Novel organic electroluminescent material and device thereof

Abstract

The invention discloses a novel organic electroluminescent material and a device thereof. The novel organic electroluminescent material has a structure as shown in formula 1, and can improve the balance of electrons and holes in an organic electroluminescent device when being applied to the organic electroluminescent device, thereby bringing excellent device effects, such as improvement of external quantum efficiency, current efficiency and service life. The organic semiconductor device is easy to prepare, and the organic semiconductor device is suitable for different types of organic semiconductor devices including but not limited to a fluorescent OLED, a phosphorescent OLED, a white light OLED, a laminated OLED, an OTFT, an OPV and the like. The invention also discloses an electroluminescent device containing the organic electroluminescent material and a compound formula.

Description

[0001] This application is a divisional application with the priority date of July 20, 2020, priority number: CN202010698126.6; the application date is June 30, 2021, application number is CN202110716169.7, and the invention name is "A new type of organic electroluminescent material and device thereof". Technical Field

[0002] The present invention relates to a novel organic electroluminescent material and a device thereof, and more particularly to an organic electroluminescent material having a structure of formula 1, an electroluminescent device containing the material and a compound formula containing the material. Background Art

[0003] 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.

[0004] 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.

[0005] 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.

[0006] 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.

[0007] 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.

[0008] Organic light-emitting display devices use hole injection layers and electron injection layers to promote charge injection. The hole injection layer is a functional layer formed by a single material or more than one material. The single material method generally uses materials with deeper LUMO, such as HATCN. The method of more than one material is formed by doping P-type, deep LUMO materials with hole transport materials. This mode can generate migrating holes (free carriers) by doping the matrix material (generally hole transport materials) with dopants, and can improve the hole injection ability of the anode and change the Fermi level of the device. Deep LUMO materials are generally conjugated system compounds with one or more strongly electron-withdrawing substituents. Deep LUMO materials are not easy to synthesize because they have strongly electron-withdrawing substituents, and it is difficult to have deep LUMO, high stability and high film-forming properties at the same time. For example, F4-TCNQ (P-type hole injection material), although it has a deep LUMO, the evaporation temperature is too low, which affects the control of deposition, the reproducibility of production performance and the thermal stability of the device; for another example, HATCN has film-forming problems in the device due to its strong crystallinity, and the LUMO is not deep enough to be used as a P-type dopant. In view of the fact that the hole injection layer has a great influence on the voltage, efficiency and life of OLED devices, it is very important and urgent in the industry to develop materials with deep LUMO, high stability and high film-forming properties. The present invention provides a series of organic electroluminescent materials with a novel dehydrogenated ring structure. These materials have LUMO energy levels of different depths and have a suitable evaporation temperature. They can be used as a single hole injection layer and are also excellent P-type dopants.

[0009] K.Suzuki, M.Tomura, S.Tanaka, Y.Yamashita, Tetrahedron Letter, 2000, 41, 8359-8364 discloses a compound having a bithiophene and bithiazole structure, wherein the structure of the specific compound is: R=H or OCH3, but this document does not disclose or teach any properties and applications of the compounds when R is other groups.

[0010] PK Nandi. K. Mandal, T. Kar, J. Molecular Structure: THEOCHEM, 2006, 760, 235-244 discloses a compound having a bithiophene structure, wherein the structure of the specific compound is The research in this document mainly focuses on the nonlinear optical properties and applications of the compounds, but does not disclose or teach the properties and applications of any compounds having a substituent structure similar to that of the present application.

[0011] H.Ishida, K.Yui, Y.Aso, T.Otsubo, F.Ogura, Bull.Chem.Soc.Jpn., 1990, 63, 2828-2835 discloses a series of compounds having structures such as thiophene and bithiophene, among which specific examples of the compounds are: However, these documents do not disclose or teach the properties and applications of any compound having a core structure similar to that of the present application.

[0012] JPH0338578 discloses a class of compounds containing structures such as bifuran and bithiophene as electron acceptors, and the disclosed general structure includes the following: However, this application does not disclose or teach the properties and applications of any compound having a core structure similar to that of the present application.

[0013] CN105176519 discloses a thiazole-containing radialene compound, wherein the compound has the general structural formula: This application focuses on the properties of radialene-type compounds, but does not disclose or teach the properties and applications of any compounds having a core structure similar to that of the present application.

[0014] It is necessary to develop a hole injection material in organic electroluminescent materials, which can improve the transmission balance of electrons and holes in OLEDs and enhance device performance. Therefore, it is crucial to develop new high-performance hole injection materials. Summary of the invention

[0015] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least part of the above problems.

[0016] According to one embodiment of the present invention, a compound is disclosed, which has a structure shown in Formula 1:

[0017]

[0018] in,

[0019] Each time L appears, it is selected from or any combination thereof;

[0020] Ring AA is a conjugated structure of 4-30 ring atoms having at least one intracyclic double bond;

[0021] n is selected from integers from 0 to 10, the same or different at each occurrence;

[0022] Each time Y appears, it may be selected from CR L and N;

[0023] Ring A is identical or different at each occurrence and is a 5-membered heterocyclic ring; and the 5-membered heterocyclic ring contains an intracyclic double bond, at least one N atom and at least one heteroatom W; W is identical or different at each occurrence and is selected from O, S, Se and NR N The group composed of;

[0024] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0025] R and R L Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0026] R, R', R", R'', R L and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0027] When L is selected from When n=0, R and R N At least one of them is a group having at least one electron-withdrawing group;

[0028] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0029] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0030] Adjacent substituents R, R L can be optionally linked to form a ring; when adjacent substituents R LWhen connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms.

[0031] According to another embodiment of the present invention, an electroluminescent device is disclosed, which comprises the compound described in the above embodiment.

[0032] According to another embodiment of the present invention, a compound formulation is also disclosed, which comprises the compound described in the above embodiment.

[0033] The compound having the structure of Formula 1 disclosed in the present invention can be applied to organic electroluminescent devices, and can improve the balance of electrons and holes in the device, thereby bringing excellent device effects, such as the improvement of external quantum efficiency, current efficiency and life span. It is easy to prepare organic semiconductor devices and is suitable for different types of organic semiconductor devices, including but not limited to fluorescent OLED, phosphorescent OLED, white light OLED, stacked OLED, OTFT, OPV, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0035] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. DETAILED DESCRIPTION

[0036] 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.

[0037] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0038] 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.

[0039] 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.

[0040] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The 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.

[0041] 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.

[0042] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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).

[0047] 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 (IRISC) 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.

[0048] 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).

[0049] Definition of Substituent Terms

[0050] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0051] 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.

[0052] 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.

[0053] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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,

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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 amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms. The invention also includes an alkyl group, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] In the compounds mentioned in the present disclosure, unless explicitly 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, 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.

[0070] In the present invention, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring structure. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the number of ring atoms. The "number of ring atoms" recorded in this article has the same meaning unless otherwise specified. For example, The number of ring atoms is 4, where · is the position of connection to ring A; The number of ring atoms is 5; The number of ring atoms is 6; The number of ring atoms is 11.

[0071] 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:

[0072]

[0073] 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:

[0074]

[0075] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other 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:

[0076]

[0077] According to one embodiment of the present invention, a compound is disclosed, which has a structure shown in Formula 1:

[0078]

[0079] in,

[0080] Each time L appears, it is selected from or any combination thereof;

[0081] Ring AA is a conjugated structure of 4-30 ring atoms having at least one intracyclic double bond;

[0082] n is selected from integers from 0 to 10, the same or different at each occurrence;

[0083] Each time Y appears, it may be selected from CR L and N;

[0084] Ring A is identical or different at each occurrence and is a 5-membered heterocyclic ring, and the 5-membered heterocyclic ring contains an intracyclic double bond, at least one N atom and at least one heteroatom W; W is identical or different at each occurrence and is selected from O, S, Se and NR N The group composed of;

[0085] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0086] R and R L Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0087] R, R', R", R'', R L and R NEach occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0088] When L is selected from When n=0, R and R N At least one of them is a group having at least one electron-withdrawing group;

[0089] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0090] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0091] Adjacent substituents R, R L can be optionally linked to form a ring; when adjacent substituents R L When connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms.

[0092] In this article, when n=0, it means that L does not exist, that is, the two rings in Formula 1 are directly connected by a double bond to form a structure such as Formula 1-1:

[0093] In this embodiment, “when L is selected from When n=0, R and R N "at least one of which is a group having at least one electron withdrawing group" is intended to express that when Formula 1 has the structure of Formula 1-1, R each time appears, the same or different represents mono-substitution, poly-substitution, or no substitution, and R and R N At least one of the substituents in the group is a group with at least one electron-withdrawing group. Obviously, when R and RN When one of them does not exist, the above-mentioned substituent group must still satisfy that at least one substituent is a group having at least one electron-withdrawing group.

[0094] In this embodiment, “L” is selected from or any combination thereof" is intended to indicate that each occurrence of L is selected from or A combination of A combination of combination.

[0095] In this context, "adjacent substituents R", R"' can optionally be linked to form a ring" is intended to mean that when X is selected from CR"R"', substituents R" and R"' can be linked to form a ring. When substituents R" and R"' are linked to form a ring, the formed ring can have 4 ring atoms or 5 ring atoms. Obviously, substituents R" and R"' may not be linked to form a ring.

[0096] As used herein, “adjacent substituents R, R L "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, between substituents R, L Between the substituents R and R L Any one or more of these substituent groups may be connected to form a ring. L When connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms; when substituents R and R L Obviously, these substituents may not be connected to form a ring.

[0097] According to one embodiment of the present invention, the substituents R, R L and R N At least one of them is a group having at least one electron withdrawing group; preferably, R and R L At least one of the groups is a group having at least one electron withdrawing group.

[0098] In this embodiment, "wherein the substituents R, R L and R N At least one of them is a group having at least one electron withdrawing group" means that when W is selected from NR N When the substituents R, R L and R N At least one of the substituents R and R is a group having at least one electron withdrawing group; when W is selected from O, S, Se, the substituents R and R LAt least one of the groups is a group having at least one electron withdrawing group.

[0099] According to one embodiment of the present invention, the substituents R, R', R", R'", R L and R N All of them are groups having at least one electron-withdrawing group.

[0100] In this embodiment, "wherein the substituents R, R L and R N At least one of them is a group having at least one electron withdrawing group” means that R and R L Each occurrence of R and R is identical or different, indicating mono-, poly-, or unsubstituted L and R N At least one of the substituents in the group of substituents is a group with at least one electron-withdrawing group. Obviously, when R, R L and R N When one of the above substituents is absent, the above substituent group still satisfies that at least one substituent is a group having at least one electron withdrawing group. For example, when W is selected from O, S, Se, the substituents R and R L At least one of the groups is a group having at least one electron withdrawing group.

[0101] According to one embodiment of the present invention, ring A contains CR, and R is a group having at least one electron withdrawing group.

[0102] According to one embodiment of the present invention, the two ends of L in Formula 1 are connected to each other. Each occurrence is the same or different and is selected from any structure represented by Formula 2 to Formula 5:

[0103]

[0104] Among them, in Formula 2 to Formula 5,

[0105] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0106] W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of;

[0107] R, R', R", R'' and R NEach occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0108] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0109] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0110] Adjacent substituents R can optionally be linked to form a ring having at least 6 ring atoms.

[0111] “**” represents the connection position of L in Formulae 2 to 5 and Formula 1.

[0112] According to one embodiment of the present invention, the substituents R, R', R", R'" and R N All of them are groups having at least one electron-withdrawing group.

[0113] According to one embodiment of the present invention, each time L appears, it is the same or different and is selected from the structures shown in Formula 6 to Formula 6A and combinations thereof:

[0114]

[0115] Wherein, in Formula 6 and Formula 6A,

[0116] n is selected from integers from 0 to 10 at each occurrence, the same or different, and m is selected from integers from 1 to 4 at each occurrence, the same or different;

[0117] Each occurrence of E is the same or different and is selected from O, S, Se and CR A R B The group composed of;

[0118] Y and Z are selected from CR L or N;

[0119] R A , R B , R L Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0120] Adjacent substituent R A and R B can optionally be linked to form a ring;

[0121] Adjacent substituent R L can be optionally linked to form a ring containing 4 or more ring atoms;

[0122] “#” and “##” represent the connection position of Formula 6 and Formula 6A to Ring A or L in Formula 1.

[0123] According to one embodiment of the present invention, the substituent R A , R B , R L All of them are groups having at least one electron-withdrawing group.

[0124] According to one embodiment of the present invention, n is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 each time it occurs, the same or different; m is selected from 1, 2, 3, 4 each time it occurs, the same or different.

[0125] According to one embodiment of the present invention, wherein L is n is 0, and the compound has any structure represented by Formula I to Formula XVI:

[0126]

[0127] Wherein, in Formula I to Formula XVI,

[0128] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0129] W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of;

[0130] R, R', R", R'' and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0131] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0132] Substituents R and R N At least one of them is a group having at least one electron-withdrawing group;

[0133] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0134] Adjacent substituents R can optionally be linked to form a ring having at least 6 ring atoms.

[0135] According to one embodiment of the present invention, the compound has any of the following structures:

[0136]

[0137] in,

[0138] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0139] W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of;

[0140] R, R', R", R'' and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0141] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0142] Substituents R and R N At least one of them is a group having at least one electron-withdrawing group;

[0143] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0144] Adjacent substituents R can optionally be linked to form a ring having at least 6 ring atoms.

[0145] According to one embodiment of the present invention, the substituents R, R', R", R'" and R N All of them are groups having at least one electron-withdrawing group.

[0146] According to one embodiment of the present invention, the compound has any one of the structures represented by Formula LI and Formula LIA:

[0147]

[0148] Wherein, in Formula LI and Formula LIA,

[0149] Y and Z each appear the same or differently selected from CR L and N;

[0150] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0151] W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of;

[0152] R, R', R", R'', R L and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0153] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0154] Adjacent substituents R", R"' can be optionally linked to form a ring;

[0155] Adjacent substituents R, R L can be optionally linked to form a ring; when adjacent substituents R L When connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms;

[0156] Preferably, R, R L and R N At least one of the groups is a group having at least one electron withdrawing group.

[0157] In this article, the structural formula Indicates that the structure can exist in cis and trans configurations. For example, when two R, two Y, two W and two X in formula LI are the same, the following structures are included When the two R in formula LI (with R 1 and R 2 Indicates that R 1 and R 2 may be the same or different), and / or two Y (represented by Y1 and Y2, Y1 and Y2 may be the same or different), and / or two W (represented by W1 and W2, W1 and W2 may be the same or different), and / or two X (represented by X1 and X2, X1 and X2 may be the same or different) when at least one of the two is different, the following structure is included

[0158] According to one embodiment of the present invention, the substituent R A , R B , R, R', R", R'', R L and R N All of them are groups having at least one electron-withdrawing group.

[0159] According to one embodiment of the present invention, the substituents R, R L Not connected to form a ring. For example, between substituents R and R, substituent R L and R L Between the substituents R and R L They are not connected to form a ring.

[0160] According to one embodiment of the present invention, the compound has a structure represented by Formula II-I:

[0161]

[0162] in,

[0163] K is selected from O, S, Se and CR in the same or different manner at each occurrence A R B The group composed of;

[0164] X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"';

[0165] W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of;

[0166] J is selected from O, S, Se and NR in the same or different manner at each occurrence NJ The group composed of;

[0167] Preferably, J is selected, identically or differently, from NR NJ ;

[0168] R A , R B , R', R", R"', R N and NR NJ Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof;

[0169] Adjacent substituent R A and R B can optionally be linked to form a ring;

[0170] In Formula II-I, R A , R B , R N and NR NJ At least one of the R is a group having at least one electron withdrawing group, and / or at least one of the K is O;

[0171] When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group;

[0172] Adjacent substituents R", R"' can be optionally linked to form a ring.

[0173] According to one embodiment of the present invention, in formula II-I, the substituent R A , R B , R N and NR NJ At least one of the R is a group having at least one electron withdrawing group, and / or at least one of the K is O.

[0174] According to one embodiment of the present invention, each occurrence of Y is identical or different and is selected from CR L and N groups.

[0175] According to one embodiment of the present invention, each occurrence of Y is identical or different and is selected from CR L .

[0176] According to one embodiment of the present invention, each occurrence of X is identically or differently selected from CR"R"'.

[0177] According to one embodiment of the present invention, W is selected from O, S or Se the same or different each time it occurs.

[0178] According to one embodiment of the present invention, W is selected from O or S the same or differently each time it occurs.

[0179] According to one embodiment of the present invention, W is O.

[0180] According to one embodiment of the present invention, each time W appears, it is selected from NR N , and R N Each occurrence is identically or differently selected from the group consisting of: 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 alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0181] According to one embodiment of the present invention, wherein R N Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0182] According to one embodiment of the present invention, at least one of the R is a group having at least one electron withdrawing group.

[0183] According to one embodiment of the present invention, R', R", R'", R L , R N and R NJ Each of is a group having at least one electron withdrawing group.

[0184] According to one embodiment of the present invention, at least one of the R represents a single substitution or a multiple substitution, and at least one of them is a group having an electron withdrawing group.

[0185] According to one embodiment of the present invention, at least one of R is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

[0186] According to one embodiment of the present invention, at least one of R is an aromatic group having 6 to 30 carbon atoms substituted with at least one electron withdrawing group, a heteroaromatic group having 3 to 30 carbon atoms substituted with at least one electron withdrawing group, or a combination thereof.

[0187] According to one embodiment of the present invention, each occurrence of R is identical or different and is a group having at least one electron withdrawing group.

[0188] According to one embodiment of the present invention, each occurrence of R is identically or differently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0189] Preferably, R at each occurrence is an aryl group having 6 to 30 carbon atoms substituted with at least one electron withdrawing group, a heteroaryl group having 3 to 30 carbon atoms substituted with at least one electron withdrawing group, or a combination thereof.

[0190] According to one embodiment of the present invention, the Hammett constant of the electron-withdrawing base is ≥0.05, preferably ≥0.3, and more preferably ≥0.5.

[0191] The Hammett substituent constant value of the electron-withdrawing group of the present invention is ≥0.05, such as ≥0.1, or ≥0.2; preferably ≥0.3, more preferably ≥0.5, and has a strong electron-withdrawing ability, which can significantly reduce the LUMO energy level of the compound, thereby achieving the effect of improving charge mobility.

[0192] It should be noted that the Hammett substituent constant value includes the Hammett substituent para constant and / or meta constant. As long as the para constant and the meta constant are both greater than zero, and one of them satisfies greater than or equal to 0.05, the group can be selected as the group of the present invention.

[0193] According to one embodiment of the present invention, the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group, or any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group: Alkyl, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0194] According to one embodiment of the present invention, the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring group: Alkyl, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0195] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: fluorine, acyl, carbonyl, ester, SF5, borane, nitrogen heteroaromatic ring group, and any of the following groups substituted by one or more of fluorine, cyano, isocyano, SCN, OCN, SF5, CF3, OCF3, SCF3, nitrogen heteroaromatic ring group: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0196] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: fluorine, acyl, carbonyl, ester, SF5, borane, nitrogen heteroaromatic ring group, and any of the following groups substituted by one or more of fluorine, cyano, isocyano, SCN, OCN, SF5, CF3, OCF3, SCF3, nitrogen heteroaromatic ring group: aromatic group having 6-30 carbon atoms, heteroaromatic group having 3-30 carbon atoms, and combinations thereof.

[0197] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of fluorine, SF5, borane, pyridyl, pyrimidinyl, imidazolyl, thiazolyl, oxazolyl, triazine, and any of the following groups substituted by one or more of fluorine, cyano, isocyano, SCN, OCN, SF5, CF3, OCF3, SCF3, pyridyl, pyrimidinyl, imidazolyl, thiazolyl, oxazolyl, triazine: phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, triazine, and combinations thereof.

[0198] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: any of the following groups substituted by one or more of fluorine, SF5, CF3, OCF3, SCF3: phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, pyridyl, pyrimidyl, triazine, and combinations thereof.

[0199] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: any of the following groups substituted by one or more of fluorine, SF5, CF3, OCF3, SCF3: an aromatic group having 6-30 carbon atoms, a heteroaromatic group having 3-30 carbon atoms, and a combination thereof.

[0200] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidine, triazine, and combinations thereof.

[0201] According to one embodiment of the present invention, each occurrence of X is identically or differently selected from the group consisting of the following structures: Se,

[0202]

[0203] Wherein, V, U and T are selected from CR v R u , NR v , a group consisting of O, S and Se;

[0204] wherein Ar is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0205] Among them, R1, Q, R a , R b , R c , R d , R e , R f , R g , R h , R v and R u is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 cycloalkyl having 7 to 30 carbon atoms, atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;

[0206] Preferably, R1 is selected, at each occurrence, identically or differently, from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidyl, triazine, and combinations thereof;

[0207] wherein Q is a group having at least one electron withdrawing group, and for any of the above structures, when R a , R b , R c , R d , R e , R f , R g , R h , R v and R u When one or more of the above are present, at least one of them is a group having at least one electron-withdrawing group; preferably, the group having at least one electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and combinations thereof;

[0208] Adjacent substituents R1, R a , R b , R c , R d , R e , R f , R g , R h , R v and R u can optionally be linked to form a ring;

[0209] "*" represents the connection position of X having the above structure and Formula 1.

[0210] According to one embodiment of the present invention, each time R1 occurs, it is identically or differently selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and combinations thereof.

[0211] According to one embodiment of the present invention, each occurrence of X is identically or differently selected from the group consisting of the following structures: Se,

[0212] According to one embodiment of the present invention, wherein X is selected from

[0213] According to one embodiment of the present invention, R, RL , R N and R NJ is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

[0214] According to one embodiment of the present invention, R, R L , R N and R NJ is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, CN, vinyl substituted by one or more of CN or CF3, acetylene substituted by one of CN or CF3 substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazine, pyridyl, diphenylboryl, oxaboranthenyl, and combinations thereof.

[0215] According to one embodiment of the present invention, R, R L , R N and R NJ are selected, at each occurrence, identically or differently, from the group consisting of:

[0216]

[0217]

[0218]

[0219] Wherein "﹋" represents R with the above structure and formula 1, R L The connection position with L; It also represents when J is selected from NR NJ When R NJ The connection position with N; "﹋" also represents when W is selected from NR N When R N The connection position with N.

[0220] According to one embodiment of the present invention, R, R L , R N and R NJ In each occurrence, identically or differently selected from the group consisting of:

[0221]

[0222]

[0223] Wherein "﹋" represents R with the above structure and formula 1, R L The connection position with L; "﹋" also represents when J is selected from NR NJ When R NJ The connection position with N; "﹋" also represents when W is selected from NR N When R N The connection position with N.

[0224] According to one embodiment of the present invention, the substituents R, R', R", R'", R L , R N , R NJ , R A and R B All are groups having at least one electron-withdrawing group.

[0225] According to one embodiment of the present invention, the substituents R, R', R", R'", R L , R N , R NJ , R A and R B It is a group that does not contain an electron-rich group. Examples of electron-rich groups include substituted or unsubstituted amino groups. When the substituent contains an electron-rich group, the LUMO energy level becomes shallower than when it contains an electron-withdrawing group, which is not conducive to hole injection.

[0226] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound I-1 to Compound I-114, Compound II-1 to Compound II-108, Compound III-1 to Compound III-108, Compound IV-1 to Compound IV-108, Compound V-1 to Compound V-108, Compound VI-1 to Compound VI-108, Compound VII-1 to Compound VII-108, Compound VIII-1 to Compound VIII-108, Compound IX-1 to Compound IX-108, Compound X-1 to Compound X-108, Compound XI-1 to Compound XI-108, Compound XII-1 to Compound XII-108, Compound XIII-1 to Compound XIII-108, Compound XIV-1 to Compound XIV-108, Compound XV-1 to Compound XV-108, Compound XVI-1 to Compound XVI-108 A group of compounds, wherein the specific structures of compounds I-1 to compound I-108, compounds II-1 to compound II-108, compounds III-1 to compound III-108, compounds IV-1 to compound IV-108, compounds V-1 to compound V-108, compounds VI-1 to compound VI-108, compounds VII-1 to compound VII-108, compounds VIII-1 to compound VIII-108, compounds IX-1 to compound IX-108, compounds X-1 to compound X-108, compounds XI-1 to compound XI-108, compounds XII-1 to compound XII-108, compounds XIII-1 to compound XIII-108, compounds XIV-1 to compound XIV-108, compounds XV-1 to compound XV-108, and compounds XVI-1 to compound XVI-108 are shown in claim 23.

[0227] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds LIO-1 to LIO-108, and compounds LIOA-1 to LIOA-66, wherein the specific structures of compounds LIO-1 to LIO-108, and compounds LIOA-1 to LIOA-66 are shown in claim 24.

[0228] According to one embodiment of the present invention, the compound is selected from the group consisting of II-IO-1 to compound II-IO-60, wherein the specific structures of II-IO-1 to compound II-IO-60 are shown in claim 25.

[0229] According to one embodiment of the present invention, an organic electronic device is disclosed, comprising:

[0230] anode,

[0231] cathode,

[0232] An organic layer is disposed between the anode and the cathode, wherein the organic layer comprises the compound described in any one of the above embodiments.

[0233] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:

[0234] anode,

[0235] cathode,

[0236] An organic layer disposed between the anode and the cathode, the organic layer comprising the compound described in any of the above embodiments. According to one embodiment of the present invention, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is formed solely by the compound.

[0237] According to one embodiment of the present invention, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer further comprises at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000;

[0238] Preferably, the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0239] According to one embodiment of the present invention, the electroluminescent device comprises a plurality of stacked layers between an anode and a cathode, the stacked layers comprising a first light-emitting layer and a second light-emitting layer, wherein the first stacked layer comprises a first light-emitting layer, the second stacked layer comprises a second light-emitting layer, and a charge generation layer is arranged between the first stacked layer and the second stacked layer, wherein the charge generation layer comprises a p-type charge generation layer and an n-type charge generation layer;

[0240] The p-type charge generation layer comprises the compound; preferably, the p-type charge generation layer further comprises at least one hole transport material, wherein the molar doping ratio of the compound to the hole transport material is 10000:1 to 1:10000; preferably, the molar doping ratio of the compound to the hole transport material is 10:1 to 1:100.

[0241] According to one embodiment of the present invention, the hole transport material comprises a compound having a triarylamine unit, a spirobifluorene compound, a pentacene compound, an oligothiophene compound, an oligophenyl compound, an oligophenylene vinyl compound, an oligofluorene compound, a porphyrin complex or a metal phthalocyanine complex.

[0242] According to one embodiment of the present invention, the charge generation layer further includes a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, and the buffer layer includes the compound.

[0243] According to an embodiment of the present invention, the electroluminescent device is prepared by a vacuum evaporation method.

[0244] According to one embodiment of the present invention, a compound formulation is also disclosed, which comprises the compound described in any of the aforementioned embodiments.

[0245] Combination with other materials

[0246] 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.

[0247] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0248] 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.

[0249] The measured LUMO energy level obtained in this paper is the electrochemical property of the compound determined by cyclic voltammetry. The electrochemical workstation model is CorrTest CS120 produced by Wuhan CorrTest Instrument Co., Ltd. The three-electrode working system is as follows: the platinum disk electrode is used as the working electrode, the Ag / AgNO3 electrode is used as the reference electrode, and the platinum wire electrode is used as the auxiliary electrode. Anhydrous DCM is used as the solvent and 0.1 mol / L tetrabutylammonium hexafluorophosphate is used as the supporting electrolyte. The target compound is prepared into 10 -3 mol / L solution, nitrogen was introduced into the solution for 10 min to remove oxygen before testing. Instrument parameter settings: scan rate 100 mV / s, potential interval 0.5 mV, test window 1 V to -0.5 V.

[0250] Material Synthesis Example

[0251] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthesis routes and preparation methods are as follows.

[0252] Synthesis Example 1: Synthesis of Compound I-6

[0253] Step 1: Synthesis of [Intermediate 1-b]

[0254]

[0255] Under nitrogen atmosphere, 1-a (9.20 g, 21.7 mmol) was added to THF (400 mL), the temperature was lowered to -72 ° C (ethanol / dry ice), LiHMDS solution (1.0 M, 100 mL) was slowly added dropwise, and then slowly raised to -30 ° C and continued to react for 0.5 h. ZnCl2 (2.0 M, 50 mL) solution was added dropwise at -30 ° C, slowly raised to 0 ° C and reacted for 10 min, and single solid iodine (23.2 g, 91.4 mmol) was added to the reaction solution and reacted at 0 ° C for 2 h. The reaction was complete, quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried with anhydrous Na2SO4, filtered and dried with the solvent. The product 1-b (12.8 g, 87% yield) was separated by silica gel column chromatography (using DCM / PE = 1 / 1 as eluent) to obtain a white solid. 1 HNMR (400MHz, CDCl3) δ = 7.59 (d, J = 8.4 Hz, 4H), 7.48 (d, J = 8.4 Hz, 4H).

[0256] Step 2: Synthesis of [Intermediate 1-c]

[0257]

[0258] Under nitrogen atmosphere, malononitrile (0.79 g, 11.9 mmol) was added to anhydrous DMF (30 mL), and NaH (0.48 g, 12.0 mmol, 60% content) was added in batches at 0 ° C, and stirred for 20 minutes. 1-b (2.0 g, 3.0 mmol) and Pd (PPh4) 3 (0.35 g, 3.0 mmol) were added, and the temperature was raised to 90 ° C for 24 h. After complete conversion, it was poured into ice water, and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a small amount of water and petroleum ether. The solid product was dissolved in acetone, the solvent was removed by rotary evaporation and dried, and then dissolved in dichloromethane (50 mL), filtered, and washed three times with dichloromethane (20 mL) to obtain a yellow solid 1-c (1.3 g, 80% yield). 1 HNMR (400MHz, d6-DMSO) δ = 7.62 (d, J = 6.8 Hz, 4H), 7.51 (d, J = 6.8 Hz, 4H).

[0259] Step 3: Synthesis of Compound I-6

[0260]

[0261] Under nitrogen atmosphere, 1-c (1.3 g, 2.4 mmol) was added to DCM (250 mL), cooled to 0 °C, PIFA (2.1 g, 4.9 mmol) was added in batches, and stirred at room temperature for 3 days. The solution was purple-black. After most of the solvent was removed by rotary evaporation, a black solid was obtained by filtration. It was washed twice with DCM / PE = 1:1 (20 mL), and finally dried to obtain a black solid I-6 (1.0 g, 77% yield). 1 HNMR (400MHz, d6-acetone) δ = 8.34 (s, 2H), 8.06 (s, 2H). The product was confirmed to be the target product with a molecular weight of 550. The CV of compound I-6 was measured in DCM, and the LUMO of the compound was obtained to be -4.81 eV. At 1.9*10 -4 Pa under vacuum conditions and heated at a constant temperature of 280°C for 12 h to obtain the product, a black solid compound I-6.

[0262] Synthesis Example 2: Synthesis of Compound I-8

[0263] Step 1: Synthesis of [Intermediate 2-b]

[0264]

[0265] Under nitrogen atmosphere, 2-a (11.5 g, 20.5 mmol) was added to THF (200 mL), the temperature was lowered to -72 °C (ethanol / dry ice), LiHMDS solution (1.0 M, 85 mL) was slowly added dropwise, and then the temperature was slowly raised to -30 °C and reacted for 0.5 h. ZnCl2 (2.0 M, 43 mL) solution was added dropwise at -30 °C, the temperature was slowly raised to 0 °C and reacted for 10 min, and elemental solid iodine (22.0 g) was added to the reaction solution and reacted at 0 °C for 2 h. After the reaction was complete, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried with anhydrous Na2SO4, filtered and dried with the solvent. The product 2-b (15.6 g, 94% yield) was separated by silica gel column chromatography (using DCM / PE = 1 / 1 as eluent) to obtain a white solid. 1 HNMR (400MHz, CDCl3) δ = 8.02 (s, 4H), 7.79 (s, 2H).

[0266] Step 2: Synthesis of [Intermediate 2-c]

[0267]

[0268] Under nitrogen atmosphere, malononitrile (2.74 g, 41.4 mmol) was added to anhydrous DMF (100 mL), and NaH (1.67 g, 41.8 mmol, 60% content) was added in batches at 0 ° C, stirred for 30 minutes, and then 2-b (8.05 g, 9.9 mmol) and Pd (PPh4) 3 (1.14 g) were added, and the temperature was raised to 90 ° C for 24 hours. After complete conversion, it was poured into ice water, and 2N dilute hydrochloric acid was used to adjust the pH <1. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a large amount of water and petroleum ether. The solid product was dissolved in acetone, the solvent was removed by rotary evaporation and dried, and then dissolved in dichloromethane (100 mL), filtered, and washed three times with DCM / PE = 1 / 1 (30 mL). Finally, the yellow solid HT355-C (6.5 g, 95% yield) was obtained by filtration. 1 HNMR (400MHz, d6-acetone) δ = 8.22 (s, 4H), 8.02 (s, 2H). .

[0269] Step 3: Synthesis of Compound I-8

[0270]

[0271] Under nitrogen atmosphere, 2-c (6.5 g, 9.4 mmol) was added to DCM (900 mL), cooled to 0 ° C, and PIFA (8.1 g, 18.9 mmol) was added in batches. Stir at room temperature for 3 days, and the solution was purple-black. Most of the solvent was removed by rotary evaporation, filtered, and washed twice with DCM / PE = 1:1 (100 mL), and finally dried to obtain a black solid I-8 (5.3 g, 82% yield). The product was confirmed to be the target product with a molecular weight of 686. The CV of compound I-8 was measured in DCM, and the LUMO of the compound was obtained to be -4.91 eV. At 4.9*10 -4 Pa under vacuum conditions and heated at 270°C for 3 h to sublime to obtain the product, a black solid compound I-8.

[0272] Synthesis Example 3: Synthesis of Compound I-109

[0273] Step 1: Synthesis of [Intermediate 5-b]

[0274]

[0275] Under nitrogen atmosphere, 5-a (10.3 g, 23.6 mmol) was added to THF (400 mL), the temperature was lowered to -72 °C (ethanol / dry ice), LiHMDS solution (1.0 M, 60 mL) was slowly added dropwise, and then the temperature was slowly raised to -30 °C and the reaction was continued for 0.5 h. ZnCl2 (2.0 M, 30 mL) solution was added dropwise at -30 °C, the temperature was slowly raised to 0 °C and the reaction was continued for 10 min, and elemental solid iodine (20.1 g, 79.1 mmol) was added to the reaction solution and the reaction was continued at 0 °C for 2 h. The reaction was complete, and the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried with anhydrous Na2SO4, filtered and the solvent was dried. The product 5-b (13.7 g, 84% yield) was separated by silica gel column chromatography (using DCM / THF / PE=4 / 1 / 4 as eluent) as a white solid. 19 FNMR (400MHz, CDCl3) δ = -88.73 (m, 4F), -139.23 (m, 4F).

[0276] Step 2: Synthesis of [Intermediate 5-c]

[0277]

[0278] Under nitrogen atmosphere, malononitrile (2.2 g, 33 mmol) was added to anhydrous DMF (150 mL), and K2CO3 (4.45 g, 32.2 mmol) was added in batches at 0 ° C, and stirred for 20 minutes. 5-b (10.4 g, 15.2 mmol) and Pd (PPh4) 3 (1.55 g, 1.3 mmol) were added, and the temperature was raised to 50 ° C for 10 hours. After complete conversion, it was poured into ice water, and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a small amount of water and petroleum ether. The solid product was dissolved with acetone, the solvent was removed by rotary evaporation and dried, and then dispersed with dichloromethane, filtered, and washed three times with dichloromethane (20 mL) to obtain a yellow solid 5-c (3.9 g, 46% yield). 19 FNMR (400MHz, d6-acetone) δ = -90.08 (m, 4F), -138.31 (m, 4F).

[0279] Step 3: Synthesis of Compound I-109

[0280]

[0281] Under nitrogen atmosphere, 5-c (3.9 g, 6.9 mmol) was added to DCM (800 mL), cooled to 0 ° C, PIFA (6.2 g, 14.4 mmol) was added in batches, and stirred at room temperature for 2 days. The solution was purple-black. After most of the solvent was removed by rotary evaporation, a black solid was obtained by filtration. It was washed twice with DCM / PE = 1:1 (20 mL) and finally dried to obtain a black solid I-109 (2.4 g, 62% yield). 19 FNMR (400MHz, d6-acetone) δ = -89.72 (s, 8F). The product was confirmed to be the target product with a molecular weight of 560. The CV of compound I-109 was measured in DCM, and the LUMO of the compound was obtained to be -5.15 eV. At 8.0*10 -4 Pa under a vacuum condition and heated at a constant temperature of 300°C for 12 hours for sublimation to obtain the product, a black solid compound I-109.

[0282] Synthesis Example 4: Synthesis of Compound I-110

[0283] Step 1: Synthesis of [Intermediate 6-b]

[0284]

[0285] Under nitrogen atmosphere, 6-a (10.4 g, 21.9 mmol) was added to THF (550 mL), the temperature was lowered to -72 °C (ethanol / dry ice), LiHMDS solution (1.0 M, 70 mL) was slowly added dropwise, and then the temperature was slowly raised to -30 °C and reacted for 0.5 h. ZnCl2 (2.0 M, 35 mL) solution was added dropwise at -30 °C, the temperature was slowly raised to 0 °C and reacted for 10 min, and elemental solid iodine (18.5 g) was added to the reaction solution and reacted at 0 °C for 2 h. After the reaction was complete, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered and dried over dry solvent. The product 6-b (14.3 g, 90% yield) was separated by silica gel column chromatography (using THF / PE = 1 / 2 as eluent) to obtain a white solid. 1 HNMR (400MHz, d6-acetone) δ = 8.09 (m, 2H), 8.01 (d, J = 8.4Hz, 2H).

[0286] Step 2: Synthesis of [Intermediate 6-c]

[0287]

[0288] Under nitrogen atmosphere, malononitrile (5.38 g, 81.5 mmol) was added to anhydrous DMF (200 mL), K2CO3 (11.2 g, 81.0 mmol), 6-b (14.3 g, 19.7 mmol) and Pd(PPh4)3 (2.185 g) were added at 0 °C, and the temperature was raised to 80 °C for 24 h. After complete conversion, it was poured into ice water, and the pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a large amount of water and petroleum ether. The solid product was dissolved with acetone, the solvent was removed by rotary evaporation and dried, and then recrystallized with THF / PE=1 / 1, and finally filtered to obtain a yellow solid 6-c (11.3 g, 95% yield). 1 HNMR (400MHz, d6-acetone) δ = 8.20 (m, 4H), 8.07 (d, J = 8.0Hz, 2H).

[0289] Step 3: Synthesis of Compound I-110

[0290]

[0291] Under nitrogen atmosphere, 6-c (11.3 g, 18.8 mmol) was added to DCM (1200 mL), cooled to 0 ° C, and PIFA (16.2 g, 37.6 mmol) was added in batches. Stir at room temperature for 3 days, and the solution was purple-black. Most of the solvent was removed by rotary evaporation, filtered, washed twice with DCM (100 mL), and finally dried to obtain a black solid I-110 (10.1 g, 90% yield). The product was confirmed to be the target product with a molecular weight of 600. The CV of compound I-8 was measured in DCM, and the LUMO of the compound was obtained to be -4.97 eV. At 1.1*10 -4 Pa under vacuum conditions and heated at a constant temperature of 340°C for 12 hours to obtain the product, a black solid compound I-110.

[0292] Synthesis Example 5: Synthesis of Compound I-111

[0293] Step 1: Synthesis of [Intermediate 7-b]

[0294]

[0295] Under nitrogen atmosphere, 7-a (6.3 g, 14.8 mmol) was added to THF (150 mL), cooled to -72 °C (ethanol / dry ice), and LiHMDS solution (1.0 M, 34 mL) was slowly added dropwise, then slowly raised to -30 °C and reacted for 0.5 h. ZnCl2 (2.0 M, 17 mL) solution was added dropwise at -30 °C, slowly raised to 0 °C and reacted for 10 min, and elemental solid iodine (11.5 g) was added to the reaction solution and reacted at 0 °C for 2 h. After the reaction was complete, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered and dried over dry solvent. The product 7-b (8.4 g, 97% yield) was separated by silica gel column chromatography (using DCM / EA / PE=4 / 1 / 4 as eluent) to obtain a white solid. 1 HNMR (400MHz, CDCl3) δ = 8.78 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H).

[0296] Step 2: Synthesis of [Intermediate 7-c]

[0297]

[0298] Under nitrogen atmosphere, malononitrile (3.52g, 53.3mmol) was added to anhydrous DMF (130mL), and NaH (2.138g, 53.5mmol, 60% content) was added at 0℃ and stirred for 20min, and then 7-b (8.3g, 12.2mmol) and Pd(PPh4)3 (1.435g) were added, and the temperature was raised to 80℃ for reaction for 24h. After complete conversion, it was poured into ice water, and pH was adjusted to <1 with 2N dilute hydrochloric acid. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a large amount of water and petroleum ether. The solid product was dissolved with acetone, the solvent was removed by rotary evaporation and dried, and then dispersed with dichloromethane, and finally filtered to obtain a yellow solid 7-c (6.6g, 96% yield). 1 HNMR (400MHz, d6-DMSO) δ = 8.75 (s, 1H), 8.08 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H).

[0299] Step 3: Synthesis of Compound I-111

[0300]

[0301] Under nitrogen atmosphere, 7-c (6.6 g, 11.9 mmol) was added to DCM (1200 mL), cooled to 0 ° C, and PIFA (10.7 g, 24.9 mmol) was added in batches. Stir at room temperature for 3 days, and the solution was purple-black. Most of the solvent was removed by rotary evaporation, filtered, washed twice with DCM (100 mL), and finally dried to obtain a black solid I-111 (5.4 g, 82% yield). The product was confirmed to be the target product with a molecular weight of 552. The CV of compound I-111 was measured in DCM, and the LUMO of the compound was obtained to be -4.92 eV. At 7.7*10 - 4 The product was heated to sublime at 300°C for 12 h under vacuum conditions of 0.3 Pa to obtain a black solid compound I-111.

[0302] Comparative Synthesis Example 1: Synthesis of Compound S

[0303]

[0304] Step 1: Synthesis of [Intermediate 3-b]

[0305]

[0306] Under nitrogen atmosphere, 3-a (2.2 g, 7.6 mmol) was added to THF (50 mL), cooled to -72 °C (ethanol / dry ice), and LiHMDS solution (1.0 M, 35 mL) was slowly added dropwise, then slowly raised to -30 °C and reacted for 0.5 h. ZnCl2 (2.0 M, 17 mL) solution was added dropwise at -30 °C, slowly raised to 0 °C and reacted for 10 min, and elemental solid iodine (7.8 g) was added to the reaction solution and reacted at 0 °C for 2 h. After the reaction was complete, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried with anhydrous Na2SO4, filtered and dried with the solvent. Silica gel column chromatography (with DCM / PE = 1 / 2 as eluent) gave the product 3-b (4.0 g, 97% yield) as a white solid. 1 HNMR (400MHz, CDCl3) δ = 7.51 (m, 4H), 7.24 (m, 6H).

[0307] Step 3: Synthesis of [Intermediate 3-c]

[0308]

[0309] Under nitrogen atmosphere, malononitrile (4.52 g, 68.4 mmol) was added to anhydrous DMF (160 mL), and NaH (2.80 g, 70.0 mmol, 60% content) was added in batches at 0 ° C, stirred for 30 minutes, and then 3-b (8.8 g, 16.3 mmol) and Pd (PPh4) 3 (1.88 g) were added, and the temperature was raised to 90 ° C for 24 hours. After complete conversion, it was poured into ice water, and 2N dilute hydrochloric acid was used to adjust the pH <1. A large amount of yellow solid precipitated, filtered, and the filter cake was washed with a large amount of water and petroleum ether. The solid product was dissolved with acetone, and the acetone was evaporated until about 50 mL of acetone remained. The yellow solid was filtered to obtain a yellow solid, washed three times with dichloromethane, and finally filtered to obtain a yellow solid 3-c (4.4 g, 65% yield). 1 HNMR (400MHz, d6-DMSO) δ = 7.50 (m, 4H), 7.30 (m, 6H), 4.07 (b, 2H).

[0310] Step 4: Synthesis of Compound S

[0311]

[0312] Under nitrogen atmosphere, 3-c (4.4 g, 10.6 mmol) was added to DCM (600 mL), cooled to 0 ° C, PIFA (9.3 g, 21.6 mmol) was added in batches, and stirred at room temperature for 3 days. The solution was purple-black. DCM was removed by rotary evaporation to leave about 20 mL, filtered, and washed twice with DCM / PE = 1:1 (50 mL) to obtain a black solid compound S (2.9 g, 66% yield). The product was confirmed to be the target product with a molecular weight of 414. The CV of compound S was measured in DCM, and the LUMO of the compound was obtained to be -4.70 eV. At 6.8*10 -4 Pa under a vacuum condition and heated at a constant temperature of 300°C for 2h for heating sublimation to obtain the product black solid compound S.

[0313] Comparative Synthesis Example 2: Synthesis of Compound T

[0314]

[0315] Step 1: Synthesis of [Intermediate 4-b]

[0316]

[0317] Under nitrogen atmosphere, LDA (40 mL, 2.0 M) was added to THF (200 mL) at -72 ° C (ethanol / dry ice), and a solution of 4-a (5.2 g, 31.0 mmol) in THF (60 mL) was slowly added dropwise, and the reaction was carried out at low temperature for 1 h. Then the temperature was raised to 0 ° C, and a solution of elemental iodine (17.3 g, 68.0 mmol) in THF (60 mL) was slowly added dropwise, and the reaction was carried out at 0 ° C for 1 h. After the reaction was complete, the reaction was quenched with a saturated NH4Cl solution, washed with a saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, and the product was completely dissolved in DCM and filtered with silica gel, and the solvent was dried. The product 4-b (8.9 g, 68% yield) was obtained by recrystallization with DCM and THF. 1 HNMR (400MHz, CDCl3) δ = 7.88 (s, 2H).

[0318] Step 2: Synthesis of [Intermediate 4-c]

[0319]

[0320] Under nitrogen atmosphere, malononitrile (0.32 g, 4.8 mmol) was added to anhydrous DMF (12 mL), and NaH (0.21 g, 5.2 mmol, 60% content) was added in batches at 0°C, stirred for 30 minutes, and then 4-b (0.5 g, 1.2 mmol) and Pd(PPh4)3 (0.14 g) were added, and the temperature was raised to 100°C for 24 hours. After complete conversion, it was poured into ice water, and 2N dilute hydrochloric acid was used to adjust the pH to <1. Solids precipitated, and the solids were filtered out. The solid product was dissolved with acetone, the solvent was dried, and then washed with DCM. Finally, a black solid 4-c (0.24 g, 68% yield) was obtained by filtration, and the solid product was directly used for the next step.

[0321] Step 3: Synthesis of Compound T

[0322]

[0323] Under nitrogen atmosphere, 4-c (0.24 g) was added to DCM (80 mL), cooled to 0°C, PIFA (0.69 g, 1.6 mmol) was added in batches, and stirred at room temperature for 2 days. The solution was purple-black. DCM was removed by rotary evaporation to leave about 10 mL, filtered, and washed twice with DCM / PE = 1:2 (10 mL) to obtain a black solid compound T (0.16 g, 67% yield). 1 HNMR (400 MHz, CDCl3) δ = 8.72 (s, 2H). The CV of compound T was measured in DCM, and the LUMO of the compound was obtained to be -4.64 eV. - 4The product compound T was not obtained by sublimation under the condition of constant temperature 300°C and heating for 30 min under the vacuum condition of Pa.

[0324] For compound T, since the substituents on the five-membered ring are only hydrogen, the molecule is highly planar and the intermolecular forces are strong, resulting in strong stacking between molecules and difficulty in sublimation.

[0325] 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.

[0326] Device Embodiment

[0327] Device Example 1:

[0328] A glass substrate with an 80 nm thick indium tin oxide (ITO) transparent electrode was treated with oxygen plasma and UV ozone. The cleaned glass substrate was dried on a hot plate in a glove box before evaporation. The following materials were heated to a vacuum of about 10 -8 In the case of support, the glass surface is sequentially evaporated at a rate of 0.2-2 angstroms / second. First, the compound I-6 of the present invention is evaporated onto the surface of the glass substrate to form a 10nm thick film as a hole injection layer (HIL). Next, the compound HT1 is evaporated onto the above-mentioned obtained film to form a 120nm thick film as a hole transport layer (HTL). Then, the compound EB1 is evaporated onto the above-mentioned obtained film to form a 5nm thick film as an electron blocking layer (EBL). Then, the compound BH and the compound BD (weight ratio of 96:4) are co-evaporated onto the above-mentioned obtained film to form a 25nm thick film as a light-emitting layer (EML). Then, the compound HB1 is evaporated onto the above-mentioned obtained film to form a 5nm thick film as a hole blocking layer (HBL). Then, 8-hydroxyquinoline-lithium (Liq) and the compound ET1 (weight ratio of 60:40) are co-evaporated onto the above-mentioned obtained film to form a 30nm thick film as an electron transport layer (ETL). Finally, Liq was evaporated to form a 1 nm thick film as an electron injection layer (EIL) and 120 nm thick aluminum was evaporated as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorber to complete the device.

[0329] Device Example 2:

[0330] Device Example 2 was fabricated in the same manner as Device Example 1, except that Compound I-8 was used as the HIL instead of Compound I-6.

[0331] Device Example 3:

[0332] Device Example 3 was prepared in the same manner as Device Example 1, except that Compound I-6 and Compound HT1 (weight ratio of 7:93) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0333] Device Example 4:

[0334] Device Example 4 was prepared in the same manner as Device Example 1, except that Compound I-6 and Compound HT1 (weight ratio of 10:90) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0335] Device Example 5:

[0336] Device Example 5 was prepared in the same manner as Device Example 1, except that Compound I-8 and Compound HT1 (weight ratio of 3:97) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0337] Device Example 6:

[0338] Device Example 6 was prepared in the same manner as Device Example 1, except that Compound I-109 and Compound HT1 (weight ratio of 3:97) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0339] Device Example 7:

[0340] Device Example 7 was prepared in the same manner as Device Example 1, except that Compound I-111 and Compound HT1 (weight ratio of 3:97) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0341] Device Comparison Example 1:

[0342] Comparative Device Example 1 was fabricated in the same manner as in Example 1, except that Comparative Compound S was used as the HIL instead of Compound I-6.

[0343] Device Comparison Example 2:

[0344] Device Comparative Example 2 was prepared in the same manner as Device Example 1, except that Compound HI1 and Compound HT1 (weight ratio of 7:93) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0345] Device comparison example 3:

[0346] Device Comparative Example 3 was prepared in the same manner as Device Example 1, except that Compound HI1 and Compound HT1 (weight ratio of 3:97) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0347] Device comparison example 4:

[0348] Device Comparative Example 4 was prepared in the same manner as Device Example 1, except that Compound S and Compound HT1 (weight ratio of 7:93) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0349] Device comparison example 5:

[0350] Device Comparative Example 5 was prepared in the same manner as Device Example 1, except that Compound S and Compound HT1 (weight ratio of 10:90) were co-evaporated onto the surface of the glass substrate to form a 10 nm thick film as a hole injection layer (HIL).

[0351] 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.

[0352] Table 1 Device structures of device embodiments and comparative examples

[0353]

[0354]

[0355] The material structure used in the device is shown below:

[0356]

[0357] The device data of Example 1, Example 2 and Comparative Example 1, at 10 mA / cm 2 The IVL characteristics were measured, and the voltage, external quantum efficiency (EQE), PE (power efficiency) and lifetime (LT97) were recorded and shown in Table 2.

[0358] Table 2 Device data of Example 1, Example 2 and Comparative Example 1

[0359] Part Number Voltage(V) PE(lm / W) EQE(%) LT97(h) Example 1 4.39 4.39 8.26 912 Example 2 4.52 4.30 8.35 313 Comparative Example 1 4.74 3.83 7.51 6

[0360] As can be seen from Table 2, compared with Comparative Example 1, when Compound I-6 and Compound I-8 of the present invention are used alone as hole injection layer materials in Examples 1 and 2, the prepared device voltage is lower, the PE value is increased by more than 12%, and the EQE is also improved compared to using Compound S alone as a hole injection layer. In particular, the life of the device is improved by more than 50 times. This shows that Compounds I-6 and I-8 disclosed in the present invention have obtained better hole injection capabilities compared to Compound S due to the introduction of substituents with electron-withdrawing groups. The performance of the compounds of the present invention when used alone as a hole injection layer proves that the compounds of the present invention are a class of excellent hole injection materials.

[0361] The device data of Examples 3-5 and Comparative Examples 2-5, at 10 mA / cm 2 The IVL characteristics were measured, and the voltage, PE (power efficiency) and life (LT97) were recorded and shown in Tables 3-5.

[0362] Table 3 Device data of Example 3 and Comparative Examples 2 and 4

[0363] Part Number Voltage(V) PE(lm / W) LT97(h) Example 3 4.29 5.03 1132 Comparative Example 2 4.25 5.09 757 Comparative Example 4 6.76 4.37 160

[0364] As can be seen from Table 3, compared with Example 3 and Comparative Example 2, when the compound I-6 of the present invention and the compound HT1 (7:93) are used in the hole injection layer, the device voltage, PE and EQE are similar compared to the use of the compound HI1 and the compound HT1 (7:93) in the hole injection layer, but the device life is increased by about 50%. Compared with Example 3 and Comparative Example 4, when the compound S and the compound HT1 (7:97) are used in the hole injection layer of Comparative Example 4, the voltage of the device is significantly increased, the PE is also significantly decreased, and the life of the device is far less than that of Example 3. The life of Example 3 is increased by 6 times relative to that of Comparative Example 4, while the life of Comparative Example 4 is too short and does not meet the requirements of commercial materials. It can be seen that when the compound of the present invention is doped for the hole injection material, excellent performance can be obtained compared to the use of the compound HI1 and the compound S in the hole injection layer, and the performance is equivalent to or better than that of the commercial HT1, and it has considerable commercial prospects.

[0365] Table 4 Device data of Example 4 and Comparative Example 5

[0366] Part Number Voltage(V) PE(lm / W) LT97(h) Example 4 4.26 4.95 710 Comparative Example 5 6.12 4.48 157

[0367] As can be seen from Table 4, it can be seen from Example 4 and Comparative Example 5 that when the ratio of dopant compound I-6 and compound S in the hole injection layer is increased to 10%, compound I-6 improves the device life by up to 3.52 times compared to compound S, and has a lower driving voltage and higher power efficiency.

[0368] Table 5 Device data of Example 5, Example 6 and Example 7 and Comparative Example 3

[0369] Part Number Voltage(V) PE(lm / W) LT97(h) Example 5 4.20 5.14 781 Example 6 4.18 5.12 780 Example 7 4.19 5.14 778 Comparative Example 3 4.21 5.10 777

[0370] Compared with Comparative Example 3, the embodiments of Example 5, Example 6 and Example 7 using the compounds I-8, I-109 and I-111 disclosed in the present invention in HIL respectively have all improved in terms of device performance, from voltage, device life to device efficiency, compared with Comparative Example 3 using the commercial material HI1. It fully demonstrates that when the compounds I-8, I-109 and I-111 of the present invention are doped as hole injection materials compared with the compound HI1, excellent device performance can be obtained, reaching performance equivalent to or better than that of the commercial HT1, and having considerable commercial prospects.

[0371] Compounds I-6, I-8, I-109 and I-111 are compounds of the present invention having the structure of Formula 1, and their substituents R are all groups containing electron-withdrawing groups, while compounds S and T are comparative compounds, and their substituents R are groups without electron-withdrawing groups. It can be seen from the device results that the compounds of the present invention in which R is a substituent having an electron-withdrawing group are applied to the device, and whether used alone or doped, more excellent device results can be obtained. When doped for hole injection materials, performance comparable to or better than commercial HT1 can be achieved, and it has considerable commercial prospects.

[0372] The LUMO energy levels of the above compounds I-6, I-8, I-109, I-111, comparative example compounds S and T of the present invention were tested by cyclic voltammetry. The results are shown in the following table:

[0373] Table 6 LUMO energy levels of materials

[0374]

[0375] It can be seen from Table 6 that the actually measured LUMO energy levels of compound S and compound T are not as deep as those of compound I-6, compound I-8, compound I-109 and compound I-111, indicating that the R substituent in the compound having the structure of formula 1 of the present invention is an electron-withdrawing substituent, which can have a deeper LUMO energy level than when R is not an electron-withdrawing substituent, and is more suitable for use as a hole injection material in an organic electronic device.

[0376] Combined with the material device data, compound I-6, compound I-8, compound I-109 and compound I-111 have better device performance than compound S, indicating that the deeper LUMO energy level of the compound is crucial to the performance of the compound device. When the material is used as a hole injection layer dopant, generally the deeper the LUMO energy level, the better the device performance. The LUMO energy level of compound T is shallower than that of compound S, and it can be inferred that the hole injection ability of compound T is also insufficient. In particular, materials with a LUMO energy level below -4.80 eV (DFT calculated LUMO energy level around -5.20 eV and below) will be excellent hole injection materials.

[0377] The LUMO energy levels of some compounds disclosed in the present invention were calculated by DFT [GAUSS-09, B3LYP / 6-311G(d)], and the relevant compounds and their LUMO values ​​are shown in Tables 7 and 8 below:

[0378] Table 7 DFT calculation results (n = 0)

[0379]

[0380] Table 8 DFT calculation results

[0381]

[0382] It can be seen from the DFT theoretical calculations in Tables 7 and 8 that the compound having the structure of Formula 1 of the present invention has a deeper LUMO energy level and is suitable for use as a hole injection material in an organic electronic device. When n=0, as shown in Table 7, R and R N At least one of the compounds has at least one electron-withdrawing group, and the LUMO energy level is -5.20 eV or below. For example, the LUMO energy levels of compounds I-6 and I-8 are much deeper than that of compound S (the LUMO energy level of compound S calculated by the same calculation method is -4.83 eV). Because of the introduction of more electron-withdrawing groups on the substituent R, the LUMO energy level of I-8 is also deeper than that of I-6. When R and R L When both are electron-withdrawing groups, compared with R and R L When at least one electron-withdrawing group is introduced into at least one of the two, the LUMO energy level is also deeper, such as compound LIOA-23 vs. compound LIOA-5.

[0383] In summary, it can be concluded from the above results that the compound having the structure of Formula 1 of the present invention has the importance of electron-withdrawing groups. The compound of the present invention is a very important charge transfer material, especially has an incomparable advantage in hole transport, is easy to prepare organic semiconductor devices, and is suitable for different types of organic electronic devices, including but not limited to fluorescent OLED, phosphorescent OLED, white light OLED, stacked OLED, OTFT, OPV, etc.

[0384] 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 shown in Formula 1: in, Each time L appears, it is selected from or any combination thereof; Ring AA is a conjugated structure of 4-30 ring atoms having at least one intracyclic double bond; n is selected from integers from 0 to 10, the same or different at each occurrence; Each time Y appears, it is selected from CR L and N; Ring A is identical or different at each occurrence and is a 5-membered heterocyclic ring, and the 5-membered heterocyclic ring contains an intracyclic double bond, at least one N atom and at least one heteroatom W; W is identical or different at each occurrence and is selected from O, S, Se and NR N The group composed of; X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"'; R and R L Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; R, R", R"', R L and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, 0 ring atoms, a heterocyclic group, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; When L is selected from When n=0, the substituents R and R N At least one of them is a group having at least one electron-withdrawing group; When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group; Adjacent substituents R", R"' can be optionally linked to form a ring; Adjacent substituents R, R L can be optionally linked to form a ring; when adjacent substituents R L When connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms.

2. The compound of claim 1, wherein the substituents R, R L and R N At least one of them is a group having at least one electron withdrawing group; preferably R and R L At least one of the groups is a group having at least one electron withdrawing group.

3. The compound as claimed in claim 1 or 2, wherein the two ends of L in Formula 1 are connected to The ring A in the formula 1 comprises CR, and R is a group having at least one electron withdrawing group; preferably, the rings connected to both sides of L in the formula 1 Each occurrence is the same or different and is selected from any structure represented by Formula 2 to Formula 5: in, In equations 2 to 5, X, W, and R have the same definitions as in claim 1; "**" represents the connection position of L in Formulae 2 to 5 and Formula 1.

4. The compound according to any one of claims 1 to 3, wherein each occurrence of L is identically or differently selected from the structures shown in Formula 6 and Formula 6A and combinations thereof: in, In Formula 6 and Formula 6A, n is selected from integers from 0 to 10, the same or different at each occurrence; Y and Z are selected from CR L or N; R L Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; Adjacent substituent R L can optionally be linked to form a ring; "#" and "##" represent the connection position of Formula 6 and Formula 6A to Ring A or L in Formula 1.

5. A compound as described in any one of claims 1 to 4, wherein L is n is 0, and the compound has any structure represented by Formula I to Formula XVI: in, In Formula I to Formula XVI, X, W, and R have the same definitions as in claim 1; Preferably, the compound has a structure represented by one of Formula I, Formula II, Formula V, Formula IX, Formula X, Formula XI and Formula XVI.

6. The compound according to any one of claims 1 to 4, wherein the compound has any structure represented by Formula LI and Formula LIA: in, In Formula LI and Formula LIA, Y and Z each appear the same or differently selected from CR L and N; X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"'; W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of; R, R", R"', R L and R N Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, 0 ring atoms, a heterocyclic group, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group; Adjacent substituents R", R"' can be optionally linked to form a ring; Adjacent substituents R, R L can be optionally linked to form a ring; when adjacent substituents R L When connected to form a ring, the formed ring has at least 4 ring atoms; when adjacent substituents R are connected to form a ring, the formed ring has at least 6 ring atoms; Preferably, R, R L and R N At least one of the groups is a group having at least one electron withdrawing group.

7. The compound according to any one of claims 1 to 4, wherein the compound has a structure represented by formula II-I: in, K is selected from O, S, Se and CR in the same or different manner at each occurrence A R B The group composed of; X is selected, at each occurrence, identically or differently, from the group consisting of Se, NR' and CR"R"'; W is selected from O, S, Se and NR at each occurrence, the same or different N The group composed of; J is selected from O, S, Se and NR in the same or different manner at each occurrence NJ The group composed of; Preferably, J is selected, identically or differently, from NR NJ ; R A , R B , R”, R”', R N and NR NJ Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; R' is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, 0 ring atoms, a heterocyclic group, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted alkynyl group having 2-20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; Adjacent substituent R A and R B can optionally be linked to form a ring; In Formula II-I, R A , R B , R N and R NJ At least one of the R is a group having at least one electron withdrawing group, and / or at least one of the K is O; When X is selected from NR' or CR"R"', at least one of R', R" and R"' is a group having at least one electron withdrawing group; Adjacent substituents R", R"' can be optionally linked to form a ring.

8. A compound as claimed in any one of claims 1 to 7, wherein Y is selected from CR L .

9. The compound as claimed in any one of claims 1 to 8, wherein X is selected identically or differently at each occurrence from CR"R"'.

10. The compound of any one of claims 1 to 9, wherein W is selected, identically or differently, from O, S or Se at each occurrence; preferably, W is selected, identically or differently, from O or S at each occurrence; more preferably, W is O.

11. The compound of any one of claims 1 to 9, wherein W is identically or differently selected from NR N , and R N each occurrence is identically or differently selected from the group consisting of: 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 alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; Preferably, R N Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

12. The compound of any one of claims 1 to 11, wherein at least one of R is a group having at least one electron withdrawing group.

13. The compound of any one of claims 1 to 11, wherein at least one of R is a group having at least one electron withdrawing group; wherein R', R", R'", R L , R N and R NJ Each of is a group having at least one electron withdrawing group.

14. The compound of any one of claims 1 to 12, wherein at least one of R is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Preferably, at least one of R is an aryl group having 6 to 30 carbon atoms substituted with at least one electron withdrawing group, a heteroaryl group having 3 to 30 carbon atoms substituted with at least one electron withdrawing group, or a combination thereof.

15. The compound of any one of claims 1 to 11, wherein R at each occurrence is identically or differently a group having at least one electron withdrawing group.

16. The compound of any one of claims 1 to 11, wherein R 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; Preferably, R, at each occurrence, has at least one electron withdrawing group substituted aryl group having 6 to 30 carbon atoms, has at least one electron withdrawing group substituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

17. The compound of any one of claims 1 to 16, wherein the Hammett constant of the electron withdrawing group is ≥ 0.05, preferably ≥ 0.3, more preferably ≥ 0.

5.

18. The compound of any one of claims 1 to 16, wherein the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring radical, or any of the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, azaaromatic ring radical: having 1-2 0 carbon atoms, alkyl groups having 0 carbon atoms, cycloalkyl groups having 3-20 ring carbon atoms, heteroalkyl groups having 1-20 carbon atoms, heterocyclyl groups having 3-20 ring atoms, aralkyl groups having 7-30 carbon atoms, alkoxy groups having 1-20 carbon atoms, aryloxy groups having 6-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alkylsilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and combinations thereof; Preferably, the electron withdrawing group is selected from the group consisting of F, CF3, CHF2, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazine, and combinations thereof.

19. A compound as described in any one of claims 1 to 8, wherein X is identically or differently selected from the group consisting of the following structures at each occurrence: With, in, Each occurrence of V, U and T is identical or different and is selected from CR v R u , NR v , a group consisting of O, S and Se; wherein Ar is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Among them, R1, Q, R a , R b , R c , R d , R e , R f , R g , R h , R v and R u is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, 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 cycloalkyl having 7 to 30 carbon atoms, atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof; Preferably, R1 is selected, at each occurrence, identically or differently, from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and its combination; wherein Q is a group having at least one electron withdrawing group, and for any of the above structures, when R a , R b , R c , R d , R e , R f , R g , R h , R v and R u When one or more of the above are present, at least one of them is a group having at least one electron-withdrawing group; preferably, the group having at least one electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazine, and combinations thereof; Adjacent substituents R1, R a , R b , R c , R d , R e , R f , R g , R h , R v and R u can optionally be linked to form a ring; "*" represents the connection position of X having the above structure and Ring A in Formula 1.

20. A compound as described in any one of claims 1 to 8 and 19, wherein X is identically or differently selected from the group consisting of the following structures at each occurrence: With, Preferably, wherein X is selected from 21. The compound according to any one of claims 1 to 11, wherein R, R L , R N and R NJ is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 3 carbon atoms, 0 carbon atom aralkyl group, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryloxy group having 6-30 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, and combinations thereof; Preferably, R, R L , R N and R NJ is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, CN, vinyl substituted by one or more of CN or CF3, acetylene substituted by one of CN or CF3 substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazine, pyridyl, diphenylboryl, oxaboranthenyl, and combinations thereof.

22. A compound as described in any one of claims 1 to 11, 21, wherein R, R L , R N and R NJ are selected, at each occurrence, identically or differently, from the group consisting of: Preferably, R, R L , R N and R NJ In each occurrence, identically or differently selected from the group consisting of: Where "﹋" represents R with the above structure and formula 1, R L The connection position with L; "﹋" also represents when J is selected from NR NJ When R NJ The connection position with N; "﹋" also represents when W is selected from NR N When R N The connection position with N.

23. The compound of claims 1 to 5, wherein the compound is selected from the group consisting of Compound I-1 to Compound I-114, Compound II-1 to Compound II-108, Compound III-1 to Compound III-108, Compound IV-1 to Compound IV-108, Compound V-1 to Compound V-108, Compound VI-1 to Compound VI-108, Compound VII-1 to Compound VII-108, Compound VIII-1 to Compound VIII-108, Compound IX-1 to Compound IX-108, Compound X-1 to Compound X-108, Compound XI-1 to Compound XI-108, Compound XII-1 to Compound XII-108, Compound XIII-1 to Compound XIII-108, Compound XIV-1 to Compound XIV-108, Compound XV-1 to Compound XV-108, Compound XVI-1 to Compound XVI-108; in, Compounds I-1 to I-108 have the structure of Formula I: In Formula I, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds II-1 to II-108 have the structure of formula II: In Formula II, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds III-1 to III-108 have the structure of formula III: In Formula III, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds IV-1 to IV-108 have the structure of formula IV: In Formula IV, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds V-1 to V-108 have the structure of formula V: In formula V, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds VI-1 to VI-108 have the structure of formula VI: In Formula VI, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds VII-1 to VII-108 have the structure of formula VII: In Formula VII, two Xs are the same, two Ws are the same, two Rs are the same, and X, W and R correspond to atoms or groups selected from the following table: Among them, compounds VIII-1 to VIII-108 have the structure of formula VIII: In Formula VIII, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds IX-1 to IX-108 have the structure of Formula IX: In Formula IX, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds X-1 to X-108 have the structure of formula X: In formula X, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XI-1 to XI-108 have the structure of formula XI: In formula XI, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XII-1 to XII-108 have the structure of formula XII: In Formula XII, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XIII-1 to XIII-108 have the structure of formula XIII: In Formula XIII, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XIV-1 to XIV-108 have the structure of formula XIV: In Formula XIV, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XV-1 to XV-108 have the structure of formula XV: In formula XV, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table: Among them, compounds XVI-1 to XVI-108 have the structure of formula XVI: In Formula XVI, two Xs are the same, two Ws are the same, two Rs are the same, and X, W, and R correspond to atoms or groups selected from the following table:

24. The compound of any one of claims 1, 3, 4 and 6, wherein the compound is selected from Compound LIO-1 to Compound LIO-108, Compound LIOA-1 to Compound LIOA-66; in, Compounds LIO-1 to LIO-108 have the structure of Formula LIO: In the formula LIO, the two Xs are the same, the two Ws are the same, the two Rs are the same, and the two Zs are the same and are CR L , and X, W, R, and R L They correspond to atoms or groups selected from the following table: Among them, compounds LIOA-1 to LIOA-66 have the structure of formula LIOA: In the formula LIOA, two Xs are the same, two Ws are the same, two Rs are the same, and four Zs are the same and are CR L , and X, W, R, and R L They correspond to atoms or groups selected from the following table: 。 25. The compound of claim 7, wherein the compound is selected from the group consisting of Compound II-IO-1 to Compound II-IO-60; in, Compounds II-IO-1 to II-IO-60 have the structure of formula II-IO: In formula II-IO, two Xs are the same, two Ws are the same, and J is NR NJ , and X, W, R NJ They correspond to atoms or groups selected from the following table: 。 26. An electroluminescent device comprising: anode, cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 25. 27 . The electroluminescent device according to claim 26 , wherein the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is formed of the compound alone.

28. The electroluminescent device of claim 26, wherein the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer further comprises at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000; Preferably, the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:

100.

29. The electroluminescent device of claim 26, wherein the electroluminescent device comprises a plurality of stacked layers between an anode and a cathode, the stacked layers comprising a first light emitting layer and a second light emitting layer, wherein: The first stacked layer includes a first light-emitting layer, the second stacked layer includes a second light-emitting layer, and the charge generation layer is disposed between the first stacked layer and the second stacked layer, wherein the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer; The p-type charge generation layer comprises the compound; preferably, the p-type charge generation layer further comprises at least one hole transport material, wherein the molar doping ratio of the compound to the hole transport material is 10000:1 to 1:10000; preferably, the molar doping ratio of the compound to the hole transport material is 10:1 to 1:

100.

30. The electroluminescent device of claim 28 or 29, wherein the hole transport material comprises a compound having a triarylamine unit, a spirobifluorene compound, a pentacene compound, an oligothiophene compound, an oligophenyl compound, an oligophenylene vinyl compound, an oligofluorene compound, a porphyrin complex or a metal phthalocyanine complex.

31. The electroluminescent device of claim 29, wherein the charge generation layer further comprises a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, wherein the buffer layer comprises the compound.

32. The electroluminescent device according to any one of claims 26 to 31, which is prepared by a vacuum evaporation method.

33. A compound formulation comprising the compound of any one of claims 1-25.

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