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 shown in a formula 1, and the compound can be used as an electron blocking material in an organic electroluminescent device. According to the compound, the voltage of the organic electroluminescent device can be greatly reduced, the efficiency of the device can be greatly improved, and better comprehensive performance of the device can be provided. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic electroluminescent devices, and more particularly to a compound having a structure of Formula 1, an organic electroluminescent device comprising the compound, and a compound composition comprising 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 photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.

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

[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

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

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

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

[0008] The present invention aims to provide a series of novel compounds having a structure of Formula 1 containing a fluorene or silafluorene spiro N-hetero seven-membered ring structure and an aromatic amine unit connected to the fluorene or silafluorene to solve at least part of the above problems. The compounds can be used in organic electroluminescent devices, for example, as electron blocking materials, etc. These novel compounds can be used in organic electroluminescent devices to significantly reduce device voltage, significantly improve device efficiency, and provide better device comprehensive performance.

[0009] According to one embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0010]

[0011] In formula 1,

[0012] n is an integer selected from 1 to 3;

[0013] X 1 To X 8 Each occurrence is selected from C, CR, either identically or differently x or N; and X 1 To X 8 n of them are selected from C and are respectively connected with L 0 connect;

[0014] Y 1 To Y 13 Each occurrence is selected from CR y or N;

[0015] Q is selected from C or Si;

[0016] L 0 , L 1 , L 2 is identically or differently selected at each occurrence 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;

[0017] Ar 1 and Ar 2 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;

[0018] R x , R yThe 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;

[0019] Adjacent substituent R x , R y Can optionally be linked to form a ring.

[0020] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound described in the above embodiment.

[0021] According to another embodiment of the present invention, a compound composition is also disclosed, wherein the compound composition comprises the compound described in the aforementioned embodiment.

[0022] The present invention discloses a series of compounds having a structure of Formula 1, which contain a fluorene or silafluorene spiro N-hetero seven-membered ring structure and an aromatic amine unit connected to the fluorene or silafluorene. The compounds can be used in organic electroluminescent devices, for example, as electron blocking materials, and can improve the performance of organic electroluminescent devices, for example, greatly reduce the device voltage, significantly improve the device efficiency, and improve the overall performance of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0024] Figure 2 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0025] 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.

[0026] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is one doped with F at a molar ratio of 50:1. 4

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0027] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0028] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0029] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0030] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0031] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0032] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0033] 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.

[0034] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0035] 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).

[0036] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0037] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0038] Definition of Substituent Terms

[0039] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0040] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0041] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0042] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.

[0043] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0044] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.

[0045] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.

[0046] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0047] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0048] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0049] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0050] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0051] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0052] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0053] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.

[0054] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.

[0055] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0056] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any one of which may be selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted cycloalkyl having 6-30 carbon atoms, unsubstituted cycloalkyl having 2-2 ... Aryl, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0057] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0058] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0059] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0060] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0061] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0062]

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

[0064]

[0065] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0066]

[0067] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0068]

[0069] According to one embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0070]

[0071] In formula 1,

[0072] n is an integer selected from 1 to 3;

[0073] X 1 To X 8 Each occurrence is selected from C, CR, either identically or differently x or N; and X 1 To X 8 n of them are selected from C and are respectively connected with L 0 connect;

[0074] Y 1 To Y 13 Each occurrence is the same or different selection from CR y or N;

[0075] Q is selected from C or Si;

[0076] L 0 , L 1 , L 2 is identically or differently selected at each occurrence 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;

[0077] Ar 1 and Ar 2 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;

[0078] R x , R yThe 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;

[0079] Adjacent substituent R x , R y Can optionally be linked to form a ring.

[0080] In this context, “the adjacent substituent R x , R y "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two adjacent substituents R x Between two adjacent substituents R y 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.

[0081] According to one embodiment of the present invention, n is selected from 1 or 2.

[0082] According to one embodiment of the present invention, n is selected from 1.

[0083] According to one embodiment of the present invention, the compound has a structure represented by Formula 2 or Formula 3:

[0084]

[0085] X 1 To X 8 Each occurrence is selected from C, CR, either identically or differently x or N; in formula 2, X 1 To X 8One of them is selected from C and combined with L 0 Connection; In formula 3, X 1 To X 4 One of them is selected from C and combined with L 0 Connect, X 5 To X 8 One of them is selected from C and combined with L 0 connect;

[0086] Y 1 To Y 13 Each occurrence is the same or different selection from CR y or N;

[0087] Q, at each occurrence, is selected from C or Si;

[0088] L 0 , L 1 , L 2 is identically or differently selected at each occurrence 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;

[0089] Ar 1 and Ar 2 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;

[0090] R x , R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an 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;

[0091] Adjacent substituent R x , R y Can optionally be linked to form a ring.

[0092] According to one embodiment of the present invention, the compound has a structure represented by any one of Formula 2-1 to Formula 2-3:

[0093]

[0094] X 1 To X 8 Each occurrence is the same or different selection from CR x or N;

[0095] Y 1 To Y 13 Each occurrence is the same or different selection from CR y or N;

[0096] Q is selected from C or Si;

[0097] L 0 , L 1 and L 2 is identically or differently selected at each occurrence 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;

[0098] Ar 1 and Ar 2 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;

[0099] R x , R yThe alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an 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;

[0100] Adjacent substituent R x , R y Can optionally be linked to form a ring.

[0101] According to one embodiment of the present invention, the compound has a structure represented by Formula 2-2 or Formula 2-3.

[0102] According to one embodiment of the present invention, the compound has a structure represented by Formula 2-3.

[0103] According to one embodiment of the present invention, wherein the L 0 , L 1 and L 2 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.

[0104] According to one embodiment of the present invention, wherein the L 0 , L 1 and L 2Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenopheneylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, or a combination thereof.

[0105] According to one embodiment of the present invention, wherein the L 0 , L 1 and L 2 is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0106] According to one embodiment of the present invention, wherein the L 0 , L 1 and L 2 All are selected from single bonds.

[0107] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or a combination thereof.

[0108] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is identically or differently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or a combination thereof.

[0109] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is identically or differently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, or a combination thereof.

[0110] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 At least one of has a structure represented by Formula 1-a or Formula 1-b:

[0111]

[0112] In Formula 1-a or Formula 1-b, Q 1 Each occurrence is selected from C or Si;

[0113] Z is selected from C, CR, or z or N;

[0114] L 3 is identically or differently selected at each occurrence 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;

[0115] R z , R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0116] Adjacent substituent R z , R' can be optionally linked to form a ring;

[0117] Indicates that the formula 1-a or formula 1-b and L in formula 1 1 or L 2 The location of the connection.

[0118] In this embodiment, “the adjacent substituent R z , R' can optionally be linked to form a ring", is intended to mean that adjacent groups of substituents, for example, two adjacent substituents R z Between two adjacent substituents R', any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0119] According to one embodiment of the present invention, wherein the R x , R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an 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.

[0120] According to one embodiment of the present invention, wherein the R x , R y Neither contain substituted or unsubstituted amino groups.

[0121] According to one embodiment of the present invention, wherein the R x , R yEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0122] According to one embodiment of the present invention, wherein the R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0123] According to one embodiment of the present invention, wherein the R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and combinations thereof.

[0124] According to one embodiment of the present invention, wherein Q is selected from C.

[0125] According to one embodiment of the present invention, wherein Q is selected from Si.

[0126] According to one embodiment of the present invention, wherein the Q 1 Selected from C.

[0127] According to one embodiment of the present invention, the compound is selected from the group consisting of compound H1 to compound H486, and the specific structures of compound H1 to compound H489 are shown in claim 9.

[0128] According to one embodiment of the present invention, hydrogen in the structures of compounds H1 to H486 can be partially or completely replaced by deuterium.

[0129] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound described in any one of the aforementioned embodiments.

[0130] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is an electron blocking layer or a hole transport layer.

[0131] According to one embodiment of the present invention, the organic layer is an electron blocking layer, and the compound is an electron blocking material.

[0132] According to an embodiment of the present invention, the organic electroluminescent device comprises a light-emitting layer, and the light-emitting layer comprises at least one phosphorescent material.

[0133] 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

[0134] Wherein, the metal M is selected from metals with a relative atomic mass greater than 40;

[0135] L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the metal M, respectively, a , L b , L c Can be the same or different;

[0136] L a , L b and L c can optionally be linked to form a multidentate ligand;

[0137] 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 metal 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;

[0138] Ligand L a It has a structure as shown in Formula 4:

[0139]

[0140] in,

[0141] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0142] Ring F is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0143] Ring D and Ring F via U a and U b condense;

[0144] U a and U b is selected identically or differently at each occurrence from C or N;

[0145] R d , R f Each occurrence of the same or different means mono-, poly- or no-substitution;

[0146] U 1 -U 4 Each occurrence is the same or different selection from CR u or N;

[0147] R d , R f , R u The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, 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;

[0148] Adjacent substituent R d , R f , R u can optionally be linked to form a ring;

[0149] Ligand L b, L c Each occurrence is identically or differently selected from the group consisting of:

[0150]

[0151] in,

[0152] R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0153] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0154] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0155] R a , R b , R c , R N1 , R N2 , R C1 and R C2 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0156] Adjacent substituent Ra , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

[0157] In this context, adjacent substituents R d , R f , R u can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R d , Substituent R f , Substituent R u When adjacent substituent groups, such as adjacent substituents R d Between and adjacent substituents R f Between and adjacent substituents R u Between and adjacent substituents R d With R f Between and adjacent substituents R d With R u Between and adjacent substituents R f With R u Any one or more of these adjacent substituent groups can be linked to form a ring. d , Substituent R f , Substituent R u When the substituent groups are not linked to form a ring.

[0158] In this embodiment, the adjacent substituent 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 RC1 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 b Can be optionally linked to form a ring, which can form one or more of the following structures including but not limited to: Wherein W is selected from O, S, Se, NR w or CR w R w ; wherein said R w , R a ', R b ' is defined in the same way as R a Obviously, these substituents may not be connected to form a ring.

[0159] According to one embodiment of the present invention, in Formula 4, the two R f Connect into a ring.

[0160] According to one embodiment of the present invention, in Formula 4, the two R f Connected to form a 5-membered unsaturated carbocyclic ring, a 5-membered heteroaromatic ring or a 6-membered aromatic ring.

[0161] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, and ring F is a benzene ring or a 6-membered heteroaromatic ring.

[0162] According to one embodiment of the present invention, in Formula 4, ring D is a 6-membered heteroaromatic ring, and ring F is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.

[0163] According to one embodiment of the present invention, in Formula 4, Ring D is a 6-membered heteroaromatic ring, Ring F is a benzene ring or a 6-membered heteroaromatic ring, and two R f Connected to form a ring, connected to form a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0164] According to one embodiment of the present invention, in Formula 4, Ring D is a 6-membered heteroaromatic ring, Ring F is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring, and the two R fConnected to form a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0165] According to one embodiment of the present invention, in Formula 4, U 1 -U 4 At least two of the following are selected from CR u , and the two R u Connect into a ring.

[0166] According to one embodiment of the present invention, in Formula 4, U 3 and U 4 Selected from CR u , and the two R u Connect into a ring.

[0167] According to one embodiment of the present invention, in Formula 4, U 3 and U 4 Selected from CR v , and the two R u Connected to form a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0168] According to one embodiment of the present invention, in Formula 4, R d , R f , R u At least one or two groups of adjacent substituents are connected to form a ring. For example, two substituents R d Connect to form a ring, or two substituents R f Connect to form a ring, or two substituents R u Connect to form a ring, or substituent R d With substituent R f Connected to form a ring, or substituent R d With substituent R u Connected to form a ring, or substituent R f With substituent R u Connected to form a ring, or two substituents R d When two substituents R are connected to form a ring f Connect to form a ring, or two substituents R d When two substituents R are connected to form a ring u Connect to form a ring, or two substituents R f When two substituents R are connected to form a ring u Connect to form a ring, substituent R f With substituent R u When two substituents R are connected to form a ring u Connect to form a ring, or substituent R d With substituent R u When two substituents R are connected to form a ring u Connect to form a ring; Rd , R f , R u A similar situation occurs when more groups of adjacent substituents are connected to form a ring.

[0169] According to one embodiment of the present invention, the ligand L b Has the following structure:

[0170]

[0171] Among them, R Ⅰ To R Ⅶ each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted 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 cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted 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 cycloalkyl having 2 -20 carbon atoms, alkynyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkylsilyl groups, substituted or unsubstituted arylsilyl groups, substituted or unsubstituted alkylgermanyl groups, substituted or unsubstituted arylgermanyl groups, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, sulfenyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

[0172] According to one embodiment of the present invention, R Ⅰ -R Ⅲ At least one of them is selected from 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, or a combination thereof; and / or R Ⅳ -R Ⅵ At least one of them 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.

[0173] According to one embodiment of the present invention, R Ⅰ -R ⅢAt least two of them are selected from 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, or a combination thereof at each occurrence; and / or R Ⅳ -R Ⅵ At least two of the above are selected, at each occurrence, identically or differently, from 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, or a combination thereof.

[0174] According to one embodiment of the present invention, R Ⅰ -R Ⅲ At least two of them are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms, or a combination thereof at each occurrence; and / or R Ⅳ -R Ⅵ At least two of the above are selected, at each occurrence, identically or differently, from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms, or a combination thereof.

[0175] 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.

[0176] 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 ) 2 Any of the structures shown in .

[0177] According to one embodiment of the present invention, the ligand L aThe compound has a structure as shown in Formula 4 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.

[0178] According to one embodiment of the present invention, in the organic electroluminescent device, the ligand L a The compound has a structure as shown in Formula 4 and comprises at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0179] According to one embodiment of the present invention, in the electroluminescent device, the ligand L a Each occurrence is identically or differently selected from any one of the group consisting of:

[0180]

[0181]

[0182]

[0183] According to one embodiment of the present invention, in the electroluminescent device, the ligand L b Each occurrence is identically or differently selected from any one of the group consisting of:

[0184]

[0185] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] According to an embodiment of the present invention, the organic electroluminescent device is a stacked device.

[0197] According to one embodiment of the present invention, a compound composition is disclosed, comprising the compound described in any one of the aforementioned embodiments.

[0198] Combination with other materials

[0199] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0200] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent 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.

[0201] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0202] Material synthesis example:

[0203] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0204] Synthesis Example 1: Synthesis of Compound H60

[0205] Step 1: Synthesis of Intermediate A

[0206]

[0207] In a 2000 mL three-necked round-bottom flask, DMSO (dimethyl sulfoxide, 600 mL), intermediate S1 (10.0 g, 59.8 mmol), intermediate S2 (25.7 g, 90.0 mmol), anhydrous K 3 PO 4 (25.4 g, 120 mmol) and CuI (0.57 g, 3.0 mmol), [BFMO] (N1, N2-bis (furan-2-ylmethyl) oxalamide, 2.48 g, 10.0 mmol), N 2 The reaction mixture was heated to 110°C for 30 min and reacted for 48 h. The reaction was complete after TLC monitoring. The reaction mixture was cooled to room temperature, filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate A (17.7 g, yield 79%).

[0208] Step 2: Synthesis of Intermediate B

[0209]

[0210] Add intermediate A (14.3 g, 38.4 mmol) to a 100 mL three-necked round-bottom flask in sequence, add THF (400 mL) under nitrogen protection, cool to -75 ° C, add n-BuLi (17 mL, 2.5 M, 42.5 mmol) dropwise, react for 2 h, add a solution of intermediate S3 (10 g, 60.0 mmol) in THF (20 mL), and then slowly warm to room temperature. TLC monitors the reaction to be complete, wash the reaction solution with water, extract with DCM, filter, remove the solvent under reduced pressure, dissolve the resulting solid residue in DCM (600 mL), and add CF dropwise. 3 SO 3 H (0.5 mL), react at room temperature for 1 h, and complete the reaction after TLC monitoring. 3 The reaction solution was washed with aqueous solution, extracted with DCM, dried, filtered, concentrated under reduced pressure, and purified by column chromatography to obtain intermediate B (12.4 g, yield 60%).

[0211] Step 3: Synthesis of compound H60

[0212]

[0213] To a 250 mL three-necked round-bottom flask, toluene (110 mL), intermediate B (6.2 g, 11.6 mmol), intermediate S4 (4.5 g, 11.2 mmol) were added in sequence. t BuONa (2.62g, 28.0mmol), N 2 20min, add Pd(OAc) 2 (120 mg, 0.535 mmol) and t-Bu 3 PHB 4 (475 mg, 1.64 mmol), heated to 120 ° C for 24 h. TLC monitored the reaction to be complete. The reaction solution was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain a white solid compound H60 (3.5 g, yield 36%). The product was confirmed to be the target product with a molecular weight of 854.37.

[0214] 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.

[0215] The method for preparing the organic electroluminescent device is not limited, and the method for preparing the device embodiment described below is only an example and should not be construed as limiting. A person skilled in the art can reasonably improve the method for preparing the device embodiment described below based on the prior art.

[0216] Device Embodiment

[0217] Device Example 1: Preparation of an organic electroluminescent device

[0218] First, a 0.7 mm thick glass substrate with a pre-patterned The thick indium tin oxide (ITO) was used as the anode. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and loaded on a rack into a vacuum chamber. The organic layers specified below were placed in a vacuum of about 10 -6 Torr's case The anode layer was deposited sequentially by vacuum thermal evaporation at a rate of: first, compound HT-1 and compound HT-2 were simultaneously deposited as a hole injection layer (HIL, weight ratio 98:2, ), the evaporated compound HT-1 was used as a hole transport layer (HTL, ), the compound H60 of the present invention is evaporated to serve as an electron blocking layer (EBL, ), and then simultaneously evaporate compound RH and compound RD as the light-emitting layer (EML, weight ratio 98:2, ). Evaporation of compound HB as a hole blocking layer (HBL, ), compound ET and Liq were co-deposited as an electron transport layer (ETL, weight ratio 40:60, ), evaporation Thick Liq is used as the electron injection layer (EIL). Finally, metal Al is evaporated as the cathode The device was then transferred back to the glove box and encapsulated with a glass cover slip to complete the device.

[0219] Device Comparison Example 1

[0220] The preparation method of device comparative example 1 is the same as that of device example 1, except that compound EB is used in the electron blocking layer instead of compound H60 of the present invention.

[0221] The detailed device layer structure and thickness are shown in Table 1. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0222] Table 1 Partial device structures of Example 1 and Comparative Example 1

[0223]

[0224] The material structure used in the device is as follows:

[0225]

[0226] Table 2 summarizes the device performance of Example 1 and Comparative Example 1. The color coordinates (CIE), voltage (V), and power efficiency (PE) are calculated at a current density of 10 mA / cm 2 Measured below.

[0227] Table 2 Device data of Example 1 and Comparative Example 1

[0228] Part Number <![CDATA[CIE x ]]> <![CDATA[CIE y ]]> Voltage (V) Power efficiency (lm / W) Example 1 0.677 0.323 4.14 17.5 Comparative Example 1 0.676 0.324 5.07 15.8

[0229] discuss:

[0230] As can be seen from the data in Table 2, the CIE data of Example 1 and Comparative Example 1 are basically consistent. The compound EB used in Comparative Example 1 is an electron blocking material with excellent performance. Compared with Comparative Example 1, the voltage of Example 1 is greatly reduced by 0.93V, which is very rare, and the power efficiency of Example 1 is significantly improved by 10.8% on the already high power efficiency level of Comparative Example 1. The data show that the compound having the structure of Formula 1 of the present invention can effectively regulate the balance of hole and electron transmission in the device, reduce the device voltage, improve the device efficiency, and provide better device comprehensive performance.

[0231] In summary, the compound having the structure of Formula 1 of the present invention is applied to an organic electroluminescent device, which can make the device have low voltage and high efficiency and can achieve a significant improvement in device performance, which proves the excellent performance and unique advantages of the compound of the present invention and indicates its broad prospects in commercial applications.

[0232] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure represented by Formula 1: In formula 1, n is an integer selected from 1 to 3; X1 to X8 are selected from C, CR, x or N; and n of X1 to X8 are selected from C and are respectively connected to L0; Y1 to Y 13 Each occurrence is selected from CR y or N; Q is selected from C or Si; L0, L1, L2 are identically or differently 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 at each occurrence; Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof; R x , R y 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 x , R y Can optionally be linked to form a ring.

2. The compound according to claim 1, wherein n is selected from 1 or 2; preferably, n is selected from 1.

3. The compound according to claim 1, wherein The compound has a structure represented by Formula 2 or Formula 3: X1 to X8 are selected from C, CR, x or N; Y1 to Y 13 Each occurrence is selected from CR y or N; Q, at each occurrence, is selected from C or Si; L0, L1, L2 are identically or differently 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 at each occurrence; Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof; R x , R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an 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 x , R y Can optionally be linked to form a ring.

4. The compound according to claim 1, which has a structure represented by any one of Formula 2-1 to Formula 2-3: X1 to X8 are selected from CR in the same or different manner at each occurrence. x or N; Y1 to Y 13 Each occurrence is selected from CR y or N; Q is selected from C or Si; L0, L1 and L2 are identically or differently 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 at each occurrence; Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof; R x , R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an 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 x , R y can optionally be linked to form a ring; Preferably, the compound has a structure represented by Formula 2-2 or Formula 2-3.

5. The compound according to any one of claims 1 to 4, wherein The L0, L1 and L2 are 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 when they appear each time; Preferably, each occurrence of L0, L1 and L2 is identically or differently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenopheneylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, or a combination thereof; More preferably, L0, L1 and L2 are identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group at each occurrence.

6. The compound according to any one of claims 1 to 4, wherein The Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, or combinations thereof, when they appear at each occurrence; Preferably, each occurrence of Ar1 and Ar2 is identically or differently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or a combination thereof; More preferably, Ar1 and Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, or a combination thereof, the same or different when they appear each time.

7. The compound according to claim 1, 3 or 4, wherein The R x , R y each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; Preferably, the R x , R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

8. The compound according to claim 1, 3 or 4, wherein The Q is selected from C.

9. The compound according to claim 1, wherein The compound is selected from the group consisting of Compound H1 to Compound H486: Optionally, hydrogen in the structures of Compounds H1 to H486 can be partially or completely replaced by deuterium.

10. 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 9.

11. The organic electroluminescent device according to claim 10, wherein: The organic layer is an electron blocking layer or a hole transport layer; Preferably, the organic layer is an electron blocking layer.

12. A compound composition comprising the compound according to any one of claims 1 to 9.

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