An organic compound, application thereof, and an organic electroluminescence device comprising the same

Abstract

The present application relates to the technical field of organic electroluminescence, in particular to an organic compound and application thereof and an organic electroluminescence device containing the compound. The compound has the structure shown in the following formula (I), wherein X is selected from C-C single bond, O, S, Se, NR 1 , CR 2 R 3 or SiR 4 R 5 , m and n are independently 0 or 1, and ring A1 and ring A2 are independently selected from C6-C60 aromatic ring and C3-C60 heteroaromatic ring. The OLED device prepared by using the compound has low starting voltage, high luminous efficiency and better service life.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and particularly to a novel heterogeneous boron-nitrogen organic compound and its applications, as well as an organic electroluminescent device containing the compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine within the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and its application is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials has become increasingly focused. This is because a high-efficiency, long-lifespan OLED device is typically the result of optimized device structure and the combination of various organic materials. To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve OLED device performance, it is necessary not only to innovate OLED device structures and manufacturing processes, but also to continuously research and innovate the optoelectronic functional materials within OLED devices to prepare functional materials with higher performance. Based on this, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and superior lifespans.

[0004] TADF materials can theoretically achieve 100% internal quantum efficiency through the upconversion process from triplet to singlet states, thus enabling highly efficient luminescence. Traditional TADF molecules have a highly twisted electron donor-acceptor structure, which cannot simultaneously accommodate high reverse intersystem crossing rates and high radiative transition rates, limiting further efficiency improvements. Furthermore, because TADF materials emit light in the CT state, their broad spectrum cannot meet the color requirements of BT.2020, thus restricting their further application in the display field. Boron-nitrogen-based multiple resonance MR-TADF materials, however, possess advantages such as high color purity and high luminous efficiency, attracting widespread attention from the scientific and industrial communities. However, because the peripheral substituents have little effect on the S1 level, it is difficult to control the material's emission color, limiting it to the blue-deep blue region. Moreover, the significant overlap between its HOMO and LUMO levels restricts ΔE... ST The relatively large size and slow reverse intersystem crossing rate greatly limit the further application of MR-TADF materials in high-resolution displays, full-color displays, and white light illumination. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides a general formula compound, specifically a heterogeneous boron-nitrogen organic compound, the structure of which is shown in general formula (Ⅰ):

[0006]

[0007] In formula (Ⅰ), rings A1, A2, A3, and A4 are each independently selected from one of the C6-C60 aromatic rings and the C3-C60 heteroaromatic rings;

[0008] X1 and X2 are each independently selected from C-C single bonds, O, S, Se, and NR. 1 CR 2 R 3 or SiR 4 R 5 m and n are independently 0 or 1;

[0009] R 1 R 2 R 3 R 4 R 5Each is independently selected from one of the following: deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C20 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0010] R 11 R 12 R 13 R 14 Each independently represents a single substituted group up to the maximum allowed number of substituted groups, R 11 R 12 R 13 R 14 Each is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C1-C20 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl, and multiple R 11 The Rs are either not connected or connected in a loop. 12 The Rs are either not connected or connected in a loop. 13 The Rs are either not connected or connected in a loop. 14 They are either not connected or connected in a loop;

[0011] The R' is selected from one of the following: deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl.

[0012] R1, R2, R3, R4, R5, R6, and R7 are each independently selected from one or a combination of two of the following: hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroaryl.

[0013] More preferably, in formula (I), ring A1, ring A2, ring A3, and ring A4 are each independently selected from one of C6-C30 aromatic rings and C3-C30 heteroaromatic rings; even more preferably, ring A1, ring A2, ring A3, and ring A4 are each independently selected from benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, furans, benzo[a]furans, dibenzo[a]furans, indole, benzo[a]indole, carbazole, and indole. The rings are selected from any one of dolocarbazole, benzothiophene, dibenzothiophene, thiophene, benzoselenene, dibenzoselenene, and selenene; more preferably, the rings A1, A2, A3, and A4 are each independently selected from any one of benzene ring, benzofluorene ring, dibenzofluorene ring, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, benzoselenene, and dibenzoselenene.

[0014] More preferably, in formula (Ⅰ), X1 and X2 are each independently selected from C-C single bonds, O, S, and NR. 1 or CR 2 R 3 More preferably, X1 and X2 are each independently selected from C-C single bonds.

[0015] More preferably, in formula (Ⅰ), the R 11 R 12 R 13 R 14 Each group is independently selected from hydrogen, deuterium, cyano, amino, or from one or a combination of two of the following groups: C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, unsubstituted or one of C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl, and multiple R 11 The Rs are either not connected or connected in a loop. 12 The Rs are either not connected or connected in a loop. 13 The Rs are either not connected or connected in a loop. 14 They are either not connected or connected in a loop;

[0016] More preferably, the R 11 R 12 R 13 R 14 Each group is independently selected from hydrogen or from one or a combination of two of the following groups: deuterium, cyano, trifluoromethyl, halogen, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans ind[a]fluorene, trimenyl, isotriin , spirotri-indene, spiroisotri-indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindoleyl, carbazoleyl, indoxarcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthreneazoleyl, pyridinazoleyl, pyrazinazoleyl, quinoxalo-imidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinazoleyl, phenanthrene Enoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanthyl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-enoxadiazolyl, 1,2, 5-Omnidiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazolyl, 1,2,3,4-Tetrazolyl, 1,2,3,5-Tetrazolyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, Diphenylboryl, Dimethylboryl, Dipentafluorophenylboryl, Di(2,4,6-Triisopropylphenyl)boryl, 9,9-Dimethylacridyl, (poly)halobenzene, (poly)cyanobenzene or (poly)trifluoromethylbenzene;

[0017] More preferably, the R 11 R 12 R 13 R14 Each group is independently selected from hydrogen or from one or a combination of two of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, biphenyl, terphenyl, diphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indeno[a]fluorenyl, Furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indenecarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthizimidazoleyl, phenanthrozimidazoleyl, pyridinzimidazoleyl, pyrazinzimidazoleyl, quinoxaline Imidazolyl, oxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenthiazinyl, azacarbazolyl, phenanthrolinel, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene, or (poly)trifluoromethylbenzene.

[0018] More preferably, in formula (I), R1, R2, R3, R4, R5, R6, and R7 are each independently selected from hydrogen or from one or a combination of two of the following groups: deuterium, cyano, halogen, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, Dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthiazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazinimidazole , quinoxaloimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthrazoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxaloyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazole alkyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, indazyl, benzothiadiazolyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl.

[0019] Further preferably, in formula (Ⅰ), X1 and X2 are the same, m and n are the same, and ring A1 and ring A4 are the same, and ring A2 and ring A3 are the same; more preferably, R 11 With R 14 Similarly, the R 12 With R 13same.

[0020] In this specification, the term "substituted or unsubstituted" can refer to a group that replaces one or more substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, the same expression means the same thing, and the range of substituents to be selected is as shown above and will not be repeated here.

[0021] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0022] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0023] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0024] Unless otherwise specified in this specification, aryl and heteroaryl groups include both monocyclic and fused-ring types. Monocyclic aryl refers to a molecule containing one or at least two phenyl groups. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by single bonds, such as phenyl, diphenyl, and terphenyl. Fused-ring aryl refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other; instead, they are fused together by sharing ring edges, such as naphthyl and anthracene. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are independent of each other and connected by single bonds, such as pyridine, furan, and thiophene. Fused-ring heteroaryl refers to a molecule formed by the fusion of at least one phenyl group and at least one heteroaryl group, or by the fusion of at least two heteroaryl rings, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, and dibenzothiophene.

[0025] In this specification, the C6-C60 aryl group is preferably a C6-C30 aryl group, and the aryl group is preferably composed of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indene, fluorenyl and their derivatives, fluoranthyl, triphenylene, pyrene, perylene, etc. The group is selected from the group consisting of 1-triphenyl-4-yl, 3-triphenyl-3-yl, 2-triphenyl-2-yl, 4-triphenyl-3-yl, 3-triphenyl-4-yl, 3-triphenyl-3-yl, and 3-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from the group consisting of 1-anthrayl, 2-anthrayl, and 9-anthrayl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9'-dimethylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl; the pyrene group is selected from the group consisting of 1-pyrene, 2-pyrene, and 4-pyrene; the tetraphenyl group is selected from the group consisting of 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl.

[0026] In this specification, the C3-C60 heteroaryl group is preferably a C4-C30 heteroaryl group, and the heteroaryl group is preferably furanyl, thiophene, pyrrole, benzofuranyl, benzothiophene, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophene, carbazole, and their derivatives. The carbazole derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.

[0027] In this specification, aryloxy groups can be exemplified by the monovalent groups formed by the above-mentioned aryl and heteroaryl groups and oxygen.

[0028] In this specification, alkoxy groups can be exemplified by the aforementioned chain alkyl groups or monovalent groups composed of cycloalkyl groups and oxygen.

[0029] Examples of C6-C60 arylamine groups mentioned in this specification include: phenylamine, methylphenylamine, naphthylamine, anthraceneamine, phenanthreneamine, biphenylamine, etc.

[0030] Examples of C6-C60 heteroaryl amino groups mentioned in this specification include pyridinylamino, pyrimidinylamino, and dibenzofuranylamino.

[0031] Furthermore, the general formula compound of the present invention (I) can preferably include the following specific structural compounds, which are only representative examples:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] The present invention also provides an organic electroluminescent device, comprising a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer comprises a compound shown in the above general formula.

[0059] Specifically, embodiments of the present invention provide an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains a compound of the general formula of the present invention shown above.

[0060] OLED devices prepared using the compounds of this invention have low start-up voltage, high color purity, high luminous efficiency, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials.

[0061] The specific reasons for the excellent performance of the compounds of the present invention as light-emitting layer materials in organic electroluminescent devices are not yet clear, but it is speculated that the reasons may be as follows:

[0062] The general formula compound of this invention has a symmetrical molecular structure, which helps reduce the difficulty of synthesis. The linking groups X1 and X2 in the core structure do not directly participate in BN multiple resonance. That is, while maintaining the molecular multiple resonance characteristics, the electron-donating ability of the outer N atom is adjusted, thereby effectively achieving spectral modulation while maintaining a narrow molecular spectrum and high luminous efficiency. The general formula compound of this invention is fused on the core of a BN-type multiple resonance material. By expanding the conjugated plane, a redshift in light color is achieved while maintaining the rigid structure of the molecule, resulting in a large oscillator strength, which is beneficial for improving luminous efficiency. It also exhibits good stability, which is beneficial for extending device lifespan. The general formula compound of this invention has multiple BN resonance units, resulting in a narrow spectral half-width and high light color purity, which can effectively improve the color gamut of the device, thus potentially further meeting the demands of ultra-high-definition displays. The general formula compound of this invention has a high molecular-level orientation, which is beneficial for improving the light extraction efficiency of OLED devices, thereby improving the luminous efficiency of the devices. Detailed Implementation

[0063] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0064] All the chemical reagents used in this invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N,N-diisopropylethylamine, and reaction intermediates, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0065] The synthesis method of the compound of the present invention is briefly described below (process (1)). First, the hydrogen atom between X1 and X2 is metallized at the ortho position using n-butyllithium or tert-butyllithium. Then, boron tribromide or the like is added to perform a lithium-boron or lithium-phosphorus metal exchange, followed by the addition of a Bronsted base such as N,N-diisopropylethylamine, thereby conducting a tandem borane-friedel-Crafts reaction to obtain the target compound.

[0066]

[0067] R 1 R 2 R 3 R 4 R 5 R 6 R 7 Each group is independently selected from hydrogen, deuterium, or substituted or unsubstituted groups from the following: C6-C48 monocyclic aromatic hydrocarbons or fused-ring aromatic hydrocarbons, C3-C48 monocyclic heteroaromatic hydrocarbons or fused-ring heteroaromatic hydrocarbons, C6-C30 arylamino, C3-C30 heteroarylamino, C1-C36 alkyl, C1-C6 alkoxy, and R 1 To R 7 Two adjacent groups may bond together to form one of the following groups, substituted or unsubstituted: C1-C10 cycloalkanes, C6-C30 aromatics or C5-C30 heteroaromatics, wherein at least one hydrogen in the formed ring may be substituted by aryl, heteroaryl, diarylamino, diarylamino, arylhelelamino, alkyl, alkoxy or aryloxy, wherein at least one hydrogen in these may be substituted by aryl, heteroaryl or alkyl;

[0068] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0069] Synthesis Examples

[0070] Synthesis Example 1: Synthesis of Compound C-1

[0071]

[0072] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a 150 mL solution of tert-butylbenzene (5 mmol) of C-1-1 at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-1 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: C,85.03;H, 4.25;B,3.64;N,7.08 Experimental values: C,85.06;H,4.24;B,3.63;N,7.07 .

[0073] Synthesis Example 2: Synthesis of Compound C-23

[0074]

[0075] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-23-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-23 (20% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1262.25 Elemental analysis results: Theoretical value: C,85.65;H, 4.87;B,1.71;N,7.77 Experimental values: C,85.69;H,4.85;B,1.71;N,7.75 .

[0076] Synthesis Example 3: Synthesis of Compound C-28

[0077]

[0078] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a 150 mL solution of tert-butylbenzene (5 mmol) of C-28-1 at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-28 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 813.75 Elemental analysis results: Theoretical value: C,85.61;H, 6.57;B,2.66;N,5.16 Experimental values: C,85.65;H,6.56;B,2.65;N,5.14 .

[0079] Synthesis Example 4: Synthesis of Compound C-47

[0080]

[0081] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-47-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-47 (18% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1258.25 Elemental analysis results: Theoretical value: C,85.92;H, 4.57;B,1.72;N,7.79 Experimental values: C,85.94;H,4.56;B,1.72;N,7.78 .

[0082] Synthesis Example 5: Synthesis of Compound C-51

[0083]

[0084] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-51-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-51 (19% yield, HPLC purity 99.49%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1114.25 Elemental analysis results: Theoretical value: C,86.24;H, 8.05;B,1.94;N,3.77 Experimental values: C,86.28;H,8.03;B,1.94;N,3.75 .

[0085] Synthesis Example 6: Synthesis of Compound C-53

[0086]

[0087] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-53-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-53 (20% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1203.35 Elemental analysis results: Theoretical value: C,85.84;H, 7.71;B,1.80;N,4.66 Experimental values: C,85.86;H,7.70;B,1.80;N,4.65 .

[0088] Synthesis Example 7: Synthesis of Compound C-57

[0089]

[0090] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-57-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-57 (19% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1027.05 Elemental analysis results: Theoretical value: C,85.37;H, 7.07;B,2.11;N,5.46 Experimental values: C,85.39;H,7.05;B,2.11;N,5.46 .

[0091] Synthesis Example 8: Synthesis of Compound C-86

[0092]

[0093] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-86-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-86 (20% yield, HPLC purity 99.67%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1486.45 Elemental analysis results: Theoretical value: C,87.27;H, 4.68;B,1.45;N,6.60 Experimental values: C,87.29;H,4.67;B,1.44;N,6.60 .

[0094] Synthesis Example 9: Synthesis of Compound C-92

[0095]

[0096] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-92-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-92 (19% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1592.65 Elemental analysis results: Theoretical value: C,85.98;H, 4.49;B,1.36;N,6.16;S,2.01 Experimental values: C,85.99;H,4.48;B,1.36;N,6.15;S,2.02 .

[0097] Synthesis Example 10: Synthesis of Compound C-96

[0098]

[0099] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-96-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-96 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1641.61 Elemental analysis results: Theoretical value: C,85.61;H, 4.54;B,1.32;N,8.53 Experimental values: C,85.63;H,4.53;B,1.32;N,8.52 .

[0100] Synthesis Example 11: Synthesis of Compound C-100

[0101]

[0102] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a 150 mL solution of tert-butylbenzene (5 mmol) of C-100-1 at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-100 (20% yield, HPLC purity 99.62%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 995.96 Elemental analysis results: Theoretical value: C,84.42;H, 6.38;B,2.17;N,7.03 Experimental values: C,84.45;H,6.36;B,2.17;N,7.02 .

[0103] Synthesis Example 12: Synthesis of Compound C-124

[0104]

[0105] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-124-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-124 (18% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 845.75 Elemental analysis results: Theoretical value: C,82.37;H, 6.32;B,2.56;N,4.97;O,3.78 Experimental values: C,82.39;H,6.30;B,2.56;N,4.98;O,3.77 .

[0106] Synthesis Example 13: Synthesis of Compound C-148

[0107]

[0108] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-148-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-148 (21% yield, HPLC purity 99.48%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: C,79.36;H, 6.09;B,2.46;N,4.79;S,7.30 Experimental values: C,79.39;H,6.08;B,2.46;N,4.77;S,7.30 .

[0109] Synthesis Example 14: Synthesis of Compound C-172

[0110]

[0111] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-172-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-172 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 971.65 Elemental analysis results: Theoretical value: C,71.70;H, 5.50;B,2.23;N,4.32;Se,16.26 Experimental values: C,71.72;H,5.50;B,2.23;N,4.32;Se,16.24 .

[0112] Synthesis Example 15: Synthesis of Compound C-196

[0113]

[0114] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-196-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-196 (18% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 897.85 Elemental analysis results: Theoretical value: C,85.61;H, 7.30;B,2.41;N,4.68 Experimental values: C,85.62;H,7.29;B,2.41;N,4.68 .

[0115] Synthesis Example 16: Synthesis of Compound C-215

[0116]

[0117] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-215-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-215 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1342.25 Elemental analysis results: Theoretical value: C,85.90;H, 5.18;B,1.61;N,7.30 Experimental values: C,85.88;H,5.20;B,1.61;N,7.30 .

[0118] Synthesis Example 17: Synthesis of Compound C-220

[0119]

[0120] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-220-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-220 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 930.05 Elemental analysis results: Theoretical value: C,80.07;H, 7.05;B,2.32;N,4.52;Si,6.04 Experimental values: C,80.09;H,7.04;B,2.32;N,4.52;Si,6.03 .

[0121] Synthesis Example 18: Synthesis of Compound C-239

[0122]

[0123] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-239-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-239 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1374.45 Elemental analysis results: Theoretical value: C,82.15;H, 5.06;B,1.57;N,7.13;Si,4.09 Experimental values: C,82.18;H,5.06;B,1.57;N,7.10;Si,4.09 .

[0124] Synthesis Example 19: Synthesis of Compound C-241

[0125]

[0126] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-241-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-241 (20% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 917.65 Elemental analysis results: Theoretical value: :C,89.00;H, 4.06;B,2.36;N,4.58 Experimental values: :C,89.05;H,4.03;B,2.36;N,4.56 .

[0127] Synthesis Example 20: Synthesis of Compound C-265

[0128]

[0129] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-265-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-265 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 949.45 Elemental analysis results: Theoretical value: C,83.46;H, 3.93;B,2.28;N,4.42;Si,5.91 Experimental values: C,83.45;H,3.93;B,2.28;N,4.42;Si,5.92 .

[0130] Synthesis Example 21: Synthesis of Compound C-289

[0131]

[0132] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-289-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-289 (20% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 921.55 Elemental analysis results: Theoretical value: C,88.61;H, 4.48;B,2.35;N,4.56 Experimental values: C,88.64;H,4.46;B,2.35;N,4.55 .

[0133] Synthesis Example 22: Synthesis of Compound C-313

[0134]

[0135] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-313-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before stopping. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-313 (21% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 953.57 Elemental analysis results: Theoretical value: C,83.11;H, 4.33;B,2.27;N,4.41;Si,5.89 Experimental values: C,83.13;H,4.33;B,2.27;N,4.41;Si,5.87 .

[0136] Synthesis Example 23: Synthesis of Compound C-337

[0137]

[0138] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-337-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-337 (19% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: C,86.20;H, 3.84;B,2.35;N,7.62 Experimental values: C,86.24;H,3.82;B,2.35;N,7.60 .

[0139] Synthesis Example 24: Synthesis of Compound C-345

[0140]

[0141] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-345-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-345 (19% yield, HPLC purity 99.58%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 919.45 Elemental analysis results: Theoretical value: C,86.20;H, 3.84;B,2.35;N,7.62 Experimental values: C,86.23;H,3.84;B,2.35;N,7.59 .

[0142] Synthesis Example 25: Synthesis of Compound C-356

[0143]

[0144] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-356-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before stopping. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-356 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1256.36 Elemental analysis results: Theoretical value: C,86.04;H, 6.66;B,1.72;N,5.57 Experimental values: C,86.07;H,6.65;B,1.72;N,5.55 .

[0145] Synthesis Example 26: Synthesis of Compound C-374

[0146]

[0147] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-374-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-374 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1019.75 Elemental analysis results: Theoretical value: C,87.16;H, 3.85;B,2.12;N,6.87 Experimental values: C,87.18;H,3.85;B,2.12;N,6.85 .

[0148] Synthesis Example 27: Synthesis of Compound C-391

[0149]

[0150] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-391-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-391 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1244.25 Elemental analysis results: Theoretical value: C,86.88;H, 5.75;B,1.74;N,5.63 Experimental values: C,86.86;H,5.76;B,1.74;N,5.64 .

[0151] Synthesis Example 28: Synthesis of Compound C-399

[0152]

[0153] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-399-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-399 (19% yield, HPLC purity 99.57%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1220.29 Elemental analysis results: Theoretical value: C,86.62;H, 5.87;B,1.77;N,5.74 Experimental values: C,86.60;H,5.88;B,1.77;N,5.75 .

[0154] Synthesis Example 29: Synthesis of Compound C-401

[0155]

[0156] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-401-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-401 (20% yield, HPLC purity 99.48%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1309.25 Elemental analysis results: Theoretical value: C,86.23;H, 5.70;B,1.65;N,6.42 Experimental values: C,86.26;H,5.69;B,1.65;N,6.40 .

[0157] Synthesis Example 30: Synthesis of Compound C-405

[0158]

[0159] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-405-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-405 (19% yield, HPLC purity 99.54%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1133.05 Elemental analysis results: Theoretical value: C,85.87;H, 4.80;B,1.91;N,7.42 Experimental values: C,85.88;H,4.80;B,1.91;N,7.41 .

[0160] Synthesis Example 31: Synthesis of Compound C-445

[0161]

[0162] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-445-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before stopping. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-445 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 769.55 Elemental analysis results: Theoretical value: C,84.30;H, 3.28;B,2.81;N,5.46;O,4.16 Experimental values: C,84.32;H,3.28;B,2.81;N,5.45;O,4.15 .

[0163] Synthesis Example 32: Synthesis of Compound C-449

[0164]

[0165] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-449-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-449 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: C,84.30;H, 3.28;B,2.81;N,5.46;O,4.16 Experimental values: C,84.32;H,3.28;B,2.81;N,5.45;O,4.15 .

[0166] Synthesis Example 33: Synthesis of Compound C-457

[0167]

[0168] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-457-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-457 (18% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 801.45 Elemental analysis results: Theoretical value: C,80.92;H, 3.14;B,2.70;N,5.24;S,8.00 Experimental values: C,80.91;H,3.14;B,2.70;N,5.24;S,8.01 .

[0169] Synthesis Example 34: Synthesis of Compound C-461

[0170]

[0171] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-461-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-461 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: C,80.92;H, 3.14;B,2.70;N,5.24;S,8.00 Experimental values: C,80.91;H,3.14;B,2.70;N,5.24;S,8.01 .

[0172] Synthesis Example 35: Synthesis of Compound C-473

[0173]

[0174] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-473-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-473 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 895.25 Elemental analysis results: Theoretical value: C,72.44;H, 2.81;B,2.41;N,4.69;Se,17.64 Experimental values: C,72.42;H,2.81;B,2.41;N,4.69;Se,17.66 .

[0175] Synthesis Example 36: Synthesis of Compound C-477

[0176]

[0177] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-477-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-477 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 895.25 Elemental analysis results: Theoretical value: C,72.44;H, 2.81;B,2.41;N,4.69;Se,17.64 Experimental values: C,72.42;H,2.81;B,2.41;N,4.69;Se,17.66 .

[0178] Synthesis Example 37: Synthesis of Compound C-481

[0179]

[0180] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-481-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-481 (19% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.36 Elemental analysis results: Theoretical value: C,87.71;H, 4.54;B,2.63;N,5.11 Experimental values: C,87.75;H,4.52;B,2.63;N,5.09 .

[0181] Synthesis Example 38: Synthesis of Compound C-485

[0182]

[0183] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-485-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-485 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.36 Elemental analysis results: Theoretical value: C,87.71;H, 4.54;B,2.63;N,5.11 Experimental values: C,87.75;H,4.52;B,2.63;N,5.09 .

[0184] Synthesis Example 39: Synthesis of Compound C-493

[0185]

[0186] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-493-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-49 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1069.25 Elemental analysis results: Theoretical value: C,89.81;H, 4.24;B,2.02;N,3.93 Experimental values: C,89.83;H,4.22;B,2.02;N,3.93 .

[0187] Synthesis Example 40: Synthesis of Compound C-497

[0188]

[0189] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-497-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-497 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1294.25 Elemental analysis results: Theoretical value: C,89.09;H, 6.00;B,1.67;N,3.25 Experimental values: C,89.09;H,6.02;B,1.67;N,3.23 .

[0190] Synthesis Example 41: Synthesis of Compound C-505

[0191]

[0192] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-505-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before stopping. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-505 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1065.45 Elemental analysis results: Theoretical value: C,90.15;H, 3.88;B,2.03;N,3.94 Experimental values: C,90.17;H,3.86;B,2.03;N,3.94 .

[0193] Synthesis Example 42: Synthesis of Compound C-509

[0194]

[0195] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-509-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-509 (19% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1065.45 Elemental analysis results: Theoretical value: C,90.15;H, 3.88;B,2.03;N,3.94 Experimental values: C,90.17;H,3.86;B,2.03;N,3.94 .

[0196] Synthesis Example 43: Synthesis of Compound C-513

[0197]

[0198] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-513-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-513 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 853.25 Elemental analysis results: Theoretical value: C,81.60;H, 4.37;B,2.53;N,4.92;Si,6.58 Experimental values: C,81.63;H,4.36;B,2.53;N,4.92;Si,6.56 .

[0199] Synthesis Example 44: Synthesis of Compound C-517

[0200]

[0201] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-517-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-517 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 853.25 Elemental analysis results: Theoretical value: C,81.60;H, 4.37;B,2.53;N,4.92;Si,6.58 Experimental values: C,81.63;H,4.36;B,2.53;N,4.92;Si,6.56 .

[0202] Synthesis Example 45: Synthesis of Compound C-526

[0203]

[0204] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-526-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-526 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1101.25 Elemental analysis results: Theoretical value: C,85.01;H, 4.12;B,1.96;N,3.81;Si,5.10 Experimental values: C,85.03;H,4.10;B,1.96;N,3.81;Si,5.10 .

[0205] Synthesis Example 46: Synthesis of Compound C-530

[0206]

[0207] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-530-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-530 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1101.25 Elemental analysis results: Theoretical value: C,85.01;H, 4.12;B,1.96;N,3.81;Si,5.10 Experimental values: C,85.03;H,4.10;B,1.96;N,3.81;Si,5.10 .

[0208] Synthesis Example 47: Synthesis of Compound C-538

[0209]

[0210] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-538-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-538 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1097.25 Elemental analysis results: Theoretical value: C,85.32;H, 3.76;B,1.97;N,3.83;Si,5.12 Experimental values: C,85.34;H,3.76;B,1.97;N,3.83;Si,5.10 .

[0211] Synthesis Example 48: Synthesis of Compound C-542

[0212]

[0213] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-542-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-542 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 593.25 Elemental analysis results: Theoretical value: 1097.25 Elemental analysis results: Theoretical value: C,85.32;H,3.76;B,1.97;N,3.83;Si,5.12 Experimental values: C,85.34;H,3.76; B,1.97;N,3.83;Si,5.10 .

[0214] Synthesis Example 49: Synthesis of Compound C-549

[0215]

[0216] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-549-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-549 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1003.38 Elemental analysis results: Theoretical value: C,86.15;H, 4.72;B,2.15;N,6.98 Experimental values: C,86.17;H,4.72;B,2.15;N,6.96 .

[0217] Synthesis Example 50: Synthesis of Compound C-557

[0218]

[0219] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-557-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-557 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1003.38 Elemental analysis results: Theoretical value: C,86.15;H, 4.72;B,2.15;N,6.98 Experimental values: C,86.17;H,4.72;B,2.15;N,6.96 .

[0220] Synthesis Example 51: Synthesis of Compound C-569

[0221]

[0222] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-569-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-569 (19% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1115.25 Elemental analysis results: Theoretical value: C,86.10;H, 5.69;B,1.94;N,6.28 Experimental values: C,86.13;H,5.68;B,1.94;N,6.26 .

[0223] Synthesis Example 52: Synthesis of Compound C-576

[0224]

[0225] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-576-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-576 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1087.25 Elemental analysis results: Theoretical value: C,86.11;H, 5.47;B,1.99;N,6.44 Experimental values: C,86.13;H,5.47;B,1.99;N,6.42 .

[0226] Synthesis Example 53: Synthesis of Compound C-586

[0227]

[0228] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-586-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-586 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1103.25 Elemental analysis results: Theoretical value: C,87.04;H, 4.66;B,1.96;N,6.34 Experimental values: C,87.06;H,4.66;B,1.96;N,6.32 .

[0229] Synthesis Example 54: Synthesis of Compound C-605

[0230]

[0231] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-605-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-605 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1103.25 Elemental analysis results: Theoretical value: C,87.04;H, 4.66;B,1.96;N,6.34 Experimental values: C,87.06;H,4.66;B,1.96;N,6.32 .

[0232] Synthesis Example 55: Synthesis of Compound C-609

[0233]

[0234] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-609-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-609 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 905.25 Elemental analysis results: Theoretical value: C,87.52;H, 5.45;B,2.39;N,4.64 Experimental values: C,87.50;H,5.45;B,2.39;N,4.66 .

[0235] Synthesis Example 56: Synthesis of Compound C-617

[0236]

[0237] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-617-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-617 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 905.25 Elemental analysis results: Theoretical value: C,87.52;H, 5.45;B,2.39;N,4.64 Experimental values: C,87.50;H,5.45;B,2.39;N,4.66 .

[0238] Synthesis Example 57: Synthesis of Compound C-623

[0239]

[0240] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-623-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-623 (19% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1153.27 Elemental analysis results: Theoretical value: C,89.51;H, 4.98;B,1.87;N,3.64 Experimental values: C,89.53;H,4.96;B,1.87;N,3.64 .

[0241] Synthesis Example 58: Synthesis of Compound C-629

[0242]

[0243] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-629-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-629 (19% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1153.27 Elemental analysis results: Theoretical value: C,89.51;H, 4.98;B,1.87;N,3.64 Experimental values: C,89.53;H,4.96;B,1.87;N,3.64 .

[0244] Synthesis Example 59: Synthesis of Compound C-633

[0245]

[0246] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-633-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-633 (18% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1149.45 Elemental analysis results: Theoretical value: C,89.82;H, 4.65;B,1.88;N,3.65 Experimental values: C,89.83;H,4.65;B,1.88;N,3.64 .

[0247] Synthesis Example 60: Synthesis of Compound C-637

[0248]

[0249] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-637-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-637 (18% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1149.45 Elemental analysis results: Theoretical value: C,89.82;H, 4.65;B,1.88;N,3.65 Experimental values: C,89.83;H,4.65;B,1.88;N,3.64 .

[0250] Synthesis Example 61: Synthesis of Compound C-641

[0251]

[0252] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-641-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-641 (19% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 937.25 Elemental analysis results: Theoretical value: C,81.96;H, 5.27;B,2.31;N,4.48;Si,5.99 Experimental values: C,81.94;H,5.28;B,2.31;N,4.48;Si,6.00 .

[0253] Synthesis Example 62: Synthesis of Compound C-649

[0254]

[0255] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-649-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-649 (19% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 937.25 Elemental analysis results: Theoretical value: C,81.96;H, 5.27;B,2.31;N,4.48;Si,5.99 Experimental values: C,81.94;H,5.28;B,2.31;N,4.48;Si,6.00 .

[0256] Synthesis Example 63: Synthesis of Compound C-655

[0257]

[0258] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-655-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-655 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1185.55 Elemental analysis results: Theoretical value: C,85.06;H, 4.84;B,1.82;N,3.54;Si,4.74 Experimental values: C,85.07;H,4.84;B,1.82;N,3.54;Si,4.73 .

[0259] Synthesis Example 64: Synthesis of Compound C-658

[0260]

[0261] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-658-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-658 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1185.55 Elemental analysis results: Theoretical value: C,85.06;H, 4.84;B,1.82;N,3.54;Si,4.74 Experimental values: C,85.07;H,4.84;B,1.82;N,3.54;Si,4.73 .

[0262] Synthesis Example 65: Synthesis of Compound C-666

[0263]

[0264] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-666-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-666 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1182.25 Elemental analysis results: Theoretical value: C,85.35;H, 4.52;B,1.83;N,3.55;Si,4.75 Experimental values: C,85.37;H,4.52;B,1.83;N,3.55;Si,4.73 .

[0265] Synthesis Example 66: Synthesis of Compound C-670

[0266]

[0267] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-670-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-670 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1182.25 Elemental analysis results: Theoretical value: C,85.35;H, 4.52;B,1.83;N,3.55;Si,4.75 Experimental values: C,85.37;H,4.52;B,1.83;N,3.55;Si,4.73 .

[0268] Synthesis Example 67: Synthesis of Compound C-682

[0269]

[0270] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-682-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-682 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1120.25 Elemental analysis results: Theoretical value: C,85.79;H, 6.03;B,1.93;N,6.25 Experimental values: C,85.79;H,6.03;B,1.94;N,6.24 .

[0271] Synthesis Example 68: Synthesis of Compound C-690

[0272]

[0273] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-690-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-690 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 970.20 Elemental analysis results: Theoretical value: C,84.21;H, 5.92;B,2.23;N,4.33;O,3.30 Experimental values: C,84.21;H,5.92;B,2.23;N,4.34;O,3.29 .

[0274] Synthesis Example 69: Synthesis of Compound C-694

[0275]

[0276] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-694-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-694 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1002.25 Elemental analysis results: Theoretical value: C,81.51;H, 5.73;B,2.16;N,4.19;S,6.40 Experimental values: C,81.51;H,5.73;B,2.16;N,4.18;S,6.41 .

[0277] Synthesis Example 70: Synthesis of Compound C-698

[0278]

[0279] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (1.60 M, 22.5 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of C-698-1 (5 mmol) at 0 °C. The temperature was then increased sequentially to 60 °C, 90 °C, and 120 °C, reacting for 4 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (27.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours before being stopped. The solvent was evaporated under vacuum, and the solution was passed through a silica gel column (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-698 (18% yield, HPLC purity 99.46%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1096.25 Elemental analysis results: Theoretical value: C,74.54;H, 5.24;B,1.97;N,3.83;Se,14.41 Experimental values: C,74.54;H,5.24;B,1.97;N,3.84;Se,14.40 .

[0280] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0281] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0282] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0283] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0284] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0285] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0286] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0287] The fabrication process of the organic electroluminescent device of the present invention is described as follows: an anode 2, a hole transport layer 3, an organic light-emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. Specifically, the organic light-emitting layer 4 is formed by co-deposition of a wide-bandgap material source, an electron donor-type material source, an electron acceptor-type material source, and a resonant TADF material source.

[0288] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0289] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0290] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~9×10 -3 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anodic layer film at a deposition rate of 0.1-0.5 nm / s;

[0291] 3. A hole transport layer is vacuum-deposited on top of the hole injection layer at a deposition rate of 0.1-0.5 nm / s.

[0292] 4. The light-emitting layer of the device is vacuum-deposited on the hole transport layer. The light-emitting layer includes the host material and TADF dye. The evaporation rate of the host material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by using a multi-source co-evaporation method to make the dye reach the preset doping ratio.

[0293] 5. The electron transport layer material of the device is vacuum-deposited on top of the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0294] 6. A LiF layer is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer on the electron transport layer, and an Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0295] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0296] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0297] Example 1

[0298] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0299] ITO / HI(10nm) / HT(30nm) / Host:3wt%:C-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0300] In this embodiment, the anode is ITO; the hole injection layer is made of HI, with a typical total thickness of 5-30 nm, and 10 nm in this example; the hole transport layer is also made of HI, with a typical total thickness of 5-500 nm, and 40 nm in this example; the host is the main material of the wide bandgap organic light-emitting layer, M... C -1 is a dye with a doping concentration of 3wt%. The thickness of the organic light-emitting layer is generally 1-200nm, and in this embodiment it is 30nm. The electron transport layer is made of ET and has a thickness of generally 5-300nm, and in this embodiment it is 30nm. The electron injection layer and cathode materials are LiF (0.5nm) and aluminum (150nm).

[0301] Example 2

[0302] The preparation method is the same as in Example 1, except that the wide-bandgap host material used in the light-emitting layer is replaced with a TADF-type host TD. The specific device structure is as follows:

[0303] ITO / HI(10nm) / HT(30nm) / TD:3wt%:C-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0304] Example 3

[0305] The preparation method is the same as in Example 1, except that the dye is replaced with C-23 instead of C-1. The specific device structure is as follows:

[0306] ITO / HI(10nm) / HT(30nm) / Host:3wt%:C-23(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0307] Example 4

[0308] The preparation method is the same as in Example 2, except that the dye is replaced with C-23 instead of C-1. The specific device structure is as follows:

[0309] ITO / HI(10nm) / HT(30nm) / TD:3wt%:C-23(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0310] Example 5

[0311] The preparation method is the same as in Example 1, except that the dye is replaced with C-28 instead of C-1. The specific device structure is as follows:

[0312] ITO / HI(10nm) / HT(30nm) / Host:3wt%:C-28(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0313] Example 6

[0314] The preparation method is the same as in Example 2, except that the dye is replaced with C-28 instead of C-1. The specific device structure is as follows:

[0315] ITO / HI(10nm) / HT(30nm) / TD:3wt%:C-28(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0316] Example 7

[0317] The preparation method is the same as in Example 1, except that the dye is replaced with C-51 instead of C-1. The specific device structure is as follows:

[0318] ITO / HI(10nm) / HT(30nm) / Host:3wt%:C-51(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0319] Example 8

[0320] The preparation method is the same as in Example 2, except that the dye is replaced with C-51 instead of C-1. The specific device structure is as follows:

[0321] ITO / HI(10nm) / HT(30nm) / TD:3wt%:C-51(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0322] Example 9

[0323] The preparation method is the same as in Example 1, except that the dye is replaced by C-86 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-86 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0324] Example 10

[0325] The preparation method is the same as in Example 2, except that the dye is replaced by C-86 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-86 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0326] Example 11

[0327] The preparation method is the same as in Example 1, except that the dye is replaced by C-100 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-100 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0328] Example 12

[0329] The preparation method is the same as in Example 2, except that the dye is replaced by C-100 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-100 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0330] Example 13

[0331] The preparation method is the same as in Example 1, except that the dye is replaced by C-124 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-124 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0332] Example 14

[0333] The preparation method is the same as in Example 2, except that the dye is replaced by C-124 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-124 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0334] Example 15

[0335] The preparation method is the same as in Example 1, except that the dye is replaced by C-148 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-148 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0336] Example 16

[0337] The preparation method is the same as in Example 2, except that the dye is replaced by C-148 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-148 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0338] Example 17

[0339] The preparation method is the same as in Example 1, except that the dye is replaced by C172 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-172 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0340] Example 18

[0341] The preparation method is the same as in Example 2, except that the dye is replaced by C-172 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-172 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0342] Example 19

[0343] The preparation method is the same as in Example 1, except that the dye is replaced by C-196 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-196 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0344] Example 20

[0345] The preparation method is the same as in Example 2, except that the dye is replaced by C-196 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-196 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0346] Example 21

[0347] The preparation method is the same as in Example 1, except that the dye is replaced by C-220 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-220 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0348] Example 22

[0349] The preparation method is the same as in Example 2, except that the dye is replaced by C-220 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-220 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0350] Example 23

[0351] The preparation method is the same as in Example 1, except that the dye is replaced by C-241 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-241 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0352] Example 24

[0353] The preparation method is the same as in Example 2, except that the dye is replaced by C-241 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-241 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0354] Example 25

[0355] The preparation method is the same as in Example 1, except that the dye is replaced by C-265 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-265 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0356] Example 26

[0357] The preparation method is the same as in Example 2, except that the dye is replaced by C-265 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-265 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0358] Example 27

[0359] The preparation method is the same as in Example 1, except that the dye is replaced by C-289 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-289 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0360] Example 28

[0361] The preparation method is the same as in Example 2, except that the dye is replaced by C-289 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-289 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0362] Example 29

[0363] The preparation method is the same as in Example 1, except that the dye is replaced by C-313 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-313 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0364] Example 30

[0365] The preparation method is the same as in Example 2, except that the dye is replaced by C-313 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-313 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0366] Example 31

[0367] The preparation method is the same as in Example 1, except that the dye is replaced by C-337 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-337 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0368] Example 32

[0369] The preparation method is the same as in Example 2, except that the dye is replaced by C-337 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-337 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0370] Example 33

[0371] The preparation method is the same as in Example 1, except that the dye is replaced by C-356 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-356 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0372] Example 34

[0373] The preparation method is the same as in Example 2, except that the dye is replaced by C-356 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-356 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0374] Example 35

[0375] The preparation method is the same as in Example 1, except that the dye is replaced by C-391 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-391 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0376] Example 36

[0377] The preparation method is the same as in Example 2, except that the dye is replaced by C-391 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-391 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0378] Example 37

[0379] The preparation method is the same as in Example 1, except that the dye is replaced by C-401 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-401 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0380] Example 38

[0381] The preparation method is the same as in Example 2, except that the dye is replaced by C-401 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-401 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0382] Example 39

[0383] The preparation method is the same as in Example 1, except that the dye is replaced by C-405 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-405 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0384] Example 40

[0385] The preparation method is the same as in Example 2, except that the dye is replaced by C-405 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-405 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0386] Example 41

[0387] The preparation method is the same as in Example 1, except that the dye is replaced by C-445 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-445 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0388] Example 42

[0389] The preparation method is the same as in Example 2, except that the dye is replaced by C-445 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-445 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0390] Example 43

[0391] The preparation method is the same as in Example 1, except that the dye is replaced by C-457 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-457 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0392] Example 44

[0393] The preparation method is the same as in Example 2, except that the dye is replaced by C-457 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-457 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0394] Example 45

[0395] The preparation method is the same as in Example 1, except that the dye is replaced by C-477 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-477 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0396] Example 46

[0397] The preparation method is the same as in Example 2, except that the dye is replaced by C-477 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-477 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0398] Example 47

[0399] The preparation method is the same as in Example 1, except that the dye is replaced by C-481 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-481 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0400] Example 48

[0401] The preparation method is the same as in Example 2, except that the dye is replaced by C-481 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-481 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0402] Example 49

[0403] The preparation method is the same as in Example 1, except that the dye is replaced by C-493 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-493 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0404] Example 50

[0405] The preparation method is the same as in Example 2, except that the dye is replaced by C-493 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-493 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0406] Example 51

[0407] The preparation method is the same as in Example 1, except that the dye is replaced by C-505 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-505 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0408] Example 52

[0409] The preparation method is the same as in Example 2, except that the dye is replaced by C-505 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-505 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0410] Example 53

[0411] The preparation method is the same as in Example 1, except that the dye is replaced by C-513 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-513 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0412] Example 54

[0413] The preparation method is the same as in Example 2, except that the dye is replaced by C-513 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-513 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0414] Example 55

[0415] The preparation method is the same as in Example 1, except that the dye is replaced by C-526 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-526 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0416] Example 56

[0417] The preparation method is the same as in Example 2, except that the dye is replaced by C-526 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-526 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0418] Example 57

[0419] The preparation method is the same as in Example 1, except that the dye is replaced by C-538 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-538 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0420] Example 58

[0421] The preparation method is the same as in Example 2, except that the dye is replaced by C-538 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-538 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0422] Example 59

[0423] The preparation method is the same as in Example 1, except that the dye is replaced by C-549 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-549 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0424] Example 60

[0425] The preparation method is the same as in Example 2, except that the dye is replaced by C-549 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-549 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0426] Example 61

[0427] The preparation method is the same as in Example 1, except that the dye is replaced by C-609 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-609 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0428] Example 62

[0429] The preparation method is the same as in Example 2, except that the dye is replaced by C-609 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-609 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0430] Example 63

[0431] The preparation method is the same as in Example 1, except that the dye is replaced by C-623 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-623 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0432] Example 64

[0433] The preparation method is the same as in Example 2, except that the dye is replaced by C-623 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-623 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0434] Example 65

[0435] The preparation method is the same as in Example 1, except that the dye is replaced by C-633 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-633 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0436] Example 66

[0437] The preparation method is the same as in Example 2, except that the dye is replaced by C-633 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-633 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0438] Example 67

[0439] The preparation method is the same as in Example 1, except that the dye is replaced by C-641 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-641 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0440] Example 68

[0441] The preparation method is the same as in Example 2, except that the dye is replaced by C-641 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-641 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0442] Example 69

[0443] The preparation method is the same as in Example 1, except that the dye is replaced by C-655 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-655 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0444] Example 70

[0445] The preparation method is the same as in Example 2, except that the dye is replaced by C-655 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-655 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0446] Example 71

[0447] The preparation method is the same as in Example 1, except that the dye is replaced by C-666 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-666 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0448] Example 72

[0449] The preparation method is the same as in Example 2, except that the dye is replaced by C-666 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-666 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0450] Example 73

[0451] The preparation method is the same as in Example 1, except that the dye is replaced by C-682 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-682 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0452] Example 74

[0453] The preparation method is the same as in Example 2, except that the dye is replaced by C-682 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-682 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0454] Example 75

[0455] The preparation method is the same as in Example 1, except that the dye is replaced by C-690 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-690 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0456] Example 76

[0457] The preparation method is the same as in Example 2, except that the dye is replaced by C-690 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-690 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0458] Example 77

[0459] The preparation method is the same as in Example 1, except that the dye is replaced by C-694 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-694 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0460] Example 78

[0461] The preparation method is the same as in Example 2, except that the dye is replaced by C-694 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-694 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0462] Example 79

[0463] The preparation method is the same as in Example 1, except that the dye is replaced by C-698 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: C-698 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0464] Example 80

[0465] The preparation method is the same as in Example 2, except that the dye is replaced by C-698 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:C-698 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0466] Comparative Device Example 1

[0467] The preparation method is the same as in Example 1, except that the dye is replaced by P-1 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: P-1 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0468] Comparative Device Example 2

[0469] The preparation method is the same as in Example 2, except that the dye is replaced by P-1 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:P-1 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0470] Comparative Device Example 3

[0471] The preparation method is the same as in Example 1, except that the dye is replaced by P-2 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: P-2 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0472] Comparative Device Example 4

[0473] The preparation method is the same as in Example 2, except that the dye is replaced by P-2 instead of C-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:P-2 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0474] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0475]

[0476]

[0477] The specific performance data of the organic electroluminescent devices D1 to D80 and devices DD1 to DD4 prepared in the above-described device embodiments are detailed in Table 1 below:

[0478] Table 1:

[0479]

[0480]

[0481]

[0482]

[0483] The experimental data above show that the novel MR-TADF material provided by this invention has high color purity and high luminous efficiency. When it is prepared and applied to organic electroluminescent devices, it achieves blue light emission under electroluminescence conditions. It is a high-performance organic light-emitting functional material and is expected to be promoted for commercial application.

[0484] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

[0485] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound having the structure shown in formula (Ⅰ): In formula (Ⅰ), rings A1, A2, A3, and A4 are each independently selected from one of the following: benzene ring, benzo[a]fluorene ring, dibenzo[a]fluorene ring, benzo[a]furan, dibenzo[a]furan, indole, benzo[a]indole, carbazole, indole[a]carbazole, benzo[a]thiophene, dibenzo[a]thiophene, benzo[a]selenide, and dibenzo[a]selenide. Furthermore, ring A1 is the same as ring A4, and ring A2 is the same as ring A3; X1 and X2 are each independently selected from C-C single bonds, O, S, Se, and NR. 1 CR 2 R 3 or SiR 4 R 5 Both m and n are 1; And X1 and X2 are the same; R 1 R 2 R 3 R 4 R 5 Each is independently selected from one of C1-C20 chain alkyl, C6-C60 aryl, or C3-C60 heteroaryl; R 11 R 12 R 13 R 14 Each independently represents a single substituted group up to the maximum allowed number of substituted groups, R 11 R 11 R 13 R 14 Each is independently selected from one or a combination of two of the following: hydrogen, deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl, and multiple R 11 The Rs are either not connected or connected in a loop. 12 The Rs are either not connected or connected in a loop. 13 The Rs are either not connected or connected in a loop. 14 The R are either not connected or connected in a loop; 11 With R 14 Similarly, the R 12 With R 13 same; R1, R2, R3, R4, R5, R6, and R7 are each independently selected from one or a combination of two of the following: hydrogen, deuterium, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that, X1 and X2 are each independently selected from C-C single bonds, O, S, and NR. 1 or CR 2 R 3 .

3. The organic compound according to claim 1, characterized in that, X1 and X2 are each independently selected from CC single bonds.

4. The organic compound according to claim 1, characterized in that, The R 11 R 12 R 13 R 14 Each group is independently selected from hydrogen or from one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, biphenyl, terphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis Or trans-indofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthizimidazoleyl, phenanzimidazoleyl Pyridinium imidazolyl, pyrazinium imidazolyl, quinoxalinium imidazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenthiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl.

5. The organic compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, and R7 are each independently selected from hydrogen or from one of the following groups: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, terphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl. Dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazole alkyl, benzimidazolyl, naphthizimidazolyl, phenanthizimidazolyl, pyridinizimidazolyl, pyrazinizimidazolyl, quinoxalinizimidazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, pyrazinyl, phenazinyl, phenthiazinyl, naphthidyl, azacarbazolyl, benzocarbazoline , phenanthroline, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indazinyl, benzothiadiazolyl.

6. An organic compound selected from the following specific structures:

7. The application of the compound according to any one of claims 1-6, wherein the application is as a functional material in organic electronic devices, said organic electronic devices including organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; The compound is used as a light-emitting layer material in organic electroluminescent devices, specifically as a light-emitting material in the light-emitting layer.

8. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode. The light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, with the light-emitting layer located between the hole transport region and the electron transport region; wherein, The light-emitting layer contains any one of the compounds described in claims 1-6.

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