Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure shown in a formula 1, and the compound can be used as an electron blocking material and the like in an organic electroluminescent device. When the compound is applied to the organic electroluminescent device, low voltage can be maintained or the voltage of the device can be reduced, the efficiency of the device is improved, especially the service life of the device is prolonged, and better comprehensive performance of the device is provided. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

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

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

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

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

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

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

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

[0008] The performance of organic electroluminescent devices, such as voltage and efficiency, is significantly related to the balance of carrier concentrations in the light-emitting layer. By designing the molecular structures of charge transport materials and carrier blocking materials, the balance of carrier concentrations in the light-emitting layer can be more reasonably regulated. Compounds with triarylamine and spirosilfluorene structures can be used as hole transport materials and electron blocking materials (light-emitting auxiliary materials) in electroluminescent devices. Currently, there have been some reports on triarylamine-spirosilfluorene compounds.

[0009] KR20220001621A discloses compounds with the structure, where A must be the structure represented by and discloses compounds such as in specific structures. However, this application does not disclose compounds with other structures for A, nor does it disclose compounds with the specific structures represented by Formula 1-1, Formula 1-2, or Formula 1-3 in the present invention.

[0010] KR20220014116A discloses compounds with the structure, where A must be the structure represented by and discloses compounds such as in specific structures. However, this application does not disclose compounds with other structures for A, nor does it disclose compounds with the specific structures represented by Formula 1-1, Formula 1-2, or Formula 1-3 in the present invention.

[0011] A previous patent application US2022359832A1 by the applicant of the present invention discloses an organic electroluminescent device including a first compound represented by the structure and a second compound represented by the structure in the organic layer. This application focuses on the application of the combination of these two compounds as hole injection materials and does not focus on the application of the second compound as an electron blocking material. This application also does not disclose that the arylamine fragment in the second compound is specifically connected to the 4-position of spirosilfluorene and that Ar1 and Ar2 are compounds with the specific structures represented by Formula 1-1, Formula 1-2, or Formula 1-3 in the present invention.

[0012] With the increasing demand for the performance of organic electroluminescent devices in the industry, OLED materials with excellent properties such as lower voltage, higher efficiency, and longer lifespan still need to be further studied and developed. Summary of the Invention

[0013] The present invention aims to provide a series of triarylamine-spirosilole compounds represented by the structure of Formula 1 to solve at least part of the above problems. These compounds can be used in organic electroluminescent devices, for example, as electron blocking materials. When applied to organic electroluminescent devices, these compounds can maintain a low voltage or reduce the device voltage, improve the device efficiency, especially the device lifetime, and provide better comprehensive device performance.

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

[0015]

[0016] Wherein, Ar1 and Ar2 are the same or different each time they appear and are independently selected from the structures represented by Formula 1-1, Formula 1-2, or Formula 1-3;

[0017]

[0018] L, L1, and L2 are the same or different each time they appear and are independently selected from a single bond, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0019] X is the same or different each time it appears and is independently selected from CR x or N;

[0020] Z is selected from CR z R z , SiR z R z , O, S, Se, or NR z ; when two R z are present simultaneously, the two R z are the same or different;

[0021] Y1 to Y 10 , Y 11 to Y 18 , Y 21 to Y 28 are the same or different each time they appear and are independently selected from C, CR y or N; and one of Y1 to Y 10 is selected from C and is connected to L1 or L2; one of Y 11 to Y 18 must be selected from C and is connected to L1 or L2; one of Y 21 to Y 28 is selected from C and is connected to L1 or L2;

[0022] R xEach occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0023] R y ,R z Each occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0024] And when the said R y ,R zWhen selected from substituted groups, the group is substituted by one or more groups selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, the structures represented by Formula 1-1, Formula 1-2, Formula 1-3, and combinations thereof;

[0025] Adjacent substituents R x , R y , R z can optionally be connected to form a ring;

[0026] "*" represents the connection position of Formula 1-1, Formula 1-2, Formula 1-3 to L1 or L2.

[0027] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound described in the foregoing embodiment.

[0028] According to another embodiment of the present invention, a compound composition is also disclosed, and the compound composition contains the compound described in the foregoing embodiment.

[0029] The present invention discloses a series of triarylamine-spirosilfluorene compounds represented by Formula 1 structure. The compounds can be used in organic electroluminescent devices, for example, as an electron blocking material, etc., which can improve the performance of organic electroluminescent devices. For example, it can maintain a low voltage or reduce the device voltage, improve the device efficiency, especially improve the device lifetime, and improve the comprehensive performance of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein.

[0031] Figure 2It is another schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein.

[0032] Figure 3 It is a schematic diagram of the structure of a typical top-emitting OLED that can contain the compounds and compound compositions disclosed herein. Detailed Description

[0033] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 The organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of which is incorporated herein by reference.

[0034] There are more examples of each of these layers. For example, U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, which is incorporated herein by reference in its entirety and was awarded to Thompson et al. 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, which include a composite cathode having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer, are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. The principles and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0035] The above-described hierarchical structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve the desired emission spectrum.

[0036] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0037] The OLED also requires a encapsulation layer, such as Figure 2 schematically and non-limitingly shows an organic light-emitting device 200, which Figure 1 differently, an encapsulation layer 102 can also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0038] A typical top-emitting OLED device structure is as Figure 3 schematically shown. Among them, the OLED device 300 includes: an anode layer 301, a hole injection layer (HIL) 302, a hole transport layer (HTL) 303, an electron blocking layer (EBL) 304 (which can also be referred to as a light-emitting auxiliary layer or prime layer), a light-emitting layer (EML) 305, a hole blocking layer (HBL) 306, and the hole blocking layer 306 is an optional layer. An electron transport layer (ETL) 307, an electron injection layer (EIL) 308, a cathode layer 309, and a capping layer 310. Among them, the anode layer 301 is a material or a combination of materials with high reflectivity, including but not limited to Ag, Al, Ti, Cr, Pt, Ni, TiN, and combinations of the above materials with ITO and / or MoOx (molybdenum oxide). Generally, the reflectivity of the anode is greater than 50%; preferably, the reflectivity of the anode is greater than 70%; more preferably, the reflectivity of the anode is greater than 80%; while the cathode layer 309 should be a semi-transparent or transparent conductive material, including but not limited to MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or combinations thereof, and its average transmittance for light with wavelengths in the visible light region is greater than 15%; preferably, the average transmittance for light with wavelengths in the visible light region is greater than 20%; more preferably, the average transmittance for light with wavelengths in the visible light region is greater than 25%.

[0039] Devices fabricated in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) with the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.

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

[0041] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, there may be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

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

[0043] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

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

[0045] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the conversion between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of singlet excited state populated back can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.

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

[0047] Definition of substituent terms

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

[0049] Alkyl – as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.

[0050] Cycloalkyl - as used herein, includes cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 ring 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. Additionally, the cycloalkyl group can be optionally substituted.

[0051] Heteroalkyl - as used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, phosphorus atoms, silicon atoms, germanium atoms, 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, 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, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group can be optionally substituted.

[0052] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The 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 - diphenylethylene, 1,2 - diphenylethylene, 1 - methylallyl, 1,1 - dimethylallyl, 2 - methylallyl, 1 - phenylallyl, 2 - phenylallyl, 3 - phenylallyl, 3,3 - diphenylallyl, 1,2 - dimethylallyl, 1 - phenyl - 1 - butenyl, 3 - phenyl - 1 - butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group can be optionally substituted.

[0053] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0054] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0055] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.

[0056] Heteroaryl - As used herein, non - fused and fused heteroaromatic groups that can contain 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and its nitrogen analogs. Additionally, the heteroaryl can be optionally substituted.

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

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

[0059] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0060] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0061] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

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

[0063] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0064] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all such analogs are determined to be included in the terms described herein.

[0065] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocycloalkyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

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

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

[0068] Among the compounds mentioned in the present disclosure, multiple substitution refers to the range including double substitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist at multiple available substitution positions on its connecting structure, and the substituents existing at multiple available substitution positions can be of the same structure or different structures.

[0069] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, otherwise adjacent substituents in the compound cannot connect to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case 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 spiro ring, bridged ring, fused ring, etc.), as well as an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0070] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

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

[0075]

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

[0077]

[0078] According to one embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0079]

[0080] Wherein, each occurrence of Ar1 and Ar2 is the same or different and is independently selected from the structures represented by Formula 1-1, Formula 1-2, or Formula 1-3;

[0081]

[0082] L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0083] Each occurrence of X is the same or different and is independently selected from CR x or N;

[0084] Z is selected from CR z R z , SiR z R z , O, S, Se, or NR z ; when two Rs z are present simultaneously, the two Rs z are the same or different;

[0085] Y1 to Y 10 , Y 11 to Y 18 , Y 21 to Y 28 are each independently selected from C, CR y or N; and one of Y1 to Y 10 is selected from C and is connected to L1 or L2; one of Y 11 to Y 18 must be selected from C and is connected to L1 or L2; one of Y 21 to Y 28 is selected from C and is connected to L1 or L2;

[0086] R xEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0087] R y ,R z Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0088] And when said R y ,R zWhen selected as a substituted group, the group is substituted by one or more groups selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, structures represented by Formula 1-1, Formula 1-2, Formula 1-3, and combinations thereof;

[0089] Adjacent substituents R x , R y , R z can optionally be linked to form a ring;

[0090] "*" represents the connection position of Formula 1-1, Formula 1-2, Formula 1-3 with L1 or L2.

[0091] In this article, "adjacent substituents R x can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, two adjacent substituents R x can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring.

[0092] In this article, "adjacent substituents R x , R y , R z can optionally be linked to form a ring" is intended to mean that any adjacent substituents R x can be linked to form a ring, adjacent substituents R z can be linked to form a ring, and also means that in Formula 1-1, any adjacent substituents R among Y1 to Y5 y can be linked to form a ring, and any adjacent substituents R among Y6 to Y 10 can be linked to form a ring, and also means that in Formula 1-2, any adjacent substituents R among Y y to Y 11 to Y 14 can be linked to form a ring, and also means that in Formula 1-3, any adjacent substituents R among Y yCapable of connecting to form a ring, Y 15 To Y 18 Any adjacent substituents R among them y Capable of connecting to form a ring, and it is also intended to indicate that in Formulas 1-3, Y 21 To Y 28 Any adjacent substituents R among them y Capable of connecting to form a ring. Obviously, these substituents may also not connect to form a ring with each other.

[0093] In this article, Formula 1-2 is connected to L1 or L2 through the positions selected from C among Y 11 To Y 18 and is not connected to L1 or L2 through Z or R z Connected to L1 or L2.

[0094] According to an embodiment of the present invention, wherein said L, L1, L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof each time they appear.

[0095] According to an embodiment of the present invention, wherein said L, L1, L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silafuorenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzoselenophenyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted spirobifluorenyl, or a combination thereof each time they appear.

[0096] According to an embodiment of the present invention, wherein said L, L1, L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene each time they appear.

[0097] According to an embodiment of the present invention, wherein said L, L1, L2 are selected from a single bond.

[0098] According to an embodiment of the present invention, wherein said X is each independently selected from CR x .

[0099] According to an embodiment of the present invention, wherein said Y1 to Y 10 , Y 11 To Y 18 , Y 21 To Y 28Each occurrence is the same or different and is selected from C or CR y 。

[0100] According to one embodiment of the present invention, at least one of the Ar1 and Ar2 has a structure represented by Formula 1-2.

[0101] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z , O, S, or NR z 。

[0102] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z 。

[0103] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z ; R z is selected from methyl or phenyl.

[0104] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z ; R z are both selected from methyl.

[0105] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z , two Rs z can optionally be connected to form a ring.

[0106] According to one embodiment of the present invention, in Formula 1-2, the Z is selected from CR z R z , two Rs z do not connect to form a ring.

[0107] According to one embodiment of the present invention, in Formula 1-2, Y 12 or Y 13 is selected from C and is connected to L1 or L2.

[0108] According to one embodiment of the present invention, in Formula 1-2, Y 12 is selected from C and is connected to L1 or L2.

[0109] According to one embodiment of the present invention, wherein the R xEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, and combinations thereof.

[0110] According to one embodiment of the present invention, wherein the R x Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, and combinations thereof.

[0111] According to one embodiment of the present invention, wherein the R x Each occurrence is the same as or different from and is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or combinations thereof.

[0112] According to one embodiment of the present invention, wherein the R x Each occurrence is the same as or different from and is selected from hydrogen, deuterium, methyl, phenyl, biphenyl, naphthyl, or combinations thereof.

[0113] According to one embodiment of the present invention, wherein the R x Is selected from hydrogen.

[0114] According to one embodiment of the present invention, wherein the R x Is a neutral group or an electron-donating group.

[0115] According to one embodiment of the present invention, wherein the R x Does not contain an electron-withdrawing group.

[0116] According to one embodiment of the present invention, wherein the R y , R z Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0117] According to one embodiment of the present invention, wherein the R y , R z is the same or different each time it appears and is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirosilafuorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof.

[0118] According to one embodiment of the present invention, wherein the R z is the same or different each time it appears and is selected from hydrogen, deuterium, methyl, phenyl, biphenyl, naphthyl, or a combination thereof.

[0119] According to one embodiment of the present invention, wherein the R y is selected from hydrogen.

[0120] According to one embodiment of the present invention, wherein the Ar1 and Ar2 are the same or different each time they appear and are selected from substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof.

[0121] According to one embodiment of the present invention, the Ar1 and Ar2 are the same or different each time they appear and are selected from substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorene, or a combination thereof.

[0122] According to one embodiment of the present invention, wherein the Ar1 and Ar2 are the same or different each time they appear and are selected from the group consisting of G1 to G68, and the specific structures of G1 to G68 are shown in claim 8.

[0123] According to one embodiment of the present invention, wherein the compound is selected from the group consisting of compound 1 to compound 2349, compound H1 to compound H82, and the specific structures of compound 1 to compound 2349, compound H1 to compound H82 are shown in claim 9.

[0124] According to one embodiment of the present invention, the hydrogen in the structures of compound 1 to compound 2349, compound H1 to compound H82 can be partially or completely replaced by deuterium.

[0125] According to one embodiment of the present invention, a compound composition is disclosed, which comprises the compound described in any one of the foregoing embodiments.

[0126] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes: an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound described in any of the foregoing embodiments.

[0127] According to an embodiment of the present invention, in the organic electroluminescent device, the organic layer is an electron blocking layer, a hole transport layer, or a light emitting layer.

[0128] According to an embodiment of the present invention, wherein the organic layer includes a first organic layer and a second organic layer;

[0129] The first organic layer contains the compound having the structure represented by Formula 1, and the specific structure of the compound is as described in any of the foregoing embodiments;

[0130] The second organic layer contains a second compound and a third compound;

[0131] The second compound has a structure represented by Formula 2:

[0132]

[0133] Wherein, L x Each occurrence is the same or different and is independently selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0134] V is the same or different each occurrence and is independently selected from C, CR v or N;

[0135] T is the same or different each occurrence and is independently selected from C, CR t or N;

[0136] R v and R tEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0137] Each occurrence of Ar is the same as or different from and is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or combinations thereof;

[0138] Adjacent substituents R v and R t can optionally be connected to form a ring;

[0139] The third compound has a structure represented by Formula 3:

[0140]

[0141] wherein, each occurrence of E1-E6 is the same as or different from and is selected from C, CR e or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and is connected to Formula A;

[0142]

[0143] wherein, each occurrence of Q is the same as or different from and is selected from the group consisting of O, S, Se, N, NR Q , CR Q R Q , SiR Q R Q , GeR Q R Q and R Q C═CR Qa group consisting of; when two Rs are present simultaneously Q the two Rs Q can be the same or different;

[0144] p is 0 or 1; r is 0 or 1;

[0145] when Q is selected from N, p is 0 and r is 1;

[0146] when Q is selected from the group consisting of O, S, Se, NR Q , CR Q R Q , SiR Q R Q , GeR Q R Q and R Q C═CR Q the group consisting of, p is 1 and r is 0;

[0147] L1, each occurrence, is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0148] Q1-Q8, each occurrence, is the same or different and is selected from C, CR q or N;

[0149] R e R Q and R qEach occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0150] “*” represents the connecting position of Formula A and Formula 3;

[0151] Adjacent substituents R e , R Q , R q can optionally be connected to form a ring.

[0152] As used herein, “adjacent substituents R v and R t can optionally be connected to form a ring” is intended to mean that among adjacent substituent groups, for example, between two substituents R v , between two substituents R t , between substituent R v and R t , between substituent R v and R g , any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may also not be connected to form a ring.

[0153] As used herein, “adjacent substituents R e , R Q , R q can optionally be connected to form a ring” is intended to mean that among adjacent substituent groups, for example, between two substituents R e , between two substituents R Q , between two substituents R q , between two substituents R Q and Rq Among them, any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring either.

[0154] According to an embodiment of the present invention, the second compound has a structure represented by one of Formula 2-1 to Formula 2-10:

[0155]

[0156] Wherein, L x is the same or different each time it appears and is selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0157] V is the same or different each time it appears and is selected from CR v or N;

[0158] T is the same or different each time it appears and is selected from CR t or N;

[0159] R v and R t are the same or different each time they appear and are selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted alkynyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl having 6-20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, a substituted or unsubstituted arylgermyl having 6-20 carbon atoms, a substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0160] Ar is the same or different each time it appears and is selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof;

[0161] Adjacent substituents R v and R t can optionally be linked to form a ring.

[0162] According to one embodiment of the present invention, in the second compound, each occurrence of Ar is the same or different and is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 25 carbon atoms, or a combination thereof.

[0163] According to one embodiment of the present invention, in the second compound, each occurrence of Ar is the same or different and is selected from phenyl, fluorophenyl, naphthyl, biphenyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, 9,9-dimethylfluorenyl, 9,9-spirobifluorenyl, cyanophenyl, or a combination thereof.

[0164] According to one embodiment of the present invention, wherein the second compound is selected from the group consisting of the following structures:

[0165]

[0166]

[0167] According to one embodiment of the present invention, in the compounds PH-1 to PH-37, the hydrogen in the structure can be partially or completely replaced by deuterium.

[0168] According to one embodiment of the present invention, in the third compound, each occurrence of E1 - E6 is the same or different and is selected from C, CR e or N, and three of E1 - E6 are N, and at least one of E1 - E6 is CR e and the R e each occurrence of which is the same or different and is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof;

[0169] and / or each occurrence of Q is the same or different and is selected from O, S, N or NR Q ;

[0170] and / or at least one or at least two of Q1 - Q8 are selected from CR q and the R q is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof;

[0171] And / or L1, each occurrence being the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof.

[0172] According to one embodiment of the present invention, in the third compound, Q1-Q8, each occurrence being the same or different, is selected from C, CR q or N, and at least one of Q1-Q8 is selected from N, for example, one or two of Q1-Q8 are selected from N.

[0173] According to one embodiment of the present invention, wherein the third compound is selected from the group consisting of the following compounds:

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] According to one embodiment of the present invention, wherein the hydrogen in the structures of Compounds H-1 to H-117 can be partially or completely replaced by deuterium.

[0181] According to one embodiment of the present invention, in the organic electroluminescent device, the first organic layer is an electron blocking layer or a hole transport layer; the second organic layer is a light emitting layer.

[0182] According to one embodiment of the present invention, in the organic electroluminescent device, the first organic layer is an electron blocking layer.

[0183] According to one embodiment of the present invention, wherein the thickness of the electron blocking layer is between 1 nm and 500 nm.

[0184] According to one embodiment of the present invention, in the organic electroluminescent device, the first organic layer is an electron blocking layer, and the compound is an electron blocking material; the second organic layer is a light emitting layer, and the second compound and the third compound are host materials.

[0185] According to one embodiment of the present invention, in the organic electroluminescent device, the light emitting layer further comprises a phosphorescent material.

[0186] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is a green light-emitting material.

[0187] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is a red light-emitting material.

[0188] According to an embodiment of the present invention, wherein the phosphorescent material is selected from the group consisting of:

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] According to an embodiment of the present invention, wherein the organic electroluminescent device is a stacked device.

[0196] In the device of the present invention, a hole transport layer may be included, and the hole transport material is a diamine compound.

[0197] In combination with other materials

[0198] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0199] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0200] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0201] Material synthesis example:

[0202] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0203] Synthesis Example 1: Synthesis of Compound 1530

[0204]

[0205] Xylene (60 mL), intermediate S1 (3.13 g, 7.79 mmol), intermediate S2 (3.0 g, 8.18 mmol) were added to a 250 mL three-necked round-bottom flask in sequence. tBuOLi (1.25 g, 15.63 mmol). Purge with N₂ for 30 min, then add Pd₂(dba)₃ (0.21 g, 0.234 mmol) and RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl, 0.22 g, 0.467 mmol), and react at 145 °C overnight. Monitor the reaction by TLC until completion. Cool the reaction mixture to room temperature, filter through celite, remove the solvent under reduced pressure, and purify by column chromatography to obtain white solid compound 1530 (2.38 g, yield 41.8%). The product was confirmed to be the target product with a molecular weight of 731.30.

[0206] Synthesis Example 2: Synthesis of Compound 96

[0207]

[0208] Add xylene (52 mL), intermediate S3 (2.63 g, 7.28 mmol), and intermediate S2 (2.8 g, 7.63 mmol) successively to a 250 mL three-necked round-bottom flask. t BuOLi (1.16 g, 14.5 mmol). Purge with N₂ for 30 min, then add Pd₂(dba)₃ (0.20 g, 0.218 mmol) and RuPhos (0.20 g, 0.44 mmol), and react at 145 °C overnight. Monitor the reaction by TLC until completion. Cool the reaction mixture to room temperature, filter through celite, remove the solvent under reduced pressure, and purify by column chromatography to obtain white solid compound 96 (2.08 g, yield 41.4%). The product was confirmed to be the target product with a molecular weight of 691.27.

[0209] Synthesis Example 3: Synthesis of Compound 1538

[0210]

[0211] Add xylene (60 mL), intermediate S4 (3 g, 6.87 mmol), and intermediate S2 (2.77 g, 7.56 mmol) successively to a 250 mL three-necked round-bottom flask. t BuOLi (1.1 g, 13.74 mmol). Purge with N₂ for 30 min, then add Pd₂(dba)₃ (0.19 g, 0.207 mmol) and RuPhos (0.19 g, 0.407 mmol), and react at 145 °C overnight. Monitor the reaction by TLC until completion. Cool the reaction mixture to room temperature, filter through celite, remove the solvent under reduced pressure, and purify by column chromatography to obtain white solid compound 1538 (1.50 g, yield 28.5%). The product was confirmed to be the target product with a molecular weight of 767.30.

[0212] Synthesis Example 4: Synthesis of Compound 1320

[0213]

[0214] To a 250 mL three-necked round-bottom flask, xylene (40 mL), intermediate S5 (1.87 g, 4.78 mmol), and intermediate S2 (2.10 g, 5.73 mmol) were successively added. t BuOLi (0.77 g, 9.55 mmol) was added, and N2 was bubbled through for 30 min. Then, Pd2(dba)3 (0.13 g, 0.143 mmol) and RuPhos (0.13 g, 0.287 mmol) were added, and the reaction was carried out at 145 °C overnight. The reaction was monitored by TLC until completion. The reaction mixture was cooled to room temperature, filtered through celite, and the solvent was removed under reduced pressure. The residue was purified by column chromatography to obtain a white solid compound 1320 (1.64 g, yield 47.5%). The product was confirmed to be the target product with a molecular weight of 721.23.

[0215] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0216] The preparation method of the organic electroluminescent device is not limited. The preparation method of the following device examples is only an example and should not be construed as a limitation. Those skilled in the art can reasonably improve the preparation method of the following device examples based on the prior art.

[0217] Device Examples

[0218] Device Example 1: Fabrication of a top-emitting organic electroluminescent device.

[0219] First, a 0.7 mm thick glass substrate with a pre-patterned indium tin oxide (ITO) / silver (Ag) / indium tin oxide (ITO) layer with a thickness of was used as the anode. The substrate was washed with deionized water and detergent, and 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 the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The following specified organic layers were deposited on the anode layer by vacuum thermal evaporation at a rate of -6 under a vacuum of about 10 Torr: First, compounds HT-1 and HT-2 were co-evaporated as the hole injection layer (HIL, weight ratio 97:3, ), compound HT-1 was evaporated as the hole transport layer (HTL, ), and the compound 96 of the present invention was evaporated as the electron blocking layer (EBL, ), then simultaneously evaporate compound PH-1, compound H-40 and compound GD1 as the emitting layer (EML, weight ratio 48:48:4, ). Evaporate compound HB as the hole blocking layer (HBL, ), co-deposit compound ET and Liq as the electron transport layer (ETL, 40:60, ), evaporate a metal Yb with a thickness of as the electron injection layer (EIL). Evaporate metal Mg and metal Ag as the cathode (Cathode, weight ratio 1:9, ). Finally, evaporate the CPL material as the capping layer (CPL, where the CPL material is a material selected to have a refractive index of approximately 1.92 at 620 nm, and the refractive index is obtained by measuring a 30-nm-thick CPL material evaporated on a silicon wafer using an ellipsometer model ES01 from Beijing Liangtuo Technology Co., Ltd.). Then transfer the device back to the glove box and encapsulate it with a glass cover to complete the device.

[0220] Device Example 2

[0221] The preparation method of Device Example 2 is the same as that of Device Example 1, except that in the electron blocking layer (EBL), compound 1530 of the present invention is used instead of compound 96 of the present invention.

[0222] Device Comparative Example 1

[0223] The preparation method of Device Comparative Example 1 is the same as that of Device Example 1, except that in the electron blocking layer (EBL), compound EB-1 is used instead of compound 96 of the present invention.

[0224] Device Comparative Example 2

[0225] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that in the electron blocking layer (EBL), compound EB-2 is used instead of compound 96 of the present invention.

[0226] Device Comparative Example 3

[0227] The preparation method of Device Comparative Example 3 is the same as that of Device Example 1, except that in the electron blocking layer (EBL), compound EB-3 is used instead of compound 96 of the present invention.

[0228] The detailed device layer structures and thicknesses are shown in Table 1 below. For the layers where more than one material is used, they are doped with different compounds in the recorded weight ratios.

[0229] Table 1 Partial device structures of Examples 1-2 and Comparative Examples 1-3

[0230]

[0231] The material structure used in the device is as follows:

[0232]

[0233]

[0234] Table 2 summarizes and shows the device performances of Examples 1-2 and Comparative Examples 1-3. Among them, the maximum emission wavelength (λ max ), voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) were measured at a current density of 10 mA / cm 2 , and the lifetime LT97 was measured at a current density of 80 mA / cm 2 . LT97 is the time taken for the device brightness to decay to 97% of the initial brightness.

[0235] Table 2 Device data of Examples 1-2 and Comparative Examples 1-3

[0236]

[0237] Discussion:

[0238] As can be seen from the data in Table 2, compared with Comparative Example 1, although the voltage of Example 1 is slightly higher than that of Comparative Example 1, it is still at a relatively low voltage level. More importantly, the current efficiency, power efficiency, and external quantum efficiency of Example 1 are significantly increased by 29.7%, 18.2%, and 25.1% respectively, and the lifetime is greatly increased by 82.0%. The above results show that the triarylamine-spirosilfluorene compound of the present invention with an arylamine fragment connected to the 4-position of spirosilfluorene, compared with the comparative example compound with an arylamine fragment connected to the 2-position of spirosilfluorene, only differs in the connection position of the arylamine fragment to spirosilfluorene. However, the current efficiency, power efficiency, and external quantum efficiency of Example 1 using the compound of the present invention are significantly improved, especially the device lifetime is unexpectedly greatly improved, demonstrating the unique performance of the compound with a specific structure represented by Formula 1 of the present invention.

[0239] Compared with Comparative Example 2, the voltage of Example 1 decreased by 0.6 V, and the current efficiency, power efficiency, and external quantum efficiency increased by 21.5%, 37.5%, and 16.0% respectively. More importantly, the lifetime increased unexpectedly by 275%. Compared with Comparative Example 2, the voltage of Example 2 decreased significantly by 1.1 V. At the same time, the current efficiency, power efficiency, and external quantum efficiency increased significantly by 18.4%, 50%, and 15% respectively. Even more unexpectedly, the lifetime increased significantly by 324%. The above results show that the compound with a specific group connected to the triarylamine fragment of the triarylamine-spirosilfluorene compound of the present invention, compared with the comparative example compound with other groups connected to the triarylamine fragment, can reduce the device voltage, and at the same time, the current efficiency, power efficiency, and external quantum efficiency are significantly improved. In particular, the device lifetime has an unexpectedly large increase, which once again proves the unique performance of the compound with the specific structure represented by Formula 1 of the present invention.

[0240] Compared with Comparative Example 3, while maintaining the same low voltage level as it, Example 1 significantly improved the current efficiency, power efficiency, and external quantum efficiency by 25.5%, 21.2%, and 19.6% respectively, and the lifetime increased significantly by 106%. The above results show that the spirosilfluorene-triarylamine compound of the present invention, compared with the silfluorene-triarylamine compound of the comparative example, has achieved a significant increase in the current efficiency, power efficiency, and external quantum efficiency, especially the lifetime, indicating the unique performance of the compound with the specific structure represented by Formula 1 of the present invention.

[0241] In summary, the compound with the specific structure represented by Formula 1 of the present invention is used in an organic light-emitting device, which can maintain a low voltage level or further reduce the voltage, significantly improve the device efficiency, especially can greatly improve the device lifetime, provide better comprehensive device performance, and has a very broad application prospect.

[0242] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A compound having a structure represented by Formula 1: Among them, Ar1 and Ar2 are each independently selected from structures represented by Formula 1-1, Formula 1-2, or Formula 1-3; L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof; X is the same as or different each time it appears and is selected from CR x or N; Z is selected from CR z R z , SiR z R z , O, S, Se, or NR z ; when two Rs are present simultaneously z , the two Rs z are the same or different; Y1 to Y 10 , Y 11 to Y 18 , Y 21 to Y 28 are each independently selected from C, CR y or N; and one of Y1 to Y 10 is selected from C and is connected to L1 or L2; one of Y 11 to Y 18 must be selected from C and is connected to L1 or L2; one of Y 21 to Y 28 is selected from C and is connected to L1 or L2; R x Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; R y , R z is the same as or different from each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; And when the R y , R z is selected from a substituted group, the group is substituted by one or more groups selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, the structures represented by Formula 1-1, Formula 1-2, Formula 1-3, and combinations thereof; Adjacent substituents R x , R y , R z can optionally be linked to form a ring; "*" represents the connecting position of Formula 1-1, Formula 1-2, Formula 1-3 to L1 or L2.

2. The compound according to claim 1, wherein, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silafuorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenophenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted spirobifluorenylene, or a combination thereof; Preferably, L, L1, and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene; More preferably, L, L1, and L2 are selected from a single bond.

3. The compound according to claim 1, wherein, Each occurrence of X is the same as or different from and is selected from CR x ; and / or Y1 to Y 10 , Y 11 to Y 18 , Y 21 to Y 28 Each occurrence is the same as or different from and is selected from C or CR y .

4. The compound according to claim 1, wherein, At least one of Ar1 and Ar2 has a structure represented by Formula 1-2; Preferably, in Formula 1-2, the Z is selected from CR z R z , O, S, or NR z ; More preferably, Z is selected from CR z R z .

5. The compound according to claim 1, wherein, Said R x is the same as or different from each other each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, and combinations thereof; Preferably, the R x is the same as or different from each other each time it appears and is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof; More preferably, said R x is the same as or different from each other each time it appears and is selected from hydrogen, deuterium, methyl, phenyl, biphenyl, naphthyl, or a combination thereof.

6. The compound according to claim 1, wherein Said R y , R z is the same as or different from each other each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; Preferably, the R y , R z is the same as or different from each other each time it appears, and is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirosilafuorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof; More preferably, said R z is the same as or different from each other and is selected from hydrogen, deuterium, methyl, phenyl, biphenyl, naphthyl, or a combination thereof each time it appears.

7. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirofluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, or a combination thereof; Preferably, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirofluorenyl, or a combination thereof.

8. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently selected from the group consisting of G1 to G68:

9. The compound according to claim 8, wherein, The compound is selected from the group consisting of Compound 1 to Compound 2349, Compound H1 to Compound H82: Among them, Compound 1 to Compound 2349 have a structure represented by Formula 1-a: Among them, Ar1 and Ar2 are respectively selected from the groups listed in the following table: The specific structures of Compound H1 to Compound H82 are as follows: Optionally, the hydrogen in the structures of Compound 1 to Compound 2349, Compound H1 to H82 can be partially or completely replaced by deuterium.

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

11. An organic electroluminescent device comprising: An anode, A cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 - 9.

12. The organic electroluminescent device according to claim 11, wherein, The organic layer comprises a first organic layer and a second organic layer; The first organic layer contains the compound, and the second organic layer contains a second compound and a third compound; The second compound has a structure represented by Formula 2: Wherein, L x each independently selected, each time it appears, from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof; V is the same as or different from each occurrence and is selected from C, CR v or N; T is the same as or different each time it appears and is selected from C, CR t or N; R v and R t each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ar is the same or different each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R v and R t can optionally be linked to form a ring; The third compound has a structure represented by Formula 3: Wherein, E1 - E6 are each independently selected from C, CR, the same or different each time they appear e or N, and at least two of E1 - E6 are N, at least one of E1 - E6 is C, and is connected to formula A; Wherein, Q, each occurrence of which is the same or different, is selected from the group consisting of O, S, Se, N, NR Q , CR Q R Q , SiR Q R Q , GeR Q R Q and R Q C═CR Q ; when two Rs are present simultaneously Q , the two Rs Q may be the same or different; p is 0 or 1; r is 0 or 1; When Q is selected from N, p is 0 and r is 1; When Q is selected from the group consisting of O, S, Se, NR Q , CR Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q , p is 1 and r is 0; L1 is the same or different each occurrence and is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1 - Q8 are each independently selected from C, CR, the same or different each time they appear q or N; R e ,R Q and R q each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; "*" represents the connection position of Formula A and Formula 3; Adjacent substituents R e , R Q , R q can optionally be linked to form a ring.

13. The organic electroluminescent device according to claim 12, wherein, The first organic layer is an electron blocking layer or a hole transport layer; the second organic layer is a light emitting layer; Preferably, the first organic layer is an electron blocking layer; More preferably, the compound is an electron blocking material, and the second compound and the third compound are host materials.

Images