A compound and an organic light-emitting device

Abstract

The present invention belongs to the technical field of organic electroluminescence, and discloses a compound and an organic electroluminescent device. The general structural formula of the compound is shown in Formula (1): wherein, Ring A is selected from the following Formula (2) or Formula (3); X1-X12 are each independently selected from CR0 or N, and X is selected from NRa, CRbRc. The compound has the advantages of high photo and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a host material in OLED light-emitting devices.

Description

[0001] This application is a divisional application of the application with the application date of January 29, 2024, the application number of 202410116662.9, and the invention title of "A Compound and an Organic Electroluminescent Device". Technical Field

[0002] The present invention belongs to the technical field of organic electroluminescence, and particularly relates to a compound and an organic electroluminescent device. Background Art

[0003] Currently, as a new generation of display technology, organic electroluminescent devices (OLEDs) have received increasing attention in both display and lighting technologies, and have a very broad application prospect. However, compared with the requirements of market applications, the performance of OLED devices such as luminous efficiency, driving voltage, and service life still needs to be further improved.

[0004] Generally speaking, the basic structure of an OLED device is that various organic functional material thin films are sandwiched between metal electrodes, just like a sandwich structure. Under the drive of current, holes and electrons are injected from the anode and cathode respectively. After moving a certain distance, the holes and electrons recombine in the light-emitting layer and are released in the form of light or heat, thereby achieving the light-emitting effect. However, the properties of phosphorescent OLEDs are not only determined by the triplet emitters used. Other types of materials, such as host materials, are also quite important. Host materials play a significant role in reducing the driving voltage of the device, improving the luminous efficiency of the device, and extending the service life of the device. Therefore, it is necessary to continue to research and develop new host materials to further improve the performance of organic electroluminescent devices.

[0005] Of the prior art There is a host material with a dibenzofuran - phenylfluorene connecting a diarylamine, and a triazine compound is used as a red light co - host material. The device efficiency of this type of material still needs to be further improved; of the prior art A host material with a phenanthrooxazole structural unit connecting a diarylamine. This type of material has strong planarity, a high evaporation temperature, and the device efficiency and service life also need to be improved. Of the prior art A material with a phenanthrobenzofuran structural unit connecting a diarylamine of a similar structure. The device performance of this type of material used as a dual - host material also needs to be further improved, especially the device service life, which needs to be further enhanced.

[0006] Therefore, there is an urgent need to provide a new compound to solve the above problems existing in the light - emitting device. Summary of the Invention

[0007] The present invention aims to solve at least one of the technical problems existing in the above - mentioned prior art. For this reason, the present invention provides a compound and an organic electroluminescent device.

[0008] The first aspect of the present invention provides a compound.

[0009] In some embodiments, a compound has a general structural formula as shown in formula (1):

[0010]

[0011] Wherein, ring A is selected from the following formula (2) or formula (3);

[0012]

[0013] Wherein, X1-X 12 are each independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 Two adjacent sites thereof are fused to the 5-membered ring containing X in formula (1);

[0014] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboron, C6-C60 arylboron, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamino; two adjacent R0s can be linked to form a fused ring;

[0015] X in formula (1) is selected from NR a , CR b R c or a chalcogen element;

[0016] R a , R b , R c are each independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, C6-C30 arylsilyl;

[0017] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene or a substituted or unsubstituted C3-C60 heteroarylene;

[0018] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl;

[0019] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, amino substituted by C1-C6 alkyl, C1-C6 hydrocarbyl substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbyl substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from monosubstitution to maximum substitution.

[0020] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C30 alkoxy, C6-C30 aryloxy, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboron, C6-C30 arylboron, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamino.

[0021] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C20 alkoxy, C6-C20 aryloxy, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboron, C6-C20 arylboron, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino or C6-C20 arylamino.

[0022] In some embodiments, the R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C3-C12 heteroaryl.

[0023] In some embodiments of the present invention, adjacent R0 refers to R0 located on adjacent carbon atoms.

[0024] In some embodiments of the present invention, the substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, amino substituted by C1-C6 alkyl, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from single substitution to maximum number of substitutions.

[0025] In some embodiments of the present invention, the substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, amino substituted by C1-C6 alkyl, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions ranges from single substitution to maximum number of substitutions.

[0026] In some embodiments, the chalcogen element is selected from O, S or Se.

[0027] In some embodiments, the R a 、R b 、R c are each independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C3-C20 alkylsilyl, C6-C20 arylsilyl.

[0028] In some embodiments, the Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.

[0029] In some embodiments, the heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl are independently selected from at least one of O, S, N, Se, Si, Ge.

[0030] In some embodiments, the structures shown in Formula (2) and Formula (3) are selected from the structures shown in the following Formula (A-1) to Formula (A-8):

[0031]

[0032] Wherein, * represents the site fused to the 5-membered ring containing X in Formula (1);

[0033] Wherein a is an integer from 0 to 10; if a ≥ 2 or a larger integer, each R0 may be the same or different, and adjacent R0s may be connected to form a fused ring.

[0034] In some embodiments, the structures shown in Formula (2) and Formula (3) are selected from the structures shown in the following Formula (A-9) to Formula (A-16):

[0035]

[0036] wherein, * represents the site fused with the 5-membered ring containing X in formula (1);

[0037] wherein a is an integer from 0 to 6; if a is ≥ 2 or a larger integer, each R0 can be the same or different, and adjacent R0s can be connected to form a fused ring.

[0038] In some embodiments, L is a substituted or unsubstituted C6-C20 arylene or heteroarylene.

[0039] In some embodiments, L is a substituted or unsubstituted C6-C20 arylene or a substituted or unsubstituted C3-C60 heteroarylene

[0040] In some embodiments, X is CR b R c , O or S.

[0041] In some embodiments, the R b , R c are each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C5-C10 heteroaryl.

[0042] In some embodiments, at least one of X1-X 12 contains an N.

[0043] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted group, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted benzocycloalkyl, substituted or unsubstituted phenanthroxazolyl, oxaspirofluorene, substituted or unsubstituted benzocarbazolyl, or a combination of at least two of the above.

[0044] In some embodiments of the present invention, the substitution is replaced by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, amino substituted with C1-C6 alkyl, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from monosubstitution to the maximum number of substitutions.

[0045] In some embodiments of the present invention, the substitution is replaced by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, amino substituted with C1-C6 alkyl, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions ranges from monosubstitution to the maximum number of substitutions.

[0046] In some embodiments of the present invention, the aryl is selected from phenyl, naphthyl, anthracenyl, phenanthryl, tetracenyl, pyrenyl, base, benzo[c]phenanthryl, benzo[g]chrysenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl.

[0047] In some embodiments of the present invention, the heteroaryl is selected from pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, dibenzothiophenyl, azadibenzofuryl, azadibenzothiophenyl, diazadibenzofuryl, diazadibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothienyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl.

[0048] In some embodiments, the compound is one of the following structural formulas, or a structure in which hydrogen in the following structural formulas is partially or completely replaced by deuterium or fluorine:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] Taking CPD435 as an example, Ar1 is an unsubstituted C6 aryl group (i.e., phenyl), and Ar2 is a substituted aryl group, and the substitution is a heteroaryl group substituted by a C1-C6 hydrocarbon group (phenyl).

[0067] The second aspect of the present invention provides an organic electroluminescent device.

[0068] Specifically, an organic electroluminescent device includes the above compound.

[0069] In some embodiments, an organic electroluminescent device includes: a cathode and an anode, the cathode and the anode are disposed opposite to each other, a light-emitting layer is provided between the cathode and the anode, and the light-emitting layer includes the above compound. The compound of the present invention can be used alone or after doping to prepare the light-emitting layer.

[0070] In one embodiment, the light-emitting layer is a red light-emitting layer, including a red light-emitting material and at least one of the above compounds. In this embodiment, the compound of the present invention serves as the host material of the red light-emitting layer.

[0071] The third aspect of the present invention provides the application of the above compound in the semiconductor field.

[0072] Specifically, the application of the above compound in the preparation of semiconductor devices.

[0073] In some embodiments, the semiconductor device includes an optoelectronic device.

[0074] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0075] The compounds of the present invention have the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as host materials in OLED light-emitting devices. At the same time, it has a relatively low melting point, which is beneficial to the evaporation stability of the material as a molten material. As a red light host material, this compound has the potential to be applied in the AMOLED industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0076] Figure 1 is the 1 1H NMR spectrum of the compound CPD231 of the present invention;

[0077] Figure 2 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0078] In order to make the technical solutions of the present invention more clearly understood by those skilled in the art, the following examples are listed for illustration. It should be noted that the following examples do not limit the scope of protection required by the present invention.

[0079] Unless otherwise specified, the raw materials, reagents or devices used in the following examples can be obtained from conventional commercial channels or can be obtained by existing known methods.

[0080] A compound having the structure shown in formula (1):

[0081]

[0082] wherein X is selected from NR a , CR b R c , O, S or Se;

[0083] wherein ring A is selected from the following formula (2) or formula (3);

[0084]

[0085] wherein X1-X 12 are independently selected from CR0 or N; and two adjacent sites among X1-X4, X5-X6, X7-X8, X9-X 12 are fused to the 5-membered ring containing X in formula (1).

[0086] R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboron, C6-C60 arylboron, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamino; two adjacent R0s may be connected to form a fused ring.

[0087] R a 、R b 、R c are each independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C3-C20 alkylsilyl, C6-C20 arylsilyl;

[0088] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene or a substituted or unsubstituted C3-C60 heteroarylene;

[0089] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl, a substituted or unsubstituted C2-C36 heteroaryl;

[0090] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, an amino group substituted by C1-C6 alkyl, a C6-C30 aryl substituted or unsubstituted by C1-C6 hydrocarbyl, a C3-C30 heteroaryl substituted or unsubstituted by C1-C6 hydrocarbyl, wherein the number of substitutions is from single substitution to maximum number of substitutions;

[0091] The heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl are independently selected from at least one of O, S, N, Se, Si, Ge;

[0092] Hereinafter, examples of each group of the compounds represented by formula (1), formula (2), and formula (3) will be described.

[0093] It should be noted that in this specification, the "carbon number a to b of the X group which is substituted or unsubstituted" in this expression means the carbon number of the X group in the case where it is not substituted, and does not include the carbon number of the substituent when the X group is substituted.

[0094] As specific examples of the alkyl group, it is a linear or branched alkyl group. Specifically, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, n-decyl and its isomers, etc. Preferably, it is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and more preferably, it is propyl, isopropyl, isobutyl, sec-butyl, tert-butyl.

[0095] As specific examples of the cycloalkyl group, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Preferably, it is cyclopentyl, cyclohexyl.

[0096] As specific examples of the alkenyl group, for example, vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, 3-hexatrienyl, etc. Preferably, it is propenyl, allyl.

[0097] As specific examples of the heteroalkyl group, it is a linear or branched alkyl group, cycloalkyl group, etc. containing atoms other than carbon and hydrogen. For example, mercaptomethylmethyl, methoxymethyl, ethoxymethyl, tert-butoxymethyl, N,N-dimethylmethyl, epoxybutyl, epoxypentyl, epoxyhexyl, etc. Preferably, it is methoxymethyl, epoxypentyl.

[0098] As specific examples of the aryl group, for example, phenyl, naphthyl, anthryl, phenanthryl, tetraphenyl, pyrenyl, -yl, benzo[c]phenanthryl, benzo[g]chrysenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl, etc. Preferably, it is phenyl, naphthyl.

[0099] As specific examples of the heteroaryl group, for example, pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, dibenzothiophenyl, azadibenzofuryl, azadibenzothiophenyl, diazadibenzofuryl, diazadibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothienyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl, etc. Preferably, it is pyridyl, pyrimidinyl, triazinyl, dibenzofuryl, dibenzothiophenyl, azadibenzofuryl, azadibenzothiophenyl, diazadibenzofuryl, diazadibenzothiophenyl, carbazolyl, azacarbazolyl, diazacarbazolyl.

[0100] The following embodiments are only for facilitating the understanding of the technical invention and should not be regarded as specific limitations on the present invention.

[0101] The raw materials, solvents, etc. involved in the synthesis of the compounds in the present invention are all purchased from well-known suppliers in the field such as Alfa and Acros.

[0102] Synthesis of compound CPD2:

[0103] The synthesis route is as follows:

[0104]

[0105]

[0106] Synthesis of compound CPD2-3:

[0107] Add CPD2-1 (30.00 g, 106.56 mmol), CPD2-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphino)ferrocene dichloropalladium (Pd(dppf)Cl2, 1.56 g, 2.13 mmol), potassium acetate (KOAc, 15.69 g, 159.84 mmol), and 1,4-dioxane (1,4-Dioxane, 450 mL) into a 1000 mL three-necked round-bottom flask, displace the vacuum with nitrogen three times, then heat the system to 100 °C and react for 2 hours. Monitor the reaction by TLC (thin-layer chromatography, ethyl acetate:n-hexane = 1:10 as the eluent). When the raw material CPD2-1 is consumed completely;

[0108] Cool down to 60 °C, concentrate under reduced pressure to remove the solvent, add ethyl acetate (700 mL), wash three times with deionized water (300 mL * 3), separate the layers, mix the sample with silica gel and load it onto the column dry, and perform silica gel column chromatography purification (200 - 300 mesh silica gel, ethyl acetate:n-hexane = 1:15 as the eluent). After elution, concentrate under reduced pressure at 70 °C for 1 hour to obtain a white solid of CPD2-3 (27.62 g, mass fraction purity: 98.01%, yield: 78.88%). The mass spectrometry characterization result: 329.12 (M + H).

[0109] Synthesis of compound CPD2-5:

[0110] CPD2-3 (25.00 g, 76.08 mmol), CPD2-4 (17.89 g, 76.08 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.75 g, 1.52 mmol), potassium carbonate (15.77 g, 114.12 mmol), tetrahydrofuran (THF, 375 mL), and deionized water (125 mL) were added to a 1000 mL three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times, and then heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the eluent), and the raw material CPD2-3 was consumed completely.

[0111] The temperature was lowered to 60 °C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and it was washed three times with deionized water (300 mL * 3). After liquid separation, it was mixed with silica gel and purified by dry-column chromatography on a silica gel column (200 - 300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as the eluent). After elution, it was concentrated under reduced pressure at 70 °C for 2 hours to obtain a white solid CPD2-5 (20.45 g, mass fraction purity: 99.21%, yield: 75.32%). The mass spectrometry characterization result was: 357.22 (M + H).

[0112] Synthesis of compound CPD2-7:

[0113] CPD2-5 (18.00 g, 50.45 mmol), CPD2-6 (25.94 g, 75.67 mmol), and tetrahydrofuran (270 mL) were added to a 1000 mL three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times, and then the temperature was lowered to 5 °C. Sodium methoxide (NaOMe, 5.45 g, 100.90 mmol) was added at one time, and the reaction was maintained at 5 °C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the eluent), and the raw material CPD2-5 was consumed completely.

[0114] Deionized water (500 mL) was added thereto, the solvent was removed by concentration under reduced pressure, and it was extracted with ethyl acetate (700 mL). After liquid separation, it was concentrated under reduced pressure at 70 °C for 1 hour to obtain a white solid CPD2-7 (18.44 g, yield: 95.00%). The mass spectrometry characterization result was: 385.04 (M + H). The obtained compound was used directly in the next step without purification.

[0115] Synthesis of compound CPD2-8:

[0116] CPD2-7 (17.00 g, 44.17 mmol) and toluene (170 mL) were added to a 500 mL three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times. Then, the system was cooled to 5 °C, and methanesulfonic acid (MsOH, 8.49 g, 88.34 mmol) was slowly added dropwise. The addition was completed in 3 minutes, and the reaction was maintained at 5 °C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the eluent), and the raw material CPD2-7 was consumed completely.

[0117] Methanol (200 mL) was added thereto, and a large amount of white solid precipitated. The solid was collected by filtration to obtain 17 g of solid. It was crystallized once with toluene (204 mL) and methanol (170 mL), filtered by suction, and the filter cake was dried in vacuo at 80 °C for 1 hour to obtain a white solid CPD2-8 (11.63 g, mass fraction purity: 99.83%, yield: 74.62%). The mass spectrometry characterization result was: 353.06 (M+H).

[0118] Synthesis of compound CPD2:

[0119] CPD2-8 (10.00 g, 28.34 mmol), CPD2-9 (7.30 g, 29.76 mmol), tris(dibenzylideneacetone)dipalladium(Pd2(dba)3, 0.52 g, 0.57 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-Phos, 0.54 g, 1.14 mmol), sodium tert-butoxide (NaOtBu, 4.09 g, 42.51 mmol) and toluene (150 ml) were added to a 500 mL three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times. Then, the system was heated to 105 °C and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the eluent), and the raw material CPD 2-8 was consumed completely.

[0120] The temperature was cooled to 60 °C, methanol (150 mL) was added, and the mixture was allowed to cool to room temperature and stirred for 30 minutes to precipitate a large amount of solid. The solid was collected by filtration to obtain 20 g of solid. Toluene (300 mL) was added, and then the system was heated to 100 °C until it was dissolved and clarified. 30 g (300 - 400 mesh) of silica gel was spread for filtration, and the surface of the silica gel was rinsed with toluene (50 mL). The filtrates were combined and concentrated to obtain 18 g. It was crystallized twice with toluene (180 mL) and methanol (90 mL), filtered by suction, and the filter cake was dried in vacuo at 90 °C for 3 hours to obtain a light yellow solid CPD2 (14.07 g, mass fraction purity: 99.94%, yield: 88.41%).

[0121] 14.07 g of crude light yellow solid CPD2 was sublimated and purified to obtain sublimation-pure CPD2 (11.26 g, mass fraction purity: 99.95%, yield: 80.02%). The results of mass spectrometry characterization: 562.22 (M+H). The results of NMR characterization: 1 H NMR (400 MHz, CDCl3) δ8.17 (d, J = 9.1 Hz, 1H), 8.07 - 8.00 (m, 1H), 7.97 - 7.87 (m, 4H), 7.85 (dd, J = 7.5, 3.0 Hz, 2H), 7.60 - 7.55 (m, 2H), 7.55 - 7.48 (m, 4H), 7.42 - 7.39 (m, 3H), 7.32 (d, J = 7.3 Hz, 1H), 7.31 - 7.24 (m, 2H), 7.16 - 7.07 (m, 5H), 7.02 - 6.97 (m, 2H).

[0122] Synthesis of compound CPD19:

[0123] Synthesis route:

[0124]

[0125] Synthesis of compound CPD19-2:

[0126] Referring to the synthesis and purification methods of compound CPD2-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound CPD19-2 (30.52 g, mass fraction purity: 99.00%, yield: 78.62%). The results of mass spectrometry characterization: 329.12 (M+H).

[0127] Synthesis of compound CPD19-3:

[0128] Referring to the synthesis and purification methods of compound CPD2-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound CPD19-3 (27.02 g, mass fraction purity: 99.33%, yield: 76.52%). The results of mass spectrometry characterization: 357.22 (M+H).

[0129] Synthesis of compound CPD19-4:

[0130] Referring to the synthesis and purification methods of compound CPD2-7, only the corresponding raw materials need to be changed to obtain the white solid as the target compound CPD19-4 (25.66 g, yield: 96.08%). The results of mass spectrometry characterization: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0131] Synthesis of compound CPD19-5:

[0132] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD19-5 as a white solid (17.95 g, mass fraction purity: 99.76%, yield: 75.55%). The mass spectrometry characterization result is: 353.06 (M+H).

[0133] Synthesis of compound CPD19:

[0134] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD19 as a light yellow solid (16.74 g, mass fraction purity: 99.95%, yield: 78.65%). After sublimation purification of 16.74 g of the light yellow solid crude product of CPD19, sublimation-pure CPD19 (13.10 g, mass fraction purity: 99.95%, yield: 78.26%) is obtained. The mass spectrometry characterization result is: 652.32 (M+H).

[0135] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.17 (d, J = 9.1 Hz, 1H), 8.08 (d, J = 2.1 Hz, 1H), 8.07 - 8.02 (m, 1H), 8.02 - 7.97 (m, 1H), 7.94 (dd, J = 8.6, 2.0 Hz, 2H), 7.92 - 7.87 (m, 1H), 7.87 - 7.81 (m, 3H), 7.66 - 7.61 (m, 1H), 7.60 - 7.55 (m, 2H), 7.55 - 7.47 (m, 4H), 7.47 - 7.36 (m, 7H), 7.36 - 7.28 (m, 3H), 7.02 - 6.97 (m, 2H).

[0136] Synthesis of compound CPD26:

[0137] Synthesis route:

[0138]

[0139] Synthesis of compound CPD26-3:

[0140] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed and the reaction temperature is 90 °C for the reaction to obtain the target compound CPD26-3 as a white solid (35.62 g, mass fraction purity: 99.83%, yield: 74.63%). The mass spectrometry characterization result is: 363.14 (M+H).

[0141] Synthesis of compound CPD26:

[0142] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD26 as a light yellow solid (17.69 g, mass fraction purity: 99.93%, yield: 75.21%). After sublimation purification of 17.69 g of the light yellow solid crude CPD26, sublimation-pure CPD26 (15.62 g, mass fraction purity: 99.93%, yield: 88.30%) was obtained. The mass spectrometry characterization result: 679.22 (M+H).

[0143] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.17 (d, J = 9.1 Hz, 1H), 8.11 (d, J = 2.2 Hz, 1H), 8.07 - 8.01 (m, 1H), 7.97 - 7.87 (m, 5H), 7.86 - 7.84 (m, 2H), 7.78 (dd, J = 8.9, 1.4 Hz, 1H), 7.60 - 7.55 (m, 2H), 7.55 - 7.47 (m, 6H), 7.45 - 7.40 (m, 7H), 7.37 - 7.29 (m, 2H), 7.10 - 7.05 (m, 2H).

[0144] Synthesis of compound CPD57:

[0145] Synthesis route:

[0146]

[0147] Synthesis of compound CPD57-2:

[0148] Referring to the synthesis and purification method of reference compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD57-2 as a white solid (28.02 g, mass fraction purity: 98.52%, yield: 77.65%). The mass spectrometry characterization result: 329.12 (M+H).

[0149] Synthesis of compound CPD57-3:

[0150] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD57-3 as a white solid (26.33 g, mass fraction purity: 99.45%, yield: 75.09%). The mass spectrometry characterization result: 357.22 (M+H).

[0151] Synthesis of compound CPD57-4:

[0152] For the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed. The target compound CPD57-4 (24.44 g, yield: 97.89%) is obtained as a white solid. The mass spectrometry characterization result is: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0153] Synthesis of compound CPD57-5:

[0154] For the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed. The target compound CPD57-5 (16.85 g, mass fraction purity: 99.79%, yield: 76.85%) is obtained as a white solid. The mass spectrometry characterization result is: 353.06 (M+H).

[0155] Synthesis of compound CPD57-7:

[0156] For the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed. The target compound CPD57-7 (20.84 g, mass fraction purity: 99.80%, yield: 77.15%) is obtained as a white solid. The mass spectrometry characterization result is: 370.12 (M+H).

[0157] Synthesis of compound CPD57:

[0158] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed. The target compound CPD57 (18.95 g, mass fraction purity: 99.93%, yield: 77.01%) is obtained as a light yellow solid. After sublimation purification of 18.95 g of the light yellow solid CPD57 crude product, sublimation-pure CPD57 (16.41 g, mass fraction purity: 99.95%, yield: 86.60%) is obtained. The mass spectrometry characterization result is: 686.22 (M+H).

[0159] Nuclear magnetic resonance characterization result: 1 H NMR(400MHz,CDCl3)δ8.64(s,1H),8.33 - 8.26(m,1H),8.14(dd,J=5.5,3.3Hz,1H),8.10 - 8.04(m,2H),8.01(d,J=8.9Hz,1H),7.98 - 7.84(m,7H),7.81 - 7.74(m,2H),7.61 - 7.54(m,2H),7.54 - 7.47(m,6H),7.44 - 7.37(m,4H),7.07(d,J=2.1Hz,1H),7.05 -

[0160] 6.97(m,3H).

[0161] Synthesis of Compound CPD78:

[0162] Synthesis Route:

[0163]

[0164] Synthesis of Compound CPD78-2:

[0165] Referring to the synthesis and purification methods of Compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD78-2 as a white solid (30.54 g, mass fraction purity: 98.44%, yield: 77.12%). The mass spectrometry characterization result: 329.12 (M+H).

[0166] Synthesis of Compound CPD78-3:

[0167] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD78-3 as a white solid (27.09 g, mass fraction purity: 99.66%, yield: 76.36%). The mass spectrometry characterization result: 357.22 (M+H).

[0168] Synthesis of Compound CPD78-4:

[0169] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD78-4 as a white solid (23.12 g, yield: 93.93%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0170] Synthesis of Compound CPD78-5:

[0171] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD78-5 as a white solid (18.08 g, mass fraction purity: 99.65%, yield: 40.20%). The mass spectrometry characterization result: 353.06 (M+H).

[0172] Synthesis of Compound CPD78-8:

[0173] Referring to the synthesis and purification methods of Compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD78-8 as a white solid (23.11 g, mass fraction purity: 99.60%, yield: 76.44%). The mass spectrometry characterization result: 337.13 (M+H).

[0174] Synthesis of Compound CPD78:

[0175] With reference to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD78 as a light yellow solid (16.76 g, mass fraction purity: 99.92%, yield: 76.22%). After sublimation purification of 16.76 g of the light yellow solid crude CPD78, sublimation-pure CPD78 (14.21 g, mass fraction purity: 99.92%, yield: 84.78%) was obtained. The mass spectrometry characterization result: 653.21 (M+H).

[0176] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.33 - 8.26 (m, 1H), 8.21 (dd, J = 17.5, 8.8 Hz, 2H), 8.13 - 8.03 (m, 2H), 8.02 - 7.79 (m, 10H), 7.55 - 7.46 (m, 3H), 7.46 - 7.39 (m, 3H), 7.34 - 7.24 (m, 3H), 7.15 - 7.06 (m, 3H), 6.98 - 6.96 (m, 1H).

[0177] Synthesis of compound CPD94:

[0178] Synthesis route:

[0179]

[0180] Synthesis of compound CPD94-3:

[0181] With reference to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD94-3 as a white solid (19.88 g, mass fraction purity: 99.57%, yield: 78.08%). The mass spectrometry characterization result: 357.04 (M+H).

[0182] Synthesis of compound CPD94-4:

[0183] With reference to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD94-4 (25.58 g, yield: 94.35%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0184] Synthesis of compound CPD94-5:

[0185] For the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD94-5 as a white solid (20.01 g, mass fraction purity: 99.74%, yield: 78.63%). The mass spectrometry characterization result is: 353.06 (M+H).

[0186] Synthesis of compound CPD94:

[0187] Referring to the synthesis and purification method of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD94 as a yellow solid (17.77 g, mass fraction purity: 99.94%, yield: 71.06%). After sublimation purification of 17.77 g of the crude yellow solid CPD94, sublimation-pure CPD94 (15.02 g, purity: 99.94%, yield: 84.52%) was obtained. The mass spectrometry characterization result is: 678.22 (M+H).

[0188] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.47 (dd, J = 7.6, 1.4 Hz, 1H), 8.16 - 8.10 (m, 1H), 8.10 - 8.02 (m, 4H), 7.93 - 7.86 (m, 3H), 7.82 (d, J = 7.1 Hz, 1H), 7.61 - 7.34 (m, 15H), 7.32 - 7.30 (m, 1H), 7.17 (dd, J = 7.2, 2.1 Hz, 1H), 7.03 - 6.97 (m, 2H), 1.74 (s, 6H).

[0189] Synthesis of compound CPD103:

[0190] Synthesis route:

[0191]

[0192] Synthesis of compound CPD103-2:

[0193] Referring to the synthesis and purification method of compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD103-2 as a white solid (32.65 g, mass fraction purity: 98.78%, yield: 79.05%). The mass spectrometry characterization result is: 345.02 (M+H).

[0194] Synthesis of compound CPD103-3:

[0195] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD103-3 as a white solid (29.63 g, mass fraction purity: 99.75%, yield: 76.03%). The mass spectrometry characterization result is 373.04 (M+H).

[0196] Synthesis of compound CPD103-4:

[0197] Referring to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD103-4 as a white solid (25.63 g, yield: 95.39%). The mass spectrometry characterization result is 401.14 (M+H). The obtained compound is directly used in the next step without purification.

[0198] Synthesis of compound CPD103-5:

[0199] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD103-5 as a white solid (20.00 g, mass fraction purity: 99.76%, yield: 78.80%). The mass spectrometry characterization result is 369.02 (M+H).

[0200] Synthesis of compound CPD103-8:

[0201] Referring to the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD103-8 as a white solid (24.23 g, mass fraction purity: 99.86%, yield: 75.63%). The mass spectrometry characterization result is 412.22 (M+H).

[0202] Synthesis of compound CPD103:

[0203] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD103 as a light yellow solid (14.33 g, mass fraction purity: 99.95%, yield: 74.63%). After sublimation purification of 14.33 g of the light yellow solid CPD103 crude product, sublimation-pure CPD103 (12.01 g, mass fraction purity: 99.95%, yield: 83.81) is obtained. The mass spectrometry characterization result is 744.24 (M+H).

[0204] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.21 (d, J = 7.1 Hz, 1H), 8.10 - 8.03 (m, 3H), 8.03 - 7.95 (m, 2H), 7.93 (d, J = 2.2 Hz, 1H), 7.91 - 7.86 (m, 3H), 7.86 - 7.81 (m, 2H), 7.76 - 7.68 (m, 2H), 7.67 - 7.60 (m, 1H), 7.60 - 7.55 (m, 2H), 7.55 - 7.47 (m, 6H), 7.47 - 7.37 (m, 6H), 7.31 (dd, J = 7.6, 2.1 Hz, 1H), 7.16 (dd, J = 7.0, 2.2 Hz, 1H), 6.97 - 6.91 (m, 2H).

[0205] Synthesis of Compound CPD123:

[0206] Synthesis Route:

[0207]

[0208] Synthesis of Compound CPD123:

[0209] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD123 as a light yellow solid (12.11 g, mass fraction purity: 99.95%, yield: 76.87%). After sublimation purification of 12.11 g of the light yellow solid crude product of CPD123, sublimation-pure CPD123 (9.87 g, mass fraction purity: 99.95%, yield: 81.51%) was obtained. The mass spectrometry characterization result: 576.32 (M + H).

[0210] Nuclear magnetic resonance characterization results: 1 1H NMR (400 MHz, CDCl3) δ 8.33 - 8.26 (m, 1H), 8.21 (dd, J = 17.5, 8.8 Hz, 2H), 8.13 - 8.03 (m, 2H), 7.99 - 7.93 (m, 2H), 7.93 - 7.82 (m, 2H), 7.55 - 7.47 (m, 2H), 7.43 (d, J = 7.5 Hz, 1H), 7.32 (dd, J = 7.6, 2.1 Hz, 1H).

[0211] Synthesis of Compound CPD132:

[0212] Synthesis Route:

[0213]

[0214] Synthesis of Compound CPD132-2:

[0215] For the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD132-2 as a white solid (23.22 g, mass fraction purity: 99.51%, yield: 75.20%). The mass spectrometry characterization result is 357.04 (M+H).

[0216] Synthesis of compound CPD132-3:

[0217] Referring to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD132-3 as a white solid (21.25 g, yield: 95.05%). The mass spectrometry characterization result is 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0218] Synthesis of compound CPD132-4:

[0219] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD132-4 as a white solid (22.12 g, mass fraction purity: 99.83%, yield: 77.05%). The mass spectrometry characterization result is 353.06 (M+H).

[0220] Synthesis of compound CPD132:

[0221] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD132 as a yellow solid (15.44 g, mass fraction purity: 99.94%, yield: 73.63%). After sublimation purification of 15.44 g of the crude yellow solid CPD132, sublimation-pure CPD132 (12.50 g, purity: 99.94%, yield: 80.96%) is obtained. The mass spectrometry characterization result is 618.24 (M+H).

[0222] Nuclear magnetic resonance characterization result: 1 H NMR(400MHz,CDCl3)δ8.79(dd,J=7.5,1.4Hz,1H),8.62-8.56(m,1H),8.35-8.28(m,1H),8.04(d,J=8.0Hz,1H),7.94-7.86(m,3H),7.61-7.46(m,8H),7.45-

[0223] 7.37(m,4H),7.18-7.12(m,3H),7.03-6.97(m,2H),6.93-6.88(m,2H),1.31(s,9H).

[0224] Synthesis of Compound CPD150:

[0225] Synthesis Route:

[0226]

[0227] Synthesis of Compound CPD150-2:

[0228] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD150-2 as a white solid (24.54 g, mass fraction purity: 99.58%, yield: 75.98%). The mass spectrometry characterization result: 357.04 (M+H).

[0229] Synthesis of Compound CPD150-3:

[0230] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD150-3 as a white solid (23.84 g, yield: 95.96%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0231] Synthesis of Compound CPD150-4:

[0232] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD150-4 as a white solid (20.52 g, mass fraction purity: 99.63%, yield: 75.82%). The mass spectrometry characterization result: 353.06 (M+H).

[0233] Synthesis of Compound CPD150-6:

[0234] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD150-6 as a white solid (25.63 g, mass fraction purity: 99.87%, yield: 74.25%). The mass spectrometry characterization result: 320.12 (M+H).

[0235] Synthesis of Compound CPD150:

[0236] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD150 as a yellow solid (17.63 g, mass fraction purity: 99.94%, yield: 77.06%). After sublimation purification of 17.63 g of the crude yellow solid CPD150, sublimation-pure CPD150 (14.76 g, mass fraction purity: 99.94%, yield: 83.72%) was obtained. The mass spectrometry characterization result: 636.22 (M+H).

[0237] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 9.2 Hz, 1H), 8.57 (d, J = 9.3 Hz, 1H), 8.50 - 8.43 (m, 1H), 8.37 (d, J = 8.3 Hz, 1H), 8.33 - 8.27 (m, 1H), 8.25 (d, J = 8.1 Hz, 1H), 8.01 - 7.95 (m, 3H), 7.92 - 7.87 (m, 5H), 7.82 (d, J = 7.2 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.56 - 7.47 (m, 4H), 7.37 (d, J = 7.1 Hz, 1H), 7.32 - 7.24 (m, 2H), 7.17 - 7.06 (m, 5H), 6.89 (dd, J = 7.5, 2.2 Hz, 1H).

[0238] Synthesis of compound CPD174:

[0239] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD174 as a light yellow solid (13.15 g, mass fraction purity: 99.93%, yield: 75.32%). After sublimation purification of 13.15 g of the crude light yellow solid CPD174, sublimation-pure CPD174 (10.05 g, purity: 99.95%, yield: 76.43%) was obtained. The mass spectrometry characterization result: 728.24 (M+H).

[0240] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.33 - 8.26 (m, 1H), 8.22 (d, J = 2.3 Hz, 1H), 8.15 (dd, J = 9.0, 2.4 Hz, 1H), 8.03 - 7.91 (m, 5H), 7.91 - 7.86 (m, 2H), 7.83 (d, J = 2.1 Hz, 1H), 7.76 - 7.68 (m, 2H), 7.67 - 7.60 (m, 1H), 7.60 - 7.55 (m, 2H), 7.55 - 7.47 (m, 6H), 7.47 - 7.37 (m, 7H), 7.31 (dd, J = 7.5, 2.2 Hz, 2H), 6.97 - 6.91 (m, 2H).

[0241] Synthesis of Compound CPD181:

[0242] Synthetic Route:

[0243]

[0244] Synthesis of Compound CPD181 - 2:

[0245] Referring to the synthesis and purification methods of Compound CPD2 - 3, only the corresponding raw materials need to be changed to obtain the target compound CPD181 - 2 as a white solid (25.63 g, mass fraction purity: 98.83%, yield: 75.82%). Mass spectrometry characterization result: 329.12 (M + H).

[0246] Synthesis of Compound CPD181 - 3:

[0247] Referring to the synthesis and purification methods of Compound CPD2 - 5, only the corresponding raw materials need to be changed to obtain the target compound CPD181 - 3 as a white solid (23.55 g, mass fraction purity: 99.48%, yield: 75.99%). Mass spectrometry characterization result: 357.22 (M + H).

[0248] Synthesis of Compound CPD181 - 4:

[0249] Referring to the synthesis and purification methods of Compound CPD2 - 7, only the corresponding raw materials need to be changed to obtain the target compound CPD181 - 4 (20.61 g, yield: 95.46%). Mass spectrometry characterization result: 385.04 (M + H). The obtained compound is directly used in the next step without purification.

[0250] Synthesis of Compound CPD181 - 5:

[0251] With reference to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD181-5 as a white solid (16.85 g, mass fraction purity: 99.80%, yield: 74.63%). The mass spectrometry characterization result is: 353.06 (M+H).

[0252] Synthesis of compound CPD181:

[0253] With reference to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD181 as a light yellow solid (15.06 g, mass fraction purity: 99.94%, yield: 77.04%). After sublimation purification of 15.06 g of the crude light yellow solid CPD181, sublimation-pure CPD181 (11.82 g, mass fraction purity: 99.94%, yield: 78.49%) was obtained. The mass spectrometry characterization result is: 653.22 (M+H).

[0254] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.35 - 8.28 (m, 1H), 8.10 (d, J = 8.1 Hz, 1H), 8.05 - 8.00 (m, 2H), 8.00 - 7.86 (m, 8H), 7.86 - 7.79 (m, 2H), 7.76 (d, J = 8.1 Hz, 1H), 7.55 - 7.39 (m, 6H), 7.34 - 7.24 (m, 3H), 7.17 - 7.12 (m, 2H), 7.12 - 7.08 (m, 1H), 6.98 - 6.96 (m, 1H).

[0255] Synthesis of compound CPD209:

[0256] Synthesis route:

[0257]

[0258] Synthesis of compound CPD209-2:

[0259] With reference to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD209-2 as a white solid (28.78 g, mass fraction purity: 99.74%, yield: 76.11%). The mass spectrometry characterization result is: 357.24 (M+H).

[0260] Synthesis of compound CPD209-3:

[0261] For the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed. The target compound CPD209-3 (22.65 g, yield: 95.63%) is obtained as a white solid. The mass spectrometry characterization result is: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0262] Synthesis of compound CPD209-4:

[0263] For the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed. The target compound CPD209-4 (15.63 g, mass fraction purity: 99.22%, yield: 40.96%) is obtained as a white solid. The mass spectrometry characterization result is: 353.06 (M+H).

[0264] Synthesis of compound CPD209:

[0265] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed. The target compound CPD209 (14.55 g, mass fraction purity: 99.93%, yield: 75.66%) is obtained as a light yellow solid. After sublimation purification of 14.55 g of crude CPD209, sublimation-pure CPD209 (11.33 g, mass fraction purity: 99.94%, yield: 77.87%) is obtained. The mass spectrometry characterization result is: 652.22 (M+H).

[0266] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.64 (d, J = 9.3 Hz, 1H), 8.46 - 8.41 (m, 1H), 8.38 (d, J = 9.6 Hz, 1H), 8.21 (d, J = 1.1 Hz, 2H), 8.04 (d, J = 9.5 Hz, 1H), 8.01 - 7.94 (m, 3H), 7.91 - 7.86 (m, 1H), 7.83 (d, J = 2.1 Hz, 1H), 7.66 - 7.61 (m, 1H), 7.60 - 7.55 (m, 2H), 7.55 - 7.49 (m, 4H), 7.46 - 7.37 (m, 7H), 7.31 (dd, J = 7.6, 2.1 Hz, 2H), 7.02 - 6.97 (m, 2H).

[0267] Synthesis of compound CPD224:

[0268] Synthesis route:

[0269]

[0270] Synthesis of compound CPD224-2:

[0271] Referring to the synthesis and purification method of reference compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD224-2 as a white solid (35.09 g, mass fraction purity: 98.06%, yield: 78.45%). The mass spectrometry characterization result is: 329.12 (M+H).

[0272] Synthesis of compound CPD224-3:

[0273] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD224-3 as a white solid (32.06 g, mass fraction purity: 99.87%, yield: 75.02%). The mass spectrometry characterization result is: 357.04 (M+H).

[0274] Synthesis of compound CPD224-4:

[0275] Referring to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD224-4 (14.32, mass fraction yield: 94.33%). The mass spectrometry characterization result is: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0276] Synthesis of compound CPD224-5:

[0277] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD224-5 as a white solid (17.07 g, mass fraction purity: 99.54%, yield: 40.63%). The mass spectrometry characterization result is: 353.06 (M+H).

[0278] Synthesis of compound CPD224:

[0279] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD224 as a light yellow solid (13.11 g, mass fraction purity: 99.93%, yield: 72.74%). After sublimation purification of 13.11 g of the light yellow solid CPD224 crude product, sublimation-pure CPD224 (10.05 g, mass fraction purity: 99.93%, yield: 76.66%) is obtained. The mass spectrometry characterization result is: 724.26 (M+H).

[0280] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.65 - 8.55 (m, 3H), 8.49 - 8.42 (m, 1H), 8.10 (d, J = 2.1 Hz, 1H), 8.03 (dd, J = 6.8, 1.4 Hz, 3H), 8.02 - 7.93 (m, 7H), 7.93 - 7.85 (m, 2H), 7.56 - 7.44 (m, 8H), 7.42 (d, J = 7.6 Hz, 1H), 7.33 - 7.23 (m, 3H), 7.21 - 7.07 (m, 4H).

[0281] Synthesis of Compound CPD231:

[0282] Synthetic Route:

[0283]

[0284] Synthesis of Compound CPD231-1:

[0285] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD231-1 as a white solid (30.68 g, mass fraction purity: 99.78%, yield: 74.62%). The mass spectrometry characterization results: 357.24 (M + H).

[0286] Synthesis of Compound CPD231-2:

[0287] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD231-2 as a white solid (24.55 g, yield: 96.33%). The mass spectrometry characterization results: 385.04 (M + H). The obtained compound was directly used in the next step without purification.

[0288] Synthesis of Compound CPD231-3:

[0289] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD231-3 as a white solid (17.99 g, mass fraction purity: 99.86%, yield: 78.63%). The mass spectrometry characterization results: 353.06 (M + H).

[0290] Synthesis of Compound CPD231:

[0291] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD231 as a light yellow solid (17.11 g, mass fraction purity: 99.95%, yield: 78.74%). After sublimation purification of 17.11 g of crude CPD231, sublimation-pure CPD231 (13.75 g, mass fraction purity: 99.95%, yield: 80.37%) was obtained. The mass spectrometry characterization result: 562.24 (M+H).

[0292] Figure 1 For the 1 1H NMR spectrum of the compound CPD231 of the present invention.

[0293] The nuclear magnetic characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.75 - 8.71 (m, 2H), 8.66 (d, J = 8.9 Hz, 1H), 8.42 (d, J = 2.2 Hz, 1H), 8.03 (dd, J = 18.4, 8.8 Hz, 2H), 7.87 (d, J = 8.7 Hz, 1H), 7.75 - 7.52 (m, 8H), 7.47 (t, J = 7.7 Hz, 2H), 7.43 - 7.30 (m, 5H), 7.26 - 7.19 (m, 4H), 7.12 - 7.11 (m, 1H).

[0294] Synthesis of compound CPD249:

[0295] Synthesis route:

[0296]

[0297] Synthesis of compound CPD249:

[0298] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD249 as a light yellow solid (15.00 g, mass fraction purity: 99.95%, yield: 73.96%). After sublimation purification of 15.00 g of the light yellow solid crude CPD249, sublimation-pure CPD249 (11.33 g, mass fraction purity: 99.95%, yield: 75.54%) was obtained. The mass spectrometry characterization result: 652.24 (M+H).

[0299] The nuclear magnetic characterization result: 11H NMR (400 MHz, CDCl3) δ 8.62 - 8.59 (m, 2H), 8.47 - 8.39 (m, 1H), 8.33 - 8.28 (m, 1H), 8.08 (d, J = 2.1 Hz, 1H), 8.03 - 7.96 (m, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.91 - 7.85 (m, 2H), 7.83 (d, J = 2.1 Hz, 1H), 7.67 - 7.59 (m, 1H), 7.59 - 7.57 (m, 1H), 7.57 - 7.47 (m, 5H), 7.47 - 7.37 (m, 7H), 7.35 - 7.28 (m, 3H), 7.03 - 6.97 (m, 2H).

[0300] Synthesis of Compound CPD265:

[0301] Synthetic Route:

[0302]

[0303] Synthesis of Compound CPD265:

[0304] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD265 as a light yellow solid (10.33 g, mass fraction purity: 99.94%, yield: 78.63%). After sublimation purification of 10.33 g of the light yellow solid crude CPD265, sublimation-pure CPD265 (8.13 g, mass fraction purity: 99.94%, yield: 78.71%) was obtained. The mass spectrometry characterization result: 668.34 (M + H).

[0305] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 - 8.39 (m, 1H), 8.33 - 8.28 (m, 1H), 8.06 (d, J = 2.2 Hz, 1H), 7.96 - 7.90 (m, 2H), 7.89 - 7.86 (m, 1H), 7.56 -

[0306] 7.47 (m, 2H), 7.42 (d, J = 7.5 Hz, 1H), 7.33 - 7.31 (m, 2H).

[0307] Synthesis of Compound CPD280:

[0308] Synthetic Route:

[0309]

[0310] Synthesis of Compound CPD280-1:

[0311] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD280-1 as a white solid (32.63 g, mass fraction purity: 99.69%, yield: 745.69%). The mass spectrometry characterization result: 357.24 (M+H).

[0312] Synthesis of compound CPD280-2:

[0313] Referring to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD280-2 as a white solid (27.96 g, yield: 94.12%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0314] Synthesis of compound CPD280-3:

[0315] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD280-3 as a white solid (21.21 g, mass fraction purity: 99.59%, yield: 74.63%). The mass spectrometry characterization result: 353.06 (M+H).

[0316] Synthesis of compound CPD280:

[0317] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD280 as a light yellow solid (16.06 g, mass fraction purity: 99.95%, yield: 74.44%). After sublimation purification of 16.06 g of the light yellow solid CPD280 crude product, sublimation-pure CPD280 (12.90 g, mass fraction purity: 99.95%, yield: 80.33%) is obtained. The mass spectrometry characterization result: 712.22 (M+H).

[0318] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.64 (d, J = 8.9 Hz, 1H), 8.47 - 8.39 (m, 1H), 8.34 - 8.24 (m, 2H), 8.19 - 8.15 (m, 3H), 8.08 (dd, J = 17.6, 7.8 Hz, 2H), 8.01 - 7.96 (m, 3H), 7.94 (d, J = 2.0 Hz, 1H), 7.92 - 7.85 (m, 1H), 7.66 (d, J = 8.0 Hz, 1H), 7.61 - 7.57 (m, 1H), 7.57 - 7.47 (m, 9H), 7.46 - 7.37 (m, 4H), 7.32 - 7.26 (m, 2H), 7.03 - 6.97 (m, 2H).

[0319] Synthesis of Compound CPD289:

[0320] Synthetic Route:

[0321]

[0322] Synthesis of Compound CPD289 - 2:

[0323] Referring to the synthesis and purification methods of Compound CPD26 - 3, only the corresponding raw materials need to be changed to obtain the target compound CPD289 - 2 as a white solid (20.06 g, mass fraction purity: 99.87%, yield: 74.63%). The mass spectrometry characterization result: 356.23 (M + H).

[0324] Synthesis of Compound CPD289 - 3:

[0325] Referring to the synthesis and purification methods of Compound CPD2 - 8, only the corresponding raw materials need to be changed to obtain the target compound CPD289 - 3 as a white solid (10.05 g, mass fraction purity: 99.43%, yield: 39.85%). The mass spectrometry characterization result: 353.06 (M + H).

[0326] Synthesis of Compound CPD289:

[0327] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD289 as a light yellow solid (10.96 g, mass fraction purity: 99.93%, yield: 78.65%). After sublimation purification of 10.96 g of the light yellow solid CPD289 crude product, sublimation - pure CPD289 (8.88 g, mass fraction purity: 99.93%, yield: 81.03%) was obtained. The mass spectrometry characterization result: 672.32 (M + H).

[0328] Nuclear Magnetic Resonance Characterization Results: 11H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 9.1, 2.3 Hz, 2H), 8.48 - 8.44 (m, 1H), 8.21 (d, J = 2.3 Hz, 1H), 8.17 (dd, J = 9.0, 2.3 Hz, 1H), 8.00 (d, J = 2.2 Hz, 1H), 7.96 (d, J = 9.3 Hz, 1H), 7.91 - 7.87 (m, 1H), 7.78 (s, 1H), 7.58 - 7.56 (m, 2H), 7.55 - 7.48 (m, 4H), 7.44 - 7.38 (m, 4H), 7.31 (dd, J = 7.5, 2.2 Hz, 1H), 7.13 (d, J = 6.6 Hz, 1H), 7.05 - 6.96 (m, 4H), 2.13 - 1.90 (m, 4H), 1.33 (s, 12H).

[0329] Synthesis of Compound CPD305:

[0330] Synthesis Route:

[0331]

[0332] Synthesis of Compound CPD305 - 3:

[0333] Referring to the synthesis and purification methods of Compound CPD26 - 3, only the corresponding raw materials need to be changed to obtain the target compound CPD305 - 3 as a white solid (25.63 g, mass fraction purity: 99.80%, yield: 75.44%). The mass spectrometry characterization result: 500.20 (M + H).

[0334] Synthesis of Compound CPD305 - 4:

[0335] Referring to the synthesis and purification methods of Compound CPD2 - 8, only the corresponding raw materials need to be changed to obtain the target compound CPD305 - 4 as a white solid (22.44 g, mass fraction purity: 99.53%, yield: 38.43%). The mass spectrometry characterization result: 353.06 (M + H).

[0336] Synthesis of Compound CPD305:

[0337] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD305 as a light yellow solid (17.89 g, mass fraction purity: 99.94%, yield: 74.85%). After sublimation purification of 17.89 g of the crude CPD305, sublimation - pure CPD305 (14.88 g, mass fraction purity: 99.94%, yield: 83.18%) was obtained. The mass spectrometry characterization result: 816.28 (M + H).

[0338] Nuclear magnetic resonance characterization results: 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 8.2 Hz, 1H), 8.62 (d, J = 9.3 Hz, 1H), 8.50 - 8.43 (m, 1H), 8.24 (d, J = 2.1 Hz, 1H), 8.11 - 8.03 (m, 3H), 7.99 - 7.92 (m, 2H), 7.92 - 7.85 (m, 1H), 7.76 (d, J = 7.1 Hz, 1H), 7.70 - 7.63 (m, 3H), 7.60 (dd, J = 8.0, 1.3 Hz, 1H), 7.56 - 7.22 (m, 19H), 7.14 - 7.06 (m, 2H), 7.03 (dd, J = 7.0, 1.4 Hz, 1H).

[0339] Synthesis of compound CPD315:

[0340] Synthesis route:

[0341]

[0342] Synthesis of compound CPD315 - 2:

[0343] Referring to the synthesis and purification methods of compound CPD26 - 3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound CPD315 - 2 (26.52 g, mass fraction purity: 99.85%, yield: 87.52%). Mass spectrometry characterization results: 363.14 (M + H).

[0344] Synthesis of compound CPD315:

[0345] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the light yellow solid as the target compound CPD315 (18.08 g, mass fraction purity: 99.94%, yield: 76.66%). After sublimation purification of 18.08 g of the light yellow solid CPD315 crude product, sublimation - pure CPD315 (14.76 g, mass fraction purity: 99.95%, yield: 81.64%) was obtained. Mass spectrometry characterization results: 679.24 (M + H).

[0346] Nuclear magnetic resonance characterization results: 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 8.2 Hz, 1H), 8.62 (d, J = 9.3 Hz, 1H), 8.50 - 8.43 (m, 1H), 8.08 - 8.03 (m, 2H), 8.00 (d, J = 7.1 Hz, 1H), 7.98 - 7.86 (m, 5H), 7.62 -

[0347] 7.55 (m, 2H), 7.55 - 7.46 (m, 5H), 7.46 - 7.38 (m, 6H), 7.35 - 7.28 (m, 2H), 7.23 (d, J = 2.1 Hz, 1H), 7.20 (dd, J = 7.1, 2.2 Hz, 1H), 7.03 - 6.97 (m, 2H).

[0348] Synthesis of compound CPD340:

[0349] Synthesis route:

[0350]

[0351] Synthesis of compound CPD340-2:

[0352] Referring to the synthesis and purification methods of compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD340-2 as a white solid (20.20 g, mass fraction purity: 99.52%, yield: 77.74%). The mass spectrometry characterization result: 357.22 (M+H).

[0353] Synthesis of compound CPD340-3:

[0354] Referring to the synthesis and purification methods of compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD340-3 as a white solid (15.86 g, yield: 94.63%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0355] Synthesis of compound CPD340-4:

[0356] Referring to the synthesis and purification methods of compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD340-4 as a white solid (14.36 g, mass fraction purity: 99.76%, yield: 76.33%). The mass spectrometry characterization result: 353.06 (M+H).

[0357] Synthesis of compound CPD340-5:

[0358] CPD340-4 (13.00 g, 36.85 mmol), CPD2-2 (11.23 g, 44.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.74 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.71 g, 1.48 mmol), potassium acetate (5.45 g, 55.28 mmol), and 1,4-dioxane (200 ml) were added to a 500-ml three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times, and then heated to 100 °C for 2 h. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the eluent), and the raw material CPD340-4 was completely consumed.

[0359] The temperature was cooled to 60 °C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (500 ml) was added, and the mixture was washed three times with deionized water (300 ml × 2). After liquid separation, the sample was mixed with silica gel and loaded onto a column by dry method, and silica gel column chromatography purification was carried out (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:12 as the eluent). After elution, the mixture was concentrated under reduced pressure at 70 °C for 1.5 h to obtain a white solid CPD340-5 (12.37 g, mass fraction purity: 98.08%, yield: 75.55%). The mass spectrometry characterization result was: 445.20 (M+H).

[0360] Synthesis of compound CPD340-7:

[0361] Referring to the synthesis and purification methods of compound CPD2-5, only the corresponding raw materials need to be changed to obtain a white solid as the target compound CPD340-7 (10.23 g, mass fraction purity: 98.88%, yield: 78.96%). The mass spectrometry characterization result was: 523.04 (M+H).

[0362] Synthesis of compound CPD340:

[0363] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain a light yellow solid as the target compound CPD340 (10.28 g, mass fraction purity: 99.95%, yield: 78.26%). After sublimation purification of 10.28 g of the light yellow solid CPD340 crude product, sublimation-pure CPD340 (8.02 g, mass fraction purity: 99.95%, yield: 78.02%) was obtained. The mass spectrometry characterization result was: 764.22 (M+H).

[0364] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.61 - 8.59 (m, 2H), 8.29 - 8.27 (m, 1H), 8.16 - 8.14 (m, 1H), 8.06 - 8.01 (m, 2H), 7.96 - 7.86 (m, 3H), 7.80 (d, J = 7.7 Hz, 1H), 7.69 (dd, J = 7.2, 2.5 Hz, 1H), 7.64 - 7.45 (m, 14H), 7.45 - 7.36 (m, 7H), 7.32 (d, J = 7.6 Hz, 1H), 6.96 - 6.91 (m, 4H).

[0365] Synthesis of Compound CPD351:

[0366] Synthetic Route:

[0367]

[0368] Synthesis of Compound CPD351-2:

[0369] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD351-2 as a white solid (18.88 g, mass fraction purity: 99.56%, yield: 74.98%). The mass spectrometry characterization result: 357.22 (M+H).

[0370] Synthesis of Compound CPD351-3:

[0371] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD351-3 as a white solid (14.84 g, yield: 95.10%). The mass spectrometry characterization result: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0372] Synthesis of Compound CPD351-4:

[0373] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD351-4 as a white solid (12.96 g, mass fraction purity: 99.64%, yield: 74.39%). The mass spectrometry characterization result: 353.06 (M+H).

[0374] Synthesis of Compound CPD351:

[0375] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD351 as a light yellow solid (12.05 g, mass fraction purity: 99.93%, yield: 76.85%). After sublimation purification of 12.05 g of the crude light yellow solid CPD351, sublimation-pure CPD351 (9.33 g, mass fraction purity: 99.95%, yield: 77.43%) was obtained. The mass spectrometry characterization result: 644.24 (M+H).

[0376] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.52 - 8.45 (m, 2H), 8.34 - 8.27 (m, 2H), 8.08 (d, J = 2.3 Hz, 1H), 7.98 - 7.92 (m, 2H), 7.61 - 7.47 (m, 8H), 7.46 - 7.38 (m, 4H), 7.31 (dd, J = 7.5, 2.2 Hz, 1H), 7.09 - 6.97 (m, 6H), 2.56 - 2.48 (m, 1H), 1.08 - 1.73 (m, 2H), 1.66 - 1.53 (m, 2H), 1.53 - 1.41 (m, 6H).

[0377] Synthesis of compound CPD358:

[0378] Synthesis route:

[0379]

[0380] Synthesis of compound CPD358:

[0381] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD358 as a light yellow solid (15.55 g, mass fraction purity: 99.95%, yield: 77.06%). After sublimation purification of 15.55 g of the crude light yellow solid CPD358, sublimation-pure CPD358 (13.11 g, mass fraction purity: 99.95%, yield: 84.31%) was obtained. The mass spectrometry characterization result: 738.24 (M+H).

[0382] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.17 (d, J = 9.1 Hz, 1H), 8.08 (d, J = 2.1 Hz, 1H), 8.05 - 8.03 (m, 3H), 7.97 - 7.91 (m, 4H), 7.91 - 7.81 (m, 7H), 7.73 - 7.71 (m, 2H), 7.59 - 7.54 (m, 4H), 7.54 - 7.48 (m, 6H), 7.43 (d, J = 7.6 Hz, 1H), 7.36 - 7.28 (m, 2H), 7.02 - 6.97 (m, 4H).

[0383] Synthesis of Compound CPD379:

[0384] Synthetic Route:

[0385]

[0386]

[0387] Synthesis of Compound CPD379-2:

[0388] Referring to the synthesis and purification methods of Compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD379-2 as a white solid (45.33 g, mass fraction purity: 98.77%, yield: 75.33%). The mass spectrometry characterization result: 322.12 (M + H).

[0389] Synthesis of Compound CPD379-4:

[0390] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD379-4 as a white solid (35.44 g, mass fraction purity: 99.52%, yield: 72.11%). The mass spectrometry characterization result: 334.04 (M + H).

[0391] Synthesis of Compound CPD379-5:

[0392] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD379-5 as a white solid (24.63 g, yield: 95.45%). The mass spectrometry characterization result: 362.09 (M + H). The obtained compound is directly used in the next step without purification.

[0393] Synthesis of Compound CPD379-6:

[0394] For the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed, and the target compound CPD379-6 (22.41 g, mass fraction purity: 99.83%, yield: 74.15%) is obtained as a white solid. The mass spectrometry characterization result: 330.02 (M+H).

[0395] Synthesis of compound CPD379-7:

[0396] For the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed, and the target compound CPD379-7 (18.77 g, mass fraction purity: 99.66%, yield: 78.54%) is obtained as a white solid. The mass spectrometry characterization result: 463.14 (M+H).

[0397] Synthesis of compound CPD379:

[0398] For the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed, and the target compound CPD379 (18.09 g, mass fraction purity: 99.93%, yield: 75.63%) is obtained as a light yellow solid. After sublimation purification of 18.09 g of the light yellow solid crude CPD379, sublimation-pure CPD379 (14.85 g, purity: 99.92%, yield: 82.09%) is obtained. The mass spectrometry characterization result: 779.24 (M+H).

[0399] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.34 (d, J = 2.1 Hz, 1H), 8.17 (d, J = 9.1 Hz, 1H), 8.12 - 8.07 (m, 2H), 8.07 - 8.02 (m, 2H), 7.99 (d, J = 7.4 Hz, 1H), 7.96 - 7.90 (m, 4H), 7.90 - 7.87 (m, 2H), 7.86 - 7.84 (m, 2H), 7.62 - 7.46 (m, 8H), 7.46 - 7.38 (m, 6H), 7.34 - 7.29 (m, 2H), 7.03 - 6.98 (m, 2H), 6.89 (dd, J = 7.5, 2.1 Hz, 1H).

[0400] Synthesis of compound CPD395:

[0401] Synthesis route:

[0402]

[0403] Synthesis of compound CPD395-2:

[0404] Referring to the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD395-2 as a white solid (20.51 g, mass fraction purity: 99.68%, yield: 76.85%). The mass spectrometry characterization result is: 452.22 (M+H).

[0405] Synthesis of compound CPD395:

[0406] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD395 as a light yellow solid (15.33 g, mass fraction purity: 99.95%, yield: 74.52%). After sublimation purification of 15.33 g of the light yellow solid crude product of CPD395, sublimation-pure CPD395 (11.06 g, mass fraction purity: 99.95%, yield: 72.15%) is obtained. The mass spectrometry characterization result is: 768.22 (M+H).

[0407] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.17 (d, J = 9.1 Hz, 1H), 8.14 - 8.12 (m, 1H), 8.08 (d, J = 2.0 Hz, 1H), 8.06 - 8.01 (m, 1H), 8.01 - 7.97 (m, 2H), 7.95 - 7.93 (m, 3H), 7.92 - 7.87 (m, 2H), 7.86 - 7.84 (m, 2H), 7.80 (d, J = 7.1 Hz, 1H), 7.57 - 7.46 (m, 4H), 7.46 - 7.40 (m, 4H), 7.38 (dd, J = 7.2, 2.1 Hz, 1H), 7.35 - 7.27 (m, 5H), 7.24 (d, J = 2.0 Hz, 1H), 7.22 - 7.13 (m, 4H).

[0408] Synthesis of compound CPD414:

[0409] Synthesis route:

[0410]

[0411] Synthesis of compound CPD414-1:

[0412] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD414-1 as a white solid (35.75 g, mass fraction purity: 99.74%, yield: 72.62%). The mass spectrometry characterization result is: 357.06 (M+H).

[0413] Synthesis of compound CPD414-2:

[0414] Referring to the synthesis and purification method of reference compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD414-2 (22.44 g, yield: 94.33%) as a white solid. The mass spectrometry characterization result is: 384.10 (M+H). The obtained compound is directly used in the next step without purification.

[0415] Synthesis of compound CPD414-3:

[0416] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD414-3 (19.74 g, mass fraction purity: 99.78%, yield: 72.52%) as a white solid. The mass spectrometry characterization result is: 353.02 (M+H).

[0417] Synthesis of compound CPD414-4:

[0418] Referring to the synthesis and purification method of reference compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD414-4 (35.49 g, mass fraction purity: 98.06%, yield: 73.62%) as a white solid. The mass spectrometry characterization result is: 322.16 (M+H).

[0419] Synthesis of compound CPD414-6:

[0420] Referring to the synthesis and purification method of reference compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD414-6 (24.63 g, mass fraction purity: 99.62%, yield: 71.63%) as a white solid. The mass spectrometry characterization result is: 363.22 (M+H)

[0421] Synthesis of compound CPD414:

[0422] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD414 (16.05 g, mass fraction purity: 99.94%, yield: 72.96%) as a light yellow solid. After sublimation purification of 16.05 g of the light yellow solid CPD414 crude product, sublimation-pure CPD414 (12.59 g, yield: 78.45%) is obtained. The mass spectrometry characterization result is: 679.20 (M+H).

[0423] Nuclear magnetic resonance characterization result: 11H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.32 - 8.27 (m, 1H), 8.04 - 7.98 (m, 2H), 7.98 - 7.86 (m, 7H), 7.78 (d, J = 2.2 Hz, 1H), 7.66 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 7.8, 2.1 Hz, 1H), 7.59 - 7.54 (m, 2H), 7.53 - 7.46 (m, 3H), 7.46 - 7.39 (m, 3H), 7.34 - 7.25 (m, 3H), 7.19 - 7.07 (m, 3H), 7.03 - 6.97 (m, 2H).

[0424] Synthesis of compound CPD442:

[0425] Synthesis route:

[0426]

[0427] Synthesis of compound CPD442:

[0428] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD442 as a light yellow solid (15.42 g, mass fraction purity: 99.94%, yield: 73.85%). After sublimation purification of 15.42 g of the crude CPD442, sublimation-pure CPD442 (11.86 g, mass fraction purity: 99.92%, yield: 76.92%) was obtained. The mass spectrometry characterization result: 653.21 (M + H).

[0429] Nuclear magnetic resonance characterization result: 1 1H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 - 8.39 (m, 1H), 8.33 - 8.28 (m, 1H), 8.08 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 2.1 Hz, 1H), 7.97 - 7.85 (m, 7H), 7.82 (d, J = 7.3 Hz, 1H), 7.56 - 7.39 (m, 6H), 7.35 - 7.24 (m, 4H), 7.17 - 7.07 (m, 3H), 6.97 (dd, J = 7.5, 2.1 Hz, 1H).

[0430] Synthesis of compound CPD450:

[0431] Synthesis route:

[0432]

[0433] Synthesis of compound CPD450-1:

[0434] Referring to the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD450-1 as a white solid (20.00 g, mass fraction purity: 99.83%, yield: 74.56%). The mass spectrometry characterization result is 539.02 (M+H).

[0435] Synthesis of compound CPD450:

[0436] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD450 as a light yellow solid (16.74 g, mass fraction purity: 99.94%, yield: 73.22%). After sublimation purification of 16.74 g of the light yellow solid CPD450 crude product, sublimation-pure CPD450 (13.05 g, yield: 77.96%) was obtained. The mass spectrometry characterization result is 855.24 (M+H).

[0437] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 - 8.39 (m, 1H), 8.34 (d, J = 2.1 Hz, 1H), 8.33 - 8.28 (m, 1H), 8.11 - 8.06 (m, 2H), 8.04 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 7.4 Hz, 1H), 7.96 - 7.85 (m, 6H), 7.76 - 7.68 (m, 2H), 7.60 - 7.55 (m, 2H), 7.55 - 7.46 (m, 8H), 7.46 - 7.37 (m, 6H), 7.35 - 7.28 (m, 2H), 6.97 - 6.91 (m, 2H), 6.89 (dd, J = 7.5, 2.1 Hz, 1H).

[0438] Synthesis of compound CPD461:

[0439] Synthesis route:

[0440]

[0441] Synthesis of compound CPD461-2:

[0442] Referring to the synthesis and purification method of reference compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD461-2 as a white solid (32.11 g, mass fraction purity: 99.74%, yield: 72.41%). The mass spectrometry characterization result is 404.12 (M+H).

[0443] Synthesis of Compound CPD461:

[0444] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD461 as a light yellow solid (17.77 g, mass fraction purity: 99.93%, yield: 74.96%). After sublimation purification of 17.77 g of the crude CPD461, sublimation-pure CPD461 (13.95 g, mass fraction purity: 99.92%, yield: 78.51%) was obtained. The mass spectrometry characterization result: 720.20 (M+H).

[0445] Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.46 - 8.41 (m, 1H), 8.34 - 8.28 (m, 1H), 8.08 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 7.2 Hz, 2H), 7.97 - 7.86 (m, 7H), 7.56 - 7.47 (m, 4H), 7.47 - 7.40 (m, 5H), 7.35 - 7.29 (m, 2H), 7.26 (d, J = 2.1 Hz, 2H), 7.20 (dd, J = 7.2, 2.1 Hz, 2H).

[0446] Synthesis of Compound CPD468:

[0447] Synthesis route:

[0448]

[0449] Synthesis of Compound CPD468-2:

[0450] Referring to the synthesis and purification methods of Compound CPD26-3, only the corresponding raw materials need to be changed to obtain the target compound CPD468-2 as a white solid (25.74 g, mass fraction purity: 99.69%, yield: 73.52%). The mass spectrometry characterization result: 502.22 (M+H).

[0451] Synthesis of Compound CPD468:

[0452] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD468 as a light yellow solid (15.01 g, mass fraction purity: 99.94%, yield: 73.22%). After sublimation purification of 15.01 g of the light yellow solid crude CPD468, sublimation-pure CPD468 (11.08 g, mass fraction purity: 99.94%, yield: 73.82%) was obtained. The mass spectrometry characterization result: 818.24 (M+H).

[0453] Nuclear magnetic characterization results: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 - 8.40 (m, 2H), 8.33 - 8.28 (m, 1H), 8.16 (d, J = 2.2 Hz, 1H), 8.08 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 7.1 Hz, 1H), 7.98 - 7.83 (m, 9H), 7.56 - 7.47 (m, 5H), 7.47 - 7.40 (m, 3H), 7.38 (dd, J = 7.2, 2.1 Hz, 1H), 7.35 - 7.27 (m, 4H), 7.24 (d, J = 2.1 Hz, 1H), 7.22 - 7.12 (m, 4H).

[0454] Synthesis of compound CPD484:

[0455] Synthesis route:

[0456]

[0457] Synthesis of compound CPD484 - 2:

[0458] Referring to the synthesis and purification methods of compound CPD2 - 3, only the corresponding raw materials need to be changed, and a white solid is obtained as the target compound CPD484 - 2 (25.77 g, mass fraction purity: 98.88%, yield: 74.12%), and the mass spectrometry characterization results: 355.12 (M + H).

[0459] Synthesis of compound CPD484 - 3:

[0460] Referring to the synthesis and purification methods of compound CPD2 - 5, only the corresponding raw materials need to be changed, and a white solid is obtained as the target compound CPD484 - 3 (20.11 g, mass fraction purity: 99.54%, yield: 71.52%), and the mass spectrometry characterization results: 383.02 (M + H).

[0461] Synthesis of compound CPD484 - 4:

[0462] Referring to the synthesis and purification methods of compound CPD2 - 7, only the corresponding raw materials need to be changed, and a white solid is obtained as the target compound CPD484 - 4 (22.53 g, yield: 95.86%), and the mass spectrometry characterization results: 411.14 (M + H). The obtained compound is directly used in the next step without purification.

[0463] Synthesis of compound CPD484 - 5:

[0464] Referring to the synthesis and purification method of reference compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD484-4 as a white solid (18.88 g, mass fraction purity: 99.75%, yield: 75.62%). The mass spectrometry characterization result is: 379.12 (M+H).

[0465] Synthesis of compound CPD484:

[0466] Referring to the synthesis and purification method of reference compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD484 as a light yellow solid (15.55 g, mass fraction purity: 99.94%, yield: 76.22%). After sublimation purification of 15.55 g of crude CPD484, sublimation-pure CPD484 (11.85 g, mass fraction purity: 99.94%, yield: 76.21%) was obtained. The mass spectrometry characterization result is: 588.20 (M+H).

[0467] Nuclear magnetic spectrum characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 9.3 Hz, 1H), 8.50 (d, J = 8.0 Hz, 1H), 8.47 - 8.39 (m, 1H), 8.26 - 8.24 (m, 1H), 8.11 - 8.03 (m, 2H), 7.94 (d, J = 8.1 Hz, 1H), 7.91 -

[0468] 7.85 (m, 1H), 7.77 (d, J = 7.1 Hz, 1H), 7.61 - 7.47 (m, 7H), 7.44 - 7.37 (m, 3H), 7.32 - 7.24 (m, 2H), 7.19 (dd, J = 7.2, 2.1 Hz, 1H), 7.17 - 7.07 (m, 3H), 7.03 - 6.97 (m, 2H), 1.80 (s, 6H).

[0469] Synthesis of compound CPD493:

[0470] Synthesis route:

[0471]

[0472] Synthesis of compound CPD493-2:

[0473] Referring to the synthesis and purification method of reference compound CPD2-3, only the corresponding raw materials need to be changed to obtain the target compound CPD493-2 as a white solid (28.77 g, mass fraction purity: 99.02%, yield: 76.74%). The mass spectrometry characterization result is: 404.14 (M+H).

[0474] Synthesis of Compound CPD493-3:

[0475] Referring to the synthesis and purification methods of Compound CPD2-5, only the corresponding raw materials need to be changed to obtain the target compound CPD493-3 as a white solid (24.85 g, mass fraction purity: 99.67%, yield: 73.62%). The mass spectrometry characterization result is: 432.21 (M+H).

[0476] Synthesis of Compound CPD493-4:

[0477] Referring to the synthesis and purification methods of Compound CPD2-7, only the corresponding raw materials need to be changed to obtain the target compound CPD493-4 as a white solid (23.41 g, yield: 96.66%). The mass spectrometry characterization result is: 460.04 (M+H). The obtained compound is directly used in the next step without purification.

[0478] Synthesis of Compound CPD493-5:

[0479] Referring to the synthesis and purification methods of Compound CPD2-8, only the corresponding raw materials need to be changed to obtain the target compound CPD493-4 as a white solid (20.00 g, mass fraction purity: 99.87%, yield: 77.01%). The mass spectrometry characterization result is: 428.02 (M+H).

[0480] Synthesis of Compound CPD493:

[0481] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD493 as a light yellow solid (18.11 g, mass fraction purity: 99.92%, yield: 75.98%). After sublimation purification of 18.11 g of the light yellow solid CPD493 crude product, sublimation-pure CPD493 (15.00 g, mass fraction purity: 99.93%, yield: 82.83%) is obtained. The mass spectrometry characterization result is: 713.24 (M+H).

[0482] Nuclear magnetic resonance characterization results: 11H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 9.0 Hz, 1H), 8.52 (d, J = 8.0 Hz, 1H), 8.47 - 8.41 (m, 1H), 8.27 - 8.22 (m, 1H), 8.14 - 8.07 (m, 2H), 8.06 - 8.04 (m, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.92 - 7.87 (m, 2H), 7.63 - 7.55 (m, 4H), 7.55 - 7.48 (m, 6H), 7.44 - 7.35 (m, 7H), 7.34 - 7.27 (m, 2H), 7.23 - 7.13 (m, 3H), 7.04 - 6.97 (m, 4H).

[0483] Synthesis of Compound CPD497:

[0484] Synthetic Route:

[0485]

[0486] Synthesis of Compound CPD497 - 2:

[0487] Referring to the synthesis and purification methods of Compound CPD2 - 3, only the corresponding raw materials need to be changed to obtain the target compound CPD497 - 2 as a white solid (20.11 g, mass fraction purity: 99.15%, yield: 74.63%). The mass spectrometry characterization result: 329.10 (M + H).

[0488] Synthesis of Compound CPD497 - 3:

[0489] Referring to the synthesis and purification methods of Compound CPD2 - 5, only the corresponding raw materials need to be changed to obtain the target compound CPD497 - 3 as a white solid (19.78 g, mass fraction purity: 99.62%, yield: 74.44%). The mass spectrometry characterization result: 519.12 (M + H).

[0490] Synthesis of Compound CPD497:

[0491] Referring to the synthesis and purification methods of Compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD497 as a light yellow solid (16.22 g, mass fraction purity: 99.93%, yield: 74.63%). After sublimation purification of 16.22 g of the light yellow solid crude CPD497, sublimation - pure CPD497 (12.86 g, mass fraction purity: 99.93%, yield: 79.29%) was obtained. The mass spectrometry characterization result: 804.26 (M + H).

[0492] Nuclear Magnetic Resonance Characterization Results: 11H NMR (400 MHz, CDCl3) δ 8.17 (dd, J = 9.2, 0.7 Hz, 1H), 8.11 (d, J = 2.4 Hz, 1H), 8.07 - 8.01 (m, 2H), 7.97 - 7.82 (m, 5H), 7.72 (dd, J = 7.3, 2.4 Hz, 2H), 7.61 - 7.56 (m, 4H), 7.56 - 7.53 (m, 2H), 7.53 - 7.47 (m, 5H), 7.46 - 7.37 (m, 8H), 7.32 (d, J = 7.3 Hz, 1H), 7.27 (t, J = 7.0 Hz, 1H), 7.17 (dd, J = 6.9, 1.2 Hz, 1H), 6.97 - 6.91 (m, 4H).

[0493] Application Example: Fabrication of Organic Electroluminescent Devices

[0494] In one embodiment, as Figure 2 shown, Figure 2 is a schematic structural diagram of an organic electroluminescent device. The organic electroluminescent device includes a glass substrate 1, an anode 2 (indium tin oxide), a hole injection layer 3, a first hole transport layer (HTL1) 4, a second hole transport layer (HTL2) 5, a light-emitting layer 6, an electron transport layer (ETL) 7, an electron injection layer 8 (EIL), and a cathode 9 which are stacked.

[0495] A glass substrate with an ITO (anode 2, indium tin oxide, 100 nm) transparent electrode of 50 mm * 50 mm * 1.0 mm was ultrasonically cleaned in ethanol for 10 minutes, then dried at 150 °C and treated with N2 Plasma (plasma gas) for 30 minutes. The washed glass substrate was mounted on the substrate holder of a vacuum evaporation device. Compound NDP - 9 and compound HTM 1 were co-evaporated at a weight ratio of 97:3 to form a hole injection layer with a film thickness of 10 nm. Immediately afterwards, a layer of HTM1 was evaporated to form a film with a thickness of 60 nm as HTL1 (hole transport layer 1). Then, a layer of HTM2 was evaporated on the HTM1 film to form a film with a thickness of 10 nm as HTL2 (hole transport layer 2). Then, on the HTM2 film layer, a light-emitting layer with a film thickness of 40 nm was co-evaporated in the form of a single host or a double host (host material: red light doping material = 97%: 3%, mass fraction), where the host materials of the single host or double host are the compound of the present invention, RH - N, and comparative compounds 1 - 5 respectively. On the light-emitting layer, the ETL (electron transport layer) material and LiQ were co-evaporated at a weight ratio of 50:50 (35 nm) as the electron transport material. Then, LiQ (1 nm) was evaporated on the electron transport material layer as the electron injection material to form an electron injection layer. Then, Mg / Ag (100 nm, mass ratio of 1:9) was co-evaporated as the cathode material to fabricate the organic electroluminescent device.

[0496] The structural formulas of NDP-9, HTM1, HTM2, ETL materials, red-light doping materials, LiQ, RH-N, and Comparative Compounds 1-5 are as follows:

[0497]

[0498] Evaluation:

[0499] The above organic light-emitting devices were subjected to device performance tests. The compounds prepared in the present invention and Comparative Compounds 1-5 were used as host materials for comparison. A constant current power supply (Keithley 2400) was used, and a fixed current density was passed through the light-emitting element. A spectro-radiometer (CS2000) was used to measure the emission spectrum. At the same time, the IVL (current-voltage-luminance) performance of the device was measured at 10 mA / cm 2 , and the LT95 device lifetime was measured at 50 mA / cm 2 . The results are shown in Tables 1 and 2 below.

[0500] The device performance data of the devices prepared by using the compounds of the present invention and Comparative Compounds 1-5 as single hosts and co-evaporating with a red-light doping material are shown in Table 1 (the examples in Table 1 use the compounds of the present invention, and the comparative examples use the comparative compounds).

[0501] Table 1

[0502]

[0503] The device data of the devices prepared by co-evaporating the compounds of the present invention, comparative compounds, and RH-N material in a 5:5 mixing ratio with a red-light doping material to form a light-emitting layer are shown in Table 2.

[0504] Table 2

[0505]

[0506]

[0507]

[0508] It can be seen from Tables 1-2 that the device lifetime corresponding to the device prepared from the compound of the present invention is significantly better than that of the devices prepared from Comparative Compounds 1-5.

[0509] Comparison of sublimation temperatures: The definition of sublimation temperature is: at a vacuum degree of 10 -7 Torr, the temperature corresponding to a sublimation rate of 1 Å per second. The test results are shown in Table 3.

[0510] Table 3

[0511] Material Sublimation temperature / °C CPD2 252 CPD26 258 CPD103 266 CPD231 257 CPD414 260 CPD484 263 Comparative compound 2 271 Comparative compound 3 284 Comparative compound 4 273

[0512] As can be seen from Table 3, the compounds of the present invention have a lower sublimation temperature compared to Comparative Compounds 2-4, which is beneficial for industrial application.

[0513] As a single-host red light material, the compounds of the present invention have a lower voltage, higher current efficiency, and longer lifespan than the comparative compounds; at the same time, when the compounds of the present invention are paired with an N-type material and used as a double-host material, due to balancing the hole and electron transport rates and broadening the exciton recombination region in the light-emitting layer, compared with Comparative Compounds 1-5, the efficiency and lifespan of the device are greatly improved.

[0514] Therefore, the compound materials of the present invention have the advantages of high photo and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device lifespan, and can be used as host materials in OLED light-emitting devices. At the same time, they have a relatively low melting point, which is beneficial for the evaporation stability of the materials as molten materials. As host materials, the compounds of the present invention have the potential to be applied in the AMOLED industry.

[0515] In addition, since it is impossible to list all the compounds of the present invention one by one, the above Tables 1-3 only list some of the compounds or device performances of the present invention. However, within the scope of the present invention's claims, especially the compounds with specific structural formulas given in the present invention all have the advantages of high photo and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device lifespan similar to CPD2.

Claims

1. A compound, characterized in that, Its structural general formula is shown in Formula (1): Among them, ring A is selected from the structures shown in the following Formula (A-1) or Formula (A-7); Among them, * represents the site fused with the 5-membered ring containing X in Formula (1); Among them, a is an integer from 0 to 10; if a ≥ 2 or a larger integer, then each R0 can be the same or different; R0 is selected from hydrogen, deuterium, C1-C10 alkyl; In formula (1), X is selected from NR a or CR b R c ; R a 、R b 、R c are each independently selected from C1-C30 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C5-C20 heteroaryl; L is selected from a single bond; Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl; The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C6-C12 aryl, wherein the substitution number is from single substitution to maximum number substitution; The heteroatoms in the heteroaryl are independently selected from at least one of O, S, N.

2. The compound according to claim 1, characterized in that, The R a 、R b 、R c are independently selected from C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C5-C20 heteroaryl; and / or, Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.

3. The compound according to claim 1 or 2, characterized in that The structure shown in the above Formula (A-1) or Formula (A-7) is selected from the structures shown in the following Formula (A-9) or Formula (A-13): Among them, * represents the site fused with the 5-membered ring containing X in Formula (1); Among them, a is an integer from 0 to 6; if a ≥ 2 or a larger integer, then each R0 can be the same or different.

4. The compound according to claim 1 or 2, wherein wherein X is CR b R c ; and / or, The R b and R c are each independently selected from C1-C10 alkyl, C3-C10 cycloalkyl, C6-C10 aryl, and C5-C10 heteroaryl.

5. The compound according to claim 1 or 2, characterized in that The Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted phenanthroxazolyl, oxaspirofluorenyl, substituted or unsubstituted benzocarbazolyl, or a combination of at least two of the foregoing.

6. A compound, characterized in that The compound is one of the following structural formulas, or a structure in which hydrogen in the following structural formulas is partially or completely substituted by deuterium or fluorine:

7. An organic electroluminescent device, characterized in that, Comprising the compound according to any one of claims 1-6.

8. The organic electroluminescent device according to claim 7, wherein Comprising a light-emitting layer, the light-emitting layer comprising the compound according to any one of claims 1-6.

Images