Boron-nitrogen compound and organic electroluminescent device thereof

Abstract

The invention discloses a boron-nitrogen compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent devices. According to the boron-nitrogen-containing organic compound provided by the invention, rigid groups are introduced, so that close packing and pi-pi interaction among molecules are effectively inhibited, the rigidity of the molecules is increased, and the vibration relaxation of the molecules is reduced. When the compound is applied to a light-emitting layer of an organic electroluminescent device, the excellent performance of high efficiency, high color purity and low-efficiency roll-off can be achieved at the same time, good thermal stability and thin film form stability are shown, the color purity of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

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

[0002] Organic light-emitting diode (OLED) technology, with its outstanding advantages such as self-illumination, high color gamut, ultra-thin and lightweight design, and flexibility, continues to see increasing demand in the high-end display field (such as 8K ultra-high-definition TVs and foldable screen phones). As OLED technology develops towards higher resolution, higher refresh rates, and longer standby times, more stringent requirements are being placed on the performance of organic functional materials, especially in terms of luminous efficiency, long-term stability, low-voltage driving, and color purity control.

[0003] In the structure of OLED devices, the emissive layer is the core region for photon radiation, and the performance of the doped materials directly determines the luminous quality and full-color display effect of the device. Boron-nitrogen compounds, as a novel class of organic functional materials, can effectively adjust the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the material due to the unique electronic effect of the BN bond, allowing it to flexibly adapt to the functional requirements of the emissive layer. Simultaneously, by controlling the substituents and conjugated framework structure of B and N atoms, the emission wavelength of the material can be precisely controlled to match luminous requirements, thus becoming one of the key research areas in the field of OLED materials. Although boron-nitrogen compounds have great potential in the field of OLED materials, they still have significant shortcomings when adapted to high-end applications. In the high-end display field, when used as an emissive layer, they suffer from insufficient color purity and severe efficiency roll-off, especially when used for GD (Glass Difference), they are prone to wavelength shift and brightness attenuation, making it difficult to meet the requirements of 8K ultra-high definition.

[0004] Based on this, developing a boron-nitrogen compound that combines high color purity, excellent thermal stability, and efficient charge transport performance is of great practical significance for the industrial application of OLED technology in high-end displays, and is also a current research challenge and core need in this field. Summary of the Invention

[0005] To address the aforementioned problems, the present invention aims to provide a boron-nitrogen compound and its organic electroluminescent device, which can improve the color purity, luminous efficiency, and lifespan of the device.

[0006] This invention provides a boron nitride compound and its organic electroluminescent device, wherein the boron nitride compound is selected from the structure shown in Formula 1:

[0007] The ring B is selected from substituted or unsubstituted C3~C20 alicyclic rings; The ring C is selected from any one of the following: unsubstituted or substituted C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaromatic rings, fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C6-C30 aromatic rings, and fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C2-C30 heteroaromatic rings; X1 is selected from single bonds, O, S, CRaRb, NRc, GeRaRb, or Se; Each of the n's is independently selected from CR2 or N; Each x is independently selected from CR5 or N, and the x connected to L is selected from C; R1, R2, R3, R5, Ra, Rb, and Rc are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, and substituted or unsubstituted C2-C20 alkyne. The following are possible combinations of: alkyl, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring; or adjacent R1 groups connected to form a substituted or unsubstituted ring. When x is selected from CR5 and is adjacent to R1, R1 and R5 can be connected to form a substituted or unsubstituted ring; When x is selected from CR5 and is adjacent to ring B, the substituent on ring B and R5 can be connected to form a substituted or unsubstituted ring; When two or more R2s exist simultaneously, the two or more R2s are the same or different, or adjacent R2s are connected to form any of the following rings.

[0008] Each of the terms 'a' is independently selected from CRd or N; Each of the X2 values ​​is independently selected from CRe or N; Each of the Us is independently selected from O, S, CRfRg, or NRh; Each of the V values ​​is independently selected from a single bond, O, S, CRfRg, or NRh; Rd, Re, Rf, Rg, Rh, and Rx are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C Any one of the following: a 6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection between adjacent Rf and Rg. When two or more Rds exist simultaneously, the two or more Rds are the same or different, or adjacent Rds are connected to form substituted or unsubstituted rings; When R5 is connected with the adjacent R1 to form a substituted or unsubstituted ring, and / or R5 is connected with the substituent on the adjacent ring B to form a substituted or unsubstituted ring, the A is selected from hydrogen, deuterium, tritium, and Al. Otherwise, A is selected from A1; The A1 is selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted amino, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic rings, or any combination of two or more of the groups shown in formulas (1-1) to (1-16).

[0009] When all three x are selected from CR5 and the two R5 not connected to L are selected from hydrogen or deuterium, A is selected from cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1~C20 alkoxy, substituted or unsubstituted C2~C20 alkenyl, substituted or unsubstituted C2~C20 alkynyl, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C3~C20 alicyclic and C6~C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C3~C20 alicyclic and C2~C30 heteroaromatic ring fused cycloalcohol, or selected from formula (1-2) to formula (1-15), or R5 is connected with adjacent R1 to form a substituted or unsubstituted ring, or R5 is connected with the substituent on adjacent ring B to form a substituted or unsubstituted ring; The ring D is selected from substituted or unsubstituted C3~C20 alicyclic rings; Each of the c's is independently selected from CRj or N; Each of the 'e's is independently selected from CRk or N; Y1 is selected from O, S, CRlRm or NRn; The Y2 is selected from O, S, or CRlRm; The X3 is selected from CRo or N; The Y3 is selected from single bonds, O, S, or CRlRm; The terms Ri, Rj, Rk, Rl, Rm, Rn, Ro, Rp, and Rv are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted... The following are possible combinations of: a substituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection of adjacent R1 and Rm. When two or more Rj exist simultaneously, the two or more Rj are the same or different, or adjacent Rj are connected to form a substituted or unsubstituted ring; When two or more Rk exist simultaneously, the two or more Rk are the same or different, or adjacent Rk are connected to form any of the following rings.

[0010] The s is selected from CRq or N; The Y4 is selected from O, S, or NRr; The Y5 is selected from CRu or N; The Y6 is selected from single bonds, O, S, CRsRt, or NRr; The Y7 is selected from O, S, CRsRt, or NRr; Rq, Rr, Rs, Rt, Ru, and Ry are each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The L is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 arylene, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroarylene; The a1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0011] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises one or more of the boron nitrogen compounds described in the present invention.

[0012] Beneficial effects

[0013] The boron-nitrogen compound of this invention is suitable for the color accuracy requirements of high-end displays. It is stable and has a more twisted molecular structure, which effectively suppresses the close packing of molecules and π-π interactions. When applied to the light-emitting layer of organic electroluminescent devices, it can improve display quality and luminous efficiency, and significantly extend the life of the device. Detailed Implementation

[0014] The technical solutions of this invention will be clearly and completely described below with reference to embodiments. Obviously, the described embodiments are only a part of this invention, and not all of it. Various equivalent modifications made by those skilled in the art after studying this invention should fall within the protection scope defined by this invention.

[0015] In the compounds of this invention, any atom that does not explicitly specify a particular isotope encompasses all stable isotopes of that atom, and includes such atoms in both natural and non-natural isotopic abundance forms.

[0016] In the instruction manual, " "This refers to the portion that is connected to another substituent." It can be attached to any optional position of the attached group / fragment. For example... express , or And so on.

[0017] In the specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , And so on.

[0018] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0019] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and particularly preferably having 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, isomeric groups 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.

[0020] The silyl group referred to in this invention is a -Si(R)3 group, wherein each R is the same or different and is selected from any of the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings. Preferably, each R is the same or different from the following groups: hydrogen, deuterium, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, tetrahydronaphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, ditert-butylphenylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc., but are not limited thereto.

[0021] The cycloalkyl group described in this invention refers to a monovalent group in a cyclic alkane molecule after removing one hydrogen atom, 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, norbornene, etc., but are not limited thereto.

[0022] The alkoxy group described in this invention is represented by -O-alkyl. Examples and preferred examples of alkyl groups are the same as described above. It may be a straight-chain alkoxy group or a straight-chain alkoxy group, preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, etc., but are not limited thereto.

[0023] The alkenyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include vinyl, propenyl, isopropenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosene, 2-ethylhexenyl, allyl, cyclohexenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, phenylvinyl, or styryl, etc., but are not limited thereto.

[0024] The alkynyl group described in this invention refers to a monovalent group in an alkyne molecule after removing one hydrogen atom. It can be a straight-chain alkynyl group or a branched-chain alkynyl group, preferably having 2 to 16 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include acetylenyl, propynyl, butynyl, pentylenyl, hexynyl, heptylenyl, methylbutynyl, phenylacetylenyl, phenylpropynyl, naphthylacetylenyl, diphenylacetylenyl, etc., but are not limited thereto.

[0025] The aryl group described in this invention is represented by -O-aryl. The aromatic hydrocarbon portion of the aryl group includes monocyclic aromatic hydrocarbons, polycyclic aromatic hydrocarbons, fused-ring aromatic hydrocarbons, and heterocyclic aromatic hydrocarbons, etc., preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms. Specific examples may include phenoxy, biphenyloxy, naphthoxy, anthraceneoxy, phenanthroxy, furanoxy, thiophenoxy, pyridinoxy, quinolinoxy, benzofuranoxy, benzothiophenoxy, benzyloxy, phenethoxy, etc., but are not limited thereto.

[0026] The aryl group mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly 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.

[0027] The heteroaryl group described in this invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 25 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazoleyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxaloyl, quinoxaloyl, benzoquinoxaloyl, benzoquinoxaloyl, o-phenanthrolinel, naphridyl, indoleyl, benzothiopheneyl, benzofuranyl, N-hexabenzothiopheneyl, N-hexabenzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, benzoindoleyl, dibenzofuranyl, N-hexadibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl. N-hexabenzothiopheneyl, benzodibenzothiopheneyl, dibenzoxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, N-hexacarbazoleyl, benzocarbazoleyl, furanocarbazoleyl, thienenocarbazoleyl, oxazolocarbazoleyl, thiazocarbazoleyl, benzofuranocarbazoleyl, benzothienenocarbazoleyl, dioxacyclohexanecarbazoleyl, dithiacyclohexanecarbazoleyl, acridineyl, 9,10-dihydro-9,9-dimethylacridyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, spirofluoroxanthyl, spirofluorenoxazanthyl, spirofluorenoxazinyl, spirofluorenthanethyl, indole-carbazoleyl, indole-phenoxazinyl, indole-phenthiazinyl, etc., but not limited to these.

[0028] The amine group described in this invention refers to a monovalent or polyvalent group formed by removing one or more hydrogen atoms from an ammonia molecule. It can be a primary amine group (-NH2), a secondary amine group (-NHR), or a tertiary amine group (-NR2), wherein R is independently hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, or substituted or unsubstituted... The group comprises any one of the following: an alkenyl group (C2-C20), a substituted or unsubstituted alkynyl group (C2-C20), a substituted or unsubstituted aryl group (C6-C30), a substituted or unsubstituted aryl group (C6-C30), a substituted or unsubstituted heteroaryl group (C2-C30), a substituted or unsubstituted amino group, a fused cycloalcoholic group (C3-C20 alicyclic ring and C6-C30 aromatic ring), or a fused cycloalcoholic group (C3-C20 alicyclic ring and C2-C30 heteroaryl ring). Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, tetrahydronaphthyl. Specific examples may include, but are not limited to, amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, methylethylamino, n-propylamino, isopropylamino, n-butylamino, tert-butylamino, isobutylamino, sec-butylamino, n-pentylamino, n-hexylamino, cyclohexylamino, benzylamino, aniline, tert-butylphenylamino, pyridineamino, dipyridineamino, pyrimidineamino, and dipyrimidineamino.

[0029] The fused alicyclic and aromatic ring groups mentioned in this invention refer to the general term for monovalent groups formed by removing one hydrogen atom after the aromatic ring and the alicyclic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The alicyclic ring preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, and particularly preferably 3 to 10 carbon atoms. Specific examples may include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0030] The fused alicyclic and heteroaromatic rings described in this invention refer to the collective term for a monovalent group remaining after aliphatic and heteroaromatic rings are fused together and one hydrogen atom is removed. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The alicyclic ring preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, and particularly preferably 3 to 10 carbon atoms. Specific examples may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc., but are not limited thereto.

[0031] The semi-fused cyclic group formed by the fusion of alicyclic and aromatic rings in this invention refers to a group with two bonding sites formed by the fusion of an alicyclic and aromatic rings, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of alicyclic and aromatic rings, the difference being that the divalent group formed by the fusion of alicyclic and aromatic rings is a divalent group.

[0032] The semi-fused cyclic group formed by the fusion of an alicyclic ring and a heteroaromatic ring as described in this invention refers to a group formed by the fusion of an alicyclic ring and a heteroaromatic ring with two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of alicyclic rings and heteroaromatic rings, the difference being that the divalent group formed by the fusion of alicyclic rings and heteroaromatic rings is a divalent group.

[0033] In the context of this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by a non-hydrogen group.

[0034] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl," refers to being independently monosubstituted or polysubstituted by the following groups: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C2... The following are possible interpretations: alkenyl group (0), substituted or unsubstituted C2-C20 alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, benzocyclopentyl, benzocyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl, tert-butyl. Phenyl, adamantyl-substituted phenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, spirofluorenoxanthyl, spirofluorenoxanthyl, spirofluorenoxanthyl, indolocarbazolyl, indolophenoxazinyl, indolophenthiaazinyl, etc., but not limited to these.

[0035] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0036] 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, benzocyclopentenyl, cyclopentene, cyclopentane, benzocyclopentane, benzocyclohexenyl, cyclohexene, cyclohexane, benzocyclohexane, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0037] This invention provides a boron-nitrogen compound, wherein the boron-nitrogen compound is selected from the structure shown in Formula 1:

[0038] The ring B is selected from substituted or unsubstituted C3~C20 alicyclic rings; The ring C is selected from any one of the following: unsubstituted or substituted C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaromatic rings, fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C6-C30 aromatic rings, and fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C2-C30 heteroaromatic rings; X1 is selected from single bonds, O, S, CRaRb, NRc, GeRaRb, or Se; Each of the n's is independently selected from CR2 or N; Each x is independently selected from CR5 or N, and the x connected to L is selected from C; R1, R2, R3, R5, Ra, Rb, and Rc are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, and substituted or unsubstituted C2-C20 alkyne. The following are possible combinations of: alkyl, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring; or adjacent R1 groups connected to form a substituted or unsubstituted ring. When x is selected from CR5 and is adjacent to R1, R1 and R5 can be connected to form a substituted or unsubstituted ring; When x is selected from CR5 and is adjacent to ring B, the substituent on ring B and R5 can be connected to form a substituted or unsubstituted ring; When two or more R2s exist simultaneously, the two or more R2s are the same or different, or adjacent R2s are connected to form any of the following rings.

[0039] Each of the terms 'a' is independently selected from CRd or N; Each of the X2 values ​​is independently selected from CRe or N; Each of the Us is independently selected from O, S, CRfRg, or NRh; Each of the V values ​​is independently selected from a single bond, O, S, CRfRg, or NRh; Rd, Re, Rf, Rg, Rh, and Rx are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C Any one of the following: a 6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection between adjacent Rf and Rg. When two or more Rds exist simultaneously, the two or more Rds are the same or different, or adjacent Rds are connected to form substituted or unsubstituted rings; When R5 is connected with the adjacent R1 to form a substituted or unsubstituted ring, and / or R5 is connected with the substituent on the adjacent ring B to form a substituted or unsubstituted ring, the A is selected from hydrogen, deuterium, tritium, and Al. Otherwise, A is selected from A1; The A1 is selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted amino, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic rings, or any combination of two or more of the groups shown in formulas (1-1) to (1-16).

[0040] When all three x are selected from CR5 and the two R5 not connected to L are selected from hydrogen or deuterium, A is selected from cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1~C20 alkoxy, substituted or unsubstituted C2~C20 alkenyl, substituted or unsubstituted C2~C20 alkynyl, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C3~C20 alicyclic and C6~C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C3~C20 alicyclic and C2~C30 heteroaromatic ring fused cycloalcohol, or selected from formula (1-2) to formula (1-15), or R5 is connected with adjacent R1 to form a substituted or unsubstituted ring, or R5 is connected with the substituent on adjacent ring B to form a substituted or unsubstituted ring; The ring D is selected from substituted or unsubstituted C3~C20 alicyclic rings; Each of the c's is independently selected from CRj or N; Each of the 'e's is independently selected from CRk or N; Y1 is selected from O, S, CRlRm or NRn; The Y2 is selected from O, S, or CRlRm; The X3 is selected from CRo or N; The Y3 is selected from single bonds, O, S, or CRlRm; The terms Ri, Rj, Rk, Rl, Rm, Rn, Ro, Rp, and Rv are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted... The following are possible combinations of: a substituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection of adjacent R1 and Rm. When two or more Rj exist simultaneously, the two or more Rj are the same or different, or adjacent Rj are connected to form a substituted or unsubstituted ring; When two or more Rk exist simultaneously, the two or more Rk are the same or different, or adjacent Rk are connected to form any of the following rings.

[0041] The s is selected from CRq or N; The Y4 is selected from O, S, or NRr; The Y5 is selected from CRu or N; The Y6 is selected from single bonds, O, S, CRsRt, or NRr; The Y7 is selected from O, S, CRsRt, or NRr; Rq, Rr, Rs, Rt, Ru, and Ry are each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The L is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 arylene, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroarylene; The a1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0042] Preferably, R1 and R3 are each independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, methyldiphenylsilyl, dimethylphenylsilyl, ditert-butylphenylsilyl, diethylphenylsilyl Diisopropylphenylsilyl, tert-butyldibenzosilyl, isopropyldiphenylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, isopropoxy, sec-butoxy, tert-butoxy, vinyl, propenyl, isopropenyl, butenyl, phenoxy, biphenyloxy, naphthoxy, anthraquinoneoxy, phenanthreneoxy, phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthrene, triphenylene, 9,9-dimethylfluorene, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, Spirofluorenyl, Furanyl, Benzofuranyl, Dibenzofuranyl, Thiopheneyl, Benzothiopheneyl, Dibenzothiopheneyl, Pyridyl, Pyrazinyl, Pyridazinyl, Quinolinyl, Isoquinolinyl, Quinazolinyl, Quinoxalinyl, Carbazoleyl, Phenoxazinyl, Phenthiazinyl, Indolyl, Imidazolyl, Oxazolyl, Thiazyl Azolyl, benzoxazole, benzothiazolyl, naphthoxazole, naphthothiazolyl, naphthofuranyl, benzofuranocarbazoyl, benzothiophenecarbazoyl, spirofluorenoxanthyl, spirofluorenoxanthyl, spirofluorenoxacridyl, spirofluorenthranyl, acridineyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclopentenyl, benzocyclohexaneyl, benzocyclohexenyl, benzocycloheptaneyl, pyridinocyclobutane, pyridinocyclopentaneyl, pyridinocyclohexaneyl, pyridinocycloheptaneyl, pyridinocyclopentenyl, pyridinocyclohexenyl, dimethylamino, diethylamino, di-n-propylamino, methylethylamino, n-propylamino, isopropylamino, n-butylamino, tert-butylamino, isobutylamino, sec-butylamino, n-pentylamino n-Hexylamino, cyclohexylamino, dicyclohexylamino, benzylamino, aniline, diphenylamino, tert-butylphenylamino, pyridineamino, dipyridineamino, pyrimidineamino, dipyrimidineamino, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norborneol Alkyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-methyl-9-phenylfluorenyl, deuterated spirofluorenyl, deuterated benzofuranyl, deuterated dibenzofuranyl yl, deuterated benzothiophene, deuterated dibenzothiophene, deuterated pyridyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl The following are all of the following: phenyl groups substituted with methyl, isopropyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, trimethylsilyl-substituted phenyl, trimethylsilyl-substituted biphenyl, trimethylsilyl-substituted naphthyl, triphenylsilyl-substituted phenyl, and deuterated diphenylamino.

[0043] Preferably, the ring B is selected from any one of the following groups:

[0044] Each of the R9s is independently selected from any one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring; k1 is selected from 0, 1, or 2; k2 is selected from 0, 1, 2, 3, or 4; k3 is selected from 0, 1, 2, 3, 4, 5, or 6; k4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; k5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; k6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0045] Preferably, the boron-nitrogen compound is selected from any one of the structures of formulas 2-1 to 2-6.

[0046] The m is selected from CR1 or N; The z is selected from CR4 or N; The X4 is selected from single bonds, O, S, CR6R7 or NR8; R4, R6, R7, and R8 are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C8, and so on. Any one of the following: a C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or R6 and R7 linked together to form a substituted or unsubstituted ring; When two or more R4s exist at the same time, the two or more R4s are the same or different, or adjacent R4s are connected to form substituted or unsubstituted rings; a2 is selected from 0, 1 or 2; a3 is selected from 0 or 1.

[0047] Preferably, among the multiple n in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0048] Preferably, among the multiple m in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0049] Preferably, among the multiple z's of each six-membered ring, at most three, at most two, or at most one is selected from N.

[0050] Preferably, among the multiple x's in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0051] More preferably, the boron-nitrogen compound is selected from any one of the structures shown below.

[0052] a4 is selected from 0, 1, 2, 3 or 4; g1 is selected from 0, 1 or 2; h1 is selected from 0, 1 or 2; The j1 is selected from 0, 1, 2, 3, 4, 5 or 6; the j2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the j3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The q1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0053] Preferably, R2, R4, and R5 are each independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, methyldiphenylsilyl, dimethylphenylsilyl, ditert-butylphenylsilyl, diethylphenylsilyl, diisopropylphenylsilyl, tert-butyldiphenylsilyl Benzosilyl, isopropyldiphenylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornel, adamantane, phenyl, biphenyl, triphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, azadibenzofuranyl, azadibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, carbazole, 9-carbazole, benzocarb Azolyl, naphthocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenthiazinyl, indoleyl, imidazole, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, naphthooxazolyl, naphthothiazolyl, naphthofuranyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzooxazolyl, naphthobenzothiazolyl, anthracene benzofuranyl, anthracene benzothiaphenyl, anthracene benzoxazolyl, anthraquinonethiazolyl, phenanthrenebenzofuranyl, phenanthrenebenzothiophenyl, phenanthrenebenzoxazolyl, phenanthrenebenzothiazolyl, benzofuranocarbazolyl, benzothiaphenecarbazolyl, benzofuranoindolyl, benzothiapheneindolyl, indole-indolyl, indolo-indolyl, spirofluoreneoxanthracenel, spirofluorenethoxanthracenel, spirofluoreneacridyl, spirofluoreneanthracenel, acrylonitrile The group consisting of any one or a combination of two or more of the following: pyridyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclopentenyl, benzocyclohexaneyl, benzocycloheptane, pyridinocyclobutane, pyridinocyclopentane, pyridinocyclohexaneyl, pyridinocycloheptane, pyridinocyclopentenyl, pyridinocyclohexenyl, dimethylamino, diethylamino, di-n-propylamino, methylethylamino, n-propylamino, isopropylamino, n-butylamino, tert-butylamino, isobutylamino, sec-butylamino, n-pentylamino, n-hexylamino, cyclohexylamino, dicyclohexylamino, benzylamino, aniline, diphenylamino, tert-butylphenylamino, pyridinamino, dipyridinamino, pyrimidineamino, and dipyrimidineamino.

[0054] Preferably, the substituents in "substituted or unsubstituted" in R2, R4, and R5 are selected from deuterium, cyano, halogen, nitro, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, phenyl, fluoranyl, tetraphenyl, pentaphenyl, fluorenyl, carbazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridyl The ring may contain any one or a combination of the following: oxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, dimethylamino, diethylamino, di-n-propylamino, methylethylamino, n-propylamino, isopropylamino, n-butylamino, tert-butylamino, isobutylamino, sec-butylamino, n-pentylamino, n-hexylamino, cyclohexylamino, dicyclohexylamino, benzylamino, aniline, diphenylamino, tert-butylphenylamino, pyridinylamino, dipyridinylamino, pyrimidineamino, and dipyrimidineamino, or adjacent substituents forming a substituted or unsubstituted ring.

[0055] Preferably, the adjacent R2s are connected to form any one of the following rings:

[0056] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2 or 3; the n3 is selected from 0, 1 or 2; the n4 is selected from 0 or 1; the n5 is selected from 0, 1, 2, 3, 4, 5 or 6; and the n6 is selected from 0, 1, 2, 3, 4 or 5.

[0057] Preferably, any one of the following rings can be formed between adjacent Rk:

[0058] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2 or 3; the m3 is selected from 0, 1 or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4 or 5.

[0059] Preferably, A1 is selected from cyano, halogen, nitro, substituted or unsubstituted groups including: methyl, ethyl, propyl, isopropyl, tert-butyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, di-tert-butylphenylsilyl, tert-butyldiphenylsilyl, tripyridylsilyl, pyridinediphenylsilyl, dipyridylphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl The following groups are permitted: dimethylamino, adamantylamino, norbornelalkyl, benzoalkyl, norbenzoalkyl, dimethylamino, diethylamino, di-tert-butylamino, methylethylamino, methyl-tert-butylamino, diphenylamino, di(tert-butyl-substituted phenyl)amino, di(silyl-substituted phenyl)amino, diphenylamino, dinaphthylamino, dipyridylamino, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, pyridocyclopentane, pyridocyclohexane, or any one of the following groups.

[0060] Each of the Rz groups is independently selected from any one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, or 3; the d4 is selected from 0, 1, or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d6 is selected from 0, 1, 2, 3, 4, 5, or 6; the d7 is selected from 0, 1, 2, 3, 4, 5, or 6; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the d11 is selected from 0 or 1. The value of e1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the value of e2 is selected from 0, 1, 2, 3, 4, 5 or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. The f1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The substituents in "substituted or unsubstituted" as described in A1 of this invention are selected from deuterium, tritium, cyano, fluorine, nitro, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, phenanthrene, fluoranyl, tetraphenyl, pentaphenyl, fluorenyl, carbazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, azizobenzofuranyl, azizobenzothiophene The following are all of the following: phenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, azabenzooxazolyl, azabenzothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl.

[0061] Preferably, L is selected from single-bonded or substituted or unsubstituted groups such as: phenylene, biphenylene, terphenylene, tetraphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, tetraphenylene, pyrene, perylene, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, spirofluorenoxanthyl, spirofluorenthixanthyl, spirofluorenoxacridyl, spiroanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentane... The following is a list of compounds: alkenyl, benzocyclohexenyl, pyridinylcyclopentyl, pyridinylcyclohexenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxazinyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, azabenzofuranyl, azabenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, benzooxazolyl, benzothiazolyl, azabenzooxazolyl, azabenzothiazolyl, dioxinyl, phenoxazinyl, and phenthiazolyl.

[0062] Particularly preferably, the boron-nitrogen compound is selected from any one of the following structures: .

[0063] The above lists some specific structural forms of compounds of Formula 1 of the present invention, but the present invention is not limited to these chemical structures. Any structure based on the structure shown in Formula 1 and with substituents as defined above should be included.

[0064] Furthermore, this invention also provides a method for preparing the compound of Formula 1, the synthetic route of which is shown below, but is not limited thereto.

[0065] Z4 is selected from any one of F, Cl, Br, and I; The main reaction types involved in this invention are Suzuki coupling reaction and Buchiwald-Hartwig coupling reaction.

[0066] In addition, the present invention provides an organic electroluminescent device comprising one or more of the boron nitrogen compounds described in the present invention.

[0067] Preferably, the organic electroluminescent device comprises a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside either the cathode or the anode, characterized in that the organic layer comprises one or more of the boron-nitrogen compounds described in this invention.

[0068] Preferably, the organic electroluminescent device comprises a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a host material and a dopant material, wherein the dopant material comprises one or more of the boron-nitrogen compounds described in this invention.

[0069] Specifically, the organic layer includes, but is not limited to, a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a light-emitting auxiliary layer.

[0070] Preferably, "the outer side of either the cathode or the anode" means the side of the cathode facing away from the anode or the side of the anode facing away from the cathode.

[0071] As the anode of the present invention, a transmission electrode, a reflection electrode, or a semi-transmission electrode can be selected. When the anode is a transmission electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), tin oxide (SnO2), or any combination thereof. When the anode is a semi-transmission electrode or a reflection electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-silver (Mg-Ag), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or any combination thereof.

[0072] As the hole injection layer of the present invention, a material with good hole-accepting ability is preferred. Specific examples include, but are not limited to, metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrene compounds, quinacridones, perylene compounds, and other substances with high hole injection capacity.

[0073] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Specific examples may include diphenylamine compounds, fluorene compounds, carbazole compounds, benzidine compounds, etc., and other materials with hole mobility of 10⁻⁶ cm⁻¹ may also be used. 2 Substances with a value of / Vs or higher, but not limited to these.

[0074] The light-emitting layer material described in this invention typically contains a dopant material and a host material. The dopant material is a boron-nitrogen compound as shown in Formula 1 of this invention. The host material of the light-emitting layer needs to possess carrier transport balance properties and also needs appropriate energy levels to effectively transfer excitation energy to the dopant material.

[0075] The main material can include a single main material or two main materials.

[0076] The dual-body material may include a first body material and a second body material, and preferably at least one of the first body material and the second body material is a TADF material.

[0077] TADF materials refer to materials exhibiting thermally activated delayed fluorescence (TADF). TADF is a process of thermally activated re-emission of triplet excitons. Specifically, after thermal activation, triplet excitons transition to higher vibrational energy levels, then reach a similar singlet vibrational energy level via reverse intersystem crossing, ultimately generating fluorescence through radiative transitions. Based on this, devices can simultaneously utilize both generated singlet and triplet excitons, maximizing the utilization rate of electroexcitons within the device to nearly 100%. Compared to traditional fluorescent materials, TADF materials possess significantly higher exciton utilization.

[0078] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material; Exciton-sensitized materials can perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-nitrogen compound shown in Formula 1 of this invention, when used in combination with exciton-sensitized materials, has a significant effect on improving device efficiency and addressing issues such as exciton annihilation and efficiency reduction in the device.

[0079] As the electron transport layer material of the present invention, materials with high electron mobility are preferred. Specific examples may include imidazoles, carbazole derivatives, oxazole derivatives, o-phenanthroline compounds, triazoles, metal chelates, azabenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, benzimidazoles, etc., but are not limited thereto.

[0080] As the electron injection layer material of the present invention, a material with a low work function is preferred. Specific examples may include: metals, 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, metal complexes, etc. Examples may include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0081] As the cathode of the present invention, a transmission electrode, a semi-reflection electrode, or a reflection electrode can be selected. When the cathode is a transmission electrode, the cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflection electrode or a reflection electrode, the cathode material can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0082] The organic layer of the aforementioned organic electroluminescent device can be deposited by vacuum deposition, spin coating, casting, Langmuir-Brønder (LB) method, etc. When using vacuum deposition, the vacuum deposition conditions vary depending on the compound.

[0083] The fabrication of the above-described organic electroluminescent device is specifically described in the following embodiments. However, the following embodiments are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.

[0084] Preparation and characterization of compounds

[0085] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0086] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0087] [Synthetic Example 1] Preparation of intermediate h-184:

[0088] Under nitrogen protection, k-184 (116.60 g, 450.00 mmol), e-184 (202.23 g, 450.00 mmol), K2CO3 (124.39 g, 900.00 mmol), Pd(PPh3)4 (5.20 g, 4.50 mmol), and 1500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate h-184 (197.02 g, 75% yield). HPLC analysis showed that the purity of the solid was ≥99.86%. Mass spectrometry m / z: 583.2869 (theoretical value: 583.2875).

[0089] [Synthetic Example 2] Preparation of intermediate h-224:

[0090] Under nitrogen protection, K-184 (116.60 g, 450.00 mmol), B'-56 (132.96 g, 450.00 mmol), sodium tert-butoxide (64.87 g, 675.00 mmol), and 1500 mL of toluene were added to a reaction flask. After purging the air three times with nitrogen, Pd(OAc)2 (1.01 g, 4.50 mmol) and P(t-Bu)3 (0.5 M toluene solution, 108 mL, 9.00 mmol) were added. The mixture was stirred at reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the filter cake was washed with distilled water. Finally, the filter cake was recrystallized from ethyl acetate to give intermediate H-224 (156.51 g, yield 76%). HPLC analysis showed that the solid purity was ≥99.85%. Mass spectrometry m / z: 457.2418 (theoretical value: 457.2406).

[0091] [Synthetic Example 3] Preparation of intermediate e-276:

[0092] Preparation of intermediate m-276: Under nitrogen protection, b'-56 (111.77 g, 400 mmol), l-276 (107.02 g, 400 mmol), and sodium tert-butoxide (57.66 g, 600 mmol) dissolved in 1200 mL toluene were added to a reaction flask with stirring. Pd2(dba)3 (3.66 g, 4.0 mmol) and X-Phos (3.81 g, 8.0 mmol) were then added, and the mixture was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded intermediate m-276 (134.23 g, 72% yield). HPLC analysis showed a solid purity ≥99.86%. Mass spectrometry m / z: 465.2214 (theoretical value: 465.2223).

[0093] Preparation of intermediate e-276: Under a nitrogen atmosphere, m-276 (144.48 g, 310 mmol), pinacol diborate (78.72 g, 310 mmol), and potassium acetate (60.85 g, 620 mmol) were added sequentially to a reaction flask. Then, 1500 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (2.5 g, 3.1 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give product e-276 (140.01 g, yield 81%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 557.3478 (theoretical value: 557.3465).

[0094] [Synthetic Example 4] Preparation of intermediate e'-467:

[0095] Following the preparation method of Synthesis Example 3, l-276 was replaced with an equimolar amount of l-467 to obtain intermediate e-467 (113.67 g), with an HPLC purity of ≥99.84%. Mass spectrometry m / z: 482.3114 (theoretical value: 482.3105).

[0096] [Synthetic Example 5] Preparation of intermediate e-469:

[0097] Following the preparation method of Synthesis Example 3, l-276 was replaced with an equimolar amount of l-469 to obtain intermediate e-469 (130.18 g), with HPLC purity ≥ 99.83%. Mass spectrometry m / z: 531.3297 (theoretical value: 531.3309).

[0098] [Synthetic Example 6] Preparation of intermediate h-554:

[0099] Following the preparation method of Synthesis Example 1, e-184 was replaced with an equimolar amount of e-36 to obtain intermediate h-554 (123.32 g), with an HPLC purity of ≥99.86%. Mass spectrometry m / z: 344.1587 (theoretical value: 344.1596).

[0100] [Synthetic Example 7] Preparation of intermediate h-571:

[0101] Following the preparation method of Synthesis Example 2, k-184 was replaced with an equimolar amount of k-571, and b'-56 was replaced with an equimolar amount of b-571 to obtain intermediate h-571 (159.26 g), with an HPLC purity ≥ 99.82%. Mass spectrometry m / z: 459.2551 (theoretical value: 459.2562).

[0102] [Synthetic Example 8] Preparation of intermediate h-649:

[0103] Following the preparation method of Synthesis Example 2, k-184 was replaced with an equimolar amount of k-571 to obtain intermediate h-649 (152.39 g), with an HPLC purity of ≥99.84%. Mass spectrometry m / z: 457.2422 (theoretical value: 457.2406).

[0104] [Synthetic Example 9] Preparation of intermediate h-657:

[0105] Following the preparation method of Synthesis Example 1, k-184 was replaced with an equimolar amount of k-657, and e-184 was replaced with an equimolar amount of e-657 to obtain intermediate h-657 (185.53 g), with an HPLC purity ≥ 99.83%. Mass spectrometry m / z: 549.2679 (theoretical value: 549.2668).

[0106] [Synthetic Example 10] Preparation of Compound 2:

[0107] Preparation of intermediate A-2: a-2 (31.65 g, 150 mmol), b-2 (153.04 g, 330 mmol), and cesium carbonate (97.75 g, 300 mmol) were dissolved in DMF (1500 mL) and refluxed under nitrogen for 10 hours. After the reaction was complete, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized from dichloromethane and methanol to give intermediate A-2 (125.23 g, yield 76%). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 1096.3458 (theoretical value: 1096.3470).

[0108] Preparation of intermediate B-2: A-2 (109.85 g, 100 mmol), c-2 (22.14 g, 110 mmol), and cesium carbonate (65.16 g, 200 mmol) were dissolved in DMF (1000 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 B-9 (98.55 g, yield 77%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 1277.4940 (theoretical value: 1277.4926).

[0109] Preparation of compound 2: Under a nitrogen atmosphere, a solution of B-2 (76.79 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 2 (20.31 g, yield 28%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1207.5666 (theoretical value: 1207.5679). Theoretical elemental content (%) C 80 H 82 BN3Si4: C, 79.50; H, 6.84; N, 3.48; Actual element content (%): C, 79.51; H, 6.85; N, 3.46.

[0110] [Synthetic Example 11] Preparation of Compound 9:

[0111] Preparation of intermediate C-9: Under a nitrogen atmosphere, d-9 (50.04 g, 220 mmol), e-9 (65.85 g, 242 mmol), potassium carbonate (60.81 g, 440 mmol), 770 mL toluene, 385 mL ethanol, and 385 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.54 g, 2.2 mmol) was added. The reaction system was heated and stirred, and refluxed for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using a toluene:ethanol ratio of 6:1 to obtain intermediate C-9 (62.67 g, yield 76%); HPLC analysis showed that the solid purity was ≥99.83%. Mass spectrometry m / z: 374.0661 (theoretical value: 374.0674).

[0112] Preparation of intermediate D-9: C-9 (56.22 g, 150 mmol), b-9 (71.21 g, 165 mmol), and cesium carbonate (97.75 g, 300 mmol) were dissolved in 1500 mL of DMF. The mixture was heated to 150 °C and refluxed for 12 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to obtain intermediate D-9 (88.47 g, 75%). HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 785.1426 (theoretical value: 785.1414).

[0113] Preparation of intermediate E-9: D-9 (78.64 g, 100 mmol), c-2 (22.14 g, 110 mmol), and cesium carbonate (65.16 g, 200 mmol) were dissolved in 1000 mL of DMF. The mixture was heated to 150 °C and refluxed for 10 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to give intermediate E-9 (75.48 g, 78%). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 966.2851 (theoretical value: 966.2869).

[0114] Preparation of compound 9: Under a nitrogen atmosphere, a solution of E-9 (58.06 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0 °C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70 °C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 9 (14.68 g, yield 26%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 940.3129 (theoretical value: 940.3117). Theoretical elemental content (%) C 66 H 45 BN2S2: C, 84.24; H, 4.82; N, 2.98; Actual element content (%): C, 84.25; H, 4.81; N, 2.97.

[0115] [Synthetic Example 12] Preparation of Compound 20:

[0116] Following the preparation method of Synthesis Example 11, d-9 was replaced with an equimolar amount of d-20, e-9 with an equimolar amount of e-20, and b-9 with an equimolar amount of b-20, yielding compound 20 (14.39 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 818.4541 (theoretical value: 818.4555). Theoretical elemental content (%) C 60 H 31 D 14 BN2: C, 88.00; H, 7.26; N, 3.42; Actual element content (%): C, 88.01; H, 7.24; N, 3.43.

[0117] [Synthetic Example 13] Preparation of Compound 30:

[0118] Preparation of intermediate F-30: Under a nitrogen atmosphere, f-30 (53.99 g, 220 mmol), e-30 (51.31 g, 242 mmol), potassium carbonate (60.81 g, 440 mmol), 770 mL toluene, 385 mL ethanol, and 38 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.54 g, 2.2 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using a toluene:ethanol ratio of 6:1 to obtain intermediate F-30 (54.16 g, yield 74%); HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 332.0202 (theoretical value: 332.0216).

[0119] Preparation of intermediate G-30: F-30 (49.91 g, 150 mmol), b-30 (98.15 g, 315 mmol), and cesium carbonate (97.75 g, 300 mmol) were dissolved in 1500 mL of DMF. The mixture was heated to 150 °C and refluxed for 15 hours under nitrogen protection. 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 G-30 (103.03 g, yield 75%). HPLC analysis showed a solid purity ≥ 99.84%. Mass spectrometry m / z: 914.3126 (theoretical value: 914.3142).

[0120] Preparation of intermediate H-30: G-30 (91.58 g, 100 mmol), c-2 (22.14 g, 110 mmol), and cesium carbonate (65.16 g, 200 mmol) were dissolved in 1000 mL of DMF. The mixture was heated to 150 °C and refluxed for 10 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to give intermediate H-30 (80.09 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 1095.4585 (theoretical value: 1095.4597).

[0121] Preparation of compound 30: Under a nitrogen atmosphere, a solution of H-30 (65.83 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was allowed to return to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 30 (18.63 g, yield 29%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1069.4858 (theoretical value: 1069.4846). Theoretical elemental content (%) C 68 H 72 BN3OSi4: C, 76.30; H, 6.78; N, 3.93; Actual element content (%): C, 76.31; H, 6.77; N, 3.94.

[0122] [Synthetic Example 14] Preparation of Compound 36:

[0123] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-36, and b-30 was replaced with an equimolar amount of b-36, yielding compound 36 (19.87 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1067.4818 (theoretical value: 1067.4806). Theoretical elemental content (%) C 77 H 62 BN3Si: C, 86.58; H, 5.85; N, 3.93; Actual element content (%): C, 86.57; H, 5.84; N, 3.95.

[0124] [Synthetic Example 15] Preparation of Compound 56:

[0125] Preparation of intermediate F-56: Under a nitrogen atmosphere, f-56 (61.36 g, 250 mmol), e-56 (47.30 g, 275 mmol), potassium carbonate (69.11 g, 500 mmol), 800 mL toluene, 400 mL ethanol, and 400 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.89 g, 2.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using toluene:ethanol = 6:1 to obtain intermediate F-56 (54.88 g, yield 75%); HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 292.0278 (theoretical value: 292.0267).

[0126] Preparation of intermediate I-56: F-56 (52.68 g, 180 mmol), b-56 (99.91 g, 200 mmol), and cesium carbonate (117.30 g, 360 mmol) were dissolved in 1500 mL of DMF. The mixture was heated to 150 °C and refluxed for 12 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to give intermediate I-56 (94.90 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.82%. Mass spectrometry m / z: 771.1768 (theoretical value: 771.1777).

[0127] Preparation of intermediate J-56: I-56 (90.28 g, 125 mmol), b'-56 (38.28 g, 137 mmol), and cesium carbonate (81.46 g, 250 mmol) were dissolved in 1100 mL of DMF. The mixture was heated to 150 °C and refluxed for 10 hours under nitrogen protection. 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 J-56 (98.01 g, yield 76%). HPLC analysis showed a solid purity ≥99.85%. Mass spectrometry m / z: 1030.3717 (theoretical value: 1030.3701).

[0128] Preparation of intermediate K-56: J-56 (87.69 g, 85 mmol), c-2 (18.92 g, 94 mmol), and cesium carbonate (55.39 g, 170 mmol) were dissolved in 850 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 K-56 (79.39 g, yield 77%). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 1211.5166 (theoretical value: 1211.5157).

[0129] Preparation of compound 56: Under a nitrogen atmosphere, a solution of K-56 (72.78 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 56 (19.22 g, yield 27%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1185.5417 (theoretical value: 1185.5405). Theoretical elemental content (%) C 86 H 68 BN3O2: C, 87.07; H, 5.78; N, 3.54; Actual element content (%): C, 87.09; H, 5.77; N, 3.53.

[0130] [Synthetic Example 16] Preparation of Compound 88:

[0131] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 with an equimolar amount of e-88, and b-30 with an equimolar amount of b-88, yielding compound 88 (23.30 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1251.5674 (theoretical value: 1251.5663). Theoretical elemental content (%) C 94 H 70BN3: C, 90.15; H, 5.63; N, 3.36; Actual element content (%): C, 90.17; H, 5.62; N, 3.35.

[0132] [Synthetic Example 17] Preparation of Compound 103:

[0133] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 with an equimolar amount of e-103, and b-30 with an equimolar amount of b-103, yielding compound 103 (15.78 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 821.3429 (theoretical value: 821.3438). Theoretical elemental content (%) C 56 H 40 BN7: C, 81.85; H, 4.91; N, 11.93; Actual element content (%): C, 81.83; H, 4.93; N, 11.92.

[0134] [Synthetic Example 18] Preparation of Compound 109:

[0135] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 with an equimolar amount of e-109, and b-30 with an equimolar amount of b-109, yielding compound 109 (24.33 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1227.7552 (theoretical value: 1227.7541). Theoretical elemental content (%) C 90 H 94 BN3: C, 87.99; H, 7.71; N, 3.42; Actual element content (%): C, 87.98; H, 7.73; N, 3.41.

[0136] [Synthetic Example 19] Preparation of Compound 130:

[0137] Preparation of intermediate L-130: Under a nitrogen atmosphere, g-130 (88.33 g, 250 mmol), e-130 (47.57 g, 275 mmol), potassium carbonate (69.11 g, 500 mmol), 800 mL toluene, 400 mL ethanol, and 400 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.89 g, 2.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using toluene:ethanol = 6:1 to obtain intermediate L-130 (68.26 g, yield 77%); HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 352.9430 (theoretical value: 352.9418).

[0138] Preparation of intermediate M-130: Under a nitrogen atmosphere, L-130 (63.82 g, 180 mmol), e'-130 (32.39 g, 200 mmol), potassium carbonate (49.76 g, 360 mmol), 550 mL toluene, 275 mL ethanol, and 275 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.08 g, 1.8 mmol) was added. The reaction system was heated and stirred, and refluxed for 5 h. After the reaction was completed, 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 = 6:1 to obtain intermediate M-130 (55.71 g, yield 79%); HPLC analysis showed that the solid purity was ≥99.84%. Mass spectrometry m / z: 391.0566 (theoretical value: 391.0575).

[0139] Preparation of intermediate N-130: M-130 (48.98 g, 125 mmol), b-130 (44.03 g, 137 mmol), and cesium carbonate (81.46 g, 250 mmol) were dissolved in 1100 mL of DMF. The mixture was heated to 150 °C and refluxed for 10 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to give intermediate N-130 (62.39 g, yield 72%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 692.1790 (theoretical value: 692.1779).

[0140] Preparation of intermediate O-130: N-130 (58.92 g, 85 mmol), c-2 (18.92 g, 94 mmol), and cesium carbonate (55.39 g, 170 mmol) were dissolved in 850 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 O-130 (57.98 g, yield 78%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 873.3225 (theoretical value: 873.3234).

[0141] Preparation of compound 130: Under a nitrogen atmosphere, a solution of O-130 (52.47 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 130 (12.72 g, yield 25%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 847.3471 (theoretical value: 847.3482). Theoretical elemental content (%) C 59 H 42 BN5O: C, 83.58; H, 4.99; N, 8.26; Actual element content (%): C, 83.57; H, 4.97; N, 8.29.

[0142] [Synthetic Example 20] Preparation of Compound 142:

[0143] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-109, b-30 was replaced with an equimolar amount of b-142, and c-2 was replaced with an equimolar amount of c-142, yielding compound 142 (16.97 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 831.2902 (theoretical value: 831.2913). Theoretical elemental content (%) C 56 H 42BN3S2: C, 80.85; H, 5.09; N, 5.05; Actual element content (%): C, 80.87; H, 5.08; N, 5.02.

[0144] [Synthetic Example 21] Preparation of Compound 156:

[0145] Following the preparation method of Synthesis Example 11, e-9 was replaced with an equimolar amount of e-156, and b-9 was replaced with an equimolar amount of b-156, yielding compound 156 (15.62 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 704.3919 (theoretical value: 704.3938). Theoretical elemental content (%) C 50 H 49 BN2O: C, 85.21; H, 7.01; N, 3.97; Actual element content (%): C, 85.23; H, 7.02; N, 3.95.

[0146] [Synthetic Example 22] Preparation of Compound 165:

[0147] Preparation of intermediate P-165: F-165 (61.36 g, 250 mmol), B-165 (135.62 g, 525 mmol), and cesium carbonate (162.91 g, 500 mmol) were dissolved in DMF (1800 mL) and refluxed under nitrogen for 12 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 P-165 (139.00 g, yield 77%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 720.1081 (theoretical value: 720.1092).

[0148] Preparation of intermediate Q-165: P-165 (122.75 g, 170 mmol) was added to the reaction flask, followed by 700 mL of ultra-dry tetrahydrofuran. Under a nitrogen atmosphere, a 2.5 M n-butyllithium solution (102 mL, dissolved in n-hexane, 255 mmol) was slowly added at -78 °C. After stirring at -78 °C for half an hour, a tetrahydrofuran solution of h-165 (45.95 g, 255 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for half an hour, then slowly heated to room temperature and stirred for 12 hours. After the reaction was complete, a saturated ammonium chloride solution was added to quench the reaction. The organic layer was extracted with dichloromethane, washed with water and brine, dried over anhydrous Na₂SO₄, filtered, and the solvent was removed by vacuum distillation. 600 mL of dichloromethane was added to the crude product, followed by 103.78 g (340 mmol) of boron trifluoride diethyl ether (46.5% by mass) under stirring at room temperature. The mixture was stirred overnight at room temperature. The reaction was quenched by adding 500 mL of saturated sodium bicarbonate solution. The mixture was then extracted with 500 mL of dichloromethane. The organic phase was washed three times with water, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography to obtain intermediate Q-165 (80.78 g, yield 59%). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 804.2444 (theoretical value: 804.2456).

[0149] Preparation of intermediate R-165: Q-165 (68.46 g, 85 mmol), c-2 (18.92 g, 94 mmol), and cesium carbonate (55.39 g, 170 mmol) were dissolved in 850 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 R-165 (62.90 g, yield 75%). The purity of the solid was ≥99.82% as determined by HPLC. Mass spectrometry m / z: 985.3923 (theoretical value: 985.3911).

[0150] Preparation of compound 165: Under a nitrogen atmosphere, a solution of R-165 (59.20 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0 °C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70 °C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 165 (16.13 g, yield 28%). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 959.4168 (theoretical value: 959.4159). Theoretical elemental content (%) C 69 H 50 BN5: C, 86.33; H, 5.25; N, 7.30; Actual element content (%): C, 86.32; H, 5.24; N, 7.33.

[0151] [Synthetic Example 23] Preparation of Compound 176:

[0152] Preparation of intermediate S-176: d-9 (56.86 g, 250 mmol), b-176 (152.25 g, 275 mmol), and cesium carbonate (162.91 g, 500 mmol) were dissolved in DMF (1600 mL) and refluxed under nitrogen for 12 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 S-176 (140.79 g, yield 74%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 759.0735 (theoretical value: 759.0724).

[0153] Preparation of intermediate T-176: S-176 (129.38 g, 170 mmol) was added to the reaction flask, followed by 700 mL of ultra-dry tetrahydrofuran. Under a nitrogen atmosphere, a 2.5 M n-butyllithium solution (102 mL, dissolved in n-hexane, 255 mmol) was slowly added at -78 °C. After stirring at -78 °C for half an hour, a tetrahydrofuran solution of h-176 (66.64 g, 255 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for half an hour, then slowly heated to room temperature and stirred for 12 hours. After the reaction was complete, a saturated ammonium chloride solution was added to quench the reaction. The organic layer was extracted with dichloromethane, washed with water and brine, dried over anhydrous Na₂SO₄, filtered, and the solvent was removed by vacuum distillation. 600 mL of dichloromethane was added to the crude product, followed by 103.78 g (340 mmol) of boron trifluoride diethyl ether (46.5% by mass) under stirring at room temperature. The mixture was stirred overnight at room temperature. The reaction was quenched by adding 500 mL of saturated sodium bicarbonate solution. The mixture was then extracted with 500 mL of dichloromethane. The organic phase was washed three times with water, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography to obtain intermediate T-176 (97.54 g, 62%). HPLC analysis showed a solid purity ≥ 99.83%. Mass spectrometry m / z: 924.2729 (theoretical value: 924.2716).

[0154] Preparation of intermediate U-176: T-176 (78.67 g, 85 mmol), c-2 (18.92 g, 94 mmol), and cesium carbonate (55.39 g, 170 mmol) were dissolved in 850 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 U-176 (70.56 g, 75% yield). HPLC analysis showed that the solid purity was ≥99.89%. Mass spectrometry m / z: 1105.4183 (theoretical value: 1105.4171).

[0155] Preparation of compound 176: Under a nitrogen atmosphere, a solution of U-176 (66.41 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0 °C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70 °C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 165 (18.15 g, yield 28%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 1079.4431 (theoretical value: 1079.4419). Theoretical elemental content (%) C 77 H 46 D5BN4O2: C, 85.62; H, 5.23; N, 5.19; Actual element content (%): C, 85.63; H, 5.25; N, 5.16.

[0156] [Synthetic Example 24] Preparation of Compound 184:

[0157] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b-36, and h-176 was replaced with an equimolar amount of h-184, yielding compound 184 (21.73 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 1167.5675 (theoretical value: 1167.5663). Theoretical elemental content (%) C 87 H 70 BN3: C, 89.44; H, 6.04; N, 3.60; Actual element content (%): C, 89.43; H, 6.03; N, 3.62.

[0158] [Synthetic Example 25] Preparation of Compound 194:

[0159] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-88, b-30 was replaced with an equimolar amount of b-194, and c-2 was replaced with an equimolar amount of c-194, yielding compound 194 (15.62 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 897.4242 (theoretical value: 897.4254). Theoretical elemental content (%) C 66 H 52 BN3: C, 88.28; H, 5.84; N, 4.68; Actual element content (%): C, 88.27; H, 5.86; N, 4.67.

[0160] [Synthetic Example 26] Preparation of Compound 205:

[0161] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 with an equimolar amount of e-205, and b-30 with an equimolar amount of b-205, yielding compound 205 (20.34 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1129.4244 (theoretical value: 1129.4235). Theoretical elemental content (%) C 80 H 56 BN3O2Si: C, 85.02; H, 4.99; N, 3.72; Actual element content (%): C, 85.03; H, 4.97; N, 3.74.

[0162] [Synthetic Example 27] Preparation of Compound 224:

[0163] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b'-56, h-176 with an equimolar amount of h-224, and c-2 with an equimolar amount of c-224, yielding compound 224 (17.41 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 1073.6229 (theoretical value: 1073.6215). Theoretical elemental content (%) C 76 H 80 BN3Si: C, 84.96; H, 7.51; N, 3.91; Actual element content (%): C, 84.94; H, 7.53; N, 3.92.

[0164] [Synthetic Example 28] Preparation of Compound 227:

[0165] Following the preparation method of Synthesis Example 10, b-2 was replaced with an equimolar amount of b-227 to obtain compound 227 (14.11 g), with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 839.5363 (theoretical value: 839.5350). Theoretical elemental content (%) C 60 H 66 BN3: C, 85.79; H, 7.92; N, 5.00; Actual element content (%): C, 85.78; H, 7.91; N, 5.02.

[0166] [Synthetic Example 29] Preparation of Compound 228:

[0167] Following the preparation method of Synthesis Example 10, b-2 was replaced with an equimolar amount of b'-56, and c-2 was replaced with an equimolar amount of c-228, yielding compound 228 (15.17 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 842.5547 (theoretical value: 842.5538). Theoretical elemental content (%) C 60 H 63 D3BN3: C, 85.48; H, 8.25; N, 4.98; Actual element content (%): C, 85.47; H, 8.27; N, 4.97.

[0168] [Synthetic Example 30] Preparation of Compound 276:

[0169] Following the preparation method of Synthesis Example 11, e-9 was replaced with an equimolar amount of e-276, and b-9 was replaced with an equimolar amount of b'-56, yielding compound 276 (19.05 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 991.5961 (theoretical value: 991.5976). Theoretical elemental content (%) C 72 H 74 BN3: C, 87.16; H, 7.52; N, 4.24; Actual element content (%): C, 87.15; H, 7.53; N, 4.25.

[0170] [Synthetic Example 31] Preparation of Compound 293:

[0171] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-109, and b-30 was replaced with an equimolar amount of b-293, yielding compound 293 (17.04 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 915.5676 (theoretical value: 915.5663). Theoretical elemental content (%) C 66 H 70 BN3: C, 86.53; H, 7.70; N, 4.59; Actual element content (%): C, 86.54; H, 7.71; N, 4.57.

[0172] [Synthetic Example 32] Preparation of Compound 348:

[0173] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-348, and b-30 was replaced with an equimolar amount of b'-56, yielding compound 348 (17.70 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 1091.6275 (theoretical value: 1091.6289). Theoretical elemental content (%) C 80 H 78 BN3: C, 87.97; H, 7.20; N, 3.85; Actual element content (%): C, 87.98; H, 7.21; N, 3.83.

[0174] [Synthetic Example 33] Preparation of Compound 404:

[0175] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 was replaced with an equimolar amount of e-404, and b-30 was replaced with an equimolar amount of b'-56, yielding compound 404 (19.25 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 971.5369 (theoretical value: 971.5384). Theoretical elemental content (%) C 68 H 70 BN3S: C, 84.01; H, 7.26; N, 4.32; Actual element content (%): C, 84.02; H, 7.25; N, 4.33.

[0176] [Synthetic Example 34] Preparation of Compound 441:

[0177] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-56, e-30 was replaced with an equimolar amount of e-441, and b-30 was replaced with an equimolar amount of b'-56, yielding compound 441 (14.93 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 956.5555 (theoretical value: 956.5564). Theoretical elemental content (%) C 67 H 69 BN4O: C, 84.08; H, 7.27; N, 5.85; Actual element content (%): C, 84.07; H, 7.26; N, 5.87.

[0178] [Synthetic Example 35] Preparation of Compound 445:

[0179] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-88, b-30 with an equimolar amount of b'-56, and c-2 with an equimolar amount of c-445, yielding compound 445 (18.24 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1047.6617 (theoretical value: 1047.6602). Theoretical elemental content (%) C 76 H 82 BN3: C, 87.08; H, 7.88; N, 4.01; Actual element content (%): C, 87.07; H, 7.86; N, 4.04.

[0180] [Synthetic Example 36] Preparation of Compound 452:

[0181] Following the preparation method of Synthesis Example 13, f-30 was replaced with an equimolar amount of f-452, and b-30 was replaced with an equimolar amount of b'-56, yielding compound 452 (20.78 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1081.6070 (theoretical value: 1081.6081). Theoretical elemental content (%) C 78 H 76 BN3O: C, 86.56; H, 7.08; N, 3.88; Actual element content (%): C, 86.58; H, 7.07; N, 3.87.

[0182] [Synthetic Example 37] Preparation of Compound 458:

[0183] Preparation of intermediate V-458: Under a nitrogen atmosphere, i-458 (72.47 g, 250 mmol), e-88 (93.47 g, 525 mmol), potassium carbonate (69.11 g, 500 mmol), 800 mL toluene, 400 mL ethanol, and 400 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2.89 g, 2.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using a toluene:ethanol ratio of 6:1 to obtain intermediate V-458 (74.34 g, yield 75%); HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 396.2052 (theoretical value: 396.2065).

[0184] Preparation of intermediate W-458: Compound V-458 (71.37 g, 180 mmol) was dissolved in 600 mL of tetrahydrofuran solution. Under nitrogen atmosphere at -20 °C, LDA (90 mL, 180 mmol, 2 M tetrahydrofuran solution) was added dropwise. After stirring for 3 hours, elemental iodine (45.69 g, 180 mmol) was added, the mixture was allowed to return to room temperature, and stirring was maintained for 6 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 give intermediate W-458 (67.70 g, 72% yield). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 522.1046 (theoretical value: 522.1031).

[0185] Preparation of intermediate X-458: W-458 (65.30 g, 125 mmol), b'-56 (73.49 g, 263 mmol), and cesium carbonate (81.46 g, 250 mmol) were dissolved in 1100 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 X-458 (92.41 g, yield 71%). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 1040.4870 (theoretical value: 1040.4881).

[0186] Preparation of intermediate Y-458: X-458 (88.50 g, 85 mmol), c-2 (18.92 g, 94 mmol), and cesium carbonate (55.39 g, 170 mmol) were dissolved in 850 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 Y-458 (78.98 g, yield 76%). The purity of the solid was ≥99.89% as determined by HPLC. Mass spectrometry m / z: 1221.6349 (theoretical value: 1221.6336).

[0187] Preparation of compound 458: Under a nitrogen atmosphere, a solution of Y-458 (73.35 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 458 (17.89 g, yield 27%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1103.7239 (theoretical value: 1103.7228). Theoretical elemental content (%) C 80 H 90 BN3: C, 87.00; H, 8.21; N, 3.80. Actual elemental content (%): C, 87.01; H, 8.20; N, 3.81.

[0188] [Synthetic Example 38] Preparation of Compound 467:

[0189] Following the preparation method of Synthesis Example 19, e-130 was replaced with an equimolar amount of e-467, e'-130 was replaced with an equimolar amount of e'-467, and b-130 was replaced with an equimolar amount of b'-56, yielding compound 467 (19.97 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1108.6567 (theoretical value: 1108.6554). Theoretical elemental content (%) C 80 H 81BN4: C, 86.62; H, 7.36; N, 5.05. Actual elemental content (%): C, 86.63; H, 7.35; N, 5.04.

[0190] [Synthetic Example 39] Preparation of Compound 469:

[0191] Following the preparation method of Synthesis Example 19, g-130 was replaced with an equimolar amount of g-469, e-130 was replaced with an equimolar amount of e-469, e'-130 was replaced with an equimolar amount of e-88, and b-130 was replaced with an equimolar amount of b'-56, yielding compound 469 (17.79 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1097.6745 (theoretical value: 1097.6758). Theoretical elemental content (%) C 80 H 84 BN3: C, 87.48; H, 7.71; N, 3.83. Actual elemental content (%): C, 87.47; H, 7.72; N, 3.84.

[0192] [Synthetic Example 40] Preparation of Compound 500:

[0193] Following the preparation method of Synthesis Example 19, e-130 was replaced with an equimolar amount of e-500, e'-130 was replaced with an equimolar amount of e'-500, and b-130 was replaced with an equimolar amount of b'-56, yielding compound 500 (17.58 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 1009.4618 (theoretical value: 1009.4601). Theoretical elemental content (%) C 72 H 60 BN3S: C, 85.61; H, 5.99; N, 4.16; Actual element content (%): C, 85.63; H, 5.97; N, 4.15.

[0194] [Synthetic Example 41] Preparation of Compound 525:

[0195] Following the preparation method of Synthesis Example 19, e-130 was replaced with an equimolar amount of e-525, e'-130 was replaced with an equimolar amount of e'-525, and b-130 was replaced with an equimolar amount of b'-56, yielding compound 525 (14.10 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 838.5382 (theoretical value: 838.5397). Theoretical elemental content (%) C 61 H 67 BN2: C, 87.32; H, 8.05; N, 3.34; Actual element content (%): C, 87.33; H, 8.04; N, 3.35.

[0196] [Synthetic Example 42] Preparation of Compound 554:

[0197] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b-293, and h-176 was replaced with an equimolar amount of h-554, yielding compound 554 (13.10 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 872.4682 (theoretical value: 872.4697). Theoretical elemental content (%) C 62 H 61 BN2Si: C, 85.29; H, 7.04; N, 3.21; Actual element content (%): C, 85.28; H, 7.03; N, 3.23.

[0198] [Synthetic Example 43] Preparation of Compound 571:

[0199] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b'-56, and h-176 was replaced with an equimolar amount of h-571, yielding compound 571 (18.68 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1003.5964 (theoretical value: 1003.5976). Theoretical elemental content (%) C 73 H 74 BN3: C, 87.31; H, 7.43; N, 4.18; Actual element content (%): C, 87.32; H, 7.44; N, 4.16.

[0200] [Synthetic Example 44] Preparation of Compound 595:

[0201] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b'-56, h-176 with an equimolar amount of h-571, and c-2 with an equimolar amount of c-595, yielding compound 595 (17.14 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 1057.6458 (theoretical value: 1057.6445). Theoretical elemental content (%) C 77 H 80 BN3: C, 87.39; H, 7.62; N, 3.97; Actual element content (%): C, 87.37; H, 7.65; N, 3.98.

[0202] [Synthetic Example 45] Preparation of Compound 602:

[0203] Following the preparation method of Synthesis Example 23, b-176 was replaced with an equimolar amount of b'-56, and h-176 was replaced with an equimolar amount of h-602, yielding compound 602 (14.06 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 836.5256 (theoretical value: 836.5241). Theoretical elemental content (%) C 61 H 65 BN2: C, 87.53; H, 7.83; N, 3.35; Actual element content (%): C, 87.54; H, 7.84; N, 3.33.

[0204] [Synthetic Example 46] Preparation of Compound 614:

[0205] Preparation of intermediate AA-614: G-469 (106.00 g, 300 mmol), B'-56 (92.21 g, 330 mmol), and cesium carbonate (195.49 g, 600 mmol) were dissolved in 1800 mL of DMF. The mixture was heated to 150 °C and refluxed for 12 hours under nitrogen protection. After the reaction was complete, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized from dichloromethane and methanol to give intermediate AA-614 (137.87 g, yield 75%). The purity of the solid was ≥99.81% as determined by HPLC. Mass spectrometry m / z: 627.0215 (theoretical value: 627.0201).

[0206] Preparation of intermediate BB-6140: AA-614 (134.80 g, 220 mmol) was added to the reaction flask, followed by 1000 mL of ultra-dry tetrahydrofuran. Under a nitrogen atmosphere, a 2.5 M n-butyllithium solution (132 mL, dissolved in n-hexane, 330 mmol) was slowly added at -78 °C. After stirring at -78 °C for half an hour, h-165 (59.47 g, 330 mmol) of tetrahydrofuran solution was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for half an hour, then slowly heated to room temperature and stirred for 12 hours. After the reaction was complete, a saturated ammonium chloride solution was added to quench the reaction. The organic layer was extracted with dichloromethane, washed with water and brine, dried over anhydrous Na₂SO₄, filtered, and the solvent was removed by vacuum distillation. 800 mL of dichloromethane was added to the crude product, followed by 134.30 g (440 mmol) of boron trifluoride diethyl ether (46.5% by mass) under stirring at room temperature. The mixture was stirred overnight at room temperature. The reaction was quenched by adding 650 mL of saturated sodium bicarbonate solution. The mixture was then extracted with 650 mL of dichloromethane. The organic phase was washed three times with water, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography to give intermediate BB-614 (87.10 g, yield 61%). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 647.1378 (theoretical value: 647.1391).

[0207] Preparation of intermediate CC-614: Under a nitrogen atmosphere, BB-614 (84.38 g, 130 mmol), e-614 (28.32 g, 143 mmol), potassium carbonate (35.93 g, 260 mmol), 450 mL toluene, 225 mL ethanol, and 225 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.50 g, 1.3 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using a toluene:ethanol ratio of 6:1 to obtain intermediate CC-614 (69.49 g, yield 74%); HPLC analysis showed that the solid purity was ≥99.82%. Mass spectrometry m / z: 721.2925 (theoretical value: 721.2912).

[0208] Preparation of intermediate DD-614: CC-614 (65.01 g, 90 mmol), c-2 (22.14 g, 110 mmol), and cesium carbonate (58.65 g, 180 mmol) were dissolved in 900 mL of DMF. The mixture was heated to 150 °C and refluxed for 10 hours under nitrogen protection. 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 DD-614 (59.37 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 902.4354 (theoretical value: 902.4367).

[0209] Preparation of compound 614: Under a nitrogen atmosphere, a solution of DD-614 (54.22 g, 60 mmol) dissolved in tert-butylbenzene (1000 mL) was stirred at 0°C, and tert-butyllithium (48 mL, 120 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (12 mL, 120.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (20 mL, 120 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 100 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 614 (14.73 g, yield 28%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 876.4628 (theoretical value: 876.4615). Theoretical elemental content (%) C 65 H 57 BN2: C, 89.02; H, 6.55; N, 3.19; Actual element content (%): C, 89.04; H, 6.54; N, 3.17.

[0210] [Synthetic Example 47] Preparation of Compound 649:

[0211] Following the preparation method of Synthesis Example 46, h-165 was replaced with an equimolar amount of h-649, and e-614 was replaced with an equimolar amount of e-649, yielding compound 649 (17.26 g) with an HPLC purity ≥ 99.79%. Mass spectrometry m / z: 1149.6518 (theoretical value: 1149.6528). Theoretical elemental content (%) C 82 H 84BN3Si: C, 85.61; H, 7.36; N, 3.65; Measured elemental content (%): C, 85.62; H, 7.35; N, 3.67.

[0212] [Synthetic Example 48] Preparation of Compound 657:

[0213] Following the preparation method of Synthesis Example 46, h-165 was replaced with an equimolar amount of h-657, and e-614 was replaced with an equimolar amount of e'-500, yielding compound 657 (19.37 g) with an HPLC purity ≥ 99.79%. Mass spectrometry m / z: 1194.6356 (theoretical value: 1194.6347). Theoretical elemental content (%) C 86 H 79 BN4O: C, 86.41; H, 6.66; N, 4.69; Measured element content (%): C, 86.43; H, 6.68; N, 4.68.

[0214] [Synthetic Example 49] Preparation of Compound 662:

[0215] Following the preparation method of Synthesis Example 22, f-165 was replaced with an equimolar amount of f-56, b-165 was replaced with an equimolar amount of b'-56, and h-165 was replaced with an equimolar amount of h-224, yielding compound 662 (18.43 g) with an HPLC purity ≥ 99.79%. Mass spectrometry m / z: 1278.7637 (theoretical value: 1278.7650). Theoretical elemental content (%) C 93 H 95 BN4: C, 87.29; H, 7.48; N, 4.38; Measured element content (%): C, 87.27; H, 7.49; N, 4.36.

[0216] [Synthetic Example 50] Preparation of Compound 671:

[0217] Preparation of intermediate EE-671: Compound J-671 (91.90 g, 300 mmol) was dissolved in 1000 mL of tetrahydrofuran solution. Under nitrogen atmosphere at -20 °C, LDA (150 mL, 300 mmol, 2 M tetrahydrofuran solution) was added dropwise. After stirring for 3 hours, elemental iodine (24.11 g, 95 mmol) was added, the mixture was allowed to return to room temperature, and stirring was maintained for 5.5 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 give intermediate EE-671 (105.03 g, yield 81%). HPLC analysis showed a solid purity ≥99.83%. Mass spectrometry m / z: 429.7079 (theoretical value: 429.7068).

[0218] Preparation of intermediate FF-671: Under a nitrogen atmosphere, EE-671 (95.09 g, 220 mmol), e-109 (53.65 g, 440 mmol), potassium carbonate (60.81 g, 440 mmol), 450 mL toluene, 225 mL ethanol, and 225 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (2.54 g, 2.20 mmol) was added. The reaction system was heated and stirred, and refluxed for 7 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 6:1 to obtain intermediate FF-671 (71.33 g, yield 76%); HPLC analysis showed that the solid purity was ≥99.78%. Mass spectrometry m / z: 425.9471 (theoretical value: 425.9484).

[0219] Preparation of intermediate GG-671: Under a nitrogen atmosphere, FF-671 (55.46 g, 130 mmol), b'-56 (36.33 g, 130 mmol), potassium carbonate (35.93 g, 260 mmol), 450 mL toluene, 225 mL ethanol, and 225 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.50 g, 1.3 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was completed, 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 = 5:1 to obtain intermediate GG-671 (66.00 g, yield 74%); HPLC analysis showed that the solid purity was ≥99.80%. Mass spectrometry m / z: 685.1417 (theoretical value: 685.1408).

[0220] Preparation of intermediate HH-671: GG-671 (65.17 g, 95 mmol) was added to the reaction flask, followed by 430 mL of ultra-dry tetrahydrofuran. Under a nitrogen atmosphere, a 2.5 M n-butyllithium solution (57 mL, dissolved in n-hexane, 143 mmol) was slowly added at -78 °C. After stirring at -78 °C for half an hour, a tetrahydrofuran solution of h-571 (43.67 g, 95 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for 0.5 h, then slowly heated to room temperature and stirred for 12 h. After the reaction was complete, a saturated ammonium chloride solution was added to quench the reaction. The organic layer was extracted with dichloromethane, washed with water and brine, dried over anhydrous Na₂SO₄, filtered, and the solvent was removed by vacuum distillation. 345 mL of dichloromethane was added to the crude product, followed by 27.70 g (190 mmol) of boron trifluoride diethyl ether (46.5% by mass) under stirring at room temperature. The mixture was stirred overnight at room temperature. The reaction was quenched by adding 280 mL of saturated sodium bicarbonate solution. The mixture was then extracted with 280 mL of dichloromethane. The organic phase was washed three times with water, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography to obtain intermediate HH-671 (71.66 g, yield 69%). HPLC analysis showed a solid purity ≥ 99.72%. Mass spectrometry m / z: 1092.4271 (theoretical value: 1092.4255).

[0221] Preparation of intermediate KK-671: HH-671 (76.53 g, 70 mmol), c-2 (15.50 g, 77 mmol), and cesium carbonate (45.61 g, 140 mmol) were dissolved in 700 mL of DMF and refluxed at 150 °C for 10 hours under nitrogen protection. 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 KK-671 (66.91 g, yield 75%). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 1273.5719 (theoretical value: 1273.5710).

[0222] Preparation of compound 671: Under a nitrogen atmosphere, a solution of KK-671 (63.73 g, 50 mmol) dissolved in tert-butylbenzene (830 mL) was stirred at 0°C, and tert-butyllithium (40 mL, 100 mmol, 2.5 M n-hexane solution) was slowly added dropwise. The resulting mixture was heated at 70°C for 3 hours. After the halide was fully activated, the reaction mixture was cooled to -40°C, and boron bromide (10 mL, 100.00 mmol) was slowly added. The reaction system was brought back to room temperature and stirred for 2 hours. Then, N,N-diisopropylethylamine (17 mL, 100 mmol, DIEA) was added dropwise at 0°C. The reaction system was heated to 150°C and stirred for 20 hours. The reaction was quenched with 85 mL of methanol and washed with dichloromethane and water. After concentration, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 7 / 1) to give compound 671 (15.03 g, yield 26%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1155.6617 (theoretical value: 1155.6602). Theoretical elemental content (%) C 85 H 82 BN3: C, 88.28; H, 7.15; N, 3.63; Actual element content (%): C, 88.29; H, 7.16; N, 3.61.

[0223] [Synthetic Example 51] Preparation of Compound 674:

[0224] Following the preparation method of Synthesis Example 46, g-469 was replaced with an equimolar amount of g-674, h-165 was replaced with an equimolar amount of h-674, and e-614 was replaced with an equimolar amount of e-30, yielding compound 674 (17.78 g) with an HPLC purity ≥ 99.79%. Mass spectrometry m / z: 1057.5131 (theoretical value: 1057.5142). Theoretical elemental content (%) C 77 H 64 BN3O: C, 87.40; H, 6.10; N, 3.97; Measured element content (%): C, 87.42; H, 6.11; N, 3.95.

[0225] [Synthetic Example 52] Preparation of Compound 707:

[0226] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-707, and b-30 was replaced with an equimolar amount of b-707, yielding compound 707 (19.12 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1224.7237 (theoretical value: 1224.7229). Theoretical elemental content (%) C 90 H 81 D5BN3: C, 88.21; H, 7.48; N, 3.43; Measured element content (%): C, 88.23; H, 7.49; N, 3.45.

[0227] [Synthetic Example 53] Preparation of Compound 738:

[0228] Following the preparation method of Synthesis Example 11, d-9 was replaced with an equimolar amount of d-738, e-9 with an equimolar amount of e-738, and b-9 with an equimolar amount of b-738, yielding compound 738 (19.23 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 1143.6617 (theoretical value: 1143.6602). Theoretical elemental content (%) C 84 H 82 BN3: C, 88.16; H, 7.22; N, 3.67; Measured element content (%): C, 88.114; H, 7.19; N, 3.65.

[0229] [Synthetic Example 54] Preparation of Compound 760:

[0230] Following the preparation method of Synthesis Example 13, e-30 was replaced with an equimolar amount of e-88, b-30 with an equimolar amount of b'-56, and c-2 with an equimolar amount of c-445, yielding compound 445 (19.12 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1224.7238 (theoretical value: 1224.7229). Theoretical elemental content (%) C 90 H 81 D5BN3: C, 88.21; H, 7.48; N, 3.43; Measured element content (%): C, 88.24; H, 7.46; N, 3.41.

[0231] [Synthetic Example 55] Preparation of Compound 822:

[0232] Following the preparation method of Synthesis Example 46, b'-56 was replaced with an equimolar amount of b-738, h-176 with an equimolar amount of h-165, and e-614 with an equimolar amount of e-649, yielding compound 822 (16.61 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 1024.5315 (theoretical value: 1024.5323). Theoretical elemental content (%) C 74 H 69 BN2Si: C, 86.69; H, 6.78; N, 2.73; Measured elemental content (%): C, 86.71; H, 6.79; N, 2.75.

[0233] Device Example 1

[0234] First, the ITO (10nm) / Ag (100nm) / ITO (10nm) glass substrate was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then, it was dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaner and cleaned for 5 minutes. After that, the substrate was transferred to an evaporation machine.

[0235] Then, HI and HT-1 with a thickness of 10 nm are deposited on the glass substrate as hole injection layers, with a mass ratio of HI to HT-1 of 3:97. HT-1 with a thickness of 100 nm is deposited on the hole injection layer as a hole transport layer. EB-1 with a thickness of 20 nm is deposited on the hole transport layer as an electron blocking layer. A light-emitting layer with a thickness of 30 nm is deposited on the electron blocking layer. The light-emitting layer structure includes H-1 and H-2 as host materials and compound 2 as a dopant material, with a mass ratio of H-1, H-2, and compound 2 of 66:33:1. Then, an HB-1 film with a thickness of 5 nm is deposited on the light-emitting layer as a hole blocking layer. An ET-1 and Liq film with a thickness of 30 nm is deposited on the hole blocking layer as an electron transport layer with a mass ratio of 1:1. A LiF film with a thickness of 1 nm is deposited on the electron transport layer as an electron injection layer. Then, a Mg:Ag alloy with a thickness of 15 nm (Mg to Ag mass ratio of 1:9) is deposited on the electron injection layer as a cathode. A CP-1 film with a thickness of 75 nm is deposited on the cathode as a capping layer, thereby fabricating an organic light-emitting device.

[0236] Device Examples 2 to 46: Using compounds 9, 20, 30, 36, 56, 88, 103, 109, 130, 142, 156, 165, 176, 184, 194, 205, 224, 227, 228, 276, 293, 348, compound 404, 441, 445, 452, and 45 of the present invention. 8. Compounds 467, 469, 500, 525, 554, 571, 595, 602, 614, 649, 657, 662, 671, 674, 707, 738, 760, and 822 were used to replace compound 2 in device example 1 as doping materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0237] Comparative Examples 1 to 6: Compound 2 in Device Example 1 was replaced by comparative compounds 1, 2, 3, 4, 5, and 6 as doping materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as Device Example 1.

[0238] The molecular structures of the relevant materials are shown below:

[0239]

[0240] A combined IVL testing system was used to test the current efficiency and peak emission of organic electroluminescent devices (OLEDs). This system consisted of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The full width at half maximum (FWHM) in the thin-film state was obtained using a Horiba Fluorolog-3 series fluorescence spectrometer. The lifetime of the OLEDs was tested using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0241] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit. The luminous efficiency, half-width at half-maximum, peak emission, and lifetime of the device are measured. The test results of the device are shown in Table 1.

[0242] Table 1: Luminescence characteristics test results of Device Examples 1 to 46 and Comparative Examples 1 to 6:

[0243]

[0244] As can be seen from the data in Table 1, when the materials of other functional layers of organic electroluminescent devices are the same, organic electroluminescent devices containing the compound of Formula 1 of this invention as a doping material have higher luminous efficiency, higher color purity, and longer lifespan.

[0245] 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 compound, characterized in that, The boron-nitrogen compound is selected from the structure shown in Formula 1: The ring B is selected from substituted or unsubstituted C3~C20 alicyclic rings; The ring C is selected from any one of the following: unsubstituted or substituted C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaromatic rings, fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C6-C30 aromatic rings, and fused rings of substituted or unsubstituted C3-C20 alicyclic rings and C2-C30 heteroaromatic rings; X1 is selected from single bonds, O, S, CRaRb, NRc, GeRaRb, or Se; Each of the n's is independently selected from CR2 or N; Each x is independently selected from CR5 or N, and the x connected to L is selected from C; R1, R2, R3, R5, Ra, Rb, and Rc are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, and substituted or unsubstituted C2-C20 alkyne. The following are possible combinations of: alkyl, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring; or adjacent R1 groups connected to form a substituted or unsubstituted ring. When x is selected from CR5 and is adjacent to R1, R1 and R5 can be connected to form a substituted or unsubstituted ring; When x is selected from CR5 and is adjacent to ring B, the substituent on ring B and R5 can be connected to form a substituted or unsubstituted ring; When two or more R2s exist simultaneously, the two or more R2s are the same or different, or adjacent R2s are connected to form any of the following rings. Each of the terms 'a' is independently selected from CRd or N; Each of the X2 values ​​is independently selected from CRe or N; Each of the Us is independently selected from O, S, CRfRg, or NRh; Each of the V values ​​is independently selected from a single bond, O, S, CRfRg, or NRh; Rd, Re, Rf, Rg, Rh, and Rx are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C Any one of the following: a 6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection between adjacent Rf and Rg. When two or more Rds exist simultaneously, the two or more Rds are the same or different, or adjacent Rds are connected to form substituted or unsubstituted rings; When R5 is connected with the adjacent R1 to form a substituted or unsubstituted ring, and / or R5 is connected with the substituent on the adjacent ring B to form a substituted or unsubstituted ring, the A is selected from hydrogen, deuterium, tritium, and Al. Otherwise, A is selected from A1; The A1 is selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted amino, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic rings, or any combination of two or more of the groups shown in formulas (1-1) to (1-16). When all three x are selected from CR5 and the two R5 not connected to L are selected from hydrogen or deuterium, A is selected from cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1~C20 alkoxy, substituted or unsubstituted C2~C20 alkenyl, substituted or unsubstituted C2~C20 alkynyl, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C3~C20 alicyclic and C6~C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C3~C20 alicyclic and C2~C30 heteroaromatic ring fused cycloalcohol, or selected from formula (1-2) to formula (1-15), or R5 is connected with adjacent R1 to form a substituted or unsubstituted ring, or R5 is connected with the substituent on adjacent ring B to form a substituted or unsubstituted ring; The ring D is selected from substituted or unsubstituted C3~C20 alicyclic rings; Each of the c's is independently selected from CRj or N; Each of the 'e's is independently selected from CRk or N; Y1 is selected from O, S, CRlRm or NRn; The Y2 is selected from O, S, or CRlRm; The X3 is selected from CRo or N; The Y3 is selected from single bonds, O, S, or CRlRm; The terms Ri, Rj, Rk, Rl, Rm, Rn, Ro, Rp, and Rv are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted... The following are possible combinations of: a substituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or a substituted or unsubstituted ring formed by the connection of adjacent R1 and Rm. When two or more Rj exist simultaneously, the two or more Rj are the same or different, or adjacent Rj are connected to form a substituted or unsubstituted ring; When two or more Rk exist simultaneously, the two or more Rk are the same or different, or adjacent Rk are connected to form any of the following rings. The s is selected from CRq or N; The Y4 is selected from O, S, or NRr; The Y5 is selected from CRu or N; The Y6 is selected from single bonds, O, S, CRsRt, or NRr; The Y7 is selected from O, S, CRsRt, or NRr; Rq, Rr, Rs, Rt, Ru, and Ry are each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The L is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 arylene, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroarylene; The a1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

2. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the structures of formulas 2-1 to 2-6. The m is selected from CR1 or N; The z is selected from CR4 or N; The X4 is selected from single bonds, O, S, CR6R7 or NR8; R4, R6, R7, and R8 are each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C8, and so on. Any one of the following: a C30 aryl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amino group, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring; or R6 and R7 linked together to form a substituted or unsubstituted ring; When two or more R4s exist at the same time, the two or more R4s are the same or different, or adjacent R4s are connected to form substituted or unsubstituted rings; a2 is selected from 0, 1 or 2; a3 is selected from 0 or 1.

3. The boron-nitrogen compound according to claim 1, characterized in that, Adjacent R2s can be connected to form any of the following types of rings. The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2 or 3; the n3 is selected from 0, 1 or 2; the n4 is selected from 0 or 1; the n5 is selected from 0, 1, 2, 3, 4, 5 or 6; and the n6 is selected from 0, 1, 2, 3, 4 or 5.

4. The boron-nitrogen compound according to claim 1, characterized in that, The adjacent Rk can form any of the following types of rings. The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2 or 3; the m3 is selected from 0, 1 or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4 or 5.

5. The boron-nitrogen compound according to claim 1, characterized in that, The A1 group is selected from cyano, halogen, nitro, and substituted or unsubstituted groups such as: methyl, ethyl, propyl, isopropyl, tert-butyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, di-tert-butylphenylsilyl, tert-butyldiphenylsilyl, tripyridylsilyl, pyridinediphenylsilyl, dipyridylphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl. adamantyl, norbornel, alkyl, norbornel, dimethylamino, diethylamino, di-tert-butylamino, methylethylamino, methyl-tert-butylamino, diphenylamino, di(tert-butyl-substituted phenyl)amino, di(silyl-substituted phenyl)amino, diphenylamino, dinaphthylamino, dipyridylamino, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, pyridocyclopentane, pyridocyclohexane, or any one of the following groups: Each of the Rz groups is independently selected from any one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, or 3; the d4 is selected from 0, 1, or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d6 is selected from 0, 1, 2, 3, 4, 5, or 6; the d7 is selected from 0, 1, 2, 3, 4, 5, or 6; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the d11 is selected from 0 or 1. The value of e1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the value of e2 is selected from 0, 1, 2, 3, 4, 5 or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. The f1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The substituents in "substituted or unsubstituted" as described in A1 are selected from deuterium, tritium, cyano, fluorine, nitro, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, phenanthrene, fluoranyl, tetraphenyl, pentaphenyl, fluorenyl, carbazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, azizobenzofuranyl, azizobenzothiophene. The group consisting of any one or a combination of the following: alkyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, azabenzooxazolyl, azabenzothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, and benzocyclohexenyl.

6. The boron-nitrogen compound according to claim 1, characterized in that, The L is selected from the following groups, either single-bonded or substituted or unsubstituted: phenylene, biphenylene, terphenylene, tetraphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, tetraphenylene, pyrenylene, perylene, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, spirofluorenoxanthyl, spirofluorenthixanthyl, spirofluorenazinyl, spirofluorenthraceneyl, spirofluorenyl-acridyl, spiroanthryl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl. Any one of the following: benzocyclohexenyl, pyridinylcyclopentyl, pyridinylcyclohexenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxazinyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, azabenzofuranyl, azabenzothiophenyl, azabenzodibenzofuranyl, azabenzothiophenyl, benzooxazolyl, benzothiazolyl, azabenzooxazolyl, azabenzothiazolyl, dioxinyl, phenoxazinyl, and phenthiazolyl.

7. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the following structures. 。 8. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises one or more of the boron nitride compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent device comprises a cathode, an anode, and an organic layer, the organic layer being disposed between the cathode and the anode or outside any one of the electrodes of the cathode and the anode, characterized in that, The organic layer comprises one or more of the boron-nitrogen compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent device comprises a cathode, an anode, and an organic layer, the organic layer being disposed between the cathode and the anode, the organic layer comprising a light-emitting layer, the light-emitting layer comprising a host material and a dopant material, characterized in that, The doped material comprises one or more boron nitride compounds according to any one of claims 1 to 7.

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