Organic Compounds and Their Applications

Abstract

Provided is an organic compound that can be used in an organic electroluminescence device. The organic compound has characteristics of high luminous efficiency, narrow spectral emission, and high stability, and an organic electroluminescence device using the compound has a higher external quantum efficiency and a longer device lifetime. [Chemical Formula 1] TIFF2025523075000467.tif51166

Description

Technical Field

[0001] The present invention relates to organic compounds, particularly to compounds used in organic electroluminescence devices, and simultaneously to organic electroluminescence devices using such organic compounds.

Background Art

[0002] An organic electroluminescence device (OLED: Organic Light Emitting Diodes) is a type of device having a quasi-sandwich structure including an organic functional material layer sandwiched between an anode film, a cathode film layer, and an electrode film layer. When a voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode, negative charges are injected from the negative electrode, and under the action of an electric field, the positive charges and negative charges move within the organic layer, meet, recombine, and emit light. Since OLED devices have advantages such as high brightness, high-speed response, wide viewing angle, simple process, and flexibility, they have attracted much attention in the new display technology field and the new lighting technology field. Currently, this technology is widely applied to display panels such as new lighting fixtures, smartphones, and tablets, and furthermore, it has also expanded to the application field of large display products such as televisions, and it is a new display technology with rapid development and high technical requirements.

[0003] As OLEDs continue to progress in the fields of lighting and displays, people are paying more attention to the research of their core materials. This is because efficient and long-lifetime OLED devices are usually the result of an optimized combination of device structures and various organic materials. To fabricate OLED light-emitting devices with lower driving voltages, higher luminous efficiencies, and longer device service lives, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structures and preparation processes of OLED devices, but also to continuously conduct research and innovation on optoelectronic functional materials in OLED devices to produce higher-performance functional materials. Based on this, the OLED materials community has been working on the development of new organic electroluminescence materials to achieve low turn-on voltages, high luminous efficiencies, and optimized service lives of devices.

[0004] In the selection of OLED light-emitting materials, singlet-emitting fluorescent materials have long lifetimes and low prices, but low efficiencies. Triplet-emitting phosphorescent materials are highly efficient but expensive, and the lifetime problem of blue light materials has not been solved. Dr. Adachi of Kyushu University in Japan proposed a new organic light-emitting material, namely, thermally activated delayed fluorescence (TADF) material. This type of material utilizes the separation of donors and acceptors to obtain a small singlet-triplet energy gap (ΔEST) (<0.3 eV), so that triplet excitons can be converted into singlet excitons through reverse intersystem crossing (RISC) to emit light, and thus the internal quantum efficiency of the device can reach 100%.

[0005] In the prior art, the "multi-resonance induced thermally activated delayed fluorescence (MR-TADF)" strategy is used to design new structural compounds. For example, Patent Application Patent Documents 1, 2, 3, etc. design to construct polycyclic aromatic compounds formed by bonding multiple aromatic rings with boron atoms and nitrogen atoms or oxygen atoms, that is, a special rigid molecular system containing boron (B) atoms and nitrogen (N) atoms. Compared with donor-acceptor type TADF compounds, MR-TADF molecules have high luminescence transition rates and narrower full-width at half-maximum values. However, the colors of the light of current BN-type MR molecules are mostly in the region from sky blue to green, and the full-width at half-maximum values are mostly about 30 nm, which cannot meet the requirements of the new generation of ultra-high-definition video standard BT.2020.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Means for Solving the Problems

[0007] In one aspect, the present invention provides an organic compound having a structure represented by formulas (1-1) and (1-2),

Chemical Formula

[0008] W1, W2, W3 are each independently a C-C single bond, O, S, Se, CR7R8, SiR9R 10 or NR 11selected from, and m1, m2, m3 are each independently selected from 0 or 1, X is BAr5(R5) n5 , a C-C single bond, O, S, Se, CR 12 R 13 , SiR 14 R 15 , NR 16 or PR 17 selected from, V is selected from C, CH or CR6, Y is a C-C single bond, O, S, Se, CR 12 R 13 , SiR 14 R 15 or NR 16 selected from,

[0009] and when y1 is 0, V is selected from CH or CR6, and X is BAr5(R5) n5 , a C-C single bond, O, S, Se, CR 12 R 13 , SiR 14 R 15 , NR 16 or PR 17 selected from, and when y1 is 1, V is C, and X is BAr5(R5) n5 and ring Ar5 is selected from a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring,

[0010] R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently selected from a substituted or unsubstituted C1-C36 linear alkyl group, a C3-C36 cycloalkyl group, a C6-C30 arylamino group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C5-C60 heteroaryl group, and between R7 and R8, they do not bond or bond to form a ring, and between R9 and R 10either do not combine with each other or combine to form a ring,

[0011] and R 12 and R 13 either do not combine with each other or combine through any one of a C-C single bond, O, S, Se, CR7R8, SiR9R 10 or NR 11 to form a ring, and R 14 and R 15 either do not combine with each other or combine through any one of a C-C single bond, O, S, Se, CR7R8, SiR9R 10 or NR 11 to form a ring,

[0012] R1, R2, R3, R4, R5, and R6 are each independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C30 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amine group, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amine group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C3-C30 heteroarylamine group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C60 arylboryl group, substituted or unsubstituted C6-C60 aryl group, and substituted or unsubstituted C3-C60 heteroaryl group,

[0013] each of R1, R2, R3, and R4 is independently bonded to the bonded ring structure through a single bond, or each of R1, R2, R3, and R4 is independently condensed with the bonded ring structure through O, S, Se, CR1R2, or NR5 to form a ring structure, n1, n2, n3, n4, and n5 are each independently selected from integers from 0 to 10,

[0014] When n1, n2, n3, and n4 are each independently an integer greater than 1, among the plurality of corresponding R1s, among the plurality of R2s, among the plurality of R3s, and among the plurality of R4s, they are respectively the same or different, and among the plurality of R1s, they do not combine or combine to form a ring, among the plurality of R2s, they do not combine or combine to form a ring, among the plurality of R3s, they do not combine or combine to form a ring, and among the plurality of R4s, they do not combine or combine to form a ring.

[0015] When substituents are respectively independently present on the above R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 and R 17 above, the substituents are each independently selected from one or a combination of two of halogen, cyano group, C1-C20 linear alkyl group, C3-C20 cycloalkyl group, C1-C10 alkoxy group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C30 aryloxy group, C6-C30 aryl group, substituted or unsubstituted C6-C60 arylborolyl group, and C3-C30 heteroaryl group. Furthermore, the ring Ar1, ring Ar2, and ring Ar3 are each independently a structure represented by formula (a) or formula (b), and the dotted double bond represents the condensation position of the group.

Chemical formula

[0016] In formula (b), Z 5is selected from O, S, NR1 or CR2R3, where R1, R2, and R3 are each independently selected from a substituted or unsubstituted C1-C20 linear alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. When substituents are independently present on R1, R2, and R3, the substituents are each independently selected from a halogen, a cyano group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C6-C30 aryl group, and a C3-C30 heteroaryl group.

[0017] Ring H is selected from a C6-C30 aromatic ring and a C3-C30 heteroaromatic ring. Preferably, H is a benzene ring, and Z is selected from S, NR1 or CR2R3.

[0018] Continuing preferably, one of the ring Ar1, ring Ar2, and ring Ar3 has a structure represented by formula (b), and the other ring structures are each independently a structure represented by formula (a).

[0019] Furthermore, the ring Ar1, ring Ar2, and ring Ar3 are each independently selected from a C6-C30 aromatic ring or a C3-C30 heteroaromatic ring. Preferably, the ring Ar1, ring Ar2, and ring Ar3 are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a furan, a benzofuran, a dibenzofuran, an indole, a benzindole, a carbazole, an indolocarbazole, a benzothiophene, a dibenzothiophene, and a thiophene. More preferably, the ring Ar1, ring Ar2, and ring Ar3 are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a furan, or a thiophene. Furthermore, n1, n2, n3, and n4 are each independently selected from integers of 1 to 5.

[0020] R1, R2, R3, R4, R5, and R6 are each independently selected from one of deuterium, halogen, cyano group, C1-C12 linear alkyl group, substituted or unsubstituted C6-C60 aryl group, and substituted or unsubstituted C3-C60 heteroaryl group.

[0021] R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently selected from one of substituted or unsubstituted C1-C10 linear alkyl group, C3-C10 cycloalkyl group, C6-C30 arylamino group, C6-C30 aryl group, C6-C30 aryloxy group, and C5-C30 heteroaryl group. Preferably, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently selected from one of C1-C10 linear alkyl group, substituted or unsubstituted benzene ring, naphthalene ring, and anthracene ring.

[0022] Preferably, in the above general formula of the present invention, X is BAr5(R5) n5 , O, S, Se, CR 12 R 13 , SiR 14 R 15 and Y is O, S, Se, CR 12 R 13 , SiR 14 R 15 . More preferably, X is BAr5(R5) n5 , O, S, CR 12 R 13 , SiR 14 R 15 and Y is O, S, CR 12 R 13 , SiR14 R 15 wherein, most preferably, said X is BAr5(R5) n5 , S, CR 12 R 13 wherein, said Y is S, CR 12 R 13 . Furthermore, the organic compound of the present invention preferably has a structure represented by any one of the following structural formulas (2-1), (2-2) or (2-3),

Chemical formula

[0023] In formulas (2-1), (2-2) and (2-3), the definitions of R1-R6, R7-R 17 , Ar1-Ar5, n1-n5, W1-W2, m1-m2, X, Y and Z are the same as the definitions in formulas (1-1) and (1-2), respectively.

[0024] More preferably, said ring Ar1, ring Ar2, ring Ar3, ring Ar4 and ring Ar5 are each independently selected from a C6-C60 aromatic ring or a C3-C30 heteroaromatic ring,

[0025] Even more preferably, ring Ar1, ring Ar2, ring Ar3, ring Ar4 and ring Ar5 are each independently selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a furan, a benzofuran, a dibenzofuran, an indole, a benzindole, a carbazole, an indolocarbazole, a benzothiophene, a dibenzothiophene, or a thiophene,

[0026] Even more preferably, ring Ar1, ring Ar2, ring Ar3, ring Ar4 and ring Ar5 are each independently any one of a benzene ring, a naphthalene ring, a dibenzofuran, a carbazole, or a dibenzothiophene, Most preferably, ring Ar1, ring Ar2, ring Ar3, ring Ar4 and ring Ar5 are each independently a benzene ring.

[0027] More preferably, when the said X is BAr5(R5) n5 , O, S, Se, CR 12 R 13 , SiR 14 R 15 and the said Y is O, S, Se, CR 12 R 13 , SiR 14 R 15 More preferably, when the said X is BAr5(R5) n5 , O, S, CR 12 R 13 , SiR 14 R 15 and the said Y is O, S, CR 12 R 13 , SiR 14 R 15 Most preferably, when the said X is BAr5(R5) n5 , S, CR 12 R 13 and the said Y is S, CR 12 R 13 .

[0028] More preferably, the said X is BAr5(R5) n5 , O, S, Se, CR 12 R 13 , SiR 14 R 15 More preferably, the said X is selected from n5 .

[0029] More preferably, the said X is BAr5(R5) n5 , C-C single bond, O, S, Se, CR 12 R 13 , SiR 14 R 15 or NR 16 and is more preferably selected from BAr5(R5) n5 or CR 12 R 13 .

[0030] Preferably, the W1 and W3 are each independently a C-C single bond, S, CR7R8 or NR 11 selected from, m1 and m3 are 1, and m2 is 0. Furthermore, the organic compound of the present invention preferably has a structure represented by any one of formulas (2) to (26),

Chemical formula

[0031] In formulas (2) to (26), the definitions of R1-R6, Ar1-Ar5, n1-n5, W1, W3, m1, m3 and Z are the same as those in formulas (1-1) and (1-2), and R 12 and R 13 do not bond to each other, or are bonded via any one of a C-C single bond, O, S, Se, CR7R8, SiR9R 10 or NR 11 to form a ring, and R 14 and R 15 do not bond to each other, or are bonded via any one of a C-C single bond, O, S, Se, CR7R8, SiR9R 10 or NR 11 to form a ring.

[0032] Furthermore, each of the above R1, R2, R3, R4, R5, and R6 is independently hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, 2-methylbutyl group, n-pentyl group, s-pentyl group, cyclopentyl group, neopentyl group, n-hexyl group, cyclohexyl group, neohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, 2-ethylhexyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysenyl group, ferrenyl group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, genyl group, terphenyl group, trimerized phenyl group, quarterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthoimidazolyl group, phenanthroimidazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthroxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,Selected from one of the substituents of 6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaphenalenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, diphenylboril group, dimethylboril group, dipentafluorophenylboril group, bis(2,4,6-triisopropylphenyl)boril group, or selected from a combination of two of the above groups.,

[0033] Said R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17is, independently of each other, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthrenyl group, a benzophenanthrenyl group, a pyrenyl group, a chrysenyl group, a ferrenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a genyl group, a terphenyl group, a trimerized phenyl group, a quarterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis or trans indenofluorenyl group, a trimerized indenyl group, an isotrimerized indenyl group, a spirotrimerized indenyl group, a spiroisotrimerized indenyl group, a furyl group, a benzofuryl group, an isobenzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5,6-quinolyl group, a benzo-6,7-quinolyl group, a benzo-7,8-quinolyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthimidazolyl group, a phenanthroimidazolyl group, a pyridinoimidazolyl group, a pyrazinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthroxazolyl group, a phenanthroxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, 4,Selected from among substituents of one of 5-diazapirenyl group, 4,5,9,10-tetraazaphenalenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, or selected from among combinations of two of the foregoing,

[0034] More preferably, each of the R1, R2, R3, R4, R5, and R6 is independently hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a trifluoromethyl group, a pentafluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis or trans indenofluorenyl group, a furyl group, a benzofuryl group, a thienyl group, a benzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a 1,3,5-triazinyl group, a diphenylborolyl group, a dimethylborolyl group, a dipentafluorophenylborolyl group, a bis(2,4,6-triisopropylphenyl)borolyl group, or a combination of two of the foregoing groups,

[0035] The R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17is independently selected from one of the substituents of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, trifluoromethyl group, pentafluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, 1,3,5-triazinyl group, diphenylborolyl group, dimethylborolyl group, dipentafluorophenylborolyl group, bis(2,4,6-triisopropylphenyl)borolyl group, or selected from a combination of two of the above groups,

[0036] Most preferably, the R1, R2, R3, R4, R5 and R6 each independently represent one of hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, trifluoromethyl group, pentafluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, spirobifluorenyl group, carbazolyl group, 1,3,5-triazinyl group, diphenylborolyl group, dimethylborolyl group, dipentafluorophenylborolyl group, bis(2,4,6-triisopropylphenyl)borolyl group, or are selected from a combination of two of the above groups,

[0037] The R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R16 and R 17 is, independently of one another, selected from among substituents of one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a cyano group, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a spirobifluorenyl group, or is selected from among combinations of two of the foregoing groups.

[0038] Unless otherwise defined below, it should be noted that all technical and scientific terms used herein are intended to have the same meaning as commonly understood by one of ordinary skill in the art. References to techniques used herein are intended to mean techniques commonly understood in the art, including technical modifications or equivalent techniques that are obvious to one of ordinary skill in the art. Although the following terms are considered to be well understood by one of ordinary skill in the art, the following definitions are provided to better explain the present invention.

[0039] In this specification, the expression Ca~Cb indicates that the number of carbon atoms of the group is a~b, and generally, unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms of the substituent. When explaining C1~C30, it includes C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., but is not limited thereto, and other numerical ranges will not be explained again.

[0040] The terms "comprising," "including," "having," "containing," or "relating to," and other variations herein, are inclusive or open-ended and do not exclude other elements or method steps not recited.

[0041] In the present invention, the expression of chemical elements includes the concept of isotopes having the same chemical properties unless otherwise specified. For example, the expression "hydrogen" includes the concepts of "deuterium" and "tritium" having the same chemical properties, and carbon (C) is12 C, 13 including C etc., which will not be described again. The heteroatom in the present invention usually refers to being selected from N, O, S, P, Si and Se, and preferably refers to being selected from N, O, S.

[0042] As used herein, the terms "heterocyclyl group" and "heterocyclic ring" have at least one ring atom that is a heteroatom selected from N, O and S, and the remaining ring atoms are C, which is saturated (i.e., heterocycloalkyl group) or partially unsaturated (i.e., having one or more double bonds and / or triple bonds in the ring) cyclic group.

[0043] As used herein, the terms "aryl (or arylene) group" and "aromatic ring" refer to a fully carbocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "heteroaryl (or heteroarylene) group" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl group" preferably represents an aryl group or a heteroaryl group-substituted alkyl group, where the aryl group, heteroaryl group and alkyl group are as defined herein. As used herein, the term "halo" or "halogen" is defined to include F, Cl, Br or I.

[0044] The term "substituted" means that one or more (e.g., one, two, three or four) hydrogens on the specified atom are replaced by selection from the specified groups, provided that it does not exceed the normal valence of the specified atom in the current situation and a stable compound is formed by the said substitution. Combinations of substituents and / or variables are permitted only when such combinations form stable compounds.

[0045] When a substituent is described as being "independently selected" from a group, each substituent is selected independently of the others. Thus, each substituent may be the same as or different from another (other) substituent. As used herein, the term "one or more" refers to one, or more than one, such as two, three, four, five, or ten, etc., under reasonable conditions. Unless otherwise specified, as used herein, the point of attachment of a substituent may be from any suitable position on the substituent. When the attachment of a substituent is represented as a bond connecting two atoms within a ring, such a substituent may be attached to any ring-forming atom within the ring that can be substituted. The term "about" refers to within ±10% of the recited numerical value, preferably within ±5%, more preferably within ±2%. In the structural formulas presented herein, the representation of a ring structure by "-" indicates that the point of attachment can be at any position on the ring structure where a bond can be formed.

[0046] Unless otherwise specified, the C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention are aromatic groups satisfying the π-conjugated system, and both include cases of monocyclic residues and condensed ring residues. The so-called monocyclic residue means that the molecule contains at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other. Exemplarily, they are bonded through a single bond such as a phenyl group, a diphenyl group, a terphenyl group, etc. The condensed ring residue refers to a molecule containing at least two benzene rings such as a naphthyl group, an anthracenyl group, a phenanthrenyl group, etc. However, the benzene rings are not independent of each other, share the edges of the ring, and are condensed with each other. The monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When one heteroaryl group and other groups (for example, an aryl group, a heteroaryl group, an alkyl group, etc.) are contained in the molecule, the heteroaryl group and the other group are independent of each other and are bonded through a single bond. Exemplarily, they are pyridine, furan, thiophene, etc. The condensed ring heteroaryl group is formed by the condensation of at least one phenyl group and at least one heteroaryl group, or by the condensation of at least two kinds of heteroaromatic rings. Exemplarily, they are quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0047] In this specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, more preferably a phenyl group, naphthyl group, anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysenyl group, ferrenyl group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, genyl group, terphenyl group, trimerized phenyl group, quarterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group. Specifically, the biphenyl group is selected from a 2-biphenyl group, 3-biphenyl group, and 4-biphenyl group; the terphenyl group includes a p-terphenyl group-4-yl, p-terphenyl group-3-yl, p-terphenyl group-2-yl, m-terphenyl group-4-yl, m-terphenyl group-3-yl, and m-terphenyl group-2-yl; the naphthyl group includes a 1-naphthyl group or 2-naphthyl group; the anthracenyl group is selected from a 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, 2-pyrenyl group, and 4-pyrenyl group; and the tetracenyl group is selected from a 1-tetracenyl group, 2-tetracenyl group, and 9-tetracenyl group. Preferred examples of the aromatic ring in the present invention include a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, indenyl group, fluorenyl group and its derivatives, fluoranthenyl group, triphenylene group, pyrenyl group, ferrenyl group, chrysenyl group, and tetracenyl group.The biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes a p-terphenyl group-4-yl, a p-terphenyl group-3-yl, a p-terphenyl group-2-yl, an m-terphenyl group-4-yl, an m-terphenyl group-3-yl, and an m-terphenyl group-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from the group consisting of a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from the group consisting of a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the fluorenyl group derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene, and benzofluorene; the pyrenyl group is selected from the group consisting of a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; and the tetracenyl group is selected from the group consisting of a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group.

[0048] In this specification, the substituted or unsubstituted C6-C60 aryl group is preferably a C6-C30 aryl group, more preferably a phenyl group, naphthyl group, anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysenyl group, ferrenyl group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, genyl group, terphenyl group, trimerized phenyl group, quarterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group. Specifically, the biphenyl group is selected from a 2-biphenyl group, 3-biphenyl group, and 4-biphenyl group; the terphenyl group includes a p-terphenyl group-4-yl, p-terphenyl group-3-yl, p-terphenyl group-2-yl, m-terphenyl group-4-yl, m-terphenyl group-3-yl, and m-terphenyl group-2-yl; the naphthyl group includes a 1-naphthyl group or 2-naphthyl group; the anthracenyl group is selected from a 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, 2-pyrenyl group, and 4-pyrenyl group; and the tetracenyl group is selected from a 1-tetracenyl group, 2-tetracenyl group, and 9-tetracenyl group. Preferred examples of the aryl group in the present invention include groups of a group consisting of a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, indenyl group, fluorenyl group and its derivatives, fluoranthenyl group, triphenylene group, pyrenyl group, ferrenyl group, ferrenyl group, and tetracenyl group.The biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes a p-terphenyl group-4-yl, a p-terphenyl group-3-yl, a p-terphenyl group-2-yl, an m-terphenyl group-4-yl, an m-terphenyl group-3-yl, and an m-terphenyl group-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from the group consisting of a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from the group consisting of a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the fluorenyl group derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene, and benzofluorene; the pyrenyl group is selected from the group consisting of a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; and the tetracenyl group is selected from the group consisting of a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. The C6-C60 aryl group of the present invention may be a group in which the above groups are singly bonded and / or condensed.

[0049] In this specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, and can be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an isobenzothienyl group, an indolyl group, an isoindolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group and its derivatives, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5,6-quinolyl group, a benzo-6,7-quinolyl group, a benzo-7,8-quinolyl group, a phenothiazinyl group, a phenazinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthimidazolyl group, a phenanthroimidazolyl group, a pyridinoimidazolyl group, a pyrazinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthraoxazolyl group, a phenanthroxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaphenalenyl group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbolinyl group, a phenanthrolinyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, 1,2,3,Heteroaromatic rings formed of a 5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, benzothiadiazole, etc. are exemplified. Preferred examples of the heteroaromatic ring in the present invention include a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, and heteroaromatic rings of derivatives thereof. Here, the carbazolyl group derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.,

[0050] In this specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an isobenzothienyl group, an indolyl group, an isoindolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group and its derivatives, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5,6-quinolyl group, a benzo-6,7-quinolyl group, a benzo-7,8-quinolyl group, a phenothiazinyl group, a phenazinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthroimidazolyl group, a pyridinoimidazolyl group, a pyrazinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthraoxazolyl group, a phenanthrooxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaphenalenyl group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbolinyl group, a phenanthrolinyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,A 5 - tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, benzothiadiazole, etc. Preferred examples of the heteroaryl group in the present invention include a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group and derivatives thereof. Here, the carbazolyl group derivative is preferably 9 - phenylcarbazole, 9 - naphthylcarbazole, benzocarbazole, dibenzocarbazole or indolocarbazole. The C3 - C60 heteroaryl group of the present invention may be a group in which the above groups are singly bonded or / and condensed.,

[0051] In this specification, the chain alkyl group also includes both straight - chain and branched - chain alkyl groups. Examples of the C1 - C20 chain alkyl group include a methyl group, an ethyl group, an n - propyl group, an isopropyl group, an n - butyl group, an isobutyl group, an s - butyl group, a t - butyl group, a 2 - methylbutyl group, an n - pentyl group, an s - pentyl group, a neopentyl group, an n - hexyl group, a neohexyl group, an n - heptyl group, an n - octyl group, a 2 - ethylhexyl group, etc. Examples of the C1 - C20 chain haloalkyl group include a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2 - trifluoroethyl group, etc.,

[0052] In this specification, the C3 - C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group. Specific examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, etc., In this specification, the alkoxy group refers to a group composed of the above - mentioned chain alkyl group and oxygen, or a group composed of the above - mentioned cycloalkyl group and oxygen.,

[0053] Examples of the C1-C20 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an s-butoxy group, an isobutoxy group, a t-butoxy group, a pentyloxy group, an isopentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, etc. Here, preferably, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a t-butoxy group, an s-butoxy group, an isobutoxy group, an isopentyloxy group are mentioned, and preferably, it is a methoxy group.

[0054] In the present specification, examples of the C1-C20 silyl group include a silyl group substituted with the groups listed above as the C1-C20 alkyl group, that is, a group formed by substituting one, two or three hydrogens on the silyl group with the above linear alkyl group or cycloalkyl group. Specifically, groups such as a methylsilyl group, a dimethylsilyl group, a trimethylsilyl group, an ethylsilyl group, a diethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a t-butyl diphenylsilyl group, etc. are mentioned.

[0055] Furthermore, the compounds described in the general formulas (1-1) and (1-2) of the present invention are preferably specific structural compounds such as A1-1 to A1-192, A2-1 to A2-57, A3-1 to A3-57, A4-1 to A4-57, A5-1 to A5-57, A6-1 to A6-57, A7-1 to A7-57, A8-1 to A8-57, B1-1 to B1-186, B2-1 to B2-57, B3-1 to B3-57, B4-1 to B4-186, B5-1 to B5-57, B6-1 to B6-57, B7-1 to B7-60, B8-1 to B8-60, C1-1 to C1-84, C2-1 to C2-76, C3-1 to C3-68, C4-1 to C4-56, C5-1 to C5-76, C6-1 to C6-72, C7-1 to C7-76, C8-1 to C8-80, C9-1 to C9-80, D1-1 to D1-954, etc. These compounds are merely representative.

Chemical formula

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0056] The structural features of this type of compound of the present invention are as follows. In the parent core structures such as formula (1-1) and formula (1-2), in the nitrogen-boron-nitrogen structure commonly used in the prior art, in the compounds of the present invention, specific X groups and Y groups are introduced at the meta-positions of the boron atoms of the central benzene ring. The X can be an arylboron, a single bond, a carbon atom, a silicon atom, a nitrogen atom, a phosphorus atom, an oxygen atom, a sulfur atom or a selenium atom, and the Y can be a single bond, a carbon atom, a silicon atom, a nitrogen atom, a phosphorus atom, an oxygen atom, a sulfur atom or a selenium atom. By introducing X and Y, the donor groups on the left or right side of the parent core can be effectively locked, thereby effectively eliminating the repulsion between the hydrogen atoms on the central benzene ring and the hydrogen atoms on the surrounding benzene rings in the nitrogen-boron-nitrogen structure. Since the central benzene ring and the surrounding aromatic rings are almost on the same plane, the deformation and vibrational relaxation of the excited state of the molecule are effectively reduced, and the stability and color purity of the molecule are improved. At the same time, X and Y introduced into the parent core structure of the compound of the present invention do not affect the basic multi-resonance characteristics of the nitrogen-boron-nitrogen structure, so the characteristics of high quantum efficiency and narrow spectrum of the multi-resonance dye are maintained. In addition, X and Y are designed as single bonds, B, C, Si, N, P, O, S, Se, and various types of these atoms or groups. By utilizing their different electronegativities, the compounds of the present invention can adjust the emission color from blue light (single bond, B), blue-green light (C, Si), green light (O, S, Se) to red light (N, P), so that the light color can be adjusted over a wide range and a relatively wide color gamut can be covered. Also, when X or Y is an arylboron, a carbon atom, a silicon atom, a nitrogen atom, or a phosphorus atom, due to its large-volume group and twisted structure, the intermolecular interaction can be effectively reduced. By reducing the intermolecular interaction force, problems such as red shift, broadening, and efficiency reduction due to molecular aggregation are alleviated, the concentration quenching effect is significantly suppressed, and the interaction between the host and the dye, and between the dyes in the device is reduced, so that the emission efficiency and lifetime are significantly improved, the stability and reproducibility of the device are improved, the doping concentration can be increased to reduce the difficulty of device preparation, and the commercial application of the material can also be facilitated.Also, when X or Y has a structure containing spiro C and spiro Si, due to the asymmetric structures on both sides of the spiro atom, the molecule has chirality, and through the perturbation of the boron-nitrogen luminescent parent core by the chiral center, the luminescence produces circular polarization characteristics. After chiral resolution, a pair of optically pure compounds are obtained, which can generate strong circularly polarized luminescence in the device, and its dissymmetry factor is of the order of 10. -3 Compared with existing BN dye molecules, the target molecule has a significantly narrower full width at half maximum (14 - 20 nm) and a longer lifetime in organic optoelectronic devices. Furthermore, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are easily available, and it is suitable for mass production and scale-up.

[0057] The second aspect of the present invention simultaneously protects the applications of the compounds represented by any one of the above general formulas (1-1) to (1-2), general formulas (2-1) to (2-3), and general formulas (2) to (26), and the applications are used as functional materials in organic electronic devices, and the organic electronic devices include organic electroluminescence devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners, or electronic papers, and preferably, they are organic electroluminescence devices.

[0058] In a third aspect, the present invention further provides an organic electroluminescence device including a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, where the organic layer contains a compound represented by any one of the above general formulas (1-1) to (1-2), general formulas (2-1) to (2-3), and general formulas (2) to (26).

[0059] Specifically, one embodiment of the present invention provides an organic electroluminescence device including a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate. The light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer. The hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is provided between the hole transport layer and the electron transport layer. Here, the light-emitting layer contains a compound of the general formula of the present invention represented by the above formula (1).

[0060] The OLED device prepared using the compound of the present invention has a low turn-on voltage, high luminous efficiency, and better service life, and can meet the requirements of current panel manufacturing enterprises for high-performance materials.

Embodiments for Carrying Out the Invention

[0061] Hereinafter, specific preparation methods of the novel compound of the present invention will be described in detail with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0062] All basic chemical raw materials used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate, etc., are purchased from Shanghai Titan Scientific Co., Ltd. and Xilong Scientific Co., Ltd. The mass spectrometer used for measuring the following compounds is a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0063] Hereinafter, the synthesis method of the compound of the present invention will be briefly described. Synthesis Example Typical Synthesis Route A:

Chemical Formula

Chem.

[0064] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (24 mL, 2.50 M, 60 mmol) was slowly added to a solution of the brominated precursor (8.49 g, 15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, and boron tribromide (15.04 g, 60 mmol) was slowly added, and the temperature was raised to 60 °C and continuously stirred for 2 hours. N,N-Diisopropylethylamine (15.52 g, 120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mL, 1.0 M, 60 mmol) was added at room temperature, and after reacting for 6 hours, the reaction was stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-1 (2.86 g, 36% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 544.23 Elemental analysis result: theoretical value: C, 86.07; H, 4.82; B, 3.97; N, 5.15; experimental value: C, 86.05; H, 4.81; B, 3.98; N, 5.17. Synthesis Example A-2: Synthesis of Compound A1-4

Chem.

[0065] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-4 (32% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 768.48 Elemental analysis result: theoretical value: C, 85.94; H, 7.61; B, 2.81; N, 3.64; experimental value: C, 85.92; H, 7.62; B, 2.82; N, 3.64. Synthesis Example A-3: Synthesis of Compound A1-8 [Chemical formula]

[0066] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the mixture is reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added. The temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature. After reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-8 (33% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1072.60 Elemental analysis result: theoretical value: C, 88.42; H, 6.95; B, 2.01; N, 2.61; experimental value: C, 88.44; H, 6.96; B, 2.00; N, 2.50. Synthesis Example A-4: Synthesis of Compound A1-10

Chemical formula

[0067] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) was added at room temperature, and after reacting for 6 hours, the reaction was stopped, the solvent was spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-10 (23% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1212.52 Elemental analysis result: theoretical value: C, 86.14; H, 5.15; B, 1.78; N, 6.93; experimental value: C, 86.13; H, 5.13; B, 1.79; N, 6.95. Synthesis Example A-5: Synthesis of Compound A1-13

Chemical Structure

[0068] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-13 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 744.29 Elemental analysis result: theoretical value: C, 88.73; H, 4.60; B, 2.90; N, 3.76; experimental value: 88.72; H, 4.61; B, 2.92; N, 3.74. Synthesis Example A-6: Synthesis of Compound A1-17 [Chemical formula]

[0069] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the mixture is reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-17 (34% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 772.51 Elemental analysis result: theoretical value: C, 85.49; H, 8.09; B, 2.80; N, 3.63; experimental value: C, 85.46; H, 8.11; B, 2.79; N, 3.63. Synthesis Example A-7: Synthesis of Compound A1-21

Chemical Structure

[0070] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-21 (20% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 874.34 Elemental analysis result: theoretical value: C, 86.51; H, 4.61; B, 2.47; N, 6.41; experimental value: C, 86.50; H, 4.63; B, 2.46; N, 6.42. Synthesis Example A-8: Synthesis of Compound A1-24 [Chemical formula]

[0071] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-24 (22% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 874.34 Elemental analysis result: theoretical value: C, 86.51; H, 4.61; B, 2.47; N, 6.41; experimental value: C, 86.52; H, 4.61; B, 2.47; N, 6.40. Synthesis Example A-9: Synthesis of Compound A1-44 [Chemical formula]

[0072] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-44 (25% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 874.34 Elemental analysis result: theoretical value: C, 86.51; H, 4.61; B, 2.47; N, 6.41; experimental value: C, 86.51; H, 4.62; B, 2.48; N, 6.39. Synthesis Example A-10: Synthesis of Compound A1-55

Chemical Structure

[0073] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added, and the temperature is raised to 60 °C and continuously stirred for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-55 (40% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 872.35 Elemental analysis result: theoretical value: C, 89.46; H, 4.85; B, 2.48; N, 3.21; experimental value: C, 89.48; H, 4.86; B, 2.47; N, 3.19. Synthesis Example A-11: Synthesis of Compound A1-65

Chemical Structure

[0074] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-65 (36% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 696.29 Elemental analysis result: theoretical value: C, 87.95; H, 4.92; B, 3.10; N, 4.02; experimental value: C, 87.96; H, 4.95; B, 3.09; N, 4.00. Synthesis Example A-12: Synthesis of Compound A1-70

Chemical Structure

[0075] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the reaction is carried out for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-70 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.49 Elemental analysis result: theoretical value: C, 85.93; H, 7.73; B, 2.76; N, 3.58; experimental value: C, 85.93; H, 7.75; B, 2.77; N, 3.55. Synthesis Example A-13: Synthesis of Compound A1-80

Chemical Structure

[0076] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-80 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 576.22 Elemental analysis result: theoretical value: C, 81.29; H, 4.55; B, 3.75; N, 4.86; experimental value: C, 81.29; H, 4.56; B, 3.73; N, 4.88. Synthesis Example A-14: Synthesis of Compound A1-81

Chemical formula

[0077] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-81 (26% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 608.17 Elemental analysis result: theoretical value: C, 76.99; H, 4.31; B, 3.55; N, 4.60; S, 10.54; experimental value: C, 76.97; H, 4.30; B, 3.56; N, 4.58; S, 10.58. Synthesis Example A-15: Synthesis of Compound A1-82

Chemical formula

[0078] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the mixture is reacted for 1 hour. After completion of the reaction, the mixture is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-82 (22% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 702.19 Elemental analysis result: theoretical value: C, 66.71; H, 3.73; B, 3.08; N, 3.99; Se, 22.49; experimental value: C, 66.74; H, 3.71; B, 3.09; N, 3.98; Se, 22.52. Synthesis Example A-16: Synthesis of Compound A1-85 [Chemical formula]

[0079] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-85 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 908.34 Elemental analysis result: theoretical value: C, 83.26; H, 5.10; B, 2.38; N, 3.08; Si, 6.18; experimental value: C, 83.27; H, 5.11; B, 2.37; N, 3.09; Si, 6.16. Synthesis Example A-17: Synthesis of Compound A1-87

Chemical Structure

[0080] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-87 (30% yield, HPLC analysis purity 99%) as an orange solid. MALDI-TOF-MS result: molecular ion peak: 560.22 Elemental analysis result: theoretical value: C, 83.61; H, 4.68; B, 3.86; N, 5.00; experimental value: C, 83.60; H, 4.66; B, 3.87; N, 5.02. Synthesis Example A-18: Synthesis of Compound A1-94 [Chemical formula]

[0081] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-87 (30% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 724.27 Elemental analysis result: theoretical value: C, 84.54; H, 4.73; B, 2.98; N, 3.87; Si, 3.88; experimental value: C, 84.53; H, 4.75; B, 2.97; N, 3.88; Si, 3.89. Synthesis Example A-19: Synthesis of Compound A1-155

Chemical formula

[0082] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-155 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 650.22 Elemental analysis result: theoretical value: C, 83.10; H, 4.34; B, 3.32; N, 4.31; S, 4.93; experimental value: C, 83.08; H, 4.35; B, 3.30; N, 4.321; S, 4.95. Synthesis Example A-20: Synthesis of Compound A1-179

Chemical Structure

[0083] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-179 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.27; H, 6.00; B, 2.62; N, 5.11. Synthesis Example A-21: Synthesis of Compound A1-180

Chemical formula

[0084] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added, and the temperature is raised to 60 °C and continuously stirred for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and the reaction is stopped after 6 hours. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-180 (34% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.26; H, 6.05; B, 2.59; N, 5.10. Synthesis Example A-22: Synthesis of Compound A1-181

Chemical formula

[0085] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-181 (30% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.26; H, 6.05; B, 2.60; N, 5.09. Synthesis Example A-23: Synthesis of Compound A1-182

Chemical Structure

[0086] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-182 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.26; H, 6.02; B, 2.61; N, 5.11. Synthesis Example A-24: Synthesis of Compound A1-183 [Chemical formula]

[0087] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the mixture is reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-183 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.27; H, 6.03; B, 2.60; N, 5.10. Synthesis Example A-25: Synthesis of Compound A1-184 [Chemical formula]

[0088] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-184 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.27; H, 6.00; B, 2.61; N, 5.12. Synthesis Example A-26: Synthesis of Compound A1-185

Chemical Structure

[0089] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the reaction is carried out for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-185 (32% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.27; H, 6.00; B, 2.60; N, 5.13. Synthesis Example A-27: Synthesis of Compound A1-186 [Chemical formula]

[0090] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A1-186 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.41 Elemental analysis result: theoretical value: C, 86.24; H, 6.01; B, 2.63; N, 5.11; experimental value: C, 86.25; H, 6.01; B, 2.62; N, 5.12. Synthesis Example A-28: Synthesis of Compound A2-4 [Chemical formula]

[0091] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A2-4 (36% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 766.46 Elemental analysis result: theoretical value: C, 86.16; H, 7.36; B, 2.82; N, 3.65; experimental value: C, 86.17; H, 7.37; B, 2.81; N, 3.64. Synthesis Example A-29: Synthesis of Compound A2-57

Chemical Structure

[0092] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A2-57 (30% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 707.27 Elemental analysis result: theoretical value: C, 86.59; H, 4.42; B, 3.06; N, 5.94; experimental value: C, 86.58; H, 4.40; B, 3.07; N, 5.95. Synthesis Example A-30: Synthesis of Compound A3-4

Chemical formula

[0093] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the reaction is carried out for 1 hour. After completion of the reaction, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added, and the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A3-4 (36% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.46 Elemental analysis result: theoretical value: C, 84.40; H, 7.21; B, 2.76; N, 3.58; O, 2.04; experimental value: C, 84.41; H, 7.22; B, 2.75; N, 3.58; O, 2.03. Synthesis Example A-31: Synthesis of Compound A4-4

Chemical formula

[0094] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the reaction is allowed to proceed for 1 hour. After completion of the reaction, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added. The temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature. After reacting for 6 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A4-4 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 798.44 Elemental analysis result: theoretical value: C, 82.71; H, 7.07; B, 2.71; N, 3.51; S, 4.01; experimental value: C, 82.73; H, 7.06; B, 2.70; N, 3.50; S, 4.02. Synthesis Example A-32: Synthesis of Compound A5-4

Chemical formula

[0095] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the mixture is reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, the reaction is stopped after 6 hours, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A5-4 (33% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.38 Elemental analysis result: theoretical value: C, 78.12; H, 6.68; B, 2.56; N, 3.31; Se, 9.34; experimental value: C, 78.11; H, 6.67; B, 2.55; N, 3.32; Se, 9.36. Synthesis Example A-33: Synthesis of Compound A6-4 [Chemical formula]

[0096] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, and boron tribromide (60 mmol) is slowly added, and the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A6-4 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 857.51 Elemental analysis result: theoretical value: C, 85.41; H, 7.17; B, 2.52; N, 4.90; experimental value: C, 85.39; H, 7.18; B, 2.51; N, 4.92. Synthesis Example A-34: Synthesis of Compound A7-4

Chemical Structure

[0097] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A7-4 (37% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 932.54 Elemental analysis result: theoretical value: C, 87.55; H, 7.13; B, 2.32; N, 3.00; experimental value: C, 87.55; H, 7.15; B, 2.31; N, 3.01. Synthesis Example A-35: Synthesis of Compound A8-4 [Chemical formula]

[0098] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and the reaction is carried out for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. A solution of phenylmagnesium bromide in tetrahydrofuran (60 mmol) is added at room temperature, and after reacting for 6 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A8-4 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 948.52 Elemental analysis result: theoretical value C, 84.80; H, 7.01; B, 2.28; N, 2.95; Si, 2.96; experimental value: C, 84.81; H, 7.00; B, 2.26; N, 2.96; Si, 2.97.

[0099] Typical synthetic route B:

Chemical formula

Chemical formula

[0100] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (24 mL, 2.50 M, 60 mmol) was slowly added to a solution of a brominated precursor (8.49 g, 15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, and boron tribromide (15.04 g, 60 mmol) was slowly added. The temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (15.52 g, 120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-1 (33% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 430.13 Elemental analysis result: theoretical value: C, 83.74; H, 3.51; B, 2.51; N, 6.51; experimental value: C, 83.72; H, 3.52; B, 2.50; N, 6.53. Synthesis Example B-2: Synthesis of Compound B1-4 [Chemical formula]

[0101] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-4 (35% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 654.38; Elemental analysis result: theoretical value: C, 84.39; H, 7.24; B, 1.65; N, 4.28; experimental value: C, 84.41; H, 7.25; B, 1.66; N, 4.25. Synthesis Example B-3: Synthesis of Compound B1-8

Chemical Structure

[0102] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-8 (34% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 958.50; Elemental analysis result: theoretical value: C, 87.66; H, 6.62; B, 1.13; N, 2.92; experimental value: C, 87.65; H, 6.61; B, 1.14; N, 2.94. Synthesis Example B-4: Synthesis of Compound B1-10

Chem.

[0103] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction was stopped, the solvent was spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-10 (28% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1098.42 Elemental analysis result: theoretical value: C, 85.24; H, 4.68; B, 0.98; N, 7.65; experimental value: C, 85.25; H, 4.70; B, 0.99; N, 7.63. Synthesis Example B-5: Synthesis of Compound B1-13

Chem.

[0104] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-13 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 630.19 Elemental analysis result: theoretical value: C, 87.63; H, 3.68; B, 1.71; N, 4.44; experimental value: C, 87.65; H, 3.67; B, 1.72; N, 4.41. Synthesis Example B-6: Synthesis of Compound B1-17 [Chemical formula]

[0105] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-17 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 658.41 Elemental analysis result: theoretical value: C, 83.87; H, 7.80; B, 1.64; N, 4.25;; experimental value: C, 83.89; H, 7.81; B, 1.61; N, 4.25;. Synthesis Example B-7: Synthesis of Compound B1-21

Chemical Structure

[0106] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and after continuing the reaction at 130 °C for 12 hours, the reaction was stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-21 (31% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 760.24. Elemental analysis result: theoretical value: C, 85.27; H, 3.84; B, 1.42; N, 7.37; experimental value: C, 85.26; H, 3.85; B, 1.40; N, 7.35. Synthesis Example B-8: Synthesis of Compound B1-24

Chemical Structure

[0107] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-24 (22% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 760.24 Elemental analysis result: theoretical value: C, 85.27; H, 3.84; B, 1.42; N, 7.37; experimental value: C, 85.27; H, 3.83; B, 1.44; N, 7.37. Synthesis Example B-9: Synthesis of Compound B1-44 [Chemical formula]

[0108] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-44 (35% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 760.24 Elemental analysis result: theoretical value: C, 85.27; H, 3.84; B, 1.42; N, 7.37; experimental value: C, 85.28; H, 3.86; B, 1.40; N, 7.36. Synthesis Example B-10: Synthesis of Compound B1-55

Chemical Structure

[0109] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours. At room temperature, a tetrahydrofuran solution of phenylmagnesium bromide (60 mmol) was added, and the reaction was stopped after 6 hours. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-55 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 758.25 Elemental analysis result: theoretical value: C, 88.66; H, 4.12; B, 1.42; N, 3.69; experimental value: C, 88.65; H, 4.14; B, 1.41; N, 3.66. Synthesis Example B-11: Synthesis of Compound B1-65

Chemical Structure

[0110] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-65 (35% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 582.19 Elemental analysis result: theoretical value: C, 86.61; H, 3.98; B, 1.86; N, 4.81; experimental value: C, 86.65; H, 4.01; B, 1.86; N, 4.84. Synthesis Example B-12: Synthesis of Compound B1-70 [Chemical formula]

[0111] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-70 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 668.39 Elemental analysis result: theoretical value: 84.42; H, 7.39; B, 1.62; N, 4.19; experimental value: 84.44; H, 7.35; B, 1.60; N, 4.21. Synthesis Example B-13: Synthesis of Compound B1-80

Chemical formula

[0112] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and after reacting at 130 °C for a further 12 hours, the reaction was stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-80 (35% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 462.12 Elemental analysis result: theoretical value: C, 77.95; H, 3.27; B, 2.34; N, 6.06; experimental value: C, 77.98; H, 3.26; B, 2.32; N, 6.05. Synthesis Example B-14: Synthesis of Compound B1-81

Chemical formula

[0113] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-81 (30% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 494.07 Elemental analysis result: theoretical value: C, 72.88; H, 3.06; B, 2.19; N, 5.67; S, 12.97 Experimental value: C, 72.87; H, 3.08; B, 2.21; N, 5.66; S, 12.99. Synthesis Example B-15: Synthesis of Compound B1-82

Chemical formula

[0114] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continued reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-82 (25% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 589.96 Elemental analysis result: theoretical value: C, 61.26; H, 2.57; B, 1.84; N, 4.76; Se, 26.85 Experimental value: C, 61.25; H, 2.55; B, 1.85; N, 4.73; Se, 26.89. Synthesis Example B-16: Synthesis of Compound B1-85

Chemical Structure

[0115] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-85 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 794.24 Elemental analysis result: theoretical value: C, 81.60; H, 4.44; B, 1.36; N, 3.52; Si, 7.07; experimental value: C, 81.55; H, 4.46; B, 1.37; N, 3.50; Si, 7.10. Synthesis Example B-17: Synthesis of Compound B1-87

Chemical formula

[0116] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-87 (34% yield, HPLC analysis purity 99%) as an orange solid. MALDI-TOF-MS result: molecular ion peak: 466.12 Elemental analysis result: theoretical value: C, 80.74; H, 3.39; B, 2.42; N, 6.28; experimental value: C, 80.77; H, 3.38; B, 2.40; N, 6.29. Synthesis Example B-18: Synthesis of Compound B1-94 [Chemical formula]

[0117] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-94 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 610.17 Elemental analysis result: theoretical value: C, 82.62; H, 3.80; B, 1.77; N, 4.59; Si, 4.60 Experimental value: C, 82.60; H, 3.82; B, 1.80; N, 4.55; Si, 4.62. Synthesis Example B-19: Synthesis of Compound B1-155 [Chemical formula]

[0118] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-155 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 536.12 Elemental analysis result: theoretical value: C, 80.61; H, 3.19; B, 2.02; N, 5.22; S, 5.98 Experimental value: C, 80.60; H, 3.15; B, 2.04; N, 5.23; S, 6.03. Synthesis Example B-20: Synthesis of Compound B1-179

Chemical Structure

[0119] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-179 (28% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30; Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.74; H, 5.38; B, 1.52; N, 6.06. Synthesis Example B-21: Synthesis of Compound B1-180 [Chemical formula]

[0120] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-180 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30; Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.73; H, 5.38; B, 1.57; N, 6.01. Synthesis Example B-22: Synthesis of Compound B1-181 [Chemical formula]

[0121] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, the reaction mixture was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C, and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-181 (31% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.70; H, 5.35; B, 1.58; N, 6.07. Synthesis Example B-23: Synthesis of Compound B1-182 [Chemical formula]

[0122] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-182 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.74; H, 5.38; B, 1.53; N, 6.04. Synthesis Example B-24: Synthesis of Compound B1-183 [Chemical formula]

[0123] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-183 (29% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.70; H, 5.40; B, 1.54; N, 6.05. Synthesis Example B-25: Synthesis of Compound B1-184

Chemical Structure

[0124] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-184 (37% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.74; H, 5.35; B, 1.54; N, 6.08. Synthesis Example B-26: Synthesis of Compound B1-185

Chemical Structure

[0125] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-185 (30% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.71; H, 5.40; B, 1.59; N, 6.03. Synthesis Example B-27: Synthesis of Compound B1-186

Chemical formula

[0126] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B1-186 (33% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 694.30 Elemental analysis result: theoretical value: C, 84.72; H, 5.37; B, 1.56; N, 6.05; experimental value: C, 84.70; H, 5.38; B, 1.54; N, 6.04. Synthesis Example B-28: Synthesis of Compound B2-4

Chemical Structure

[0127] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and after continuing the reaction at 130 °C for 12 hours, the reaction was stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B2-4 (33% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 638.38. Elemental analysis result: theoretical value C, 86.50; H, 7.42; B, 1.69; N, 4.39; experimental value: C, 86.52; H, 7.45; B, 1.68; N, 4.34. Synthesis Example B-29: Synthesis of Compound B2-57

Chemical Structure

[0128] Under a nitrogen gas atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B2-57 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 583.22 Elemental analysis result: theoretical value C, 86.45; H, 4.49; B, 1.85; N, 7.20 Experimental value: C, 86.47; H, 4.45; B, 1.86; N, 7.18. Synthesis Example B-30: Synthesis of Compound B3-4 [Chemical formula]

[0129] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B3-4 (30% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 788.44 Elemental analysis result: theoretical value: C, 83.74; H, 7.41; B, 1.37; N, 3.55; P, 3.93; experimental value: C, 83.70; H, 7.45; B, 1.36; N, 3.58; P, 3.88. Synthesis Example B-31: Synthesis of Compound B4-4 [Chemical formula]

[0130] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B4-4 (34% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 670.36 Elemental analysis result: theoretical value C, 82.37; H, 7.06; B, 1.61; N, 4.18; S, 4.78; experimental value: C, 82.32; H, 7.05; B, 1.63; N, 4.14; S, 4.81. Synthesis Example B-32: Synthesis of Compound B5-4

Chemical Structure

[0131] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B5-4 (33% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 718.30 Elemental analysis result: theoretical value: C, 76.99; H, 6.60; B, 1.51; N, 3.90; Se, 11.00; experimental value: C, 7.02; H, 6.57; B, 1.54; N, 3.88; Se, 11.05. Synthesis Example B-33: Synthesis of Compound B6-4 [Chemical formula]

[0132] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B6-4 (37% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 729.43 Elemental analysis result: theoretical value: C, 85.58; H, 7.18; B, 1.48; N, 5.76; experimental value: C, 85.66; H, 7.14; B, 1.52; N, 5.71. Synthesis Example B-34: Synthesis of Compound B7-4 [Chemical formula]

[0133] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After the reaction was completed, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B7-4 (37% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 804.46 Elemental analysis result: theoretical value C, 88.04; H, 7.14; B, 1.34; N, 3.48; experimental value: C, 88.05; H, 7.16; B, 1.36; N, 3.44. Synthesis Example B-35: Synthesis of Compound B8-4

Chemical Structure

[0134] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, the mixture was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B8-4 (38% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 820.44 Elemental analysis result: theoretical value: C, 84.85; H, 7.00; B, 1.32; N, 3.41; Si, 3.42; experimental value: C, 84.82; H, 7.02; B, 1.33; N, 3.40; Si, 3.44. Synthesis Example B-36: Synthesis of Compound B4-162

Chemical Structure

[0135] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, the reaction is continued at 130 °C for 12 hours and then stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B4-162 (35% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 664.22 Elemental analysis result: theoretical value C, 79.51; H, 5.00; B, 1.63; N, 4.21; S, 9.65; experimental value: C, 79.53; H, 5.02; B, 1.60; N, 4.20; S, 9.69. Synthesis Example B-37: Synthesis of Compound B4-186 [Chemical formula]

[0136] In a nitrogen gas atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) was added, and the reaction was continued at 130 °C for 12 hours and then stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B4-186 (37% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 723.29; Elemental analysis result: theoretical value C, 82.98; H, 5.29; B, 1.49; N, 5.81; S, 4.43; experimental value: C, 82.97; H, 5.30; B, 1.50; N, 5.80; S, 4.45. Synthesis Example B-38: Synthesis of Compound B7-45

Chemical Structure

[0137] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B7-45 (27% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 798.32 Elemental analysis result: theoretical value: C, 85.70; H, 5.43; B, 1.35; N, 3.51; S, 4.01; experimental value: C, 85.67; H, 5.40; B, 1.32; N, 3.54; S, 4.07. Synthesis Example B-39: Synthesis of Compound B7-58 [Chemical formula]

[0138] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B7-58 (30% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 857.39 Elemental analysis result: theoretical value: C, 88.20; H, 5.64; B, 1.26; N, 4.90; experimental value: C, C, 88.20; H, 5.65; B, 1.25; N, 4.88. Synthesis Example B-40: Synthesis of Compound B7-59

Chemical Structure

[0139] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B7-59 (33% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.31; elemental analysis result: theoretical value: C, 85.92; H, 5.19; B, 1.36; N, 3.52; S, 4.02; experimental value: C, 85.95; H, 5.17; B, 1.35; N, 3.53; S, 4.00. Synthesis Example B-41: Synthesis of Compound B7-60

Chemical Structure

[0140] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B7-60 (37% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 855.38 Elemental analysis result: theoretical value: C, 88.41; H, 5.42; B, 1.26; N, 4.91; experimental value: C, 88.38; H, 5.40; B, 1.27; N, 4.95. Synthesis Example B-42: Synthesis of Compound B8-45 [Chemical formula]

[0141] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After the reaction is completed, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours and then stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B8-45 (29% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 814.30 Elemental analysis result: theoretical value C, 82.54; H, 5.32; B, 1.33; N, 3.44; S, 3.93; Si, 3.45; experimental value: C, 82.55; H, 5.33; B, 1.31; N, 3.45; S, 3.95; Si, 3.42. Synthesis Example B-43: Synthesis of Compound B8-58

Chemical Structure

[0142] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. At room temperature, N,N-diisopropylethylamine (120 mmol) is added, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped. The solvent is spin-dried in vacuo and passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B8-58 (33% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 873.37 Elemental analysis result: theoretical value: C, 85.21; H, 5.54; B, 1.24; N, 4.81; Si, 3.21; experimental value: C, 85.20; H, 5.57; B, 1.23; N, 4.82; Si, 3.18. Synthesis Example B-44: Synthesis of Compound B8-59

Chemical formula

[0143] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature was raised to 25 °C and reacted for 1 hour. After completion of the reaction, it was cooled to -30 °C, boron tribromide (60 mmol) was slowly added, the temperature was raised to 60 °C and stirring was continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) was added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction was stopped. The solvent was spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B8-59 (34% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 812.29 Elemental analysis result: theoretical value: C, 82.74; H, 5.08; B, 1.33; N, 3.45; S, 3.94; Si, 3.45; experimental value: C, 82.75; H, 5.09; B, 1.37; N, 3.41; S, 3.95; Si, 3.42. Synthesis Example B-45: Synthesis of Compound B8-60

Chemical formula

[0144] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of the brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and after continuing the reaction at 130 °C for 12 hours, the reaction is stopped, the solvent is spin-dried in vacuo, and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound B8-60 (35% yield, HPLC analysis purity 99%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 871.36 Elemental analysis result: theoretical value: C, 85.40; H, 5.32; B, 1.24; N, 4.82; Si, 3.22; experimental value: C, 85.40; H, 5.33; B, 1.22; N, 4.80; Si, 3.25.

[0145] Typical synthetic route C: [Chemical formula] More specifically, the method for synthesizing a typical compound of the present invention is shown below. Synthesis Example C-1: Synthesis of compound C1-1 [Chemical formula]

[0146] In a nitrogen gas atmosphere, a pentane solution of n-butyllithium (60 mmol) is slowly added to a solution of a brominated precursor (15 mmol) in t-butylbenzene (150 mL) at 0 °C, and then the temperature is raised to 25 °C and reacted for 1 hour. After completion of the reaction, it is cooled to -30 °C, boron tribromide (60 mmol) is slowly added, the temperature is raised to 60 °C and stirring is continued for 2 hours. N,N-Diisopropylethylamine (120 mmol) is added at room temperature, and the reaction is continued at 130 °C for 12 hours. The solvent is spin-dried in vacuo and passed through a silica gel column (developing agent: dichloromethane: petroleum ether = 1:10) to obtain the target compound C1-1 (32% yield, HPLC analysis purity 99%) as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 602.2159; elemental analysis result: theoretical values C, 81.75; H, 4.69; B, 3.59; N, 4.65; S, 5.32; experimental values: C, 81.78; H, 4.62; B, 3.52; N, 4.61; S, 5.37. Synthesis Example C-2: Synthesis of Compound C1-32

Chemical formula

[0147] The specific experimental method is the same as that of Synthesis Example C-1, except that the corresponding brominated precursor is exchanged. The target compound C1-32 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 711.3017; elemental analysis result: theoretical values: C, 86.10; H, 4.96; B, 3.04; N, 5.91; experimental values: C, 86.16; H, 4.91; B, 3.07; N, 5.96. Synthesis Example C-3: Synthesis of Compound C1-47

Chemical formula

[0148] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C1-47 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 850.3691. Elemental analysis result: theoretical values: C, 88.95; H, 5.21; B, 2.54; N, 3.29; experimental values: C, 88.91; H, 5.26; B, 2.52; N, 3.27. Synthesis Example C-4: Synthesis of Compound C1-65

Chemical Structure

[0149] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C1-65 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 623.2704. Elemental analysis result: theoretical values: C, 84.78; H, 5.01; B, 3.47; N, 6.74; experimental values: C, 84.71; H, 5.07; B, 3.41; N, 6.76. Synthesis Example C-5: Synthesis of Compound C1-84

Chemical Structure

[0150] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C1-84 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 767.2738. Elemental analysis result: theoretical values: C, 82.94; H, 4.60; B, 2.82; N, 5.47; S, 4.18; experimental values: C, 82.96; H, 4.62; B, 2.85; N, 5.42; S, 4.15. Synthesis Example C-6: Synthesis of Compound C2-1

Chemical Structure

[0151] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C2-1 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 598.2250; Elemental analysis result: theoretical value: C, 80.26; H, 5.22; B, 1.81; N, 4.68; O, 2.67; S, 5.36; experimental value: C, 80.26; H, 5.22; B, 1.81; N, 4.68; O, 2.67; S, 5.36. Synthesis Example C-7: Synthesis of Compound C2-23

Chemical Structure

[0152] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C2-23 (29% yield, HPLC analysis purity 99%) is obtained as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 710.2278; Elemental analysis result: theoretical value: C, 84.51; H, 3.83; B, 1.52; N, 7.88; O, 2.25; experimental value: C, 84.52; H, 3.84; B, 1.56; N, 7.81; O, 2.22. Synthesis Example C-8: Synthesis of Compound C2-40

Chemical Structure

[0153] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C2-40 (32% yield, HPLC analysis purity 99%) is obtained as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 749.2638; Elemental analysis result: theoretical value: C, 86.52; H, 4.30; B, 1.44; N, 5.61; O, 2.13; experimental value: C, 86.57; H, 4.31; B, 1.42; N, 5.65; O, 2.11. Synthesis Example C-9: Synthesis of Compound C2-63 [Chemical formula]

[0154] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C2-63 (31% yield, HPLC analysis purity 99%) is obtained as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 613.1420; Elemental analysis result: theoretical values: C, 80.27; H, 3.29; B, 1.76; N, 6.85; O, 2.61; S, 5.23; experimental values: C, 80.22; H, 3.21; B, 1.73; N, 6.84; O, 2.65; S, 5.21. Synthesis Example C-10: Synthesis of Compound C2-75 [Chemical formula]

[0155] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C2-75 (32% yield, HPLC analysis purity 99%) is obtained as an orange-yellow solid. MALDI-TOF-MS result: molecular ion peak: 604.1781; Elemental analysis result: theoretical values: C, 81.46; H, 4.17; B, 1.79; N, 4.63; O, 2.65; S, 5.30; experimental values: C, 81.47; H, 4.12; B, 1.72; N, 4.69; O, 2.61; S, 5.38. Synthesis Example C-11: Synthesis of Compound C3-11 [Chemical formula]

[0156] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C3-11 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 639.1940 Elemental analysis result: theoretical value: C, 82.63; H, 4.10; B, 1.69; N, 6.57; S, 5.01; experimental value: C, 82.61; H, 4.14; B, 1.67; N, 6.52; S, 5.03. Synthesis Example C-12: Synthesis of Compound C3-30

Chemical formula

[0157] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C3-30 (35% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 649.2689 Elemental analysis result: theoretical value: C, 86.90; H, 4.97; B, 1.66; N, 6.47; experimental value: C, 86.93; H, 4.96; B, 1.63; N, 6.46. Synthesis Example C-13: Synthesis of Compound C3-40

Chemical formula

[0158] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C3-40 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 731.2533 Elemental analysis result: theoretical value: C, 88.65; H, 4.13; B, 1.48; N, 5.74; experimental value: C, 88.62; H, 4.14; B, 1.47; N, 5.77. Synthesis Example C-14: Synthesis of Compound C3-52

Chemical formula

[0159] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C3-52 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 763.3159. Elemental analysis result: theoretical value: C, 88.07; H, 5.02; B, 1.42; N, 5.50; experimental value: C, 88.03; H, 5.07; B, 1.44; N, 5.57. Synthesis Example C-15: Synthesis of Compound C3-63

Chemical Structure

[0160] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C3-63 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 647.1627. Elemental analysis result: theoretical value: C, 83.47; H, 3.42; B, 1.67; N, 6.49; S, 4.95; experimental value: C, 83.42; H, 3.47; B, 1.63; N, 6.43; S, 4.97. Synthesis Example C-16: Synthesis of Compound C4-33

Chemical Structure

[0161] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C4-33 (25% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 748.2273. Elemental analysis result: theoretical value: C, 81.82; H, 4.58; B, 1.44; N, 3.74; P, 4.14; S, 4.28; experimental value: C, 81.87; H, 4.53; B, 1.44; N, 3.77; P, 4.12; S, 4.26. Synthesis Example C-17: Synthesis of Compound C4-51 [Chemical formula]

[0162] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C4-51 (26% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 747.2069 Elemental analysis result: theoretical value: C, 80.32; H, 4.18; B, 1.45; N, 5.62; P, 4.14; S, 4.29; experimental value: C, 80.31; H, 4.13; B, 1.46; N, 5.64; P, 4.12; S, 4.24. Synthesis Example C-18: Synthesis of Compound C5-11 [Chemical formula]

[0163] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C5-11 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 671.1661 Elemental analysis result: theoretical value: C, 78.69; H, 3.90; B, 1.61; N, 6.26; S, 9.55; experimental value: C, 78.61; H, 3.93; B, 1.66; N, 6.22; S, 9.53. Synthesis Example C-19: Synthesis of Compound C5-23 [Chemical formula]

[0164] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C5-23 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 726.2049. Elemental analysis result: theoretical values: C, 82.64; H, 3.75; B, 1.49; N, 7.71; S, 4.41; experimental values: C, 82.61; H, 3.78; B, 1.42; N, 7.76; S, 4.48. Synthesis Example C-20: Synthesis of Compound C5-39 [Chemical Structure]

[0165] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C5-39 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 763.2253. Elemental analysis result: theoretical values: C, 84.93; H, 3.96; B, 1.42; N, 5.50; S, 4.20; experimental values: C, 84.94; H, 3.96; B, 1.47; N, 5.53; S, 4.26. Synthesis Example C-21: Synthesis of Compound C5-63 [Chemical Structure]

[0166] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C5-63 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 629.1192. Elemental analysis result: theoretical values: C, 78.22; H, 3.20; B, 1.72; N, 6.67; S, 10.18; experimental values: C, 78.26; H, 3.21; B, 1.73; N, 6.66; S, 10.13. Synthesis Example C-22: Synthesis of Compound C5-69 [Chemical Structure]

[0167] The specific experimental method is the same as that of Synthesis Example C-1, except that the corresponding brominated precursor is exchanged. The target compound C5-69 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 581.1192. Elemental analysis result: theoretical values: C, 76.42; H, 3.47; B, 1.86; N, 7.23; S, 11.03; experimental values: C, 76.46; H, 3.42; B, 1.84; N, 7.28; S, 11.06. Synthesis Example C-23: Synthesis of Compound C6-11

Chemical Structure

[0168] The specific experimental method is the same as that of Synthesis Example C-1, except that the corresponding brominated precursor is exchanged. The target compound C6-11 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 719.1106. Elemental analysis result: theoretical values: C, 73.55; H, 3.65; B, 1.50; N, 5.85; S, 4.46; Se, 10.99; experimental values: C, 73.52; H, 3.62; B, 1.55; N, 5.88; S, 4.42; Se, 10.96. Synthesis Example C-24: Synthesis of Compound C6-27

Chemical Structure

[0169] The specific experimental method is the same as that in Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C6-27 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 729.1855 Elemental analysis result: theoretical value: C, 77.48; H, 4.43; B, 1.48; N, 5.77; Se, 10.84; experimental value: C, 77.43; H, 4.45; B, 1.43; N, 5.75; Se, 10.87. Synthesis Example C-25: Synthesis of Compound C6-50

Chemical Structure

[0170] The specific experimental method is the same as that in Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C6-50 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 761.1542 Elemental analysis result: theoretical value: C, 78.96; H, 3.71; B, 1.42; N, 5.52; Se, 10.38; experimental value: C, 78.92; H, 3.77; B, 1.47; N, 5.54; Se, 10.36. Synthesis Example C-26: Synthesis of Compound C7-6

Chemical Structure

[0171] The specific experimental method is the same as that in Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C7-6 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 667.1348 Elemental analysis result: theoretical value: C, 79.16; H, 3.32; B, 1.62; N, 6.29; S, 9.60; experimental value: C, 79.14; H, 3.36; B, 1.62; N, 6.39; S, 9.65. Synthesis Example C-27: Synthesis of Compound C7-22 [Chemical formula]

[0172] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C7-22 (27% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 673.3264; Elemental analysis result: theoretical values: C, 83.80; H, 5.99; B, 1.60; N, 6.24; O, 2.37; experimental values: C, 83.85; H, 5.93; B, 1.61; N, 6.25; O, 2.33. Synthesis Example C-28: Synthesis of Compound C7-38 [Chemical formula]

[0173] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C7-38 (27% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 678.2049; Elemental analysis result: theoretical values: C, 81.42; H, 4.01; B, 1.59; N, 8.26; S, 4.72; experimental values: C, 81.47; H, 4.05; B, 1.52; N, 8.23; S, 4.77. Synthesis Example C-29: Synthesis of Compound C7-48 [Chemical formula]

[0174] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C7-48 (25% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 822.2955; Elemental analysis result: theoretical values: C, 87.59; H, 4.29; B, 1.31; N, 6.81; experimental values: C, 87.52; H, 4.23; B, 1.36; N, 6.86. Synthesis Example C-30: Synthesis of Compound C7-70

Chemical Structure

[0175] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C7-70 (32% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 688.1893; Elemental analysis result: theoretical value: C, 81.98; H, 3.66; B, 1.57; N, 8.14; S, 4.66; experimental value: C, 81.92; H, 3.66; B, 1.53; N, 8.11; S, 4.65. Synthesis Example C-31: Synthesis of Compound C8-2

Chemical Structure

[0176] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C8-2 (35% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 740.1552; Elemental analysis result: theoretical value: C, 82.70; H, 3.40; B, 1.46; N, 3.78; S, 8.66; experimental value: C, 82.73; H, 3.45; B, 1.46; N, 3.71; S, 8.63. Synthesis Example C-32: Synthesis of Compound C8-23

Chemical Structure

[0177] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C8-23 (30% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 695.2376. Elemental analysis result: theoretical values: C, 88.31; H, 4.07; B, 1.56; N, 6.06; experimental values: C, 88.33; H, 4.06; B, 1.51; N, 6.05. Synthesis Example C-33: Synthesis of Compound C8-36

Chemical Structure

[0178] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C8-36 (30% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 692.1552. Elemental analysis result: theoretical values: C, 81.50; H, 3.64; B, 1.56; N, 4.04; S, 9.26; experimental values: C, 81.52; H, 3.67; B, 1.51; N, 4.07; S, 9.23. Synthesis Example C-34: Synthesis of Compound C8-48

Chemical Structure

[0179] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C8-48 (34% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 939.3785. Elemental analysis result: theoretical values: C, 89.45; H, 4.93; B, 1.15; N, 4.47; experimental values: C, 89.41; H, 4.96; B, 1.13; N, 4.46. Synthesis Example C-35: Synthesis of Compound C8-60

Chemical Structure

[0180] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C8-60 (37% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 824.3363; Elemental analysis result: theoretical value: C, 90.28; H, 5.01; B, 1.31; N, 3.40; experimental value: C, 90.23; H, 5.01; B, 1.36; N, 3.41. Synthesis Example C-36: Synthesis of Compound C8-74

Chemical Structure

[0181] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C8-74 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 803.2566; Elemental analysis result: theoretical value: C, 85.17; H, 4.26; B, 1.34; N, 5.23; S, 3.99; experimental value: C, 85.16; H, 4.24; B, 1.32; N, 5.21; S, 3.93. Synthesis Example C-37: Synthesis of Compound C9-2

Chemical Structure

[0182] The specific experimental method is the same as that of Synthesis Example C-1, and only the corresponding brominated precursor is exchanged. The target compound C9-2 (29% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 756.1321; Elemental analysis result: theoretical value: C, 79.36; H, 3.33; B, 1.43; N, 3.70; S, 8.47; Si, 3.71; experimental value: C, 79.34; H, 3.36; B, 1.47; N, 3.71; S, 8.43; Si, 3.77. Synthesis Example C-38: Synthesis of Compound C9-22

Chem.

[0183] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C9-22 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 825.2772; Elemental analysis result: theoretical value: C, 85.84; H, 4.37; B, 1.32; N, 5.09; Si, 3.40; experimental value: C, 85.81; H, 4.39; B, 1.31; N, 5.02; Si, 3.45. Synthesis Example C-39: Synthesis of Compound C9-39

Chem.

[0184] The specific experimental method is the same as that of Synthesis Example C-1, only by exchanging the corresponding brominated precursor. The target compound C9-39 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 788.2455; Elemental analysis result: theoretical value: C, 85.27; H, 4.22; B, 1.37; N, 3.55; O, 2.03; Si, 3.56; experimental value: C, 85.22; H, 4.25; B, 1.35; N, 3.57; O, 2.07; Si, 3.52. Synthesis Example C-40: Synthesis of Compound C9-69

Chem.

[0185] The specific experimental method is the same as that in Synthesis Example C-1, except that the corresponding brominated precursor is exchanged. The target compound C9-69 (31% yield, HPLC analysis purity 99%) is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 701.2459; Elemental analysis result: theoretical values: C, 83.87; H, 4.60; B, 1.54; N, 5.99; Si, 4.00; experimental values: C, 83.82; H, 4.66; B, 1.52; N, 5.95; Si, 4.06.

[0186] Synthesis Route D: Example D-1. Synthesis of Compound D1-1

Chemical Structure

[0187] In a two-necked flask, under a nitrogen gas atmosphere, Compound I-1-1 (15.7 mmol), carbazole (31.4 mmol), and cesium carbonate (61 mmol) are dissolved in 150 mL of N,N-dimethylformamide (DMF), heated to 150 °C, and reacted for 16 hours. After the reaction is completed and cooled, it is poured into cold water, filtered, washed twice with 100 mL of water, then washed once with 10 mL of methanol, and dried to obtain the target compound I-1-2 as a pale yellow solid.

[0188] In a two-necked flask, under a nitrogen gas atmosphere, compound I-1-2 (5 mmol) is dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 6 ml) is added, and the reaction is carried out at this temperature for 1 hour. I-1-3 is dissolved in 40 ml of dry tetrahydrofuran previously cooled to -78 °C, and then the solution is slowly poured into the solution of I-1-2 at -78 °C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction is completed, a small amount of methanol is added for quenching, the solvent is evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid are added, and then the temperature is raised for refluxing. After reacting for 2 hours, it is neutralized with a saturated aqueous sodium carbonate solution, extracted with dichloromethane, separated, and the organic phase is collected. The organic phase is dried over anhydrous sodium sulfate, then filtered and the organic phase is concentrated. The compound is separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing agent to obtain compound I-1-4.

[0189] In a sealed tube, compound I-1-4 (1 mmol) is dissolved in 20 mL of t-butylbenzene, cooled to -78 °C, and then a pentane solution of t-butyllithium (1 M, 2.5 mL) is added, and then the temperature is raised to 30 °C and reacted for 1 hour. It is cooled to -78 °C again, boron tribromide (3 mmol) is slowly added, and then the temperature is raised to 30 °C and stirring is continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) is added, and then the temperature is raised to 160 °C and reacted for 12 hours. The solvent is dried under vacuum, and the target compound D1-1 (HPLC analysis purity 99.43%) is obtained as a yellow solid by passing through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent. MALDI-TOF-MS result: molecular ion peak: 628.2112; elemental analysis result: theoretical value: C, 89.812; H, 4.014; B, 1.722; N, 4.464 (%); experimental value: C, 89.820; H, 4.099; B, 1.622; N, 4.368 (%).

[0190] The synthesis methods of the following synthesis examples are all the same as those of Example D-1. It is only necessary to replace the carbazole in the first step with the corresponding carbazole derivative and replace I-1-3 with the aromatic ketone raw material of the corresponding fragment in the example.

Chemical Structure

[0191] Target compound D1-2 (HPLC analysis purity 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 684.2721; elemental analysis result: theoretical value: C, 89.468; H, 4.857; B, 1.579; N, 4.092 (%); experimental value: C, 89.470; H, 4.854; B, 1.678; N, 4.008 (%).

[0192] Target compound D1-3 (HPLC analysis purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 852.4652; elemental analysis result: theoretical value: C, 88.707; H, 6.735; B, 1.272; N, 3.278 (%); experimental value: C, 88.700; H, 6.686; B, 1.218; N, 3.263 (%).

[0193] Target compound D1-10 (HPLC analysis purity 99.73%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 728.1951; elemental analysis result: theoretical value: C, 84.075; H, 2.913; B, 1.475; N, 11.541 (%); experimental value: C, 84.070; H, 2.910; B, 1.566; N, 11.464 (%).

[0194] Target compound D1-23 (HPLC analytical purity: 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 828.2725; elemental analysis result: theoretical values: C, 91.302; H, 4.009; B, 1.304; N, 3.376 (%); experimental values: C, 91.310; H, 4.020; B, 1.396; N, 3.354 (%).

[0195] Target compound D1-29 (HPLC analytical purity: 99.65%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 958.3335; elemental analysis result: theoretical values: C, 88.934; H, 4.101; B, 1.133; N, 5.836 (%); experimental values: C, 88.940; H, 4.140; B, 1.068; N, 5.788 (%).

[0196] Target compound D1-41 (HPLC analytical purity: 99.72%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 768.3735; elemental analysis result: theoretical values: C, 89.045; H, 5.897; B, 1.406; N, 3.643 (%); experimental values: C, 89.050; H, 5.802; B, 1.437; N, 3.616 (%).

[0197] Target compound D1-50 (HPLC analytical purity: 99.88%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 790.3353; elemental analysis result: theoretical values: C, 86.583; H, 4.969; B, 1.367; N, 7.086 (%); experimental values: C, 86.570; H, 4.905; B, 1.415; N, 7.015 (%).

[0198] Target compound D1-53 (HPLC analytical purity: 99.90%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.3125; elemental analysis result: theoretical values: C, 85.923; H, 5.193; B, 1.358; N, 3.518; S, 4.015 (%); experimental values: C, 85.930; H, 5.109; B, 1.395; N, 3.608; S, 4.033 (%).

[0199] Target compound D1-54 (HPLC analytical purity 99.66%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 780.3353; elemental analysis result: theoretical values: C, 87.694; H, 5.291; B, 1.380; N, 3.585; O, 2.046 (%); experimental values: C, 87.700; H, 5.285; B, 1.432; N, 3.515; O, 1.950 (%).

[0200] Target compound D1-59 (HPLC analytical purity 99.80%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 903.3862; elemental analysis result: theoretical values: C, 89.032; H, 5.126; B, 1.196; N, 4.654 (%); experimental values: C, 89.040; H, 5.087; B, 1.228; N, 4.652 (%).

[0201] Target compound D1-60 (HPLC analytical purity 99.34%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 830.3563; elemental analysis result: theoretical values: C, 88.184; H, 5.219; B, 1.297; N, 3.371; O, 1.933 (%); experimental values: C, 88.180; H, 5.222; B, 1.237; N, 3.426; O, 1.977 (%).

[0202] Target compound D1-61 (HPLC analytical purity 99.54%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3236; elemental analysis result: theoretical values: C, 86.511; H, 5.118; B, 1.280; N, 3.305; S, 3.790 (%); experimental values: C, 86.520; H, 5.219; B, 1.202; N, 3.236; S, 3.728 (%).

[0203] Target compound D1-65 (HPLC analytical purity 99.18%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.2723; elemental analysis result: theoretical values: C, 81.969; H, 4.845; B, 1.206; N, 3.126; Se, 8.840 (%); experimental values: C, 81.970; H, 4.840; B, 1.117; N, 3.157; Se, 8.742 (%).

[0204] The target compound D1-75 (HPLC analytical purity: 99.78%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3263; elemental analysis result: theoretical values: C, 86.512; H, 5.118; B, 1.283; N, 3.311; S, 3.785 (%); experimental values: C, 86.510; H, 5.138; B, 1.340; N, 3.289; S, 3.780 (%).

[0205] The target compound D1-77 (HPLC analytical purity: 99.41%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 905.3963; elemental analysis result: theoretical values: C, 88.829; H, 5.344; B, 1.189; N, 4.641 (%); experimental values: C, 88.820; H, 5.387; B, 1.180; N, 4.704 (%).

[0206] The target compound D1-78 (HPLC analytical purity: 99.62%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 903.3826; elemental analysis result: theoretical values: C, 89.032; H, 5.125; B, 1.199; N, 4.649 (%); experimental values: C, 89.040; H, 5.206; B, 1.185; N, 4.666 (%).

[0207] The target compound D1-85 (HPLC analytical purity: 99.86%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.2772; elemental analysis result: theoretical values: C, 81.968; H, 4.849; B, 1.212; N, 3.130; Se, 8.836 (%); experimental values: C, 81.980; H, 4.794; B, 1.309; N, 3.033; Se, 8.775 (%).

[0208] The target compound D1-86 (HPLC analytical purity: 99.40%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3223; elemental analysis result: theoretical values: C, 86.508; H, 5.123; B, 1.280; N, 3.306; S, 3.786 (%); experimental values: C, 86.500; H, 5.085; B, 1.258; N, 3.284; S, 3.817 (%).

[0209] The target compound D1-167 (HPLC analytical purity: 99.16%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 852.4623; elemental analysis result: theoretical values: C, 88.705; H, 6.735; B, 1.272; N, 3.279 (%); experimental values: C, 88.710; H, 6.831; B, 1.217; N, 3.281 (%).

[0210] The target compound D1-170 (HPLC analytical purity: 99.25%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 950.1873; elemental analysis result: theoretical values: C, 69.486; H, 2.437; B, 1.138; F, 23.981; N, 2.945 (%); experimental values: C, 69.490; H, 2.456; B, 1.133; F, 24.063; N, 2.974 (%).

[0211] The target compound D1-181 (HPLC analytical purity: 99.59%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 1032.3272; elemental analysis result: theoretical values: C, 87.205; H, 3.612; B, 1.052; N, 8.142 (%); experimental values: C, 87.220; H, 3.651; B, 1.125; N, 8.057 (%).

[0212] The target compound D1-183 (HPLC analytical purity: 99.45%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 892.255; elemental analysis result: theoretical values: C, 84.759; H, 3.730; B, 1.205; N, 3.135; O, 7.166 (%); experimental values: C, 84.750; H, 3.689; B, 1.127; N, 3.202; O, 7.107 (%).

[0213] The target compound D1-184 (HPLC analytical purity: 99.17%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 956.1624; elemental analysis result: theoretical values: C, 79.068; H, 3.477; B, 1.134; N, 2.929; S, 13.404 (%); experimental values: C, 79.060; H, 3.391; B, 1.199; N, 2.847; S, 13.434 (%).

[0214] The target compound D1-189 (HPLC analytical purity 99.75%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 840.1935; elemental analysis result: theoretical values: C, 84.282; H, 3.475; B, 1.287; N, 3.328; S, 7.628 (%); experimental values: C, 84.290; H, 3.430; B, 1.381; N, 3.260; S, 7.697 (%).

[0215] The target compound D1-194 (HPLC analytical purity 99.86%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 958.3357; elemental analysis result: theoretical values: C, 88.929; H, 4.104; B, 1.128; N, 5.839 (%); experimental values: C, 88.920; H, 4.189; B, 1.065; N, 5.877 (%).

[0216] The target compound D1-197 (HPLC analytical purity 99.16%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 840.1968; elemental analysis result: theoretical values: C, 84.276; H, 3.475; B, 1.293; N, 3.325; S, 7.633 (%); experimental values: C, 84.270; H, 3.517; B, 1.383; N, 3.351; S, 7.640 (%).

[0217] The target compound D1-201 (HPLC analytical purity 99.29%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 840.1979; elemental analysis result: theoretical values: C, 84.275; H, 3.475; B, 1.286; N, 3.333; S, 7.632 (%); experimental values: C, 84.270; H, 3.446; B, 1.352; N, 3.417; S, 7.675 (%).

[0218] Target compound D1-203 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 840.1953; elemental analysis result: theoretical values: C, 84.279; H, 3.480; B, 1.285; N, 3.329; S, 7.627 (%); experimental values: C, 84.280; H, 3.492; B, 1.336; N, 3.405; S, 7.660 (%).

[0219] Target compound D1-205 (HPLC analytical purity 99.04%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 768.3735; elemental analysis result: theoretical values: C, 89.052; H, 5.895; B, 1.406; N, 3.636 (%); experimental values: C, 89.050; H, 5.997; B, 1.486; N, 3.671 (%).

[0220] Target compound D1-207 (HPLC analytical purity 99.14%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 876.3135; elemental analysis result: theoretical values: C, 78.089; H, 4.484; B, 1.232; F, 13.003; N, 3.201 (%); experimental values: C, 78.090; H, 4.385; B, 1.220; F, 12.928; N, 3.284 (%).

[0221] Target compound D1-209 (HPLC analytical purity 99.23%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 800.3623; elemental analysis result: theoretical values: C, 85.486; H, 5.663; B, 1.350; N, 3.503; O, 3.997 (%); experimental values: C, 85.500; H, 5.597; B, 1.377; N, 3.506; O, 3.901 (%).

[0222] Target compound D1-210 (HPLC analytical purity 99.11%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 928.4745; elemental analysis result: theoretical values: C, 86.619; H, 6.176; B, 1.160; N, 6.026 (%); experimental values: C, 86.620; H, 6.142; B, 1.163; N, 6.043 (%).

[0223] Target compound D1-217 (HPLC analytical purity 99.56%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.3146; elemental analysis result: theoretical values: C, 85.919; H, 5.190; B, 1.362; N, 3.518; S, 4.021 (%); experimental values: C, 85.930; H, 5.107; B, 1.276; N, 3.591; S, 4.098 (%).

[0224] Target compound D1-218 (HPLC analytical purity 99.33%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 780.3374; elemental analysis result: theoretical values: C, 87.694; H, 5.289; B, 1.376; N, 3.592; O, 2.053 (%); experimental values: C, 87.700; H, 5.283; B, 1.472; N, 3.580; O, 2.108 (%).

[0225] Target compound D1-221 (HPLC analytical purity 99.40%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 830.3555; elemental analysis result: theoretical values: C, 88.179; H, 5.224; B, 1.303; N, 3.373; O, 1.934 (%); experimental values: C, 88.170; H, 5.204; B, 1.294; N, 3.332; O, 2.003 (%).

[0226] Target compound D1-224 (HPLC analytical purity 99.77%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 830.3524; elemental analysis result: theoretical values: C, 88.184; H, 5.223; B, 1.302; N, 3.365; O, 1.927 (%); experimental values: C, 88.180; H, 5.302; B, 1.385; N, 3.321; O, 1.863 (%).

[0227] Target compound D1-225 (HPLC analytical purity: 99.81%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3212; elemental analysis result: theoretical values: C, 86.508; H, 5.120; B, 1.275; N, 3.305; S, 3.786 (%); experimental values: C, 86.510; H, 5.103; B, 1.238; N, 3.409; S, 3.746 (%).

[0228] Target compound D1-230 (HPLC analytical purity: 99.00%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.2725; elemental analysis result: theoretical values: C, 81.968; H, 4.848; B, 1.211; N, 3.129; Se, 8.839 (%); experimental values: C, 81.970; H, 4.913; B, 1.288; N, 3.085; Se, 8.747 (%).

[0229] Target compound D1-239 (HPLC analytical purity: 99.33%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 922.3652; elemental analysis result: theoretical values: C, 87.186; H, 5.126; B, 1.173; N, 3.037; S, 3.472 (%); experimental values: C, 87.200; H, 5.119; B, 1.119; N, 2.968; S, 3.384 (%).

[0230] Target compound D1-241 (HPLC analytical purity: 99.35%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 667.2235; elemental analysis result: theoretical values: C, 88.161; H, 3.930; B, 1.615; N, 6.285 (%); experimental values: C, 88.150; H, 3.898; B, 1.532; N, 6.337 (%).

[0231] Target compound D1-242 (HPLC analytical purity: 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 723.2825; elemental analysis result: theoretical values: C, 87.964; H, 4.743; B, 1.490; N, 5.813 (%); experimental values: C, 87.960; H, 4.672; B, 1.531; N, 5.794 (%).

[0232] Target compound D1-243 (HPLC analytical purity 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 891.4763; elemental analysis result: theoretical values: C, 87.524; H, 6.549; B, 1.213; N, 4.711 (%); experimental values: C, 87.510; H, 6.480; B, 1.242; N, 4.810 (%).

[0233] Target compound D1-246 (HPLC analytical purity 99.49%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 939.1747; elemental analysis result: theoretical values: C, 67.745; H, 2.360; B, 1.146; F, 24.263; N, 4.474 (%); experimental values: C, 67.760; H, 2.452; B, 1.077; F, 24.187; N, 4.445 (%).

[0234] Target compound D1-247 (HPLC analytical purity 99.08%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 839.39; elemental analysis result: theoretical values: C, 81.518; H, 5.515; B, 1.287; N, 11.670 (%); experimental values: C, 81.520; H, 5.551; B, 1.303; N, 11.734 (%).

[0235] Target compound D1-249 (HPLC analytical purity 99.12%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 787.2612; elemental analysis result: theoretical values: C, 80.818; H, 4.345; B, 1.367; N, 5.325; O, 8.121 (%); experimental values: C, 80.810; H, 4.349; B, 1.366; N, 5.322; O, 8.097 (%).

[0236] Target compound D1-257 (HPLC analytical purity 99.60%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 879.2236; elemental analysis result: theoretical values: C, 83.269; H, 3.437; B, 1.233; N, 4.783; S, 7.290 (%); experimental values: C, 83.270; H, 3.535; B, 1.258; N, 4.877; S, 7.387 (%).

[0237] Target compound D1-263 (HPLC analytical purity 99.21%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 899.3564; elemental analysis result: theoretical values: C, 89.423; H, 4.698; B, 1.203; N, 4.672 (%); experimental values: C, 89.420; H, 4.728; B, 1.268; N, 4.748 (%).

[0238] Target compound D1-265 (HPLC analytical purity 99.06%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 879.2236; elemental analysis result: theoretical values: C, 83.268; H, 3.441; B, 1.229; N, 4.783; S, 7.292 (%); experimental values: C, 83.280; H, 3.525; B, 1.287; N, 4.700; S, 7.252 (%).

[0239] Target compound D1-269 (HPLC analytical purity 99.13%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 879.2346; elemental analysis result: theoretical values: C, 83.268; H, 3.441; B, 1.227; N, 4.784; S, 7.291 (%); experimental values: C, 83.270; H, 3.526; B, 1.178; N, 4.811; S, 7.336 (%).

[0240] Target compound D1-273 (HPLC analytical purity 99.83%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 807.3823; elemental analysis result: theoretical values: C, 85.404; H, 4.862; B, 1.304; N, 8.441 (%); experimental values: C, 85.400; H, 4.838; B, 1.271; N, 8.513 (%).

[0241] Target compound D1-275 (HPLC analytical purity 99.34%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 829.3434; elemental analysis result: theoretical values: C, 87.724; H, 5.740; B, 1.337; N, 5.204 (%); experimental values: C, 87.730; H, 5.765; B, 1.294; N, 5.167 (%).

[0242] The target compound D1-281 (HPLC analytical purity 99.06%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 834.3223; elemental analysis result: theoretical values: C, 84.782; H, 5.064; B, 1.294; N, 5.032; S, 3.839 (%); experimental values: C, 84.790; H, 4.994; B, 1.261; N, 5.062; S, 3.827 (%).

[0243] The target compound D1-282 (HPLC analytical purity 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 818.3525; elemental analysis result: theoretical values: C, 86.438; H, 5.161; B, 1.315; N, 5.132; O, 1.950 (%); experimental values: C, 86.450; H, 5.249; B, 1.292; N, 5.060; O, 1.933 (%).

[0244] The target compound D1-285 (HPLC analytical purity 99.38%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 869.3678; elemental analysis result: theoretical values: C, 86.992; H, 5.096; B, 1.243; N, 4.826; O, 1.841 (%); experimental values: C, 86.990; H, 5.091; B, 1.316; N, 4.834; O, 1.800 (%).

[0245] The target compound D1-289 (HPLC analytical purity 99.30%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 885.3323; elemental analysis result: theoretical values: C, 85.405; H, 5.007; B, 1.222; N, 4.742; S, 3.617 (%); experimental values: C, 85.410; H, 4.921; B, 1.146; N, 4.710; S, 3.692 (%).

[0246] The target compound D1-291 (HPLC analytical purity 99.03%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 944.4136; elemental analysis result: theoretical values: C, 87.704; H, 5.234; B, 1.135; N, 5.934 (%); experimental values: C, 87.710; H, 5.135; B, 1.063; N, 5.953 (%).

[0247] The target compound D1-293 (HPLC analytical purity 99.72%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 933.2857; elemental analysis results: theoretical values: C, 81.120; H, 4.745; B, 1.157; N, 4.500; Se, 8.468 (%); experimental values: C, 81.110; H, 4.662; B, 1.068; N, 4.505; Se, 8.492 (%).

[0248] The target compound D1-303 (HPLC analytical purity 99.61%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 885.3386; elemental analysis results: theoretical values: C, 85.411; H, 5.007; B, 1.217; N, 4.737; S, 3.617 (%); experimental values: C, 85.400; H, 5.011; B, 1.157; N, 4.685; S, 3.552 (%).

[0249] The target compound D1-304 (HPLC analytical purity 99.09%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 933.2835; elemental analysis results: theoretical values: C, 81.119; H, 4.750; B, 1.161; N, 4.496; Se, 8.474 (%); experimental values: C, 81.120; H, 4.753; B, 1.238; N, 4.431; Se, 8.538 (%).

[0250] The target compound D1-305 (HPLC analytical purity 99.63%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 944.4112; elemental analysis results: theoretical values: C, 87.696; H, 5.227; B, 1.138; N, 5.931 (%); experimental values: C, 87.710; H, 5.261; B, 1.215; N, 5.985 (%).

[0251] Target compound D1-308 (HPLC analytical purity: 99.59%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 885.3345; elemental analysis result: theoretical values: C, 85.405; H, 5.012; B, 1.215; N, 4.743; S, 3.615 (%); experimental values: C, 85.400; H, 5.017; B, 1.203; N, 4.780; S, 3.581 (%).

[0252] Target compound D1-313 (HPLC analytical purity: 99.22%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 797.3754; elemental analysis result: theoretical values: C, 88.828; H, 4.549; B, 1.358; N, 5.265 (%); experimental values: C, 88.840; H, 4.494; B, 1.271; N, 5.304 (%).

[0253] Target compound D1-315 (HPLC analytical purity: 99.90%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 847.3275; elemental analysis result: theoretical values: C, 89.250; H, 4.523; B, 1.276; N, 4.964 (%); experimental values: C, 89.250; H, 4.553; B, 1.198; N, 4.993 (%).

[0254] Target compound D1-316 (HPLC analytical purity: 99.73%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 727.2335; elemental analysis result: theoretical values: C, 84.178; H, 4.160; B, 1.493; N, 5.767; S, 4.405 (%); experimental values: C, 84.180; H, 4.068; B, 1.570; N, 5.683; S, 4.314 (%).

[0255] Target compound D1-317 (HPLC analytical purity: 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 711.2546; elemental analysis result: theoretical values: C, 86.083; H, 4.252; B, 1.521; N, 5.896; O, 2.245 (%); experimental values: C, 86.070; H, 4.187; B, 1.526; N, 5.901; O, 2.318 (%).

[0256] The target compound D1-318 (HPLC analytical purity 99.71%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 711.2574; elemental analysis result: theoretical values: C, 86.083; H, 4.247; B, 1.520; N, 5.901; O, 2.252 (%); experimental values: C, 86.090; H, 4.285; B, 1.444; N, 5.816; O, 2.251 (%).

[0257] The target compound D1-320 (HPLC analytical purity 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.3957; elemental analysis result: theoretical values: C, 87.240; H, 5.289; B, 1.206; N, 6.264 (%); experimental values: C, 87.250; H, 5.291; B, 1.223; N, 6.280 (%).

[0258] The target compound D1-324 (HPLC analytical purity 99.34%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 725.2168; elemental analysis result: theoretical values: C, 84.413; H, 3.888; B, 1.493; N, 5.791; S, 4.420 (%); experimental values: C, 84.410; H, 3.803; B, 1.464; N, 5.808; S, 4.418 (%).

[0259] The target compound D1-326 (HPLC analytical purity 99.12%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 691.2379; elemental analysis result: theoretical values: C, 83.352; H, 4.371; B, 1.557; N, 6.083; S, 4.635 (%); experimental values: C, 83.340; H, 4.368; B, 1.540; N, 6.019; S, 4.662 (%).

[0260] The target compound D1-327 (HPLC analytical purity 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 890.4846; elemental analysis result: theoretical values: C, 84.921; H, 7.126; B, 1.208; N, 3.138; S, 3.604 (%); experimental values: C, 84.930; H, 7.067; B, 1.276; N, 3.216; S, 3.555 (%).

[0261] The target compound D1-331 (HPLC analytical purity 99.48%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 854.3879; elemental analysis result: theoretical values: C, 78.738; H, 6.125; B, 1.287; N, 10.016; S, 3.823 (%); experimental values: C, 78.740; H, 6.129; B, 1.376; N, 9.969; S, 3.904 (%).

[0262] The target compound D1-334 (HPLC analytical purity 99.14%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 724.1635; elemental analysis result: theoretical values: C, 79.563; H, 2.920; B, 1.493; N, 11.596; S, 4.415 (%); experimental values: C, 79.570; H, 2.950; B, 1.584; N, 11.597; S, 4.326 (%).

[0263] The target compound D1-341 (HPLC analytical purity 99.59%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 866.2986; elemental analysis result: theoretical values: C, 87.294; H, 4.534; B, 1.247; N, 3.231; S, 3.700 (%); experimental values: C, 87.300; H, 4.555; B, 1.270; N, 3.327; S, 3.634 (%).

[0264] The target compound D1-365 (HPLC analytical purity 99.79%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 748.3642; elemental analysis result: theoretical values: C, 86.618; H, 6.057; B, 1.439; N, 3.744; O, 2.135 (%); experimental values: C, 86.630; H, 6.119; B, 1.480; N, 3.804; O, 2.096 (%).

[0265] Target compound D1-374 (HPLC analytical purity 99.72%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 797.2857; elemental analysis result: theoretical values: C, 82.970; H, 4.635; B, 1.377; N, 8.963; O, 2.045 (%); experimental values: C, 82.980; H, 4.727; B, 1.416; N, 8.927; O, 2.050 (%).

[0266] Target compound D1-377 (HPLC analytical purity 99.82%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 776.3352; elemental analysis result: theoretical values: C, 83.501; H, 5.322; B, 1.391; N, 3.612; O, 2.062; S, 4.130 (%); experimental values: C, 83.500; H, 5.419; B, 1.448; N, 3.675; O, 2.113; S, 4.215 (%).

[0267] Target compound D1-378 (HPLC analytical purity 99.64%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 771.3157; elemental analysis result: theoretical values: C, 84.036; H, 4.959; B, 1.395; N, 5.454; O, 4.148 (%); experimental values: C, 84.050; H, 4.993; B, 1.478; N, 5.371; O, 4.224 (%).

[0268] Target compound D1-385 (HPLC analytical purity 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 826.3235; elemental analysis result: theoretical values: C, 84.248; H, 5.239; B, 1.311; N, 3.390; O, 1.926; S, 3.882 (%); experimental values: C, 84.240; H, 5.333; B, 1.395; N, 3.376; O, 1.973; S, 3.919 (%).

[0269] Target compound D1-404 (HPLC analytical purity 99.61%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 830.2964; elemental analysis result: theoretical values: C, 82.396; H, 4.845; B, 1.296; F, 2.285; N, 3.372; O, 1.933; S, 3.862 (%); experimental values: C, 82.410; H, 4.802; B, 1.395; F, 2.215; N, 3.349; O, 2.013; S, 3.802 (%).

[0270] Target compound D1-405 (HPLC analytical purity 99.67%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 814.3247; elemental analysis result: theoretical values: C, 84.032; H, 4.952; B, 1.328; F, 2.328; N, 3.438; O, 3.441 (%); experimental values: C, 84.040; H, 4.983; B, 1.410; F, 2.354; N, 3.383; O, 3.833 (%).

[0271] Target compound D1-408 (HPLC analytical purity 99.32%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 651.2358; elemental analysis result: theoretical values: C, 86.925; H, 4.761; B, 1.704; N, 6.605 (%); experimental values: C, 86.920; H, 4.680; B, 1.627; N, 6.670 (%).

[0272] Target compound D1-409 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 803.4469; elemental analysis result: theoretical values: C, 86.659; H, 6.769; B, 1.339; N, 5.228 (%); experimental values: C, 86.650; H, 6.836; B, 1.269; N, 5.143 (%).

[0273] Target compound D1-416 (HPLC analytical purity: 99.66%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 679.1770; elemental analysis result: theoretical values: C, 81.307; H, 2.670; B, 1.591; N, 14.432 (%); experimental values: C, 81.310; H, 2.751; B, 1.568; N, 14.520 (%).

[0274] Target compound D1-427 (HPLC analytical purity: 99.16%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 791.1780; elemental analysis result: theoretical values: C, 81.916; H, 3.306; B, 1.373; N, 5.313; S, 8.099 (%); experimental values: C, 81.910; H, 3.276; B, 1.307; N, 5.298; S, 8.184 (%).

[0275] Target compound D1-433 (HPLC analytical purity: 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 731.3197; elemental analysis result: theoretical values: C, 85.358; H, 5.233; B, 1.477; N, 5.738; O, 2.193 (%); experimental values: C, 85.360; H, 5.189; B, 1.492; N, 5.789; O, 2.095 (%).

[0276] Target compound D1-435 (HPLC analytical purity: 99.01%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 781.3307; elemental analysis result: theoretical values: C, 86.036; H, 5.164; B, 1.381; N, 5.377; O, 2.050 (%); experimental values: C, 86.030; H, 5.063; B, 1.352; N, 5.443; O, 1.952 (%).

[0277] Target compound D1-436 (HPLC analytical purity: 99.76%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 872.3557; elemental analysis result: theoretical values: C, 86.910; H, 5.292; B, 1.259; N, 6.539 (%); experimental values: C, 86.900; H, 5.354; B, 1.327; N, 6.467 (%).

[0278] Target compound D1-439 (HPLC analytical purity 99.51%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 797.3643; elemental analysis result: theoretical values: C, 84.306; H, 5.046; B, 1.353; N, 5.272; S, 4.024 (%); experimental values: C, 84.310; H, 4.974; B, 1.415; N, 5.305; S, 3.923 (%).

[0279] Target compound D1-444 (HPLC analytical purity 99.11%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 845.2575; elemental analysis result: theoretical values: C, 79.621; H, 4.765; B, 1.282; N, 4.971; Se, 9.351 (%); experimental values: C, 79.630; H, 4.785; B, 1.329; N, 4.971; Se, 9.370 (%).

[0280] Target compound D1-449 (HPLC analytical purity 99.79%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 797.3689; elemental analysis result: theoretical values: C, 84.308; H, 5.052; B, 1.349; N, 5.266; S, 4.024 (%); experimental values: C, 84.300; H, 5.106; B, 1.251; N, 5.306; S, 4.117 (%).

[0281] Target compound D1-451 (HPLC analytical purity 99.29%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 856.3786; elemental analysis result: theoretical values: C, 86.912; H, 5.286; B, 1.262; N, 6.536 (%); experimental values: C, 86.920; H, 5.372; B, 1.185; N, 6.571 (%).

[0282] Target compound D1-456 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 759.2864; elemental analysis result: theoretical values: C, 88.533; H, 4.508; B, 1.423; N, 5.532 (%); experimental values: C, 88.520; H, 4.490; B, 1.480; N, 5.486 (%).

[0283] Target compound D1-461 (HPLC analytical purity 99.06%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 639.1957; elemental analysis result: theoretical values: C, 83.005; H, 4.241; B, 1.616; N, 6.313; S, 4.815 (%); experimental values: C, 83.020; H, 4.153; B, 1.525; N, 6.243; S, 4.733 (%).

[0284] Target compound D1-462 (HPLC analytical purity 99.73%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 806.3654; elemental analysis result: theoretical values: C, 86.338; H, 5.368; B, 1.344; N, 6.941 (%); experimental values: C, 86.350; H, 5.323; B, 1.371; N, 6.876 (%).

[0285] Target compound D1-465 (HPLC analytical purity 99.36%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 982.5123; elemental analysis result: theoretical values: C, 86.737; H, 6.458; B, 1.099; N, 5.697 (%); experimental values: C, 86.750; H, 6.421; B, 1.060; N, 5.763 (%).

[0286] Target compound D1-472 (HPLC analytical purity 99.76%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 858.2557; elemental analysis result: theoretical values: C, 82.523; H, 3.166; B, 1.256; N, 13.054 (%); experimental values: C, 82.520; H, 3.210; B, 1.164; N, 13.107 (%).

[0287] Target compound D1-487 (HPLC analytical purity 99.80%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 895.1968; elemental analysis result: theoretical values: C, 81.783; H, 3.380; B, 1.208; N, 4.693; O, 1.794; S, 7.159 (%); experimental values: C, 81.770; H, 3.338; B, 1.142; N, 4.654; O, 1.800; S, 7.108 (%).

[0288] The target compound D1-503 (HPLC analytical purity 99.49%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 839.3579; elemental analysis result: theoretical values: C, 84.365; H, 5.519; B, 1.285; N, 5.002; S, 3.818 (%); experimental values: C, 84.380; H, 5.498; B, 1.274; N, 4.975; S, 3.830 (%).

[0289] The target compound D1-512 (HPLC analytical purity 99.03%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 861.3108; elemental analysis result: theoretical values: C, 82.217; H, 4.680; B, 1.252; N, 8.126; S, 3.718 (%); experimental values: C, 82.210; H, 4.767; B, 1.173; N, 8.077; S, 3.746 (%).

[0290] The target compound D1-515 (HPLC analytical purity 99.27%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 867.2934; elemental analysis result: theoretical values: C, 81.646; H, 4.879; B, 1.253; N, 4.842; S, 7.392 (%); experimental values: C, 81.650; H, 4.973; B, 1.327; N, 4.898; S, 7.448 (%).

[0291] The target compound D1-520 (HPLC analytical purity 99.21%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 992.3557; elemental analysis result: theoretical values: C, 84.804; H, 4.782; B, 1.136; N, 5.903; S, 3.380 (%); experimental values: C, 84.810; H, 4.751; B, 1.122; N, 5.886; S, 3.465 (%).

[0292] Target compound D1-523 (HPLC analytical purity 99.01%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 943.3668; elemental analysis results: theoretical values: C, 82.685; H, 5.338; B, 1.150; N, 4.449; S, 3.397; Si, 2.971 (%); experimental values: C, 82.700; H, 5.402; B, 1.158; N, 4.467; S, 3.371; Si, 3.035 (%).

[0293] Target compound D1-537 (HPLC analytical purity 99.55%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 943.3635; elemental analysis results: theoretical values: C, 82.688; H, 5.343; B, 1.151; N, 4.449; S, 3.401; Si, 2.974 (%); experimental values: C, 82.700; H, 5.378; B, 1.111; N, 4.412; S, 3.352; Si, 3.010 (%).

[0294] Target compound D1-539 (HPLC analytical purity 99.61%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 1002.4357; elemental analysis results: theoretical values: C, 85.009; H, 5.533; B, 1.078; N, 5.589; Si, 2.795 (%); experimental values: C, 85.020; H, 5.574; B, 1.088; N, 5.497; Si, 2.812 (%).

[0295] Target compound D1-548 (HPLC analytical purity 99.23%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 684.2768; elemental analysis results: theoretical values: C, 89.467; H, 4.863; B, 1.584; N, 4.091 (%); experimental values: C, 89.470; H, 4.939; B, 1.584; N, 4.047 (%).

[0296] Target compound D1-556 (HPLC analytical purity: 99.66%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 728.1997; elemental analysis result: theoretical values: C, 84.084; H, 2.912; B, 1.479; N, 11.542 (%); experimental values: C, 84.090; H, 2.981; B, 1.477; N, 11.555 (%).

[0297] Target compound D1-563 (HPLC analytical purity: 99.24%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.3153; elemental analysis result: theoretical values: C, 85.917; H, 5.185; B, 1.361; N, 3.518; S, 4.018 (%); experimental values: C, 85.910; H, 5.244; B, 1.427; N, 3.484; S, 3.989 (%).

[0298] Target compound D1-568 (HPLC analytical purity: 99.18%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.3746; elemental analysis result: theoretical values: C, 88.934; H, 5.050; B, 1.226; N, 4.792 (%); experimental values: C, 88.940; H, 4.986; B, 1.154; N, 4.766 (%).

[0299] Target compound D1-569 (HPLC analytical purity: 99.44%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.2757; elemental analysis result: theoretical values: C, 81.966; H, 4.854; B, 1.210; N, 3.132; Se, 8.837 (%); experimental values: C, 81.980; H, 4.795; B, 1.213; N, 3.091; Se, 8.780 (%).

[0300] Target compound D1-572 (HPLC analytical purity: 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 905.3923; elemental analysis result: theoretical values: C, 88.827; H, 5.344; B, 1.187; N, 4.639 (%); experimental values: C, 88.820; H, 5.284; B, 1.145; N, 4.689 (%).

[0301] Target compound D1-574 (HPLC analytical purity 99.27%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3264; elemental analysis result: theoretical values: C, 86.512; H, 5.119; B, 1.279; N, 3.306; S, 3.785 (%); experimental values: C, 86.500; H, 5.124; B, 1.350; N, 3.222; S, 3.881 (%).

[0302] Target compound D1-577 (HPLC analytical purity 99.47%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 894.2757; elemental analysis result: theoretical values: C, 81.974; H, 4.848; B, 1.214; N, 3.131; Se, 8.838 (%); experimental values: C, 81.960; H, 4.773; B, 1.233; N, 3.155; Se, 8.934 (%).

[0303] Target compound D1-603 (HPLC analytical purity 99.54%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 780.2723; elemental analysis result: theoretical values: C, 90.772; H, 4.261; B, 1.382; N, 3.594 (%); experimental values: C, 90.770; H, 4.299; B, 1.356; N, 3.685 (%).

[0304] Target compound D1-614 (HPLC analytical purity 99.71%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 989.3746; elemental analysis result: theoretical values: C, 87.350; H, 4.476; B, 1.086; N, 7.071 (%); experimental values: C, 87.360; H, 4.403; B, 1.148; N, 6.972 (%).

[0305] Target compound D1-625 (HPLC analytical purity 99.59%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 836.2523; elemental analysis result: theoretical values: C, 87.551; H, 3.976; B, 1.288; N, 3.346; S, 3.829 (%); experimental values: C, 87.560; H, 3.931; B, 1.310; N, 3.283; S, 3.777 (%).

[0306] Target compound D1-630 (HPLC analytical purity: 99.30%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 811.2346; elemental analysis result: theoretical values: C, 85.815; H, 3.726; B, 1.326; N, 5.181; S, 3.949 (%); experimental values: C, 85.830; H, 3.774; B, 1.272; N, 5.253; S, 3.938 (%).

[0307] Target compound D1-661 (HPLC analytical purity: 99.41%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 830.2623; elemental analysis result: theoretical values: C, 88.194; H, 3.764; B, 1.295; N, 6.742 (%); experimental values: C, 88.190; H, 3.793; B, 1.399; N, 6.725 (%).

[0308] Target compound D1-671 (HPLC analytical purity: 99.62%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 897.3346; elemental analysis result: theoretical values: C, 89.626; H, 4.487; B, 1.201; N, 4.676 (%); experimental values: C, 89.630; H, 4.449; B, 1.295; N, 4.677 (%).

[0309] Target compound D1-682 (HPLC analytical purity: 99.77%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 771.2857; elemental analysis result: theoretical values: C, 88.712; H, 4.437; B, 1.404; N, 5.445 (%); experimental values: C, 88.710; H, 4.537; B, 1.477; N, 5.382 (%).

[0310] Target compound D1-685 (HPLC analytical purity: 99.13%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 945.3368; elemental analysis result: theoretical values: C, 90.149; H, 4.261; B, 1.136; N, 4.441 (%); experimental values: C, 90.140; H, 4.214; B, 1.178; N, 4.386 (%).

[0311] Target compound D1-715 (HPLC analytical purity 99.39%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 731.2523; elemental analysis result: theoretical values: C, 88.649; H, 4.132; B, 1.475; N, 5.737 (%); experimental values: C, 88.640; H, 4.213; B, 1.462; N, 5.748 (%).

[0312] Target compound D1-722 (HPLC analytical purity 99.34%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 770.1864; elemental analysis result: theoretical values: C, 79.481; H, 3.532; B, 1.398; N, 7.265; S, 8.323 (%); experimental values: C, 79.490; H, 3.552; B, 1.487; N, 7.315; S, 8.272 (%).

[0313] Target compound D1-740 (HPLC analytical purity 99.80%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 846.3326; elemental analysis result: theoretical values: C, 87.935; H, 4.171; B, 1.283; N, 6.623 (%); experimental values: C, 87.940; H, 4.128; B, 1.253; N, 6.556 (%).

[0314] Target compound D1-771 (HPLC analytical purity 99.45%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 724.2723; elemental analysis result: theoretical values: C, 87.844; H, 4.591; B, 1.485; N, 3.867; O, 2.207 (%); experimental values: C, 87.850; H, 4.507; B, 1.511; N, 3.859; O, 2.281 (%).

[0315] Target compound D1-782 (HPLC analytical purity 99.56%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 995.4246; elemental analysis result: theoretical values: C, 86.816; H, 5.061; B, 1.094; N, 7.033 (%); experimental values: C, 86.830; H, 4.985; B, 1.077; N, 7.015 (%).

[0316] Target compound D1-783 (HPLC analytical purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 893.3237; elemental analysis result: theoretical values: C, 85.989; H, 4.513; B, 1.211; N, 4.696; S, 3.586 (%); experimental values: C, 85.980; H, 4.502; B, 1.199; N, 4.785; S, 3.642 (%).

[0317] Target compound D1-793 (HPLC analytical purity 99.74%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 816.2435; elemental analysis result: theoretical values: C, 85.288; H, 4.065; B, 1.323; N, 3.428; O, 1.961; S, 3.934 (%); experimental values: C, 85.290; H, 4.010; B, 1.317; N, 3.369; O, 2.018; S, 4.010 (%).

[0318] Target compound D1-796 (HPLC analytical purity 99.78%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 901.3646; elemental analysis result: theoretical values: C, 89.216; H, 4.921; B, 1.199; N, 4.656 (%); experimental values: C, 89.220; H, 4.946; B, 1.210; N, 4.726 (%).

[0319] Target compound D1-827 (HPLC analytical purity 99.25%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 769.2757; elemental analysis result: theoretical values: C, 88.953; H, 4.189; B, 1.400; N, 5.461 (%); experimental values: C, 88.950; H, 4.240; B, 1.372; N, 5.501 (%).

[0320] Target compound D1-838 (HPLC analytical purity 99.44%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 1028.3824; elemental analysis result: theoretical values: C, 86.366; H, 4.408; B, 1.045; N, 8.174 (%); experimental values: C, 86.380; H, 4.504; B, 0.996; N, 8.146 (%).

[0321] Target compound D1-849 (HPLC analytical purity 99.77%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 800.2246; elemental analysis result: theoretical values: C, 84.004; H, 3.651; B, 1.352; N, 7.001; S, 4.002 (%); experimental values: C, 84.010; H, 3.700; B, 1.351; N, 6.971; S, 3.960 (%).

[0322] Target compound D1-884 (HPLC analytical purity 99.37%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 852.3557; elemental analysis result: theoretical values: C, 83.087; H, 5.322; B, 1.272; N, 6.571; S, 3.759 (%); experimental values: C, 83.090; H, 5.342; B, 1.241; N, 6.580; S, 3.713 (%).

[0323] Target compound D1-895 (HPLC analytical purity 99.31%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 968.3186; elemental analysis result: theoretical values: C, 85.530; H, 4.267; B, 1.121; N, 5.782; S, 3.305 (%); experimental values: C, 85.530; H, 4.345; B, 1.140; N, 5.867; S, 3.382 (%).

[0324] Target compound D1-904 (HPLC analytical purity 99.51%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 816.2232; elemental analysis result: theoretical values: C, 82.352; H, 3.584; B, 1.323; N, 6.857; O, 1.964; S, 3.933 (%); experimental values: C, 82.340; H, 3.516; B, 1.290; N, 6.780; O, 1.868; S, 3.847 (%).

[0325] Target compound D1-909 (HPLC analytical purity 99.88%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 950.3234; elemental analysis result: theoretical values: C, 87.145; H, 4.132; B, 1.142; N, 5.889; O, 1.684 (%); experimental values: C, 87.160; H, 4.045; B, 1.177; N, 5.858; O, 1.639 (%). Example D-2. Synthesis of Compound D1-93

Chemical formula

[0326] In a two-necked flask, under a nitrogen gas atmosphere, compound I-93-1 (10.4 mmol), carbazole (10.4 mmol), and cesium carbonate (40 mmol) are dissolved in 150 mL of N,N-dimethylformamide (DMF), heated to 150 °C, and reacted for 12 hours. After the reaction is completed and cooled, it is poured into cold water, filtered, washed twice with 100 mL of water, then washed once with 10 mL of methanol, and dried to obtain the target compound I-93-2 as a pale yellow solid.

[0327] In a two-necked flask, under a nitrogen gas atmosphere, compound I-93-2 (10 mmol), compound 4,4'-di-t-butyl diphenylamine (10 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), and sodium t-butoxide (12 mmol) are sequentially added, 100 ml of dry toluene is added and heated to 110 °C, and reacted for 12 hours. After cooling, liquid separation is carried out, separation is performed, and the organic phase is collected. The organic phase is dried with anhydrous sodium sulfate, then filtered, and the organic phase is concentrated. The compound is separated by a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent to obtain compound I-93-3.

[0328] In a two-necked flask, under a nitrogen gas atmosphere, Compound I-93-3 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 6 ml) was added, and the reaction was carried out at this temperature for 1 hour. Benzo[a]fluorenone was dissolved in 40 ml of dry tetrahydrofuran previously cooled to -78°C, and then the solution was slowly poured into the solution of I-93-3 at -78°C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added for quenching, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised for reflux. After reacting for 2 hours, it was neutralized with a saturated aqueous sodium carbonate solution, extracted with dichloromethane, separated, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered, and the organic phase was concentrated. The compound was separated by silica gel column using petroleum ether:dichloromethane = 5:1 as the developing agent to obtain Compound I-93-4.

[0329] In a sealed tube, Compound I-93-4 (1 mmol) was dissolved in 20 mL of t-butylbenzene, cooled to -78°C, and then a pentane solution of t-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30°C and reacted for 1 hour. It was cooled to -78°C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30°C and stirred continuously for 1 hour. After cooling to 0°C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160°C and reacted for 12 hours. The solvent was dried under vacuum, and the target compound D1-93 (HPLC analysis purity 99.32%) was obtained as a yellow solid by passing through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent. MALDI-TOF-MS results: molecular ion peak: 742.3523; elemental analysis results: theoretical values: C, 88.938; H, 5.842; B, 1.461; N, 3.766 (%); experimental values: C, 88.940; H, 5.930; B, 1.413; N, 3.711 (%).

[0330] The synthesis methods of the following synthesis examples are all the same as those of Example D-2, except that the carbazole in the first step is replaced with the corresponding carbazole derivative, the secondary amine in the second step is replaced with the corresponding secondary amine, and fluorenone is replaced with the aromatic ketone raw material of the corresponding fragment in the example.

Chemical formula

[0331] Target compound D1-95 (HPLC analytical purity 99.10%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 907.4175; elemental analysis results: theoretical values: C, 88.630; H, 5.552; B, 1.189; N, 4.634 (%); experimental values: C, 88.620; H, 5.498; B, 1.151; N, 4.727 (%).

[0332] Target compound D1-97 (HPLC analytical purity 99.25%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 896.2835; elemental analysis results: theoretical values: C, 81.791; H, 5.062; B, 1.205; N, 3.132; Se, 8.823 (%); experimental values: C, 81.800; H, 5.010; B, 1.114; N, 3.048; Se, 8.920 (%).

[0333] Target compound D1-98 (HPLC analytical purity 99.65%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 896.2824; elemental analysis results: theoretical values: C, 81.786; H, 5.062; B, 1.205; N, 3.130; Se, 8.823 (%); experimental values: C, 81.780; H, 5.093; B, 1.224; N, 3.049; Se, 8.739 (%).

[0334] Target compound D1-105 (HPLC analytical purity 99.57%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 907.4164; elemental analysis result: theoretical values: C, 88.632; H, 5.548; B, 1.186; N, 4.630 (%); experimental values: C, 88.620; H, 5.510; B, 1.097; N, 4.568 (%).

[0335] Target compound D1-107 (HPLC analytical purity 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 848.3442; elemental analysis result: theoretical values: C, 86.306; H, 5.336; B, 1.268; N, 3.296; S, 3.775 (%); experimental values: C, 86.310; H, 5.411; B, 1.337; N, 3.248; S, 3.788 (%).

[0336] Target compound D1-109 (HPLC analytical purity 99.82%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 798.32462; elemental analysis result: theoretical values: C, 85.701; H, 5.426; B, 1.353; N, 3.510; S, 4.007 (%); experimental values: C, 85.710; H, 5.441; B, 1.421; N, 3.549; S, 3.980 (%).

[0337] Target compound D1-110 (HPLC analytical purity 99.14%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.354; elemental analysis result: theoretical values: C, 87.461; H, 5.540; B, 1.375; N, 3.578; O, 2.040 (%); experimental values: C, 87.460; H, 5.475; B, 1.384; N, 3.637; O, 1.970 (%).

[0338] Target compound D1-114 (HPLC analytical purity 99.85%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 792.3446; elemental analysis result: theoretical values: C, 86.360; H, 5.211; B, 1.363; N, 7.065 (%); experimental values: C, 86.360; H, 5.292; B, 1.353; N, 6.991 (%).

[0339] The target compound D1-125 (HPLC analytical purity 99.13%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 712.1875; elemental analysis results: theoretical values: C, 84.266; H, 3.543; B, 1.515; N, 3.934; O, 2.252; S, 4.497 (%); experimental values: C, 84.270; H, 3.587; B, 1.497; N, 3.870; O, 2.214; S, 4.550 (%).

[0340] The target compound D1-127 (HPLC analytical purity 99.90%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 792.1846; elemental analysis results: theoretical values: C, 75.771; H, 2.930; B, 1.360; F, 14.380; N, 3.525; O, 2.015 (%); experimental values: C, 75.770; H, 2.850; B, 1.409; F, 14.449; N, 3.555; O, 1.989 (%).

[0341] The target compound D1-130 (HPLC analytical purity 99.05%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 706.2057; elemental analysis results: theoretical values: C, 84.986; H, 3.279; B, 1.530; N, 7.934; O, 2.257 (%); experimental values: C, 84.980; H, 3.265; B, 1.531; N, 7.884; O, 2.313 (%).

[0342] The target compound D1-140 (HPLC analytical purity 99.25%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 772.2723; elemental analysis results: theoretical values: C, 88.596; H, 4.301; B, 1.400; N, 3.634; O, 2.065 (%); experimental values: C, 88.610; H, 4.371; B, 1.496; N, 3.591; O, 2.090 (%).

[0343] Target compound D1-583 (HPLC analytical purity 99.66%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.2975; elemental analysis result: theoretical values: C, 90.526; H, 4.511; B, 1.384; N, 3.582 (%); experimental values: C, 90.530; H, 4.486; B, 1.369; N, 3.646 (%).

[0344] Target compound D1-586 (HPLC analytical purity 99.09%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 707.2543; elemental analysis result: theoretical values: C, 88.260; H, 4.268; B, 1.527; N, 5.940 (%); experimental values: C, 88.250; H, 4.233; B, 1.549; N, 6.022 (%).

[0345] Target compound D1-589 (HPLC analytical purity 99.26%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 707.2343; elemental analysis result: theoretical values: C, 84.873; H, 3.698; B, 1.526; N, 9.897 (%); experimental values: C, 84.880; H, 3.633; B, 1.610; N, 9.888 (%).

[0346] Target compound D1-599 (HPLC analytical purity 99.35%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 899.3557; elemental analysis result: theoretical values: C, 89.418; H, 4.701; B, 1.195; N, 4.671 (%); experimental values: C, 89.420; H, 4.617; B, 1.144; N, 4.619 (%).

[0347] Target compound D1-636 (HPLC analytical purity 99.88%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 687.1975; elemental analysis result: theoretical values: C, 83.836; H, 3.813; B, 1.567; N, 6.113; S, 4.656 (%); experimental values: C, 83.840; H, 3.808; B, 1.635; N, 6.161; S, 4.666 (%).

[0348] Target compound D1-643 (HPLC analytical purity: 99.44%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.2923; elemental analysis result: theoretical values: C, 90.530; H, 4.507; B, 1.379; N, 3.583 (%); experimental values: C, 90.520; H, 4.567; B, 1.296; N, 3.558 (%).

[0349] Target compound D1-654 (HPLC analytical purity: 99.79%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 991.3886; elemental analysis result: theoretical values: C, 87.183; H, 4.667; B, 1.094; N, 7.058 (%); experimental values: C, 87.190; H, 4.571; B, 1.017; N, 7.137 (%).

[0350] Target compound D1-690 (HPLC analytical purity: 99.33%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 758.2546; elemental analysis result: theoretical values: C, 88.663; H, 4.119; B, 1.418; N, 3.694; O, 2.113 (%); experimental values: C, 88.650; H, 4.130; B, 1.367; N, 3.758; O, 2.161 (%).

[0351] Target compound D1-691 (HPLC analytical purity: 99.50%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 721.2368; elemental analysis result: theoretical values: C, 86.545; H, 3.906; B, 1.497; N, 5.822; O, 2.221 (%); experimental values: C, 86.560; H, 3.868; B, 1.579; N, 5.769; O, 2.270 (%).

[0352] Target compound D1-695 (HPLC analytical purity: 99.27%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 733.2723; elemental analysis result: theoretical values: C, 88.400; H, 4.398; B, 1.472; N, 5.725 (%); experimental values: C, 88.410; H, 4.494; B, 1.561; N, 5.687 (%).

[0353] Target compound D1-704 (HPLC analytical purity 99.11%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 769.3457; elemental analysis result: theoretical values: C, 84.260; H, 5.241; B, 1.399; N, 9.096 (%); experimental values: C, 84.260; H, 5.150; B, 1.500; N, 9.052 (%).

[0354] Target compound D1-714 (HPLC analytical purity 99.70%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 644.2325; elemental analysis result: theoretical values: C, 80.138; H, 3.601; B, 1.677; F, 5.902; N, 8.693 (%); experimental values: C, 80.130; H, 3.656; B, 1.581; F, 5.984; N, 8.598 (%).

[0355] Target compound D1-745 (HPLC analytical purity 99.31%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 787.3257; elemental analysis result: theoretical values: C, 88.432; H, 4.855; B, 1.368; N, 5.332 (%); experimental values: C, 88.440; H, 4.780; B, 1.312; N, 5.325 (%).

[0356] Target compound D1-748 (HPLC analytical purity 99.45%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 688.1923; elemental analysis result: theoretical values: C, 81.977; H, 3.661; B, 1.569; N, 8.136; S, 4.660 (%); experimental values: C, 81.990; H, 3.575; B, 1.670; N, 8.130; S, 4.593 (%).

[0357] Target compound D1-752 (HPLC analytical purity 99.65%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 762.2846; elemental analysis result: theoretical values: C, 88.190; H, 4.634; B, 1.416; N, 3.669; O, 2.103 (%); experimental values: C, 88.190; H, 4.548; B, 1.348; N, 3.612; O, 2.186 (%).

[0358] Target compound D1-763 (HPLC analytical purity 99.26%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 890.3857; elemental analysis result: theoretical values: C, 90.321; H, 5.324; B, 1.208; N, 3.139 (%); experimental values: C, 90.310; H, 5.294; B, 1.197; N, 3.070 (%).

[0359] Target compound D1-766 (HPLC analytical purity 99.54%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 971.3832; elemental analysis result: theoretical values: C, 85.269; H, 4.769; B, 1.105; N, 7.208; O, 1.651 (%); experimental values: C, 85.280; H, 4.742; B, 1.150; N, 7.199; O, 1.702 (%).

[0360] Target compound D1-800 (HPLC analytical purity 99.39%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 822.2346; elemental analysis result: theoretical values: C, 83.199; H, 4.286; B, 1.307; N, 3.398; S, 7.788 (%); experimental values: C, 83.200; H, 4.209; B, 1.258; N, 3.457; S, 7.857 (%).

[0361] Target compound D1-804 (HPLC analytical purity 99.67%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 683.1757; elemental analysis result: theoretical values: C, 79.055; H, 3.832; B, 1.576; N, 6.145; S, 9.381 (%); experimental values: C, 79.050; H, 3.894; B, 1.532; N, 6.242; S, 9.307 (%).

[0362] Target compound D1-808 (HPLC analytical purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.368; elemental analysis result: theoretical values: C, 89.163; H, 4.421; B, 1.316; N, 5.113 (%); experimental values: C, 89.170; H, 4.429; B, 1.390; N, 5.017 (%).

[0363] The target compound D1-810 (HPLC analytical purity 99.53%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 746.2635; elemental analysis result: theoretical values: C, 86.859; H, 4.177; B, 1.453; N, 7.502 (%); experimental values: C, 86.870; H, 4.216; B, 1.521; N, 7.428 (%).

[0364] The target compound D1-823 (HPLC analytical purity 99.18%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 938.3657; elemental analysis result: theoretical values: C, 88.272; H, 4.622; B, 1.150; N, 5.974 (%); experimental values: C, 88.260; H, 4.555; B, 1.186; N, 5.952 (%).

[0365] The target compound D1-861 (HPLC analytical purity 99.72%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 736.2846; elemental analysis result: theoretical values: C, 86.409; H, 4.522; B, 1.465; N, 7.611 (%); experimental values: C, 86.410; H, 4.511; B, 1.423; N, 7.568 (%).

[0366] The target compound D1-864 (HPLC analytical purity 99.72%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 867.2968; elemental analysis result: theoretical values: C, 85.808; H, 4.407; B, 1.253; N, 4.836; S, 3.685 (%); experimental values: C, 85.810; H, 4.392; B, 1.319; N, 4.757; S, 3.780 (%).

[0367] The target compound D1-868 (HPLC analytical purity 99.58%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 904.3846; elemental analysis result: theoretical values: C, 83.610; H, 5.464; B, 1.190; N, 6.185; S, 3.544 (%); experimental values: C, 83.610; H, 5.510; B, 1.097; N, 6.228; S, 3.506 (%).

[0368] The target compound D1-875 (HPLC analytical purity 99.54%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 955.3232; elemental analysis result: theoretical values: C, 86.696; H, 4.435; B, 1.134; N, 4.46; S, 3.354 (%); experimental values: C, 86.79; H, 4.33; B, 1.23; N, 4.3; S, 3.45 (%).

[0369] The target compound D1-912 (HPLC analytical purity 99.51%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 833.2164; elemental analysis result: theoretical values: C, 82.114; H, 3.869; B, 1.296; N, 5.036; S, 7.690 (%); experimental values: C, 82.110; H, 3.839; B, 1.331; N, 5.082; S, 7.633 (%).

[0370] The target compound D1-916 (HPLC analytical purity 99.20%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 772.1957; elemental analysis result: theoretical values: C, 79.267; H, 3.777; B, 1.397; N, 7.249; S, 8.297 (%); experimental values: C, 79.280; H, 3.736; B, 1.314; N, 7.206; S, 8.388 (%). Example D-3. Synthesis of Compound D1-145

Chemical formula

[0371] In a two-necked flask, under a nitrogen gas atmosphere, compound I-145-1 (10.4 mmol), 3,6-di-t-butylcarbazole (10.4 mmol), and cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF), heated to 150 °C, and reacted for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, then washed once with 10 mL of methanol, and dried to obtain the target compound I-145-2 as a pale yellow solid.

[0372] In a two-necked flask, under a nitrogen gas atmosphere, compound I-145-2 (10 mmol), compound 4,4′-dimethyl diphenylamine (10 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), and sodium tert-butoxide (12 mmol) were sequentially added. 100 ml of dry toluene was added and the temperature was raised to 110 °C, and the reaction was carried out for 12 hours. After cooling, liquid separation was carried out, separation was carried out, and the organic phase was collected. The organic phase was dried with anhydrous sodium sulfate, then filtered, and the organic phase was concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent to obtain compound I-145-3.

[0373] In a two-necked flask, under a nitrogen gas atmosphere, compound I-145-3 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 6 ml) was added, and the reaction was carried out at this temperature for 1 hour. Benzo[a]fluorenone was dissolved in 40 ml of dry tetrahydrofuran previously cooled to -78 °C, and then this solution was slowly poured into the solution of I-145-3 at -78 °C, slowly warmed to room temperature, and reacted for 12 hours. After completion of the reaction, a small amount of methanol was added for quenching, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with a saturated aqueous sodium carbonate solution, extracted with dichloromethane, liquid separation was carried out, and the organic phase was collected. The organic phase was dried with anhydrous sodium sulfate, then filtered, and the organic phase was concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing agent to obtain compound I-145-4.

[0374] Dissolve compound I-145-4 (1 mmol) in 20 mL of t-butylbenzene in a sealed tube, cool it to -78 °C, then add a pentane solution of t-butyllithium (1 M, 2.5 mL), and then warm it to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then warm it to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), then warm it to 160 °C and react for 12 hours. Dry the solvent under vacuum, and pass it through a silica gel column using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound D1-145 (HPLC analysis purity 99.16%) as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 770.3868; elemental analysis result: theoretical values: C, 88.817; H, 6.146; B, 1.398; N, 3.631 (%); experimental values: C, 88.810; H, 6.092; B, 1.477; N, 3.560 (%).

[0375] The synthesis methods in the following synthesis examples are all the same as those in Example D-3. Just replace the carbazole in the first step with the corresponding carbazole derivative, replace the secondary amine in the second step with the corresponding secondary amine, and replace fluorenone with the aromatic ketone raw material of the corresponding fragment in the example.

Chemical formula

[0376] Target compound D1-147 (HPLC analysis purity 99.21%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 878.3323; elemental analysis result: theoretical values: C, 77.914; H, 4.704; B, 1.229; F, 12.968; N, 3.188 (%); experimental values: C, 77.920; H, 4.752; B, 1.269; F, 13.000; N, 3.183 (%).

[0377] Target compound D1-151 (HPLC analytical purity 99.05%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 828.4446; elemental analysis result: theoretical values: C, 85.494; H, 6.450; B, 1.303; N, 6.757 (%); experimental values: C, 85.490; H, 6.496; B, 1.369; N, 6.687 (%).

[0378] Target compound D1-154 (HPLC analytical purity 99.79%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 792.3456; elemental analysis result: theoretical values: C, 86.363; H, 5.206; B, 1.364; N, 7.068 (%); experimental values: C, 86.360; H, 5.205; B, 1.386; N, 7.039 (%).

[0379] Target compound D1-157 (HPLC analytical purity 99.87%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 782.3835; elemental analysis result: theoretical values: C, 88.986; H, 6.054; B, 1.381; N, 3.581 (%); experimental values: C, 88.990; H, 6.105; B, 1.394; N, 3.600 (%).

[0380] Target compound D1-159 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 816.3223; elemental analysis result: theoretical values: C, 85.486; H, 5.663; B, 1.349; N, 3.497; S, 4.002 (%); experimental values: C, 85.480; H, 5.671; B, 1.305; N, 3.529; S, 3.921 (%).

[0381] Target compound D1-160 (HPLC analytical purity 99.42%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 784.3356; elemental analysis result: theoretical values: C, 87.234; H, 5.776; B, 1.382; N, 3.574; O, 2.042 (%); experimental values: C, 87.230; H, 5.699; B, 1.375; N, 3.578; O, 1.965 (%).

[0382] Target compound D1-162 (HPLC analytical purity 99.86%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.3657; elemental analysis result: theoretical values: C, 87.430; H, 5.691; B, 1.364; N, 3.524; O, 2.009 (%); experimental values: C, 87.420; H, 5.726; B, 1.345; N, 3.565; O, 2.100 (%).

[0383] Target compound D1-164 (HPLC analytical purity 99.57%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 829.3679; elemental analysis result: theoretical values: C, 88.292; H, 5.339; B, 1.298; N, 5.059 (%); experimental values: C, 88.280; H, 5.256; B, 1.211; N, 5.009 (%). Example D-4. Synthesis of compound D1-117

Chemical formula

[0384] In a two-necked flask, under a nitrogen gas atmosphere, compound I-117-1 (10 mmol), compound 9,9-dimethyl-9,10-dihydroacridine (22 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), and sodium t-butoxide (12 mmol) were sequentially added. 100 ml of dry toluene was added and the temperature was raised to 110 °C, and the reaction was carried out for 12 hours. After cooling, liquid separation was performed, separation was carried out, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered, and the organic phase was concentrated. The compound was separated by silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent to obtain compound I-117-2.

[0385] In a two-necked flask, under a nitrogen gas atmosphere, compound I-117-2 (5 mmol) is dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 6 ml) is added, and the reaction is carried out at this temperature for 1 hour. Benzo[a]fluorenone is dissolved in 40 ml of dry tetrahydrofuran previously cooled to -78 °C, and then this solution is slowly poured into the solution of I-117-2 at -78 °C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction is completed, a small amount of methanol is added for quenching, the solvent is evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid are added, and then the temperature is raised for refluxing. After reacting for 2 hours, it is neutralized with a saturated aqueous sodium carbonate solution, extracted with dichloromethane, separated, and the organic phase is collected. The organic phase is dried over anhydrous sodium sulfate, then filtered and the organic phase is concentrated. The compound is separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing agent to obtain compound I-117-3.

[0386] In a sealed tube, compound I-117-3 (1 mmol) is dissolved in 20 mL of t-butylbenzene, cooled to -78 °C, and then a pentane solution of t-butyllithium (1 M, 2.5 mL) is added, and then the temperature is raised to 30 °C and reacted for 1 hour. It is cooled to -78 °C again, boron tribromide (3 mmol) is slowly added, and then the temperature is raised to 30 °C and continuously stirred for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) is added, and then the temperature is raised to 160 °C and reacted for 12 hours. The solvent is dried under vacuum, and the target compound D1-117 (HPLC analysis purity 99.80%) is obtained as a yellow solid by passing through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing agent. MALDI-TOF-MS results: molecular ion peak: 712.3657; elemental analysis results: theoretical values: C, 89.318; H, 5.234; B, 1.519; N, 3.931 (%); experimental values: C, 89.330; H, 5.161; B, 1.478; N, 3.934 (%).

[0387] The synthesis methods of the following synthesis examples are all the same as those of Example D-4. It is only necessary to replace the secondary amine in the first step with the corresponding secondary amine and replace fluorenone with the aromatic ketone raw material of the corresponding fragment in the example.

Chemical formula

[0388] Target compound D1-119 (HPLC analysis purity 99.01%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 692.1635; elemental analysis result: theoretical values: C, 81.501; H, 3.636; B, 1.556; N, 4.042; S, 9.262 (%); experimental values: C, 81.490; H, 3.636; B, 1.640; N, 4.058; S, 9.288 (%).

[0389] Target compound D1-120 (HPLC analysis purity 99.58%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 788.0435; elemental analysis result: theoretical values: C, 71.779; H, 3.203; B, 1.373; N, 3.555; Se, 20.083 (%); experimental values: C, 71.790; H, 3.197; B, 1.311; N, 3.490; Se, 20.153 (%).

[0390] Target compound D1-121 (HPLC analysis purity 99.41%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 684.246; elemental analysis result: theoretical values: C, 85.971; H, 3.684; B, 1.577; N, 4.094; O, 4.665 (%); experimental values: C, 85.980; H, 3.646; B, 1.668; N, 4.139; O, 4.715 (%).

[0391] Target compound D1-124 (HPLC analysis purity 99.83%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 806.2657; elemental analysis result: theoretical values: C, 87.843; H, 3.869; B, 1.339; N, 6.952 (%); experimental values: C, 87.850; H, 3.962; B, 1.276; N, 6.935 (%).

[0392] Target compound D1-580 (HPLC analytical purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 732.2232; elemental analysis result: theoretical values: C, 83.609; H, 3.442; B, 1.480; N, 11.469 (%); experimental values: C, 83.610; H, 3.516; B, 1.575; N, 11.545 (%).

[0393] Target compound D1-581 (HPLC analytical purity 99.49%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 704.2643; elemental analysis result: theoretical values: C, 80.128; H, 3.579; B, 1.532; F, 10.793; N, 3.982 (%); experimental values: C, 80.140; H, 3.674; B, 1.571; F, 10.829; N, 4.062 (%).

[0394] Target compound D1-920 (HPLC analytical purity 99.69%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 800.3434; elemental analysis result: theoretical values: C, 85.488; H, 5.662; B, 1.345; N, 3.495; S, 3.997 (%); experimental values: C, 85.480; H, 5.730; B, 1.417; N, 3.455; S, 4.016 (%).

[0395] Target compound D1-925 (HPLC analytical purity 99.63%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 736.2446; elemental analysis result: theoretical values: C, 84.788; H, 3.974; B, 1.467; N, 7.614; O, 2.173 (%); experimental values: C, 84.780; H, 3.998; B, 1.503; N, 7.589; O, 2.127 (%).

[0396] Target compound D1-928 (HPLC analytical purity 99.65%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 808.2123; elemental analysis result: theoretical values: C, 75.763; H, 3.367; B, 1.335; F, 14.097; N, 3.461; O, 1.982 (%); experimental values: C, 75.750; H, 3.431; B, 1.386; F, 14.037; N, 3.395; O, 1.885 (%).

[0397] Target compound D1-931 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 898.4246; elemental analysis result: theoretical values: C, 86.845; H, 5.720; B, 1.197; N, 6.226 (%); experimental values: C, 86.860; H, 5.702; B, 1.231; N, 6.281 (%).

[0398] Target compound D1-936 (HPLC analytical purity 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 853.3757; elemental analysis result: theoretical values: C, 84.389; H, 5.674; B, 1.274; N, 4.919; S, 3.751 (%); experimental values: C, 84.400; H, 5.633; B, 1.257; N, 4.846; S, 3.717 (%).

[0399] Target compound D1-938 (HPLC analytical purity 99.36%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 800.3468; elemental analysis result: theoretical values: C, 85.487; H, 5.662; B, 1.348; N, 3.499; S, 3.995 (%); experimental values: C, 85.480; H, 5.631; B, 1.336; N, 3.432; S, 4.099 (%).

[0400] Target compound D1-941 (HPLC analytical purity 99.05%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 855.3535; elemental analysis result: theoretical values: C, 82.796; H, 5.421; B, 1.257; N, 4.905; O, 1.869; S, 3.745 (%); experimental values: C, 82.810; H, 5.470; B, 1.216; N, 4.947; O, 1.939; S, 3.700 (%).

[0401] Target compound D1-944 (HPLC analytical purity 99.29%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 734.1846; elemental analysis result: theoretical values: C, 76.844; H, 3.981; B, 1.465; F, 5.169; N, 3.805; S, 8.729 (%); experimental values: C, 76.840; H, 3.993; B, 1.454; F, 5.261; N, 3.814; S, 8.824 (%).

[0402] Target compound D1-948 (HPLC analytical purity 99.43%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 879.2532; elemental analysis result: theoretical values: C, 72.357; H, 3.212; B, 1.231; F, 12.955; N, 4.779; O, 1.823; S, 3.643 (%); experimental values: C, 72.360; H, 3.159; B, 1.258; F, 12.898; N, 4.761; O, 1.886; S, 3.665 (%).

[0403] Target compound D1-951 (HPLC analytical purity 99.78%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 698.2946; elemental analysis result: theoretical values: C, 89.385; H, 5.050; B, 1.552; N, 4.012 (%); experimental values: C, 89.390; H, 5.009; B, 1.484; N, 4.018 (%). Example D-5. Synthesis of Compound D1-166

Chemical Structure

[0404] Dissolve 2-bromo-1-(2-bromophenyl)naphthalene (19.69 mmol) in 50 ml of ultra-dry THF in a two-necked flask, cool it to -78 °C, add a pentane solution of n-butyllithium (2.5 M, 16 ml), and react at this temperature for 2 hours. Dissolve silicon tetrachloride (11.28 ml) in 30 ml of ultra-dry THF and cool it to -78 °C. Dropwise add the 2-bromo-1-(2-bromophenyl)naphthalene solution to the silicon tetrachloride solution, slowly warm it to room temperature, and stir overnight. Remove the solvent under reduced pressure to obtain the I-166-1 crude product as an oily liquid.

[0405] I-166-2 can be obtained by the same method as in Example 1. Dissolve I-166-2 (5 mmol), 2-bromo-3,6-dimethylcarbazole (6 mmol), and cesium carbonate (10 mmol) in DMF in a flask, warm it to 150 °C, and react for 12 hours. After the reaction is completed and cooled, pour it into cold water, filter it, wash it twice with 100 mL of water, then wash it once with 10 mL of methanol, and dry it to obtain the target compound I-166-3 as a pale yellow solid.

[0406] Dissolve I-166-3 (3 mmol) in 20 ml of ultra-dry THF in a two-necked flask, cool it to -78 °C, add a pentane solution of n-butyllithium (2.5 M, 1.2 ml), and react at this temperature for 2 hours. Dissolve I-166-1 (5 mmol) in 10 ml of ultra-dry THF solution and cool it to -78 °C. Dropwise add the I-166-3 solution to the I-166-1 solution, slowly warm it to room temperature, and stir overnight. Remove the solvent under reduced pressure and pass it through a silica gel column (petroleum ether:dichloromethane 10:1) to obtain I-166-4 as a pale yellow solid.

[0407] The synthesis from I-166-4 to compound D1-166 is the same as the last step of Example D-4, and compound D1-166 is obtained as a yellow solid. MALDI-TOF-MS result: molecular ion peak: 700.2557; elemental analysis result: theoretical values: C, 85.695; H, 4.749; B, 1.538; N, 3.999; Si, 4.013 (%); experimental values: C, 85.700; H, 4.709; B, 1.602; N, 4.059; Si, 3.911 (%). The synthesis methods of the following synthesis examples are all the same as those of Example D-5, and only the corresponding silanes and raw materials need to be replaced. [Chemical formula]

[0408] Target compound D1-214 (HPLC analysis purity 99.49%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 722.2135; elemental analysis result: theoretical values: C, 83.098; H, 3.769; B, 1.497; N, 7.751; Si, 3.893 (%); experimental values: C, 83.100; H, 3.679; B, 1.534; N, 7.743; Si, 3.938 (%).

[0409] Target compound D1-250 (HPLC analysis purity 99.69%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 783.1857; elemental analysis result: theoretical values: C, 79.697; H, 2.826; B, 1.377; N, 12.511; Si, 3.582 (%); experimental values: C, 79.710; H, 2.843; B, 1.405; N, 12.538; Si, 3.501 (%).

[0410] Target compound D1-314 (HPLC analysis purity 99.63%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 863.2968; elemental analysis result: theoretical values: C, 86.204; H, 4.431; B, 1.248; N, 4.861; Si, 3.248 (%); experimental values: C, 86.200; H, 4.482; B, 1.165; N, 4.817; Si, 3.190 (%).

[0411] Target compound D1-367 (HPLC analytical purity 99.65%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 914.3379; elemental analysis result: theoretical values: C, 73.522; H, 4.961; B, 1.178; F, 12.460; N, 3.064; O, 1.749 (%); experimental values: C, 73.530; H, 4.955; B, 1.255; F, 12.474; N, 3.126; O, 1.838 (%).

[0412] Target compound D1-407 (HPLC analytical purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 595.1753; elemental analysis result: theoretical values: C, 82.693; H, 3.717; B, 1.816; N, 7.062; Si, 4.719 (%); experimental values: C, 82.680; H, 3.678; B, 1.769; N, 6.982; Si, 4.658 (%).

[0413] Target compound D1-455 (HPLC analytical purity 99.68%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 725.2568; elemental analysis result: theoretical values: C, 84.405; H, 4.444; B, 1.488; N, 5.789; Si, 3.869 (%); experimental values: C, 84.410; H, 4.374; B, 1.453; N, 5.723; Si, 3.822 (%).

[0414] Target compound D1-469 (HPLC analytical purity 99.36%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 946.41; elemental analysis result: theoretical values: C, 78.626; H, 5.426; B, 1.141; N, 11.825; Si, 2.967 (%); experimental values: C, 78.630; H, 5.498; B, 1.071; N, 11.833; Si, 2.888 (%).

[0415] Target compound D1-549 (HPLC analytical purity 99.05%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 868.4435; elemental analysis result: theoretical values: C, 85.687; H, 6.608; B, 1.237; N, 3.224; Si, 3.231 (%); experimental values: C, 85.690; H, 6.616; B, 1.216; N, 3.194; Si, 3.239 (%).

[0416] Target compound D1-615 (HPLC analytical purity 99.29%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 963.3275; elemental analysis result: theoretical values: C, 87.207; H, 4.388; B, 1.123; N, 4.360; Si, 2.907 (%); experimental values: C, 87.200; H, 4.294; B, 1.108; N, 4.291; Si, 3.000 (%).

[0417] Target compound D1-639 (HPLC analytical purity 99.43%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 798.2797; elemental analysis result: theoretical values: C, 87.209; H, 4.421; B, 1.346; N, 3.510; Si, 3.521 (%); experimental values: C, 87.200; H, 4.346; B, 1.328; N, 3.436; Si, 3.597 (%).

[0418] Target compound D1-667 (HPLC analytical purity 99.78%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 948.3135; elemental analysis result: theoretical values: C, 88.587; H, 4.349; B, 1.142; N, 2.949; Si, 2.959 (%); experimental values: C, 88.590; H, 4.335; B, 1.223; N, 2.883; Si, 3.012 (%).

[0419] Target compound D1-717 (HPLC analytical purity 99.36%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 797.2257; elemental analysis result: theoretical values: C, 82.812; H, 3.535; B, 1.356; N, 8.778; Si, 3.517 (%); experimental values: C, 82.820; H, 3.626; B, 1.293; N, 8.799; Si, 3.614 (%).

[0420] Target compound D1-767 (HPLC analytical purity 99.05%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 961.3168; elemental analysis result: theoretical values: C, 83.646; H, 4.608; B, 1.123; N, 4.365; S, 3.332; Si, 2.921 (%); experimental values: C, 83.640; H, 4.646; B, 1.187; N, 4.401; S, 3.373; Si, 2.983 (%).

[0421] Target compound D1-807 (HPLC analytical purity 99.29%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 837.2896; elemental analysis result: theoretical values: C, 86.006; H, 4.326; B, 1.287; N, 5.017; Si, 3.345 (%); experimental values: C, 86.020; H, 4.295; B, 1.348; N, 4.933; Si, 3.323 (%).

[0422] Target compound D1-855 (HPLC analytical purity 99.43%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 851.2634; elemental analysis result: theoretical values: C, 84.600; H, 4.016; B, 1.272; N, 4.929; O, 1.884; Si, 3.299 (%); experimental values: C, 84.590; H, 4.027; B, 1.313; N, 5.025; O, 1.957; Si, 3.293 (%).

[0423] Target compound D1-885 (HPLC analytical purity 99.78%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 851.2357; elemental analysis result: theoretical values: C, 81.783; H, 3.553; B, 1.272; N, 8.220; O, 1.877; Si, 3.302 (%); experimental values: C, 81.780; H, 3.582; B, 1.277; N, 8.293; O, 1.952; Si, 3.218 (%). The optical properties of the representative condensed ring compound of the present invention prepared in the synthesis example of the present invention are shown in Table 1.

[0424]

Table 1

[0425] Note: In Table 1, the quantum efficiency is the ratio of the average number of photoelectrons generated per unit time at a specific wavelength to the number of incident photons, and the compound is 10 -5 mol / L concentration is dissolved in toluene to prepare a test sample, and then measured by deoxygenating with nitrogen gas. The instrument is Edinburg FLS1000 (UK), and the full width at half maximum is the peak width at half of the peak height of the fluorescence spectrum at room temperature, that is, the distance between the two points where a straight line drawn parallel to the peak bottom through the midpoint of the peak height intersects both sides of the peak. Here, the fluorescence spectrum is measured using a fluorescence spectrometer (Edinburg FLS1000 (UK)) after preparing a test sample by dissolving the compound in toluene at a concentration of 10 -5 mol / L.

[0426] As can be seen from Table 1, the condensed ring compound of the example provided by the present invention has a higher quantum efficiency (>85%), and at the same time, the luminescent compound provided by the present invention exhibits a narrower full width at half maximum (<25 nm).

[0427] Next, the technical effects and advantages of the present invention are demonstrated and verified by specifically applying the compound of the present invention to an organic electroluminescence device and measuring the actual use performance.

[0428] The organic electroluminescence device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material can be divided into a plurality of regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0429] As the material of the anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. As the material of the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination between them can be used.

[0430] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL) including only one kind of compound or a single-layer hole transport layer including a plurality of kinds of compounds. The hole transport region may also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0431] The material in the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, polyphenylene vinylene, 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), conductive polymers such as aromatic amine derivatives, or polymers containing conductive dopants, etc.

[0432] The light-emitting layer contains a light-emitting dye (i.e., dopant, Dopant) that can emit different wavelength spectra, and can also contain a sensitizer and a host material (host) at the same time. The light-emitting layer may be a single-color light-emitting layer that emits a single color such as red, green, or blue. A plurality of single-color light-emitting layers of different colors can be arranged or laminated on a plane according to the pixel pattern to form a colored light-emitting layer. When light-emitting layers of different colors are laminated, they can be separated from each other or connected to each other. The light-emitting layer may also be a single-color light-emitting layer that can emit different colors such as red, green, and blue at the same time.

[0433] The electron transport region can be an electron transport layer (ETL) with a single-layer structure, including a single-layer electron transport layer containing only one kind of compound and a single-layer electron transport layer containing a plurality of kinds of compounds. The electron transport region may also have a multilayer structure including at least one layer among an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Specifically, the manufacturing method of the organic electroluminescence device of the present invention includes the following steps.

[0434] 1. The glass plate coated with the anode material is ultrasonically treated with a commercially available detergent, rinsed with deionized water, the oil is removed by ultrasound in an acetone:ethanol mixed solvent, baked in a clean environment until the moisture is completely gone, washed with ultraviolet light and ozone, and irradiated with a low-energy positive ion beam on the surface.

[0435] 2. Place the glass plate with the anode in a vacuum chamber and evacuate it to a vacuum of 1×10 -5 ~8×10 -4 Pa. Then, vacuum deposit a hole injection material onto the anode layer film to form a hole injection layer, and the deposition rate is 0.1 - 0.5 nm / s. 3. Vacuum deposit a hole transport material onto the hole injection layer to form a hole transport layer, and the deposition rate is 0.1 - 0.5 nm / s.

[0436] 4. Vacuum deposit the organic light-emitting layer of the device onto the hole transport layer. The organic light-emitting layer material includes a host material, a sensitizer, and a dye. Using the multi-source co-evaporation method, adjust the deposition rates of the host material, the sensitizer material, and the dye so that the dye reaches a preset doping ratio. 5. Vacuum deposit the electron transport material of the device onto the organic light-emitting layer to form an electron transport layer, and its deposition rate is 0.1 - 0.5 nm / s. 6. Vacuum deposit LiF as an electron injection layer on the electron transport layer at a rate of 0.1 - 0.5 nm / s, and vacuum deposit an Al layer as the cathode of the device at a rate of 0.5 - 1 nm / s.

[0437] Embodiments of the present invention further provide a display device, and the display device includes the above-mentioned organic electroluminescence device. Specifically, the display device can be a display device such as an OLED display, and any product or component having a display function, such as a TV, a digital camera, a mobile phone, a tablet, etc., that includes the display device. The display device has the same advantages as the above-mentioned organic electroluminescence device compared to the prior art, but will not be described again here. Hereinafter, the organic electroluminescence device of the present invention will be further described through specific examples.

[0438] Examples A-1 to A-35, B-1 to B-45, and C-1 to C-40 of the present invention are organic electroluminescence devices manufactured using the compounds of the present invention. Comparative Examples 1 to 4 are parallel comparison devices manufactured by using the prior art compounds C1, C2, C3, and C4 according to the same manufacturing method as the compounds of the present invention. The structural schemes of all the manufactured devices are as follows. Device Implementation A Device Example A-1 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0439] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0440] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 to 30 nm, and in this example, it is 5 nm. The material of the hole transport layer is HT, generally the overall thickness is 5 to 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer, the sensitizer is a sensitizer, and the doping concentration is 20 wt%. A1-1 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 to 200 nm, and in this example, it is 30 nm. The material of the electron transport layer is ET, generally the thickness is 5 to 300 nm, and in this example, it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-2 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0441] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0442] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-4 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metallic aluminum(150 nm). Device Example A-3 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0443] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1-8(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0444] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-8 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metallic aluminum(150 nm). Device Example A-4 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0445] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-10(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0446] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a host material with a wide bandgap of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-10 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials are LiF(0.5 nm) and metal aluminum(150 nm) are selected. Device Example A-5 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0447] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-13(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0448] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material for the organic light-emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-13 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-6 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0449] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1-17(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0450] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material for the organic light-emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-17 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-7 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0451] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-21(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0452] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a host material with a wide bandgap of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-21 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials are LiF(0.5 nm) and metal aluminum(150 nm) are selected. Device Example A-8 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0453] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-24(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0454] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light-emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-24 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, the electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-9 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0455] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1-44(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0456] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light-emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-44 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, the electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-10 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0457] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-55(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0458] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20wt%, A1-55 is a dye, and the doping concentration is 2wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials are LiF(0.5nm) and metal aluminum (150nm) are selected. Device Example A-11 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0459] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-65(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0460] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-65 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-12 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0461] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-70(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0462] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-70 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-13 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0463] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-80(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0464] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a host material with a wide bandgap of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-80 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, the electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-14 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0465] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-81(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0466] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1 - 81 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 15 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0467] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1 - 82(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0468] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light emitting layer, Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1 - 82 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 16 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0469] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-85(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0470] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20wt%. A1-85 is a dye, and the doping concentration is 2wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5nm) and metal aluminum(150nm). Device Example A-17 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0471] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-87(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0472] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a host material with a wide bandgap of the organic light-emitting layer. Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A1 - 87 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 18 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0473] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1 - 94(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0474] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a host material with a wide bandgap of the organic light-emitting layer. Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A1 - 94 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 19 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0475] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-155(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0476] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20wt%. A1-155 is a dye, and the doping concentration is 2wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and cathode materials select LiF(0.5nm) and metal aluminum (150nm). Device Example A-20 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0477] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-179(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0478] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material for the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A1 - 179 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 21 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0479] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1 - 180(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0480] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material for the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A1 - 180 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 22 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0481] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-181(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0482] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20wt%, A1-181 is a dye, and the doping concentration is 2wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, the electron injection layer and cathode materials are LiF(0.5nm) and metal aluminum(150nm). Device Example A-23 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0483] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-182(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0484] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-182 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-24 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0485] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1-183(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0486] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-183 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A-25 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0487] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-184(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0488] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a host material with a wide bandgap in the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20wt%. A1-184 is a dye, and the doping concentration is 2wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5nm) and metallic aluminum(150nm). Device Example A-26 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0489] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A1-185(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0490] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-185 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-27 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0491] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A1-186(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0492] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a wide bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A1-186 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-28 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0493] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A2-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0494] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, in this example it is 5 nm, the hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, in this example it is 30 nm, the host is a host material with a wide bandgap of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%, A2-4 is a dye, and the doping concentration is 2 wt%, generally the thickness of the organic light-emitting layer is 1 - 200 nm, in this example it is 30 nm, the electron transport layer material is ET, generally the thickness is 5 - 300 nm, in this example it is 30 nm, and the electron injection layer and cathode materials are LiF(0.5 nm) and metal aluminum (150 nm) are selected. Device Example A-29 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0495] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A2-57(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0496] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The material of the hole transport layer is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A2 - 57 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The material of the electron transport layer is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 30 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0497] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% A3 - 4(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0498] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The material of the hole transport layer is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A3 - 4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The material of the electron transport layer is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum(150 nm). Device Example A - 31 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0499] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A4-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0500] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A4-4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-32 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0501] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A5-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0502] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a host material with a wide bandgap of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A5-4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-33 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0503] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A6-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0504] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a host material with a wide bandgap of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A6-4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum (150 nm). Device Example A-34 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0505] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A7-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0506] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20wt%. A7-4 is a dye, and the doping concentration is 2wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5nm) and metal aluminum (150nm). Device Example A-35 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0507] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% A8-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0508] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material for the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. A8-4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example B Device Example B-1 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0509] ITO / HI(5 nm) / HT(30 nm) / Host: 20 wt% Sensitizer: 2 wt% B1-1(30 nm) / ET(30 nm) / LiF(0.5 nm) / Al(150 nm)

[0510] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material for the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. B1-1 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and cathode materials select LiF(0.5 nm) and metal aluminum (150 nm). Device Example B-2 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0511] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% B1-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0512] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example it is 30 nm. The host is a wide-bandgap host material of the organic light-emitting layer. The Sensitizer is a sensitizer, and the doping concentration is 20 wt%. B1-4 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example it is 30 nm. The electron injection layer and the cathode material select LiF(0.5 nm) and metal aluminum (150 nm). Device Example B-3 The structure of the organic electroluminescence device manufactured in this example is as follows.

[0513] ITO / HI(5nm) / HT(30nm) / Host: 20wt% Sensitizer: 2wt% B1-8(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0514] Here, the anode material is ITO, the hole injection layer material is HI, generally the overall thickness is 5 - 30 nm, and in this example, it is 5 nm. The hole transport layer material is HT, generally the overall thickness is 5 - 500 nm, and in this example, it is 30 nm. The host is a wide-bandgap host material for the organic light-emitting layer, the Sensitizer is a sensitizer, and the doping concentration is 20 wt%. B1 - 8 is a dye, and the doping concentration is 2 wt%. Generally, the thickness of the organic light-emitting layer is 1 - 200 nm, and in this example, it is 30 nm. The electron transport layer material is ET, generally the thickness is 5 - 300 nm, and in this example, it is 30 nm. The electron injection layer and cathode materials select LiF(0.5 nm) a...

Claims

1. An organic compound having a structure represented by the following formula (1-1) or formula (1-2), 【Chemical 1】 where Ring Ar １ , Ring Ar ２ , Ring Ar ３ , Ring Ar ４ is each independently selected from a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring, Z is selected from N or C, W １ , W ２ , W ３ are each independently selected from a C-C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ and m1, m2, m3 are each independently selected from 0 or 1. X is BAR ５ (R ５ ) ｎ５ , a C-C single bond, O, S, Se, CR １２ R １３ , SiR １４ R １５ , NR １６ or PR １７ is selected from V is C, CH or CR ６ selected from Y is selected from C-C single bond, O, S, Se, CR １２ R １３ , SiR １４ R １５ or NR １６ and is selected from and when y1 is 0, V is CH or CR ６ is selected from, X is BAr ５ (R ５ ) ｎ５ , C-C single bond, O, S, Se, CR １２ R １３ , SiR １４ R １５ , NR １６ or PR １７ is selected from, when y1 is 1, V is C, X is BAr ５ (R ５ ) ｎ５ and Ring Ar ５ is selected from a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring, R ７ 、 R ８ 、 R ９ 、 R １０ 、 R １１ 、 R １２ 、 R １３ 、 R １４ 、 R １５ 、 R １６ and R １７ are each independently selected from one of a substituted or unsubstituted C1-C36 linear alkyl group, a C3-C36 cycloalkyl group, a C6-C30 arylamino group, a C6-C60 aryl group, a C6-C60 aryloxy group, and a C5-C60 heteroaryl group; and R ７ and R ８ do not combine with each other or combine to form a ring, and R ９ and R １０ do not combine with each other or combine to form a ring, and R １２ and R １３ either do not combine, or are combined via any one of C-C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ to form a ring, and between R １４ and R １５ either do not combine, or are combined via any one of C-C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ to form a ring, R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C30 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amine group, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amine group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C3-C30 heteroarylamine group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C60 arylboryl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, R １ 、 R ２ 、 R ３ 、 R ４ Each independently is bonded to the fused ring structure via a single bond, or R １ 、 R ２ 、 R ３ 、 R ４ each independently condenses with the fused ring structure via O, S, Se, CR １ R ２ or NR ５ to form a ring structure, n1, n2, n3, n4 and n5 are each independently selected from integers of 0 to 10, When n1, n2, n3, and n4 are each independently integers greater than 1, a plurality of corresponding Rs １ among a plurality of Rs ２ among a plurality of Rs ３ among a plurality of Rs ４ among them are each the same or different, and among a plurality of Rs １ among them do not combine or combine to form a ring, among a plurality of Rs ２ among them do not combine or combine to form a ring, among a plurality of Rs ３ among them do not combine or combine to form a ring, among a plurality of Rs ４ among them do not combine or combine to form a ring, said R １ 、R ２ 、R ３ 、R ４ 、R ５ 、R ６ 、R ７ 、R ８ 、R ９ 、R １０ 、R １１ 、R １２ 、R １３ 、R １４ 、R １５ 、R １６ and R １７ When substituents are independently present on each of them, the substituents are each independently selected from halogen, cyano group, C1-C20 linear alkyl group, C3-C20 cycloalkyl group, C1-C10 alkoxy group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C30 aryloxy group, C6-C30 aryl group, substituted or unsubstituted C6-C60 arylboryl group, and one or a combination of two of C3-C30 heteroaryl groups characterized in that it is an organic compound.

2. The ring Ar １ , the ring Ar ２ , the ring Ar ３ is each independently a structure represented by the following formula (a) or formula (b), and the dotted double bond represents the condensation position of the group: [Chemical Formula 2] In formula (a), Z １ , Z ２ , Z ３ , Z ４ is each independently selected from C, CH or N, In formula (b), Z ５ is selected from O, S, NR １ or CR2R3, where R1, R2, and R3 are each independently selected from a substituted or unsubstituted C1-C20 linear alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. When substituents are present independently on R1, R2, and R3, the substituents are each independently selected from a halogen, a cyano group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C6-C30 aryl group, and a C3-C30 heteroaryl group. The organic compound according to claim 1, wherein ring H is selected from one of a C6-C30 aromatic ring and a C3-C30 heteroaromatic ring

3. The organic compound according to claim 2. H is a benzene ring, and Z is S, NR １ or CR ２ R ３ selected from

4. The organic compound according to claim 2. The ring Ar １ , the ring Ar ２ , the ring Ar ３ One of them has a structure represented by formula (b), and the other ring structures are each independently a structure represented by formula (a).

5. The organic compound according to claim 1. the ring r １ , the ring Ar ２ , the ring Ar ３ is independently selected from a C6-C30 aromatic ring or a C3-C30 heteroaromatic ring, Preferably, ring Ar １ ring Ar ２ ring Ar ３ is each independently selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, furan, benzofuran, dibenzofuran, indole, benzindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, and thiophene, More preferably, the ring Ar １ ring Ar ２ ring Ar ３ is independently selected from one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene

6. In formula (1), n1, n2, n3 and n4 are each independently selected from integers of 1 to 5, The organic compound according to claim 1. Said R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently selected from one of deuterium, a halogen, a cyano group, a C1-C12 linear alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, said R ７ 、R ８ 、R ９ 、R １０ 、R １１ 、R １２ 、R １３ 、R １４ 、R １５ 、R １６ and R １７ are each independently selected from one of a substituted or unsubstituted C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C6-C30 arylamino group, a C6-C30 aryl group, a C6-C30 aryloxy group, and a C5-C30 heteroaryl group, Preferably, the R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ and R １７ are each independently selected from any one of C1-C10 chain alkyl groups, substituted or unsubstituted benzene rings, naphthalene rings, and anthracene rings

7. The organic compound according to claim 1. wherein X is BAR ５ (R ５ ) ｎ５ , O, S, Se, CR １２ R １３ , SiR １４ R １５ when, Y is O, S, Se, CR １２ R １３ , SiR １４ R １５ and Preferably, said X is BAr ５ (R ５ ) ｎ５ , O, S, CR １２ R １３ , SiR １４ R １５ When it is, said Y is O, S, CR １２ R １３ , SiR １４ R １５ and More preferably, X is BAr ５ (R ５ ) ｎ５ , S, CR １２ R １３ , and when Y is S, CR １２ R １３ it is

8. The organic compound according to claim 1. In formula (1-1), said X is BAr ５ (R ５ ) ｎ５ , O, S, Se, CR １２ R １３ , SiR １４ R １５ wherein Preferably, said X is BAR ５ (R ５ ) ｎ５ selected from

9. The organic compound according to claim 1. In formula (1-2), said X is BAr ５ (R ５ ) ｎ５ , a C-C single bond, O, S, Se, CR １２ R １３ , SiR １４ R １５ or NR １６ and is selected from Preferably, said X is BAR ５ (R ５ ) ｎ５ or CR １２ R １３ selected from

10. The organic compound according to claim 1 or 7. Said W １ , W ３ are each independently a C-C single bond, S, CR ７ R ８ or NR １１ is selected from, m1 and m3 are 1, and m2 is 0

11. Having a structure represented by any one of the following formulas (2-1), (2-2) or (2-3), The organic compound according to claim 1. 【Chemical 3】 In formulas (2-1), (2-2) and (2-3), R １ -R ６ 、R ７ -R １７ 、Ar １ -Ar ５ 、n1 - n5, W １ -W ２ 、The definitions of m1 - m2, X, Y and Z are the same as those in formulas (1-1) and (1-2), respectively.

12. Having a structure represented by any one of the following formulas (2), (3), (4), (5), (6), (7) or (8), The organic compound according to claim 1. 【Chemical Formula 4】 【Chem.】 Here, R １ -R ６ , n1 - n5, Ar １ -Ar ５ , W １ , W ３ , the definitions of m1 and m3 are the same as those in Formula (1-1), respectively

13. Having a structure represented by any one of the following formulas (10), (11), (12), (13), (14), (15), (16) or (17), The organic compound according to claim 1. 【Chemical Formula 5】 【Chem.】 Here, R １ -R ６ 、R １３ 、R １４ 、R １５ 、R １６ and R １７ 、n1 - n5, Ar １ -Ar ５ 、W １ 、W ３ 、the definitions of m1 and m3 are all the same as the definitions in formula (1-1), respectively, R １２ and R １３ either do not combine or are combined via any one of C-C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ to form a ring, and either do not combine or are combined via any one of C-C single bond, O, S, Se, CR １４ and R １５ either do not combine or are combined via any one of C-C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ to form a ring

14. Having a structure represented by any one of the following formulas (18), (19), (20), (21), (22), (23), (24), (25) or (26), The organic compound according to claim 1. ​ 【Chem.】 Here, R １ -R ６ 、R １３ 、R １４ 、R １５ 、R １６ and R １７ 、n1 - n5, Ar １ -Ar ５ 、W １ 、W ３ 、the definitions of m1 and m3 are all the same as the definitions in Formula (1-1), respectively, R １２ and R １３ either do not combine or are combined via any one of C—C single bond, O, S, Se, CR ７ R ８ , SiR ９ R １０ or NR １１ to form a ring, and either do not combine or are combined via any one of C—C single bond, O, S, Se, CR １４ R １５ and R ７ R ８ , SiR ９ R １０ or NR １１ to form a ring

15. n1, n2, n3 and n4 are each independently selected from integers of 1 to 5, Said R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently selected from among deuterium, a halogen, a cyano group, a C1-C12 linear alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. The organic compound according to any one of claims 12, 13 or 14. The ring Ar １ , the ring Ar ２ , the ring Ar ３ is each independently selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, furan, benzofuran, dibenzofuran, indole, benzindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, and thiophene, Preferably, the ring Ar １ ring Ar ２ ring Ar ３ is each independently selected from one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene

16. The organic compound according to any one of claims 1, 12, 13 or 14. said R １ R ２ R ３ R ４ R ５ and R ６ is, independently of each other, hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, 2-methylbutyl group, n-pentyl group, s-pentyl group, cyclopentyl group, neopentyl group, n-hexyl group, cyclohexyl group, neohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, 2-ethylhexyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysenyl group, ferrenyl group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, genyl group, terphenyl group, trimerized phenyl group, quarterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthoimidazolyl group, phenanthroimidazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthroxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,Selected from a substituent of one of 8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaphenalenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5_oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, diphenylboril group, dimethylboril group, dipentafluorophenylboril group, bis(2,4,6-triisopropylphenyl)boril group, or selected from a combination of two of the above, the aforementioned R ７ R ８ R ９ R １０ R １１ R １２ R １３ R １４ R １５ R １６ and R １７ is, independently of each other, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthrenyl group, a benzophenanthrenyl group, a pyrenyl group, a chrysenyl group, a ferrenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a genyl group, a terphenyl group, a trimerized phenyl group, a quarterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis or trans indenofluorenyl group, a trimerized indenyl group, an isotrimerized indenyl group, a spirotrimerized indenyl group, a spiroisotrimerized indenyl group, a furyl group, a benzofuryl group, an isobenzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5,6-quinolyl group, a benzo-6,7-quinolyl group, a benzo-7,8-quinolyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthroimidazolyl group, a pyridinoimidazolyl group, a pyrazinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthroxazolyl group, a phenanthroxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, 4,Selected from a substituent of one of 5-diazapirenyl group, 4,5,9,10-tetraazaphenalenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, or selected from a combination of two of the above, Preferably, the R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently selected from hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, trifluoromethyl group, pentafluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, 1,3,5-triazinyl group, diphenylborolyl group, dimethylborolyl group, dipentafluorophenylborolyl group, bis(2,4,6-triisopropylphenyl)borolyl group, or a combination of two of the above groups, Preferably, the R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ and R １７ are each independently selected from a substituent of one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a trifluoromethyl group, a pentafluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis or trans indenofluorenyl group, a furyl group, a benzofuryl group, a thienyl group, a benzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a 1,3,5-triazinyl group, a diphenylboryl group, a dimethylboryl group, a dipentafluorophenylboryl group, a bis(2,4,6-triisopropylphenyl)boryl group, or selected from a combination of two of the foregoing. Most preferably, the R １ , R ２ , R ３ , R ４ , R ５ and R ６ each independently represents one of hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, trifluoromethyl group, pentafluoroethyl group, cyano group, halogen, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, spirobifluorenyl group, carbazolyl group, 1,3,5-triazinyl group, diphenylborolyl group, dimethylborolyl group, dipentafluorophenylborolyl group, bis(2,4,6-triisopropylphenyl)borolyl group, or is selected from a combination of two of the above groups, Most preferably, the R ７ 、R ８ 、R ９ 、R １０ 、R １１ 、R １２ 、R １３ 、R １４ 、R １５ 、R １６ and R １７ are each independently selected from a substituent of one of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyano group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, spirobifluorenyl group, or selected from a combination of two of the above groups

17. Selected from compounds having the following structure The compound according to claim 1. 【Chemical Formula 7】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 [Chemical] 【Chem.】 [Chemical] [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】

18. An application of the compound according to any one of claims 1 to 17, ​ The application is used as a functional material in an organic electronic device, and the organic electronic device is selected from an organic electroluminescence device, an optical sensor, a solar cell, an illumination device, an organic thin film transistor, an organic field effect transistor, an information label, an electronic artificial skin sheet, a sheet scanner or an electronic paper. Furthermore, the application of the compound is used as a light-emitting layer material in an organic electroluminescence device, specifically as a light-emitting material in the light-emitting layer. The application of the compound characterized thereby.

19. An organic electroluminescence device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of Claims 1 to 17. Furthermore, the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is formed on the first electrode layer, the second electrode layer is formed on the electron transport region, and between the hole transport region and the electron transport region is the light-emitting layer, where the light-emitting layer contains the compound according to any one of Claims 1 to 17. The organic electroluminescence device characterized thereby.

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