Arylamine compound, composition containing arylamine compound and organic light-emitting device

Abstract

The invention discloses an arylamine compound, a composition containing the arylamine compound and an organic light-emitting device. The structure of the arylamine compound is as shown in the following formula (1): # imgabs0 # formula (1). Wherein ring A is selected from substituted or unsubstituted phenanthrene ring; b is selected from structural substituents as shown in the following formula (2); # imgabs 1 # formula (2). And ring C is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring and a substituted or unsubstituted phenanthrene ring. The arylamine compound provided by the invention has a series of excellent physical and chemical characteristics, and has a good application prospect in the photoelectric field. Specifically, the arylamine compound has excellent photoelectric stability, can effectively resist performance degradation caused by illumination and current change, and ensures stable output of the device in long-time operation. The light-emitting diode has the advantages of low sublimation temperature, low driving voltage, high light-emitting efficiency and long device service life.

Description

Technical Field

[0001] The present application relates to the field of organic light-emitting technology, and in particular to an aromatic amine compound, a composition containing the aromatic amine compound, and an organic light-emitting device. Background Art

[0002] Currently, organic light-emitting devices (OLEDs), which are leading the trend of future display and lighting technologies, are attracting much attention due to their wide application potential. OLED technology not only shines in consumer electronic products such as smartphones, tablets, and high-definition TVs, but also gradually penetrates into multiple fields such as wearable devices, automotive displays, and indoor lighting, showing extremely broad development prospects. However, despite the significant progress made in OLED technology, its commercialization process still faces challenges, especially in key performance indicators such as improving luminous efficiency, reducing driving voltage, and extending service life, which still need in-depth research and continuous optimization.

[0003] The core structure of OLED devices is a multi-layer stacked "sandwich" structure, in which metal electrodes serve as the upper and lower boundaries, and a variety of organic thin film layers with different functions are precisely arranged in the middle. Under the action of the electric field, electrons are injected from the cathode and holes are injected from the anode. The two move toward each other inside the device and eventually meet and recombine in the light-emitting layer. This recombination process is not only accompanied by the emission of photons, but may also be dissipated in the form of heat energy, which directly affects the luminous efficiency of OLEDs. In order to maximize the light energy output, researchers are committed to optimizing the design of the light-emitting layer, especially focusing on the research of phosphorescent OLEDs, whose efficient triplet luminescence mechanism has opened up new ways to improve brightness and efficiency.

[0004] It is worth noting that the performance of phosphorescent OLEDs is not only restricted by the choice of the luminescent body, but also deeply affected by the characteristics of the host material. As an important component of the light-emitting layer, the energy level structure, mobility and stability of the host material have a crucial impact on the performance of the device. Optimizing the host material can significantly reduce the operating voltage of the device, improve the energy conversion efficiency, and effectively extend the service life of the device.

[0005] Therefore, the development of new high-performance host materials is of great significance to the development of the OLED field. Summary of the invention

[0006] The present application aims to solve at least one of the technical problems existing in the prior art. To this end, the present application proposes a compound, which, when used in the preparation of an OLED main material, can significantly reduce the device's driving voltage, improve the device's luminous efficiency, and increase the device's service life.

[0007] A first aspect of the present application provides an aromatic amine compound.

[0008] In some embodiments, the structure of the aromatic amine compound is shown in the following formula (1): Formula (1) In the formula, ring A is selected from substituted or unsubstituted phenanthrene ring; X is selected from oxygen group elements, CR a R b or NR c ; R a , R b and 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 or C6-C30 arylsilyl; each R1 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, or C6-C60 arylamine; a is an integer from 0 to 4; if a ≥ 2, each R1 is the same or different; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; B is selected from the structural substituents represented by the following formula (2); Formula (2) In the formula, ring C is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Y is selected from O, S or Se; represents the connection site with L2 in formula (1); Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl; The substitution in L1, L2, Ar1 and Ar2 each independently represents substitution 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 or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, and the number of substitutions ranges from single substitution to the maximum number of substitutions; The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group or heterocycloalkyl group are each independently selected from at least one of O, S, N, Se, Si and Ge.

[0009] Compared with the prior art, the beneficial effects of this application are as follows: The aromatic amine compounds of the present application scheme have a series of superior physical and chemical properties and have good application prospects in the field of optoelectronics. Specifically, aromatic amine compounds perform well in terms of optoelectronic stability, can effectively resist the performance degradation caused by changes in light and current, and ensure the stable output of the device under long-term operation. In addition, its unique sublimation characteristics are reflected in the lower sublimation temperature, which significantly reduces the energy consumption and cost of the material during vacuum evaporation, while improving the controllability and uniformity of the evaporation process, which is conducive to the preparation of high-quality optoelectronic device films. In terms of electrical properties, the aromatic amine compound exhibits the dual advantages of low driving voltage and high luminous efficiency. Low driving voltage means that under the same conditions, the device can consume less electrical energy to achieve the same brightness, which is of great significance for improving energy utilization efficiency and extending the battery life of portable electronic devices. High luminous efficiency is directly related to the light output quality and energy conversion efficiency of the device, and is an important technical support for achieving energy conservation and emission reduction. At the same time, the aromatic amine compound also has a long device life, thanks to its excellent chemical stability and thermal stability, which can resist the erosion of the material structure by the external environment, thereby extending the overall service life of the optoelectronic device and reducing the cost of replacement and maintenance.

[0010] During the material evaporation process, the lower melting point not only simplifies the processing flow, but also enhances the material stability during the evaporation process, reduces material decomposition or deterioration caused by high temperature, and further improves the performance and reliability of the device.

[0011] Additional aspects and advantages of the present application will be given in part in the description below, and in part will become apparent from the description below, or will be learned through the practice of the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] The present application is further described below with reference to the accompanying drawings and embodiments, wherein: Figure 1 Compound A50 prepared in Example 2 of the present application 1 HNMR spectrum.

[0013] Figure 2 This is a schematic diagram of the structure of an organic light-emitting device prepared in the application example of this application.

[0014] Explanation of the accompanying drawings: 1. glass substrate; 2. anode; 3. hole injection layer; 4. first hole transport layer; 5. second hole transport layer; 6. light-emitting layer; 7. electron transport layer; 8. electron injection layer; 9. cathode. DETAILED DESCRIPTION

[0015] The following will be combined with the embodiments to clearly and completely describe the concept of the present application and the technical effects produced, so as to fully understand the purpose, features and effects of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all of them. Based on the embodiments of the present application, other embodiments obtained by technicians in this field without creative work are within the scope of protection of the present application. The test methods used in the embodiments are conventional methods unless otherwise specified; the materials, reagents, etc. used, unless otherwise specified, can be reagents and materials obtained from commercial channels. Unless otherwise specified, the same parameter in each embodiment has the same value. The embodiments described below are exemplary and are only used to explain the present application, and cannot be understood as limitations on the present application.

[0016] In the description of this application, the description of reference terms such as "some embodiments" means that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of this application. In this specification, the schematic representation of the above terms does not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments or examples in a suitable manner.

[0017] In the description of this application, if there is a description of first, second, third, etc., it is only for the purpose of distinguishing technical features, and it cannot be understood as indicating or implying relative importance or implicitly indicating the number of the indicated technical features or implicitly indicating the order of the indicated technical features.

[0018] A first aspect of the present application provides an aromatic amine compound.

[0019] Specifically, the structure of the aromatic amine compound is shown in the following formula (1): Formula (1) In the formula, ring A is selected from substituted or unsubstituted phenanthrene ring; X is selected from oxygen group elements, CR a R b or NR c ; R a , Rb and 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 or C6-C30 arylsilyl; each R1 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, or C6-C60 arylamine; a is an integer from 0 to 4; if a ≥ 2, each R1 is the same or different; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; B is selected from the structural substituents represented by the following formula (2); Formula (2) In the formula, ring C is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Y is selected from O, S or Se; represents the connection site with L2 in formula (1); Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group; The substitutions in L1, L2, Ar1 and Ar2 each independently represent substitutions 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, and the number of substitutions is from single substitution to the maximum number of substitutions; the heteroatoms in the heteroarylene, heteroaryl, heteroalkyl or heterocycloalkyl are each independently selected from at least one of O, S, N, Se, Si and Ge.

[0020] Specific examples of aromatic groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrene, chrysene, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl, etc. In some specific embodiments of the present application, aromatic groups are phenyl or naphthyl.

[0021] Specific examples of heteroaryl groups include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazine, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, and quinazolinyl. In some specific embodiments of the present application, the heteroaryl group is pyridyl, pyrimidinyl, triazine, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, carbazolyl, azacarbazolyl or diazacarbazolyl.

[0022] In some embodiments, the chalcogen element is selected from O, S or Se.

[0023] In some embodiments, the heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl are each independently selected from at least one of O, S, N, Se, Si and Ge. a , R b and R c Each is independently selected from a C1-C20 alkyl group, a C1-C20 heteroalkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, a C3-C20 alkylsilyl group or a C6-C20 arylsilyl group.

[0024] In some embodiments, the R a , R b and R c Each is independently selected from a C1-C10 alkyl group, a C1-C10 heteroalkyl group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C6-C10 aryl group, a C3-C10 heteroaryl group, a C3-C10 alkylsilyl group or a C6-C10 arylsilyl group.

[0025] In some embodiments, R1 is selected from at least one of 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, C3-C30 heteroaryl, C1-C30 alkoxy, C6-C30 aryloxy, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, or C6-C30 arylamine.

[0026] In some embodiments, R1 is selected from at least one of hydrogen, 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, C3-C20 heteroaryl, C1-C20 alkoxy, C6-C20 aryloxy, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, or C6-C20 arylamine.

[0027] In some embodiments, a is 0 or 4.

[0028] In some embodiments, if a is 4, at least one R1 is deuterium, and may be all or partly deuterium.

[0029] In some embodiments, a is an integer of 1-4, such as 2 or 3.

[0030] In some embodiments, the ring A is selected from the structures shown in any one of the following formulas (A-1) to (A-4):

[0031] In the formula, represents the fusion site with the five-membered ring containing X in formula (1); The substituent R2 of ring A is selected from at least one of 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, or C6-C60 arylamine; b is an integer from 0 to 8; if b≥2, each R2 is the same or different.

[0032] In some embodiments, R2 is selected from at least one of 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, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, or C6-C30 arylamine.

[0033] In some embodiments, R2 is selected from at least one of hydrogen, 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, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, or C6-C20 arylamine.

[0034] In some embodiments, b is 0 or 7. If b is 7, at least one R2 is deuterium. All or part of R2 may be deuterium.

[0035] In some embodiments, b is an integer of 1-8, such as 2, 3, 4, 5, 6, 7 or 8.

[0036] In some embodiments, the ring C is selected from the structures represented by the following formula (C-1) to formula (C-7):

[0037] In the formula, represents the fusion site with the N-containing five-membered ring in formula (2); The substituent R3 of ring C 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 or C6-C60 arylamine; c is an integer from 0 to 8; if c≥2, each R3 is the same or different.

[0038] In some embodiments, R3 is independently selected from at least one of 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, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, or C6-C30 arylamine.

[0039] In some embodiments, R3 is independently selected from at least one of hydrogen, 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, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, or C6-C20 arylamine.

[0040] In some embodiments, c is 0, 3, 5 or 7. If c is 3, 5 or 7, at least one R3 is deuterium. It can be all deuterium or partly deuterium.

[0041] In some embodiments, c is an integer of 1-8, such as 2, 3, 4, 5, 6, 7 or 8.

[0042] In some embodiments, at least one of R1, R2, and R3 is deuterium. When a, b, and c are all non-zero, at least one of R1, R2, and R3 is deuterium.

[0043] In some embodiments, X is O or S. In some embodiments, L1 and L2 are each independently selected from a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C6-C30 heteroarylene group.

[0044] In some embodiments, L1 and L2 are each independently selected from a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C6-C20 heteroarylene group.

[0045] In some embodiments, L1 and L2 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0046] In some embodiments, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group.

[0047] In some embodiments, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group.

[0048] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysene, 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, or a combination of at least two of the foregoing.

[0049] In some embodiments, Ar1 and Ar2 are each independently selected from a phenyl group containing a deuterium substitution, a biphenyl group containing a deuterium substitution, or a naphthyl group containing a deuterium substitution.

[0050] In some embodiments, the aromatic amine compound is one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

[0051] .

[0052] A second aspect of the present application provides a composition for an organic light-emitting device.

[0053] Specifically, the composition comprises a first host compound and a second host compound, wherein the first host compound has a structure as shown in formula (1), and the second host compound has a structure as shown in formula (3): Formula (3) In the formula, ring D is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Z is selected from NR d , CR e R for oxygen group element; Z1, Z2 and Z3 are each independently selected from N or CR g ; R d , R e and R f 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 or C6-C30 arylsilyl; R4 and R g Each 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 or C6-C60 arylamine; d is an integer from 0 to 4; if d ≥ 2, each R1 is the same or different; L3 to L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group; The substitutions in the rings D, L3, L4, L5, Ar3 and Ar4 each independently represent substitutions 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, and the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0054] In some embodiments, the chalcogen element is selected from O, S or Se.

[0055] In some embodiments, R d , R e and R f Each is independently selected from a C1-C20 alkyl group, a C1-C20 heteroalkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, a C3-C20 alkylsilyl group or a C6-C20 arylsilyl group.

[0056] In some embodiments, R d , R e and R f Each is independently selected from a C1-C10 alkyl group, a C1-C10 heteroalkyl group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C6-C10 aryl group, a C3-C10 heteroaryl group, a C3-C10 alkylsilyl group or a C6-C10 arylsilyl group.

[0057] In some embodiments, R4 and R g Each is independently 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, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino or C6-C30 arylamine.

[0058] In some embodiments, R4 and R g Each is independently 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-C20 aryl, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino or C6-C20 arylamine.

[0059] In some embodiments, d is an integer of 1-4, such as 2 or 3.

[0060] In some embodiments, X or Z is independently selected from O or S.

[0061] In some embodiments, L3 to L5 are each independently selected from a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C6-C20 heteroarylene group.

[0062] In some embodiments, L3 to L5 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene.

[0063] In some embodiments, the L1 to L5 are each independently selected from a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C6-C20 heteroarylene group.

[0064] In some embodiments, the L1 to L5 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene.

[0065] In some embodiments, Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0066] In some embodiments, Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heteroaryl group.

[0067] In some embodiments, Ar1 to Ar4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylenyl, or a combination of at least two of the above.

[0068] In some embodiments, Ar1 to Ar4 are each independently selected from a phenyl group containing a deuterium substitution, a biphenyl group containing a deuterium substitution, or a naphthyl group containing a deuterium substitution.

[0069] In some embodiments, the second host compound is selected from one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; .

[0070] In some embodiments, the mass ratio of the first host compound to the second host compound is 8:2-2:8.

[0071] In some embodiments, the composition further comprises at least one third host compound, wherein the third host compound has a structure as shown in Formula (1) or Formula (3), and the structures of the first, second and third host compounds are different.

[0072] In some embodiments, in the composition, the mass ratio of the compound of the structure shown in formula (1) to the compound of the structure shown in formula (3) is 8:2-2:8. The third main compound belongs to the structure shown in formula (1) or formula (3), and the total mass of the third main compound and the first main compound or the second main compound satisfies the above-mentioned proportional relationship. If it is formula (1), the total mass of the third main compound and the first main compound accounts for 20% to 80% of the total composition. Since it is the same as formula (1), the proportion in formula (1) is unlimited, 0 to 100%. Similarly, if it is formula (2), the total mass of the third main compound and the second main compound accounts for 20% to 80% of the total composition. Since it is the same as formula (2), the proportion in formula (2) is unlimited, 0 to 100%.

[0073] The third aspect of the present application provides the application of the above aromatic amine compound or composition.

[0074] Specifically, the third aspect of the present application provides the application of the above aromatic amine compound or composition in the semiconductor field.

[0075] Specifically, an organic light-emitting device comprises the above aromatic amine compound or composition.

[0076] In some embodiments, an organic light-emitting device (OLED) includes a cathode and an anode, wherein the cathode is arranged opposite to the anode, and a light-emitting layer is arranged between the cathode and the anode, and the light-emitting layer includes the above-mentioned aromatic amine compound or composition. The aromatic amine compound and composition described in the present application can be used alone or after doping to prepare the light-emitting layer.

[0077] In some embodiments, in the device, the aromatic amine compound or the composition is used as a red light-emitting material of a light-emitting layer.

[0078] In some embodiments, the light-emitting layer is a red light-emitting layer, and the aromatic amine compound or composition serves as a host material of the red light-emitting layer.

[0079] Specifically, the above aromatic amine compound or composition is used in the preparation of semiconductor devices. In some embodiments, a semiconductor device includes the above organic light-emitting device, and the semiconductor device is at least one of an organic light-emitting cell, an organic light-emitting field effect tube, an organic OLED display (which may be an organic light-emitting diode panel (AMOLED), an organic electroluminescent sensor (Organic Light-Emitting Sensor, OLES), etc.

[0080] In some embodiments, the organic light-emitting field effect transistor includes an organic light-emitting transistor (OLET).

[0081] In some embodiments, the organic electroluminescent transistor may be an organic light-emitting thin-film transistor (OLETFT).

[0082] definition Unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art, but for a better understanding of the present application, the definitions of some terms are provided below. When the definitions of terms provided in the present application are inconsistent with the meanings commonly understood by those skilled in the art, the definitions and interpretations of the terms provided in the present application shall prevail.

[0083] The term "heteroalkyl" means that at least one carbon atom on the basis of an alkyl group is replaced by a non-carbon atom or a group containing a non-carbon atom, and the non-carbon atom can be selected from at least one of O, S, N, P, B, Si, Ge or Se, but does not include the case where the carbon atom connected to the main structure in the alkyl group is replaced by a non-carbon atom (such as alkoxy, alkylsilyl, alkylboryl). Non-limiting examples of heteroalkyl groups include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, butylene oxide, cyclopentyl or hexyl oxide, etc. In some specific embodiments of the present application, the heteroalkyl group is methoxymethane or cyclopentyl.

[0084] The term "alkoxy" refers to a group having an -O-alkyl group, ie, an alkyl group as defined above attached to a given group or given formula via an oxygen atom. Non-limiting examples of alkoxy groups include: methoxy, ethoxy, and tert-butoxy.

[0085] The term "heterocycloalkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, and the non-carbon atom can be selected from at least one of O, S, N, P, B, Si, Ge or Se. The number of carbon atoms in the heterocycloalkyl group can be 3 to 30, 3 to 20, 3 to 12, 3 to 10 or 3 to 6. Non-limiting examples of heterocycloalkyl groups include: butylene oxide, pentylene oxide and hexylene oxide.

[0086] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group or a polycyclic aromatic group. At least one ring in a polycyclic aromatic group is an aromatic ring system. Multiple rings in a polycyclic aromatic group can be connected to each other via a single bond or can be fused to each other. The number of carbon atoms of the aryl group can be 6 to 30, 6 to 20, 6 to 12 or 6 to 10. For example, when the polycyclic aromatic group contains a fused ring structure, it can be specifically formed by condensing a C3-C30 aliphatic ring (a saturated or unsaturated aliphatic ring containing 3 to 30 ring skeleton carbon atoms) and a C3-C30 aromatic ring (an aromatic ring containing 3 to 30 ring skeleton carbon atoms), more specifically, by condensing a C3-C20 aliphatic ring and a C6-C30 aromatic ring. It can be understood that the term "arylene" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing two hydrogen atoms.

[0087] The term "heteroaryl" refers to a monovalent group in which at least one carbon atom based on an aromatic group is replaced by a non-carbon atom, wherein the non-carbon atom can be selected from a heterocyclic aromatic system of O, S, N, P, B, Se, Si or Ge, but does not include the case where the aromatic group is connected to the main structure through a non-carbon atom group (for example, an aryloxy group, an arylsilyl group, an arylboryl group, an arylphosphino group, an arylamine group).

[0088] The term "arylphosphino" may be a monoarylphosphino, a diarylphosphino, a triarylphosphino, and the like.

[0089] It is understood that the term "heteroarylene" refers to a divalent group having the same structure as a heteroaryl group.

[0090] The "carbon number a to b" in the expression "substituted or unsubstituted R group having a to b carbon atoms" means the carbon number when the R group is unsubstituted, and does not include the carbon number of the substituent when the R group is substituted.

[0091] The "substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and unless otherwise limited by the definition, it also includes that one or more hydrogen atoms are replaced by a group formed by connecting two or more of the above-mentioned substituents.

[0092] The following embodiments are only for facilitating the understanding of the technical application and should not be regarded as specific limitations of the present application.

[0093] The raw materials and solvents involved in the synthesis of the compounds in this application were purchased from suppliers familiar to those skilled in the art such as Alfa and Acros.

[0094] Synthesis of Compound A2

[0095] Synthesis of Compound A2-3 Compound A2-1 (20.00 g, 71.04 mmol), compound A2-2 (21.65 g, 85.25 mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (0.52 g, 0.71 mmol), potassium acetate (17.43 g, 177.60 mol), and 1,4-dioxane (350 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. The system was then heated to 100 °C for 4 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The compound A2-1 was completely consumed.

[0096] 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 mixture was washed three times with deionized water (300 ml × 3). The mixture was separated, and the sample was 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 mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid, which was compound A2-3 (18.52 g, purity: 99.37%, yield: 79.34%), with a mass spectrum of 329.10 (M+H).

[0097] Synthesis of Compound A2-5 Compound A2-3 (18.00 g, 54.78 mmol), compound A2-4 (10.14 g, 54.78 mmol), tetrakis(triphenylphosphine)palladium (0.63 g, 0.55 mmol), potassium carbonate (18.93 g, 136.95 mmol), tetrahydrofuran (375 ml), and deionized water (125 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, 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). Compound A2-3 was completely consumed.

[0098] 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 × 3). The product was separated, and the sample was 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 the eluent). After elution, the product was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid, which was compound A2-5 (12.38 g, purity: 99.41%, yield: 73.68%), with a mass spectrum of 307.04 (M+H).

[0099] Synthesis of Compound A2-7 Compound A2-5 (12.00 g, 39.12 mmol), compound A2-6 (20.12 g, 58.68 mmol), and tetrahydrofuran (270 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was cooled to 5°C, and sodium methoxide (4.23 g, 78.24 mmol) was added at one time. 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). Compound A2-5 was completely consumed.

[0100] Deionized water (500 ml) was added, the solvent was removed by concentrating under reduced pressure, ethyl acetate (500 ml) was added for extraction, the liquids were separated, and the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid compound A2-7 (11.86 g, yield: 90.55%), mass spectrum: 335.07 (M+H). The obtained compound was used directly in the next step without purification.

[0101] Synthesis of Compound A2-8 Compound A2-7 (11.50 g, 34.35 mmol) and toluene (150 ml) were added into a 500 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then the system was cooled to 5°C, and methanesulfonic acid (6.60 g, 68.70 mmol) was slowly added dropwise. The addition was completed within 3 minutes, and the reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A2-7 was completely consumed.

[0102] Methanol (200 ml) was added thereto to precipitate a large amount of white solid, which was filtered off to obtain 9 g of solid. Toluene (190 ml) and methanol (150 ml) were used for crystallization once, and the filter cake was filtered off under vacuum at 80°C for 1 hour to obtain a white solid, which was compound A2-8 (7.64 g, purity: 99.76%, yield: 73.47%), mass spectrum: 303.05 (M+H).

[0103] Synthesis of Compound A2-11 Compound A2-9 (10.00 g, 36.48 mmol), compound A2-10 (6.17 g, 36.48 mmol), tri(dibenzylideneacetone)dipalladium (0.67 g, 0.73 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.70 g, 1.146 mmol), cesium carbonate (29.72 g, 91.20 mmol), and toluene (150 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 90 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A2-9 was completely consumed.

[0104] The temperature was lowered to 60°C, methanol (150 ml) was added, and the mixture was naturally cooled to room temperature and stirred for 30 minutes to precipitate a large amount of solids. The mixture was filtered to obtain 15 g of solids. Toluene (200 ml) was added, and the system was then heated to 100°C to dissolve and clarify. 30 g of silica gel (300-400 mesh) was spread and filtered. The surface of the silica gel was rinsed with toluene (50 ml), and the filtrate was combined and concentrated to obtain 13 g. Toluene (170 ml) and methanol (80 ml) were used for crystallization twice, and the mixture was filtered. The filter cake was vacuum dried at 90°C for 3 hours to obtain a light yellow solid, which was compound A2-11 (9.28 g, purity: 99.59%, yield: 70.19%), with a mass spectrum of 363.14 (M+H).

[0105] Synthesis of Compound A2 Compound A2-8 (7.50 g, 24.77 mmol), compound A2-11 (8.98 g, 24.77 mmol), tri(dibenzylideneacetone)dipalladium (0.45 g, 0.50 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.47 g, 0.99 mmol), sodium tert-butoxide (5.95 g, 61.93 mmol), and toluene (135 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, 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). Compound A2-8 was completely consumed.

[0106] The temperature was lowered to 60°C, methanol (150ml) was added, and the mixture was naturally cooled to room temperature and stirred for 30 minutes to precipitate a large amount of solids. The mixture was filtered to obtain 14g of solids. Toluene (300ml) was added, and the system was then heated to 100°C to dissolve and clarify. 30g (300-400 mesh) of silica gel was spread and filtered. The surface of the silica gel was rinsed with toluene (50ml), and the filtrate was combined and concentrated to obtain 12g. Toluene (170ml) and methanol (80ml) were used for crystallization twice, and the mixture was filtered and the filter cake was vacuum dried at 90°C for 3 hours to obtain a light yellow solid compound A2 (11.75g, purity: 99.94%, yield: 75.44%). 11.75g ​​of crude compound A2 was purified by sublimation to obtain sublimation pure compound A2 (7.67g, purity: 99.94%, yield: 65.27%), with a mass spectrum of 629.21 (M+H).

[0107] 1 H NMR (400 MHz, CDCl3) δ 8.98 (dd, J = 14.1, 3.8 Hz, 1H), 8.22 (d, J= 2.9 Hz, 1H), 8.21 – 8.16 (m, 2H), 8.14 – 8.03 (m, 3H), 7.94 – 7.87 (m, 1H),7.79- 7.70(m, 3H), 7.70 – 7.58 (m, 5H), 7.58 – 7.53 (m, 2H), 7.52 – 7.33 (m,7H), 7.31 – 7.25 (m, 2H), 7.23 – 7.14 (m, 1H). Synthesis of compound A50:

[0108] Synthesis of Compound A50-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A50-2 (18.91 g, purity: 99.23%, yield: 81.01%), mass spectrum: 329.10 (M+H).

[0109] Synthesis of Compound A50-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A50-3 (13.24 g, purity: 99.51%, yield: 76.67%), mass spectrum: 307.04 (M+H).

[0110] Synthesis of Compound A50-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A50-4 (12.81 g, yield: 90.28%), mass spectrum: 335.07 (M+H).

[0111] Synthesis of Compound A50-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A50-5 (7.28 g, purity: 99.71%, yield: 70.84%), mass spectrum: 303.05 (M+H).

[0112] Synthesis of Compound A50-7 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A50-7 (11.35 g, purity: 99.47%, yield: 67.84%), mass spectrum: 306.06 (M+H).

[0113] Synthesis of Compound A50-9 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A50-9 (10.87 g, purity: 99.78%, yield: 68.90%), mass spectrum: 363.15 (M+H).

[0114] Synthesis of compound A50 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A50 (11.35 g, purity: 99.96%, yield: 69.65%). 11.35 g of crude compound A50 was purified by sublimation to obtain sublimation pure compound A50 (7.17 g, purity: 99.93%, yield: 63.17%), mass spectrum: 629.22 (M+H). Its NMR characterization results are as follows Figure 1 The specific data are as follows: 1 H NMR (400 MHz, CDCl3) δ 9.27 (d, J = 8.5 Hz, 1H), 8.59 (d, J = 8.8 Hz,1H), 8.29 (d, J = 3.7 Hz, 2H), 8.01 – 7.95 (m, 1H), 7.95 – 7.60 (m, 9H), 7.58 –7.30 (m, 11H), 7.30 – 7.19 (m, 2H), 7.16 (t, J = 7.2 Hz, 1H). Synthesis of Compound A68

[0115] Synthesis of Compound A68-3 Compound A68-1 (5.00 g, 25.82 mmol), pyridine (4.09 g, 51.64 mmol) and dry tetrahydrofuran (150 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was stirred for 10 min in an ice bath, and then compound A68-2 (3.76 g, 25.82 mmol) was added. Stirring was continued for 15 min, and then the reaction was carried out at room temperature for 4 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A68-1 was completely consumed.

[0116] Toluene (100 ml) was added, and the mixture was washed three times with deionized water (300 ml x 3). The organic phase was separated and concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid compound A68-3 (7.13 g, yield: 91.20%), with a mass spectrum of 303.08 (M+H). The obtained compound was used directly in the next step without purification.

[0117] Synthesis of Compound A68-4 Compound A68-3 (7.00 g, 23.12 mmol), p-toluenesulfonic acid (7.96 g, 46.24 mmol) and toluene (150 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. The system was then heated to 120 °C for 3 hours and the water was separated by a water separator. The reaction was monitored by TLC (dichloromethane:n-hexane = 1:2 as the developing solvent). Compound A68-3 was completely consumed.

[0118] Cool to room temperature, add dichloromethane (100ml) and water (100ml), extract, separate, and concentrate the organic phase at 60℃ under reduced pressure for 20min to obtain a white solid compound. Add toluene (100ml), then heat the system to 100℃ to dissolve and clarify, pave 30g (300-400 mesh) silica gel for filtration, rinse the silica gel surface with toluene (50ml), and combine the filtrate for concentration to obtain 7g. Crystallize twice with toluene (100ml) and methanol (50ml), filter, and vacuum dry the filter cake at 90℃ for 3 hours to obtain a light yellow solid compound A68-4 (4.81g, purity: 99.34%, yield: 73.06%), mass spectrum: 285.07 (M+H).

[0119] Synthesis of Compound A68-6 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A68-6 (3.92 g, purity: 99.71%, yield: 71.60%), mass spectrum: 347.19 (M+H).

[0120] Synthesis of Compound A68 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A68 (4.18 g, purity: 99.90%, yield: 67.53%). 4.18 g of crude compound A68 was purified by sublimation to obtain sublimation pure compound A68 (2.59 g, purity: 99.94%, yield: 61.96%), mass spectrum: 613.26 (M+H).

[0121] 1 H NMR (400 MHz, CDCl3) δ8.98 (dd, J = 14.1, 3.8 Hz, 1H), 8.15 – 7.96(m, 4H), 7.93 – 7.87 (m, 1H), 7.75 (dd, J = 14.9, 3.0 Hz, 1H), 7.72 – 7.59(m, 3H), 7.58 – 7.51 (m, 2H), 7.42 (dd, J = 15.0, 2.9 Hz, 1H), 7.33 (dd, J =15.0, 2.9 Hz, 1H), 7.11 (d, J = 3.0 Hz, 1H), 7.05 (d, J = 14.8 Hz, 1H). Synthesis of Compound A79

[0122] Synthesis of Compound A79-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A79-2 (15.92 g, purity: 99.25%, yield: 69.48%), mass spectrum: 371.17 (M+H).

[0123] Synthesis of Compound A79-4 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A79-4 (11.04 g, purity: 99.47%, yield: 68.88%), mass spectrum: 383.07 (M+H).

[0124] Synthesis of Compound A79-5 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A79-5 (10.53 g, yield: 89.19%), mass spectrum: 411.10 (M+H).

[0125] Synthesis of Compound A79-6 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A79-6 (7.12 g, purity: 99.68%, yield: 73.54%), mass spectrum: 379.08 (M+H).

[0126] Synthesis of Compound A79 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A79 (7.61 g, purity: 99.96%, yield: 65.51%). 7.61 g of crude compound A79 was purified by sublimation to obtain sublimation pure compound A79 (4.82 g, purity: 99.93%, yield: 63.33%), mass spectrum: 629.21 (M+H).

[0127] 1 H NMR (400 MHz, CDCl3) δ 9.13 (d, J = 3.1 Hz, 1H), 8.22 – 8.15 (m,2H), 8.14 – 8.01 (m, 4H), 7.97 (d, J = 2.9 Hz, 1H), 7.83 – 7.71 (m, 5H), 7.70– 7.54 (m, 4H), 7.53 – 7.45 (m, 2H), 7.44-7.36 (m, 1H), 7.31 – 7.13 (m, 5H), 7.12 – 7.04 (m, 2H), 7.04 – 6.95 (m, 1H). Synthesis of Compound A81

[0128] Synthesis of Compound A81-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A81-2 (14.38 g, purity: 99.35%, yield: 66.26%), mass spectrum: 307.04 (M+H).

[0129] Synthesis of Compound A81-3 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A81-3 (13.81 g, yield: 90.38%), mass spectrum: 335.07 (M+H).

[0130] Synthesis of Compound A81-4 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A81-4 (8.71 g, yield: 71.35%), mass spectrum: 303.05 (M+H).

[0131] Synthesis of Compound A81 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A81 (12.26 g, purity: 99.94%, yield: 69.45%). 12.26 g of crude compound A81 was purified by sublimation to obtain sublimation pure compound A81 (7.61 g, purity: 99.94%, yield: 62.07%), mass spectrum: 629.21 (M+H).

[0132] 1 H NMR (400 MHz, CDCl3) δ 9.04 (d, J = 2.9 Hz, 1H), 8.22 – 8.15 (m,2H), 8.13 – 8.04 (m, 3H), 8.03 – 7.95 (m, 2H), 7.81 – 7.69 (m, 4H), 7.68 – 7.60 (m, 3H), 7.59 – 7.46 (m, 4H), 7.44 – 7.30 (m, 4H), 7.29 – 7.19 (m, 2H), 7.12 – 7.05 (m, 2H), 7.04 – 6.95 (m, 1H). Synthesis of Compound A84

[0133] Synthesis of Compound A84-1 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A84-1 (12.56 g, purity: 98.97%, yield: 71.46%), mass spectrum: 322.15 (M+H).

[0134] Synthesis of Compound A84-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A84-3 (9.81 g, purity: 99.57%, yield: 73.79%), mass spectrum: 356.07 (M+H).

[0135] Synthesis of Compound A84-4 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A84-4 (7.81 g, purity: 99.32%, yield: 70.92%), mass spectrum: 413.15 (M+H).

[0136] Synthesis of Compound A84 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A84 (8.14 g, purity: 99.95%, yield: 65.95%). 8.14 g of crude compound A84 was purified by sublimation to obtain sublimation pure compound A84 (5.02, purity: 99.95%, yield: 61.67%), mass spectrum: 679.23 (M+H).

[0137] 1 H NMR (400 MHz, CDCl3) δ 9.01 (d, J = 3.0 Hz, 1H), 8.22 – 8.15 (m,2H), 8.14 – 8.04 (m, 3H), 8.03 – 7.94 (m, 2H), 7.84 (dd, J = 14.9, 3.0 Hz,1H), 7.80-7.69 (m, 4H), 7.68 – 7.60 (m, 3H), 7.59 – 7.46 (m, 3H), 7.43-7.36(m, 2H), 7.35 – 7.29 (m, 2H), 7.29 – 7.20 (m, 2H), 7.17 (t, J = 2.9 Hz, 1H),7.14 – 7.04 (m, 3H), 7.04 – 6.95 (m, 1H). Synthesis of Compound A99

[0138] Synthesis of Compound A99-1 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A99-1 (12.61 g, yield: 75.84%), mass spectrum: 334.05 (M+H).

[0139] Synthesis of Compound A99-2 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A99-2 (11.73 g, purity: 99.05%, yield: 90.17%), mass spectrum: 362.08 (M+H).

[0140] Synthesis of Compound A99-3 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A99-3 (7.69 g, purity: 99.74%, yield: 73.37%), mass spectrum: 330.06 (M+H).

[0141] Synthesis of Compound A99-4 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A99-4 (6.72 g, purity: 99.81%, yield: 76.46%), mass spectrum: 387.14 (M+H).

[0142] Synthesis of Compound A99 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A99 (8.47 g, purity: 99.94%, yield: 77.15%). 8.47 g of crude compound A99 was purified by sublimation to obtain sublimation pure compound A99 (5.53 g, purity: 99.94%, yield: 65.28%), mass spectrum: 653.21 (M+H).

[0143] 1 H NMR (400 MHz, CDCl3) δ 9.15 (d, J = 2.9 Hz, 1H), 8.89 (d, J = 3.1Hz, 1H), 8.22 – 8.14 (m, 2H), 8.14 – 8.02 (m, 7H), 7.98 (dd, J = 14.6, 3.4Hz, 1H), 7.92 (dd, J = 15.0, 2.8 Hz, 1H), 7.83 (dd, J = 15.0, 3.0 Hz, 1H), 7.78 – 7.60 (m, 6H), 7.54 (dd, J = 14.7, 3.4 Hz, 1H), 7.44-7.35 (m, 1H), 7.32(dd, J = 14.7, 3.4 Hz, 1H), 7.29 – 7.19 (m, 2H), 7.11 – 7.04 (m, 2H), 7.04 –6.95 (m, 1H). Synthesis of Compound A116

[0144] Synthesis of Compound A116-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A116-2 (10.83 g, purity: 99.51%, yield: 74.85%), mass spectrum: 307.04 (M+H).

[0145] Synthesis of Compound A116-3 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A116-3 (10.51 g, yield: 91.71%), mass spectrum: 335.07 (M+H).

[0146] Synthesis of Compound A116-4 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A116-4 (6.84 g, purity: 99.78%, yield: 72.04%), mass spectrum: 303.05 (M+H).

[0147] Synthesis of Compound A116 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A116 (9.37 g, purity: 99.92%, yield: 69.42%). 9.37 g of crude compound A116 was purified by sublimation to obtain sublimation pure compound A116 (5.97 g, purity: 99.94%, yield: 63.71%), mass spectrum: 629.22 (M+H).

[0148] 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 15.0 Hz, 1H), 8.22 – 8.14 (m,2H), 8.14 – 8.05 (m, 2H),8.0- 7.95 (m, 3H), 7.95 – 7.89 (m, 1H), 7.85 – 7.60(m, 6H), 7.60 – 7.45 (m, 4H), 7.44 – 7.20 (m, 6H), 7.12 – 7.05 (m, 2H), 7.04– 6.95 (m, 1H). Synthesis of Compound A121

[0149] Synthesis of Compound A121-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A121-3 (12.86 g, purity: 99.47%, yield: 73.41%), mass spectrum: 329.06 (M+H).

[0150] Synthesis of Compound A121-4 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A121-4 (11.34 g, purity: 99.14%, yield: 70.97%), mass spectrum: 421.19 (M+H).

[0151] Synthesis of Compound A121-5 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A121-5 (8.65 g, purity: 99.69%, yield: 76.35%), mass spectrum: 433.09 (M+H).

[0152] Synthesis of Compound A121-6 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A121-6 (8.07 g, yield: 89.16%), mass spectrum: 461.12 (M+H).

[0153] Synthesis of Compound A121-7 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A121-7 (5.62 g, purity: 99.65%, yield: 75.50%), mass spectrum: 429.09 (M+H).

[0154] Synthesis of Compound A121 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A121 (6.71 g, purity: 99.90%, yield: 69.32%). 6.71 g of crude compound A121 was purified by sublimation to obtain sublimation pure compound A121 (4.29 g, purity: 99.96%, yield: 63.93%), mass spectrum: 755.26 (M+H).

[0155] 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J = 15.0 Hz, 1H), 8.56 (d, J = 2.8Hz, 1H), 8.23 ​​– 8.14 (m, 2H), 8.14 – 7.96 (m, 7H), 7.92 (dd, J = 14.9, 2.9Hz, 1H), 7.87 (dd, J = 15.0, 3.1 Hz, 1H), 7.77 (dd, J = 14.8, 3.1 Hz, 1H), 7.71 (dd, J = 11.1, 3.9 Hz, 1H), 7.69 – 7.59 (m, 6H), 7.59 – 7.47 (m, 5H),7.42 – 7.33 (m, 3H), 7.30 – 7.19 (m, 2H), 7.13 – 7.05 (m, 2H), 7.04 – 6.95 (m, 1H). Synthesis of Compound A143

[0156] Synthesis of Compound A143-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A143-2 (15.62 g, purity: 99.54%, yield: 71.97%), mass spectrum: 307.04 (M+H).

[0157] Synthesis of Compound A143-3 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A143-3 (15.17 g, yield: 89.67%), mass spectrum: 335.08 (M+H).

[0158] Synthesis of Compound A143-4 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A143-4 (9.67 g, purity: 99.73%, yield: 71.29%), mass spectrum: 303.05 (M+H).

[0159] Synthesis of Compound A143-5 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A143-5 (10.87 g, purity: 99.78%, yield: 68.90%), mass spectrum: 439.17 (M+H).

[0160] Synthesis of Compound A143 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A143 (15.20 g, purity: 99.91%, yield: 68.73%). 15.20 g of crude compound A143 was purified by sublimation to obtain sublimation pure compound A143 (9.97 g, purity: 99.96%, yield: 65.59%), mass spectrum: 705.25 (M+H).

[0161] 1 H NMR (400 MHz, CDCl3) δ 8.64 (dd, J = 14.3, 3.7 Hz, 1H), 8.23 ​​– 8.14(m, 2H), 8.11 (d, J = 1.9 Hz, 2H), 7.98 (dd, J = 14.6, 3.4 Hz, 1H), 7.95-7.88(m, 1H), 7.80 – 7.60 (m, 10H), 7.59 – 7.45 (m, 8H), 7.45 – 7.34 (m, 6H),7.34-7.27 (m, 1H). Synthesis of Compound A167

[0162] Synthesis of Compound A167-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A167-2 (17.56 g, purity: 99.33%, yield: 75.22%), mass spectrum: 329.10 (M+H).

[0163] Synthesis of Compound A167-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A167-3 (13.17 g, purity: 99.36%, yield: 80.62%), mass spectrum: 307.04 (M+H).

[0164] Synthesis of Compound A167-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A167-4 (12.91 g, yield: 90.99%), mass spectrum: 335.08 (M+H).

[0165] Synthesis of Compound A167-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A167-5 (5.31 g, purity: 99.37%, yield: 45.52%), mass spectrum: 303.05 (M+H).

[0166] Synthesis of Compound A167-7 Referring to the synthesis and purification method of compound A68-3, it is only necessary to change the corresponding raw materials to obtain the target compound A167-7 (6.92 g, yield: 90.01%), mass spectrum: 298.05 (M+H).

[0167] Synthesis of Compound A167-8 Referring to the synthesis and purification method of compound A68-4, it is only necessary to change the corresponding raw materials to obtain the target compound A167-8 (4.72 g, yield: 72.81%), mass spectrum: 280.04 (M+H).

[0168] Synthesis of Compound A167-10 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A167-10 (5.19 g, yield: 69.75%), mass spectrum: 463.17 (M+H).

[0169] Synthesis of Compound A167 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A167 (5.28 g, purity: 99.90%, yield: 67.02%). 5.28 g of crude compound A167 was purified by sublimation to obtain sublimation pure compound A167 (3.27 g, purity: 99.90%, yield: 61.93%), mass spectrum: 729.24 (M+H).

[0170] 1H NMR (400 MHz, CDCl3) δ 9.27 (s, 1H), 8.85 (dd, J = 14.1, 3.8 Hz,1H), 8.30 (d, J = 3.1 Hz, 1H), 8.23 ​​– 8.14 (m, 2H), 8.12 – 7.96 (m, 4H), 7.95– 7.87 (m, 2H), 7.75 (dd, J = 15.0, 2.9 Hz, 1H), 7.72 – 7.61 (m, 7H), 7.60 –7.51 (m, 6H), 7.42 (dd, J = 15.0, 3.0 Hz, 1H), 7.40 – 7.31 (m, 4H), 7.11 (d,J = 3.0 Hz, 1H), 7.05 (d, J = 14.8 Hz, 1H). Synthesis of Compound A182

[0171] Synthesis of Compound A182-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A182-2 (25.29 g, purity: 99.25%, yield: 72.23%), mass spectrum: 329.10 (M+H).

[0172] Synthesis of Compound A182-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A182-3 (15.38 g, purity: 99.76%, yield: 65.90%), mass spectrum: 307.04 (M+H).

[0173] Synthesis of Compound A182-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A182-4 (15.27 g, yield: 93.27%), mass spectrum: 335.08 (M+H).

[0174] Synthesis of Compound A182-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A182-5 (5.97 g, purity: 99.42%, yield: 44.01%), mass spectrum: 303.05 (M+H).

[0175] Synthesis of Compound A182-7 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A182-7 (8.17 g, purity: 99.75%, yield: 69.73%), mass spectrum: 322.15 (M+H).

[0176] Synthesis of Compound A182-9 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A182-9 (6.71 g, purity: 99.84%, yield: 74.33%), mass spectrum: 363.14 (M+H).

[0177] Synthesis of Compound A182 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A182 (6.94 g, purity: 99.95%, yield: 66.84%). 6.94 g of crude compound A182 was purified by sublimation to obtain sublimation pure compound A182 (4.75 g, purity: 99.90%, yield: 68.41%), mass spectrum: 629.21 (M+H).

[0178] 1 H NMR (400 MHz, CDCl3) δ 9.01 (s, 1H), 8.84 (dd, J = 14.2, 3.7 Hz,1H), 8.54 (d, J = 3.1 Hz, 1H), 8.26 – 8.14 (m, 3H), 8.09 (d, J = 2.9 Hz, 1H),7.96 – 7.87 (m, 2H), 7.84 (d, J = 14.9 Hz, 1H), 7.80 – 7.70 (m, 2H), 7.70 –7.59 (m, 5H), 7.58 – 7.52 (m, 2H), 7.46 (d, J = 15.0 Hz, 1H), 7.40 – 7.34 (m,2H), 7.31 (dd, J = 14.9, 3.0 Hz, 1H), 7.28 – 7.18 (m, 2H), 7.12 – 7.05 (m,2H), 7.04 – 6.95 (m, 1H). Synthesis of Compound A207

[0179] Synthesis of Compound A207-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A207-3 (6.79 g, purity: 99.17%, yield: 64.96%), mass spectrum: 305.06 (M+H).

[0180] Synthesis of Compound A207-6 Compound A207-3 (6.50 g, 21.33 mmol), compound A207-4 (0.13 g, 1.07 mmol), compound A207-5 (6.21 g, 31.99 mmol), palladium acetate (0.24 g, 1.07 mol), 1,3-dimethyl-2-imidazolidinone (60 ml) and hexafluorobenzene (40 ml) were added into a 250 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then the system was heated to 95 °C for 4 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). Compound A207-3 was completely consumed.

[0181] The temperature was lowered to 60°C, dichloromethane (200 ml) was added, and the mixture was washed three times with deionized water (50 ml × 3). The mixture was separated, and the sample was 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 = 1:10 as the eluent). After elution, the mixture was concentrated under reduced pressure at 60°C for 1 hour to obtain a white solid, which was compound A207-6 (4.36 g, purity: 99.31%, yield: 67.52%), with a mass spectrum of 303.05 (M+H).

[0182] Synthesis of Compound A207 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A207 (5.84 g, purity: 99.89%, yield: 70.30%). 5.84 g of crude compound A207 was purified by sublimation to obtain sublimation pure compound A207 (3.69 g, purity: 99.90%, yield: 63.18%), mass spectrum: 629.21 (M+H).

[0183] 1H NMR (400 MHz, CDCl3) δ 8.98 (dd, J = 14.2, 3.7 Hz, 1H), 8.85 (d, J= 15.0 Hz, 1H), 8.47 (d, J = 3.1 Hz, 1H), 8.24 – 8.14 (m, 2H), 8.11 (dd, J =14.3, 3.7 Hz, 1H), 7.98 (dd, J = 14.6, 3.4 Hz, 1H), 7.80 – 7.60 (m, 8H), 7.60– 7.49 (m, 4H), 7.41 – 7.32 (m, 3H), 7.32 – 7.18 (m, 3H), 7.12 – 7.05 (m,2H), 7.05 – 6.94 (m, 1H). Synthesis of compound A234

[0184] Synthesis of Compound A234-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A234-2 (13.17 g, purity: 99.07%, yield: 76.15%), mass spectrum: 355.15 (M+H).

[0185] Synthesis of Compound A234-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A234-3 (8.69 g, purity: 99.69%, yield: 71.24%), mass spectrum: 333.09 (M+H).

[0186] Synthesis of Compound A234-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A234-4 (8.31 g, yield: 90.16%), mass spectrum: 361.13 (M+H).

[0187] Synthesis of Compound A234-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A234-5 (5.14 g, purity: 99.31%, yield: 70.51%), mass spectrum: 329.10 (M+H).

[0188] Synthesis of Compound A234-7 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A234-7 (6.14 g, purity: 99.79%, yield: 70.98%), mass spectrum: 556.19 (M+H).

[0189] Synthesis of compound A234 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A234 (6.39 g, purity: 99.93%, yield: 69.78%). 6.39 g of crude compound A234 was purified by sublimation to obtain sublimation pure compound A234 (4.16 g, purity: 99.96%, yield: 65.10%), mass spectrum: 848.32 (M+H).

[0190] 1 H NMR (400 MHz, CDCl3) δ 8.98 (dd, J = 14.1, 3.8 Hz, 1H), 8.23 ​​– 8.15 (m, 6H), 8.08 (dd, J = 15.0, 3.0 Hz, 1H), 7.93 – 7.85 (m, 2H), 7.79 (d, J =3.1 Hz, 1H), 7.77 – 7.72 (m, 4H), 7.71 – 7.67 (m, 2H), 7.67 – 7.60 (m, 7H), 7.58 – 7.50 (m, 7H), 7.40 – 7.34 (m, 4H), 1.75 (s, 6H). Synthesis of Compound A248

[0191] Synthesis of Compound A248-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A248-2 (15.69 g, purity: 99.29%, yield: 69.30%), mass spectrum: 404.15 (M+H).

[0192] Synthesis of Compound A248-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A248-3 (10.27 g, purity: 99.69%, yield: 70.05%), mass spectrum: 382.09 (M+H).

[0193] Synthesis of Compound A248-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A248-4 (9.65 g, yield: 89.91%), mass spectrum: 410.12 (M+H).

[0194] Synthesis of Compound A248-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A248-5 (5.94 g, purity: 99.63%, yield: 67.12%), mass spectrum: 378.09 (M+H).

[0195] Synthesis of Compound A248-6 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A248-6 (8.19 g, purity: 99.56%, yield: 67.95%), mass spectrum: 337.12 (M+H).

[0196] Synthesis of Compound A248 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A248 (7.15 g, purity: 99.96%, yield: 70.97%). 7.15 g of crude compound A248 was purified by sublimation to obtain sublimation pure compound A248 (5.04 g, purity: 99.97%, yield: 70.48%), mass spectrum: 678.25 (M+H).

[0197] 1 H NMR (400 MHz, CDCl3) δ 8.95 (dd, J = 14.1, 3.8 Hz, 1H), 8.34 (d, J= 15.0 Hz, 1H), 8.27 – 8.21 (m, 1H), 8.21 – 8.14 (m, 2H), 8.14 – 8.04 (m,2H), 7.94 – 7.86 (m, 1H), 7.75 (dd, J = 15.0, 3.0 Hz, 1H), 7.70 – 7.46 (m,12H), 7.42 (dd, J = 15.0, 2.9 Hz, 1H), 7.30 – 7.19 (m, 4H), 7.12 – 7.03 (m,4H), 7.03 – 6.96 (m, 1H). Synthesis of compound A259

[0198] Synthesis of Compound A259-1 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A259-1 (7.68 g, purity: 99.49%, yield: 68.38%), mass spectrum: 368.17 (M+H).

[0199] Synthesis of compound A259 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A259 (8.31 g, purity: 99.91%, yield: 68.83%). 8.31 g of crude compound A259 was purified by sublimation to obtain sublimation pure compound A259 (5.69 g, purity: 99.95%, yield: 68.47%), mass spectrum: 634.25 (M+H).

[0200] 1 H NMR (400 MHz, CDCl3) δ 8.89 (d, J = 15.0 Hz, 1H), 8.21 – 8.14 (m,2H), 8.14 – 8.05 (m, 2H), 8.02 – 7.89 (m, 4H), 7.84-7.74 (m, 2H), 7.73-7.69(m, 1H), 7.68 – 7.60 (m, 3H), 7.59 – 7.49 (m, 4H), 7.43 – 7.26 (m, 4H). Synthesis of Compound A268 ;

[0201] Synthesis of Compound A268-2 Referring to the synthesis and purification method of compound A68-3, it is only necessary to change the corresponding raw materials to obtain the target compound A268-2 (14.37 g, yield: 90.92%), mass spectrum: 297.02 (M+H).

[0202] Synthesis of Compound A268-3 Referring to the synthesis and purification method of compound A68-4, it is only necessary to change the corresponding raw materials to obtain the target compound A268-3 (8.19 g, purity: 99.36%, yield: 62.28%), mass spectrum: 279.01 (M+H).

[0203] Synthesis of Compound A268-4 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A268-4 (6.34 g, purity: 99.51%, yield: 71.18%), mass spectrum: 311.09 (M+H).

[0204] Synthesis of Compound A268-5 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A268-5 (5.18 g, purity: 99.48%, yield: 72.03%), mass spectrum: 373.20 (M+H).

[0205] Synthesis of Compound A268-7 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A268-7 (7.62 g, purity: 99.70%, yield: 73.32%), mass spectrum: 333.09 (M+H).

[0206] Synthesis of Compound A268-8 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A268-8 (7.29 g, yield: 89.64%), mass spectrum: 361.13 (M+H).

[0207] Synthesis of Compound A268-9 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A268-9 (4.07 g, purity: 99.53%, yield: 62.04%), mass spectrum: 329.10 (M+H).

[0208] Synthesis of Compound A268 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A268 (5.06 g, purity: 99.94%, yield: 71.50%). 5.06 g of crude compound A268 was purified by sublimation to obtain sublimation pure compound A268 (3.26 g, purity: 99.93%, yield: 64.42%), mass spectrum: 665.33 (M+H).

[0209] 1H NMR (400 MHz, CDCl3) δ 8.86 (d, J = 15.0 Hz, 1H), 8.27-8.17 (m,2H), 8.08 (dd, J = 14.7, 2.9 Hz, 1H), 7.97-7.89 (m, 2H), 7.85 – 7.67 (m, 5H), 7.59 – 7.46 (m, 4H), 7.41 – 7.29 (m, 3H), 1.75 (s, 6H). Synthesis of compound A277 ;

[0210] Synthesis of Compound A277-2 Referring to the synthesis and purification method of compound A68-3, it is only necessary to change the corresponding raw materials to obtain the target compound A277-2 (14.23 g, yield: 90.04%), mass spectrum: 297.02 (M+H).

[0211] Synthesis of Compound A277-3 Referring to the synthesis and purification method of compound A68-4, it is only necessary to change the corresponding raw materials to obtain the target compound A277-3 (8.74 g, purity: 99.43%, yield: 66.46%), mass spectrum: 279.01 (M+H).

[0212] Synthesis of Compound A277-4 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A277-4 (7.21 g, purity: 99.38%, yield: 76.19%), mass spectrum: 311.09 (M+H).

[0213] Synthesis of Compound A277-5 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A277-5 (5.63 g, purity: 99.76%, yield: 67.11%), mass spectrum: 373.20 (M+H).

[0214] Synthesis of Compound A277-8 Compound A277-6 (10.00 g, 40.63 mmol), compound A277-7 (12.74 g, 60.95 mmol), cuprous iodide (0.39 g, 2.03 mmol), potassium phosphate (21.56 g, 101.58 mol), 1,2-diaminocyclohexane (0.47 g, 4.06 mol), and 1,4-dioxane (250 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 100 ° C for 7 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A277-6 was completely consumed.

[0215] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (300 ml) was added, and the mixture was washed three times with deionized water (300 ml × 3). The mixture was separated, and the sample was 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 = 1:10 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid as compound A277-8 (9.46 g, purity: 99.37%, yield: 71.15%), with a mass spectrum of 327.05 (M+H).

[0216] Synthesis of Compound A277-9 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A277-9 (7.75 g, purity: 99.28%, yield: 75.28%), mass spectrum: 375.22 (M+H).

[0217] Synthesis of Compound A277-10 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A277-10 (5.61 g, purity: 99.60%, yield: 72.37%), mass spectrum: 387.12 (M+H).

[0218] Synthesis of Compound A277-11 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A277-11 (5.34 g, yield: 90.53%), mass spectrum: 415.15 (M+H).

[0219] Synthesis of Compound A277-12 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A277-12 (3.63 g, purity: 99.68%, yield: 74.22%), mass spectrum: 383.13 (M+H).

[0220] Synthesis of compound A277 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A277 (4.11 g, purity: 99.90%, yield: 62.54%). 4.11 g of crude compound A277 was purified by sublimation to obtain sublimation pure compound A277 (2.57 g, purity: 99.93%, yield: 62.53%), mass spectrum: 719.36 (M+H).

[0221] 1 H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 15.0 Hz, 1H), 8.31 – 8.24 (m,1H), 8.22 – 8.16 (m, 1H), 8.15-8.04 (m, 2H), 7.98 (t, J = 2.9 Hz, 1H), 7.95 –7.72 (m, 4H), 7.62 – 7.31 (m, 6H), 7.26 – 7.13 (m, 2H). Synthesis of compound A280

[0222] Synthesis of Compound A280-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A280-3 (11.53 g, purity: 99.46%, yield: 77.47%), mass spectrum: 354.09 (M+H).

[0223] Synthesis of Compound A280-4 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A280-4 (9.31 g, purity: 99.01%, yield: 64.32%), mass spectrum: 446.22 (M+H).

[0224] Synthesis of Compound A280-5 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A280-5 (6.43 g, purity: 99.67%, yield: 69.48%), mass spectrum: 458.12 (M+H).

[0225] Synthesis of Compound A280-6 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A280-6 (6.14 g, yield: 90.40%), mass spectrum: 486.15 (M+H).

[0226] Synthesis of Compound A280-7 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A280-7 (3.89 g, purity: 99.66%, yield: 69.41%), mass spectrum: 454.13 (M+H).

[0227] Synthesis of compound A280 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A280 (4.93 g, purity: 99.85%, yield: 75.03%). 4.93 g of crude compound A280 was purified by sublimation to obtain sublimation pure compound A280 (3.37 g, purity: 99.90%, yield: 68.35%), mass spectrum: 785.33 (M+H).

[0228] 1 H NMR (400 MHz, CDCl3) δ 8.86 (d, J = 14.9 Hz, 1H), 8.47 (d, J = 2.9Hz, 1H), 8.27 (d, J = 15.0 Hz, 1H), 8.20 – 8.12 (m, 2H), 8.11 – 8.02 (m, 2H),7.94-7.86 (m, 2H), 7.80 – 7.71 (m, 4H), 7.71 – 7.67 (m, 1H), 7.66 – 7.55 (m,7H), 7.54-7.43 (m, 8H), 7.42 – 7.31 (m, 3H). Synthesis of Compound A284

[0229] Synthesis of Compound A284-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound A284-2 (12.75 g, purity: 99.38%, yield: 73.39%), mass spectrum: 345.08 (M+H).

[0230] Synthesis of Compound A284-3 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A284-3 (8.11 g, purity: 99.65%, yield: 69.27%), mass spectrum: 323.02 (M+H).

[0231] Synthesis of Compound A284-4 Referring to the synthesis and purification method of compound A2-7, it is only necessary to change the corresponding raw materials to obtain the target compound A284-4 (7.84 g, yield: 90.16%), mass spectrum: 351.05 (M+H).

[0232] Synthesis of Compound A284-5 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound A284-5 (5.09 g, purity: 99.70%, yield: 71.81%), mass spectrum: 319.03 (M+H).

[0233] Synthesis of Compound A284-7 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A284-7 (8.29 g, purity: 99.64%, yield: 66.63%), mass spectrum: 381.13 (M+H).

[0234] Synthesis of Compound A284 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A284 (5.99 g, purity: 99.90%, yield: 68.76%). 5.99 g of crude compound A284 was purified by sublimation to obtain sublimation pure compound A284 (3.88 g, purity: 99.95%, yield: 64.77%), mass spectrum: 663.18 (M+H).

[0235] 1H NMR (400 MHz, CDCl3) δ 8.98 (dd, J = 14.1, 3.8 Hz, 1H), 8.35 (d, J= 15.0 Hz, 1H), 8.22 – 8.14 (m, 2H), 8.14 – 8.05 (m, 2H), 7.98 (d, J = 2.9Hz, 1H), 7.93 – 7.87 (m, 1H), 7.80 – 7.59 (m, 9H), 7.58 – 7.46 (m, 3H), 7.41 – 7.33 (m, 2H), 7.21 – 7.12 (m, 2H), 7.09 – 6.99 (m, 3H). Synthesis of compound A290

[0236] Synthesis of Compound A290-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound A290-2 (10.37 g, purity: 99.75%, yield: 71.39%), mass spectrum: 322.04 (M+H).

[0237] Synthesis of Compound A290-3 Referring to the synthesis and purification method of compound A2-11, it is only necessary to change the corresponding raw materials to obtain the target compound A290-3 (8.57 g, purity: 99.60%, yield: 72.87%), mass spectrum: 379.12 (M+H).

[0238] Synthesis of compound A290 Referring to the synthesis and purification method of compound A2, only the corresponding raw materials need to be changed to obtain the target compound A290 (7.28 g, purity: 99.96%, yield: 68.37%). 7.28 g of crude compound A290 was purified by sublimation to obtain sublimation pure compound A290 (4.95 g, purity: 99.95%, yield: 67.98%), mass spectrum: 645.19 (M+H).

[0239] 1H NMR (400 MHz, CDCl3) δ 8.88 (d, J = 15.0 Hz, 1H), 8.28 (dd, J =15.0, 3.1 Hz, 1H), 8.14 – 7.88 (m, 9H), 7.83 (dd, J = 15.0, 3.1 Hz, 1H), 7.72(t, J = 14.9 Hz, 1H), 7.60 – 7.49 (m, 6H), 7.44 – 7.19 (m, 6H), 7.12 – 6.95(m, 3H). Synthesis of compound B25

[0240] Synthesis of compound B25-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound B25-2 (24.53 g, purity: 99.42%, yield: 77.41%), mass spectrum: 421.19 (M+H).

[0241] Synthesis of compound B25 Referring to the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B25 (12.11 g, purity: 99.95%, yield: 79.06%) as a white solid. 12.11 grams of crude compound B25 was purified by sublimation to obtain sublimation pure compound B25 (9.99 g, purity: 99.95%, yield: 82.50%), mass spectrum: 576.24 (M+H).

[0242] 1 H NMR (400 MHz, CDCl3) δ 9.41 (s, 1H), 9.35 (d, J = 8.7 Hz, 1H), 8.91 – 8.88 (m, 3H), 8.73 (d, J = 7.3 Hz, 1H), 8.14 (d, J = 7.5 Hz, 1H), 8.08(d, J = 8.7 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.82 – 7.57 (m, 10H), 7.44 –7.34 (m, 3H), 7.26 (s, 1H), 6.96 (t, J = 7.5 Hz, 1H), 6.79 (d, J = 7.9 Hz,1H). Synthesis of compound B27

[0243] Synthesis of compound B27 Referring to the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B27 (6.82 g, purity: 99.96%, yield: 65.93%). 6.82 g of crude compound B27 was purified by sublimation to obtain sublimation pure compound B27 (4.14 g, purity: 99.95%, yield: 66.02%), mass spectrum: 601.22 (M+H).

[0244] 1 H NMR (400 MHz, CDCl3) δ 9.02 (dd, J = 14.2, 3.7 Hz, 1H), 8.95 (dd, J= 14.2, 3.7 Hz, 1H), 8.34 – 8.27 (m, 2H), 8.23 ​​(s, 1H), 8.02 – 7.90 (m, 3H), 7.89 – 7.82 (m, 2H), 7.81 – 7.70 (m, 3H), 7.63 – 7.45 (m, 10H), 7.44 – 7.27(m, 5H). Synthesis of compound B54

[0245] Synthesis of compound B54-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B54-2 (20.00 g, purity: 99.1%, yield: 75.63%), mass spectrum: 257.03 (M+H).

[0246] Synthesis of compound B54-3 Referring to the synthesis and purification method of compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound B54-3 (16.78 g, yield: 96.06%) as a white solid, with a mass spectrum of 285.06 (M+H). The obtained compound was used directly in the next step without purification.

[0247] Synthesis of compound B54-4 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B54-4 (15.63 g, purity: 99.78%, yield: 75.12%), mass spectrum: 253.03 (M+H).

[0248] Synthesis of compound B54-5 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B54-5 (15.12 g, purity: 99.43%, yield: 76.51%), mass spectrum: 345.16 (M+H).

[0249] Synthesis of compound B54-7 Compound B54-5 (20.00 g, 58.10 mmol), compound B54-6 (19.35 g, 58.10 mmol), tetrakis(triphenylphosphine)palladium (0.67 g, 0.58 mmol), potassium carbonate (12.04 g, 87.15 mmol), tetrahydrofuran (300 ml), and deionized water (100 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 65 ° C for 6 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound B54-5 was completely consumed.

[0250] The temperature was lowered to 60°C and the solvent was removed by concentrating under reduced pressure. Ethyl acetate (700 ml) was added and the mixture was washed three times with deionized water (300 ml × 3). The mixture was separated and the sample was 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 the eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid compound B54-7 (18.53 g, purity: 99.21%, yield: 75.32%), with a mass spectrum of 423.22 (M+H).

[0251] Synthesis of compound B54-8 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B54-8 (12.12 g, purity: 99.03%, yield: 78.06%), mass spectrum: 471.22 (M+H).

[0252] Synthesis of compound B54 Referring to the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B54 (15.12 g, purity: 99.94%, yield: 77.63%) as a light yellow solid. 15.12 g of crude compound B54 was purified by sublimation to obtain sublimation pure compound B54 (12.57 g, purity: 99.94%, yield: 83.14%), mass spectrum: 576.20 (M+H).

[0253] 1H NMR (400 MHz, CDCl3) δ 8.41 (t, J = 2.2 Hz, 1H), 8.24 (t, J = 2.2Hz, 1H), 8.18 (d, J = 8.3 Hz, 1H), 8.11 – 8.06 (m, 5H), 8.06 – 7.99 (m, 3H),7.96 – 7.94 (m, 1H), 7.79 – 7.77 (m, 1H), 7.71 – 7.69 (m, 1H), 7.67 – 7.57(m, 2H), 7.55 – 7.38 (m, 8H), 7.32 (d, J = 7.3 Hz, 1H). Synthesis of compound B71

[0254] Synthesis of compound B71-1 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B71-1 (9.16 g, purity: 99.17%, yield: 79.67%), mass spectrum: 422.18 (M+H).

[0255] Synthesis of compound B71 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound B71 (10.21 g, purity: 99.93%, yield: 77.50%). After sublimation and purification of 10.21 grams of crude compound B71, sublimation pure compound B71 (6.25 g, purity: 99.93%, yield: 61.21%) was obtained, mass spectrum: 617.20 (M+H).

[0256] 1 H NMR (400 MHz, CDCl3) δ 9.69 (d, J = 2.9 Hz, 1H), 8.52 (dd, J =15.0, 3.0 Hz, 1H), 8.42 – 8.31 (m, 2H), 8.22 – 8.13 (m, 3H), 8.11 (d, J = 1.4Hz, 2H), 7.98 (dd, J = 14.6, 3.4 Hz, 1H), 7.92 (m, 1H), 7.75 (dd, J = 15.0,3.0 Hz, 1H), 7.70 – 7.45 (m, 10H), 7.45 – 7.35 (m, 1H), 7.31 (m, 1H). Synthesis of compound B80

[0257] Synthesis of compound B80-2 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound B80-2 (14.19 g, purity: 99.34%, yield: 68.27%), mass spectrum: 334.08 (M+H).

[0258] Synthesis of compound B80-3 Referring to the synthesis and purification method of compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound B80-3 (13.71 g, yield: 90.34%), mass spectrum: 362.08 (M+H). The obtained compound was used directly in the next step without purification.

[0259] Synthesis of compound B80-4 Referring to the synthesis and purification method of compound A2-8, it is only necessary to change the corresponding raw materials to obtain the target compound B80-4 (7.96 g, purity: 99.71%, yield: 63.75%), mass spectrum: 330.06 (M+H).

[0260] Synthesis of compound B80-5 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound B80-5 (7.25 g, purity: 99.29%, yield: 75.67%), mass spectrum: 422.21 (M+H).

[0261] Synthesis of compound B80 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound B80 (7.06 g, purity: 99.93%, yield: 68.90%). After sublimation and purification of 7.06 grams of crude compound B80, sublimation pure compound B80 (4.71 g, purity: 99.93%, yield: 66.71%) was obtained, mass spectrum: 617.19 (M+H).

[0262] 1H NMR (400 MHz, CDCl3) δ 9.11 (d, J = 15.0 Hz, 1H), 8.88-8.82 (m,1H), 8.41 – 8.32 (m, 2H), 8.25 – 8.15 (m, 4H), 8.14-8.03 (m, 2H), 7.98 (dd, J= 14.6, 3.4 Hz, 1H), 7.92 (t, J = 1.4 Hz, 2H), 7.78 (d, J = 15.0 Hz, 1H), 7.70 – 7.46 (m, 8H), 7.44-7.26 (m, 2H). Synthesis of compound B96

[0263] Synthesis of compound B96 Referring to the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B96 (7.84 g, purity: 99.95%, yield: 70.09%). 7.84 g of crude compound B96 was sublimated and purified to obtain sublimation pure compound B96 (5.46 g, purity: 99.95%, yield: 69.70%), mass spectrum: 648.24 (M+H).

[0264] 1 H NMR (400 MHz, CDCl3) δ 9.08 (dd, J = 14.6, 3.4 Hz, 1H), 8.84 (dd, J= 14.2, 3.7 Hz, 1H), 8.41 – 8.31 (m, 3H), 8.25 (d, J = 2.9 Hz, 1H), 8.17 (dd,J = 14.6, 3.4 Hz, 1H), 8.09 (d, J = 15.0 Hz, 1H), 7.94 – 7.84 (m, 4H), 7.78 (dd,J = 15.0, 2.9 Hz, 1H), 7.74 – 7.57 (m, 7H), 7.54 – 7.47 (m, 3H), 7.39-7.30 (m, 1H), 7.29 – 7.17 (m, 5H). Synthesis of compound B104

[0265] Synthesis of compound B104 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain a light yellow solid as the target compound B104 (21.69 g, purity: 99.93%, yield: 87.70%). 21.69 grams of the crude compound B104 was sublimated and purified to obtain the sublimation pure compound B104 (17.85 g, purity: 99.93%, yield: 82.29%), mass spectrum: 550.20 (M+H).

[0266] 1 H NMR (400 MHz, CDCl3) δ 10.33 (s, 1H), 9.04 (d, J = 8.5 Hz, 1H), 8.92 – 8.76 (m, 4H), 8.51 (d, J = 7.6 Hz, 1H), 8.19 (d, J = 8.2 Hz, 1H), 8.11(d, J = 9.3 Hz, 1H), 8.09 – 7.98 (m, 2H), 7.87 (d, J = 7.8 Hz, 1H), 7.75 –7.65 (m, 5H), 7.60 – 7.50 (m, 3H), 7.26 – 7.21 (m, 3H). Synthesis of compound B128

[0267] Synthesis of compound B128-2 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound B128-2 (9.14 g, purity: 99.41%, yield: 74.93%), mass spectrum: 262.20 (M+H).

[0268] Synthesis of compound B128-4 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound B128-4 (8.01 g, purity: 99.62%, yield: 68.31%), mass spectrum: 340.06 (M+H).

[0269] Synthesis of compound B128-5 Referring to the synthesis and purification method of compound A2-3, it is only necessary to change the corresponding raw materials to obtain the target compound B128-5 (6.59 g, purity: 99.38%, yield: 72.37%), mass spectrum: 388.25 (M+H).

[0270] Synthesis of compound B128 Referring to the synthesis and purification method of compound A2-5, it is only necessary to change the corresponding raw materials to obtain the target compound B128 (6.34 g, purity: 99.96%, yield: 77.24%). After sublimation and purification of 6.34 grams of crude compound B128, sublimation pure compound B128 (4.39 g, purity: 99.96%, yield: 69.24%) was obtained, mass spectrum: 583.26 (M+H).

[0271] 1 H NMR (400 MHz, CDCl3) δ 9.07 (t, J = 3.0 Hz, 1H), 8.50 (dd, J =14.9, 3.0 Hz, 1H), 8.41 – 8.31 (m, 2H), 8.14 (dd, J = 15.0, 3.1 Hz, 1H),8.02-7.94 (m, 2H), 7.63 – 7.46 (m, 8H), 7.41-7.35 (m, 2H), 7.34-7.26 (m, 1H). Example: Examples 1 to 8 provide an aromatic amine compound, which corresponds to compounds A2, A50, A68, A79, A81, A99, A116, and A234 obtained by the above operations.

[0272] Embodiments 9 to 31 provide a composition for an organic light-emitting device, the composition comprising a first host material and a second host material, wherein the aromatic amine compound (A2, A50, A68, A79, A81, A84, A99, A116, A121, A143, A167, A182, A207, A234, A248, A259, A268, A277, A280, A284, A290) prepared by the above operation is used as the first host material, and the second host compound (B25, B27, B54, B71, B80, B96, B104, B128) satisfying the structure of formula (3) is used as the second host material. The mass ratio of the first host material to the second host material is 5:5.

[0273] Embodiment 32 provides a composition for an organic light-emitting device, the composition comprising a first host material and a second host material, wherein the aromatic amine compound A50 prepared by the above operation is used as the first host material, and the second host compound B25 satisfying the structure of formula (3) is used as the second host material. The mass ratio of the first host material to the second host material is 2:8.

[0274] Embodiment 33 provides a composition for an organic light-emitting device, the composition comprising a first host material and a second host material, wherein the aromatic amine compound A68 prepared by the above operation is used as the first host material, and the second host compound B54 satisfying the structure of formula (3) is used as the second host material. The mass ratio of the first host material to the second host material is 8:2.

[0275] For specific combinations, please refer to the performance test results table listed below.

[0276] Comparative Examples: Comparative Examples 1 to 4 provide a compound that can be used in an organic light-emitting device, which correspond to RH-N, comparative compound 2, comparative compound 3 and comparative compound 4, respectively.

[0277] Comparative Examples 5 to 10 provide a composition that can be used in an organic light-emitting device, the composition consisting of a first host material and a second host material, wherein the aromatic amine compound (A50) or comparative compounds 1 to 4 prepared by the above operation is used as the first host material, and the second host compound (B25, B54) or RH-N that satisfies the structure of formula (3) is used as the second host material. The mass ratio of the first host material to the second host material is 5:5. When the first host material is A50, the second host material is RH-N. The specific combination method is listed in the performance test result table below.

[0278] The structural formulas of comparative compounds 1 to 4 are as follows: .

[0279] Application examples: Fabrication of organic light-emitting devices As attached Figure 2 As shown, the organic light-emitting 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, an electron transport layer 7 (ETL), an electron injection layer 8 (EIL), and a cathode 9.

[0280] The specific production process is as follows: a 50mm×50mm×1.0mm glass substrate with an ITO (indium tin oxide, 100nm) transparent electrode is ultrasonically cleaned in ethanol for 10 minutes, dried at 150°C, and treated with N2Plasma (plasma gas) for 30 minutes. The washed glass substrate is mounted on a substrate holder of a vacuum evaporation device, and the compound NDP-9 and the compound HTM 1 are evaporated at a weight ratio of 97:3 to form a hole injection layer with a thickness of 10nm, followed by evaporation of a layer of HTM1 to form a film with a thickness of 60nm as HTL1 (hole transport layer 1), and then a layer of HTM2 is evaporated on HTL1 to form a film with a thickness of 10nm as HTL2 (hole transport layer 2).

[0281] Then, a light-emitting layer with a thickness of 40 nm was evaporated on HTL2, wherein the raw materials of the light-emitting layer consisted of a main material and a red light-doping material, the mass fraction of the main material was 97%, the mass fraction of the red light-doping material was 3%, and the main material was the compound or composition in the above-mentioned embodiments and comparative examples.

[0282] An electron transport layer with a thickness of 35 nm is formed by vapor deposition on the light-emitting layer, wherein a raw material of the electron transport layer is a mixture of ETL and LiQ, wherein the mass ratio of ETL to LiQ in the mixture is 50:50.

[0283] Then, LiQ was evaporated on the electron transport layer as an electron injection material (thickness of 1 nm), and then Mg / Ag (thickness of 100 nm, mass ratio of Mg to Ag of 1:9) was evaporated as a cathode material using a co-evaporation mode to produce an organic light-emitting device.

[0284] The structural formulas of NDP-9, HTM1, HTM2, ETL materials, red light doping materials, LiQ, and RH-N are as follows: .

[0285] evaluate: The above organic light-emitting device was tested for device performance, and the compound prepared in the present application and the comparative compounds 1-4 were used as the main materials for comparison. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and the luminescence spectrum was tested using a spectroscopic radiation system (CS 2000). At the same time, the luminescence spectrum was measured at 10 mA / cm 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm 2 The life of LT95 devices was tested under the following conditions. The results are shown in Tables 1 and 2 below.

[0286] Table 1 shows the device performance test data of using the aromatic amine compounds in Examples 1 to 8 of the present application or comparative compounds 1-4 as a single host and co-evaporating with a red light doping material to form a light-emitting layer.

[0287] Table 1

[0288] The performance test data of devices prepared as dual-host materials using the compositions in Examples 9-33 of the present application and Comparative Examples 5-10, and co-evaporated with red light-emitting doping materials to form a light-emitting layer are shown in Table 2.

[0289] Table 2

[0290] It can be seen from Tables 1-2 that the device life and luminous efficiency of the devices prepared using the compounds and compositions in the examples of the present application are significantly better than those of the devices prepared using the compounds and compositions in the comparative examples, and the voltage is significantly lower than that of the devices prepared using the compounds and compositions in the comparative examples.

[0291] Sublimation temperature comparison: Sublimation temperature is defined as: at 10 -7 The vacuum degree is 10000 Torr, and the temperature corresponding to the sublimation rate is 1 angstrom per second. The test results of some compounds of the examples of the present invention and comparative compounds 1 to 4 are shown in Table 3.

[0292] Table 3

[0293] It can be seen from Table 3 that the compounds of the examples of the present application have lower sublimation temperatures than the comparative compounds 1-4, which is conducive to industrial application.

[0294] The compound of the present application, as a single-host red light material, has lower voltage, higher current efficiency and longer life than the comparative compound; at the same time, when the compound of the present application is combined with an N-type second host compound as a dual-host material, it has a balanced hole and electron transfer rate and broadens the exciton recombination area in the light-emitting layer, which greatly improves the efficiency and life of the device compared with the comparative compound 1-1.

[0295] Therefore, the compound material of the present application has the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a main material in OLED light-emitting devices. At the same time, it has a low melting point, which is beneficial to the stability of material evaporation as a molten material. As a main material, the compound of the present application has the possibility of being applied to the AMOLED industry. Furthermore, as a red light main material, the aromatic amine compound has shown broad application prospects in display and lighting technologies such as LED, OLED (organic light-emitting diode), and AMOLED (active matrix organic light-emitting diode). Red light, as one of the three primary colors, is also crucial to achieving full-color display and efficient lighting. Therefore, with its unique molecular structure and excellent optoelectronic properties, the aromatic amine compound of the present application scheme not only provides an efficient and stable luminescent core for red light devices, but also leads a new direction for full-color display and efficient lighting.

[0296] In addition, since it is impossible to list all the compounds of the present application one by one, the above Tables 1-3 only list some of the compounds or device performances of the present application. However, within the scope of protection requested by the present application, especially the compounds with specific structural formulas given in the present application, all have the advantages similar to A2, such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

[0297] The embodiments of the present application are described in detail above, but the present application is not limited to the above embodiments, and various changes can be made within the knowledge scope of ordinary technicians in the relevant technical field without departing from the purpose of the present application.

Claims

1. An aromatic amine compound, characterized in that: The structure of the aromatic amine compound is shown in the following formula (1): Formula (1) In the formula, ring A is selected from substituted or unsubstituted phenanthrene ring; X is selected from oxygen group elements, CR a R b or NR c ; R a , R b and 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 or C6-C30 arylsilyl; each R1 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, or C6-C60 arylamine; a is an integer from 0 to 4; if a ≥ 2, each R1 is the same or different; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; B is selected from the structural substituents represented by the following formula (2); Formula (2) In the formula, ring C is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Y is selected from O, S or Se; represents the connection site with L2 in formula (1); Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group; The substitution in L1, L2, Ar1 and Ar2 each independently represents substitution 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 or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, and the number of substitutions ranges from single substitution to the maximum number of substitutions; The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group or heterocycloalkyl group are each independently selected from at least one of O, S, N, Se, Si and Ge.

2. The aromatic amine compound according to claim 1, characterized in that: The oxygen group element is selected from O, S or Se; and / or, The R a , R b and R c Each is independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl or C6-C20 arylsilyl; and / or, L1 and L2 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene or substituted or unsubstituted naphthylene; and / or, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysene, 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, or a combination of at least two of the above.

3. The aromatic amine compound according to claim 1, characterized in that: The ring A is selected from the structures shown in any one of the following formulas (A-1) to (A-4): In the formula, represents the fusion site with the five-membered ring containing X in formula (1); The substituent R2 of ring A is selected from at least one of 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, or C6-C60 arylamine; b is an integer from 0 to 8; if b≥2, each R2 is the same or different.

4. The aromatic amine compound according to claim 1 or 3, characterized in that: The ring C is selected from the structures represented by the following formula (C-1) to formula (C-7): In the formula, represents the fusion site with the N-containing five-membered ring in formula (2); The substituent R3 of ring C 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 or C6-C60 arylamine; c is an integer from 0 to 8; if c≥2, each R3 is the same or different.

5. The aromatic amine compound according to claim 4, characterized in that: The R1, R2, and R3 are each independently selected from at least one of 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, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, or C6-C30 arylamine.

6. The aromatic amine compound according to claim 4, characterized in that: The aromatic amine compound satisfies at least one of the following conditions: 1) a is 0 or 4. If a is 4, at least one R1 is deuterium; 2) b is 0 or 7. If b is 7, at least one R2 is deuterium; 3) c is 0, 3, 5 or 7. If c is 3, 5 or 7, at least one R3 is deuterium; 4) X is O or S.

7. The aromatic amine compound according to claim 1, 2 or 3, characterized in that: The aromatic amine compound is one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 8. A composition for an organic light-emitting device, characterized in that: The composition comprises a first host compound and a second host compound, wherein the first host compound is the aromatic amine compound according to any one of claims 1 to 7, and the second host compound has a structure as shown in formula (3): Formula (3) In the formula, ring D is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Z is selected from NR d , CR e R f or oxygen group element; Z1, Z2 and Z3 are each independently selected from N or CR g ; R d , R e and R f 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 or C6-C30 arylsilyl; R4 and R g Each 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 or C6-C60 arylamine; d is an integer from 0 to 4; if d ≥ 2, each R1 is the same or different; L3 to L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group; The substitutions in the rings D, L3, L4, L5, Ar3 and Ar4 each independently represent substitutions 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, and the number of substitutions ranges from a single substitution to a maximum number of substitutions.

9. The composition for an organic light-emitting device according to claim 8, characterized in that: The L1 to L5 are each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted naphthylene group.

10. The composition for an organic light-emitting device according to claim 8, characterized in that: The Ar1 to Ar4 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a fluoranthene group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted triphenylene group, or a combination of at least two of the above.

11. The composition for an organic light-emitting device according to claim 10, characterized in that: Ar1 to Ar4 are each independently selected from a phenyl group containing a deuterium substitution, a biphenyl group containing a deuterium substitution, or a naphthyl group containing a deuterium substitution.

12. The composition for an organic light-emitting device according to any one of claims 8 to 11, characterized in that: The second main compound is selected from one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 13. The composition for an organic light-emitting device according to claim 8, characterized in that: The mass ratio of the first host compound to the second host compound is 8:2-2:

8.

14. The composition for an organic light-emitting device according to claim 8, characterized in that: The composition further comprises at least one third main compound, wherein the third main compound has a structure as shown in formula (1) or formula (3), and the structures of the first, second and third main compounds are different.

15. An organic light-emitting device, characterized in that: A composition for an organic light-emitting device comprising the aromatic amine compound according to any one of claims 1 to 7 or according to any one of claims 8 to 14.

16. The organic light emitting device according to claim 15, characterized in that: The invention comprises a cathode and an anode, wherein the cathode is arranged opposite to the anode, a light-emitting layer is arranged between the cathode and the anode, and the light-emitting layer comprises the aromatic amine compound according to any one of claims 1 to 7 or the composition for an organic light-emitting device according to any one of claims 8 to 14.

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