Boron-containing compound and organic electroluminescent device thereof

Abstract

The invention provides a boron-containing compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. According to the boron-containing organic compound provided by the invention, a hydrogenated carbazole skeleton is constructed by a fused benzene ring and an aliphatic ring, so that the molecular structure has excellent conjugacy and planarity, and the rigidity and stability of the compound molecule are improved; the solubility and the purifiability of molecules are improved by introducing an aliphatic ring, and the purity of the compound is improved, so that the luminous efficiency and the service life of an organic electroluminescent device are improved, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like, and has a good application effect and a good industrialization prospect.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a boron-containing compound and its organic electroluminescent device. Background Technology

[0002] OLED (Organic Light-Emitting Diode) is a self-emissive display technology. Its core advantages are self-illumination, high contrast, flexibility, and thinness. It has been widely used in mobile phone displays, tablet displays, automotive displays, and other applications.

[0003] The basic structure of an OLED consists of a thin, transparent indium tin oxide (ITO) electrode with semiconductor properties connected to a positive electrode, plus a metal cathode, forming a sandwich structure. This sandwich structure includes a hole transport layer (HTL), an emissive layer (EL), and an electron transport layer (ETL). When an appropriate voltage is applied, holes from the positive electrode and charges from the cathode combine in the EL to form excitons. These excitons excite the light-emitting material (doped material) in the EL, releasing energy as light. By adjusting the formulation of the doped material in the EL, red, green, and blue primary colors can be emitted, which can then be combined to create various colors. Therefore, the doped material in the EL is a core factor determining the device's luminous efficiency, color purity, and lifetime.

[0004] Based on the light-emitting mechanism, emissive layer doping materials are mainly classified into three categories: fluorescent doping materials, phosphorescent doping materials, and thermally activated delayed fluorescence (TADF) doping materials. Among them, TADF materials, through a donor-acceptor structure, minimize the energy difference between singlet and triplet states. Triplet excitons can undergo thermal activation to transition to singlet excitons, thereby emitting light. Theoretically, they possess 100% quantum efficiency, high color purity, good stability, and require no precious metals, making them a core development direction for next-generation OLEDs. However, current TADF doping materials suffer from poor stability, reduced lifetime due to concentration quenching sensitivity, decreased luminous efficiency, and reduced color purity. Therefore, developing higher-performance TADF doping materials is crucial to overcoming the current technological bottlenecks in OLEDs. Summary of the Invention

[0005] The purpose of this invention is to provide a boron-containing compound and an organic electroluminescent device thereof. When the boron-containing compound provided by this invention is applied to the light-emitting layer of an organic electroluminescent device, the luminous efficiency and lifespan of the organic electroluminescent device can be improved, thus solving the problems of low luminous efficiency and short lifespan of existing organic electroluminescent devices.

[0006] Specifically, the present invention provides a boron-containing compound having the general formula shown in structural formula 1.

[0007] The rings A and B are either the same or different and are selected from any one of C3-C15 cycloalkanes or C3-C15 cycloolefins that are R1 substituted or unsubstituted. R1, R5, and R6 are selected from the following groups, either identically or differently: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted amino. R2 and R3 are selected from any one of the following groups, either identically or differently: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted amino groups; or two adjacent R2 groups or two R3 groups are interconnected to form substituted or unsubstituted rings, and at least one of R2 and R3 is not selected from hydrogen; b is selected from 1, 2, or 3; c is selected from 1, 2, or 3. R7 is selected from any one of cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R7 are connected to each other to form a substituted or unsubstituted ring; The v is selected from C (H) or N atoms, either the same or different, and the v at the bonding site is selected from C.

[0008] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the boron-containing compound described in the present invention.

[0009] Beneficial effects: The boron-containing organic compound provided by this invention has excellent conjugation and planarity in its molecular structure by constructing a hydrogenated carbazole skeleton through fused benzene ring and aliphatic ring, which improves the rigidity and stability of the compound molecule. Furthermore, the introduction of aliphatic ring improves the solubility and purifurability of the molecule, thereby increasing the purity of the compound and thus improving the luminous efficiency and lifespan of organic light-emitting devices. It can be widely used in fields such as organic thin-film transistors and panel displays, and has good application effects and industrialization prospects. Detailed Implementation

[0010] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0011] In the compounds of this invention, any atom not specified as a particular isotope contains any stable isotope of that atom, and contains atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0012] Examples of halogens described in this invention may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0013] In this invention, "C1-C15" in "substituted or unsubstituted C1-C15 alkyl groups" refers to the number of carbon atoms in the unsubstituted alkyl group, excluding the number of carbon atoms in the substituents. Similarly, "C6-C30" in "substituted or unsubstituted C6-C30 aryl groups" refers to the number of carbon atoms in the unsubstituted aryl group, excluding the number of carbon atoms in the substituents. And so on.

[0014] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has 1 to 15 carbon atoms, preferably 1 to 10. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0015] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0016] The alkenyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an olefin molecule, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. Examples may include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, etc., but are not limited thereto.

[0017] The alkoxy group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkoxy hydrocarbon molecule, preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Examples may include methoxy, ethoxy, propoxy, butoxy, etc., but are not limited thereto.

[0018] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, phenanthrene, triphenylene, anthracene, pyrene, fluorenyl, spirodifluorenyl, spiroanthracenefluorenyl, benzo[a]fluorenyl, benzo[a]spirodifluorenyl, etc.

[0019] The alicyclic group described in this invention refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage-like structure, such as adamantane, norbornane, camphene, etc., but are not limited thereto.

[0020] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Examples of fused alicyclic and aromatic ring groups include, but are not limited to, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, and benzocycloheptenyl. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 18, and even more preferably 6 to 12. The linking site of the fused ring group can be on the aromatic ring or on the alicyclic ring, but is preferably on the aromatic ring.

[0021] The heteroaryl group described in this invention refers to a monovalent group in which at least one aromatic carbon atom is replaced by a heteroatom. The heteroaryl group has 2 to 30 carbon atoms, preferably 2 to 15, and even more preferably 2 to 10. The heteroatom includes, but is not limited to, the atoms listed below: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, the groups listed below: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, carbazoleyl, etc., but are not limited thereto.

[0022] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. The term "alkylsilyl" refers to at least one substituent R of a silyl (-SiH3) group. k It is an alkyl group, and the preferred alkylsilyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the "arylsilyl" refers to at least one substituent R of the alkyl (-SiH3) group. k It is an aryl group, and preferred arylsilyl groups specifically include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are not limited to these.

[0023] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom in an aromatic hydrocarbon molecule. The arylene group has a carbon number of C6 to C30, preferably C6 to C20, and even more preferably C6 to C10. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene groups include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, perylene, pyrene, indene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, etc.

[0024] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Examples of fused alicyclic and aromatic rings may include, but are not limited to, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, and naphthocyclopentane. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 18. The bonding sites of the fused alicyclic ring groups may all be on the aromatic ring, all on the alicyclic ring, or one on the aromatic ring and the other on the alicyclic ring, but preferably all on the aromatic ring.

[0025] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C20, and even more preferably C2 to C10. The heteroatom includes, but is not limited to, the following atoms: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl groups include, but are not limited to, the following groups: pyridylene, pyrimidinylene, quinolineylene, isoquinolineylene, furanylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thiophenylene, benzothiophenylene, dibenzothiophenylene, benzodibenzothiophenylene, etc.

[0026] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: halogen atom, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocyclic alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, preferably halogen atom, cyano, nitro The alkyl group (C1-C12), alicyclic group (C3-C12), heterocyclic alkyl group (C3-C12), aryl group (C6-C30), and heteroaryl group (C3-C30), wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: fluorine atom, cyano, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted Cyclobutyl, ethyl-substituted cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyridine The following groups are used: pyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazoyl, dibenzofuranyl, and dibenzothiopheneyl. When substituted with multiple substituents, the multiple substituents may be the same or different from each other.

[0027] In this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , And so on.

[0028] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0029] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0030] In this invention, "adjacent groups can connect with each other to form substituted or unsubstituted rings" refers to the formation of substituted or unsubstituted hydrocarbon rings or substituted or unsubstituted heterocycles by the combination of adjacent groups and optional aromatization. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Examples are shown below:

[0031] .

[0032] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0033] This invention provides a boron-containing compound having the general formula shown in structural formula 1.

[0034] The rings A and B are either the same or different and are selected from any one of C3-C15 cycloalkanes or C3-C15 cycloolefins that are R1 substituted or unsubstituted. R1, R5, and R6 are selected from the following groups, either identically or differently: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted amino. R2 and R3 are selected from any one of the following groups, either identically or differently: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted amino groups; or two adjacent R2 groups or two R3 groups are interconnected to form substituted or unsubstituted rings, and at least one of R2 and R3 is not selected from hydrogen; b is selected from 1, 2, or 3; c is selected from 1, 2, or 3. R7 is selected from any one of cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R7 are connected to each other to form a substituted or unsubstituted ring; The v is selected from C (H) or N atoms, either the same or different, and the v at the bonding site is selected from C.

[0035] Preferably, ring A and ring B are selected from any one of the following groups, either the same or different:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] R1 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl Triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and amino groups, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other; The a is independently selected from 0, 1, 2, 3, 4, 5, or 6; the a1 is independently selected from 0, 1, 2, 3, or 4; the a2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the a3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the a4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and the a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0042] Preferably, R7 is selected from any one of the following groups: cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, or combinations thereof:

[0043]

[0044] The T1 may be selected from O atoms, S atoms, C(R) atoms, or different atoms. a R b ) or N(R c ); The T2 is independently selected from O atoms, S atoms, or N(R) atoms. d ); T3 and T4 are independently selected from O atoms or S atoms; One of T5 and T6 is selected from a single bond, and the other is selected from an O atom, a S atom, or a C(R) atom. f R g ) or N(R h ); The ring D is selected from substituted or unsubstituted C3-C15 alicyclic groups; The t is selected from N atoms or C (H); the t at the bonding site is selected from C; The R4s are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or combinations thereof; or adjacent R4s may be interconnected to form substituted or unsubstituted rings; The R a R b R f R g Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or combinations thereof; or said R a and R b They can connect to each other to form substituted or unsubstituted rings; or the R f and R g They can connect with each other to form substituted or unsubstituted rings; The R c R d R hIndependently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or combinations thereof; or said R c R d R h It serves as a connecting bond, bonding with the rest of Equation 1; The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d4 is selected from 0, 1, 2, 3 or 4; the d5 is selected from 0, 1 or 2; and the d6 is selected from 0, 1, 2 or 3.

[0045] Preferably, R7 is selected from cyano, halogen, nitro, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, any one of the following groups or combinations thereof:

[0046]

[0047]

[0048]

[0049]

[0050]

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[0055]

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[0058]

[0059]

[0060]

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[0064]

[0065]

[0066]

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[0069]

[0070]

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[0075]

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[0080]

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[0086]

[0087]

[0088] The R4, R 44 The following groups, selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be used, either identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, Any one or more of isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzooxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R4s are connected to each other to form substituted or unsubstituted rings; The R c R d R h The following groups, selected from hydrogen, deuterium, substituted or unsubstituted, may be used, either identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, tri- The Rc is any one or more of the following: phenylene, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other; or the Rc is bonded as a linking bond to the remainder of Formula 1. The d1 is independently selected from 0, 1, 2, 3, 4, or 5; the d2 is independently selected from 0, 1, 2, 3, or 4; the d3 is independently selected from 0, 1, or 2; the d4 is independently selected from 0, 1, 2, or 3; the d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d6 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the d 12 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the d 13 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the d 14 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; the d 15 Select independently from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16.

[0089] Preferably, R5 and R6 are selected from hydrogen, deuterium, cyano, halogen, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl The substituents are any one or more of the following: dihydronaphthyl, anthraceneyl, phenanthreneyl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl, furanyl, thiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, silyl, amino, tetrahydrocarbazoleyl, and hexahydrocarbazoleyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other.

[0090] Preferably, R2 and R3 are selected from hydrogen, deuterium, cyano, halogen, nitro, and the following substituted or unsubstituted groups: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, etc. The substituted ring comprises one or more of the following: quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl, furanyl, thiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, silyl, and amino. When substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R2s or the two R3s are interconnected to form a substituted or unsubstituted ring, and at least one of the R2s and R3s is not selected from hydrogen.

[0091] Preferably, the boron-containing compound satisfies at least one of the following conditions: i. One of R2 and / or one of R3 is selected from any of the following groups, substituted or unsubstituted: phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl; ii. b is selected from 2 or 3, and two adjacent R2s are connected to each other to form substituted or unsubstituted groups of the following: benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, furan ring, thiophene ring, oxazole ring, thiazole ring, benzofuran ring, benzothiophene ring, indole ring; iii. c is selected from 2 or 3, and two adjacent R3s are connected to each other to form substituted or unsubstituted groups of the following: benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, furan ring, thiophene ring, oxazole ring, thiazole ring, benzofuran ring, benzothiophene ring, indole ring.

[0092] Preferably, when R1 and R7 are interconnected to form a substituted or unsubstituted ring, Formula 1 is selected from any of the following structures:

[0093]

[0094]

[0095] The R q The following groups, selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthraceneyl phenanthrene, triphenylene, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthiarinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, silyl, any one or more of the following, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R groups are... q They connect to each other to form substituted or unsubstituted rings; The R qq The following groups, selected from hydrogen, deuterium, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, and silyl, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other; h1 is independently selected from 0, 1, 2, 3, 4 or 5; h2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; h3 is independently selected from 0, 1, 2, 3 or 4; h4 is independently selected from 0, 1, 2, 3 or 4; the definitions of ring A, ring B, R2, R3, v, b, and c are the same as those in Equation 1.

[0096] Preferably, in each six-membered ring, at most two or at most one of the multiple v's are selected from N.

[0097] Most preferably, the boron-containing compound represented by Formula 1 is selected from any one of the following chemical structures:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361] .

[0362] The above lists some specific chemical structures of boron-containing compounds of structural formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. All compounds based on boron-containing compounds of structural formula 1 with substituents as defined above should be included.

[0363] Furthermore, the present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains a boron-containing compound as shown in Formula 1 of the present invention.

[0364] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the hole transport region and the electron transport region, and the light-emitting layer contains a boron-containing compound as shown in Formula 1 of the present invention.

[0365] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the hole transport region and the electron transport region, and the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains a boron-containing compound as shown in Formula 1 of the present invention.

[0366] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole injection layer is located between the anode and the cathode, the hole transport layer is located between the hole injection layer and the cathode, and the electron blocking layer is located between the hole transport layer and the cathode.

[0367] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device or a multilayer organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the multilayer organic electroluminescent device is an organic electroluminescent device formed by connecting N (N≥2) independent light-emitting units in series through a charge generation layer.

[0368] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, wherein an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0369] Preferably, the organic electroluminescent device of the present invention is a stacked organic electroluminescent device, wherein a first light-emitting unit emitting light of a first color, an Nth light-emitting unit emitting light of an Nth color, and a charge generation layer uniformly controlling the charge between the first light-emitting unit and the Nth light-emitting unit are formed between the anode and the cathode, and an n-type charge generation layer and a p-type charge generation layer are included between adjacent light-emitting units.

[0370] Preferably, the organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, wherein the capping layer is located on the side of the cathode opposite to the anode.

[0371] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, quartz, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0372] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below: The anode described in this invention preferably uses a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO); indium tin oxide containing silicon or silicon oxide; indium zinc oxide; indium oxide containing tungsten oxide and zinc oxide; and graphene. Furthermore, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[0373] The hole injection material described in this invention is used to facilitate hole injection from the anode to the light-emitting layer. The hole injection material is capable of receiving holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material lies between the work function of the anode material and the HOMO of the functional material of the film layer on the side away from the anode (e.g., the hole transport material of the hole transport layer). Specific examples may include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0374] The hole transport material described in this invention is preferably a material capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer, and possesses high hole mobility and good stability. The hole transport material described in this invention is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer, and can be a single-layer structure or a multi-layer structure. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc., can be used as the hole transport layer material. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4', 4”-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), etc., but not limited to these.

[0375] The preferred electron blocking layer material of this invention has a triplet (T1) energy level higher than the T1 energy level of the host material in the emissive layer, thus blocking energy loss from the emissive layer material. The HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the host material in the emissive layer, facilitating hole injection from the positive electrode into the emissive layer. Simultaneously, the electron blocking layer material is required to have high hole mobility to facilitate hole transport and reduce the power consumption of the device. The LUMO energy level of the electron blocking layer material is higher than the LUMO energy level of the host material in the emissive layer, serving as an electron blocker; that is, the electron blocking layer material is required to have a wide bandgap (Eg). Electron blocking layer materials meeting the above conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. For example, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine; dibenzofuran derivatives, such as N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, but not limited thereto.

[0376] The light-emitting layer material described in this invention typically contains a guest (doped) material and a host material. The guest material can be a simple fluorescent material, phosphorescent material, or TADF material, or a combination of fluorescent and phosphorescent materials.

[0377] The host material of the luminescent layer described in this invention preferably uses substances with a higher LUMO and a lower HOMO than the guest material, such as pyrene derivatives, styrylamine derivatives, thionylamine derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and tetraphenyl derivatives. Specific examples include 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1 3-Bis(N-carbazolyl)benzene (MCP), Tris(8-hydroxyquinoline)aluminum (Alq3), Bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), Bis(8-hydroxyquinoline)zinc (Znq2), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (YGAPA), 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBAPA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazol-3-amine (2PCAPA), 9-diphenyl-N-(4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazol-3-amine (PCAPBA), N,N,N',N' -Tetra(4-methylphenyl)-tetraphenyl-5,11-diamine (p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (p-mPhAFD), etc., but not limited to these.

[0378] As the guest material of the luminescent layer in this invention, it may include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCABPhA), N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), 4 4'-bis(4-(9H-carbazole-9-yl)styryl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 5,6,11 The following compounds are permitted, but are not limited to: 12-tetraphenylbenzotetraphenyl (Rubrene), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium(III)(Ir(npy)2acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy)3), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac), and boron-containing compounds of Formula 1 of the present invention. Preferably, the boron-containing compounds of Formula 1 of the present invention are preferred.

[0379] The hole-blocking layer material described in this invention needs to have good hole-blocking ability in order to block holes within the light-emitting layer. Materials such as imidazole derivatives, phenanthroline derivatives, metal complexes, and triazine derivatives are examples. Specific examples may include 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, but are not limited thereto.

[0380] The electron transport layer material described in this invention can be used to efficiently transport electrons. The electron transport material is preferably a material with high electron mobility, which can skillfully receive electrons injected from the negative electrode and transfer them to the light-emitting layer. The electron transport layer can utilize metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and polymeric compounds. Specific examples include, but are not limited to, Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), BAlq, Znq, ZnPBO, ZnBTZ, 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (p-EtTAZ), phenanthroline (BPhen), copper bath (BCP), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (PF-Py), etc.

[0381] Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (Liq), and benzimidazole-based compounds, but are not limited to these.

[0382] The electron injection layer material described in this invention is used to effectively inject electrons from the cathode into the light-emitting layer. The electron injection layer material comprises metals, metal oxides, complexes, metal halides, etc., and specific examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, lithium 8-hydroxyquinoline (LiQ), cesium oxide (Cs2O), etc. Furthermore, multiple of these compounds can be used in combination.

[0383] The cathode of this invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, 3.8 eV or less). Specific examples may include: metals or alloys thereof, multilayer materials, such as Ag (silver), Mg (magnesium), Cu (copper), Al (aluminum), Pt (platinum), Pd (palladium), Au (gold), Ni (nickel), Nd (neodymium), Ir (iridium), Cr (chromium), Li (lithium), Ca (calcium), LiF / Ca (lithium fluoride / calcium), LiF / Al (lithium fluoride / aluminum), Mo (molybdenum), Ti (titanium), including compounds thereof or mixtures thereof, but not limited thereto.

[0384] The anode and cathode described in this invention can each be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials forming the anode and cathode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a side-emitting type.

[0385] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, heterocyclic compounds, etc. Specific examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, aluminum(III)tris(8-hydroxyquinoline) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), etc., but is not limited to these.

[0386] The n-type charge-generating material described in this invention can be selected from one of the following materials or combinations thereof: tri-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-phenololine)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1 10-Phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternating-2,7-(9 Examples of materials that can be used include, but are not limited to, 9-dioctylfluorene (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). Additionally, auxiliary N-type charge-generating materials may also be included. For example, auxiliary N-type charge-generating materials may be alkali metals, such as Li, Cs, K, Rb, Na, or Fr, but are not limited to, or alkaline earth metals, such as Be, Mg, Ca, Sr, Ba, or Ra, but are not limited to.

[0387] The p-type charge-generating material of this invention may comprise one of the following materials or combinations thereof: 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPD), 1,4,5,8,9 ,11-hexaazatriphenylhexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, but not limited to these.

[0388] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., can be used, but are not limited to these. There are no particular limitations on the film thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[0389] The organic electroluminescent device of the present invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, televisions, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, lighting equipment, etc.

[0390] Synthesis Examples

[0391] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0392] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0393] There are no particular limitations on the preparation method of the boron-containing compound of structural formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, the boron-containing compound of structural formula 1 of the present invention can be prepared using the synthetic route shown below.

[0394]

[0395] P1, P2, and P3 are independently selected from any one of I, Br, Cl, and F; The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0396] Preparation and characterization of compounds

[0397] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0398] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0399] [Synthetic Example 1] Preparation of intermediate C-151:

[0400] Under nitrogen protection, m-151 (75.04 g, 300.00 mmol), n-151 (45.71 g, 360.00 mmol), K2CO3 (58.05 g, 420.00 mmol), Pd(dppf)Cl2 (2.63 g, 3.60 mmol), and 1.50 L of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 7 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to obtain intermediate C-151 (56.78 g, 75%). HPLC analysis showed that the purity of the solid was ≥99.73%. Mass spectrometry m / z: 252.1667 (theoretical value: 252.1675).

[0401] By substituting the raw materials accordingly, intermediate C can be prepared according to the preparation method of intermediate C-151 in Synthesis Example 1. The raw materials are shown in the table below:

[0402] [Synthetic Example 2] Preparation of intermediate b-343:

[0403] Under nitrogen protection, c-8 (74.20 g, 300.00 mmol), s-343 (64.53 g, 315.00 mmol), sodium tert-butoxide (43.25 g, 450.00 mmol), Pd2(dba)3 (2.75 g, 3.00 mmol), X-Phos (2.86 g, 6.00 mmol), and 2 L of toluene were added to a reaction flask, and the mixture was stirred under reflux for 10 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound b-343 (80.20 g, 72% yield). HPLC analysis showed that the solid purity was ≥99.76%. Mass spectrometry m / z: 377.1977 (theoretical value: 371.1995).

[0404] [Synthetic Example 3] Preparation of intermediate b-767:

[0405] Under nitrogen protection, p-767 (98.84 g, 400.00 mmol), s-767 (62.94 g, 400.00 mmol), K2CO3 (77.40 g, 560.00 mmol), Pd(dppf)Cl2 (3.51 g, 4.80 mmol), and 2 L of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 9 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to obtain intermediate l-767 (85.04 g, 76%). HPLC analysis showed that the purity of the solid was ≥99.74%. Mass spectrometry m / z: 279.0440 (theoretical value: 279.0451).

[0406] Under nitrogen protection, l-767 (78.32 g, 280.00 mmol), pinacol diborate (74.66 g, 294.00 mmol), potassium carbonate (46.44 g, 336.00 mmol), tetrakis(triphenylphosphine)palladium (3.24 g, 2.80 mmol), and 1 L of dimethylformamide were added to a reaction flask. The mixture was stirred under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. The mixture was recrystallized from toluene / ethanol in a 6:1 ratio to give b-767 (63.95 g, 79% yield). HPLC analysis showed that the solid purity was ≥99.78%. Mass spectrometry m / z: 289.0901 (theoretical value: 289.0910).

[0407] [Synthetic Example 4] Preparation of Compound 8:

[0408] Preparation of intermediate A-8: Compounds a-8 (45.49 g, 200.00 mmol), b-8 (62.90 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (0.69 g, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-8 (61.28 g, 84%). HPLC analysis showed a solid purity ≥99.83%. Mass spectrometry m / z: 364.0485 (theoretical value: 364.0466).

[0409] Preparation of intermediate B-8: Intermediate A-8 (54.72 g, 150.00 mmol), compound c-8 (44.52 g, 180.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate B-8 (72.83 g, 82%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 591.1749 (theoretical value: 591.1765).

[0410] Preparation of intermediate C-8: Intermediate B-8 (59.21 g, 100.00 mmol), compound d-8 (20.55 g, 120.00 mmol), and cesium carbonate (65.16 g, 200.00 mmol) were dissolved in DMF (1000 mL) and refluxed under nitrogen for 6 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate C-8 (58.72 g, 79%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 742.2736 (theoretical value: 742.2751).

[0411] Preparation of compound 8: Intermediate C-8 (44.60 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 8 (14.19 g, 33%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 716.2981 (theoretical value: 716.2999). Theoretical elemental content (%) C 52 H 37 BN2O: C, 87.15; H, 5.20; N, 3.91. Actual elemental content (%): C, 87.12; H, 5.22; N, 3.88.

[0412] [Synthetic Example 5] Preparation of Compound 22:

[0413] Preparation of intermediate A-22: Compound a-22 (33.31 g, 200.00 mmol), compound b-22 (104.56 g, 240.00 mmol), and cesium carbonate (130.33 g, 400.00 mmol) were dissolved in DMF (2000 mL) and refluxed under nitrogen for 10 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate A-22 (94.31 g, 81%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 581.2677 (theoretical value: 581.2661).

[0414] Preparation of intermediate B-22: Intermediate A-22 (87.33 g, 150.00 mmol), compound c-8 (44.52 g, 180.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate B-22 (95.93 g, 79%). The purity of the solid was ≥99.81% as determined by HPLC. Mass spectrometry m / z: 808.3971 (theoretical value: 808.3960).

[0415] Preparation of intermediate C-22: Intermediate B-22 (80.95 g, 100.00 mmol), compound d-8 (20.55 g, 120.00 mmol), and cesium carbonate (65.16 g, 200.00 mmol) were dissolved in DMF (1000 mL) and refluxed under nitrogen for 6 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate C-22 (73.98 g, 77%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 959.4929 (theoretical value: 959.4945).

[0416] Preparation of compound 22: Intermediate C-22 (57.65 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 22 (16.25 g, 29%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 933.5181 (theoretical value: 933.5193). Theoretical elemental content (%) C 68 H 64 BN3: C, 87.44; H, 6.91; N, 4.50. Actual elemental content (%): C, 87.41; H, 6.94; N, 4.53.

[0417] [Synthetic Example 6] Preparation of Compound 54:

[0418] Preparation of intermediate A-54: Compounds a-54 (49.09 g, 200.00 mmol), b-54 (29.26 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (693 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-54 (40.76 g, 84%). HPLC analysis showed a solid purity ≥99.84%. Mass spectrometry m / z: 242.0120 (theoretical value: 242.0110).

[0419] Preparation of intermediate B-54: Intermediate A-54 (36.39 g, 150.00 mmol), compound c-8 (89.04 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate B-54 (77.16 g, 82%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 696.2717 (theoretical value: 696.2708).

[0420] Preparation of intermediate C-54: Intermediate B-54 (62.73 g, 100.00 mmol), compound d-8 (20.55 g, 120.00 mmol), and cesium carbonate (65.16 g, 200.00 mmol) were dissolved in DMF (1000 mL) and refluxed under nitrogen for 6 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate C-54 (67.03 g, 79%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 847.3681 (theoretical value: 847.3693).

[0421] Preparation of compound 54: Intermediate C-54 (50.91 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 54 (15.77 g, 32%). HPLC analysis showed a solid purity of ≥99.96%. Mass spectrometry m / z: 821.3959 (theoretical value: 821.3941). Theoretical elemental content (%) C 60 H 48 BN3: C, 87.68; H, 5.89; N, 5.11. Actual elemental content (%): C, 87.66; H, 5.92; N, 5.07.

[0422] [Synthetic Example 7] Preparation of Compound 110:

[0423] According to the preparation method in Synthesis Example 4, a-54 and b-54 in Synthesis Example 4 were replaced with a-110 and b-110, respectively, while other steps remained unchanged, to obtain compound 110 (18.15 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1079.4822 (theoretical value: 1079.4806). Theoretical elemental content (%) C 78 H 62 BN3Si: C, 86.72; H, 5.79; N, 3.89. Actual elemental content (%): C, 86.70; H, 5.76; N, 3.87.

[0424] [Synthetic Example 8] Preparation of Compound 128:

[0425] According to the preparation method in Synthesis Example 4, a-54 and b-54 in Synthesis Example 4 were replaced with a-110 and b-128, respectively, while other steps remained unchanged, to obtain compound 128 (16.59 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 861.3876 (theoretical value: 861.3890). Theoretical elemental content (%) C 62 H 48 BN3O: C, 86.40; H, 5.61; N, 4.88. Actual element content (%): C, 86.38; H, 5.64; N, 4.83.

[0426] [Synthetic Example 9] Preparation of Compound 151:

[0427] According to the preparation method in Synthesis Example 3, a-22 and b-22 in Synthesis Example 3 were replaced with a-151 and b-151, respectively, while other steps remained unchanged, to obtain compound 151 (14.32 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 761.3275 (theoretical value: 761.3262). Theoretical elemental content (%) C 54 H 32 D5BN2O2: C, 85.15; H, 5.56; N, 3.68. Actual elemental content (%): C, 85.13; H, 5.54; N, 3.70.

[0428] [Synthetic Example 10] Preparation of Compound 273:

[0429] Preparation of intermediate A-273: Compounds a-110 (49.09 g, 200.00 mmol), b-273 (61.48 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (693 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-273 (61.05 g, 81%). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 376.1219 (theoretical value: 376.1206).

[0430] Preparation of intermediate B-273: Intermediate A-273 (56.53 g, 150.00 mmol), compound c-8 (133.56 g, 540.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate B-273 (122.30 g, 77%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 1057.5119 (theoretical value: 1057.5102).

[0431] Preparation of compound 273: Intermediate B-273 (63.53 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 273 (17.34 g, 28%). HPLC analysis showed a solid purity of ≥99.95%. Mass spectrometry m / z: 1031.5336 (theoretical value: 1031.5350). Theoretical elemental content (%) C 76 H 66 BN3: C, 88.44; H, 6.45; N, 4.07. Actual elemental content (%): C, 88.40; H, 6.48; N, 4.10.

[0432] [Synthetic Example 11] Preparation of Compound 298:

[0433] Preparation of intermediate A-298: Compounds a-298 (70.67 g, 200.00 mmol), b-298 (65.31 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (693 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-298 (82.12 g, 82%). HPLC analysis showed a solid purity ≥99.86%. Mass spectrometry m / z: 499.9651 (theoretical value: 499.9640).

[0434] Preparation of intermediate B-298: Compounds A-298 (75.11 g, 150.00 mmol), c-298 (39.97 g, 180.00 mmol), and potassium carbonate (37.32 g, 270.00 mmol) were dissolved in a mixture of THF and water (540 mL: 140 mL). Pd(PPh3)4 (520 mg, 0.45 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate B-298 (77.10 g, 80%). HPLC analysis showed a solid purity ≥99.81%. Mass spectrometry m / z: 642.0669 (theoretical value: 642.0656).

[0435] Preparation of intermediate C-298: Intermediate B-298 (64.25 g, 100.00 mmol), compound c-8 (59.36 g, 240.00 mmol), and cesium carbonate (65.16 g, 200.00 mmol) were dissolved in DMF (1000 mL) and refluxed under nitrogen for 6 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate C-298 (84.48 g, 77%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 1096.3236 (theoretical value: 1096.3253).

[0436] Preparation of compound 298: Intermediate C-298 (65.83 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 298 (17.62 g, 30%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 978.4178 (theoretical value: 978.4155). Theoretical elemental content (%) C 74 H 51BN2: C, 90.78; H, 5.25; N, 2.86. Actual elemental content (%): C, 90.74; H, 5.21; N, 2.89.

[0437] [Synthetic Example 12] Preparation of Compound 339:

[0438] Preparation of intermediate A-339: Compound a-339 (36.90 g, 200.00 mmol), compound d-8 (82.20 g, 480.00 mmol), and cesium carbonate (130.33 g, 400.00 mmol) were dissolved in DMF (2000 mL) and refluxed under nitrogen for 10 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate A-339 (77.92 g, 80%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 486.1666 (theoretical value: 486.1674).

[0439] Preparation of intermediate B-339: Intermediate A-339 (73.05 g, 150.00 mmol), compound c-8 (89.04 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate B-339 (110.17 g, 78%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 940.4287 (theoretical value: 940.4272).

[0440] Preparation of compound 339: Intermediate B-339 (56.50 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 339 (15.37 g, 28%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 914.4535 (theoretical value: 914.4520). Theoretical elemental content (%) C 66 H 55 BN4: C, 86.64; H, 6.06; N, 6.12. Actual elemental content (%): C, 86.61; H, 6.04; N, 6.16.

[0441] [Synthetic Example 13] Preparation of Compound 343:

[0442] Preparation of intermediate A-343: Compounds a-343 (61.27 g, 200.00 mmol), b-343 (178.21 g, 480.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixed solution of THF and water (720.00 mL: 180.00 mL). Pd(PPh3)4 (693.00 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-343 (129.51 g, 81%). HPLC analysis showed a solid purity ≥99.85%. Mass spectrometry m / z: 798.3415 (theoretical value: 798.3428).

[0443] Preparation of intermediate B-343: Intermediate A-343 (119.92 g, 150.00 mmol), compound c-8 (89.04 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500.00 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate B-343 (150.49 g, 80%). The purity of the solid was ≥99.82% as determined by HPLC. Mass spectrometry m / z: 1252.6037 (theoretical value: 1252.6026).

[0444] Preparation of compound 343: Intermediate B-343 (75.25 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.5 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100.00 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 343 (22.09 g, 30%). HPLC analysis showed a solid purity of ≥99.94%. Mass spectrometry m / z: 1226.6283 (theoretical value: 1226.6274). Theoretical elemental content (%) C 90 H 63 D8BN4: C, 88.07; H, 6.49; N, 4.56. Actual elemental content (%): C, 88.04; H, 6.50; N, 4.57.

[0445] [Synthetic Example 14] Preparation of Compound 370:

[0446] According to the preparation method in Synthesis Example 9, a-298, b-298, and c-298 in Synthesis Example 9 were replaced with a-370, b-370, and c-370, respectively, while other steps remained unchanged, yielding compound 370 (14.81 g, 29%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 850.3899 (theoretical value: 850.3891). Theoretical elemental content (%) C 61 H 39D5BN3O: C, 86.11; H, 5.80; N, 4.94. Actual elemental content (%): C, 86.10; H, 5.83; N, 4.95.

[0447] [Synthetic Example 15] Preparation of Compound 508:

[0448] Preparation of intermediate A-508: Compounds a-508 (52.68 g, 200.00 mmol), b-370 (42.73 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180.00 mL). Pd(PPh3)4 (693.00 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-343 (54.48 g, 86%). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 316.0635 (theoretical value: 316.0642).

[0449] Preparation of intermediate C-508: Intermediate A-508 (47.51 g, 150.00 mmol), compound c-8 (89.04 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate B-343 (148.97 g, 81%). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 1224.5844 (theoretical value: 1224.5837).

[0450] Preparation of compound 508: Intermediate C-508 (73.56 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.5 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 508 (23.03 g, 32%). HPLC analysis showed a solid purity of ≥99.95%. Mass spectrometry m / z: 1198.6093 (theoretical value: 1198.6085). Theoretical elemental content (%) C 88 H 75 BN4: C, 88.12; H, 6.30; N, 4.67. Actual elemental content (%): C, 88.14; H, 6.31; N, 4.65.

[0451] [Synthetic Example 16] Preparation of Compound 664:

[0452] According to the preparation method in Synthesis Example 9, a-298, b-298, c-298, and c-8 in Synthesis Example 9 were replaced with a-370, b-664, c-664, and d-664, respectively, while other steps remained unchanged, yielding compound 664 (20.28 g, 33%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1023.4713 (theoretical value: 1023.4724). Theoretical elemental content (%) C 76 H 58 BN3: C, 89.13; H, 5.71; N, 4.10. Actual elemental content (%): C, 89.10; H, 5.72; N, 4.14.

[0453] [Synthetic Example 17] Preparation of Compound 725:

[0454] According to the preparation method of Synthesis Example 11, a-343, b-343, and c-8 in Synthesis Example 9 were replaced with a-725, b-725, and c-725, respectively, while other steps remained unchanged, yielding compound 725 (18.01 g, 34%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 882.3886 (theoretical value: 882.3894). Theoretical elemental content (%) C 64 H 47 BN4: C, 87.06; H, 5.37; N, 6.35. Actual element content (%): C, 87.04; H, 5.35; N, 6.38.

[0455] [Synthetic Example 18] Preparation of Compound 741:

[0456] Preparation of intermediate C-741: Compounds a-741 (40.93 g, 200.00 mmol), c-8 (118.72 g, 480.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixed solution of THF and water (720.00 mL: 180.00 mL). Pd(PPh3)4 (693.00 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate C-741 (109.45 g, 83%). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 658.3127 (theoretical value: 658.3115).

[0457] Preparation of compound 741: Intermediate C-741 (39.56 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100.00 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 741 (13.29 g, 35%). HPLC analysis showed a solid purity of ≥99.96%. Mass spectrometry m / z: 632.3355 (theoretical value: 632.3363). Theoretical elemental content (%) C 46 H 41 BN2: C, 87.33; H, 6.53; N, 4.43. Actual elemental content (%): C, 87.30; H, 6.56; N, 4.42.

[0458] [Synthetic Example 19] Preparation of Compound 747:

[0459] According to the preparation method in Synthesis Example 2, a-8, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with a-747, b-747, c-747, and d-747, respectively, while other steps remained unchanged, yielding compound 747 (14.76 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 773.3637 (theoretical value: 773.3626). Theoretical elemental content (%) C 56 H 36 D5BN2O: C, 86.92; H, 5.99; N, 3.62. Actual elemental content (%): C, 86.89; H, 5.97; N, 3.65.

[0460] [Synthetic Example 20] Preparation of Compound 767:

[0461] Preparation of intermediate A-767: Compounds a-747 (45.49 g, 200.00 mmol), b-767 (69.38 g, 240.00 mmol), and potassium carbonate (49.75 g, 360.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (693 mg, 0.60 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-767 (64.26 g, 82%). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 391.0589 (theoretical value: 391.0575).

[0462] Preparation of intermediate B-767: Intermediate A-767 (58.77 g, 150.00 mmol), compound c-767 (89.40 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate B-767 (103.09 g, 81%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 847.3061 (theoretical value: 847.3078).

[0463] Preparation of compound 767: Intermediate B-767 (50.91 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 339 (14.30 g, 29%). HPLC analysis showed a solid purity of ≥99.95%. Mass spectrometry m / z: 821.3342 (theoretical value: 821.3326). Theoretical elemental content (%) C 57 H 40BN5O: C, 83.31; H, 4.91; N, 8.52. Actual elemental content (%): C, 83.28; H, 4.87; N, 8.57.

[0464] [Synthetic Example 21] Preparation of Compound 784:

[0465] According to the preparation method in Synthesis Example 18, a-747, b-767, and c-767 in Synthesis Example 18 were replaced with a-8, b-784, and c-8, respectively, while other steps remained unchanged, to obtain compound 784 (14.45 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 752.3379 (theoretical value: 752.3363). Theoretical elemental content (%) C 56 H 41 BN2: C, 89.35; H, 5.49; N, 3.72. Actual elemental content (%): C, 89.31; H, 5.46; N, 3.76.

[0466] [Synthetic Example 22] Preparation of Compound 794:

[0467] According to the preparation method in Synthesis Example 18, a-747, b-767, and c-767 in Synthesis Example 18 were replaced with a-8, b-794, and c-8, respectively, while other steps remained unchanged, yielding compound 794 (15.54 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 892.3987 (theoretical value: 892.3989). Theoretical elemental content (%) C 67 H 49 BN2: C, 90.12; H, 5.53; N, 3.14. Actual elemental content (%): C, 90.10; H, 5.55; N, 3.11.

[0468] [Synthetic Example 23] Preparation of Compound 800:

[0469] Preparation of intermediate A-800: Compound a-22 (33.31 g, 200.00 mmol), compound b-800 (50.23 g, 240.00 mmol), and cesium carbonate (130.33 g, 400.00 mmol) were dissolved in DMF (2000 mL) and refluxed under nitrogen for 10 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate A-800 (56.93 g, 80%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 355.0952 (theoretical value: 355.0939).

[0470] Preparation of intermediate B-800: Intermediate A-800 (53.37 g, 150.00 mmol), compound c-8 (89.04 g, 360.00 mmol), and cesium carbonate (97.75 g, 300.00 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate B-800 (94.83 g, 78%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 809.3558 (theoretical value: 809.3537).

[0471] Preparation of compound 800: Intermediate B-800 (48.63 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 800 (14.58 g, 31%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 783.3773 (theoretical value: 783.3785). Theoretical elemental content (%) C 57 H 46 BN3: C, 87.34; H, 5.92; N, 5.36. Actual elemental content (%): C, 87.30; H, 5.95; N, 5.38.

[0472] [Synthetic Example 24] Preparation of Compound 873:

[0473] According to the preparation method in Synthesis Example 3, b-22, c-8, and d-8 in Synthesis Example 3 were replaced with b-873, c-873, and d-873, respectively, while other steps remained unchanged, yielding compound 873 (15.91 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 929.4388 (theoretical value: 929.4370). Theoretical elemental content (%) C 63 H 60 BN3SSi: C, 81.35; H, 6.50; N, 4.52. Actual elemental content (%): C, 81.34; H, 6.48; N, 4.50.

[0474] [Synthetic Example 25] Preparation of Compound 874:

[0475]

[0476] Preparation of intermediate A1-874: Compounds a-298 (106.00 g, 300.00 mmol), b-874 (85.71 g, 360.00 mmol), and potassium carbonate (74.63 g, 540.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (1.04 g, 0.90 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 14 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A1-874 (116.21 g, 83%). HPLC analysis showed a solid purity ≥99.85%. Mass spectrometry m / z: 465.9790 (theoretical value: 465.9797).

[0477] Preparation of intermediate A-874: Compounds A1-874 (112.01 g, 240.00 mmol), c-874 (67.32 g, 290.00 mmol), and potassium carbonate (60.81 g, 440.00 mmol) were dissolved in a mixture of THF and water (720 mL: 180 mL). Pd(PPh3)4 (832 mg, 0.72 mmol) was added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 13 hours. After the reaction was complete, the mixture was washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether = 6:1) to give intermediate A-874 (118.76 g, 80%). HPLC analysis showed a solid purity ≥99.84%. Mass spectrometry m / z: 618.1586 (theoretical value: 618.1595).

[0478] Preparation of intermediate B-874: Intermediate A-874 (111.34 g, 180 mmol), compound d-874 (80.30 g, 270 mmol), and cesium carbonate (117.30 g, 360.00 mmol) were dissolved in DMF (1800.00 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate B-874 (135.47 g, 84%). The purity of the solid was ≥99.82% as determined by HPLC. Mass spectrometry m / z: 895.3061 (theoretical value: 895.3050).

[0479] Preparation of intermediate C-874: Intermediate B-874 (107.51 g, 120.00 mmol), compound e-874 (35.33 g, 180.00 mmol), and cesium carbonate (78.20 g, 240.00 mmol) were dissolved in DMF (1200.00 mL) and refluxed under nitrogen for 8 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate C-874 (109.36 g, 85%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 1071.3980 (theoretical value: 1071.3988).

[0480] Preparation of compound 874: Intermediate C-874 (64.33 g, 60.00 mmol) was dissolved in 1000 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 8 hours. The mixture was then cooled to 0 °C and BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was complete, the reaction was quenched with 100 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 874 (17.75 g, 31%). HPLC analysis showed a solid purity of ≥99.95%. Mass spectrometry m / z: 953.4891 (theoretical value: 953.4880). Theoretical elemental content (%) C 70 H 60 BN3: C, 88.12; H, 6.34; N, 4.40. Actual elemental content (%): C, 88.14; H, 6.33; N, 4.43.

[0481] [Synthetic Example 26] Preparation of Compound 876:

[0482] According to the preparation method in Synthesis Example 2, a-8, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with a-747, b-876, c-876, and c-8, respectively, while other steps remained unchanged, yielding compound 876 (12.23 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 657.3054 (theoretical value: 657.3064). Theoretical elemental content (%) C 45 H 36 BN5: C, 82.19; H, 5.52; N, 10.65. Actual element content (%): C, 82.17; H, 5.56; N, 10.60.

[0483] [Synthetic Example 27] Preparation of Compound 877:

[0484] According to the preparation method in Synthesis Example 2, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with b-877, c-877, and d-877, respectively, while other steps remained unchanged, yielding compound 877 (15.61 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 928.4398 (theoretical value: 928.4384). Theoretical elemental content (%) C 67 H 57 BN2Si: C, 86.61; H, 6.18; N, 3.02. Actual elemental content (%): C, 86.58; H, 6.21; N, 3.06.

[0485] [Synthetic Example 28] Preparation of Compound 909:

[0486] Following the preparation method of Synthesis Example 4, b-54 and c-8 in Synthesis Example 4 were replaced with b-909 and c-909, respectively, while other steps remained unchanged, yielding compound 909 (13.69 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 786.3955 (theoretical value: 786.3973). Theoretical elemental content (%) C 57 H 43 D3BN3: C, 87.01; H, 6.28; N, 5.34. Actual elemental content (%): C, 87.04; H, 6.31; N, 5.30.

[0487] [Synthetic Example 29] Preparation of Compound 913:

[0488] According to the preparation method in Synthesis Example 4, b-54, c-8, and d-8 in Synthesis Example 4 were replaced with b-913, c-913, and d-913, respectively, while other steps remained unchanged, yielding compound 913 (16.38 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1063.5623 (theoretical value: 1063.5612). Theoretical elemental content (%) C 77 H 70 BN3O: C, 86.90; H, 6.63; N, 3.95. Actual elemental content (%): C, 86.88; H, 6.62; N, 3.97.

[0489] [Synthetic Example 30] Preparation of Compound 974:

[0490] According to the preparation method in Synthesis Example 2, a-8, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with a-747, b-974, c-974, and d-974, respectively, while other steps remained unchanged, yielding compound 974 (13.18 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 665.3019 (theoretical value: 665.3002). Theoretical elemental content (%) C 48 H 36 BN3: C, 86.61; H, 5.45; N, 6.31. Actual elemental content (%): C, 86.58; H, 5.49; N, 6.34.

[0491] [Synthetic Example 31] Preparation of Compound 1091:

[0492] Preparation of intermediate A-1091: Compound a-8 (45.49 g, 200.00 mmol), compound d-1091 (53.11 g, 240.00 mmol), and cesium carbonate (130.33 g, 400.00 mmol) were dissolved in DMF (2000.00 mL) and refluxed under nitrogen for 10 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate A-1091 (103.32 g, 82%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 628.1264 (theoretical value: 628.1281).

[0493] Preparation of intermediate B-1091: Weigh 63.00 g (100.00 mmol) of intermediate A-1091 into a 1000 mL three-necked round-bottom flask, add 480 mL of ultra-dry tetrahydrofuran, purge the solution with nitrogen three times and cool it to below -70 °C, then slowly add 60.00 mL (150.00 mmol) of 2.50 M n-butyllithium solution. After stirring at -70 °C for half an hour, slowly add a tetrahydrofuran solution of c-1091 (43.86 g (150.00 mmol) dropwise. After the addition is complete, stir at -70 °C for half an hour, then slowly restore to room temperature and stir overnight. After the reaction was complete, a saturated ammonium chloride solution was added to quench the reaction. The mixture was extracted three times with 450 mL of dichloromethane, and the organic phase was washed three times with water. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by vacuum distillation. 450 mL of dichloromethane was added to the obtained solid, and 29.16 g (200.00 mmol) of boron trifluoride diethyl ether (46.5% by mass) was added with stirring at room temperature. The mixture was stirred overnight at room temperature. 300 mL of saturated sodium bicarbonate solution was added to quench the reaction. The mixture was extracted with 300 mL of dichloromethane, and the organic phase was washed three times with water, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography to obtain intermediate B-1091 (66.04 g, 80%). HPLC analysis showed a solid purity ≥99.81%. Mass spectrometry m / z: 824.3909 (theoretical value: 824.3897).

[0494] Preparation of compound 1091: Intermediate B-1091 (49.53 g, 60.00 mmol) was dissolved in 1000.00 mL of tert-butylbenzene. Under nitrogen atmosphere at 0 °C, n-butyllithium (36.00 mL, 90.00 mmol, 2.50 M n-hexane solution) was added dropwise. The mixture was then heated to 70 °C and stirred for 8 hours. After cooling to 0 °C, BBr3 (12.00 mL, 120.00 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 10 hours. N,N-diisopropylethylamine (20.00 mL, 120.00 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 48 hours. After the reaction was completed, the reaction was quenched with 100.00 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether: dichloromethane = 8:1) to give compound 1091 (13.90 g, 29%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 798.4129 (theoretical value: 798.4145). Theoretical elemental content (%) C 59 H 51 BN2: C, 88.71; H, 6.44; N, 3.51. Actual elemental content (%): C, 88.68; H, 6.46; N, 3.54.

[0495] [Synthetic Example 32] Preparation of Compound 1104:

[0496] According to the preparation method in Synthesis Example 2, a-8, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with a-747, b-1104, b-1091, and c-8, respectively, while other steps remained unchanged, yielding compound 1104 (14.19 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 716.2440 (theoretical value: 716.2422). Theoretical elemental content (%) C 46 H 30 BF5N2: C, 77.11; H, 4.22; N, 3.91. Actual elemental content (%): C, 77.14; H, 4.19; N, 3.95.

[0497] [Synthetic Example 33] Preparation of Compound 1113: According to the preparation method in Synthesis Example 2, a-8, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with a-747, b-1113, c-1113, and d-1113, respectively, while other steps remained unchanged, yielding compound 1113 (14.74 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 767.3206 (theoretical value: 767.3220). Theoretical elemental content (%) C 54 H 38 BN5: C, 84.48; H, 4.99; N, 9.12. Actual element content (%): C, 84.46; H, 4.96; N, 9.08.

[0498] [Synthetic Example 34] Preparation of Compound 1120:

[0499] According to the preparation method in Synthesis Example 2, b-8, c-8, and d-8 in Synthesis Example 2 were replaced with b-1120, b-1091, and d-1120, respectively, while other steps remained unchanged, to obtain compound 1120 (13.86 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 769.2822 (theoretical value: 769.2805). Theoretical elemental content (%) C 52 H 32 D5BN2S2: C, 81.13; H, 5.50; N, 3.64. Actual elemental content (%): C, 81.10; H, 5.52; N, 3.61.

[0500] [Synthetic Example 35] Preparation of Compound 1199:

[0501] According to the preparation method of Synthesis Example 31, b-1091 and c-1091 in Synthesis Example 31 were replaced with b-1199 and b-1199 respectively, while other steps remained unchanged, to obtain compound 1199 (12.68 g, 27%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 782.3476 (theoretical value: 782.3468). Theoretical elemental content (%) C 57 H 43 BN2O: C, 87.46; H, 5.54; N, 3.58; Actual element content (%): C, 87.45; H, 5.55; N, 3.56.

[0502] Device Examples

[0503] In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0504] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. The emission spectrum of the device prepared according to this invention was tested at atmospheric pressure and room temperature, as well as at a current density of 10 mA / cm². 2 The luminous efficiency was measured. The lifetime of the device fabricated in this invention was tested using a McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Table 1.

[0505] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s, while the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0506] The following are compounds other than the boron-containing compound shown in Formula 1 used in the device fabrication examples:

[0507]

[0508]

[0509] Example 1: Fabrication of Organic Electroluminescent Device 1

[0510] An ITO / Ag / ITO layer was used as the anode on a glass substrate. A 60 nm layer of HI-1 was vacuum-deposited on the anode to form a hole injection layer. A 120 nm layer of HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer. A 5 nm layer of EB-1 was vacuum-deposited on the hole transport layer to form an electron blocking layer. A 35 nm layer of GH-1:GH-2:D-1:compound 8 (mixed in a mass ratio of 47%:47%:4%:2%) was vacuum-deposited on the electron blocking layer to form a light-emitting layer. A 5 nm layer of HB-1 was vacuum-deposited on the light-emitting layer to form a hole blocking layer. A 20 nm layer of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum-deposited on the hole blocking layer to form an electron transport layer. A 1.0 nm layer of LiF was vacuum-deposited on the electron transport layer to form an electron injection layer. A 15 nm layer of Mg and Ag (mass ratio of 1:9) was vacuum-deposited on the electron injection layer to form a cathode. An 80 nm layer of compound CP-1 was deposited on the cathode to form a capping layer.

[0511] Examples 2-31: Fabrication of Organic Electroluminescent Devices 2-31

[0512] Replacing compound 8 in the luminescent layer of Example 1 with compounds 22, 54, 110, 128, 151, 273, 298, 339, 343, 370, 508, 664, 725, 741, 747, 767, 784, 794, 800, 873, 874, 876, 877, 909, 913, 974, 1091, 1104, 1113, 1120, and 1199, respectively, while maintaining the same other steps, organic electroluminescent devices 2-32 were obtained.

[0513] Comparative Examples 1-4: Fabrication of Comparative Organic Electroluminescent Devices 1-4

[0514] By replacing compound 8 in the light-emitting layer of Example 1 with R-1, R-2, R-3, and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 4 were obtained.

[0515] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 32 and Comparative Examples 1 to 4 of the present invention are shown in Table 1.

[0516] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0517]

[0518] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%; As can be seen from Table 1, compared with Comparative Examples 1 to 4, when the boron-containing compound of Formula 1 of the present invention is used in the light-emitting layer of an organic electroluminescent device, the efficiency of the organic electroluminescent device is effectively improved, the lifespan of the device is improved, and the half-width at half-maximum of the device is narrowed, thereby improving the color purity of the device, further demonstrating that the compound of the present invention has excellent light-emitting performance.

[0519] In summary, the boron-containing compounds provided by this invention are a class of high-performance OLED materials with promising application prospects.

[0520] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A boron-containing compound characterized in that, having the general formula of structural formula 1, the ring A, ring B are the same or different, selected from any one of R1-substituted or unsubstituted C3-C15 cycloalkane, R1-substituted or unsubstituted C3-C15 cycloalkene; the R1, R5, R6 are the same or different, selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C30 aryl ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted amino group; the R2, R3 are the same or different, selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C30 aryl ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted amino group, or the adjacent two R2, two R3 are connected to form a substituted or unsubstituted ring, and at least one of the R2, R3 is not hydrogen; the b is selected from 1, 2 or 3; the c is selected from 1, 2 or 3; the R7 is selected from any one of cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C30 aryl ring, substituted or unsubstituted C2-C30 heteroaryl group, or the R1 and R7 are connected to form a substituted or unsubstituted ring; the v is the same or different, selected from C(H) or N atom, the v at the bonding site is selected from C.

2. The boron-containing compound according to claim 1, characterized in that, the ring A, ring B are the same or different, selected from any one of the following groups: R1is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, any one or more of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, cycloheptanoyl, cyclooctanoyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, indanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, amino, in case of being substituted with multiple substituents, the multiple substituents are the same or different from each other; a is independently selected from 0, 1, 2, 3, 4, 5 or 6; a1 is independently selected from 0, 1, 2, 3 or 4; a2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; a4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

3. The boron-containing compound of claim 1, wherein, R7 is selected from the group consisting of cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C1-C12 alkoxyl, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, the following group or a combination thereof: said T1is selected from the group consisting of O atom, S atom, C(R a R b ) or N(R c ) said T2is independently selected from an O atom, an S atom or N(R d ) ; T3, T4 are independently selected from O atom or S atom; one of said T5, T6is selected from a single bond, the other one is selected from an O atom, an S atom, a C(R f R g ) or N(R h ); ring D is selected from substituted or unsubstituted C3-C15 alicyclic group; t is selected from N atom or C(H); t at the bonding site is selected from C; R4 is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or a combination thereof; or two adjacent R4 can be connected to each other to form a substituted or unsubstituted ring; said R a , R b , R f , R g are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted condensed ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or a combination thereof; or said R a and R b may be connected to each other to form a substituted or unsubstituted ring; or said R f and R g may be connected to each other to form a substituted or unsubstituted ring; said R c , R d , R h are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 cycloalkyl and C6-C30 aryl fused ring group, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, or a combination thereof; or said R c , R d , R h are bonded to the rest of Formula 1 as a linking bond; said d1 is selected from 0, 1, 2, 3, 4 or 5; said d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d4 is selected from 0, 1, 2, 3 or 4; said d5 is selected from 0, 1 or 2; said d6 is selected from 0, 1, 2 or 3.

4. The boron-containing compound of claim 1, wherein, R7 is selected from cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyl dimethylsilyl, propyl dimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, any one of the following groups or a combination thereof: R4, R 44 are identically or differently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, any one or more of substituted or unsubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclooctan- yl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthylidinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl, in case of being substituted with a plurality of substituents, the plurality of substituents being identical or different from each other, or the two adjacent R4are connected to each other to form a substituted or unsubstituted ring; said R c , R d , R h are identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptananyl, adamantyl, norbornanyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, indolyl, furanyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, silyl, in case of being substituted with multiple substituents, the multiple substituents are identical or different from each other; or said Rc is bonded as a linking group to the rest of Formula 1 ; said d1 is independently selected from 0, 1, 2, 3, 4, or 5; said d2 is independently selected from 0, 1, 2, 3, or 4; said d3 is independently selected from 0, 1, or 2; said d4 is independently selected from 0, 1, 2, or 3; said d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; said d6 is independently selected from 0, 1, 2, 3, 4, 5, or 6; said d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said d 10 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; said d 11 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; said d 12 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; said d 13 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; said d 14 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; said d 15 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16.

5. The boron-containing compound of claim 1, wherein, said R5, R6 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, indolyl, furanyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl, amino, tetrahydrocarbazolyl, hexahydrocarbazolyl, any one or more of which is substituted with multiple substituents which are the same or different from each other.

6. The boron-containing compound of claim 5, wherein, said Formula 1 is selected from any one of the following structures when said R1 and R7 are connected to each other to form a substituted or unsubstituted ring: said R q are identically or differently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, any one or more of substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclooctan- yl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl groups, in case of being substituted with multiple substituents, the multiple substituents being identical or different from each other, or said two adjacent R q are connected to each other to form a substituted or unsubstituted ring; said R qq are identically or differently selected from the group consisting of hydrogen, deuterium, any one or more of the following radicals which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexan- yl, cycloheptan-yl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthylidinyl, indolyl, furanyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl, in case of being substituted with a plurality of substituents, the plurality of substituents being identical or different from each other; said h1 is independently selected from 0, 1, 2, 3, 4 or 5; said h2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said h3 is independently selected from 0, 1, 2, 3 or 4; said h4 is independently selected from 0, 1, 2, 3 or 4; said ring A, ring B, R2, R3, v, b, c are defined the same as in Formula 1.

7. The boron-containing compound of claim 1, wherein, said Formula 1 represents a boron-containing compound selected from any one of the following chemical structures: 。 8. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being positioned between the anode and the cathode or outside one or more of the electrodes, characterized in that, said organic layer contains the boron-containing compound of any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that said organic layer is located between an anode and a cathode, said organic layer includes at least one of a hole transport region, a light emitting layer, an electron transport region, said light emitting layer is located between the hole transport region and the electron transport region, said light emitting layer contains the boron-containing compound of any one of claims 1-7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between an anode and a cathode, and includes at least one of a hole transport region, a light emitting layer, and an electron transport region, the light emitting layer is located between the hole transport region and the electron transport region, the light emitting layer includes a host material and a dopant material, the dopant material includes the boron-containing compound of any one of claims 1-7.

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