Compound and organic light-emitting device

Abstract

The present invention relates to the technical field of organic electroluminescence. Disclosed are a compound and an organic light-emitting device (OLED). The general structural formula of the compound is represented by formula (1): formula (1), wherein ring A is selected from the following formula (2) or formula (3); and formula (2) and formula (3), X1-X12 are each independently selected from CR0 or N, and X is selected from NRa, CRbRc, or a chalcogen. The compound has advantages such as high photostability and electro-stability, low sublimation temperature, low driving voltage, high light-emitting efficiency, and long device lifetime, and can be used as a host material in OLEDs.

Description

Compound and organic electroluminescent device Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and in particular relates to a compound and an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs), a next-generation display technology, are gaining increasing attention in both display and lighting applications, boasting a broad range of applications. However, compared to market requirements, OLED device performance, including luminous efficiency, driving voltage, and lifespan, still requires further improvement.

[0003] Generally speaking, the basic structure of an OLED device consists of thin films of various organic functional materials sandwiched between metal electrodes, creating a sandwich-like structure. Driven by an electric current, holes and electrons are injected from the cathode and anode, respectively. After traveling a certain distance, the holes and electrons recombine in the light-emitting layer and release the light as light or heat, thus producing the luminescent effect. However, the properties of phosphorescent OLEDs are not only determined by the triplet emitter used. Other materials, such as the host material, are also crucial. The host material plays a significant role in reducing the device's driving voltage, improving its luminous efficiency, and extending its lifespan. Therefore, it is necessary to continue researching and developing new host materials to further improve the performance of organic electroluminescent devices.

[0004] Prior art The host material has dibenzofuranophenylfluorene connected to diarylamine, and is used in combination with triazine compounds as a red light co-host material. The device efficiency of this type of material needs to be further improved; the existing technology The main material of the phenanthroline oxazole structural unit connected to the diarylamine has a strong planarity and a high evaporation temperature, and the device efficiency and lifespan need to be improved. The performance of devices using similar phenanthrobenzofuran structural units connected to diarylamine materials as dual-host materials needs to be further improved, especially in terms of device lifespan.

[0005] Therefore, there is an urgent need to provide a new compound for solving the above-mentioned problems existing in light-emitting devices. Summary of the Invention

[0006] The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention provides a compound and an organic electroluminescent device.

[0007] A first aspect of the present invention provides a compound.

[0008] In some embodiments, a compound has a general structural formula as shown in formula (1):

[0009] Wherein, ring A is selected from the following formula (2) or formula (3);

[0010] Among them, X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1);

[0011] 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 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; two adjacent R0 may be connected to form a ring;

[0012] In formula (1), X is selected from NR a , CR b R c or oxygen group elements;

[0013] R a 、R b 、R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, and C6-C30 arylsilyl;

[0014] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0015] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl;

[0016] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbon-substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

[0017] 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 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamine.

[0018] 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 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino, or C6-C20 arylamine.

[0019] In some embodiments, 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.

[0020] In some embodiments of the present invention, adjacent R0 refers to R0 located on adjacent carbon atoms.

[0021] In some embodiments of the present invention, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0022] In some embodiments of the present invention, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0023] In some embodiments, the chalcogen element is selected from O, S or Se.

[0024] In some embodiments, the R a 、R b 、R c They are independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C3-C20 alkylsilyl and C6-C20 arylsilyl.

[0025] In some embodiments, Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups.

[0026] In some embodiments, the heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si and Ge.

[0027] In some embodiments, the structures represented by formula (2) and formula (3) are selected from the structures represented by the following formulas (A-1) to (A-8):

[0028] Wherein, * represents the site fused to the 5-membered ring containing X in formula (1);

[0029] Wherein a is an integer of 0-10; if a≥2 or a larger integer, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

[0030] In some embodiments, the structures represented by formula (2) and formula (3) are selected from the structures represented by the following formulas (A-9) to (A-16):

[0031] Wherein, * represents the site fused to the 5-membered ring containing X in formula (1);

[0032] Wherein a is an integer of 0-6; if a≥2 or a larger integer, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

[0033] In some embodiments, L is a substituted or unsubstituted C6-C20 arylene or heteroarylene group.

[0034] In some embodiments, L is a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C60 heteroarylene group.

[0035] In some embodiments, X is CR b R c , O or S.

[0036] In some embodiments, the R b 、R c They are independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, and C5-C10 heteroaryl.

[0037] In some embodiments, X1-X 12 Contains at least one N.

[0038] In some embodiments, 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 benzocycloalkyl, substituted or unsubstituted phenanthroxazolyl, oxaspirofluorenyl, substituted or unsubstituted benzocarbazolyl, or a combination of at least two of the foregoing.

[0039] In some embodiments of the present invention, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0040] In some embodiments of the present invention, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0041] In some embodiments of the present invention, aryl is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacene, pyrenyl, phenyl, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl.

[0042] In some embodiments of the present invention, the heteroaryl group is selected from pyrrolyl, pyrazinyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, and quinazolinyl.

[0043] In some embodiments, the compound is one of the following structural formulas, or a structure in which hydrogen is partially or completely replaced by deuterium or fluorine:

[0044] Taking CPD435 as an example, Ar1 is an unsubstituted C6 aryl group (i.e., phenyl group), and Ar2 is a substituted aryl group, wherein the substitution is a heteroaryl group substituted by a C1-C6 hydrocarbon group (phenyl group).

[0045] A second aspect of the present invention provides an organic electroluminescent device.

[0046] Specifically, an organic electroluminescent device includes the above compound.

[0047] In some embodiments, an organic electroluminescent device includes a cathode and an anode, the cathode and the anode being disposed opposite each other, and a light-emitting layer disposed between the cathode and the anode, the light-emitting layer comprising the aforementioned compound. The compounds of the present invention can be used alone or after doping to prepare the light-emitting layer.

[0048] In one embodiment, the light-emitting layer is a red light-emitting layer, comprising a red light-emitting material and at least one of the above compounds. In this embodiment, the compound of the present invention serves as a host material of the red light-emitting layer.

[0049] The third aspect of the present invention provides use of the above compound in the semiconductor field.

[0050] Specifically, the above compound is used in the preparation of semiconductor devices.

[0051] In some embodiments, the semiconductor device comprises an optoelectronic device.

[0052] Compared with the prior art, the present invention has the following beneficial effects:

[0053] The compound described in the present invention has advantages such as low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a host material in OLED light-emitting devices. It also has a low melting point, which improves the stability of the material vapor deposition as a molten material. As a red light host material, this compound has potential application in the AMOLED industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0054] Figure 1 shows the compound CPD231 of the present invention. 1 H NMR spectrum;

[0055] FIG2 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION

[0056] In order to make the technical solution of the present invention more clearly understood by those skilled in the art, the following examples are given for illustration. It should be noted that the following examples do not limit the scope of protection claimed by the present invention.

[0057] Unless otherwise specified, the raw materials, reagents, or devices used in the following examples can be obtained from conventional commercial sources or by existing known methods.

[0058] A compound having the structure shown in formula (1):

[0059] Wherein, X is selected from NR a , CR b R c , O, S or Se;

[0060] Wherein, ring A is selected from the following formula (2) or formula (3);

[0061] Among them, X1-X 12 are independently selected from CR0 or N; and X1-X4, X5-X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1).

[0062] 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 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; two adjacent R0 can be connected to form a ring.

[0063] R a 、R b 、R c 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;

[0064] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0065] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl;

[0066] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions;

[0067] The heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si and Ge;

[0068] Hereinafter, examples of each group of the compounds represented by formula (1), formula (2), and formula (3) will be described.

[0069] In the present specification, the "carbon number a to b" in the expression "substituted or unsubstituted X group having a to b carbon atoms" refers to the carbon number of the unsubstituted X group and does not include the carbon number of the substituent when the X group is substituted.

[0070] Specific examples of the alkyl group include linear or branched alkyl groups, specifically, 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 methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and more preferably propyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.

[0071] Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl, and cyclopentyl and cyclohexyl are preferred.

[0072] Specific examples of the alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, and 3-hexatrienyl, with propenyl and allyl being preferred.

[0073] Specific examples of heteroalkyl groups include linear or branched alkyl groups and cycloalkyl groups containing atoms other than carbon and hydrogen, such as mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, butylene oxide, cyclopentyl, and hexyl oxide, preferably methoxymethane and cyclopentyl.

[0074] Specific examples of the aryl group include phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacene, pyrenyl, phenyl, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl, etc., preferably phenyl or naphthyl.

[0075] Specific examples of heteroaryl groups include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthroline ... The oxazine group includes oxadiazolyl, oxadiazolyl, furazanyl, thienyl, benzothienyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl, etc., preferably pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, azadibenzothienyl, diazadibenzofuranyl, diazadibenzothienyl, carbazolyl, azacarbazolyl, diazacarbazolyl.

[0076] The following embodiments are only for facilitating understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0077] The raw materials and solvents involved in the synthesis of the compounds of the present invention were purchased from suppliers well known to those skilled in the art, such as Alfa and Acros.

[0078] Synthesis of compound CPD2:

[0079] The synthetic route is:

[0080] Synthesis of compound CPD2-3:

[0081] CPD2-1 (30.00 g, 106.56 mmol), CPD2-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphine)diphenylferric palladium chloride (Pd(dppf)Cl2, 1.56 g, 2.13 mmol), potassium acetate (KOAc, 15.69 g, 159.84 mmol), and 1,4-dioxane (450 mL) were added to a 1000 mL three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 100° C. for 2 hours. The reaction was monitored by TLC (thin layer chromatography, ethyl acetate:n-hexane = 1:10 as the developing solvent). The raw material CPD2-1 was completely consumed.

[0082] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and the product was washed three times with deionized water (300 mL*3). The product was separated, mixed with silica gel, and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:15 as eluent). After elution, the product was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid CPD2-3 (27.62 g, mass fraction purity: 98.01%, yield: 78.88%). The mass spectrometry characterization result was 329.12 (M+H).

[0083] Synthesis of compound CPD2-5:

[0084] 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 vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 75°C for 3 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent). The raw material CPD2-3 was completely consumed.

[0085] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and the product was washed three times with deionized water (300 mL*3). The product was separated, mixed with silica gel, and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the product 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).

[0086] Synthesis of compound CPD2-7:

[0087] 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 vacuum atmosphere was replaced with nitrogen three times. The system was then cooled to 5°C and sodium methoxide (NaOMe, 5.45 g, 100.90 mmol) was added all at once. The reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent). The starting material CPD2-5 was completely consumed.

[0088] Deionized water (500 mL) was added, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added for extraction. The mixture was separated and concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid, CPD2-7 (18.44 g, yield: 95.00%). Mass spectrometry analysis revealed a mass spectral density of 385.04 (M+H). The resulting compound was used directly in the next step without further purification.

[0089] Synthesis of compound CPD2-8:

[0090] CPD2-7 (17.00 g, 44.17 mmol) and toluene (170 mL) were added to a 500 mL three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times. The system was then cooled to 5°C and methanesulfonic acid (MsOH, 8.49 g, 88.34 mmol) was slowly added dropwise over 3 minutes. The reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:15 as the developing solvent). The starting material CPD2-7 was completely consumed.

[0091] Methanol (200 mL) was added thereto to precipitate a large amount of white solid, which was filtered to obtain 17 g of solid. The solid was crystallized once with toluene (204 mL) and methanol (170 mL), filtered, and the filter cake was dried under vacuum 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).

[0092] Synthesis of compound CPD2:

[0093] 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 vacuum was replaced with nitrogen three times, and the system was heated to 105 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The raw material CPD 2-8 was completely consumed.

[0094] The mixture was cooled to 60°C, methanol (150 mL) was added, and the temperature was naturally lowered to room temperature and stirred for 30 minutes to precipitate a large amount of solid. Filtering with suction yielded 20 g of solid. Toluene (300 mL) was added, and the system was then heated to 100°C to dissolve and clarify. Filtering was then performed over 30 g of silica gel (300-400 mesh). The silica gel surface was rinsed with toluene (50 mL), and the combined filtrates were concentrated to yield 18 g. Crystallization was performed twice using toluene (180 mL) and methanol (90 mL), followed by filtration. The filter cake was vacuum-dried at 90°C for 3 hours to yield CPD2 (14.07 g, 99.94% purity by mass, 88.41% yield) as a pale yellow solid.

[0095] 14.07 g of pale yellow solid CPD2 crude product was purified by sublimation to obtain sublimation-purified CPD2 (11.26 g, mass fraction purity: 99.95%, yield: 80.02%), with mass spectrometry results of 562.22 (M+H). 1 H NMR (400MHz, CDCl3) δ8.17(d,J=9.1Hz,1H),8.07-8.00(m,1H),7.97-7.87(m,4H),7.85(dd,J=7.5,3.0Hz,2H),7.60-7.55(m ,2H),7.55-7.48(m,4H),7.42-7.39(m,3H),7.32(d,J=7.3Hz,1H),7.31-7.24(m,2H),7.16-7.07(m,5H),7.02-6.97(m,2H).

[0096] Synthesis of compound CPD19:

[0097] Synthesis route:

[0098] Synthesis of compound CPD19-2:

[0099] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD19-2 (30.52 g, mass fraction purity: 99.00%, yield: 78.62%), and the mass spectrometry characterization result is: 329.12 (M+H).

[0100] Synthesis of compound CPD19-3:

[0101] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD19-3 (27.02 g, mass fraction purity: 99.33%, yield: 76.52%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0102] Synthesis of compound CPD19-4:

[0103] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD19-4 as a white solid (25.66 g, yield: 96.08%). The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0104] Synthesis of compound CPD19-5:

[0105] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD19-5 (17.95 g, mass fraction purity: 99.76%, yield: 75.55%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0106] Synthesis of compound CPD19:

[0107] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD19 (16.74 g, mass fraction purity: 99.95%, yield: 78.65%) as a light yellow solid. 16.74 g of the crude light yellow solid CPD19 was purified by sublimation to obtain sublimation-purified CPD19 (13.10 g, mass fraction purity: 99.95%, yield: 78.26%). The mass spectrometry result was 652.32 (M+H).

[0108] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.17(d,J=9.1Hz,1H),8.08(d,J=2.1Hz,1H),8.07-8.02(m,1H),8.02-7.97(m,1H),7.94(dd,J=8.6,2.0Hz,2H),7.92-7.8 7(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).

[0109] Synthesis of compound CPD26:

[0110] Synthesis route:

[0111] Synthesis of compound CPD26-3:

[0112] Referring to the synthesis and purification method of compound CPD2, only the corresponding raw materials need to be changed and the reaction temperature is 90°C to obtain a white solid as the target compound CPD26-3 (35.62 g, mass fraction purity: 99.83%, yield: 74.63%), with mass spectrometry characterization results: 363.14 (M+H).

[0113] Synthesis of compound CPD26:

[0114] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD26 (17.69 g, 99.93% purity, 75.21% yield) as a pale yellow solid. 17.69 g of the crude pale yellow solid CPD26 was purified by sublimation to obtain sublimation-purified CPD26 (15.62 g, 99.93% purity, 88.30% yield), characterized by a mass spectrometry result of 679.22 (M+H).

[0115] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.17(d,J=9.1Hz,1H),8.11(d,J=2.2Hz,1H),8.07-8.01(m,1H),7.97-7.87(m,5H),7.86-7.84(m,2H), 7.78(dd,J=8.9,1.4Hz,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).

[0116] Synthesis of compound CPD57:

[0117] Synthesis route:

[0118] Synthesis of compound CPD57-2:

[0119] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD57-2 (28.02 g, mass fraction purity: 98.52%, yield: 77.65%), and the mass spectrometry characterization result is: 329.12 (M+H).

[0120] Synthesis of compound CPD57-3:

[0121] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD57-3 (26.33 g, mass fraction purity: 99.45%, yield: 75.09%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0122] Synthesis of compound CPD57-4:

[0123] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD57-4 (24.44 g, yield: 97.89%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0124] Synthesis of compound CPD57-5:

[0125] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD57-5 (16.85 g, mass fraction purity: 99.79%, yield: 76.85%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0126] Synthesis of compound CPD57-7:

[0127] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD57-7 (20.84 g, mass fraction purity: 99.80%, yield: 77.15%), and the mass spectrometry characterization result is: 370.12 (M+H).

[0128] Synthesis of compound CPD57:

[0129] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD57 (18.95 g, mass fraction purity: 99.93%, yield: 77.01%) as a light yellow solid. 18.95 g of the crude light yellow solid CPD57 was purified by sublimation to obtain sublimation-purified CPD57 (16.41 g, mass fraction purity: 99.95%, yield: 86.60%). The mass spectrometry result was 686.22 (M+H).

[0130] NMR characterization results: 1H 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),7.05-6.97(m,3H).

[0131] Synthesis of compound CPD78:

[0132] Synthesis route:

[0133] Synthesis of compound CPD78-2:

[0134] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD78-2 (30.54 g, mass fraction purity: 98.44%, yield: 77.12%), and the mass spectrometry characterization result is: 329.12 (M+H).

[0135] Synthesis of compound CPD78-3:

[0136] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD78-3 (27.09 g, mass fraction purity: 99.66%, yield: 76.36%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0137] Synthesis of compound CPD78-4:

[0138] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD78-4 (23.12 g, yield: 93.93%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0139] Synthesis of compound CPD78-5:

[0140] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD78-5 (18.08 g, mass fraction purity: 99.65%, yield: 40.20%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0141] Synthesis of compound CPD78-8:

[0142] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD78-8 (23.11 g, mass fraction purity: 99.60%, yield: 76.44%), and the mass spectrometry characterization result is: 337.13 (M+H).

[0143] Synthesis of compound CPD78:

[0144] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD78 (16.76 g, mass fraction purity: 99.92%, yield: 76.22%) as a light yellow solid. 16.76 g of the crude light yellow solid CPD78 was purified by sublimation to obtain sublimation-purified CPD78 (14.21 g, mass fraction purity: 99.92%, yield: 84.78%). The mass spectrometry result was 653.21 (M+H).

[0145] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.33-8.26(m,1H),8.21(dd,J=17.5,8.8Hz,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).

[0146] Synthesis of compound CPD94:

[0147] Synthesis route:

[0148] Synthesis of compound CPD94-3:

[0149] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD94-3 (19.88 g, mass fraction purity: 99.57%, yield: 78.08%), and the mass spectrometry characterization result is: 357.04 (M+H).

[0150] Synthesis of compound CPD94-4:

[0151] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD94-4 (25.58 g, yield: 94.35%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0152] Synthesis of compound CPD94-5:

[0153] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD94-5 (20.01 g, mass fraction purity: 99.74%, yield: 78.63%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0154] Synthesis of compound CPD94:

[0155] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD94 (17.77 g, mass fraction purity: 99.94%, yield: 71.06%) as a yellow solid. 17.77 g of crude yellow solid CPD94 was purified by sublimation to obtain sublimation-purified CPD94 (15.02 g, purity: 99.94%, yield: 84.52%). The mass spectrometry result was 678.22 (M+H).

[0156] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.47(dd,J=7.6,1.4Hz,1H),8.16-8.10(m,1H),8.10-8.02(m,4H),7.93-7.86(m,3H),7.82(d ,J=7.1Hz,1H),7.61-7.34(m,15H),7.32-7.30(m,1H),7.17(dd,J=7.2,2.1Hz,1H),7.03-6.97(m,2H),1.74(s,6H).

[0157] Synthesis of compound CPD103:

[0158] Synthesis route:

[0159] Synthesis of compound CPD103-2:

[0160] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD103-2 (32.65 g, mass fraction purity: 98.78%, yield: 79.05%), and the mass spectrometry characterization result is: 345.02 (M+H).

[0161] Synthesis of compound CPD103-3:

[0162] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD103-3 (29.63 g, mass fraction purity: 99.75%, yield: 76.03%), and the mass spectrometry characterization result is: 373.04 (M+H).

[0163] Synthesis of compound CPD103-4:

[0164] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD103-4 (25.63 g, yield: 95.39%) as a white solid. The mass spectrometry result was 401.14 (M+H). The obtained compound was used directly in the next step without purification.

[0165] Synthesis of compound CPD103-5:

[0166] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD103-5 (20.00 g, mass fraction purity: 99.76%, yield: 78.80%), and the mass spectrometry characterization result is: 369.02 (M+H).

[0167] Synthesis of compound CPD103-8:

[0168] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD103-8 (24.23 g, mass fraction purity: 99.86%, yield: 75.63%), and the mass spectrometry characterization result is: 412.22 (M+H).

[0169] Synthesis of compound CPD103:

[0170] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD103 (14.33 g, 99.95% purity, 74.63% yield) as a pale yellow solid. 14.33 g of the crude pale yellow solid CPD103 was purified by sublimation to obtain sublimation-purified CPD103 (12.01 g, 99.95% purity, 83.81% yield), characterized by a mass spectrometry result of 744.24 (M+H).

[0171] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.21 (d, J = 7.1Hz, 1H), 8.10-8.03 (m, 3H), 8.03-7.95 (m, 2 H),7.93(d,J=2.2Hz,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=7.6,2.1Hz,1H),7.16(dd,J=7.0,2.2Hz,1H),6.97-6.91(m,2H).

[0172] Synthesis of compound CPD123:

[0173] Synthesis route:

[0174] Synthesis of compound CPD123:

[0175] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD123 (12.11 g, 99.95% purity, 76.87% yield) as a pale yellow solid. 12.11 g of the crude pale yellow solid CPD123 was purified by sublimation to obtain sublimation-purified CPD123 (9.87 g, 99.95% purity, 81.51% yield), characterized by a mass spectrometry result of 576.32 (M+H).

[0176] NMR characterization results: 1H NMR(400MHz, CDCl3)δ8.33-8.26(m,1H),8.21(dd,J=17.5,8.8Hz,2H),8.13-8.03(m,2H),7.99-7.9 3(m,2H),7.93-7.82(m,2H),7.55-7.47(m,2H),7.43(d,J=7.5Hz,1H),7.32(dd,J=7.6,2.1Hz,1H).

[0177] Synthesis of compound CPD132:

[0178] Synthesis route:

[0179] Synthesis of compound CPD132-2:

[0180] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD132-2 (23.22 g, mass fraction purity: 99.51%, yield: 75.20%), and the mass spectrometry characterization result is: 357.04 (M+H).

[0181] Synthesis of compound CPD132-3:

[0182] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD132-3 as a white solid (21.25 g, yield: 95.05%). The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0183] Synthesis of compound CPD132-4:

[0184] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD132-4 (22.12 g, mass fraction purity: 99.83%, yield: 77.05%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0185] Synthesis of compound CPD132:

[0186] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD132 (15.44 g, 99.94% purity, 73.63% yield) as a yellow solid. 15.44 g of crude yellow solid CPD132 was purified by sublimation to obtain sublimation-purified CPD132 (12.50 g, 99.94% purity, 80.96% yield), characterized by a mass spectrometry result of 618.24 (M+H).

[0187] NMR characterization results: 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),7.45-7.37(m,4H),7.18-7.12(m,3H),7.03-6.97(m,2H),6.93-6.88(m,2H),1.31(s,9H).

[0188] Synthesis of compound CPD150:

[0189] Synthesis route:

[0190] Synthesis of compound CPD150-2:

[0191] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD150-2 (24.54 g, mass fraction purity: 99.58%, yield: 75.98%), and the mass spectrometry characterization result is: 357.04 (M+H).

[0192] Synthesis of compound CPD150-3:

[0193] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD150-3 as a white solid (23.84 g, yield: 95.96%). The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0194] Synthesis of compound CPD150-4:

[0195] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD150-4 (20.52 g, mass fraction purity: 99.63%, yield: 75.82%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0196] Synthesis of compound CPD150-6:

[0197] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD150-6 (25.63 g, mass fraction purity: 99.87%, yield: 74.25%), and the mass spectrometry characterization result is: 320.12 (M+H).

[0198] Synthesis of compound CPD150:

[0199] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials need to be changed to obtain the target compound CPD150 (17.63 g, mass fraction purity: 99.94%, yield: 77.06%) as a yellow solid. 17.63 g of crude yellow solid CPD150 was purified by sublimation to obtain sublimation-purified CPD150 (14.76 g, mass fraction purity: 99.94%, yield: 83.72%). Mass spectrometry analysis showed a mass spectrometric index of 636.22 (M+H).

[0200] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.62(d,J=9.2Hz,1H),8.57(d,J=9.3Hz,1H),8.50-8.43(m,1H) ,8.37(d,J=8.3Hz,1H),8.33-8.27(m,1H),8.25(d,J=8.1Hz,1H),8.01-7.95(m,3H),7 .92-7.87(m,5H),7.82(d,J=7.2Hz,1H),7.73(d,J=2.0Hz,1H),7.56-7.47(m,4H),7.3 7(d,J=7.1Hz,1H),7.32-7.24(m,2H),7.17-7.06(m,5H),6.89(dd,J=7.5,2.2Hz,1H).

[0201] Synthesis of compound CPD174:

[0202] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD174 (13.15 g, mass fraction purity: 99.93%, yield: 75.32%) as a light yellow solid. 13.15 g of the crude light yellow solid CPD174 was purified by sublimation to obtain sublimation-purified CPD174 (10.05 g, purity: 99.95%, yield: 76.43%). The mass spectrometry result was 728.24 (M+H).

[0203] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.33-8.26(m,1H),8.22(d,J=2.3Hz,1H),8.15(dd,J=9.0,2.4Hz,1H),8.03-7.91(m,5H),7.91-7.86(m,2H),7.83(d,J=2.1Hz, 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=7.5,2.2Hz,2H),6.97-6.91(m,2H).

[0204] Synthesis of compound CPD181:

[0205] Synthesis route:

[0206] Synthesis of compound CPD181-2:

[0207] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD181-2 (25.63 g, mass fraction purity: 98.83%, yield: 75.82%), and the mass spectrometry characterization result is: 329.12 (M+H).

[0208] Synthesis of compound CPD181-3:

[0209] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD181-3 (23.55 g, mass fraction purity: 99.48%, yield: 75.99%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0210] Synthesis of compound CPD181-4:

[0211] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD181-4 (20.61 g, yield: 95.46%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0212] Synthesis of compound CPD181-5:

[0213] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD181-5 (16.85 g, mass fraction purity: 99.80%, yield: 74.63%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0214] Synthesis of compound CPD181:

[0215] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD181 (15.06 g, 99.94% purity, 77.04% yield) as a pale yellow solid. 15.06 g of the crude pale yellow solid CPD181 was purified by sublimation to obtain sublimation-purified CPD181 (11.82 g, 99.94% purity, 78.49% yield). Mass spectrometry analysis revealed a mass spectrometric index of 653.22 (M+H).

[0216] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.35-8.28(m,1H),8.10(d,J=8.1Hz,1H),8.05-8.00(m,2H),8.00-7.86(m,8H),7.86-7.79(m,2H) ,7.76(d,J=8.1Hz,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).

[0217] Synthesis of compound CPD209:

[0218] Synthesis route:

[0219] Synthesis of compound CPD209-2:

[0220] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD209-2 (28.78 g, mass fraction purity: 99.74%, yield: 76.11%), and the mass spectrometry characterization result is: 357.24 (M+H).

[0221] Synthesis of compound CPD209-3:

[0222] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD209-3 (22.65 g, yield: 95.63%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0223] Synthesis of compound CPD209-4:

[0224] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD209-4 (15.63 g, mass fraction purity: 99.22%, yield: 40.96%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0225] Synthesis of compound CPD209:

[0226] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD209 (14.55 g, 99.93% purity, 75.66% yield) as a pale yellow solid. 14.55 g of crude CPD209 was purified by sublimation to obtain sublimation-purified CPD209 (11.33 g, 99.94% purity, 77.87% yield), characterized by a mass spectrometry result of 652.22 (M+H).

[0227] NMR characterization results: 1H NMR(400MHz, CDCl3)δ8.64(d,J=9.3Hz,1H),8.46-8.41(m,1H),8.38(d,J=9.6H z,1H),8.21(d,J=1.1Hz,2H),8.04(d,J=9.5Hz,1H),8.01-7.94(m,3H),7.91-7 .86(m,1H),7.83(d,J=2.1Hz,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=7.6,2.1Hz,2H),7.02-6.97(m,2H).

[0228] Synthesis of compound CPD224:

[0229] Synthesis route:

[0230] Synthesis of compound CPD224-2:

[0231] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD224-2 (35.09 g, mass fraction purity: 98.06%, yield: 78.45%), and the mass spectrometry characterization result is: 329.12 (M+H).

[0232] Synthesis of compound CPD224-3:

[0233] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD224-3 (32.06 g, mass fraction purity: 99.87%, yield: 75.02%), and the mass spectrometry characterization result is: 357.04 (M+H).

[0234] Synthesis of compound CPD224-4:

[0235] Following the synthesis and purification methods for compound CPD2-7, only the corresponding starting materials were modified to obtain the target compound CPD224-4 (14.32 g, 94.33% mass fraction yield) as a white solid. Mass spectrometry revealed a mass of 385.04 (M+H). The resulting compound was used directly in the next step without further purification.

[0236] Synthesis of compound CPD224-5:

[0237] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD224-5 (17.07 g, mass fraction purity: 99.54%, yield: 40.63%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0238] Synthesis of compound CPD224:

[0239] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD224 (13.11 g, 99.93% purity, 72.74% yield) as a pale yellow solid. 13.11 g of the crude pale yellow solid CPD224 was purified by sublimation to obtain sublimation-purified CPD224 (10.05 g, 99.93% purity, 76.66% yield). Mass spectrometry analysis revealed a mass index of 724.26 (M+H).

[0240] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.65-8.55(m,3H),8.49-8.42(m,1H),8.10(d,J=2.1Hz,1H),8.03(dd,J=6.8,1.4Hz,3H),8.0 2-7.93(m,7H),7.93-7.85(m,2H),7.56-7.44(m,8H),7.42(d,J=7.6Hz,1H),7.33-7.23(m,3H),7.21-7.07(m,4H).

[0241] Synthesis of compound CPD231:

[0242] Synthesis route:

[0243] Synthesis of compound CPD231-1:

[0244] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD231-1 (30.68 g, mass fraction purity: 99.78%, yield: 74.62%), and the mass spectrometry characterization result is: 357.24 (M+H).

[0245] Synthesis of compound CPD231-2:

[0246] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD231-2 (24.55 g, yield: 96.33%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0247] Synthesis of compound CPD231-3:

[0248] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD231-3 (17.99 g, mass fraction purity: 99.86%, yield: 78.63%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0249] Synthesis of compound CPD231:

[0250] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD231 (17.11 g, 99.95% purity, 78.74% yield) as a pale yellow solid. 17.11 g of crude CPD231 was purified by sublimation to obtain sublimation-purified CPD231 (13.75 g, 99.95% purity, 80.37% yield), characterized by a mass spectrometry result of 562.24 (M+H).

[0251] Figure 1 shows the compound CPD231 of the present invention. 1 H NMR spectrum.

[0252] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.75-8.71(m,2H),8.66(d,J=8.9Hz,1H),8.42(d,J=2.2Hz,1H),8.03(dd,J=18.4,8.8Hz,2H),7. 87(d,J=8.7Hz,1H),7.75-7.52(m,8H),7.47(t,J=7.7Hz,2H),7.43-7.30(m,5H),7.26-7.19(m,4H),7.12-7.11(m,1H).

[0253] Synthesis of compound CPD249:

[0254] Synthesis route:

[0255] Synthesis of compound CPD249:

[0256] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD249 (15.00 g, mass fraction purity: 99.95%, yield: 73.96%) as a light yellow solid. 15.00 g of the crude light yellow solid CPD249 was purified by sublimation to obtain sublimation-purified CPD249 (11.33 g, mass fraction purity: 99.95%, yield: 75.54%). Mass spectrometry analysis revealed a mass spectrometric index of 652.24 (M+H).

[0257] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.62-8.59(m,2H),8.47-8.39(m,1H),8.33-8.28(m, 1H),8.08(d,J=2.1Hz,1H),8.03-7.96(m,1H),7.94(d,J=8.1Hz,1H),7.91- 7.85(m,2H),7.83(d,J=2.1Hz,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).

[0258] Synthesis of compound CPD265:

[0259] Synthesis route:

[0260] Synthesis of compound CPD265:

[0261] 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 (10.33 g, mass fraction purity: 99.94%, yield: 78.63%) as a light yellow solid. 10.33 g of the crude light yellow solid CPD265 was purified by sublimation to obtain sublimation-purified CPD265 (8.13 g, mass fraction purity: 99.94%, yield: 78.71%). The mass spectrometry result was 668.34 (M+H).

[0262] NMR characterization results: 1H NMR(400MHz, CDCl3)δ8.61(dd,J=8.5,3.7Hz,2H),8.47-8.39(m,1H),8.33-8.28(m,1H),8.06(d,J=2.2Hz ,1H),7.96-7.90(m,2H),7.89-7.86(m,1H),7.56-7.47(m,2H),7.42(d,J=7.5Hz,1H),7.33-7.31(m,2H).

[0263] Synthesis of compound CPD280:

[0264] Synthesis route:

[0265] Synthesis of compound CPD280-1:

[0266] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD280-1 (32.63 g, mass fraction purity: 99.69%, yield: 745.69%), and the mass spectrometry characterization result is: 357.24 (M+H).

[0267] Synthesis of compound CPD280-2:

[0268] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD280-2 (27.96 g, yield: 94.12%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0269] Synthesis of compound CPD280-3:

[0270] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD280-3 (21.21 g, mass fraction purity: 99.59%, yield: 74.63%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0271] Synthesis of compound CPD280:

[0272] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD280 (16.06 g, mass fraction purity: 99.95%, yield: 74.44%) as a light yellow solid. 16.06 g of the crude light yellow solid CPD280 was purified by sublimation to obtain sublimation-purified CPD280 (12.90 g, mass fraction purity: 99.95%, yield: 80.33%). Mass spectrometry analysis revealed a mass spectrometric index of 712.22 (M+H).

[0273] NMR characterization results: 1 H NMR(400MHz, CDCl3)8.64(d,J=8.9Hz,1H),8.47-8.39(m,1H),8.34-8.24(m, 2H),8.19-8.15(m,3H),8.08(dd,J=17.6,7.8Hz,2H),8.01-7.96(m,3H),7.94 (d,J=2.0Hz,1H),7.92-7.85(m,1H),7.66(d,J=8.0Hz,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).

[0274] Synthesis of compound CPD289:

[0275] Synthesis route:

[0276] Synthesis of compound CPD289-2:

[0277] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD289-2 (20.06 g, mass fraction purity: 99.87%, yield: 74.63%), and the mass spectrometry characterization result is: 356.23 (M+H).

[0278] Synthesis of compound CPD289-3:

[0279] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD289-3 (10.05 g, mass fraction purity: 99.43%, yield: 39.85%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0280] Synthesis of compound CPD289:

[0281] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials needed to be changed to obtain the target compound CPD289 (10.96 g, mass fraction purity: 99.93%, yield: 78.65%) as a light yellow solid. 10.96 g of the crude light yellow solid CPD289 was purified by sublimation to obtain sublimation-purified CPD289 (8.88 g, mass fraction purity: 99.93%, yield: 81.03%). Mass spectrometry analysis revealed a mass spectrometric index of 672.32 (M+H).

[0282] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.61(dd,J=9.1,2.3Hz,2H),8.48-8.44(m,1H),8.21(d,J=2.3Hz,1H ),8.17(dd,J=9.0,2.3Hz,1H),8.00(d,J=2.2Hz,1H),7.96(d,J=9.3Hz,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 .5,2.2Hz,1H),7.13(d,J=6.6Hz,1H),7.05-6.96(m,4H),2.13-1.90(m,4H),1.33(s,12H).

[0283] Synthesis of compound CPD305:

[0284] Synthesis route:

[0285] Synthesis of compound CPD305-3:

[0286] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD305-3 (25.63 g, mass fraction purity: 99.80%, yield: 75.44%), and the mass spectrometry characterization result is: 500.20 (M+H).

[0287] Synthesis of compound CPD305-4:

[0288] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD305-4 (22.44 g, mass fraction purity: 99.53%, yield: 38.43%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0289] Synthesis of compound CPD305:

[0290] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD305 (17.89 g, 99.94% purity, 74.85% yield) as a pale yellow solid. 17.89 g of crude CPD305 was purified by sublimation to obtain sublimation-purified CPD305 (14.88 g, 99.94% purity, 83.18% yield), characterized by a mass spectrometry result of 816.28 (M+H).

[0291] NMR characterization results: 1 H NMR(400MHz, CDCl3) δ8.69(d,J=8.2Hz,1H),8.62(d,J=9.3Hz,1H),8.50-8. 43(m,1H),8.24(d,J=2.1Hz,1H),8.11-8.03(m,3H),7.99-7.92(m,2H),7.92 -7.85(m,1H),7.76(d,J=7.1Hz,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, 1.4Hz, 1H).

[0292] Synthesis of compound CPD315:

[0293] Synthesis route:

[0294] Synthesis of compound CPD315-2:

[0295] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD315-2 (26.52 g, mass fraction purity: 99.85%, yield: 87.52%), and the mass spectrometry characterization result is: 363.14 (M+H).

[0296] Synthesis of compound CPD315:

[0297] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD315 (18.08 g, mass fraction purity: 99.94%, yield: 76.66%) as a light yellow solid. 18.08 g of the crude light yellow solid CPD315 was purified by sublimation to obtain sublimation-purified CPD315 (14.76 g, mass fraction purity: 99.95%, yield: 81.64%). The mass spectrometry result was 679.24 (M+H).

[0298] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.69(d,J=8.2Hz,1H),8.62(d,J=9.3Hz,1H),8.50-8.43(m,1H),8.08-8.03(m,2H),8.00(d,J=7.1Hz,1H),7.98-7.86(m,5H), 7.62-7.55(m,2H),7.55-7.46(m,5H),7.46-7.38(m,6H),7.35-7.28(m,2 H),7.23(d,J=2.1Hz,1H),7.20(dd,J=7.1,2.2Hz,1H),7.03-6.97(m,2H).

[0299] Synthesis of compound CPD340:

[0300] Synthesis route:

[0301] Synthesis of compound CPD340-2:

[0302] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD340-2 (20.20 g, mass fraction purity: 99.52%, yield: 77.74%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0303] Synthesis of compound CPD340-3:

[0304] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD340-3 (15.86 g, yield: 94.63%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0305] Synthesis of compound CPD340-4:

[0306] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD340-4 (14.36 g, mass fraction purity: 99.76%, yield: 76.33%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0307] Synthesis of compound CPD340-5:

[0308] CPD340-4 (13.00 g, 36.85 mmol), CPD2-2 (11.23 g, 44.22 mmol), tris(dibenzylideneacetone)dipalladium (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 vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 100°C for 2 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent). The starting material CPD340-4 was completely consumed.

[0309] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (500 ml) was added, and the product was washed three times with deionized water (300 ml*2). The product was separated, mixed with silica gel, and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:12 as eluent). After elution, the product was concentrated under reduced pressure at 70°C for 1.5 hours to obtain a white solid CPD340-5 (12.37 g, mass fraction purity: 98.08%, yield: 75.55%). The mass spectrometry result was 445.20 (M+H).

[0310] Synthesis of compound CPD340-7:

[0311] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD340-7 (10.23 g, mass fraction purity: 98.88%, yield: 78.96%), and the mass spectrometry characterization result is: 523.04 (M+H).

[0312] Synthesis of compound CPD340:

[0313] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD340 (10.28 g, mass fraction purity: 99.95%, yield: 78.26%) as a light yellow solid. 10.28 g of the crude light yellow solid CPD340 was purified by sublimation to obtain sublimation-purified CPD340 (8.02 g, mass fraction purity: 99.95%, yield: 78.02%). The mass spectrometry result was 764.22 (M+H).

[0314] NMR characterization results: 1H NMR (400MHz, CDCl3) δ8.61-8.59(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=7.7Hz,1H),7.69(dd,J=7.2,2.5Hz,1H),7.64-7.45(m,14H),7.45-7.36(m,7H),7.32(d,J=7.6Hz,1H),6.96-6.91(m,4H).

[0315] Synthesis of compound CPD351:

[0316] Synthesis route:

[0317] Synthesis of compound CPD351-2:

[0318] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD351-2 (18.88 g, mass fraction purity: 99.56%, yield: 74.98%), and the mass spectrometry characterization result is: 357.22 (M+H).

[0319] Synthesis of compound CPD351-3:

[0320] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD351-3 (14.84 g, yield: 95.10%) as a white solid. The mass spectrometry result was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0321] Synthesis of compound CPD351-4:

[0322] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD351-4 (12.96 g, mass fraction purity: 99.64%, yield: 74.39%), and the mass spectrometry characterization result is: 353.06 (M+H).

[0323] Synthesis of compound CPD351:

[0324] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD351 (12.05 g, 99.93% purity, 76.85% yield) as a pale yellow solid. 12.05 g of the crude pale yellow solid CPD351 was purified by sublimation to obtain sublimation-purified CPD351 (9.33 g, 99.95% purity, 77.43% yield), characterized by a mass spectrometry result of 644.24 (M+H).

[0325] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.52-8.45(m,2H),8.34-8.27(m,2H),8.08(d,J=2.3Hz,1H),7.98-7.92(m,2H),7.61-7.47(m,8H),7.46-7.38 (m,4H),7.31(dd,J=7.5,2.2Hz,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).

[0326] Synthesis of compound CPD358:

[0327] Synthesis route:

[0328] Synthesis of compound CPD358:

[0329] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD358 (15.55 g, 99.95% purity, 77.06% yield) as a pale yellow solid. 15.55 g of the crude pale yellow solid CPD358 was purified by sublimation to obtain sublimation-purified CPD358 (13.11 g, 99.95% purity, 84.31% yield). Mass spectrometry analysis revealed a mass spectrometric index of 738.24 (M+H).

[0330] NMR characterization results: 1H NMR (400MHz, CDCl3) δ8.17(d,J=9.1Hz,1H),8.08(d,J=2.1Hz,1H),8.05-8.03(m,3H),7.97-7.91(m,4H),7.91-7.81(m,7 H),7.73-7.71(m,2H),7.59-7.54(m,4H),7.54-7.48(m,6H),7.43(d,J=7.6Hz,1H),7.36-7.28(m,2H),7.02-6.97(m,4H).

[0331] Synthesis of compound CPD379:

[0332] Synthesis route:

[0333] Synthesis of compound CPD379-2:

[0334] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD379-2 (45.33 g, mass fraction purity: 98.77%, yield: 75.33%), and the mass spectrometry characterization result is: 322.12 (M+H).

[0335] Synthesis of compound CPD379-4:

[0336] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD379-4 (35.44 g, mass fraction purity: 99.52%, yield: 72.11%), and the mass spectrometry characterization result is: 334.04 (M+H).

[0337] Synthesis of compound CPD379-5:

[0338] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD379-5 (24.63 g, yield: 95.45%) as a white solid. The mass spectrometry result was 362.09 (M+H). The obtained compound was used directly in the next step without purification.

[0339] Synthesis of compound CPD379-6:

[0340] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD379-6 (22.41 g, mass fraction purity: 99.83%, yield: 74.15%), and the mass spectrometry characterization result is: 330.02 (M+H).

[0341] Synthesis of compound CPD379-7:

[0342] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD379-7 (18.77 g, mass fraction purity: 99.66%, yield: 78.54%), and the mass spectrometry characterization result is: 463.14 (M+H).

[0343] Synthesis of compound CPD379:

[0344] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD379 (18.09 g, 99.93% purity, 75.63% yield) as a pale yellow solid. 18.09 g of the crude pale yellow solid CPD379 was purified by sublimation to obtain sublimation-purified CPD379 (14.85 g, 99.92% purity, 82.09% yield), characterized by a mass spectrometry result of 779.24 (M+H).

[0345] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.34(d,J=2.1Hz,1H),8.17(d,J=9.1Hz,1H),8.12-8.07(m,2H) ,8.07-8.02(m,2H),7.99(d,J=7.4Hz,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=7.5,2.1Hz,1H).

[0346] Synthesis of compound CPD395:

[0347] Synthesis route:

[0348] Synthesis of compound CPD395-2:

[0349] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD395-2 (20.51 g, mass fraction purity: 99.68%, yield: 76.85%), and the mass spectrometry characterization result is: 452.22 (M+H).

[0350] Synthesis of compound CPD395:

[0351] Referring to the synthesis and purification methods of compound CPD2, only the corresponding starting materials were changed to obtain the target compound CPD395 (15.33 g, mass fraction purity: 99.95%, yield: 74.52%) as a light yellow solid. 15.33 g of the crude light yellow solid CPD395 was purified by sublimation to obtain sublimation-purified CPD395 (11.06 g, mass fraction purity: 99.95%, yield: 72.15%). The mass spectrometry result was 768.22 (M+H).

[0352] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.17(d,J=9.1Hz,1H),8.14-8.12(m,1H),8.08(d,J=2.0Hz,1 H),8.06-8.01(m,1H),8.01-7.97(m,2H),7.95-7.93(m,3H),7.92-7.87(m,2H),7.8 6-7.84(m,2H),7.80(d,J=7.1Hz,1H),7.57-7.46(m,4H),7.46-7.40(m,4H),7.38( dd,J=7.2,2.1Hz,1H),7.35-7.27(m,5H),7.24(d,J=2.0Hz,1H),7.22-7.13(m,4H).

[0353] Synthesis of compound CPD414:

[0354] Synthesis route:

[0355] Synthesis of compound CPD414-1:

[0356] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD414-1 (35.75 g, mass fraction purity: 99.74%, yield: 72.62%), and the mass spectrometry characterization result is: 357.06 (M+H).

[0357] Synthesis of compound CPD414-2:

[0358] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD414-2 (22.44 g, yield: 94.33%) as a white solid. The mass spectrometry result was 384.10 (M+H). The obtained compound was used directly in the next step without purification.

[0359] Synthesis of compound CPD414-3:

[0360] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD414-3 (19.74 g, mass fraction purity: 99.78%, yield: 72.52%), and the mass spectrometry characterization result is: 353.02 (M+H).

[0361] Synthesis of compound CPD414-4:

[0362] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD414-4 (35.49 g, mass fraction purity: 98.06%, yield: 73.62%), and the mass spectrometry characterization result is: 322.16 (M+H).

[0363] Synthesis of compound CPD414-6:

[0364] Referring to the synthesis and purification method of 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)

[0365] Synthesis of compound CPD414:

[0366] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD414 (16.05 g, mass fraction purity: 99.94%, yield: 72.96%) as a pale yellow solid. 16.05 g of the crude pale yellow solid CPD414 was purified by sublimation to obtain sublimation-purified CPD414 (12.59 g, yield: 78.45%). Mass spectrometry analysis revealed a mass spectrometric index of 679.20 (M+H).

[0367] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.62(s,1H),8.32-8.27(m,1H),8.04-7.98(m,2H),7.98-7.86(m,7H),7.78(d,J=2.2Hz,1H),7.66(d,J=2.0Hz,1H),7. 63(dd,J=7.8,2.1Hz,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).

[0368] Synthesis of compound CPD442:

[0369] Synthesis route:

[0370] Synthesis of compound CPD442:

[0371] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD442 (15.42 g, 99.94% purity, 73.85% yield) as a pale yellow solid. 15.42 g of crude CPD442 was purified by sublimation to obtain pure CPD442 (11.86 g, 99.92% purity, 76.92% yield), characterized by a mass spectrometry result of 653.21 (M+H).

[0372] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.61(dd,J=8.5,3.7Hz,2H),8.47-8.39(m,1H),8.33-8.28(m,1H),8.08(d,J=2.0Hz,1H),8.00(d,J=2.1Hz,1 H),7.97-7.85(m,7H),7.82(d,J=7.3Hz,1H),7.56-7.39(m,6H),7.35-7.24(m,4H),7.17-7.07(m,3H),6.97(dd,J=7.5,2.1Hz,1H).

[0373] Synthesis of compound CPD450:

[0374] Synthesis route:

[0375] Synthesis of compound CPD450-1:

[0376] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD450-1 (20.00 g, mass fraction purity: 99.83%, yield: 74.56%), and the mass spectrometry characterization result is: 539.02 (M+H).

[0377] Synthesis of compound CPD450:

[0378] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD450 (16.74 g, mass fraction purity: 99.94%, yield: 73.22%) as a pale yellow solid. 16.74 g of the crude pale yellow solid CPD450 was purified by sublimation to obtain sublimation-purified CPD450 (13.05 g, yield: 77.96%). Mass spectrometry analysis revealed a mass spectrometric index of 855.24 (M+H).

[0379] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.61 (dd, J=8.5, 3.7Hz, 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=8.0Hz,1H),7.99(d,J=7.4H z,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=7.5,2.1Hz,1H).

[0380] Synthesis of compound CPD461:

[0381] Synthesis route:

[0382] Synthesis of compound CPD461-2:

[0383] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD461-2 (32.11 g, mass fraction purity: 99.74%, yield: 72.41%), and the mass spectrometry characterization result is: 404.12 (M+H).

[0384] Synthesis of compound CPD461:

[0385] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD461 (17.77 g, 99.93% purity, 74.96% yield) as a pale yellow solid. 17.77 g of crude CPD461 was purified by sublimation to obtain sublimation-purified CPD461 (13.95 g, 99.92% purity, 78.51% yield). Mass spectrometry analysis revealed a mass index of 720.20 (M+H).

[0386] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.61(dd,J=8.5,3.7Hz,2H),8.46-8.41(m,1H),8.34-8.28(m,1H),8.08(d,J=2.0Hz,1H),8.00(d,J=7.2Hz,2 H),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=2.1Hz,2H),7.20(dd,J=7.2,2.1Hz,2H).

[0387] Synthesis of compound CPD468:

[0388] Synthesis route:

[0389] Synthesis of compound CPD468-2:

[0390] Referring to the synthesis and purification method of compound CPD26-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD468-2 (25.74 g, mass fraction purity: 99.69%, yield: 73.52%), and the mass spectrometry characterization result is: 502.22 (M+H).

[0391] Synthesis of compound CPD468:

[0392] 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 (15.01 g, mass fraction purity: 99.94%, yield: 73.22%) as a light yellow solid. 15.01 g of crude light yellow solid CPD468 was purified by sublimation to obtain sublimation-purified CPD468 (11.08 g, mass fraction purity: 99.94%, yield: 73.82%). Mass spectrometry analysis revealed a mass spectrometric index of 818.24 (M+H).

[0393] NMR characterization results: 1H NMR (400MHz, CDCl3) δ8.61 (dd, J=8.5, 3.7Hz, 2H), 8.47-8.40 (m, 2H), 8.33- 8.28(m,1H),8.16(d,J=2.2Hz,1H),8.08(d,J=2.0Hz,1H),8.00(d,J=7.1Hz, 1H),7.98-7.83(m,9H),7.56-7.47(m,5H),7.47-7.40(m,3H),7.38(dd,J=7 .2,2.1Hz,1H),7.35-7.27(m,4H),7.24(d,J=2.1Hz,1H),7.22-7.12(m,4H).

[0394] Synthesis of compound CPD484:

[0395] Synthesis route:

[0396] Synthesis of compound CPD484-2:

[0397] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD484-2 (25.77 g, mass fraction purity: 98.88%, yield: 74.12%), and the mass spectrometry characterization result is: 355.12 (M+H).

[0398] Synthesis of compound CPD484-3:

[0399] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD484-3 (20.11 g, mass fraction purity: 99.54%, yield: 71.52%), and the mass spectrometry characterization result is: 383.02 (M+H).

[0400] Synthesis of compound CPD484-4:

[0401] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD484-4 (22.53 g, yield: 95.86%) as a white solid. The mass spectrometry result was 411.14 (M+H). The obtained compound was used directly in the next step without purification.

[0402] Synthesis of compound CPD484-5:

[0403] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD484-4 (18.88 g, mass fraction purity: 99.75%, yield: 75.62%), and the mass spectrometry characterization result is: 379.12 (M+H).

[0404] Synthesis of compound CPD484:

[0405] Referring to the synthesis and purification methods for compound CPD2, only the corresponding starting materials were modified to obtain the target compound CPD484 (15.55 g, 99.94% purity, 76.22% yield) as a pale yellow solid. 15.55 g of crude CPD484 was purified by sublimation to obtain sublimation-purified CPD484 (11.85 g, 99.94% purity, 76.21% yield), characterized by a mass spectrometry result of 588.20 (M+H).

[0406] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.62(d,J=9.3Hz,1H),8.50(d,J=8.0Hz,1H),8.47-8.39(m, 1H),8.26-8.24(m,1H),8.11-8.03(m,2H),7.94(d,J=8.1Hz,1H),7.91-7.85(m,1 H),7.77(d,J=7.1Hz,1H),7.61-7.47(m,7H),7.44-7.37(m,3H),7.32-7.24(m,2H ),7.19(dd,J=7.2,2.1Hz,1H),7.17-7.07(m,3H),7.03-6.97(m,2H),1.80(s,6H).

[0407] Synthesis of compound CPD493:

[0408] Synthesis route:

[0409] Synthesis of compound CPD493-2:

[0410] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD493-2 (28.77 g, mass fraction purity: 99.02%, yield: 76.74%), and the mass spectrometry characterization result is: 404.14 (M+H).

[0411] Synthesis of compound CPD493-3:

[0412] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD493-3 (24.85 g, mass fraction purity: 99.67%, yield: 73.62%), and the mass spectrometry characterization result is: 432.21 (M+H).

[0413] Synthesis of compound CPD493-4:

[0414] By referring to the synthesis and purification methods of compound CPD2-7, only the corresponding starting materials were changed to obtain the target compound CPD493-4 (23.41 g, yield: 96.66%) as a white solid. The mass spectrometry result was 460.04 (M+H). The obtained compound was used directly in the next step without purification.

[0415] Synthesis of compound CPD493-5:

[0416] Referring to the synthesis and purification method of compound CPD2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD493-4 (20.00 g, mass fraction purity: 99.87%, yield: 77.01%), and the mass spectrometry characterization result is: 428.02 (M+H).

[0417] Synthesis of compound CPD493:

[0418] Referring to the synthesis and purification methods of compound CPD2, only the corresponding raw materials were changed to obtain the target compound CPD493 (18.11 g, mass fraction purity: 99.92%, yield: 75.98%) as a light yellow solid. 18.11 g of the crude light yellow solid CPD493 was purified by sublimation to obtain sublimation-purified CPD493 (15.00 g, mass fraction purity: 99.93%, yield: 82.83%). The mass spectrometry result was 713.24 (M+H).

[0419] NMR characterization results: 1 H NMR(400MHz, CDCl3)δ8.60(d,J=9.0Hz,1H),8.52(d,J=8.0Hz,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=8.1Hz,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).

[0420] Synthesis of compound CPD497:

[0421] Synthesis route:

[0422] Synthesis of compound CPD497-2:

[0423] Referring to the synthesis and purification method of compound CPD2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD497-2 (20.11 g, mass fraction purity: 99.15%, yield: 74.63%), and the mass spectrometry characterization result is: 329.10 (M+H).

[0424] Synthesis of compound CPD497-3:

[0425] Referring to the synthesis and purification method of compound CPD2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound CPD497-3 (19.78 g, mass fraction purity: 99.62%, yield: 74.44%), and the mass spectrometry characterization result is: 519.12 (M+H).

[0426] Synthesis of compound CPD497:

[0427] 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 (16.22 g, mass fraction purity: 99.93%, yield: 74.63%) as a light yellow solid. 16.22 g of the crude light yellow solid CPD497 was purified by sublimation to obtain sublimation-purified CPD497 (12.86 g, mass fraction purity: 99.93%, yield: 79.29%). The mass spectrometry result was 804.26 (M+H).

[0428] NMR characterization results: 1 H NMR (400MHz, CDCl3) δ8.17 (dd, J=9.2, 0.7Hz, 1H), 8.11 (d, J=2.4Hz, 1H), 8.0 7-8.01(m,2H),7.97-7.82(m,5H),7.72(dd,J=7.3,2.4Hz,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=7.3H z, 1H), 7.27 (t, J = 7.0Hz, 1H), 7.17 (dd, J = 6.9, 1.2Hz, 1H), 6.97-6.91 (m, 4H).

[0429] Application example: Fabrication of organic electroluminescent devices

[0430] In one embodiment, as shown in Figure 2, Figure 2 is a schematic diagram of the structure of an organic electroluminescent device, which includes a stacked 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.

[0431] A 50 mm*50 mm*1.0 mm glass substrate with an ITO (anode 2, indium tin oxide, 100 nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150° C., and then treated with N 2 plasma for 30 minutes. The washed glass substrate was mounted on a substrate holder of a vacuum evaporation apparatus, and compound NDP-9 and compound HTM 1 were evaporated at a weight ratio of 97:3 to form a hole injection layer with a thickness of 10 nm, followed by evaporation of a layer of HTM1 to form a thin film with a thickness of 60 nm as HTL1 (hole transport layer 1), and then a layer of HTM2 was evaporated on the HTM1 film to form a thin film with a thickness of 10 nm as HTL2 (hole transport layer 2), and then, a light-emitting layer with a thickness of 40 nm was co-evaporated on the HTM2 film layer in the form of a single host or a double host (host material: red light doping material = 97%: 3%, mass fraction), wherein the host materials of the single host or the double host were the compound of the present invention, RH-N, and comparative compounds 1-5, respectively. On the light-emitting layer, ETL (electron transport layer) material and LiQ are co-evaporated (35nm) in a weight ratio of 50:50 as an electron transport material, and then LiQ (1nm) is evaporated on the electron transport material layer as an electron injection material to form an electron injection layer. Then, Mg / Ag (100nm, mass ratio of 1:9) is evaporated as the cathode material using a co-evaporation mode to produce an organic electroluminescent device.

[0432] 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:

[0433] evaluate:

[0434] The organic electroluminescent device was tested for device performance. The compounds prepared in the present invention and comparative compounds 1-5 were used as the main materials for comparison. A constant current source (Keithley 2400) was used to flow a fixed current density through the light-emitting element. The luminescence spectrum was measured using a spectroradiometer (CS2000). At the same time, the current density was 10 mA / cm 2The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm 2 The LT95 device lifespan was tested under the following conditions. The results are shown in Tables 1 and 2 below.

[0435] The device performance data using the compounds of the present invention and comparative compounds 1-5 as single hosts and co-evaporated with red light doping materials to form a light-emitting layer 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).

[0436] Table 1

[0437] Table 2 shows the device data of the light-emitting layer formed by co-evaporating the compound of the present invention, the comparative compound and the RH-N material in a mixing ratio of 5:5 with the red light doping material.

[0438] Table 2

[0439] As can be seen from Table 1-2, the device lifespan of the device prepared using the compound of the present invention is significantly better than that of the device prepared using the comparative compound 1-5.

[0440] Sublimation temperature comparison: Sublimation temperature is defined as: -7 The vacuum degree is 1000 Torr and the temperature corresponding to the sublimation rate is 1 angstrom per second. The test results are shown in Table 3.

[0441] Table 3

[0442] As can be seen from Table 3, the compounds of the present invention have lower sublimation temperatures than comparative compounds 2-4, which is conducive to industrial application.

[0443] As a single-host red light-emitting material, the compound of the present invention has lower voltage, higher current efficiency and longer life than the comparative compound; at the same time, when the compound of the present invention is combined with an N-type material as a dual-host material, it has balanced hole and electron transfer rates and broadened the exciton recombination area in the light-emitting layer, greatly improving the efficiency and life of the device compared with comparative compounds 1-5.

[0444] Therefore, the compound material of the present invention has advantages such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a host material in OLED light-emitting devices. Furthermore, its low melting point, as a molten material, facilitates material evaporation stability. As a host material, the compound of the present invention has potential application in the AMOLED industry.

[0445] In addition, since it is impossible to enumerate all the compounds of the present invention, the above Tables 1-3 only list the properties of some of the compounds or devices of the present invention. However, within the scope of protection claimed in the present invention, especially the compounds with specific structural formulas given in the present invention, all have advantages similar to CPD2, such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

Claims

1. A compound, characterized in that Its general structural formula is shown in formula (1): Wherein, ring A is selected from the following formula (2) or formula (3); Among them, X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1); 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 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; two adjacent R0 may be connected to form a ring; In formula (1), X is selected from NR a , CR b R c or oxygen group elements; R a 、R b 、R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, and C6-C30 arylsilyl; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ar1 and Ar2 are 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, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbon-substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

2. The compound according to claim 1, characterized in that The 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 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine; and / or The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

3. The compound according to claim 2, characterized in that The 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 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino or C6-C20 arylamine; and / or The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

4. The compound according to claim 1, characterized in that The chalcogen element is selected from O, S or Se.

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

6. The compound according to claim 1, characterized in that The heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si and Ge.

7. The compound according to any one of claims 1 to 6, characterized in that The structures represented by formula (2) and formula (3) are selected from the structures represented by the following formulas (A-1) to (A-8): Wherein, * represents the site fused to the 5-membered ring containing X in formula (1); Wherein a is an integer of 0-10; if a≥2 or a larger integer, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

8. The compound according to any one of claims 1 to 6, characterized in that The structures represented by formula (2) and formula (3) are selected from the structures represented by the following formulas (A-9) to (A-16): Wherein, * represents the site fused to the 5-membered ring containing X in formula (1); Wherein a is an integer of 0-6; if a≥2 or a larger integer, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

9. The compound according to any one of claims 1 to 6, characterized in that L is a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C60 heteroarylene group; and / or, X is CR b R c , O or S; and / or, The R b 、R c are independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C5-C10 heteroaryl; and / or, X1-X 12 Contains at least one N.

10. The compound according to any one of claims 1 to 6, 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 benzocycloalkyl, substituted or unsubstituted phenanthroxazolyl, oxaspirofluorenyl, substituted or unsubstituted benzocarbazolyl, or a combination of at least two of the foregoing.

11. The compound according to claim 1, characterized in that The aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrenyl, phenyl, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl.

12. The compound according to claim 1, characterized in that The heteroaryl group is selected from pyrrolyl, pyrazinyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, and quinazolinyl.

13. The compound according to any one of claims 1 to 6, characterized in that The compound is one of the following structural formulas, or a structure in which hydrogen is partially or completely replaced by deuterium or fluorine:

14. An organic electroluminescent device, characterized in that: The invention comprises the compound according to any one of claims 1 to 13.

15. The organic electroluminescent device according to claim 14, characterized in that: The invention comprises a light-emitting layer, wherein the light-emitting layer comprises the compound according to any one of claims 1 to 13.

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