A compound having a dehydrodiaryl skeleton

Abstract

Disclosed are a compound with a dehydrogenated bi-cyclic skeleton. The compound has a structure of H=L=H, the compound has a LUMO energy level of different depths, and can be used as a single hole injection material and an excellent P-type doping material, which is of great significance for developing a new high-performance hole injection material. Also disclosed are an organic electroluminescent device containing the compound and a compound composition containing the compound.

Description

TECHNICAL FIELD

[0001] The present application relates to a compound. More particularly, it relates to a compound having a H= L= H structure, and an organic electroluminescent device comprising the compound and a compound composition comprising the compound. BACKGROUND

[0002] Organic electronic devices include, but are not limited to, the following kinds: 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-quench devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

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

[0004] OLEDs can be categorized into three different types according to their light emission mechanism. OLED invented by Tang and van Slyke is fluorescent OLED. It only uses singlet emission. The triplet states generated in the device are wasted through a nonradiative decay channel. Therefore, the internal quantum efficiency (IQE) of fluorescent OLED is only 25%. This limitation hinders the commercialization of OLED. In 1997, Forrest and Thompson reported phosphorescent OLED, which uses triplet emission from heavy metals containing complexes as emitters. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gaps, making it possible for excitons to return from triplet to singlet states. 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 materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be quite large as long as it has a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

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

[0007] The emission color of OLEDs can be achieved by light-emitting material structure design. OLEDs can include one or more light-emitting layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime and high operating voltage. Commercial full-color OLED displays usually use a hybrid strategy, using blue fluorescent and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have more saturated emission spectrum, higher efficiency and longer device lifetime.

[0008] Organic electroluminescent devices convert electrical energy into light by applying a voltage across the device. Generally, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the electroluminescent device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, etc. According to the different functions of the materials, the materials constituting the organic layer can be divided into hole injection materials, hole transport materials, electron blocking materials, host materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. When a bias voltage is applied to the device, holes are injected from the anode to the light-emitting layer, and electrons are injected from the cathode to the light-emitting layer. Holes and electrons meet to form excitons, and excitons recombine to emit light. The hole injection layer is one of the important functional layers that affect the performance of the organic electroluminescent device, and the selection and collocation of the materials thereof can have an important influence on the performance of the organic electroluminescent device, such as the driving voltage, the efficiency, and the service life, etc. It is therefore very crucial to develop new hole injection layers for obtaining organic electroluminescent devices with low driving voltage, high efficiency, long service life, etc.

[0009] At present, the hole injection layer is generally composed of a single material or multiple materials. The single material is generally a material with a relatively deep LUMO energy level, such as HATCN. The multiple materials refer to the doping of a P-type, deep LUMO material in a hole transport material. This mode can generate free carriers by doping the dopant into the base material (generally a hole transport material), and can improve the hole injection capacity of the anode and change the Fermi level of the device. Since the LUMO of HATCN is not deep enough, it cannot be used as a P-type dopant. The deep LUMO material is generally a conjugated system compound with one or more strong electron-withdrawing substituents. The hole injection layer formed by doping the deep LUMO material in the hole transport material can improve the hole mobility of the hole injection layer, reduce the voltage of the organic electroluminescent device, and thus improve the efficiency and service life of the device.

[0010]

[0011] CN105176519 discloses a kind of thiazole structure containing axi compound, wherein the structure general formula of compound is: This application discloses the properties of axi compound, but it does not disclose or teach any compound with similar mother nucleus structure as the application and its application.

[0012] JPH0338578 discloses a kind of compound containing bithiophene, bithiophene structure as electron acceptor, which contains the following structure general formula: However, this application does not disclose or teach any properties and applications of the compounds having similar mother nucleus structure as the present application, nor does it concern the LUMO energy level of the compounds.

[0013] In view of the great influence of the hole injection layer on the voltage, efficiency and life of the OLED device, it is necessary to develop a deep LUMO hole injection material in organic electroluminescent materials. Such materials have a deep LUMO energy level, which can improve the balance of electron and hole transport in the device, so it is crucial to develop new high-performance hole injection materials. SUMMARY

[0014] The present application aims to provide a series of compounds with H=L=H structure to solve at least part of the above problems.

[0015] According to one embodiment of the present application, a compound having a structure of H=L=H is disclosed, wherein L has a structure represented by formula 1:

[0016]

[0017] wherein,

[0018] Z1and Z2are the same or different at each occurrence and are selected from CR L or N;

[0019] E is the same or different at each occurrence and is selected from the group consisting of O, S, Se, CR A R B and NR C ;

[0020] The two Hs can be the same or different, and each has a structure represented by formula 2:

[0021]

[0022] wherein,

[0023] W is the same or different at each occurrence and is selected from the group consisting of O, S, Se and NR N ;

[0024] R', R" are at each occurrence, identically or differently, selected from the group consisting of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphoroxy, azaheteroaromatic ring group, and any of the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphoroxy, azaheteroaromatic ring group: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0025] R, R L , R A , R B , R C and R N are at each occurrence, identically or differently, selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphoroxy, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilane having 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having 3-20 carbon atoms, substituted or unsubstituted aryl germanium having 6-20 carbon atoms, and combinations thereof;

[0026] adjacent substituents R', R" can optionally be linked to form a ring;

[0027] adjacent substituents R, R L , R A , R B , R C and R Nmay optionally be linked to form a ring;

[0028] "#" represents the linking position of L with structure of Formula 1 to H with structure of Formula 2.

[0029] According to another embodiment of the present application, an organic electroluminescent device is also disclosed, which comprises: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one layer of the organic layer comprising the compound described in the above embodiments.

[0030] According to another embodiment of the present application, a compound composition is also disclosed, which comprises the compound described in the above embodiments.

[0031] The present application provides a series of novel compounds with H=L=H structure of novel dehydrogenated bi-cyclic skeleton, which have deep LUMO energy level, can be used as single hole injection material, and can be used as excellent P-type dopant applied to hole injection layer, which has important significance for developing novel high-performance hole injection material. BRIEF DESCRIPTION OF DRAWINGS

[0032] Figure 1 is a schematic diagram of an organic light emitting device that can contain the compounds and compound compositions disclosed herein.

[0033] Figure 2 is another schematic diagram of an organic light emitting device that can contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0034] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light emitting device 100 is schematically, non-limitingly illustrated. The figures are not necessarily drawn to scale, and some layer structures in the figures can be omitted as desired. 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 the layers, as well as exemplary materials, are described in more detail in U.S. Patent No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated herein by reference.

[0035] Each of these layers has more examples. For example, flexible and transparent substrate-anode combinations are disclosed in U.S. Patent No. 5,844,363, incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated 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 by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entirety, disclose examples of cathodes, including composite cathodes with a thin layer of metal such as Mg:Ag overlying a transparent, conductive, sputter-deposited ITO layer. The principles and use of a blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0036] The layered structure described above is provided by way of non-limiting example. The function of an OLED can be achieved by combining various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, an emissive layer can have two sub-layers of different emissive materials to achieve a desired emission spectrum.

[0037] In one embodiment, an OLED can be described as having a "layer" disposed between the anode and the cathode. The layer can include one or more sub-layers.

[0038] OLEDs also require encapsulation layers, such as Figure 2 An illustrative, non-limiting organic light emitting device 200 is shown, which is similar to Figure 1Differently, the cathode 190 can also include an encapsulation layer 102 on top to prevent harmful species 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 organic-inorganic hybrid layers. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, which is incorporated herein by reference in its entirety.

[0039] Devices fabricated in accordance with embodiments of the application can be incorporated into a variety of consumer products, which have one or more electronic component modules (or units) that incorporate the device. Some examples of these consumer products include a flat panel display, a monitor, a medical monitor, a television, a billboard, a lamp for indoor or outdoor illumination and / or signaling, a heads up display, a fully or partially transparent display, a flexible display, a smart phone, a tablet computer, a phablet, a wearable device, a smart watch, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3-D display, a vehicle display and tail lamp.

[0040] The materials and structures described herein can also be used in other organic electronic devices, which are listed above.

[0041] As used herein, "top" means farthest from the substrate and "bottom" means closest to the substrate. Where a first layer is described as "disposed" on a second layer, the first layer is disposed farther from the substrate. Unless specified that a first layer is "in contact with" a second layer, there can be other layers between the first and second layers. For example, a cathode can be described as "disposed on" an anode even though various organic layers are between the cathode and the anode.

[0042] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium, either in solution or suspension form.

[0043] A ligand can be referred to as "photosensitizing" when it is believed to directly contribute to the photoactive properties of the emissive material. A ligand can be referred to as "auxiliary" when it is believed not to contribute to the photoactive properties of the emissive material, but an auxiliary ligand can alter the properties of a photosensitizing ligand.

[0044] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can be exceeded by 25% of the spin-statistics limit by delayed fluorescence. Delayed fluorescence can be generally classified into two types, P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0045] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds capable of E-type delayed fluorescence need to have a small singlet-triplet gap so that the conversion between the states can occur. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable 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 non-radiative decay from triplet, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of spin statistics for electroluminescent excitons.

[0046] E-type delayed fluorescence characteristics can be seen in exciplex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires that the light emitting material have a small singlet-triplet energy gap (ΔΕ S-T ). Organic non-metal containing donor-acceptor light emitting materials can be able to achieve this. The emission of these materials is often characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds often results in a small ΔΕ S-T . These states can include CT states. Typically, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (such as an amino or carbazole derivative) with an electron acceptor moiety (such as a N-containing six-membered aromatic ring).

[0047] Definitions of terms regarding substituents

[0048] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0049] Alkyl - as used herein, includes straight chain and branched chain alkyl groups. Alkyl groups can be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-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. Of the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, alkyl groups can be optionally substituted.

[0050] Cycloalkyl - As used herein, cycloalkyl includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl group can be optionally substituted.

[0051] Heteroalkyl - As used herein, heteroalkyl includes groups in which one or more carbons of an alkyl group are replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. Heteroalkyl groups can be heteroalkyl groups having 1 to 20 carbon atoms, preferably heteroalkyl groups having 1 to 10 carbon atoms, more preferably heteroalkyl groups having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxy methyl, ethoxymethoxy methyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethygermylmethyl, triethygermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group can be optionally substituted.

[0052] Alkenyl - As used herein, alkenyl encompasses straight-chain, branched, and cyclic alkene groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, 1 -methylvinyl, phenethenyl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1 -methylallyl, 1,1 -dimethylallyl, 2-methylallyl, 1 -phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1 -phenyl- 1 -butenyl, 3-phenyl- 1 -butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group can be optionally substituted.

[0053] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl groups can be optionally substituted.

[0054] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

[0055] Heterocyclic group or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothiol. Additionally, heterocyclyl groups may be optionally substituted.

[0056] Heteroaryl - As used herein, a non-fused and fused heteroaromatic group that can contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group can be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoseleophene, carbazole, indolocarbazole, pyridinoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazol, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, benzofuro[3,2-d]pyridine, furo[3,2-d]dipyridine, benzothieno[3,2-d]pyridine, thieno[3,2-d]dipyridine, benzoseleto[3,2-d]pyridine, seleto[3,2-d]dipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and nitrogen analogs thereof. Additionally, the heteroaryl group can be optionally substituted.

[0057] Alkoxy - As used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. The alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy group can be optionally substituted.

[0058] Aryloxy - As used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. Additionally, the aryloxy group can be optionally substituted.

[0059] Arylalkyl - as used herein, encompasses an aryl group substituted with an alkyl group. The arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Of the foregoing, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred. Additionally, the arylalkyl group can be optionally substituted.

[0060] Silyl - as used herein, encompasses a silicon group substituted with an alkyl group. The silyl group can be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of silyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, methyldi-t-butylsilyl. Additionally, the silyl group can be optionally substituted.

[0061] Silyl - as used herein, encompasses a silicon group substituted with an alkyl group. The silyl group can be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of silyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, methyldi-t-butylsilyl. Additionally, the silyl group can be optionally substituted.

[0062] Alkylgermyl - As used herein, encompasses an alkyl-substituted germyl group. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of alkylgermyl groups include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tri-t-butylgermyl, triisobutylgermyl, dimethyl-t-butylgermyl, methyldi-t-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0063] Arylgermyl - As used herein, encompasses a at least one aryl or heteroaryl substituted germyl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of arylgermyl groups include triphenylgermyl, phenyldiphenylgermyl, diphenylphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyl diisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyl-t-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0064] The term "aza" in azadibenzofurans, azadibenzothiophenes and the like refers to one or more C-H groups in the corresponding aromatic fragment being replaced with a nitrogen atom. For example, azatriphenylenes include 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 aza derivatives can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as described herein.

[0065] In the present disclosure, when any of the terms from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, and substituted phosphine, is used, unless otherwise defined, it means that any of the alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine groups can be substituted with one or more of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl 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 alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof.

[0066] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, it can be written by its name according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered to be equivalent.

[0067] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds can be preferred due to its enhanced efficiency and stability of the device.

[0068] In the compounds mentioned in the present disclosure, multiple substitution means including double substitution up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure represents multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent can exist at multiple available substitution positions on the structure to which it is connected, and the substituent that exists at multiple available substitution positions can be the same structure or different structures.

[0069] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a single ring or a multiple ring (including a spiro ring, a bridged ring, a fused ring, etc.), and an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a 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 further away carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0070] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to the same carbon atom are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

[0074] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to further away carbon atoms are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0075]

[0076] In addition, the expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0077]

[0078] According to one embodiment of the present application, a compound having the structure of H=L=H is disclosed, wherein L has the structure of

[0079] Formula 1:

[0080]

[0081] wherein,

[0082] Z1and Z2are the same or different at each occurrence selected from the group consisting of CR L or N;

[0083] E is the same or different at each occurrence selected from the group consisting of O, S, Se, CR A R B and NR C ;

[0084] Both of the H can be the same or different and both have the structure of Formula 2:

[0085]

[0086] wherein,

[0087] W is the same or different at each occurrence selected from the group consisting of O, S, Se and NR N ;

[0088] R’, R” are the same or different at each occurrence selected from the group consisting of halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring, and any of the following groups of alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof, substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring;

[0089] R, R L , R A , R B , R C and R Nat each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof;

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

[0091] adjacent substituents R, R L , R A , R B , R C and R N may optionally be linked to form a ring;

[0092] "#" represents the linking position of L having the structure of Formula 1 with H having the structure of Formula 2.

[0093] In the present embodiment, "adjacent substituents R', R" can optionally be linked to form a ring" is intended to mean that among the adjacent substituent groups, for example, substituents R' and R" can be linked to form a ring. It is obvious that these substituents can also not be linked to form a ring.

[0094] In the present embodiment, "adjacent substituents R, R L , R A , R B , R C and R N may optionally be linked to form a ring" is intended to mean that among the adjacent substituent groups, for example, between two substituents R L , between substituents R and R L , between substituents R and R A , between substituents R and R B , between substituents R and RC Between, the substituent R N and R A Between, the substituent R N and R B Between, the substituent R N and R C Between, the substituent R L and R N Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0095] According to one embodiment of the present invention, the substituents R, R L and R N At least one of the groups is a group having at least one electron-withdrawing group.

[0096] According to one embodiment of the present invention, the substituents R and R L At least one of the groups is a group having at least one electron-withdrawing group.

[0097] According to one embodiment of the present invention, R A , R B , R C Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphino, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms The invention also includes an alkoxy group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof.

[0098] According to one embodiment of the present invention, R A , R B , R Ceach occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, cyano, isocyano, SCN, OCN, SF5, boryl, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0099] According to one embodiment of the present application, wherein R A , R B , R C each occurrence is the same or different selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or combinations thereof.

[0100] According to one embodiment of the present application, wherein the W is the same or different at each occurrence selected from O, S, or Se.

[0101] According to one embodiment of the present application, wherein the W is the same or different at each occurrence selected from O or S.

[0102] According to one embodiment of the present application, wherein the W is O.

[0103] According to one embodiment of the present application, wherein W is the same or different at each occurrence selected from NR N .

[0104] According to one embodiment of the present application, wherein Z1and Z2are the same or different at each occurrence selected from CR L .

[0105] According to one embodiment of the present application, wherein R Neach occurrence is the same or different selected from the group consisting of substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof.

[0106] According to one embodiment of the present application, wherein R N each occurrence is the same or different selected from the group consisting of substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0107] According to one embodiment of the present application, wherein E is, at each occurrence, the same or different selected from the group consisting of O, S, Se.

[0108] According to one embodiment of the present application, wherein R is, at each occurrence, the same or different a group having at least one electron withdrawing group.

[0109] According to one embodiment of the present application, wherein R L and each of R N is a group having at least one electron withdrawing group.

[0110] According to one embodiment of the present application, wherein at least one of R is a group having at least one electron withdrawing group; and / or each of R L and R N is a group having at least one electron withdrawing group.

[0111] According to one embodiment of the present application, wherein R is, at each occurrence, the same or different selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or combinations thereof.

[0112] According to one embodiment of the present application, wherein R is, at each occurrence, the same or different, selected from an aryl group having 6-30 carbon atoms having at least one electron withdrawing group substitution, a heteroaryl group having 3-30 carbon atoms having at least one electron withdrawing group substitution, or a combination thereof.

[0113] According to one embodiment of the present application, wherein the Hammett constant of the electron withdrawing group is > 0.05.

[0114] According to one embodiment of the present application, wherein the Hammett constant of the electron withdrawing group is > 0.3.

[0115] According to one embodiment of the present application, wherein the Hammett constant of the electron withdrawing group is > 0.5.

[0116] According to one embodiment of the present application, wherein the Hammett constant of the electron withdrawing group is > 0.05.

[0117] It is noted that the Hammett constant value of the electron withdrawing group includes the para constant and / or the meta constant of the Hammett substituent, as long as one of the para constant and the meta constant is greater than or equal to 0.05, it can be used as a preferred selection group of the present application.

[0118] According to one embodiment of the present application, wherein the electron withdrawing group is selected from the group consisting of halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphine oxide, azaheteroaromatic ring group, and any one of the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxyl, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphine oxide, azaheteroaromatic ring group: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclyl having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0119] According to one embodiment of the present application, wherein the electron withdrawing group is selected from the group consisting of F, CF3, CHF2, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazinyl, and combinations thereof.

[0120] According to one embodiment of the present application, wherein R', R" are at each occurrence the same or different selected from the group consisting of: halogen, nitro, ester, cyano, isocyano, SCN, OCN, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring, and any of the following groups substituted with one or more of halogen, nitro, ester, cyano, isocyano, SCN, OCN, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring atoms, alkoxy having 1-20 carbon atoms, aryloxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0121] According to one embodiment of the present application, wherein R', R" are at each occurrence the same or different selected from the group consisting of:

[0122]

[0123] " " represents the position of attachment of R', R" having the structure described above to Formula 2.

[0124] According to one embodiment of the present application, wherein R', R" are selected from

[0125] According to one embodiment of the present application, wherein R, R L and R N are at each occurrence the same or different selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphinyl, hydroxyl, thiol, 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 heterocycloalkyl 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof.

[0126] According to one embodiment of the present application, wherein R, R L and R N are, at each occurrence, independently selected from the group consisting of hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, CN, vinyl substituted with one or more of CN or CF3, ethynyl substituted with one CN or CF3, dimethylphosphinyl, diphenylphosphinyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazinyl, pyridyl, diphenylborinyl, oxaboraanthracenyl, and combinations thereof.

[0127] According to one embodiment of the present application, wherein R, R L and R N are, at each occurrence, independently selected from the group consisting of:

[0128]

[0129]

[0130]

[0131] In the above structures, Ph represents phenyl;

[0132] wherein “ ” represents R L having the above structure at the connecting position with Formula 1, R L having the above structure at the connecting position with Formula 2; “ ” also represents R N at the connecting position with N when W is selected from NR N .

[0133] According to one embodiment of the present application, wherein R, R L and R N are, at each occurrence, independently selected from the group consisting of:

[0134]

[0135] wherein “ ” represents R L having the above structure at the connecting position with Formula 1, R L having the above structure at the connecting position with Formula 2; “ " also represents that when W is selected from NR N N and the position of the connection of N.

[0136] According to one embodiment of the present application, wherein the compound is selected from any one structure consisting of compound 1 to compound 396; wherein the specific structure of the compound 1 to compound 396 is described in claim 11.

[0137] According to one embodiment of the present application, an organic electroluminescence device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one layer of the organic layer comprising the compound of any one of the preceding embodiments.

[0138] According to one embodiment of the present application, 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.

[0139] According to one embodiment of the present application, wherein the organic layer is a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer further comprises at least one hole transport material; wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000.

[0140] According to one embodiment of the present application, wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0141] According to one embodiment of the present application, wherein the organic electroluminescence device comprises a plurality of stacked layers between the anode and the cathode, the stacked layers comprising a first light-emitting layer and a second light-emitting layer, wherein the first stacked layer comprises the first light-emitting layer, the second stacked layer comprises the second light-emitting layer, and a charge generation layer is disposed between the first stacked layer and the second stacked layer, wherein the charge generation layer comprises a p-type charge generation layer and an n-type charge generation layer; wherein the p-type charge generation layer comprises the compound.

[0142] According to one embodiment of the present application, the p-type charge generation layer further comprises at least one hole transport material, wherein the molar doping ratio of the compound to the hole transport material is from 10000:1 to 1:10000.

[0143] According to one embodiment of the present application, wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:100.

[0144] ​According to one embodiment of the present application, 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 vinylene compound, an oligofluorene compound, a porphyrin complex, or a metallophthalocyanine complex.

[0145] According to one embodiment of the present application, the charge generation layer further comprises a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, the buffer layer comprising the compound.

[0146] According to one embodiment of the present application, the organic electroluminescent device is prepared by a vacuum evaporation method.

[0147] According to one embodiment of the present application, a compound composition comprising the compound according to any one of the preceding embodiments is also disclosed.

[0148] Combination with other materials

[0149] The materials described herein for specific layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. The combinations of these materials are described in detail in US Patent Application US2016 / 0359122A1 at paragraphs 0132-0161, which is incorporated by reference herein in its entirety. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and the skilled person can readily consult the literature to identify other materials that can be used in combination.

[0150] The materials described herein as being useful for specific layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in conjunction with a variety of light emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that can be present. The combinations of these materials are described in detail in US Patent Application US2015 / 0349273A1 at paragraphs 0080-0101, which is incorporated by reference herein in its entirety. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and the skilled person can readily consult the literature to identify other materials that can be used in combination.

[0151] In the examples of material synthesis, unless otherwise specified, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and property testing using one or more devices (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai Raytian Technology's fluorescence spectrophotometer, Wuhan Kestern's electrochemical workstation, Anhui Beiyeke's sublimation instrument, etc.) of the art, and in a manner well known to those skilled in the art. Since those skilled in the art are all aware of the above-mentioned device usage, testing methods, etc. related content, the inherent data of the sample can be obtained definitely and unaffectedly, therefore the above-mentioned related content will not be expanded and elaborated in this patent.

[0152] The measured LUMO level obtained herein is determined by cyclic voltammetry to measure the electrochemical properties of the compound. A CorrTest CS120 electrochemical workstation produced by Wuhan Kestern Instrument Co., Ltd. is used. A three-electrode working system: a platinum disc electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. Anhydrous DCM or DMF is used as the solvent, 0.1 mol / L tetrabutylammonium hexafluorophosphate is used as the supporting electrolyte, the target compound is prepared into a 10 -3 mol / L solution, and nitrogen is introduced into the solution for 10 min to remove oxygen before testing. The instrument parameter settings are: scan rate is 100 mV / s, potential interval is 0.5 mV, and test window is 1V to -0.5V.

[0153] Material synthesis examples:

[0154] The preparation method of the compound of the present application is not limited, and the following compounds are exemplified typically but not limitatively, and the synthetic routes and preparation methods thereof are as follows.

[0155] Synthesis Example 1: Synthesis of compound 4

[0156] Step 1: Synthesis of [intermediate 1-a]

[0157]

[0158] In a 1 L flask, diphenyl furandicarboxylate (13.7 g, 44.5 mmol) was dissolved in DMF (320 mL), 4-trifluoromethylbenzisocyanide (32.3 g, 175 mmol) was added, then NaH (0.26 g, 6.5 mmol, 60% content) was slowly added, and the reaction was carried out under dry air for 4 days. The reaction was monitored by GC-MS, and after the reaction was completed, the solvent was directly rotary evaporated, and the product 1-a (17.8 g, 82% yield) was obtained as a yellow solid by silica gel column chromatography (DCM / PE = 1 / 1 as eluent).

[0159] Step 2: Synthesis of [intermediate 1-b]

[0160]

[0161] Under nitrogen atmosphere, 1-a (17.8 g, 36.3 mmol) was added to THF (50 mL), cooled to -72 °C (ethanol / dry ice), and a solution of LiHMDS (lithium bis(trimethylsilyl)amide) (1.0 M, 150 mL) was slowly added dropwise, then slowly warmed to -30 °C and reacted for 0.5 h. A solution of ZnCl2(2.0 M, 75 mL) was added dropwise at -30 °C, slowly warmed to 0 °C and reacted for 10 min, and solid iodine (37.2 g, 146 mmol) was added to the reaction solution, which was reacted at 0 °C for 2 h. After the reaction was completed, the reaction was quenched with saturated NH4Cl solution, washed with saturated sodium thiosulfate solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and the solvent was rotary evaporated. The product 1-b (25.3 g, 93% yield) was obtained as a yellow solid by silica gel column chromatography (eluted with DCM / PE = 1 / 2).

[0162] Step 3: Synthesis of [intermediate 1-c]

[0163]

[0164] Under nitrogen atmosphere, malononitrile (9.7 g, 147 mmol) was added to anhydrous DMF (360 mL), K2CO3(20.5 g, 148 mmol) was added in portions at 0 °C, stirred for 30 min, then 1-b (25.3 g, 34.0 mmol) and Pd(PPh4)3(2.94 g, 2.54 mmol) were added, and the reaction was carried out at 80 °C for 24 h. After complete conversion, it was poured into ice water, 2N dilute hydrochloric acid was added to adjust pH < 1, a large amount of yellow solid was precipitated, and the filter cake was washed with a large amount of water and petroleum ether. The solid product was dissolved in acetone, rotary evaporated to about 50 mL of acetone, filtered to obtain a yellow solid, and then recrystallized from acetonitrile and dichloromethane, respectively, and finally filtered to obtain a yellow solid 1-c (20.3 g, 97% yield).

[0165] Step 4: Synthesis of compound 4

[0166]

[0167] Compound 4 (9.0 g, 44% yield) was obtained as black solid. The product was confirmed as the target product with a molecular weight of 616.1. CV of compound 4 was measured in DMF, which gave the LUMO of the compound as -4.79 eV.

[0168] Synthesis Example 2: Synthesis of compound 5

[0169] Step 1: Synthesis of [intermediate 2-a]

[0170]

[0171] In a 500 mL flask, diphenyl furandicarboxylate (6.5 g, 21.1 mmol) was dissolved in THF (240 mL), 3,5-bistrifluoromethylbenzyl isonitrile (25.5 g, 101 mmol) was added, followed by slow addition of Ag2CO3(0.52 g, 1.9 mmol), and the reaction was allowed to proceed for 4 days under dry air. The reaction was monitored by GC-MS, and after completion of the reaction, the solvent was directly evaporated, and the product 2-a (10.9 g, 82% yield) was obtained as a light yellow solid by purification on a silica gel column (eluent: DCM / PE = 1 / 2).

[0172] Step 2: Synthesis of [intermediate 2-b]

[0173]

[0174] Under nitrogen atmosphere, 2-a (10.9 g, 17.4 mmol) was added into THF (180 mL) and cooled to -72 °C (ethanol / dry ice), then LiHMDS solution (1.0 M, 70 mL) was added dropwise slowly, followed by slowly warming to -30 °C and continuing the reaction for 2 h. A solution of ZnCl2(2.0 M, 35 mL) was added dropwise at -30 °C, and the solution was slowly warmed to 0 °C and reacted for 10 min. Elemental solid iodine (17.7 g, 69.7 mmol) was added into the reaction solution, and the solution was warmed to room temperature and reacted for 1 h. After the reaction was completed, the reaction was quenched with saturated NH4Cl solution, washed with saturated Na2S2O3 solution, extracted with DCM, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography (eluted with DCM / PE = 1 / 4) to obtain yellow solid 2-b (13.7 g, 90% yield).

[0175] Step 3: Synthesis of [intermediate 2-c]

[0176]

[0177] Under nitrogen atmosphere, malononitrile (4.40 g, 66.7 mmol) was added into anhydrous DMF (180 mL), and K2CO3(8.63 g, 62.4 mmol) was added portionwise at 0 °C and stirred for 30 min. 2-b (13.7 g, 15.6 mmol) and Pd(PPh4)3(1.85 g, 1.60 mmol) were added, and the solution was warmed to 80 °C and reacted for 24 h. After complete conversion, the solution was poured into ice water, and the pH was adjusted to <1 with 2N dilute hydrochloric acid, and a large amount of yellow solid was precipitated, which was filtered, and the filter cake was washed with a small amount of water and petroleum ether. The solid product was dissolved in acetone, the solvent was evaporated by rotary evaporation and dried, and then it was slurried twice with acetonitrile and dichloromethane, filtered, and washed three times with dichloromethane (20 mL) to obtain yellow solid 2-c (9.3 g, 79% yield).

[0178] Step 4: Synthesis of compound 5

[0179]

[0180] Under nitrogen atmosphere, 2-c (9.3 g, 12.3 mmol) was added into DCM (1200 mL) and cooled to 0 °C, and PIFA (10.6 g, 24.7 mmol) was added portionwise, and the solution was stirred at room temperature for 2 days, and the solution was ink blue. DCM was evaporated by rotary evaporation, and 100 mL of n-heptane was added to precipitate the solid, which was filtered to obtain black solid. The product was washed twice with DCM / PE = 1:1, and finally black solid 5 (5.1 g, 55% yield) was obtained. The product was confirmed as the target product with a molecular weight of 752.1. The CV of compound 5 was measured in DCM to obtain the LUMO of the compound = -4.89 eV.

[0181] The LUMO energy levels of some of the compounds disclosed in the present application are calculated by DFT [GAUSS-09, B3LYP / 6-311G(d)], and the related compounds and the calculated LUMO values thereof are shown in Table 1 below:

[0182] Table 1 DFT calculation results

[0183] Compound LUMO (eV) Compound LUMO (eV) 4 -5.06 5 -5.17 6 -5.04 16 -5.18 17 -5.29 18 -5.14 28 -5.32 29 -5.45 40 -5.66 41 -5.80

[0184] The structures of the compounds in Table 1 are shown below:

[0185]

[0186] Discussion:

[0187] From the actually measured data, it can be seen that the actually measured LUMO energy levels of the compound 4 and the compound 5 of the embodiment of the present application are -4.79 eV and -4.89 eV respectively, which are deeper than the LUMO energy level of HATCN, -4.33 eV (measured in DCM solvent by the test method in the present application), indicating that the compound 4 and the compound 5 both have excellent hole injection ability.

[0188] The LUMO energy level values calculated by DFT of representative compounds with H=L=H structure in Table 1 are listed, and from the data, it can be seen that the compounds with different structures in the present application all have deep LUMO energy levels, further indicating that the compounds with H=L=H structure disclosed in the present application all have deep LUMO energy levels, and are a kind of potential compounds that can be used as hole injection materials in organic electronic devices.

[0189] The LUMO energy level calculation data of some of the compounds as shown in Table 1, wherein the substituents R and R L of the compounds with H=L=H structure are all compounds with electron-withdrawing groups, and the LUMO energy level of the compound with at least one electron-withdrawing group in one of R and R L is deeper, for example, compound 16 vs. compound 4, compound 17 vs. compound 5, and compound 18 vs. compound 6; the LUMO energy level of the compound with both Z in the structure of formula 1 being N is deeper than that of the compound with one Z being N, for example, compound 40 vs. compound 28, and for example, compound 41 vs. compound 29. The above indicates that it is very important to introduce electron-withdrawing groups to the compounds with H=L=H structure in the present application, which can reduce the LUMO energy level value of the compound, and has important significance in the research of hole transport materials.

[0190] In summary, the compounds of the present invention have a relatively deep LUMO energy level and are very important charge transfer materials, especially with unparalleled advantages in hole transport. They can be applied to organic semiconductor devices and are suitable for different types of organic semiconductor devices, including but not limited to fluorescent OLEDs, phosphorescent OLEDs, white light OLEDs, stacked OLEDs, OTFTs (organic thin film transistors), OPVs, etc.

[0191] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure of H=L=H, wherein L has a structure represented by Formula 1: in, Z1 and Z2 are selected from CR in the same or different ways each time they appear. L or N; Each occurrence of E is the same or different and is selected from the group consisting of O, S, and Se; The two H are the same and both have a structure represented by Formula 2: in, W is selected from the group consisting of O, S, Se at each occurrence, either identically or differently; R', R" are selected from R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; R L Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, cyano; The substituted aryl group having 6 to 30 carbon atoms and the substituted heteroaryl group having 3 to 30 carbon atoms refer to any one of the aryl group and the heteroaryl group which may be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, unsubstituted heteroaryl group having 3 to 30 carbon atoms, cyano group, and combinations thereof; "#" represents the connection position of L having the structure of Formula 1 and H having the structure of Formula 2.

2. The compound according to claim 1, wherein at least one of the substituents R is a group having at least one electron-withdrawing group; the electron-withdrawing group is selected from the group consisting of: halogen, cyano, and any of the following groups substituted by one or more of halogen and cyano: an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms; and / or the substituent R L At least one of them is a group having at least one electron-withdrawing group; the electron-withdrawing group is selected from the group consisting of: halogen, cyano.

3. The compound of claim 1, wherein W is selected from O or S, identically or differently at each occurrence.

4. The compound of claim 1, wherein W is O.

5. The compound of claim 1, wherein each occurrence of R is identical or different and is a group having at least one electron withdrawing group; the electron withdrawing group is selected from the group consisting of: halogen, cyano, and any of the following groups substituted by one or more of halogen and cyano: alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms; and / or R L Each of the groups is a group having at least one electron-withdrawing group; the electron-withdrawing group is selected from the group consisting of: halogen, cyano.

6. The compound of claim 1, wherein R is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.

7. The compound of claim 6, wherein R is selected, at each occurrence, identically or differently, from an aryl group having 6 to 30 carbon atoms substituted with at least one electron-withdrawing group, a heteroaryl group having 3 to 30 carbon atoms substituted with at least one electron-withdrawing group, or a combination thereof; the electron-withdrawing group is selected from the group consisting of: halogen, cyano, and any of the following groups substituted with one or more of halogen and cyano: an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms. The compound according to claim 2 , wherein the Hammett constant of the electron-withdrawing group is ≥0.

05. The compound of claim 8 , wherein the Hammett constant of the electron-withdrawing group is ≥0.

3. The compound of claim 8 , wherein the Hammett constant of the electron-withdrawing group is ≥0.

5.

11. The compound of claim 7, wherein the electron withdrawing group is selected from the group consisting of halogen, cyano, and any of the following groups substituted with one or more of halogen and cyano: an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms.

12. The compound of claim 7, wherein the electron withdrawing group is selected from the group consisting of F, CF3, CHF2, OCF3, cyano.

13. The compound according to claim 1, wherein R L At each occurrence, identically or differently selected from the group consisting of: R is selected, identically or differently at each occurrence, from the group consisting of: in Represents R having the above structure L The connection position with Formula 1, and the connection position with R having the above structure with Formula 2.

14. The compound of claim 13, wherein the compound is selected from any one of the structures consisting of Compound 1, Compound 3 to Compound 7, Compound 9 to Compound 13, Compound 15 to Compound 19, Compound 21 to Compound 25, Compound 27 to Compound 31, Compound 33 to Compound 37, Compound 39 to Compound 43, Compound 45 to Compound 49, Compound 51 to Compound 55, Compound 57 to Compound 61, Compound 63 to Compound 67, Compound 69 to Compound 73, Compound 75 to Compound 79, Compound 81 to Compound 85, Compound 87 to Compound 91, and Compound 93 to Compound 124; wherein, Compound 1, Compound 3 to Compound 7, Compound 9 to Compound 13, Compound 15 to Compound 19, Compound 21 to Compound 25, Compound 27 to Compound 31, Compound 33 to Compound 37, Compound 39 to Compound 43, Compound 45 to Compound 49, Compound 51 to Compound 55, Compound 57 to Compound 61, Compound 63 to Compound 67, Compound 69 to Compound 73, Compound 75 to Compound 79, Compound 81 to Compound 85, Compound 87 to Compound 91, Compound 93 to Compound 124 have the structure of Formula 1-1: In formula 1-1, two R's are the same, two R"s are the same, two Ws are the same, two Rs are the same, and R', R", W, R, Z1, Z2 and E correspond to atoms or groups selected from the following table:

15. An organic electroluminescent device, comprising: anode, cathode, An organic layer is provided between the anode and the cathode, wherein at least one layer of the organic layer comprises the compound according to any one of claims 1 to 14. 16 . The organic electroluminescent device according to claim 15 , 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.

17. The organic electroluminescent device according to claim 15, 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. 18 . The organic electroluminescent device according to claim 17 , wherein the molar doping ratio of the compound to the hole transport material is from 10:1 to 1:

100.

19. The organic electroluminescent device of claim 15, wherein the electroluminescent device comprises a plurality of stacked layers between an anode and a cathode, the stacked layers comprising a first light-emitting layer and a second light-emitting layer, wherein: The first stacked layer includes a first light-emitting layer, the second stacked layer includes a second light-emitting layer, and the charge generation layer is disposed between the first stacked layer and the second stacked layer, wherein the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer; The p-type charge generating layer comprises the compound. 20 . The organic electroluminescent device according to claim 19 , wherein the p-type charge generation layer further comprises at least one hole transport material, wherein a molar doping ratio of the compound to the hole transport material is 10,000:1 to 1:10,000. 21 . The organic electroluminescent device according to claim 20 , wherein the molar doping ratio of the compound to the hole transport material is 10:1 to 1:

100.

22. The organic electroluminescent device according to claim 17 or 20, wherein the hole transport material comprises a compound having a triarylamine unit, a spirobifluorene compound, a pentacene compound, an oligothiophene compound, an oligophenyl compound, an oligophenylene vinyl compound, an oligofluorene compound, a porphyrin complex or a metal phthalocyanine complex. 23 . The organic electroluminescent device according to claim 19 , wherein the charge generation layer further comprises a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, wherein the buffer layer comprises the compound.

24. A compound composition comprising the compound according to any one of claims 1-14.

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