An organic compound and an organic electroluminescent device using the same

Abstract

The present invention relates to the technical field of organic electroluminescence, and in particular to an organic compound and its application and an organic electroluminescent device containing the compound, and specifically to a novel thermally activated delayed fluorescent material having the structure of the following formula (1): 1 , D 2 , D 3 , D 4 , D 5 The same or different, each independently selected from the structure shown in formula (d1), formula (d2), formula (d3), formula (d4) or selected from substituted or unsubstituted C3-C60 heteroaryl. When the compound of the present invention is used as a light-emitting layer material in an OLED device, it has a higher photoluminescence quantum efficiency, a faster reverse intersystem crossing rate, and can show excellent device efficiency and device life. The present invention also protects an organic electroluminescent device using the above organic compound.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, in particular to an organic compound and application thereof, and an organic electroluminescent device containing the compound, and specifically to a thermally activated delayed fluorescent material. Background Art

[0002] Organic light emitting diodes (OLED) are a type of device with a sandwich-like structure, including positive and negative electrode film layers and organic functional material layers sandwiched between the electrode film layers. When voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode and negative charges are injected from the negative electrode. Under the action of the electric field, the positive and negative charges migrate in the organic layer and meet to combine and emit light. Due to the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility, OLED devices have attracted much attention in the fields of new display technology and new lighting technology. At present, this technology has been widely used in display panels of new lighting fixtures, smart phones, tablet computers and other products, and will further expand to the application fields of large-size display products such as TVs. It is a new display technology with fast development and high technical requirements.

[0003] As OLED continues to advance in the two major fields of lighting and display, people are paying more attention to the research on its core materials. This is because an OLED device with good efficiency and long life is usually the result of an optimized combination of device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials of various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guests (dyes), etc.

[0004] In order to prepare OLED light-emitting devices with lower driving voltage, better luminous efficiency and longer device life, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously study and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED material industry has been committed to developing new organic electroluminescent materials to achieve low device starting voltage, high luminous efficiency and better device life. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides an organic compound which can be applied to the field of organic electroluminescence.

[0006] The organic compound of the present invention has a structure shown in the following formula (1):

[0007]

[0008] In formula (1), D 1 , D 2 , D 3 , D 4 , D 5 Same or different, D 1 , D 2 , D 3 , D 4 , D 5 Each is independently selected from the following structures represented by formula (d1), formula (d2), formula (d3) or formula (d4), or selected from substituted or unsubstituted C3-C60 heteroaryl groups; and D 1 , D 2 , D 3 , D 4 , D 5 At least one of them is selected from the structure shown in one of formulas (d1) to (d4), and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl;

[0009] When there is a substituent on the above heteroaryl group, the substituent is selected from one or a combination of two of cyano, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, nitro, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl;

[0010]

[0011] In formula (d1), each R is the same or different, and R is independently selected from one of hydrogen, deuterium, cyano, halogen, C1-C6 chain alkyl, C1-C6 halogenated chain alkyl, C1-C6 alkoxy, and C1-C6 alkylsilyl, and each R is not hydrogen at the same time;

[0012] In formula (d4), each R1 is the same or different, and R1 is independently selected from one of hydrogen, deuterium, cyano, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3~C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl.

[0013] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0014] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0015] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0016] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0017] In the present invention, the expression of chemical elements, unless otherwise specified, usually includes the concept of isotopes thereof. For example, the expression "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be repeated here.

[0018] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0019] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0020] In the present invention, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed ring forms.

[0021] In the present invention, the substituted or unsubstituted C6-C60 aryl includes a monocyclic aryl and a condensed aryl, preferably a C6-C30 aryl, and more preferably a C6-C20 aryl. The so-called monocyclic aryl refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed aryl refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms to condense each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, peryl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacenyl group is selected from 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0022] The C3-C60 heteroaryl mentioned in the present invention includes monocyclic heteroaryl and condensed ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. Condensed ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl groups include benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl and the like.

[0023] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0024] In the present invention, arylamino represents a group formed by substituting one or two aryl groups for hydrogen on amino, wherein the connection point of the arylamino can be connected to the aryl group in the arylamino or to N in the arylamino, and the exemplary carbon number and specific group of the aryl group in the arylamino are the same as described above.

[0025] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0026] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.

[0027] The chain alkyl mentioned in the present invention, unless otherwise specified, includes straight chain alkyl and branched chain alkyl. Specifically, the substituted or unsubstituted C1-C30 chain alkyl is preferably a substituted or unsubstituted C1-C16 chain alkyl, and more preferably a substituted or unsubstituted C1-C10 chain alkyl. The substituted or unsubstituted C1-C10 chain alkyl includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0028] In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein the monocycloalkyl group refers to an alkyl group containing a single cyclic structure; the polycycloalkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; the C3-C20 cycloalkyl group can be exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0029] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0030] Further preferably, in the organic compound of the present invention, D 1 , D 2 , D 3 , D 4 , D 5 There is a structure selected from one of formulas (d1) to (d4), and D 1 , D 2 , D 3 , D 4 , D 5 Four of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, D 1 , D 2 , D 3 , D 4 , D 5 There are two identical or different ones, and the two are independently selected from the structures shown in any one of formulas (d1) to (d4), and D 1 , D 2 , D 3 , D 4 , D 5 The other three are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

[0031] Further preferably, in the organic compound of the present invention, the D1 , D 2 , D 3 , D 4 , D 5 There is a structure selected from formula (d1), and D 1 , D 2 , D 3 , D 4 , D 5 wherein four of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D 1 , D 2 , D 3 , D 4 , D 5 There are two structures independently selected from formula (d1), and D 1 , D 2 , D 3 , D 4 , D 5 Three of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl;

[0032] More preferably, in formula (d1), R is independently selected from hydrogen, deuterium, benzonitrile or trifluoromethylphenyl, and each R is not hydrogen at the same time;

[0033] More preferably, the formula (d1) has the structure shown below:

[0034]

[0035] Further preferably, in the organic compound of the present invention, the D 1 , D 2 , D 3 , D 4 , D 5 There is a structure selected from formula (d2) or formula (d3), and D 1 , D 2 , D 3 , D 4 , D 5 wherein four of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D 1 , D 2 , D 3 , D 4 , D 5 There are two structures independently selected from formula (d2) or formula (d3), and D 1 , D 2 , D 3 , D 4 , D 5Three of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

[0036] Further preferably, in the organic compound of the present invention, the D 1 , D 2 , D 3 , D 4 , D 5 There is a structure selected from formula (d4), and D 1 , D 2 , D 3 , D 4 , D 5 wherein four of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D 1 , D 2 , D 3 , D 4 , D 5 There are two structures independently selected from formula (d4), and D 1 , D 2 , D 3 , D 4 , D 5 Three of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

[0037] More preferably, in the organic compound of the present invention, when D 1 , D 2 , D 3 , D 4 , D 5 When they are independently selected from substituted or unsubstituted C3-C60 heteroaryl, they are selected from one of the following substituted or unsubstituted structural formulas:

[0038]

[0039] When there is a substituent in the above structural formula, the substituent is selected from one or a combination of two of deuterium, cyano, halogen, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl;

[0040] More preferably, in the organic compound of the present invention, when D 1 , D 2 , D 3 , D 4 , D 5 When they are independently selected from substituted or unsubstituted C3-C60 heteroaryl, they are selected from one of the following substituted or unsubstituted structural formulas:

[0041]

[0042] When there is a substituent in the above structural formula, the substituent is selected from one of deuterium, C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.

[0043] The structural design feature of the organic compound of the present invention is that, in addition to containing a cyano group as an electron acceptor, at least one benzonitrile, trifluoromethylphenyl, boro-oxygen heterocycle or xanthanone group is introduced as a second acceptor. The presence of the cyano group on the central benzene ring can ensure the matching of the LUMO orbital energy level of the molecule with the light color of the material, and ensure that the molecule has a smaller singlet-triplet energy level difference. At the same time, the cyano group can be protected by the surrounding large conjugated steric hindered groups, so that the LUMO orbit is distributed as much as possible around the cyano group, without interacting with the outside world, and avoiding the excited state quenching process. Benzonitrile, trifluoromethylphenyl, boro-oxygen heterocycle and xanthanone groups are used as the second acceptor. These four groups all have at least one conjugated aromatic ring and strong electron-withdrawing ability, and can disperse the charge on the central benzene ring of the molecule through the conjugation effect, reduce the charge density of the benzene ring, and increase the BDE- of the CN bond in the molecule, which is conducive to improving the molecular stability, thereby achieving a longer device life. The selected heteroaromatic electron donor and acceptor structures have high local triplet energy levels, which can achieve a small singlet-triplet energy difference. The combination of multiple acceptor groups can form LUMO orbital energy levels with similar energy (including LUMO, LUMO+1, LUMO+2, etc.), and multiple donor groups in the molecule can also form HOMO orbital energy levels with similar energy (including HOMO, HOMO-1, HOMO-2, HOMO-3, etc.). These molecular orbitals with similar energy can generate excited state energy levels with similar energy during the excitation process. There is a second-order perturbation effect between these excited state energy levels, which enhances the excited state coupling and can greatly improve the reverse intersystem crossing rate and radiation transition rate of the material at the same time, thereby achieving higher device efficiency. All heteroaromatic groups such as carbazole derivatives, carboline derivatives, benzofuran carbazole, benzothiophene carbazole, etc. used in the electron donor have similar electron donating capabilities, and the molecules have predictable similar performance.

[0044] Furthermore, the compounds of the general formula (1) of the present invention can preferably include the following specific structural compounds, which are only representative:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

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[0065]

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[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

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[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

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[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

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[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] The present invention also protects the application of the compound represented by the above formula (1), wherein the application is as a functional material in an organic electronic device, and the organic electronic device includes: an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper, preferably an organic electroluminescent device.

[0110] The present invention also provides an organic electroluminescent device, comprising a substrate, 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 the compound represented by the above-mentioned formula (1) of the present invention, or includes any one of the above-mentioned specific compounds A1-G184 of the present invention.

[0111] Specifically, an embodiment of the present invention provides an organic electroluminescent device, comprising 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 layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, 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 a light-emitting layer is provided between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains the compound represented by formula (1) of the present invention, or includes any one of the specific compounds A1-G184 of the present invention.

[0112] The OLED device prepared by using the compound of the present invention has low starting voltage, high luminous efficiency and better service life.

[0113] The specific reasons why the above-mentioned compounds of the present invention have excellent performance when used in organic electroluminescent devices are not yet clear. The following are speculations of the inventors, but these speculations do not limit the protection scope of the present invention. DETAILED DESCRIPTION

[0114] The specific preparation method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0115] The synthesis method of the compound of the present invention is briefly described below.

[0116] Synthesis Example

[0117] Synthesis of intermediate 1:

[0118]

[0119] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (6.36 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 1, weighing 8.9 g, with a yield of 82%.

[0120] Synthesis of intermediate 2:

[0121]

[0122] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), 4-trifluoromethylphenylboronic acid (8.23 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 2, weighing 10.5 g, with a yield of 83%.

[0123] Synthesis of intermediate 3:

[0124]

[0125] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), (2,12-di-tert-butyl-5,9-dioxa-13b-borazin[3,2,1-de]anthracen-7-yl)boric acid (18.46 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 3, weighing 14.5 g, with a yield of 66%.

[0126] Synthesis of intermediate 4:

[0127]

[0128] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), (3,11-di-tert-butyl-5,9-dioxa-13b-borano[3,2,1-de]anthracen-7-yl)boric acid (18.46 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 4, weighing 15.8 g, with a yield of 72%.

[0129] Synthesis of intermediate 5:

[0130]

[0131] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), xanthanone-2-boric acid (10.4 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 5, weighing 10.9 g, with a yield of 75%.

[0132] Synthesis of intermediate 6:

[0133]

[0134] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), xanthanone-1-boric acid (10.4 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 5, weighing 10.9 g, with a yield of 75%.

[0135] Synthesis of intermediate 7:

[0136]

[0137] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), xanthanone-3-boric acid (10.4 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated under reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 5, weighing 10.9 g, with a yield of 75%.

[0138] Synthesis of intermediate 8:

[0139]

[0140] 3-Bromo-2,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), xanthanone-4-boric acid (10.4 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 5, weighing 10.9 g, with a yield of 75%.

[0141] Synthesis Example A1:

[0142]

[0143] Intermediate 1 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A1 as a yellow solid with a yield of 93%. Mass spectrum: m / z 865.01, elemental analysis experimental values: C, 86.09; H, 4.20; N, 9.72.

[0144] Synthesis Example A2:

[0145] The synthesis method is similar to A1, yellow solid, yield 89%. Mass spectrum: m / z 921.12, elemental analysis experimental values: C, 86.06; H, 4.82; N, 9.12.

[0146] Synthesis Example A3:

[0147] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 977.23, elemental analysis experimental values: C, 86.04; H, 5.36; N, 8.60.

[0148] Synthesis Example A4:

[0149] The synthesis method is similar to A1, yellow solid, yield 80%. Mass spectrum: m / z 1033.34, elemental analysis experimental values: C, 86.01; H, 5.85; N, 8.13.

[0150] Synthesis Example A5:

[0151] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 1201.66, elemental analysis experimental values: C, 85.96; H, 7.05; N, 6.99.

[0152] Synthesis Example A6:

[0153] The synthesis method is similar to A1, yellow solid, yield 89%. Mass spectrum: m / z 1089.44, elemental analysis experimental values: C, 85.99; H, 6.29; N, 7.71.

[0154] Synthesis Example A7:

[0155] The synthesis method is similar to A1, yellow solid, yield 86%. Mass spectrum: m / z 1313.88, elemental analysis experimental values: C, 85.93; H, 7.67; N, 6.40.

[0156] Synthesis Example A8:

[0157] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 1153.74, elemental analysis experimental values: C, 77.04; H, 5.94; N, 7.28; Si, 9.74.

[0158] Synthesis Example A9:

[0159] The synthesis method is similar to A1, yellow solid, yield 76%. Mass spectrum: m / z 1442.47, elemental analysis experimental values: C, 71.61; H, 6.99; N, 5.83; Si, 15.58.

[0160] Synthesis Example A10:

[0161] The synthesis method is similar to A1, yellow solid, yield 65%. Mass spectrum: m / z 965.05, elemental analysis experimental values: C, 82.14; H, 3.34; N, 14.51.

[0162] Synthesis Example A11:

[0163] The synthesis method is similar to A1, yellow solid, yield 72%. Mass spectrum: m / z 1065.09, elemental analysis experimental values: C, 78.94; H, 2.65; N, 18.41.

[0164] Synthesis Example A12:

[0165] The synthesis method is similar to A1, yellow solid, yield 70%. Mass spectrum: m / z 1169.40, elemental analysis experimental values: C, 88.33; H, 4.48; N, 7.19.

[0166] Synthesis Example A13:

[0167] The synthesis method is similar to A1, yellow solid, yield 53%. Mass spectrum: m / z 1473.80, elemental analysis experimental values: C, 89.65; H, 4.65; N, 5.70.

[0168] Synthesis Example A14:

[0169] The synthesis method is similar to A1, yellow solid, yield 77%. Mass spectrum: m / z 1137.00, elemental analysis experimental values: C, 69.72; H, 2.84; F, 20.05; N, 7.39.

[0170] Synthesis Example A15:

[0171] The synthesis method is similar to A1, yellow solid, yield 81%. Mass spectrum: m / z 1409.00, elemental analysis experimental values: C, 59.67; H, 2.00; F, 32.36; N, 5.96.

[0172] Synthesis Example A16:

[0173] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 1337.73, elemental analysis experimental values: C, 87.99; H, 5.73; N, 6.28.

[0174] Synthesis Example A17:

[0175] The synthesis method is similar to A1, yellow solid, yield 79%. Mass spectrum: m / z 1810.44, elemental analysis experimental values: C, 88.90; H, 6.46; N, 4.64.

[0176] Synthesis Example A18:

[0177] The synthesis method is similar to A1, yellow solid, yield 85%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0178] Synthesis Example A19:

[0179] The synthesis method is similar to A1, yellow solid, yield 86%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0180] Synthesis Example A20:

[0181] The synthesis method is similar to A1, yellow solid, yield 70%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0182] Synthesis Example A21:

[0183] The synthesis method is similar to A1, yellow solid, yield 55%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0184] Synthesis Example A35:

[0185] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0186] Synthesis Example A36:

[0187] The synthesis method is similar to A1, yellow solid, yield 72%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0188] Synthesis Example A37:

[0189] The synthesis method is similar to A1, yellow solid, yield 56%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0190] Synthesis Example A38:

[0191] The synthesis method is similar to A1, yellow solid, yield 40%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0192] Synthesis Example A39:

[0193] The synthesis method is similar to A1, yellow solid, yield 80%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0194] Synthesis Example A40:

[0195] The synthesis method is similar to A1, yellow solid, yield 60%. Mass spectrum: m / z 1225.34, elemental analysis experimental values: C, 84.30; H, 3.62; N, 6.86; O, 5.22.

[0196] Synthesis Example A41:

[0197] The synthesis method is similar to A1, yellow solid, yield 70%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0198] Synthesis Example A42:

[0199] The synthesis method is similar to A1, yellow solid, yield 59%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0200] Synthesis Example A43:

[0201] The synthesis method is similar to A1, yellow solid, yield 55%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0202] Synthesis Example A44:

[0203] The synthesis method is similar to A1, yellow solid, yield 71%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0204] Synthesis Example A45:

[0205] The synthesis method is similar to A1, yellow solid, yield 68%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0206] Synthesis Example A46:

[0207] The synthesis method is similar to A1, yellow solid, yield 64%. Mass spectrum: m / z 1289.58, elemental analysis experimental values: C, 80.10; H, 3.44; N, 6.52; S, 9.94.

[0208] Synthesis Example A47:

[0209]

[0210] Intermediate 2 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A47 as a yellow solid with a yield of 93%. Mass spectrum: m / z 907.29, elemental analysis experimental values: C, 82.01; H, 4.00; F, 6.28; N, 7.71.

[0211] Synthesis Example A52:

[0212] The synthesis method is similar to A47, yellow solid, yield 89%. Mass spectrum: m / z 1131.54, elemental analysis experimental values: C, 82.73; H, 6.05; F, 5.03; N, 6.18.

[0213] Synthesis Example A53:

[0214] The synthesis method is similar to A47, yellow solid, yield 83%. Mass spectrum: m / z 1355.79, elemental analysis experimental values: C, 83.21; H, 7.43; F, 4.20; N, 5.16.

[0215] Synthesis Example A54:

[0216] The synthesis method is similar to A47, yellow solid, yield 80%. Mass spectrum: m / z 1195.45, elemental analysis experimental values: C, 74.27; H, 5.73; F, 4.76; N, 5.85; Si, 9.39.

[0217] Synthesis Example A55:

[0218] The synthesis method is similar to A47, yellow solid, yield 83%. Mass spectrum: m / z 1483.61, elemental analysis experimental values: C, 69.54; H, 6.79; F, 3.84; N, 4.71; Si, 15.13.

[0219] Synthesis Example A58:

[0220] The synthesis method is similar to A47, yellow solid, yield 89%. Mass spectrum: m / z 1211.42, elemental analysis experimental values: C, 85.20; H, 4.32; F, 4.70; N, 5.78.

[0221] Synthesis Example A81:

[0222] The synthesis method is similar to A47, yellow solid, yield 86%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0223] Synthesis Example A82:

[0224] The synthesis method is similar to A47, yellow solid, yield 83%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0225] Synthesis Example A83:

[0226] The synthesis method is similar to A47, yellow solid, yield 76%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0227] Synthesis Example A84:

[0228] The synthesis method is similar to A47, yellow solid, yield 65%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0229] Synthesis Example A85:

[0230] The synthesis method is similar to A47, yellow solid, yield 72%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0231] Synthesis Example A86:

[0232] The synthesis method is similar to A47, yellow solid, yield 70%. Mass spectrum: m / z 1267.33, elemental analysis experimental values: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0233] Synthesis Example A87:

[0234] The synthesis method is similar to A47, yellow solid, yield 53%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0235] Synthesis Example A88:

[0236] The synthesis method is similar to A47, yellow solid, yield 77%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0237] Synthesis Example A89:

[0238] The synthesis method is similar to A47, yellow solid, yield 81%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0239] Synthesis Example A90:

[0240] The synthesis method is similar to A47, yellow solid, yield 83%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0241] Synthesis Example A91:

[0242] The synthesis method is similar to A47, yellow solid, yield 79%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0243] Synthesis Example A92:

[0244] The synthesis method is similar to A47, yellow solid, yield 85%. Mass spectrum: m / z 1331.24, elemental analysis experimental values: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0245] Synthesis Example A93:

[0246]

[0247] Intermediate 3 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound A93 as a yellow solid with a yield of 63%. Mass spectrum: m / z 1143.47, elemental analysis experimental values: C, 85.03; H, 5.11; B, 0.94; N, 6.12; O, 2.80.

[0248] Synthesis Example A98:

[0249] The synthesis method is similar to A93, yellow solid, yield 70%. Mass spectrum: m / z 1367.72, elemental analysis experimental values: C, 85.13; H, 6.63; B, 0.79; N, 5.12; O, 2.34.

[0250] Synthesis Example A99:

[0251] The synthesis method is similar to A1, yellow solid, yield 55%. Mass spectrum: m / z 1591.97, elemental analysis experimental values: C, 85.20; H, 7.72; B, 0.68; N, 4.40; O, 2.01.

[0252] Synthesis Example A100:

[0253] The synthesis method is similar to A1, yellow solid, yield 83%. Mass spectrum: m / z 1431.63, elemental analysis experimental values: C, 77.95; H, 6.33; B, 0.75; N, 4.89; O, 2.23; Si, 7.84.

[0254] Synthesis Example A101:

[0255] The synthesis method is similar to A1, yellow solid, yield 72%. Mass spectrum: m / z 1719.78, elemental analysis experimental values: C, 73.25; H, 7.14; B, 0.63; N, 4.07; O, 1.86; Si, 13.05.

[0256] Synthesis Example A104:

[0257] The synthesis method is similar to A1, yellow solid, yield 56%. Mass spectrum: m / z 1447.59, elemental analysis experimental values: C, 87.06; H, 5.15; B, 0.75; N, 4.83; O, 2.21.

[0258] Synthesis Example A127:

[0259] The synthesis method is similar to A1, yellow solid, yield 40%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0260] Synthesis Example A128:

[0261] The synthesis method is similar to A1, yellow solid, yield 80%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0262] Synthesis Example A129:

[0263] The synthesis method is similar to A1, yellow solid, yield 60%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0264] Synthesis Example A130:

[0265] The synthesis method is similar to A1, yellow solid, yield 70%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0266] Synthesis Example A131:

[0267] The synthesis method is similar to A1, yellow solid, yield 59%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0268] Synthesis Example A132:

[0269] The synthesis method is similar to A1, yellow solid, yield 55%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0270] Synthesis Example A133:

[0271] The synthesis method is similar to A1, yellow solid, yield 71%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0272] Synthesis Example A134:

[0273] The synthesis method is similar to A1, yellow solid, yield 68%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0274] Synthesis Example A135:

[0275] The synthesis method is similar to A1, yellow solid, yield 64%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0276] Synthesis Example A136:

[0277] The synthesis method is similar to A1, yellow solid, yield 71%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0278] Synthesis Example A137:

[0279] The synthesis method is similar to A1, yellow solid, yield 68%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0280] Synthesis Example A138:

[0281] The synthesis method is similar to A1, yellow solid, yield 64%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0282] Synthesis Example A139:

[0283]

[0284] Intermediate 4 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A139 as a yellow solid with a yield of 63%. Mass spectrum: m / z 1143.47, elemental analysis experimental values: C, 85.03; H, 5.11; B, 0.94; N, 6.12; O, 2.80.

[0285] Synthesis Example A144:

[0286] The synthesis method is similar to A139, yellow solid, yield 70%. Mass spectrum: m / z 1367.72, elemental analysis experimental values: C, 85.13; H, 6.63; B, 0.79; N, 5.12; O, 2.34.

[0287] Synthesis Example A145:

[0288] The synthesis method is similar to that of A139, yellow solid, yield 55%. Mass spectrum: m / z 1591.97, elemental analysis experimental values: C, 85.20; H, 7.72; B, 0.68; N, 4.40; O, 2.01.

[0289] Synthesis Example A146:

[0290] The synthesis method is similar to A139, yellow solid, yield 83%. Mass spectrum: m / z 1431.63, elemental analysis experimental values: C, 77.95; H, 6.33; B, 0.75; N, 4.89; O, 2.23; Si, 7.84.

[0291] Synthesis Example A147:

[0292] The synthesis method is similar to A139, yellow solid, yield 72%. Mass spectrum: m / z 1719.78, elemental analysis experimental values: C, 73.25; H, 7.14; B, 0.63; N, 4.07; O, 1.86; Si, 13.05.

[0293] Synthesis Example A150:

[0294] The synthesis method is similar to A139, yellow solid, yield 56%. Mass spectrum: m / z 1447.59, elemental analysis experimental values: C, 87.06; H, 5.15; B, 0.75; N, 4.83; O, 2.21.

[0295] Synthesis Example A173:

[0296] The synthesis method is similar to A139, yellow solid, yield 40%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0297] Synthesis Example A174:

[0298] The synthesis method is similar to that of A139, yellow solid, yield 80%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0299] Synthesis Example A175:

[0300] The synthesis method is similar to that of A139, yellow solid, yield 60%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0301] Synthesis Example A176:

[0302] The synthesis method is similar to A139, yellow solid, yield 70%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0303] Synthesis Example A177:

[0304] The synthesis method is similar to that of A139, yellow solid, yield 59%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0305] Synthesis Example A178:

[0306] The synthesis method is similar to that of A139, yellow solid, yield 80%. Mass spectrum: m / z 1503.51, elemental analysis experimental values: C, 83.82; H, 4.42; B, 0.72; N, 4.65; O, 6.38.

[0307] Synthesis Example A179:

[0308] The synthesis method is similar to that of A139, yellow solid, yield 79%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0309] Synthesis Example A180:

[0310] The synthesis method is similar to that of A139, yellow solid, yield 78%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0311] Synthesis Example A181:

[0312] The synthesis method is similar to A139, yellow solid, yield 88%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0313] Synthesis Example A182:

[0314] The synthesis method is similar to that of A139, yellow solid, yield 87%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0315] Synthesis Example A183:

[0316] The synthesis method is similar to that of A139, yellow solid, yield 86%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0317] Synthesis Example A184:

[0318] The synthesis method is similar to A139, yellow solid, yield 83%. Mass spectrum: m / z 1567.42, elemental analysis experimental values: C, 80.39; H, 4.24; B, 0.69; N, 4.46; O, 2.04; S, 8.17.

[0319] Synthesis Example A185:

[0320]

[0321] Intermediate 5 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A185 as a yellow solid with a yield of 63%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0322] Synthesis Example A190:

[0323] The synthesis method is similar to A185, yellow solid, yield 75%. Mass spectrum: m / z 1181.56, elemental analysis experimental values: C, 85.32; H, 6.05; N, 5.92; O, 2.71.

[0324] Synthesis Example A191:

[0325] The synthesis method is similar to A185, yellow solid, yield 91%. Mass spectrum: m / z 1405.81, elemental analysis experimental values: C, 85.37; H, 7.38; N, 4.98; O, 2.27.

[0326] Synthesis Example A192:

[0327] The synthesis method is similar to A185, yellow solid, yield 82%. Mass spectrum: m / z 1245.47, elemental analysis experimental values: C, 77.07; H, 5.74; N, 5.62; O, 2.57; Si, 9.01.

[0328] Synthesis Example A193:

[0329] The synthesis method is similar to A185, yellow solid, yield 79%. Mass spectrum: m / z 1533.63, elemental analysis experimental values: C, 71.96; H, 6.76; N, 4.56; O, 2.08; Si, 14.63.

[0330] Synthesis Example A196:

[0331] The synthesis method is similar to that of A185, yellow solid, yield 73%. Mass spectrum: m / z 1261.44, elemental analysis experimental values: C, 87.53; H, 4.39; N, 5.55; O, 2.53.

[0332] Synthesis Example A231:

[0333]

[0334] Intermediate 6 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A231 as a yellow solid with a yield of 63%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0335] Synthesis Example A236:

[0336] The synthesis method is similar to A231, yellow solid, yield 83%. Mass spectrum: m / z 1181.56, elemental analysis experimental values: C, 85.32; H, 6.05; N, 5.92; O, 2.71.

[0337] Synthesis Example A237:

[0338] The synthesis method is similar to A231, yellow solid, yield 81%. Mass spectrum: m / z 1405.81, elemental analysis experimental values: C, 85.37; H, 7.38; N, 4.98; O, 2.27.

[0339] Synthesis Example A238:

[0340] The synthesis method is similar to A231, yellow solid, yield 83%. Mass spectrum: m / z 1245.47, elemental analysis experimental values: C, 77.07; H, 5.74; N, 5.62; O, 2.57; Si, 9.01.

[0341] Synthesis Example A239:

[0342] The synthesis method is similar to A231, yellow solid, yield 73%. Mass spectrum: m / z 1533.63, elemental analysis experimental values: C, 71.96; H, 6.76; N, 4.56; O, 2.08; Si, 14.63.

[0343] Synthesis Example A242:

[0344] The synthesis method is similar to A231, yellow solid, yield 82%. Mass spectrum: m / z 1261.44, elemental analysis experimental values: C, 87.53; H, 4.39; N, 5.55; O, 2.53.

[0345] Synthesis Example A277:

[0346]

[0347] Intermediate 7 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A277 as a yellow solid with a yield of 63%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0348] Synthesis Example A282:

[0349] The synthesis method is similar to A231, yellow solid, yield 73%. Mass spectrum: m / z 1181.56, elemental analysis experimental values: C, 85.32; H, 6.05; N, 5.92; O, 2.71.

[0350] Synthesis Example A283:

[0351] The synthesis method is similar to A231, yellow solid, yield 69%. Mass spectrum: m / z 1405.81, elemental analysis experimental values: C, 85.37; H, 7.38; N, 4.98; O, 2.27.

[0352] Synthesis Example A284:

[0353] The synthesis method is similar to A231, yellow solid, yield 65%. Mass spectrum: m / z 1245.47, elemental analysis experimental values: C, 77.07; H, 5.74; N, 5.62; O, 2.57; Si, 9.01.

[0354] Synthesis Example A285:

[0355] The synthesis method is similar to A231, yellow solid, yield 54%. Mass spectrum: m / z 1533.63, elemental analysis experimental values: C, 71.96; H, 6.76; N, 4.56; O, 2.08; Si, 14.63.

[0356] Synthesis Example A288:

[0357] The synthesis method is similar to A231, yellow solid, yield 74%. Mass spectrum: m / z 1261.44, elemental analysis experimental values: C, 87.53; H, 4.39; N, 5.55; O, 2.53.

[0358] Synthesis Example A323:

[0359]

[0360] Intermediate 8 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound A323 as a yellow solid with a yield of 63%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0361] Synthesis Example A328:

[0362] The synthesis method is similar to A323, yellow solid, yield 84%. Mass spectrum: m / z 1181.56, elemental analysis experimental values: C, 85.32; H, 6.05; N, 5.92; O, 2.71.

[0363] Synthesis Example A329:

[0364] The synthesis method is similar to A323, yellow solid, yield 63%. Mass spectrum: m / z 1405.81, elemental analysis experimental values: C, 85.37; H, 7.38; N, 4.98; O, 2.27.

[0365] Synthesis Example A330:

[0366] The synthesis method is similar to A323, yellow solid, yield 64%. Mass spectrum: m / z 1245.47, elemental analysis experimental values: C, 77.07; H, 5.74; N, 5.62; O, 2.57; Si, 9.01.

[0367] Synthesis Example A331:

[0368] The synthesis method is similar to A323, yellow solid, yield 69%. Mass spectrum: m / z 1533.63, elemental analysis experimental values: C, 71.96; H, 6.76; N, 4.56; O, 2.08; Si, 14.63.

[0369] Synthesis Example A334:

[0370] The synthesis method is similar to A323, yellow solid, yield 73%. Mass spectrum: m / z 1261.44, elemental analysis experimental values: C, 87.53; H, 4.39; N, 5.55; O, 2.53.

[0371] Synthesis of intermediate 9:

[0372]

[0373] 2-Bromo-3,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (6.36 g, 43.31 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (2.27 g, 1.97 mmol) and 20 mL of potassium carbonate aqueous solution (10.88 g, 78.57 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 9, weighing 8.9 g, with a yield of 82%.

[0374] Synthesis of intermediate 10:

[0375]

[0376] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 79%.

[0377] Synthesis of intermediate 11:

[0378]

[0379] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 68%.

[0380] Synthesis of intermediate 12:

[0381]

[0382] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 73%.

[0383] Synthesis of intermediate 13:

[0384]

[0385] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 55%.

[0386] Synthesis of intermediate 14:

[0387]

[0388] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 70%.

[0389] Synthesis of intermediate 15:

[0390]

[0391] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 68%.

[0392] Synthesis of intermediate 16:

[0393]

[0394] The synthesis method is similar to that of intermediate 9, white solid, with a yield of 77%.

[0395] Synthesis Example B1:

[0396]

[0397] Intermediate 9 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B1 as a yellow solid with a yield of 93%. Mass spectrum: m / z 865.01, elemental analysis experimental values: C, 86.09; H, 4.20; N, 9.72.

[0398] Synthesis Example B2:

[0399] The synthesis method is similar to that of B1, yellow solid, yield 89%. Mass spectrum: m / z 921.12, elemental analysis experimental values: C, 86.06; H, 4.82; N, 9.12.

[0400] Synthesis Example B3:

[0401] The synthesis method is similar to that of B1, yellow solid, yield 83%. Mass spectrum: m / z 977.23, elemental analysis experimental values: C, 86.04; H, 5.36; N, 8.60.

[0402] Synthesis Example B4:

[0403] The synthesis method is similar to that of B1, yellow solid, yield 80%. Mass spectrum: m / z 1033.34, elemental analysis experimental values: C, 86.01; H, 5.85; N, 8.13.

[0404] Synthesis Example B5:

[0405] The synthesis method is similar to that of B1, yellow solid, yield 83%. Mass spectrum: m / z 1201.66, elemental analysis experimental values: C, 85.96; H, 7.05; N, 6.99.

[0406] Synthesis Example B6:

[0407] The synthesis method is similar to that of B1, yellow solid, yield 89%. Mass spectrum: m / z 1089.44, elemental analysis experimental values: C, 85.99; H, 6.29; N, 7.71.

[0408] Synthesis Example B7:

[0409] The synthesis method is similar to that of B1, yellow solid, yield 86%. Mass spectrum: m / z 1313.88, elemental analysis experimental values: C, 85.93; H, 7.67; N, 6.40.

[0410] Synthesis Example B8:

[0411] The synthesis method is similar to that of B1, yellow solid, yield 83%. Mass spectrum: m / z 1153.74, elemental analysis experimental values: C, 77.04; H, 5.94; N, 7.28; Si, 9.74.

[0412] Synthesis Example B9:

[0413] The synthesis method is similar to that of B1, yellow solid, yield 76%. Mass spectrum: m / z 1442.47, elemental analysis experimental values: C, 71.61; H, 6.99; N, 5.83; Si, 15.58.

[0414] Synthesis Example B10:

[0415] The synthesis method is similar to that of B1, yellow solid, yield 65%. Mass spectrum: m / z 965.05, elemental analysis experimental values: C, 82.14; H, 3.34; N, 14.51.

[0416] Synthesis Example B11:

[0417] The synthesis method is similar to that of B1, yellow solid, yield 72%. Mass spectrum: m / z 1065.09, elemental analysis experimental values: C, 78.94; H, 2.65; N, 18.41.

[0418] Synthesis Example B12:

[0419] The synthesis method is similar to that of B1, yellow solid, yield 70%. Mass spectrum: m / z 1169.40, elemental analysis experimental values: C, 88.33; H, 4.48; N, 7.19.

[0420] Synthesis Example B13:

[0421] The synthesis method is similar to that of B1, yellow solid, yield 53%. Mass spectrum: m / z 1473.80, elemental analysis experimental values: C, 89.65; H, 4.65; N, 5.70.

[0422] Synthesis Example B14:

[0423] The synthesis method is similar to that of B1, yellow solid, yield 77%. Mass spectrum: m / z 1137.00, elemental analysis experimental values: C, 69.72; H, 2.84; F, 20.05; N, 7.39.

[0424] Synthesis Example B15:

[0425] The synthesis method is similar to that of B1, yellow solid, yield 81%. Mass spectrum: m / z 1409.00, elemental analysis experimental values: C, 59.67; H, 2.00; F, 32.36; N, 5.96.

[0426] Synthesis Example B16:

[0427] The synthesis method is similar to that of B1, yellow solid, yield 83%. Mass spectrum: m / z 1337.73, elemental analysis experimental values: C, 87.99; H, 5.73; N, 6.28.

[0428] Synthesis Example B17:

[0429] The synthesis method is similar to that of B1, yellow solid, yield 79%. Mass spectrum: m / z 1810.44, elemental analysis experimental values: C, 88.90; H, 6.46; N, 4.64.

[0430] Synthesis Example B18:

[0431] The synthesis method is similar to that of B1, yellow solid, yield 85%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0432] Synthesis Example B19:

[0433] The synthesis method is similar to that of B1, yellow solid, yield 86%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0434] Synthesis Example B20:

[0435] The synthesis method is similar to that of B1, yellow solid, yield 70%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0436] Synthesis Example B21:

[0437] The synthesis method is similar to that of B1, yellow solid, yield 55%. Mass spectrum: m / z 868.96, elemental analysis experimental values: C, 80.17; H, 3.71; N, 16.12.

[0438] Synthesis Example B22:

[0439] The synthesis method is similar to that of B1, yellow solid, yield 59%. Mass spectrum: m / z 929.01, elemental analysis experimental values: C, 80.16; H, 3.91; N, 9.05; O, 6.89.

[0440] Synthesis Example B23:

[0441] The synthesis method is similar to that of B1, yellow solid, yield 58%. Mass spectrum: m / z 993.25, elemental analysis experimental values: C, 74.97; H, 3.65; N, 8.46; S, 12.91.

[0442] Synthesis Example B24:

[0443]

[0444] Intermediate 10 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B24 as a yellow solid with a yield of 93%. Mass spectrum: m / z 907.29, elemental analysis experimental values: C, 82.01; H, 4.00; F, 6.28; N, 7.71.

[0445] Synthesis Example B29:

[0446] The synthesis method is similar to that of B24, yellow solid, yield 89%. Mass spectrum: m / z 1131.54, elemental analysis experimental values: C, 82.73; H, 6.05; F, 5.03; N, 6.18.

[0447] Synthesis Example B30:

[0448] The synthesis method is similar to that of B24, yellow solid, yield 83%. Mass spectrum: m / z 1355.79, elemental analysis experimental values: C, 83.21; H, 7.43; F, 4.20; N, 5.16.

[0449] Synthesis Example B31:

[0450] The synthesis method is similar to that of B24, yellow solid, yield 80%. Mass spectrum: m / z 1195.45, elemental analysis experimental values: C, 74.27; H, 5.73; F, 4.76; N, 5.85; Si, 9.39.

[0451] Synthesis Example B32:

[0452] The synthesis method is similar to that of B24, yellow solid, yield 83%. Mass spectrum: m / z 1483.61, elemental analysis experimental values: C, 69.54; H, 6.79; F, 3.84; N, 4.71; Si, 15.13.

[0453] Synthesis Example B35:

[0454] The synthesis method is similar to that of B24, yellow solid, yield 89%. Mass spectrum: m / z 1211.42, elemental analysis experimental values: C, 85.20; H, 4.32; F, 4.70; N, 5.78.

[0455] Synthesis Example B47:

[0456]

[0457] Intermediate 11 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B47 as a yellow solid with a yield of 63%. Mass spectrum: m / z 1143.47, elemental analysis experimental values: C, 85.03; H, 5.11; B, 0.94; N, 6.12; O, 2.80.

[0458] Synthesis Example B70:

[0459]

[0460] Intermediate 12 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B70 as a yellow solid with a yield of 63%. Mass spectrum: m / z 1143.47, elemental analysis experimental values: C, 85.03; H, 5.11; B, 0.94; N, 6.12; O, 2.80.

[0461] Synthesis Example B93:

[0462]

[0463] Intermediate 13 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B93 as a yellow solid with a yield of 58%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0464] Synthesis Example B116:

[0465] Intermediate 14 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B116 as a yellow solid with a yield of 55%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0466] Synthesis Example B139:

[0467] Intermediate 15 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B139 as a yellow solid with a yield of 59%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0468] Synthesis Example B162:

[0469] Intermediate 16 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound B162 as a yellow solid with a yield of 61%. Mass spectrum: m / z 957.31, elemental analysis experimental values: C, 85.25; H, 4.10; N, 7.31; O, 3.34.

[0470] Synthesis of intermediate 17:

[0471]

[0472] 3,5-Dibromo-2,4,6-trifluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (13.27 g, 69.87 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (1.83 g, 1.59 mmol) and 20 mL of potassium carbonate aqueous solution (8.78 g, 63.51 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 17, weighing 7.9 g, with a yield of 69%.

[0473] Synthesis of intermediate 18-24:

[0474]

[0475] The synthesis method is similar to that of intermediate 17. Intermediates 18-24 are all white solids with yields of 61%, 40%, 45%, 50%, 48%, 55% and 61%, respectively.

[0476] Synthesis Example C1:

[0477]

[0478] Intermediate 17 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C1 as a yellow solid with a yield of 83%. Mass spectrum: m / z 800.93, elemental analysis experimental values: C, 85.48; H, 4.03; N, 10.49.

[0479] Synthesis Example C2:

[0480] The synthesis method is similar to C1, yellow solid, yield 79%. Mass spectrum: m / z 842.32, elemental analysis experimental values: C, 85.49; H, 4.54; N, 9.97.

[0481] Synthesis Example C3:

[0482] The synthesis method is similar to C1, yellow solid, yield 70%. Mass spectrum: m / z 884.36, elemental analysis experimental values: C, 85.49; H, 5.01; N, 9.50.

[0483] Synthesis Example C4:

[0484] The synthesis method is similar to that of C1, yellow solid, yield 72%. Mass spectrum: m / z 926.41, elemental analysis experimental values: C, 85.50; H, 5.44; N, 9.06.

[0485] Synthesis Example C5:

[0486] The synthesis method is similar to C1, yellow solid, yield 71%. Mass spectrum: m / z 1052.55, elemental analysis experimental values: C, 85.52; H, 6.51; N, 7.98.

[0487] Synthesis Example C6:

[0488] The synthesis method is similar to C1, yellow solid, yield 78%. Mass spectrum: m / z 968.46, elemental analysis experimental values: C, 85.51; H, 5.82; N, 8.67.

[0489] Synthesis Example C7:

[0490] The synthesis method is similar to C1, yellow solid, yield 79%. Mass spectrum: m / z 1136.64, elemental analysis experimental values: C, 85.52; H, 7.09; N, 7.39.

[0491] Synthesis Example C8:

[0492] The synthesis method is similar to C1, yellow solid, yield 78%. Mass spectrum: m / z 1016.39, elemental analysis experimental values: C, 77.91; H, 5.55; N, 8.26; Si, 8.28.

[0493] Synthesis Example C9:

[0494] The synthesis method is similar to C1, yellow solid, yield 79%. Mass spectrum: m / z 1218.49, elemental analysis experimental values: C, 72.85; H, 6.44; N, 6.89; Si, 13.81.

[0495] Synthesis Example C10:

[0496] The synthesis method is similar to that of C1, yellow solid, yield 70%. Mass spectrum: m / z 875.25, elemental analysis experimental values: C, 82.27; H, 3.34; N, 14.39.

[0497] Synthesis Example C11:

[0498] The synthesis method is similar to C1, yellow solid, yield 73%. Mass spectrum: m / z 950.24, elemental analysis experimental values: C, 79.57; H, 2.76; N, 17.67.

[0499] Synthesis Example C12:

[0500] The synthesis method is similar to C1, yellow solid, yield 76%. Mass spectrum: m / z 1028.36, elemental analysis experimental values: C, 87.53; H, 4.31; N, 8.17.

[0501] Synthesis Example C13:

[0502] The synthesis method is similar to C1, yellow solid, yield 79%. Mass spectrum: m / z 1256.46, elemental analysis experimental values: C, 88.83; H, 4.49; N, 6.68.

[0503] Synthesis Example C14:

[0504] The synthesis method is similar to C1, yellow solid, yield 69%. Mass spectrum: m / z 1004.23, elemental analysis experimental values: C, 71.71; H, 2.91; F, 17.01; N, 8.36.

[0505] Synthesis Example C15:

[0506] The synthesis method is similar to C1, yellow solid, yield 80%. Mass spectrum: m / z 1208.19, elemental analysis experimental values: C, 62.59; H, 2.17; F, 28.29; N, 6.95.

[0507] Synthesis Example C16:

[0508] The synthesis method is similar to C1, yellow solid, yield 75%. Mass spectrum: m / z 1154.50, elemental analysis experimental values: C, 87.32; H, 5.41; N, 7.27.

[0509] Synthesis Example C17:

[0510] The synthesis method is similar to C1, yellow solid, yield 75%. Mass spectrum: m / z 1508.74, elemental analysis experimental values: C, 88.29; H, 6.14; N, 5.57.

[0511] Synthesis Example C18:

[0512] The synthesis method is similar to that of C1, yellow solid, yield 79%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0513] Synthesis Example C19:

[0514] The synthesis method is similar to C1, yellow solid, yield 70%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0515] Synthesis Example C20:

[0516] The synthesis method is similar to C1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0517] Synthesis Example C21:

[0518] The synthesis method is similar to C1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0519] Synthesis Example C22:

[0520] The synthesis method is similar to C1, yellow solid, yield 81%. Mass spectrum: m / z 848.25, elemental analysis experimental values: C, 80.65; H, 3.80; N, 9.90; O, 5.65.

[0521] Synthesis Example C23:

[0522] The synthesis method is similar to C1, yellow solid, yield 70%. Mass spectrum: m / z 896.19, elemental analysis experimental values: C, 76.32; H, 3.60; N, 9.37; S, 10.72.

[0523] Synthesis Example C24:

[0524] Intermediate 18 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C24 as a yellow solid with a yield of 83%. Mass spectrum: m / z 886.25, elemental analysis experimental values: C, 77.19; H, 3.64; F, 12.85; N, 6.32.

[0525] Synthesis Example C25:

[0526] The synthesis method is similar to that of C24, yellow solid, yield 70%. Mass spectrum: m / z 928.30, elemental analysis experimental values: C, 77.58; H, 4.12; F, 12.27; N, 6.03

[0527] Synthesis Example C26:

[0528] The synthesis method is similar to that of C24, yellow solid, yield 71%. Mass spectrum: m / z 970.35, elemental analysis experimental values: C, 77.92; H, 4.57; F, 11.74; N, 5.77

[0529] Synthesis Example C27:

[0530] The synthesis method is similar to that of C24, yellow solid, yield 73%. Mass spectrum: m / z 1012.39, elemental analysis experimental values: C, 78.24; H, 4.97; F, 11.25; N, 5.53

[0531] Synthesis Example C28:

[0532] The synthesis method is similar to that of C24, yellow solid, yield 69%. Mass spectrum: m / z 1138.53, elemental analysis experimental values: C, 79.06; H, 6.02; F, 10.00; N, 4.92

[0533] Synthesis Example C29:

[0534] The synthesis method is similar to that of C24, yellow solid, yield 67%. Mass spectrum: m / z 1054.44, elemental analysis experimental values: C, 78.54; H, 5.35; F, 10.80; N, 5.31

[0535] Synthesis Example C30:

[0536] The synthesis method is similar to that of C24, yellow solid, yield 66%. Mass spectrum: m / z 1222.63, elemental analysis experimental values: C, 79.51; H, 6.59; F, 9.32; N, 4.58

[0537] Synthesis Example C31:

[0538] The synthesis method is similar to that of C24, yellow solid, yield 80%. Mass spectrum: m / z 1102.37, elemental analysis experimental values: C, 71.84; H, 5.12; F, 10.33; N, 5.08; Si, 7.64

[0539] Synthesis Example C32:

[0540] The synthesis method is similar to that of C24, yellow solid, yield 73%. Mass spectrum: m / z 1304.47, elemental analysis experimental values: C, 68.06; H, 6.02; F, 8.73; N, 4.29; Si, 12.90

[0541] Synthesis Example C33:

[0542] The synthesis method is similar to that of C24, yellow solid, yield 72%. Mass spectrum: m / z 961.24, elemental analysis experimental values: C, 74.92; H, 3.04; F, 11.85; N, 10.19

[0543] Synthesis Example C34:

[0544] The synthesis method is similar to that of C24, yellow solid, yield 71%. Mass spectrum: m / z 1036.22, elemental analysis experimental values: C, 72.97; H, 2.53; F, 10.99; N, 13.51

[0545] Synthesis Example C35:

[0546] The synthesis method is similar to that of C24, yellow solid, yield 69%. Mass spectrum: m / z 1114.35, elemental analysis experimental values: C, 80.78; H, 3.98; F, 10.22; N, 5.02

[0547] Synthesis Example C36:

[0548] The synthesis method is similar to that of C24, yellow solid, yield 59%. Mass spectrum: m / z 1342.44, elemental analysis experimental values: C, 83.14; H, 4.20; F, 8.48; N, 4.17

[0549] Synthesis Example C37:

[0550] The synthesis method is similar to that of C24, yellow solid, yield 58%. Mass spectrum: m / z 1090.22, elemental analysis experimental values: C, 66.06; H, 2.68; F, 26.12; N, 5.14

[0551] Synthesis Example C38:

[0552] The synthesis method is similar to that of C24, yellow solid, yield 67%. Mass spectrum: m / z 1294.18, elemental analysis experimental values: C, 58.44; H, 2.02; F, 35.21; N, 4.33

[0553] Synthesis Example C39:

[0554] The synthesis method is similar to that of C24, yellow solid, yield 78%. Mass spectrum: m / z 1240.49, elemental analysis experimental values: C, 81.27; H, 5.03; F, 9.18; N, 4.51

[0555] Synthesis Example C40:

[0556] The synthesis method is similar to that of C24, yellow solid, yield 70%. Mass spectrum: m / z 1594.72, elemental analysis experimental values: C, 83.54; H, 5.81; F, 7.14; N, 3.51

[0557] Synthesis Example C41:

[0558] The synthesis method is similar to that of C24, yellow solid, yield 75%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0559] Synthesis Example C42:

[0560] The synthesis method is similar to that of C24, yellow solid, yield 80%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0561] Synthesis Example C43:

[0562] The synthesis method is similar to that of C24, yellow solid, yield 82%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0563] Synthesis Example C44:

[0564] The synthesis method is similar to that of C24, yellow solid, yield 79%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0565] Synthesis Example C45:

[0566] The synthesis method is similar to that of C24, yellow solid, yield 79%. Mass spectrum: m / z 934.24, elemental analysis experimental values: C, 73.23; H, 3.45; F, 12.19; N, 5.99; O, 5.13

[0567] Synthesis Example C46:

[0568] The synthesis method is similar to that of C24, yellow solid, yield 75%. Mass spectrum: m / z 982.17, elemental analysis experimental values: C, 69.64; H, 3.28; F, 11.60; N, 5.70; S, 9.78

[0569] Synthesis Example C47:

[0570] Intermediate 19 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C47 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0571] Synthesis Example C52:

[0572] The synthesis method is similar to that of C47, yellow solid, yield 70%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[0573] Synthesis Example C53:

[0574] The synthesis method is similar to that of C47, yellow solid, yield 74%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[0575] Synthesis Example C54:

[0576] The synthesis method is similar to that of C47, yellow solid, yield 75%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[0577] Synthesis Example C55:

[0578] The synthesis method is similar to that of C47, yellow solid, yield 73%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[0579] Synthesis Example C58:

[0580] The synthesis method is similar to that of C47, yellow solid, yield 69%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[0581] Synthesis Example C59:

[0582] The synthesis method is similar to that of C47, yellow solid, yield 69%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[0583] Synthesis Example C60:

[0584] The synthesis method is similar to that of C47, yellow solid, yield 78%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[0585] Synthesis Example C61:

[0586] The synthesis method is similar to that of C47, yellow solid, yield 74%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[0587] Synthesis Example C70:

[0588] Intermediate 20 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C70 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0589] Synthesis Example C75:

[0590] The synthesis method is similar to that of C70, yellow solid, yield 73%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[0591] Synthesis Example C73:

[0592] The synthesis method is similar to that of C70, yellow solid, yield 70%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[0593] Synthesis Example C77:

[0594] The synthesis method is similar to that of C70, yellow solid, yield 68%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[0595] Synthesis Example C78:

[0596] The synthesis method is similar to that of C70, yellow solid, yield 66%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[0597] Synthesis Example C81:

[0598] The synthesis method is similar to that of C70, yellow solid, yield 77%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[0599] Synthesis Example C82:

[0600] The synthesis method is similar to that of C70, yellow solid, yield 77%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[0601] Synthesis Example C83:

[0602] The synthesis method is similar to that of C70, yellow solid, yield 74%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[0603] Synthesis Example C84:

[0604] The synthesis method is similar to that of C70, yellow solid, yield 71%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[0605] Synthesis Example C93:

[0606] Intermediate 21 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C93 as a yellow solid with a yield of 85%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[0607] Synthesis Example C94:

[0608] The synthesis method is similar to that of C93, yellow solid, yield 71%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0609] Synthesis Example C95:

[0610] The synthesis method is similar to that of C93, yellow solid, yield 70%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0611] Synthesis Example C96:

[0612] The synthesis method is similar to that of C93, yellow solid, yield 59%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0613] Synthesis Example C97:

[0614] The synthesis method is similar to that of C93, yellow solid, yield 58%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0615] Synthesis Example C98:

[0616] The synthesis method is similar to that of C93, yellow solid, yield 55%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54

[0617] Synthesis Example C99:

[0618] The synthesis method is similar to that of C93, yellow solid, yield 59%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0619] Synthesis Example C100:

[0620] The synthesis method is similar to that of C93, yellow solid, yield 61%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0621] Synthesis Example C101:

[0622] The synthesis method is similar to that of C93, yellow solid, yield 63%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0623] Synthesis Example C102:

[0624] The synthesis method is similar to that of C93, yellow solid, yield 73%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0625] Synthesis Example C103:

[0626] The synthesis method is similar to that of C93, yellow solid, yield 72%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0627] Synthesis Example C104:

[0628] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0629] Synthesis Example C105:

[0630] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0631] Synthesis Example C106:

[0632] The synthesis method is similar to that of C93, yellow solid, yield 74%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0633] Synthesis Example C107:

[0634] The synthesis method is similar to that of C93, yellow solid, yield 69%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0635] Synthesis Example C108:

[0636] The synthesis method is similar to that of C93, yellow solid, yield 55%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[0637] Synthesis Example C109:

[0638] The synthesis method is similar to that of C93, yellow solid, yield 80%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[0639] Synthesis Example C110:

[0640] The synthesis method is similar to that of C93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0641] Synthesis Example C111:

[0642] The synthesis method is similar to that of C93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0643] Synthesis Example C112:

[0644] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0645] Synthesis Example C113:

[0646] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0647] Synthesis Example C114:

[0648] The synthesis method is similar to that of C93, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[0649] Synthesis Example C115:

[0650] The synthesis method is similar to that of C93, yellow solid, yield 72%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[0651] Synthesis Example C116:

[0652] Intermediate 22 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C116 as a yellow solid with a yield of 83%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[0653] Synthesis Example C117:

[0654] The synthesis method is similar to that of C116, yellow solid, yield 77%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0655] Synthesis Example C118:

[0656] The synthesis method is similar to that of C116, yellow solid, yield 75%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0657] Synthesis Example C119:

[0658] The synthesis method is similar to that of C116, yellow solid, yield 78%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0659] Synthesis Example C120:

[0660] The synthesis method is similar to that of C116, yellow solid, yield 60%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0661] Synthesis Example C121:

[0662] The synthesis method is similar to that of C116, yellow solid, yield 59%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[0663] Synthesis Example C122:

[0664] The synthesis method is similar to that of C116, yellow solid, yield 55%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0665] Synthesis Example C123:

[0666] The synthesis method is similar to that of C116, yellow solid, yield 80%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0667] Synthesis Example C124:

[0668] The synthesis method is similar to that of C116, yellow solid, yield 81%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0669] Synthesis Example C125:

[0670] The synthesis method is similar to that of C116, yellow solid, yield 83%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0671] Synthesis Example C126:

[0672] The synthesis method is similar to that of C116, yellow solid, yield 88%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0673] Synthesis Example C127:

[0674] The synthesis method is similar to that of C116, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0675] Synthesis Example C128:

[0676] The synthesis method is similar to that of C116, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0677] Synthesis Example C129:

[0678] The synthesis method is similar to that of C116, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0679] Synthesis Example C130:

[0680] The synthesis method is similar to that of C116, yellow solid, yield 75%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0681] Synthesis Example C131:

[0682] The synthesis method is similar to that of C116, yellow solid, yield 67%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[0683] Synthesis Example C132:

[0684] The synthesis method is similar to that of C116, yellow solid, yield 53%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[0685] Synthesis Example C133:

[0686] The synthesis method is similar to that of C116, yellow solid, yield 70%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0687] Synthesis Example C134:

[0688] The synthesis method is similar to that of C116, yellow solid, yield 80%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0689] Synthesis Example C135:

[0690] The synthesis method is similar to that of C116, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0691] Synthesis Example C136:

[0692] The synthesis method is similar to that of C116, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0693] Synthesis Example C137:

[0694] The synthesis method is similar to that of C116, yellow solid, yield 71%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[0695] Synthesis Example C138:

[0696] The synthesis method is similar to that of C116, yellow solid, yield 71%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[0697] Synthesis Example C139:

[0698] Intermediate 23 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound C139 as a yellow solid with a yield of 73%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0699] Synthesis Example C140:

[0700] The synthesis method is similar to that of C139, yellow solid, yield 74%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0701] Synthesis Example C141:

[0702] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0703] Synthesis Example C142:

[0704] The synthesis method is similar to that of C139, yellow solid, yield 75%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0705] Synthesis Example C143:

[0706] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0707] Synthesis Example C144:

[0708] The synthesis method is similar to that of C139, yellow solid, yield 88%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[0709] Synthesis Example C145:

[0710] The synthesis method is similar to that of C139, yellow solid, yield 80%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0711] Synthesis Example C146:

[0712] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0713] Synthesis Example C147:

[0714] The synthesis method is similar to that of C139, yellow solid, yield 83%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0715] Synthesis Example C148:

[0716] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0717] Synthesis Example C149:

[0718] The synthesis method is similar to that of C139, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0719] Synthesis Example C150:

[0720] The synthesis method is similar to that of C139, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0721] Synthesis Example C151:

[0722] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0723] Synthesis Example C152:

[0724] The synthesis method is similar to that of C139, yellow solid, yield 75%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0725] Synthesis Example C153:

[0726] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0727] Synthesis Example C154:

[0728] The synthesis method is similar to that of C139, yellow solid, yield 69%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[0729] Synthesis Example C155:

[0730] The synthesis method is similar to that of C139, yellow solid, yield 79%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[0731] Synthesis Example C156:

[0732] The synthesis method is similar to that of C139, yellow solid, yield 58%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0733] Synthesis Example C157:

[0734] The synthesis method is similar to that of C139, yellow solid, yield 83%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0735] Synthesis Example C158:

[0736] The synthesis method is similar to that of C139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0737] Synthesis Example C159:

[0738] The synthesis method is similar to that of C139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0739] Synthesis Example C160:

[0740] The synthesis method is similar to that of C139, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[0741] Synthesis Example C161:

[0742] The synthesis method is similar to that of C139, yellow solid, yield 59%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[0743] Synthesis Example C162:

[0744] Intermediate 19 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound C162 as a yellow solid with a yield of 76%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0745] Synthesis Example C163:

[0746] The synthesis method is similar to that of C162, yellow solid, yield 75%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0747] Synthesis Example C164:

[0748] The synthesis method is similar to that of C162, yellow solid, yield 74%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0749] Synthesis Example C165:

[0750] The synthesis method is similar to that of C162, yellow solid, yield 73%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0751] Synthesis Example C166:

[0752] The synthesis method is similar to that of C162, yellow solid, yield 71%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0753] Synthesis Example C167:

[0754] The synthesis method is similar to that of C162, yellow solid, yield 70%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[0755] Synthesis Example C168:

[0756] The synthesis method is similar to that of C162, yellow solid, yield 70%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0757] Synthesis Example C169:

[0758] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0759] Synthesis Example C170:

[0760] The synthesis method is similar to that of C162, yellow solid, yield 70%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0761] Synthesis Example C171:

[0762] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0763] Synthesis Example C172:

[0764] The synthesis method is similar to that of C162, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0765] Synthesis Example C173:

[0766] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0767] Synthesis Example C174:

[0768] The synthesis method is similar to that of C162, yellow solid, yield 75%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0769] Synthesis Example C175:

[0770] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0771] Synthesis Example C176:

[0772] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0773] Synthesis Example C177:

[0774] The synthesis method is similar to that of C162, yellow solid, yield 58%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[0775] Synthesis Example C178:

[0776] The synthesis method is similar to that of C162, yellow solid, yield 67%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[0777] Synthesis Example C179:

[0778] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0779] Synthesis Example C180:

[0780] The synthesis method is similar to that of C162, yellow solid, yield 59%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0781] Synthesis Example C181:

[0782] The synthesis method is similar to that of C162, yellow solid, yield 76%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0783] Synthesis Example C182:

[0784] The synthesis method is similar to that of C162, yellow solid, yield 82%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0785] Synthesis Example C183:

[0786] The synthesis method is similar to that of C162, yellow solid, yield 73%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[0787] Synthesis Example C184:

[0788] The synthesis method is similar to that of C162, yellow solid, yield 79%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[0789] Synthesis of intermediate 25:

[0790]

[0791] 2,6-Dibromo-3,4,5-trifluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (13.27 g, 69.87 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (1.83 g, 1.59 mmol) and 20 mL of potassium carbonate aqueous solution (8.78 g, 63.51 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 25, weighing 6.8 g, with a yield of 59%.

[0792] Synthesis of intermediate 26-32:

[0793]

[0794] The synthesis method is similar to that of intermediate 25. Intermediates 25-32 are all white solids with yields of 59%, 58%, 49%, 70%, 66%, 51% and 47%, respectively.

[0795] Synthesis Example D1:

[0796] Intermediate 25 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound D1 as a yellow solid with a yield of 76%. Mass spectrum: m / z 800.93, elemental analysis experimental values: C, 85.48; H, 4.03; N, 10.49.

[0797] Synthesis Example D2:

[0798] The synthesis method is similar to D1, yellow solid, yield 79%. Mass spectrum: m / z 842.32, elemental analysis experimental values: C, 85.49; H, 4.54; N, 9.97.

[0799] Synthesis Example D3:

[0800] The synthesis method is similar to D1, yellow solid, yield 70%. Mass spectrum: m / z 884.36, elemental analysis experimental values: C, 85.49; H, 5.01; N, 9.50.

[0801] Synthesis Example D4:

[0802] The synthesis method is similar to that of D1, yellow solid, yield 72%. Mass spectrum: m / z 926.41, elemental analysis experimental values: C, 85.50; H, 5.44; N, 9.06.

[0803] Synthesis Example D5:

[0804] The synthesis method is similar to D1, yellow solid, yield 71%. Mass spectrum: m / z 1052.55, elemental analysis experimental values: C, 85.52; H, 6.51; N, 7.98.

[0805] Synthesis Example D6:

[0806] The synthesis method is similar to D1, yellow solid, yield 78%. Mass spectrum: m / z 968.46, elemental analysis experimental values: C, 85.51; H, 5.82; N, 8.67.

[0807] Synthesis Example D7:

[0808] The synthesis method is similar to D1, yellow solid, yield 79%. Mass spectrum: m / z 1136.64, elemental analysis experimental values: C, 85.52; H, 7.09; N, 7.39.

[0809] Synthesis Example D8:

[0810] The synthesis method is similar to D1, yellow solid, yield 78%. Mass spectrum: m / z 1016.39, elemental analysis experimental values: C, 77.91; H, 5.55; N, 8.26; Si, 8.28.

[0811] Synthesis Example D9:

[0812] The synthesis method is similar to D1, yellow solid, yield 79%. Mass spectrum: m / z 1218.49, elemental analysis experimental values: C, 72.85; H, 6.44; N, 6.89; Si, 13.81.

[0813] Synthesis Example D10:

[0814] The synthesis method is similar to D1, yellow solid, yield 70%. Mass spectrum: m / z 875.25, elemental analysis experimental values: C, 82.27; H, 3.34; N, 14.39.

[0815] Synthesis Example D11:

[0816] The synthesis method is similar to D1, yellow solid, yield 73%. Mass spectrum: m / z 950.24, elemental analysis experimental values: C, 79.57; H, 2.76; N, 17.67.

[0817] Synthesis Example D12:

[0818] The synthesis method is similar to D1, yellow solid, yield 76%. Mass spectrum: m / z 1028.36, elemental analysis experimental values: C, 87.53; H, 4.31; N, 8.17.

[0819] Synthesis Example D13:

[0820] The synthesis method is similar to D1, yellow solid, yield 79%. Mass spectrum: m / z 1256.46, elemental analysis experimental values: C, 88.83; H, 4.49; N, 6.68. Synthesis Example D14:

[0821] The synthesis method is similar to D1, yellow solid, yield 69%. Mass spectrum: m / z 1004.23, elemental analysis experimental values: C, 71.71; H, 2.91; F, 17.01; N, 8.36.

[0822] Synthesis Example D15:

[0823] The synthesis method is similar to D1, yellow solid, yield 80%. Mass spectrum: m / z 1208.19, elemental analysis experimental values: C, 62.59; H, 2.17; F, 28.29; N, 6.95.

[0824] Synthesis Example D16:

[0825] The synthesis method is similar to D1, yellow solid, yield 75%. Mass spectrum: m / z 1154.50, elemental analysis experimental values: C, 87.32; H, 5.41; N, 7.27.

[0826] Synthesis Example D17:

[0827] The synthesis method is similar to D1, yellow solid, yield 75%. Mass spectrum: m / z 1508.74, elemental analysis experimental values: C, 88.29; H, 6.14; N, 5.57.

[0828] Synthesis Example D18:

[0829] The synthesis method is similar to D1, yellow solid, yield 79%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0830] Synthesis Example D19:

[0831] The synthesis method is similar to that of D1, yellow solid, yield 70%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0832] Synthesis Example D20:

[0833] The synthesis method is similar to D1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0834] Synthesis Example D21:

[0835] The synthesis method is similar to that of D1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[0836] Synthesis Example D22:

[0837] The synthesis method is similar to D1, yellow solid, yield 81%. Mass spectrum: m / z 848.25, elemental analysis experimental values: C, 80.65; H, 3.80; N, 9.90; O, 5.65.

[0838] Synthesis Example D23:

[0839] The synthesis method is similar to D1, yellow solid, yield 70%. Mass spectrum: m / z 896.19, elemental analysis experimental values: C, 76.32; H, 3.60; N, 9.37; S, 10.72.

[0840] Synthesis Example D24:

[0841] Intermediate 26 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound D24 as a yellow solid with a yield of 83%. Mass spectrum: m / z 886.25, elemental analysis experimental values: C, 77.19; H, 3.64; F, 12.85; N, 6.32.

[0842] Synthesis Example D25:

[0843] The synthesis method is similar to that of D24, yellow solid, yield 70%. Mass spectrum: m / z 928.30, elemental analysis experimental values: C, 77.58; H, 4.12; F, 12.27; N, 6.03

[0844] Synthesis Example D26:

[0845] The synthesis method is similar to that of D24, yellow solid, yield 71%. Mass spectrum: m / z 970.35, elemental analysis experimental values: C, 77.92; H, 4.57; F, 11.74; N, 5.77

[0846] Synthesis Example D27:

[0847] The synthesis method is similar to that of D24, yellow solid, yield 73%. Mass spectrum: m / z 1012.39, elemental analysis experimental values: C, 78.24; H, 4.97; F, 11.25; N, 5.53

[0848] Synthesis Example D28:

[0849] The synthesis method is similar to that of D24, yellow solid, yield 69%. Mass spectrum: m / z 1138.53, elemental analysis experimental values: C, 79.06; H, 6.02; F, 10.00; N, 4.92

[0850] Synthesis Example D29:

[0851] The synthesis method is similar to that of D24, yellow solid, yield 67%. Mass spectrum: m / z 1054.44, elemental analysis experimental values: C, 78.54; H, 5.35; F, 10.80; N, 5.31

[0852] Synthesis Example D30:

[0853] The synthesis method is similar to that of D24, yellow solid, yield 66%. Mass spectrum: m / z 1222.63, elemental analysis experimental values: C, 79.51; H, 6.59; F, 9.32; N, 4.58

[0854] Synthesis Example D31:

[0855] The synthesis method is similar to that of D24, yellow solid, yield 80%. Mass spectrum: m / z 1102.37, elemental analysis experimental values: C, 71.84; H, 5.12; F, 10.33; N, 5.08; Si, 7.64

[0856] Synthesis Example D32:

[0857] The synthesis method is similar to that of D24, yellow solid, yield 73%. Mass spectrum: m / z 1304.47, elemental analysis experimental values: C, 68.06; H, 6.02; F, 8.73; N, 4.29; Si, 12.90

[0858] Synthesis Example D33:

[0859] The synthesis method is similar to that of D24, yellow solid, yield 72%. Mass spectrum: m / z 961.24, elemental analysis experimental values: C, 74.92; H, 3.04; F, 11.85; N, 10.19

[0860] Synthesis Example D34:

[0861] The synthesis method is similar to that of D24, yellow solid, yield 71%. Mass spectrum: m / z 1036.22, elemental analysis experimental values: C, 72.97; H, 2.53; F, 10.99; N, 13.51

[0862] Synthesis Example D35:

[0863] The synthesis method is similar to that of D24, yellow solid, yield 69%. Mass spectrum: m / z 1114.35, elemental analysis experimental values: C, 80.78; H, 3.98; F, 10.22; N, 5.02

[0864] Synthesis Example D36:

[0865] The synthesis method is similar to that of D24, yellow solid, yield 59%. Mass spectrum: m / z 1342.44, elemental analysis experimental values: C, 83.14; H, 4.20; F, 8.48; N, 4.17

[0866] Synthesis Example D37:

[0867] The synthesis method is similar to that of D24, yellow solid, yield 58%. Mass spectrum: m / z 1090.22, elemental analysis experimental values: C, 66.06; H, 2.68; F, 26.12; N, 5.14

[0868] Synthesis Example D38:

[0869] The synthesis method is similar to that of D24, yellow solid, yield 67%. Mass spectrum: m / z 1294.18, elemental analysis experimental values: C, 58.44; H, 2.02; F, 35.21; N, 4.33

[0870] Synthesis Example D39:

[0871] The synthesis method is similar to that of D24, yellow solid, yield 78%. Mass spectrum: m / z 1240.49, elemental analysis experimental values: C, 81.27; H, 5.03; F, 9.18; N, 4.51

[0872] Synthesis Example D40:

[0873] The synthesis method is similar to that of D24, yellow solid, yield 70%. Mass spectrum: m / z 1594.72, elemental analysis experimental values: C, 83.54; H, 5.81; F, 7.14; N, 3.51

[0874] Synthesis Example D41:

[0875] The synthesis method is similar to that of D24, yellow solid, yield 75%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0876] Synthesis Example D42:

[0877] The synthesis method is similar to that of D24, yellow solid, yield 80%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0878] Synthesis Example D43:

[0879] The synthesis method is similar to that of D24, yellow solid, yield 82%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0880] Synthesis Example D44:

[0881] The synthesis method is similar to that of D24, yellow solid, yield 79%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[0882] Synthesis Example D45:

[0883] The synthesis method is similar to that of D24, yellow solid, yield 79%. Mass spectrum: m / z 934.24, elemental analysis experimental values: C, 73.23; H, 3.45; F, 12.19; N, 5.99; O, 5.13

[0884] Synthesis Example D46:

[0885] The synthesis method is similar to that of D24, yellow solid, yield 75%. Mass spectrum: m / z 982.17, elemental analysis experimental values: C, 69.64; H, 3.28; F, 11.60; N, 5.70; S, 9.78

[0886] Synthesis Example D47:

[0887] Intermediate 27 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound D47 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0888] Synthesis Example D52:

[0889] The synthesis method is similar to that of D47, yellow solid, yield 70%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[0890] Synthesis Example D53:

[0891] The synthesis method is similar to that of D47, yellow solid, yield 74%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[0892] Synthesis Example D54:

[0893] The synthesis method is similar to that of D47, yellow solid, yield 75%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[0894] Synthesis Example D55:

[0895] The synthesis method is similar to that of D47, yellow solid, yield 73%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[0896] Synthesis Example D58:

[0897] The synthesis method is similar to that of D47, yellow solid, yield 69%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[0898] Synthesis Example D59:

[0899] The synthesis method is similar to that of D47, yellow solid, yield 69%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[0900] Synthesis Example D60:

[0901] The synthesis method is similar to that of D47, yellow solid, yield 78%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[0902] Synthesis Example D61:

[0903] The synthesis method is similar to that of D47, yellow solid, yield 74%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[0904] Synthesis Example D70:

[0905] Intermediate 28 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound D70 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[0906] Synthesis Example D75:

[0907] The synthesis method is similar to that of D70, yellow solid, yield 73%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[0908] Synthesis Example D73:

[0909] The synthesis method is similar to that of D70, yellow solid, yield 70%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[0910] Synthesis Example D77:

[0911] The synthesis method is similar to that of D70, yellow solid, yield 68%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[0912] Synthesis Example D78:

[0913] The synthesis method is similar to that of D70, yellow solid, yield 66%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[0914] Synthesis Example D81:

[0915] The synthesis method is similar to that of D70, yellow solid, yield 77%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[0916] Synthesis Example D82:

[0917] The synthesis method is similar to that of D70, yellow solid, yield 77%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[0918] Synthesis Example D83:

[0919] The synthesis method is similar to that of D70, yellow solid, yield 74%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[0920] Synthesis Example D84:

[0921] The synthesis method is similar to that of D70, yellow solid, yield 71%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[0922] Synthesis Example D93:

[0923] Intermediate 29 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound D93 as a yellow solid with a yield of 85%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[0924] Synthesis Example D94:

[0925] The synthesis method is similar to that of D93, yellow solid, yield 71%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0926] Synthesis Example D95:

[0927] The synthesis method is similar to that of D93, yellow solid, yield 70%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0928] Synthesis Example D96:

[0929] The synthesis method is similar to that of D93, yellow solid, yield 59%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0930] Synthesis Example D97:

[0931] The synthesis method is similar to that of D93, yellow solid, yield 58%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0932] Synthesis Example D98:

[0933] The synthesis method is similar to that of D93, yellow solid, yield 55%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54

[0934] Synthesis Example D99:

[0935] The synthesis method is similar to that of D93, yellow solid, yield 59%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0936] Synthesis Example D100:

[0937] The synthesis method is similar to that of D93, yellow solid, yield 61%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0938] Synthesis Example D101:

[0939] The synthesis method is similar to that of D93, yellow solid, yield 63%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0940] Synthesis Example D102:

[0941] The synthesis method is similar to that of D93, yellow solid, yield 73%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0942] Synthesis Example D103:

[0943] The synthesis method is similar to that of D93, yellow solid, yield 72%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0944] Synthesis Example D104:

[0945] The synthesis method is similar to that of D93, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0946] Synthesis Example D105:

[0947] The synthesis method is similar to that of D93, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0948] Synthesis Example D106:

[0949] The synthesis method is similar to that of D93, yellow solid, yield 74%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0950] Synthesis Example D107:

[0951] The synthesis method is similar to that of D93, yellow solid, yield 69%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0952] Synthesis Example D108:

[0953] The synthesis method is similar to that of D93, yellow solid, yield 55%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[0954] Synthesis Example D109:

[0955] The synthesis method is similar to that of D93, yellow solid, yield 80%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[0956] Synthesis Example D110:

[0957] The synthesis method is similar to that of D93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0958] Synthesis Example D111:

[0959] The synthesis method is similar to that of D93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0960] Synthesis Example D112:

[0961] The synthesis method is similar to that of D93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0962] Synthesis Example D113:

[0963] The synthesis method is similar to that of D93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[0964] Synthesis Example D114:

[0965] The synthesis method is similar to that of D93, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[0966] Synthesis Example D115:

[0967] The synthesis method is similar to that of D93, yellow solid, yield 72%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[0968] Synthesis Example D116:

[0969] Intermediate 30 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound D116 as a yellow solid with a yield of 83%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[0970] Synthesis Example D117:

[0971] The synthesis method is similar to that of D116, yellow solid, yield 77%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[0972] Synthesis Example D118:

[0973] The synthesis method is similar to that of D116, yellow solid, yield 75%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[0974] Synthesis Example D119:

[0975] The synthesis method is similar to that of D116, yellow solid, yield 78%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[0976] Synthesis Example D120:

[0977] The synthesis method is similar to that of D116, yellow solid, yield 60%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[0978] Synthesis Example D121:

[0979] The synthesis method is similar to that of D116, yellow solid, yield 59%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[0980] Synthesis Example D122:

[0981] The synthesis method is similar to that of D116, yellow solid, yield 55%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[0982] Synthesis Example D123:

[0983] The synthesis method is similar to that of D116, yellow solid, yield 80%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[0984] Synthesis Example D124:

[0985] The synthesis method is similar to that of D116, yellow solid, yield 81%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[0986] Synthesis Example D125:

[0987] The synthesis method is similar to that of D116, yellow solid, yield 83%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[0988] Synthesis Example D126:

[0989] The synthesis method is similar to that of D116, yellow solid, yield 88%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[0990] Synthesis Example D127:

[0991] The synthesis method is similar to that of D116, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[0992] Synthesis Example D128:

[0993] The synthesis method is similar to that of D116, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[0994] Synthesis Example D129:

[0995] The synthesis method is similar to that of D116, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[0996] Synthesis Example D130:

[0997] The synthesis method is similar to that of D116, yellow solid, yield 75%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[0998] Synthesis Example D131:

[0999] The synthesis method is similar to that of D116, yellow solid, yield 67%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1000] Synthesis Example D132:

[1001] The synthesis method is similar to that of D116, yellow solid, yield 53%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1002] Synthesis Example D133:

[1003] The synthesis method is similar to that of D116, yellow solid, yield 70%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1004] Synthesis Example D134:

[1005] The synthesis method is similar to that of D116, yellow solid, yield 80%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1006] Synthesis Example D135:

[1007] The synthesis method is similar to that of D116, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1008] Synthesis Example D136:

[1009] The synthesis method is similar to that of D116, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1010] Synthesis Example D137:

[1011] The synthesis method is similar to that of D116, yellow solid, yield 71%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1012] Synthesis Example D138:

[1013] The synthesis method is similar to that of D116, yellow solid, yield 71%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1014] Synthesis Example D139:

[1015] Intermediate 31 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound D139 as a yellow solid with a yield of 73%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1016] Synthesis Example D140:

[1017] The synthesis method is similar to that of D139, yellow solid, yield 74%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1018] Synthesis Example D141:

[1019] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1020] Synthesis Example D142:

[1021] The synthesis method is similar to that of D139, yellow solid, yield 75%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1022] Synthesis Example D143:

[1023] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1024] Synthesis Example D144:

[1025] The synthesis method is similar to that of D139, yellow solid, yield 88%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1026] Synthesis Example D145:

[1027] The synthesis method is similar to that of D139, yellow solid, yield 80%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1028] Synthesis Example D146:

[1029] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1030] Synthesis Example D147:

[1031] The synthesis method is similar to that of D139, yellow solid, yield 83%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1032] Synthesis Example D148:

[1033] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1034] Synthesis Example D149:

[1035] The synthesis method is similar to that of D139, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1036] Synthesis Example D150:

[1037] The synthesis method is similar to that of D139, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1038] Synthesis Example D151:

[1039] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1040] Synthesis Example D152:

[1041] The synthesis method is similar to that of D139, yellow solid, yield 75%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1042] Synthesis Example D153:

[1043] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1044] Synthesis Example D154:

[1045] The synthesis method is similar to that of D139, yellow solid, yield 69%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1046] Synthesis Example D155:

[1047] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1048] Synthesis Example D156:

[1049] The synthesis method is similar to that of D139, yellow solid, yield 58%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1050] Synthesis Example D157:

[1051] The synthesis method is similar to that of D139, yellow solid, yield 83%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1052] Synthesis Example D158:

[1053] The synthesis method is similar to that of D139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1054] Synthesis Example D159:

[1055] The synthesis method is similar to that of D139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1056] Synthesis Example D160:

[1057] The synthesis method is similar to that of D139, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1058] Synthesis Example D161:

[1059] The synthesis method is similar to that of D139, yellow solid, yield 59%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1060] Synthesis Example D162:

[1061] Intermediate 32 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound D162 as a yellow solid with a yield of 76%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1062] Synthesis Example D163:

[1063] The synthesis method is similar to that of D162, yellow solid, yield 75%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1064] Synthesis Example D164:

[1065] The synthesis method is similar to that of D162, yellow solid, yield 74%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1066] Synthesis Example D165:

[1067] The synthesis method is similar to that of D162, yellow solid, yield 73%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1068] Synthesis Example D166:

[1069] The synthesis method is similar to that of D162, yellow solid, yield 71%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1070] Synthesis Example D167:

[1071] The synthesis method is similar to that of D162, yellow solid, yield 70%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1072] Synthesis Example D168:

[1073] The synthesis method is similar to that of D162, yellow solid, yield 70%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1074] Synthesis Example D169:

[1075] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1076] Synthesis Example D170:

[1077] The synthesis method is similar to that of D162, yellow solid, yield 70%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1078] Synthesis Example D171:

[1079] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1080] Synthesis Example D172:

[1081] The synthesis method is similar to that of D162, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1082] Synthesis Example D173:

[1083] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1084] Synthesis Example D174:

[1085] The synthesis method is similar to that of D162, yellow solid, yield 75%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1086] Synthesis Example D175:

[1087] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1088] Synthesis Example D176:

[1089] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1090] Synthesis Example D177:

[1091] The synthesis method is similar to that of D162, yellow solid, yield 58%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1092] Synthesis Example D178:

[1093] The synthesis method is similar to that of D162, yellow solid, yield 67%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1094] Synthesis Example D179:

[1095] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1096] Synthesis Example D180:

[1097] The synthesis method is similar to that of D162, yellow solid, yield 59%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1098] Synthesis Example D181:

[1099] The synthesis method is similar to that of D162, yellow solid, yield 76%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1100] Synthesis Example D182:

[1101] The synthesis method is similar to that of D162, yellow solid, yield 82%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1102] Synthesis Example D183:

[1103] The synthesis method is similar to that of D162, yellow solid, yield 73%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1104] Synthesis Example D184:

[1105] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1106] Synthesis of intermediate 33:

[1107]

[1108] 2,5-Dibromo-3,4,6-trifluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (13.27 g, 69.87 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (1.83 g, 1.59 mmol) and 20 mL of potassium carbonate aqueous solution (8.78 g, 63.51 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 33, weighing 7.2 g, with a yield of 63%.

[1109] Synthesis of intermediate 34-40:

[1110]

[1111] The synthesis method is similar to that of intermediate 33. Intermediates 34-40 are all white solids with yields of 69%, 74%, 59%, 72%, 76%, 61%, and 58%, respectively.

[1112] Synthesis Example E1:

[1113] Intermediate 33 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E1 as a yellow solid with a yield of 76%. Mass spectrum: m / z 800.93, elemental analysis experimental values: C, 85.48; H, 4.03; N, 10.49.

[1114] Synthesis Example E2:

[1115] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 842.32, elemental analysis experimental values: C, 85.49; H, 4.54; N, 9.97.

[1116] Synthesis Example E3:

[1117] The synthesis method is similar to that of E1, yellow solid, yield 70%. Mass spectrum: m / z 884.36, elemental analysis experimental values: C, 85.49; H, 5.01; N, 9.50.

[1118] Synthesis Example E4:

[1119] The synthesis method is similar to that of E1, yellow solid, yield 72%. Mass spectrum: m / z 926.41, elemental analysis experimental values: C, 85.50; H, 5.44; N, 9.06.

[1120] Synthesis Example E5:

[1121] The synthesis method is similar to that of E1, yellow solid, yield 71%. Mass spectrum: m / z 1052.55, elemental analysis experimental values: C, 85.52; H, 6.51; N, 7.98.

[1122] Synthesis Example E6:

[1123] The synthesis method is similar to that of E1, yellow solid, yield 78%. Mass spectrum: m / z 968.46, elemental analysis experimental values: C, 85.51; H, 5.82; N, 8.67.

[1124] Synthesis Example E7:

[1125] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 1136.64, elemental analysis experimental values: C, 85.52; H, 7.09; N, 7.39.

[1126] Synthesis Example E8:

[1127] The synthesis method is similar to that of E1, yellow solid, yield 78%. Mass spectrum: m / z 1016.39, elemental analysis experimental values: C, 77.91; H, 5.55; N, 8.26; Si, 8.28.

[1128] Synthesis Example E9:

[1129] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 1218.49, elemental analysis experimental values: C, 72.85; H, 6.44; N, 6.89; Si, 13.81.

[1130] Synthesis Example E10:

[1131] The synthesis method is similar to that of E1, yellow solid, yield 70%. Mass spectrum: m / z 875.25, elemental analysis experimental values: C, 82.27; H, 3.34; N, 14.39.

[1132] Synthesis Example E11:

[1133] The synthesis method is similar to that of E1, yellow solid, yield 73%. Mass spectrum: m / z 950.24, elemental analysis experimental values: C, 79.57; H, 2.76; N, 17.67.

[1134] Synthesis Example E12:

[1135] The synthesis method is similar to that of E1, yellow solid, yield 76%. Mass spectrum: m / z 1028.36, elemental analysis experimental values: C, 87.53; H, 4.31; N, 8.17.

[1136] Synthesis Example E13:

[1137] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 1256.46, elemental analysis experimental values: C, 88.83; H, 4.49; N, 6.68.

[1138] Synthesis Example E14:

[1139] The synthesis method is similar to that of E1, yellow solid, yield 69%. Mass spectrum: m / z 1004.23, elemental analysis experimental values: C, 71.71; H, 2.91; F, 17.01; N, 8.36.

[1140] Synthesis Example E15:

[1141] The synthesis method is similar to that of E1, yellow solid, yield 80%. Mass spectrum: m / z 1208.19, elemental analysis experimental values: C, 62.59; H, 2.17; F, 28.29; N, 6.95.

[1142] Synthesis Example E16:

[1143] The synthesis method is similar to that of E1, yellow solid, yield 75%. Mass spectrum: m / z 1154.50, elemental analysis experimental values: C, 87.32; H, 5.41; N, 7.27.

[1144] Synthesis Example E17:

[1145] The synthesis method is similar to that of E1, yellow solid, yield 75%. Mass spectrum: m / z 1508.74, elemental analysis experimental values: C, 88.29; H, 6.14; N, 5.57.

[1146] Synthesis Example E18:

[1147] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1148] Synthesis Example E19:

[1149] The synthesis method is similar to that of E1, yellow solid, yield 70%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1150] Synthesis Example E20:

[1151] The synthesis method is similar to that of E1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1152] Synthesis Example E21:

[1153] The synthesis method is similar to that of E1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1154] Synthesis Example E22:

[1155] The synthesis method is similar to that of E1, yellow solid, yield 81%. Mass spectrum: m / z 848.25, elemental analysis experimental values: C, 80.65; H, 3.80; N, 9.90; O, 5.65.

[1156] Synthesis Example E23:

[1157] The synthesis method is similar to that of E1, yellow solid, yield 70%. Mass spectrum: m / z 896.19, elemental analysis experimental values: C, 76.32; H, 3.60; N, 9.37; S, 10.72.

[1158] Synthesis Example E24:

[1159] Intermediate 34 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E24 as a yellow solid with a yield of 83%. Mass spectrum: m / z 886.25, elemental analysis experimental values: C, 77.19; H, 3.64; F, 12.85; N, 6.32.

[1160] Synthesis Example E25:

[1161] The synthesis method is similar to that of E24, yellow solid, yield 70%. Mass spectrum: m / z 928.30, elemental analysis experimental values: C, 77.58; H, 4.12; F, 12.27; N, 6.03

[1162] Synthesis Example E26:

[1163] The synthesis method is similar to that of E24, yellow solid, yield 71%. Mass spectrum: m / z 970.35, elemental analysis experimental values: C, 77.92; H, 4.57; F, 11.74; N, 5.77

[1164] Synthesis Example E27:

[1165] The synthesis method is similar to that of E24, yellow solid, yield 73%. Mass spectrum: m / z 1012.39, elemental analysis experimental values: C, 78.24; H, 4.97; F, 11.25; N, 5.53

[1166] Synthesis Example E28:

[1167] The synthesis method is similar to that of E24, yellow solid, yield 69%. Mass spectrum: m / z 1138.53, elemental analysis experimental values: C, 79.06; H, 6.02; F, 10.00; N, 4.92

[1168] Synthesis Example E29:

[1169] The synthesis method is similar to that of E24, yellow solid, yield 67%. Mass spectrum: m / z 1054.44, elemental analysis experimental values: C, 78.54; H, 5.35; F, 10.80; N, 5.31

[1170] Synthesis Example E30:

[1171] The synthesis method is similar to that of E24, yellow solid, yield 66%. Mass spectrum: m / z 1222.63, elemental analysis experimental values: C, 79.51; H, 6.59; F, 9.32; N, 4.58

[1172] Synthesis Example E31:

[1173] The synthesis method is similar to that of E24, yellow solid, yield 80%. Mass spectrum: m / z 1102.37, elemental analysis experimental values: C, 71.84; H, 5.12; F, 10.33; N, 5.08; Si, 7.64

[1174] Synthesis Example E32:

[1175] The synthesis method is similar to that of E24, yellow solid, yield 73%. Mass spectrum: m / z 1304.47, elemental analysis experimental values: C, 68.06; H, 6.02; F, 8.73; N, 4.29; Si, 12.90

[1176] Synthesis Example E33:

[1177] The synthesis method is similar to that of E24, yellow solid, yield 72%. Mass spectrum: m / z 961.24, elemental analysis experimental values: C, 74.92; H, 3.04; F, 11.85; N, 10.19

[1178] Synthesis Example E34:

[1179] The synthesis method is similar to that of E24, yellow solid, yield 71%. Mass spectrum: m / z 1036.22, elemental analysis experimental values: C, 72.97; H, 2.53; F, 10.99; N, 13.51

[1180] Synthesis Example E35:

[1181] The synthesis method is similar to that of E24, yellow solid, yield 69%. Mass spectrum: m / z 1114.35, elemental analysis experimental values: C, 80.78; H, 3.98; F, 10.22; N, 5.02

[1182] Synthesis Example E36:

[1183] The synthesis method is similar to that of E24, yellow solid, yield 59%. Mass spectrum: m / z 1342.44, elemental analysis experimental values: C, 83.14; H, 4.20; F, 8.48; N, 4.17

[1184] Synthesis Example E37:

[1185] The synthesis method is similar to that of E24, yellow solid, yield 58%. Mass spectrum: m / z 1090.22, elemental analysis experimental values: C, 66.06; H, 2.68; F, 26.12; N, 5.14

[1186] Synthesis Example E38:

[1187] The synthesis method is similar to that of E24, yellow solid, yield 67%. Mass spectrum: m / z 1294.18, elemental analysis experimental values: C, 58.44; H, 2.02; F, 35.21; N, 4.33

[1188] Synthesis Example E39:

[1189] The synthesis method is similar to that of E24, yellow solid, yield 78%. Mass spectrum: m / z 1240.49, elemental analysis experimental values: C, 81.27; H, 5.03; F, 9.18; N, 4.51

[1190] Synthesis Example E40:

[1191] The synthesis method is similar to that of E24, yellow solid, yield 70%. Mass spectrum: m / z 1594.72, elemental analysis experimental values: C, 83.54; H, 5.81; F, 7.14; N, 3.51

[1192] Synthesis Example E41:

[1193] The synthesis method is similar to that of E24, yellow solid, yield 75%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1194] Synthesis Example E42:

[1195] The synthesis method is similar to that of E24, yellow solid, yield 80%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1196] Synthesis Example E43:

[1197] The synthesis method is similar to that of E24, yellow solid, yield 82%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1198] Synthesis Example E44:

[1199] The synthesis method is similar to that of E24, yellow solid, yield 79%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1200] Synthesis Example E45:

[1201] The synthesis method is similar to that of E24, yellow solid, yield 79%. Mass spectrum: m / z 934.24, elemental analysis experimental values: C, 73.23; H, 3.45; F, 12.19; N, 5.99; O, 5.13

[1202] Synthesis Example E46:

[1203] The synthesis method is similar to that of E24, yellow solid, yield 75%. Mass spectrum: m / z 982.17, elemental analysis experimental values: C, 69.64; H, 3.28; F, 11.60; N, 5.70; S, 9.78

[1204] Synthesis Example E47:

[1205] Intermediate 35 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E47 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1206] Synthesis Example E52:

[1207] The synthesis method is similar to that of E47, yellow solid, yield 70%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1208] Synthesis Example E53:

[1209] The synthesis method is similar to that of E47, yellow solid, yield 74%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1210] Synthesis Example E54:

[1211] The synthesis method is similar to that of E47, yellow solid, yield 75%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1212] Synthesis Example E55:

[1213] The synthesis method is similar to that of E47, yellow solid, yield 73%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1214] Synthesis Example E58:

[1215] The synthesis method is similar to that of E47, yellow solid, yield 69%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1216] Synthesis Example E59:

[1217] The synthesis method is similar to that of E47, yellow solid, yield 69%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1218] Synthesis Example E60:

[1219] The synthesis method is similar to that of E47, yellow solid, yield 78%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[1220] Synthesis Example E61:

[1221] The synthesis method is similar to that of E47, yellow solid, yield 74%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[1222] Synthesis Example E70:

[1223] Intermediate 36 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E70 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1224] Synthesis Example E75:

[1225] The synthesis method is similar to that of E70, yellow solid, yield 73%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1226] Synthesis Example E73:

[1227] The synthesis method is similar to that of E70, yellow solid, yield 70%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1228] Synthesis Example E77:

[1229] The synthesis method is similar to that of E70, yellow solid, yield 68%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1230] Synthesis Example E78:

[1231] The synthesis method is similar to that of E70, yellow solid, yield 66%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1232] Synthesis Example E81:

[1233] The synthesis method is similar to that of E70, yellow solid, yield 77%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1234] Synthesis Example E82:

[1235] The synthesis method is similar to that of E70, yellow solid, yield 77%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1236] Synthesis Example E83:

[1237] The synthesis method is similar to that of E70, yellow solid, yield 74%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[1238] Synthesis Example E84:

[1239] The synthesis method is similar to that of E70, yellow solid, yield 71%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[1240] Synthesis Example E93:

[1241] Intermediate 37 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E93 as a yellow solid with a yield of 85%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1242] Synthesis Example E94:

[1243] The synthesis method is similar to that of E93, yellow solid, yield 71%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1244] Synthesis Example E95:

[1245] The synthesis method is similar to that of E93, yellow solid, yield 70%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1246] Synthesis Example E96:

[1247] The synthesis method is similar to that of E93, yellow solid, yield 59%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1248] Synthesis Example E97:

[1249] The synthesis method is similar to that of E93, yellow solid, yield 58%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1250] Synthesis Example E98:

[1251] The synthesis method is similar to that of E93, yellow solid, yield 55%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54

[1252] Synthesis Example E99:

[1253] The synthesis method is similar to that of E93, yellow solid, yield 59%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1254] Synthesis Example E100:

[1255] The synthesis method is similar to that of E93, yellow solid, yield 61%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1256] Synthesis Example E101:

[1257] The synthesis method is similar to that of E93, yellow solid, yield 63%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1258] Synthesis Example E102:

[1259] The synthesis method is similar to that of E93, yellow solid, yield 73%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1260] Synthesis Example E103:

[1261] The synthesis method is similar to that of E93, yellow solid, yield 72%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1262] Synthesis Example E104:

[1263] The synthesis method is similar to that of E93, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1264] Synthesis Example E105:

[1265] The synthesis method is similar to that of E93, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1266] Synthesis Example E106:

[1267] The synthesis method is similar to that of E93, yellow solid, yield 74%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1268] Synthesis Example E107:

[1269] The synthesis method is similar to that of E93, yellow solid, yield 69%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1270] Synthesis Example E108:

[1271] The synthesis method is similar to that of E93, yellow solid, yield 55%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1272] Synthesis Example E109:

[1273] The synthesis method is similar to that of E93, yellow solid, yield 80%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1274] Synthesis Example E110:

[1275] The synthesis method is similar to that of E93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1276] Synthesis Example E111:

[1277] The synthesis method is similar to that of E93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1278] Synthesis Example E112:

[1279] The synthesis method is similar to that of E93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1280] Synthesis Example E113:

[1281] The synthesis method is similar to that of E93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1282] Synthesis Example E114:

[1283] The synthesis method is similar to that of E93, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1284] Synthesis Example E115:

[1285] The synthesis method is similar to that of E93, yellow solid, yield 72%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1286] Synthesis Example E116:

[1287] Intermediate 38 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E116 as a yellow solid with a yield of 83%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1288] Synthesis Example E117:

[1289] The synthesis method is similar to that of E116, yellow solid, yield 77%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1290] Synthesis Example E118:

[1291] The synthesis method is similar to that of E116, yellow solid, yield 75%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1292] Synthesis Example E119:

[1293] The synthesis method is similar to that of E116, yellow solid, yield 78%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1294] Synthesis Example E120:

[1295] The synthesis method is similar to that of E116, yellow solid, yield 60%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1296] Synthesis Example E121:

[1297] The synthesis method is similar to that of E116, yellow solid, yield 59%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1298] Synthesis Example E122:

[1299] The synthesis method is similar to that of E116, yellow solid, yield 55%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1300] Synthesis Example E123:

[1301] The synthesis method is similar to that of E116, yellow solid, yield 80%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1302] Synthesis Example E124:

[1303] The synthesis method is similar to that of E116, yellow solid, yield 81%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1304] Synthesis Example E125:

[1305] The synthesis method is similar to that of E116, yellow solid, yield 83%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1306] Synthesis Example E126:

[1307] The synthesis method is similar to that of E116, yellow solid, yield 88%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1308] Synthesis Example E127:

[1309] The synthesis method is similar to that of E116, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1310] Synthesis Example E128:

[1311] The synthesis method is similar to that of E116, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1312] Synthesis Example E129:

[1313] The synthesis method is similar to that of E116, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1314] Synthesis Example E130:

[1315] The synthesis method is similar to that of E116, yellow solid, yield 75%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1316] Synthesis Example E131:

[1317] The synthesis method is similar to that of E116, yellow solid, yield 67%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1318] Synthesis Example E132:

[1319] The synthesis method is similar to that of E116, yellow solid, yield 53%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1320] Synthesis Example E133:

[1321] The synthesis method is similar to that of E116, yellow solid, yield 70%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1322] Synthesis Example E134:

[1323] The synthesis method is similar to that of E116, yellow solid, yield 80%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1324] Synthesis Example E135:

[1325] The synthesis method is similar to that of E116, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1326] Synthesis Example E136:

[1327] The synthesis method is similar to that of E116, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1328] Synthesis Example E137:

[1329] The synthesis method is similar to that of E116, yellow solid, yield 71%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1330] Synthesis Example E138:

[1331] The synthesis method is similar to that of E116, yellow solid, yield 71%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1332] Synthesis Example E139:

[1333] Intermediate 39 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E139 as a yellow solid with a yield of 73%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1334] Synthesis Example E140:

[1335] The synthesis method is similar to that of E139, yellow solid, yield 74%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1336] Synthesis Example E141:

[1337] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1338] Synthesis Example E142:

[1339] The synthesis method is similar to that of E139, yellow solid, yield 75%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1340] Synthesis Example E143:

[1341] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1342] Synthesis Example E144:

[1343] The synthesis method is similar to that of E139, yellow solid, yield 88%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1344] Synthesis Example E145:

[1345] The synthesis method is similar to that of E139, yellow solid, yield 80%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1346] Synthesis Example E146:

[1347] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1348] Synthesis Example E147:

[1349] The synthesis method is similar to that of E139, yellow solid, yield 83%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1350] Synthesis Example E148:

[1351] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1352] Synthesis Example E149:

[1353] The synthesis method is similar to that of E139, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1354] Synthesis Example E150:

[1355] The synthesis method is similar to that of E139, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1356] Synthesis Example E151:

[1357] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1358] Synthesis Example E152:

[1359] The synthesis method is similar to that of E139, yellow solid, yield 75%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1360] Synthesis Example E153:

[1361] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1362] Synthesis Example E154:

[1363] The synthesis method is similar to that of E139, yellow solid, yield 69%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1364] Synthesis Example E155:

[1365] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1366] Synthesis Example E156:

[1367] The synthesis method is similar to that of E139, yellow solid, yield 58%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1368] Synthesis Example E157:

[1369] The synthesis method is similar to that of E139, yellow solid, yield 83%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1370] Synthesis Example E158:

[1371] The synthesis method is similar to that of E139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1372] Synthesis Example E159:

[1373] The synthesis method is similar to that of E139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1374] Synthesis Example E160:

[1375] The synthesis method is similar to that of E139, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1376] Synthesis Example E161:

[1377] The synthesis method is similar to that of E139, yellow solid, yield 59%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1378] Synthesis Example E162:

[1379] Intermediate 40 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound E162 as a yellow solid with a yield of 76%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1380] Synthesis Example E163:

[1381] The synthesis method is similar to that of E162, yellow solid, yield 75%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1382] Synthesis Example E164:

[1383] The synthesis method is similar to that of E162, yellow solid, yield 74%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1384] Synthesis Example E165:

[1385] The synthesis method is similar to that of E162, yellow solid, yield 73%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1386] Synthesis Example E166:

[1387] The synthesis method is similar to that of E162, yellow solid, yield 71%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1388] Synthesis Example E167:

[1389] The synthesis method is similar to that of E162, yellow solid, yield 70%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1390] Synthesis Example E168:

[1391] The synthesis method is similar to that of E162, yellow solid, yield 70%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1392] Synthesis Example E169:

[1393] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1394] Synthesis Example E170:

[1395] The synthesis method is similar to that of E162, yellow solid, yield 70%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1396] Synthesis Example E171:

[1397] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1398] Synthesis Example E172:

[1399] The synthesis method is similar to that of E162, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1400] Synthesis Example E173:

[1401] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1402] Synthesis Example E174:

[1403] The synthesis method is similar to that of E162, yellow solid, yield 75%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1404] Synthesis Example E175:

[1405] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1406] Synthesis Example E176:

[1407] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1408] Synthesis Example E177:

[1409] The synthesis method is similar to that of E162, yellow solid, yield 58%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1410] Synthesis Example E178:

[1411] The synthesis method is similar to that of E162, yellow solid, yield 67%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1412] Synthesis Example E179:

[1413] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1414] Synthesis Example E180:

[1415] The synthesis method is similar to that of E162, yellow solid, yield 59%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1416] Synthesis Example E181:

[1417] The synthesis method is similar to that of E162, yellow solid, yield 76%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1418] Synthesis Example E182:

[1419] The synthesis method is similar to that of E162, yellow solid, yield 82%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1420] Synthesis Example E183:

[1421] The synthesis method is similar to that of E162, yellow solid, yield 73%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1422] Synthesis Example E184:

[1423] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1424] Synthesis of intermediate 41:

[1425]

[1426] 2,5-Dibromo-3,4,6-trifluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (13.27 g, 69.87 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (1.83 g, 1.59 mmol) and 20 mL of potassium carbonate aqueous solution (8.78 g, 63.51 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 41, weighing 7.2 g, with a yield of 63%.

[1427] Synthesis of intermediates 42-48:

[1428]

[1429] The synthesis method is similar to that of intermediate 41. Intermediates 42-48 are all white solids with yields of 55%, 64%, 58%, 62%, 66%, 51%, and 55%, respectively.

[1430] Synthesis Example F1:

[1431] Intermediate 41 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F1 as a yellow solid with a yield of 76%. Mass spectrum: m / z 800.93, elemental analysis experimental values: C, 85.48; H, 4.03; N, 10.49.

[1432] Synthesis Example F2:

[1433] The synthesis method is similar to F1, yellow solid, yield 79%. Mass spectrum: m / z 842.32, elemental analysis experimental values: C, 85.49; H, 4.54; N, 9.97.

[1434] Synthesis Example F3:

[1435] The synthesis method is similar to F1, yellow solid, yield 70%. Mass spectrum: m / z 884.36, elemental analysis experimental values: C, 85.49; H, 5.01; N, 9.50.

[1436] Synthesis Example F4:

[1437] The synthesis method is similar to F1, yellow solid, yield 72%. Mass spectrum: m / z 926.41, elemental analysis experimental values: C, 85.50; H, 5.44; N, 9.06.

[1438] Synthesis Example F5:

[1439] The synthesis method is similar to that of F1, yellow solid, yield 71%. Mass spectrum: m / z 1052.55, elemental analysis experimental values: C, 85.52; H, 6.51; N, 7.98.

[1440] Synthesis Example F6:

[1441] The synthesis method is similar to that of F1, yellow solid, yield 78%. Mass spectrum: m / z 968.46, elemental analysis experimental values: C, 85.51; H, 5.82; N, 8.67.

[1442] Synthesis Example F7:

[1443] The synthesis method is similar to that of F1, yellow solid, yield 79%. Mass spectrum: m / z 1136.64, elemental analysis experimental values: C, 85.52; H, 7.09; N, 7.39.

[1444] Synthesis Example F8:

[1445] The synthesis method is similar to F1, yellow solid, yield 78%. Mass spectrum: m / z 1016.39, elemental analysis experimental values: C, 77.91; H, 5.55; N, 8.26; Si, 8.28.

[1446] Synthesis Example F9:

[1447] The synthesis method is similar to F1, yellow solid, yield 79%. Mass spectrum: m / z 1218.49, elemental analysis experimental values: C, 72.85; H, 6.44; N, 6.89; Si, 13.81.

[1448] Synthesis Example F10:

[1449] The synthesis method is similar to that of F1, yellow solid, yield 70%. Mass spectrum: m / z 875.25, elemental analysis experimental values: C, 82.27; H, 3.34; N, 14.39.

[1450] Synthesis Example F11:

[1451] The synthesis method is similar to F1, yellow solid, yield 73%. Mass spectrum: m / z 950.24, elemental analysis experimental values: C, 79.57; H, 2.76; N, 17.67.

[1452] Synthesis Example F12:

[1453] The synthesis method is similar to that of F1, yellow solid, yield 76%. Mass spectrum: m / z 1028.36, elemental analysis experimental values: C, 87.53; H, 4.31; N, 8.17.

[1454] Synthesis Example F13:

[1455] The synthesis method is similar to F1, yellow solid, yield 79%. Mass spectrum: m / z 1256.46, elemental analysis experimental values: C, 88.83; H, 4.49; N, 6.68.

[1456] Synthesis Example F14:

[1457] The synthesis method is similar to that of F1, yellow solid, yield 69%. Mass spectrum: m / z 1004.23, elemental analysis experimental values: C, 71.71; H, 2.91; F, 17.01; N, 8.36.

[1458] Synthesis Example F15:

[1459] The synthesis method is similar to that of F1, yellow solid, yield 80%. Mass spectrum: m / z 1208.19, elemental analysis experimental values: C, 62.59; H, 2.17; F, 28.29; N, 6.95.

[1460] Synthesis Example F16:

[1461] The synthesis method is similar to that of F1, yellow solid, yield 75%. Mass spectrum: m / z 1154.50, elemental analysis experimental values: C, 87.32; H, 5.41; N, 7.27.

[1462] Synthesis Example F17:

[1463] The synthesis method is similar to F1, yellow solid, yield 75%. Mass spectrum: m / z 1508.74, elemental analysis experimental values: C, 88.29; H, 6.14; N, 5.57.

[1464] Synthesis Example F18:

[1465] The synthesis method is similar to that of F1, yellow solid, yield 79%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1466] Synthesis Example F19:

[1467] The synthesis method is similar to F1, yellow solid, yield 70%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1468] Synthesis Example F20:

[1469] The synthesis method is similar to that of F1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1470] Synthesis Example F21:

[1471] The synthesis method is similar to that of F1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1472] Synthesis Example F22:

[1473] The synthesis method is similar to that of F1, yellow solid, yield 81%. Mass spectrum: m / z 848.25, elemental analysis experimental values: C, 80.65; H, 3.80; N, 9.90; O, 5.65.

[1474] Synthesis Example F23:

[1475] The synthesis method is similar to that of F1, yellow solid, yield 70%. Mass spectrum: m / z 896.19, elemental analysis experimental values: C, 76.32; H, 3.60; N, 9.37; S, 10.72.

[1476] Synthesis Example F24:

[1477] Intermediate 42 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F24 as a yellow solid with a yield of 83%. Mass spectrum: m / z 886.25, elemental analysis experimental values: C, 77.19; H, 3.64; F, 12.85; N, 6.32.

[1478] Synthesis Example F25:

[1479] The synthesis method is similar to that of F24, yellow solid, yield 70%. Mass spectrum: m / z 928.30, elemental analysis experimental values: C, 77.58; H, 4.12; F, 12.27; N, 6.03

[1480] Synthesis Example F26:

[1481] The synthesis method is similar to that of F24, yellow solid, yield 71%. Mass spectrum: m / z 970.35, elemental analysis experimental values: C, 77.92; H, 4.57; F, 11.74; N, 5.77

[1482] Synthesis Example F27:

[1483] The synthesis method is similar to that of F24, yellow solid, yield 73%. Mass spectrum: m / z 1012.39, elemental analysis experimental values: C, 78.24; H, 4.97; F, 11.25; N, 5.53

[1484] Synthesis Example F28:

[1485] The synthesis method is similar to that of F24, yellow solid, yield 69%. Mass spectrum: m / z 1138.53, elemental analysis experimental values: C, 79.06; H, 6.02; F, 10.00; N, 4.92

[1486] Synthesis Example F29:

[1487] The synthesis method is similar to that of F24, yellow solid, yield 67%. Mass spectrum: m / z 1054.44, elemental analysis experimental values: C, 78.54; H, 5.35; F, 10.80; N, 5.31

[1488] Synthesis Example F30:

[1489] The synthesis method is similar to that of F24, yellow solid, yield 66%. Mass spectrum: m / z 1222.63, elemental analysis experimental values: C, 79.51; H, 6.59; F, 9.32; N, 4.58

[1490] Synthesis Example F31:

[1491] The synthesis method is similar to that of F24, yellow solid, yield 80%. Mass spectrum: m / z 1102.37, elemental analysis experimental values: C, 71.84; H, 5.12; F, 10.33; N, 5.08; Si, 7.64

[1492] Synthesis Example F32:

[1493] The synthesis method is similar to that of F24, yellow solid, yield 73%. Mass spectrum: m / z 1304.47, elemental analysis experimental values: C, 68.06; H, 6.02; F, 8.73; N, 4.29; Si, 12.90

[1494] Synthesis Example F33:

[1495] The synthesis method is similar to that of F24, yellow solid, yield 72%. Mass spectrum: m / z 961.24, elemental analysis experimental values: C, 74.92; H, 3.04; F, 11.85; N, 10.19

[1496] Synthesis Example F34:

[1497] The synthesis method is similar to that of F24, yellow solid, yield 71%. Mass spectrum: m / z 1036.22, elemental analysis experimental values: C, 72.97; H, 2.53; F, 10.99; N, 13.51

[1498] Synthesis Example F35:

[1499] The synthesis method is similar to that of F24, yellow solid, yield 69%. Mass spectrum: m / z 1114.35, elemental analysis experimental values: C, 80.78; H, 3.98; F, 10.22; N, 5.02

[1500] Synthesis Example F36:

[1501] The synthesis method is similar to that of F24, yellow solid, yield 59%. Mass spectrum: m / z 1342.44, elemental analysis experimental values: C, 83.14; H, 4.20; F, 8.48; N, 4.17

[1502] Synthesis Example F37:

[1503] The synthesis method is similar to that of F24, yellow solid, yield 58%. Mass spectrum: m / z 1090.22, elemental analysis experimental values: C, 66.06; H, 2.68; F, 26.12; N, 5.14

[1504] Synthesis Example F38:

[1505] The synthesis method is similar to that of F24, yellow solid, yield 67%. Mass spectrum: m / z 1294.18, elemental analysis experimental values: C, 58.44; H, 2.02; F, 35.21; N, 4.33

[1506] Synthesis Example F39:

[1507] The synthesis method is similar to that of F24, yellow solid, yield 78%. Mass spectrum: m / z 1240.49, elemental analysis experimental values: C, 81.27; H, 5.03; F, 9.18; N, 4.51

[1508] Synthesis Example F40:

[1509] The synthesis method is similar to that of F24, yellow solid, yield 70%. Mass spectrum: m / z 1594.72, elemental analysis experimental values: C, 83.54; H, 5.81; F, 7.14; N, 3.51

[1510] Synthesis Example F41:

[1511] The synthesis method is similar to that of F24, yellow solid, yield 75%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1512] Synthesis Example F42:

[1513] The synthesis method is similar to that of F24, yellow solid, yield 80%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1514] Synthesis Example F43:

[1515] The synthesis method is similar to that of F24, yellow solid, yield 82%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1516] Synthesis Example F44:

[1517] The synthesis method is similar to that of F24, yellow solid, yield 79%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; F, 12.81; N, 11.02

[1518] Synthesis Example F45:

[1519] The synthesis method is similar to that of F24, yellow solid, yield 79%. Mass spectrum: m / z 934.24, elemental analysis experimental values: C, 73.23; H, 3.45; F, 12.19; N, 5.99; O, 5.13

[1520] Synthesis Example F46:

[1521] The synthesis method is similar to that of F24, yellow solid, yield 75%. Mass spectrum: m / z 982.17, elemental analysis experimental values: C, 69.64; H, 3.28; F, 11.60; N, 5.70; S, 9.78

[1522] Synthesis Example F47:

[1523] Intermediate 43 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F47 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1524] Synthesis Example F52:

[1525] The synthesis method is similar to that of F47, yellow solid, yield 70%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1526] Synthesis Example F53:

[1527] The synthesis method is similar to that of F47, yellow solid, yield 74%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1528] Synthesis Example F54:

[1529] The synthesis method is similar to that of F47, yellow solid, yield 75%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1530] Synthesis Example F55:

[1531] The synthesis method is similar to that of F47, yellow solid, yield 73%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1532] Synthesis Example F58:

[1533] The synthesis method is similar to that of F47, yellow solid, yield 69%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1534] Synthesis Example F59:

[1535] The synthesis method is similar to that of F47, yellow solid, yield 69%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1536] Synthesis Example F60:

[1537] The synthesis method is similar to that of F47, yellow solid, yield 78%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[1538] Synthesis Example F61:

[1539] The synthesis method is similar to that of F47, yellow solid, yield 74%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[1540] Synthesis Example F70:

[1541] Intermediate 44 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound F70 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1542] Synthesis Example F75:

[1543] The synthesis method is similar to that of F70, yellow solid, yield 73%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1544] Synthesis Example F73:

[1545] The synthesis method is similar to that of F70, yellow solid, yield 70%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1546] Synthesis Example F77:

[1547] The synthesis method is similar to that of F70, yellow solid, yield 68%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1548] Synthesis Example F78:

[1549] The synthesis method is similar to that of F70, yellow solid, yield 66%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1550] Synthesis Example F81:

[1551] The synthesis method is similar to that of F70, yellow solid, yield 77%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1552] Synthesis Example F82:

[1553] The synthesis method is similar to that of F70, yellow solid, yield 77%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1554] Synthesis Example F83:

[1555] The synthesis method is similar to that of F70, yellow solid, yield 74%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; F, 10.94; N, 3.58; O, 4.09.

[1556] Synthesis Example F84:

[1557] The synthesis method is similar to that of F70, yellow solid, yield 71%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; F, 19.35; N, 3.17; O, 3.62.

[1558] Synthesis Example F93:

[1559] Intermediate 45 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F93 as a yellow solid with a yield of 85%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1560] Synthesis Example F94:

[1561] The synthesis method is similar to that of F93, yellow solid, yield 71%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1562] Synthesis Example F95:

[1563] The synthesis method is similar to that of F93, yellow solid, yield 70%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1564] Synthesis Example F96:

[1565] The synthesis method is similar to that of F93, yellow solid, yield 59%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1566] Synthesis Example F97:

[1567] The synthesis method is similar to that of F93, yellow solid, yield 58%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1568] Synthesis Example F98:

[1569] The synthesis method is similar to that of F93, yellow solid, yield 55%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54

[1570] Synthesis Example F99:

[1571] The synthesis method is similar to that of F93, yellow solid, yield 59%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1572] Synthesis Example F100:

[1573] The synthesis method is similar to that of F93, yellow solid, yield 61%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1574] Synthesis Example F101:

[1575] The synthesis method is similar to that of F93, yellow solid, yield 63%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1576] Synthesis Example F102:

[1577] The synthesis method is similar to that of F93, yellow solid, yield 73%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1578] Synthesis Example F103:

[1579] The synthesis method is similar to that of F93, yellow solid, yield 72%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1580] Synthesis Example F104:

[1581] The synthesis method is similar to that of F93, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1582] Synthesis Example F105:

[1583] The synthesis method is similar to that of F93, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1584] Synthesis Example F106:

[1585] The synthesis method is similar to that of F93, yellow solid, yield 74%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1586] Synthesis Example F107:

[1587] The synthesis method is similar to that of F93, yellow solid, yield 69%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1588] Synthesis Example F108:

[1589] The synthesis method is similar to that of F93, yellow solid, yield 55%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1590] Synthesis Example F109:

[1591] The synthesis method is similar to that of F93, yellow solid, yield 80%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1592] Synthesis Example F110:

[1593] The synthesis method is similar to that of F93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1594] Synthesis Example F111:

[1595] The synthesis method is similar to that of F93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1596] Synthesis Example F112:

[1597] The synthesis method is similar to that of F93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1598] Synthesis Example F113:

[1599] The synthesis method is similar to that of F93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1600] Synthesis Example F114:

[1601] The synthesis method is similar to that of F93, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1602] Synthesis Example F115:

[1603] The synthesis method is similar to that of F93, yellow solid, yield 72%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1604] Synthesis Example F116:

[1605] Intermediate 46 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F116 as a yellow solid with a yield of 83%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1606] Synthesis Example F117:

[1607] The synthesis method is similar to that of F116, yellow solid, yield 77%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1608] Synthesis Example F118:

[1609] The synthesis method is similar to that of F116, yellow solid, yield 75%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1610] Synthesis Example F119:

[1611] The synthesis method is similar to that of F116, yellow solid, yield 78%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1612] Synthesis Example F120:

[1613] The synthesis method is similar to that of F116, yellow solid, yield 60%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1614] Synthesis Example F121:

[1615] The synthesis method is similar to that of F116, yellow solid, yield 59%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1616] Synthesis Example F122:

[1617] The synthesis method is similar to that of F116, yellow solid, yield 55%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1618] Synthesis Example F123:

[1619] The synthesis method is similar to that of F116, yellow solid, yield 80%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1620] Synthesis Example F124:

[1621] The synthesis method is similar to that of F116, yellow solid, yield 81%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1622] Synthesis Example F125:

[1623] The synthesis method is similar to that of F116, yellow solid, yield 83%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1624] Synthesis Example F126:

[1625] The synthesis method is similar to that of F116, yellow solid, yield 88%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1626] Synthesis Example F127:

[1627] The synthesis method is similar to that of F116, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1628] Synthesis Example F128:

[1629] The synthesis method is similar to that of F116, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1630] Synthesis Example F129:

[1631] The synthesis method is similar to that of F116, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1632] Synthesis Example F130:

[1633] The synthesis method is similar to that of F116, yellow solid, yield 75%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1634] Synthesis Example F131:

[1635] The synthesis method is similar to that of F116, yellow solid, yield 67%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1636] Synthesis Example F132:

[1637] The synthesis method is similar to that of F116, yellow solid, yield 53%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1638] Synthesis Example F133:

[1639] The synthesis method is similar to that of F116, yellow solid, yield 70%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1640] Synthesis Example F134:

[1641] The synthesis method is similar to that of F116, yellow solid, yield 80%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1642] Synthesis Example F135:

[1643] The synthesis method is similar to that of F116, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1644] Synthesis Example F136:

[1645] The synthesis method is similar to that of F116, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1646] Synthesis Example F137:

[1647] The synthesis method is similar to that of F116, yellow solid, yield 71%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1648] Synthesis Example F138:

[1649] The synthesis method is similar to that of F116, yellow solid, yield 71%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1650] Synthesis Example F139:

[1651] Intermediate 47 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F139 as a yellow solid with a yield of 73%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1652] Synthesis Example F140:

[1653] The synthesis method is similar to that of F139, yellow solid, yield 74%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1654] Synthesis Example F141:

[1655] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1656] Synthesis Example F142:

[1657] The synthesis method is similar to that of F139, yellow solid, yield 75%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1658] Synthesis Example F143:

[1659] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1660] Synthesis Example F144:

[1661] The synthesis method is similar to that of F139, yellow solid, yield 88%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1662] Synthesis Example F145:

[1663] The synthesis method is similar to that of F139, yellow solid, yield 80%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1664] Synthesis Example F146:

[1665] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1666] Synthesis Example F147:

[1667] The synthesis method is similar to that of F139, yellow solid, yield 83%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1668] Synthesis Example F148:

[1669] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1670] Synthesis Example F149:

[1671] The synthesis method is similar to that of F139, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1672] Synthesis Example F150:

[1673] The synthesis method is similar to that of F139, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1674] Synthesis Example F151:

[1675] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1676] Synthesis Example F152:

[1677] The synthesis method is similar to that of F139, yellow solid, yield 75%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1678] Synthesis Example F153:

[1679] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1680] Synthesis Example F154:

[1681] The synthesis method is similar to that of F139, yellow solid, yield 69%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1682] Synthesis Example F155:

[1683] The synthesis method is similar to that of F139, yellow solid, yield 79%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1684] Synthesis Example F156:

[1685] The synthesis method is similar to that of F139, yellow solid, yield 58%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1686] Synthesis Example F157:

[1687] The synthesis method is similar to that of F139, yellow solid, yield 83%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1688] Synthesis Example F158:

[1689] The synthesis method is similar to that of F139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1690] Synthesis Example F159:

[1691] The synthesis method is similar to that of F139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1692] Synthesis Example F160:

[1693] The synthesis method is similar to that of F139, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1694] Synthesis Example F161:

[1695] The synthesis method is similar to that of F139, yellow solid, yield 59%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1696] Synthesis Example F162:

[1697] Intermediate 48 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound F162 as a yellow solid with a yield of 76%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1698] Synthesis Example F163:

[1699] The synthesis method is similar to that of F162, yellow solid, yield 75%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1700] Synthesis Example F164:

[1701] The synthesis method is similar to that of F162, yellow solid, yield 74%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1702] Synthesis Example F165:

[1703] The synthesis method is similar to that of F162, yellow solid, yield 73%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1704] Synthesis Example F166:

[1705] The synthesis method is similar to that of F162, yellow solid, yield 71%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1706] Synthesis Example F167:

[1707] The synthesis method is similar to that of F162, yellow solid, yield 70%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1708] Synthesis Example F168:

[1709] The synthesis method is similar to that of F162, yellow solid, yield 70%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1710] Synthesis Example F169:

[1711] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1712] Synthesis Example F170:

[1713] The synthesis method is similar to that of F162, yellow solid, yield 70%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1714] Synthesis Example F171:

[1715] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1716] Synthesis Example F172:

[1717] The synthesis method is similar to that of F162, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1718] Synthesis Example F173:

[1719] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1720] Synthesis Example F174:

[1721] The synthesis method is similar to that of F162, yellow solid, yield 75%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1722] Synthesis Example F175:

[1723] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; F, 14.36; N, 4.70; O, 5.37.

[1724] Synthesis Example F176:

[1725] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; F, 24.51; N, 4.02; O, 4.59.

[1726] Synthesis Example F177:

[1727] The synthesis method is similar to that of F162, yellow solid, yield 58%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1728] Synthesis Example F178:

[1729] The synthesis method is similar to that of F162, yellow solid, yield 67%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1730] Synthesis Example F179:

[1731] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1732] Synthesis Example F180:

[1733] The synthesis method is similar to that of F162, yellow solid, yield 59%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1734] Synthesis Example F181:

[1735] The synthesis method is similar to that of F162, yellow solid, yield 76%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1736] Synthesis Example F182:

[1737] The synthesis method is similar to that of F162, yellow solid, yield 82%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1738] Synthesis Example F183:

[1739] The synthesis method is similar to that of F162, yellow solid, yield 73%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1740] Synthesis Example F184:

[1741] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1742] Synthesis of intermediate 49:

[1743]

[1744] 2,3-Dibromo-4,5,6-trifluorobenzonitrile (10 g, 39.37 mmol), 4-cyanophenylboronic acid (13.27 g, 69.87 mmol) were dissolved in 150 mL of toluene, tetrakistriphenylphosphine palladium (1.83 g, 1.59 mmol) and 20 mL of potassium carbonate aqueous solution (8.78 g, 63.51 mmol) were added, and heated to reflux for 24 h. After cooling, the mixture was separated, extracted, dried, and column chromatography (petroleum ether: dichloromethane = 3:1) was performed to obtain a white solid intermediate 49, weighing 6.6 g, with a yield of 58%.

[1745] Synthesis of intermediates 50-56:

[1746]

[1747] The synthesis method is similar to that of intermediate 49. Intermediates 50-56 are all white solids with yields of 60%, 71%, 68%, 59%, 74%, 69%, and 66%, respectively.

[1748] Synthesis Example G1:

[1749] Intermediate 49 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h, cooled and poured into cold water, pH was adjusted to neutral with dilute hydrochloric acid, precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G1 as a yellow solid with a yield of 76%. Mass spectrum: m / z 800.93, elemental analysis experimental values: C, 85.48; H, 4.03; N, 10.49.

[1750] Synthesis Example G2:

[1751] The synthesis method is similar to that of G1, yellow solid, yield 79%. Mass spectrum: m / z 842.32, elemental analysis experimental values: C, 85.49; H, 4.54; N, 9.97.

[1752] Synthesis Example G3:

[1753] The synthesis method is similar to that of G1, yellow solid, yield 70%. Mass spectrum: m / z 884.36, elemental analysis experimental values: C, 85.49; H, 5.01; N, 9.50.

[1754] Synthesis Example G4:

[1755] The synthesis method is similar to that of G1, yellow solid, yield 72%. Mass spectrum: m / z 926.41, elemental analysis experimental values: C, 85.50; H, 5.44; N, 9.06.

[1756] Synthesis Example G5:

[1757] The synthesis method is similar to that of G1, yellow solid, yield 71%. Mass spectrum: m / z 1052.55, elemental analysis experimental values: C, 85.52; H, 6.51; N, 7.98.

[1758] Synthesis Example G6:

[1759] The synthesis method is similar to that of G1, yellow solid, yield 78%. Mass spectrum: m / z 968.46, elemental analysis experimental values: C, 85.51; H, 5.82; N, 8.67.

[1760] Synthesis Example G7:

[1761] The synthesis method is similar to that of G1, yellow solid, yield 79%. Mass spectrum: m / z 1136.64, elemental analysis experimental values: C, 85.52; H, 7.09; N, 7.39.

[1762] Synthesis Example G8:

[1763] The synthesis method is similar to that of G1, yellow solid, yield 78%. Mass spectrum: m / z 1016.39, elemental analysis experimental values: C, 77.91; H, 5.55; N, 8.26; Si, 8.28.

[1764] Synthesis Example G9:

[1765] The synthesis method is similar to that of G1, yellow solid, yield 79%. Mass spectrum: m / z 1218.49, elemental analysis experimental values: C, 72.85; H, 6.44; N, 6.89; Si, 13.81.

[1766] Synthesis Example G10:

[1767] The synthesis method is similar to that of G1, yellow solid, yield 70%. Mass spectrum: m / z 875.25, elemental analysis experimental values: C, 82.27; H, 3.34; N, 14.39.

[1768] Synthesis Example G11:

[1769] The synthesis method is similar to that of G1, yellow solid, yield 73%. Mass spectrum: m / z 950.24, elemental analysis experimental values: C, 79.57; H, 2.76; N, 17.67.

[1770] Synthesis Example G12:

[1771] The synthesis method is similar to that of G1, yellow solid, yield 76%. Mass spectrum: m / z 1028.36, elemental analysis experimental values: C, 87.53; H, 4.31; N, 8.17.

[1772] Synthesis Example G13:

[1773] The synthesis method is similar to G1, yellow solid, yield 79%. Mass spectrum: m / z 1256.46, elemental analysis experimental values: C, 88.83; H, 4.49; N, 6.68.

[1774] Synthesis Example G14:

[1775] The synthesis method is similar to that of G1, yellow solid, yield 69%. Mass spectrum: m / z 1004.23, elemental analysis experimental values: C, 71.71; H, 2.91; G, 17.01; N, 8.36.

[1776] Synthesis Example G15:

[1777] The synthesis method is similar to that of G1, yellow solid, yield 80%. Mass spectrum: m / z 1208.19, elemental analysis experimental values: C, 62.59; H, 2.17; G, 28.29; N, 6.95.

[1778] Synthesis Example G16:

[1779] The synthesis method is similar to that of G1, yellow solid, yield 75%. Mass spectrum: m / z 1154.50, elemental analysis experimental values: C, 87.32; H, 5.41; N, 7.27.

[1780] Synthesis Example G17:

[1781] The synthesis method is similar to G1, yellow solid, yield 75%. Mass spectrum: m / z 1508.74, elemental analysis experimental values: C, 88.29; H, 6.14; N, 5.57.

[1782] Synthesis Example G18:

[1783] The synthesis method is similar to that of G1, yellow solid, yield 79%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1784] Synthesis Example G19:

[1785] The synthesis method is similar to that of G1, yellow solid, yield 70%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1786] Synthesis Example G20:

[1787] The synthesis method is similar to that of G1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1788] Synthesis Example G21:

[1789] The synthesis method is similar to that of G1, yellow solid, yield 69%. Mass spectrum: m / z 803.25, elemental analysis experimental values: C, 80.68; H, 3.64; N, 15.68.

[1790] Synthesis Example G22:

[1791] The synthesis method is similar to that of G1, yellow solid, yield 81%. Mass spectrum: m / z 848.25, elemental analysis experimental values: C, 80.65; H, 3.80; N, 9.90; O, 5.65.

[1792] Synthesis Example G23:

[1793] The synthesis method is similar to that of G1, yellow solid, yield 70%. Mass spectrum: m / z 896.19, elemental analysis experimental values: C, 76.32; H, 3.60; N, 9.37; S, 10.72.

[1794] Synthesis Example G24:

[1795] Intermediate 50 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G24 as a yellow solid with a yield of 83%. Mass spectrum: m / z 886.25, elemental analysis experimental values: C, 77.19; H, 3.64; G, 12.85; N, 6.32.

[1796] Synthesis Example G25:

[1797] The synthesis method is similar to that of G24, yellow solid, yield 70%. Mass spectrum: m / z 928.30, elemental analysis experimental values: C, 77.58; H, 4.12; G, 12.27; N, 6.03

[1798] Synthesis Example G26:

[1799] The synthesis method is similar to that of G24, yellow solid, yield 71%. Mass spectrum: m / z 970.35, elemental analysis experimental values: C, 77.92; H, 4.57; G, 11.74; N, 5.77

[1800] Synthesis Example G27:

[1801] The synthesis method is similar to that of G24, yellow solid, yield 73%. Mass spectrum: m / z 1012.39, elemental analysis experimental values: C, 78.24; H, 4.97; G, 11.25; N, 5.53

[1802] Synthesis Example G28:

[1803] The synthesis method is similar to that of G24, yellow solid, yield 69%. Mass spectrum: m / z 1138.53, elemental analysis experimental values: C, 79.06; H, 6.02; G, 10.00; N, 4.92

[1804] Synthesis Example G29:

[1805] The synthesis method is similar to that of G24, yellow solid, yield 67%. Mass spectrum: m / z 1054.44, elemental analysis experimental values: C, 78.54; H, 5.35; G, 10.80; N, 5.31

[1806] Synthesis Example G30:

[1807] The synthesis method is similar to that of G24, yellow solid, yield 66%. Mass spectrum: m / z 1222.63, elemental analysis experimental values: C, 79.51; H, 6.59; G, 9.32; N, 4.58

[1808] Synthesis Example G31:

[1809] The synthesis method is similar to that of G24, yellow solid, yield 80%. Mass spectrum: m / z 1102.37, elemental analysis experimental values: C, 71.84; H, 5.12; G, 10.33; N, 5.08; Si, 7.64

[1810] Synthesis Example G32:

[1811] The synthesis method is similar to that of G24, yellow solid, yield 73%. Mass spectrum: m / z 1304.47, elemental analysis experimental values: C, 68.06; H, 6.02; G, 8.73; N, 4.29; Si, 12.90

[1812] Synthesis Example G33:

[1813] The synthesis method is similar to that of G24, yellow solid, yield 72%. Mass spectrum: m / z 961.24, elemental analysis experimental values: C, 74.92; H, 3.04; G, 11.85; N, 10.19

[1814] Synthesis Example G34:

[1815] The synthesis method is similar to that of G24, yellow solid, yield 71%. Mass spectrum: m / z 1036.22, elemental analysis experimental values: C, 72.97; H, 2.53; G, 10.99; N, 13.51

[1816] Synthesis Example G35:

[1817] The synthesis method is similar to that of G24, yellow solid, yield 69%. Mass spectrum: m / z 1114.35, elemental analysis experimental values: C, 80.78; H, 3.98; G, 10.22; N, 5.02

[1818] Synthesis Example G36:

[1819] The synthesis method is similar to that of G24, yellow solid, yield 59%. Mass spectrum: m / z 1342.44, elemental analysis experimental values: C, 83.14; H, 4.20; G, 8.48; N, 4.17

[1820] Synthesis Example G37:

[1821] The synthesis method is similar to that of G24, yellow solid, yield 58%. Mass spectrum: m / z 1090.22, elemental analysis experimental values: C, 66.06; H, 2.68; G, 26.12; N, 5.14

[1822] Synthesis Example G38:

[1823] The synthesis method is similar to that of G24, yellow solid, yield 67%. Mass spectrum: m / z 1294.18, elemental analysis experimental values: C, 58.44; H, 2.02; G, 35.21; N, 4.33

[1824] Synthesis Example G39:

[1825] The synthesis method is similar to that of G24, yellow solid, yield 78%. Mass spectrum: m / z 1240.49, elemental analysis experimental values: C, 81.27; H, 5.03; G, 9.18; N, 4.51

[1826] Synthesis Example G40:

[1827] The synthesis method is similar to that of G24, yellow solid, yield 70%. Mass spectrum: m / z 1594.72, elemental analysis experimental values: C, 83.54; H, 5.81; G, 7.14; N, 3.51

[1828] Synthesis Example G41:

[1829] The synthesis method is similar to that of G24, yellow solid, yield 75%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; G, 12.81; N, 11.02

[1830] Synthesis Example G42:

[1831] The synthesis method is similar to that of G24, yellow solid, yield 80%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; G, 12.81; N, 11.02

[1832] Synthesis Example G43:

[1833] The synthesis method is similar to that of G24, yellow solid, yield 82%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; G, 12.81; N, 11.02

[1834] Synthesis Example G44:

[1835] The synthesis method is similar to that of G24, yellow solid, yield 79%. Mass spectrum: m / z 889.24, elemental analysis experimental values: C, 72.89; H, 3.28; G, 12.81; N, 11.02

[1836] Synthesis Example G45:

[1837] The synthesis method is similar to that of G24, yellow solid, yield 79%. Mass spectrum: m / z 934.24, elemental analysis experimental values: C, 73.23; H, 3.45; G, 12.19; N, 5.99; O, 5.13

[1838] Synthesis Example G46:

[1839] The synthesis method is similar to that of G24, yellow solid, yield 75%. Mass spectrum: m / z 982.17, elemental analysis experimental values: C, 69.64; H, 3.28; G, 11.60; N, 5.70; S, 9.78

[1840] Synthesis Example G47:

[1841] Intermediate 51 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G47 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1842] Synthesis Example G52:

[1843] The synthesis method is similar to that of G47, yellow solid, yield 70%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1844] Synthesis Example G53:

[1845] The synthesis method is similar to that of G47, yellow solid, yield 74%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1846] Synthesis Example G54:

[1847] The synthesis method is similar to that of G47, yellow solid, yield 75%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1848] Synthesis Example G55:

[1849] The synthesis method is similar to that of G47, yellow solid, yield 73%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1850] Synthesis Example G58:

[1851] The synthesis method is similar to that of G47, yellow solid, yield 69%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1852] Synthesis Example G59:

[1853] The synthesis method is similar to that of G47, yellow solid, yield 69%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1854] Synthesis Example G60:

[1855] The synthesis method is similar to that of G47, yellow solid, yield 78%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; G, 10.94; N, 3.58; O, 4.09.

[1856] Synthesis Example G61:

[1857] The synthesis method is similar to that of G47, yellow solid, yield 74%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; G, 19.35; N, 3.17; O, 3.62.

[1858] Synthesis Example G70:

[1859] Intermediate 52 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G70 as a yellow solid with a yield of 83%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1860] Synthesis Example G75:

[1861] The synthesis method is similar to that of G70, yellow solid, yield 73%. Mass spectrum: m / z 1526.79, elemental analysis experimental values: C, 84.13; H, 6.60; B, 1.42; N, 3.67; O, 4.19.

[1862] Synthesis Example G73:

[1863] The synthesis method is similar to that of G70, yellow solid, yield 70%. Mass spectrum: m / z 1694.98, elemental analysis experimental values: C, 84.28; H, 7.37; B, 1.27; N, 3.30; O, 3.77.

[1864] Synthesis Example G77:

[1865] The synthesis method is similar to that of G70, yellow solid, yield 68%. Mass spectrum: m / z 1574.72, elemental analysis experimental values: C, 79.27; H, 6.40; B, 1.37; N, 3.56; O, 4.06; Si, 5.35.

[1866] Synthesis Example G78:

[1867] The synthesis method is similar to that of G70, yellow solid, yield 66%. Mass spectrum: m / z 1790.84, elemental analysis experimental values: C, 75.72; H, 6.97; B, 1.21; N, 3.13; O, 3.57; Si, 9.40.

[1868] Synthesis Example G81:

[1869] The synthesis method is similar to that of G70, yellow solid, yield 77%. Mass spectrum: m / z 1586.70, elemental analysis experimental values: C, 85.49; H, 5.59; B, 1.36; N, 3.53; O, 4.03.

[1870] Synthesis Example G82:

[1871] The synthesis method is similar to that of G70, yellow solid, yield 77%. Mass spectrum: m / z 1814.79, elemental analysis experimental values: C, 86.65; H, 5.55; B, 1.19; N, 3.09; O, 3.52.

[1872] Synthesis Example G83:

[1873] The synthesis method is similar to that of G70, yellow solid, yield 74%. Mass spectrum: m / z 1562.57, elemental analysis experimental values: C, 75.29; H, 4.71; B, 1.38; G, 10.94; N, 3.58; O, 4.09.

[1874] Synthesis Example G84:

[1875] The synthesis method is similar to that of G70, yellow solid, yield 71%. Mass spectrum: m / z 1766.53, elemental analysis experimental values: C, 68.64; H, 3.99; B, 1.22; G, 19.35; N, 3.17; O, 3.62.

[1876] Synthesis Example G93:

[1877] Intermediate 53 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G93 as a yellow solid with a yield of 85%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1878] Synthesis Example G94:

[1879] The synthesis method is similar to that of G93, yellow solid, yield 71%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1880] Synthesis Example G95:

[1881] The synthesis method is similar to that of G93, yellow solid, yield 70%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1882] Synthesis Example G96:

[1883] The synthesis method is similar to that of G93, yellow solid, yield 59%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1884] Synthesis Example G97:

[1885] The synthesis method is similar to that of G93, yellow solid, yield 58%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1886] Synthesis Example G98:

[1887] The synthesis method is similar to that of G93, yellow solid, yield 55%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54

[1888] Synthesis Example G99:

[1889] The synthesis method is similar to that of G93, yellow solid, yield 59%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1890] Synthesis Example G100:

[1891] The synthesis method is similar to that of G93, yellow solid, yield 61%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1892] Synthesis Example G101:

[1893] The synthesis method is similar to that of G93, yellow solid, yield 63%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1894] Synthesis Example G102:

[1895] The synthesis method is similar to that of G93, yellow solid, yield 73%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1896] Synthesis Example G103:

[1897] The synthesis method is similar to that of G93, yellow solid, yield 72%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1898] Synthesis Example G104:

[1899] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1900] Synthesis Example G105:

[1901] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1902] Synthesis Example G106:

[1903] The synthesis method is similar to that of G93, yellow solid, yield 74%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; G, 14.36; N, 4.70; O, 5.37.

[1904] Synthesis Example G107:

[1905] The synthesis method is similar to that of G93, yellow solid, yield 69%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; G, 24.51; N, 4.02; O, 4.59.

[1906] Synthesis Example G108:

[1907] The synthesis method is similar to that of G93, yellow solid, yield 55%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1908] Synthesis Example G109:

[1909] The synthesis method is similar to that of G93, yellow solid, yield 80%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1910] Synthesis Example G110:

[1911] The synthesis method is similar to that of G93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1912] Synthesis Example G111:

[1913] The synthesis method is similar to that of G93, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1914] Synthesis Example G112:

[1915] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1916] Synthesis Example G113:

[1917] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1918] Synthesis Example G114:

[1919] The synthesis method is similar to that of G93, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1920] Synthesis Example G115:

[1921] The synthesis method is similar to that of G93, yellow solid, yield 72%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1922] Synthesis Example G116:

[1923] Intermediate 54 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G116 as a yellow solid with a yield of 83%. Mass spectrum: m / z 986.29, elemental analysis experimental values: C, 83.96; H, 3.88; N, 5.68; O, 6.48.

[1924] Synthesis Example G117:

[1925] The synthesis method is similar to that of G116, yellow solid, yield 77%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1926] Synthesis Example G118:

[1927] The synthesis method is similar to that of G116, yellow solid, yield 75%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1928] Synthesis Example G119:

[1929] The synthesis method is similar to that of G116, yellow solid, yield 78%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1930] Synthesis Example G120:

[1931] The synthesis method is similar to that of G116, yellow solid, yield 60%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1932] Synthesis Example G121:

[1933] The synthesis method is similar to that of G116, yellow solid, yield 59%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1934] Synthesis Example G122:

[1935] The synthesis method is similar to that of G116, yellow solid, yield 55%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1936] Synthesis Example G123:

[1937] The synthesis method is similar to that of G116, yellow solid, yield 80%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1938] Synthesis Example G124:

[1939] The synthesis method is similar to that of G116, yellow solid, yield 81%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1940] Synthesis Example G125:

[1941] The synthesis method is similar to that of G116, yellow solid, yield 83%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1942] Synthesis Example G126:

[1943] The synthesis method is similar to that of G116, yellow solid, yield 88%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1944] Synthesis Example G127:

[1945] The synthesis method is similar to that of G116, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1946] Synthesis Example G128:

[1947] The synthesis method is similar to that of G116, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1948] Synthesis Example G129:

[1949] The synthesis method is similar to that of G116, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; G, 14.36; N, 4.70; O, 5.37.

[1950] Synthesis Example G130:

[1951] The synthesis method is similar to that of G116, yellow solid, yield 75%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; G, 24.51; N, 4.02; O, 4.59.

[1952] Synthesis Example G131:

[1953] The synthesis method is similar to that of G116, yellow solid, yield 67%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[1954] Synthesis Example G132:

[1955] The synthesis method is similar to that of G116, yellow solid, yield 53%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[1956] Synthesis Example G133:

[1957] The synthesis method is similar to that of G116, yellow solid, yield 70%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1958] Synthesis Example G134:

[1959] The synthesis method is similar to that of G116, yellow solid, yield 80%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1960] Synthesis Example G135:

[1961] The synthesis method is similar to that of G116, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1962] Synthesis Example G136:

[1963] The synthesis method is similar to that of G116, yellow solid, yield 75%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[1964] Synthesis Example G137:

[1965] The synthesis method is similar to that of G116, yellow solid, yield 71%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[1966] Synthesis Example G138:

[1967] The synthesis method is similar to that of G116, yellow solid, yield 71%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[1968] Synthesis Example G139:

[1969] Intermediate 55 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography was performed to obtain compound G139 as a yellow solid with a yield of 73%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[1970] Synthesis Example G140:

[1971] The synthesis method is similar to that of G139, yellow solid, yield 74%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[1972] Synthesis Example G141:

[1973] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[1974] Synthesis Example G142:

[1975] The synthesis method is similar to that of G139, yellow solid, yield 75%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[1976] Synthesis Example G143:

[1977] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[1978] Synthesis Example G144:

[1979] The synthesis method is similar to that of G139, yellow solid, yield 88%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[1980] Synthesis Example G145:

[1981] The synthesis method is similar to that of G139, yellow solid, yield 80%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[1982] Synthesis Example G146:

[1983] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[1984] Synthesis Example G147:

[1985] The synthesis method is similar to that of G139, yellow solid, yield 83%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[1986] Synthesis Example G148:

[1987] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[1988] Synthesis Example G149:

[1989] The synthesis method is similar to that of G139, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[1990] Synthesis Example G150:

[1991] The synthesis method is similar to that of G139, yellow solid, yield 73%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[1992] Synthesis Example G151:

[1993] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[1994] Synthesis Example G152:

[1995] The synthesis method is similar to that of G139, yellow solid, yield 75%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; G, 14.36; N, 4.70; O, 5.37.

[1996] Synthesis Example G153:

[1997] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; G, 24.51; N, 4.02; O, 4.59.

[1998] Synthesis Example G154:

[1999] The synthesis method is similar to that of G139, yellow solid, yield 69%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[2000] Synthesis Example G155:

[2001] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[2002] Synthesis Example G156:

[2003] The synthesis method is similar to that of G139, yellow solid, yield 58%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2004] Synthesis Example G157:

[2005] The synthesis method is similar to that of G139, yellow solid, yield 83%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2006] Synthesis Example G158:

[2007] The synthesis method is similar to that of G139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2008] Synthesis Example G159:

[2009] The synthesis method is similar to that of G139, yellow solid, yield 72%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2010] Synthesis Example G160:

[2011] The synthesis method is similar to that of G139, yellow solid, yield 74%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[2012] Synthesis Example G161:

[2013] The synthesis method is similar to that of G139, yellow solid, yield 59%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[2014] Synthesis Example G162:

[2015] Intermediate 56 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF, heated to 80°C and stirred for 12 h. After cooling, the reaction system was poured into cold water, the pH was adjusted to neutral with dilute hydrochloric acid, the precipitate was collected by filtration, dried, and column chromatography to obtain compound G162 as a yellow solid with a yield of 76%. Mass spectrum: m / z 1358.61, elemental analysis experimental values: C, 83.94; H, 5.64; B, 1.59; N, 4.12; O, 4.71.

[2016] Synthesis Example G163:

[2017] The synthesis method is similar to that of G162, yellow solid, yield 75%. Mass spectrum: m / z 1028.34, elemental analysis experimental values: C, 84.03; H, 4.31; N, 5.44; O, 6.22.

[2018] Synthesis Example G164:

[2019] The synthesis method is similar to that of G162, yellow solid, yield 74%. Mass spectrum: m / z 1070.38, elemental analysis experimental values: C, 84.09; H, 4.70; N, 5.23; O, 5.97.

[2020] Synthesis Example G165:

[2021] The synthesis method is similar to that of G162, yellow solid, yield 73%. Mass spectrum: m / z 1112.43, elemental analysis experimental values: C, 84.15; H, 5.07; N, 5.03; O, 5.75.

[2022] Synthesis Example G166:

[2023] The synthesis method is similar to that of G162, yellow solid, yield 71%. Mass spectrum: m / z 1238.57, elemental analysis experimental values: C, 84.30; H, 6.02; N, 4.52; O, 5.16.

[2024] Synthesis Example G167:

[2025] The synthesis method is similar to that of G162, yellow solid, yield 70%. Mass spectrum: m / z 1154.48, elemental analysis experimental values: C, 84.20; H, 5.41; N, 4.85; O, 5.54.

[2026] Synthesis Example G168:

[2027] The synthesis method is similar to that of G162, yellow solid, yield 70%. Mass spectrum: m / z 1322.66, elemental analysis experimental values: C, 84.38; H, 6.55; N, 4.23; O, 4.83.

[2028] Synthesis Example G169:

[2029] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1202.41, elemental analysis experimental values: C, 77.84; H, 5.19; N, 4.65; O, 5.32; Si, 7.00.

[2030] Synthesis Example G170:

[2031] The synthesis method is similar to that of G162, yellow solid, yield 70%. Mass spectrum: m / z 1418.53, elemental analysis experimental values: C, 73.58; H, 6.10; N, 3.95; O, 4.51; Si, 11.87.

[2032] Synthesis Example G171:

[2033] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1061.28, elemental analysis experimental values: C, 81.42; H, 3.32; N, 9.23; O, 6.03.

[2034] Synthesis Example G172:

[2035] The synthesis method is similar to that of G162, yellow solid, yield 77%. Mass spectrum: m / z 1136.26, elemental analysis experimental values: C, 79.22; H, 2.84; N, 12.32; O, 5.63.

[2036] Synthesis Example G173:

[2037] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1214.38, elemental analysis experimental values: C, 85.98; H, 4.15; N, 4.61; O, 5.27.

[2038] Synthesis Example G174:

[2039] The synthesis method is similar to that of G162, yellow solid, yield 75%. Mass spectrum: m / z 1442.48, elemental analysis experimental values: C, 87.36; H, 4.33; N, 3.88; O, 4.43.

[2040] Synthesis Example G175:

[2041] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1190.25, elemental analysis experimental values: C, 72.61; H, 2.96; G, 14.36; N, 4.70; O, 5.37.

[2042] Synthesis Example G176:

[2043] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1394.21, elemental analysis experimental values: C, 64.57; H, 2.31; G, 24.51; N, 4.02; O, 4.59.

[2044] Synthesis Example G177:

[2045] The synthesis method is similar to that of G162, yellow solid, yield 58%. Mass spectrum: m / z 1340.52, elemental analysis experimental values: C, 85.94; H, 5.11; N, 4.18; O, 4.77.

[2046] Synthesis Example G178:

[2047] The synthesis method is similar to that of G162, yellow solid, yield 67%. Mass spectrum: m / z 1694.76, elemental analysis experimental values: C, 87.10; H, 5.82; N, 3.30; O, 3.77

[2048] Synthesis Example G179:

[2049] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2050] Synthesis Example G180:

[2051] The synthesis method is similar to that of G162, yellow solid, yield 59%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2052] Synthesis Example G181:

[2053] The synthesis method is similar to that of G162, yellow solid, yield 76%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2054] Synthesis Example G182:

[2055] The synthesis method is similar to that of G162, yellow solid, yield 82%. Mass spectrum: m / z 989.28, elemental analysis experimental values: C, 80.07; H, 3.56; N, 9.90; O, 6.46.

[2056] Synthesis Example G183:

[2057] The synthesis method is similar to that of G162, yellow solid, yield 73%. Mass spectrum: m / z 1034.27, elemental analysis experimental values: C, 80.07; H, 3.70; N, 5.41; O, 10.82.

[2058] Synthesis Example G184:

[2059] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1082.21, elemental analysis experimental values: C, 76.51; H, 3.54; N, 5.17; O, 5.91; S, 8.88.

[2060] The technical effects and advantages of the present invention are demonstrated and verified by applying the compound of the present invention to an organic electroluminescent device to test the actual performance.

[2061] An organic electroluminescent device includes an anode, a cathode, and an organic material layer between the two electrodes. The organic material can be divided into multiple regions, for example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[2062] The material of the anode can be indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof. The material of the cathode can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and other metals or alloys and any combination thereof.

[2063] 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 multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[2064] The material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, 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.

[2065] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[2066] The electron transport region may 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 may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[2067] The organic electroluminescent device preparation process in the embodiment of the present invention is as follows:

[2068] An anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode are sequentially deposited on a substrate, and then packaged. When preparing the organic light-emitting layer, the organic light-emitting layer is formed by co-evaporation of an electron donor material source, an electron acceptor material source, and the TADF material source of the present invention.

[2069] The specific steps include:

[2070] 1. The glass plate coated with the anode material was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[2071] 2. Place the glass plate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, vacuum evaporating a hole injection material on the anode layer to form a hole injection layer at a rate of 0.1-0.5 nm / s;

[2072] 3. Vacuum evaporation of hole transport material on the hole injection layer to form a hole transport layer at a rate of 0.1-0.5nm / s.

[2073] 4. Vacuum-evaporating an organic light-emitting layer of the device on the hole transport layer, wherein the organic light-emitting layer material includes a main material and the compound of the present invention as a dye, and using a multi-source co-evaporation method, adjusting the evaporation rate of the main material and the evaporation rate of the dye so that the dye reaches a preset doping ratio;

[2074] 5. Vacuum-deposit the electron transport material of the device on the organic light-emitting layer to form an electron transport layer, with the evaporation rate being 0.1-0.5 nm / s;

[2075] 6. LiF was vacuum evaporated at 0.1-0.5nm / s on the electron transport layer as the electron injection layer, and Al was vacuum evaporated at 0.5-1nm / s as the cathode of the device.

[2076] The embodiment of the present invention further provides a display device, which includes the organic electroluminescent device provided above. The display device can specifically be a display device such as an OLED display, and any product or component with a display function such as a television, a digital camera, a mobile phone, a tablet computer, etc. that includes the display device. The display device has the same advantages as the above-mentioned organic electroluminescent device over the prior art, which will not be repeated here.

[2077] The organic electroluminescent device of the present invention is further described below through specific embodiments.

[2078] In the following embodiments of the present invention, the OLED includes an anode / hole injection layer / hole transport layer / first exciton blocking layer / light-emitting layer / second exciton blocking layer / electron transport layer / electron injection layer / cathode stacked in sequence. Among them, the anode is ITO; the hole injection layer is HATCN; the hole transport layer is NPB; the first exciton blocking layer is TCTA; the main material of the light-emitting layer is DPEPO, in which the thermally activated delayed fluorescent material of the present invention (any one of A-1 to A-152) is doped as a luminescent dye, and the mass percentage concentration of the doping is 20%; the second exciton blocking layer is DCzPm; the electron transport layer is DPyPA co-evaporated; the electron injection layer is LiF; and the cathode is Al.

[2079]

[2080] The structures of the comparative compounds are:

[2081]

[2082]

[2083] Example 1

[2084] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment to completely remove the water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[2085] HATCN was vacuum-deposited on the ITO transparent conductive layer as the hole injection layer of the device, with a deposition rate of 0.1 nm / s and a total deposition film thickness of 5 nm;

[2086] NPB was vacuum-deposited on the hole injection layer as the hole transport layer of the device, with a deposition rate of 0.1 nm / s and a total deposition film thickness of 30 nm.

[2087] TCTA was vacuum-deposited on the hole transport layer as the first exciton blocking layer at a rate of 0.1 nm / s and a total film thickness of 10 nm.

[2088] The light-emitting layer of the device is vacuum-deposited on the first exciton blocking layer. The light-emitting layer of the present invention includes a main material and a dye material. The main material is DPEPO, and the thermally activated delayed fluorescent material A1 of the present invention is used as the dye material. The evaporation rate of the above main materials is adjusted to 0.1nm / s, and the evaporation rate of the dye in the light-emitting layer is adjusted to 20% of the main evaporation rate. The total film thickness of the light-emitting layer is 30nm;

[2089] DPyPA was vacuum co-evaporated on the light-emitting layer as the electron transport material of the device, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 30 nm;

[2090] LiF with a thickness of 0.5 nm was vacuum evaporated on the electron transport layer as an electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[2091] Examples 2 to 348 are prepared in the same manner as in Example 1, except that the luminescent dye in the luminescent layer is replaced by Compound A-2 to G174 of the present invention from Compound A1 of the present invention. Comparative Examples 1 to 21 are prepared in the same manner as in Example 1, except that the luminescent dye in the luminescent layer is replaced by Compound A-2 to G174 of the present invention from Compound A1 of the present invention from Compound A-2 to G174 of the present invention.

[2092] The performance of the organic electroluminescent devices prepared in the above-mentioned embodiments is shown in Table 1 below.

[2093] Table 1:

[2094]

[2095]

[2096]

[2097]

[2098]

[2099]

[2100]

[2101]

[2102]

[2103] It can be seen from Table 1 that when the compound of the present invention is used as a luminescent dye in the luminescent layer of an organic electroluminescent device, when the brightness is required to be 1000 cd / m 2 When the driving voltage is as low as 4V, the current efficiency is as high as 50cd / A, and the T95 life is greater than 200h.

[2104] The light-emitting layer materials used in Comparative Examples 1-13 and 17 have two cyano groups on the central benzene ring in common, which will cause the electron cloud to be enriched on the central benzene ring, reduce the CN bond dissociation energy between carbazole and the central benzene ring, and lead to poor device life. At the same time, the presence of two cyano groups will cause the molecule's LUMO energy level to be too deep, electron capture will be more serious, and the device efficiency will be low.

[2105] The light-emitting layer material used in Comparative Example 13 has four electron-withdrawing groups, including three benzonitrile groups and one cyano group. This structure causes the LUMO energy level to be greatly deepened, the device voltage is high, and the life span is poor. Comparative Examples 14 and 15 use electron donors and acceptors arranged alternately, the donor is a carbazole group, and the acceptor is a benzonitrile group or an isophthalonitrile group. Such acceptor groups have insufficient electron-withdrawing ability, and the singlet and triplet energy level difference of the molecule is large, making it difficult to maintain the thermally activated delayed fluorescence properties, resulting in significantly low device efficiency. At the same time, unlike the structure in which the central benzene ring is directly connected to the cyano group, the cyano group of this structure is all exposed on the outermost side of the molecule, that is, the LUMO orbit is distributed on the outermost side of the molecule, and it is easy to have an excited state quenching process with other molecules, resulting in a low device life span. Comparative Examples 16 and 17 further reduce the electron-withdrawing groups on the basis of Comparative Examples 14 and 15, retaining two and one benzonitrile groups as electron acceptors, respectively, further increasing the band gap, and the device exhibits extremely high driving voltage and low efficiency.

[2106] Compounds T10 and T13 used in Comparative Examples 20 and 21 are similar to those in Comparative Examples 14 and 15, with benzonitrile or phenyltrifluoromethyl as electron-withdrawing groups, in which cyano and trifluoromethyl are exposed on the outside of the molecule, which are prone to exciton quenching, resulting in a relatively short device life.

[2107] The above results show that the molecular design concept of introducing multiple electron acceptors in the present invention for organic electroluminescent devices can effectively reduce the lighting voltage, improve the current efficiency, and have good stability performance, and is a thermally activated delayed fluorescent dye with good performance.

[2108] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. An organic compound having a structure shown in the following formula (1): In formula (1), D 1 , D 2 , D 3 , D 4 , D 5 Same or different, D 1 , D 2 , D 3 , D 4 , D 5 Each is independently selected from the following structures represented by formula (d2) or formula (d3), or selected from substituted or unsubstituted C3-C60 heteroaryl groups; The D 1 , D 2 , D 3 , D 4 , D 5 There is a structure selected from formula (d2) or formula (d3), and D 1 , D 2 , D 3 , D 4 , D 5 Four of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; Alternatively, the D 1 , D 2 , D 3 , D 4 , D 5 There are two structures independently selected from formula (d2) or formula (d3), and D 1 , D 2 , D 3 , D 4 , D 5 Three of them are independently selected from substituted or unsubstituted C3-C60 heteroaryl; When there is a substituent on the above heteroaryl group, the substituent is selected from one or a combination of two of cyano, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, nitro, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl; 2. The organic compound according to claim 1, characterized in that When D 1 , D 2 , D 3 , D 4 , D 5 When they are independently selected from substituted or unsubstituted C3-C60 heteroaryl, they are selected from one of the following substituted or unsubstituted structural formulas: When there are substituents in the above structural formula, the substituents are selected from one or a combination of two of deuterium, cyano, halogen, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl.

3. The organic compound according to claim 1, characterized in that When D 1 , D 2 , D 3 , D 4 , D 5 When they are independently selected from substituted or unsubstituted C3-C60 heteroaryl, they are selected from one of the following substituted or unsubstituted structural formulas: When there is a substituent in the above structural formula, the substituent is selected from one of deuterium, C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.

4. An organic compound selected from the following structures:

5. Use of the compound according to any one of claims 1 to 4, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device comprises: Organic electroluminescent device, optical sensor, solar cell, lighting element, organic thin film transistor, organic field effect transistor, organic thin film solar cell, information tag, electronic artificial skin sheet, sheet-type scanner or electronic paper; The said material is used as a light-emitting layer material in an organic electroluminescent device, specifically as a light-emitting dye of the light-emitting layer.

6. 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 layer contains the compound according to any one of claims 1 to 4.

7. The organic electroluminescent device according to claim 6, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is formed on the anode layer, and the cathode layer is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region, and the light-emitting layer contains the compound described in any one of claims 1 to 4.

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