An organic electroluminescent material and its device

Abstract

An organic electroluminescent material and device are disclosed. The organic electroluminescent material is a novel compound containing dehydrobenzoxazole, dehydrobenzothiazole, dehydrobenzoseleazole, dehydrobenzimidazole and their similar structures. These novel compounds have properties such as a deep LUMO, strong electron-accepting ability, strong charge transfer ability, and low volatility. Due to the unique properties of these novel compounds, they have broad potential application prospects in the field of organic semiconductors, especially their potential uses as p-type conductive doping materials, charge transport layer materials, hole injection layer materials, and electrode materials for organic semiconductors.

Description

Technical Field

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound having the structure of Formula 1, and an organic electroluminescent device and a compound combination comprising the compound. Background Art

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

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

[0004] OLEDs can be classified into three different types according to their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are 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 use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlet and triplet states, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have 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 energy gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have an exact structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.

[0006] There are various methods for manufacturing OLEDs. 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. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.

[0007] The emission color of OLEDs can be achieved through the design of the emitter structure. OLEDs can include one or more emission layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue color unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.

[0008] Most of the current electron acceptor materials have various problems and are difficult to be used commercially. For example, the sublimation temperatures of common inorganic materials such as FeCl3 and MoO3 are very high, they are unstable in the manufacturing process, or have poor thermal stability. And FeCl3, for example, has strong corrosiveness and causes great damage to the evaporation equipment. Another example is that the LUMO of the organic material HATCN is relatively shallow, its electron acceptance ability is weak, and its charge transfer ability is weak. So when used as a p-type conductive dopant, the effect is very poor. Moreover, HATCN has strong crystallinity and there are problems with film formation in the device. Although F4-TCNQ and F6-TCNNQ have relatively deep LUMOs and strong charge transfer abilities and are widely used as p-type conductive dopants in the field of electroluminescence, because of their high volatility (the sublimation temperature of F4-TCNQ is only 120 °C under a vacuum of 2.2×10 - 4 Pa), and low evaporation temperature, which affects the control of the deposition of this material in the manufacturing process of OLED devices, as well as the reproducibility during the production process and the thermal stability of the device. So their application in the commercial field is relatively cautious. Given that the hole injection layer has a great impact on the voltage, efficiency and lifespan of OLED devices, it is very important and urgent in the industry to develop p-type conductive doping materials with high thermal stability, high film-forming property and deep LUMO. The structures of the above-mentioned HATCN, F4-TCNQ and F6-TCNNQ are as follows:

[0009] Summary of the Invention

[0010] The present invention aims to provide a series of compounds with the structure of Formula 1 to solve at least part of the above problems. The compounds are novel compounds containing dehydrobenzoxazole, dehydrobenzothiazole, dehydrobenzoseleazole, dehydrobenzimidazole and their similar structures. These novel compounds have strong electron acceptance ability and relatively large electron affinity. Due to the unique properties of these novel compounds, they have potential broad application prospects in the field of organic semiconductors, especially their potential uses as p-type conductive doping materials, charge transport layer materials, hole injection layer materials and electrode materials for organic semiconductors.

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

[0012]

[0013] Wherein Y is the same or different each time it appears and is selected from CR’’R”’, NR’, O, S or Se;

[0014] W is the same or different each time it appears and is selected from O, S, Se or NR N ;

[0015] X1 to X3 are the same as or different from each other each time they appear and are independently selected from CR or N;

[0016] L is the same as or different from each other each time it appears and is independently selected from a cyclic conjugated structure having 4 to 30 ring atoms with at least one double bond within the ring and substituted with one or more substituents R L ';

[0017] R, R N , R', R", R''' and R L ' are the same as or different from each other each time they appear and are independently selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphinyl, 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 heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, and combinations thereof;

[0018] wherein at least one of R, R N , R', R" and R''' is a group having at least one electron-withdrawing group;

[0019] m, n are integers selected from 0 to 1;

[0020] Adjacent substituents R, R N , R', R", R''' and R L ' can optionally be connected to form a ring.

[0021] According to another embodiment of the present invention, there is also disclosed an electroluminescent device, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound described in the above embodiment.

[0022] According to another embodiment of the present invention, there is also disclosed a compound combination, which contains the compound described in the above embodiment.

[0023] The compounds with the structure of Formula 1 disclosed by the present invention are novel compounds containing dehydrobenzoxazole, dehydrobenzothiazole, dehydrobenzisoselenazole, dehydrobenzimidazole and their similar structures. These novel compounds have properties such as deep LUMO, strong electron-accepting ability, strong charge transfer ability, and low volatility. Due to the unique properties of these novel compounds, they have broad potential application prospects in the field of organic semiconductors, especially their potential uses as p-type conductive doping materials, charge transport layer materials, hole injection layer materials, and electrode materials for organic semiconductors. Brief Description of the Drawings

[0024] Figure 1 It is a schematic diagram of an organic light-emitting device that can contain the compounds and compound combinations disclosed herein.

[0025] Figure 2 It is a schematic diagram of another organic light-emitting device that can contain the compounds and compound combinations disclosed herein. Detailed Description of the Invention

[0026] OLEDs can be fabricated on various substrates such as glass, plastic, and metal. Figure 1 Schematically and non-limitingly shows an organic light-emitting device 100. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The device 100 can 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 fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.

[0027] Each of these layers has more examples. For example, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. 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, incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety. U.S. Patents Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of the barrier layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties. Examples of the injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety.

[0028] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. 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 sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve a desired emission spectrum.

[0029] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0030] The OLED also requires a encapsulation layer, as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0031] Devices manufactured in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) incorporating the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0032] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0033] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, there may be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

[0034] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0035] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0036] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical limit by 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).

[0037] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of singlet excited state repopulation can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.

[0038] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that 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 as donor-acceptor charge transfer (CT) type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) with an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0039] Definition of substituent terms

[0040] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0041] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls 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. Additionally, the alkyl can be optionally substituted.

[0042] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The 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, and 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0043] Heteroalkyl - as used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0044] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 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 - methylethenyl, styryl, 2,2 - diphenylethenyl, 1,2 - diphenylethenyl, 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, cycloheptatrieneyl, cyclooctenyl, cyclooctatetraeneyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0045] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 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, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0046] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl 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-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylenyl, 3,4-xylenyl, 2,5-xylenyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0047] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.

[0048] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and its nitrogen - containing analogues. Additionally, the heteroaryl can be optionally substituted.

[0049] Alkoxy - As used herein, it is represented by -O - alkyl, -O - cycloalkyl, -O - heteroalkyl or -O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl are the same as those described above. The 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, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0050] Aryloxy - As used herein, it is represented by -O - aryl or -O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0051] 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,

[0052] 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.

[0053] 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.

[0054] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.

[0055] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.

[0056] 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.

[0057] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 - 20 carbon atoms, unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, unsubstituted heteroalkyl having 1 - 20 carbon atoms, unsubstituted heterocycloalkyl having 3 - 20 ring atoms, unsubstituted aralkyl having 7 - 30 carbon atoms, unsubstituted alkoxy having 1 - 20 carbon atoms, unsubstituted aryloxy having 6 - 30 carbon atoms, unsubstituted alkenyl having 2 - 20 carbon atoms, unsubstituted alkynyl having 2 - 20 carbon atoms, unsubstituted aryl having 6 - 30 carbon atoms, unsubstituted heteroaryl having 3 - 30 carbon atoms, unsubstituted alkylsilyl having 3 - 20 carbon atoms, unsubstituted arylsilyl having 6 - 20 carbon atoms, unsubstituted alkylgermyl having 3 - 20 carbon atoms, unsubstituted arylgermyl having 6 - 20 carbon atoms, unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0058] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.

[0059] In the compounds mentioned in the present disclosure, the 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. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0060] Among the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure indicates polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituents present at multiple available substitution positions can be of the same structure or different structures.

[0061] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring, the adjacent substituents in the compounds cannot be linked to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, which includes both the case where adjacent substituents can be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be linked to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, 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.

[0062] In the present invention, the number of ring atoms represents the number of atoms constituting the ring itself of a compound with a structure in which atoms are bonded in a ring (for example: monocyclic compound, fused ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the number of ring atoms. Regarding the "number of ring atoms" described herein, it has the same meaning unless otherwise specified.

[0063] The expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0064]

[0065] The expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0066]

[0067] The expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away being linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0068]

[0069] In addition, the expression that adjacent substituents can optionally be joined to form a ring is also intended to be taken to mean that, in the case where one of two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following formula:

[0070]

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

[0072]

[0073] wherein Y is the same or different each occurrence and is selected from CR”R”’, NR’, O, S or Se;

[0074] W is the same or different each occurrence and is selected from O, S, Se or NR N ;

[0075] X1 to X3 are the same or different each occurrence and are selected from CR or N;

[0076] L is the same or different each occurrence and is selected from a cyclic conjugated structure having 4 to 30 ring atoms with at least one double bond in the ring and substituted with one or more substituents R L ’;

[0077] R, R N , R’, R”, R”’ and R L’Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphonyloxy, hydroxy, mercapto, 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 heterocyclic group 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof;

[0078] wherein at least one of R, R N , R', R'' and R''' is a group having at least one electron-withdrawing group;

[0079] m, n are integers selected from 0-1;

[0080] The adjacent substituents R, R N , R', R'', R''' and R L ' can optionally be linked to form a ring.

[0081] In this embodiment, "the adjacent substituents R, R N , R', R'', R''' and R L ' can optionally be linked to form a ring" means that any two adjacent substituents among the substituents R, R N , R', R'', R''' and R L ', for example, between two Rs, between two R L ', between R and R N , between R'' and R''', any one or more of these substituents can optionally be linked to form a ring. Obviously, these adjacent substituents R, R N , R', R'', R''' and R L ' may also not be linked to form a ring.

[0082] In this embodiment, when m or n is 0, it means that the L does not exist. At this time, Y is directly connected to the six-membered and five-membered conjugated ring containing X1 to X3 and W in Formula 1.

[0083] According to one embodiment of the present invention, wherein each occurrence of W is independently selected from O, S or Se.

[0084] According to one embodiment of the present invention, wherein each occurrence of W is independently selected from O or S.

[0085] According to one embodiment of the present invention, wherein each occurrence of W is independently O.

[0086] According to one embodiment of the present invention, wherein m + n ≤ 1.

[0087] According to one embodiment of the present invention, wherein m + n = 0.

[0088] According to one embodiment of the present invention, at least one of X1 to X3 is selected from CR.

[0089] According to one embodiment of the present invention, at least two of X1 to X3 are selected from CR.

[0090] According to one embodiment of the present invention, each occurrence of Y is independently selected from CR”R”’ or NR’, and R’, R” and R”’ are groups having at least one electron-withdrawing group.

[0091] According to one embodiment of the present invention, each occurrence of Y is independently selected from CR”R”’ or NR’, and R, R N , R’, R” and R”’ are groups having at least one electron-withdrawing group.

[0092] According to one embodiment of the present invention, each occurrence of Y is independently selected from CR”R”’ or NR’, and R, R N , R’, R”, R”’ and R L ’ are groups having at least one electron-withdrawing group.

[0093] According to one embodiment of the present invention, the Hammett constant of the electron-withdrawing group is ≥ 0.05, preferably ≥ 0.3, more preferably ≥ 0.5.

[0094] The Hammett substituent constant value of the electron-withdrawing group of the present invention is ≥ 0.05, and the electron-withdrawing ability is strong, which can significantly reduce the LUMO energy level of the compound and achieve the effect of improving the charge mobility.

[0095] It should be noted that the Hammett substituent constant values include Hammett para-substituent constants and / or meta-substituent constants. As long as one of the para-substituent constant and the meta-substituent constant satisfies being greater than or equal to 0.05, it can be used as the preferred electron-withdrawing group of the present invention.

[0096] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphonyloxy, azaaryl, and any of the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphonyloxy, azaaryl: 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof.

[0097] 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, pyrimidinyl, triazinyl, and combinations thereof.

[0098] According to one embodiment of the present invention, Y is the same or different each time it appears and is selected from the group consisting of the following structures: O, S, Se,

[0099]

[0100] Wherein, each occurrence of R1 is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphinyl, 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 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof;

[0101] Preferably, each occurrence of R1 is the same as or different from each other and is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazinyl, and combinations thereof;

[0102] Wherein, each occurrence of V and W is the same as or different from each other and is selected from CR v R w ,NR v ,O, S, Se;

[0103] Wherein, each occurrence of Ar is the same as or different from each other and is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms;

[0104] Wherein, A, R a ,R b ,R c ,R d ,R e ,R f ,R g ,R h ,R v and R wThe same or different at each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphinyl, 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 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof;

[0105] wherein A is a group having at least one electron-withdrawing group, and for any of said structures, when R a , R b , R c , R d , R e , R f , R g , R h , R v and R w appears one or more times, at least one of R a , R b , R c , R d , R e , R f , R g , R h , R v and R w 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, triazinyl, and combinations thereof.

[0106] In this embodiment, "*" represents the position where Y is connected to L described in Formula 1 or the six-membered and five-membered conjugated ring containing X1 to X3 and W. When m or n is 0, "*" represents the position where Y is connected to the six-membered and five-membered conjugated ring containing X1 to X3 and W described in Formula 1, and when m or n is 1, "*" represents the position where Y is connected to L described in Formula 1.

[0107] According to one embodiment of the present invention, wherein Y is the same or different each time it appears and is selected from the group consisting of:

[0108] O, S, Se,

[0109] In this embodiment, "*" represents the position where Y is connected to L described in Formula 1 or the six-membered and five-membered conjugated ring containing X1 to X3 and W. That is, when m or n is 0, "*" represents the position where Y is connected to the six-membered and five-membered conjugated ring containing X1 to X3 and W described in Formula 1, and when m or n is 1, "*" represents the position where Y is connected to L described in Formula 1.

[0110] According to one embodiment of the present invention, wherein R and R

[0111] In this embodiment, "*" represents the position where Y is connected to L described in Formula 1 or the six-membered and five-membered conjugated ring containing X1 to X3 and W. That is, when m or n is 0, "*" represents the position where Y is connected to the six-membered and five-membered conjugated ring containing X1 to X3 and W described in Formula 1, and when m or n is 1, "*" represents the position where Y is connected to L described in Formula 1.

[0112] According to one embodiment of the present invention, wherein, R and R NEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphinyl, an unsubstituted alkyl having 1 to 20 carbon atoms, an unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted alkoxy having 1 to 20 carbon atoms, an unsubstituted alkenyl having 2 to 20 carbon atoms, an unsubstituted aryl having 6 to 30 carbon atoms, an unsubstituted heteroaryl having 3 to 30 carbon atoms, and any of the following groups substituted with one or more groups selected from halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, and phosphinyl: an alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 20 ring carbon atoms, an alkoxy having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0113] According to one embodiment of the present invention, wherein R and R N Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, a vinyl substituted with one or more of CN or CF3, an ethynyl substituted with one of CN or CF3, dimethylphosphinyl, diphenylphosphinyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, a phenyl or biphenyl substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazinyl, diphenylboranyl, oxaboranthryl, and combinations thereof.

[0114] According to one embodiment of the present invention, wherein L each occurrence is the same as or different from and is selected from the group consisting of the following structures:

[0115]

[0116] wherein,

[0117] W L Each occurrence is the same as or different from and is selected from O, S, Se or NR N ';

[0118] X LEach occurrence is the same as or different from and is selected from CR L or N;

[0119] R L and R N ' are each occurrence the same as or different from and are selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphinyl, hydroxyl, mercapto, 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 heterocyclic group 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof;

[0120] "*" represents the position where the formula L-1 to formula L-13 are connected to the Y group in formula 1;

[0121] "#" represents the position where the formula L-1 to formula L-13 are connected to the six-membered and five-membered conjugated ring containing X1 to X3 and W in formula 1;

[0122] Adjacent substituents R L and R N ' can optionally be connected to form a ring.

[0123] In this embodiment, "adjacent substituents R L and R N ' can optionally be connected to form a ring" means any two adjacent substituents among the substituents R L and R N ', for example, between two R L s, between R L and R N ', any one or more of these substituents can optionally be connected to form a ring. Obviously, these adjacent substituents R L and R N ' may also not be connected to form a ring.

[0124] According to one embodiment of the present invention, L is the same or different each time it appears and is selected from L-2, L-11 or L-12.

[0125] According to one embodiment of the present invention, the compound has a structure represented by any one of Formula F1 to Formula F10:

[0126]

[0127] Wherein,

[0128] Y is the same or different each time it appears and is selected from O, S, Se, CR”R”’ or NR’;

[0129] W is the same or different each time it appears and is selected from O, S, Se or NR N ;

[0130] X1 to X3 are the same or different each time they appear and are selected from CR or N;

[0131] W L is the same or different each time it appears and is selected from O, S, Se or NR N ’;

[0132] X L is the same or different each time it appears and is selected from CR L or N;

[0133] R, R N ,R L ,R’, R”, R”’ and R N ’ are the same or different each time they appear and are selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boranyl, sulfinyl, sulfonyl, phosphonyloxy, 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 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, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, and combinations thereof;

[0134] R, R N , R’, R” and R”’ are each independently a group having at least one electron-withdrawing group;

[0135] Adjacent substituents R, R N , R L , R’, R”, R”’ and R N ’ may optionally be linked to form a ring.

[0136] In this embodiment, “adjacent substituents R, R N , R L , R’, R”, R”’ and R N ’ may optionally be linked to form a ring” means that any two adjacent substituents among substituents R, R N , R’, R”, R”’, R L and R N ’, for example, between two R’s, between two R L ’s, between R and R N ’, between R” and R”’, between R L and R N ’, any one or more of these substituents may optionally be linked to form a ring. Obviously, these adjacent substituents R, R N , R L , R’, R”, R”’ and R N ’ may also not be linked to form a ring.

[0137] According to one embodiment of the present invention, wherein R, R L , R N , R N ’ are each independently selected, each time they appear, from the group consisting of the following structures:

[0138]

[0139]

[0140]

[0141] wherein represents the connection position of the R group having the above structure to the six-membered ring containing X1 to X3 in Formula 1; or represents the connection position of the R L group to the group L; or represents the connection position of R N to N when W is selected from NR N ; or represents the connection position of R L ’ to N when W N ’ is selected from NR N ’.

[0142] According to one embodiment of the present invention, the compound is selected from the group consisting of compound F1-1 to compound F1-436, compound F2-1 to compound F2-160, compound F3-1 to compound F3-160, compound F4-1 to compound F4-96, compound F5-1 to compound F5-96, compound F6-1 to compound F6-96, and compound F7-1 to compound F7-96;

[0143] Among them, compound F1-1 to compound F1-436 have the structure shown in formula F1:

[0144]

[0145] In formula F1, two Ys are the same, and Y, X1, X2, X3, and W are respectively selected from the atoms or groups in the following table:

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] Among them, compound F2-1 to compound F2-160 have the structure shown in formula F2':

[0153]

[0154] In formula F2', two Ys are the same, and Y, X2, X L , W, W L are respectively selected from the atoms or groups in the following table:

[0155]

[0156]

[0157] Among them, compound F3-1 to compound F3-160 have the structure shown in formula F3':

[0158]

[0159] In formula F3', two Ys are the same, and Y, X2, X L , W, W LCorrespond to atoms or groups selected from the following table respectively:

[0160]

[0161]

[0162] Among them, compounds F4-1 to F4-96 have the structure shown in formula F4':

[0163]

[0164] In formula F4', the two Ys are the same, and Y, X2, X L , and W correspond to atoms or groups selected from the following table respectively:

[0165]

[0166]

[0167]

[0168] Among them, compounds F5-1 to F5-96 have the structure shown in formula F5':

[0169]

[0170] In formula F5', the two Ys are the same, and Y, X2, X L , and W correspond to atoms or groups selected from the following table respectively:

[0171]

[0172]

[0173] Among them, compounds F6-1 to F6-96 have the structure shown in formula F6':

[0174]

[0175] In formula F6', the two Ys are the same, and X2 is the same as X L , and Y, X2, X L , W, W L correspond to atoms or groups selected from the following table respectively:

[0176]

[0177]

[0178] Among them, compounds F7-1 to F7-96 have the structure shown in formula F7':

[0179]

[0180] In formula F7', the two Ys are the same, and X2 is the same as X L same, and Y, X2, X L , W, W L are respectively selected from the atoms or groups in the following table:

[0181]

[0182]

[0183] In this embodiment, compound F1-1 has the structure represented by formula F1:

[0184] wherein, the two Ys are the same, both being A1 X1 is C-B1 (C represents a carbon atom, B1 is ), X2 and X3 are C-B16 (C represents a carbon atom, B16 is ), W is O, that is, the structure of compound F1-1 is Similarly, the structures of other compounds in this embodiment can be clearly known.

[0185] According to an embodiment of the present invention, an electroluminescent device is also disclosed, which includes: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compound described in any of the foregoing embodiments.

[0186] According to an embodiment of the present invention, 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 solely by the compound.

[0187] According to an embodiment of the present invention, 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 contains 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.

[0188] According to an embodiment of the present invention, 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 contains at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0189] According to an embodiment of the present invention, the electroluminescent device includes at least two light-emitting units, the organic layer is a charge generation layer and is disposed between the at least two light-emitting units, and the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer.

[0190] According to an embodiment of the present invention, the p-type charge generation layer contains the compound.

[0191] According to an embodiment of the present invention, the p-type charge generation layer further contains at least one hole transport material, and the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000.

[0192] According to an embodiment of the present invention, the p-type charge generation layer further contains at least one hole transport material, and the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0193] According to an embodiment of the present invention, the hole transport material contains a compound having a triarylamine unit, a spirobifluorene compound, a pentacene compound, an oligothiophene compound, an oligophenyl compound, an oligo(phenylene vinylene) compound, an oligofluorene compound, a porphyrin complex or a metal phthalocyanine complex.

[0194] According to an embodiment of the present invention, the charge generation layer further contains a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, and the buffer layer also contains the compound.

[0195] According to an embodiment of the present invention, the electroluminescent device is prepared by a vacuum evaporation method.

[0196] According to an embodiment of the present invention, a compound combination is also disclosed, which contains the compound described in any of the foregoing embodiments.

[0197] In combination with other materials

[0198] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132-0161 of US Patent Application US2016 / 0359122A1, the entire content of which is 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.

[0199] The materials described herein as being specific layers useful in organic light emitting devices can be used in combination with a variety of other materials present in the devices. For example, the compounds disclosed herein can be used alone as a hole injection layer or in combination with a hole transport material (in a molar doping ratio from 10,000:1 to 1:10,000) as a hole injection layer, and can be combined with a variety of light emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of U.S. Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non - limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0200] In the organic light emitting device described in the present invention, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer can be included; wherein the light emitting layer includes at least one light emitting dopant and at least one host compound, and the light emitting dopant can be a fluorescent light emitting dopant, a delayed fluorescence light emitting dopant, and / or a phosphorescent light emitting dopant. Figure 1 An organic light emitting device 100 is schematically and non - restrictively shown. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6 - 10 of U.S. Patent US7,279,704B2, the entire content of which is incorporated herein by reference.

[0201] Conventional hole transport materials in the prior art can be used in the hole transport layer. For example, the hole transport layer can typically but non - restrictively include the following hole transport materials:

[0202]

[0203] Conventional electron transport materials in the prior art can be used in the electron transport layer. For example, the electron transport layer can typically but non - restrictively include the following electron transport materials:

[0204]

[0205] Conventional light emitting materials and host materials in the prior art can be used in the light emitting layer. For example, the light emitting layer can typically but non - restrictively include the following fluorescent light emitting materials, delayed fluorescence light emitting materials, fluorescent host materials, and delayed fluorescence host materials:

[0206]

[0207] The light-emitting layer may also typically but not limitedly include the following phosphorescent light-emitting materials and phosphorescent host materials:

[0208]

[0209]

[0210] Conventional electron blocking materials in the prior art may be used in the electron blocking layer. For example, the electron blocking layer may typically but not limitedly include the following electron blocking materials:

[0211]

[0212] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the method well known to those skilled in the art has been carried out to confirm the structure and test the characteristics. Because those skilled in the art are aware of the related contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned related contents are no longer expanded and repeated in this patent.

[0213] Material Synthesis Example

[0214] 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.

[0215] Synthesis Example 1: Synthesis of Compound F1-194

[0216] Step 1: Synthesis of intermediate F1-194-A

[0217]

[0218] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, 500 mL of concentrated sulfuric acid, Tf2O (trifluoromethanesulfonic anhydride, 4.86 g, 17.2 mmol), and NIS (N-iodosuccinimide, 20.37 g, 90.5 mmol) were successively added. The reaction was carried out at room temperature for 30 minutes, then SM1 (40 g, 172.4 mmol) was added, and the reaction continued for 30 minutes. Again, NIS (20.37 g, 90.5 mmol) was added, and the reaction was carried out at room temperature for 1 hour. The reaction was monitored by GCMS until completion. The reaction solution was slowly poured into ice water, and saturated Na2SO3 solution was added until solid precipitation occurred. The solid was filtered out, dissolved in dichloromethane, and the organic phase was washed with aqueous sodium sulfite solution and aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, concentrated, and crystallized with dichloromethane and n-heptane. The solid was filtered to obtain intermediate F1-194-A (37.3 g, yield 60%).

[0219] Step 2: Synthesis of intermediate F1-194-B

[0220]

[0221] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, F1-194-A (24.5 g, 68.45 mmol), potassium phosphate (29.06 g, 136.9 mmol), SM2 (20.83 g, 80.77 mmol), Pd(OAc)2 (0.63 g, 0.68 mmol), TFP (tris(2-furyl)phosphine, 0.8 g, 3.42 mmol), and 850 mL of toluene were successively added. The mixture was heated to 115 °C and reacted overnight. The reaction was monitored by GCMS until completion, cooled to room temperature, filtered through diatomaceous earth, concentrated, and purified by column chromatography to obtain white solid F1-194-B (26 g, yield 85.5%).

[0222] Step 3: Synthesis of intermediate F1-194-C

[0223]

[0224] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, F1-194-B (26 g, 58.5 mmol) and 1L of dichloromethane were added. The temperature was lowered to 0 °C, and then BBr3 (8 mL, 70.3 mmol) was added dropwise. The reaction was carried out at room temperature for 1 hour. The reaction was monitored by TLC until completion. The reaction solution was slowly poured into ice water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated to obtain crude product F1-194-C, which could be directly used in the next step without further purification.

[0225] Step 4: Synthesis of intermediate F1-194-D

[0226]

[0227] In a 1 L two-necked round-bottom flask, under a nitrogen atmosphere, add F1-194-C, FeCl3 (1.03 g, 6.3 mmol), activated carbon (0.38 g, 31.52 mmol), 200 mL of toluene, and 200 mL of absolute ethanol. Heat to 80 °C and slowly add hydrazine hydrate (40 mL, 378.3 mmol) dropwise. Finish adding dropwise over 3 hours and continue to react at 80 °C for 2 hours. Monitor the reaction to completion by TLC. Cool the reaction solution to room temperature, filter through diatomaceous earth, and concentrate to obtain 27 g of crude oil product F1-194-D, which is directly used for the next step without further purification.

[0228] Step 5: Synthesis of intermediate F1-194-E

[0229]

[0230] In a 1 L two-necked round-bottom flask, under a nitrogen atmosphere, sequentially add F1-194-D (27 g, 67.5 mmol), Y(OTf)3 (yttrium trifluoromethanesulfonate, 1.81 g, 3.37 mmol), HC(OEt)3 (triethyl orthoformate, 30 g, 202.4 mmol), and 340 mL of DMSO. Heat to 120 °C and react for 2 hours. Monitor the reaction to completion by TLC. Cool to room temperature, slowly pour the reaction solution into ice water, extract with dichloromethane, and concentrate and purify by column chromatography to obtain F1-194-E (20 g, three-step yield 71.9%).

[0231] Step 6: Synthesis of intermediate F1-194-F

[0232]

[0233] In a 500 mL three-necked round-bottom flask, under a nitrogen atmosphere, sequentially add F1-194-E (9 g, 21.9 mmol) and 220 mL of THF. Cool to -30 °C and slowly add LiHMDS (lithium bis(trimethylsilyl)amide, 23 mL, 23 mmol). Continue to react at this temperature for 30 minutes, then add I2 (8.4 g, 32.9 mmol), warm to room temperature and react for 30 minutes. Monitor the reaction to completion by HPLC, quench with saturated aqueous sodium sulfite solution, extract with dichloromethane, and concentrate and purify by column chromatography to obtain white solid F1-194-F (8 g, yield 68%).

[0234] Step 7: Synthesis of intermediate F1-194-G

[0235]

[0236] In a 500 mL two-necked round-bottom flask, under a nitrogen atmosphere, F1-194-F (5.7 g, 10.65 mmol), potassium phosphate trihydrate (17.0 g, 64 mmol), malononitrile (2.11 g, 32 mmol), Pd(OAc)2 (72 mg, 0.32 mmol), tris(4-methoxyphenyl)phosphine (Trianisylphosphine, 259 mg, 0.852 mmol) and 200 mL of DMAc (N,N-dimethylacetamide) were successively added, and the mixture was heated to 130 °C and reacted for 36 hours. The reaction was monitored by HPLC until completion. The reaction solution was slowly poured into dilute hydrochloric acid, and a large amount of yellow solid crude product was precipitated. The crude product was recrystallized with an appropriate amount of acetone to obtain a white solid F1-194-G (4.8 g, yield 98%).

[0237] Step 8: Synthesis of compound F1-194

[0238]

[0239] In a 2 L two-necked round-bottom flask, under a nitrogen atmosphere, F1-194-G (4.8 g, 10.45 mmol) and 1 L of dichloromethane were successively added. PIFA (bis(trifluoroacetoxy)iodobenzene, 9 g, 20.9 mmol) was added in batches, and the mixture was reacted at room temperature for 5 days. It was concentrated to an appropriate volume, and then n-hexane was added and filtered to obtain a purple-black solid F1-194 (1.7 g, yield 35%). The product was confirmed to be the target product, and the molecular weight was: 457.

[0240] Synthesis Example 2: Synthesis of compound F1-248

[0241] Step 1: Synthesis of intermediate F1-248-L1

[0242]

[0243] In a 2 L two-necked round-bottom flask, under a nitrogen atmosphere, SM3 (24.5 g, 68.45 mmol), potassium phosphate (49.06 g, 231 mmol), SM4 (38.8 g, 150.5 mmol), Pd(PPh3)4 (2.66 g, 2.31 mmol) and 1 L of toluene were successively added, and the mixture was heated to 110 °C and reacted overnight. The reaction was monitored by GCMS until completion, cooled to room temperature, filtered through diatomaceous earth, concentrated, and purified by column chromatography to obtain a white solid F1-248-L1 (32 g, yield 80%).

[0244] Step 2: Synthesis of intermediate F1-248-L2

[0245]

[0246] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, F1-248-L1 (31.7 g, 90.8 mmol), B2Pin2 (bis(pinacolato)diboron, 25.4 g, 100 mmol), potassium acetate (17.8 g, 182 mmol), Pd(OAc)2 (203 mg, 0.908 mmol), SPhos (dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine, 1.17 g, 2.724 mmol) and 900 mL of toluene were successively added, and the mixture was heated to 100 °C and reacted overnight. The reaction was monitored by GCMS until completion, cooled to room temperature, filtered through diatomaceous earth, concentrated, and purified by column chromatography to obtain white solid F1-248-L2 (25 g, yield 63%).

[0247] Step 3: Synthesis of intermediate F1-248-B

[0248]

[0249] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, F1-194-A (19.3 g, 54 mmol), F1-248-L2 (23.6 g, 53.5 mmol), palladium acetate (121.5 mg, 0.54 mmol), TFP (376 mg, 1.62 mmol), cesium carbonate (35.2 g, 108 mmol) and 1L of toluene were successively added, and the mixture was heated to 110 °C and reacted overnight. The reaction was monitored by GCMS until completion, cooled to room temperature, filtered through diatomaceous earth, concentrated, and purified by column chromatography to obtain white solid F1-248-B (16 g, yield 54%).

[0250] Step 4: Synthesis of intermediate F1-248-C

[0251]

[0252] In a 2L two-necked round-bottom flask, under a nitrogen atmosphere, F1-248-B (16 g, 29.4 mmol) and 600 mL of dichloromethane were added, the temperature was lowered to 0 °C, BBr3 (3.62 ml, 38.2 mmol) was added dropwise, and the reaction was carried out at room temperature for 1 hour. The reaction was monitored by TLC until completion, the reaction solution was slowly poured into ice water, extracted with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated to obtain F1-248-C, which was directly used in the next step without further purification.

[0253] Step 5: Synthesis of intermediate F1-248-D

[0254]

[0255] In a 1L two-necked round-bottom flask, under a nitrogen atmosphere, add F1-248-C, FeCl3 (292 mg, 1.8 mmol), activated carbon (180 mg, 15 mmol), 150 mL of toluene and 150 mL of absolute ethanol, then add hydrazine hydrate (15 g, 150 mmol), and heat to 75 °C for reaction for 2 hours. Monitor the reaction to completion by TLC, cool to room temperature, filter through diatomaceous earth, and concentrate the filtrate to obtain the crude product F1-248-D, which is directly used for the next step without further purification.

[0256] Step 6: Synthesis of Intermediate F1-248-E

[0257]

[0258] In a 1L two-necked round-bottom flask, under a nitrogen atmosphere, sequentially add F1-248-D, Y(OTf)3 (482 mg, 0.88 mmol), 150 mL of DMSO and HC(OEt)3 (17.70 g, 120 mmol), and heat to 120 °C for reaction for 2 hours. Monitor the reaction to completion by TLC, cool to room temperature, slowly pour the reaction solution into ice water, a large amount of solid precipitates, filter out the solid, and then crystallize with petroleum ether and dichloromethane to obtain the yellow solid F1-248-E (11.20 g, total yield of three steps 73%).

[0259] Step 7: Synthesis of Intermediate F1-248-F

[0260]

[0261] In a 500 mL two-necked round-bottom flask, under a nitrogen atmosphere, sequentially add F1-248-E (9 g, 21.9 mmol) and 250 mL of THF, cool to -30 °C, dropwise add LiHMDS (26.2 mL, 26.2 mmol), continue the reaction at this temperature for 1 hour, then add I2 (9.07 g, 35.7 mmol), raise the temperature to room temperature and react for 30 minutes. Monitor the reaction to completion by HPLC, add saturated Na2SO3 solution to quench, extract with dichloromethane, concentrate and purify by column chromatography to obtain the white solid F1-248-F (12 g, yield 80%).

[0262] Step 8: Synthesis of Intermediate F1-248-G

[0263]

[0264] In a 500 mL two-necked round-bottom flask, under a nitrogen atmosphere, add F1-248-F (4.0 g, 6.29 mmol), potassium phosphate trihydrate (16.70 g, 63 mmol), malononitrile (2.5 g, 37.7 mmol), Pd(PPh3)4 (363 mg, 0.32 mmol) and 200 mL of DMAc, and heat to 120 °C for reaction overnight. Monitor the reaction by HPLC until completion, cool to room temperature, slowly pour the reaction solution into dilute hydrochloric acid, a large amount of yellow solid precipitates, filter out the crude product, and purify by column chromatography to obtain a pale yellow solid F1-248-G (3.5 g, yield 99%).

[0265] Step 9: Synthesis of Compound F1-248

[0266]

[0267] In a 2 L two-necked flask, under a nitrogen atmosphere, add F1-248-G (3.5 g, 6.245 mmol) and 1 L of dichloromethane, then add PIFA (5.92 g, 12.86 mmol) in batches, react at room temperature for 5 days, concentrate, add an appropriate amount of n-hexane, filter out the crude black solid, and then wash the crude product with an appropriate amount of dichloromethane and n-hexane, filter to obtain compound F1-248 (3.1 g, yield 88%). The product is confirmed to be the target product, and the molecular weight is: 558.

[0268] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0269] The measured LUMO energy level obtained herein was determined by cyclic voltammetry (CV) to measure the electrochemical properties of the compound. The test was carried out using an electrochemical workstation of model CorrTest CS120 produced by Wuhan Koster Instrument Co., Ltd. Three-electrode working system: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. Using anhydrous DCM as the solvent and 0.1 mol / L tetrabutylammonium hexafluorophosphate as the supporting electrolyte, the target compound was prepared into a 10 -3 mol / L solution, and nitrogen was introduced into the solution for 10 min to remove oxygen before the test. Instrument parameter settings: scanning rate is 100 mV / s, potential interval is 0.5 mV, and the test window is from 1 V to -0.5 V.

[0270] The LUMO values of the selected compounds of the present invention were determined by cyclic voltammetry. The LUMO value of compound F1-194 measured in anhydrous dichloromethane was -4.96 eV, and the LUMO value of compound F1-248 measured in anhydrous dichloromethane was -4.95 eV. It is worth noting that the LUMO energy level of the hole injection layer material HATCN measured by the same CV method in anhydrous dichloromethane was -4.33 eV, and the LUMO energy level of the p-dopant material F4-TCNQ was -4.94 eV.

[0271] The structures of the said HATCN and F4-TCNQ are shown as follows:

[0272]

[0273] By comparison, it can be seen that the LUMO energy levels of compounds F1-194 and F1-248 are 0.63 eV and 0.62 eV deeper than that of HATCN respectively, and are comparable to that of F4-TCNQ. Therefore, it can be proved that compounds F1-194 and F1-248 are similar to F4-TCNQ, and they are all strong electron-deficient materials, excellent electron acceptor materials and charge transfer materials, and have great potential for wide application in the field of electroluminescence. In addition, such materials also have low volatility. For example, the sublimation temperature of compound F1-194 is as high as 200 °C under a vacuum of 2.2×10 -4 Pa, which is 80 °C higher than the sublimation temperature of F4-TCNQ under the same conditions at the same vacuum degree. This shows that the compounds of the present invention have lower volatility, which is obviously beneficial to better control the deposition of the compounds of the present invention in the OLED preparation process and the reproducibility in the production process. From these data, it can be seen that compounds F1-194 and F1-248 of the present invention have great potential and excellent application prospects whether as hole injection layer materials or p-dopant materials.

[0274] In one embodiment, the LUMO values of the selected compounds of the present invention were calculated by DFT [GAUSS-09, B3LYP / 6-311G(d)], and the related compounds and their LUMO values are shown below:

[0275]

[0276]

[0277]

[0278]

[0279]

[0280] The difference between the measured LUMO (-4.96 eV) and the DFT-calculated LUMO (-5.55 eV) of the compound F1-194 of the present invention is 0.59 eV. The difference between the measured LUMO (-4.95 eV) and the DFT-calculated LUMO (-5.42 eV) of the compound F1-248 is 0.47 eV. The difference between the measured LUMO (-4.33 eV) and the DFT-calculated LUMO (-4.80 eV) of HATCN is 0.47 eV. The difference between the measured LUMO (-4.94 eV) and the DFT-calculated LUMO (-5.50 eV) of F4-TCNQ is 0.56 eV. From the above comparisons, it can be seen that for compounds with various different skeletons, the difference between the CV measured data and the DFT calculation results is about 0.53 eV. Thus, it can be seen that the DFT calculation results have high reference value. According to the DFT calculation results of the compounds of the present invention described above, it can be seen that the compounds disclosed in the present invention all have deep LUMO energy levels, are all very good electron acceptor materials and charge transfer materials, have the potential to become excellent hole injection materials and excellent p-type conductive doping materials, and have very broad industrial application prospects.

[0281] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Thus, 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 as to why the present invention works are not intended to be limiting.

Claims

1. A compound having the structure of formula F1: wherein Y is selected from W is selected from O or S; X1 to X3 are the same or different each time they appear and are selected from CR; R is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof; and at least one of R is a group having at least one electron-withdrawing group; the electron-withdrawing group is selected from the group consisting of: halogen, cyano, azaaromatic group, and any one of the following groups substituted by one or more of halogen, cyano, azaaromatic group: alkyl having 1 - 20 carbon atoms, alkoxy having 1 - 20 carbon atoms, aryl having 6 - 30 carbon atoms, heteroaryl having 3 - 30 carbon atoms, and combinations thereof; The substituted aryl having 6 - 30 carbon atoms and the substituted heteroaryl having 3 - 30 carbon atoms mean that any one of the aryl and heteroaryl groups can be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 - 20 carbon atoms, unsubstituted alkoxy having 1 - 20 carbon atoms, unsubstituted aryl having 6 - 30 carbon atoms, unsubstituted heteroaryl having 3 - 30 carbon atoms, cyano, and combinations thereof.

2. The compound according to claim 1, wherein W is selected from O.

3. The compound according to claim 1, one of X1 to X3 is selected from CR, and the R is selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms.

4. The compound according to claim 1, wherein the Hammett constant of the electron-withdrawing group is ≥0.

05.

5. The compound according to claim 4, wherein the Hammett constant of the electron-withdrawing group ≥0.

3.

6. The compound according to claim 4, wherein the Hammett constant of the electron-withdrawing group ≥0.

5.

7. The compound according to claim 4, wherein the electron-withdrawing group is selected from the group consisting of: halogen, cyano, azaaromatic group, and any one of the following groups substituted by one or more of halogen, cyano, azaaromatic group: alkyl having 1 - 20 carbon atoms, aryl having 6 - 30 carbon atoms, heteroaryl having 3 - 30 carbon atoms, and combinations thereof.

8. The compound according to claim 7, the electron-withdrawing group is selected from the group consisting of: F, CF3, cyano, pyrimidinyl, triazinyl, and combinations thereof.

9. The compound according to claim 1, wherein each occurrence of R is the same or different and is selected from the group consisting of hydrogen, deuterium, cyano, and an aryl group having 6 - 30 carbon atoms substituted with one or more groups selected from halogen and cyano, and combinations thereof.

10. The compound according to claim 1, wherein each occurrence of R is the same or different and is selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethylphenyl, bis(trifluoromethyl)phenyl, biphenyl substituted with one or more of F, CN, or CF3, and combinations thereof.

11. The compound according to claim 1, wherein each occurrence of R is the same or different and is selected from the group consisting of the following structures: wherein represents the connection position of the R group having the above structure to the six - membered ring containing X1 to X3 in Formula F1.

12. The compound according to claim 11, wherein the compound is selected from compound F1 - 1, compound F1 - 6, compound F1 - 21, compound F1 - 24, compound F1 - 25, compound F1 - 27 to compound F1 - 33, compound F1 - 39 to compound F1 - 47, compound F1 - 53 to compound F1 - 60, compound F1 - 66 to compound F1 - 80, compound F1 - 93, compound F1 - 94, compound F1 - 97 to compound F1 - 101, compound F1 - 104 to compound F1 - 125, compound F1 - 130, compound F1 - 145, compound F1 - 148 to compound F1 - 149, compound F1 - 151 to compound F1 - 157, compound F1 - 163 to compound F1 - 171, compound F1 - 177 to compound F1 - 184, compound F1 - 190 to compound F1 - 204, compound F1 - 217, compound F1 - 218, compound F1 - 221 to compound F1 - 225, compound F1 - 228 to compound F1 - 249, compound F1 - 254, compound F1 - 269, compound F1 - 272, compound F1 - 273, compound F1 - 275 to compound F1 - 281, compound F1 - 287 to compound F1 - 295, compound F1 - 301 to compound F1 - 308, compound F1 - 314 to compound F1 - 328, compound F1 - 341, compound F1 - 342, compound F1 - 345 to compound F1 - 349, compound F1 - 352 to compound F1 - 372; wherein,Compound F1-1, Compound F1-6, Compound F1-21, Compound F1-24, Compound F1-25, Compounds F1-27 to F1-33, Compounds F1-39 to F1-47, Compounds F1-53 to F1-60, Compounds F1-66 to F1-80, Compound F1-93, Compound F1-94, Compounds F1-97 to F1-101, Compounds F1-104 to F1-125, Compound F1-130, Compound F1-145, Compounds F1-148 to F1-149, Compounds F1-151 to F1-157, Compounds F1-163 to F1-171, Compounds F1-177 to F1-184, Compounds F1-190 to F1-204, Compound F1-217, Compound F1-218, Compounds F1-221 to F1-225, Compounds F1-228 to F1-249, Compound F1-254, Compound F1-269, Compound F1-272, Compound F1-273, Compounds F1-275 to F1-281, Compounds F1-287 to F1-295, Compounds F1-301 to F1-308, Compounds F1-314 to F1-328, Compound F1-341, Compound F1-342, Compounds F1-345 to F1-349, Compounds F1-352 to F1-372 have the structure shown in Formula F1: In Formula F1, two Ys are the same, and Y, X1, X2, X3, and W are respectively selected from the atoms or groups in the following table:

13. An electroluminescent device, comprising: Anode, Cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compound according to any one of claims 1 to 12.

14. The electroluminescent device according to claim 13, 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.

15. The electroluminescent device according to claim 14, 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 10,000:1 to 1:10,000.

16. The electroluminescent device according to claim 15, wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:

100.

17. The electroluminescent device according to claim 13, wherein, The electroluminescent device includes at least two light-emitting units, and the organic layer is a charge generation layer disposed between the at least two light-emitting units, wherein the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer.

18. The electroluminescent device according to claim 17, wherein, The p-type charge generation layer contains the compound.

19. The electroluminescent device according to claim 18, wherein, The p-type charge generation layer further contains at least one hole transport material, and the molar doping ratio of the compound to the hole transport material is from 10,000:1 to 1:10,000.

20. The electroluminescent device according to claim 19, wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:

100.

21. The electroluminescent device according to claim 15, 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 oligo(phenylene vinyl) compound, an oligofluorene compound, a porphyrin complex or a metal phthalocyanine complex.

22. The electroluminescent device according to claim 17, 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, and the buffer layer also comprises the compound.

23. A compound combination, which comprises the compound according to any one of claims 1-12.

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