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 relatively large steric hindrance, strong rigidity and small molecular vibration, and can realize narrow-spectrum emission and improve the color purity of light; meanwhile, the distance between molecules is increased, the acting force between the molecules is small, quenching caused by aggregation can be overcome, the luminous efficiency of the device is improved, and the service life of the device is 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 the characteristics of being thin and light, having a wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They have been widely used in the fields of lighting and display and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] OLED devices have a cathode and an anode, with a light-emitting layer sandwiched between them. This layer contains a luminescent material (guest material). When the device is powered on, holes and electrons are injected from the anode and cathode, respectively, reaching the light-emitting layer. They recombine to generate excitons, releasing energy. Under the influence of an electric field, the excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state. Because the excited state is unstable, the electrons return to the ground state, releasing energy as light, thus producing luminescence. Guest materials are generally classified as phosphorescent materials and fluorescent materials. In traditional OLED fluorescent materials, the radiative transition of electrons from the triplet energy level to the ground state is forbidden; the triplet energy is deactivated through non-radiative transitions, resulting in an internal quantum efficiency of only 25%. Phosphorescent materials, utilizing spin-orbit coupling, can achieve an internal quantum efficiency of up to 100%. However, most phosphorescent materials contain precious metals, leading to problems such as high cost and poor color purity.

[0004] In recent years, novel thermally activated delayed fluorescence materials (MR-TADF) with multiple resonance effects have become a research hotspot in the OLED field due to their advantages such as high efficiency and narrow spectral emission. Generally, boron-nitrogen heterocyclic compounds with resonance structures are more likely to achieve narrow half-peak emission. However, they are prone to aggregation-induced quenching in doped films, leading to reduced luminous efficiency and color purity of the devices. Therefore, there is an urgent need to develop MR-TADF materials with superior performance. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides a boron-nitrogen heterocyclic compound having the structure shown in formula (I):

[0006]

[0007] Wherein, x1, x2, and x3 are independently selected from CR x Or N, wherein y1, y2, y3, and y4 are independently selected from CR yOr N, wherein z1, z2, z3, z4 are independently selected from CR z Or N, wherein u1, u2, u3, u4, u5 are independently selected from CR u Or N, the R mentioned x R y R z R u Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C6-C30 aromatic amino group, and combinations thereof, and has at most one R. y Selected from substituted or unsubstituted C1-C12 alkyl groups, and having at most one R. u Selected from substituted or unsubstituted C1-C12 alkyl groups, or two adjacent R groups x Connected to form a loop, or two adjacent Rs y Connected to form a loop, or two adjacent Rs z Connected to form a loop, or two adjacent Rs u They can be connected to form a loop, or z4 and u5 can be connected by Y, in which case both z4 and u5 are C;

[0008] X is selected from one of single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; Y is selected from one of single bond, O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6; and R1, R2, R3, R4, R5, and R6 are independently selected from substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C12 alkyl groups, and substituted or unsubstituted C3-C10 cyclic groups. An alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R1 and R2 linked together to form a ring, or R4 and R5 linked together to form a ring;

[0009] The 'a' is selected from 0, 1, or 2;

[0010] Each time R0 appears, it is selected, either identically or differently, from one of the following groups: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or combinations thereof:

[0011]

[0012] Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the h mentioned 11 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 i 11 Each time it appears, it is selected from 0, 1, or 2, either the same or different.

[0013] The R mentioned 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or two adjacent R groups. 11 Connected to form a ring;

[0014] The R mentioned 12 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C10 cycloalkyl group;

[0015] The R mentioned 13 Selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0016] X1 is selected from O, S, and CR. 14 R 15 or NR 16 X2 is selected from O, S or NR. 17 The R mentioned 14 R 15 R 16 R 17 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, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R 14 R 15 Connected to form a ring;

[0017] The L is selected from a single bond, one of the following groups:

[0018]

[0019] Wherein, the a 101 Each 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 the same or different;

[0020] The R mentioned101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0021] 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, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted silyl group;

[0022] The ring A and ring B are independently selected from one of the following: a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring.

[0023] The ring C is selected from one of the following: a substituted or unsubstituted aromatic ring of C6 to C30, a substituted or unsubstituted heteroaromatic ring of C3 to C11, a fused ring of a substituted or unsubstituted aromatic ring of C6 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7, and a fused ring of a substituted or unsubstituted heteroaromatic ring of C3 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7.

[0024] The boron-nitrogen heterocyclic compound is not one of the following compounds:

[0025]

[0026] The present invention also provides an organic electroluminescent device containing the boron-nitrogen heterocyclic compound described in this invention.

[0027] 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 contains the boron-nitrogen heterocyclic compound described in the present invention.

[0028] 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 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 the present invention.

[0029] Beneficial effects:

[0030] The boron-nitrogen heterocyclic compounds provided by this invention have large steric hindrance, high rigidity, and low molecular vibration, enabling narrow-spectrum emission and improving the color purity of light. At the same time, the increased intermolecular distance and weak intermolecular forces can overcome quenching caused by aggregation, thereby improving the luminous efficiency and lifespan of the device. Detailed Implementation

[0031] 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.

[0032] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and comprises 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.

[0033] 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".

[0034] The halogens mentioned in this invention refer to fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0035] 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 kThe 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... k The 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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, thiophene, pyrrole, imidazole, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiophene, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, or pyridyl.

[0042] 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 the monovalent group formed by the fusion of an aliphatic ring and an aromatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, and naphthocyclohexyl. The linkage site of the group may be on the aromatic ring or on the aliphatic ring, but is preferably on the aromatic ring.

[0043] 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 heteroatom includes, but is 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 may include furanyl, thiophene, pyrrole, imidazolyl, pyridinyl, 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. The linkage site of the group can be on a heteroaromatic ring or on an aliphatic ring, but is preferably on a heteroaromatic ring.

[0044] 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.

[0045] 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.

[0046] 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 with two bonding sites, i.e., a divalent group. The above description of groups formed by the fusion of an aromatic ring and an aliphatic ring can be applied, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group. The bonding sites of the group can all be on the aromatic ring, or both on the aliphatic ring, or one on the aromatic ring and the other on the aliphatic ring, but preferably both on the aromatic ring.

[0047] 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 with 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. The bonding sites of the group can all be on the heteroaromatic ring, or both on the aliphatic ring, or one on the heteroaromatic ring and the other on the aliphatic ring, but preferably both on the heteroaromatic ring.

[0048] 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.

[0049] 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, etc. 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.

[0050] 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 of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0051] 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 Can represent Can represent And so on.

[0052] 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:

[0053]

[0054] 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.

[0055] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0056] 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.

[0057] 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.

[0058] This invention provides a boron-nitrogen heterocyclic compound having the structure shown in formula (I):

[0059]

[0060] Wherein, x1, x2, and x3 are independently selected from CR x Or N, wherein y1, y2, y3, and y4 are independently selected from CR y Or N, wherein z1, z2, z3, z4 are independently selected from CR z Or N, wherein u1, u2, u3, u4, u5 are independently selected from CR u Or N, the R mentioned x R y R z R u Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C6-C30 aromatic amino group, and combinations thereof, and has at most one R. y Selected from substituted or unsubstituted C1-C12 alkyl groups, and having at most one R. u Selected from substituted or unsubstituted C1-C12 alkyl groups, or two adjacent R groups x Connected to form a loop, or two adjacent Rs y Connected to form a loop, or two adjacent Rs z Connected to form a loop, or two adjacent Rs u They can be connected to form a loop, or z4 and u5 can be connected by Y, in which case both z4 and u5 are C;

[0061] X is selected from one of single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; Y is selected from one of single bond, O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6; and R1, R2, R3, R4, R5, and R6 are independently selected from substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C12 alkyl groups, and substituted or unsubstituted C3-C10 cyclic groups. An alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R1 and R2 linked together to form a ring, or R4 and R5 linked together to form a ring;

[0062] The 'a' is selected from 0, 1, or 2;

[0063] Each time R0 appears, it is selected, either identically or differently, from one of the following groups: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or combinations thereof:

[0064]

[0065]

[0066] Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the h mentioned 11 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 i 11 Each time it appears, it is selected from 0, 1, or 2, either the same or different.

[0067] The R mentioned 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or two adjacent R groups. 11 Connected to form a ring;

[0068] The R mentioned12 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C10 cycloalkyl group;

[0069] The R mentioned 13 Selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0070] X1 is selected from O, S, and CR. 14 R 15 or NR 16 X2 is selected from O, S or NR. 17 The R mentioned 14 R 15 R 16 R 17 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, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R 14 R 15 Connected to form a ring;

[0071] The L is selected from a single bond, one of the following groups:

[0072]

[0073] Wherein, the a 101 Each 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 101Each 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 the same or different;

[0074] The R mentioned 101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0075] 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, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted silyl group;

[0076] The ring A and ring B are independently selected from one of the following: a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring.

[0077] The ring C is selected from one of the following: a substituted or unsubstituted aromatic ring of C6 to C30, a substituted or unsubstituted heteroaromatic ring of C3 to C11, a fused ring of a substituted or unsubstituted aromatic ring of C6 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7, and a fused ring of a substituted or unsubstituted heteroaromatic ring of C3 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7.

[0078] The boron-nitrogen heterocyclic compound is not one of the following compounds:

[0079]

[0080] 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.

[0081] Preferably, at most 2 or at most 1 of x1, x2, and x3 are selected from N; at most 2 or at most 1 of y1, y2, y3, and y4 are selected from N; at most 2 or at most 1 of z1, z2, z3, and z4 are selected from N; and at most 3, at most 2, or at most 1 of u1, u2, u3, u4, and u5 are selected from N.

[0082] Preferably, the boron-nitrogen heterocyclic compound has a structure shown in one of formulas (II-A) to (II-F):

[0083]

[0084]

[0085] In equations (II-A) and (II-C), z4 and u5 are not connected by Y';

[0086] X' is selected from one of O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3;

[0087] The Y' is selected from one of O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6.

[0088] Preferably, the R x R y R z R u Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane Alkyl; norbornel alkyl; deuterated, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl The following groups, substituted or unsubstituted, are selected 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: benzene One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0089] Preferably, there is at most one R. x Selected from substituted or unsubstituted C1 to C12 alkyl groups.

[0090] Preferably, there is at most one R. z Selected from substituted or unsubstituted C1 to C12 alkyl groups.

[0091] Preferably, there is at most one R. xIt is selected from halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C6-C30 aromatic amino, and combinations thereof.

[0092] Preferably, there is at most one R. y It is selected from halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C6-C30 aromatic amino, and combinations thereof.

[0093] Preferably, there is at most one R. z It is selected from halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C6-C30 aromatic amino, and combinations thereof.

[0094] Preferably, there is at most one R. u It is selected from halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C6-C30 aromatic amino, and combinations thereof.

[0095] Preferably, there is at most one R. x Selected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0096] Preferably, there is at most one R. ySelected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0097] Preferably, there is at most one R. zSelected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0098] Preferably, there is at most one R. uSelected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane.

[0099] Preferably, two adjacent R x Linked in a substituted or unsubstituted manner: benzene ring, naphthalene ring, pyridine ring; preferably, two adjacent R... y Linked in a substituted or unsubstituted manner: benzene ring, naphthalene ring, pyridine ring; preferably, two adjacent R... z Linked in a substituted or unsubstituted manner: benzene ring, naphthalene ring, pyridine ring; preferably, two adjacent R... u Linked into substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring.

[0100] Preferably, the boron-nitrogen heterocyclic compound has a structure shown in one of formulas (III-A) to (III-F):

[0101]

[0102] Wherein, X' is selected from one of O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3;

[0103] The Y' is selected from one of O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6;

[0104] The R mentioned x1 R y1 R z1 R u1 Each time it appears, it is selected from hydrogen atoms or deuterium atoms, either the same or different.

[0105] The R mentioned x2 R y2 R z2 R u2 Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane Alkyl; norbornel alkyl; deuterated, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl The following groups, substituted or unsubstituted, are selected 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: benzene One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane;

[0106] And at most one R x2Selected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane;

[0107] And at most one R y2Selected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane;

[0108] And at most one R z2Selected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane;

[0109] And at most one R u2Selected from fluorine atoms; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, naphthyl, anthracene, phenanthrene The following groups, substituted or unsubstituted, are: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0110] Preferably, R1, R2, R3, R4, R5, and R6 are independently selected from trimethylsilyl; methyl; trifluoromethyl; deuterated methyl; 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; fluorine atom; cyano; trimethylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl The following groups are substituted or unsubstituted with one or more of the following groups: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinoxalinyl, quinazolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0111] Preferably, R1 and R2 are connected to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring; preferably, R4 and R5 are connected to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring. More preferably, R1 and R2 are connected to form a substituted or unsubstituted ring: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, adamantane ring, norbornane ring; even more preferably, R4 and R5 are connected to form a substituted or unsubstituted ring: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, adamantane ring, norbornane ring.

[0112] Preferably, ring A and ring B are independently selected from one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted triphenylene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted isoquinoline ring, substituted or unsubstituted quinoxaline ring, and substituted or unsubstituted quinazoline ring.

[0113] Preferably, the ring C is selected from one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted triphenylene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted isoquinoline ring, substituted or unsubstituted quinoxaline ring, and substituted or unsubstituted quinazoline ring.

[0114]

[0115] Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the e mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the g mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7, either the same or different.

[0116] The R mentioned 21Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane Alkyl; norbornel alkyl; deuterated, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl The following groups, substituted or unsubstituted, are selected 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: benzene One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0117] Preferably, the R 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, fluorine, cyano, trimethylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted... One of the following: phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0118] Preferably, the R 12 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, fluorine atom, cyano group, trimethylsilyl group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornel group.

[0119] Preferably, the R 13 Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthalene. One of the following: alkyl, deuterated naphthyl, biphenyl, deuterated biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0120] Preferably, the R 14 R 15 R 16 R 17 Independently selected from methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterium One of the following: substituted biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0121] Preferably, each time R0 appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, fluorine atom, cyano group, trimethylsilyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, adamantane group, norbornyl group:

[0122]

[0123]

[0124] Preferably, at most one of the R0 atoms is not a hydrogen atom, deuterium atom, fluorine atom, cyano, trimethylsilyl, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, or deuterated tert-butyl.

[0125] Preferably, the boron-nitrogen heterocyclic compound is selected from one of the following compounds:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] The boron-nitrogen heterocyclic compound represented by formula (I) of this invention can be prepared by the following synthetic route: Synthetic route one:

[0159]

[0160] Synthesis Route 2:

[0161]

[0162] Synthesis Route 3 (when a is not 0):

[0163]

[0164] Wherein, x1, x2, x3, y1, y2, y3, y4, z1, z2, z3, z4, u1, u2, u3, u4, u5, X, a, R0, L, ring A, ring B, and ring C are all as described in this invention.

[0165] The Z and W are independently selected from fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms;

[0166] The V mentioned is selected from B(OH)2 or

[0167] The above synthetic route employs reaction types commonly used in organic synthesis, and there are no particular limitations 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.

[0168] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the boron-nitrogen heterocyclic compound described in the present invention.

[0169] 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.

[0170] 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 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 the present invention.

[0171] 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.

[0172] 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.

[0173] Preferably, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0174] Preferably, the light-emitting layer comprises a first host material, a second host material, an exciton sensitizing material, and a guest material, wherein the guest material contains the boron-nitrogen heterocyclic compound described in this invention.

[0175] 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.

[0176] 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 to HT-17, and compounds p-1 to p-3, but not limited to these.

[0177]

[0178]

[0179] 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 concentration 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-17 as shown above, but not limited thereto.

[0180] 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, and 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-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and compounds HT-1 to HT-17 as shown above, but not limited to these.

[0181] 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 complexes, 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. The boron-nitrogen heterocyclic compounds described in this invention are preferred.

[0182] The exciton-sensitizing material described in this invention refers to a material that enables the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers in organic electroluminescent devices may perform functions such as exciton trapping, exciton conversion, and exciton transport. The exciton-sensitizing material may be a complex containing a metal element, such as an iridium complex, but is not limited to this.

[0183] 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.

[0184] 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.

[0185] 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 use aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymers, etc. Examples 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), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but is not limited to these.

[0186] 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 selected material must have 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 selected material must be lower than that of the main 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.

[0187] 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.

[0188] 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.

[0189] Preferably, the organic electroluminescent device further includes a capping layer on the side of the cathode facing away from the anode.

[0190] 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, compound CP-1, compound CP-2, compound CP-3, and compound CP-4, but are not limited thereto.

[0191]

[0192] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, immersion, screen printing, etc. There are no special limitations on the thickness of each layer, as long as good device performance is obtained.

[0193] The organic layers mentioned above are preferably prepared using vacuum evaporation, inkjet printing, or spin coating methods.

[0194] 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.

[0195] 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.

[0196] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0197] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent.

[0198] 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.

[0199] Synthesis Example 1: Synthesis of Intermediate BB

[0200] Synthesis of intermediate BB-144:

[0201]

[0202] Under nitrogen protection, compound aa-144 (79.46 g, 200 mmol), pinacol diboronic acid ester (51.30 g, 202 mmol), Pd(dppf)Cl2 (1.75 g, 2.39 mmol), KOAc (29.44 g, 300 mmol), and 1,4-dioxane (1 L) were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, the solvent was concentrated by rotary evaporation, and crystals were precipitated by cooling. The solid was filtered, and the obtained solid was recrystallized from toluene to give intermediate BB-144 (70.96 g, yield 79.85%); HPLC purity ≥99.88%. Mass spectrometry m / z: 444.2031 (theoretical value: 444.2009).

[0203] Synthesis of intermediate BB-208:

[0204]

[0205] By replacing compound aa-144 with an equimolar amount of compound aa-208, and following the same steps as the synthesis of intermediate BB-144, intermediate BB-208 (65.07 g, yield 77.96%) was obtained; HPLC purity ≥99.85%. Mass spectrometry m / z: 417.1666 (theoretical value: 417.1649).

[0206] Synthesis of intermediate BB-439:

[0207]

[0208] By replacing compound aa-144 with an equimolar amount of compound aa-439, and following the same steps as the synthesis of intermediate BB-144, intermediate BB-439 (83.43 g, yield 80.31%) was obtained; HPLC purity ≥99.89%. Mass spectrometry m / z: 519.2383 (theoretical value: 519.2370).

[0209] Synthesis Example 2: Synthesis of Compound 39

[0210]

[0211] Compounds AA-39 (67.07 g, 200 mmol), BB-39 (61.47 g, 220 mmol), and cesium carbonate (107.52 g, 330 mmol) were dissolved in DMF (1700 mL) and refluxed under nitrogen for 9 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate CC-39 (110.80 g, yield 93.15%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 592.9989 (theoretical value: 592.9982).

[0212] Under nitrogen protection, intermediate CC-39 (89.21 g, 150 mmol), compound DD-39 (70.11 g, 150 mmol), potassium carbonate (31.10 g, 225 mmol), and Pd(PPh3)4 (2.08 g, 1.8 mmol) were dissolved in 750 mL of a toluene / ethanol / water (2:1:1) mixture and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake with toluene / ethanol (8:1 v / v) to obtain intermediate EE-39 (100.96 g, yield 83.27%), with an HPLC purity ≥98.96%. Mass spectrometry m / z: 806.2078 (theoretical value: 806.2063).

[0213] Under nitrogen protection, tris(dibenzylacetone)dipalladium (2.20 g, 2.4 mmol), tri-tert-butylphosphine (1.46 g, 7.2 mmol), intermediate EE-39 (97.00 g, 120 mmol), and compound FF-39 (22.34 g, 132 mmol) were dissolved in anhydrous toluene (960 mL), heated to reflux (110 °C), and reacted at this temperature for 10 h. After the reaction system cooled to room temperature, the reaction solution was diluted, filtered, and the filtrate was concentrated. Then, silica gel column chromatography was performed using a 1:1 (v / v) mixture of dichloromethane and n-hexane as eluent to obtain intermediate GG-39 (102.05 g, yield 94.85%). The solid purity was ≥99.77% as determined by HPLC. Mass spectrometry m / z: 895.3681 (theoretical value: 895.3693).

[0214] Intermediate GG-39 (26.90 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). Under nitrogen atmosphere at 0 °C, n-butyllithium (18 mL, 45 mmol, 2.5 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 2 hours. The mixture was then cooled to 0 °C and BBr3 (5.75 mL, 60 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 12 hours. After the reaction was complete, the reaction was quenched with 51 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to give compound 39 (8.50 g, yield 32.58%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 869.3956 (theoretical value: 869.3941). Theoretical elemental content (%) C 64 H 48BN3: C, 88.37; H, 5.56; N, 4.83. Measured elemental content (%): C, 88.39; H, 5.53; N, 4.85.

[0215] Synthesis Example 3: Synthesis of Compound 45

[0216]

[0217] Replacing DD-39 with an equimolar amount of DD-45 and FF-39 with an equimolar amount of FF-45, while adhering to the same steps as in Synthesis Example 2, yielded compound 45 (9.06 g, yield 32.74%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 921.4269 (theoretical value: 921.4254). Theoretical elemental content (%) C 68 H 52 BN3: C, 88.58; H, 5.69; N, 4.56. Measured elemental content (%): C, 88.55; H, 5.74; N, 4.55.

[0218] Synthesis Example 4: Synthesis of Compound 118

[0219]

[0220] Under nitrogen protection, compounds AA-118 (42.20 g, 200 mmol), DD-45 (73.45 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and Pd(PPh3)4 (2.77 g, 2.4 mmol) were dissolved in 1 L of a toluene / ethanol / water (2:1:1) mixture and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake with toluene / ethanol (8:1 v / v) to give intermediate CC-118 (65.78 g, yield 88.56%), with an HPLC purity ≥98.98%. Mass spectrometry m / z: 371.0937 (theoretical value: 371.0922).

[0221] Intermediate CC-118 (55.70 g, 150 mmol) was dissolved in 500 mL of tetrahydrofuran solution. Under nitrogen atmosphere at -20 °C, lithium diisopropylamino (LDA, 75 mL, 150 mmol, 2 M tetrahydrofuran solution) was added dropwise. After stirring for 1 hour, elemental iodine (38.07 g, 150 mmol) was added, and the mixture was allowed to return to room temperature and stirred for another 4 hours. After the reaction was complete, the mixture was washed with sodium thiosulfate solution and dichloromethane. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate DD-118 (66.21 g, yield 88.76%). HPLC analysis showed a solid purity ≥99.86%. Mass spectrometry m / z: 496.9875 (theoretical value: 496.9888).

[0222] Compounds DD-118 (49.73 g, 100 mmol), FF-45 (35.36 g, 110 mmol), and cesium carbonate (53.76 g, 165 mmol) were dissolved in DMF (850 mL) and refluxed under nitrogen for 8.5 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate FF-118 (73.31 g, yield 91.79%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 798.1356 (theoretical value: 798.1343).

[0223] Intermediate FF-118 (39.93 g, 50 mmol), compound GG-118 (18.39 g, 110 mmol), and cesium carbonate (53.76 g, 165 mmol) were dissolved in DMF (625 mL) and refluxed under nitrogen for 9 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate HH-118 (49.54 g, yield 90.65%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 1092.2678 (theoretical value: 1092.2689).

[0224] Intermediate HH-118 (32.79 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). Under nitrogen atmosphere at 0 °C, n-butyllithium (18 mL, 45 mmol, 2.5 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 2 hours. The mixture was then cooled to 0 °C and BBr3 (5.75 mL, 60 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 12 hours. After the reaction was complete, the reaction was quenched with 51 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to give compound 118 (9.06 g, yield 30.97%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 974.3569 (theoretical value: 974.3581). Theoretical elemental content (%) C 72 H 43 BN4: C, 88.70; H, 4.45; N, 5.75. Measured elemental content (%): C, 88.75; H, 4.41; N, 5.72.

[0225] Synthesis Example 5: Synthesis of Compound 140

[0226]

[0227] Under nitrogen protection, compounds AA-140 (45.49 g, 200 mmol), BB-140 (95.89 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and Pd(PPh3)4 (2.77 g, 2.4 mmol) were dissolved in 1 L of a toluene / ethanol / water (2:1:1) mixture and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake with toluene / ethanol (8:1 v / v) to give intermediate CC-140 (87.97 g, yield 87.96%), with an HPLC purity ≥98.91%. Mass spectrometry m / z: 499.1859 (theoretical value: 499.1878).

[0228] Intermediate CC-140 (75.00 g, 150 mmol), compound GG-118 (55.18 g, 330 mmol), and cesium carbonate (161.28 g, 495 mmol) were dissolved in DMF (1900 mL) and refluxed under nitrogen for 9 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate EE-140 (109.69 g, yield 92.05%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 793.3238 (theoretical value: 793.3224).

[0229] Intermediate EE-140 (23.83 g, 30 mmol) was dissolved in tert-butylbenzene (510 mL). Under nitrogen atmosphere at 0 °C, n-butyllithium (18 mL, 45 mmol, 2.5 M n-hexane solution) was added dropwise, followed by heating to 70 °C and stirring for 2 hours. The mixture was then cooled to 0 °C and BBr3 (5.75 mL, 60 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 12 hours. After the reaction was complete, the reaction was quenched with 51 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to give compound 140 (8.07 g, yield 35.03%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 767.3488 (theoretical value: 767.3472). Theoretical elemental content (%) C 56 H 42 BN3: C, 87.60; H, 5.51; N, 5.47. Measured elemental content (%): C, 87.63; H, 5.53; N, 5.45.

[0230] Synthesis Example 6: Synthesis of Compound 144

[0231]

[0232] Replacing BB-140 with an equimolar amount of BB-144, and following the same steps as in Synthesis Example 5, yielded compound 144 (7.73 g, yield 35.18%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 732.2497 (theoretical value: 732.2485). Theoretical elemental content (%) C 53 H 29 BN4: C, 86.89; H, 3.99; N, 7.65. Measured elemental content (%): C, 86.87; H, 4.05; N, 7.61.

[0233] Synthesis Example 7: Synthesis of Compound 161

[0234]

[0235] By replacing BB-140 with an equimolar amount of BB-161 and GG-118 with an equimolar amount of DD-161, and following the same steps as in Synthesis Example 5, compound 161 (6.80 g, yield 33.86%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 669.3079 (theoretical value: 669.3099). Theoretical elemental content (%) C 48 H 12 D 14 BN3: C, 86.09; H, 6.02; N, 6.28. Measured elemental content (%): C, 86.03; H, 6.07; N, 6.27.

[0236] Synthesis Example 8: Synthesis of Compound 171

[0237]

[0238] By replacing BB-140 with an equimolar amount of DD-171 and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 171 (8.65 g, yield 32.78%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 879.4739 (theoretical value: 879.4724). Theoretical elemental content (%) C 64 H 58 BN3: C, 87.35; H, 6.64; N, 4.78. Measured elemental content (%): C, 87.33; H, 6.69; N, 4.75.

[0239] Synthesis Example 9: Synthesis of Compound 178

[0240]

[0241] Replacing DD-39 with an equimolar amount of DD-45 and FF-39 with an equimolar amount of GG-118, while adhering to the same steps as in Synthesis Example 2, yielded compound 178 (7.31 g, yield 31.73%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 767.3485 (theoretical value: 767.3472). Theoretical elemental content (%) C 56 H 42 BN3: C, 87.60; H, 5.51; N, 5.47. Measured elemental content (%): C, 87.62; H, 5.54; N, 5.42.

[0242] Synthesis Example 10: Synthesis of Compound 185

[0243]

[0244] By replacing BB-140 with an equimolar amount of BB-185 and GG-118 with an equimolar amount of DD-185, and following the same steps as in Synthesis Example 5, compound 185 (8.25 g, yield 31.25%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 879.4735 (theoretical value: 879.4724). Theoretical elemental content (%) C 64 H 58 BN3: C, 87.35; H, 6.64; N, 4.78. Measured elemental content (%): C, 87.33; H, 6.62; N, 4.79.

[0245] Synthesis Example 11: Synthesis of Compound 191

[0246]

[0247] By replacing BB-39 with an equimolar amount of BB-191, DD-39 with an equimolar amount of DD-191, and FF-39 with an equimolar amount of GG-118, and following the same steps as in Synthesis Example 2, compound 191 (6.57 g, yield 31.56%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 693.3178 (theoretical value: 693.3160). Theoretical elemental content (%) C 50 H 20 D 10 BN3: C, 86.57; H, 5.81; N, 6.06. Measured elemental content (%): C, 86.55; H, 5.86; N, 6.02.

[0248] Synthesis Example 12: Synthesis of Compound 208

[0249]

[0250] Replacing BB-140 with an equimolar amount of BB-208 and GG-118 with an equimolar amount of BB-39, while adhering to the same steps as in Synthesis Example 5, yielded compound 208 (8.64 g, yield 30.98%). HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 929.4617 (theoretical value: 929.4629). Theoretical elemental content (%) C 66 H 56BN5: C, 85.24; H, 6.07; N, 7.53. Measured elemental content (%): C, 85.26; H, 6.02; N, 7.56.

[0251] Synthesis Example 13: Synthesis of Compound 211

[0252]

[0253] By replacing BB-140 with an equimolar amount of BB-211 and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 211 (9.45 g, yield 30.53%) was obtained. HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 1031.5369 (theoretical value: 1031.5350). Theoretical elemental content (%) C 76 H 66 BN3: C, 88.44; H, 6.45; N, 4.07. Measured elemental content (%): C, 88.40; H, 6.49; N, 4.09.

[0254] Synthesis Example 14: Synthesis of Compound 221

[0255]

[0256] By replacing BB-140 with an equimolar amount of BB-221 and GG-118 with an equimolar amount of BB-191, and following the same steps as in Synthesis Example 5, compound 221 (6.45 g, yield 30.17%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 712.2778 (theoretical value: 712.2798). Theoretical elemental content (%) C 51 H 33 BN4: C, 85.95; H, 4.67; N, 7.86. Measured elemental content (%): C, 85.93; H, 4.65; N, 7.89.

[0257] Synthesis Example 15: Synthesis of Compound 227

[0258]

[0259] By replacing BB-140 with an equimolar amount of DD-45 and GG-118 with an equimolar amount of DD-227, and following the same steps as in Synthesis Example 5, compound 227 (8.99 g, yield 31.75%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 943.3817 (theoretical value: 943.3801). Theoretical elemental content (%) C 60 H58 BN3Si4: C, 76.32; H, 6.19; N, 4.45. Measured elemental content (%): C, 76.36; H, 6.12; N, 4.46.

[0260] Synthesis Example 16: Synthesis of Compound 228

[0261]

[0262] By replacing BB-140 with an equimolar amount of DD-171 and GG-118 with an equimolar amount of DD-228, and following the same steps as in Synthesis Example 5, compound 228 (6.73 g, yield 30.85%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 727.1856 (theoretical value: 727.1843). Theoretical elemental content (%) C 48 H 22 BF4N3: C, 79.24; H, 3.05; N, 5.78. Measured elemental content (%): C, 79.22; H, 3.01; N, 5.75.

[0263] Synthesis Example 17: Synthesis of Compound 230

[0264]

[0265] By replacing BB-39 with an equimolar amount of BB-230, DD-39 with an equimolar amount of DD-230, and FF-39 with an equimolar amount of GG-118, and following the same steps as in Synthesis Example 2, compound 230 (7.76 g, yield 32.03%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 807.2859 (theoretical value: 807.2846). Theoretical elemental content (%) C 60 H 34 BN3: C, 89.22; H, 4.24; N, 5.20. Measured elemental content (%): C, 89.20; H, 4.21; N, 5.25.

[0266] Synthesis Example 18: Synthesis of Compound 233

[0267]

[0268] Replacing BB-140 with an equimolar amount of DD-171 and GG-118 with an equimolar amount of BB-230, while following the same steps as in Synthesis Example 5, yielded compound 233 (9.40 g, yield 32.63%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 959.3483 (theoretical value: 959.3472). Theoretical elemental content (%) C 72 H 42 BN3: C, 90.09; H, 4.41; N, 4.38. Measured elemental content (%): C, 90.06; H, 4.48; N, 4.34.

[0269] Synthesis Example 19: Synthesis of Compound 252

[0270]

[0271] Replacing BB-39 with an equimolar amount of DD-45 and DD-39 with an equimolar amount of BB-252, while following the same steps as in Synthesis Example 5, yielded compound 252 (11.40 g, yield 32.09%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1183.5990 (theoretical value: 1183.5976). Theoretical elemental content (%) C 88 H 74 BN3: C, 89.24; H, 6.30; N, 3.55. Measured elemental content (%): C, 89.28; H, 6.28; N, 3.51.

[0272] Synthesis Example 20: Synthesis of Compound 285

[0273]

[0274] By replacing BB-140 with an equimolar amount of DD-45 and GG-118 with an equimolar amount of DD-285, and following the same steps as in Synthesis Example 5, compound 285 (8.45 g, yield 32.91%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 855.2869 (theoretical value: 855.2846). Theoretical elemental content (%) C 64 H 34 BN3: C, 89.82; H, 4.00; N, 4.91. Measured elemental content (%): C, 89.87; H, 3.96; N, 4.91.

[0275] Synthesis Example 21: Synthesis of Compound 294

[0276]

[0277] Replacing DD-39 with an equimolar amount of DD-171 and FF-39 with an equimolar amount of BB-230, while adhering to the same steps as in Synthesis Example 2, yielded compound 294 (8.77 g, yield 31.77%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 919.4085 (theoretical value: 919.4098). Theoretical elemental content (%) C 68 H 50 BN3: C, 88.78; H, 5.48; N, 4.57. Measured elemental content (%): C, 88.77; H, 5.45; N, 4.59.

[0278] Synthesis Example 22: Synthesis of Compound 296

[0279]

[0280] Replacing BB-140 with an equimolar amount of BB-296, and following the same steps as in Synthesis Example 5, yielded compound 296 (7.08 g, yield 32.25%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 731.2548 (theoretical value: 731.2533). Theoretical elemental content (%) C 54 H 30 BN3: C, 88.65; H, 4.13; N, 5.74. Measured elemental content (%): C, 88.63; H, 4.10; N, 5.78.

[0281] Synthesis Example 23: Synthesis of Compound 309

[0282]

[0283] By replacing BB-140 with an equimolar amount of BB-309 and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 309 (9.15 g, yield 31.89%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 955.5021 (theoretical value: 955.5037). Theoretical elemental content (%) C 70 H 62 BN3: C, 87.94; H, 6.54; N, 4.40. Measured elemental content (%): C, 87.90; H, 6.58; N, 4.43.

[0284] Synthesis Example 24: Synthesis of Compound 346

[0285]

[0286] By replacing AA-140 with an equimolar amount of AA-346, BB-140 with an equimolar amount of DD-45, and GG-118 with an equimolar amount of DD-346, and following the same steps as in Synthesis Example 5, compound 346 (7.60 g, yield 30.76%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 823.4081 (theoretical value: 823.4098). Theoretical elemental content (%) C 60 H 50 BN3: C, 87.47; H, 6.12; N, 5.10. Measured elemental content (%): C, 87.45; H, 6.18; N, 5.05.

[0287] Synthesis Example 25: Synthesis of Compound 351

[0288]

[0289] By replacing AA-140 with an equimolar amount of AA-346, BB-140 with an equimolar amount of DD-191, and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 351 (7.97 g, yield 30.20%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 879.4745 (theoretical value: 879.4724). Theoretical elemental content (%) C 64 H 58 BN3: C, 87.35; H, 6.64; N, 4.78. Measured elemental content (%): C, 87.39; H, 6.60; N, 4.75.

[0290] Synthesis Example 26: Synthesis of Compound 365

[0291]

[0292] By replacing AA-140 with an equimolar amount of AA-346, BB-140 with an equimolar amount of BB-365, and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 365 (8.77 g, yield 30.57%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 955.5048 (theoretical value: 955.5037). Theoretical elemental content (%) C 70 H 62 BN3: C, 87.94; H, 6.54; N, 4.40. Measured elemental content (%): C, 87.91; H, 6.55; N, 4.43.

[0293] Synthesis Example 27: Synthesis of Compound 419

[0294]

[0295] By replacing AA-39 with an equimolar amount of AA-419, DD-39 with an equimolar amount of DD-45, and FF-39 with an equimolar amount of FF-419, and following the same steps as in Synthesis Example 2, compound 419 (6.94 g, yield 30.04%) was obtained. HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 769.3395 (theoretical value: 769.3377). Theoretical elemental content (%) C 54 H 40 BN5: C, 84.26; H, 5.24; N, 9.10. Measured elemental content (%): C, 84.28; H, 5.26; N, 9.13.

[0296] Synthesis Example 28: Synthesis of Compound 424

[0297]

[0298] By replacing AA-39 with an equimolar amount of AA-419, DD-39 with an equimolar amount of DD-191, and FF-39 with an equimolar amount of BB-230, and following the same steps as in Synthesis Example 2, compound 424 (8.41 g, yield 30.48%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 919.4078 (theoretical value: 919.4098). Theoretical elemental content (%) C 68 H 50 BN3: C, 88.78; H, 5.48; N, 4.57. Measured elemental content (%): C, 88.73; H, 5.51; N, 4.60.

[0299] Synthesis Example 29: Synthesis of Compound 439

[0300]

[0301] By replacing AA-140 with an equimolar amount of AA-346, BB-140 with an equimolar amount of BB-439, and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 5, compound 439 (9.35 g, yield 30.21%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1031.5363 (theoretical value: 1031.5350). Theoretical elemental content (%) C 76 H 66BN3: C, 88.44; H, 6.45; N, 4.07. Measured elemental content (%): C, 88.48; H, 6.40; N, 4.09.

[0302] Synthesis Example 30: Synthesis of Compound 468

[0303]

[0304] Under nitrogen protection, compounds AA-346 (45.49 g, 200 mmol), DD-45 (73.45 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and Pd(PPh3)4 (2.77 g, 2.4 mmol) were dissolved in 1 L of a toluene / ethanol / water (2:1:1) mixture and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake with toluene / ethanol (8:1 v / v) to give intermediate CC-468 (68.45 g, yield 88.25%), with an HPLC purity ≥98.96%. Mass spectrometry m / z: 387.0638 (theoretical value: 387.0626).

[0305] Intermediate CC-468 (58.17 g, 150 mmol), compound GG-118 (55.18 g, 330 mmol), and cesium carbonate (161.28 g, 495 mmol) were dissolved in DMF (1900 mL) and refluxed under nitrogen for 9 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate EE-468 (94.42 g, yield 92.27%). The purity of the solid was ≥99.89% as determined by HPLC. Mass spectrometry m / z: 681.1988 (theoretical value: 681.1972).

[0306] Intermediate EE-468 (81.87 g, 120 mmol) was dissolved in tert-butylbenzene (2050 mL). Under nitrogen atmosphere at 0 °C, n-butyllithium (72 mL, 180 mmol, 2.5 M n-hexane solution) was added dropwise. The mixture was then heated to 70 °C and stirred for 2 hours. After cooling to 0 °C, BBr3 (23 mL, 240 mmol) was added dropwise. The reaction mixture was allowed to return to room temperature and stirred for 1 hour. N,N-diisopropylethylamine (39.60 mL, 240 mmol, DIEA) was added dropwise again at 0 °C. The reaction mixture was then heated to 150 °C and stirred for 12 hours. After the reaction was completed, the reaction was quenched with 204 mL of methanol, followed by washing with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain intermediate FF-468 (28.30 g, yield 35.98%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 655.2241 (theoretical value: 655.2220).

[0307] Under nitrogen protection, intermediate FF-468 (26.22 g, 40 mmol) and NBS (7.12 g, 40 mmol) were dissolved in 900 mL of chloroform and reacted at room temperature for 12 hours. After the reaction was complete, the solvent was evaporated and the solution was passed through a neutral silica gel column (eluent: dichloromethane and petroleum ether) to give intermediate GG-468 (24.96 g, yield 84.96%). The purity was 99.65% according to HPLC analysis, and the mass spectrometry m / z was 733.1339 (theoretical value: 733.1325).

[0308] Under nitrogen protection, intermediate GG-468 (22.03 g, 30 mmol), compound HH-468 (11.08 g, 30 mmol), potassium carbonate (6.22 g, 45 mmol), and Pd(PPh3)4 (0.42 g, 0.36 mmol) were dissolved in 150 mL of a toluene / ethanol / water (2:1:1) mixture and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene / ethanol (8:1 v / v) to give compound 468 (22.51 g, yield 83.67%) with HPLC purity ≥99.98%. Mass spectrometry m / z: 896.3111 (theoretical value: 896.3111). Theoretical elemental content (%) C 66 H 37 BN4: C, 88.39; H, 4.16; N, 6.25. Measured elemental content (%): C, 88.35; H, 4.13; N, 6.28.

[0309] Synthesis Example 31: Synthesis of Compound 484

[0310]

[0311] Replacing GG-118 with an equimolar amount of BB-39 and HH-468 with an equimolar amount of HH-484, while adhering to the same steps as in Synthesis Example 30, yielded compound 484 (23.75 g, yield 82.79%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 955.5056 (theoretical value: 955.5037). Theoretical elemental content (%) C 70 H 62 BN3: C, 87.94; H, 6.54; N, 4.40. Measured elemental content (%): C, 87.98; H, 6.56; N, 4.37.

[0312] Synthesis Example 32: Synthesis of Compound 492

[0313]

[0314] Replacing DD-45 with an equimolar amount of DD-171, FF-45 with an equimolar amount of GG-118, and GG-118 with an equimolar amount of BB-39, while following the same steps as in Synthesis Example 4, yielded compound 492 (9.75 g, yield 31.08%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1044.5321 (theoretical value: 1044.5302). Theoretical elemental content (%) C 76 H 65 BN4: C, 87.34; H, 6.27; N, 5.36. Measured elemental content (%): C, 87.38; H, 6.21; N, 5.39.

[0315] Synthesis Example 33: Synthesis of Compound 598

[0316]

[0317] By replacing AA-118 with an equimolar amount of AA-598, FF-45 with an equimolar amount of BB-230, and GG-118 with an equimolar amount of BB-39, and following the same steps as in Synthesis Example 4, compound 598 (10.97 g, yield 30.55%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1196.5940 (theoretical value: 1196.5928). Theoretical elemental content (%) C 88 H 73 BN4: C, 88.27; H, 6.15; N, 4.68. Measured elemental content (%): C, 88.25; H, 6.18; N, 4.65.

[0318] Synthesis Example 34: Synthesis of Compound 643

[0319]

[0320] By replacing BB-39 with an equimolar amount of BB-643, DD-39 with an equimolar amount of DD-643, and FF-39 with an equimolar amount of FF-643, and following the same steps as in Synthesis Example 2, compound 643 (8.66 g, yield 32.88%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 877.3678 (theoretical value: 877.3662). Theoretical elemental content (%) C 62 H 48 BN3S: C, 84.82; H, 5.51; N, 4.79. Measured elemental content (%): C, 84.88; H, 5.48; N, 4.74.

[0321] Synthesis Example 35: Synthesis of Compound 696

[0322]

[0323] Replacing FF-45 with an equimolar amount of EE-696 and GG-118 with an equimolar amount of GG-696, while following the same steps as in Synthesis Example 4, yielded compound 696 (9.11 g, yield 30.40%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 998.3658 (theoretical value: 998.3644). Theoretical elemental content (%) C 66 H 51 BN4O2Si2: C, 79.34; H, 5.15; N, 5.61. Measured elemental content (%): C, 79.36; H, 5.18; N, 5.64.

[0324] Synthesis Example 36: Synthesis of Compound 720

[0325]

[0326] By replacing BB-39 with an equimolar amount of GG-118, DD-39 with an equimolar amount of DD-45, and FF-39 with an equimolar amount of FF-720, and following the same steps as in Synthesis Example 2, compound 720 (7.34 g, yield 32.75%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 746.2657 (theoretical value: 746.2642). Theoretical elemental content (%) C 54 H 31BN4: C, 86.86; H, 4.18; N, 7.50. Measured elemental content (%): C, 86.83; H, 4.13; N, 7.57.

[0327] Synthesis Example 37: Synthesis of Compound 729

[0328]

[0329] Replacing DD-39 with an equimolar amount of DD-171 and FF-39 with an equimolar amount of BB-643, while adhering to the same steps as in Synthesis Example 2, yielded compound 729 (7.91 g, yield 32.95%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 878.799.3181 (theoretical value: 799.3192). Theoretical elemental content (%) C 56 H 42 BN3S: C, 84.09; H, 5.29; N, 5.25. Measured elemental content (%): C, 84.13; H, 5.21; N, 5.27.

[0330] Synthesis Example 38: Synthesis of Compound 741

[0331]

[0332] Replacing DD-39 with an equimolar amount of DD-741 and FF-39 with an equimolar amount of GG-696, while adhering to the same steps as in Synthesis Example 2, yielded compound 741 (8.82 g, yield 32.83%). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 895.4691 (theoretical value: 895.4673). Theoretical elemental content (%) C 64 H 58 BN3O: C, 85.79; H, 6.53; N, 4.69. Measured elemental content (%): C, 85.77; H, 6.58; N, 4.64.

[0333] Synthesis Example 39: Synthesis of Compound 752

[0334]

[0335] By replacing BB-39 with an equimolar amount of BB-230, DD-39 with an equimolar amount of DD-171, and FF-39 with an equimolar amount of GG-752, and following the same steps as in Synthesis Example 2, compound 752 (8.32 g, yield 32.65%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 849.3328 (theoretical value: 849.3315). Theoretical elemental content (%) C 63 H 40 BN3: C, 89.04; H, 4.74; N, 4.94. Measured elemental content (%): C, 89.09; H, 4.70; N, 4.97.

[0336] Synthesis Example 40: Synthesis of Compound 810

[0337]

[0338] Replacing DD-45 with an equimolar amount of DD-171, FF-45 with an equimolar amount of BB-643, and GG-118 with an equimolar amount of BB-39, while following the same steps as in Synthesis Example 4, yielded compound 810 (9.87 g, yield 30.55%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1076.5041 (theoretical value: 1076.5023). Theoretical elemental content (%) C 76 H 65 BN4S: C, 84.74; H, 6.08; N, 5.20. Measured elemental content (%): C, 84.77; H, 6.03; N, 5.24.

[0339] Synthesis Example 41: Synthesis of Compound 859

[0340]

[0341] By replacing BB-140 with an equimolar amount of DD-171 and GG-118 with an equimolar amount of DD-859, and following the same steps as in Synthesis Example 5, compound 859 (9.89 g, yield 34.91%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 943.4181 (theoretical value: 943.4165). Theoretical elemental content (%) C 64 H 58 BN3S2: C, 81.42; H, 6.19; N, 4.45. Measured elemental content (%): C, 81.38; H, 6.14; N, 4.49.

[0342] Synthesis Example 42: Synthesis of Compound 870

[0343]

[0344] By replacing AA-140 with an equimolar amount of AA-346, BB-140 with an equimolar amount of DD,45, and GG-118 with an equimolar amount of GG-696, and following the same steps as in Synthesis Example 5, compound 870 (6.97 g, yield 33.78%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 687.2131 (theoretical value: 687.2118). Theoretical elemental content (%) C 48 H 26 BN3O2: C, 83.85; H, 3.81; N, 6.11. Measured elemental content (%): C, 83.89; H, 3.84; N, 6.06.

[0345] Synthesis Example 43: Synthesis of Compound 889

[0346]

[0347] Replacing FF-45 with an equimolar amount of GG-696 and GG-118 with an equimolar amount of GG-696, while following the same steps as in Synthesis Example 4, yielded compound 889 (8.17 g, yield 31.33%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 868.2637 (theoretical value: 868.2646). Theoretical elemental content (%) C 60 H 33 BN4O3: C, 82.95; H, 3.83; N, 6.45. Measured elemental content (%): C, 82.94; H, 3.86; N, 6.40.

[0348] The following are compounds other than the boron-nitrogen heterocyclic compound shown in formula (I) used in the device fabrication examples:

[0349]

[0350] 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 Tables 1 and 2.

[0351] Comparative device fabrication example 1: Comparative device 1

[0352] 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.

[0353] The following layers were deposited layer by layer on the ITO / Ag / ITO glass substrate: a) HT-12 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-12 as hole transport layer with a thickness of 120 nm; c) MCBP and compound ref-1 (mass ratio 99:1) as light-emitting layer with a thickness of 30 nm; d) TPBi as hole blocking layer with a thickness of 5 nm; e) BCP and Liq (mass ratio 1:1) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 1:9) as cathode with a thickness of 15 nm; h) CP-4 as capping layer with a thickness of 75 nm.

[0354] Comparative device fabrication examples 2-5: Comparative devices 2-5

[0355] By sequentially replacing ref-1 in the light-emitting layer with ref-2, ref-3, ref-4, and ref-5, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 5 can be obtained.

[0356] Device fabrication examples 1-42: Light-emitting devices 1-42

[0357] The ref-1 in the luminescent layer is sequentially replaced with compounds 39, 45, 118, 140, 144, 161, 171, 178, 185, 191, 208, 211, 221, 227, 228, 230, 233, 252, 285, 294, 296, 309, 346, 351, 365, 419, 424, 439, 468, 484, 492, 598, 643, 696, 720, 729, 741, 752, 810, 859, 870, and 889. All other steps are the same as in Comparative Device Preparation Example 1, thus obtaining luminescent devices 1 to 42.

[0358] Table 1

[0359]

[0360]

[0361] Comparative device fabrication example 6: Comparative device 6

[0362] 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.

[0363] The following layers were deposited layer by layer on the ITO / Ag / ITO glass substrate: a) HT-12 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-12 as hole transport layer with a thickness of 120 nm; c) MCBP, Ir(ppy)2(acac) and compound ref-1 (mass ratio 79:20:1) as light-emitting layer with a thickness of 30 nm; d) TPBi as hole blocking layer with a thickness of 5 nm; e) BCP and Liq (mass ratio 1:1) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 1:9) as cathode with a thickness of 15 nm; h) CP-4 as capping layer with a thickness of 75 nm.

[0364] Comparative device fabrication examples 7-10: Comparative devices 7-10

[0365] By sequentially replacing ref-1 in the light-emitting layer with ref-2, ref-3, ref-4, and ref-5, and following the same steps as in Comparative Device Preparation Example 6, Comparative Devices 7 to 10 can be obtained.

[0366] Device fabrication examples 43-84: Light-emitting devices 43-84

[0367] The ref-1 in the luminescent layer is sequentially replaced with compounds 39, 45, 118, 140, 144, 161, 171, 178, 185, 191, 208, 211, 221, 227, 228, 230, 233, 252, 285, 294, 296, 309, 346, 351, 365, 419, 424, 439, 468, 484, 492, 598, 643, 696, 720, 729, 741, 752, 810, 859, 870, and 889. All other steps are the same as in Comparative Device Preparation Example 6, thus obtaining luminescent devices 43–84.

[0368] Table 2

[0369]

[0370]

[0371]

[0372] The device data in Tables 1 and 2 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.

[0373] 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 in that, The boron-nitrogen heterocyclic compound has the structure shown in formula (I): Wherein, x1, x2, and x3 are independently selected from CR x Or N, wherein y1, y2, y3, and y4 are independently selected from CR y Or N, wherein z1, z2, z3, z4 are independently selected from CR z Or N, wherein u1, u2, u3, u4, u5 are independently selected from CR u Or N, the R mentioned x R y R z R u Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C6-C30 aromatic amino group, and combinations thereof, and has at most one R. y Selected from substituted or unsubstituted C1-C12 alkyl groups, and having at most one R. u Selected from substituted or unsubstituted C1-C12 alkyl groups, or two adjacent R groups x Connected to form a loop, or two adjacent Rs y Connected to form a loop, or two adjacent Rs z Connected to form a loop, or two adjacent Rs u They can be connected to form a loop, or z4 and u5 can be connected by Y, in which case both z4 and u5 are C; X is selected from one of single bond, O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; Y is selected from one of single bond, O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6; and R1, R2, R3, R4, R5, and R6 are independently selected from substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C12 alkyl groups, and substituted or unsubstituted C3-C10 cyclic groups. An alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R1 and R2 linked together to form a ring, or R4 and R5 linked together to form a ring; The 'a' is selected from 0, 1, or 2; Each time R0 appears, it is selected, either identically or differently, from one of the following groups: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or combinations thereof: Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the h mentioned 11 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 i 11 Each time it appears, it is selected from 0, 1, or 2, either the same or different. The R mentioned 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or two adjacent R groups. 11 Connected to form a ring; The R mentioned 12 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C10 cycloalkyl group; The R mentioned 13 Selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof; X1 is selected from O, S, and CR. 14 R 15 or NR 16 X2 is selected from O, S or NR. 17 The R mentioned 14 R 15 R 16 R 17 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, a monovalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof, or R 14 R 15 Connected to form a ring; The L is selected from a single bond, one of the following groups: Wherein, the a 101 Each 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 the same or different; The R mentioned 101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic 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, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted silyl group; The ring A and ring B are independently selected from one of the following: a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring, a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a fused ring of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring. The ring C is selected from one of the following: a substituted or unsubstituted aromatic ring of C6 to C30, a substituted or unsubstituted heteroaromatic ring of C3 to C11, a fused ring of a substituted or unsubstituted aromatic ring of C6 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7, and a fused ring of a substituted or unsubstituted heteroaromatic ring of C3 to C30 and a substituted or unsubstituted aliphatic ring of C3 to C7. The boron-nitrogen heterocyclic compound is not one of the following compounds:

2. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, The boron-nitrogen heterocyclic compound has a structure shown in one of formulas (II-A) to (II-F): In equations (II-A) and (II-C), z4 and u5 are not connected by Y'; X' is selected from one of O, S, Se, CR1R2, SiR1R2, GeR1R2, and NR3; The Y' is selected from one of O, S, Se, CR4R5, SiR4R5, GeR4R5, and NR6.

3. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, The R mentioned x R y R z R u Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane Alkyl; norbornel alkyl; deuterated, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl The following groups, substituted or unsubstituted, are selected 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: benzene One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

4. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, and R6 are independently selected from trimethylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornel; deuterium atom; fluorine atom; cyano; trimethylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; The following groups, substituted or unsubstituted, are selected from the following groups: isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, and quinazolinyl: phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

5. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, The rings A, B, and C are independently selected from one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthyl ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted triphenylene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted isoquinoline ring, substituted or unsubstituted quinoxaline ring, and substituted or unsubstituted quinazoline ring.

6. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, The aforementioned Selected from one of the following groups, wherein Indicates the connection key with L: Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the e mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the g mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7, either the same or different. The R mentioned 21 Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; trifluoromethyl; deuterated methyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane Alkyl; norbornel alkyl; deuterated, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl The following groups, substituted or unsubstituted, are selected 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: benzene One of the following: yl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, fluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

7. The boron-nitrogen heterocyclic compound according to claim 1, characterized in that, The boron-nitrogen heterocyclic compound is selected from one of the following compounds:

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises the boron-nitrogen heterocyclic compound as described in any one of claims 1 to 7.

9. 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, characterized in that, The organic layer contains the boron-nitrogen heterocyclic compound as described in any one of claims 1 to 7.

10. 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 includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The light-emitting layer contains the boron-nitrogen heterocyclic compound as described in any one of claims 1 to 7.

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