An organic compound and use thereof

Abstract

This invention relates to an organic compound and to organic electroluminescent devices employing the organic compound. The organic compound of this invention has a structure as shown in formula (1), (2), or (3), or a structure formed by the polymerization of any two of formulas (1-1), (1-2), and (1-3). Organic electroluminescent devices employing the compound of this invention exhibit excellent device performance and stability.

Description

Technical Field

[0001] This invention relates to an organic compound, and more particularly to a compound that can be used in organic electroluminescent devices, and also to organic electroluminescent devices employing the organic 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 is receiving increasing attention. 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, innovation in OLED device structure and manufacturing processes is necessary, along with ongoing research and innovation in the optoelectronic functional materials used in OLED devices to develop higher-performance functional materials. Based on this, the OLED materials community has been dedicated 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.

[0005] Existing technologies employ the "multiple resonance-induced thermally activated delayed fluorescence (MR-TADF)" strategy for the design and development of novel compound structures. Patent applications CN107851724, CN108431984, and CN110407858, for example, design polycyclic aromatic compounds formed by linking multiple aromatic rings with boron, nitrogen, or oxygen atoms, thus constructing a unique rigid molecular system containing boron (B) and nitrogen (N) atoms. Compared to donor-acceptor type TADF compounds, MR-TADF molecules possess both high radiative transition rates and narrow half-maximum widths (WHMs). However, currently, BN-type MR molecules mostly exhibit light colors in the sky-blue to green region, with WHMs mostly around 30 nm, which fails to meet the requirements of the next-generation ultra-high-definition video standard BT.2020. Summary of the Invention

[0006] In one aspect, the present invention provides an organic compound having a structure as shown in formula (1), formula (2) or formula (3), or having a structure formed by the polymerization of any two of formulas (1-1), (1-2), and (1-3):

[0007]

[0008] Cycles Ar1, Ar2, Ar3, and Ar4 are each independently selected from aromatic rings of C6 to C60 or heteroaromatic rings of C3 to C60;

[0009] Ring Ar3 and ring Ar4 are not connected, or they are connected by a single CC key, or by O, S or Se, or by CR6R7 or NR8;

[0010] Ring Ar1 and ring Ar2 are not connected, or are connected by a single CC key, or by O, S or Se, or by CR6R7 or NR8;

[0011] R1, R2, R3, R4, R5, R6 and R7 are each independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0012] n1, n2, n3, and n4 are each independently selected from integers between 0 and 4;

[0013] When n1, n2, n3, and n4 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, and multiple R4s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, and the multiple R4s are either not connected or connected in a cycle.

[0014] R8, R9 and R 10 Each is independently selected from one of the following: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0015] When the above R1-R 10When each of the above substituents is present independently, each substituent is independently selected from one or a combination of two of the following: halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 arylboryl, and C3-C30 heteroaryl.

[0016] 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.

[0017] 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.

[0018] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0019] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] In this specification, aryloxy groups can be exemplified by the monovalent groups formed by the above-mentioned aryl and heteroaryl groups and oxygen.

[0024] In this specification, alkoxy groups can be exemplified by the aforementioned chain alkyl groups or monovalent groups composed of cycloalkyl groups and oxygen.

[0025] Examples of C6-C60 arylamine groups mentioned in this specification include: phenylamine, methylphenylamine, naphthylamine, anthraceneamine, phenanthreneamine, biphenylamine, etc.

[0026] Examples of C6-C60 heteroaryl amino groups mentioned in this specification include pyridinylamino, pyrimidinylamino, and dibenzofuranylamino.

[0027] Furthermore, in equations (1-1), (1-2), and (1-3), n1, n2, n3, and n4 are each independently selected from integers of equations 1-2;

[0028] Each of R1-R7 is independently selected from one of deuterium, halogen, cyano, C1-C12 chain alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl. When each of R1-R7 has a substituent, the substituent is independently selected from one or a combination of two of halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0029] Preferably, each of R1-R7 is independently selected from one of deuterium, halogen, cyano, C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0030] More preferably, each of R1-R7 is independently selected from any one of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring;

[0031] Most preferably, each of R1-R7 is independently a substituted or unsubstituted benzene ring, and the substituent is selected from one or a combination of two of the following: halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0032] Furthermore, each of the rings Ar1, Ar2, Ar3, and Ar4 is independently selected from an aromatic ring of C6 to C30 or a heteroaromatic ring of C3 to C20;

[0033] The preferred Ar1, cyclic Ar2, cyclic Ar3 and cyclic Ar4 are each independently selected from any one of benzene ring, naphthyl ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene or thiophene;

[0034] More preferably, each of the rings Ar1, Ar2, Ar3 and Ar4 is independently a benzene ring, a naphthyl ring, a dibenzofuran, a carbazole, or a dibenzothiophene.

[0035] Most preferably, Ar1, cyclic Ar2, cyclic Ar3 and cyclic Ar4 are each independently a benzene ring or a naphthalene ring.

[0036] Furthermore, each of R1-R7 is independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenoxy, diphenylamino, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, biphenyl, amphoteric. Triphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, cis or trans indofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, oxazolyl Benzoxazolyl, naphthooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1 One of 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, pteridyl, indazinyl, benzothiadiazolyl, diphenylboryl, diphenylboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups;

[0037] The R8-R 10Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, 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, phenanthreneazoleyl, pyridinazoleyl, pyrazinazoleyl, quinoxalinazoleyl , oxazolyl, benzoxazolyl, naphthoxazolyl, anthraxazolyl, phenanthazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 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, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, 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, or a combination thereof;

[0038] Preferably, R1-R7 are independently represented as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenoxy, diphenylamino, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thiophene, benzothiophene, pyrroleyl, isoyindolyl, carbazoleyl, indene One of the following groups: carbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination thereof;

[0039] Preferably, the R8-R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrroleyl, isoyindolyl, carbazoleyl, indocarbazoleyl, pyridine One of the following groups: yl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups.

[0040] Furthermore, R1-R7 are each independently represented as one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenoxy, diphenylamino, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, carbazole, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups;

[0041] The R8-R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyano, phenyl, naphthyl, anthracene, fluorenyl, and spirodifluorenyl.

[0042] Furthermore, R1 is connected to the meta and / or para positions of the B atom connection sites in ring Ar1, R4 is connected to the meta and / or para positions of the B atom connection sites in ring Ar4, R3 is connected to the meta and / or para positions of the N atom connection sites in ring Ar3, and R2 is connected to the meta and / or para positions of the N atom connection sites in ring Ar2.

[0043] Preferably, R1 is connected at a meta site of the B atom connection site in ring Ar1, R4 is connected at a meta site of the B atom connection site in ring Ar4, R3 is connected at a meta site of the N atom connection site in ring Ar3, and R2 is connected at a meta site of the N atom connection site in ring Ar2.

[0044] In the compounds of the present invention, the structures formed by the polymerization of any two of formulas (1-1), (1-2), and (1-3) are as shown in any one of formulas (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6):

[0045]

[0046] The definitions of rings Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, R6, R7, n1, n2, n3, and n4 are the same as those in equations (1-1), (1-2), and (1-3).

[0047] More preferably, the compounds of the above general formula of the present invention can preferably include the following specific structural compounds: A-1 to A-240, B-1 to B-147, C-1 to C-210. These compounds are only representative examples.

[0048]

[0049]

[0050]

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[0059]

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[0065]

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[0070]

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[0081]

[0082] The compounds of this invention are designed with core structures such as general formulas (1-1), (1-2), (1-3), (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6). In the commonly used nitrogen-boron-nitrogen structures of the prior art, at least one carbonyl group is introduced at the meta position of the boron atom in the central benzene ring. On the one hand, the different donor-acceptor properties of the carbonyl group and the nitrogen atom cause a significant blue shift in the emitted light color. On the other hand, the newly added carbonyl group locks in the donor on one side, forming a planar rigid framework structure with the central benzene ring, which reduces the relaxation degree of the excited state structure. This results in the target molecule possessing high luminous efficiency, high color purity, and high stability. Furthermore, by changing the peripheral donor groups, the emitted light color can be adjusted by utilizing the different electron-donating abilities and HOMO conjugation degrees of these groups. Moreover, the introduction of the n-π* transition characteristics of the carbonyl group can improve the TADF performance of the molecule, thereby increasing the upconversion rate of the material, improving exciton utilization, and obtaining high-performance OLED devices. When general formulas (1-1), (1-2), and (1-3) are polymerized to form structures of formulas (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6), the overall molecular structure remains planar and rigid, and provides a wider range of photochromic modulation capabilities. Compared with existing BN dye molecules, our proposed target molecule has a significantly narrower half-maximum width and higher efficiency and lifetime in organic optoelectronic devices.

[0083] In addition, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production scale-up.

[0084] A second aspect of the invention also protects the use of any of the compounds shown in formulas (1), (2) and (3) as functional materials in organic electronic devices, including: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

[0085] Thirdly, the present invention also provides an organic electroluminescent device, including 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 contains any of the compounds shown in the above general formula (1), formula (2) and formula (3).

[0086] Specifically, one embodiment of the present invention provides 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 the light-emitting layer contains the general formula compound of the present invention shown in formulas (1), (2) and (3) above.

[0087] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials. Detailed Implementation

[0088] 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.

[0089] All the chemical reagents used in this invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, and potassium carbonate, 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).

[0090] The synthesis method of the compounds of the present invention will be briefly described below.

[0091] Synthesis Examples

[0092] Representative synthetic pathways:

[0093]

[0094]

[0095] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0096] Synthesis Examples

[0097] Synthesis Example 1:

[0098] Synthesis of compound A1

[0099]

[0100] Weigh 5 mmol of compound A-1-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-1-2, which is a yellow solid.

[0101] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-1-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-1 (26% yield, HPLC purity 99.62%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 442.13; Elemental analysis results: Theoretical values: C, 84.19; H, 3.42; B, 2.44; N, 6.33; Experimental values: C, 84.19; H, 3.43; B, 2.44; N, 6.32.

[0102] Synthesis Example 2:

[0103] Synthesis of compound A-4

[0104]

[0105] Weigh 5 mmol of compound A-4-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-4-2, which is a yellow solid.

[0106] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-4-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-4 (24% yield, HPLC purity 99.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 666.38; Elemental analysis results: Theoretical values: C, 84.67; H, 7.11; B, 1.62; N, 4.20; Experimental values: C, 84.67; H, 7.12; B, 1.62; N, 4.20.

[0107] Synthesis Example 3:

[0108] Synthesis of compound A8

[0109]

[0110] Weigh 5 mmol of compound A-8-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-8-2, which is a yellow solid.

[0111] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-8-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-8 (17% yield, HPLC purity 98.26%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 970.50; Elemental analysis results: Theoretical values: C, 87.82; H, 6.54; B, 1.11; N, 2.88; Experimental values: C, 87.81; H, 6.54; B, 1.11; N, 2.87.

[0112] Synthesis Example 4:

[0113] Synthesis of compound A10

[0114]

[0115] Weigh 5 mmol of compound A-10-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-10-2, which is a yellow solid.

[0116] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-10-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-10 (19% yield, HPLC purity 98.56%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1110.42; Elemental analysis results: Theoretical values: C, 85.40; H, 4.63; B, 0.97; N, 7.56; Experimental values: C, 85.41; H, 4.63; B, 0.98; N, 7.56.

[0117] Synthesis Example 5:

[0118] Synthesis of compound A-13

[0119]

[0120] Weigh 5 mmol of compound A-13-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-13-2 as a yellow solid.

[0121] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-13-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound A-13 (25% yield, HPLC purity 99.17%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 642.19; Elemental analysis results: Theoretical values: C, 87.86; H, 3.61; B, 1.68; N, 4.36; Experimental values: C, 87.86; H, 3.62; B, 1.68; N, 4.36.

[0122] Synthesis Example 6:

[0123] Synthesis of compound A-17

[0124]

[0125] Weigh 5 mmol of compound A-17-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-17-2, which is a yellow solid.

[0126] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-17-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-17 (24% yield, HPLC purity 99.25%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 670.41; Elemental analysis results: Theoretical values: C, 84.16; H, 7.66; B, 1.61; N, 4.18; Experimental values: C, 84.17; H, 7.66; B, 1.61; N, 4.18.

[0127] Synthesis Example 7:

[0128] Synthesis of compound A-21

[0129]

[0130] Compound A-21-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound A-21-2, a yellow solid.

[0131] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-21-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound A-21 (27% yield, HPLC purity 98.36%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 772.24; Elemental analysis results: Theoretical values: C, 85.50; H, 3.78; B, 1.40; N, 7.25; Experimental values: C, 85.51; H, 3.78; B, 1.40; N, 7.26.

[0132] Synthesis Example 8:

[0133] Synthesis of compound A-24

[0134]

[0135] Compound A-24-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain the intermediate compound A-24-2, a yellow solid.

[0136] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-24-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-24 (27% yield, HPLC purity 98.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 772.24; Elemental analysis results: Theoretical values: C, 85.50; H, 3.78; B, 1.40; N, 7.25; Experimental values: C, 85.50; H, 3.78; B, 1.40; N, 7.26.

[0137] Synthesis Example 9:

[0138] Synthesis of compound A-44

[0139]

[0140] Compound A-44-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-44-2, a yellow solid.

[0141] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-44-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to give the target compound A-44 (25% yield, HPLC purity 97.75%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 772.24; Elemental analysis results: Theoretical values: C, 85.50; H, 3.78; B, 1.40; N, 7.25; Experimental values: C, 85.50; H, 3.78; B, 1.41; N, 7.27.

[0142] Synthesis Example 10:

[0143] Synthesis of compound A-55

[0144]

[0145] Weigh 5 mmol of compound A-55-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-55-2, which is a yellow solid.

[0146] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-55-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-55 (25% yield, HPLC purity 97.68%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 770.25; Elemental analysis results: Theoretical values: C, 88.83; H, 4.05; B, 1.40; N, 3.63; Experimental values: C, 88.81; H, 4.02; B, 1.40; N, 3.66.

[0147] Synthesis Example 11:

[0148] Synthesis of compound A-65

[0149]

[0150] Compound A-65-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound A-65-2, a yellow solid.

[0151] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-65-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-65 (21% yield, HPLC purity 98.36%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 594.19; Elemental analysis results: Theoretical values: C, 86.88; H, 3.90; B, 1.82; N, 4.71; Experimental values: C, 86.88; H, 3.90; B, 1.83; N, 4.72.

[0152] Synthesis Example 12:

[0153] Synthesis of compound A-70

[0154]

[0155] Weigh 5 mmol of compound A-70-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-70-2, which is a yellow solid.

[0156] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-70-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-70 (19% yield, HPLC purity 97.23%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 680.39; Elemental analysis results: Theoretical values: C, 84.69; H, 7.26; B, 1.59; N, 4.12; Experimental values: C, 84.69; H, 7.26; B, 1.58; N, 4.13.

[0157] Synthesis Example 13:

[0158] Synthesis of compound A-80

[0159]

[0160] Compound A-80-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-80-2, a yellow solid.

[0161] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-80-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-80 (22% yield, HPLC purity 98.79%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 474.12; Elemental analysis results: Theoretical values: C, 78.51; H, 3.19; B, 2.28; N, 5.91; Experimental values: C, 78.51; H, 3.17; B, 2.28; N, 5.92.

[0162] Synthesis Example 14:

[0163] Synthesis of compound A-81

[0164]

[0165] Compound A-81-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. Anhydrous sodium sulfate was added and the organic phase was dried. The solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound A-81-2, a yellow solid.

[0166] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-81-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound A-81 (25% yield, HPLC purity 97.75%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 506.07; Elemental analysis results: Theoretical values: C, 73.53; H, 2.99; B, 2.13; N, 5.53; S, 12.66; Experimental values: C, 73.53; H, 2.99; B, 2.14; N, 5.53; S, 12.66.

[0167] Synthesis Example 15:

[0168] Synthesis of compound A-82

[0169]

[0170] Compound A-82-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. Anhydrous sodium sulfate was added and the organic phase was dried. The solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound A-82-2, a yellow solid.

[0171] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-82-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-82 (26% yield, HPLC purity 98.32%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 601.96; Elemental analysis results: Theoretical values: C, 62.03; H, 2.52; B, 1.80; N, 4.67; Se, 26.31; Experimental values: C, 62.03; H, 2.52; B, 1.81; N, 4.67; Se, 26.31.

[0172] Synthesis Example 16:

[0173] Synthesis of compound A-85

[0174]

[0175] Compound A-85-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound A-85-2, a yellow solid.

[0176] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-85-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-85 (25% yield, HPLC purity 97.75%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 806.24; Elemental analysis results: Theoretical values: C, 81.87; H, 4.37; B, 1.34; N, 3.47; Si, 6.96; Experimental values: C, 81.87; H, 4.37; B, 1.35; N, 3.46; Si, 6.96.

[0177] Synthesis Example 17:

[0178] Synthesis of compound A-87

[0179]

[0180] Compound A-87-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound A-87-2, a yellow solid.

[0181] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-87-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-87 (23% yield, HPLC purity 97.45%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 458.12; Elemental analysis results: Theoretical values: C, 81.25; H, 3.30; B, 2.36; N, 6.11; Experimental values: C, 81.25; H, 3.31; B, 2.36; N, 6.12.

[0182] Synthesis Example 18:

[0183] Synthesis of compound A-94

[0184]

[0185] Compound A-94-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound A-94-2, a yellow solid.

[0186] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-94-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-94 (25% yield, HPLC purity 99.12%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 622.17; Elemental analysis results: Theoretical values: C, 82.96; H, 3.72; B, 1.74; N, 4.50; Si, 4.51; Experimental values: C, 82.96; H, 3.72; B, 1.75; N, 4.50; Si, 4.51.

[0187] Synthesis Example 19:

[0188] Synthesis of compound A-155

[0189]

[0190] Weigh 5 mmol of compound A-155-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-155-2, which is a yellow solid.

[0191] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-155-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to obtain the target compound A-155 (22% yield, HPLC purity 96.94%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 548.12; Elemental analysis results: Theoretical values: C, 81.03; H, 3.12; B, 1.97; N, 5.11; S, 5.85; Experimental values: C, 81.03; H, 3.12; B, 1.98; N, 5.11; S, 5.85.

[0192] Synthesis Example 20:

[0193] Synthesis of compound A-179

[0194]

[0195] Weigh 5 mmol of compound A-179-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound A-179-2, which is a yellow solid.

[0196] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-179-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-179 (24% yield, HPLC purity 97.79%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.32; B, 1.50; N, 5.82.

[0197] Synthesis Example 21:

[0198] Synthesis of compound A-180

[0199]

[0200] Compound A-180-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-180-2, which was a yellow solid.

[0201] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-180-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-180 (26% yield, HPLC purity 98.53%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.32; B, 1.51; N, 5.84.

[0202] Synthesis Example 22:

[0203] Synthesis of compound A-181

[0204]

[0205] Weigh 5 mmol of compound A-181-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound A-181-2, which is a yellow solid.

[0206] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-181-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 6:1) to obtain the target compound A-181 (21% yield, HPLC purity 98.13%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.12; H, 5.32; B, 1.51; N, 5.84.

[0207] Synthesis Example 23:

[0208] Synthesis of compound A-182

[0209]

[0210] Compound A-182-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-182-2, which was a yellow solid.

[0211] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-182-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-182 (22% yield, HPLC purity 97.89%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.33; B, 1.50; N, 5.85.

[0212] Synthesis Example 24:

[0213] Synthesis of compound A-183

[0214]

[0215] Weigh 5 mmol of compound A-183-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-183-2, which is a yellow solid.

[0216] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-183-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-183 (25% yield, HPLC purity 96.68%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.33; B, 1.50; N, 5.84.

[0217] Synthesis Example 25:

[0218] Synthesis of compound A-184

[0219]

[0220] Weigh 5 mmol of compound A-184-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound A-184-2, which is a yellow solid.

[0221] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-184-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-184 (23% yield, HPLC purity 97.55%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.32; B, 1.50; N, 5.86.

[0222] Synthesis Example 26:

[0223] Synthesis of compound A-185

[0224]

[0225] Compound A-185-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound A-185-2, a yellow solid.

[0226] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-185-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to obtain the target compound A-185 (25% yield, HPLC purity 98.22%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.11; H, 5.32; B, 1.52; N, 5.83.

[0227] Synthesis Example 27:

[0228] Synthesis of compound A-186

[0229]

[0230] Compound A-186-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-186-2, which was a yellow solid.

[0231] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-186-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-186 (23% yield, HPLC purity 98.65%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 719.31; Elemental analysis results: Theoretical values: C, 85.11; H, 5.32; B, 1.50; N, 5.84; Experimental values: C, 85.13; H, 5.31; B, 1.50; N, 5.84.

[0232] Synthesis Example 28:

[0233] Synthesis of compound B-1

[0234]

[0235] Weigh 5 mmol of compound B-1-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain the intermediate compound B-1-2, which is a yellow solid.

[0236] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-1-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound B-1 (27% yield, HPLC purity 99.21%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 468.11; Elemental analysis results: Theoretical values: C, 82.08; H, 2.80; B, 2.31; N, 5.98; Experimental values: C, 82.06; H, 2.80; B, 2.31; N, 5.99.

[0237] Synthesis Example 29:

[0238] Synthesis of compound B-4

[0239]

[0240] Weigh 5 mmol of compound B-4-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-4-2, which is a yellow solid.

[0241] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-4-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound B-4 (21% yield, HPLC purity 96.98%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 692.36; Elemental analysis results: Theoretical values: C, 83.23; H, 6.55; B, 1.56; N, 4.04; Experimental values: C, 83.23; H, 6.56; B, 1.56; N, 4.04.

[0242] Synthesis Example 30:

[0243] Synthesis of compound B-5

[0244]

[0245] Weigh 5 mmol of compound B-5-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound B-5-2, which is a yellow solid.

[0246] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-5-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to give the target compound B-5 (24% yield, HPLC purity 98.35%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 772.23; Elemental analysis results: Theoretical values: C, 87.05; H, 3.78; B, 1.40; N, 3.63; Experimental values: C, 87.05; H, 3.78; B, 1.38; N, 3.65.

[0247] Synthesis Example 31:

[0248] Synthesis of compound B-11

[0249]

[0250] Weigh 5 mmol of compound B-11-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a DMF solution containing 12 mmol of NBS dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-11-2, which is a yellow solid.

[0251] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-11-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 80 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-11 (22% yield, HPLC purity 98.68%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 696.39; Elemental analysis results: Theoretical values: C, 82.75; H, 7.09; B, 1.55; N, 4.02; Experimental values: C, 82.76; H, 7.08; B, 1.55; N, 4.02.

[0252] Synthesis Example 32:

[0253] Synthesis of compound B-23

[0254]

[0255] Weigh 5 mmol of compound B-23-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-23-2 as a yellow solid.

[0256] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-23-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-23 (23% yield, HPLC purity 97.33%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 633.16; Elemental analysis results: Theoretical values: C, 83.43; H, 3.18; B, 1.71; N, 6.63; Experimental values: C, 83.42; H, 3.18; B, 1.71; N, 6.62.

[0257] Synthesis Example 33:

[0258] Synthesis of compound B-25

[0259]

[0260] Weigh 5 mmol of compound B-25-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a DMF solution containing 12 mmol of NBS dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain the intermediate compound B-25-2, which is a yellow solid.

[0261] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-25-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-25 (21% yield, HPLC purity 98.21%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 532.05; Elemental analysis results: Theoretical values: C, 72.19; H, 2.46; B, 2.03; N, 5.26; S, 12.04; Experimental values: C, 72.20; H, 2.46; B, 2.02; N, 5.26; S, 12.04.

[0262] Synthesis Example 34:

[0263] Synthesis of compound B-29

[0264]

[0265] Weigh 5 mmol of compound B-29-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-29-2, which is a yellow solid.

[0266] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-29-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to give the target compound B-29 (22% yield, HPLC purity 98.76%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 832.22; Elemental analysis results: Theoretical values: C, 80.76; H, 3.99; B, 1.30; N, 3.36; Si, 6.74; Experimental values: C, 80.76; H, 3.99; B, 1.30; N, 3.36; Si, 6.74.

[0267] Synthesis Example 35:

[0268] Synthesis of compound B-43

[0269]

[0270] Weigh 5 mmol of compound B-43-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-43-2, which is a yellow solid.

[0271] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-43-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-43 (22% yield, HPLC purity 97.89%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 574.09; Elemental analysis results: Theoretical values: C, 79.46; H, 2.63; B, 1.88; N, 4.88; S, 5.58; Experimental values: C, 79.48; H, 2.62; B, 1.88; N, 4.88; S, 5.58.

[0272] Synthesis Example 36:

[0273] Synthesis of compound B-46

[0274]

[0275] Weigh 5 mmol of compound B-46-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-46-2, which is a yellow solid.

[0276] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-46-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 80 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound B-46 (22% yield, HPLC purity 98.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 586.19; Elemental analysis results: Theoretical values: C, 83.97; H, 3.95; B, 1.84; N, 4.78; Experimental values: C, 83.97; H, 3.95; B, 1.86; N, 4.78.

[0277] Synthesis Example 37:

[0278] Synthesis of compound B-59

[0279]

[0280] Weigh 5 mmol of compound B-59-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 2:1) to obtain the intermediate compound B-59-2, which is a yellow solid.

[0281] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-59-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 80 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 5:1) to obtain the target compound B-59 (23% yield, HPLC purity 99.65%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 798.22; Elemental analysis results: Theoretical values: C, 84.22; H, 3.41; B, 1.35; N, 7.02; Experimental values: C, 84.22; H, 3.42; B, 1.36; N, 7.03.

[0282] Synthesis Example 38:

[0283] Synthesis of compound B-83

[0284]

[0285] Weigh 5 mmol of compound B-83-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-83-2, which is a yellow solid.

[0286] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-83-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 80 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-83 (24% yield, HPLC purity 98.85%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 680.08; Elemental analysis results: Theoretical values: C, 77.65; H, 2.52; B, 1.59; N, 4.12; S, 9.42; Experimental values: C, 77.66; H, 2.52; B, 1.60; N, 4.12; S, 9.42.

[0287] Synthesis Example 39:

[0288] Synthesis of compound C-1

[0289]

[0290] Weigh 5 mmol of compound C-1-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-1-2, which is a yellow solid.

[0291] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-1-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to give the target compound C-1 (21% yield, HPLC purity 97.57%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 606.19; Elemental analysis results: Theoretical values: C, 87.14; H, 3.82; B, 1.78; N, 4.62; Experimental values: C, 87.14; H, 3.82; B, 1.78; N, 4.61.

[0292] Synthesis Example 40:

[0293] Synthesis of compound C-4

[0294]

[0295] Weigh 5 mmol of compound C-4-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-4-2, which is a yellow solid.

[0296] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-4-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-4 (21% yield, HPLC purity 98.64%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 830.44; Elemental analysis results: Theoretical values: C, 86.73; H, 6.67; B, 1.30; N, 3.37; Experimental values: C, 86.72; H, 6.68; B, 1.30; N, 3.37.

[0297] Synthesis Example 41:

[0298] Synthesis of compound C-5

[0299]

[0300] Weigh 5 mmol of compound C-5-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound C-5-2 as a yellow solid.

[0301] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-5-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 5:1) to obtain the target compound C-5 (22% yield, HPLC purity 98.92%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 910.32; Elemental analysis results: Theoretical values: C, 89.67; H, 4.32; B, 1.19; N, 3.08; Experimental values: C, 89.68; H, 4.32; B, 1.19; N, 3.08.

[0302] Synthesis Example 42:

[0303] Synthesis of compound C-11

[0304]

[0305] Weigh 5 mmol of compound C-11-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-11-2, which is a yellow solid.

[0306] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-11-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-11 (18% yield, HPLC purity 97.51%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 834.47; Elemental analysis results: Theoretical values: C, 86.31; H, 7.12; B, 1.29; N, 3.36; Experimental values: C, 86.31; H, 7.12; B, 1.31; N, 3.36.

[0307] Synthesis Example 43:

[0308] Synthesis of compound C-23

[0309]

[0310] Weigh 5 mmol of compound C-23-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-23-2 as a yellow solid.

[0311] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-23-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound C-23 (22% yield, HPLC purity 97.78%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 771.25; Elemental analysis results: Theoretical values: C, 87.16; H, 3.92; B, 1.40; N, 5.45; Experimental values: C, 87.16; H, 3.92; B, 1.40; N, 5.46.

[0312] Synthesis Example 44:

[0313] Synthesis of compound C-25

[0314]

[0315] Weigh 5 mmol of compound C-25-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-25-2 as a yellow solid.

[0316] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-25-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to give the target compound C-25 (26% yield, HPLC purity 98.75%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 670.13; Elemental analysis results: Theoretical values: C, 78.81; H, 3.46; B, 1.61; N, 4.18; S, 9.56; Experimental values: C, 78.81; H, 3.46; B, 1.61; N, 4.18; S, 9.56.

[0317] Synthesis Example 45:

[0318] Synthesis of compound C-29

[0319]

[0320] Weigh 5 mmol of compound C-29-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound C-29-2, which is a yellow solid.

[0321] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-29-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-29 (23% yield, HPLC purity 98.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 970.30; Elemental analysis results: Theoretical values: C, 84.11; H, 4.46; B, 1.11; N, 2.88; Si, 5.78; Experimental values: C, 84.11; H, 4.45; B, 1.11; N, 2.88; Si, 5.78.

[0322] Synthesis Example 46:

[0323] Synthesis of compound C-43

[0324]

[0325] Weigh 5 mmol of compound C-43-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-43-2, which is a yellow solid.

[0326] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-43-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 12:1) to obtain the target compound C-43 (22% yield, HPLC purity 97.96%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 712.18; Elemental analysis results: Theoretical values: C, 84.27; H, 3.54; B, 1.52; N, 3.93; S, 4.50; Experimental values: C, 84.27; H, 3.55; B, 1.52; N, 3.92; S, 4.51.

[0327] Synthesis Example 47:

[0328] Synthesis of compound C-46

[0329]

[0330] Compound C-46-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain the intermediate compound C-46-2, a yellow solid.

[0331] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-46-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound C-46 (21% yield, HPLC purity 99.22%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 724.27; Elemental analysis results: Theoretical values: C, 87.84; H, 4.59; B, 1.49; N, 3.87; Experimental values: C, 87.84; H, 4.59; B, 1.51; N, 3.87.

[0332] Synthesis Example 48:

[0333] Synthesis of compound C-59

[0334]

[0335] Compound C-59-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound C-59-2, a yellow solid.

[0336] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-59-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-59 (23% yield, HPLC purity 98.15%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 936.31; Elemental analysis results: Theoretical values: C, 87.18; H, 3.98; B, 1.15; N, 5.98; Experimental values: C, 87.18; H, 3.98; B, 1.18; N, 5.96.

[0337] Synthesis Example 49:

[0338] Synthesis of compound C-83

[0339]

[0340] Compound C-83-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain the intermediate compound C-83-2, a yellow solid.

[0341] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-83-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 5:1) to obtain the target compound C-83 (22% yield, HPLC purity 98.77%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 818.17; Elemental analysis results: Theoretical values: C, 82.15; H, 3.32; B, 1.32; N, 3.42; S, 7.83; Experimental values: C, 82.16; H, 3.31; B, 1.31; N, 3.41; S, 7.83.

[0342] Synthesis Example 50:

[0343] Synthesis of compound C-94

[0344]

[0345] Weigh 5 mmol of compound C-94-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-94-2, which is a yellow solid.

[0346] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-94-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, the mixture was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound C-94 (20% yield, HPLC purity 98.28%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 604.17; Elemental analysis results: Theoretical values: C, 87.43; H, 3.50; B, 1.79; N, 4.63; Experimental values: C, 87.41; H, 3.50; B, 1.80; N, 4.63.

[0347] Synthesis Example 51:

[0348] Synthesis of compound C-97

[0349]

[0350] Weigh 5 mmol of compound C-97-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-97-2, which is a yellow solid.

[0351] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-97-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to give the target compound C-97 (22% yield, HPLC purity 98.90%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 828.43; Elemental analysis results: Theoretical values: C, 86.94; H, 6.45; B, 1.30; N, 3.38; Experimental values: C, 86.94; H, 6.45; B, 1.31; N, 3.38.

[0352] Synthesis Example 52:

[0353] Synthesis of compound C-98

[0354]

[0355] Weigh 5 mmol of compound C-98-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a DMF solution containing 6 mmol of NBS dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound C-98-2, which is a yellow solid.

[0356] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-98-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified with HCl solution to pH 1-2 and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined and washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were then added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added and stirred for 15 h. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to give the target compound C-98 (25% yield, HPLC purity 98.62%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 908.30; Elemental analysis results: Theoretical values: C, 89.86; H, 4.10; B, 1.19; N, 3.08; Experimental values: C, 89.86; H, 4.11; B, 1.18; N, 3.08.

[0357] Synthesis Example 53:

[0358] Synthesis of compound C-116

[0359]

[0360] Weigh 5 mmol of compound C-116-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a DMF solution containing 6 mmol of NBS dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound C-116-2, which is a yellow solid.

[0361] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-116-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-116 (19% yield, HPLC purity 99.08%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 769.23; Elemental analysis results: Theoretical values: C, 87.39; H, 3.67; B, 1.40; N, 5.46; Experimental values: C, 87.36; H, 3.68; B, 1.38; N, 5.46.

[0362] Synthesis Example 54:

[0363] Synthesis of compound C-122

[0364]

[0365] Weigh 5 mmol of compound C-122-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound C-122-2, which is a yellow solid.

[0366] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-122-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-122 (23% yield, HPLC purity 98.35%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 968.29; Elemental analysis results: Theoretical values: C, 84.28; H, 4.26; B, 1.12; N, 2.89; Si, 5.80; Experimental values: C, 84.28; H, 4.26; B, 1.12; N, 2.89; Si, 5.81.

[0367] Synthesis Example 55:

[0368] Synthesis of compound C-140

[0369]

[0370] Weigh 5 mmol of compound C-140-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a DMF solution containing 6 mmol of NBS dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound C-140-2, which is a yellow solid.

[0371] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-140-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-140 (22% yield, HPLC purity 97.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 934.29; Elemental analysis results: Theoretical values: C, 87.37; H, 3.77; B, 1.16; N, 5.99; Experimental values: C, 87.37; H, 3.78; B, 1.17; N, 5.99.

[0372] Synthesis Example 56:

[0373] Synthesis of compound C-150

[0374]

[0375] Weigh 5 mmol of compound C-150-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-150-2, which is a yellow solid.

[0376] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-150-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-150 (22% yield, HPLC purity 98.87%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 816.15; Elemental analysis results: Theoretical values: C, 82.35; H, 3.09; B, 1.32; N, 3.43; S, 7.85; Experimental values: C, 82.35; H, 3.09; B, 1.32; N, 3.41; S, 7.86.

[0377] Synthesis Example 57:

[0378] Synthesis of compound A-173

[0379]

[0380] Weigh 5 mmol of compound A-173-1 into a 250 mL two-necked flask, then add 120 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 40 mL of NBS (12 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-173-2, which is a yellow solid.

[0381] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-173-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.28 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound A-173 (21% yield, HPLC purity 99.53%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 810.24; Elemental analysis results: Theoretical values: C, 82.99; H, 3.48; B, 2.67; N, 6.91; Experimental values: C, 82.97; H, 3.49; B, 2.66; N, 6.93.

[0382] Synthesis Example 58:

[0383] Synthesis of compound B-49

[0384]

[0385] Weigh 5 mmol of compound B-49-1 into a 250 mL two-necked flask, then add 120 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 40 mL of NBS (24 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound B-49-2, which is a yellow solid.

[0386] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 24 mmol) was slowly added to a tert-butylbenzene (80 mL) solution of intermediate compound B-49-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (40 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (40 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 40 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.56 mol) and NaCl (0.12 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (40 ml) / HCl (6 M, 120 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound B-49 (18% yield, HPLC purity 99.33%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 862.20; Elemental analysis results: Theoretical values: C, 80.77; H, 2.80; B, 2.51; N, 6.50; Experimental values: C, 80.80; H, 2.79; B, 2.49; N, 6.53.

[0387] Synthesis Example 59:

[0388] Synthesis of compound A-206

[0389]

[0390] Compound A-206-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 2:1) to obtain the intermediate compound A-206-2, a yellow solid.

[0391] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-206-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to obtain the target compound A-206 (21% yield, HPLC purity 98.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 854.53; Elemental analysis results: Theoretical values: C, 85.69; H, 7.90; B, 1.26; N, 3.28; Experimental values: C, 85.69; H, 7.91; B, 1.26; N, 3.28.

[0392] Synthesis Example 60:

[0393] Synthesis of compound A-215

[0394]

[0395] Weigh 5 mmol of compound A-215-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound A-215-2, which is a yellow solid.

[0396] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound A-215-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 5:1) to obtain the target compound A-215 (22% yield, HPLC purity 99.21%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 767.40; Elemental analysis results: Theoretical values: C, 84.47; H, 6.56; B, 1.41; N, 5.47; Experimental values: C, 84.47; H, 6.58; B, 1.41; N, 5.47.

[0397] Synthesis Example 61:

[0398] Synthesis of compound B-113

[0399]

[0400] Weigh 5 mmol of compound B-113-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain the intermediate compound B-113-2, which is a yellow solid.

[0401] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-113-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 80 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound B-113 (20% yield, HPLC purity 97.81%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 880.51; Elemental analysis results: Theoretical values: C, 84.52; H, 7.44; B, 1.23; N, 3.18; Experimental values: C, 84.52; H, 7.41; B, 1.26; N, 3.18.

[0402] Synthesis Example 62:

[0403] Synthesis of compound B-122

[0404]

[0405] Weigh 5 mmol of compound B-122-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of a 12 mmol NBS solution to the DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound B-122-2, which is a yellow solid.

[0406] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 12 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound B-122-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.25 mol) and NaCl (0.06 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 80 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 12:1) to obtain the target compound B-122 (22% yield, HPLC purity 97.68%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 793.38; Elemental analysis results: Theoretical values: C, 83.22; H, 6.10; B, 1.36; N, 5.29; Experimental values: C, 83.22; H, 6.10; B, 1.36; N, 5.31.

[0407] Synthesis Example 63:

[0408] Synthesis of compound C-158

[0409]

[0410] Weigh 5 mmol of compound C-158-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain intermediate compound C-158-2, which is a yellow solid.

[0411] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-158-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-158 (25% yield, HPLC purity 98.43%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 904.46; Elemental analysis results: Theoretical values: C, 87.59; H, 6.35; B, 1.19; N, 3.10; Experimental values: C, 87.59; H, 6.35; B, 1.19; N, 3.11.

[0412] Synthesis Example 64:

[0413] Synthesis of compound C-168

[0414]

[0415] Weigh 5 mmol of compound C-168-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 2:1) to obtain intermediate compound C-168-2, which is a yellow solid.

[0416] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-168-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to obtain the target compound C-168 (22% yield, HPLC purity 98.88%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1026.38; Elemental analysis results: Theoretical values: C, 90.05; H, 4.61; B, 1.05; N, 2.73; Experimental values: C, 90.06; H, 4.58; B, 1.06; N, 2.73.

[0417] Synthesis Example 65:

[0418] Synthesis of compound C-176

[0419]

[0420] Compound C-176-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain the intermediate compound C-176-2, a yellow solid.

[0421] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-176-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 8:1) to obtain the target compound C-176 (21% yield, HPLC purity 98.31%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1016.58; Elemental analysis results: Theoretical values: C, 87.38; H, 7.23; B, 1.06; N, 2.75; Experimental values: C, 87.38; H, 7.23; B, 1.05; N, 2.76.

[0422] Synthesis Example 66:

[0423] Synthesis of compound C-187

[0424]

[0425] Compound C-187-1 (5 mmol) was weighed into a 250 mL two-necked flask. Then, 80 mL of N,N-dimethylformamide (DMF) was added to the flask, and the mixture was stirred until dissolved. Then, 20 mL of a DMF solution containing 6 mmol of NBS was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was allowed to heat naturally and stirred at room temperature for 20 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane and poured into water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation of the filtered organic phase. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 4:1) to obtain the intermediate compound C-187-2, which was a yellow solid.

[0426] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-187-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-187 (22% yield, HPLC purity 99.01%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1035.32; Elemental analysis results: Theoretical values: C, 86.95; H, 3.70; B, 1.04; N, 6.76; Experimental values: C, 86.96; H, 3.68; B, 1.05; N, 6.76.

[0427] Synthesis Example 67:

[0428] Synthesis of compound C-197

[0429]

[0430] Weigh 5 mmol of compound C-197-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 3:1) to obtain intermediate compound C-197-2, which is a yellow solid.

[0431] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-197-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. After cooling to room temperature, ice water (20 ml) / HCl (6 M, 60 ml) was added, and the mixture was stirred for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 10:1) to obtain the target compound C-197 (20% yield, HPLC purity 98.65%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 959.29; Elemental analysis results: Theoretical values: C, 86.34; H, 3.57; B, 1.13; N, 7.30; Experimental values: C, 86.34; H, 3.57; B, 1.13; N, 7.31.

[0432] Synthesis Example 68:

[0433] Synthesis of compound C-209

[0434]

[0435] Weigh 5 mmol of compound C-209-1 into a 250 mL two-necked flask, then add 80 mL of N,N-dimethylformamide (DMF) to the flask. After stirring to dissolve, slowly add 20 mL of NBS (6 mmol) in DMF solution dropwise in an ice-water bath. After the addition is complete, allow the temperature to rise naturally and stir at room temperature for 20 hours. After the reaction is complete, dilute the reaction solution with dichloromethane and pour it into water to separate the organic phase. Dry the solution with anhydrous sodium sulfate, and remove the solvent by rotary evaporation of the filtered organic phase. Purify the crude product by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to obtain intermediate compound C-209-2, which is a yellow solid.

[0436] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (2.50 M, 6 mmol) was slowly added to a tert-butylbenzene (50 mL) solution of intermediate compound C-209-2 (3 mmol), and the mixture was stirred at -78 °C for 1 hour. Dry CO2 gas was then passed through the reaction system for 30 minutes, and the temperature was raised to 25 °C for another 30 minutes. After the reaction was complete, it was quenched with H2O (20 mL), and the pH was adjusted to 12-14 with NaOH solution. The mixture was then washed with Et2O (20 mL), and the resulting aqueous layer was acidified to pH 1-2 with HCl solution and extracted with EtOAc (2 × 20 mL). The resulting organic layers were combined, washed with water (20 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation to obtain crude carboxylic acid. Then, anhydrous AlCl3 (0.14 mol) and NaCl (0.03 mol) were added to the crude carboxylic acid, and the mixture was stirred at 160 °C for 2 hours. The mixture was then cooled to room temperature, and ice water (20 ml) / HCl (6 M, 60 ml) was added, followed by stirring for 15 hours. The crude product was obtained by filtration and dissolved in dichloromethane. The solvent was removed by rotary evaporation, and the product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-209 (24% yield, HPLC purity 97.28%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 890.27; Elemental analysis results: Theoretical values: C, 79.55; H, 4.30; B, 1.21; F, 6.40; N, 3.14; S, 3.60; Experimental values: C, 79.55; H, 4.30; B, 1.20; F, 6.40; N, 3.14; S, 3.61.

[0437] The photophysical properties of the representative fused-ring compounds prepared in the above-described synthetic examples of the present invention are shown in Table 1.

[0438] Table 1:

[0439]

[0440]

[0441]

[0442]

[0443] Note: In Table 1, quantum efficiency is the ratio of the average number of photoelectrons generated per unit time to the number of incident photons at a specific wavelength. This is calculated by using compounds with a quantum efficiency of 10... -5 The sample was prepared by dissolving the compound in toluene at a concentration of mol / L, and then measured after deoxygenation under nitrogen. The instrument was an Edinburgh FLS1000 (UK). The half-width at half-maximum (WHM) is the width of the peak at half the peak height of the fluorescence spectrum at room temperature. It is calculated by drawing a straight line parallel to the base of the peak through the midpoint of the peak height, and finding the distance between the two points where this line intersects the peak. The fluorescence spectrum is obtained by measuring the compound at 10 mol / L concentrations. -5 The sample was prepared by dissolving it in toluene at a concentration of mol / L and then tested using a fluorescence spectrometer (Edinburg FLS1000 (UK)).

[0444] As can be seen from Table 1, the fused ring compounds in the embodiments provided by the present invention have high quantum efficiency (≥85%), while the luminescent compounds provided by the present invention exhibit narrow half-width (≤20nm).

[0445] 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.

[0446] 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.

[0447] 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).

[0448] 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).

[0449] 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.

[0450] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include sensitizers and host materials. 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.

[0451] 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).

[0452] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0453] 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.

[0454] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~8×10 -4 Pa, a hole injection layer is formed by vacuum evaporation of hole injection material on the above-mentioned anolyte film, with an evaporation rate of 0.1-0.5 nm / s;

[0455] 3. A hole transport layer is formed by vacuum evaporation of hole transport material on top of the hole injection layer, with an evaporation rate of 0.1-0.5 nm / s;

[0456] 4. An organic light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The organic light-emitting layer material includes a host material, a sensitizer, and a 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 a preset doping ratio.

[0457] 5. An electron transport layer is formed by vacuum evaporating the electron transport material of the device on top of the organic light-emitting layer, with an evaporation rate of 0.1-0.5 nm / s;

[0458] 6. On the electron transport layer, LiF is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer, and Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0459] 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.

[0460] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0461] Device Example 1

[0462] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0463] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0464] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-1 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0465] Device Example 2

[0466] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0467] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0468] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-4 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0469] Device Example 3

[0470] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0471] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-8(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0472] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-8 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0473] Device Example 4

[0474] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0475] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-10(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0476] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-10 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0477] Device Example 5

[0478] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0479] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-13(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0480] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-13 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0481] Device Example 6

[0482] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0483] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-17(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0484] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-17 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0485] Device Example 7

[0486] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0487] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-21(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0488] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-21 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0489] Device Example 8

[0490] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0491] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-24(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0492] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-24 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0493] Device Example 9

[0494] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0495] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-44(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0496] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-44 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0497] Device Example 10

[0498] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0499] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-55(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0500] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-55 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0501] Device Example 11

[0502] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0503] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-65(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0504] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-65 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0505] Device Example 12

[0506] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0507] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-70(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0508] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-70 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0509] Device Example 13

[0510] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0511] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-80(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0512] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-80 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0513] Device Example 14

[0514] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0515] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-81(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0516] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-81 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0517] Device Example 15

[0518] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0519] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-82(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0520] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-82 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0521] Device Example 16

[0522] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0523] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-85(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0524] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-85 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0525] Device Example 17

[0526] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0527] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-87(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0528] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-87 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0529] Device Example 18

[0530] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0531] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-94(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0532] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-94 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0533] Device Example 19

[0534] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0535] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-155(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0536] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-155 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0537] Device Example 20

[0538] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0539] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-179(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0540] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-179 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0541] Device Example 21

[0542] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0543] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-180(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0544] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-180 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0545] Device Example 22

[0546] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0547] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-181(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0548] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, A-181 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0549] Device Example 23

[0550] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0551] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-182(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0552] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-182 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0553] Device Example 24

[0554] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0555] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-183(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0556] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-183 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0557] Device Example 25

[0558] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0559] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-184(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0560] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-184 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0561] Device Example 26

[0562] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0563] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-185(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0564] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-185 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0565] Device Example 27

[0566] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0567] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-186(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0568] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-186 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0569] Device Example 28

[0570] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0571] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0572] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-1 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0573] Device Example 29

[0574] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0575] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0576] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0577] Device Example 30

[0578] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0579] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-5(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0580] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-5 ​​is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0581] Device Example 31

[0582] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0583] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-11(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0584] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-11 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0585] Device Example 32

[0586] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0587] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-23(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0588] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-23 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0589] Device Example 33

[0590] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0591] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-25(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0592] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-25 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this example); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0593] Device Example 34

[0594] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0595] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-29(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0596] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-29 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0597] Device Example 35

[0598] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0599] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-43(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0600] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-43 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0601] Device Example 36

[0602] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0603] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-46(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0604] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-46 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0605] Device Example 37

[0606] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0607] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-59(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0608] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-59 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0609] Device Example 38

[0610] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0611] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-83(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0612] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-83 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0613] Device Example 39

[0614] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0615] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0616] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-1 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0617] Device Example 40

[0618] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0619] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0620] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0621] Device Example 41

[0622] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0623] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-5(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0624] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-5 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0625] Device Example 42

[0626] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0627] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-11(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0628] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-11 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0629] Device Example 43

[0630] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0631] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-23(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0632] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-23 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0633] Device Example 44

[0634] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0635] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-25(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0636] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-25 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0637] Device Example 45

[0638] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0639] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-29(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0640] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is the sensitizer with a doping concentration of 20 wt%, C-29 is the dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0641] Device Example 46

[0642] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0643] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-43(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0644] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is the sensitizer with a doping concentration of 20 wt%, C-43 is the dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0645] Device Example 47

[0646] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0647] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-46(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0648] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-46 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0649] Device Example 48

[0650] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0651] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-59(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0652] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-59 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are selected as LiF (0.5 nm) and metallic aluminum (150 nm).

[0653] Device Example 49

[0654] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0655] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-83(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0656] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-83 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0657] Device Example 50

[0658] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0659] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-94(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0660] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-94 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0661] Device Example 51

[0662] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0663] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-97(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0664] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-97 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0665] Device Example 52

[0666] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0667] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-98(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0668] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-98 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0669] Device Example 53

[0670] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0671] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-116(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0672] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-116 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0673] Device Example 54

[0674] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0675] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-122(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0676] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-122 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0677] Device Example 55

[0678] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0679] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-140(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0680] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-140 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0681] Device Example 56

[0682] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0683] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-150(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0684] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-150 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0685] Device Example 57

[0686] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0687] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-173(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0688] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-173 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0689] Device Example 58

[0690] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0691] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-49(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0692] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-49 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0693] Device Example 59

[0694] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0695] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-206(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0696] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-206 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0697] Device Example 60

[0698] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0699] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-215(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0700] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-215 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0701] Device Example 61

[0702] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0703] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-113(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0704] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-113 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0705] Device Example 62

[0706] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0707] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-122(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0708] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-122 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0709] Device Example 63

[0710] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0711] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-158(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0712] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-158 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this example); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0713] Device Example 64

[0714] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0715] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-168(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0716] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-168 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0717] Device Example 65

[0718] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0719] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-176(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0720] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-176 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0721] Device Example 66

[0722] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0723] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-187(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0724] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-187 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0725] Device Example 67

[0726] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0727] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-197(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0728] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-197 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0729] Device Example 68

[0730] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0731] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-209(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0732] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-209 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this example); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0733] Comparative Device Example 1

[0734] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0735] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0736] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and Cl is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0737] Comparative Device Example 2

[0738] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0739] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0740] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C2 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0741] Comparative Device Example 3

[0742] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0743] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0744] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C3 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0745] Comparative Device Example 4

[0746] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0747] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0748] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0749] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0750]

[0751]

[0752]

[0753] The C1-C4 compounds mentioned above as comparative compounds are compounds in the prior art. Their synthesis methods can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509, etc., and will not be repeated here.

[0754] The performance of the organic electroluminescent devices prepared in the above embodiments and comparative examples is shown in Table 2 below.

[0755] Table 2:

[0756]

[0757]

[0758]

[0759]

[0760] Compared to Comparative Examples 1-68 and 1-4, with other materials remaining the same in the organic electroluminescent device structure, the compounds of this invention exhibit a narrower electroluminescence spectrum. Furthermore, compared to the multi-resonance TADF dyes with nitrogen-boron-nitrogen structures in the comparative examples, the devices prepared from the compounds provided by this invention have higher external quantum efficiency and longer lifetime. This is because the compounds of this invention, by introducing carbonyl groups, can lock the donor, forming a planar rigid framework structure with the central benzene ring, thus reducing the relaxation degree of the excited state structure. Moreover, the emission color can be tuned by changing the peripheral donor groups, utilizing their different electron-donating abilities and HOMO conjugation degrees. Furthermore, the n-π* transition characteristics of the carbonyl group can improve the TADF performance of the molecule, thereby increasing the upconversion rate of the material, improving exciton utilization, and obtaining high-performance OLED devices. Thus, the target molecule possesses both high luminous efficiency, narrow spectral emission, and high stability.

[0761] The experimental data above show that the novel organic material of this invention, as the light-emitting object of organic electroluminescent devices, is a high-performance organic light-emitting functional material and is expected to be promoted for commercial application.

[0762] 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.

[0763] Obviously, the above embodiments are merely examples for clear illustration 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, and any obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound having a structure as shown in formula (1-1), formula (1-2), or formula (1-3), or having a structure formed by the polymerization of any two of formulas (1-1), (1-2), or (1-3): Equation (1-1) Equation (1-2) Equation (1-3) in: Cycles Ar1, Ar2, Ar3, and Ar4 are each independently selected from aromatic rings of C6 to C30 or heteroaromatic rings of C3 to C30; Ar3and Ar4are not linked, or are linked by a C-C single bond, or by O, S or Se, or by CR8R9or NR 10 linked; Ar1and Ar2are not linked, or are linked by a C-C single bond, or by O, S or Se, or by CR8R9or NR 10 linked; R1, R2, R3, R4, R5, R6 and R7 are each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; n1, n2, n3, and n4 are each independently selected from integers between 0 and 4; When n1, n2, n3, and n4 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, and multiple R4s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, and the multiple R4s are either not connected or connected in a cycle. R8, R9and R 10 each independently selected from one of deuterium, halogen, cyano, substituted or unsubstituted C1-C10 acyclic alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; When the above R1-R 10 When each of the above substituents exists independently, each substituent is independently selected from one of halogen, cyano, C1-C20 chain alkyl, C6-C30 arylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 arylboryl, and C3-C30 heteroaryl.

2. The organic compound according to claim 1, wherein in formulas (1-1), (1-2), and (1-3), n1, n2, n3, and n4 are each independently selected from integers of formulas 1-2; Each of R1-R7 is independently selected from one of deuterium, halogen, cyano, C1-C12 chain alkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl. When each of R1-R7 has a substituent, the substituent is independently selected from one of halogen, cyano, C1-C10 chain alkyl, C6-C30 aryloxy, C6-C30 aryl, or C3-C30 heteroaryl.

3. The organic compound according to claim 1, wherein each of R1-R7 is independently selected from one of deuterium, halogen, cyano, C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and each of the substituents is independently selected from one of halogen, cyano, C1-C10 chain alkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

4. The organic compound according to claim 1 or 2, wherein Ar1, cyclic Ar2, cyclic Ar3 and cyclic Ar4 are each independently selected from one of the following: benzene ring, naphthyl ring, anthracene ring, fluorene ring, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, and thiophenyl.

5. The organic compound according to claim 1 or 2, wherein Ar1, cyclic Ar2, cyclic Ar3 and cyclic Ar4 are each independently a benzene ring or a naphthalene ring.

6. The organic compound according to claim 1, wherein each of R1-R7 is independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenoxy. Diphenylamino, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, cis or trans indo[a]fluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrroleyl, isoindolyl, carbazole, indo[a]carbazole, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5, 6-Quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, oxazolyl, benzooxazolyl, naphthooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazanthyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2, One of 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, purine, pteridinyl, indazinyl, benzothiadiazolyl, diphenylboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups; The R8-R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a] Pyrene, biphenyl, amphylphenyl, 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, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5, 6-Quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthemidazoleyl, phenanthrenemidazoleyl, pyridinidazoleyl, pyrazinidazoleyl, quinoxalinidazoleyl, oxazolyl, benzooxazolyl, naphthemidazoleyl, anthraquinoxazolyl, phenanthrenemidazoleyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalyl, 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-triazolyl, 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, 1,2,3-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, One of 5-tetraazinyl, purinyl, pteridinyl, inazinyl, benzothiadiazolyl, diphenylboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups.

7. The organic compound according to claim 1, wherein R1-R7 are independently represented as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenoxy, diphenylamino, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indene. One of the following groups: fluorenyl, furanyl, benzofuranyl, thiopheneyl, benzothiopheneyl, pyrroleyl, isoindolyl, carbazoyl, indocarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazolyl-1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridinyl, benzopyridinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups; The R8-R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thiopheneyl, benzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazolyl 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3, One of 5-triazinyl, diphenylboryl, dipentafluorophenylboryl, and di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups.

8. The organic compound according to claim 1, wherein R1-R7 are each independently represented as one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenoxy, diphenylamino, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, carbazole, 1,3,5-triazinyl, diphenylboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups; The R8-R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyano, phenyl, naphthyl, anthracene, fluorenyl, and spirodifluorenyl.

9. The organic compound according to claim 1, wherein R1 is connected at the meta and / or para position of the B atom connection site in ring Ar1, R4 is connected at the meta and / or para position of the B atom connection site in ring Ar4, R3 is connected at the meta and / or para position of the N atom connection site in ring Ar3, and R2 is connected at the meta and / or para position of the N atom connection site in ring Ar2.

10. The organic compound according to claim 1, wherein R1 is connected at a meta position at the B atom connection site in ring Ar1, R4 is connected at a meta position at the B atom connection site in ring Ar4, R3 is connected at a meta position at the N atom connection site in ring Ar3, and R2 is connected at a meta position at the N atom connection site in ring Ar2.

11. The organic compound according to claim 1, wherein the structure formed by the polymerization of any two of formulas (1-1), (1-2), and (1-3) is as shown in any one of formulas (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6): in, The definitions of rings Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R5, R6, R7, n1, n2, n3, and n4 are the same as those in claim 1.

12. An organic compound selected from compounds with the following specific structures: 。 13. The compound according to any one of claims 1-12 as a functional material in an organic electronic device, wherein the organic electronic device is selected from organic electroluminescent devices, solar cells, 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 luminescent material in the luminescent layer of an organic electroluminescent device.

14. 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, wherein the light-emitting functional layers contain a compound according to any one of claims 1-12.

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