Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure as shown in a formula 1, can be used as a host material in an organic electroluminescent device, and can provide better device performance, such as higher efficiency, especially unexpected life prolonging. Also disclosed are an organic electroluminescent device, a compound composition, and an electronic device comprising the compound.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a compound having a structure of Formula 1, and an organic electroluminescent device, a compound composition, and an electronic device containing the compound. Background Art

[0002] Organic electronic devices include, but are not limited to, the following categories: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmonic light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be categorized based on the form of the materials used, as small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

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

[0007] The luminescent color of OLEDs can be achieved through the structural design of luminescent materials. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life, and high operating voltage. Commercial full-color OLED displays generally adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which remains a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency, and longer device life.

[0008] KR1020150077220A discloses an organic electroluminescent compound having the following structure: The disclosed general formula compound X1 may be N(Ar1), but it does not disclose or teach the organic compounds formed by connecting indole-fused nitrogen macrocyclic structural units with fused ring thiazole and similar structural units and their unique advantages.

[0009] However, the main materials reported so far still have room for improvement. In order to meet the industry's increasing demands, especially the demand for high device efficiency and longer device life performance, new materials still need further research and development. Summary of the Invention

[0010] The present invention aims to provide a series of compounds having a structure having a specific indole-pyrrole-fused aza-macrocyclic structure and a specific fused thiazole (oxazole) structure connected by L, forming a structure having Formula 1, to address at least some of the above-mentioned problems. These compounds can be used as host materials in organic electroluminescent devices. These novel compounds can provide improved device performance.

[0011] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0012]

[0013] in,

[0014] A1, A2 and A3 are each selected from N or CR, the same or different at each occurrence; Ring A, Ring B and Ring C are each selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 18 carbon atoms, the same or different at each occurrence; Ring D is selected from a fused heteroaromatic ring having 8 to 30 carbon atoms or a fused aromatic ring having 10 to 30 carbon atoms;

[0015] R x , R t Each occurrence of the same or different means mono-, poly- or no-substitution;

[0016] Z is O or S;

[0017] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0018] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0019] R, R t and R xEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0020] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0021] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer arranged between the anode and the cathode, wherein the organic layer contains a compound having the structure of Formula 1, and the specific structure of the compound is shown in the aforementioned embodiment.

[0022] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the compound having the structure of Formula 1. The specific structure of the compound is shown in the aforementioned embodiment.

[0023] According to another embodiment of the present invention, an electronic device is disclosed, which includes an organic electroluminescent device. The specific structure of the organic electroluminescent device is as shown in the above embodiment.

[0024] The novel compounds having the structure of Formula 1 disclosed in the present invention can be used as host materials in electroluminescent devices. These novel compounds can provide better device performance, higher efficiency, and especially unexpectedly improved lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0026] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0027] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0028] There are many more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0029] The above layered structures are provided by way of non-limiting examples. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.

[0030] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0031] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1 The difference is that an encapsulation layer 102 can also be included above cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0032] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0033] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0034] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.

[0035] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0036] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.

[0037] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0038] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap so as to convert between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.

[0039] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0040] Definition of Substituent Terms

[0041] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0042] Alkyl - as used herein, includes straight chain and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0043] Cycloalkyl - as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0044] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbon atoms in the alkyl chain substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl can be optionally substituted.

[0045] Alkenyl - as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, alkenyl groups can be optionally substituted.

[0046] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl groups can be optionally substituted.

[0047] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

[0048] Heterocyclic group or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothiol. Additionally, heterocyclyl groups may be optionally substituted.

[0049] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain from 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group may have from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, and more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0050] Alkoxy - as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

[0051] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenyloxy. In addition, the aryloxy group may be optionally substituted.

[0052] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,

[0053] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0054] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0055] Alkylgermanyl - As used herein, alkyl-substituted germanium groups are encompassed. The alkylgermanyl group can be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyl-tert-butylgermanyl, and methyldi-tert-butylgermanyl. Additionally, the alkylgermanyl group can be optionally substituted.

[0056] Arylgermanyl - As used herein, encompasses germanium groups substituted with at least one aryl or heteroaryl group. The arylgermanyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyltert-butylgermanyl. Additionally, the arylgermanyl group may be optionally substituted.

[0057] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., means that one or more CH groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.

[0058] In the present disclosure, unless otherwise defined, when any one term in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, Substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups refer to any one of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylgermanyl groups, arylgermanyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups and phosphino groups, which may be substituted by one or more of deuterium, halogen groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 ring carbon atoms, unsubstituted heterocyclyl groups having 3 to 20 ring carbon atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms , unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0059] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.

[0060] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in compounds may be preferred because it enhances device efficiency and stability.

[0061] In the compounds described herein, polysubstitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0062] In the compounds mentioned in the present disclosure, unless clearly defined, such as adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including the situation where adjacent substituents can be connected to form a ring, and also including the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0063] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0064]

[0065] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other via a chemical bond to form a ring, as can be exemplified by the following formula:

[0066]

[0067] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to further distant carbon atoms are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0068]

[0069] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0070]

[0071] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0072]

[0073] in,

[0074] A1, A2 and A3 are each selected from N or CR, the same or different at each occurrence; Ring A, Ring B and Ring C are each selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 18 carbon atoms, the same or different at each occurrence; Ring D is selected from a fused heteroaromatic ring having 8 to 30 carbon atoms or a fused aromatic ring having 10 to 30 carbon atoms;

[0075] R x , R t Each occurrence of the same or different means mono-, poly- or no-substitution;

[0076] Z is O or S;

[0077] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0078] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0079] R, R t and R xEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0080] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0081] Herein, "ring D is selected from a fused heteroaromatic ring having 8 to 30 carbon atoms, or a fused aromatic ring having 10 to 30 carbon atoms" is intended to mean that ring D itself is a fused aromatic ring formed by fusion of two or more monocyclic aromatic rings, a fused heteroaromatic ring formed by fusion of two or more monocyclic aromatic rings and at least one monocyclic heteroaromatic ring, or a fused heteroaromatic ring formed by fusion of two or more monocyclic heteroaromatic rings. For example, naphthyl is a fused aromatic ring formed by fusion of two benzene rings, phenanthrenyl is a fused aromatic ring formed by fusion of three phenyl rings, and isoquinolinyl is a fused heteroaromatic ring formed by fusion of a benzene ring and a pyridine ring.

[0082] In this context, adjacent substituents R, R t , R x can be optionally linked to form a ring, which is intended to indicate that adjacent substituent groups, for example, between adjacent substituents R, adjacent substituents R t Between adjacent substituents R x Between adjacent substituents R x and R t Between, and between adjacent substituents R and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0083] In this embodiment, when Ar is selected from substituted aryl, substituted heteroaryl, the aryl, heteroaryl is replaced by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0084] When L is selected from a single bond, a substituted arylene group, or a substituted heteroarylene group, the arylene group or the heteroarylene group is replaced by one or more selected from deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, The group consisting of an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, an unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group and a combination thereof.

[0085] When the R twherein each occurrence is identically or differently selected from substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl or substituted phosphino, means that alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino are replaced by one or more radicals selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted alkyl having 3 to 20 ring carbon atoms cycloalkyl, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0086] According to one embodiment of the present invention, wherein the ring A, ring B and ring C are identically or differently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms each time they appear.

[0087] According to one embodiment of the present invention, the ring A, ring B and ring C are selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring, the same or different when each occurs.

[0088] According to one embodiment of the present invention, the ring D is selected from a fused heteroaromatic ring having 8 to 20 carbon atoms, or a fused aromatic ring having 10 to 20 carbon atoms.

[0089] According to one embodiment of the present invention, the ring D is selected from a naphthalene ring, a naphthalene aza ring, a phenanthrene ... aza ring, an anthracene ring, and an azaanthracene ring.

[0090] According to one embodiment of the present invention, the compound has a structure represented by any one of Formulas 1-a to 1-d:

[0091]

[0092] wherein A1 to A3 are each selected from N or CR, the same or different at each occurrence, and X1 to X 10 Each occurrence is the same or different selection from N or CR x ;

[0093] Z is O or S;

[0094] Each occurrence of T1 to T8 is identically or differently selected from C, CR t or N;

[0095] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0096] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0097] R, R t and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0098] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0099] According to one embodiment of the present invention, the compound has a structure represented by Formula 1-a, 1-b or 1-c.

[0100] According to one embodiment of the present invention, A1 to A3 are selected from CR the same or differently each time they appear, X1 to X 10 Each occurrence is the same or different selection from CR x , T to T each time it appears, select CR the same or different t .

[0101] According to one embodiment of the present invention, one of T1 to T4 is selected from C.

[0102] According to one embodiment of the present invention, T2 or T3 is selected from C.

[0103] According to one embodiment of the present invention, R, R t and R x each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;

[0104] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0105] According to one embodiment of the present invention, R, R t and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof;

[0106] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0107] According to one embodiment of the present invention, R, R t and R xwherein at least one of the following is selected from deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;

[0108] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0109] According to one embodiment of the present invention, R, R t and R x At least one of the following is selected from deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, or a combination thereof;

[0110] Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

[0111] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0112] According to one embodiment of the present invention, L is selected from a single bond, a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a trimphenylene group, or a combination thereof.

[0113] According to one embodiment of the present invention, wherein L is selected from a single bond.

[0114] According to one embodiment of the present invention, Ar is selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

[0115] According to one embodiment of the present invention, wherein Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, triphenylene, phenanthrenyl, dibenzoselenophene, silanyl, 1-Hydroxy-1-Methyl-1-piperidinyl, ...

[0116] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-362, wherein the specific structures of Compound A-1 to Compound A-362 are shown in Claim 10.

[0117] According to one embodiment of the present invention, the hydrogen in the structures of Compounds A-1 to A-362 can be partially or completely replaced by deuterium.

[0118] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising:

[0119] anode,

[0120] cathode,

[0121] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula 1, and the specific structure of the compound is as described in any of the aforementioned embodiments.

[0122] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, a hole transport layer or an electron blocking layer.

[0123] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the compound is a host material.

[0124] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, the light-emitting layer contains a second compound, and the second compound is a host material.

[0125] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, the light-emitting layer contains a second compound, the second compound is a host material, and the second compound has a structure represented by Formula 2:

[0126]

[0127] In formula 2,

[0128] L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0129] Ar 21 to Ar 23 Each occurrence is identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or a combination thereof.

[0130] According to one embodiment of the present invention, the second compound has a structure shown in Formula 2-1:

[0131]

[0132] Each occurrence of V1-V6 is identically or differently selected from C, N or CR v , and one of V1-V6 is C and connected to L 23 connected;

[0133] L1 to L3 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0134] Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0135] R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkene having 2 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0136] Adjacent substituent R v Can optionally be linked to form a ring.

[0137] In this context, adjacent substituents R v can be optionally linked to form a ring, which is intended to indicate that any adjacent substituent Rv Obviously, any adjacent substituents R v They can also not be connected to form a ring.

[0138] According to one embodiment of the present invention, the second compound has a structure shown in Formula 2-1-1 or Formula 2-1-2:

[0139]

[0140] Wherein in formula 2-1-1, V1-V5 are selected from C, N or CR at each occurrence, the same or different v , V 11 -V 15 Each occurrence is the same or different selection from N or CR v1 , and one of V1-V5 is C and is connected to L 23 Connected; In formula 2-1-2, V1-V4 are selected from C, N or CR each time they appear, the same or different v , V 11 -V 14 Each occurrence is the same or different selection from N or CR v1 , and one of V1-V4 is C and connected to L 23 connected;

[0141] V is selected from O, S or Se;

[0142] L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0143] Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0144] R v , R v1Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkene having 2 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0145] Adjacent substituent R v , R v1 Can optionally be linked to form a ring.

[0146] In this context, adjacent substituents R v , R v1 can be optionally linked to form a ring, which is intended to indicate adjacent groups of substituents, for example, adjacent substituents R v Between adjacent substituents R v1 Between, and adjacent substituents R v and R v1 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0147] According to one embodiment of the present invention, in Formula 2-1-2, V is selected from O or S.

[0148] According to one embodiment, in Formula 2-1-2, V is O.

[0149] According to one embodiment of the present invention, in Formula 2-1-1, V1 to V5 are selected from C or CR the same or differently each time they appear. v , V 11 To V 15 Each occurrence is the same or different selection from CR v1 In formula 2-1-2, V1 to V4 are selected from C or CR at each occurrence, either identically or differently. v , V11 To V 14 Each occurrence is the same or different selection from CR v1 .

[0150] According to one embodiment of the present invention, wherein said R v , R v1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0151] According to one embodiment of the present invention, in Formula 2-1-1, at least one of V1 to V5 is selected from CR v , or V 11 To V 15 At least one of CR v1 In formula 2-1-2, at least one of V1 to V4 is selected from CR v , or V 11 To V 14 At least one of CR v1 ; and said R v , R v1 and are selected, identically or differently on each occurrence, from substituted or unsubstituted aryl radicals having 6 to 30 carbon atoms.

[0152] According to one embodiment of the present invention, wherein the R v , R v1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0153] According to one embodiment of the present invention, wherein the Ar 21 and Ar 22 At least one of them has a structure of two condensed rings or three condensed rings.

[0154] According to one embodiment of the present invention, wherein Ar 21 and Ar 22 Each occurrence is identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, or a combination thereof.

[0155] According to one embodiment of the present invention, wherein Ar 21 and Ar 22is selected, at each occurrence, identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted indolocarbazolyl, or a combination thereof.

[0156] According to one embodiment of the present invention, L 21 To L 23 Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

[0157] According to one embodiment of the present invention, L 21 To L 23 Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.

[0158] According to one embodiment of the present invention, the second compound is selected from the group consisting of Compound B-1 to Compound B-255, wherein the specific structures of Compound B-1 to Compound B-255 are described in claim 13.

[0159] According to one embodiment of the present invention, the hydrogen in the structures of Compounds B-1 to B-255 can be partially or completely replaced by deuterium.

[0160] According to one embodiment of the present invention, in the preparation of a device, when the compound of the present invention and the second compound are co-evaporated with a light-emitting material to form a light-emitting layer, the light-emitting layer can be formed by placing the compound of the present invention, the second compound and the light-emitting material in different evaporation sources for co-evaporation. Alternatively, a pre-mixed mixture of the compound of the present invention and the second compound can be placed in the same evaporation source and then co-evaporated with the light-emitting material placed in another evaporation source to form a light-emitting layer. This pre-mixing method can further save evaporation sources.

[0161] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer contains at least one phosphorescent material.

[0162] According to one embodiment of the present invention, the phosphorescent material is a metal complex having M(L a) m (L b ) n (L c ) q The general formula of

[0163] M is selected from metals with a relative atomic mass greater than 40;

[0164] L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the M respectively; L a , L b and L c can optionally be linked to form multidentate ligands;

[0165] L a , L b and L c The 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, q is equal to 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;

[0166] L a Each occurrence is identical or different and is selected from the structure shown in Formula 3:

[0167]

[0168] in,

[0169] Ring F is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0170] Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0171] Ring F and Ring E via U a and U b condensed;

[0172] U a and U b Each occurrence is identically or differently selected from C or N;

[0173] R d and R e Each occurrence of the same or different means mono-, poly- or no-substitution;

[0174] V 31 To V 34 Each occurrence is the same or different selection from CR v3or N;

[0175] R d , R e and R v3 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkene having 2 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0176] Adjacent substituent R d , R e and R v3 can optionally be linked to form a ring;

[0177] L b and L c Each occurrence is identical or different and is selected from any one of the following structures:

[0178]

[0179]

[0180] in,

[0181] R a , R b and R c Each occurrence is identical or different and represents mono-, poly-, or unsubstituted;

[0182] X b Each occurrence is identical or different and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0183] X c and Xd Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0184] R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0185] The ligand L b , L c In the structure of a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

[0186] In this context, adjacent substituents R d , R e , R v3 can be optionally linked to form a ring, which is intended to indicate that when a substituent R d , substituent R e , substituent R v3 When adjacent substituent groups, such as adjacent substituents R d Between and adjacent substituents R eBetween and adjacent substituents R v3 Between and adjacent substituents R d With R e Between and adjacent substituents R d With R v3 Between and adjacent substituents R e With R v3 Between, any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when there is a substituent R d , substituent R e , substituent R v3 When , these substituent groups may not be linked to form a ring.

[0187] In this context, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be linked to form a ring. For example, The adjacent substituent R a , R bCan optionally be linked to form rings, which may form one or more of the following structures including but not limited to:

[0188] Wherein, W is selected from O, S, Se, NR w1 or CR w1 R w1 wherein said R w1 , R a ', R b 'The definition of R a Obviously, these substituents may not be connected to form a ring.

[0189] According to one embodiment of the present invention, in Formula 3, two adjacent substituents R e Connect to form a ring.

[0190] According to one embodiment of the present invention, in Formula 3, two adjacent substituents R e They are connected to form a 5-membered unsaturated carbon ring, a 5-membered heteroaromatic ring or a benzene ring.

[0191] According to one embodiment of the present invention, in Formula 3, ring F is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring.

[0192] According to one embodiment of the present invention, in Formula 3, ring F is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.

[0193] According to one embodiment of the present invention, in Formula 3, ring F is a 6-membered heteroaromatic ring, ring E is a benzene ring or a 6-membered heteroaromatic ring, and two adjacent substituents R e Connect to form a benzene ring or a 6-membered heteroaromatic ring.

[0194] According to one embodiment of the present invention, in Formula 3, Ring F is a 6-membered heteroaromatic ring, Ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring, and the two adjacent substituents R e Connect to form a benzene ring or a 6-membered heteroaromatic ring.

[0195] According to one embodiment of the present invention, in Formula 3, R d , R e , R v3 At least one or two groups of adjacent substituents are connected to form a ring. For example, two substituents R d Connected to form a ring, or two substituents R e Connected to form a ring, or two substituents R v3 Connected to form a ring, or substituent R d With substituent R eConnected to form a ring, or substituent R d With substituent R v3 Connected to form a ring, or substituent R e With substituent R v3 Connected to form a ring, or two substituents R d When two substituents R are connected to form a ring e Connected to form a ring, or two substituents R d When two substituents R are connected to form a ring v3 Connected to form a ring, or two substituents R e When two substituents R are connected to form a ring v3 Connected to form a ring, substituent R e With substituent R v3 When two substituents R are connected to form a ring v3 Connected to form a ring, or substituent R d With substituent R v3 When two substituents R are connected to form a ring v3 Connect to form a ring; R d 、R e 、R v3 A similar situation occurs when more groups of adjacent substituents are connected to form a ring.

[0196] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is a metal complex having M(L a ) m (L b ) n The general formula of

[0197] M is selected from metals with a relative atomic mass greater than 40;

[0198] L a , L b are the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally be linked to form multidentate ligands;

[0199] m is 1, 2 or 3; n is 0, 1 or 2; the sum of m and n is equal to the oxidation state of M; when m is greater than or equal to 2, multiple L a Can be the same or different; when n is 2, the two L b Can be the same or different;

[0200] L a Each occurrence is identical or different and is selected from the structure shown in Formula 3:

[0201]

[0202] in,

[0203] Ring F is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0204] Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0205] Ring F and Ring E via U a and U b condensed;

[0206] U a and U b Each occurrence is identically or differently selected from C or N;

[0207] R d and R e Each occurrence of the same or different means mono-, poly- or no-substitution;

[0208] V 31 To V 34 Each occurrence is the same or different selection from CR v3 or N;

[0209] R d , R e and R v3 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkene having 2 to 20 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0210] Adjacent substituent R d , R e and R v3 can optionally be linked to form a ring;

[0211] wherein the ligand L b Each occurrence is identically or differently selected from the following structures:

[0212]

[0213] wherein R1 to R7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0214] According to one embodiment of the present invention, in the organic electroluminescent device, the ligand L b Each occurrence is identically or differently selected from the following structures:

[0215]

[0216] wherein at least one of R1 to R3 is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and / or at least one of R4 to R6 is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0217] According to one embodiment of the present invention, in the organic electroluminescent device, the ligand L b Each occurrence is identically or differently selected from the following structures:

[0218]

[0219] wherein at least two of R1 to R3 are, at each occurrence, identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or a combination thereof; and / or at least two of R4 to R6 are, at each occurrence, identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or a combination thereof.

[0220] According to one embodiment of the present invention, in the organic electroluminescent device, the ligand L b Each occurrence is identically or differently selected from the following structures:

[0221]

[0222] wherein at least two of R1 to R3 are, at each occurrence, identically or differently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof; and / or at least two of R4 to R6 are, at each occurrence, identically or differently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof.

[0223] 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.

[0224] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex having Ir(L 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 structure shown in 2.

[0225] According to one embodiment of the present invention, wherein L aThe compound has a structure as shown in Formula 3 and comprises at least one structural unit selected from the group consisting of a 6-membered and 6-membered aromatic ring, a 6-membered and 6-membered heteroaromatic ring, a 6-membered and 5-membered aromatic ring and a 6-membered and 5-membered heteroaromatic ring.

[0226] According to one embodiment of the present invention, in the organic electroluminescent device, L a The compound has a structure as shown in Formula 3 and includes at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0227] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a Each occurrence is identical or different and is selected from any one of the following structures:

[0228]

[0229]

[0230]

[0231] In the structure, TMS represents trimethylsilyl.

[0232] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L b , the L b Each occurrence is identical or different and is selected from any one of the following structures:

[0233]

[0234] 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:

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] In the structures, TMS represents trimethylsilyl.

[0244] According to another embodiment of the present invention, a compound composition is also disclosed, which includes a compound having a structure of Formula 1, and the specific structure of the compound is shown in any of the aforementioned embodiments.

[0245] According to one embodiment of the present invention, the compound composition comprises a second compound having a structure represented by Formula 2:

[0246]

[0247] In formula 2,

[0248] L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0249] Ar 21 to Ar 23 Each occurrence is identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or a combination thereof.

[0250] According to another embodiment of the present invention, an electronic device is disclosed, which includes an organic electroluminescent device. The specific structure of the organic electroluminescent device is as shown in any of the above embodiments.

[0251] Combination with other materials

[0252] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0253] The materials described herein as being useful in specific layers of an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0254] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kosite's electrochemical workstation, Anhui Beiyi Ke's sublimator, etc.), and is tested for structure confirmation and characteristics using methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical testing system, life test system, Beijing Liangtuo's ellipsometer, etc.), and are tested using methods well known to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, testing methods and other related content, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related content is no longer expanded in this patent.

[0255] Material synthesis example:

[0256] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0257] Synthesis Example 1: Synthesis of Compound A-1

[0258]

[0259] Under nitrogen, intermediate 1 (2 g, 6.05 mmol), intermediate 2 (2.06 g, 6.05 mmol), palladium acetate (67.95 mg, 0.3 mmol), S-phos (248.52 mg, 0.61 mmol), sodium tert-butoxide (1.16 g, 12.07 mmol), and xylene (40 mL) were added to a three-necked flask and reacted at 140°C overnight. After completion of the reaction, the mixture was cooled to room temperature and distilled water was added. The precipitated solid was filtered to obtain a crude product, which was recrystallized from toluene to obtain A-1 (1.5 g, 42% yield), a yellow solid. The product was confirmed to be the desired product with a molecular weight of 589.2.

[0260] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0261] Device Example 1

[0262] First, a glass substrate with a 120 nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were deposited at a vacuum of approximately 10-8 Torr. Compound HT and compound HI were co-evaporated to form a hole injection layer (HIL, weight ratio 97:3) with a thickness of Compound HT was used as the hole transport layer (HTL) with a thickness of Compound EB is used as electron blocking layer (EBL) with a thickness of Then, the compound A-1 of the present invention as the first host, the compound B-227 as the second host, and the compound RD as the dopant were co-evaporated to form an emitting layer (EML, weight ratio 39.2:58.8:2) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, weight ratio 40:60) with a thickness of Finally, evaporation Thickness of 8-hydroxyquinoline-lithium (Liq) as the electron injection layer (EIL), and evaporated The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

[0263] Device Comparative Example 1

[0264] The device of Comparative Example 1 was carried out in the same manner as in Example 1, except that Compound A was used as the first host in the emission layer (EML) instead of Compound A-1 of the present invention.

[0265] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.

[0266] Table 1 Partial device structures of device embodiments and comparative examples

[0267]

[0268] The material structure used in the device is shown below:

[0269]

[0270] Table 2 lists the 2 The maximum emission wavelength (λ max ), external quantum efficiency (EQE) and at 80mA / cm 2 The device lifespan (LT97) was tested under constant current. The device lifespan (LT97) refers to the time required for the device brightness to decay to 97% of its initial brightness.

[0271] Table 2 Device data

[0272] Device ID <![CDATA[λ max (nm)]]> EQE (%) LT97(h) Example 1 622 22.9 572.5 Comparative Example 1 622 21.3 140

[0273] discuss:

[0274] As can be seen from the data in Table 2, the maximum emission wavelength of device embodiment 1 and device comparative example 1 remains consistent; the main difference between device embodiment 1 and device comparative example 1 is that the fused ring connected to the specific indole and pyrrole fused nitrogen macrocyclic structural unit is different. In terms of external quantum efficiency (EQE), compared with comparative example 1, embodiment 1 is greatly improved by 7.5%. While the efficiency is significantly improved, the life span of embodiment 1 is unexpectedly greatly improved compared with comparative example 1, with an increase of 309%. The above data show that the compound with the structure of formula 1 of the present invention can make the hole transport in the device more stable, can better recombine with the electrons in the device, thereby significantly improving the life span of the device. It is proved that the compound of the present invention with the structure of formula 1 can be applied as a main material in an organic electroluminescent device to obtain higher efficiency, especially greatly improve the life span, can show more excellent performance, and has broad commercial development prospects and application value.

[0275] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. A compound having the structure of Formula 1: in, A1, A2 and A3 are each selected from N or CR, the same or different at each occurrence; Ring A, Ring B and Ring C are each selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 18 carbon atoms, the same or different at each occurrence; Ring D is selected from a fused heteroaromatic ring having 8 to 30 carbon atoms or a fused aromatic ring having 10 to 30 carbon atoms; R x , R t Each occurrence of the same or different means mono-, poly- or no-substitution; Z is O or S; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R, R t and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R, R t , R x Can optionally be linked to form a ring.

2. The compound according to claim 1, wherein the ring A, ring B and ring C are each identically or differently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms; Preferably, the ring A, ring B and ring C are identically or differently selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring at each occurrence.

3. The compound according to claim 1, wherein the ring D is selected from a fused heteroaromatic ring having 8 to 20 carbon atoms, or a fused aromatic ring having 10 to 20 carbon atoms; Preferably, the ring D is selected from a naphthalene ring, an azanaphthalene ring, a phenanthrene ring, an azaphenanthrene ring, an anthracene ring, and an azaanthracene ring.

4. The compound according to claim 1, wherein the compound has a structure represented by any one of Formula 1-a to Formula 1-d: in, A1 to A3 are each selected from N or CR, the same or different at each occurrence, X1 to X 10 Each occurrence is the same or different selection from N or CR x ; Z is O or S; Each occurrence of T1 to T8 is identically or differently selected from C, CR t or N; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R, R t and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R, R t , R x can optionally be linked to form a ring; Preferably, the compound has a structure represented by Formula 1-a, 1-b or 1-c.

5. The compound according to claim 4, wherein A1 to A3 are selected from CR at each occurrence, the same or different, X1 to X 10 Each occurrence is the same or different selection from CR x , T1 to T8 are each selected from C or CR, the same or different at each occurrence t ; Preferably, one of T1 to T4 is selected from C; More preferably, T2 or T3 is selected from C.

6. The compound according to claim 1 or 4, wherein R, R t and R x each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Adjacent substituents R, R t , R x can optionally be linked to form a ring; Preferably, R, R t and R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

7. The compound according to claim 1 or 4, wherein R, R t and R x wherein at least one of the following is selected from deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R, R t , R x can optionally be linked to form a ring; Preferably, R, R t and R x At least one of the following is selected from deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuterated methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl, phenylpyridyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, or a combination thereof.

8. The compound according to claim 1 or 4, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Preferably, L is selected from a single bond, phenylene, naphthylene, biphenylene, terphenylene, trimphenylene, or a combination thereof; More preferably, L is selected from a single bond.

9. The compound of claim 1 or 4, wherein Ar is selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Preferably, Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, triphenylene, phenanthrenyl, dibenzoselenophene, silanyl, 1-Hydroxy-1-Methyl-1-piperidinyl, ...

10. The compound of claim 1, wherein the compound is selected from the group consisting of: Optionally, hydrogen in the structures of Compound A-1 to Compound A-362 can be partially or completely replaced by deuterium.

11. An organic electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, wherein the organic layer is a light-emitting layer, a hole transport layer or an electron blocking layer; Preferably, the organic layer is a light-emitting layer, and the compound is a host material.

13. The organic electroluminescent device according to claim 12, wherein the organic layer is a light-emitting layer, and the organic layer further comprises a second compound, and the second compound is a host material; Preferably, the second compound has a structure represented by Formula 2: In formula 2, L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 21 to Ar 23 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; More preferably, wherein the second compound is selected from the group consisting of: Optionally, hydrogen in the structures of Compound B-1 to Compound B-255 can be partially or completely replaced by deuterium. 14 . The organic electroluminescent device according to claim 11 , wherein the organic layer is a light-emitting layer, and the light-emitting layer comprises at least one phosphorescent light-emitting material.

15. The organic electroluminescent device according to claim 14, wherein the phosphorescent material is a metal complex having M(L a ) m (L b ) n (L c ) q The general formula of M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are respectively the first ligand, the second ligand and the third ligand coordinated with the M; L a , L b and L c can optionally be linked to form multidentate ligands; L a , L b and L c can be the 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, q is equal to the oxidation state of M; when m is greater than or equal to 2, multiple L a Can be the same or different; when n is 2, the two L b Can be the same or different; when q is 2, the two L c Can be the same or different; L a Each occurrence is identical or different and is selected from the structure shown in Formula 3: in, Ring F is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; Ring F and Ring E via U a and U b condensed; U a and U b Each occurrence is identically or differently selected from C or N; R d and R e Each occurrence of the same or different means mono-, poly- or no-substitution; V 31 To V 34 Each occurrence is the same or different selection from CR v3 or N; R d , R e and R v3 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R d , R e and R v3 can optionally be linked to form a ring; L b and L c Each occurrence is identical or different and is selected from any one of the following structures: in, R a , R b and R c Each occurrence is identical or different and represents mono-, poly-, or unsubstituted; X b Each occurrence is identical or different and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

16. A compound composition comprising the compound according to any one of claims 1 to 10. 17 . An electronic device comprising the organic electroluminescent device according to claim 11 .

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