Compound and light-emitting device

Abstract

Provided in the present invention are a compound and a light-emitting device. The compound of the present invention has a structure as shown in formula (1). In the present invention, the compound obtained by connecting substituted alkyl fluorene to a nitrogen heterocyclic ring has the advantages of good light stability, electrical stability and heat stability, high luminous efficiency, low voltage, long lifetime, etc., and can be used in light-emitting devices; and in particular, the compound is expected to be applied to the AMOLED industry as a hole blocking layer material and an electron transport layer material.

Description

A compound and a light-emitting device Technical Field

[0001] The present application relates to the field of organic electroluminescence technology, and in particular to an organic light-emitting material suitable for use in a light-emitting device, and more particularly to a compound in which a substituted alkylfluorene is connected to a nitrogen heterocycle and a light-emitting device thereof. Background Art

[0002] Currently, light-emitting devices, as a next-generation display technology, are gaining increasing attention in both display and lighting technologies, with promising applications. However, compared to market application requirements, performance of light-emitting devices, such as luminous efficiency, driving voltage, and service life, still needs to be further enhanced and improved, especially for OLED devices.

[0003] Generally speaking, the basic structure of an OLED device consists of thin films of organic functional materials with various functions sandwiched between metal electrodes, like a sandwich. 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 energy as light or heat, thus generating the OLED's luminescence. However, organic functional materials are the core components of light-emitting devices, and the material's thermal stability, photochemical stability, electrochemical stability, quantum yield, film-forming stability, crystallinity, and color saturation are all major factors affecting device performance.

[0004] Patent document 1 (CN106132937A) records Compounds in which 9,9-diphenylfluorene is bonded to a triazine ring via a linker can be used as electron injection and transport materials in light-emitting devices. The device voltage is high, while the efficiency and lifespan need to be further improved. Patent document 2 (CN111433190A) describes Compounds in which cyclohexylfluorene is bonded to a triazine ring via a linker can be used as host materials and electron transport materials for light-emitting devices, and the efficiency of the devices needs to be improved. Patent document 3 (CN110615759B) describes Compounds in which adamantyl fluorene is bonded to a triazine ring via a linker are used as electron transport layer materials in light-emitting devices, but their luminous efficiency, lifespan and other performances need to be further improved. Patent Document 4 (CN114763341A) describes Compounds in which a norbornyl fluorenyl group is bonded to a nitrogen heterocycle via a linker are used as electron transport layer materials in light-emitting devices. However, their material stability, luminous efficiency, lifespan and other performance aspects need to be further improved. Patent document 5 (KR1020210156912A) describes Compounds in which benzoheterocyclic and fluorenyl groups are bonded to nitrogen heterocycles via linkers are used as electron transport layer materials in light-emitting devices. They have strong planarity, high sublimation temperature, and poor material stability. At the same time, the device's luminous efficiency, lifespan and other performance aspects need to be further improved.

[0005] Summary of the Invention

[0006] The present application has been made to solve the above-mentioned problems, and an object of the present application is to provide a high-performance light-emitting device and a novel material that can realize such a light-emitting device.

[0007] The present applicant has conducted intensive studies to achieve the aforementioned object and has found that a high-performance light-emitting device can be obtained by using a compound represented by the following formula (1).

[0008] One of the objectives of this application is to provide a compound comprising a substituted alkylfluorene linked to a nitrogen heterocycle. This compound exhibits excellent film-forming properties, excellent optical, electrical, and thermal stability, high luminous efficiency, low voltage, and long life, and can be used in light-emitting devices. In particular, it has potential applications in the AMOLED industry as a hole-blocking layer material and an electron-transporting layer material.

[0009] To achieve the above objectives, this application adopts the following technical solutions:

[0010] A compound, the structural formula of which is shown in formula (1):

[0011] wherein X is independently selected from C(R4)2, O, S, NR5;

[0012] wherein n is independently selected from 0 or an integer of 1-6; when n=0, they are not connected to form a ring; when n≥1, they are connected to form a ring; when n≥2, each X is the same or different;

[0013] Wherein, X1, X2, X3 are independently selected from N or CR6, and at least one is N;

[0014] R1, R2, and R3 are ring substituents independently selected from 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, C5-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;

[0015] R4, R5, and R6 are each 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, C5-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;

[0016] L is selected from a single bond, or a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 30 ring atoms;

[0017] wherein a, b, c are independently selected from integers ranging from 0 to 8,

[0018] wherein Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0019] The heteroatoms in each heteroaryl, heteroalkyl or heterocycloalkyl group are independently selected from at least one heteroatom of O, S, N, Se, Si and Ge;

[0020] The substitution is substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amino, C6-C12 aryl, cyano, isocyano or phosphino, and the number of substitutions of each substituent group is independently selected from one of single substitution to the maximum number of substitutions.

[0021] In some embodiments, a compound is selected from the structures shown in the following formula (2) and formula (3);

[0022] When n=0, they are not connected to form a ring and X does not exist; when n≥1, they are connected to form a ring; when n≥2, X is multiple C(R4)2; or a combination of one or more C(R4)2 and one of O, S, and NR5.

[0023] In some embodiments, in the formulas (1)-(3) Selected from the structures shown in the following formulas A-1 to A-8;

[0024] In some embodiments, wherein L is selected from a single bond and the structures shown in the following formulas B-1 to B-18;

[0025] wherein R is a substituent, each R being independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamine;

[0026] m is selected from integers of 0-4.

[0027] In some embodiments, each R is independently selected from deuterium or C1-C4 alkyl.

[0028] In some embodiments, X1-X3 contain at least two Ns;

[0029] R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamine;

[0030] R6 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-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine.

[0031] wherein two of X1-X3 are N and the remaining one is CH or N; and R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino, or C6-C30 arylamine.

[0032] X1-X3 are all N, or X1 and X2 are N and X3 is CH; R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C5-C12 heteroaryl, C1-C10 alkoxy, C6-C12 aryloxy, or C6-C12 arylamine.

[0033] In some embodiments, X1-X3 are all N, and a, b, and c are all 0.

[0034] In some embodiments, wherein Ar1 and Ar2 are each independently selected from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, pyrenyl, phenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylenyl or a combination of at least two of the foregoing.

[0035] As a compound in some embodiments, wherein the structure of formula (1) contains at least one deuterium atom. As a compound in some embodiments, selected from but not limited to the following structures;

[0036] One of the purposes of the present application is also to provide a light-emitting device comprising the above-mentioned compound, which comprises an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers comprises the above-mentioned compound.

[0037] The material of the present application is used as the material of at least one of the light-emitting layer, the hole blocking layer, and the electron transport layer in the organic layer in the light-emitting device.

[0038] The material of the present application is used as a hole blocking layer material in a light-emitting device.

[0039] The light-emitting device of the present application may be an organic light-emitting device or a quantum dot light-emitting device. In some embodiments, when the light-emitting device is an organic light-emitting device, the compound may be used as a material for the light-emitting layer, hole-blocking layer, or electron-transporting layer; when the light-emitting device is a quantum dot light-emitting device, the compound may be used as a material for the hole-blocking layer or electron-transporting layer.

[0040] In some embodiments, the light emitting device is an organic electroluminescent device.

[0041] The materials in this application have advantages such as good film-forming properties, excellent optical, electrical, and thermal stability, high luminous efficiency, low voltage, and long life, and can be used in organic light-emitting devices. In particular, as hole-blocking layer materials and electron-transport layer materials, they have potential applications in the AMOLED industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 shows the structure of compound CPD 108. 1 HNMR spectrum.

[0043] FIG2 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application. DETAILED DESCRIPTION

[0044] A compound, the structural formula of which is shown in formula (1):

[0045] wherein X is independently selected from C(R4)2, O, S, NR5;

[0046] wherein n is independently selected from 0 or an integer of 1-6; when n=0, they are not connected to form a ring; when n≥1, they are connected to form a ring; when n≥2, each X is the same or different;

[0047] As an embodiment of the present invention, when n=0, they are not connected to form a ring and X does not exist; when n≥1, they are connected to form a ring; when n≥2, X is multiple C(R4)2; or a combination of one or more C(R4)2 and one of O, S, and NR5.

[0048] Wherein, X1, X2, X3 are independently selected from N or CR6, and at least one is N;

[0049] R1, R2, and R3 are each independently selected from 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, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 monoarylphosphino, C6-C60 diarylphosphino, or C6-C60 arylamine;

[0050] R4, R5, and R6 are each 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, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 monoarylphosphino, C6-C60 diarylphosphino, or C6-C60 arylamine;

[0051] L is selected from a single bond, or a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 30 ring atoms;

[0052] wherein a, b, and c are independently selected from integers of 0 to 8, and R1, R2, and R3 are substituents on the corresponding rings. When a, b, and c are 0, the corresponding positions on the rings are hydrogen and there is no substituent.

[0053] wherein Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0054] The heteroatom in the heteroaryl, heteroalkyl or heterocycloalkyl group is selected from at least one heteroatom of O, S, N, Se, Si and Ge;

[0055] The substitution is substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amino, C6-C12 aryl, cyano, isocyano or phosphino, and the number of substitutions of each substituent group is independently selected from one of single substitution to the maximum number of substitutions.

[0056] The embodiments are only for facilitating understanding of the technical invention and should not be regarded as specific limitations of the present application.

[0057] The raw materials and solvents involved in the synthesis of the compounds in this application were purchased from suppliers well known to those skilled in the art, such as Alfa and Acros.

[0058] Example:

[0059] 1. Synthesis route of compound CPD 4

[0060] Synthesis of compound CPD 4-3

[0061] Compound CPD 4-1 (50.00 g, 186.88 mmol) and dry tetrahydrofuran (750 ml) were added to a 2000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was cooled to -78°C. Then, a solution of n-butyllithium in n-hexane (121.47 ml, 242.95 mmol, 2 mol / L) was added dropwise over 1 hour, controlling the internal temperature to remain below -70°C. The addition was complete, and the mixture was stirred at -78°C for 1 hour. Finally, CPD 4-2 (33.02 g, 261.63 mmol) was added all at once, and stirring was continued at -78°C for 1.5 hours. TLC (ethyl acetate:n-hexane = 1:30 as the developing solvent) confirmed the complete consumption of the starting material CPD 4-1, with the majority of CPD 4-3 generated. Deionized water (300 ml) was added dropwise to the system to quench the reaction. After warming to room temperature, the mixture was separated directly. The aqueous phase was extracted once with ethyl acetate (500 ml). The combined organic phases were concentrated under reduced pressure at 65°C for 1 hour to obtain a light yellow solid. The sample was mixed with silica gel and dry-loaded onto a chromatography column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:30 as eluent). After elution, the mixture was concentrated under reduced pressure at 65°C for 1.5 hours to obtain CPD 4-3 (38.51 g, purity: 99.78%, yield: 65.45%) as a white solid. Mass spectrum: 315.15 (M+H).

[0062] Synthesis of compound CPD 4-4

[0063] CPD 4-3 (37.00 g, 117.52 mmol) and dichloromethane (370 ml) were added to a 1000 ml three-necked round-bottom flask. The system was then cooled to 0°C and trifluoromethanesulfonic acid (35.27 g, 235.03 mmol) was added dropwise over 15 minutes. The temperature was maintained with stirring for 30 minutes. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:30 as the developing solvent). The starting material CPD 4-3 was completely consumed. Deionized water (100 ml) was added dropwise to the system to quench the reaction. The mixture was separated and the sample was dry-loaded onto a silica gel chromatography column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:50 as eluent). After elution, the mixture was concentrated under reduced pressure at 65°C for 2 hours to give CPD 4-4 (29.92 g, purity: 99.91%, yield: 85.76%) as a white solid. Mass spectrum: 297.12 (M+H).

[0064] Synthesis of compounds CPD 4-6

[0065] CPD 4-4 (35.00 g, 117.91 mmol), CPD 4-5 (35.93 g, 141.49 mmol), tris(dibenzylideneacetone)dipalladium (2.16 g, 2.36 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (2.25 g, 4.72 mmol), potassium acetate (23.14 g, 235.82 mmol), and 1,4-dioxane (350 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 (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material CPD 4-4 was completely consumed. The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (800 ml) was added, and the mixture was washed with deionized water (300 ml*3). The liquids were separated, and the sample was mixed with silica gel and dry-loaded onto a chromatography 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 mixture was concentrated under reduced pressure at 65°C for 1 hour to obtain a white solid, CPD 4-6 (38.95 g, purity: 99.00%, yield: 85.06%), with a mass spectrum of 389.26 (M+H).

[0066] Synthesis of compound CPD 4

[0067] CPD 4-7 (20.00 g, 47.63 mmol), CPD 4-6 (19.42 g, 50.01 mmol), bis(4-dimethylaminophenyldi-tert-butylphosphine)palladium dichloride (0.697 g, 0.95 mmol), potassium carbonate (13.16 g, 95.26 mmol), toluene (300 ml), ethanol (100 ml), and deionized water (100 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 65°C for 2 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent), indicating complete consumption of the starting material CPD 4-7. The temperature was cooled to room temperature, and methanol (300 ml) was added. The mixture was stirred at room temperature for 1 hour, resulting in the precipitation of a large amount of solid. Toluene (450 ml) was added, the system was heated to 100°C for dissolution, then cooled to room temperature and filtered through 300-400 mesh silica gel (50 g). Methanol (450 ml) was added to the filtrate at room temperature, stirred at room temperature for 1 hour, and filtered to obtain a wet white solid. The solid was dried at 80°C for 1 hour to obtain 25.38 g of a white solid. The solid was added to a 100 ml single-necked round-bottom flask and recrystallized once with toluene (254 ml) and methanol (127 ml). The mixture was filtered and the filter cake was dried under vacuum at 80°C for 5 hours to obtain CPD 4 (22.18 g, purity: 99.96%, yield: 72.11%) as a white solid. 22.18 g of the crude CPD 4 was purified by sublimation to obtain pure CPD 4 (17.96 g, purity: 99.97%, yield: 80.98%). Mass spectrum: 646.22 (M+H). 1 H NMR (400MHz, CDCl3) δ8.35-8.33(m,1H),8.30-8.22(m,5H),8.13-8.11(m,1H),8.07(s,1H),8.04-8.00(m,4H),7.92-7.88(m,4H) ,7.82-7.79(m,1H),7.76-7.73(m,6H),7.69-7.61(m,2H),2.61-2.58(m,2H),2.36-2.30(m,2H),1.91-1.88(m,4H),1.20(s,6H).

[0068] 2. Synthesis route of compound CPD 34

[0069] Synthesis of compound CPD 34-2

[0070] Referring to the synthesis and purification methods of compound CPD 4-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 34-2 (35.12 g, purity: 99.81%, yield: 66.35%), mass spectrum: 355.12 (M+H).

[0071] Synthesis of compound CPD 34-3

[0072] Referring to the synthesis and purification methods of compound CPD 4-4, only the corresponding raw materials need to be changed to obtain the target compound CPD 34-3 (27.56 g, purity: 99.91%, yield: 84.36%), mass spectrum: 337.42 (M+H).

[0073] Synthesis of compound CPD 34-4

[0074] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD 34-4 (29.64 g, purity: 99.87%, yield: 86.33%), mass spectrum: 429.02 (M+H).

[0075] Synthesis of compound CPD 34

[0076] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 34 (38.45 g, purity: 99.93%, yield: 74.12%). 38.45 g of crude CPD 34 was purified by sublimation to obtain pure CPD 34 (31.68 g, purity: 99.94%, yield: 82.40%), mass spectrum: 610.32 (M+H). 1 HNMR(400MHz, CDCl3)δ8.12-8.04(m,2H),8.00(dd,J=9.6,2.1Hz,1H),7.97-7.89(m ,3H),7.79(dd,J=6.7,1.1Hz,1H),7.73(d,J=2.0Hz,1H),7.72-7.66(m,2H),7.60-7 .55(m,2H),7.55-7.44(m,4H),7.44-7.37(m,3H),7.36-7.27(m,2H),2.38-2.33(m, 2H),2.13-2.08(m,2H),1.71(t,J=6.1Hz,4H),1.52-1.45(m,4H),1.43-1.33(m,6H).

[0077] 3. Synthesis of compound CPD 63

[0078] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 63 (32.42 g, purity: 99.94%, yield: 76.32%). 32.42 g of crude CPD 63 was purified by sublimation to obtain pure CPD 63 (26.02 g, purity: 99.94%, yield: 80.26%), mass spectrum: 570.22 (M+H). 1 H NMR (400MHz, CDCl3) δ8.12-8.04(m,4H),8.02(d,J=7.7Hz,1H),7.97-7.91(m,2H),7.80-7.78(m,1H),7.72-7.64(m ,3H),7.55-7.44(m,8H),7.36-7.27(m,2H),2.28-2.22(m,2H),2.02-1.97(m,2H),1.56-1.53(m,4H),1.21(s,6H).

[0079] 4. Synthesis of compound CPD 83

[0080] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 83 (28.88 g, purity: 99.95%, yield: 75.00%). 28.88 g of crude CPD 83 was purified by sublimation to obtain pure CPD 83 (22.80 g, purity: 99.95%, yield: 78.95%), mass spectrum: 570.22 (M+H). 1 H NMR (400MHz, CDCl3) δ8.20(t,J=2.1Hz,1H),8.02(d,J=7.9Hz,1H),7.90-7.85(m,4H),7.85-7.80(m,2H),7.79-7.77(m,2H),7.64-7.62(m,1H), 7.57-7.53(m,1H),7.49-7.42(m,6H),7.36(s,1H),7.36-7.27(m,2H),2 .28-2.22(m,2H),2.02-1.97(m,2H),1.56(t,J=6.3Hz,4H),1.20(s,6H).

[0081] 5. Synthesis of compound CPD 90

[0082] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 90 (29.06 g, purity: 99.93%, yield: 76.52%). 29.06 g of crude CPD 90 was purified by sublimation to obtain pure CPD 90 (22.56 g, purity: 99.94%, yield: 77.64%), mass spectrum: 660.00 (M+H). 1 H NMR(400MHz, CDCl3)δ8.21(t,J=2.1Hz,1H),8.12-8.04(m,3H),8.02(d,J=7.9 Hz,1H),7.99-7.89(m,2H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.72(d,J=2 .2Hz,1H),7.67-7.59(m,2H),7.59-7.38(m,7H),7.36(s,1H),7.35-7.27(m,2 H),2.28-2.22(m,2H),2.02-1.97(m,2H),1.56(t,J=6.3Hz,4H),1.22(s,6H).

[0083] 6. Synthesis of compound CPD 108

[0084] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 108 (25.11 g, purity: 99.97%, yield: 74.52%). 25.11 g of crude CPD 108 was purified by sublimation to obtain pure CPD 108 (18.85 g, purity: 99.97%, yield: 75.07%), mass spectrum: 646.21 (M+H). 1 H NMR (400MHz, CDCl3) δ9.07 (s, 1H), 8.83 (d, J = 6.8Hz, 5H), 8.01 (s, 1H), 7.94-7.91 (m, 2H), 7.87-7.85 (m, 1H), 7.82-7 .80(m,1H),7.79-7.56(m,12H),7.41(t,J=7.3Hz,1H),7.35(t,J=7.2Hz,1H),1.96(m,2H),1.82(m,6H),1.25(s,6H).

[0085] 7. Synthesis route of compound CPD 119

[0086] Synthesis of compound CPD 119-3

[0087] CPD 119-1 (25.00 g, 72.71 mmol), CPD 119-2 (21.97 g, 94.53 mmol), tetrakis(triphenylphosphine)palladium (1.68 g, 1.45 mmol), potassium carbonate (20.10 g, 145.42 mmol), tetrahydrofuran (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 70°C for 4 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent). The starting material CPD 119-1 was completely consumed. The solvent was directly concentrated and removed, dichloromethane (500 ml) was added, and the product was washed with deionized water (150 ml * 3). The liquids were separated, and the sample was mixed with silica gel and dry-loaded onto a chromatography 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 65°C for 1 hour to obtain a white solid CPD 119-3 (29.97 g, purity: 99.32%, yield: 83.10%), mass spectrum: 496.20 (M+H).

[0088] Synthesis of compound CPD 119

[0089] CPD 119-3 (25.00 g, 50.40 mmol), CPD 4-6 (23.49 g, 60.48 mmol), tris(dibenzylideneacetone)dipalladium (0.92 g, 1.00 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.95 g, 2.00 mmol), cesium carbonate (35.56 g, 100.80 mmol), toluene (375 ml), ethanol (125 ml), and deionized water (125 ml) were added to a 2000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 90°C for 12 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent), indicating complete consumption of the starting material CPD 119-3. The mixture was cooled to room temperature, and methanol (300 ml) was added. The mixture was stirred at room temperature for 1 hour, resulting in the precipitation of a large amount of solid. Toluene (500 ml) was added, the system was heated to 120°C for dissolution, then cooled to room temperature and filtered through 300-400 mesh silica gel (60 g). Methanol (200 ml) was added to the filtrate at room temperature, stirred at room temperature for 1 hour, and filtered to obtain a wet white solid. The solid was dried at 100°C for 1 hour to obtain 30.68 g of a white solid. The solid was added to a 1000 ml single-necked round-bottom flask and recrystallized once with toluene (301 ml) and methanol (154 ml). The solid was filtered and the filter cake was dried under vacuum at 100°C for 12 hours to obtain CPD 119 (27.65 g, purity: 99.94%, yield: 76.00%) as a white solid. 27.65 g of the crude CPD 119 was purified by sublimation to obtain pure CPD 119 (22.55 g, purity: 99.94%, yield: 81.56%). Mass spectrum: 722.32 (M+H). 1 H NMR(400MHz, CDCl3)δ8.21(t,J=2.1Hz,1H),8.12(t,J=1.8Hz,1H),8.10-8.04(m,2H),8.0 2(d,J=7.9Hz,1H),7.90-7.82(m,2H),7.81-7.75(m,2H),7.71(t,J=2.2Hz,1H),7.65-7.63 (m,1H),7.58-7.54(m,7H),7.52-7.46(m,4H),7.42(d,J=1.9Hz,1H),7.41-7.36(m,3H),7. 36-7.27(m,3H),2.28-2.22(m,2H),2.04-1.98(m,2H),1.58(t,J=6.3Hz,4H),1.19(s,6H).

[0090] 8. Synthesis route of compound CPD 128

[0091] Synthesis of compound CPD 128-3

[0092] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 128-3 (30.05 g, purity: 99.23%, yield: 82.78%), mass spectrum: 358.10 (M+H).

[0093] Synthesis of compound CPD 128-4

[0094] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD 128-4 (34.66 g, purity: 98.09%, yield: 85.74%), mass spectrum: 450.20 (M+H).

[0095] Synthesis of compound CPD 128-6

[0096] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 128-6 (28.41 g, purity: 99.52%, yield: 85.09%), mass spectrum: 448.14 (M+H).

[0097] Synthesis of compound CPD 128

[0098] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 128 (16.01 g, purity: 99.93%, yield: 76.00%). 16.01 g of crude CPD 128 was purified by sublimation to obtain pure CPD 128 (12.79 g, purity: 99.95%, yield: 79.89%), with a mass spectrum of 674.36 (M+H). 1 H NMR (400MHz, CDCl3) δ8.12-8.05(m,5H),8.02(d,J=7.9Hz,1H),7.86-7.84(m,1H),7.81-7.75(m,3H),7.60-7.58(m,1H),7. 55-7.44(m,7H),7.38-7.27(m,5H),2.40(s,6H),2.28-2.21(m,2H),2.03-1.96(m,2H),1.58(t,J=6.3Hz,4H),1.19(s,6H).

[0099] 9. Synthesis route of compound CPD 136

[0100] Synthesis of compound CPD 136-2

[0101] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 136-2 (45.61 g, purity: 99.46%, yield: 80.00%), mass spectrum: 510.13 (M+H).

[0102] Synthesis of compound CPD 136

[0103] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 136 (27.13 g, purity: 99.95%, yield: 75.19%). 27.13 g of crude CPD 136 was purified by sublimation to obtain pure CPD 136 (21.28 g, purity: 99.95%, yield: 78.44%), with a mass spectrum of 736.42 (M+H). 1 H NMR (400MHz, CDCl3) δ8.21(t,J=2.1Hz,1H),8.12-7.99(m,4H),7.90-7.83(m,2H),7.81-7.75(m,2H),7.71(t,J=2.2Hz,1H),7.65-7.59(m,2H),7.5 8-7.53(m,4H),7.53-7.46(m,5H),7.45-7.41(m,2H),7.38-7.23(m,4H), 2.26-2.21(m,2H),2.04-1.97(m,2H),1.58(t,J=6.3Hz,4H),1.20(s,6H).

[0104] 10. Synthesis route of compound CPD 160

[0105] Synthesis of compound CPD 160-2

[0106] Referring to the synthesis and purification methods of compound CPD 4-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 160-2 (32.56 g, purity: 99.51%, yield: 66.85%), mass spectrum: 357.02 (M+H).

[0107] Synthesis of compound CPD 160-3

[0108] Referring to the synthesis and purification methods of compound CPD 4-4, only the corresponding raw materials need to be changed to obtain the target compound CPD 160-3 (28.02 g, purity: 99.90%, yield: 83.65%), mass spectrum: 339.14 (M+H).

[0109] Synthesis of compound CPD 160-4

[0110] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD 160-4 (30.67 g, purity: 99.90%, yield: 86.23%), mass spectrum: 431.22 (M+H).

[0111] Synthesis of compound CPD 160-6

[0112] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 160-6 (28.06 g, purity: 99.42%, yield: 82.00%), mass spectrum: 420.32 (M+H).

[0113] Synthesis of compound CPD 160

[0114] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 160 (22.96 g, purity: 99.96%, yield: 76.48%). 22.96 g of crude CPD 160 was purified by sublimation to obtain pure CPD 160 (18.25 g, purity: 99.96%, yield: 79.49%), with a mass spectrum of 688.32 (M+H). 1 H NMR (400MHz, CDCl3) δ8.12-8.04(m,4H),7.97-7.91(m,2H),7.81-7.75(m,2H),7.72 -7.64(m,3H),7.60-7.44(m,10H),7.38-7.28(m,4H),3.53-3.50(m,4H),2.3 9-2.34(m,2H),2.14-2.08(m,2H),1.69(t,J=6.2Hz,4H),1.50-1.44(m,4H).

[0115] 11. Synthesis route of compound CPD 179

[0116] Synthesis of compound CPD 179-2

[0117] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 179-2 (25.33 g, purity: 99.89%, yield: 82.96%), mass spectrum: 496.16 (M+H).

[0118] Synthesis of compound CPD 179

[0119] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 179 (24.63 g, purity: 99.94%, yield: 73.56%). 24.63 g of crude CPD 179 was purified by sublimation to obtain pure CPD 179 (20.82 g, purity: 99.96%, yield: 84.54%), with a mass spectrum of 722.30 (M+H). 1 H NMR(400MHz, CDCl3)δ8.21(t,J=2.1Hz,1H),8.12-8.04(m,4H),8.02(d,J=7.9 Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.71(t,J=2.2Hz,2H),7.65-7. 62(m,1H),7.60-7.55(m,5H),7.53-7.45(m,8H),7.36(s,1H),7.36-7.28(m,3 H),2.29-2.21(m,2H),2.01-1.96(m,2H),1.57(t,J=6.3Hz,4H),1.20(s,6H).

[0120] 12. Synthesis route of compound CPD 223

[0121] Synthesis of compound CPD 223-3

[0122] Compound CPD 223-1 (50.00 g, 177.60 mmol) and dry tetrahydrofuran (750 ml) were added to a 2000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was cooled to -78°C. Then, n-butyllithium in n-hexane (97.68 ml, 195.36 mmol, 2 mol / L) was added dropwise, controlling the internal temperature to not exceed -70°C. The addition was completed over 1 hour, and the mixture was maintained at -78°C with stirring for 1 hour. CPD 223-2 (38.89 g, 266.40 mmol) was slowly added dropwise over 10 minutes. The mixture was allowed to warm naturally with stirring for 1 hour. TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent) confirmed that the starting material CPD 223-1 was completely consumed, and most of CPD 223-3 was generated. Aqueous hydrochloric acid solution was added dropwise to the system to quench the reaction (2 mol / L, 100 ml), and a large amount of solid precipitated. The mixture was stirred at room temperature for 1 hour and filtered to obtain a white solid. The mixture was slurried with n-hexane (100 ml) at room temperature for 1 hour, filtered, and the filter cake was dried under vacuum at 65° C. for 3 hours to obtain a white solid CPD 223-3 (36.84 g, purity: 98.06%, yield: 84.16%), mass spectrum: 247.04 (M+H).

[0123] Synthesis of compound CPD 223-4

[0124] Referring to the synthesis and purification methods of compound CPD 119-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 223-4 (27.80 g, purity: 99.54%, yield: 78.96%), mass spectrum: 434.26 (M+H).

[0125] Synthesis of compound CPD 223

[0126] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 223 (23.30 g, purity: 99.96%, yield: 76.60%). 23.30 g of crude CPD 223 was purified by sublimation to obtain pure CPD 223 (18.64 g, purity: 99.96%, yield: 80.00%), with a mass spectrum of 660.20 (M+H). 1H NMR (400MHz, CDCl3) δ8.17 (d, J = 2.7Hz, 1H), 8.12-8.03 (m, 6H), 7.92 -7.85(m,2H),7.81-7.74(m,2H),7.68(dd,J=7.8,2.1Hz,1H),7.58-7.44(m,8H),7.38 -7.28(m,3H),2.28-2.21(m,2H),2.00-1.96(m,2H),1.56(t,J=6.3Hz,4H),1.21(s,6H).

[0127] 13. Synthesis route of compound CPD 255

[0128] Synthesis of compound CPD 255-3

[0129] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding raw materials need to be changed. The reaction solvent is toluene and deionized water. The reaction is carried out at 90°C for 8 hours to obtain the target compound CPD 255-3 (18.24 g, purity: 99.67%, yield: 67.15%), mass spectrum: 354.12 (M+H).

[0130] Synthesis of compound CPD 255

[0131] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 255 (18.31 g, purity: 99.94%, yield: 74.52%). 18.31 g of crude CPD 255 was purified by sublimation to obtain pure CPD 255 (14.85 g, purity: 99.96%, yield: 81.11%), with a mass spectrum of 580.34 (M+H). 1 H NMR (400MHz, CDCl3) δ8.21(t,J=2.1Hz,1H),8.02(d,J=7.8Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.65-7.63(m,1H),7.5 7-7.53(m,1H),7.49-7.46(m,1H),7.38-7.27(m,3H),2.27-2.21(m,2H),2.00-1.95(m,2H),1.54(t,J=6.3Hz,4H),1.21(s,6H).

[0132] 14. Synthesis route of compound CPD 262

[0133] Synthesis of compound CPD 262-1

[0134] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD 262-1 (20.33 g, purity: 99.75%, yield: 67.15%), mass spectrum: 446.22 (M+H).

[0135] Synthesis of compound CPD 262-3

[0136] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding raw materials need to be changed to obtain the target compound CPD 262-3 (13.56 g, purity: 99.89%, yield: 78.06%), mass spectrum: 430.14 (M+H).

[0137] Synthesis of compound CPD 262

[0138] Referring to the synthesis and purification methods for compound CPD 119, only the corresponding starting materials needed to be modified to obtain the target compound CPD 262 (14.36 g, purity: 99.96%, yield: 78.47%). 14.36 g of crude CPD 262 was purified by sublimation to obtain pure CPD 262 (11.01 g, purity: 99.96%, yield: 76.68%), with a mass spectrum of 656.34 (M+H). 1 H NMR(400MHz, CDCl3)δ8.21(t,J=2.1Hz,1H),8.02(d,J=7.8Hz,1H),7.8-7.77(m,3H), 7.71(t,J=2.2Hz,1H),7.65-7.63(m,1H),7.60-7.52(m,3H),7.52-7.43(m,2H),7.36 -7.27(m,3H),2.26-2.21(m,2H),2.00-1.96(m,2H),1.57(t,J=6.3Hz,4H),1.19(s,6H).

[0139] 15. Synthesis route of compound CPD 266

[0140] Synthesis of compound CPD 266-1

[0141] CPD 4-2 (50.00 g, 396.20 mmol), anhydrous potassium carbonate (54.76 g, 396.20 mmol), and heavy water (500 g) were added to a 1000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was sealed for reaction. The system was then heated to 80°C for 48 hours. The reaction was monitored by GC-MS and hydrogen spectrum. The raw material CPD 4-2 was completely consumed.

[0142] The mixture was cooled to room temperature and separated directly. Dichloromethane (200 ml) was added to the organic phase, and the mixture was filtered through a 300-400 mesh silica gel chromatography column (60 g). The filtrates were combined and concentrated under reduced pressure at 50° C. for 3 hours to give a colorless liquid, CPD 266-1 (20.33 g, purity: 99.90%, deuteration rate of four Ds: 99%, yield: 80.74%), mass spectrum: 131.12 (M+H).

[0143] Synthesis of compound CPD 266-2

[0144] Referring to the synthesis and purification methods of compound CPD 4-3, only the corresponding raw materials need to be changed to obtain the target compound CPD 266-2 (39.61 g, purity: 99.77%, yield: 64.71%), mass spectrum: 319.16 (M+H).

[0145] Synthesis of compound CPD 266-3

[0146] Referring to the synthesis and purification methods of compound CPD 4-4, only the corresponding raw materials need to be changed to obtain the target compound CPD 266-3 (28.42 g, purity: 99.90%, yield: 86.06%), mass spectrum: 301.02 (M+H).

[0147] Synthesis of compound CPD 266-4

[0148] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD 266-4 (26.52 g, purity: 99.01%, yield: 81.33%), mass spectrum: 393.22 (M+H).

[0149] Synthesis of compound CPD 266

[0150] Referring to the synthesis and purification methods for compound CPD 119-3, only the corresponding starting materials needed to be changed to obtain the target compound CPD 266 (24.50 g, purity: 99.97%, yield: 76.12%). 24.50 g of crude CPD 266 was purified by sublimation to obtain pure CPD 266 (19.28 g, purity: 99.97%, yield: 78.70%), with a mass spectrum of 650.24 (M+H). 1H NMR (400MHz, CDCl3) δ8.21(t,J=2.1Hz,1H),8.16(d,J=7.7Hz,1H),8.12-8.04(m,4H),8.00-7.95(m,1H),7.86-7.75(m,3H),7.7 -7.64(m,2H),7.60 -7.44(m,12H),7.35-7.29(m,1H),2.22-2.12(m,4H),1.22(s,6H).

[0151] 16. Synthesis route of compound CPD 274

[0152] Synthesis of compound CPD 274-2

[0153] Referring to the synthesis and purification methods of compound CPD 4-3, only the corresponding raw materials need to be changed to obtain the target compound CPD274-2 (36.41 g, purity: 99.52%, yield: 62.22%), mass spectrum: 327.16 (M+H).

[0154] Synthesis of compound CPD 274-3

[0155] Referring to the synthesis and purification methods of compound CPD 4-4, only the corresponding raw materials need to be changed to obtain the target compound CPD274-3 (27.41 g, purity: 99.89%, yield: 83.45%), mass spectrum: 309.12 (M+H).

[0156] Synthesis of compound CPD 274-4

[0157] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD274-4 (32.41 g, purity: 98.89%, yield: 86.56%), mass spectrum: 401.26 (M+H).

[0158] Synthesis of compound CPD 274-7

[0159] CPD 274-5 (25.00 g, 57.43 mmol), CPD 274-6 (12.98 g, 63.17 mmol), 1,1-bis(diphenylphosphino)diphenylferric palladium chloride (0.841 g, 1.15 mmol), potassium carbonate (15.87 g, 114.86 mmol), toluene (375 ml), ethanol (125 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 60°C for 4 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent), indicating complete consumption of the starting material CPD 274-5. The mixture was cooled to room temperature, and methanol (300 ml) was added. The mixture was stirred at room temperature for 1 hour, resulting in the precipitation of a large amount of solid. Toluene (600 ml) was added, the system was heated to 100° C. and dissolved by heating, then cooled to room temperature and filtered once through 300-400 mesh silica gel (60 g). Methanol (450 ml) was added to the filtrate at room temperature, stirred at room temperature for 1 hour, and filtered to obtain a wet white solid. The product was dried at 80° C. for 1 hour to obtain 21.63 g of a white solid. The solid was added to a 500 ml single-necked round-bottom flask and recrystallized once using tetrahydrofuran (130 ml) and methanol (130 ml). The product was filtered and the filter cake was dried in vacuo at 80° C. for 8 hours to obtain CPD 274-7 (18.72 g, purity: 99.51%, yield: 75.12%) as a white solid. Mass spectrum: 433.14 (M+H).

[0160] Synthesis of compound CPD 274

[0161] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 274 (15.69 g, purity: 99.95%, yield: 75.41%). 15.69 g of crude CPD 274 was purified by sublimation to obtain pure CPD 274 (12.55 g, purity: 99.95%, yield: 79.99%), with a mass spectrum of 672.20 (M+H). 1 HNMR(400MHz, CDCl3)δ8.18(t,J=2.2Hz,1H),8.11-8.04(m,4H),8.02(d,J=7.9Hz ,1H),7.93(d,J=2.4Hz,1H),7.87-7.85(m,1H),7.80-7.77(m,2H),7.60-7.55(m,2 H),7.55-7.43(m,8H),7.38-7.32(m,2H),7.32-7.27(m,2H),2.41(d,J=1.0Hz,3H ),2.35-2.31(m,2H),2.10-2.05(m,2H),1.61(t,J=5.4Hz,4H),1.53-1.51(m,6H).

[0162] 17. Synthesis route of compound CPD 276

[0163] Synthesis of compound CPD 276-2

[0164] Referring to the synthesis and purification methods of compound CPD 4-3, only the corresponding raw materials need to be changed to obtain the target compound CPD276-2 (32.0 g, purity: 99.63%, yield: 63.52%), mass spectrum: 370.12 (M+H).

[0165] Synthesis of compound CPD 276-3

[0166] Referring to the synthesis and purification methods of compound CPD 4-4, only the corresponding raw materials need to be changed to obtain the target compound CPD276-3 (25.14 g, purity: 99.68%, yield: 82.63%), mass spectrum: 352.18 (M+H).

[0167] Synthesis of compound CPD 276-4

[0168] Referring to the synthesis and purification methods of compound CPD 4-6, only the corresponding raw materials need to be changed to obtain the target compound CPD276-4 (26.84 g, purity: 98.53%, yield: 83.59%), mass spectrum: 444.26 (M+H).

[0169] Synthesis of compound CPD 276

[0170] Referring to the synthesis and purification methods of compound CPD 4, only the corresponding starting materials need to be changed to obtain the target compound CPD 276 (16.87 g, purity: 99.94%, yield: 73.52%). 16.87 g of crude CPD 276 was purified by sublimation to obtain pure CPD 276 (13.26 g, purity: 99.95%, yield: 78.61%), with a mass spectrum of 715.32 (M+H). 1HNMR (400MHz, CDCl3) δ8.18 (t, J = 2.1 Hz, 1H), 8.12-8.04 (m, 4H), 8.02 (d, J = 7. 9Hz,1H),7.93(d,J=2.4Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.62-7. 41(m,10H),7.37-7.29(m,4H),2.54-2.49(m,4H),2.41(s,3H),2.39-2.34(m, 2H),2.33(s,3H),2.14-2.08(m,2H),1.78(t,J=6.2Hz,4H),1.57-1.52(m,4H).

[0171] Application example: Fabrication of organic electroluminescent devices

[0172] As shown in FIG2 , the organic electroluminescent device includes a stacked glass substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4 (HTL1), a second hole transport layer 5 (HTL2), a light-emitting layer 6, a hole blocking layer 7 (HBL), an electron transport layer 8 (ETL), and a cathode 9.

[0173] The method for preparing the organic electroluminescent device comprises:

[0174] A 50mm*50mm*1.0mm glass substrate 1 with ITO (100nm) transparent electrodes (anode 2 and cathode 9) was ultrasonically cleaned in ethanol for 10 minutes, dried at 150°C, and then treated with N2 plasma for 30 minutes. The cleaned glass substrate was mounted on a substrate holder in a vacuum evaporation apparatus. First, the compound HATCN was evaporated on the surface with the transparent electrode lines, covering the transparent electrode to form a 5nm thick film (hole injection layer 3). Next, a layer of HTM1 was evaporated to form a 60nm thick film as HTL1 (first hole transport layer 4). A layer of HTM2 was then evaporated on the HTM1 film to form a 10nm thick film as HTL2 (second hole transport layer 5). Finally, a host material and guest material (with a weight ratio of 98%:2%) were co-evaporated on the HTM2 film to form a 25nm thick light-emitting layer 6. A 5nm-thick hole-blocking layer (HBL) and a 350nm-thick electron-transporting layer (ETL) were formed on the light-emitting layer using evaporation. The HBL was made from the present compound or a comparative compound, while the ETL was made from an ETL material or the present compound: LiQ (1:1 weight ratio). Mg / Ag (100nm, 1:9 ratio) was then co-evaporated as the cathode material.

[0175] evaluate:

[0176] The above devices were tested for device performance. In each embodiment and comparative example, a constant current source (Keithley 2400) was used to flow a fixed current density through the light emitting element, and the luminescence spectrum was measured using a spectroradiometer (CS2000). At the same time, the current density was 10 mA / cm 2 Under these conditions, the device voltage, efficiency, and the time it takes for the test brightness to reach 95% of the initial brightness (LT95) were measured. The results are shown in Table 1:

[0177] Table 1:

[0178] From the data comparison in the above table, it can be seen that the use of the compounds of the present application in organic electroluminescent devices as hole blocking layer materials and electron transport layer materials shows superior performance in driving voltage, luminous efficiency and device life compared to the comparative compounds.

[0179] The above results indicate that the compounds of this application have advantages such as good optical, electrical, and thermal stability, high luminous efficiency, low voltage, and long life, and can be used in organic light-emitting devices. In particular, they have the potential to be applied in the AMOLED industry as hole-blocking layer materials and electron-transport layer materials.

Claims

1. A compound, whose structural formula is shown in formula (1): in, X is independently selected from C(R4)2, O, S, NR5; Wherein n is independently selected from an integer of 0 or 1-6, when n=0, they are not connected to form a ring; when n≥1, they are connected to form a ring; when n≥2, each X is the same or different; Wherein, X1, X2, and X3 are independently selected from N or CR6, and at least one is N; R1, R2, and R3 are each independently selected from 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, C5-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; R4, R5, and R6 are ring substituents, each 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, C5-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; L is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms; wherein a, b, c are independently selected from integers ranging from 0 to 8, wherein Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The heteroatom in the heteroaryl, heteroalkyl or heterocycloalkyl group is selected from at least one heteroatom of O, S, N, Se, Si and Ge; The substitution is substitution by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amine, C6-C12 aryl, cyano, isocyano or phosphino, and the number of substitutions of each substituent group is independently selected from one of single substitution to the maximum number of substitutions.

2. A compound according to claim 1, selected from one of the structures represented by the following formula (2) and formula (3); 3. A compound according to claim 2, wherein when n=0, they are not connected to form a ring and X does not exist; when n≥1, they are connected to form a ring; when n≥2, X is a plurality of C(R4)2; or a combination of one or more C(R4)2 and one of O, S, and NR5.

4. A compound according to claim 2, wherein the formula (1)-(3) Selected from one of the structures shown in the following formula A-1 to formula A-8; 5. A compound according to claim 1, wherein L in the formula (1) is selected from a single bond and one of the structures shown in the following formulas B-1 to B-18; wherein each R is independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine, and m is selected from an integer of 0-4.

6. A compound according to claim 5, wherein each R is independently selected from deuterium or a C1-C4 alkyl group.

7. A compound according to claim 4, wherein X1-X3 contains at least two N, and R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamine; R6 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-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino A phosphine group or a C6-C30 arylamine group.

8. A compound according to claim 7, wherein in, Two of X1-X3 are N, and the other one is CH or N, and R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl, C6-C20 monoarylphosphinyl, C6-C20 diarylphosphinyl, or C6-C30 arylamine.

9. A compound according to claim 8, wherein X1-X3 are all N, or X1 and X2 are N, and X3 is CH; R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C5-C12 heteroaryl, C1-C10 alkoxy, C6-C12 aryloxy, or C6-C12 arylamine.

10. A compound according to claim 9, wherein X1-X3 are all N, and a, b, and c are all 0.

11. A compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, trideuterated methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, pyrenyl, phenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene radical or a combination of at least two of the foregoing.

12. A compound according to any one of claims 1 to 11, wherein formula (1) contains at least one deuterium atom.

13. A compound according to claim 1, selected from one of the following structures; 14. A light-emitting device comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the organic layers comprises the compound according to any one of claims 1 to 13.

15. The light-emitting device according to claim 14, wherein the compound according to any one of claims 1 to 13 is used as a material in any one of a light-emitting layer, a hole blocking layer and an electron transport layer in an organic layer.

16. The light-emitting device according to claim 15, wherein the compound according to any one of claims 1 to 13 is used as a hole blocking layer material.

17. The light-emitting device according to any one of claims 14 to 16, wherein the light-emitting device is an organic electroluminescent device.

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