invention relates to organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a light-emitting layer comprising at least three host materials, wherein the first compound and the second compound have the same carrier transport properties and |HOMO 第一化合物 -HOMO 第二化合物 | Organic electroluminescent devices with a voltage of ≥0.05eV and electronic devices comprising such organic electroluminescent devices. Background Technology

[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both 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. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art 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. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for 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 classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] Patent application US20210135142A1 discloses an organic electroluminescent device, wherein the light-emitting layer comprises a host material and a guest material. The host material of the light-emitting layer comprises a first, a second, and a third organic compound. The first and second organic compounds have different carrier transport properties. The third organic compound is doped into the mixture or stack interface formed by the first and second organic compounds and forms an intramolecular excitopolymer. The guest material in the light-emitting layer is a fluorescent organic compound. The patent application does not disclose or teach that the combination of the first and second compounds with the same carrier transport properties that satisfy a certain energy level difference can improve the device performance.

[0009] The emissive layer is one of the key functional layers affecting the performance of organic light-emitting devices (OLEDs). The combination of organic materials has a significant impact on device performance. Energy level matching and synergistic effects between different materials can improve carrier transport efficiency and reduce charge accumulation. Therefore, optimizing the combination of organic materials is crucial for improving the performance of OLED devices. However, the selection and combination of host materials in the emissive layer still face technical challenges such as high voltage, low efficiency, and energy level mismatch. Therefore, optimizing the energy level matching of host materials, improving carrier transport efficiency, and reducing charge accumulation to enhance the overall performance of the device remains a significant challenge. Summary of the Invention

[0010] The present invention aims to provide an organic electroluminescent device to solve at least some of the aforementioned problems. The light-emitting layer of the organic electroluminescent device of the present invention comprises a host material and a light-emitting material, wherein the host material comprises at least a first compound, a second compound, and a third compound, the first compound and the second compound having the same carrier transport properties, and |HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV, the third compound has different carrier transport properties from the first compound, the luminescent material contains at least one phosphorus luminescent material, and the organic electroluminescent device of the present invention can provide better device performance, such as significantly improving the power efficiency of the device.

[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 a host material and a light-emitting material, wherein the host material comprises at least a first compound, a second compound and a third compound;

[0015] The first compound and the second compound have the same carrier transport performance, and the HOMO level of the first compound is HOMO. 第一化合物 The HOMO energy level of the second compound is HOMO. 第二化合物 , and |HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV;

[0016] The third compound has different carrier transport properties from the first compound;

[0017] The luminescent material comprises at least one phosphorescent luminescent material.

[0018] According to another embodiment of the present invention, an electronic device is disclosed, which includes the organic electroluminescent device described in the above embodiments.

[0019] This invention discloses a novel organic electroluminescent device. The organic electroluminescent device of this invention includes a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode. The light-emitting layer includes a host material and a light-emitting material, wherein the host material includes at least a first compound, a second compound, and a third compound. The first compound and the second compound have the same carrier transport performance, and |HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV, the third compound has different carrier transport properties from the first compound; the luminescent material comprises at least one phosphorescent material. The organic electroluminescent device of the present invention can provide better device performance, such as significantly improving the power efficiency of the device. Attached Figure Description

[0020] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent devices disclosed herein.

[0021] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent devices disclosed herein. Detailed Implementation

[0022] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. 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. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0023] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein 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 herein 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 herein 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 herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0024] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may 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 may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0025] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0026] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation 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 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0027] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0028] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0029] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0030] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0031] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0032] 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: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0033] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0034] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0035] Definition of the term "substituent group"

[0036] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0037] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0038] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group 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, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0039] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0040] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0041] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 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, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0042] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. 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, fenene, fluorene, pyrene, etc. 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'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0043] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. 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, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. 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 ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0044] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0045] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can 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, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0046] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0047] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0048] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can 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, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0049] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0050] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0051] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0052] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment 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 aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0053] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0054] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0055] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0056] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0057] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0058] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0059]

[0060] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0061]

[0062] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0063]

[0064] Furthermore, the statement that adjacent substituents can optionally connect 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 bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0065]

[0066] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:

[0067] anode,

[0068] cathode,

[0069] And a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising a host material and a light-emitting material, wherein the host material comprises at least a first compound, a second compound and a third compound;

[0070] The first compound and the second compound have the same carrier transport performance, and the HOMO level of the first compound is HOMO. 第一化合物 The HOMO energy level of the second compound is HOMO. 第二化合物 , and |HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV;

[0071] The third compound has different carrier transport properties from the first compound;

[0072] The luminescent material comprises at least one phosphorescent luminescent material.

[0073] In this paper, "the first compound and the second compound have the same carrier transport performance" means that the first compound and the second compound have the same carrier transport characteristics, such as the first compound and the second compound having stronger hole transport performance than electron transport performance, and the first compound and the second compound being p-type compounds. "The third compound has different carrier transport performance from the first compound" means that the third compound and the first compound have different carrier transport characteristics, such as the third compound having stronger electron transport performance than hole transport performance, the third compound being an N-type compound, and the first compound and the second compound having stronger hole transport performance than electron transport performance, and the first compound and the second compound being p-type compounds.

[0074] According to an embodiment of the present invention, the |HOMO of the first compound and the second compound is... 第一化合物 -HOMO 第二化合物 |≥0.06eV.

[0075] According to an embodiment of the present invention, the |HOMO of the first compound and the second compound is... 第一化合物 -HOMO 第二化合物 |≥0.08eV.

[0076] According to one embodiment of the present invention, wherein the first compound and the second compound have a 0.05 eV ≤ |HOMO| 第一化合物 -HOMO 第二化合物 | < 0.2 eV.

[0077] According to one embodiment of the present invention, wherein the first compound and the second compound have a 0.06 eV ≤ |HOMO| 第一化合物 -HOMO 第二化合物 | < 0.2 eV.

[0078] According to one embodiment of the present invention, the F values ​​of the first compound and the second compound are both less than 1, the F value of the third compound is greater than 1, and F = V HOD @J50 / V EOD @J50.

[0079] In this article, V HOD @J50 indicates that the hole device current density is only 50mA / cm². 2 The voltage corresponding to the time represents the hole transmission performance; the smaller the voltage value, the stronger the hole transmission capability. V EOD @J50 indicates that only electronic devices have a current density of 50mA / cm². 2 The voltage corresponding to the time represents the electron transport performance; the smaller the voltage value, the stronger the electron transport capability.

[0080] According to one embodiment of the present invention, the first compound is a P-type compound, the second compound is a P-type compound, and the third compound is an N-type compound.

[0081] In this paper, P-type compounds are those in which hole transport is stronger than electron transport, and N-type compounds are those in which electron transport is stronger than hole transport.

[0082] According to an embodiment of the present invention, the HOMO energy level relationship between the first compound and the second compound satisfies: HOMO 第一化合物 <HOMO> 第二化合物 .

[0083] According to an embodiment of the present invention, the HOMO energy level relationship between the first compound and the second compound satisfies: HOMO 第二化合物 -HOMO 第一化合物 ≥0.06eV.

[0084] According to an embodiment of the present invention, the HOMO energy level relationship between the first compound and the second compound satisfies: HOMO 第二化合物 -HOMO 第一化合物 ≥0.08eV.

[0085] According to one embodiment of the present invention, the HOMO energy level relationship between the first compound and the second compound satisfies: 0.06 eV ≤ HOMO 第二化合物 -HOMO 第一化合物 <0.2eV.

[0086] According to one embodiment of the present invention, the HOMO energy level relationship between the first compound and the second compound satisfies: 0.08 eV ≤ HOMO 第二化合物 -HOMO 第一化合物 <0.2eV.

[0087] According to one embodiment of the present invention, wherein HOMO 第一化合物 ≤-5.33eV.

[0088] According to one embodiment of the present invention, wherein HOMO 第一化合物 ≤-5.34eV.

[0089] According to one embodiment of the present invention, wherein HOMO 第二化合物 ≥-5.30eV.

[0090] According to one embodiment of the present invention, wherein HOMO 第二化合物 ≥-5.29eV.

[0091] According to one embodiment of the present invention, wherein HOMO 第二化合物 ≥-5.284eV.

[0092] According to one embodiment of the present invention, the first compound and the second compound are aromatic amine compounds.

[0093] According to one embodiment of the present invention, the first compound and the second compound further comprise at least one chemical group selected from the group consisting of: oxazole, thiazole, benzoxazole, benzothiazole, naphthoxazole, naphthothiazole, benzothiophene, benzimazole, benzofuran, dibenzothiophene, dibenzofuran, azadibenzothiophene, azadibenzofuran, dibenzoselenophene, benzene, pyridine, pyrimidine, fused-ring carbazole, indolocarbazole, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0094] According to one embodiment of the present invention, the first compound and the second compound further comprise at least one chemical group selected from the group consisting of: benzoxazole, benzothiazole, benzimidazole, naphthoxazole, and naphthothiazole.

[0095] According to one embodiment of the present invention, the third compound is an N-type compound, and the LUMO energy level of the third compound is LUMO. 第三化合物 , and LUMO 第三化合物 ≥-3.0eV.

[0096] According to one embodiment of the present invention, the third compound is an N-type compound, and the LUMO energy level of the third compound is LUMO. 第三化合物 , and LUMO 第三化合物 ≥-2.9eV.

[0097] According to one embodiment of the present invention, the third compound is an N-type compound, and the LUMO energy level of the third compound is LUMO. 第三化合物 , and LUMO 第三化合物 ≥-2.829eV.

[0098] According to one embodiment of the present invention, the third compound is a triazine compound.

[0099] According to one embodiment of the present invention, the first compound has a structure represented by Formula 1:

[0100]

[0101] in,

[0102] G2 is selected from O or S;

[0103] G1 is selected from O, S, Se, CR1R2, SiR3R4, or NR. n ;

[0104] X1 to X4 are selected from CR each time they appear, either identically or differently. x Or N;

[0105] Y1 to Y3 are selected from CR each time they appear, either in the same or different ways. y Or N;

[0106] When Y4 to Y7 appear, they are selected from C or CR, either identically or differently. y Or N; one of Y4 to Y7 is selected from C and connected to L1;

[0107] L1 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0108] Ar1 and Ar2, each time appearing, are selected from the same or different aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), cycloalkyl groups having 3-20 cyclic carbon atoms (substituted or unsubstituted), or combinations thereof.

[0109] R x R y R n R”1, R”2, R”3, and R”4, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The following are substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0110] Adjacent substituent R x They can be arbitrarily connected to form a loop;

[0111] Adjacent substituent R y They can be arbitrarily connected to form a ring.

[0112] In this paper, "adjacent substituent R" x "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein x They can connect to form a ring. It is obvious that any adjacent substituents R... x They can also be left unconnected to form a loop.

[0113] In this paper, "adjacent substituent R" y "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein y They can connect to form a ring. It is obvious that any adjacent substituents R... yThey can also be left unconnected to form a loop.

[0114] According to one embodiment of the present invention, the first compound has a structure represented by one of Formulas 1-1 to 1-3:

[0115]

[0116] in,

[0117] G2 is selected from O or S;

[0118] G1 is selected from O, S, Se, CR1R2, SiR3R4, or NR. n ;

[0119] X1 to X8 are selected from CR each time they appear, either identically or differently. x Or N;

[0120] Y1 to Y3 are selected from CR each time they appear, either in the same or different ways. y Or N;

[0121] When Y4 to Y7 appear, they are selected from C or CR, either identically or differently. y Or N; one of Y4 to Y7 is selected from C and connected to L1;

[0122] L1 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0123] Ar1 and Ar2, each time appearing, are selected from the same or different aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), cycloalkyl groups having 3-20 cyclic carbon atoms (substituted or unsubstituted), or combinations thereof.

[0124] R x R y R nR”1, R”2, R”3, and R”4, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The following are substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0125] Adjacent substituent R x They can be arbitrarily connected to form a loop;

[0126] Adjacent substituent R y They can be arbitrarily connected to form a ring.

[0127] According to one embodiment of the present invention, Y1 to Y3 are selected from CR each time they appear, either identically or differently. y Each occurrence of Y4 to Y7 is either identical or different and is selected from C or CR. y One of Y4 to Y7 is selected from C and connected to L1.

[0128] According to one embodiment of the present invention, Y7 is selected from CR y One of Y4, Y5, or Y6 is C and connected to L1.

[0129] According to one embodiment of the present invention, Y5 is C and connected to L1.

[0130] According to one embodiment of the present invention, G2 is selected from O; G1 is selected from O, S, CR1R2, SiR3R4, or NR. n .

[0131] According to one embodiment of the present invention, G2 is selected from O; G1 is selected from O, S, CR1R2 or NR. n .

[0132] According to one embodiment of the present invention, G2 is selected from O; G1 is selected from O, S or CR1R2.

[0133] According to one embodiment of the present invention, R x R y R n R”1, R”2, R”3 and R”4 are selected from the group consisting of the following, either identically or differently, each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0134] Adjacent substituent R x They can be arbitrarily connected to form a loop;

[0135] Adjacent substituent R y They can be arbitrarily connected to form a ring.

[0136] According to one embodiment of the present invention, R x R y R n R”1, R”2, R”3, and R”4 are selected from the group consisting of the following groups, either identically or differently, each time they appear: hydrogen, deuterium, fluorine, phenyl, pyridyl, pyrimidinyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, carbazoleyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

[0137] According to one embodiment of the present invention, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0138] According to one embodiment of the present invention, at least one of Ar1 and Ar2 is selected from the following structures:

[0139]

[0140] U1 to U9 are selected from C and CR, respectively, each time appearing in the same or different ways. u Or N; one of U1 to U5 is selected from C and one of U6 to U9 is selected from C;

[0141] U' 10 toU' 11 Each time it appears, it is selected from CR in the same or different ways. u Or N;

[0142] R u Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0143] Adjacent substituent R u They can be arbitrarily connected to form a loop;

[0144] Where “*” indicates the connection position of Ar1 and / or Ar2 with N shown in Equation 1.

[0145] In this paper, "adjacent substituent R" u "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein u They can connect to form a ring. It is obvious that any adjacent substituents R... u They can also be left unconnected to form a loop.

[0146] According to one embodiment of the present invention, at least one of Ar1 and Ar2 is selected from the following structures:

[0147]

[0148] U1 to U9 are selected from C and CR, respectively, each time appearing in the same or different ways. u Or N; one of U1 to U5 is selected from C and one of U6 to U9 is selected from C;

[0149] U 10 toU 13 Each time it appears, it is selected from CR in the same or different ways. u Or N;

[0150] R u Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkynyl groups having 2-20 carbon atoms. The following are substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, cyano, isocyano, hydroxyl, mercapto groups, and combinations thereof having 0-20 carbon atoms.

[0151] Adjacent substituent R u They can be arbitrarily connected to form a loop;

[0152] Where “*” indicates the connection position of Ar1 and / or Ar2 with N shown in Equation 1.

[0153] According to one embodiment of the invention, Ar1 and Ar2, each time they appear, are selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted... The group, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzoxazolyl, or combinations thereof.

[0154] According to one embodiment of the invention, Ar1 and Ar2, each time they appear, are selected from the group consisting of: phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenylnaphthyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, dibenzoselenyl, fluorenyl, silylfluorenyl. The groups are: carbazolyl, pyridinyl, pyrimidinyl, benzoxazole, and combinations thereof.

[0155] According to one embodiment of the present invention, L1 is selected from single bonds, substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, or combinations thereof.

[0156] According to one embodiment of the present invention, L1 is selected from single bond, phenylene, naphthylene, biphenylene, phenanthrene, pyridylene, or a combination thereof.

[0157] According to one embodiment of the present invention, the first compound is selected from the group consisting of:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] According to one embodiment of the present invention, the hydrogen in the structure of compounds A-1 to A-54, and compounds A-58 to A-60 is partially or completely replaced by deuterium.

[0165] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2:

[0166]

[0167] in,

[0168] Z is selected from NR' n O or S;

[0169] Ar 21 To Ar 23 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0170] If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;

[0171] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;

[0172] L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0173] R w , R' n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0174] Adjacent substituent R w They can be connected arbitrarily to form a loop.

[0175] In this paper, "adjacent substituent R" w "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein w They can connect to form a ring. It is obvious that any adjacent substituents R... w They can also be left unconnected to form a loop.

[0176] According to one embodiment of the present invention, Z1 or Z4 is selected from C and connected to a six-membered ring containing W1 to W5.

[0177] According to one embodiment of the present invention, Z4 is selected from C and connected to a six-membered ring comprising W1 to W5.

[0178] According to one embodiment of the present invention, R zEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and when R z When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is selected from one or more of deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 ring atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, and unsubstituted groups having... The group consisting of alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, unsubstituted aryl groups with 6-30 carbon atoms, unsubstituted heteroaryl groups with 3-30 carbon atoms, unsubstituted alkylsilyl groups with 3-20 carbon atoms, unsubstituted arylsilyl groups with 6-20 carbon atoms, unsubstituted alkylgermanium groups with 3-20 carbon atoms, unsubstituted arylgermanium groups with 6-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphinyl groups, and combinations thereof.

[0179] According to one embodiment of the present invention, Z is selected from O or S.

[0180] According to one embodiment of the present invention, Z is selected from O.

[0181] According to one embodiment of the present invention, L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, or combinations thereof.

[0182] According to one embodiment of the present invention, L2 is selected from single bonds, or substituted or unsubstituted aryl groups having 6-20 carbon atoms.

[0183] According to one embodiment of the present invention, L2 is selected from single bond, phenylene, naphthylene, biphenylene, or phenanthrene.

[0184] According to one embodiment of the invention, W1 to W5 are selected from C or CR each time they appear, either identically or differently. w And one of W1 to W5 is selected from C and connected to L2.

[0185] According to one embodiment of the invention, W1 to W5 are selected from C or CR each time they appear, either identically or differently. w And one of W2, W3 and W4 is C and connected to L2.

[0186] According to one embodiment of the invention, W1 to W5 are selected from C or CR each time they appear, either identically or differently. w And W3 is C and connected to L2.

[0187] According to one embodiment of the present invention, R w R z , R' n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and combinations thereof.

[0188] According to one embodiment of the present invention, R w R z , R' n Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiopheneyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

[0189] According to one embodiment of the present invention, Ar 21 Ar 22 Ar 23Selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, or combinations thereof.

[0190] According to one embodiment of the present invention, Ar 21 Ar 22 Ar 23 Each occurrence is selected, either identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... The group is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fused-ring carbazolyl group, or a combination thereof.

[0191] According to one embodiment of the present invention, Ar 21 Ar 22 Ar 23 Each occurrence is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, carbazole, fused-ring carbazole, dibenzofuranyl, dibenzothiophene, fluorenyl, silylfluorenyl, or similar compounds. Base, or a combination thereof.

[0192] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2-1:

[0193]

[0194] in,

[0195] Z is selected from NR' n O or S;

[0196] Ar 21 Ar 23 Ar 24 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;

[0197] Ring A is selected from fused-ring aromatic rings having 10-30 carbon atoms, fused-ring heteroaromatic rings having 8-30 carbon atoms, or combinations thereof;

[0198] R 21 R 22 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0199] If Z1 to Z4 appear the same or different each time, choose C; CR zOr N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;

[0200] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;

[0201] L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0202] R w , R' n R z R 21 R 22 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0203] Adjacent substituent R w They can be connected arbitrarily to form a loop.

[0204] According to one embodiment of the present invention, ring A is selected from fused-ring aromatic rings having 10-20 carbon atoms, fused-ring heteroaromatic rings having 8-20 carbon atoms, or combinations thereof.

[0205] According to one embodiment of the present invention, ring A is selected from fused-ring aromatic rings having 10-12 carbon atoms, fused-ring heteroaromatic rings having 8-12 carbon atoms, or combinations thereof.

[0206] According to one embodiment of the present invention, ring A is selected from naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring, quinoline ring, isoquinoline ring, dibenzofuran ring, dibenzothiophene ring, dibenzoselenene ring, silylfluorene ring, fluorene ring, spirofluorene ring, and spirosilylfluorene ring. Rings, or combinations thereof.

[0207] According to one embodiment of the present invention, the second compound is selected from the group consisting of:

[0208]

[0209]

[0210]

[0211]

[0212] According to one embodiment of the present invention, the hydrogen in the structure of compounds A1-1 to A1-34, and compounds A1-36 to A1-42 can be partially or completely replaced by deuterium.

[0213] According to one embodiment of the present invention, the third compound has a structure represented by Formula 3:

[0214]

[0215] In Equation 3,

[0216] L 31 To L 33 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0217] Ar 31 To Ar 33 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0218] According to one embodiment of the present invention, the third compound has the structure shown in Formula 3-1:

[0219]

[0220] V1-V6 each time they appear, they are either selected from C, N, or CR, either in the same or different ways. v And one of V1-V6 is C and is associated with L.33 Connected;

[0221] L 31 To L 33 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0222] Ar 31 and Ar 32 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0223] R v Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0224] Adjacent substituent R v They can be arbitrarily connected to form a ring.

[0225] In this paper, adjacent substituents R v They can be optionally linked to form a ring, intended to represent any adjacent substituent R therein. v They can connect to form a ring. It is obvious that any adjacent substituents R... v They can also be left unconnected to form a loop.

[0226] According to one embodiment of the present invention, the third compound has the structure shown in Formula 3-1-1 or Formula 3-1-2:

[0227]

[0228] In Equation 3-1-1, V1-V5 are selected from C, N, or CR each time they appear, either identically or differently. v V 11 -V 15 Each occurrence is either identically or differently selected from N or CR v1 And one of V1-V5 is C and is associated with L. 33 Connected; in Equation 3-1-2, V1-V4 are selected from C, N, or CR each time they appear, either identically or differently. v V 11 -V 14 Each occurrence is either identically or differently selected from N or CR v1 And one of V1-V4 is C and is associated with L 33 Connected;

[0229] V is selected from O, S, or Se;

[0230] L 31 To L 33 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0231] Ar 31 and Ar 32 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0232] R v R v1Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0233] Adjacent substituent R v R v1 They can be arbitrarily connected to form a ring.

[0234] In this paper, adjacent substituents R v R v1 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, adjacent substituent R. v Between, adjacent substituents R v1 Between, and adjacent substituents R v and R v1 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0235] According to one embodiment of the present invention, in formula 3-1-2, V is selected from O or S.

[0236] According to one embodiment, V is O in Equation 3-1-2.

[0237] According to one embodiment of the present invention, in formula 3-1-1, V1 to V5 are selected from C or CR each time they appear, either identically or differently. v V 11 To V 15 Each time it appears, it is selected from CR in the same or different ways. v1 In Equation 3-1-2, V1 to V4 are selected from C or CR each time they appear, either identically or differently. v V11 To V 14 Each time it appears, it is selected from CR in the same or different ways. v1 .

[0238] According to one embodiment of the present invention, wherein R v R v1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0239] According to one embodiment of the present invention, in formula 3-1-1, at least one of V1 to V5 is selected from CR. v , or V 11 To V 15 At least one of them is selected from CR v1 In Equation 3-1-2, at least one of V1 to V4 is selected from CR. v , or V 11 To V 14 At least one of them is selected from CR v1 And the R v R v1 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, either identically or differently.

[0240] According to one embodiment of the present invention, wherein R v R v1 Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0241] According to one embodiment of the present invention, wherein the Ar 31 and Ar 32 At least one of them has a structure with two or three fused rings.

[0242] According to one embodiment of the present invention, Ar 31 and Ar 32 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof, either identically or differently.

[0243] According to one embodiment of the present invention, Ar 31 and Ar 32Each occurrence is selected, either identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted... The group, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted indolocarbazolyl, or combinations thereof.

[0244] According to one embodiment of the present invention, L 31 To L 33 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0245] According to one embodiment of the present invention, L 31 To L 33 Each time it appears, it is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or combinations thereof, either identically or differently.

[0246] According to one embodiment of the present invention, the third compound is selected from the group consisting of:

[0247]

[0248]

[0249]

[0250]

[0251]

[0252] According to one embodiment of the present invention, the hydrogen in the structure of compounds B-1 to B-50 is partially or completely replaced by deuterium.

[0253] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 0.1-99.9:0.1-99.9:0.1-99.9.

[0254] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 1-99:1-99:1-99.

[0255] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 10-90:10-90:10-90.

[0256] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 20-50:20-60:20-50.

[0257] According to one embodiment of the present invention, the luminescent material is a phosphorescent luminescent material.

[0258] According to one embodiment of the present invention, the maximum emission wavelength of the phosphorescent material is greater than or equal to 400 nm and less than or equal to 800 nm.

[0259] According to one embodiment of the present invention, the maximum emission wavelength of the phosphorescent material is greater than or equal to 450 nm and less than or equal to 700 nm.

[0260] According to one embodiment of the present invention, the maximum emission wavelength of the phosphorescent material is greater than or equal to 580 nm and less than or equal to 650 nm.

[0261] According to one embodiment of the present invention, the phosphorescent material is a metal complex, and the metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0262] M is selected from metals with a relative atomic mass greater than 40;

[0263] L a L b and L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b and L c They can be selectively linked to form multidentate ligands;

[0264] L a L b and L c Same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, and q equals the oxidation state of M; when m is greater than or equal to 2, multiple L a Same or different; when n is 2, the two L b Same or different; when q is 2, the two L c Same or different;

[0265] L a Each occurrence may be selected from the structure shown in Equation 4, either identically or differently:

[0266]

[0267] in,

[0268] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0269] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0270] Rings D and E via U a and U b Condensation;

[0271] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0272] R d and R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0273] V 31 To V 34 Each time it appears, it is selected from CR in the same or different ways. v3 Or N;

[0274] R d R e and R v3Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0275] Adjacent substituent R d R e and R v3 They can be arbitrarily connected to form a loop;

[0276] L b and L c Each occurrence may be selected from any of the following structures, either identically or differently:

[0277]

[0278]

[0279] in,

[0280] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0281] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0282] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2;

[0283] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0284] The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0285] In this paper, adjacent substituents R d R e R v3 The ability to optionally connect to form a ring is intended to indicate the presence of a substituent R. d Substituent R e Substituent R v3 When, adjacent substituent groups, such as adjacent substituent R d Substituents R between and adjacent e Substituents R between and adjacent v3 Substituents R between and adjacent d With Re Substituents R between and adjacent d With R v3 Between and adjacent substituents R e With R v3 Between these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... d , substituent R e , substituent R v3 At the same time, these substituent groups may not be connected to form a ring.

[0286] In this paper, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 Between these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to:

[0287]

[0288] Where W is selected from O, S, Se, NR w1 or CR w1 R w1 ; wherein R w1 R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.

[0289] According to one embodiment of the present invention, in Formula 4, two adjacent substituents R e The connection forms a loop.

[0290] According to one embodiment of the present invention, in Formula 4, two adjacent substituents R e They can be linked to form 5-membered unsaturated carbon rings, 5-membered heteroaromatic rings, or benzene rings.

[0291] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring.

[0292] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.

[0293] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, ring E is a benzene ring or a 6-membered heteroaromatic ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.

[0294] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbide ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.

[0295] According to one embodiment of the present invention, in formula 4, R d R e R v3 At least one or two sets of adjacent substituents are linked to form a ring. For example, two substituents R d The connection forms a ring, or two substituents R e The connection forms a ring, or two substituents R v3 Linkage to form a ring, or substituent R d With substituent R e The links between them form a ring, or the substituent R d With substituent R v3 The links between them form a ring, or the substituent R eWith substituent R v3 The two substituents R are connected to form a ring or a ring. d The two substituents R connect to form a ring. e The connection forms a ring, or two substituents R d The two substituents R connect to form a ring. v3 The connection forms a ring, or two substituents R e The two substituents R connect to form a ring. v3 Linkage forms a ring, substituent R e With substituent R v3 The two substituents R are linked to form a ring. v3 Linkage to form a ring, or substituent R d With substituent R v3 The two substituents R are linked to form a ring. v3 The connection forms a loop; R d R e R v3 A similar situation occurs when more adjacent substituents are linked to form a ring.

[0296] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is a metal complex, and the metal complex has M(L) a ) m (L b ) n The general formula;

[0297] M is selected from metals with a relative atomic mass greater than 40;

[0298] L a L b The first and second ligands, respectively, coordinate with M; L a L b They can be selectively linked to form multidentate ligands;

[0299] m is 1, 2, or 3; n is 0, 1, or 2; the sum of m and n equals the oxidation state of M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different;

[0300] L a Each occurrence may be selected from the structure shown in Equation 4, either identically or differently:

[0301]

[0302] in,

[0303] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0304] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0305] Rings D and E via U a and U b Condensation;

[0306] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0307] R d and R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0308] V 31 To V 34 Each time it appears, it is selected from CR in the same or different ways. v3 Or N;

[0309] R d R e and R v3 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0310] Adjacent substituent R d R e and R v3 They can be arbitrarily connected to form a loop;

[0311] The ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0312]

[0313] R1 to R7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0314] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0315]

[0316] Wherein, at least one of R1 to R3 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and / or at least one of R4 to R6 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

[0317] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0318]

[0319] Wherein, at least two of R1 to R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

[0320] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0321]

[0322] Wherein, at least two of R1 to R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.

[0323] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex, a Pt complex, or an Os complex.

[0324] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and has Ir(L) oxidizing properties. a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a (L) b )2、Ir(L a )2(L c ) or Ir(L a (L) c Any of the structures shown in )2.

[0325] According to one embodiment of the present invention, wherein L aIt has the structure shown in Formula 4 and contains at least one structural unit selected from the group consisting of a 6-membered 6-membered aromatic ring, a 6-membered 6-membered heteroaromatic ring, a 6-membered 5-membered aromatic ring and a 6-membered 5-membered heteroaromatic ring.

[0326] According to an embodiment of the present invention, in the organic electroluminescent device, wherein L a It has the structure shown in Formula 4 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0327] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. a The L a Each time it appears, choose either the same or different one from any of the following groups of structures:

[0328]

[0329]

[0330]

[0331]

[0332] In the structure described, TMS represents trimethylsilyl.

[0333] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. b The L b Each time it appears, choose either the same or different one from any of the following groups of structures:

[0334]

[0335]

[0336] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345] In the structure described, TMS represents trimethylsilyl.

[0346] According to another embodiment of the present invention, an electronic device is disclosed that includes the organic electroluminescent device described in the above embodiments.

[0347] Combination with other materials

[0348] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein 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.

[0349] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are 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 herein 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.

[0350] The first, second, and third compounds used in this invention can be obtained by referring to the preparation methods in the prior art, or the first compound can be easily prepared by referring to patent applications such as CN202410557117.3, the second compound can be easily prepared by referring to patent applications such as CN115109051A, and the third compound can be easily prepared by referring to patent applications such as CN118946179A. The preparation methods will not be elaborated here. The preparation method of the electroluminescent device is not limited; the preparation method in the following embodiments is merely an example and should not be construed as limiting. Those skilled in the art can reasonably improve the preparation methods of the following embodiments based on the prior art. For example, the proportions of various materials in the light-emitting layer are not particularly limited; those skilled in the art can reasonably select them within a certain range based on the prior art. For instance, based on the total weight of the light-emitting layer materials, the main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 90%-98%, and the light-emitting material can account for 2%-10%. In the embodiments of the device, the characteristics of the device are also tested using conventional equipment in the art (including but not limited to vapor deposition machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) and methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the sample reliably and unaffected, the above-mentioned related content will not be elaborated in this patent.

[0351] This invention has found that by combining the light-emitting layer materials in the device, such as selecting a three-body system that meets certain energy level differences, a more precise control can be achieved in the carrier injection, transport, and recombination processes, improving the carrier distribution and transport paths. By optimizing carrier injection and transport, carriers in the three-body system can be more evenly distributed, thereby improving the power efficiency of the device and significantly enhancing its overall performance.

[0352] In this paper, the method for fabricating a hole-only device (HOD) containing the test compound is as follows: a 0.7 mm thick glass substrate is used, on which a pre-patterned... A thick layer of indium tin oxide (ITO) is used as the anode, with a sheet resistance of 14–20 Ω / sq and an effective light-emitting area of ​​4 mm². 2 The substrate was cleaned with deionized water and detergent, followed by treatment of the ITO surface with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support frame into the vacuum chamber. The organic layer specified below was applied at a vacuum level of approximately 10... -6In the case of Torr, The deposition rate was achieved sequentially on the anode layer via vacuum thermal evaporation: first, compounds HT and HI were simultaneously deposited as hole injection layers (weight ratio 97:3). ), the vapor-deposited compound HT is used as a hole transport layer. Compound EB is used as an electron blocking layer Next, the compound layer to be tested is deposited by vapor deposition. The HT compound deposited on it serves as an electron transport layer. Then, compounds HT and HI are simultaneously deposited as electron injection layers (weight ratio 97:3). Finally, metallic aluminum is vapor-deposited as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device. That is, the device is a hole-only device with ITO. / HT:HI(97:3, ) / HT / EB / Compound layer to be tested / HT / HT:HI(97:3, ) / Al The structure.

[0353] The structures of compounds HT, HI, and EB are as follows:

[0354]

[0355] In this paper, the method for fabricating the electron-only device (EOD) containing the test compound is as follows: using a 0.7 mm thick glass substrate, on which a pre-patterned... A thick layer of indium tin oxide (ITO) is used as the anode, with a sheet resistance of 14–20 Ω / sq and an effective light-emitting area of ​​4 mm². 2 The substrate was cleaned with deionized water and detergent, followed by treatment of the ITO surface with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support frame into the vacuum chamber. The organic layer specified below was applied at a vacuum level of approximately 10... -6 In the case of Torr, The rate is achieved by sequentially depositing the compound 8-hydroxyquinoline-lithium (Liq) onto the anode layer via vacuum thermal evaporation: the evaporated compound is used as the hole injection layer. Simultaneously deposited on it are compounds ET and 8-hydroxyquinoline-lithium (Liq) as hole transport layers (weight ratio 40:60). ), vapor deposition of the compound layer to be tested Compound B-1 is deposited on it as an electron blocking layer. ET and the compound 8-hydroxyquinoline-lithium (Liq) (weight ratio 40:60) are then simultaneously deposited on it. This serves as an electron transport layer, followed by the deposition of 8-hydroxyquinoline-lithium (Liq). Finally, as the electron injection layer, metallic aluminum is vapor-deposited as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device. That is, the device is an electronic-only device with ITO. / Liq / ET:Liq (weight ratio 40:60, ) / Test compound layer / B-1 / ET:Liq (weight ratio 40:60, ) / Liq / Al The structure.

[0356] The structural formulas of compounds ET,Liq,B-1 are shown below:

[0357]

[0358] Using the IVL photoelectric testing system (model S-1000GA4) from Suzhou Fushida Scientific Instruments Co., Ltd., the JV curves of the hole-only device and the electron-only device were tested respectively, and the results were obtained at 50 mA / cm². 2 The driving voltage (volts, V) at the current density, i.e., V HOD @J50 and V EOD @J50, data are shown in Table 1. The structures of compounds A-41, A-14, A1-1, and B-26 are described in Table 3.

[0359] Table 1. V of the compounds EOD @J50, V HOD @J50 and F value

[0360] A-41 3.52 8.67 0.41 A-14 3.45 8.17 0.42 A1-1 3.45 11.27 0.31 B-26 20 6.72 2.98

[0361] V HOD @J50 indicates that the compound being tested only has a hole device at 50 mA / cm. 2 The voltage corresponding to the current density represents the hole transport performance of the compound under test. V EOD @J50 indicates that the test compound only has electronic devices at 50mA / cm. 2The voltage corresponding to the current density represents the electron transport performance of the compound under test. F is defined as F = V. HOD @J50 / V EOD @J50, under the conditions of this test structure, when the F value of the test compound is less than 1, it indicates that the hole transport performance of the test compound is stronger than that of the electron transport performance, and it is a P-type compound. For example, for two compounds with F values ​​both less than 1 or multiple compounds with F values ​​both less than 1, we consider these compounds to have the same carrier transport characteristics, i.e., "have the same carrier transport performance" as stated in the text. When the F value of the test compound is greater than 1, it indicates that the electron transport performance of the test compound is stronger than that of the hole transport performance, and it is an N-type compound. For example, for two compounds with F values ​​both greater than 1 or multiple compounds with F values ​​both greater than 1, we also consider these compounds to have the same carrier transport characteristics, i.e., "have the same carrier transport performance" as stated in the text. For example, when the F values ​​of one compound are all greater than 1 and the F values ​​of another compound are all less than 1, we consider these two compounds to have different carrier transport characteristics, i.e., "have different carrier transport performance" as stated in the text. As shown in Table 1, compounds A-41, A-14, and A1-1 all have F < 1, exhibiting the same carrier transport performance and are all P-type compounds; compound B-26 has F > 1, and is an N-type compound. Compound B-26 has different carrier transport performance from compounds A-41, A-14, and A1-1.

[0362] In this paper, the HOMO (highest occupied orbital) and LUMO (lowest unoccupied orbital) values ​​for all compounds were obtained by cyclic voltammetry (CV). The tests were conducted using a CorrTest CS120 electrochemical workstation (manufactured by Wuhan CorrTest Instruments Co., Ltd.) with a three-electrode system: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. The test temperature was 25℃, and anhydrous DCM or DMF was used as the solvent, with 0.1 mol / L tetrabutylammonium hexafluorophosphate as the supporting electrolyte. The test compounds were prepared into 10... -3 A mol / L solution was used, and nitrogen gas was bubbled into the solution for 10 min to remove oxygen before the test. Instrument parameters were set as follows: scan rate 100 mV / s, potential interval 0.5 mV, and test window 1 V to -0.5 V. In this paper, for all "HOMO levels" and "LUMO levels," the smaller the value (i.e., the larger the absolute value), the deeper the energy level; the larger the value (i.e., the smaller the absolute value), the shallower the energy level. For example, in this paper, "HOMO of the first compound..." 第一化合物"≤-5.34" means that the HOMO energy level of the first compound is greater than or equal to 5.34 eV in absolute value, for example, the HOMO energy level of the first compound is -5.344 eV; "the HOMO energy level of the second compound" means that the HOMO energy level of the second compound is greater than or equal to 5.34 eV in absolute value. 第二化合物 "≥-5.29eV" means that the HOMO level of the second compound is less than or equal to 5.29eV in absolute value, for example, the HOMO level of the second compound is -5.284eV; "LUMO level of the third compound" 第三化合物 "≥-3.0eV" means that the LUMO energy level of the third compound is less than or equal to 3.0eV in absolute value. For example, the LUMO energy level of the third compound is -2.829eV.

[0363] Table 2 shows the HOMO and LUMO energy levels of some compounds.

[0364]

[0365] As shown in Table 2, the |HOMO of the first compound A-41 and the second compound A1-1 is... 第一化合物 -HOMO 第二化合物 | 0.081 eV, the HOMO of the first compound A-14 and the second compound A1-1 第一化合物 -HOMO 第二化合物 | 0.06 eV all satisfy | HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV.

[0366] Device Examples

[0367] Example 1: Preparation of red phosphorescent organic electroluminescent device.

[0368] First, a 0.7mm thick glass substrate is used, on which a pre-patterned design is applied. A thick indium tin oxide (ITO) substrate was used as the anode. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support and transferred to a vacuum chamber. The organic layer specified below was applied at a vacuum degree of approximately 10... -6 In the case of Torr, The rate was achieved by sequentially depositing compounds HT and HI onto the anode layer via vacuum thermal evaporation: first, compounds HT and HI were simultaneously deposited as hole injection layers (HIL, 97:3). ), the vapor-deposited compound HT is used as a hole transport layer (HTL, ), the vapor-deposited compound EB is used as an electron blocking layer (EBL, Compounds A-41, A1-1, B-26, and RD are simultaneously deposited on it as the luminescent layer (EML, 29:39:29:3). ), and the vapor-deposited compound B-1 serves as a hole-blocking layer (HBL). Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL, 40:60). ), 8-hydroxyquinoline-lithium (Liq) was deposited by vapor deposition as an electron injection layer (EIL, Finally, metallic aluminum is vapor-deposited as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device.

[0369] Example 2: The preparation method is the same as in Example 1, except that compound A-14 selected in this invention is used instead of compound A-41 selected in this invention in the light-emitting layer.

[0370] Comparative Example 1: The preparation method is the same as in Example 1, except that compound A-14 selected in this invention is used instead of compound A1-1 selected in this invention in the light-emitting layer.

[0371] Comparative Example 2: The preparation method was the same as in Example 1, except that compound A-41 and compound A1-1 were replaced with compound A-14 in the luminescent layer, and the weight ratio of A-14 and B-226 was adjusted to (58.2:38.8).

[0372] The detailed device layer structure and thickness are shown in Table 3 below. The layers used are made of multiple materials, obtained by doping different compounds in the specified weight ratios.

[0373] Table 3. Partial device structures of Examples 1 and 2 and Comparative Examples 1 and 2.

[0374]

[0375] The material structure used in the device is shown below:

[0376]

[0377] Table 4 lists the device performance of Examples 1 and 2 and Comparative Examples 1 and 2. The power efficiency PE is measured at a current density of 10 mA / cm². 2 The measurements were taken below. These data were recorded and shown in Table 4.

[0378] Table 4. Device data for Examples 1 and 2 and Comparative Examples 1 and 2

[0379]

[0380]

[0381] discuss:

[0382] As shown in Table 4, the only difference between Example 1 and Comparative Example 1 is whether the absolute value of the HOMO energy level difference between the two p-type compounds is greater than or equal to 0.05 eV. Compared with Comparative Example 1, the power efficiency of Example 1 is significantly improved by 15%. The above data indicates that the |HOMO energy level difference between the two p-type compounds is greater than or equal to 0.05 eV. 第一化合物 -HOMO 第二化合物 |=0.081eV satisfies|HOMO 第一化合物 -HOMO 第二化合物 | ≥0.05 eV HOMO energy level difference between two p-type compounds in Example 1 | HOMO 第一化合物 -HOMO 第二化合物 | = 0.021 eV does not satisfy | HOMO 第一化合物 -HOMO 第二化合物 It is truly remarkable that Comparative Example 1, with a power efficiency of ≥0.05 eV, achieved a further significant improvement on top of its already high power efficiency. The only difference between Example 1 and Comparative Example 2 is whether the emitting layer contains two P-type compounds. Compared to Comparative Example 2, Example 1 showed a substantial 14% improvement in power efficiency. These figures demonstrate that Example 1, with two P-type compounds, achieved a further significant improvement on top of the high power efficiency already achieved in Comparative Example 2, which only had one P-type compound, which is quite unexpected.

[0383] Example 2 modifies the first compound with a different structure based on Example 1, and the |HOMO of Example 2 is different. 第一化合物 -HOMO 第二化合物 |=0.06, Example 2 achieved a similar high power efficiency as Example 1. Compared with Comparative Example 1 and Comparative Example 2, the power efficiency of Example 2 was significantly improved by 12% and 11%, respectively. The above data once again demonstrates the unique advantages of the organic electroluminescent device of the present invention.

[0384] Comparative Example 1 replaces compound A-14 with compounds A-41 and A-14, based on Comparative Example 2. The absolute value of the HOMO energy level difference between compounds A-41 and A-14 is 0.021 eV. The power efficiency of Comparative Example 1 and Comparative Example 2 is comparable, without any further significant improvement. The above data further demonstrates the importance of the specific energy level relationship between the first and second compounds of this application.

[0385] In summary, organic electroluminescent devices in which the host material of the luminescent layer includes at least a first compound, a second compound, and a third compound, and the luminescent material includes at least one phosphorescent luminescent material, exhibit excellent device performance, such as significantly improved power efficiency. They hold great promise for commercial applications.

[0386] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the 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 substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

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 a host material and a light-emitting material, wherein the host material comprises at least a first compound, a second compound and a third compound; The first compound and the second compound have the same carrier transport performance, and the HOMO level of the first compound is HOMO. 第一化合物 The HOMO energy level of the second compound is HOMO. 第二化合物 , and |HOMO 第一化合物 -HOMO 第二化合物 |≥0.05eV; The third compound has different carrier transport properties from the first compound; The luminescent material comprises at least one phosphorescent luminescent material.

2. The organic electroluminescent device as described in claim 1, wherein the first compound is a P-type compound, the second compound is a P-type compound, and the third compound is an N-type compound.

3. The organic electroluminescent device as described in claim 1, wherein the HOMO energy level relationship between the first compound and the second compound satisfies: HOMO 第一化合物 <HOMO> 第二化合物 ; Preferably, HOMO 第二化合物 -HOMO 第一化合物 ≥0.06eV.

4. The organic electroluminescent device as described in claim 1, wherein the HOMO 第一化合物 ≤-5.34eV, HOMO 第二化合物 ≥-5.29eV.

5. The organic electroluminescent device according to claim 1, wherein the first compound and the second compound are aromatic amine compounds; Preferably, the first and second compounds further comprise at least one chemical group selected from the group consisting of: oxazole, thiazole, benzoxazole, benzothiazole, naphthoxazole, naphthothiazole, benzothiophene, benzimazole, benzofuran, dibenzothiophene, dibenzofuran, azadibenzothiophene, azadibenzofuran, dibenzoselenophene, benzene, pyridine, pyrimidine, fused-ring carbazole, indolocarbazole, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof; More preferably, the first and second compounds further comprise at least one chemical group selected from the group consisting of: benzoxazole, benzothiazole, benzimidazole, naphthoxazole, and naphthothiazole.

6. The organic electroluminescent device of claim 1, wherein the third compound is an N-type compound, and the LUMO level of the third compound is LUMO. 第三化合物 , and LUMO 第三化合物 ≥-3.0eV; Preferably, the third compound is an N-type compound, and LUMO 第三化合物 ≥-2.9eV.

7. The organic electroluminescent device of claim 1, wherein the third compound is a triazine compound.

8. The organic electroluminescent device of claim 1, wherein the first compound has a structure represented by Formula 1: in, G2 is selected from O or S; G1 is selected from O, S, Se, CR1R2, SiR3R4, or NR. n ; X1 to X4 are selected from CR each time they appear, either identically or differently. x Or N; Y1 to Y3 are selected from CR each time they appear, either in the same or different ways. y Or N; Y4 through Y7 are selected from C, CR each time they appear, either identically or differently. y Or N; one of Y4 to Y7 is selected from C and connected to L1; L1 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar1 and Ar2, each time appearing, are selected from the same or different aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), cycloalkyl groups having 3-20 cyclic carbon atoms (substituted or unsubstituted), or combinations thereof. R x R y R n R”1, R”2, R”3, and R”4, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The following are substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms. Adjacent substituent R x They can be arbitrarily connected to form a loop; Adjacent substituent R y They can be arbitrarily connected to form a ring.

9. The organic electroluminescent device of claim 1, wherein the second compound has a structure represented by formula 2: in, Z is selected from NR' n O or S; Ar 21 To Ar 23 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5; If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L; L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; R w , R' n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R w They can be connected arbitrarily to form a loop.

10. The organic electroluminescent device of claim 1, wherein the maximum emission wavelength of the phosphorescent material is greater than or equal to 400 nm and less than or equal to 800 nm; Preferably, the maximum emission wavelength of the phosphorescent material is greater than or equal to 450 nm and less than or equal to 700 nm; More preferably, the maximum emission wavelength of the phosphorescent material is greater than or equal to 580 nm and less than or equal to 650 nm.

11. An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 10.

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