A heterocyclic compound having a cyano group

Abstract

Disclosed is a heterocyclic compound having a cyano substituent. The compound has a structure represented by Formula 1, and the novel compound can be applied to an electroluminescent device to provide better device performance, particularly, an improvement in device efficiency, such as power efficiency, current efficiency, and external quantum efficiency. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a heterocyclic compound having a cyano-substituted group, an organic electroluminescent device comprising the compound, and a compound composition comprising the compound. Background Technology

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

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

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from a complexed heavy metal as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

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

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

[0008] WO2019132545A1 discloses an organic light-emitting device comprising a compound having the following structure: Where X2 is O or S; R 21 R 22 R 23 and R 23 Each is -L 21 -Ar1 or hydrogen; R 31 R 32 R 33 and R 34 Each is -L 22 -Ar2 or hydrogen; Ar1 ​​has the following structure: And at least one of Y1 is selected from N; Ar2 is selected from any one of the following structures: Furthermore, at least one of Y2 is selected from N. The application discloses the following compounds in their specific structures: The application discloses and teaches compounds in which both benzene rings of dibenzofuran (thiophene) are heteroaryl substituents, but does not disclose compounds in which dibenzofuran (thiophene) is aryl substituent or has a cyano substituent at a specific position, and their effects on device performance.

[0009] CN108250189A discloses an organic compound having the following structure and an organic light-emitting device comprising the compound: Where X is O, S, or SiR5R6; R 1a To R 4a Each is independently L1-HAr1 or A1, R 1a To R 4a At least one of them is -HAr1; R 1b To R 4b Each is independently L2-HAr2 or A2, R 1b To R 4b At least one of them is -HAr2; HAr1 and HAr2 can be independently -HAr2. Furthermore, at least two of X1 to X3 are selected from N. The application discloses the following compounds in their specific structures: This application discloses and teaches heterocyclic compounds of dibenzofuran (thiophene, thiophene) in which both phenyl groups are attached to heteroaryl groups, and their application in organic electroluminescent devices. This application does not disclose or teach compounds of dibenzofuran (thiophene) having aryl and heteroaryl substituents at specific positions on the two benzene rings, or compounds having cyano substituents at specific positions, and their effects on device performance.

[0010] CN107619412A discloses an organic compound having the following structure and an organic light-emitting device containing said compound: Where Y1 is O or S, and X1 to X3 are independently N or CR respectively. 11And at least one of X1 to X3 is N. The application discloses the following compounds in specific structures: This application discloses and teaches heterocyclic compounds with an indole fused-ring backbone structure and their applications in organic electroluminescent devices. This application does not disclose or teach non-fused-ring backbones or heterocyclic compounds with cyano substitution at specific positions and their effects on device performance. Summary of the Invention

[0011] This invention aims to provide a series of heterocyclic compounds with cyano substitution to solve at least some of the problems mentioned above. These novel compounds have the structure represented by Formula 1 and can be applied in organic electroluminescent devices, providing better device performance, especially improved device efficiency.

[0012] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0013]

[0014] in,

[0015] X is selected from O, S, or Se;

[0016] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0017] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0018] When ring A and ring B appear, they are selected from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or combinations thereof, whether they are the same or different.

[0019] R y The same or different occurrences of R1 each indicate monosubstituted, polysubstituted, or unsubstituted.

[0020] R2 may appear the same or different each time, indicating either mono- or poly-substitution;

[0021] At least one of R2 is selected from cyano groups;

[0022] R xR2, when appearing in the same or different manner, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0023] R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 6-30 carbon atoms. Aryl, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0024] R1, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. The group includes alkenyl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, isocyanate, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0025] Adjacent substituent R x R y They can be arbitrarily connected to form a loop;

[0026] Adjacent substituents R1 and R2 can optionally be linked to form a ring.

[0027] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises the compound described in the foregoing embodiments.

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

[0029] This invention discloses a series of heterocyclic compounds with cyano substitution. These novel compounds can be applied in organic electroluminescent devices, providing better device performance, especially improved device efficiency, such as power efficiency, current efficiency, and external quantum efficiency. Attached Figure Description

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

[0031] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. Detailed Implementation

[0032] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0033] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0034] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0035] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0036] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0037] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0038] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0039] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0040] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0041] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, it can be called a "photosensitive" ligand. When a ligand is believed not to contribute to the photosensitivity of the emitting material, it can be called a "auxiliary" ligand, but auxiliary ligands can alter the properties of photosensitivity ligands.

[0042] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0043] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0044] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0045] Definition of the term "substituent group"

[0046] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0047] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0048] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0049] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0050] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0051] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0052] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0053] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0054] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0055] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0056] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0057] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0058] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0059] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0060] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0061] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0062] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or at least two CH groups of the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0063] In this disclosure, unless otherwise defined, the term "substituted alkyl", "substituted cycloalkyl", "substituted heteroalkyl", "substituted heterocyclic", "substituted aralkyl", "substituted alkoxy", "substituted aryl", "substituted alkenyl", "substituted alkynyl", "substituted heteroaryl", "substituted alkylsilyl", "substituted arylsilyl", "substituted alkylgermanium", "substituted arylgermanium", "substituted amino", "substituted acyl", "substituted carbonyl", "substituted carboxyl" are used interchangeably. Acid group, substituted ester group, substituted sulfinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine. One or at least two of these groups may be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having 3-20 carbon atoms. Cycloalkyl groups with 1-20 carbon atoms, unsubstituted heteroalkyl groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0064] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0065] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0066] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0067] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

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

[0069]

[0070] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0071]

[0072] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0073]

[0074] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0075]

[0076] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0077]

[0078] in,

[0079] X is selected from O, S, or Se;

[0080] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0081] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0082] When ring A and ring B appear, they are selected from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or combinations thereof, whether they are the same or different.

[0083] R y The same or different occurrences of R1 each indicate monosubstituted, polysubstituted, or unsubstituted.

[0084] R2 may appear the same or different each time, indicating either mono- or poly-substitution;

[0085] At least one of R2 is selected from cyano groups;

[0086] R xR2, when appearing in the same or different manner, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0087] R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 6-30 carbon atoms. Aryl, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0088] R1, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. The group includes alkenyl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, isocyanate, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0089] Adjacent substituent R x R y They can be arbitrarily connected to form a loop;

[0090] Adjacent substituents R1 and R2 can optionally be linked to form a ring.

[0091] In this embodiment, "adjacent substituent R" x R y "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R x Between the two substituents R y Between, substituent R x and R y Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0092] In this embodiment, "adjacent substituents R1, R2 can optionally connect to form a ring" is intended to indicate that any one or more of adjacent substituent groups, such as between two substituents R1, between two substituents R2, or between substituents R1 and R2, can connect to form a ring. Obviously, these substituents may also not connect to form a ring.

[0093] According to one embodiment of the present invention, wherein adjacent substituents R y Connect to form carbon rings, preferably R y They connect to form an aromatic ring.

[0094] According to one embodiment of the invention, at least one of R2 is selected from cyano groups, and the cyano group is substituted at the meta or para position in ring B relative to ring A. For example, when ring B is selected from phenyl groups, the structure is as follows when at least one cyano group is substituted at the meta position in ring B relative to ring A: When at least one cyano group is substituted in ring B at the para position relative to ring A, the structure is as follows: The same applies when ring B is selected from other aryl or heteroaryl groups.

[0095] According to one embodiment of the present invention, X is selected from O or S.

[0096] According to one embodiment of the present invention, X is selected from O.

[0097] According to one embodiment of the present invention, X1-X6 are selected from CR each time they appear, either identically or differently. x .

[0098] According to one embodiment of the present invention, at least one of X1-X6 is selected from N. For example, one of X1-X6 is selected from N or two are selected from N.

[0099] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0100] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0101] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0102] According to one embodiment of the present invention, R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0103] According to one embodiment of the present invention, R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0104] According to one embodiment of the present invention, R y Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0105] According to one embodiment of the invention, R1 is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0106] According to one embodiment of the invention, R1 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, each time it appears.

[0107] According to one embodiment of the invention, R1 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof each time it appears.

[0108] According to one embodiment of the invention, R2 is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, cyano groups, and combinations thereof.

[0109] According to one embodiment of the invention, R2 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, cyano groups, and combinations thereof, each time it appears.

[0110] According to one embodiment of the invention, R2 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, cyano, and combinations thereof each time it appears.

[0111] According to one embodiment of the invention, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0112] According to one embodiment of the invention, Ar, each time it appears, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.

[0113] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds A-1 to A-714, wherein the specific structures of compounds A-1 to A-714 are as described in claim 8.

[0114] According to one embodiment of the present invention, the hydrogen in compounds A-1 to A-714 can be partially or completely replaced by deuterium.

[0115] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises a compound as described in any of the preceding embodiments.

[0116] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is the light-emitting layer, the compound is the host compound, and the light-emitting layer contains at least a first metal complex.

[0117] According to an embodiment of the present invention, the first metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0118] Metal M is selected from metals with a relative atomic mass greater than 40;

[0119] ligand L a L b L c The first ligand, second ligand, and third ligand, respectively, are coordinated with the metal M, and ligand L is... a L b L c They can be the same or different;

[0120] ligand L a L b L c They can be optionally linked to form polydentate ligands; for example, L a L b and L c Any two of them can be connected to form a tetradentate ligand; for example, L a L b and L c They can connect to form hexadecantal ligands; or, for example, L a L b L c They are not connected and therefore do not form multidentate ligands;

[0121] m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different; when q is 2, the two Ls c They can be the same or different;

[0122] ligand L a It has the structure shown in Equation 2:

[0123]

[0124] When ring C1 and ring C2 appear in the same or different ways, they are selected from aromatic rings having 5-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof;

[0125] Q1 and Q2 are selected from C or N each time they appear, either the same or different.

[0126] R 11 and R 12 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0127] R 11 and R 12Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0128] Adjacent substituent R 11 R 12 They can be arbitrarily connected to form a loop;

[0129] ligand L b and L c Each occurrence may be the same or different, selected from monoanionic bidentate ligands.

[0130] According to one embodiment of the present invention, wherein the ligand L b L c Each occurrence may be selected from one or both of the following structures, either identically or differently:

[0131]

[0132] in,

[0133] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0134] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0135] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0136] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0137] Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0138] In this embodiment, "adjacent substituent R" a R b R c R N1 R N2 R C1 and R C2 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent Rb and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, and R C1 and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0139] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of, but not limited to, GD1 to GD76, wherein the specific structures of GD1 to GD76 are as described in claim 12.

[0140] According to one embodiment of the present invention, the organic layer in the organic electroluminescent device is an electron transport layer, and the compound is an electron transport compound.

[0141] According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a second compound, the second compound comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0142] According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a second compound, the second compound comprising at least one chemical group selected from the group consisting of benzene, carbazole, indolecarbazole, fluorene, silylfluorene, and combinations thereof.

[0143] According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a second compound, wherein the compound having the structure of Formula 1 and the second compound can be simultaneously evaporated from two evaporation sources to form the light-emitting layer, and the compound having the structure of Formula 1 and the second compound can also be stably co-evaporated from a single evaporation source by premixing to form the light-emitting layer, the latter of which can further save evaporation sources.

[0144] According to one embodiment of the present invention, the second compound in the organic electroluminescent device has a structure represented by Formula 3:

[0145]

[0146] in,

[0147] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0148] T is selected from C and CR each time it appears, either identically or differently. t Or N;

[0149] R t Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0150] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0151] Adjacent substituent R t They can be arbitrarily connected to form a ring.

[0152] In this paper, "adjacent substituent R" t "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, any two substituents R tBetween these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0153] According to one embodiment of the present invention, the second compound in the organic electroluminescent device has a structure represented by Formula 4:

[0154]

[0155] in,

[0156] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;

[0157] T is selected from C and CR each time it appears, either identically or differently. t Or N;

[0158] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0159] R t R g Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0160] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0161] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.

[0162] In this paper, "adjacent substituent R" t R g "Can be optionally linked to form a ring" is intended to indicate adjacent substituents R t Substituents R between and adjacent t and R g Between these adjacent substituent groups, one or more can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.

[0163] According to one embodiment of the present invention, the second compound in the organic electroluminescent device has a structure represented by one of formulas 3-a to 3-j:

[0164]

[0165] in,

[0166] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0167] T is selected from CR each time it appears, either the same or different. t Or N;

[0168] R t Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0169] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0170] Adjacent substituent R t They can be arbitrarily connected to form a ring.

[0171] According to one embodiment of the present invention, the second compound in the organic electroluminescent device has a structure represented by one of formulas 4-a to 4-f:

[0172]

[0173] in,

[0174] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;

[0175] T is selected from CR each time it appears, either the same or different. t Or N;

[0176] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0177] R t R g Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0178] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0179] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.

[0180] According to one embodiment of the invention, at least one of all T is selected from N, for example, one or both of them are N.

[0181] According to one embodiment of the present invention, the organic electroluminescent device emits green light.

[0182] According to one embodiment of the present invention, the organic electroluminescent device emits white light.

[0183] According to one embodiment of the present invention, the first metal complex is doped into the compound and the second compound, wherein the first compound accounts for 1% to 30% of the total weight of the first organic layer.

[0184] According to one embodiment of the present invention, the first metal complex is doped into the compound and the second compound, wherein the first compound accounts for 3% to 13% of the total weight of the first organic layer.

[0185] According to one embodiment of the present invention, a compound composition comprising the compounds described in any of the foregoing embodiments is disclosed.

[0186] According to one embodiment of the present invention, an electronic device is disclosed, which includes the organic electroluminescent device described in any of the foregoing embodiments.

[0187] Combination with other materials

[0188] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0189] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of hosts, a variety of light-emitting dopants, transport layers, barrier layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0190] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0191] In device fabrication, when two or more host materials and a luminescent material are co-deposited to form a luminescent layer, the luminescent layer can be formed by co-depositing the two or more host materials and the luminescent material in different evaporation sources, or by placing a pre-mixed mixture of the two or more host materials in the same evaporation source and then co-depositing it with the luminescent material placed in another evaporation source. This pre-mixing method can further save on evaporation sources. Taking this invention as an example, the luminescent layer can be formed by co-depositing the first compound, the second compound, and the luminescent material in different evaporation sources, or by placing a pre-mixed mixture of the first compound and the second compound in the same evaporation source and then co-depositing it with the luminescent material placed in another evaporation source.

[0192] Material synthesis examples:

[0193] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0194] Synthesis Example 1: Synthesis of compound A-2

[0195] Step 1: Synthesis of intermediate C

[0196]

[0197] In a 500 mL three-necked round-bottom flask, A (25 g, 170 mmol), B (39 g, 204 mmol), Pd(PPh3)4 (3.93 g, 3.4 mmol), and Na2CO3 (36 g, 340 mmol) were added to toluene (80 mL), EtOH (20 mL), and H2O (20 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 3:1) to give a white solid intermediate C (33.3 g, 155.8 mmol), with a yield of 91.6%.

[0198] Step 2: Synthesis of intermediate E

[0199]

[0200] In a 1000 mL three-necked round-bottom flask, C (33.3 g, 155.8 mmol), D (59.3 g, 233.7 mmol), Pd(OAc)₂ (0.7 g, 3.1 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 3.0 g, 6.2 mmol), and AcOK (31 g, 311.6 mmol) were added to 1,4-dioxane (300 mL). The mixture was purged three times with N₂ and heated under reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate E (28.2 g, 92.5 mmol), with a yield of 59.0%.

[0201] Step 3: Synthesis of intermediate G

[0202]

[0203] In a 1000 mL three-necked round-bottom flask, E (24.4 g, 80 mmol), F (27 g, 120 mmol), Pd(PPh3)4 (1.85 g, 1.6 mmol), and Na2CO3 (25 g, 240 mmol) were added to THF (400 mL) and H2O (100 mL). The mixture was purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 1:1) to give a white solid intermediate G (12.2 g, 33 mmol), with a yield of 41.3%.

[0204] Step 4: Synthesis of compound A-2

[0205]

[0206] In a 250 mL three-necked round-bottom flask, H (3.52 g, 9.5 mmol), G (3.5 g, 9.5 mmol), Pd(PPh3)4 (0.22 g, 0.19 mmol), and K2CO3 (2.62 g, 19.0 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (5.0 g, 8.7 mmol), with a yield of 91.0%. The product was identified as the target compound A-2, with a molecular weight of 576.2.

[0207] Synthesis Example 2: Synthesis of compound A-5

[0208] Step 1: Synthesis of intermediate J

[0209]

[0210] In a 1000 mL three-necked round-bottom flask, E (10.0 g, 32.8 mmol), I (11.9 g, 39.3 mmol), Pd(PPh3)4 (1.1 g, 0.98 mmol), and Na2CO3 (6.9 g, 65.6 mmol) were added to THF (320 mL) and H2O (80 mL). The mixture was purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 1:1) to give a white solid intermediate J (4.0 g, 9.0 mmol), with a yield of 27.4%.

[0211] Step 2: Synthesis of compound A-5

[0212]

[0213] In a 250 mL three-necked round-bottom flask, H (3.3 g, 9.0 mmol), J (4.0 g, 9.0 mmol), Pd(PPh3)4 (0.21 g, 0.18 mmol), and K2CO3 (2.5 g, 18.0 mmol) were added to toluene (60 mL), EtOH (15 mL), and H2O (15 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene to give a white solid (4.0 g, 6.1 mmol), with a yield of 68.0%. The product was identified as the target compound A-5, with a molecular weight of 652.2.

[0214] Synthesis Example 3: Synthesis of compound A-8

[0215] Step 1: Synthesis of intermediate L

[0216]

[0217] In a 1000 mL three-necked round-bottom flask, E (10.0 g, 32.8 mmol), K (11.9 g, 39.3 mmol), Pd(PPh3)4 (1.1 g, 0.98 mmol), and Na2CO3 (6.9 g, 65.6 mmol) were added to THF (320 mL) and H2O (80 mL). The mixture was purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 1:1) to give a white solid intermediate L (4.0 g, 9.0 mmol), with a yield of 27.4%.

[0218] Step 2: Synthesis of compound A-8

[0219]

[0220] In a 250 mL three-necked round-bottom flask, H (3.3 g, 9.0 mmol), L (4.0 g, 9.0 mmol), Pd(PPh3)4 (0.21 g, 0.18 mmol), and K2CO3 (2.5 g, 18.0 mmol) were added to toluene (60 mL), EtOH (15 mL), and H2O (15 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene to give a white solid (3.9 g, 6.0 mmol), with a yield of 66.7%. The product was identified as the target compound A-8, with a molecular weight of 652.2.

[0221] Synthesis Example 4: Synthesis of compound A-57

[0222] Step 1: Synthesis of intermediate N

[0223]

[0224] In a 1000 mL three-necked round-bottom flask, A (20.0 g, 136.1 mmol), M (31.3 g, 163.3 mmol), Pd(PPh3)4 (1.57 g, 1.36 mmol), and Na2CO3 (28.9 g, 272.2 mmol) were added to toluene (280 mL), EtOH (70 mL), and H2O (70 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 3:1) to give a white solid intermediate N (26.0 g, 121.8 mmol), with a yield of 91.6%.

[0225] Step 2: Synthesis of intermediate O

[0226]

[0227] In a 500 mL three-necked round-bottom flask, N (26.0 g, 121.8 mmol), D (61.9 g, 243.6 mmol), Pd(OAc)₂ (1.4 g, 6.1 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 5.8 g, 12.2 mmol), and AcOK (23.9 g, 243.6 mmol) were added to 1,4-dioxane (200 mL). The mixture was purged three times with N₂ and heated under reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate O (28.0 g, 91.7 mmol), with a yield of 75.3%.

[0228] Step 3: Synthesis of intermediate P

[0229]

[0230] In a 500 mL three-necked round-bottom flask, O (6.1 g, 20.0 mmol), I (9.1 g, 30.0 mmol), Pd(PPh3)4 (1.1 g, 0.95 mmol), and Na2CO3 (6.4 g, 60.0 mmol) were added to THF (120 mL) and H2O (30 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 3:1 to 1:1) to give a white solid intermediate P (6.0 g, 13.5 mmol), with a yield of 67.5%.

[0231] Step 4: Synthesis of compound A-57

[0232]

[0233] In a 250 mL three-necked round-bottom flask, H (3.7 g, 9.9 mmol), P (4.2 g, 9.4 mmol), Pd(PPh3)4 (0.54 g, 0.47 mmol), and K2CO3 (3.9 g, 28.2 mmol) were added to toluene (80 mL), EtOH (20 mL), and H2O (20 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene to give a white solid (4.7 g, 7.2 mmol), with a yield of 76.5%. The product was identified as the target compound A-57, with a molecular weight of 652.2.

[0234] Synthesis Example 5: Synthesis of compound A-60

[0235] Step 1: Synthesis of intermediate Q

[0236]

[0237] In a 250 mL three-necked round-bottom flask, O (6.1 g, 20.0 mmol), K (9.1 g, 30.0 mmol), Pd(PPh3)4 (1.1 g, 0.98 mmol), and Na2CO3 (6.4 g, 60.0 mmol) were added to THF (120 mL) and H2O (30 mL). The mixture was purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 1:1) to give a white solid intermediate Q (6.0 g, 13.5 mmol), with a yield of 67.5%.

[0238] Step 2: Synthesis of compound A-60

[0239]

[0240] In a 250 mL three-necked round-bottom flask, H (3.9 g, 10.5 mmol), Q (4.45 g, 10.0 mmol), Pd(PPh3)4 (0.54 g, 0.47 mmol), and K2CO3 (3.9 g, 28.2 mmol) were added to toluene (80 mL), EtOH (20 mL), and H2O (20 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene to give a white solid (5.7 g, 8.7 mmol), with a yield of 87.0%. The product was identified as the target compound A-60, with a molecular weight of 652.2.

[0241] Synthesis Example 6: Synthesis of compound A-177

[0242] Step 1: Synthesis of intermediate S

[0243]

[0244] In a 250 mL three-necked round-bottom flask, R (8.0 g, 22.9 mmol), 4-biphenylboronic acid (5.9 g, 29.7 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and K2CO3 (9.5 g, 68.7 mmol) were added to 1,4-dioxane (100 mL) and H2O (25 mL). The mixture was heated under nitrogen protection and refluxed overnight. Heating was then stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 40:1 to 15:1) to give a white solid intermediate S (7.0 g, 19.7 mmol), with a yield of 86.1%.

[0245] Step 2: Synthesis of intermediate T

[0246]

[0247] In a 250 mL three-necked round-bottom flask, S (7.0 g, 19.7 mmol), D (10.0 g, 39.4 mmol), Pd(OAc)₂ (0.2 g, 1.0 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 0.9 g, 2.0 mmol), and KOAc (5.8 g, 59.1 mmol) were added to 1,4-dioxane (100 mL). The mixture was heated under nitrogen protection and refluxed overnight. Heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 4:1 to 2:1) to give a white solid intermediate T (6.0 g, 13.4 mmol), with a yield of 68.2%.

[0248] Step 3: Synthesis of compound A-177

[0249]

[0250] In a 250 mL three-necked round-bottom flask, T (4.5 g, 10.0 mmol), G (3.5 g, 9.5 mmol), Pd(PPh3)4 (0.5 g, 0.43 mmol), and K2CO3 (3.9 g, 28.5 mmol) were added to toluene (80 mL), EtOH (20 mL), and H2O (20 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (4.5 g, 6.9 mmol), with a yield of 72.6%. The product was identified as the target compound A-177, with a molecular weight of 652.2.

[0251] Synthesis Example 7: Synthesis of compound A-352

[0252] Step 1: Synthesis of intermediate U

[0253]

[0254] In a 250 mL three-necked round-bottom flask, R (6.0 g, 17.1 mmol), 3-biphenylboronic acid (3.70 g, 18.81 mmol), Pd(PPh3)4 (0.59 g, 0.51 mmol), and K2CO3 (4.72 g, 34.2 mmol) were added to toluene (58 mL), EtOH (14 mL), and H2O (14 mL). The mixture was heated under nitrogen protection and refluxed overnight. Heating was then stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 50:1) to give a colorless oily intermediate U (5.6 g, 15.8 mmol), with a yield of 92.3%.

[0255] Step 2: Synthesis of intermediate V

[0256]

[0257] In a 250 mL three-necked round-bottom flask, U (6.0 g, 17.47 mmol), D (6.65 g, 26.2 mmol), Pd(OAc)₂ (0.08 g, 0.35 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 0.33 g, 0.67 mmol), and KOAc (3.43 g, 34.94 mmol) were added to 1,4-dioxane (87 mL). The mixture was heated under nitrogen protection and refluxed overnight. Heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 4:1 to 2:1) to give a white solid intermediate V (4.71 g, 10.55 mmol), with a yield of 60.4%.

[0258] Step 3: Synthesis of compound A-352

[0259]

[0260] In a 250 mL three-necked round-bottom flask, V (4.46 g, 10.0 mmol), G (3.68 g, 10.0 mmol), Pd(PPh3)4 (0.23 g, 0.20 mmol), and K2CO3 (2.76 g, 20.0 mmol) were added to toluene (48 mL), EtOH (12 mL), and H2O (12 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (5.9 g, 9.0 mmol), with a yield of 90.4%. The product was identified as the target compound A-352, with a molecular weight of 652.2.

[0261] Synthesis Example 8: Synthesis of Compound A-1

[0262] Step 1: Synthesis of intermediate X

[0263]

[0264] In a 500 mL three-necked round-bottom flask, W (12.5 g, 85.1 mmol), B (15.5 g, 81.0 mmol), Pd(PPh3)4 (1.8 g, 1.6 mmol), and Na2CO3 (27.9 g, 202.5 mmol) were added to 1,4-dioxane (120 mL) and H2O (30 mL). The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. Ethyl acetate was added to extract the mixture. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 3:1) to give a white solid intermediate X (6.7 g, 31.4 mmol), with a yield of 38.8%.

[0265] Step 2: Synthesis of intermediate Y

[0266]

[0267] In a 250 mL three-necked round-bottom flask, X (6.7 g, 31.4 mmol), D (12.0 g, 47.1 mmol), Pd(OAc)₂ (0.35 g, 1.6 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 1.5 g, 3.1 mmol), and AcOK (6.2 g, 62.8 mmol) were added to 1,4-dioxane (60 mL). The mixture was heated under reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate Y (6.9 g, 22.6 mmol), with a yield of 72.0%.

[0268] Step 3: Synthesis of intermediate Z

[0269]

[0270] In a 250 mL three-necked round-bottom flask, Y (6.9 g, 22.6 mmol), F (10.2 g, 45.2 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and Na2CO3 (4.8 g, 45.2 mmol) were added to THF (80 mL) and H2O (20 mL). The mixture was heated to reflux under N2 protection. After 12 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 2:1 to 1:1) to give a white solid intermediate Z (2.8 g, 7.6 mmol), with a yield of 33.6%.

[0271] Step 4: Synthesis of compound A-1

[0272]

[0273] In a 250 mL three-necked round-bottom flask, H (2.75 g, 7.4 mmol), Z (2.74 g, 7.4 mmol), Pd(PPh3)4 (0.43 g, 0.37 mmol), and K2CO3 (2.0 g, 14.8 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene to give a white solid (2.8 g, 4.9 mmol), with a yield of 65.6%. The product was identified as the target compound A-1, with a molecular weight of 576.2.

[0274] Synthesis Example 9: Synthesis of Compound A-3

[0275] Step 1: Synthesis of intermediate AB

[0276]

[0277] In a 500 mL three-necked round-bottom flask, AA (18.0 g, 122.5 mmol), B (28.0 g, 147.0 mmol), Pd(PPh3)4 (2.83 g, 2.45 mmol), and Na2CO3 (26.0 g, 245.0 mmol) were added to toluene (120 mL), EtOH (30 mL), and H2O (30 mL). The mixture was heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 10:1 to 4:1) to give a white solid intermediate AB (22.0 g, 103.0 mmol), with a yield of 84.1%.

[0278] Step 2: Synthesis of intermediate AC

[0279]

[0280] In a 250 mL three-necked round-bottom flask, AB (22.0 g, 103.0 mmol), D (39.2 g, 154.5 mmol), Pd(OAc)₂ (0.46 g, 2.1 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 1.96 g, 4.12 mmol), and AcOK (20.2 g, 206.0 mmol) were added to 1,4-dioxane (200 mL). The mixture was heated under reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate AC (28.5 g, 93.4 mmol), with a yield of 90.7%.

[0281] Step 3: Synthesis of intermediate AD

[0282]

[0283] In a 500 mL three-necked round-bottom flask, AC (5.0 g, 16.4 mmol), F (9.3 g, 41.0 mmol), Pd(PPh3)4 (0.57 g, 0.49 mmol), and Na2CO3 (3.48 g, 32.8 mmol) were added to THF (128 mL) and H2O (32 mL). The mixture was heated to reflux under N2 protection. After 4 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 3:1 to 1:1) to give a white solid intermediate AD (3.7 g, 10.0 mmol), with a yield of 61.2%.

[0284] Step 4: Synthesis of compound A-3

[0285]

[0286] In a 250 mL three-necked round-bottom flask, H (3.70 g, 10.0 mmol), AD (3.69 g, 10.0 mmol), Pd(PPh3)4 (0.23 g, 0.20 mmol), and K2CO3 (2.76 g, 20.0 mmol) were added to toluene (48 mL), EtOH (12 mL), and H2O (12 mL). The mixture was purged three times with N2 and heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene to give a white solid (5.2 g, 9.0 mmol), with a yield of 90.1%. The product was identified as the target compound A-3, with a molecular weight of 576.2.

[0287] Synthesis Example 10: Synthesis of compound A-54

[0288] Step 1: Synthesis of intermediate AE

[0289]

[0290] In a 500 mL three-necked round-bottom flask, O (14.0 g, 45.87 mmol), F (16.6 g, 73.4 mmol), Pd(PPh3)4 (1.59 g, 1.38 mmol), and Na2CO3 (9.72 g, 91.74 mmol) were added to THF (240 mL) and H2O (60 mL). The mixture was heated to reflux under N2 protection. After 8 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 2:1 to 1:1) to give a white solid intermediate AE (10.6 g, 28.74 mmol), with a yield of 62.7%.

[0291] Step 2: Synthesis of compound A-54

[0292]

[0293] In a 250 mL three-necked round-bottom flask, H (3.70 g, 10.0 mmol), AE (3.69 g, 10.0 mmol), Pd(PPh3)4 (0.35 g, 0.30 mmol), and K2CO3 (2.76 g, 20.0 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). The mixture was heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The mixture was then filtered under reduced pressure, and the resulting solid was washed successively with water and methanol. The solid was recrystallized from toluene to give a white solid (4.7 g, 8.2 mmol), with a yield of 82.0%. The product was identified as the target compound A-54, with a molecular weight of 576.2.

[0294] Synthesis Example 11: Synthesis of compound A-55

[0295] Step 1: Synthesis of intermediate AF

[0296]

[0297] In a 500 mL three-necked round-bottom flask, AA (21.0 g, 143.0 mmol), M (32.8 g, 171.6 mmol), Pd(PPh3)4 (3.3 g, 2.86 mmol), and Na2CO3 (30.3 g, 286.0 mmol) were added to toluene (200 mL), EtOH (50 mL), and H2O (50 mL). The mixture was heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 10:1 to 3:1) to give a white solid intermediate AF (27.6 g, 129.2 mmol), with a yield of 90.3%.

[0298] Step 2: Synthesis of intermediate AG

[0299]

[0300] In a 500 mL three-necked round-bottom flask, AF (27.6 g, 129.2 mmol), D (49.2 g, 193.8 mmol), Pd(OAc)₂ (0.58 g, 2.58 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 2.46 g, 5.16 mmol), and AcOK (25.2 g, 256.4 mmol) were added to 1,4-dioxane (260 mL). The mixture was heated under reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate AG (34.2 g, 112.0 mmol), with a yield of 86.7%.

[0301] Step 3: Synthesis of intermediate AH

[0302]

[0303] In a 500 mL three-necked round-bottom flask, AG (12.2 g, 40.0 mmol), F (14.5 g, 64.0 mmol), Pd(PPh3)4 (1.39 g, 1.2 mmol), and Na2CO3 (8.5 g, 80.2 mmol) were added to THF (200 mL) and H2O (50 mL). The mixture was heated to reflux under N2 protection. After 7 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from ethanol to give a white solid (8.4 g, 22.8 mmol), with a yield of 57.0%.

[0304] Step 4: Synthesis of compound A-55

[0305]

[0306] In a 250 mL three-necked round-bottom flask, H (4.44 g, 12.0 mmol), AH (4.4 g, 12.0 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and K2CO3 (3.3 g, 24.0 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). The mixture was heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The mixture was then filtered under reduced pressure, and the resulting solid was washed successively with water and ethanol. The solid was recrystallized from toluene to give a white solid (5.9 g, 10.2 mmol), with a yield of 85.3%. The product was identified as the target compound A-55, with a molecular weight of 576.2.

[0307] Synthesis Example 12: Synthesis of compound A-229

[0308] Step 1: Synthesis of compound A-229

[0309]

[0310] In a 250 mL three-necked round-bottom flask, T (4.1 g, 9.1 mmol), AE (3.2 g, 8.7 mmol), Pd(PPh3)4 (0.50 g, 0.44 mmol), and K2CO3 (3.6 g, 26.1 mmol) were added to toluene (80 mL), EtOH (20 mL), and H2O (20 mL). The mixture was heated under reflux overnight under nitrogen protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The mixture was then filtered under reduced pressure, and the resulting solid was washed successively with water and ethanol. The solid was recrystallized from toluene to give a white solid (4.5 g, 6.9 mmol), with a yield of 79.2%. The product was identified as the target compound A-229, with a molecular weight of 652.2.

[0311] Synthesis Example 13: Synthesis of compound A-404

[0312] Step 1: Synthesis of compound A-404

[0313]

[0314] In a 250 mL three-necked round-bottom flask, V (3.63 g, 8.13 mmol), AE (3.0 g, 8.13 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and K2CO3 (2.26 g, 16.26 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). The mixture was heated under reflux overnight under N2 protection. The reaction was confirmed by TLC spotting. Heating was stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 4:1 to 1:1) to give a white solid (4.0 g, 6.13 mmol), with a yield of 75.4%. The product was identified as the target compound A-404, with a molecular weight of 652.2.

[0315] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0316] Device Examples

[0317] Device Example 1

[0318] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, ITO anodes were sequentially deposited at a rate of 0.2-2 Å / s via thermal vacuum evaporation. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound H1 was used as the electron blocking layer (EBL). Then, compound GD1, as a dopant, was co-deposited with compound H1 and compound A-2 of the present invention as the light-emitting layer (EML). Compound H2 was used as the hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer, and a 120 nm thick layer of aluminum was deposited as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0319] Device Example 2

[0320] The fabrication of device example 2 was the same as that of device example 1, except that compound A-5 was used instead of compound A-2 in the light-emitting layer (EML).

[0321] Device Example 3

[0322] The fabrication of device example 3 was the same as that of device example 1, except that compound A-8 was used instead of compound A-2 in the light-emitting layer (EML).

[0323] Device Example 4

[0324] The fabrication of device example 4 was the same as that of device example 1, except that compound A-57 was used instead of compound A-2 in the light-emitting layer (EML).

[0325] Device Example 5

[0326] The fabrication of device example 5 was the same as that of device example 1, except that compound A-60 was used instead of compound A-2 in the light-emitting layer (EML).

[0327] Device Example 6

[0328] The fabrication of device example 6 was the same as that of device example 1, except that compound A-177 was used instead of compound A-2 in the light-emitting layer (EML).

[0329] Device Example 7

[0330] The fabrication of device example 7 was the same as that of device example 1, except that compound A-352 was used instead of compound A-2 in the light-emitting layer (EML).

[0331] Device Comparison Example 1

[0332] The fabrication of Comparative Example 1 was the same as that of Example 1, except that compound C-1 was used instead of compound A-2 in the light-emitting layer (EML).

[0333] Device Comparison Example 2

[0334] The fabrication of Comparative Example 2 was the same as that of Example 1, except that compound C-2 was used instead of compound A-2 in the light-emitting layer (EML).

[0335] Device Comparison Example 3

[0336] The fabrication of Comparative Example 3 was the same as that of Example 1, except that compound C-3 was used instead of compound A-2 in the light-emitting layer (EML).

[0337] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0338] Table 1. Device structures of Examples 1 to 7 and Comparative Examples 1 to 3.

[0339]

[0340]

[0341] The material structure used in the device is shown below:

[0342]

[0343]

[0344] Table 2 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current.

[0345] Table 2 Device data for Examples 1 to 7 and Comparative Examples 1 to 3

[0346]

[0347]

[0348] discuss:

[0349] In Examples 1 to 7 and Comparative Example 1, the first metal complex GD1 was doped into the compounds of the present invention and non-inventive compound C-1, respectively. Compared with Comparative Example 1, the EQE of Examples 1 to 7 was improved by 31.2% to 34.8%, CE was improved by approximately 32.9%, and PE was improved by 35.1% to 45.6%; at the same time, the driving voltage was also reduced. This demonstrates that the compounds of the present invention with an aryl substituent at the 1-position of dibenzofuran, compared with compounds with a heteroaryl substituent at the 1-position of dibenzofuran, can improve device performance, especially device efficiency (EQE, PE, and CE), when applied to electroluminescent devices.

[0350] In Examples 1 to 7 and Comparative Example 2, the first metal complex GD1 was doped into the compounds of the present invention and the non-present invention compound C-2, respectively. Compared with Comparative Example 2, the EQE of Examples 1 to 7 was improved by 13.3% to 16.4%, CE was improved by approximately 14.1%, and PE was improved by 20.3% to 29.6%; the driving voltage was also reduced. This indicates that the compounds of the present invention with cyano substituents on ring B, compared with the comparative compound C-2 with cyano substituents on ring A, can improve device performance, especially device efficiency, when applied to electroluminescent devices.

[0351] In Examples 1 to 7 and Comparative Example 3, the first metal complex GD1 was doped into the compounds of the present invention and non-the present invention compound C-3, respectively. It should be noted that C-3 is a currently commercially available main material. Compared to Comparative Example 3, although the driving voltage of Examples 1 to 7 was slightly increased, their EQE was improved by 11.5% to 14.6%, CE was improved by approximately 11.5%, and PE was also improved. Therefore, the compounds of the present invention can meet commercial performance requirements and have superior device efficiency, making them a class of compounds with commercial potential.

[0352] Device Example 8

[0353] The preparation of device example 8 is the same as that of device example 2, except that compound GD2 is used instead of compound GD1 in the light-emitting layer (EML) and H1:A-5:GD2 = 72:24:4.

[0354] Device Example 9

[0355] The fabrication of device example 9 was the same as that of device example 8, except that compound A-57 was used instead of compound A-5 in the light-emitting layer (EML).

[0356] Device Example 10

[0357] The fabrication of device example 10 was the same as that of device example 8, except that compound A-177 was used instead of compound A-5 in the light-emitting layer (EML).

[0358] Device Example 11

[0359] The fabrication of device example 11 was the same as that of device example 8, except that compound A-352 was used instead of compound A-5 in the light-emitting layer (EML).

[0360] Device Comparison Example 4

[0361] The fabrication of Comparative Example 4 was the same as that of Example 8, except that compound C-2 was used instead of compound A-5 in the light-emitting layer (EML).

[0362] Device Comparison Example 5

[0363] The fabrication of Comparative Example 5 was the same as that of Example 8, except that compound C-3 was used instead of compound A-5 in the light-emitting layer (EML).

[0364] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0365] Table 3. Device structures of Examples 8 to 11 and Comparative Examples 4 to 5.

[0366]

[0367] The structure of the new material used in the device is shown below:

[0368]

[0369] Table 4 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current.

[0370] Table 4. Device data for Examples 8 to 11 and Comparative Examples 4 to 5.

[0371]

[0372]

[0373] discuss:

[0374] In Examples 8 to 11 and Comparative Example 4, the first metal complex GD2 was doped into compounds A-5, A-57, A-177, and A-352 of the present invention, respectively, and into compound C-2 of the non-present invention. Compared with Comparative Example 4, the EQE of Examples 8 to 11 was increased by 8.4%, 10.4%, 9.7%, and 9.6%, respectively, while CE and PE were also improved, and the driving voltage was reduced. This indicates that the compounds of the present invention with cyano substituents on ring B, compared to the comparative compound C-2 with cyano substituents on ring A, can improve device performance, especially the EQE, when applied to electroluminescent devices.

[0375] In Examples 8 to 11 and Comparative Example 5, the first metal complex GD2 was doped into compounds A-5, A-57, A-177, and A-352 of the present invention, respectively, and into compound C-3 of the non-present invention. Compared with Comparative Example 5, the driving voltages of Examples 8 to 11 were comparable to those of the comparative example, but their EQE was improved by 10.7%, 12.8%, 12.1%, and 11.9%, respectively, while CE and PE were also improved. Therefore, the compounds of the present invention can meet the performance requirements for commercial use and have superior device efficiency, making them a class of compounds with commercial potential.

[0376] Device Example 12

[0377] The fabrication of device example 12 was the same as that of device example 1, except that compound GD3 was used instead of compound GD1 in the light-emitting layer (EML).

[0378] Device Example 13

[0379] The fabrication of device example 13 was the same as that of device example 12, except that compound A-5 was used instead of compound A-2 in the light-emitting layer (EML).

[0380] Device Example 14

[0381] The fabrication of device example 14 was the same as that of device example 12, except that compound A-8 was used instead of compound A-2 in the light-emitting layer (EML).

[0382] Device Example 15

[0383] The fabrication of device example 15 was the same as that of device example 12, except that compound A-57 was used instead of compound A-2 in the light-emitting layer (EML).

[0384] Device Example 16

[0385] The fabrication of device example 16 was the same as that of device example 12, except that compound A-60 was used instead of compound A-2 in the light-emitting layer (EML).

[0386] Device Comparison Example 6

[0387] The fabrication of Comparative Example 6 was the same as that of Example 12, except that compound C-1 was used instead of compound A-2 in the light-emitting layer (EML).

[0388] Device Comparison Example 7

[0389] The fabrication of Comparative Example 7 was the same as that of Example 12, except that compound C-2 was used instead of compound A-2 in the light-emitting layer (EML).

[0390] Device Comparison Example 8

[0391] The fabrication of Comparative Example 8 was the same as that of Example 12, except that compound C-3 was used instead of compound A-2 in the light-emitting layer (EML).

[0392] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0393] Table 5. Device structures of Examples 12 to 16 and Comparative Examples 6 to 8.

[0394]

[0395] The structure of the new material used in the device is shown below:

[0396]

[0397] Table 6 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current.

[0398] Table 6. Device data for Examples 12 to 16 and Comparative Examples 6 to 8.

[0399]

[0400] discuss:

[0401] In Examples 12 to 16 and Comparative Example 6, the first metal complex GD3 was doped into the compounds of the present invention and non-the present invention compound C-1, respectively. Compared with Comparative Example 6, the EQE of Examples 12 to 16 was improved by 18.3% to 24.2%, CE was improved by 18.7% to 25%, and PE was improved by 25.4% to 35.1%; at the same time, the driving voltage was also reduced. This shows that the compounds of the present invention with an aryl substituent at the 1-position of dibenzofuran, compared with compounds with a heteroaryl substituent at the 1-position of dibenzofuran, can improve device performance, especially the EQE, when applied to electroluminescent devices.

[0402] In Examples 12 to 16 and Comparative Example 7, the first metal complex GD3 was doped into the compounds of the present invention and into non-present compound C-2, respectively. Compared with Comparative Example 7, the EQE of Examples 12 to 16 was improved by 8.1% to 13.5%, while CE and PE were significantly improved, and the driving voltage was also reduced. This indicates that the compounds of the present invention with cyano substituents on ring B, compared to the comparative compound C-2 with cyano substituents on ring A, can improve device performance, especially the EQE, when applied to electroluminescent devices.

[0403] In Examples 12 to 16 and Comparative Example 8, the first metal complex GD3 was doped into the compounds of the present invention and into non-inventive compound C-3, respectively. Compared to Comparative Example 8, the driving voltage of Examples 12 to 16 was slightly increased, but their EQE was improved by 12.7% to 18.3%, while CE and PE were also improved. Therefore, the compounds of the present invention can meet commercial performance requirements and have superior device efficiency, making them a class of compounds with commercial potential.

[0404] Device Example 17

[0405] The fabrication of device example 17 was the same as that of device example 1, except that compound GD4 was used instead of compound GD1 in the light-emitting layer (EML).

[0406] Device Example 18

[0407] The fabrication of device example 18 was the same as that of device example 17, except that compound A-5 was used instead of compound A-2 in the light-emitting layer (EML).

[0408] Device Example 19

[0409] The fabrication of device example 19 was the same as that of device example 17, except that compound A-60 was used instead of compound A-2 in the light-emitting layer (EML).

[0410] Device Comparison Example 9

[0411] The fabrication of Comparative Example 9 was the same as that of Example 17, except that compound C-1 was used instead of compound A-2 in the light-emitting layer (EML).

[0412] Device Comparison Example 10

[0413] The fabrication of Comparative Example 10 was the same as that of Example 17, except that compound C-2 was used instead of compound A-2 in the light-emitting layer (EML).

[0414] Device Comparison Example 11

[0415] The fabrication of Comparative Example 11 was the same as that of Example 17, except that compound C-3 was used instead of compound A-2 in the light-emitting layer (EML).

[0416] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0417] Table 7. Device structures of Examples 17 to 19 and Comparative Examples 9 to 11

[0418]

[0419] The structure of the new material used in the device is shown below:

[0420]

[0421] Table 8 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current.

[0422] Table 8 Device data for Examples 17 to 19 and Comparative Examples 9 to 11

[0423]

[0424]

[0425] discuss:

[0426] In Examples 17 to 19 and Comparative Example 9, the first metal complex GD4 was doped into compounds A-2, A-5, and A-60 of the present invention and compound C-1 of the non-present invention, respectively. Compared with Comparative Example 9, the EQE of Examples 17 to 19 was increased by 20.4%, 21.1%, and 19.2%, respectively, while CE and PE were significantly improved, and the driving voltage was also reduced. This demonstrates that the compounds of the present invention with an aryl substituent at the 1-position of dibenzofuran, compared with compounds with a heteroaryl substituent at the 1-position of dibenzofuran, can improve device performance, especially the EQE, when applied to electroluminescent devices.

[0427] In Examples 17 to 19 and Comparative Example 10, the first metal complex GD4 was doped into compounds A-2, A-5, and A-60 of the present invention, respectively, and into compound C-2 of the non-present invention. Compared with Comparative Example 10, the driving voltages of Examples 17 to 19 were comparable or lower, but their EQE was increased by 9.4%, 10.1%, and 8.3%, respectively, while CE and PE were also improved. This indicates that the compounds of the present invention with cyano substituents on ring B, compared to the comparative compound C-2 with cyano substituents on ring A, can improve device performance, especially the EQE, when applied to electroluminescent devices.

[0428] In Examples 17 to 19 and Comparative Example 11, the first metal complex GD4 was doped into compounds A-2, A-5, and A-60 of the present invention, respectively, and into compound C-3 of the non-present invention. Compared with Comparative Example 11, the driving voltage of Examples 17 to 19 was slightly increased, but their EQE was improved by 14.4%, 15.1%, and 13.3%, respectively, while CE and PE were also improved. Therefore, the compounds of the present invention can meet the performance requirements for commercial use and have superior device efficiency, making them a class of compounds with commercial potential.

[0429] Device Example 20

[0430] The fabrication of device example 20 was the same as that of device example 8, except that compound A-1 was used instead of compound A-5 in the light-emitting layer (EML).

[0431] Device Example 21

[0432] The fabrication of device example 21 was the same as that of device example 8, except that compound A-55 was used instead of compound A-5 in the light-emitting layer (EML).

[0433] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0434] Table 9. Device structures of Examples 20 and 21

[0435]

[0436] The structure of the new material used in the device is shown below:

[0437]

[0438] Table 10 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current.

[0439] Table 10 Device data for Examples 20 and 21, and Comparative Examples 4 and 5.

[0440]

[0441] In Examples 20 and 21, the first metal complex GD2 was doped into compounds A-1 and A-55 of the present invention, respectively. The devices exhibited high luminous efficiency, particularly high EQE. In Examples 20 to 21 and Comparative Example 4, the first metal complex GD2 was doped into compounds A-1 and A-55 of the present invention, respectively, and compound C-2 of a non-present invention. Compared to Comparative Example 4, the EQE of Examples 20 to 21 increased by 8.5% and 9.3%, respectively, while CE increased by 8.8% and 9.6%, PE increased by 17.6% and 22%, respectively, and the driving voltage was also reduced. This demonstrates that the compounds of the present invention with cyano substituents on ring B, compared to the comparative compound C-2 with cyano substituents on ring A, can improve device performance in all aspects, especially the overall improvement in device efficiency, when applied to electroluminescent devices.

[0442] In Examples 20 and 21 and Comparative Example 5, the first metal complex GD2 was doped into compounds A-1 and A-55 of the present invention, respectively, and compound C-3 of the non-present invention. Compared with Comparative Example 5, the driving voltages of Examples 20 and 21 were comparable to those of the comparative example, but their EQE was improved by 10.8% and 11.7%, respectively, while CE was improved by 10.1% and 10.8%, respectively, and PE was improved by 9.4% and 13.6%, respectively. Therefore, the compounds of the present invention can meet the performance requirements for commercial use and have superior device efficiency, making them a class of compounds with commercial potential.

[0443] In summary, the compounds of Formula 1 in this invention, when applied to organic electroluminescent devices, improve the electron-hole transport balance of the material. Compared to compounds not in this invention (without specific cyano substitution or a non-Formula 1 framework), device performance is significantly improved, with a marked increase in EQE, CE, and PE. This is of great benefit to the industry.

[0444] Device Example 22

[0445] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, the ITO anode was sequentially evaporated at a rate of 0.2-2 Å / s via thermal vacuum evaporation. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound H1 was used as the electron blocking layer (EBL). Then, compound GD23 was doped into compound H1 and compound NH-1 and co-evaporated as the light-emitting layer (EML). Compound H2 was used as the hole blocking layer (HBL). On the hole blocking layer, compound A-2 of the present invention and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as the electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was evaporated as the electron injection layer, and a 120 nm thick layer of aluminum was evaporated as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0446] Device Comparison Example 12

[0447] The fabrication of Comparative Example 12 was the same as that of Comparative Example 22, except that compound ET was used instead of compound A-2 in the electron transport layer (ETL).

[0448] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0449] Table 11 Partial device structures of Device Example 22 and Comparative Example 12

[0450]

[0451] The structure of the new material used in the device is shown below:

[0452]

[0453] Table 12 shows the results at 15 mA / cm 2CIE data, driving voltage (V), and external quantum efficiency (EQE) measured under constant current; and at 80 mA / cm 2 Device lifetime (LT97) measured under constant current.

[0454] Table 12 Device data for Example 22 and Comparative Example 12

[0455]

[0456] discuss:

[0457] In Example 22 and Comparative Example 12, compound A-2 of the present invention and compound ET of the non-present invention were used as electron transport materials, respectively. Compared with Comparative Example 12, although the driving voltage of Example 22 was slightly increased, its EQE was comparable and the device lifetime was improved by 9%. It should be noted that compound ET is a currently commercially available electron transport material. Compared with compound ET, the compound of the present invention, when applied to electroluminescent devices, can further improve device lifetime, demonstrating that the compound of the present invention is also an excellent electron transport material.

[0458] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A compound having the structure of Formula 1: in, X is selected from O; X1to X6are the same or different selected from CR x ; Ar is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms; Ring A and ring B are selected from benzene rings; R y and R1identically or differently on each occurrence, represent mono-, poly- or non- substitution; R2 may appear the same or different each time, indicating either mono- or poly-substitution; At least one of R2 is selected from cyano groups; R2 is selected from the following groups, either identically or differently, each time it appears: hydrogen, deuterium, cyano; R x at each occurrence, is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having from 1 to 12 carbon atoms; R y is independently at each occurrence selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having from 1 to 12 carbon atoms, substituted or unsubstituted aryl having from 6 to 20 carbon atoms; R1 is selected from the group consisting of the following groups, either identically or differently each time it appears: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-12 carbon atoms; Wherein, substituted alkyl and substituted aryl refer to any one of the alkyl and aryl groups that can be replaced by one or at least two unsubstituted alkyl groups selected from deuterium and having 1 to 20 carbon atoms.

2. The compound of claim 1, wherein, R1, R x and R y are, identically or differently at each occurrence, selected from the group consisting of hydrogen, deuterium.

3. The compound of claim 1, wherein, R y each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl group having from 6-12 carbon atoms.

4. The compound of claim 1, wherein, R y independently at each occurrence selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl.

5. The compound of claim 1, wherein, R2 is selected from cyano.

6. The compound of claim 1, wherein, Ar is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted fluorene.

7. The compound of claim 1, wherein, The compounds are selected from the group consisting of the following compounds: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， , , , , , , , , , , ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Optionally, the hydrogen in compounds A-1 to A-39, A-49 to A-91, A-101 to A-112, A-176 to A-214, A-224 to A-266, A-276 to A-287, A-339, A-351 to A-389, A-399 to A-441, A-451 to A-462, A-526 to A-575, and A-585 to A-598 is partially or completely replaced by deuterium.

8. An organic electroluminescent device comprising: An anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises a compound according to any one of claims 1-7; The organic layer is a light-emitting layer, the compound is a host compound, and the light-emitting layer comprises at least a first metal complex; the first metal complex has a general formula of M(L a ) m (L b ) n (L c ) q ​ Metal M is selected from metals with a relative atomic mass greater than 40; L a , L b , L c are a first, a second and a third ligand, respectively, coordinating to the metal M, the ligands L a , L b , L c may be the same or different; Ligand L a , L b , L c may optionally be linked to form a polydentate ligand; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of the metal M; when m is equal to or greater than 2, the plurality of L a may be the same or different; when n is 2, the two L b may be the same or different; when q is 2, the two L c may be the same or different; Ligand L a having a structure as shown in Formula 2: When ring C1 and ring C2 appear in the same or different ways, they are selected from aromatic rings having 5-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof; Q1 and Q2 are selected from C or N each time they appear, either the same or different. R 11 and R 12 identically or differently in each occurrence, represent mono-, poly- or no substitution; R 11 and R 12 Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Substituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, carboxylic acid, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; adjacent substituents R 11 , R 12 may optionally be joined to form a ring; wherein the ligand L b , L c is selected at each occurrence, identically or differently, from any one or two of the following structures: ， ， ， ， ， ， ， ， ， ， ， ； in, R a , R b and R c each, on each occurrence, identically or differently, represent mono-, poly- or no substitution; X b at each occurrence, is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d are at each occurrence, identically or differently, selected from the group consisting of O, S, Se and NR N2 ; R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, etc. The following are substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, carboxylic acid, cyano, isocyano, hydroxy, and mercapto groups. adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may optionally be joined to form a ring; Substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkenyl, aryl, heteroaryl, alkylsilyl, alkylgermanium, arylgermanium, amino, which can be one or at least two 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 heteroalkyl having 3-20 ring atoms. Cycloyl, unsubstituted aralkyl with 7-30 carbon atoms, unsubstituted alkoxy with 1-20 carbon atoms, unsubstituted aroxy with 6-30 carbon atoms, unsubstituted alkenyl with 2-20 carbon atoms, unsubstituted alkynyl with 2-20 carbon atoms, unsubstituted aryl with 6-30 carbon atoms, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, carboxylic acid, cyano, isocyano, mercapto, and combinations thereof.

9. The organic electroluminescent device of claim 8, wherein the first metal complex is selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ， ， ， ， ， ， ， 。 10. The organic electroluminescent device according to claim 8, wherein The light-emitting layer also contains a second compound having a structure represented by Formula 3 or Formula 4: ， ； in, G is, on each occurrence, identically or differently, selected from C(R g )2, NR g , O or S; L T each occurrence is selected, identically or differently, from a single bond, substituted or unsubstituted alkylene having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having from 3 to 20 carbon atoms, substituted or unsubstituted arylene having from 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having from 3 to 20 carbon atoms, or a combination thereof; T is, on each occurrence, identically or differently, selected from C, CR t or N; R t R g Each time it appears, it is selected from the group consisting of, either identically or differently from, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted... Or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, carboxylic acid, cyano, isocyano, hydroxyl, mercapto; Ar1 is selected, either identically or differently, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or from substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; adjacent substituents R t , R g may optionally be joined to form a ring.

11. The organic electroluminescent device of claim 10, wherein the second compound has a structure represented by any one of formulas 3-a to 3-j and 4-a to 4-f: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； wherein In formula 3-a to formula 3-j, T, L T , the definition of Ar1 has the same definition as in formula 3; wherein, in formula 4-a to formula 4-f, T, G, L T , the definition of Ar1 has the same definition as in formula 4.

12. A compound composition comprising the compound according to any one of claims 1-7.

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