Boron-nitrogen heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a boron-nitrogen heterocyclic compound and an organic electroluminescent device thereof. The boron-nitrogen heterocyclic compound provided by the invention has the advantages of large steric hindrance, strong rigidity, small molecular vibration, realization of narrow spectrum emission, improvement of light color purity, increase of intermolecular distance, reduction of intermolecular acting force, and reduction of intermolecular overlapping on one hand, so as to overcome quenching caused by aggregation; the luminous efficiency and the service life of the device are improved; and on the other hand, the material also has relatively proper charge transmission capability, and has relatively high energy level matching degree with a main body material and other functional layer materials, so that the luminous efficiency and the service life of the device are further improved and prolonged.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to a boron-nitrogen heterocyclic compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have shown broad application potential in the display and lighting fields due to their advantages such as being lightweight, ultra-thin, having a wide viewing angle, fast response, wide temperature range applicability, low power consumption, high efficiency, high color purity, clear display, and flexible characteristics. They are a widely recognized and promising technology.

[0003] A typical OLED device includes a cathode, an anode, and a multilayered functional structure between them: a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The emissive layer contains guest material that serves as the light-emitting center. Under an applied current, holes and electrons are injected from the anode and cathode, respectively, and recombine in the emissive layer to form excitons. These excitons migrate under the influence of an electric field, transferring energy to the guest material, causing electrons in its molecules to transition from the ground state to an excited state. Subsequently, the electrons return from the unstable excited state to the ground state, releasing energy in the form of light, thus achieving light emission.

[0004] Guest materials are mainly divided into two categories: fluorescence and phosphorescence. Traditional OLED fluorescent materials are limited by the radiative transition from the triplet energy level to the ground state, and their internal quantum efficiency is only up to 25%. While phosphorescent materials can achieve 100% internal quantum efficiency, they mostly rely on precious metals, resulting in drawbacks such as high cost and insufficient color purity.

[0005] In recent years, thermally activated delayed fluorescence materials (MR-TADF) with multiple resonance effects have become a research hotspot in the OLED field due to their combination of high efficiency and narrow spectral emission characteristics. Unlike traditional fluorescent materials that rely on localized state emission, TADF emission mainly originates from energy level transitions in intramolecular charge-transfer states. Currently, most TADF molecules employ a split DA structure where electron donors and electron acceptors are connected in a conjugated or non-conjugated manner. However, such structures are often accompanied by significant configurational changes between the ground and excited states and rich molecular vibrational modes, resulting in generally broad emission spectra, with full width at half maximum (FWHM) often exceeding 100 nm. While the broad spectrum is suitable for lighting needs, it is difficult to meet the high color purity requirements of display technology. Therefore, developing TADF materials with narrow spectral characteristics has become an important research direction in this field. Summary of the Invention

[0006] To solve the above-mentioned technical problems, the present invention provides a boron-nitrogen heterocyclic compound having the structure shown in formula (I):

[0007] Wherein, X, Y, and Z are independently selected from one of the following: none, single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; R1, R2, and R3 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by fusion of substituted or unsubstituted C3-C12 aliphatic rings and C6-C30 aromatic rings. R1 and R2 can be linked together to form a ring. The rings A, B, C, D, E, and F are independently selected from one of the following: substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted C6-C30 heteroaromatic rings, and substituted or unsubstituted C3-C10 saturated or unsaturated aliphatic rings. Each time v appears, it is selected from N or CR, either the same or different. v The R mentioned v Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. v Can be connected to form a loop, or R v It connects to the carbon atom on ring A to form a ring; The Ar is selected from the group represented by formula (IA) or formula (IB):

[0008] Wherein, the ring G is selected from one of the substituted or unsubstituted C3~C10 aliphatic rings; The R is selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time u appears, it is selected from N or CR, either the same or different. u The R mentioned uEach time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. u They can be connected to form a ring; The L is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0009] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains one of the boron-nitrogen heterocyclic compounds described in the present invention.

[0010] Beneficial effects: The boron-nitrogen heterocyclic compounds provided by this invention have, on the one hand, large steric hindrance, high rigidity, and low molecular vibration, enabling narrow-spectrum emission and improving the color purity of light. They also increase the distance between molecules, reduce intermolecular forces, and decrease intermolecular overlap, thereby overcoming quenching caused by aggregation and improving the luminous efficiency and lifespan of the device. On the other hand, they also have appropriate charge transport capabilities and high energy level matching with the host material and other functional layer materials, further improving the luminous efficiency and lifespan of the device. Detailed Implementation

[0011] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0012] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes 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.

[0013] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0014] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0015] In this invention, "silyl group" refers to a -SiH3 group, and "substituted or unsubstituted silyl group" means that one or more H atoms on the silyl group are substituted or unsubstituted. The "substituted or unsubstituted silyl group" can be formed from -Si(R... k )3 indicates that each R k The groups are selected, either identically or differently, 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 groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The groups are selected, either identically or differently, from the following: hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, and substituted or unsubstituted C6-C60 aryl groups. 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, 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, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinoline. Preferably, the substituted silane alkyl group specifically includes, but is not limited to, trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, vinyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, phenyldimethylsilane alkyl, diphenylpyridylsilane alkyl, phenyldipyridylsilane alkyl, tripyridylsilane alkyl, etc. The aforementioned substituted silane alkyl group is preferably trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, or phenyldimethylsilane alkyl.

[0016] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0017] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0018] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The cycloalkenyl groups described above are preferably cyclopentenyl or cyclohexenyl.

[0019] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0020] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0021] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include furanyl, thiopheneyl, pyrroloyl, imidazoleyl, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiopheneyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiopheneyl, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazoyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, o-phenanthrolinel, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, or o-phenanthroline.

[0022] The monovalent group formed by the fusion of an aromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkane, cycloene, cycloyne) fused with an aromatic ring. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. It may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto. The aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms. It may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of aliphatic and aromatic rings may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, and naphthocyclohexyl.

[0023] The monovalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkanes, cycloalkenes, cycloalkynes) fused with a heteroaromatic ring. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. It can include furanyl, thiophene, pyrrole, imidazolyl, pyridyl, pyrimidine, benzothiophene, benzofuranyl, indole, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodi... Benzothiophene, carbazole, benzocarbazole, acridine, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiayl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, etc., but not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of an aliphatic ring and a heteroaromatic ring may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidocyclopentyl, pyrimidocyclohexyl, etc., but not limited thereto.

[0024] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0025] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0026] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0027] The divalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of a heteroaromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. The above description of groups formed by the fusion of a heteroaromatic ring and an aliphatic ring can be applied, the difference being that the divalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring is a divalent group.

[0028] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0029] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, substituted or unsubstituted silyl, 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: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, cyclopentane, 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, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene The following substances are used: deuterated 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-phenylcarbazolyl, benzofuranyl, benzothiophene, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzoxazolyl, benzothiazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the multiple substituents may be the same or different from each other, and two adjacent substituents may be linked together to form a ring.

[0030] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any optional position on the ring.

[0031] Any one of the points. For example, Can represent , , . Can represent , , ; Can represent , , , , , , , , , And so on.

[0032] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site 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 , , . Can represent or And so on.

[0033] The linked ring structures described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic rings) refer to groups connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0034] .

[0035] 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 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.

[0036] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0037] The statement that a certain layer is located "above" another layer or electrode in this invention can be interpreted as being directly above another layer or electrode, or it can be that other layer structures exist in between.

[0038] The term "a certain layer" in this invention, which is "between" two layers, two electrodes, or one layer and an electrode, can be interpreted as the only layer structure between the two, or as having one or more layer structures between them.

[0039] This invention provides a boron-nitrogen heterocyclic compound having the structure shown in formula (I):

[0040] Wherein, X, Y, and Z are independently selected from one of the following: none, single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; R1, R2, and R3 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by fusion of substituted or unsubstituted C3-C12 aliphatic rings and C6-C30 aromatic rings. R1 and R2 can be linked together to form a ring. The rings A, B, C, D, E, and F are independently selected from one of the following: substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted C6-C30 heteroaromatic rings, and substituted or unsubstituted C3-C10 saturated or unsaturated aliphatic rings. Each time v appears, it is selected from N or CR, either the same or different. v The R mentioned vEach time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. v Can be connected to form a loop, or R v It connects to the carbon atom on ring A to form a ring; The Ar is selected from the group represented by formula (IA) or formula (IB):

[0041] Wherein, the ring G is selected from one of the substituted or unsubstituted C3~C10 aliphatic rings; The R is selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time u appears, it is selected from N or CR, either the same or different. u The R mentioned u Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. u They can be connected to form a ring; The L is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0042] Preferably, the substituents in "substituted or unsubstituted" are independently selected from deuterium atom; fluorine atom; cyano group; methyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; ethyl group; n-propyl group; isopropyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; n-butyl group; sec-butyl group; isobutyl group; tert-butyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; and groups substituted or unsubstituted by one or more of deuterium atom, methyl group, ethyl group, isopropyl group, and tert-butyl group. The following groups, substituted or unsubstituted, are included: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; groups substituted or unsubstituted by one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; phenyl. Naphthyl, anthracene, phenanthrene, phenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl; methyl, ethyl, n-propyl, isopropyl, n-butyl One or more of the following substituents, tert-butyl, phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl, anthraceneyl, phenanthrene, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and 9,9-dimethylfluorenyl, may be substituted or unsubstituted silyl groups, wherein when there are multiple substituents, the multiple substituents may be the same or different.

[0043] Preferably, the boron-nitrogen heterocyclic compound has one of the structures shown in formulas (II-A) to (II-R):

[0044] Wherein, X1 and Y1 are independently selected from one of O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3.

[0045] Preferably, the boron-nitrogen heterocyclic compound has one of the structures shown in formulas (III-A) to (III-P): .

[0046] Preferably, rings A, B, C, D, E, and F are independently selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted anthracene rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted triphenylene rings, substituted or unsubstituted benzo[a]cyclopropane rings, substituted or unsubstituted benzo[a]cyclobutane rings, substituted or unsubstituted benzo[a]cyclopentane rings, substituted or unsubstituted benzo[a]cyclohexane rings, substituted or unsubstituted benzo[a]cycloheptane rings, substituted or unsubstituted pyridine rings, substituted or unsubstituted pyrazine rings, substituted or unsubstituted pyridazine rings, substituted or unsubstituted quinoline rings, substituted or unsubstituted isoquinoline rings, substituted or unsubstituted quinazoline rings, substituted or unsubstituted quinoxaline rings, substituted or unsubstituted benzo[a]furan rings, and substituted or unsubstituted... The substituted benzothiophene ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted dibenzothiophene ring, substituted or unsubstituted benzonaphthofuran ring, substituted or unsubstituted benzonaphthothiophene ring, substituted or unsubstituted indole ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted fluorene ring, substituted or unsubstituted benzoxazole ring, substituted or unsubstituted benzothiazole ring, substituted or unsubstituted benzimidazole ring, substituted or unsubstituted cyclopropane ring, substituted or unsubstituted cyclobutane ring, substituted or unsubstituted cyclopentane ring, substituted or unsubstituted cyclohexane ring, substituted or unsubstituted cycloheptane ring, substituted or unsubstituted cyclopropylene ring, substituted or unsubstituted cyclobutene ring, substituted or unsubstituted cyclopentene ring, substituted or unsubstituted cyclohexene ring, substituted or unsubstituted cycloheptene ring.

[0047] More preferably, the substituents in "substituted or unsubstituted" are selected, each time appearing, from the same or different groups: deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl Triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted benzene The following are substituted or unsubstituted phenyl groups: phenyl with fluorine atom substituted, phenyl with cyano substituted, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. The following groups are included: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0048] Preferred, R v It is linked to the carbon atom on ring A to form a ring, including Chinese R v It connects to a carbon atom on ring A to form a ring, thereby forming one of the following structures:

[0049] Ra, Rb, and Rc are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by fusion of substituted or unsubstituted C3-C12 aliphatic rings and C6-C30 aromatic rings. Ra and Rb can be linked together to form a ring.

[0050] Preferably, Ra, Rb, and Rc are independently selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl Deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridine The following groups, substituted or unsubstituted, are pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, and one or more of the groups shown in formulas (IA) and (IB): phenyl, biphenyl, naphthyl, anthraceneyl, phenanthrene. The active ingredients are triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane, wherein Ra and Rb are linked together to form a ring, preferably linked together to form a fluorene ring.

[0051] When Ra and Rb are linked to form a ring, they are either substituted or unsubstituted by the corresponding groups in Ra and Rb.

[0052] More preferably, R v It is linked to the carbon atom on ring A to form a ring, including Chinese R v It connects to a carbon atom on ring A to form a ring, thereby forming one of the following structures:

[0053] Wherein, each occurrence of x is selected from N or CR, either identically or differently. x The R mentioned xEach time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. x They can be connected to form a ring.

[0054] Preferred, R x Selected from, or not selected from, deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl di Phenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted The following groups, substituted or unsubstituted, are derived from the following groups: phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane: phenyl One of the following: biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0055] Preferably, in each structure, at most three, at most two, or at most one x are selected from N.

[0056] Preferably, R1, R2, and R3 are independently selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl Silyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl The following groups, substituted or unsubstituted, are found in the following groups: anthraceneyl, phenanthreneyl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane: phenyl, biphenyl, naphthyl, anthraceneyl. The R1 and R2 are selected from phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane, wherein the R1 and R2 are linked together to form a ring.

[0057] Preferably, the R vEach time it appears, the same or different elements are selected from hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornyl; deuterium atom Fungi, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The phenyl group is substituted with one or more of the following: trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiaphene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0058] Preferably, the Ar is selected from one of the following groups:

[0059] Wherein, a1 is selected from 0, 1, 2, 3 or 4; b1 is selected from 0, 1, 2, 3, 4, 5 or 6; c1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; d1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; e1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; The R mentioned 11Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

[0060] Preferably, the R u Each time it appears, the same or different elements are selected from hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; Fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl The following are substituted or unsubstituted phenyl groups: silyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraceneyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. The following groups are: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, or one of the following, or two adjacent R groups. u Those that can be linked together to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, carbazole ring, benzofuran ring, benzothiophene ring.

[0061] Preferably, the R 11Each time it appears, the same or different elements are selected from one of the following: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornenealkyl.

[0062] Preferably, R is selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyldiphenylsilyl. Methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl. Naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, one or more substituted or unsubstituted groups of the following: phenyl, biphenyl One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0063] Preferably, among the multiple u in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0064] Preferably, the L is selected from a single bond or one of the following groups:

[0065] Wherein, the a 101Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

[0066] Preferably, the R 101Each time it appears, the same or different elements are selected from hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornyl; deuterium atom Fungi, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The phenyl group is substituted with one or more of the following: trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiaphene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0067] Preferably, the R 102 Each time it appears, the same or different elements are selected from one of the following: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornenealkyl.

[0068] Preferably, the boron-nitrogen heterocyclic compound is selected from one of the following compounds: .

[0069] The boron-nitrogen heterocyclic compound represented by formula (I) of this invention can be prepared by the following synthetic route:

[0070] First, compound (Y1) and compound (Y2) undergo a cyclization reaction to obtain intermediate (M); then, intermediate (M) undergoes a boron ring synthesis reaction to obtain the target compound (I).

[0071] The boron-nitrogen heterocyclic compound represented by formula (I) of this invention can also be prepared via the following synthetic route:

[0072] First, compound (Y1) is synthesized into an intermediate (N) through a boron ring synthesis reaction; then, the intermediate (N) and compound (Y2) undergo a cyclization reaction to obtain the target compound (I).

[0073] Wherein, X, Y, Z, ring A, ring B, ring C, ring D, ring E, ring F, v, Ar, and L are all as described in this invention.

[0074] Q1 and Q2 are independently selected from fluorine atoms, chlorine atoms, bromine atoms or iodine atoms.

[0075] The above synthetic route employs reaction types commonly used in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation method utilizes readily available raw materials, has a simple process, and yields excellent results. This invention can also employ other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0076] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains the boron-nitrogen heterocyclic compound described in the present invention.

[0077] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer contains the boron-nitrogen heterocyclic compound described in this invention.

[0078] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0079] Preferably, the light-emitting layer comprises a first host material, a second host material, and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0080] Preferably, the luminescent layer comprises a host material, a sensitizer, and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0081] Preferably, the light-emitting layer comprises a first host material, a second host material, a sensitizer, and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0082] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Alternatively, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer.

[0083] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4''-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1~HT-18, compounds p-1~p-5, but not limited to these.

[0084] .

[0085] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a value of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0086] The light-emitting auxiliary layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1 '-Biphenyl]-4-amine, compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0087] The luminescent layer of this invention comprises a guest material and a host material, and a dual-host material formed from two host materials can be used. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, aromatic amine compounds, etc. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 9,10-bis(2-naphthyl)anthracene (ADN), etc., but is not limited to these. The guest material includes, but is not limited to, aromatic amine derivatives, boron compounds, metal complexes, etc. Specific examples may include, but are not limited to, tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), and the boron-nitrogen heterocyclic compounds described in this invention. Preferably, the guest material is selected from the boron-nitrogen heterocyclic compounds described in this invention.

[0088] The light-emitting layer of this invention may further include a sensitizer. The sensitizer refers to a material that enables the light-emitting material in the light-emitting layer to fully utilize electroexcitons, thereby improving the performance of the OLED device. In organic electroluminescent devices, the sensitizer may perform functions such as exciton trapping, exciton conversion, and exciton transfer. The sensitizer is mainly classified into phosphorescent sensitizers, TADF sensitizers, and excitocomplex sensitizers. Examples of phosphorescent sensitizers include iridium complexes and platinum complexes. TADF sensitizers mainly use TADF materials, and excitocomplex sensitizers consist of donor and acceptor materials.

[0089] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0090] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0091] The electron transport 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. It can utilize high-electron-transporting materials such as aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, and polymers. Examples of electron transport materials for the electron transport layer include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), and 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited to these.

[0092] The hole blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The hole blocking material used in the hole blocking layer requires a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the hole blocking material must be lower than that of the host material of the emissive layer to effectively block holes. Further, the electron mobility of the hole blocking layer material used is 10... -6 cm 2A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq, but these are not limited to these.

[0093] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0094] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0095] The capping layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. 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, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, and compounds CP-1 to CP-7, but are not limited thereto.

[0096]

[0097] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0098] The thickness of each of the aforementioned organic layers is typically between 1 nanometer and 100 micrometers, preferably between 5 nanometers and 1000 nanometers, and more preferably between 5 nanometers and 200 nanometers. The thickness of the anode and cathode is adjusted according to the required transparency.

[0099] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0100] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0101] The mass spectrometry of the compounds of this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments Ltd., UK, 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.

[0102] [Synthetic Example 1] Preparation of intermediates DD-8, DD-18, DD-25, DD-94, DD-104, DD-149, DD-280, DD-349, DD-355, DD-405, DD-491, and DD-693:

[0103] Under nitrogen protection, aa-8 (25.91 g, 100 mmol), bb-8 (20.03 g, 100 mmol), and sodium tert-butoxide (14.42 g, 150 mmol) dissolved in 600 mL toluene were added to a reaction flask. Pd₂(dba)₃ (0.92 g, 1.00 mmol) and X-Phos (1.43 g, 3.00 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. 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. Recrystallization from toluene yielded intermediate DD-8 (28.46 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.83%. Mass spectrometry m / z: 379.1949 (theoretical value: 379.1936).

[0104] Following the method described above, the following intermediates were synthesized by equimolar substitution of raw materials aa-8 and bb-8.

[0105] [Synthetic Example 2] Preparation of intermediates DD-15, DD-169, DD-174, DD-175, DD-224, DD-325, DD-660, and DD-684:

[0106] Under nitrogen protection, aa-15 (25.91 g, 100.00 mmol), cc-15 (37.33 g, 100.00 mmol), and K2CO3 (27.64 g, 200.00 mmol) were dissolved in 50 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.90 g, 2.00 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, 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 give intermediate DD-15 (34.04 g, 80% yield); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 425.1795 (theoretical value: 425.1780).

[0107] Following the method described above, the following intermediates were synthesized by equimolar substitution of raw materials aa-15 and cc-15.

[0108] [Synthetic Example 3] Preparation of intermediate DD-16:

[0109] Under nitrogen protection, aa-16 (33.80 g, 100 mmol), bb-16 (17.12 g, 200 mmol), and sodium tert-butoxide (28.83 g, 300 mmol) dissolved in 600 mL toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (1.83 g, 2.00 mmol) and X-Phos (1.91 g, 4.00 mmol) were then added. The mixture of the above reactants was heated under reflux for 7 h. 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. Recrystallization from toluene yielded intermediate DD-16 (36.31 g, 70% yield). HPLC analysis showed a solid purity ≥ 99.82%. Mass spectrometry m / z: 518.2369 (theoretical value: 518.2358).

[0110] [Synthetic Example 4] Preparation of intermediate DD-194:

[0111] Under nitrogen protection, hh-194 (37.52 g, 150.00 mmol), kk-194 (39.03 g, 150.00 mmol), and K2CO3 (41.46 g, 300.00 mmol) were dissolved in 650 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (3.37 g, 3.00 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, 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 give intermediate II-194 (36.87 g, yield 81%); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 303.1999 (theoretical value: 303.1987).

[0112] Under nitrogen protection, II-194 (30.34 g, 100 mmol), dd-194 (28.29 g, 100 mmol), and sodium tert-butoxide (14.42 g, 150 mmol) dissolved in 450 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (1.37 g, 1.50 mmol) and X-Phos (1.43 g, 3.00 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.5 h. 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. Recrystallization from toluene yielded intermediate HH-194 (34.38 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.83%. Mass spectrometry m / z: 457.1427 (theoretical value: 457.1405).

[0113] Under nitrogen protection, HH-194 (27.51 g, 60.00 mmol), ee-194 (18.37 g, 60.00 mmol), and K2CO3 (16.59 g, 120.00 mmol) were dissolved in 500 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.35 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, 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 give intermediate DD-194 (26.77 g, 80% yield); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 557.2730 (theoretical value: 557.2719).

[0114] [Synthetic Example 5] Preparation of intermediates DD-200, DD-226, DD-237, DD-245, DD-255, DD-326, DD-526, and DD-698:

[0115] Under nitrogen protection, bb-16 (17.12 g, 100 mmol), dd-200 (28.29 g, 100 mmol), and sodium tert-butoxide (14.42 g, 150 mmol) dissolved in 350 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (1.37 g, 1.50 mmol) and X-Phos (1.43 g, 3.00 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. 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. Recrystallization from toluene yielded intermediate HH-200 (24.47 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.83%. Mass spectrometry m / z: 325.0480 (theoretical value: 325.0466).

[0116] Under nitrogen protection, HH-200 (19.57 g, 60.00 mmol), ee-194 (18.37 g, 60.00 mmol), and K2CO3 (16.59 g, 120.00 mmol) were dissolved in 650 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.35 g, 1.20 mmol) was added with stirring, and the mixture was heated to reflux for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol (9:1) to give intermediate DD-200 (34.04 g, 80% yield); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 425.1793 (theoretical value: 425.1780).

[0117] Following the method described above, the following intermediates were synthesized by equimolar substitution of raw materials bb-16, dd-200, and ee-194.

[0118] [Synthetic Example 6] Preparation of Compound 8:

[0119] Preparation of intermediate CC-8: 800 mL of anhydrous N,N-dimethylformamide solution containing AA-8 (34.11 g, 150.00 mmol) was slowly added dropwise to 375 mL of anhydrous N,N-dimethylformamide solution containing cesium carbonate (97.75 g, 300.00 mmol). After stirring at room temperature for 2 h, 350 mL of anhydrous N,N-dimethylformamide solution containing BB-8 (50.16 g, 300.00 mmol) was added dropwise. The reaction system was stirred at 160 °C for 24 h. The mixture was then cooled to room temperature and poured into 3.5 L of ice water. The solid was filtered off, dried under vacuum, and purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent, yielding intermediate CC-8 (54.79 g, 70%). HPLC analysis showed the solid purity to be ≥99.65%. Mass spectrometry m / z: 520.0353 (theoretical value: 520.0342).

[0120] Preparation of intermediate EE-8: CC-8 (52.18 g, 100.00 mmol) was dissolved in 500 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 74.4 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 3 h, 280 mL of tetrahydrofuran solution of the starting material DD-8 (41.75 g, 110 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. The aqueous layer was then separated and extracted with dichloromethane. The sample was dried over sodium sulfate, filtered, and concentrated by rotary evaporation followed by column chromatography to obtain intermediate EE-8 (53.09 g, 66%). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 803.3081 (theoretical value: 803.3067). Preparation of compound 8: Under a nitrogen atmosphere, a hexane solution (750 mL) containing 54 mL of tert-butyllithium was slowly added to a 350 mL tert-butylbenzene solution at 0 °C containing intermediate EE-8 (32.18 g, 40.00 mmol). The mixture was slowly heated to 60 °C and stirred for 2 h. Hexane was then removed under vacuum, and the mixture was cooled to -40 °C. 7.5 mL of boron tribromide (80 mmol) was added, and the reaction mixture was stirred at room temperature for 30 min. Next, 15.1 mL of N,N-diisopropylethylamine (80 mL) was added at 0 °C. The reaction mixture was then heated to 120 °C and stirred for 4 h, followed by cooling to room temperature. 25 mL of methanol was added to quench any remaining boron tribromide. The reaction mixture was concentrated under vacuum, purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent, yielding compound 8 (8.40 g, 27%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 777.3325 (theoretical value: 777.3315). Theoretical elemental content (%) C 57 H 40 BN3: C, 88.02; H, 5.18; N, 5.40. Actual element content (%): C, 88.05; H, 5.19; N, 5.35.

[0121] [Synthetic Example 7] Preparation of Compound 15:

[0122] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-15, respectively, with other steps remaining unchanged, to obtain compound 15 (11.74 g, yield 28%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1047.5651 (theoretical value: 1047.5663). Theoretical elemental content (%) C 77 H 70 BN3: C, 88.23; H, 6.73; N, 4.01. Actual element content (%): C, 88.24; H, 6.75; N, 4.06.

[0123] [Synthetic Example 8] Preparation of Compound 16:

[0124] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-16, respectively, with other steps remaining unchanged, to obtain compound 16 (11.87 g, yield 26%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1140.6255 (theoretical value: 1140.6241). Theoretical elemental content (%) C 83H 77 BN4: C, 87.34; H, 6.80; N, 4.91. Actual element content (%): C, 87.33; H, 6.75; N, 4.94.

[0125] [Synthetic Example 9] Preparation of Compound 18:

[0126] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-18, respectively, with other steps remaining unchanged, to obtain compound 18 (11.22 g, yield 28%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1001.5828 (theoretical value: 1001.5819). Theoretical elemental content (%) C 73 H 72 BN3: C, 87.49; H, 7.24; N, 4.19. Actual element content (%): C, 87.53; H, 7.25; N, 4.14.

[0127] [Synthetic Example 10] Preparation of Compound 25:

[0128] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-25 and DD-25, respectively, while other steps remained unchanged, yielding compound 25 (13.28 g, yield 26%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1275.6620 (theoretical value: 1275.6602). Theoretical elemental content (%) C 95 H 82 BN3: C, 89.39; H, 6.48; N, 3.29. Actual element content (%): C, 89.34; H, 6.45; N, 3.24.

[0129] [Synthetic Example 11] Preparation of Compound 29:

[0130] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-29 and DD-29, respectively, while other steps remained unchanged, yielding compound 29 (9.72 g, yield 25%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 971.5361 (theoretical value: 971.5350). Theoretical elemental content (%) C 71 H 66BN3: C, 87.72; H, 6.84; N, 4.32. Actual element content (%): C, 87.70; H, 6.85; N, 4.34.

[0131] [Synthetic Example 12] Preparation of Compound 45:

[0132] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-45 and DD-25, respectively, while other steps remained unchanged, yielding compound 45 (11.64 g, yield 24%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1211.3881 (theoretical value: 1211.3894). Theoretical elemental content (%) C 87 H 50 BN3O4: C, 86.20; H, 4.16; N, 3.47. Actual element content (%): C, 86.21; H, 4.15; N, 3.44.

[0133] [Synthetic Example 13] Preparation of Compound 94:

[0134] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-94, respectively, while other steps remained unchanged, yielding compound 94 (10.90 g, yield 26%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1047.5680 (theoretical value: 1047.5663). Theoretical elemental content (%) C 77 H 70 BN3: C, 88.23; H, 6.73; N, 4.01. Actual element content (%): C, 88.21; H, 6.75; N, 4.04.

[0135] [Synthetic Example 14] Preparation of Compound 104:

[0136] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-104 and DD-104, respectively, with other steps remaining unchanged, to obtain compound 104 (12.79 g, yield 29%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1101.5840 (theoretical value: 1101.5823). Theoretical elemental content (%) C 81 H 36 D 20BN3: C, 88.26; H, 6.95; N, 3.81. Actual element content (%): C, 88.21; H, 6.93; N, 3.84.

[0137] [Synthetic Example 15] Preparation of Compound 149:

[0138] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-149, respectively, with other steps remaining unchanged, to obtain compound 149 (10.63 g, yield 26%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1021.5517 (theoretical value: 1021.5506). Theoretical elemental content (%) C 75 H 68 BN3: C, 88.13; H, 6.71; N, 4.11. Actual element content (%): C, 88.11; H, 6.73; N, 4.14.

[0139] [Synthetic Example 16] Preparation of Compound 169:

[0140] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-15, respectively, while other steps remained unchanged, yielding compound 169 (12.16 g, yield 29%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1047.5677 (theoretical value: 1047.5663). Theoretical elemental content (%) C 77 H 70 BN3: C, 88.23; H, 6.73; N, 4.01. Actual element content (%): C, 88.21; H, 6.75; N, 4.04.

[0141] [Synthetic Example 17] Preparation of Compound 174:

[0142] According to the preparation method in Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-174, respectively, while other steps remained unchanged, to obtain compound 174 (10.78 g, yield 25%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1077.6136 (theoretical value: 1077.6132). Theoretical elemental content (%) C 79 H 76BN3: C, 88.00; H, 7.10; N, 3.90. Actual element content (%): C, 88.01; H, 7.15; N, 3.94.

[0143] [Synthetic Example 18] Preparation of Compound 175:

[0144] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-175, respectively, with other steps remaining unchanged, to obtain compound 175 (10.79 g, yield 24%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1123.5988 (theoretical value: 1123.5976). Theoretical elemental content (%) C 83 H 74 BN3: C, 88.67; H, 6.63; N, 3.74. Actual element content (%): C, 88.71; H, 6.65; N, 3.72.

[0145] [Synthetic Example 19] Preparation of Compound 194:

[0146] Following the preparation method of Synthesis Example 6, DD-8 in Synthesis Example 6 was replaced with DD-194, with other steps remaining unchanged, to obtain compound 194 (9.56 g, yield 25%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 955.4087 (theoretical value: 955.4098). Theoretical elemental content (%) C 71 H 50 BN3: C, 89.20; H, 5.27; N, 4.40. Actual element content (%): C, 89.21; H, 5.25; N, 4.42.

[0147] [Synthetic Example 20] Preparation of Compound 200:

[0148] Preparation of intermediate BB'-200: 950 mL of anhydrous N,N-dimethylformamide solution containing AA-8 (45.49 g, 200.00 mmol) was slowly added dropwise to 450 mL of anhydrous N,N-dimethylformamide solution containing cesium carbonate (130.33 g, 400.00 mmol). After stirring at room temperature for 2 h, 280 mL of anhydrous N,N-dimethylformamide solution containing BB-15 (55.89 g, 200.00 mmol) was added dropwise. The reaction system was stirred at 150 °C for 24 h. The mixture was then cooled to room temperature, poured into 3 L of ice water, and the solid was filtered off. The solid was dried under vacuum and purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent, yielding intermediate BB'-200 (73.03 g, 75%). HPLC analysis showed the solid purity to be ≥99.85%. Mass spectrometry m / z: 485.0934 (theoretical value: 485.0921).

[0149] Preparation of intermediate CC-200: 800 mL of anhydrous N,N-dimethylformamide solution containing intermediate BB'-200 (63.29 g, 130.00 mmol) was slowly added dropwise to 330 mL of anhydrous N,N-dimethylformamide solution containing cesium carbonate (84.71 g, 260.00 mmol). After stirring at room temperature for 2 h, 200 mL of anhydrous N,N-dimethylformamide solution containing starting material GG-200 (41.52 g, 130.00 mmol) was added dropwise. The reaction system was stirred at 150 °C for 24 h. The mixture was then cooled to room temperature and poured into 2.5 L of ice water. The solid was filtered off, dried under vacuum, and purified by column chromatography using petroleum ether:dichloromethane (9:1 v / v) as the eluent to obtain intermediate CC-200 (71.55 g, 70%). HPLC analysis showed a solid purity ≥99.72%. Mass spectrometry m / z: 784.2233 (theoretical value: 784.2220).

[0150] Preparation of intermediate EE-200: CC-200 (62.90 g, 80.00 mmol) was dissolved in 500 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 59.5 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 3 h, 200 mL of tetrahydrofuran solution of the starting material DD-200 (38.30 g, 90.00 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. The aqueous layer was then separated and extracted with dichloromethane. The sample was dried over sodium sulfate, filtered, and concentrated by rotary evaporation followed by column chromatography to obtain intermediate EE-200 (57.97 g, 65%). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 1113.4773 (theoretical value: 1113.4789).

[0151] Preparation of compound 200: Under a nitrogen atmosphere, a hexane solution (750 mL) containing 54 mL of tert-butyllithium was slowly added to a 350 mL tert-butylbenzene solution at 0 °C containing intermediate EE-200 (39.02 g, 35.00 mmol). The mixture was slowly heated to 60 °C and stirred for 2 h. Hexane was then removed under vacuum, and the mixture was cooled to -40 °C. 6.6 mL of boron tribromide (70 mmol) was added, and the reaction mixture was stirred at room temperature for 30 min. Next, 12 mL of N,N-diisopropylethylamine (70 mL) was added at 0 °C. The reaction mixture was then heated to 120 °C and stirred for 4 h, followed by cooling to room temperature. 23 mL of methanol was added to the reaction mixture to quench any remaining boron tribromide. The reaction system was concentrated under vacuum, purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent, yielding compound 200 (9.52 g, 25%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1087.5050 (theoretical value: 1087.5037). Theoretical elemental content (%) C 81 H 62 BN3: C, 89.40; H, 5.74; N, 3.86. Actual element content (%): C, 89.39; H, 5.79; N, 3.88.

[0152] [Synthetic Example 21] Preparation of Compound 210:

[0153] According to the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-210, DD-169, and GG-210, respectively, while other steps remained unchanged, to obtain compound 210 (10.78 g, yield 26%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1183.4321 (theoretical value: 1183.4309). Theoretical elemental content (%) C 87 H 54 BN3O2: C, 88.24; H, 4.60; N, 3.55. Actual element content (%): C, 88.21; H, 4.65; N, 3.52.

[0154] [Synthetic Example 22] Preparation of Compound 217:

[0155] According to the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-15, DD-169, and GG-217, respectively, while other steps remained unchanged, to obtain compound 217 (10.19 g, yield 23%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1265.5579 (theoretical value: 1265.5568). Theoretical elemental content (%) C 93 H 68 BN5: C, 88.20; H, 5.41; N, 5.53. Actual element content (%): C, 88.21; H, 5.45; N, 5.52.

[0156] [Synthetic Example 23] Preparation of Compound 224:

[0157] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-224 and DD-224, respectively, with other steps remaining unchanged, to obtain compound 224 (11.40 g, yield 23%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1237.5221 (theoretical value: 1237.5209). Theoretical elemental content (%) C 83 H 76 BN3Si4: C, 80.48; H, 6.18; N, 3.39. Actual elemental content (%): C, 80.47; H, 6.15; N, 3.42.

[0158] [Synthetic Example 24] Preparation of Compound 226:

[0159] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with GG-200 and DD-226, respectively, with other steps remaining unchanged, to obtain compound 226 (12.73 g, yield 27%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1177.4555 (theoretical value: 1177.4567). Theoretical elemental content (%) C 89 H 56 BN3: C, 90.73; H, 4.79; N, 3.57. Actual element content (%): C, 90.77; H, 4.75; N, 3.58.

[0160] [Synthetic Example 25] Preparation of Compound 230:

[0161] According to the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-169 and GG-230, respectively, while other steps remained unchanged, to obtain compound 230 (9.07 g, yield 25%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1035.4738 (theoretical value: 1035.4724). Theoretical elemental content (%) C 77 H 58 BN3: C, 89.26; H, 5.64; N, 4.06. Actual element content (%): C, 89.21; H, 5.65; N, 4.02.

[0162] [Synthetic Example 26] Preparation of Compound 237:

[0163] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-237 and GG-237, respectively, with other steps remaining unchanged, to obtain compound 237 (8.29 g, yield 24%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 986.4533 (theoretical value: 986.4520). Theoretical elemental content (%) C 72 H 55 BN4: C, 87.61; H, 5.62; N, 5.68. Actual element content (%): C, 87.62; H, 5.65; N, 5.72.

[0164] [Synthetic Example 27] Preparation of Compound 245:

[0165] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-15 and DD-245, respectively, while other steps remained unchanged, yielding compound 245 (10.10 g, yield 23%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1097.5829 (theoretical value: 1097.5819). Theoretical elemental content (%) C 81 H 72 BN3: C, 88.58; H, 6.61; N, 3.83. Actual element content (%): C, 88.57; H, 6.65; N, 3.85.

[0166] [Synthetic Example 28] Preparation of Compound 254:

[0167] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-254 and DD-254, respectively, with other steps remaining unchanged, to obtain compound 254 (11.62 g, yield 25%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1161.4681 (theoretical value: 1161.4690). Theoretical elemental content (%) C 83 H 56 BN7: C, 85.78; H, 4.86; N, 8.44. Actual element content (%): C, 85.77; H, 4.84; N, 8.45.

[0168] [Synthetic Example 29] Preparation of Compound 255:

[0169] According to the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-255 and GG-255, respectively, while other steps remained unchanged, to obtain compound 255 (8.29 g, yield 23%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1029.4785 (theoretical value: 1029.4768). Theoretical elemental content (%) C 75 H 52 D4BN3O: C, 87.45; H, 5.87; N, 4.08. Actual element content (%): C, 87.42; H, 5.85; N, 4.03.

[0170] [Synthetic Example 30] Preparation of Compound 256:

[0171] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-169 and GG-256, respectively, with other steps remaining unchanged, to obtain compound 256 (10.08 g, yield 24%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1199.4491 (theoretical value: 1199.4478). Theoretical elemental content (%) C 85 H 62 D4BN3S: C, 85.05; H, 5.21; N, 3.50. Actual elemental content (%): C, 85.02; H, 5.25; N, 3.52.

[0172] [Synthetic Example 31] Preparation of Compound 267:

[0173] Preparation of intermediate CC-267: 850 mL of anhydrous N,N-dimethylformamide solution containing AA-267 (40.78 g, 150.00 mmol) was slowly added dropwise to 400 mL of anhydrous N,N-dimethylformamide solution containing cesium carbonate (97.75 g, 300.00 mmol). After stirring at room temperature for 2 h, 280 mL of anhydrous N,N-dimethylformamide solution containing BB-15 (83.83 g, 300.00 mmol) was added dropwise. The reaction system was stirred at 150 °C for 24 h. The mixture was then cooled to room temperature, poured into 3 L of ice water, and the solid was filtered off. The solid was dried under vacuum and purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent to obtain intermediate CC-267 (83.03 g, 70%). HPLC analysis showed the solid purity to be ≥99.88%. Mass spectrometry m / z: 788.2360 (theoretical value: 788.2341) Synthesis of intermediate EE-267: CC-267 (71.17 g, 90.00 mmol) was dissolved in 450 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 66.9 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 3 h, 350 mL of tetrahydrofuran solution of starting material DD-25 (69.19 g, 198 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with NaHCO3 aqueous solution. The aqueous layer was then separated and extracted with dichloromethane. The sample was dried over sodium sulfate, filtered, and concentrated by rotary evaporation followed by column chromatography to obtain intermediate EE-267 (58.31 g, 50%). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 1294.6872 (theoretical value: 1294.6852). Synthesis of compound 267: Under a nitrogen atmosphere, a hexane solution (750 mL) containing 54 mL of tert-butyllithium was slowly added to a 350 mL tert-butylbenzene solution at 0 °C containing intermediate EE-267 (45.35 g, 35.00 mmol). The mixture was slowly heated to 60 °C and stirred for 2 h. Hexane was then removed under vacuum, and the mixture was cooled to -40 °C. 6.6 mL of boron tribromide (70 mmol) was added, and the reaction mixture was stirred at room temperature for 30 min. Next, 12 mL of N,N-diisopropylethylamine (70 mL) was added at 0 °C. The reaction mixture was then heated to 120 °C and stirred for 4 h, before cooling to room temperature. 23 mL of methanol was added to the reaction mixture to quench any remaining boron tribromide. The reaction system was concentrated under vacuum, purified by column chromatography using petroleum ether:dichloromethane (v / v 10:1) as the eluent, yielding compound 267 (10.04 g, 22%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1302.6730 (theoretical value: 1302.6711). Theoretical elemental content (%) C 96 H 83 BN4: C, 88.45; H, 6.42; N, 4.30. Actual element content (%): C, 88.47; H, 6.44; N, 4.35.

[0174] [Synthetic Example 32] Preparation of Compound 280:

[0175] According to the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-280 and GG-280, respectively, while other steps remained unchanged, to obtain compound 280 (8.99 g, yield 23%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1115.5088 (theoretical value: 1115.5098). Theoretical elemental content (%) C 81 H 62 BN5: C, 87.16; H, 5.60; N, 6.27. Actual element content (%): C, 87.12; H, 5.65; N, 6.26.

[0176] [Synthetic Example 33] Preparation of Compound 325:

[0177] Following the preparation method of Synthesis Example 20, DD-200 in Synthesis Example 20 was replaced with DD-325, with other steps remaining unchanged, to obtain compound 325 (9.66 g, yield 25%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1103.4999 (theoretical value: 1103.4986). Theoretical elemental content (%) C 81 H 62 BN3O: C, 88.11; H, 5.66; N, 3.81. Actual element content (%): C, 88.12; H, 5.65; N, 3.86.

[0178] [Synthetic Example 34] Preparation of Compound 326:

[0179] Following the preparation method of Synthesis Example 6, BB-8 and DD-8 in Synthesis Example 6 were replaced with BB-326 and DD-326, respectively, with other steps remaining unchanged, to obtain compound 326 (9.45 g, yield 26%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 908.3632 (theoretical value: 908.3645). Theoretical elemental content (%) C 63 H 25 D 13 BN3OS: C, 83.25; H, 5.65; N, 4.62. Actual element content (%): C, 83.27; H, 5.64; N, 4.65.

[0180] [Synthetic Example 35] Preparation of Compound 349:

[0181] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-349 and GG-349, respectively, with other steps remaining unchanged, to obtain compound 349 (8.00 g, yield 24%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 951.4374 (theoretical value: 951.4360). Theoretical elemental content (%) C 69 H 54 BN3O: C, 87.05; H, 5.72; N, 4.41. Actual element content (%): C, 87.02; H, 5.75; N, 4.46.

[0182] [Synthetic Example 36] Preparation of Compound 355:

[0183] According to the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-25, DD-355, and GG-349, respectively, while other steps remained unchanged, to obtain compound 355 (9.00 g, yield 25%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1027.4688 (theoretical value: 1027.4673). Theoretical elemental content (%) C 75 H 58 BN3O: C, 87.62; H, 5.69; N, 4.09. Actual element content (%): C, 87.63; H, 5.65; N, 4.06.

[0184] [Synthetic Example 37] Preparation of Compound 364:

[0185] Following the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with GG-200, DD-104, and GG-349, respectively, with other steps remaining unchanged, to obtain compound 364 (8.94 g, yield 27%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 945.3899 (theoretical value: 945.3890). Theoretical elemental content (%) C 69 H 48 BN3O: C, 87.61; H, 5.11; N, 4.44. Actual element content (%): C, 87.63; H, 5.15; N, 4.46.

[0186] [Synthetic Example 38] Preparation of Compound 405:

[0187] According to the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-405, DD-405, and GG-349, respectively, while other steps remained unchanged, to obtain compound 405 (9.96 g, yield 28%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1015.3751 (theoretical value: 1015.3734). Theoretical elemental content (%) C 75 H 46 BN3O: C, 88.66; H, 4.56; N, 4.14. Actual element content (%): C, 88.63; H, 4.55; N, 4.16.

[0188] [Synthetic Example 39] Preparation of Compound 491:

[0189] Following the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-15, DD-491, and GG-491, respectively, while other steps remained unchanged, yielding compound 491 (8.80 g, yield 26%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 966.4477 (theoretical value: 966.4469). Theoretical elemental content (%) C 69 H 55 BN4O: C, 85.70; H, 5.73; N, 5.79. Actual element content (%): C, 85.66; H, 5.75; N, 5.76.

[0190] [Synthetic Example 40] Preparation of Compound 526:

[0191] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-526 and GG-526, respectively, with other steps remaining unchanged, to obtain compound 526 (8.95 g, yield 24%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1064.5579 (theoretical value: 1064.5564). Theoretical elemental content (%) C 76 H 69 BN4O: C, 85.69; H, 6.53; N, 5.26. Actual element content (%): C, 85.68; H, 6.55; N, 5.24.

[0192] [Synthetic Example 41] Preparation of Compound 630:

[0193] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-169 and GG-630, respectively, with other steps remaining unchanged, to obtain compound 630 (9.15 g, yield 27%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 967.4145 (theoretical value: 967.4131). Theoretical elemental content (%) C 69 H 54 BN3S: C, 85.61; H, 5.62; N, 4.34. Actual element content (%): C, 85.66; H, 5.65; N, 4.32.

[0194] [Synthetic Example 42] Preparation of Compound 657:

[0195] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-657 and GG-657, respectively, with other steps remaining unchanged, to obtain compound 657 (9.59 g, yield 28%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 977.4897 (theoretical value: 977.4880). Theoretical elemental content (%) C 72 H 60 BN3: C, 88.42; H, 6.18; N, 4.30. Actual element content (%): C, 88.46; H, 6.15; N, 4.33.

[0196] [Synthetic Example 43] Preparation of Compound 660:

[0197] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-660 and GG-630, respectively, with other steps remaining unchanged, to obtain compound 660 (9.89 g, yield 25%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1129.5554 (theoretical value: 1129.5540). Theoretical elemental content (%) C 81 H 72 BN3S: C, 86.07; H, 6.42; N, 3.72. Actual elemental content (%): C, 86.06; H, 6.45; N, 3.73.

[0198] [Synthetic Example 44] Preparation of Compound 664:

[0199] Following the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-664, DD-169, and GG-630, respectively, with other steps remaining unchanged, to obtain compound 664 (9.17 g, yield 22%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1189.4360 (theoretical value: 1189.4349). Theoretical elemental content (%) C 85 H 56 BN5S: C, 85.77; H, 4.74; N, 5.88. Actual element content (%): C, 85.76; H, 4.75; N, 5.83.

[0200] [Synthetic Example 45] Preparation of Compound 684:

[0201] According to the preparation method of Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-684, DD-684, and GG-684, respectively, while other steps remained unchanged, to obtain compound 684 (9.37 g, yield 23%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1162.4985 (theoretical value: 1162.4997). Theoretical elemental content (%) C 81 H 67 BN4Si2: C, 83.62; H, 5.80; N, 4.82. Actual elemental content (%): C, 83.66; H, 5.85; N, 4.83.

[0202] [Synthetic Example 46] Preparation of Compound 693:

[0203] According to the preparation method in Synthesis Example 20, BB-15, DD-200, and GG-200 in Synthesis Example 20 were replaced with BB-693, DD-693, and GG-630, respectively, while other steps remained unchanged, yielding compound 693 (7.63 g, yield 24%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 907.3689 (theoretical value: 907.3675). Theoretical elemental content (%) C 63 H 38 D6BN3OS: C, 83.34; H, 5.55; N, 4.63. Actual elemental content (%): C, 83.36; H, 5.54; N, 4.68.

[0204] [Synthetic Example 47] Preparation of Compound 698:

[0205] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-698 and GG-349, respectively, with other steps remaining unchanged, to obtain compound 698 (7.99 g, yield 23%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 991.4689 (theoretical value: 991.4673). Theoretical elemental content (%) C 72 H 58 BN3O: C, 87.17; H, 5.89; N, 4.24. Actual element content (%): C, 87.16; H, 5.84; N, 4.26.

[0206] [Synthetic Example 48] Preparation of Compound 724:

[0207] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-25 and BB-25, respectively, while other steps remained unchanged, yielding compound 724 (9.86 g, yield 25%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1125.6149 (theoretical value: 1125.6132). Theoretical elemental content (%) C 83 H 76 BN3: C, 88.51; H, 6.80; N, 3.73. Actual element content (%): C, 88.56; H, 6.84; N, 3.76.

[0208] [Synthetic Example 49] Preparation of Compound 727:

[0209] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-169 and GG-727, respectively, with other steps remaining unchanged, to obtain compound 727 (9.56 g, yield 26%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1049.5831 (theoretical value: 1049.5819). Theoretical elemental content (%) C 77 H 72 BN3: C, 88.06; H, 6.91; N, 4.00. Actual element content (%): C, 88.05; H, 6.89; N, 4.05.

[0210] [Synthetic Example 50] Preparation of Compound 732:

[0211] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-732 and BB'-727, respectively, with other steps remaining unchanged, to obtain compound 732 (9.07 g, yield 24%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1079.6271 (theoretical value: 1079.6289). Theoretical elemental content (%) C 79 H 78 BN3: C, 87.83; H, 7.28; N, 3.89. Actual element content (%): C, 87.85; H, 7.29; N, 3.86.

[0212] [Synthetic Example 51] Preparation of Compound 741:

[0213] Following the preparation method of Synthesis Example 20, DD-200 and GG-200 in Synthesis Example 20 were replaced with DD-169 and BB-8, respectively, while other steps remained unchanged, yielding compound 741 (8.88 g, yield 27%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 939.4736 (theoretical value: 939.4724). Theoretical elemental content (%) C 69 H 58 BN3: C, 88.16; H, 6.22; N, 4.47. Actual element content (%): C, 88.15; H, 6.19; N, 4.49.

[0214] The following are other compounds besides the boron-nitrogen heterocyclic compounds described in this invention used in the device fabrication examples:

[0215] 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 (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Table 1.

[0216] Comparative device fabrication example 1: Comparative device 1

[0217] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0218] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-7 and p-3 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-7 as hole transport layer with a thickness of 120 nm; c) HT-17 as light-emitting auxiliary layer with a thickness of 30 nm; PhCbBCz, Ir(ppy)2(m-bppy) and ref-1 (mass ratio 78:20:2) as light-emitting layer with a thickness of 30 nm; d) TPBi as hole blocking layer with a thickness of 10 nm; e) TMPyPB and Liq (mass ratio 1:1) as electron transport layer with a thickness of 30 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 10:1) as cathode with a thickness of 10 nm; h) CP-2 as capping layer with a thickness of 120 nm.

[0219] Comparative device fabrication examples 2-4: Comparative devices 2-4

[0220] By replacing ref-1 in the overlay layer with ref-2, ref-3, and ref-4 in sequence, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 4 can be obtained.

[0221] Device fabrication examples 1-46: Light-emitting devices 1-46

[0222] Replace ref-1 in the overlay layer sequentially with compounds 8, 15, 16, 18, 25, 29, 45, 94, 104, 149, 169, 174, 175, 194, 200, 210, 217, 224, 226, 230, 237, 245, 254, 255, and 2... Compounds 56, 267, 280, 325, 326, 349, 355, 364, 405, 491, 526, 630, 657, 660, 664, 684, 693, 698, 724, 727, 732, and 741, with the other steps being the same as in Comparative Device Preparation Example 1, can be used to obtain light-emitting devices 1 to 46.

[0223] Table 1

[0224]

[0225] The device data in Table 1 show that, as a doping material for the light-emitting layer, the boron-nitrogen heterocyclic compound provided by this invention results in a narrower half-width at half-maximum (WHM) of the emitted light compared to existing technologies, thereby improving the color purity of the device and also increasing its luminous efficiency and lifespan.

[0226] 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-nitrogen heterocyclic compound, characterized by, The boron-nitrogen heterocyclic compound has a structure shown in formula (I): X, Y, and Z are independently selected from one of nothing, a single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; R1, R2, and R3 are independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a monovalent group formed by fusing a C3-C12 alicyclic ring and a C6-C30 aromatic ring, wherein R1 and R2 can be connected to form a ring; Ring A, ring B, ring C, ring D, ring E, and ring F are independently selected from one of substituted or unsubstituted C6-C30 aromatic ring, substituted or unsubstituted C6-C30 heteroaromatic ring, and substituted or unsubstituted C3-C10 saturated or unsaturated alicyclic ring; v is selected, on each occurrence and identically or differently, from N or CR v R v is selected, on each occurrence and identically or differently, from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C12 aliphatic ring and C6-C30 aromatic ring fused monovalent groups, or adjacent two R v may be linked to form a ring, or R v is linked to a carbon atom on ring A to form a ring; Ar is selected from a group shown in formula (I-A) or formula (I-B): Ring G is selected from one of substituted or unsubstituted C3-C10 alicyclic ring; R is selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a monovalent group formed by fusing a C3-C12 alicyclic ring and a C6-C30 aromatic ring; u is, on each occurrence, identically or differently selected from N or CR u , R u is, on each occurrence, identically or differently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, or substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused monovalent groups, or two adjacent R u may be linked to form a ring; L is selected from one of a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, and a divalent group formed by fusing a C3-C12 alicyclic ring and a C6-C30 aromatic ring.

2. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The boron-nitrogen heterocyclic compound has one of structures shown in formula (II-A) to (II-R): X1 and Y1 are independently selected from one of O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; Ring A, ring B, ring C, ring D, ring E, ring F, v, Ar, L, and Z are as described in claim 1.

3. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The boron-nitrogen heterocyclic compound has one of structures shown in formula (III-A) to (III-P): X, Y, ring A, ring B, ring C, ring D, ring E, ring F, v, Ar, and L are as described in claim 1.

4. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The rings A, B, C, D, E, F are independently selected from one of the following: a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted benzocyclopropane ring, a substituted or unsubstituted benzocyclobutane ring, a substituted or unsubstituted benzocyclopentane ring, a substituted or unsubstituted benzocyclohexane ring, a substituted or unsubstituted benzocycloheptane ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted pyrazine ring, a substituted or unsubstituted pyridazine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted benzonaphthofuran ring, a substituted or unsubstituted benzonaphthothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzoxazole ring, a substituted or unsubstituted benzothiazole ring, a substituted or unsubstituted benzimidazole ring, a substituted or unsubstituted cyclopropane ring, a substituted or unsubstituted cyclobutane ring, a substituted or unsubstituted cyclopentane ring, a substituted or unsubstituted cyclohexane ring, a substituted or unsubstituted cycloheptane ring, a substituted or unsubstituted cyclopropene ring, a substituted or unsubstituted cyclobutene ring, a substituted or unsubstituted cyclopentene ring, a substituted or unsubstituted cyclohexene ring, a substituted or unsubstituted cycloheptene ring.

5. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The Ar is selected from one of the following: wherein a1 is selected from 0, 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, 4, 5, or 6; c1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; d1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; e1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group; 11 R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group; The u, R are as defined in claim 1.

6. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The L is selected from a single bond or one of the following: wherein said a 101 at each occurrence, the same or different, is selected from 0, 1, 2, 3, or 4; said b 101 at each occurrence, the same or different, is selected from 0, 1, 2, 3, 4, 5, or 6; said c 101 at each occurrence, the same or different, is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said d 101 at each occurrence, the same or different, is selected from 0, 1, or 2; said e 101 at each occurrence, the same or different, is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said f 101 at each occurrence, the same or different, is selected from 0, 1, 2, or 3; said g 101 at each occurrence, the same or different, is selected from 0, 1, 2, 3, 4, or 5; R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group fused from substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, at each occurrence, identically or differently; 101 R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group fused from substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, at each occurrence, identically or differently; R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group. 102 R is selected from the group consisting of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, and substituted or unsubstituted silyl group.

7. The boron-nitrogen heterocyclic compound according to claim 1, characterized by The boron-nitrogen heterocyclic compound is selected from one of the following: 。 8. An organic electroluminescent device comprising an anode, a cathode, an organic layer, said organic layer being located between said cathode and said anode, characterized in that The organic layer contains the boron-nitrogen heterocyclic compound of any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transport region, a light emitting region, and an electron transport region. The light-emitting layer contains the boron-nitrogen heterocyclic compound of any one of claims 1-7.

10. An organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material and a guest material, characterized in that, The guest material contains the boron-nitrogen heterocyclic compound of any one of claims 1-7.

Images