Organic electroluminescent material and device thereof

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound having a structure of Formula 1, which can be used in an organic electroluminescent device, for example, as an electron blocking material, etc. The application of these compounds in an organic electroluminescent device can reduce the device voltage, improve the device efficiency, and especially can greatly improve the device lifetime, providing better overall performance of the device. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic electroluminescent devices. More particularly, it relates to a compound having the structure of Formula 1, an organic electroluminescent device comprising the compound, and a compound composition comprising the compound. Background Technology

[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 photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. 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 luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. 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). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, 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 OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

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

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] The efficiency, lifetime, and other performance characteristics of organic electroluminescent devices are closely related to the balance of carrier concentration in the emitting layer. This balance can be more effectively controlled through the molecular structure design of charge transport materials and carrier blocking materials. Compounds with spiroacridine structural fragments have been reported as potential hole transport materials, electron blocking materials (light-emitting auxiliary materials), or host materials in electroluminescent devices.

[0009] CN110818635A discloses that has Compounds with the structure, wherein L1–L4 each independently represent one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms; m, n, p, and q each independently are integers from 0 to 4, and m, n, p, and q are not simultaneously 0; A1–A4 each independently represent Ar1–Ar4, One or more of the following: Ar1 to Ar8, each independently representing one or more aromatic hydrocarbon groups having 6 to 30 carbon atoms optionally substituted with one or more R1 groups, or aromatic heterocyclic groups having 5 to 30 carbon atoms optionally substituted with one or more R1 groups; X represents C(R1)2, O, S, SO2, P(=O)R1, Si(R1)2, Ge(R1)2, NR1, a single bond, or an unbonded bond. Furthermore, this application discloses compounds in numerous specific structures. This application does not disclose or teach that the substituent -L2-A2 on the acridine ring can be linked to form a ring, nor does it disclose or teach the particular advantages of compounds having additional fused rings on the acridine ring and their impact on device performance. Furthermore, the compounds disclosed in this application are used as host materials in electroluminescent devices, and it does not disclose or teach the effects of said compounds as other materials on device performance.

[0010] WO2014017844A1 discloses having Compounds with a structure wherein X is selected from C, O, P, S, Se, or Si, and the specific structure of the compound is disclosed. The silicon-containing compounds disclosed in this application all contain silicon fluorene fragments, and the acridine / spiroacidine fragments do not have additional fused ring structures. This application does not disclose or teach compounds containing fused spiroacidine structures and aryl / heteroaryl silicon-based fragments, nor their effects on device performance. Furthermore, the compounds disclosed in this application are used as host materials in electroluminescent devices, and it does not disclose or teach the effects of these compounds as other materials on device performance.

[0011] CN114790170A discloses that has Compounds with the structure Ar1 being a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar2 having The structure represented, Q1 is O, S, SO, SO2, Se, CO, C(R) 11 (R) 12 ), Si(R) 11 (R) 12 ), Ge(R) 11 (R) 12 ), B(R) 13 ), N(R 14 ), P(R 15 ), PO(R) 16 ), PS(R 17 ) or by Equation 3 Among the numerous specific structures disclosed, the group represented by silicon-containing compounds is only one compound. The silicon-containing compounds disclosed in this application all contain silicon fluorene fragments, and the acridine / spiroacidine fragments do not have additional fused ring structures. This application focuses on the impact of their Q1 and / or Ar1 on device performance, and does not focus on the special advantages of compounds containing fused acridine spirocyclic structures and aryl / heteroaryl silicon-based fragments and their impact on device performance.

[0012] As the industry's demands for the performance of organic electroluminescent devices continue to increase, OLED materials with superior properties such as lower voltage, higher efficiency, and longer lifespan still require in-depth research and development. Summary of the Invention

[0013] This invention aims to provide a series of compounds in which fused acridine spirocyclic structural segments, represented by Formula 1, are linked at specific positions to aryl / heteroaryl silicon-based structural segments to solve at least some of the aforementioned problems. These compounds can be used in organic electroluminescent devices, for example, as electron blocking materials. The application of these compounds in organic electroluminescent devices can reduce device voltage, improve device efficiency, and especially significantly extend device lifetime, providing better overall device performance.

[0014] According to one embodiment of the present invention, a compound is disclosed having a structure represented by Formula 1:

[0015]

[0016] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0017] L is selected from arylene groups having 6-30 carbon atoms, heteroarylene groups having 3-30 carbon atoms, or combinations thereof; wherein the arylene groups and heteroarylene groups are unsubstituted or can optionally be substituted by one or more groups R1.

[0018] Q is selected from CR'R", SiR'R", NR N O or S;

[0019] W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ;

[0020] R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0021] R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0022] Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0023] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound described in the foregoing embodiments.

[0024] According to another embodiment of the present invention, a compound composition comprising the compounds described in the foregoing embodiments is also disclosed.

[0025] This invention discloses a series of compounds in which fused acridine spirocyclic structural segments, represented by Formula 1, are linked at specific positions to aryl / heteroaryl silicon-based structures. These compounds can be used in organic light-emitting devices (OLEDs) to significantly improve their performance, for example, by reducing device voltage, increasing device efficiency, and especially by substantially extending device lifetime and enhancing overall device performance. Attached Figure Description

[0026] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0027] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. Detailed Implementation

[0028] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0029] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated 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, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0030] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may 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 may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0031] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0032] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0033] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0034] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0035] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0036] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0037] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0038] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0039] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0040] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0041] Definition of the term "substituent group"

[0042] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0043] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 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 group may optionally be substituted.

[0044] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group 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, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0045] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0046] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefin groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptanetrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0047] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 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, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0048] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. 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, fenene, fluorene, pyrene, etc. 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'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0049] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. 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. 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 ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0050] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. 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 heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0051] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An 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, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0052] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups 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 groups. Additionally, the aryloxy group may optionally be substituted.

[0053] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and 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 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 The compounds include alkyl groups, such as 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. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0054] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0055] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0056] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0057] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0058] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0059] In this disclosure, unless otherwise defined, the term "substituted alkyl", "substituted cycloalkyl", "substituted heteroalkyl", "substituted heterocyclic", "substituted aralkyl", "substituted alkoxy", "substituted aryl", "substituted alkenyl", "substituted alkynyl", "substituted heteroaryl", "substituted alkylsilyl", "substituted arylsilyl", "substituted alkylgermanium", "substituted arylgermanium", "substituted amino", "substituted acyl", "substituted carbonyl", and "substituted carboxylic acid" are used interchangeably. The substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl groups. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms. Cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, and unsubstituted alkyne groups having 6-30 carbon atoms. Aryl, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof with 0-20 carbon atoms.

[0060] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0061] In the compounds mentioned in this 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. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0062] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0063] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0064] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0065]

[0066] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0067]

[0068] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, as exemplified by the following formula:

[0069]

[0070] Furthermore, the statement that adjacent substituents can optionally connect 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 bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0071]

[0072] According to one embodiment of the present invention, a compound is disclosed having a structure represented by Formula 1:

[0073]

[0074] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0075] L is selected from arylene groups having 6-30 carbon atoms, heteroarylene groups having 3-30 carbon atoms, or combinations thereof; wherein the arylene groups and heteroarylene groups are unsubstituted or can optionally be substituted by one or more groups R1.

[0076] Q is selected from CR'R", SiR'R", NR N O or S;

[0077] W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ;

[0078] R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0079] R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0080] Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0081] In this article, “adjacent substituents R1, R2, R3, R4, R', R”, R N "Optionally connected to form a ring" is intended to indicate adjacent substituent groups, for example, between two substituents R1, between two substituents R2, between two substituents R3, between two substituents R4, between substituents R' and R'", between substituents R2 and R3, between substituents R3 and R4, between substituents R4 and R'". N Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0082] According to one embodiment of the present invention, when W is selected from a single bond, any adjacent substituents R1 and R2 cannot be connected to form a ring.

[0083] According to one embodiment of the present invention, when W is selected from a single bond, any adjacent substituent R3 cannot be connected to form a ring.

[0084] According to one embodiment of the present invention, any adjacent substituents R1 and R2 cannot be connected to form a ring.

[0085] According to one embodiment of the present invention, any adjacent substituents R3 cannot be connected to form a ring.

[0086] According to one embodiment of the present invention, Ar and L cannot be connected to form a ring.

[0087] According to one embodiment of the invention, R2, each time it appears, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The group comprises alkynyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof, wherein the substituted or unsubstituted aryl groups having 6-30 carbon atoms do not include ortho-biphenyl groups.

[0088] According to one embodiment of the present invention, wherein the L is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0089] According to one embodiment of the present invention, wherein the L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted silylfluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or combinations thereof.

[0090] According to one embodiment of the present invention, the L is selected from substituted or unsubstituted phenylene.

[0091] According to one embodiment of the present invention, the compound has a structure represented by Formula 2:

[0092]

[0093] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0094] Each time Z1 to Z5 appears, they are selected from C, CR1 or N in the same or different ways, and one of Z1 to Z5 is C and connected to Si;

[0095] Q is selected from CR'R", SiR'R", NR N O or S;

[0096] W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ;

[0097] R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0098] R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0099] Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0100] According to one embodiment of the present invention, the W is selected from single bonds, O, S, or CR'R.

[0101] According to one embodiment of the present invention, the W is selected from single bonds.

[0102] According to one embodiment of the present invention, the compound has a structure represented by any one of formulas 2-1, 2-2, 2-3, 2-4, 2-5, and 2-6:

[0103]

[0104] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0105] Each time Z1 to Z5 appears, they are selected from C, CR1 or N in the same or different ways, and one of Z1 to Z5 is C and connected to Si;

[0106] Q is selected from CR'R", SiR'R", NR N O or S;

[0107] R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0108] R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0109] Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0110] According to one embodiment of the present invention, the compound has a structure represented by formula 2-1, formula 2-3, formula 2-4 or formula 2-5.

[0111] According to one embodiment of the present invention, Q is selected from CR'R.

[0112] According to one embodiment of the invention, wherein Q is selected from CR'R", and R', R" are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.

[0113] According to one embodiment of the invention, wherein Q is selected from CR'R", and R', R" are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and combinations thereof.

[0114] According to one embodiment of the present invention, Z2 or Z3 is C and connected to Si.

[0115] According to one embodiment of the present invention, at least two adjacent substituents R2 are connected to form a ring.

[0116] According to one embodiment of the present invention, at least two adjacent substituents R2 are connected to form an aromatic ring or a heteroaromatic ring.

[0117] According to one embodiment of the present invention, the compound has a structure represented by Formula 3:

[0118]

[0119] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0120] Each time Z1 to Z5 appears, they are selected from C, CR1 or N in the same or different ways, and one of Z1 to Z5 is C and connected to Si;

[0121] Q is selected from CR'R", SiR'R", NR N O or S;

[0122] X is selected from CR'R", SiR'R", NR N O or S;

[0123] R1, R3, R4, and R5, when they appear in the same or different ways, represent monosubstitution, polysubstitution, or no substitution.

[0124] R1, R3, R4, R5, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0125] Adjacent substituents R1, R3, R4, R5, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0126] In this article, “adjacent substituents R1, R3, R4, R5, R', R”, R N "Optionally connected to form a ring" is intended to indicate adjacent substituent groups, for example, between two substituents R1, between two substituents R3, between two substituents R4, between two substituents R5, between substituents R' and R'", between substituents R1 and R4, between substituents R1 and R5, between substituents R3 and R4, between substituents R3 and R5, between substituents R4 and R'". N Between, and substituents R5 and R N Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0127] According to one embodiment of the present invention, the compound has a structure represented by any one of formulas 3-1 to 3-12:

[0128]

[0129]

[0130] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0131] X is selected from CR'R", SiR'R", NR N O or S;

[0132] R1, R3, R4, and R5, when they appear in the same or different ways, represent monosubstitution, polysubstitution, or no substitution.

[0133] R1, R3, R4, R5, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0134] Adjacent substituents R1, R3, R4, R5, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0135] According to one embodiment of the present invention, the compound has a structure represented by formula 3-1, formula 3-2, formula 3-9 or formula 3-10.

[0136] According to one embodiment of the present invention, wherein X is selected from CR'R", NR". N , O or S.

[0137] According to one embodiment of the present invention, wherein X is selected from CR'R.

[0138] According to one embodiment of the invention, wherein X is selected from CR'R", and R', R" are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.

[0139] According to one embodiment of the invention, wherein X is selected from CR'R", and R', R" is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and combinations thereof.

[0140] According to one embodiment of the present invention, the compound has a structure represented by Formula 4:

[0141]

[0142] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0143] Each time Z1 to Z5 appears, they are selected from C, CR1 or N in the same or different ways, and one of Z1 to Z5 is C and connected to Si;

[0144] Q is selected from CR'R", SiR'R", NR N O or S;

[0145] W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ;

[0146] R1, R3, R4, and R5, when they appear in the same or different ways, represent monosubstitution, polysubstitution, or no substitution.

[0147] R1, R3, R4, R5, R', R", R NEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0148] Adjacent substituents R1, R3, R4, R5, R', R'', R'' N They can be arbitrarily connected to form a ring.

[0149] According to one embodiment of the present invention, wherein the Ar, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-25 carbon atoms, or combinations thereof.

[0150] According to one embodiment of the present invention, wherein the Ar, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, or combinations thereof.

[0151] According to one embodiment of the invention, wherein the Ar, each time it appears, is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyreneyl, or combinations thereof.

[0152] According to one embodiment of the invention, the Ar is selected from substituted or unsubstituted phenyl groups each time it appears.

[0153] According to one embodiment of the invention, at least one of the Ar groups, each time appearing, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, either identically or differently.

[0154] According to one embodiment of the invention, at least one of the Ar groups, each time appearing, is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, either identically or differently.

[0155] According to one embodiment of the invention, at least one of the Ar groups, each time appearing, is selected from substituted or unsubstituted aryl groups having 6-18 carbon atoms, either identically or differently.

[0156] According to one embodiment of the invention, wherein at least one of the Ars, each time appearing, is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyreneyl, or combinations thereof.

[0157] According to one embodiment of the present invention, wherein R1, R2, R3, R4, R', R'', R''' are... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0158] According to one embodiment of the present invention, wherein R1, R2, R3, R4, R', R'', R''' are... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and combinations thereof.

[0159] According to one embodiment of the present invention, wherein R1, R3, R4, R5, R' ... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0160] According to one embodiment of the present invention, wherein R1, R3, R4, R5, R' ... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and combinations thereof.

[0161] According to one embodiment of the present invention, the compound is selected from the group consisting of compound 1 to compound 470, and the specific structures of compound 1 to compound 470 are given in claim 11.

[0162] According to one embodiment of the present invention, the hydrogen in the structure of compounds 1 to 470 can be partially or completely replaced by deuterium.

[0163] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound described in any of the foregoing embodiments.

[0164] According to one embodiment of the present invention, the organic layer is an electron blocking layer, a hole injection layer, a hole transport layer, or a light-emitting layer.

[0165] According to one embodiment of the present invention, the organic layer is an electron blocking layer and the compound is an electron blocking material.

[0166] According to one embodiment of the present invention, the thickness of the electron blocking layer is between 1 nm and 800 nm.

[0167] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a host material.

[0168] According to one embodiment of the present invention, the light-emitting layer comprises a phosphorescent material.

[0169] According to one embodiment of the present invention, the organic electroluminescent device emits red light.

[0170] According to one embodiment of the present invention, the organic electroluminescent device emits green light.

[0171] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer, wherein the electron blocking layer comprises the compound described in any of the foregoing embodiments.

[0172] According to one embodiment of the present invention, the electron blocking layer is in direct contact with the hole transport layer, and the electron blocking layer is in direct contact with the light-emitting layer.

[0173] According to one embodiment of the present invention, the hole transport layer comprises a hole transport material, wherein the hole transport material comprises a monotriarylamine compound or a bistriarylamine compound.

[0174] According to one embodiment of the present invention, a compound composition comprising the compounds described in any of the foregoing embodiments is disclosed.

[0175] Combination with other materials

[0176] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein 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.

[0177] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein 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.

[0178] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0179] Material synthesis examples:

[0180] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0181] Synthesis Example 1: Synthesis of Compound 1

[0182] Step 1: Synthesis of Intermediate A

[0183]

[0184] Under a nitrogen atmosphere, intermediates SM1 (27 g, 95.6 mmol), SM2 (20 g, 95.6 mmol), sodium tert-butoxide (18.4 g, 191.2 mmol), Pd2(dba)3 (1.75 g, 1.91 mmol), dppf (1,1'-bis(diphenylphosphine)ferrocene) (3.18 g, 5.74 mmol), and toluene (1000 mL) were added sequentially to a 2000 mL reaction flask. The temperature was raised to 120 °C and the reaction was carried out for 3 h. The reaction was monitored by TLC until it was complete. The temperature was then cooled to room temperature, filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate A (30 g, yield 86.2%).

[0185] Step 2: Synthesis of Intermediate B

[0186]

[0187] Under a nitrogen atmosphere, intermediate A (30 g, 82.35 mmol) and THF (240 mL) were added to a 500 mL two-necked flask. The temperature was lowered to -75 °C, and n-BuLi (73 mL, 182.5 mmol) was added dropwise. The mixture was stirred for 1 h, and then a THF (50 mL) solution of intermediate SM3 (14.8 g, 82.35 mmol) was added dropwise. The reaction temperature was restored to room temperature and stirred for 3 h. The reaction was monitored by TLC until it was complete. The reaction was quenched with an appropriate amount of dilute hydrochloric acid. The mixture was separated into liquid and liquid phases. The aqueous phase was extracted with DCM, and the organic phases were combined and concentrated under reduced pressure. The solid intermediate B (24 g, yield 62.7%) was purified by column chromatography.

[0188] Step 3: Synthesis of intermediate C

[0189]

[0190] Under N2 atmosphere, intermediate B (24 g, 51.5 mmol) and DCM (300 mL) were added to a 500 mL two-necked flask. TFA (trifluoroacetic acid, 24 mL) was added dropwise at room temperature. The mixture was stirred overnight at room temperature. The reaction was monitored by TLC until it was complete. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate C (21.3 g, yield 92.2%).

[0191] Step 4: Synthesis of Compound 1

[0192]

[0193] Under a nitrogen atmosphere, intermediates SM4 (6 g, 14.43 mmol), C (6.45 g, 14.43 mmol), sodium tert-butoxide (2.76 g, 28.86 mmol), and Pd2(dba)3 (264 mg, 0.288 mmol) were added sequentially to a 500 mL reaction flask. t Bu3PHBF4 (417 mg, 1.44 mmol) and xylene (150 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was restored to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give compound 1 (8.53 g, yield 75.5%), a white solid. The product was identified as the target product with a molecular weight of 781.32.

[0194] Synthesis Example 2: Synthesis of Compound 2

[0195]

[0196] Under a nitrogen atmosphere, intermediates SM5 (2 g, 4.81 mmol), C (2.15 g, 4.81 mmol), sodium tert-butoxide (0.92 g, 9.62 mmol), and Pd2(dba)3 (88 mg, 0.096 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (139 mg, 0.48 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was restored to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 2 (2.26 g, yield 59.5%). The product was identified as the target product with a molecular weight of 781.32.

[0197] Synthesis Example 3: Synthesis of Compound 5

[0198] Step 1: Synthesis of intermediate D

[0199]

[0200] Under a nitrogen atmosphere, intermediates SM2 (14.07 g, 67.3 mmol), SM6 (20 g, 67.3 mmol), sodium tert-butoxide (13.1 g, 136.4 mmol), Pd2(dba)3 (1.23 g, 1.35 mmol), dppf (3.73 g, 6.73 mmol), and toluene (673 mL) were added sequentially to a 2000 mL reaction flask. The temperature was raised to 120 °C and the reaction was carried out for 3 h. The reaction was monitored by TLC until it was complete. The reaction temperature was then restored to room temperature, filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate D (16.5 g, yield 65%).

[0201] Step 2: Synthesis of intermediate E

[0202]

[0203] Under a nitrogen atmosphere, intermediate D (16.5 g, 43.6 mmol) and THF (130 mL) were added to a 500 mL two-necked flask. The temperature was lowered to -82 °C, and n-BuLi (37 mL, 92.5 mmol) was added dropwise. The mixture was stirred for 1 h, and then a THF (20 mL) solution of intermediate SM3 (9.4 g, 52.3 mmol) was added dropwise. The reaction temperature was restored to room temperature and stirred for 3 h. The reaction was monitored by TLC until it was complete. The reaction was quenched with an appropriate amount of dilute hydrochloric acid. The mixture was separated into liquid and liquid phases. The aqueous phase was extracted with DCM, and the organic phases were combined and concentrated under reduced pressure. The solid intermediate E (10.7 g, yield 48.4%) was purified by column chromatography.

[0204] Step 3: Synthesis of intermediate F

[0205]

[0206] Under N2 atmosphere, intermediate E (10.7 g, 22.3 mmol) and DCM (50 mL) were added to a 100 mL two-necked flask. TFA (11 mL) was added dropwise at room temperature. The mixture was stirred overnight at room temperature. The reaction was monitored by TLC until it was complete. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate F (10.3 g, 100% yield).

[0207] Step 4: Synthesis of Compound 5

[0208]

[0209] Under a nitrogen atmosphere, intermediates SM5 (3 g, 7.22 mmol), F (3.34 g, 7.22 mmol), sodium tert-butoxide (1.39 g, 14.44 mmol), and Pd2(dba)3 (132 mg, 0.144 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (210 mg, 0.722 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was restored to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 5 (5 g, yield 87%). The product was identified as the target product with a molecular weight of 795.33.

[0210] Synthesis Example 4: Synthesis of Compound 4

[0211]

[0212] Under a nitrogen atmosphere, intermediates SM4 (2 g, 4.81 mmol), F (2.22 g, 4.81 mmol), sodium tert-butoxide (0.92 g, 9.62 mmol), and Pd2(dba)3 (88 mg, 0.096 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (139 mg, 0.48 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was reduced to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 4 (2.6 g, yield 67.9%). The product was identified as the target product with a molecular weight of 795.33.

[0213] Synthesis Example 5: Synthesis of Compound 9

[0214] Step 1: Synthesis of intermediate G:

[0215]

[0216] Under a nitrogen atmosphere, intermediate A (10 g, 27.4 mmol) and THF (80 mL) were added to a 500 mL two-necked flask. The temperature was lowered to -80 °C, and n-BuLi (23 mL, 57.5 mmol) was added dropwise. The mixture was stirred for 1 h, and then a THF (10 mL) solution of intermediate SM6 (9.6 g, 32.9 mmol) was added dropwise. The reaction temperature was restored to room temperature and stirred for 3 h. The reaction was monitored by TLC until it was complete. The reaction was quenched with an appropriate amount of dilute hydrochloric acid. The mixture was separated into liquid and liquid phases. The aqueous phase was extracted with DCM, and the organic phases were combined and concentrated under reduced pressure. The solid intermediate G (12.6 g, yield 79.7%) was purified by column chromatography.

[0217] Step 2: Synthesis of intermediate H:

[0218]

[0219] Under N2 atmosphere, intermediate G (12.6 g, 21.8 mmol) and DCM (120 mL) were added to a 200 mL two-necked flask. TFA (13 mL) was added dropwise at room temperature. The mixture was stirred overnight at room temperature. The reaction was monitored by TLC until it was complete. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate H (11 g, yield 91.67%).

[0220] Step 3: Synthesis of Compound 9

[0221]

[0222] Under a nitrogen atmosphere, intermediates SM5 (3 g, 7.22 mmol), H (3.97 g, 7.22 mmol), sodium tert-butoxide (1.39 g, 14.44 mmol), and Pd2(dba)3 (132 mg, 0.144 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (210 mg, 0.722 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was restored to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 9 (2.35 g, yield 36.2%). The product was identified as the target product with a molecular weight of 893.44.

[0223] Synthesis Example 6: Synthesis of Compound 198

[0224]

[0225] Under a nitrogen atmosphere, intermediates SM7 (2.36 g, 4.81 mmol), F (2.22 g, 4.81 mmol), sodium tert-butoxide (0.92 g, 9.62 mmol), and Pd2(dba)3 (88 mg, 0.096 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (139 mg, 0.48 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the mixture was cooled to room temperature, filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 198 (2.6 g, yield 61.9%). The product was identified as the target product with a molecular weight of 871.36.

[0226] Synthesis Example 7: Synthesis of Compound 12

[0227] Step 1: Synthesis of Intermediate I:

[0228]

[0229] Under a nitrogen atmosphere, intermediates SM2 (14.07 g, 67.3 mmol), SM8 (20 g, 67.3 mmol), sodium tert-butoxide (13.1 g, 136.4 mmol), Pd2(dba)3 (1.23 g, 1.35 mmol), dppf (3.73 g, 6.73 mmol), and toluene (673 mL) were added sequentially to a 2000 mL reaction flask. The temperature was raised to 120 °C and the reaction was carried out for 3 h. The reaction was monitored by TLC until it was complete. The temperature was then cooled to room temperature, filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to obtain a white solid intermediate I (16.5 g, yield 65%).

[0230] Step 2: Synthesis of intermediate J

[0231]

[0232] Under a nitrogen atmosphere, intermediate I (10.4 g, 27.4 mmol) and THF (80 mL) were added to a 500 mL two-necked flask. The temperature was lowered to -80 °C, and n-BuLi (23 mL, 57.5 mmol) was added dropwise. The mixture was stirred for 1 h, and then a THF (10 mL) solution of intermediate SM6 (9.6 g, 32.9 mmol) was added dropwise. The reaction temperature was restored to room temperature and stirred for 3 h. The reaction was monitored by TLC until it was complete. The reaction was quenched with an appropriate amount of dilute hydrochloric acid. The mixture was separated into liquid and liquid phases. The aqueous phase was extracted with DCM, and the organic phases were combined. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate J (2.6 g, yield 16%).

[0233] Step 3: Synthesis of intermediate K:

[0234]

[0235] Under N2 atmosphere, intermediate J (2.6 g, 4.4 mmol) and DCM (50 mL) were added to a 200 mL two-necked flask. TFA (5 mL) was added dropwise at room temperature. The mixture was stirred overnight at room temperature. The reaction was monitored by TLC until it was complete. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate K (2.52 g, 100% yield).

[0236] Step 4: Synthesis of Compound 12

[0237]

[0238] Under a nitrogen atmosphere, intermediates SM5 (1.82 g, 4.399 mmol), K (2.6 g, 4.39 mmol), sodium tert-butoxide (0.92 g, 9.62 mmol), and Pd2(dba)3 (88 mg, 0.096 mmol) were added sequentially to a 250 mL reaction flask. t Bu3PHBF4 (139 mg, 0.48 mmol) and xylene (50 mL) were reacted overnight at 145 °C. After the reaction was complete as monitored by TLC, the reaction temperature was restored to room temperature. The mixture was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by column chromatography to give a white solid compound 12 (1.02 g, yield 25.6%). The product was identified as the target product with a molecular weight of 907.46.

[0239] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0240] The fabrication methods for organic electroluminescent devices are not limited. The fabrication methods of the device embodiments described below are merely examples and should not be construed as limiting. Those skilled in the art can make reasonable improvements to the fabrication methods of the device embodiments described below based on existing technology.

[0241] Device Examples

[0242] Device Example 1: Fabrication of an organic electroluminescent device.

[0243] First, a 0.7mm thick glass substrate is used, on which a pre-patterned design is applied. A thick indium tin oxide (ITO) substrate was used as the anode. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support and transferred into a vacuum chamber. The organic layer specified below was applied at a vacuum degree of approximately 10... -6 In the case of Torr, The deposition rate was achieved by sequentially depositing compounds HT and HI on the anode layer via vacuum thermal evaporation: first, compounds HT and HI were simultaneously deposited as a hole injection layer (HIL, weight ratio 97:3). ), the vapor-deposited compound HT is used as a hole transport layer (HTL, Compound 1 of the present invention is deposited by vapor deposition as an electron blocking layer (EBL). Then, compounds H-1, H-2, and GD were simultaneously deposited as an luminescent layer (EML, weight ratio 47:47:6). ). Evaporated compound HB serves as a hole-blocking layer (HBL, Compounds ET and Liq were co-deposited as an electron transport layer (ETL, weight ratio 40:60). ), vapor deposition Thick Liq as an electron injection layer (EIL) Finally, metallic aluminum is vapor-deposited as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device.

[0244] Device Example 2: The preparation method of Device Example 2 is the same as that of Device Example 1, except that Compound 2 of the present invention is used instead of Compound 1 of the present invention in the electron blocking layer (EBL).

[0245] Device Example 3: The preparation method of Device Example 3 is the same as that of Device Example 1, except that Compound 5 of the present invention is used instead of Compound 1 of the present invention in the electron blocking layer (EBL).

[0246] Device Example 4: Device Example 4 was prepared in the same manner as Device Example 1, except that Compound 9 of the present invention was used instead of Compound 1 of the present invention in the electron blocking layer (EBL).

[0247] Device Example 5: Device Example 5 was prepared in the same manner as Device Example 1, except that Compound 198 of the present invention was used instead of Compound 1 of the present invention in the electron blocking layer (EBL).

[0248] Device Example 6: Device Example 6 is prepared in the same way as Device Example 1, except that compound 12 of the present invention is used instead of compound 1 of the present invention in the electron blocking layer (EBL).

[0249] Comparative Device Example 1: The preparation method of Comparative Device Example 1 is the same as that of Device Example 1, except that compound EB-1 is used instead of compound 1 of the present invention in the electron blocking layer (EBL).

[0250] The detailed device layer structure and thickness are shown in Table 1 below. The layers used are made of more than one material, and are obtained by doping different compounds in the weight ratios specified herein.

[0251] Table 1. Partial device structures of Examples 1-6 and Comparative Example 1

[0252]

[0253]

[0254] The material structure used in the device is as follows:

[0255]

[0256]

[0257] At 10mA / cm 2 The CIE of Examples 1-6 and Comparative Example 1 was measured at current density, and the maximum emission wavelength λ was determined. max Voltage and power efficiency (PE) at 80 mA / cm 2 The lifetime (LT97) of Examples 1-6 and Comparative Example 1 was measured at current density. For a more intuitive comparison, the LT97 of Comparative Example 1 was set to 1, and the LT97 of Examples 1-6 were calculated relative to Comparative Example 1. These data were recorded and are shown in Table 2.

[0258] Table 2 Device data for Examples 1-6 and Comparative Example 1

[0259] Device Number CIE(x,y) <![CDATA[λ max (nm)]]> Voltage (V) Power efficiency (lm / W) LT97 Example 1 (0.348,0.627) 531 3.50 75.0 220 Example 2 (0.350,0.625) 531 3.50 77.0 160 Example 3 (0.355,0.622) 531 3.40 73.0 400 Example 4 (0.351,0.624) 530 4.38 60.0 112 Example 5 (0.351,0.624) 531 3.36 76.2 190 Example 6 (0.351,0.624) 531 4.33 60.8 108 Comparative Example 1 (0.350,0.625) 531 4.50 59.9 1

[0260] discuss:

[0261] As can be seen from the data in Table 2, the CIE values ​​and maximum emission wavelengths of Examples 1-6 and Comparative Example 1 are basically consistent.

[0262] Compared to Comparative Example 1, the voltage of Example 1 was significantly reduced by 1V, while the power efficiency was greatly improved by 25.2%. More importantly, the lifetime was unexpectedly increased by 219 times. Both Compound 1 of the present invention and Compound EB-1 of the comparative example have spiroacridine and arylsilane structural segments, the only difference being whether the acridine structural segment has an additional specific fused structure. However, the device performance of the two is very different, indicating that the compound of the present invention, due to having a specific fused acridine spirocyclic structural segment, can significantly reduce the device voltage, greatly improve the device efficiency, and especially unexpectedly improve the device lifetime, thus providing better overall performance in the device.

[0263] Examples 2-6 demonstrate the device performance of more compounds of the present invention. These compounds have adjusted the connection positions of the fused acridine spirocyclic segment and the silicon-based segment, and / or adjusted the substituents of the fused acridine spirocyclic segment or the silicon-based segment. As shown in Table 2, Examples 2-6 also exhibit excellent device performance. Compared to Comparative Example 1, Example 2 shows a 1V reduction in voltage, a significant 28.5% increase in power efficiency, and a 159-fold increase in lifetime; Example 3 shows a 1.1V reduction in voltage, a significant 21.9% increase in power efficiency, and an unexpectedly large 399-fold increase in lifetime; Example 4 shows a 0.12V reduction in voltage, maintaining a substantially high level of power efficiency, and a 111-fold increase in lifetime; Example 5 shows a 1.14V reduction in voltage, a significant 27.2% increase in power efficiency, and a 189-fold increase in lifetime; Example 6 shows a 0.17V reduction in voltage, maintaining a substantially high level of power efficiency, and a 107-fold increase in lifetime. These results further demonstrate the excellent performance of the compounds of the present invention.

[0264] In summary, the compounds with specific structures represented by Formula 1 of the present invention, when used in organic electroluminescent devices, can significantly reduce device voltage, improve device efficiency, and especially greatly extend device lifespan, providing better overall device performance, and have very broad application prospects.

[0265] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the 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 substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A compound having a structure represented by Formula 1: in, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; L is selected from arylene groups having 6-30 carbon atoms, heteroarylene groups having 3-30 carbon atoms, or combinations thereof; wherein the arylene groups and heteroarylene groups are unsubstituted or can optionally be substituted by one or more groups R1. Q is selected from CR'R", SiR'R", NR N O or S; W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ; R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution; R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

2. The compound of claim 1, wherein, The L is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof; Preferably, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted silylfluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or combinations thereof.

3. The compound of claim 1, wherein, The compound has a structure represented by Formula 2: Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof. Z1 to Z5 are selected from C, CR1, or N each time they appear, and one of Z1 to Z5 is C and connected to Si; Q is selected from CR'R", SiR'R", NR. N O or S; W is selected from single bonds, O, S, CR'R", SiR'R", or NR. N ; R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution; R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a ring.

4. The compound of claim 3, wherein, The compound has a structure represented by any one of formulas 2-1, 2-2, 2-3, 2-4, 2-5, and 2-6: Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof. Z1 to Z5 are selected from C, CR1, or N each time they appear, and one of Z1 to Z5 is C and connected to Si; Q is selected from CR'R", SiR'R", NR. N O or S; R2, R3, and R4 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution; R1, R2, R3, R4, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R1, R2, R3, R4, R', R'', R'' N They can be arbitrarily connected to form a loop; Preferably, the compound has a structure represented by formula 2-1, formula 2-3, formula 2-4 or formula 2-5.

5. The compound of claim 4, wherein, The Q is selected from CR'R”; Preferably, the R' and R'" appear in the same or different ways each time they appear, and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; More preferably, the R' and R" are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and combinations thereof, each time they appear.

6. The compound of claim 4, wherein, The compound has a structure represented by any one of Formulas 3-1 to 3-12: Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof. X is selected from CR'R", SiR'R", NR N O or S; R1, R3, R4, and R5, when they appear in the same or different ways, represent monosubstitution, polysubstitution, or no substitution. R1, R3, R4, R5, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R1, R3, R4, R5, R', R'', R'' N They can be arbitrarily connected to form a loop; Preferably, the compound has a structure represented by formula 3-1, formula 3-2, formula 3-9 or formula 3-10.

7. The compound of claim 6, wherein, The X is selected from CR'R", NR N O or S; Preferably, X is selected from CR'R".

8. The compound according to any one of claims 1-7, wherein, Each time Ar appears, it is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-25 carbon atoms, or combinations thereof; Preferably, the Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, or combinations thereof; More preferably, the Ar, each time it appears, is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyreneyl, or combinations thereof.

9. The compound according to any one of claims 1-4, wherein, The R1, R2, R3, R4, R' ... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 cyclic atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof; Preferably, R1, R2, R3, R4, R' ... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and combinations thereof.

10. The compound of claim 6, wherein, The R1, R3, R4, R5, R', R", R N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 cyclic atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof; Preferably, R1, R3, R4, R5, R' ... N Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and combinations thereof.

11. The compound of claim 1, wherein, The compounds are selected from the group consisting of compounds 1 to 470: Optionally, the hydrogen in the structure of compounds 1 to 470 can be partially or completely replaced by deuterium.

12. An organic electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising any one of claims 1-11.

13. The organic electroluminescent device as described in claim 12, wherein, The organic layer is an electron blocking layer, a hole injection layer, a hole transport layer, or a light-emitting layer; Preferably, the organic layer is an electron blocking layer, and the compound is an electron blocking material.

14. A compound composition comprising any one of the compounds of claims 1-11.

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