CN115745869A - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- CN115745869A CN115745869A CN202211369364.8A CN202211369364A CN115745869A CN 115745869 A CN115745869 A CN 115745869A CN 202211369364 A CN202211369364 A CN 202211369364A CN 115745869 A CN115745869 A CN 115745869A
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- yellow solid
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- 229910052805 deuterium Inorganic materials 0.000 claims description 11
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- 125000001769 aryl amino group Chemical group 0.000 claims description 8
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C—CHEMISTRY; METALLURGY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound, application thereof and an organic electroluminescent device containing the compound, and specifically relates to a novel thermal activation delayed fluorescent material, which has a structure as shown in the following formula (1):
D 1 、D 2 、D 3 、D 4 、D 5 the same or different, each independently selected from the structures shown in formula (d 1), formula (d 2), formula (d 3) and formula (d 4) or selected from substituted or unsubstituted C3-C60 heteroaryl. When the compound is used as a light-emitting layer material in an OLED device, the compound has higher photoluminescence quantum efficiency and faster reverse intersystem crossing rate, and can show excellent device efficiency and device service life. The invention also protects an organic electroluminescent device adopting the organic compound.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound, application thereof and an organic electroluminescent device containing the compound, and specifically relates to a thermal activation delayed fluorescent material.
Background
Organic Light Emission Diodes (OLED) are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and migrating and meeting the positive and negative charges in the organic layer under the action of an electric field to realize composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, so that the technology is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
Disclosure of Invention
In order to solve the technical problem, the invention provides an organic compound which can be applied to the field of organic electroluminescence.
The organic compound of the present invention has a structure represented by the following formula (1):
in the formula (1), D 1 、D 2 、D 3 、D 4 、D 5 Identical or different, D 1 、D 2 、D 3 、D 4 、D 5 Each independently selected from the following structures as shown in formula (d 1), formula (d 2), formula (d 3) or formula (d 4), or selected from substituted or unsubstituted C3-C60 heteroaryl; and D 1 、D 2 、D 3 、D 4 、D 5 At least one is selected from the structures shown in one of formulas (d 1) to (d 4), and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl;
when a substituent is present 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;
in the formula (d 1), each R is the same or different, 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 alkyl silicon group, and each R is not hydrogen at the same time;
in the formula (d 4), each R 1 Identical or different, R 1 Each independently selected from one of hydrogen, deuterium, cyano, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and heteroaryl of C5-C60.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb represents that the group has a carbon number of a to b, and generally the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure means that the linking site is located at an arbitrary position on the loop structure capable of forming a bond.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present invention, unless otherwise specified, the expression of a chemical element generally includes the concept of its isotope, for example, the expression "hydrogen (H)" includes the concept of its isotope 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be described in detail.
The hetero atom in the present invention generally means an atom or an atomic group selected from N, O, S, P, si and Se, and preferably selected from N, O and S.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, both aryl and heteroaryl groups include monocyclic and fused rings unless otherwise specified.
In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, as exemplified by: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group 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. The fused ring aryl group means a group having at least two aromatic rings in a molecule, and the aromatic rings are not independent of each other but are fused to each other with two adjacent carbon atoms in common. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,
And mesitylene, and derivatives thereof. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and9-fluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9' -spirobifluorene and benzofluorenyl.
The C3 to C60 heteroaryl group mentioned in the present invention includes monocyclic heteroaryl and fused heteroaryl, preferably C3 to C30 heteroaryl, more preferably C4 to C20 heteroaryl, and still more preferably C5 to C12 heteroaryl. The monocyclic heteroaryl group means that at least one heteroaryl group is contained in the molecule, and when one heteroaryl group and another group (for example, aryl group, heteroaryl group, alkyl group, etc.) are contained in the molecule, the heteroaryl group and the other group are independently connected by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl and the like. The fused ring heteroaryl group means a group which has at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in a molecule, and which are not independent of each other but share two adjacent atoms fused with each other. Examples of fused heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
In the present invention, the aryloxy group includes a monovalent group composed of the above-mentioned aryl group, heteroaryl group and oxygen.
In the present invention, arylamino represents a group formed by substituting one or two aryl groups for hydrogen on an amino group, wherein the linking site of the arylamino group may be linked to an aryl group in the arylamino group or to N in the arylamino group, and exemplary carbon numbers and specific groups of the aryl group in the arylamino group are the same as described above.
Examples of the C6 to C30 arylamino group mentioned in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino and the like.
Examples of the C3 to C30 heteroarylamino group mentioned in the present invention include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
The chain alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, the substituted or unsubstituted C1 to C30 chain alkyl group is preferably a substituted or unsubstituted C1 to C16 chain alkyl group, and more preferably a substituted or unsubstituted C1 to C10 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include: 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 and the like.
In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl means an alkyl group containing a single cyclic structure; polycyclic alkyl refers to a structure in which two or more cycloalkyl groups share one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
It is noted that the possible actions of the various groups/features are described separately herein for ease of illustration, but that this does not mean that the groups/features act in isolation. In fact, the reason for obtaining good performance is essentially an optimized combination of the whole molecule, as a result of synergy between the individual groups, rather than the effect of a single group.
Further preferably, in the organic compound of the present invention, D 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures shown in one of formulas (D1) to (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, D 1 、D 2 、D 3 、D 4 、D 5 Two of which are the same or different,the two are independently selected from structures represented by any one of formulas (D1) to (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each of the other three is independently selected from substituted or unsubstituted C3-C60 heteroaryl.
Further preferably, in the organic compound of the present invention, D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures represented by the formula (D1), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D is 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures represented by the formula (D1), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl;
still more preferably, in formula (d 1), R is independently selected from hydrogen, deuterium, benzonitrile or trifluoromethylphenyl, and each R is not simultaneously hydrogen;
more preferably, the formula (d 1) has a structure shown below:
further preferably, in the organic compound of the present invention, D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures shown in one of the formulas (D2) and (D3), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D is 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures shown in formula (D2) or formula (D3), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl.
Further preferably, in the organic compound of the present invention, D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures represented by the formula (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, the D is 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures represented by the formula (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl.
Still preferably, in the organic compound of the present invention, when D 1 、D 2 、D 3 、D 4 、D 5 Each independently selected from substituted or unsubstituted C3-C60 heteroaryl, selected from substituted or unsubstituted one of the following structural formulae:
when a substituent is present on 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;
more preferably, in the organic compounds of the present invention, when D 1 、D 2 、D 3 、D 4 、D 5 Each independently selected from substituted or unsubstituted C3-C60 heteroaryl, selected from substituted or unsubstituted one of the following structural formulae:
when a substituent group exists on the structural formula, the substituent group is one selected from deuterium, C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
The structural design of the organic compounds of the invention is characterized in that, in addition to a cyano group as electron acceptor, at least one benzonitrile, trifluoromethylphenyl, boroxine or xanthone group is simultaneously introduced as second acceptor. The existence of the cyano group on the central benzene ring can ensure the matching of the LUMO orbital energy level of the molecule and the material light color, ensure that the molecule has smaller singlet state triplet state energy level difference, and simultaneously ensure that the cyano group can be protected by the surrounding large conjugated steric hindrance group, so that the LUMO orbital is distributed by taking the cyano group as the center as far as possible, does not interact with the outside, and avoids the quenching process of an excited state. The benzonitrile, the trifluoromethyl phenyl, the boron oxygen heterocycle and the xanthone group are used as second receptors, the four groups have at least one conjugated aromatic ring and strong electron-withdrawing capability, charges on a benzene ring at the center of a molecule can be dispersed through a conjugation effect, the charge density of the benzene ring is reduced, the BDE-of a C-N bond in the molecule is improved, the stability of the molecule is improved, and the service life of a device is prolonged. The selected heteroaryl electron donor and acceptor structures have higher local triplet energy levels and can realize smaller singlet triplet energy difference, multiple acceptor groups can be matched to form LUMO orbital energy levels (including LUMO, LUMO +1, LUMO +2 and the like) with similar energy, multiple donor groups in molecules can also form HOMO orbital energy levels (including HOMO, HOMO-1, HOMO-2, HOMO-3 and the like) with similar energy, the molecular orbitals with similar energy can generate excited state energy levels with similar energy in the excitation process, and second-order perturbation effects exist among the excited state energy levels, so that excited state coupling is enhanced, the transition rate and radiation transition rate between reverse systems of the material can be greatly improved, and higher device efficiency is realized. The electron donor adopts carbazole derivatives, carboline derivatives, benzofurocarbazole, benzothiophenocarbazole and other heteroaryl groups which have similar electron donating capability, and molecules have similar expected performance.
Further, the compounds represented by the general formula (1) of the present invention may preferably be compounds of the following specific structures, which are merely representative:
the present invention also provides the use of a compound of formula (1) as a functional material in an organic electronic device comprising: 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 label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, preferably an organic electroluminescent device.
The present invention also provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises the compound represented by formula (1) of the present invention described above or any one of the specific compounds A1 to G184 of the present invention described above.
Specifically, embodiments of the present invention provide an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; among them, the light-emitting layer preferably contains the compound represented by the formula (1) of the present invention or contains any of the specific compounds A1 to G184 of the present invention.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life.
The specific reason why the above-mentioned compound of the present invention is excellent when used as an organic electroluminescent device is not clear, and the following is the presumption of the inventors, but these presumptions do not limit the scope of the present invention.
Detailed Description
The specific production 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 production method of the present invention is not limited to these synthesis examples.
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Synthesis of intermediate 1:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), 4-cyanophenylboronic acid (6.36g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 1 as a white solid, weighing 8.9g, with a yield of 82%.
Synthesis of intermediate 2:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), 4-trifluoromethylphenylboronic acid (8.23g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (2.27g, 1.97mmol) and 20mL of aqueous potassium carbonate (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 2 as a white solid, weighing 10.5g, with a yield of 83%.
Synthesis of intermediate 3:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), (2, 12-di-tert-butyl-5, 9-dioxa-13 b-boranonaphthalene [3,2,1-de ] anthracen-7-yl) boronic acid (18.46g, 43.31mmol) was dissolved in 150mL of toluene, palladium tetratriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 3 as a white solid, weighing 14.5g, with a yield of 66%.
Synthesis of intermediate 4:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), (3, 11-di-tert-butyl-5, 9-dioxa-13 b-boranonaphthalene [3,2,1-de ] anthracen-7-yl) boronic acid (18.46g, 43.31mmol) was dissolved in 150mL of toluene, palladium tetrakistriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 4 as a white solid, weighing 15.8g, with a yield of 72%.
Synthesis of intermediate 5:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), xanthone-2-boronic acid (10.4g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetrakistriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 5 as a white solid, weighing 10.9g, with a yield of 75%.
Synthesis of intermediate 6:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), xanthone-1-boronic acid (10.4g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (2.27g, 1.97mmol) and 20mL of aqueous potassium carbonate (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 5 as a white solid weighing 10.9g with a yield of 75%.
Synthesis of intermediate 7:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), xanthone-3-boronic acid (10.4g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetrakistriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 5 as a white solid weighing 10.9g with a yield of 75%.
Synthesis of intermediate 8:
3-bromo-2, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), xanthone-4-boronic acid (10.4g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetrakistriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 5 as a white solid weighing 10.9g with a yield of 75%.
Synthetic example A1:
weighing intermediate 1 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound A1, which is a yellow solid with a yield of 93%. Mass spectrum: m/z 865.01, elemental analysis experimental value: c,86.09; h,4.20; and N,9.72.
Synthesis example A2:
the synthesis was analogous to A1 as a yellow solid in 89% yield. Mass spectrum: m/z 921.12, elemental analysis experimental value: c,86.06; h,4.82; and N,9.12.
Synthesis example A3:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 977.23, elemental analysis experimental value: c,86.04; h,5.36; and N,8.60.
Synthesis example A4:
the synthesis was analogous to A1 as a yellow solid in 80% yield. Mass spectrum: m/z 1033.34, elemental analysis Experimental value: c,86.01; h,5.85; and N,8.13.
Synthesis example A5:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 1201.66, elemental analysis experimental value: c,85.96; h,7.05; and N,6.99.
Synthetic example A6:
the synthesis was analogous to A1 as a yellow solid in 89% yield. Mass spectrum: m/z 1089.44, elemental analysis experimental value: c,85.99; h,6.29; and N,7.71.
Synthesis example A7:
the synthesis was analogous to A1 as a yellow solid in 86% yield. Mass spectrum: m/z 1313.88, elemental analysis experimental value: c,85.93; h,7.67; and N,6.40.
Synthesis example A8:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 1153.74, elemental analysis experiment value: c,77.04; h,5.94; n,7.28; si,9.74.
Synthesis example A9:
the synthesis was analogous to A1 as a yellow solid in 76% yield. Mass spectrum: m/z 1442.47, elemental analysis experimental value: c,71.61; h,6.99; n,5.83; si,15.58.
Synthetic example a10:
the synthesis was analogous to A1 as a yellow solid in 65% yield. Mass spectrum: m/z 965.05, elemental analysis experiment value: c,82.14; h,3.34; n,14.51.
Synthesis example a11:
the synthesis was analogous to A1 as a yellow solid in 72% yield. Mass spectrum: m/z 1065.09, elemental analysis experiment value: c,78.94; h,2.65; n,18.41.
Synthetic example a12:
the synthesis was analogous to A1 as a yellow solid in 70% yield. Mass spectrum: m/z 1169.40, elemental analysis experimental value: c,88.33; h,4.48; and N,7.19.
Synthetic example a13:
the synthesis was analogous to A1 as a yellow solid in 53% yield. Mass spectrum: m/z 1473.80, elemental analysis experimental value: c,89.65; h,4.65; and N,5.70.
Synthesis example a14:
the synthesis was analogous to A1 as a yellow solid in 77% yield. Mass spectrum: m/z 1137.00, elemental analysis experimental value: c,69.72; h,2.84; f,20.05; and N,7.39.
Synthetic example a15:
the synthesis was analogous to A1 as a yellow solid in 81% yield. Mass spectrum: m/z 1409.00, elemental analysis experimental value: c,59.67; h,2.00; f,32.36; and N,5.96.
Synthetic example a16:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 1337.73, elemental analysis experimental value: c,87.99; h,5.73; and N,6.28.
Synthesis example a17:
the synthesis was analogous to A1 as a yellow solid in 79% yield. Mass spectrum: m/z 1810.44, elemental analysis experimental value: c,88.90; h,6.46; and N,4.64.
Synthetic example a18:
the synthesis was similar to A1, yellow solid, 85% yield. Mass spectrum: m/z 868.96, elemental analysis experimental value: c,80.17; h,3.71; n,16.12.
Synthetic example a19:
the synthesis was analogous to A1 as a yellow solid in 86% yield. Mass spectrum: m/z 868.96, elemental analysis experimental value: c,80.17; h,3.71; n,16.12.
Synthesis example a20:
the synthesis was analogous to A1 as a yellow solid in 70% yield. Mass spectrum: m/z 868.96, elemental analysis experiment value: c,80.17; h,3.71; n,16.12.
Synthesis example a21:
the synthesis was analogous to A1 as a yellow solid in 55% yield. Mass spectrum: m/z 868.96, elemental analysis experimental value: c,80.17; h,3.71; and N,16.12.
Synthetic example a35:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; and O,5.22.
Synthetic example a36:
the synthesis was analogous to A1 as a yellow solid in 72% yield. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; and O,5.22.
Synthetic example a37:
the synthesis was analogous to A1 as a yellow solid in 56% yield. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; and O,5.22.
Synthetic example a38:
the synthesis was analogous to A1 as a yellow solid with a yield of 40%. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; and O,5.22.
Synthetic example a39:
the synthesis was analogous to A1 as a yellow solid in 80% yield. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; o,5.22.
Synthesis example a40:
the synthesis was analogous to A1 as a yellow solid in 60% yield. Mass spectrum: m/z 1225.34, elemental analysis Experimental value: c,84.30; h,3.62; n,6.86; and O,5.22.
Synthesis example a41:
the synthesis was analogous to A1 as a yellow solid in 70% yield. Mass spectrum: m/z 1289.58, elemental analysis experiment value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthesis example a42:
the synthesis was analogous to A1 as a yellow solid in 59% yield. Mass spectrum: m/z 1289.58, elemental analysis experimental value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthetic example a43:
the synthesis was analogous to A1 as a yellow solid in 55% yield. Mass spectrum: m/z 1289.58, elemental analysis experimental value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthesis example a44:
the synthesis was analogous to A1 as a yellow solid in 71% yield. Mass spectrum: m/z 1289.58, elemental analysis experimental value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthesis example a45:
the synthesis was analogous to A1 as a yellow solid in 68% yield. Mass spectrum: m/z 1289.58, elemental analysis experimental value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthesis example a46:
the synthesis was analogous to A1 as a yellow solid in 64% yield. Mass spectrum: m/z 1289.58, elemental analysis experimental value: c,80.10; h,3.44; n,6.52; and S,9.94.
Synthesis example a47:
weighing intermediate 2 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound A47, a yellow solid with a yield of 93%. Mass spectrum: m/z 907.29, elemental analysis experimental value: c,82.01; h,4.00; f,6.28; and N,7.71.
Synthesis example a52:
the synthesis was analogous to a47 as a yellow solid in 89% yield. Mass spectrum: m/z 1131.54, elemental analysis experimental value: c,82.73; h,6.05; f,5.03; and N,6.18.
Synthesis example a53:
the synthesis was analogous to a47 as a yellow solid in 83% yield. Mass spectrum: m/z 1355.79, elemental analysis experimental value: c,83.21; h,7.43; f,4.20; and N,5.16.
Synthetic example a54:
the synthesis was analogous to a47 as a yellow solid in 80% yield. Mass spectrum: m/z 1195.45, elemental analysis experimental value: c,74.27; h,5.73; f,4.76; n,5.85; si,9.39.
Synthesis example a55:
the synthesis was analogous to a47 as a yellow solid in 83% yield. Mass spectrum: m/z 1483.61, elemental analysis experimental value: c,69.54; h,6.79; f,3.84; n,4.71; si,15.13.
Synthetic example a58:
the synthesis was analogous to a47 as a yellow solid in 89% yield. Mass spectrum: m/z 1211.42, elemental analysis experimental value: c,85.20; h,4.32; f,4.70; n,5.78.
Synthetic example a81:
the synthesis was analogous to a47 as a yellow solid in 86% yield. Mass spectrum: m/z 1267.33, elemental analysis experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthetic example a82:
the synthesis was analogous to a47 as a yellow solid in 83% yield. Mass spectrum: m/z 1267.33, elemental analysis experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthetic example a83:
the synthesis was analogous to a47 as a yellow solid in 76% yield. Mass spectrum: m/z 1267.33, elemental analysis experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthetic example a84:
the synthesis was analogous to a47 as a yellow solid in 65% yield. Mass spectrum: m/z 1267.33, elemental analysis experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthetic example a85:
the synthesis was analogous to a47 as a yellow solid in 72% yield. Mass spectrum: m/z 1267.33, elemental analysis experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthesis example a86:
the synthesis was analogous to a47 as a yellow solid in 70% yield. Mass spectrum: m/z 1267.33, elemental analysis Experimental value: c,81.44; h,3.50; f,4.49; n,5.52; and O,5.05.
Synthetic example a87:
the synthesis was analogous to a47 as a yellow solid in 53% yield. Mass spectrum: m/z 1331.24, elemental analysis experiment value: c,77.52; h,3.33; f,4.28; n,5.26; s,9.62.
Synthetic example a88:
the synthesis was analogous to a47 as a yellow solid in 77% yield. Mass spectrum: m/z 1331.24, elemental analysis experimental value: c,77.52; h,3.33; f,4.28; n,5.26; s,9.62.
Synthesis example a89:
the synthesis was analogous to a47 as a yellow solid in 81% yield. Mass spectrum: m/z 1331.24, elemental analysis experiment value: c,77.52; h,3.33; f,4.28; n,5.26; and S,9.62.
Synthetic example a90:
the synthesis was analogous to a47 as a yellow solid in 83% yield. Mass spectrum: m/z 1331.24, elemental analysis experiment value: c,77.52; h,3.33; f,4.28; n,5.26; and S,9.62.
Synthetic example a91:
the synthesis was analogous to a47 as a yellow solid in 79% yield. Mass spectrum: m/z 1331.24, elemental analysis experimental value: c,77.52; h,3.33; f,4.28; n,5.26; and S,9.62.
Synthetic example a92:
the synthesis was analogous to a47 as a yellow solid in 85% yield. Mass spectrum: m/z 1331.24, elemental analysis experimental value: c,77.52; h,3.33; f,4.28; n,5.26; s,9.62.
Synthetic example a93:
weighing intermediate 3 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound A93 as a yellow solid with the yield of 63%. Mass spectrum: m/z 1143.47, elemental analysis experimental value: c,85.03; h,5.11; b,0.94; n,6.12; o,2.80.
Synthetic example a98:
the synthesis was analogous to a93 as a yellow solid in 70% yield. Mass spectrum: m/z 1367.72, elemental analysis experimental value: c,85.13; h,6.63; b,0.79; n,5.12; o,2.34.
Synthesis example a99:
the synthesis was analogous to A1 as a yellow solid in 55% yield. Mass spectrum: m/z 1591.97, elemental analysis Experimental value: c,85.20; h,7.72; b,0.68; n,4.40; and O,2.01.
Synthetic example a100:
the synthesis was analogous to A1 as a yellow solid in 83% yield. Mass spectrum: m/z 1431.63, elemental analysis experimental value: c,77.95; h,6.33; b,0.75; n,4.89; o,2.23; si,7.84.
Synthesis example a101:
the synthesis was analogous to A1 as a yellow solid in 72% yield. Mass spectrum: m/z 1719.78, elemental analysis experimental value: c,73.25; h,7.14; b,0.63; n,4.07; o,1.86; si,13.05.
Synthetic example a104:
the synthesis was analogous to A1 as a yellow solid in 56% yield. Mass spectrum: m/z 1447.59, elemental analysis experimental value: c,87.06; h,5.15; b,0.75; n,4.83; o,2.21.
Synthetic example a127:
the synthesis was analogous to A1 as a yellow solid with a yield of 40%. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a128:
the synthesis was analogous to A1 as a yellow solid in 80% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; o,6.38.
Synthetic example a129:
the synthesis was analogous to A1 as a yellow solid in 60% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthesis example a130:
the synthesis was analogous to A1 as a yellow solid in 70% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthesis example a131:
the synthesis was analogous to A1 as a yellow solid in 59% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; o,6.38.
Synthetic example a132:
the synthesis was analogous to A1 as a yellow solid in 55% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a133:
the synthesis was analogous to A1 as a yellow solid in 71% yield. Mass spectrum: m/z 1567.42, elemental analysis experiment value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a134:
the synthesis was analogous to A1 as a yellow solid in 68% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthesis example a135:
the synthesis was analogous to A1 as a yellow solid in 64% yield. Mass spectrum: m/z 1567.42, elemental analysis experiment value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a136:
the synthesis was analogous to A1 as a yellow solid in 71% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthesis example a137:
the synthesis was analogous to A1 as a yellow solid in 68% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a138:
the synthesis was analogous to A1 as a yellow solid in 64% yield. Mass spectrum: m/z 1567.42, elemental analysis experiment value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a139:
weighing intermediate 4 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound A139 as yellow solid with yield of 63%. Mass spectrum: m/z 1143.47, elemental analysis experimental value: c,85.03; h,5.11; b,0.94; n,6.12; o,2.80.
Synthesis example a144:
the synthesis was analogous to a139 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1367.72, elemental analysis experimental value: c,85.13; h,6.63; b,0.79; n,5.12; o,2.34.
Synthetic example a145:
the synthesis was analogous to a139 as a yellow solid in 55% yield. Mass spectrum: m/z 1591.97, elemental analysis experimental value: c,85.20; h,7.72; b,0.68; n,4.40; and O,2.01.
Synthetic example a146:
the synthesis was analogous to a139 as a yellow solid in 83% yield. Mass spectrum: m/z 1431.63, elemental analysis Experimental value: c,77.95; h,6.33; b,0.75; n,4.89; o,2.23; si,7.84.
Synthetic example a147:
the synthesis was analogous to a139 as a yellow solid in 72% yield. Mass spectrum: m/z 1719.78, elemental analysis experimental value: c,73.25; h,7.14; b,0.63; n,4.07; o,1.86; si,13.05.
Synthesis example a150:
the synthesis was analogous to a139 as a yellow solid in 56% yield. Mass spectrum: m/z 1447.59, elemental analysis experimental value: c,87.06; h,5.15; b,0.75; n,4.83; o,2.21.
Synthetic example a173:
the synthesis was analogous to a139 as a yellow solid with a yield of 40%. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a174:
the synthesis was analogous to a139 as a yellow solid in 80% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; o,6.38.
Synthetic example a175:
the synthesis was analogous to a139 as a yellow solid in 60% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a176:
the synthesis was analogous to a139 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; o,6.38.
Synthetic example a177:
the synthesis was analogous to a139 as a yellow solid in 59% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a178:
the synthesis was analogous to a139 as a yellow solid in 80% yield. Mass spectrum: m/z 1503.51, elemental analysis experimental value: c,83.82; h,4.42; b,0.72; n,4.65; and O,6.38.
Synthetic example a179:
the synthesis was analogous to a139 as a yellow solid in 79% yield. Mass spectrum: m/z 1567.42, elemental analysis experiment value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a180:
the synthesis was analogous to a139 as a yellow solid in 78% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a181:
the synthesis was analogous to a139 as a yellow solid in 88% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a182:
the synthesis was analogous to a139 as a yellow solid in 87% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a183:
the synthesis was analogous to a139 as a yellow solid in 86% yield. Mass spectrum: m/z 1567.42, elemental analysis experiment value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthetic example a184:
the synthesis was analogous to a139 as a yellow solid in 83% yield. Mass spectrum: m/z 1567.42, elemental analysis experimental value: c,80.39; h,4.24; b,0.69; n,4.46; o,2.04; and S,8.17.
Synthesis example a185:
weighing intermediate 5 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound A185, namely a yellow solid, with the yield of 63%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthetic example a190:
the synthesis was analogous to a185 as a yellow solid in 75% yield. Mass spectrum: m/z 1181.56, elemental analysis experimental value: c,85.32; h,6.05; n,5.92; o,2.71.
Synthetic example a191:
the synthesis was analogous to a185 as a yellow solid in 91% yield. Mass spectrum: m/z 1405.81, elemental analysis experiment value: c,85.37; h,7.38; n,4.98; o,2.27.
Synthetic example a192:
the synthesis was analogous to a185 as a yellow solid in 82% yield. Mass spectrum: m/z 1245.47, elemental analysis experimental value: c,77.07; h,5.74; n,5.62; o,2.57; and 9.01 of Si.
Synthetic example a193:
the synthesis was analogous to a185 as a yellow solid in 79% yield. Mass spectrum: m/z 1533.63, elemental analysis experimental value: c,71.96; h,6.76; n,4.56; o,2.08; si,14.63.
Synthetic example a196:
the synthesis was analogous to a185 as a yellow solid in 73% yield. Mass spectrum: m/z 1261.44, elemental analysis experiment value: c,87.53; h,4.39; n,5.55; o,2.53.
Synthetic example a231:
weighing intermediate 6 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound A231 as a yellow solid with the yield of 63%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthetic example a236:
the synthesis was analogous to a231 as a yellow solid in 83% yield. Mass spectrum: m/z 1181.56, elemental analysis experimental value: c,85.32; h,6.05; n,5.92; o,2.71.
Synthesis example a237:
the synthesis was analogous to a231 as a yellow solid in 81% yield. Mass spectrum: m/z 1405.81, elemental analysis experiment value: c,85.37; h,7.38; n,4.98; o,2.27.
Synthetic example a238:
the synthesis was analogous to a231 as a yellow solid in 83% yield. Mass spectrum: m/z 1245.47, elemental analysis experiment value: c,77.07; h,5.74; n,5.62; o,2.57; and 9.01 of Si.
Synthetic example a239:
the synthesis was analogous to a231 as a yellow solid in 73% yield. Mass spectrum: m/z 1533.63, elemental analysis experimental value: c,71.96; h,6.76; n,4.56; o,2.08; si,14.63.
Synthetic example a242:
the synthesis was analogous to a231 as a yellow solid in 82% yield. Mass spectrum: m/z 1261.44, elemental analysis experimental value: c,87.53; h,4.39; n,5.55; o,2.53.
Synthetic example a277:
weighing intermediate 7 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound A277, namely a yellow solid, wherein the yield is 63%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthetic example a282:
the synthesis was analogous to a231 as a yellow solid in 73% yield. Mass spectrum: m/z 1181.56, elemental analysis experimental value: c,85.32; h,6.05; n,5.92; o,2.71.
Synthesis example a283:
the synthesis was analogous to a231 as a yellow solid in 69% yield. Mass spectrum: m/z 1405.81, elemental analysis experimental value: c,85.37; h,7.38; n,4.98; o,2.27.
Synthesis example a284:
the synthesis was analogous to a231 as a yellow solid in 65% yield. Mass spectrum: m/z 1245.47, elemental analysis experimental value: c,77.07; h,5.74; n,5.62; o,2.57; and Si,9.01.
Synthetic example a285:
the synthesis was analogous to a231 as a yellow solid in 54% yield. Mass spectrum: m/z 1533.63, elemental analysis experimental value: c,71.96; h,6.76; n,4.56; o,2.08; si,14.63.
Synthetic example a288:
the synthesis was analogous to a231 as a yellow solid in 74% yield. Mass spectrum: m/z 1261.44, elemental analysis experiment value: c,87.53; h,4.39; n,5.55; o,2.53.
Synthetic example a323:
weighing intermediate 8 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound A323 which is a yellow solid and has a yield of 63%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthetic example a328:
the synthesis was analogous to a323 as a yellow solid in 84% yield. Mass spectrum: m/z 1181.56, elemental analysis experimental value: c,85.32; h,6.05; n,5.92; o,2.71.
Synthetic example a329:
the synthesis was analogous to a323 as a yellow solid in 63% yield. Mass spectrum: m/z 1405.81, elemental analysis experimental value: c,85.37; h,7.38; n,4.98; o,2.27.
Synthetic example a330:
the synthesis was analogous to a323 as a yellow solid in 64% yield. Mass spectrum: m/z 1245.47, elemental analysis experimental value: c,77.07; h,5.74; n,5.62; o,2.57; and 9.01 of Si.
Synthetic example a331:
the synthesis was analogous to a323 as a yellow solid in 69% yield. Mass spectrum: m/z 1533.63, elemental analysis experimental value: c,71.96; h,6.76; n,4.56; o,2.08; si,14.63.
Synthetic example a334:
the synthesis was analogous to a323 as a yellow solid in 73% yield. Mass spectrum: m/z 1261.44, elemental analysis experimental value: c,87.53; h,4.39; n,5.55; o,2.53.
Synthesis of intermediate 9:
2-bromo-3, 4,5, 6-tetrafluorobenzonitrile (10g, 39.37mmol), 4-cyanobenzoic acid (6.36g, 43.31mmol) were dissolved in 150mL of toluene, palladium tetrakistriphenylphosphine (2.27g, 1.97mmol) and 20mL of an aqueous potassium carbonate solution (10.88g, 78.57mmol) were added, and the mixture was refluxed for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 9 as a white solid weighing 8.9g with a yield of 82%.
Synthesis of intermediate 10:
the synthesis was similar to intermediate 9, white solid, yield 79%.
Synthesis of intermediate 11:
the synthesis was similar to intermediate 9, white solid, yield 68%.
Synthesis of intermediate 12:
the synthesis was similar to intermediate 9, white solid, 73% yield.
Synthesis of intermediate 13:
the synthesis was similar to intermediate 9, white solid, 55% yield.
Synthesis of intermediate 14:
the synthesis was similar to intermediate 9, white solid, yield 70%.
Synthesis of intermediate 15:
the synthesis was similar to intermediate 9, white solid, yield 68%.
Synthesis of intermediate 16:
the synthesis was similar to intermediate 9, white solid, 77% yield.
Synthesis example B1:
weighing intermediate 9 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound B1, namely a yellow solid, wherein the yield is 93%. Mass spectrum: m/z 865.01, elemental analysis experimental value: c,86.09; h,4.20; and N,9.72.
Synthesis example B2:
the synthesis was analogous to B1 as a yellow solid in 89% yield. Mass spectrum: m/z 921.12, elemental analysis experimental value: c,86.06; h,4.82; and N,9.12.
Synthesis example B3:
the synthesis was analogous to B1 as a yellow solid in 83% yield. Mass spectrum: m/z 977.23, elemental analysis experimental value: c,86.04; h,5.36; and N,8.60.
Synthesis example B4:
the synthesis was analogous to B1 as a yellow solid in 80% yield. Mass spectrum: m/z 1033.34, elemental analysis Experimental value: c,86.01; h,5.85; and N,8.13.
Synthesis example B5:
the synthesis was analogous to B1 as a yellow solid in 83% yield. Mass spectrum: m/z 1201.66, elemental analysis experimental value: c,85.96; h,7.05; and N,6.99.
Synthesis example B6:
the synthesis was analogous to B1 as a yellow solid in 89% yield. Mass spectrum: m/z 1089.44, elemental analysis experimental value: c,85.99; h,6.29; and N,7.71.
Synthesis example B7:
the synthesis was analogous to B1 as a yellow solid in 86% yield. Mass spectrum: m/z 1313.88, elemental analysis experimental value: c,85.93; h,7.67; and N,6.40.
Synthesis example B8:
the synthesis was analogous to B1 as a yellow solid in 83% yield. Mass spectrum: m/z 1153.74, elemental analysis experiment value: c,77.04; h,5.94; n,7.28; si,9.74.
Synthesis example B9:
the synthesis was analogous to B1 as a yellow solid in 76% yield. Mass spectrum: m/z 1442.47, elemental analysis experimental value: c,71.61; h,6.99; n,5.83; si,15.58.
Synthesis example B10:
the synthesis was similar to B1, yellow solid, 65% yield. Mass spectrum: m/z 965.05, elemental analysis experiment value: c,82.14; h,3.34; n,14.51.
Synthetic example B11:
the synthesis was analogous to B1 as a yellow solid in 72% yield. Mass spectrum: m/z 1065.09, elemental analysis experimental value: c,78.94; h,2.65; n,18.41.
Synthesis example B12:
the synthesis was analogous to B1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1169.40, elemental analysis experimental value: c,88.33; h,4.48; and N,7.19.
Synthesis example B13:
the synthesis was analogous to B1 as a yellow solid in 53% yield. Mass spectrum: m/z 1473.80, elemental analysis experimental value: c,89.65; h,4.65; and N,5.70.
Synthesis example B14:
the synthesis was analogous to B1 as a yellow solid in 77% yield. Mass spectrum: m/z 1137.00, elemental analysis experimental value: c,69.72; h,2.84; f,20.05; and N,7.39.
Synthesis example B15:
the synthesis was analogous to B1 as a yellow solid in 81% yield. Mass spectrum: m/z 1409.00, elemental analysis experimental value: c,59.67; h,2.00; f,32.36; and N,5.96.
Synthesis example B16:
the synthesis was analogous to B1 as a yellow solid in 83% yield. Mass spectrum: m/z 1337.73, elemental analysis experimental value: c,87.99; h,5.73; and N,6.28.
Synthesis example B17:
the synthesis was analogous to B1 as a yellow solid in 79% yield. Mass spectrum: m/z 1810.44, elemental analysis experimental value: c,88.90; h,6.46; and N,4.64.
Synthesis example B18:
the synthesis was similar to B1, yellow solid, 85% yield. Mass spectrum: m/z 868.96, elemental analysis experiment value: c,80.17; h,3.71; and N,16.12.
Synthesis example B19:
the synthesis was analogous to B1 as a yellow solid in 86% yield. Mass spectrum: m/z 868.96, elemental analysis experimental value: c,80.17; h,3.71; and N,16.12.
Synthesis example B20:
the synthesis was analogous to B1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 868.96, elemental analysis experiment value: c,80.17; h,3.71; and N,16.12.
Synthesis example B21:
the synthesis was analogous to B1 as a yellow solid in 55% yield. Mass spectrum: m/z 868.96, elemental analysis experimental value: c,80.17; h,3.71; and N,16.12.
Synthesis example B22:
the synthesis was analogous to B1 as a yellow solid in 59% yield. Mass spectrum: m/z 929.01, elemental analysis experimental value: c,80.16; h,3.91; n,9.05; and O,6.89.
Synthetic example B23:
the synthesis was analogous to B1 as a yellow solid in 58% yield. Mass spectrum: m/z 993.25, elemental analysis experimental value: c,74.97; h,3.65; n,8.46; and S,12.91.
Synthesis example B24:
weighing intermediate 10 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound B24 which is yellow solid and has the yield of 93%. Mass spectrum: m/z 907.29, elemental analysis experimental value: c,82.01; h,4.00; f,6.28; and N,7.71.
Synthetic example B29:
the synthesis was analogous to B24 as a yellow solid in 89% yield. Mass spectrum: m/z 1131.54, elemental analysis experimental value: c,82.73; h,6.05; f,5.03; and N,6.18.
Synthesis example B30:
the synthesis was similar to B24, yellow solid, 83% yield. Mass spectrum: m/z 1355.79, elemental analysis experimental value: c,83.21; h,7.43; f,4.20; and N,5.16.
Synthetic example B31:
the synthesis was analogous to B24 as a yellow solid in 80% yield. Mass spectrum: m/z 1195.45, elemental analysis experimental value: c,74.27; h,5.73; f,4.76; n,5.85; si,9.39.
Synthetic example B32:
the synthesis was similar to B24, yellow solid, 83% yield. Mass spectrum: m/z 1483.61, elemental analysis experimental value: c,69.54; h,6.79; f,3.84; n,4.71; si,15.13.
Synthetic example B35:
the synthesis was analogous to B24 as a yellow solid in 89% yield. Mass spectrum: m/z 1211.42, elemental analysis experiment value: c,85.20; h,4.32; f,4.70; n,5.78.
Synthesis example B47:
weighing intermediate 11 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound B47 which is a yellow solid and has a yield of 63%. Mass spectrum: m/z 1143.47, elemental analysis experiment value: c,85.03; h,5.11; b,0.94; n,6.12; o,2.80.
Synthesis example B70:
weighing intermediate 12 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound B70 as a yellow solid with the yield of 63%. Mass spectrum: m/z 1143.47, elemental analysis experimental value: c,85.03; h,5.11; b,0.94; n,6.12; o,2.80.
Synthetic example B93:
weighing intermediate 13 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound B93 as a yellow solid with the yield of 58%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthesis example B116:
weighing intermediate 14 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound B116 as a yellow solid with the yield of 55%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; o,3.34.
Synthetic example B139:
weighing intermediate 15 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound B139 as a yellow solid with the yield of 59%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; and O,3.34.
Synthesis example B162:
weighing intermediate 16 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound B162 as a yellow solid with the yield of 61%. Mass spectrum: m/z 957.31, elemental analysis experiment value: c,85.25; h,4.10; n,7.31; o,3.34.
Synthesis of intermediate 17:
3, 5-dibromo-2, 4, 6-trifluorobenzonitrile (10g, 39.37mmol), 4-cyanophenylboronic acid (13.27g, 69.87mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (1.83g, 1.59mmol) and 20mL of an aqueous potassium carbonate solution (8.78g, 63.51mmol) were added, and the mixture was refluxed for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 17 as a white solid, weighing 7.9g, yield 69%.
Synthesis of intermediates 18-24:
the synthesis method is similar to intermediate 17, and intermediates 18-24 are all white solids with yields of 61%, 40%, 45%, 50%, 48%, 55%, 61%, respectively.
Synthesis example C1:
weighing intermediate 17 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C1, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 800.93, elemental analysis experimental value: c,85.48; h,4.03; n,10.49.
Synthesis example C2:
the synthesis was similar to C1, yellow solid, 79% yield. Mass spectrum: m/z 842.32, elemental analysis experimental value: c,85.49; h,4.54; and N,9.97.
Synthesis example C3:
the synthesis was similar to C1, yellow solid, 70% yield. Mass spectrum: m/z 884.36, elemental analysis experimental value: c,85.49; h,5.01; and N,9.50.
Synthesis example C4:
the synthesis was similar to C1, yellow solid, yield 72%. Mass spectrum: m/z 926.41, elemental analysis experimental value: c,85.50; h,5.44; and N,9.06.
Synthesis example C5:
the synthesis was similar to C1, yellow solid, 71% yield. Mass spectrum: m/z 1052.55, elemental analysis experimental value: c,85.52; h,6.51; and N,7.98.
Synthesis example C6:
the synthesis was similar to C1, yellow solid, 78% yield. Mass spectrum: m/z 968.46, elemental analysis experimental value: c,85.51; h,5.82; n,8.67.
Synthesis example C7:
the synthesis was analogous to C1 as a yellow solid in 79% yield. Mass spectrum: m/z 1136.64, elemental analysis experimental value: c,85.52; h,7.09; and N,7.39.
Synthesis example C8:
the synthesis was similar to C1, yellow solid, 78% yield. Mass spectrum: m/z 1016.39, elemental analysis experiment value: c,77.91; h,5.55; n,8.26; si,8.28.
Synthesis example C9:
the synthesis was analogous to C1 as a yellow solid in 79% yield. Mass spectrum: m/z 1218.49, elemental analysis experimental value: c,72.85; h,6.44; n,6.89; si,13.81.
Synthesis example C10:
the synthesis was similar to C1, yellow solid, 70% yield. Mass spectrum: m/z 875.25, elemental analysis experimental value: c,82.27; h,3.34; n,14.39.
Synthesis example C11:
the synthesis was similar to C1, yellow solid, 73% yield. Mass spectrum: m/z 950.24, elemental analysis experimental value: c,79.57; h,2.76; n,17.67.
Synthesis example C12:
the synthesis was analogous to C1 as a yellow solid in 76% yield. Mass spectrum: m/z 1028.36, elemental analysis experimental value: c,87.53; h,4.31; and N,8.17.
Synthesis example C13:
the synthesis was similar to C1, yellow solid, 79% yield. Mass spectrum: m/z 1256.46, experimental value of elemental analysis: c,88.83; h,4.49; and N,6.68.
Synthesis example C14:
the synthesis was similar to C1, yellow solid, 69% yield. Mass spectrum: m/z 1004.23, elemental analysis experimental value: c,71.71; h,2.91; f,17.01; and N,8.36.
Synthesis example C15:
the synthesis was similar to C1, yellow solid, yield 80%. Mass spectrum: m/z 1208.19, elemental analysis experimental value: c,62.59; h,2.17; f,28.29; and N,6.95.
Synthesis example C16:
the synthesis was similar to C1, yellow solid, 75% yield. Mass spectrum: m/z 1154.50, elemental analysis experimental value: c,87.32; h,5.41; and N,7.27.
Synthetic example C17:
the synthesis was analogous to C1 as a yellow solid in 75% yield. Mass spectrum: m/z 1508.74, elemental analysis experimental value: c,88.29; h,6.14; n,5.57.
Synthesis example C18:
the synthesis was similar to C1, yellow solid, 79% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example C19:
the synthesis was similar to C1, yellow solid, 70% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example C20:
the synthesis was similar to C1, yellow solid, 69% yield. Mass spectrum: m/z 803.25, elemental analysis experiment value: c,80.68; h,3.64; n,15.68.
Synthesis example C21:
the synthesis was analogous to C1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example C22:
the synthesis was analogous to C1 as a yellow solid in 81% yield. Mass spectrum: m/z 848.25, elemental analysis experimental value: c,80.65; h,3.80; n,9.90; o,5.65.
Synthesis example C23:
the synthesis was similar to C1, yellow solid, 70% yield. Mass spectrum: m/z 896.19, elemental analysis experiment value: c,76.32; h,3.60; n,9.37; s,10.72.
Synthesis example C24:
weighing intermediate 18 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C24 which is yellow solid with the yield of 83%. Mass spectrum: m/z 886.25, elemental analysis experimental value: c,77.19; h,3.64; f,12.85; and N,6.32.
Synthesis example C25:
the synthesis was similar to C24, yellow solid, 70% yield. Mass spectrum: m/z 928.30, elemental analysis experimental value: c,77.58; h,4.12; f,12.27; n,6.03
Synthesis example C26:
the synthesis was similar to C24, a yellow solid, 71% yield. Mass spectrum: m/z 970.35, elemental analysis experimental value: c,77.92; h,4.57; f,11.74; n,5.77
Synthesis example C27:
the synthesis was similar to C24, yellow solid, 73% yield. Mass spectrum: m/z 1012.39, elemental analysis experimental value: c,78.24; h,4.97; f,11.25; n,5.53
Synthesis example C28:
the synthesis was similar to C24, a yellow solid, 69% yield. Mass spectrum: m/z 1138.53, elemental analysis experimental value: c,79.06; h,6.02; f,10.00; n,4.92
Synthetic example C29:
the synthesis was similar to C24, yellow solid, 67% yield. Mass spectrum: m/z 1054.44, elemental analysis experimental value: c,78.54; h,5.35; f,10.80; n,5.31
Synthesis example C30:
the synthesis was similar to C24, yellow solid, 66% yield. Mass spectrum: m/z 1222.63, elemental analysis experimental value: c,79.51; h,6.59; f,9.32; n,4.58
Synthesis example C31:
the synthesis was similar to C24, a yellow solid, 80% yield. Mass spectrum: m/z 1102.37, elemental analysis experimental value: c,71.84; h,5.12; f,10.33; n,5.08; si,7.64
Synthetic example C32:
the synthesis was similar to C24, yellow solid, 73% yield. Mass spectrum: m/z 1304.47, elemental analysis Experimental value: c,68.06; h,6.02; f,8.73; n,4.29; si,12.90
Synthetic example C33:
the synthesis was similar to C24, a yellow solid, 72% yield. Mass spectrum: m/z 961.24, elemental analysis experimental value: c,74.92; h,3.04; f,11.85; n,10.19
Synthesis example C34:
the synthesis was similar to C24, a yellow solid, 71% yield. Mass spectrum: m/z 1036.22, elemental analysis experimental value: c,72.97; h,2.53; f,10.99; n,13.51
Synthesis example C35:
the synthesis was similar to C24, a yellow solid, 69% yield. Mass spectrum: m/z 1114.35, elemental analysis experimental value: c,80.78; h,3.98; f,10.22; n,5.02
Synthesis example C36:
the synthesis was analogous to C24 as a yellow solid in 59% yield. Mass spectrum: m/z 1342.44, elemental analysis experimental value: c,83.14; h,4.20; f,8.48; n,4.17
Synthetic example C37:
the synthesis was similar to C24, a yellow solid, 58% yield. Mass spectrum: m/z 1090.22, elemental analysis experimental value: c,66.06; h,2.68; f,26.12; n,5.14
Synthesis example C38:
the synthesis was similar to C24, yellow solid, 67% yield. Mass spectrum: m/z 1294.18, elemental analysis experimental value: c,58.44; h,2.02; f,35.21; n,4.33
Synthesis example C39:
the synthesis was similar to C24, a yellow solid, 78% yield. Mass spectrum: m/z 1240.49, elemental analysis experimental value: c,81.27; h,5.03; f,9.18; n,4.51
Synthesis example C40:
the synthesis was similar to C24, yellow solid, 70% yield. Mass spectrum: m/z 1594.72, elemental analysis experiment value: c,83.54; h,5.81; f,7.14; n,3.51
Synthesis example C41:
the synthesis was similar to C24, yellow solid, 75% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example C42:
the synthesis was similar to C24, yellow solid, 80% yield. Mass spectrum: m/z 889.24, elemental analysis experimental values: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example C43:
the synthesis was similar to C24, a yellow solid, 82% yield. Mass spectrum: m/z 889.24, elemental analysis experimental values: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example C44:
the synthesis was similar to C24, yellow solid, 79% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example C45:
the synthesis was analogous to C24 as a yellow solid in 79% yield. Mass spectrum: m/z 934.24, elemental analysis experimental value: c,73.23; h,3.45; f,12.19; n,5.99; o,5.13
Synthesis example C46:
the synthesis was similar to C24, yellow solid, 75% yield. Mass spectrum: m/z 982.17, elemental analysis experimental value: c,69.64; h,3.28; f,11.60; n,5.70; s,9.78
Synthesis example C47:
weighing intermediate 19 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C47, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example C52:
the synthesis was analogous to C47 as a yellow solid with 70% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthesis example C53:
the synthesis was analogous to C47 as a yellow solid in 74% yield. 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.
Synthesis example C54:
the synthesis was similar to C47, yellow solid, 75% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example C55:
the synthesis was similar to C47 as a yellow solid in 73% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example C58:
the synthesis was similar to C47, yellow solid, 69% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthetic example C59:
the synthesis was analogous to C47 as a yellow solid in 69% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; and O,3.52.
Synthesis example C60:
the synthesis was analogous to C47 as a yellow solid in 78% yield. Mass spectrum: m/z 1562.57, elemental analysis experiment value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example C61:
the synthesis was analogous to C47 as a yellow solid in 74% yield. Mass spectrum: m/z 1766.53, elemental analysis experiment value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; o,3.62.
Synthesis example C70:
weighing intermediate 20 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C70, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example C75:
the synthesis was similar to C70, a yellow solid, 73% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthetic example C73:
the synthesis was similar to C70, a yellow solid, in 70% yield. 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.
Synthesis example C77:
the synthesis was similar to C70, a yellow solid, 68% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example C78:
the synthesis was similar to C70, a yellow solid, 66% yield. Mass spectrum: m/z 1790.84, elemental analysis experiment value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example C81:
the synthesis was similar to C70, a yellow solid, 77% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example C82:
the synthesis was analogous to C70, a yellow solid, 77% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; o,3.52.
Synthesis example C83:
the synthesis was similar to C70, a yellow solid, 74% yield. Mass spectrum: m/z 1562.57, elemental analysis experimental value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example C84:
the synthesis was similar to C70, a yellow solid, 71% yield. Mass spectrum: m/z 1766.53, elemental analysis experiment value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; and O,3.62.
Synthetic example C93:
weighing intermediate 21 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C93, a yellow solid and a yield of 85%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthesis example C94:
the synthesis was similar to C93, a yellow solid, 71% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example C95:
the synthesis was similar to C93, a yellow solid, 70% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthesis example C96:
the synthesis was analogous to C93, a yellow solid, 59% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example C97:
the synthesis was analogous to C93, a yellow solid, 58% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example C98:
the synthesis was similar to C93, a yellow solid, 55% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54
Synthesis example C99:
the synthesis was similar to C93, a yellow solid, 59% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthesis example C100:
the synthesis was similar to C93, a yellow solid, 61% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example C101:
the synthesis was similar to C93, a yellow solid, 63% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example C102:
the synthesis was similar to C93, a yellow solid, 73% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthesis example C103:
the synthesis was similar to C93, a yellow solid, 72% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example C104:
the synthesis was analogous to C93, a yellow solid, yield 79%. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example C105:
the synthesis was similar to C93, a yellow solid, 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; o,4.43.
Synthesis example C106:
the synthesis was similar to C93, a yellow solid, 74% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthetic example C107:
the synthesis was similar to C93, a yellow solid, 69% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthesis example C108:
the synthesis was similar to C93, a yellow solid, 55% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example C109:
the synthesis was similar to C93, a yellow solid, 80% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example C110:
the synthesis was similar to C93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C111:
the synthesis was similar to C93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C112:
the synthesis was analogous to C93, a yellow solid, yield 79%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C113:
the synthesis was similar to C93, a yellow solid, 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C114:
the synthesis was similar to C93, a yellow solid, 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example C115:
the synthesis was similar to C93, a yellow solid, 72% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example C116:
weighing intermediate 22 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C116, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthesis example C117:
the synthesis was analogous to C116 as a yellow solid in 77% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; o,6.22.
Synthesis example C118:
the synthesis was analogous to C116 as a yellow solid in 75% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthetic example C119:
the synthesis was analogous to C116 as a yellow solid in 78% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example C120:
the synthesis was similar to C116 as a yellow solid with 60% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example C121:
the synthesis was similar to C116 as a yellow solid in 59% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example C122:
the synthesis was similar to C116 as a yellow solid in 55% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthesis example C123:
the synthesis was similar to C116, a yellow solid, 80% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example C124:
the synthesis was similar to C116 as a yellow solid in 81% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example C125:
the synthesis was similar to C116 as a yellow solid in 83% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthesis example C126:
the synthesis was analogous to C116 as a yellow solid in 88% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthetic example C127:
the synthesis was analogous to C116 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example C128:
the synthesis was similar to C116 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example C129:
the synthesis was analogous to C116 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example C130:
the synthesis was similar to C116 as a yellow solid in 75% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthesis example C131:
the synthesis was analogous to C116 as a yellow solid in 67% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example C132:
the synthesis was analogous to C116 as a yellow solid in 53% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example C133:
the synthesis was similar to C116, a yellow solid, 70% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C134:
the synthesis was similar to C116, a yellow solid, 80% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C135:
the synthesis was similar to C116 as a yellow solid in 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C136:
the synthesis was similar to C116 as a yellow solid in 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C137:
the synthesis was analogous to C116 as a yellow solid in 71% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example C138:
the synthesis was similar to C116 as a yellow solid in 71% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example C139:
weighing intermediate 23 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound C139 as yellow solid with yield of 73%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example C140:
the synthesis was similar to C139 as a yellow solid in 74% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; o,6.22.
Synthesis example C141:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthesis example C142:
the synthesis was similar to C139 as a yellow solid with 75% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example C143:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example C144:
the synthesis was similar to C139 as a yellow solid with 88% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example C145:
the synthesis was similar to C139 as a yellow solid with 80% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthesis example C146:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example C147:
the synthesis was similar to C139 as a yellow solid in 83% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example C148:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example C149:
the synthesis was similar to C139 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example C150:
the synthesis was similar to C139 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experiment value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example C151:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example C152:
the synthesis was similar to C139 as a yellow solid in 75% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example C153:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example C154:
the synthesis was similar to C139 as a yellow solid in 69% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example C155:
the synthesis was similar to C139 as a yellow solid with 79% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example C156:
the synthesis was similar to C139 as a yellow solid in 58% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C157:
the synthesis was similar to C139 as a yellow solid in 83% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C158:
the synthesis was similar to C139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C159:
the synthesis was similar to C139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C160:
the synthesis was similar to C139 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example C161:
the synthesis was similar to C139 as a yellow solid with 59% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example C162:
weighing intermediate 19 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound C162, a yellow solid and a yield of 76%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example C163:
the synthesis was similar to C162 as a yellow solid in 75% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example C164:
the synthesis was similar to C162 as a yellow solid in 74% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthetic example C165:
the synthesis was similar to C162 as a yellow solid in 73% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example C166:
the synthesis was similar to C162 as a yellow solid in 71% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example C167:
the synthesis was similar to C162 as a yellow solid in 70% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54.
Synthesis example C168:
the synthesis was similar to C162 as a yellow solid in 70% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthesis example C169:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example C170:
the synthesis was analogous to C162 as a yellow solid in 70% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example C171:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthesis example C172:
the synthesis was analogous to C162 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example C173:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example C174:
the synthesis was analogous to C162 as a yellow solid in 75% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example C175:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example C176:
the synthesis was analogous to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthetic example C177:
the synthesis was similar to C162 as a yellow solid in 58% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthesis example C178:
the synthesis was similar to C162 as a yellow solid in 67% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example C179:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example C180:
the synthesis was analogous to C162 as a yellow solid in 59% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example C181:
the synthesis was similar to C162 as a yellow solid in 76% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example C182:
the synthesis was similar to C162 as a yellow solid in 82% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example C183:
the synthesis was similar to C162 as a yellow solid in 73% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example C184:
the synthesis was similar to C162 as a yellow solid in 79% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis of intermediate 25:
2, 6-dibromo-3, 4, 5-trifluorobenzonitrile (10g, 39.37mmol), 4-cyanophenylboronic acid (13.27g, 69.87mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (1.83g, 1.59mmol) and 20mL of an aqueous potassium carbonate solution (8.78g, 63.51mmol) were added, and the mixture was refluxed for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 25 as a white solid weighing 6.8g with a yield of 59%.
Synthesis of intermediates 26-32:
the synthesis method is similar to that of the intermediate 25, and the intermediates 25 to 32 are white solids with the yields of 59%, 58%, 49%, 70%, 66%, 51% and 47%, respectively.
Synthesis example D1:
weighing intermediate 25 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound D1, a yellow solid, with a yield of 76%. Mass spectrum: m/z 800.93, elemental analysis experimental value: c,85.48; h,4.03; n,10.49.
Synthesis example D2:
the synthesis was analogous to D1 as a yellow solid in 79% yield. Mass spectrum: m/z 842.32, elemental analysis experimental value: c,85.49; h,4.54; and N,9.97.
Synthesis example D3:
the synthesis was analogous to D1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 884.36, elemental analysis experimental values: c,85.49; h,5.01; and N,9.50.
Synthesis example D4:
the synthesis was analogous to D1 as a yellow solid in 72% yield. Mass spectrum: m/z 926.41, elemental analysis experiment value: c,85.50; h,5.44; and N,9.06.
Synthesis example D5:
the synthesis was analogous to D1 as a yellow solid in 71% yield. Mass spectrum: m/z 1052.55, elemental analysis experimental value: c,85.52; h,6.51; and N,7.98.
Synthetic example D6:
the synthesis was analogous to D1 as a yellow solid in 78% yield. Mass spectrum: m/z 968.46, elemental analysis experimental value: c,85.51; h,5.82; n,8.67.
Synthetic example D7:
the synthesis was analogous to D1 as a yellow solid in 79% yield. Mass spectrum: m/z 1136.64, elemental analysis experimental value: c,85.52; h,7.09; and N,7.39.
Synthesis example D8:
the synthesis was analogous to D1 as a yellow solid in 78% yield. Mass spectrum: m/z 1016.39, elemental analysis experimental value: c,77.91; h,5.55; n,8.26; si,8.28.
Synthetic example D9:
the synthesis was analogous to D1 as a yellow solid in 79% yield. Mass spectrum: m/z 1218.49, elemental analysis experimental value: c,72.85; h,6.44; n,6.89; si,13.81.
Synthesis example D10:
the synthesis was analogous to D1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 875.25, elemental analysis experimental value: c,82.27; h,3.34; n,14.39.
Synthetic example D11:
the synthesis was analogous to D1 as a yellow solid in 73% yield. Mass spectrum: m/z 950.24, elemental analysis experimental value: c,79.57; h,2.76; n,17.67.
Synthesis example D12:
the synthesis was analogous to D1 as a yellow solid with 76% yield. Mass spectrum: m/z 1028.36, elemental analysis experimental value: c,87.53; h,4.31; and N,8.17.
Synthetic example D13:
the synthesis was analogous to D1 as a yellow solid with 79% yield. Mass spectrum: m/z 1256.46, elemental analysis experimental value: c,88.83; h,4.49; and N,6.68. Synthesis example D14:
the synthesis was analogous to D1 as a yellow solid in 69% yield. Mass spectrum: m/z 1004.23, elemental analysis experimental value: c,71.71; h,2.91; f,17.01; and N,8.36.
Synthetic example D15:
the synthesis was analogous to D1 as a yellow solid in 80% yield. Mass spectrum: m/z 1208.19, elemental analysis experimental value: c,62.59; h,2.17; f,28.29; and N,6.95.
Synthesis example D16:
the synthesis was analogous to D1 as a yellow solid in 75% yield. Mass spectrum: m/z 1154.50, elemental analysis experimental value: c,87.32; h,5.41; and N,7.27.
Synthetic example D17:
the synthesis was analogous to D1 as a yellow solid in 75% yield. Mass spectrum: m/z 1508.74, elemental analysis experimental value: c,88.29; h,6.14; n,5.57.
Synthesis example D18:
the synthesis was analogous to D1 as a yellow solid with 79% yield. Mass spectrum: m/z 803.25, elemental analysis experiment value: c,80.68; h,3.64; n,15.68.
Synthetic example D19:
the synthesis was analogous to D1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example D20:
the synthesis was analogous to D1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example D21:
the synthesis was analogous to D1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experiment value: c,80.68; h,3.64; n,15.68.
Synthesis example D22:
the synthesis was analogous to D1 as a yellow solid in 81% yield. Mass spectrum: m/z 848.25, elemental analysis experimental value: c,80.65; h,3.80; n,9.90; and O,5.65.
Synthesis example D23:
the synthesis was analogous to D1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 896.19, elemental analysis experiment value: c,76.32; h,3.60; n,9.37; s,10.72.
Synthetic example D24:
weighing intermediate 26 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound D24, which is a yellow solid with a yield of 83%. Mass spectrum: m/z 886.25, elemental analysis experimental value: c,77.19; h,3.64; f,12.85; and N,6.32.
Synthesis example D25:
the synthesis was analogous to D24 as a yellow solid with 70% yield. Mass spectrum: m/z 928.30, elemental analysis experimental value: c,77.58; h,4.12; f,12.27; n,6.03
Synthesis example D26:
the synthesis was analogous to D24 as a yellow solid in 71% yield. Mass spectrum: m/z 970.35, elemental analysis experimental value: c,77.92; h,4.57; f,11.74; n,5.77
Synthesis example D27:
the synthesis was analogous to D24 as a yellow solid in 73% yield. Mass spectrum: m/z 1012.39, elemental analysis experiment value: c,78.24; h,4.97; f,11.25; n,5.53
Synthesis example D28:
the synthesis was analogous to D24 as a yellow solid in 69% yield. Mass spectrum: m/z 1138.53, elemental analysis experimental value: c,79.06; h,6.02; f,10.00; n,4.92
Synthetic example D29:
the synthesis was analogous to D24 as a yellow solid in 67% yield. Mass spectrum: m/z 1054.44, elemental analysis experimental value: c,78.54; h,5.35; f,10.80; n,5.31
Synthesis example D30:
the synthesis was similar to D24 as a yellow solid in 66% yield. Mass spectrum: m/z 1222.63, elemental analysis experimental value: c,79.51; h,6.59; f,9.32; n,4.58
Synthetic example D31:
the synthesis was analogous to D24 as a yellow solid in 80% yield. Mass spectrum: m/z 1102.37, elemental analysis experiment value: c,71.84; h,5.12; f,10.33; n,5.08; si,7.64
Synthetic example D32:
the synthesis was analogous to D24 as a yellow solid in 73% yield. Mass spectrum: m/z 1304.47, elemental analysis Experimental value: c,68.06; h,6.02; f,8.73; n,4.29; si,12.90
Synthetic example D33:
the synthesis was analogous to D24 as a yellow solid with 72% yield. Mass spectrum: m/z 961.24, elemental analysis experimental value: c,74.92; h,3.04; f,11.85; n,10.19
Synthesis example D34:
the synthesis was analogous to D24 as a yellow solid in 71% yield. Mass spectrum: m/z 1036.22, elemental analysis experimental value: c,72.97; h,2.53; f,10.99; n,13.51
Synthetic example D35:
the synthesis was analogous to D24 as a yellow solid in 69% yield. Mass spectrum: m/z 1114.35, elemental analysis experimental value: c,80.78; h,3.98; f,10.22; n,5.02
Synthetic example D36:
the synthesis was analogous to D24 as a yellow solid in 59% yield. Mass spectrum: m/z 1342.44, elemental analysis experimental value: c,83.14; h,4.20; f,8.48; n,4.17
Synthetic example D37:
the synthesis was analogous to D24 as a yellow solid in 58% yield. Mass spectrum: m/z 1090.22, elemental analysis experimental value: c,66.06; h,2.68; f,26.12; n,5.14
Synthetic example D38:
the synthesis was similar to D24 as a yellow solid in 67% yield. Mass spectrum: m/z 1294.18, elemental analysis experimental value: c,58.44; h,2.02; f,35.21; n,4.33
Synthetic example D39:
the synthesis was analogous to D24 as a yellow solid in 78% yield. Mass spectrum: m/z 1240.49, elemental analysis experimental value: c,81.27; h,5.03; f,9.18; n,4.51
Synthesis example D40:
the synthesis was analogous to D24 as a yellow solid with 70% yield. Mass spectrum: m/z 1594.72, elemental analysis experimental value: c,83.54; h,5.81; f,7.14; n,3.51
Synthesis example D41:
the synthesis was analogous to D24 as a yellow solid in 75% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example D42:
the synthesis was analogous to D24 as a yellow solid in 80% yield. Mass spectrum: m/z 889.24, elemental analysis experimental values: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example D43:
the synthesis was analogous to D24 as a yellow solid in 82% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example D44:
the synthesis was analogous to D24 as a yellow solid in 79% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example D45:
the synthesis was analogous to D24 as a yellow solid in 79% yield. Mass spectrum: m/z 934.24, elemental analysis experimental value: c,73.23; h,3.45; f,12.19; n,5.99; o,5.13
Synthesis example D46:
the synthesis was similar to D24 as a yellow solid in 75% yield. Mass spectrum: m/z 982.17, elemental analysis experimental value: c,69.64; h,3.28; f,11.60; n,5.70; s,9.78
Synthesis example D47:
weighing intermediate 27 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound D47, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example D52:
the synthesis was analogous to D47 as a yellow solid in 70% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthetic example D53:
the synthesis was analogous to D47 as a yellow solid in 74% yield. 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.
Synthesis example D54:
the synthesis was analogous to D47 as a yellow solid with 75% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example D55:
the synthesis was analogous to D47 as a yellow solid in 73% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example D58:
the synthesis was analogous to D47 as a yellow solid in 69% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example D59:
the synthesis was analogous to D47 as a yellow solid in 69% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; o,3.52.
Synthesis example D60:
the synthesis was analogous to D47 as a yellow solid in 78% yield. Mass spectrum: m/z 1562.57, elemental analysis experimental value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example D61:
the synthesis was analogous to D47 as a yellow solid in 74% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; and O,3.62.
Synthesis example D70:
weighing intermediate 28 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound D70, which is a yellow solid with a yield of 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example D75:
the synthesis was analogous to D70 as a yellow solid in 73% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; and O,4.19.
Synthetic example D73:
the synthesis was analogous to D70 as a yellow solid in 70% yield. 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.
Synthetic example D77:
the synthesis was analogous to D70 as a yellow solid in 68% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example D78:
the synthesis was analogous to D70 as a yellow solid in 66% yield. Mass spectrum: m/z 1790.84, elemental analysis experiment value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthetic example D81:
the synthesis was analogous to D70 as a yellow solid in 77% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example D82:
the synthesis was analogous to D70 as a yellow solid in 77% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; o,3.52.
Synthesis example D83:
the synthesis was analogous to D70 as a yellow solid in 74% yield. Mass spectrum: m/z 1562.57, elemental analysis experiment value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example D84:
the synthesis was analogous to D70 as a yellow solid in 71% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; o,3.62.
Synthetic example D93:
weighing intermediate 29 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound D93, a yellow solid with yield of 85%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; o,6.48.
Synthesis example D94:
the synthesis was similar to D93, a yellow solid, 71% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example D95:
the synthesis was analogous to D93, a yellow solid, in 70% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthesis example D96:
the synthesis was analogous to D93 as a yellow solid in 59% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example D97:
the synthesis was analogous to D93, a yellow solid, 58% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example D98:
the synthesis was analogous to D93 as a yellow solid in 55% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54
Synthesis example D99:
the synthesis was analogous to D93, a yellow solid, 59% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthesis example D100:
the synthesis was analogous to D93, a yellow solid, 61% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example D101:
the synthesis was analogous to D93, a yellow solid, in 63% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example D102:
the synthesis was similar to D93 as a yellow solid in 73% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthetic example D103:
the synthesis was similar to D93, a yellow solid, 72% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example D104:
the synthesis was analogous to D93, a yellow solid, yield 79%. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthesis example D105:
the synthesis was analogous to D93, a yellow solid, yield 79%. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example D106:
the synthesis was analogous to D93 as a yellow solid in 74% yield. Mass spectrum: m/z 1190.25, elemental analysis experiment value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthetic example D107:
the synthesis was similar to D93 as a yellow solid in 69% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example D108:
the synthesis was analogous to D93 as a yellow solid in 55% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example D109:
the synthesis was analogous to D93, a yellow solid, 80% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example D110:
the synthesis was similar to D93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example D111:
the synthesis was similar to D93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D112:
the synthesis was analogous to D93, a yellow solid, yield 79%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D113:
the synthesis was analogous to D93, a yellow solid, yield 79%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example D114:
the synthesis was analogous to D93 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example D115:
the synthesis was similar to D93, a yellow solid, 72% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example D116:
weighing intermediate 30 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound D116 as yellow solid with the yield of 83%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthesis example D117:
the synthesis was analogous to D116 as a yellow solid in 77% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthetic example D118:
the synthesis was similar to D116 as a yellow solid in 75% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example D119:
the synthesis was analogous to D116 as a yellow solid in 78% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example D120:
the synthesis was analogous to D116 as a yellow solid in 60% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example D121:
the synthesis was analogous to D116 as a yellow solid in 59% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54.
Synthetic example D122:
the synthesis was analogous to D116 as a yellow solid in 55% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthetic example D123:
the synthesis was analogous to D116 as a yellow solid in 80% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthetic example D124:
the synthesis was analogous to D116 as a yellow solid in 81% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example D125:
the synthesis was analogous to D116 as a yellow solid in 83% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example D126:
the synthesis was analogous to D116 as a yellow solid in 88% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthetic example D127:
the synthesis was analogous to D116 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthesis example D128:
the synthesis was analogous to D116 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; o,4.43.
Synthesis example D129:
the synthesis was analogous to D116 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experiment value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example D130:
the synthesis was analogous to D116 as a yellow solid in 75% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example D131:
the synthesis was analogous to D116 as a yellow solid in 67% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example D132:
the synthesis was analogous to D116 as a yellow solid in 53% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example D133:
the synthesis was analogous to D116 as a yellow solid in 70% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D134:
the synthesis was analogous to D116 as a yellow solid in 80% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example D135:
the synthesis was analogous to D116 as a yellow solid in 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D136:
the synthesis was analogous to D116 as a yellow solid in 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example D137:
the synthesis was analogous to D116 as a yellow solid in 71% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example D138:
the synthesis was analogous to D116 as a yellow solid in 71% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthetic example D139:
weighing intermediate 31 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound D139 as a yellow solid with the yield of 73%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example D140:
the synthesis was analogous to D139 as a yellow solid in 74% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example D141:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthesis example D142:
the synthesis was similar to D139 as a yellow solid with 75% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example D143:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example D144:
the synthesis was analogous to D139 as a yellow solid in 88% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example D145:
the synthesis was analogous to D139 as a yellow solid with 80% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthesis example D146:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example D147:
the synthesis was similar to D139 as a yellow solid in 83% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example D148:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthetic example D149:
the synthesis was analogous to D139 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example D150:
the synthesis was analogous to D139 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthesis example D151:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis of example D152:
the synthesis was analogous to D139 as a yellow solid in 75% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example D153:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthesis example D154:
the synthesis was analogous to D139 as a yellow solid in 69% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example D155:
the synthesis was analogous to D139 as a yellow solid in 79% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example D156:
the synthesis was analogous to D139 as a yellow solid in 58% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D157:
the synthesis was similar to D139 as a yellow solid in 83% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example D158:
the synthesis was analogous to D139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example D159:
the synthesis was analogous to D139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D160:
the synthesis was analogous to D139 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example D161:
the synthesis was analogous to D139 as a yellow solid in 59% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example D162:
weighing intermediate 32 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound D162 as a yellow solid with the yield of 76%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthetic example D163:
the synthesis was analogous to D162 as a yellow solid in 75% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example D164:
the synthesis was analogous to D162 as a yellow solid in 74% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example D165:
the synthesis was analogous to D162 as a yellow solid in 73% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthetic example D166:
the synthesis was analogous to D162 as a yellow solid with 71% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example D167:
the synthesis was analogous to D162 as a yellow solid with 70% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example D168:
the synthesis was analogous to D162 as a yellow solid with 70% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthetic example D169:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example D170:
the synthesis was analogous to D162 as a yellow solid in 70% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example D171:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthesis example D172:
the synthesis was analogous to D162 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example D173:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis of example D174:
the synthesis was similar to D162 as a yellow solid in 75% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; o,4.43.
Synthesis example D175:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthetic example D176:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthetic example D177:
the synthesis was analogous to D162 as a yellow solid in 58% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthesis example D178:
the synthesis was analogous to D162 as a yellow solid in 67% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example D179:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example D180:
the synthesis was analogous to D162 as a yellow solid in 59% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example D181:
the synthesis was analogous to D162 as a yellow solid in 76% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example D182:
the synthesis was analogous to D162 as a yellow solid in 82% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example D183:
the synthesis was analogous to D162 as a yellow solid in 73% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example D184:
the synthesis was analogous to D162 as a yellow solid in 79% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis of intermediate 33:
2, 5-dibromo-3, 4, 6-trifluorobenzonitrile (10g, 39.37mmol), 4-cyanobenzeneboronic acid (13.27g, 69.87mmol) were dissolved in 150mL of toluene, and palladium tetratriphenylphosphine (1.83g, 1.59mmol) and 20mL of an aqueous potassium carbonate solution (8.78g, 63.51mmol) were added, followed by heating and refluxing for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 33 as a white solid, which was weighed at 7.2g, in 63% yield.
Synthesis of intermediates 34-40:
the synthesis method is similar to that of the intermediate 33, and the intermediates 34 to 40 are white solids with the yields of 69%, 74%, 59%, 72%, 76%, 61% and 58% respectively.
Synthesis example E1:
weighing intermediate 33 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound E1, namely a yellow solid, with the yield of 76%. Mass spectrum: m/z 800.93, elemental analysis experimental value: c,85.48; h,4.03; n,10.49.
Synthesis example E2:
the synthesis was analogous to E1 as a yellow solid with 79% yield. Mass spectrum: m/z 842.32, elemental analysis experimental value: c,85.49; h,4.54; and N,9.97.
Synthesis example E3:
the synthesis was analogous to E1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 884.36, elemental analysis experimental value: c,85.49; h,5.01; and N,9.50.
Synthesis example E4:
the synthesis was analogous to E1 as a yellow solid in 72% yield. Mass spectrum: m/z 926.41, elemental analysis experiment value: c,85.50; h,5.44; and N,9.06.
Synthesis example E5:
the synthesis was analogous to E1 as a yellow solid with 71% yield. Mass spectrum: m/z 1052.55, elemental analysis experimental value: c,85.52; h,6.51; and N,7.98.
Synthesis example E6:
the synthesis was analogous to E1 as a yellow solid in 78% yield. Mass spectrum: m/z 968.46, elemental analysis experimental value: c,85.51; h,5.82; n,8.67.
Synthesis example E7:
the synthesis was analogous to E1 as a yellow solid in 79% yield. Mass spectrum: m/z 1136.64, elemental analysis experimental value: c,85.52; h,7.09; and N,7.39.
Synthesis example E8:
the synthesis was analogous to E1 as a yellow solid in 78% yield. Mass spectrum: m/z 1016.39, elemental analysis experiment value: c,77.91; h,5.55; n,8.26; si,8.28.
Synthesis example E9:
the synthesis was analogous to E1 as a yellow solid in 79% yield. Mass spectrum: m/z 1218.49, elemental analysis experimental value: c,72.85; h,6.44; n,6.89; si,13.81.
Synthesis example E10:
the synthesis was analogous to E1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 875.25, elemental analysis experiment value: c,82.27; h,3.34; n,14.39.
Synthesis example E11:
the synthesis was analogous to E1 as a yellow solid in 73% yield. Mass spectrum: m/z 950.24, elemental analysis experimental value: c,79.57; h,2.76; n,17.67.
Synthesis example E12:
the synthesis was analogous to E1 as a yellow solid in 76% yield. Mass spectrum: m/z 1028.36, elemental analysis experimental value: c,87.53; h,4.31; and N,8.17.
Synthesis example E13:
the synthesis was analogous to E1 as a yellow solid in 79% yield. Mass spectrum: m/z 1256.46, elemental analysis experimental value: c,88.83; h,4.49; and N,6.68.
Synthesis example E14:
the synthesis was analogous to E1 as a yellow solid in 69% yield. Mass spectrum: m/z 1004.23, elemental analysis experimental value: c,71.71; h,2.91; f,17.01; and N,8.36.
Synthesis example E15:
the synthesis was analogous to E1 as a yellow solid in 80% yield. Mass spectrum: m/z 1208.19, elemental analysis experimental value: c,62.59; h,2.17; f,28.29; and N,6.95.
Synthesis example E16:
the synthesis was analogous to E1 as a yellow solid in 75% yield. Mass spectrum: m/z 1154.50, elemental analysis experimental value: c,87.32; h,5.41; and N,7.27.
Synthesis example E17:
the synthesis was analogous to E1 as a yellow solid in 75% yield. Mass spectrum: m/z 1508.74, elemental analysis experiment value: c,88.29; h,6.14; n,5.57.
Synthesis example E18:
the synthesis was analogous to E1 as a yellow solid with 79% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example E19:
the synthesis was analogous to E1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 803.25, elemental analysis experiment value: c,80.68; h,3.64; n,15.68.
Synthesis example E20:
the synthesis was analogous to E1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example E21:
the synthesis was analogous to E1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example E22:
the synthesis was analogous to E1 as a yellow solid in 81% yield. Mass spectrum: m/z 848.25, elemental analysis experimental value: c,80.65; h,3.80; n,9.90; o,5.65.
Synthesis example E23:
the synthesis was analogous to E1 as a yellow solid with a yield of 70%. Mass spectrum: m/z 896.19, elemental analysis experimental value: c,76.32; h,3.60; n,9.37; s,10.72.
Synthesis example E24:
weighing intermediate 34 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound E24, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 886.25, elemental analysis experimental values: c,77.19; h,3.64; f,12.85; and N,6.32.
Synthesis example E25:
the synthesis was analogous to E24 as a yellow solid with a yield of 70%. Mass spectrum: m/z 928.30, elemental analysis experimental value: c,77.58; h,4.12; f,12.27; n,6.03
Synthesis example E26:
the synthesis was analogous to E24 as a yellow solid in 71% yield. Mass spectrum: m/z 970.35, elemental analysis experimental value: c,77.92; h,4.57; f,11.74; n,5.77
Synthesis example E27:
the synthesis was analogous to E24 as a yellow solid in 73% yield. Mass spectrum: m/z 1012.39, elemental analysis experimental value: c,78.24; h,4.97; f,11.25; n,5.53
Synthesis example E28:
the synthesis was analogous to E24 as a yellow solid in 69% yield. Mass spectrum: m/z 1138.53, elemental analysis experimental value: c,79.06; h,6.02; f,10.00; n,4.92
Synthetic example E29:
the synthesis was analogous to E24 as a yellow solid in 67% yield. Mass spectrum: m/z 1054.44, elemental analysis experimental value: c,78.54; h,5.35; f,10.80; n,5.31
Synthesis example E30:
the synthesis was similar to E24 as a yellow solid in 66% yield. Mass spectrum: m/z 1222.63, elemental analysis experiment: c,79.51; h,6.59; f,9.32; n,4.58
Synthesis example E31:
the synthesis was analogous to E24 as a yellow solid in 80% yield. Mass spectrum: m/z 1102.37, elemental analysis experimental value: c,71.84; h,5.12; f,10.33; n,5.08; si,7.64
Synthesis example E32:
the synthesis was analogous to E24 as a yellow solid in 73% yield. Mass spectrum: m/z 1304.47, elemental analysis Experimental value: c,68.06; h,6.02; f,8.73; n,4.29; si,12.90
Synthetic example E33:
the synthesis was analogous to E24 as a yellow solid with 72% yield. Mass spectrum: m/z 961.24, elemental analysis experiment value: c,74.92; h,3.04; f,11.85; n,10.19
Synthesis example E34:
the synthesis was analogous to E24 as a yellow solid in 71% yield. Mass spectrum: m/z 1036.22, elemental analysis experimental value: c,72.97; h,2.53; f,10.99; n,13.51
Synthetic example E35:
the synthesis was analogous to E24 as a yellow solid in 69% yield. Mass spectrum: m/z 1114.35, elemental analysis experimental value: c,80.78; h,3.98; f,10.22; n,5.02
Synthesis example E36:
the synthesis was analogous to E24 as a yellow solid in 59% yield. Mass spectrum: m/z 1342.44, elemental analysis experimental value: c,83.14; h,4.20; f,8.48; n,4.17
Synthetic example E37:
the synthesis was analogous to E24 as a yellow solid in 58% yield. Mass spectrum: m/z 1090.22, elemental analysis experimental value: c,66.06; h,2.68; f,26.12; n,5.14
Synthesis example E38:
the synthesis was analogous to E24 as a yellow solid in 67% yield. Mass spectrum: m/z 1294.18, elemental analysis experimental value: c,58.44; h,2.02; f,35.21; n,4.33
Synthesis example E39:
the synthesis was analogous to E24 as a yellow solid with 78% yield. Mass spectrum: m/z 1240.49, elemental analysis experimental value: c,81.27; h,5.03; f,9.18; n,4.51
Synthesis example E40:
the synthesis was analogous to E24 as a yellow solid with 70% yield. Mass spectrum: m/z 1594.72, elemental analysis experimental value: c,83.54; h,5.81; f,7.14; n,3.51
Synthesis example E41:
the synthesis was analogous to E24 as a yellow solid in 75% yield. Mass spectrum: m/z 889.24, elemental analysis experimental values: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example E42:
the synthesis was analogous to E24 as a yellow solid in 80% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example E43:
the synthesis was analogous to E24 as a yellow solid in 82% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example E44:
the synthesis was analogous to E24 as a yellow solid with 79% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example E45:
the synthesis was analogous to E24 as a yellow solid in 79% yield. Mass spectrum: m/z 934.24, elemental analysis experimental value: c,73.23; h,3.45; f,12.19; n,5.99; o,5.13
Synthesis example E46:
the synthesis was analogous to E24 as a yellow solid in 75% yield. Mass spectrum: m/z 982.17, elemental analysis experimental value: c,69.64; h,3.28; f,11.60; n,5.70; s,9.78
Synthesis example E47:
weighing intermediate 35 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound E47, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example E52:
the synthesis was analogous to E47 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthesis example E53:
the synthesis was analogous to E47 as a yellow solid in 74% yield. 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.
Synthesis example E54:
the synthesis was analogous to E47 as a yellow solid in 75% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example E55:
the synthesis was analogous to E47 as a yellow solid in 73% yield. Mass spectrum: m/z 1790.84, elemental analysis experiment value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example E58:
the synthesis was analogous to E47 as a yellow solid in 69% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthetic example E59:
the synthesis was analogous to E47 as a yellow solid in 69% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; and O,3.52.
Synthesis example E60:
the synthesis was analogous to E47 as a yellow solid in 78% yield. Mass spectrum: m/z 1562.57, elemental analysis experiment value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthetic example E61:
the synthesis was analogous to E47 as a yellow solid in 74% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; and O,3.62.
Synthesis example E70:
weighing intermediate 36 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound E70, which is a yellow solid, with a yield of 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example E75:
the synthesis was analogous to E70 as a yellow solid in 73% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthesis example E73:
the synthesis was analogous to E70 as a yellow solid with a yield of 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.
Synthesis example E77:
the synthesis was analogous to E70 as a yellow solid in 68% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example E78:
the synthesis was analogous to E70 as a yellow solid in 66% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example E81:
the synthesis was analogous to E70 as a yellow solid in 77% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example E82:
the synthesis was analogous to E70 as a yellow solid in 77% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; o,3.52.
Synthetic example E83:
the synthesis was analogous to E70 as a yellow solid in 74% yield. Mass spectrum: m/z 1562.57, elemental analysis experiment value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example E84:
the synthesis was analogous to E70 as a yellow solid in 71% yield. Mass spectrum: m/z 1766.53, elemental analysis experiment value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; and O,3.62.
Synthetic example E93:
weighing intermediate 37 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound E93, a yellow solid and a yield of 85%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthesis example E94:
the synthesis was analogous to E93 as a yellow solid in 71% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example E95:
the synthesis was analogous to E93 as a yellow solid in 70% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthesis example E96:
the synthesis was analogous to E93 as a yellow solid in 59% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example E97:
the synthesis was analogous to E93 as a yellow solid in 58% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example E98:
the synthesis was analogous to E93, a yellow solid, 55% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54
Synthesis example E99:
the synthesis was analogous to E93 as a yellow solid in 59% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthesis example E100:
the synthesis was analogous to E93 as a yellow solid in 61% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example E101:
the synthesis was analogous to E93, a yellow solid, in 63% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example E102:
the synthesis was analogous to E93, a yellow solid, 73% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthetic example E103:
the synthesis was analogous to E93 as a yellow solid in 72% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example E104:
the synthesis was analogous to E93 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example E105:
the synthesis was analogous to E93 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example E106:
the synthesis was analogous to E93, a yellow solid, 74% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example E107:
the synthesis was analogous to E93, a yellow solid, 69% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example E108:
the synthesis was analogous to E93 as a yellow solid in 55% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example E109:
the synthesis was analogous to E93 as a yellow solid in 80% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example E110:
the synthesis was analogous to E93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E111:
the synthesis was analogous to E93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E112:
the synthesis was analogous to E93 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example E113:
the synthesis was analogous to E93 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E114:
the synthesis was analogous to E93, a yellow solid, 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example E115:
the synthesis was analogous to E93, a yellow solid, in 72% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example E116:
weighing intermediate 38 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound E116 as a yellow solid with the yield of 83%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthesis example E117:
the synthesis was analogous to E116 as a yellow solid in 77% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example E118:
the synthesis was analogous to E116 as a yellow solid in 75% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthesis example E119:
the synthesis was analogous to E116 as a yellow solid in 78% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example E120:
the synthesis was analogous to E116 as a yellow solid with 60% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example E121:
the synthesis was analogous to E116 as a yellow solid in 59% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example E122:
the synthesis was analogous to E116 as a yellow solid in 55% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthesis example E123:
the synthesis was analogous to E116 as a yellow solid in 80% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example E124:
the synthesis was analogous to E116 as a yellow solid in 81% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example E125:
the synthesis was analogous to E116 as a yellow solid in 83% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthesis example E126:
the synthesis was analogous to E116 as a yellow solid in 88% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example E127:
the synthesis was analogous to E116 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthesis example E128:
the synthesis was analogous to E116 as a yellow solid with 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example E129:
the synthesis was analogous to E116 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example E130:
the synthesis was analogous to E116 as a yellow solid in 75% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example E131:
the synthesis was analogous to E116 as a yellow solid in 67% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthesis example E132:
the synthesis was analogous to E116 as a yellow solid in 53% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example E133:
the synthesis was analogous to E116 as a yellow solid with 70% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E134:
the synthesis was analogous to E116 as a yellow solid in 80% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E135:
the synthesis was analogous to E116 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E136:
the synthesis was analogous to E116 as a yellow solid in 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E137:
the synthesis was analogous to E116 as a yellow solid with 71% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example E138:
the synthesis was analogous to E116 as a yellow solid in 71% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example E139:
weighing intermediate 39 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound E139 as a yellow solid with the yield of 73%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example E140:
the synthesis was analogous to E139 as a yellow solid in 74% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example E141:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthesis example E142:
the synthesis was analogous to E139 as a yellow solid in 75% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example E143:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example E144:
the synthesis was analogous to E139 as a yellow solid with 88% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example E145:
the synthesis was analogous to E139 as a yellow solid with 80% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthesis example E146:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example E147:
the synthesis was analogous to E139 as a yellow solid in 83% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example E148:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthesis example E149:
the synthesis was analogous to E139 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example E150:
the synthesis was analogous to E139 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experiment value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example E151:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; o,4.43.
Synthesis example E152:
the synthesis was analogous to E139 as a yellow solid with 75% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example E153:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example E154:
the synthesis was analogous to E139 as a yellow solid in 69% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthesis example E155:
the synthesis was analogous to E139 as a yellow solid in 79% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example E156:
the synthesis was analogous to E139 as a yellow solid in 58% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E157:
the synthesis was analogous to E139 as a yellow solid in 83% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E158:
the synthesis was analogous to E139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E159:
the synthesis was analogous to E139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E160:
the synthesis was analogous to E139 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example E161:
the synthesis was analogous to E139 as a yellow solid in 59% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example E162:
weighing intermediate 40 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality with dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound E162 as yellow solid with yield of 76%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example E163:
the synthesis was analogous to E162 as a yellow solid in 75% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; o,6.22.
Synthesis example E164:
the synthesis was analogous to E162 as a yellow solid in 74% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthetic example E165:
the synthesis was analogous to E162 as a yellow solid in 73% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthesis example E166:
the synthesis was analogous to E162 as a yellow solid in 71% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example E167:
the synthesis was analogous to E162 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example E168:
the synthesis was analogous to E162 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example E169:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example E170:
the synthesis was analogous to E162 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example E171:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthesis example E172:
the synthesis was analogous to E162 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthesis example E173:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example E174:
the synthesis was analogous to E162 as a yellow solid in 75% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example E175:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example E176:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthesis example E177:
the synthesis was analogous to E162 as a yellow solid in 58% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthesis example E178:
the synthesis was analogous to E162 as a yellow solid in 67% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example E179:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example E180:
the synthesis was analogous to E162 as a yellow solid in 59% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example E181:
the synthesis was analogous to E162 as a yellow solid in 76% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E182:
the synthesis was analogous to E162 as a yellow solid in 82% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example E183:
the synthesis was analogous to E162 as a yellow solid in 73% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example E184:
the synthesis was analogous to E162 as a yellow solid in 79% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis of intermediate 41:
2, 5-dibromo-3, 4, 6-trifluorobenzonitrile (10g, 39.37mmol), 4-cyanobenzeneboronic acid (13.27g, 69.87mmol) were dissolved in 150mL of toluene, and palladium tetratriphenylphosphine (1.83g, 1.59mmol) and 20mL of an aqueous potassium carbonate solution (8.78g, 63.51mmol) were added, followed by heating and refluxing for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 41 as a white solid, which was weighed at 7.2g, in 63% yield.
Synthesis of intermediates 42-48:
the synthesis method is similar to intermediate 41, and intermediates 42-48 are all white solids with yields of 55%, 64%, 58%, 62%, 66%, 51% and 55%, respectively.
Synthesis example F1:
weighing intermediate 41 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F1, namely a yellow solid, with the yield of 76%. Mass spectrum: m/z 800.93, elemental analysis experimental value: c,85.48; h,4.03; n,10.49.
Synthesis example F2:
the synthesis was similar to F1, yellow solid, 79% yield. Mass spectrum: m/z 842.32, elemental analysis experimental value: c,85.49; h,4.54; and N,9.97.
Synthesis example F3:
the synthesis was similar to F1, yellow solid, 70% yield. Mass spectrum: m/z 884.36, elemental analysis experimental value: c,85.49; h,5.01; and N,9.50.
Synthesis example F4:
the synthesis was similar to F1, yellow solid, 72% yield. Mass spectrum: m/z 926.41, elemental analysis experiment value: c,85.50; h,5.44; and N,9.06.
Synthesis example F5:
the synthesis was similar to F1, yellow solid, 71% yield. Mass spectrum: m/z 1052.55, elemental analysis experimental value: c,85.52; h,6.51; and N,7.98.
Synthesis example F6:
the synthesis was analogous to F1 as a yellow solid in 78% yield. Mass spectrum: m/z 968.46, elemental analysis experiment value: c,85.51; h,5.82; n,8.67.
Synthetic example F7:
the synthesis was analogous to F1 as a yellow solid in 79% yield. Mass spectrum: m/z 1136.64, elemental analysis experimental value: c,85.52; h,7.09; and N,7.39.
Synthesis example F8:
the synthesis was similar to F1, yellow solid, 78% yield. Mass spectrum: m/z 1016.39, elemental analysis experimental value: c,77.91; h,5.55; n,8.26; si,8.28.
Synthetic example F9:
the synthesis was similar to F1, yellow solid, 79% yield. Mass spectrum: m/z 1218.49, elemental analysis experimental value: c,72.85; h,6.44; n,6.89; si,13.81.
Synthesis example F10:
the synthesis was similar to F1, yellow solid, 70% yield. Mass spectrum: m/z 875.25, elemental analysis experimental value: c,82.27; h,3.34; n,14.39.
Synthesis example F11:
the synthesis was similar to F1 as a yellow solid in 73% yield. Mass spectrum: m/z 950.24, elemental analysis experimental value: c,79.57; h,2.76; n,17.67.
Synthesis example F12:
the synthesis was analogous to F1 as a yellow solid in 76% yield. Mass spectrum: m/z 1028.36, elemental analysis experimental value: c,87.53; h,4.31; and N,8.17.
Synthesis example F13:
the synthesis was analogous to F1 as a yellow solid in 79% yield. Mass spectrum: m/z 1256.46, experimental value of elemental analysis: c,88.83; h,4.49; and N,6.68.
Synthesis example F14:
the synthesis was similar to F1, yellow solid, 69% yield. Mass spectrum: m/z 1004.23, elemental analysis experimental value: c,71.71; h,2.91; f,17.01; and N,8.36.
Synthesis example F15:
the synthesis was similar to F1, yellow solid, yield 80%. Mass spectrum: m/z 1208.19, elemental analysis experimental value: c,62.59; h,2.17; f,28.29; and N,6.95.
Synthetic example F16:
the synthesis was analogous to F1 as a yellow solid in 75% yield. Mass spectrum: m/z 1154.50, elemental analysis experimental value: c,87.32; h,5.41; and N,7.27.
Synthesis example F17:
the synthesis was analogous to F1 as a yellow solid in 75% yield. Mass spectrum: m/z 1508.74, elemental analysis experimental value: c,88.29; h,6.14; n,5.57.
Synthetic example F18:
the synthesis was similar to F1, yellow solid, 79% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthetic example F19:
the synthesis was similar to F1, yellow solid, 70% yield. Mass spectrum: m/z 803.25, elemental analysis experiment value: c,80.68; h,3.64; n,15.68.
Synthesis example F20:
the synthesis was analogous to F1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example F21:
the synthesis was analogous to F1 as a yellow solid in 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example F22:
the synthesis was similar to F1, yellow solid, 81% yield. Mass spectrum: m/z 848.25, elemental analysis experimental value: c,80.65; h,3.80; n,9.90; o,5.65.
Synthetic example F23:
the synthesis was similar to F1, yellow solid, 70% yield. Mass spectrum: m/z 896.19, elemental analysis experiment value: c,76.32; h,3.60; n,9.37; s,10.72.
Synthetic example F24:
weighing intermediate 42 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F24 which is a yellow solid and has the yield of 83%. Mass spectrum: m/z 886.25, elemental analysis experimental value: c,77.19; h,3.64; f,12.85; and N,6.32.
Synthesis example F25:
the synthesis was similar to F24 as a yellow solid with a yield of 70%. Mass spectrum: m/z 928.30, elemental analysis experimental value: c,77.58; h,4.12; f,12.27; n,6.03
Synthetic example F26:
the synthesis was similar to F24 as a yellow solid in 71% yield. Mass spectrum: m/z 970.35, elemental analysis experimental value: c,77.92; h,4.57; f,11.74; n,5.77
Synthetic example F27:
the synthesis was similar to F24 as a yellow solid in 73% yield. Mass spectrum: m/z 1012.39, elemental analysis experimental value: c,78.24; h,4.97; f,11.25; n,5.53
Synthetic example F28:
the synthesis was similar to F24 as a yellow solid in 69% yield. Mass spectrum: m/z 1138.53, elemental analysis experimental value: c,79.06; h,6.02; f,10.00; n,4.92
Synthetic example F29:
the synthesis was similar to F24 as a yellow solid in 67% yield. Mass spectrum: m/z 1054.44, elemental analysis experimental value: c,78.54; h,5.35; f,10.80; n,5.31
Synthesis example F30:
the synthesis was similar to F24 as a yellow solid in 66% yield. Mass spectrum: m/z 1222.63, elemental analysis experiment: c,79.51; h,6.59; f,9.32; n,4.58
Synthetic example F31:
the synthesis was similar to F24, a yellow solid, 80% yield. Mass spectrum: m/z 1102.37, elemental analysis experimental value: c,71.84; h,5.12; f,10.33; n,5.08; si,7.64
Synthetic example F32:
the synthesis was similar to F24 as a yellow solid in 73% yield. Mass spectrum: m/z 1304.47, elemental analysis experimental value: c,68.06; h,6.02; f,8.73; n,4.29; si,12.90
Synthetic example F33:
the synthesis was similar to F24 as a yellow solid with 72% yield. Mass spectrum: m/z 961.24, elemental analysis experimental value: c,74.92; h,3.04; f,11.85; n,10.19
Synthetic example F34:
the synthesis was analogous to F24 as a yellow solid with 71% yield. Mass spectrum: m/z 1036.22, elemental analysis experimental value: c,72.97; h,2.53; f,10.99; n,13.51
Synthesis example F35:
the synthesis was similar to F24 as a yellow solid in 69% yield. Mass spectrum: m/z 1114.35, elemental analysis experimental value: c,80.78; h,3.98; f,10.22; n,5.02
Synthesis example F36:
the synthesis was analogous to F24 as a yellow solid in 59% yield. Mass spectrum: m/z 1342.44, elemental analysis experimental value: c,83.14; h,4.20; f,8.48; n,4.17
Synthetic example F37:
the synthesis was analogous to F24 as a yellow solid in 58% yield. Mass spectrum: m/z 1090.22, elemental analysis experimental value: c,66.06; h,2.68; f,26.12; n,5.14
Synthetic example F38:
the synthesis was similar to F24 as a yellow solid in 67% yield. Mass spectrum: m/z 1294.18, elemental analysis experimental value: c,58.44; h,2.02; f,35.21; n,4.33
Synthetic example F39:
the synthesis was similar to F24 as a yellow solid in 78% yield. Mass spectrum: m/z 1240.49, elemental analysis experimental value: c,81.27; h,5.03; f,9.18; n,4.51
Synthesis example F40:
the synthesis was similar to F24 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1594.72, elemental analysis experimental value: c,83.54; h,5.81; f,7.14; n,3.51
Synthesis example F41:
the synthesis was similar to F24 as a yellow solid in 75% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example F42:
the synthesis was similar to F24, a yellow solid, 80% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthetic example F43:
the synthesis was similar to F24 as a yellow solid in 82% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; f,12.81; n,11.02
Synthesis example F44:
the synthesis was analogous to F24 as a yellow solid in 79% yield. Mass spectrum: m/z 889.24, elemental analysis experimental values: c,72.89; h,3.28; f,12.81; n,11.02
Synthetic example F45:
the synthesis was similar to F24 as a yellow solid in 79% yield. Mass spectrum: m/z 934.24, elemental analysis experimental value: c,73.23; h,3.45; f,12.19; n,5.99; o,5.13
Synthesis example F46:
the synthesis was similar to F24 as a yellow solid in 75% yield. Mass spectrum: m/z 982.17, elemental analysis experimental value: c,69.64; h,3.28; f,11.60; n,5.70; s,9.78
Synthesis example F47:
weighing intermediate 43 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F47 which is a yellow solid and has the yield of 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example F52:
the synthesis was analogous to F47 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; and O,4.19.
Synthetic example F53:
the synthesis was analogous to F47 as a yellow solid in 74% yield. 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.
Synthetic example F54:
the synthesis was analogous to F47 as a yellow solid with 75% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example F55:
the synthesis was analogous to F47 as a yellow solid in 73% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example F58:
the synthesis was analogous to F47 as a yellow solid in 69% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example F59:
the synthesis was analogous to F47 as a yellow solid in 69% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; and O,3.52.
Synthesis example F60:
the synthesis was analogous to F47 as a yellow solid in 78% yield. Mass spectrum: m/z 1562.57, elemental analysis experimental value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthetic example F61:
the synthesis was analogous to F47 as a yellow solid in 74% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; o,3.62.
Synthesis example F70:
weighing intermediate 44 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F70, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthetic example F75:
the synthesis was similar to F70 as a yellow solid in 73% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthesis example F73:
the synthesis was similar to F70, a yellow solid, in 70% yield. 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.
Synthetic example F77:
the synthesis was similar to F70 as a yellow solid in 68% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example F78:
the synthesis was similar to F70, a yellow solid, 66% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthesis example F81:
the synthesis was analogous to F70 as a yellow solid in 77% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthesis example F82:
the synthesis was similar to F70, a yellow solid, 77% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; o,3.52.
Synthetic example F83:
the synthesis was analogous to F70 as a yellow solid in 74% yield. Mass spectrum: m/z 1562.57, elemental analysis experiment value: c,75.29; h,4.71; b,1.38; f,10.94; n,3.58; and O,4.09.
Synthesis example F84:
the synthesis was similar to F70, a yellow solid, 71% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; f,19.35; n,3.17; and O,3.62.
Synthetic example F93:
weighing intermediate 45 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F93, a yellow solid and a yield of 85%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthetic example F94:
the synthesis was similar to F93, a yellow solid, 71% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example F95:
the synthesis was analogous to F93, a yellow solid, in 70% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthetic example F96:
the synthesis was analogous to F93, a yellow solid, 59% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example F97:
the synthesis was similar to F93 as a yellow solid in 58% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example F98:
the synthesis was similar to F93 as a yellow solid in 55% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54
Synthesis example F99:
the synthesis was similar to F93 as a yellow solid in 59% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthesis example F100:
the synthesis was similar to F93 as a yellow solid in 61% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example F101:
the synthesis was analogous to F93, a yellow solid, in 63% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example F102:
the synthesis was similar to F93 as a yellow solid in 73% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example F103:
the synthesis was analogous to F93, a yellow solid, in 72% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthesis example F104:
the synthesis was similar to F93, a yellow solid, 79% yield. Mass spectrum: m/z 1214.38, elemental analysis experiment value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example F105:
the synthesis was analogous to F93, a yellow solid, yield 79%. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example F106:
the synthesis was similar to F93 as a yellow solid in 74% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthetic example F107:
the synthesis was similar to F93 as a yellow solid in 69% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example F108:
the synthesis was analogous to F93, a yellow solid, 55% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example F109:
the synthesis was similar to F93, a yellow solid, 80% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example F110:
the synthesis was analogous to F93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example F111:
the synthesis was analogous to F93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example F112:
the synthesis was analogous to F93, a yellow solid, yield 79%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example F113:
the synthesis was analogous to F93, a yellow solid, yield 79%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example F114:
the synthesis was analogous to F93, a yellow solid, 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example F115:
the synthesis was similar to F93, a yellow solid, 72% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example F116:
weighing intermediate 46 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound F116, a yellow solid with the yield of 83%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; o,6.48.
Synthesis example F117:
the synthesis was analogous to F116 as a yellow solid in 77% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthetic example F118:
the synthesis was analogous to F116 as a yellow solid in 75% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example F119:
the synthesis was analogous to F116 as a yellow solid in 78% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthetic example F120:
the synthesis was similar to F116 as a yellow solid with 60% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example F121:
the synthesis was similar to F116 as a yellow solid in 59% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthetic example F122:
the synthesis was similar to F116 as a yellow solid in 55% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example F123:
the synthesis was similar to F116 as a yellow solid in 80% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example F124:
the synthesis was analogous to F116 as a yellow solid in 81% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example F125:
the synthesis was analogous to F116 as a yellow solid in 83% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example F126:
the synthesis was analogous to F116 as a yellow solid in 88% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthesis example F127:
the synthesis was similar to F116 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthetic example F128:
the synthesis was analogous to F116 as a yellow solid with 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example F129:
the synthesis was analogous to F116 as a yellow solid with 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example F130:
the synthesis was analogous to F116 as a yellow solid in 75% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example F131:
the synthesis was analogous to F116 as a yellow solid in 67% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example F132:
the synthesis was similar to F116 as a yellow solid in 53% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example F133:
the synthesis was similar to F116 as a yellow solid with a yield of 70%. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example F134:
the synthesis was similar to F116 as a yellow solid in 80% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example F135:
the synthesis was analogous to F116 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example F136:
the synthesis was analogous to F116 as a yellow solid in 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example F137:
the synthesis was similar to F116 as a yellow solid in 71% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example F138:
the synthesis was similar to F116 as a yellow solid in 71% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example F139:
weighing intermediate 47 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying, and carrying out column chromatography to obtain compound F139 as yellow solid with the yield of 73%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example F140:
the synthesis was similar to F139 as a yellow solid in 74% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; o,6.22.
Synthesis example F141:
the synthesis was analogous to F139 as a yellow solid in 79% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthesis example F142:
the synthesis was analogous to F139 as a yellow solid in 75% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example F143:
the synthesis was similar to F139 as a yellow solid with 79% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example F144:
the synthesis was analogous to F139 as a yellow solid with 88% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54.
Synthesis example F145:
the synthesis was analogous to F139 as a yellow solid with 80% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example F146:
the synthesis was similar to F139 as a yellow solid with 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthetic example F147:
the synthesis was similar to F139 as a yellow solid in 83% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthesis example F148:
the synthesis was similar to F139 as a yellow solid with 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example F149:
the synthesis was analogous to F139 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthesis example F150:
the synthesis was analogous to F139 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthesis example F151:
the synthesis was similar to F139 as a yellow solid with 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example F152:
the synthesis was analogous to F139 as a yellow solid in 75% yield. Mass spectrum: m/z 1190.25, elemental analysis experiment value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthesis example F153:
the synthesis was similar to F139 as a yellow solid with 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; and O,4.59.
Synthesis example F154:
the synthesis was similar to F139 as a yellow solid in 69% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example F155:
the synthesis was analogous to F139 as a yellow solid in 79% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example F156:
the synthesis was analogous to F139 as a yellow solid in 58% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example F157:
the synthesis was analogous to F139 as a yellow solid in 83% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example F158:
the synthesis was similar to F139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example F159:
the synthesis was similar to F139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example F160:
the synthesis was similar to F139 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example F161:
the synthesis was similar to F139 as a yellow solid with 59% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthetic example F162:
weighing intermediate 48 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound F162 as a yellow solid with the yield of 76%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example F163:
the synthesis was similar to F162 as a yellow solid in 75% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example F164:
the synthesis was similar to F162 as a yellow solid in 74% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example F165:
the synthesis was similar to F162 as a yellow solid in 73% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthetic example F166:
the synthesis was similar to F162 as a yellow solid in 71% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example F167:
the synthesis was similar to F162 as a yellow solid in 70% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthesis example F168:
the synthesis was analogous to F162 as a yellow solid with 70% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example F169:
the synthesis was similar to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example F170:
the synthesis was analogous to F162 as a yellow solid with 70% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example F171:
the synthesis was similar to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthesis example F172:
the synthesis was similar to F162 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthetic example F173:
the synthesis was similar to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthesis example F174:
the synthesis was similar to F162 as a yellow solid in 75% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example F175:
the synthesis was similar to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; f,14.36; n,4.70; o,5.37.
Synthetic example F176:
the synthesis was analogous to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; f,24.51; n,4.02; o,4.59.
Synthetic example F177:
the synthesis was analogous to F162 as a yellow solid in 58% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example F178:
the synthesis was analogous to F162 as a yellow solid in 67% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthesis example F179:
the synthesis was similar to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example F180:
the synthesis was analogous to F162 as a yellow solid in 59% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example F181:
the synthesis was similar to F162 as a yellow solid in 76% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example F182:
the synthesis was analogous to F162 as a yellow solid in 82% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example F183:
the synthesis was similar to F162 as a yellow solid in 73% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthesis example F184:
the synthesis was analogous to F162 as a yellow solid in 79% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis of intermediate 49:
2, 3-dibromo-4, 5, 6-trifluorobenzonitrile (10g, 39.37mmol), 4-cyanophenylboronic acid (13.27g, 69.87mmol) were dissolved in 150mL of toluene, palladium tetratriphenylphosphine (1.83g, 1.59mmol) and 20mL of an aqueous potassium carbonate solution (8.78g, 63.51mmol) were added, and the mixture was refluxed for 24 hours. After cooling, liquid separation, extraction, drying and column chromatography (petroleum ether: dichloromethane = 3) gave intermediate 49 as a white solid weighing 6.6g with a yield of 58%.
Synthesis of intermediates 50 to 56:
the synthesis method is similar to that of intermediate 49, and intermediates 50-56 are all white solids with yields of 60%, 71%, 68%, 59%, 74%, 69% and 66%, respectively.
Synthetic example G1:
weighing intermediate 49 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound G1, yellow solid with yield of 76%. Mass spectrum: m/z 800.93, elemental analysis experimental value: c,85.48; h,4.03; n,10.49.
Synthesis example G2:
the synthesis was similar to G1, yellow solid, 79% yield. Mass spectrum: m/z 842.32, elemental analysis experimental value: c,85.49; h,4.54; and N,9.97.
Synthetic example G3:
the synthesis was similar to G1, yellow solid, 70% yield. Mass spectrum: m/z 884.36, elemental analysis experimental value: c,85.49; h,5.01; and N,9.50.
Synthetic example G4:
the synthesis was similar to G1, yellow solid, 72% yield. Mass spectrum: m/z 926.41, elemental analysis experimental value: c,85.50; h,5.44; and N,9.06.
Synthesis example G5:
the synthesis was analogous to G1 as a yellow solid in 71% yield. Mass spectrum: m/z 1052.55, elemental analysis experimental value: c,85.52; h,6.51; and N,7.98.
Synthetic example G6:
the synthesis was similar to G1, yellow solid, 78% yield. Mass spectrum: m/z 968.46, elemental analysis experimental value: c,85.51; h,5.82; n,8.67.
Synthetic example G7:
the synthesis was similar to G1, yellow solid, 79% yield. Mass spectrum: m/z 1136.64, elemental analysis experimental value: c,85.52; h,7.09; and N,7.39.
Synthesis example G8:
the synthesis was analogous to G1 as a yellow solid in 78% yield. Mass spectrum: m/z 1016.39, elemental analysis experiment value: c,77.91; h,5.55; n,8.26; si,8.28.
Synthesis example G9:
the synthesis was similar to G1, yellow solid, 79% yield. Mass spectrum: m/z 1218.49, elemental analysis experimental value: c,72.85; h,6.44; n,6.89; si,13.81.
Synthesis example G10:
the synthesis was similar to G1, yellow solid, 70% yield. Mass spectrum: m/z 875.25, elemental analysis experiment value: c,82.27; h,3.34; n,14.39.
Synthetic example G11:
the synthesis was analogous to G1 as a yellow solid in 73% yield. Mass spectrum: m/z 950.24, elemental analysis experimental value: c,79.57; h,2.76; n,17.67.
Synthetic example G12:
the synthesis was similar to G1, yellow solid, 76% yield. Mass spectrum: m/z 1028.36, elemental analysis experimental value: c,87.53; h,4.31; and N,8.17.
Synthetic example G13:
the synthesis was analogous to G1 as a yellow solid in 79% yield. Mass spectrum: m/z 1256.46, experimental value of elemental analysis: c,88.83; h,4.49; and N,6.68.
Synthesis example G14:
the synthesis was similar to G1, yellow solid, 69% yield. Mass spectrum: m/z 1004.23, elemental analysis experimental value: c,71.71; h,2.91; g,17.01; and N,8.36.
Synthesis example G15:
the synthesis was similar to G1, yellow solid, 80% yield. Mass spectrum: m/z 1208.19, elemental analysis experimental value: c,62.59; h,2.17; g,28.29; and N,6.95.
Synthetic example G16:
the synthesis was similar to G1, yellow solid, 75% yield. Mass spectrum: m/z 1154.50, elemental analysis experimental value: c,87.32; h,5.41; and N,7.27.
Synthetic example G17:
the synthesis was analogous to G1 as a yellow solid in 75% yield. Mass spectrum: m/z 1508.74, elemental analysis experiment value: c,88.29; h,6.14; n,5.57.
Synthesis example G18:
the synthesis was analogous to G1 as a yellow solid in 79% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthetic example G19:
the synthesis was similar to G1, yellow solid, 70% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example G20:
the synthesis was similar to G1, yellow solid, 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthetic example G21:
the synthesis was similar to G1, yellow solid, 69% yield. Mass spectrum: m/z 803.25, elemental analysis experimental value: c,80.68; h,3.64; n,15.68.
Synthesis example G22:
the synthesis was similar to G1, yellow solid, 81% yield. Mass spectrum: m/z 848.25, elemental analysis experimental value: c,80.65; h,3.80; n,9.90; o,5.65.
Synthetic example G23:
the synthesis was similar to G1, yellow solid, 70% yield. Mass spectrum: m/z 896.19, elemental analysis experiment value: c,76.32; h,3.60; n,9.37; s,10.72.
Synthesis example G24:
weighing intermediate 50 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound G24, a yellow solid with the yield of 83%. Mass spectrum: m/z 886.25, elemental analysis experimental values: c,77.19; h,3.64; g,12.85; and N,6.32.
Synthesis example G25:
the synthesis was analogous to G24 as a yellow solid in 70% yield. Mass spectrum: m/z 928.30, elemental analysis experimental value: c,77.58; h,4.12; g,12.27; n,6.03
Synthesis example G26:
the synthesis was similar to G24, a yellow solid, 71% yield. Mass spectrum: m/z 970.35, elemental analysis experimental value: c,77.92; h,4.57; g,11.74; n,5.77
Synthesis example G27:
the synthesis was similar to G24, yellow solid, 73% yield. Mass spectrum: m/z 1012.39, elemental analysis experimental value: c,78.24; h,4.97; g,11.25; n,5.53
Synthesis example G28:
the synthesis was similar to G24, a yellow solid, 69% yield. Mass spectrum: m/z 1138.53, elemental analysis experimental value: c,79.06; h,6.02; g,10.00; n,4.92
Synthetic example G29:
the synthesis was similar to G24, yellow solid, 67% yield. Mass spectrum: m/z 1054.44, elemental analysis experimental value: c,78.54; h,5.35; g,10.80; n,5.31
Synthetic example G30:
the synthesis was similar to G24, yellow solid, 66% yield. Mass spectrum: m/z 1222.63, elemental analysis experiment: c,79.51; h,6.59; g,9.32; n,4.58
Synthetic example G31:
the synthesis was similar to G24, a yellow solid, 80% yield. Mass spectrum: m/z 1102.37, elemental analysis experiment value: c,71.84; h,5.12; g,10.33; n,5.08; si,7.64
Synthetic example G32:
the synthesis was similar to G24, yellow solid, 73% yield. Mass spectrum: m/z 1304.47, elemental analysis Experimental value: c,68.06; h,6.02; g,8.73; n,4.29; si,12.90
Synthetic example G33:
the synthesis was similar to G24, a yellow solid, in 72% yield. Mass spectrum: m/z 961.24, elemental analysis experiment value: c,74.92; h,3.04; g,11.85; n,10.19
Synthesis example G34:
the synthesis was similar to G24, a yellow solid, 71% yield. Mass spectrum: m/z 1036.22, elemental analysis experimental value: c,72.97; h,2.53; g,10.99; n,13.51
Synthetic example G35:
the synthesis was similar to G24, a yellow solid, 69% yield. Mass spectrum: m/z 1114.35, elemental analysis experimental value: c,80.78; h,3.98; g,10.22; n,5.02
Synthetic example G36:
the synthesis was analogous to G24 as a yellow solid in 59% yield. Mass spectrum: m/z 1342.44, elemental analysis experimental value: c,83.14; h,4.20; g,8.48; n,4.17
Synthetic example G37:
the synthesis was analogous to G24 as a yellow solid in 58% yield. Mass spectrum: m/z 1090.22, elemental analysis experimental value: c,66.06; h,2.68; g,26.12; n,5.14
Synthetic example G38:
the synthesis was similar to G24, yellow solid, 67% yield. Mass spectrum: m/z 1294.18, elemental analysis experimental value: c,58.44; h,2.02; g,35.21; n,4.33
Synthetic example G39:
the synthesis was analogous to G24 as a yellow solid in 78% yield. Mass spectrum: m/z 1240.49, elemental analysis experimental value: c,81.27; h,5.03; g,9.18; n,4.51
Synthetic example G40:
the synthesis was similar to G24, yellow solid, 70% yield. Mass spectrum: m/z 1594.72, elemental analysis experimental value: c,83.54; h,5.81; g,7.14; n,3.51
Synthesis example G41:
the synthesis was similar to G24, yellow solid, 75% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; g,12.81; n,11.02
Synthesis example G42:
the synthesis was similar to G24, a yellow solid, 80% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; g,12.81; n,11.02
Synthetic example G43:
the synthesis was similar to G24, yellow solid, 82% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; g,12.81; n,11.02
Synthetic example G44:
the synthesis was analogous to G24 as a yellow solid in 79% yield. Mass spectrum: m/z 889.24, elemental analysis experimental value: c,72.89; h,3.28; g,12.81; n,11.02
Synthetic example G45:
the synthesis was similar to G24, yellow solid, 79% yield. Mass spectrum: m/z 934.24, elemental analysis experimental value: c,73.23; h,3.45; g,12.19; n,5.99; o,5.13
Synthetic example G46:
the synthesis was similar to G24, yellow solid, 75% yield. Mass spectrum: m/z 982.17, elemental analysis experimental value: c,69.64; h,3.28; g,11.60; n,5.70; s,9.78
Synthetic example G47:
weighing intermediate 51 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound G47, a yellow solid with a yield of 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example G52:
the synthesis was similar to G47 as a yellow solid with a yield of 70%. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; and O,4.19.
Synthetic example G53:
the synthesis was analogous to G47 as a yellow solid in 74% yield. 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.
Synthetic example G54:
the synthesis was similar to G47 as a yellow solid in 75% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthetic example G55:
the synthesis was similar to G47 as a yellow solid in 73% yield. Mass spectrum: m/z 1790.84, elemental analysis experiment value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthetic example G58:
the synthesis was analogous to G47 as a yellow solid in 69% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthetic example G59:
the synthesis was similar to G47 as a yellow solid in 69% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; and O,3.52.
Synthesis example G60:
the synthesis was analogous to G47 as a yellow solid with 78% yield. Mass spectrum: m/z 1562.57, elemental analysis experimental value: c,75.29; h,4.71; b,1.38; g,10.94; n,3.58; and O,4.09.
Synthetic example G61:
the synthesis was analogous to G47 as a yellow solid in 74% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; g,19.35; n,3.17; and O,3.62.
Synthesis example G70:
weighing intermediate 52 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound G70, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example G75:
the synthesis was similar to G70, a yellow solid, 73% yield. Mass spectrum: m/z 1526.79, elemental analysis experimental value: c,84.13; h,6.60; b,1.42; n,3.67; o,4.19.
Synthetic example G73:
the synthesis was similar to G70, a yellow solid, in 70% yield. 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.
Synthetic example G77:
the synthesis was similar to G70, a yellow solid, 68% yield. Mass spectrum: m/z 1574.72, elemental analysis experimental value: c,79.27; h,6.40; b,1.37; n,3.56; o,4.06; si,5.35.
Synthesis example G78:
the synthesis was similar to G70, yellow solid, 66% yield. Mass spectrum: m/z 1790.84, elemental analysis experimental value: c,75.72; h,6.97; b,1.21; n,3.13; o,3.57; si,9.40.
Synthetic example G81:
the synthesis was similar to G70, a yellow solid, 77% yield. Mass spectrum: m/z 1586.70, elemental analysis experimental value: c,85.49; h,5.59; b,1.36; n,3.53; and O,4.03.
Synthetic example G82:
the synthesis was similar to G70, a yellow solid, 77% yield. Mass spectrum: m/z 1814.79, elemental analysis experimental value: c,86.65; h,5.55; b,1.19; n,3.09; and O,3.52.
Synthetic example G83:
the synthesis was analogous to G70 as a yellow solid in 74% yield. Mass spectrum: m/z 1562.57, elemental analysis experimental value: c,75.29; h,4.71; b,1.38; g,10.94; n,3.58; and O,4.09.
Synthetic example G84:
the synthesis was similar to G70, a yellow solid, 71% yield. Mass spectrum: m/z 1766.53, elemental analysis experimental value: c,68.64; h,3.99; b,1.22; g,19.35; n,3.17; and O,3.62.
Synthetic example G93:
weighing intermediate 53 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting pH to neutrality by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain compound G93, a yellow solid and a yield of 85%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; and O,6.48.
Synthetic example G94:
the synthesis was similar to G93, a yellow solid, 71% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthesis example G95:
the synthesis was similar to G93, a yellow solid, 70% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthesis example G96:
the synthesis was similar to G93, a yellow solid, 59% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthetic example G97:
the synthesis was analogous to G93, a yellow solid, 58% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example G98:
the synthesis was similar to G93, a yellow solid, 55% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54
Synthesis example G99:
the synthesis was similar to G93, a yellow solid, 59% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example G100:
the synthesis was similar to G93, a yellow solid, 61% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthetic example G101:
the synthesis was similar to G93, a yellow solid, 63% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example G102:
the synthesis was similar to G93, a yellow solid, 73% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthetic example G103:
the synthesis was similar to G93, a yellow solid, 72% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthetic example G104:
the synthesis was similar to G93, a yellow solid, 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthetic example G105:
the synthesis was similar to G93, a yellow solid, 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example G106:
the synthesis was similar to G93, a yellow solid, 74% yield. Mass spectrum: m/z 1190.25, elemental analysis experiment value: c,72.61; h,2.96; g,14.36; n,4.70; o,5.37.
Synthetic example G107:
the synthesis was similar to G93, a yellow solid, 69% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; g,24.51; n,4.02; and O,4.59.
Synthetic example G108:
the synthesis was similar to G93, a yellow solid, 55% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example G109:
the synthesis was similar to G93, a yellow solid, 80% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example G110:
the synthesis was similar to G93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G111:
the synthesis was similar to G93, a yellow solid, 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G112:
the synthesis was similar to G93, a yellow solid, 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example G113:
the synthesis was similar to G93, a yellow solid, in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example G114:
the synthesis was similar to G93, a yellow solid, 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example G115:
the synthesis was similar to G93, a yellow solid, in 72% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthetic example G116:
weighing intermediate 54 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound G116, namely a yellow solid, wherein the yield is 83%. Mass spectrum: m/z 986.29, elemental analysis experimental value: c,83.96; h,3.88; n,5.68; o,6.48.
Synthesis example G117:
the synthesis was similar to G116 as a yellow solid in 77% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthetic example G118:
the synthesis was analogous to G116 as a yellow solid in 75% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example G119:
the synthesis was similar to G116 as a yellow solid in 78% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthetic example G120:
the synthesis was similar to G116 as a yellow solid in 60% yield. Mass spectrum: m/z 1238.57, elemental analysis Experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example G121:
the synthesis was similar to G116 as a yellow solid in 59% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthetic example G122:
the synthesis was analogous to G116 as a yellow solid in 55% yield. Mass spectrum: m/z 1322.66, elemental analysis experimental value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example G123:
the synthesis was similar to G116 as a yellow solid in 80% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthetic example G124:
the synthesis was analogous to G116 as a yellow solid in 81% yield. Mass spectrum: m/z 1418.53, elemental analysis experiment value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example G125:
the synthesis was similar to G116 as a yellow solid in 83% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthetic example G126:
the synthesis was analogous to G116 as a yellow solid in 88% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; and O,5.63.
Synthetic example G127:
the synthesis was similar to G116 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthetic example G128:
the synthesis was analogous to G116 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example G129:
the synthesis was analogous to G116 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; g,14.36; n,4.70; o,5.37.
Synthesis example G130:
the synthesis was similar to G116 as a yellow solid in 75% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; g,24.51; n,4.02; and O,4.59.
Synthetic example G131:
the synthesis was analogous to G116 as a yellow solid in 67% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example G132:
the synthesis was analogous to G116 as a yellow solid in 53% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example G133:
the synthesis was similar to G116 as a yellow solid in 70% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G134:
the synthesis was similar to G116 as a yellow solid in 80% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G135:
the synthesis was analogous to G116 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G136:
the synthesis was analogous to G116 as a yellow solid in 75% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthesis example G137:
the synthesis was analogous to G116 as a yellow solid in 71% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example G138:
the synthesis was similar to G116 as a yellow solid in 71% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthetic example G139:
weighing intermediate 55 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolving in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound G139 as a yellow solid with the yield of 73%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example G140:
the synthesis was similar to G139 as a yellow solid in 74% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; o,6.22.
Synthesis example G141:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; o,5.97.
Synthetic example G142:
the synthesis was analogous to G139 as a yellow solid in 75% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; and O,5.75.
Synthesis example G143:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthesis example G144:
the synthesis was analogous to G139 as a yellow solid in 88% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; and O,5.54.
Synthetic example G145:
the synthesis was similar to G139 as a yellow solid with 80% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; o,4.83.
Synthetic example G146:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experiment value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthesis example G147:
the synthesis was similar to G139 as a yellow solid in 83% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example G148:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; and O,6.03.
Synthetic example G149:
the synthesis was similar to G139 as a yellow solid with 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthetic example G150:
the synthesis was analogous to G139 as a yellow solid in 73% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; o,5.27.
Synthetic example G151:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthesis example G152:
the synthesis was similar to G139 as a yellow solid with 75% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; g,14.36; n,4.70; o,5.37.
Synthetic example G153:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; g,24.51; n,4.02; and O,4.59.
Synthesis example G154:
the synthesis was similar to G139 as a yellow solid in 69% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example G155:
the synthesis was similar to G139 as a yellow solid in 79% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example G156:
the synthesis was analogous to G139 as a yellow solid in 58% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G157:
the synthesis was similar to G139 as a yellow solid in 83% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G158:
the synthesis was similar to G139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G159:
the synthesis was similar to G139 as a yellow solid with 72% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthesis example G160:
the synthesis was similar to G139 as a yellow solid in 74% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example G161:
the synthesis was analogous to G139 as a yellow solid in 59% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
Synthesis example G162:
weighing intermediate 56 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) to dissolve in anhydrous DMF, heating to 80 ℃ and stirring for 12h, cooling, pouring the reaction system into cold water, adjusting the pH value to be neutral by using diluted hydrochloric acid, filtering, collecting precipitate, drying and carrying out column chromatography to obtain a compound G162 as a yellow solid with the yield of 76%. Mass spectrum: m/z 1358.61, elemental analysis experimental value: c,83.94; h,5.64; b,1.59; n,4.12; o,4.71.
Synthesis example G163:
the synthesis was similar to G162 as a yellow solid in 75% yield. Mass spectrum: m/z 1028.34, elemental analysis experimental value: c,84.03; h,4.31; n,5.44; and O,6.22.
Synthetic example G164:
the synthesis was similar to G162 as a yellow solid in 74% yield. Mass spectrum: m/z 1070.38, elemental analysis experimental value: c,84.09; h,4.70; n,5.23; and O,5.97.
Synthetic example G165:
the synthesis was similar to G162 as a yellow solid in 73% yield. Mass spectrum: m/z 1112.43, elemental analysis experimental value: c,84.15; h,5.07; n,5.03; o,5.75.
Synthetic example G166:
the synthesis was analogous to G162 as a yellow solid in 71% yield. Mass spectrum: m/z 1238.57, elemental analysis experimental value: c,84.30; h,6.02; n,4.52; and O,5.16.
Synthetic example G167:
the synthesis was similar to G162 as a yellow solid in 70% yield. Mass spectrum: m/z 1154.48, elemental analysis experimental value: c,84.20; h,5.41; n,4.85; o,5.54.
Synthetic example G168:
the synthesis was similar to G162 as a yellow solid in 70% yield. Mass spectrum: m/z 1322.66, elemental analysis experiment value: c,84.38; h,6.55; n,4.23; and O,4.83.
Synthetic example G169:
the synthesis was similar to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1202.41, elemental analysis experimental value: c,77.84; h,5.19; n,4.65; o,5.32; si,7.00.
Synthetic example G170:
the synthesis was similar to G162 as a yellow solid in 70% yield. Mass spectrum: m/z 1418.53, elemental analysis experimental value: c,73.58; h,6.10; n,3.95; o,4.51; si,11.87.
Synthetic example G171:
the synthesis was analogous to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1061.28, elemental analysis experimental value: c,81.42; h,3.32; n,9.23; o,6.03.
Synthesis example G172:
the synthesis was similar to G162 as a yellow solid in 77% yield. Mass spectrum: m/z 1136.26, elemental analysis experimental value: c,79.22; h,2.84; n,12.32; o,5.63.
Synthetic example G173:
the synthesis was similar to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1214.38, elemental analysis Experimental value: c,85.98; h,4.15; n,4.61; and O,5.27.
Synthetic example G174:
the synthesis was similar to G162 as a yellow solid in 75% yield. Mass spectrum: m/z 1442.48, elemental analysis experimental value: c,87.36; h,4.33; n,3.88; and O,4.43.
Synthetic example G175:
the synthesis was similar to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1190.25, elemental analysis experimental value: c,72.61; h,2.96; g,14.36; n,4.70; o,5.37.
Synthetic example G176:
the synthesis was analogous to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1394.21, elemental analysis experimental value: c,64.57; h,2.31; g,24.51; n,4.02; o,4.59.
Synthetic example G177:
the synthesis was analogous to G162 as a yellow solid in 58% yield. Mass spectrum: m/z 1340.52, elemental analysis experimental value: c,85.94; h,5.11; n,4.18; o,4.77.
Synthetic example G178:
the synthesis was analogous to G162 as a yellow solid in 67% yield. Mass spectrum: m/z 1694.76, elemental analysis experimental values: c,87.10; h,5.82; n,3.30; o,3.77
Synthetic example G179:
the synthesis was similar to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G180:
the synthesis was analogous to G162 as a yellow solid in 59% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G181:
the synthesis was similar to G162 as a yellow solid in 76% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; and O,6.46.
Synthetic example G182:
the synthesis was analogous to G162 as a yellow solid in 82% yield. Mass spectrum: m/z 989.28, elemental analysis experimental value: c,80.07; h,3.56; n,9.90; o,6.46.
Synthetic example G183:
the synthesis was similar to G162 as a yellow solid in 73% yield. Mass spectrum: m/z 1034.27, elemental analysis experimental value: c,80.07; h,3.70; n,5.41; o,10.82.
Synthetic example G184:
the synthesis was analogous to G162 as a yellow solid in 79% yield. Mass spectrum: m/z 1082.21, elemental analysis experimental value: c,76.51; h,3.54; n,5.17; o,5.91; and S,8.88.
The technical effects and advantages of the invention are shown and verified by testing practical use performance through specific application of the compound to an organic electroluminescent device.
An organic electroluminescent device includes an anode, a cathode, and an organic material layer between the two electrodes. The organic material may be divided into a plurality of regions, for example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), or zinc oxide (ZnO), or any combination thereof may be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) having a single-layer structure, including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, 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, and the like.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The preparation process of the organic electroluminescent device in the embodiment of the invention is as follows:
and sequentially depositing an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode on the substrate, and then packaging. Wherein, when the organic light emitting layer is prepared, the organic light emitting layer is formed by a method of co-evaporation of an electron donor type material source, an electron acceptor type material source and the TADF material source of the present invention.
The method specifically comprises the following steps:
1. the anode material coated glass plate was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
2. placing the glass plate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 PaVacuum evaporating hole injecting material on the anode layer film to form hole injecting layer with evaporating rate of 0.1-0.5 nm/s;
3. vacuum evaporating hole transport material on the hole injection layer to form a hole transport layer with an evaporation rate of 0.1-0.5 nm/s,
4. an organic light-emitting layer of the device is vacuum evaporated on the hole transport layer, the organic light-emitting layer material comprises a main material and the compound of the invention as dyes, and the evaporation rate of the main material and the evaporation rate of the dyes are adjusted by a multi-source co-evaporation method to enable the dyes to reach a preset doping proportion;
5. forming an electron transport layer on the organic light-emitting layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5 nm/s;
6. LiF is evaporated on the electron transport layer in vacuum at 0.1-0.5 nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically 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 and the like which comprises the display device. The advantages of the display device are the same as the advantages of the organic electroluminescent device compared with the prior art, and are not described in detail herein.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
In the following embodiments of the present invention, the OLED includes an anode/a hole injection layer/a hole transport layer/a first exciton blocking layer/an emission layer/a second exciton blocking layer/an electron transport layer/an electron injection layer/a cathode, which are sequentially stacked. Wherein 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 luminescent layer is DPEPO, wherein the thermal activation delayed fluorescence material (any one of A-1 to A-152) is doped as luminescent dye, and the doping mass percentage concentration is 20%; the second exciton blocking layer is DCzPm; the electron transport layer is DPyPA co-evaporation; the electron injection layer is LiF; the cathode is Al.
The structure of the comparative compound is:
example 1
The glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
carrying out vacuum evaporation on the ITO transparent conductive layer to form HATCN serving as a hole injection layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5nm;
NPB is evaporated on the hole injection layer in vacuum to be used as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30nm;
TCTA is evaporated on the hole transport layer in vacuum to serve as a first exciton blocking layer, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 10nm;
the light-emitting layer of the device is vacuum evaporated on the first exciton blocking layer, the light-emitting layer comprises a host material and a dye material, the host material is DPEPO, and the thermal activation delayed fluorescence material A1 is used as the dye material. The evaporation rate of the main body material is adjusted to be 0.1nm/s, the evaporation rate of the dye in the luminescent layer is adjusted to be 20% of the evaporation rate of the main body, and the total thickness of the luminescent layer in evaporation is 30nm;
DPyPA is co-evaporated on the luminescent layer in vacuum to be used as an electron transport material of the device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm is subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
Examples 2 to 348 are the same as those in example 1 except that the light-emitting dye in the light-emitting layer was replaced with the compound A1 of the present invention and the compounds a-2 to G174 of the present invention, respectively. Comparative examples 1 to 21 were each prepared in the same manner as in example 1 except that the luminescent dye in the light-emitting layer was replaced with the compound A1 of the present invention by the above comparative compound, respectively.
The properties of the organic electroluminescent devices prepared in the above examples are shown in table 1 below.
Table 1:
as can be seen from Table 1 above, when the compound of the present invention is used for a luminescent dye in a light-emitting layer of an organic electroluminescent device, a luminance of 1000cd/m is required 2 When the voltage is low, the driving voltage is lower than 4V, the current efficiency is higher than 50cd/A, and the service life of T95 is longer than 200h.
The common point of the luminescent layer materials used in comparative examples 1-13 and 17 is that two cyano groups are arranged on a central benzene ring, which can cause the enrichment of electron cloud on the central benzene ring and reduce the C-N bond dissociation energy between carbazole and the central benzene ring, resulting in poor device life, and the existence of two cyano groups can cause the excessively deep LUMO energy level of molecules, more serious electron capture and lower device efficiency.
The light emitting layer material used in comparative example 13, which has four electron withdrawing groups, three benzonitrile and one cyano group, results in a greatly deepened LUMO level, a higher device voltage and a poor lifetime. In comparative examples 14 and 15, electron donors and acceptors are alternately arranged, the donors are carbazole groups, the acceptors are benzonitrile groups or isophthalonitrile groups, and the electron-withdrawing capability of the acceptor groups is insufficient, the singlet state triplet state energy level difference of molecules is large, the thermal activation delayed fluorescence property is difficult to maintain, and the efficiency of the device is obviously low. Meanwhile, the structure is different from the structure that a central benzene ring is directly connected with a cyano group, the cyano group of the structure is completely exposed at the outermost side of the molecule, namely, the LUMO orbit is distributed at the outermost side of the molecule, and an excited state quenching process is easily generated with other molecules, so that the service life of the device is low. Comparative examples 16 and 17 further reduced the electron-withdrawing group on the basis of comparative examples 14 and 15, and retained two and one benzonitrile groups as electron acceptors, respectively, further increased the band gap, and the device showed extremely high driving voltage and lower efficiency.
The compound T10 and the compound T13 used in comparative examples 20 and 21 are similar to those of comparative examples 14 and 15, in which cyanophenyl or phenyltrifluoromethyl group, in which cyano group and trifluoromethyl group are exposed on the outside of the molecule, is liable to exciton quenching, resulting in a lower device life.
The results show that the molecular design concept of introducing a plurality of electron acceptors is used for the organic electroluminescent device, the lighting voltage can be effectively reduced, the current efficiency is improved, and the thermal activation delayed fluorescent dye has good stability and good performance.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An organic compound having a structure represented by the following formula (1):
in the formula (1), D 1 、D 2 、D 3 、D 4 、D 5 Identical or different, D 1 、D 2 、D 3 、D 4 、D 5 Each independently selected from the following structures as shown in formula (d 1), formula (d 2), formula (d 3) or formula (d 4), or selected from substituted or unsubstituted C3-C60 heteroaryl;
and D 1 、D 2 、D 3 、D 4 、D 5 At least one is selected from the structures shown in one of formulas (d 1) to (d 4), and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl;
when a substituent is present 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;
in the formula (d 1), each R is the same or different, R is independently selected from one of hydrogen, deuterium, cyano-group, halogen, C1-C6 chain alkyl, C1-C6 halogenated chain alkyl, C1-C6 alkoxy and C1-C6 alkyl silicon group, and each R is not hydrogen at the same time;
in the formula (d 4), each R 1 Identical or different, R 1 Each independently selected from one of hydrogen, deuterium, cyano, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60 and heteroaryl of C5-C60.
2. An organic compound according to claim 1, wherein D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures shown in one of formulas (D1) to (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl;
or, D 1 、D 2 、D 3 、D 4 、D 5 Two of which are the same or different, are each independently selected from the structures represented by any one of formulae (D1) to (D4), and D 1 、D 2 、D 3 、D 4 、D 5 And the other three of (a) are each independently selected from substituted or unsubstituted C3-C60 heteroaryl.
3. The organic compound according to claim 1 or 2, wherein D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures represented by the formula (D1), and D 1 、D 2 、D 3 、D 4 、D 5 OfEach independently selected from substituted or unsubstituted C3-C60 heteroaryl;
or, the D is 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures represented by the formula (D1), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl;
preferably, in formula (d 1), R is independently selected from hydrogen, deuterium, benzonitrile or trifluoromethylphenyl, and each R is not simultaneously hydrogen;
more preferably, the formula (d 1) has a structure shown below:
4. the organic compound of claim 1, wherein D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures shown in one of the formulas (D2) and (D3), and D 1 、D 2 、D 3 、D 4 、D 5 Each four of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl;
or, the D is 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures shown in formula (D2) or formula (D3), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl.
5. The organic compound of claim 1, wherein D is 1 、D 2 、D 3 、D 4 、D 5 One of them is selected from the structures represented by the formula (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Four of (a) are each independently selected from substituted or substitutedUnsubstituted C3-C60 heteroaryl;
or, said D 1 、D 2 、D 3 、D 4 、D 5 Two of them are independently selected from the structures represented by the formula (D4), and D 1 、D 2 、D 3 、D 4 、D 5 Each three of (a) is independently selected from substituted or unsubstituted C3-C60 heteroaryl.
6. An organic compound according to any one of claims 1 to 5, wherein D is the number D 1 、D 2 、D 3 、D 4 、D 5 Independently selected from substituted or unsubstituted C3-C60 heteroaryl, selected from one of the following substituted or unsubstituted structural formulas:
when a substituent is present on 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;
preferably, when D 1 、D 2 、D 3 、D 4 、D 5 Independently selected from substituted or unsubstituted C3-C60 heteroaryl, selected from one of the following substituted or unsubstituted structural formulas:
when a substituent group exists on the structural formula, the substituent group is one selected from deuterium, C1-C6 chain alkyl, C3-C6 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
7. An organic compound according to claim 1, wherein the compound is selected from the following structures:
8. use of a compound according to any one of claims 1 to 7 as a functional material in an organic electronic device comprising: 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 label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper;
preferably, the application is as a light emitting layer material in an organic electroluminescent device, in particular as a light emitting layer luminescent dye.
9. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting functional layer comprises a hole transporting region, a light-emitting layer, and an electron transporting region, the hole transporting region is formed on the anode layer, the cathode layer is formed on the electron transporting region, the light-emitting layer is disposed between the hole transporting region and the electron transporting region, and the light-emitting layer contains the compound according to any one of claims 1 to 7.
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