An aromatic amine compound, a composition containing the same, and an organic light-emitting device

Abstract

The present application discloses an aromatic amine compound, a composition containing the same, and an organic light-emitting device. The structure of the aromatic amine compound is shown in the following formula (1): Formula (1). Among them, ring A is selected from a substituted or unsubstituted phenanthrene ring; B is selected from the structural substituents shown in the following formula (2); Formula (2). 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 aromatic amine compound of the solution of the present application has a series of excellent physical and chemical properties and has good application prospects in the optoelectronic field. Specifically, the aromatic amine compound shows excellent performance in terms of optoelectronic stability, can effectively resist the performance degradation caused by light and current changes, and ensure the stable output of the device during long-term operation. It has a low sublimation temperature, a low driving voltage, and a high luminous efficiency. At the same time, it also has a long device life.

Description

Technical Field

[0001] This application relates to the field of organic light-emitting technology, and particularly to an arylamine compound, a composition containing the same, and an organic light-emitting device. Background Art

[0002] Currently, organic light-emitting devices (OLEDs), which lead the future trends in display and lighting technologies, have attracted much attention due to their extensive application potential. OLED technology not only shines in consumer electronics 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 improving key performance indicators such as luminous efficiency, reducing driving voltage, and extending service life, which still require in-depth research and continuous optimization.

[0003] The core structure of an OLED device is a multi-layer stacked "sandwich" structure, where metal electrodes serve as the upper and lower boundaries, and various organic thin film layers with different functions are precisely arranged in the middle. Under the action of an electric field, electrons are injected from the cathode, holes are injected from the anode, and the two move towards each other inside the device and finally meet and recombine in the light-emitting layer. This recombination process is not only accompanied by the emission of photons but also may dissipate in the form of heat energy, directly affecting the luminous efficiency of the OLED. 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 emission 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 emitters but also deeply affected by the characteristics of the host materials. As an important component of the light-emitting layer, the energy level structure, mobility, and stability of the host materials have a crucial impact on the device performance. Optimizing the host materials 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 for the development of the OLED field. Summary of the Invention

[0006] This application aims to solve at least one of the technical problems existing in the prior art. For this purpose, this application proposes a compound, which can significantly reduce the driving voltage of the device, improve the luminous efficiency of the device, and extend the service life of the device when used in the preparation of OLED host materials.

[0007] The first aspect of this application provides an arylamine compound.

[0008] In some embodiments, the structure of the arylamine compound is as shown in the following formula (1):

[0009] Formula (1)

[0010] In the formula, ring A is selected from a substituted or unsubstituted phenanthrene ring;

[0011] X is selected from chalcogens, CR a R b or NR c ; R a , R b and R c are each independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl or C6-C30 arylsilyl;

[0012] 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 alkylboron, C6-C60 arylboron, C6-C60 arylphosphino or C6-C60 arylamino;

[0013] a is an integer from 0 to 4; if a≥2, then each R1 is the same or different;

[0014] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene;

[0015] B is selected from the structural substituents shown in the following formula (2);

[0016] Formula (2)

[0017] 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;

[0018] Y is selected from O, S or Se;

[0019] represents the connection site with L2 in formula (1);

[0020] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl;

[0021] The substitutions in L1, L2, Ar1 and Ar2 each independently represent being substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, amino substituted by C1-C6 alkyl, C1-C6 hydrocarbyl-substituted or unsubstituted C6-C30 aryl or C1-C6 hydrocarbyl-substituted or unsubstituted C3-C30 heteroaryl, and the number of substitutions is from single substitution to maximum substitution;

[0022] The heteroatoms in the heteroarylene, heteroaryl, heteroalkyl or heterocycloalkyl each independently selected from at least one of O, S, N, Se, Si and Ge.

[0023] Compared with the prior art, the beneficial effects of the present application are as follows:

[0024] The arylamine compound of the present application scheme has a series of superior physical and chemical properties and has good application prospects in the optoelectronic field. Specifically, the arylamine compound shows excellent performance in optoelectronic stability, can effectively resist the performance decline caused by light and current changes, and ensure the stable output of the device during long-term operation. In addition, its unique sublimation property is reflected in the lower sublimation temperature, which significantly reduces the energy consumption and cost of the material during vacuum evaporation, improves the controllability and uniformity of the evaporation process, and is conducive to the preparation of high-quality optoelectronic device films. In terms of electrical properties, the arylamine compound shows the dual advantages of low driving voltage and high luminous efficiency. The 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. The 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 realizing energy conservation and emission reduction. At the same time, the arylamine compound also has a long device life, which benefits from its excellent chemical stability and thermal stability, can resist the erosion of the external environment on the material structure, thus extending the overall service life of the optoelectronic device and reducing the replacement and maintenance costs.

[0025] During the material evaporation process, the lower melting point not only simplifies the processing process, but also enhances the material stability during evaporation, reduces the material decomposition or deterioration phenomenon caused by high temperature, and further improves the performance and reliability of the device.

[0026] The additional aspects and advantages of the present application will be partly given in the following description, partly will become obvious from the following description, or be understood through the practice of the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] The present application will be further described below in conjunction with the accompanying drawings and embodiments, where:

[0028] Figure 1 It is the 1 HNMR spectrum of compound A50 prepared in Example 2 of the present application.

[0029] Figure 2 It is a schematic structural diagram of an organic light-emitting device prepared in the application example of the present application.

[0030] Explanation of reference numerals: 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 implementation manners

[0031] The concept of the present application and the technical effects generated will be clearly and completely described below in conjunction with the embodiments to fully understand the purpose, features, and effects of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments of the present application, other embodiments obtained by those skilled in the art without creative efforts shall fall within the scope of protection of the present application. The test methods used in the embodiments are all conventional methods unless otherwise specified; the materials, reagents, etc. used, unless otherwise specified, are all reagents and materials that can be obtained from commercial channels. Unless otherwise specified, the same parameter values are taken in each embodiment. The embodiments described below are exemplary and are only used to explain the present application and should not be construed as a limitation to the present application.

[0032] In the description of the present application, the description referring to terms such as "some embodiments" means that the specific features, structures, materials, or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the present 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 a suitable manner in any one or more embodiments or examples.

[0033] In the description of the present application, if the first, second, third, etc. are described, they are only for the purpose of distinguishing technical features and should not be understood as indicating or implying relative importance or implicitly indicating the quantity of the indicated technical features or implicitly indicating the sequence of the indicated technical features.

[0034] The first aspect of the present application provides an aromatic amine compound.

[0035] Specifically, the structure of the aromatic amine compound is shown in the following formula (1):

[0036] Formula (1)

[0037] In the formula, ring A is selected from a substituted or unsubstituted phenanthrene ring;

[0038] X is selected from a chalcogen element, CR a R b or NR c ; R a 、R b and R c are each independently selected from a C1-C30 alkyl group, a C1-C30 heteroalkyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C3-C30 alkylsilyl group or a C6-C30 arylsilyl group;

[0039] Each R1 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, a C1-C40 alkyl group, a C1-C40 heteroalkyl group, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C3-C40 cycloalkyl group, a C3-C40 heterocycloalkyl group, a C6-C60 aryl group, a C3-C60 heteroaryl group, a C1-C40 alkoxy group, a C6-C60 aryloxy group, a C3-C40 alkylsilyl group, a C6-C60 arylsilyl group, a C1-C40 alkylboron group, a C6-C60 arylboron group, a C6-C60 arylphosphino group or a C6-C60 arylamino group;

[0040] a is an integer from 0 to 4; if a ≥ 2, then each R1 is the same or different;

[0041] 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;

[0042] B is selected from a structural substituent represented by the following formula (2);

[0043] Formula (2)

[0044] 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;

[0045] Y is selected from O, S or Se;

[0046] represents the connection site with L2 in formula (1);

[0047] 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;

[0048] Each substitution in L1, L2, Ar1, and Ar2 independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, amino substituted by C1-C6 alkyl, C6-C30 aryl substituted or unsubstituted by C1-C6 hydrocarbyl, or C3-C30 heteroaryl substituted or unsubstituted by C1-C6 hydrocarbyl, and the number of substitutions ranges from single substitution to maximum substitution; the heteroatoms in the heteroarylene, heteroaryl, heteroalkyl, or heterocycloalkyl each independently selected from at least one of O, S, N, Se, Si, and Ge.

[0049] Specific examples of the aryl include, for example, phenyl, naphthyl, anthryl, phenanthryl, tetraphenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, fluoranthenyl, etc. In some specific embodiments of the present application, the aryl is phenyl or naphthyl.

[0050] Specific examples of the heteroaryl include, for example, pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, dibenzothiophenyl, azadibenzofuryl, azadibenzothiophenyl, diazadibenzofuryl, diazadibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthroline, phenazine, phenothiazine, phenoxazine, oxazolinyl, oxadiazolyl, furazanyl, thiophenyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl. In some specific embodiments of the present application, the heteroaryl is pyridyl, pyrimidinyl, triazinyl, dibenzofuryl, dibenzothiophenyl, azadibenzofuryl, azadibenzothiophenyl, diazadibenzofuryl, diazadibenzothiophenyl, carbazolyl, azacarbazolyl, or diazacarbazolyl.

[0051] In some embodiments, the chalcogen element is selected from O, S, or Se.

[0052] In some embodiments, the heteroatoms in the heteroaryl, heteroalkyl, or heterocycloalkyl each independently selected from at least one of O, S, N, Se, Si, and Ge. In some embodiments, the R a , R b and R c each 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.

[0053] In some embodiments, the R a , Rb and R c each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C3-C10 heteroaryl, C3-C10 alkylsilyl or C6-C10 arylsilyl.

[0054] 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 alkylboron, C6-C30 arylboron, C6-C30 arylphosphino or C6-C30 arylamino.

[0055] 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 alkylboron, C6-C20 arylboron, C6-C20 arylphosphino or C6-C20 arylamino.

[0056] In some embodiments, a is 0 or 4.

[0057] In some embodiments, if a is 4, then at least one R1 is deuterium. It can be all deuterium or partially deuterium.

[0058] In some embodiments, a is an integer from 1 to 4. Such as 2 or 3.

[0059] In some embodiments, ring A is selected from the structures shown by any one of the following formulas (A-1) to (A-4):

[0060]

[0061] In the formula, represents the fusion site with the five-membered ring containing X in formula (1);

[0062] 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 alkylboron, C6-C60 arylboron, C6-C60 arylphosphino or C6-C60 arylamino;

[0063] b is an integer from 0 to 8; if b≥2, then each R2 is the same or different.

[0064] In some embodiments, the 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 alkylboron, C6-C30 arylboron, C6-C30 arylphosphino or C6-C30 arylamino.

[0065] In some embodiments, the 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 alkylboron, C6-C20 arylboron, C6-C20 arylphosphino or C6-C20 arylamino.

[0066] In some embodiments, the b is 0 or 7. If b is 7, then at least one R2 is deuterium. It can be all deuterium or partially deuterium.

[0067] In some embodiments, the b is an integer from 1 to 8. Such as 2, 3, 4, 5, 6, 7 or 8, etc.

[0068] In some embodiments, the ring C is selected from the structures shown by the following formula (C-1) to formula (C-7):

[0069]

[0070] In the formula, represents the fused site of the N-containing five-membered ring in formula (2);

[0071] 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 alkylboron, C6-C60 arylboron, C6-C60 arylphosphino or C6-C60 arylamino;

[0072] c is an integer from 0 to 8; if c ≥ 2, then each R3 is the same or different.

[0073] In some embodiments, the 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 alkylboron, C6-C30 arylboron, C6-C30 arylphosphino or C6-C30 arylamino.

[0074] In some embodiments, the 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 alkylboron, C6-C20 arylboron, C6-C20 arylphosphino or C6-C20 arylamino.

[0075] In some embodiments, the c is 0, 3, 5 or 7. If c is 3, 5 or 7, then at least one R3 is deuterium. It can be all deuterium or partially deuterium.

[0076] In some embodiments, the c is an integer from 1 to 8. Such as 2, 3, 4, 5, 6, 7 or 8, etc.

[0077] 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.

[0078] In some embodiments, X is O or S. In some embodiments, L1 and L2 are each independently selected from substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C6-C30 heteroarylene.

[0079] In some embodiments, L1 and L2 are each independently selected from substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C6-C20 heteroarylene.

[0080] In some embodiments, L1 and L2 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0081] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heteroaryl.

[0082] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl.

[0083] 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 anthryl, 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 phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzo[ghi]perylenyl, or a combination of at least two of the above.

[0084] In some embodiments, Ar1 and Ar2 are each independently selected from phenyl substituted with deuterium, biphenyl substituted with deuterium, or naphthyl substituted with deuterium.

[0085] In some embodiments, the aromatic amine compound is one of the following structural formulas, or one of the structures in which hydrogen in the following structural formulas is partially or completely replaced by deuterium or fluorine:

[0086] ;

[0087] ；

[0088] ；

[0089] ；

[0090] ；

[0091] ；

[0092] ； ；

[0093] ；

[0094] ；

[0095] ；

[0096] ；

[0097] ；

[0098] ；

[0099] ；

[0100] ；

[0101] ；

[0102] ；

[0103] ；

[0104] ；

[0105] ；

[0106] ；

[0107] ；

[0108] ；

[0109] ；

[0110] ；

[0111] ；

[0112] ;

[0113] ;

[0114]

[0115] 。

[0116] The second aspect of the present application provides a composition for an organic light-emitting device.

[0117] Specifically, the composition comprises a first host compound and a second host compound, the first host compound has a structure shown in formula (1), and the second host compound has a structure shown in formula (3):

[0118] Formula (3)

[0119] 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;

[0120] Z is selected from NR d , CR e R f or a chalcogen element; Z1, Z2 and Z3 are each independently selected from N or CR g ;

[0121] R d , R e and R f are each independently selected from an alkyl group having 1 to 30 carbon atoms, a heteroalkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, an alkylsilyl group having 3 to 30 carbon atoms or an arylsilyl group having 6 to 30 carbon atoms;

[0122] R4 and R g are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, an alkyl group having 1 to 40 carbon atoms, a heteroalkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 3 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 3 to 60 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 3 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphino group having 6 to 60 carbon atoms or an arylamino group having 6 to 60 carbon atoms;

[0123] d is an integer from 0 to 4; if d≥2, then each R1 is the same or different;

[0124] L3 to L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene, or a substituted or unsubstituted C3-C60 heteroarylene;

[0125] Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C36 aryl, or a substituted or unsubstituted C2-C36 heteroaryl;

[0126] The substitution in the ring D, L3, L4, L5, Ar3, and Ar4 each independently means being substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, an amino group substituted by C1-C6 alkyl, a C1-C6 hydrocarbyl-substituted or unsubstituted C6-C30 aryl, or a C1-C6 hydrocarbyl-substituted or unsubstituted C3-C30 heteroaryl, and the number of substitutions ranges from single substitution to the maximum number of substitutions.

[0127] In some embodiments, the chalcogen element is selected from O, S, or Se.

[0128] In some embodiments, R d , R e and R f are each 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.

[0129] In some embodiments, R d , R e and R f are each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C3-C10 heteroaryl, C3-C10 alkylsilyl, or C6-C10 arylsilyl.

[0130] In some embodiments, R4 and R g are each 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 alkylboron, C6-C30 arylboron, C6-C30 arylphosphino, or C6-C30 arylamino.

[0131] In some embodiments, R4 and R g are each 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 alkylboron, C6-C20 arylboron, C6-C20 arylphosphino or C6-C20 arylamino.

[0132] In some embodiments, d is an integer from 1 to 4. Such as 2 or 3.

[0133] In some embodiments, X or Z is independently selected from O or S.

[0134] In some embodiments, L3 to L5 are each independently selected from substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C6-C20 heteroarylene.

[0135] In some embodiments, L3 to L5 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene.

[0136] In some embodiments, L1 to L5 are each independently selected from substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C6-C20 heteroarylene.

[0137] In some embodiments, L1 to L5 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene.

[0138] In some embodiments, Ar3 and Ar4 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.

[0139] In some embodiments, Ar3 and Ar4 are each independently selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl.

[0140] In some embodiments, each of Ar1 to Ar4 is independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, fluoranthenyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted benzotriazolyl, a substituted or unsubstituted benzophenanthryl, or a combination of at least two of the above.

[0141] In some embodiments, Ar1 to Ar4 are each independently selected from a phenyl group having deuterium substitution, a biphenyl group having deuterium substitution, or a naphthyl group having deuterium substitution.

[0142] In some embodiments, the second host compound is selected from one of the following structural formulas, or from one of the structures in which hydrogen is partially or completely substituted by deuterium or fluorine in the following structural formulas: ;

[0143] ;

[0144] ;

[0145] ;

[0146] ;

[0147] ;

[0148] ;

[0149] ;

[0150] ;

[0151] ;

[0152] ;

[0153] ; ;

[0154] ;

[0155] ;

[0156] ;

[0157] 。

[0158] In some embodiments, the mass ratio of the first host compound to the second host compound is 8:2 - 2:8.

[0159] In some embodiments, the composition further comprises at least one third host compound having a structure represented by formula (1) or formula (3), and the structures of the first, second, and third host compounds are all different.

[0160] In some embodiments, in the composition, the mass ratio of the compound represented by formula (1) to the compound represented by formula (3) is 8:2 - 2:8. The third host compound belongs to the structure represented by formula (1) or formula (3), and the total mass thereof with the first host compound or the second host compound satisfies the above proportional relationship. If it is of formula (1), the total amount with the first host compound accounts for 20% - 80% in the composition. Since they are all of formula (1), the proportion in formula (1) is not limited, 0 - 100%. Similarly, if it is of formula (2), the total amount with the second host compound accounts for 20% - 80% in the composition. Since they are all of formula (2), the proportion in formula (2) is not limited, 0 - 100%.

[0161] The third aspect of the present application provides the use of the above arylamine compound or composition.

[0162] Specifically, the third aspect of the present application provides the use of the above arylamine compound or composition in the semiconductor field.

[0163] Specifically, an organic light-emitting device comprises the above arylamine compound or composition.

[0164] In some embodiments, an organic light-emitting device (OLED) includes a cathode and an anode, the cathode is disposed opposite to the anode, and a light-emitting layer is provided between the cathode and the anode, and the light-emitting layer comprises the above arylamine compound or composition. The arylamine compound and composition of the present application can be used alone or after doping to prepare the light-emitting layer.

[0165] In some embodiments, in the device, the arylamine compound or the composition is used as a red light material for the light-emitting layer.

[0166] In some embodiments, the light-emitting layer is a red light-emitting layer, and the arylamine compound or composition is used as the host material of the red light-emitting layer.

[0167] Specifically, the application of the above-mentioned arylamine compound or composition in the preparation of semiconductor devices. In some embodiments, a semiconductor device includes the above-mentioned organic light-emitting device, and the semiconductor device is at least one of an organic light-emitting battery, an organic light-emitting field-effect transistor, and an organic OLED display screen (which can be an active-matrix organic light-emitting diode panel (AMOLED), an organic electroluminescent sensor (Organic Light-Emitting Sensor, OLES), etc.).

[0168] In some embodiments, the organic light-emitting field-effect transistor includes an organic light-emitting transistor (Organic Light-Emitting Transistor, OLET).

[0169] In some embodiments, the organic light-emitting transistor can be an organic light-emitting thin-film transistor (Organic Light-Emitting Thin-Film Transistor, OLETFT).

[0170] Definition

[0171] Unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of this application, the definitions of some terms are provided below. When the definitions of the terms provided in this application do not conform to the meanings commonly understood by those skilled in the art, the definitions and explanations provided in this application shall prevail.

[0172] The term "heteroalkyl" means that at least one carbon atom in the alkyl group is replaced by a non-carbon atom or a group containing a non-carbon atom. 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, alkylboron). Non-limiting examples of heteroalkyl include mercaptomethylmethyl, methoxymethyl, ethoxymethyl, tert-butoxymethyl, N,N-dimethylmethyl, epoxybutyl, epoxypropyl, or epoxyhexyl, etc. In some specific embodiments of this application, the heteroalkyl is methoxymethyl or epoxypropyl.

[0173] The term "alkoxy" means a group having -O-alkyl, that is, the alkyl group defined above is connected to a given group or a given structural formula via an oxygen atom. Non-limiting examples of alkoxy include: methoxy, ethoxy, and tert-butoxy.

[0174] The term "heterocycloalkyl" means that on the basis of cycloalkyl, 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 heterocycloalkyl can be 3 to 30, 3 to 20, 3 to 12, 3 to 10 or 3 to 6. Non-limiting examples of heterocycloalkyl include: oxetanyl, oxolanyl and oxanyl.

[0175] The term "aryl" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and can be a monocyclic aryl or a polycyclic aryl. At least one ring in the polycyclic aryl is an aromatic ring system. The multiple rings in the polycyclic aryl can be connected to each other via a single bond or can be fused to each other. The number of carbon atoms in aryl can be 6 to 30, 6 to 20, 6 to 12 or 6 to 10. For example, when the polycyclic aryl contains a fused ring structure, specifically, it can be formed by the fusion of a C3-C30 aliphatic ring (a saturated or unsaturated aliphatic ring containing 3 to 30 ring backbone carbon atoms) and a C3-C30 aromatic ring (an aromatic ring containing 3 to 30 ring backbone carbon atoms), and more specifically, by the fusion of a C3-C20 aliphatic ring and a C6-C30 aromatic ring. It can be understood that the term "arylene" means an aromatic hydrocarbon group derived by removing two hydrogen atoms from an aromatic ring compound.

[0176] The term "heteroaryl" means a monovalent group of a heterocyclic aromatic system in which at least one carbon atom in the aryl is replaced by a non-carbon atom, where the non-carbon atom can be selected from O, S, N, P, B, Se, Si or Ge, but does not include the case where the aryl is connected to the main structure through a non-carbon atom group (such as aryloxy, arylsilyl, arylboron, arylphosphino, arylamino).

[0177] The term "arylphosphino" can be monoarylphosphino, diarylphosphino, triarylphosphino, etc.

[0178] It can be understood that the term "heteroarylene" means a divalent group having the same structure as heteroaryl.

[0179] In the expression "R group with a carbon number of a~b, substituted or unsubstituted", the "carbon number of a~b" represents the carbon number of the R group in the unsubstituted case, and does not include the carbon number of the substituent when the R group is substituted.

[0180] "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 restricted by definition, it also includes the case where one or more hydrogen atoms are replaced by a group formed by the connection of two or more of the above substituents.

[0181] The following examples are only for facilitating the understanding of the technical application and should not be regarded as specific limitations to this application.

[0182] The raw materials, solvents, etc. involved in the synthesis of the compounds in this application are all purchased from well-known suppliers in the art such as Alfa and Acros.

[0183] Synthesis of Compound A2

[0184]

[0185] Synthesis of Compound A2-3

[0186] Add Compound A2-1 (20.00 g, 71.04 mmol), Compound A2-2 (21.65 g, 85.25 mmol), 1,1-bis(diphenylphosphino)ferrocene dichloropalladium (0.52 g, 0.71 mmol), potassium acetate (17.43 g, 177.60 mmol), and 1,4-dioxane (350 ml) into a 1000 ml three-necked round-bottom flask. Replace the vacuum with nitrogen three times. Then heat the system to 100 °C and react for 4 hours. Monitor the reaction by TLC (using ethyl acetate:n-hexane = 1:15 as the eluent). When Compound A2-1 is completely consumed.

[0187] Cool down to 60 °C, concentrate the solvent under reduced pressure, add ethyl acetate (500 ml), wash with deionized water three times (300 ml × 3), separate the layers, mix with silica gel and load the column by dry method, and perform silica gel column chromatography purification (using 200 - 300 mesh silica gel and ethyl acetate:n-hexane = 1:15 as the eluent). After elution, concentrate under reduced pressure at 70 °C for 1 hour to obtain a white solid, which is Compound A2-3 (18.52 g, purity: 99.37%, yield: 79.34%). Mass spectrum: 329.10 (M + H).

[0188] Synthesis of Compound A2-5

[0189] Add 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) into a 1000 ml three-necked round-bottom flask. Replace the vacuum with nitrogen three times. Then heat the system to 75 °C and react for 3 hours. Monitor the reaction by TLC (using ethyl acetate:n-hexane = 1:10 as the eluent). When Compound A2-3 is completely consumed.

[0190] Cool down to 60 °C, concentrate under reduced pressure to remove the solvent, add ethyl acetate (500 ml), wash three times with deionized water (300 ml × 3), separate the layers, mix the sample with silica gel and load the column by dry method, and perform silica gel column chromatography purification (200 - 300 mesh silica gel, ethyl acetate:n - hexane = 1:20 as the eluent). After elution, concentrate under reduced pressure at 70 °C for 2 hours to obtain a white solid, which is compound A2 - 5 (12.38 g, purity: 99.41%, yield: 73.68%). Mass spectrum: 307.04 (M + H).

[0191] Synthesis of compound A2 - 7

[0192] Add compound A2 - 5 (12.00 g, 39.12 mmol), compound A2 - 6 (20.12 g, 58.68 mmol), and tetrahydrofuran (270 ml) into a 1000 ml three - necked round - bottom flask, displace the vacuum with nitrogen three times, then cool the system to 5 °C, and add sodium methoxide (4.23 g, 78.24 mmol) in one portion. Maintain the reaction at 5 °C for 1 hour and monitor the reaction by TLC (ethyl acetate:n - hexane = 1:10 as the developing agent). Compound A2 - 5 is consumed completely.

[0193] Add deionized water (500 ml) thereto, concentrate under reduced pressure to remove the solvent, extract with ethyl acetate (500 ml), separate the layers, and concentrate under reduced pressure at 70 °C for 1 hour to obtain a white solid, which is compound A2 - 7 (11.86 g, yield: 90.55%). Mass spectrum: 335.07 (M + H). The obtained compound is used directly in the next step without purification.

[0194] Synthesis of compound A2 - 8

[0195] Add compound A2 - 7 (11.50 g, 34.35 mmol) and toluene (150 ml) into a 500 ml three - necked round - bottom flask, displace the vacuum with nitrogen three times, then cool the system to 5 °C, and slowly add methanesulfonic acid (6.60 g, 68.70 mmol). Finish the addition in 3 minutes, maintain the reaction at 5 °C for 1 hour, and monitor the reaction by TLC (ethyl acetate:n - hexane = 1:15 as the developing agent). Compound A2 - 7 is consumed completely.

[0196] Add methanol (200 ml) thereto, a large amount of white solid precipitates. Filter by suction to obtain 9 g of solid, crystallize once with toluene (190 ml) and methanol (150 ml), filter by suction, and dry the filter cake under vacuum at 80 °C for 1 hour to obtain a white solid, which is compound A2 - 8 (7.64 g, purity: 99.76%, yield: 73.47%). Mass spectrum: 303.05 (M + H).

[0197] Synthesis of compound A2 - 11

[0198] Compound A2-9 (10.00 g, 36.48 mmol), compound A2-10 (6.17 g, 36.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.67 g, 0.73 mmol), 2-dicyclohexylphosphino-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. The system was evacuated and filled with nitrogen three times, and then heated to 90 °C and reacted for 2 hours. The reaction was monitored by TLC (using ethyl acetate: n-hexane = 1:15 as the eluent), and compound A2-9 was consumed completely.

[0199] The temperature was cooled to 60 °C, methanol (150 ml) was added, and the mixture was allowed to cool to room temperature and stirred for 30 minutes to precipitate a large amount of solid. The solid was filtered by suction to obtain 15 g of solid. Toluene (200 ml) was added, and the system was heated to 100 °C until it was dissolved and clarified. Then, 30 g of silica gel (300-400 mesh) was spread and used for filtration. The surface of the silica gel was rinsed with toluene (50 ml), and the filtrates were combined and concentrated to obtain 13 g. Crystallization was performed twice with toluene (170 ml) and methanol (80 ml), and the solid was filtered by suction. The filter cake was dried in vacuo at 90 °C for 3 hours to obtain a light yellow solid, compound A2-11 (9.28 g, purity: 99.59%, yield: 70.19%). Mass spectrum: 363.14 (M+H).

[0200] Synthesis of Compound A2

[0201] Compound A2-8 (7.50 g, 24.77 mmol), compound A2-11 (8.98 g, 24.77 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.45 g, 0.50 mmol), 2-dicyclohexylphosphino-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. The system was evacuated and filled with nitrogen three times, and then heated to 105 °C and reacted for 2 hours. The reaction was monitored by TLC (using ethyl acetate: n-hexane = 1:15 as the eluent), and compound A2-8 was consumed completely.

[0202] Cool down to 60 °C, add methanol (150 ml), and let it cool to room temperature naturally. Stir for 30 minutes to precipitate a large amount of solid. Filter by suction to obtain 14 g of solid. Add toluene (300 ml), then heat the system to 100 °C until it dissolves and becomes clear. Filter through a pad of 30 g of silica gel (300 - 400 mesh), rinse the surface of the silica gel with toluene (50 ml), and concentrate the combined filtrate to obtain 12 g. Crystallize twice with toluene (170 ml) and methanol (80 ml), filter by suction, and dry the filter cake under vacuum at 90 °C for 3 hours to obtain a light yellow solid, which is compound A2 (11.75 g, purity: 99.94%, yield: 75.44%). After sublimation purification of 11.75 g of the crude compound A2, sublimation-pure compound A2 (7.67 g, purity: 99.94%, yield: 65.27%) is obtained. Mass spectrum: 629.21 (M+H).

[0203] 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).

[0204] Synthesis of compound A50:

[0205]

[0206] Synthesis of compound A50-2

[0207] Referring to the synthesis and purification methods of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A50-2 (18.91 g, purity: 99.23%, yield: 81.01%). Mass spectrum: 329.10 (M+H).

[0208] Synthesis of compound A50-3

[0209] Referring to the synthesis and purification methods of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A50-3 (13.24 g, purity: 99.51%, yield: 76.67%). Mass spectrum: 307.04 (M+H).

[0210] Synthesis of Compound A50-4

[0211] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A50-4 (12.8 g, yield: 90.28%), and the mass spectrum is 335.07 (M+H).

[0212] Synthesis of Compound A50-5

[0213] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A50-5 (7.28 g, purity: 99.71%, yield: 70.84%), and the mass spectrum is 303.05 (M+H).

[0214] Synthesis of Compound A50-7

[0215] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A50-7 (11.35 g, purity: 99.47%, yield: 67.84%), and the mass spectrum is 306.06 (M+H).

[0216] Synthesis of Compound A50-9

[0217] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A50-9 (10.87 g, purity: 99.78%, yield: 68.90%), and the mass spectrum is 363.15 (M+H).

[0218] Synthesis of Compound A50

[0219] Referring to the synthesis and purification methods 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%). After sublimation purification of 11.35 g of the crude product of Compound A50, the sublimated pure Compound A50 (7.17 g, purity: 99.93%, yield: 63.17%) was obtained, and the mass spectrum was 629.22 (M+H). The NMR characterization results are as Figure 1 shown. The specific data are as follows:

[0220] 1 H NMR (400 MHz, CDCl3) δ 9.27 (d, J J = 8.5 Hz, 1H), 8.59 (d, J 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).

[0221] Synthesis of Compound A68

[0222]

[0223] Synthesis of Compound A68-3

[0224] 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. The system was evacuated and filled with nitrogen three times. Then, the system was stirred in an ice bath for 10 min, 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 h. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the eluent), and Compound A68-1 was completely consumed.

[0225] Toluene (100 ml) was added, and the mixture was washed three times with deionized water (300 ml × 3). After liquid separation, the organic phase was concentrated under reduced pressure at 70 °C for 1 h to obtain a white solid, Compound A68-3 (7.13 g, yield: 91.20%). Mass spectrum: 303.08 (M+H). The obtained compound was used directly in the next step without purification.

[0226] Synthesis of Compound A68-4

[0227] 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. The system was evacuated and filled with nitrogen three times. Then, the system was heated to 120 °C and reacted for 3 h with water separation using a water separator. The reaction was monitored by TLC (dichloromethane: n-hexane = 1:2 as the eluent), and Compound A68-3 was completely consumed.

[0228] Cool to room temperature, add dichloromethane (100 ml) and water (100 ml), extract, separate the layers, and concentrate the organic phase under reduced pressure at 60 °C for 20 min to obtain a white solid as the compound. Add toluene (100 ml), then heat the system to 100 °C until dissolved and clarified, filter through a bed of 30 g (300 - 400 mesh) silica gel, rinse the silica gel surface with toluene (50 ml), combine the filtrates and concentrate to obtain 7 g. Crystallize twice with toluene (100 ml) and methanol (50 ml), filter by suction, and dry the filter cake under vacuum at 90 °C for 3 hours to obtain a light yellow solid as compound A68 - 4 (4.81 g, purity: 99.34%, yield: 73.06%), MS: 285.07 (M + H).

[0229] Synthesis of Compound A68 - 6

[0230] Referring to the synthesis and purification methods of compound A2 - 11, only the corresponding raw materials need to be changed to obtain the target compound A68 - 6 (3.92 g, purity: 99.71%, yield: 71.60%), MS: 347.19 (M + H).

[0231] Synthesis of Compound A68

[0232] Referring to the synthesis and purification methods 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%). After sublimation purification of 4.18 g of the crude product of compound A68, the sublimation - pure compound A68 (2.59 g, purity: 99.94%, yield: 61.96%) was obtained, MS: 613.26 (M + H).

[0233] 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).

[0234] Synthesis of Compound A79

[0235]

[0236] Synthesis of Compound A79-2

[0237] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A79-2 (15.92 g, purity: 99.25%, yield: 69.48%). Mass spectrum: 371.17 (M+H).

[0238] Synthesis of Compound A79-4

[0239] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A79-4 (11.04 g, purity: 99.47%, yield: 68.88%). Mass spectrum: 383.07 (M+H).

[0240] Synthesis of Compound A79-5

[0241] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A79-5 (10.53 g, yield: 89.19%). Mass spectrum: 411.10 (M+H).

[0242] Synthesis of Compound A79-6

[0243] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A79-6 (7.12 g, purity: 99.68%, yield: 73.54%). Mass spectrum: 379.08 (M+H).

[0244] Synthesis of Compound A79

[0245] Referring to the synthesis and purification methods 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%). After sublimation purification of 7.61 g of the crude product of Compound A79, sublimation-pure Compound A79 (4.82 g, purity: 99.93%, yield: 63.33%) was obtained. Mass spectrum: 629.21 (M+H).

[0246] 11H 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).

[0247] Synthesis of Compound A81

[0248]

[0249] Synthesis of Compound A81-2

[0250] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A81-2 (14.38 g, purity: 99.35%, yield: 66.26%). Mass spectrum: 307.04 (M+H).

[0251] Synthesis of Compound A81-3

[0252] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A81-3 (13.81 g, yield: 90.38%). Mass spectrum: 335.07 (M+H).

[0253] Synthesis of Compound A81-4

[0254] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A81-4 (8.71 g, yield: 71.35%). Mass spectrum: 303.05 (M+H).

[0255] Synthesis of Compound A81

[0256] Referring to the synthesis and purification methods 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%). After sublimation purification of 12.26 g of the crude product of Compound A81, the sublimation-pure Compound A81 (7.61 g, purity: 99.94%, yield: 62.07%) was obtained. Mass spectrum: 629.21 (M+H).

[0257] 1 1H 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).

[0258] Synthesis of Compound A84

[0259]

[0260] Synthesis of Compound A84-1

[0261] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A84-1 (12.56 g, purity: 98.97%, yield: 71.46%). Mass spectrum: 322.15 (M+H).

[0262] Synthesis of Compound A84-3

[0263] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A84-3 (9.81 g, purity: 99.57%, yield: 73.79%). Mass spectrum: 356.07 (M+H).

[0264] Synthesis of Compound A84-4

[0265] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A84-4 (7.81 g, purity: 99.32%, yield: 70.92%). Mass spectrum: 413.15 (M+H).

[0266] Synthesis of Compound A84

[0267] Referring to the synthesis and purification methods 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%). After sublimation purification of 8.14 g of the crude product of Compound A84, sublimation-pure Compound A84 (5.02, purity: 99.95%, yield: 61.67%) was obtained. Mass spectrum: 679.23 (M+H).

[0268] 1 1H 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).

[0269] Synthesis of Compound A99

[0270]

[0271] Synthesis of Compound A99-1

[0272] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A99-1 (12.61 g, yield: 75.84%), mass spectrum: 334.05 (M+H).

[0273] Synthesis of Compound A99-2

[0274] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A99-2 (11.73 g, purity: 99.05%, yield: 90.17%), mass spectrum: 362.08 (M+H).

[0275] Synthesis of Compound A99-3

[0276] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A99-3 (7.69 g, purity: 99.74%, yield: 73.37%), mass spectrum: 330.06 (M+H).

[0277] Synthesis of Compound A99-4

[0278] Referring to the synthesis and purification method of compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A99-4 (6.72 g, purity: 99.81%, yield: 76.46%). Mass spectrum: 387.14 (M+H).

[0279] Synthesis of Compound A99

[0280] 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%). After sublimation purification of 8.47 g of the crude product of compound A99, the sublimation-pure compound A99 (5.53 g, purity: 99.94%, yield: 65.28%) was obtained. Mass spectrum: 653.21 (M+H).

[0281] 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).

[0282] Synthesis of Compound A116

[0283]

[0284] Synthesis of Compound A116-2

[0285] 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 A116-2 (10.83 g, purity: 99.51%, yield: 74.85%). Mass spectrum: 307.04 (M+H).

[0286] Synthesis of Compound A116-3

[0287] Referring to the synthesis and purification method of reference compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A116-3 (10.51 g, yield: 91.71%), and the mass spectrum is 335.07 (M+H).

[0288] Synthesis of compound A116-4

[0289] Referring to the synthesis and purification method of reference compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A116-4 (6.84 g, purity: 99.78%, yield: 72.04%), and the mass spectrum is 303.05 (M+H).

[0290] Synthesis of compound A116

[0291] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 9.37 g of the crude product of compound A116, the sublimation-pure compound A116 (5.97 g, purity: 99.94%, yield: 63.71%) was obtained, and the mass spectrum is 629.22 (M+H).

[0292] 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).

[0293] Synthesis of compound A121

[0294]

[0295] Synthesis of compound A121-3

[0296] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A121-3 (12.86 g, purity: 99.47%, yield: 73.41%), and the mass spectrum is 329.06 (M+H).

[0297] Synthesis of compound A121-4

[0298] Referring to the synthesis and purification method of reference compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A121-4 (11.34 g, purity: 99.14%, yield: 70.97%), mass spectrometry: 421.19 (M+H).

[0299] Synthesis of compound A121-5

[0300] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A121-5 (8.65 g, purity: 99.69%, yield: 76.35%), mass spectrometry: 433.09 (M+H).

[0301] Synthesis of compound A121-6

[0302] Referring to the synthesis and purification method of reference compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A121-6 (8.07 g, yield: 89.16%), mass spectrometry: 461.12 (M+H).

[0303] Synthesis of compound A121-7

[0304] Referring to the synthesis and purification method of reference compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A121-7 (5.62 g, purity: 99.65%, yield: 75.50%), mass spectrometry: 429.09 (M+H).

[0305] Synthesis of compound A121

[0306] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 6.71 g of the crude product of compound A121, sublimation-pure compound A121 (4.29 g, purity: 99.96%, yield: 63.93%) was obtained, mass spectrometry: 755.26 (M+H).

[0307] 11H 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).

[0308] Synthesis of Compound A143

[0309]

[0310] Synthesis of Compound A143-2

[0311] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A143-2 (15.62 g, purity: 99.54%, yield: 71.97%), mass spectrum: 307.04 (M+H).

[0312] Synthesis of Compound A143-3

[0313] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A143-3 (15.17 g, yield: 89.67%), mass spectrum: 335.08 (M+H).

[0314] Synthesis of Compound A143-4

[0315] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A143-4 (9.67 g, purity: 99.73%, yield: 71.29%), mass spectrum: 303.05 (M+H).

[0316] Synthesis of Compound A143-5

[0317] Referring to the synthesis and purification method of compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A143-5 (10.87 g, purity: 99.78%, yield: 68.90%). Mass spectrum: 439.17 (M+H).

[0318] Synthesis of compound A143

[0319] 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%). After sublimation purification of 15.20 g of the crude product of compound A143, the sublimation-pure compound A143 (9.97 g, purity: 99.96%, yield: 65.59%) was obtained. Mass spectrum: 705.25 (M+H).

[0320] 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).

[0321] Synthesis of compound A167

[0322]

[0323] Synthesis of compound A167-2

[0324] Referring to the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A167-2 (17.56 g, purity: 99.33%, yield: 75.22%). Mass spectrum: 329.10 (M+H).

[0325] Synthesis of compound A167-3

[0326] 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 A167-3 (13.17 g, purity: 99.36%, yield: 80.62%). Mass spectrum: 307.04 (M+H).

[0327] Synthesis of compound A167-4

[0328] Referring to the synthesis and purification method of reference compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A167-4 (12.91 g, yield: 90.99%), mass spectrum: 335.08 (M+H).

[0329] Synthesis of compound A167-5

[0330] Referring to the synthesis and purification method of reference compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A167-5 (5.31 g, purity: 99.37%, yield: 45.52%), mass spectrum: 303.05 (M+H).

[0331] Synthesis of compound A167-7

[0332] Referring to the synthesis and purification method of reference compound A68-3, only the corresponding raw materials need to be changed to obtain the target compound A167-7 (6.92 g, yield: 90.01%), mass spectrum: 298.05 (M+H).

[0333] Synthesis of compound A167-8

[0334] Referring to the synthesis and purification method of reference compound A68-4, only the corresponding raw materials need to be changed to obtain the target compound A167-8 (4.72 g, yield: 72.81%), mass spectrum: 280.04 (M+H).

[0335] Synthesis of compound A167-10

[0336] Referring to the synthesis and purification method of reference compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A167-10 (5.19 g, yield: 69.75%), mass spectrum: 463.17 (M+H).

[0337] Synthesis of compound A167

[0338] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 5.28 g of the crude product of compound A167, the sublimation-pure compound A167 (3.27 g, purity: 99.90%, yield: 61.93%) was obtained, mass spectrum: 729.24 (M+H).

[0339] 11H 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).

[0340] Synthesis of Compound A182

[0341]

[0342] Synthesis of Compound A182-2

[0343] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A182-2 (25.29 g, purity: 99.25%, yield: 72.23%), mass spectrum: 329.10 (M+H).

[0344] Synthesis of Compound A182-3

[0345] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A182-3 (15.38 g, purity: 99.76%, yield: 65.90%), mass spectrum: 307.04 (M+H).

[0346] Synthesis of Compound A182-4

[0347] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A182-4 (15.27 g, yield: 93.27%), mass spectrum: 335.08 (M+H).

[0348] Synthesis of Compound A182-5

[0349] Referring to the synthesis and purification method of reference compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A182-5 (5.97 g, purity: 99.42%, yield: 44.01%), and the mass spectrum is 303.05 (M+H).

[0350] Synthesis of compound A182-7

[0351] Referring to the synthesis and purification method of reference compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A182-7 (8.17 g, purity: 99.75%, yield: 69.73%), and the mass spectrum is 322.15 (M+H).

[0352] Synthesis of compound A182-9

[0353] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A182-9 (6.71 g, purity: 99.84%, yield: 74.33%), and the mass spectrum is 363.14 (M+H).

[0354] Synthesis of compound A182

[0355] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 6.94 g of the crude product of compound A182, the sublimation-pure compound A182 (4.75 g, purity: 99.90%, yield: 68.41%) is obtained, and the mass spectrum is 629.21 (M+H).

[0356] 11H 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).

[0357] Synthesis of Compound A207

[0358]

[0359] Synthesis of Compound A207-3

[0360] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A207-3 (6.79 g, purity: 99.17%, yield: 64.96%). Mass spectrum: 305.06 (M+H).

[0361] Synthesis of Compound A207-6

[0362] 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 to a 250 ml three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times, and then heated to 95 °C for 4 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the eluent), and Compound A207-3 was consumed completely.

[0363] Cool to 60 °C, add dichloromethane (200 ml), wash three times with deionized water (50 ml × 3), separate the liquid, mix with silica gel and load the column by dry method, carry out silica gel column chromatography purification (200 - 300 mesh silica gel, ethyl acetate: n-hexane = 1:10 as the eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain a white solid, which is compound A207-6 (4.36 g, purity: 99.31%, yield: 67.52%), MS: 303.05 (M+H).

[0364] Synthesis of Compound A207

[0365] Referring to the synthesis and purification methods 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%). After sublimation purification of 5.84 g of the crude product of compound A207, sublimation-pure compound A207 (3.69 g, purity: 99.90%, yield: 63.18%) was obtained, MS: 629.21 (M+H).

[0366] 1 H 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).

[0367] Synthesis of Compound A234

[0368]

[0369] Synthesis of Compound A234-2

[0370] Referring to the synthesis and purification methods of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A234-2 (13.17 g, purity: 99.07%, yield: 76.15%), MS: 355.15 (M+H).

[0371] Synthesis of Compound A234-3

[0372] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A234-3 (8.69 g, purity: 99.69%, yield: 71.24%). Mass spectrum: 333.09 (M+H).

[0373] Synthesis of compound A234-4

[0374] Referring to the synthesis and purification method of reference compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A234-4 (8.31 g, yield: 90.16%). Mass spectrum: 361.13 (M+H).

[0375] Synthesis of compound A234-5

[0376] Referring to the synthesis and purification method of reference compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A234-5 (5.14 g, purity: 99.31%, yield: 70.51%). Mass spectrum: 329.10 (M+H).

[0377] Synthesis of compound A234-7

[0378] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A234-7 (6.14 g, purity: 99.79%, yield: 70.98%). Mass spectrum: 556.19 (M+H).

[0379] Synthesis of compound A234

[0380] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 6.39 g of the crude product of compound A234, sublimation-pure compound A234 (4.16 g, purity: 99.96%, yield: 65.10%) was obtained. Mass spectrum: 848.32 (M+H).

[0381] 11H 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).

[0382] Synthesis of Compound A248

[0383]

[0384] Synthesis of Compound A248-2

[0385] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A248-2 (15.69 g, purity: 99.29%, yield: 69.30%). Mass spectrum: 404.15 (M+H).

[0386] Synthesis of Compound A248-3

[0387] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A248-3 (10.27 g, purity: 99.69%, yield: 70.05%). Mass spectrum: 382.09 (M+H).

[0388] Synthesis of Compound A248-4

[0389] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A248-4 (9.65 g, yield: 89.91%). Mass spectrum: 410.12 (M+H).

[0390] Synthesis of Compound A248-5

[0391] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A248-5 (5.94 g, purity: 99.63%, yield: 67.12%). Mass spectrum: 378.09 (M+H).

[0392] Synthesis of Compound A248-6

[0393] Referring to the synthesis and purification method of reference compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A248-6 (8.19 g, purity: 99.56%, yield: 67.95%). Mass spectrum: 337.12 (M+H).

[0394] Synthesis of Compound A248

[0395] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 7.15 g of the crude product of compound A248, sublimation-pure compound A248 (5.04 g, purity: 99.97%, yield: 70.48%) was obtained. Mass spectrum: 678.25 (M+H).

[0396] 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).

[0397] Synthesis of Compound A259

[0398]

[0399] Synthesis of Compound A259-1

[0400] Referring to the synthesis and purification method of reference compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A259-1 (7.68 g, purity: 99.49%, yield: 68.38%). Mass spectrum: 368.17 (M+H).

[0401] Synthesis of Compound A259

[0402] Referring to the synthesis and purification method of reference 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%). After sublimation purification of 8.31 g of the crude product of compound A259, sublimation-pure compound A259 (5.69 g, purity: 99.95%, yield: 68.47%) was obtained, and the mass spectrum was 634.25 (M+H).

[0403] 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).

[0404] Synthesis of compound A268

[0405] ;

[0406]

[0407] Synthesis of compound A268-2

[0408] Referring to the synthesis and purification method of reference compound A68-3, only the corresponding raw materials need to be changed to obtain the target compound A268-2 (14.37 g, yield: 90.92%), and the mass spectrum was 297.02 (M+H).

[0409] Synthesis of compound A268-3

[0410] Referring to the synthesis and purification method of reference compound A68-4, only the corresponding raw materials need to be changed to obtain the target compound A268-3 (8.19 g, purity: 99.36%, yield: 62.28%), and the mass spectrum was 279.01 (M+H).

[0411] Synthesis of compound A268-4

[0412] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A268-4 (6.34 g, purity: 99.51%, yield: 71.18%), and the mass spectrum was 311.09 (M+H).

[0413] Synthesis of Compound A268-5

[0414] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A268-5 (5.18 g, purity: 99.48%, yield: 72.03%). Mass spectrum: 373.20 (M+H).

[0415] Synthesis of Compound A268-7

[0416] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A268-7 (7.62 g, purity: 99.70%, yield: 73.32%). Mass spectrum: 333.09 (M+H).

[0417] Synthesis of Compound A268-8

[0418] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A268-8 (7.29 g, yield: 89.64%). Mass spectrum: 361.13 (M+H).

[0419] Synthesis of Compound A268-9

[0420] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A268-9 (4.07 g, purity: 99.53%, yield: 62.04%). Mass spectrum: 329.10 (M+H).

[0421] Synthesis of Compound A268

[0422] Referring to the synthesis and purification methods 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%). After sublimation purification of 5.06 g of the crude product of Compound A268, sublimation-pure Compound A268 (3.26 g, purity: 99.93%, yield: 64.42%) was obtained. Mass spectrum: 665.33 (M+H).

[0423] 11H 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).

[0424] Synthesis of Compound A277

[0425] ;

[0426]

[0427] Synthesis of Compound A277-2

[0428] Referring to the synthesis and purification methods of Compound A68-3, only the corresponding raw materials need to be changed to obtain the target compound A277-2 (14.23 g, yield: 90.04%), MS: 297.02 (M+H).

[0429] Synthesis of Compound A277-3

[0430] Referring to the synthesis and purification methods of Compound A68-4, only the corresponding raw materials need to be changed to obtain the target compound A277-3 (8.74 g, purity: 99.43%, yield: 66.46%), MS: 279.01 (M+H).

[0431] Synthesis of Compound A277-4

[0432] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A277-4 (7.21 g, purity: 99.38%, yield: 76.19%), MS: 311.09 (M+H).

[0433] Synthesis of Compound A277-5

[0434] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A277-5 (5.63 g, purity: 99.76%, yield: 67.11%), MS: 373.20 (M+H).

[0435] Synthesis of Compound A277-8

[0436] Compound A277-6 (10.00 g, 40.63 mmol), compound A277-7 (12.74 g, 60.95 mmol), copper(I) iodide (0.39 g, 2.03 mmol), potassium phosphate (21.56 g, 101.58 mmol), 1,2-diaminocyclohexane (0.47 g, 4.06 mmol), and 1,4-dioxane (250 ml) were added to a 500-ml three-necked round-bottom flask. The system was evacuated and filled with nitrogen three times, and then heated to 100 °C for reaction for 7 hours. The reaction was monitored by TLC (using ethyl acetate:n-hexane = 1:15 as the eluent), and compound A277-6 was consumed completely.

[0437] 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). After liquid separation, the sample was mixed with silica gel and loaded onto a column by dry method, and silica gel column chromatography purification was carried out (using 200-300 mesh silica gel and ethyl acetate:n-hexane = 1:10 as the eluent). After elution, the solvent was concentrated under reduced pressure at 70 °C for 1 hour to obtain a white solid, which was compound A277-8 (9.46 g, purity: 99.37%, yield: 71.15%). Mass spectrum: 327.05 (M+H).

[0438] Synthesis of compound A277-9

[0439] Referring to the synthesis and purification methods of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A277-9 (7.75 g, purity: 99.28%, yield: 75.28%). Mass spectrum: 375.22 (M+H).

[0440] Synthesis of compound A277-10

[0441] Referring to the synthesis and purification methods of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A277-10 (5.61 g, purity: 99.60%, yield: 72.37%). Mass spectrum: 387.12 (M+H).

[0442] Synthesis of compound A277-11

[0443] Referring to the synthesis and purification methods of compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A277-11 (5.34 g, yield: 90.53%). Mass spectrum: 415.15 (M+H).

[0444] Synthesis of compound A277-12

[0445] Referring to the synthesis and purification method of compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A277-12 (3.63 g, purity: 99.68%, yield: 74.22%). Mass spectrum: 383.13 (M+H).

[0446] Synthesis of Compound A277

[0447] 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%). After sublimation purification of 4.11 g of the crude product of compound A277, sublimation-pure compound A277 (2.57 g, purity: 99.93%, yield: 62.53%) was obtained. Mass spectrum: 719.36 (M+H).

[0448] 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).

[0449] Synthesis of Compound A280

[0450]

[0451] Synthesis of Compound A280-3

[0452] 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 A280-3 (11.53 g, purity: 99.46%, yield: 77.47%). Mass spectrum: 354.09 (M+H).

[0453] Synthesis of Compound A280-4

[0454] Referring to the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A280-4 (9.31 g, purity: 99.01%, yield: 64.32%). Mass spectrum: 446.22 (M+H).

[0455] Synthesis of Compound A280-5

[0456] 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 A280-5 (6.43 g, purity: 99.67%, yield: 69.48%). Mass spectrum: 458.12 (M+H).

[0457] Synthesis of compound A280-6

[0458] 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 A280-6 (6.14 g, yield: 90.40%). Mass spectrum: 486.15 (M+H).

[0459] Synthesis of compound A280-7

[0460] Referring to the synthesis and purification method of compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A280-7 (3.89 g, purity: 99.66%, yield: 69.41%). Mass spectrum: 454.13 (M+H).

[0461] Synthesis of compound A280

[0462] 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%). After sublimation purification of 4.93 g of the crude product of compound A280, sublimation-pure compound A280 (3.37 g, purity: 99.90%, yield: 68.35%) was obtained. Mass spectrum: 785.33 (M+H).

[0463] 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).

[0464] Synthesis of compound A284

[0465]

[0466] Synthesis of Compound A284-2

[0467] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A284-2 (12.75 g, purity: 99.38%, yield: 73.39%). Mass spectrometry: 345.08 (M+H).

[0468] Synthesis of Compound A284-3

[0469] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A284-3 (8.11 g, purity: 99.65%, yield: 69.27%). Mass spectrometry: 323.02 (M+H).

[0470] Synthesis of Compound A284-4

[0471] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the target compound A284-4 (7.84 g, yield: 90.16%). Mass spectrometry: 351.05 (M+H).

[0472] Synthesis of Compound A284-5

[0473] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound A284-5 (5.09 g, purity: 99.70%, yield: 71.81%). Mass spectrometry: 319.03 (M+H).

[0474] Synthesis of Compound A284-7

[0475] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A284-7 (8.29 g, purity: 99.64%, yield: 66.63%). Mass spectrometry: 381.13 (M+H).

[0476] Synthesis of Compound A284

[0477] Referring to the synthesis and purification methods 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%). After sublimation purification of 5.99 g of the crude product of Compound A284, the sublimation-pure Compound A284 (3.88 g, purity: 99.95%, yield: 64.77%) was obtained. Mass spectrometry: 663.18 (M+H).

[0478] 11H 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).

[0479] Synthesis of Compound A290

[0480]

[0481] Synthesis of Compound A290-2

[0482] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A290-2 (10.37 g, purity: 99.75%, yield: 71.39%). Mass spectrum: 322.04 (M+H).

[0483] Synthesis of Compound A290-3

[0484] Referring to the synthesis and purification methods of Compound A2-11, only the corresponding raw materials need to be changed to obtain the target compound A290-3 (8.57 g, purity: 99.60%, yield: 72.87%). Mass spectrum: 379.12 (M+H).

[0485] Synthesis of Compound A290

[0486] Referring to the synthesis and purification methods 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%). After sublimation purification of 7.28 g of the crude product of Compound A290, the sublimation-pure Compound A290 (4.95 g, purity: 99.95%, yield: 67.98%) was obtained. Mass spectrum: 645.19 (M+H).

[0487] 11H 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).

[0488] Synthesis of Compound B25

[0489]

[0490] Synthesis of Compound B25-2

[0491] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B25-2 (24.53 g, purity: 99.42%, yield: 77.41%). Mass spectrum: 421.19 (M+H).

[0492] Synthesis of Compound B25

[0493] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B25 (12.11 g, purity: 99.95%, yield: 79.06%). After sublimation purification of 12.11 g of the crude product of Compound B25, sublimation-pure Compound B25 (9.99 g, purity: 99.95%, yield: 82.50%) was obtained. Mass spectrum: 576.24 (M+H).

[0494] 1 1H 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).

[0495] Synthesis of Compound B27

[0496]

[0497] Synthesis of Compound B27

[0498] Referring to the synthesis and purification methods 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%). After sublimation purification of 6.82 g of the crude product of Compound B27, sublimation-pure Compound B27 (4.14 g, purity: 99.95%, yield: 66.02%) was obtained, and the mass spectrum was 601.22 (M+H).

[0499] 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).

[0500] Synthesis of Compound B54

[0501]

[0502] Synthesis of Compound B54-2

[0503] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B54-2 (20.00 g, purity: 99.1%, yield: 75.63%), and the mass spectrum was 257.03 (M+H).

[0504] Synthesis of Compound B54-3

[0505] Referring to the synthesis and purification methods of Compound A2-7, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B54-3 (16.78 g, yield: 96.06%), and the mass spectrum was 285.06 (M+H). The obtained compound was directly used in the next step without purification.

[0506] Synthesis of Compound B54-4

[0507] Referring to the synthesis and purification method of compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound B54-4 as a white solid (15.63 g, purity: 99.78%, yield: 75.12%), and the mass spectrum is 253.03 (M+H).

[0508] Synthesis of compound B54-5

[0509] Referring to the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B54-5 as a white solid (15.12 g, purity: 99.43%, yield: 76.51%), and the mass spectrum is 345.16 (M+H).

[0510] Synthesis of compound B54-7

[0511] Add 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) into a 1000 ml three-necked round-bottom flask. Replace the vacuum with nitrogen three times, then heat the system to 65 °C and react for 6 hours. Monitor the reaction by TLC (using ethyl acetate: n-hexane = 1:15 as the eluent), and when compound B54-5 is completely consumed.

[0512] Cool down to 60 °C and concentrate under reduced pressure to remove the solvent. Add ethyl acetate (700 ml), wash three times with deionized water (300 ml × 3), separate the layers, mix with silica gel and load onto the column by dry method, and perform silica gel column chromatography purification (using 200-300 mesh silica gel and ethyl acetate: n-hexane = 1:20 as the eluent). After elution, concentrate under reduced pressure at 70 °C for 2 hours to obtain the target compound B54-7 as a white solid (18.53 g, purity: 99.21%, yield: 75.32%), and the mass spectrum is 423.22 (M+H).

[0513] Synthesis of compound B54-8

[0514] Referring to the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B54-8 as a white solid (12.12 g, purity: 99.03%, yield: 78.06%), and the mass spectrum is 471.22 (M+H).

[0515] Synthesis of compound B54

[0516] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B54 as a light yellow solid (15.12 g, purity: 99.94%, yield: 77.63%). After sublimation purification of 15.12 g of the crude product of compound B54, sublimation-pure compound B54 (12.57 g, purity: 99.94%, yield: 83.14%) was obtained, and the mass spectrum was 576.20 (M+H).

[0517] 1 H 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).

[0518] Synthesis of compound B71

[0519]

[0520] Synthesis of compound B71-1

[0521] Referring to the synthesis and purification method of reference compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B71-1 as a white solid (9.16 g, purity: 99.17%, yield: 79.67%), and the mass spectrum was 422.18 (M+H).

[0522] Synthesis of compound B71

[0523] Referring to the synthesis and purification method of reference compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B71 (10.21 g, purity: 99.93%, yield: 77.50%). After sublimation purification of 10.21 g of the crude product of compound B71, sublimation-pure compound B71 (6.25 g, purity: 99.93%, yield: 61.21%) was obtained, and the mass spectrum was 617.20 (M+H).

[0524] 11H 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).

[0525] Synthesis of Compound B80

[0526]

[0527] Synthesis of Compound B80-2

[0528] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B80-2 (14.19 g, purity: 99.34%, yield: 68.27%). Mass spectrum: 334.08 (M+H).

[0529] Synthesis of Compound B80-3

[0530] Referring to the synthesis and purification methods 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 is directly used in the next step without purification.

[0531] Synthesis of Compound B80-4

[0532] Referring to the synthesis and purification methods of Compound A2-8, only the corresponding raw materials need to be changed to obtain the target compound B80-4 (7.96 g, purity: 99.71%, yield: 63.75%). Mass spectrum: 330.06 (M+H).

[0533] Synthesis of Compound B80-5

[0534] Referring to the synthesis and purification methods of Compound A2-3, only the corresponding raw materials need to be changed to obtain the white solid target compound B80-5 (7.25 g, purity: 99.29%, yield: 75.67%). Mass spectrum: 422.21 (M+H).

[0535] Synthesis of Compound B80

[0536] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B80 (7.06 g, purity: 99.93%, yield: 68.90%). After sublimation purification of 7.06 g of the crude product of Compound B80, sublimation-pure Compound B80 (4.71 g, purity: 99.93%, yield: 66.71%) was obtained. Mass spectrum: 617.19 (M+H).

[0537] 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).

[0538] Synthesis of Compound B96

[0539]

[0540] Synthesis of Compound B96

[0541] Referring to the synthesis and purification methods 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%). After sublimation purification of 7.84 g of the crude product of Compound B96, sublimation-pure Compound B96 (5.46 g, purity: 99.95%, yield: 69.70%) was obtained. Mass spectrum: 648.24 (M+H).

[0542] 11H 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).

[0543] Synthesis of Compound B104

[0544]

[0545] Synthesis of Compound B104

[0546] Referring to the synthesis and purification methods of Compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound B104 as a light yellow solid (21.69 g, purity: 99.93%, yield: 87.70%). After sublimation purification of 21.69 g of the crude product of Compound B104, sublimation-pure Compound B104 (17.85 g, purity: 99.93%, yield: 82.29%) was obtained. Mass spectrum: 550.20 (M+H).

[0547] 1 1H 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).

[0548] Synthesis of Compound B128

[0549]

[0550] Synthesis of Compound B128-2

[0551] Referring to the synthesis and purification method of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B128-2 (9.14 g, purity: 99.41%, yield: 74.93%), mass spectrometry: 262.20 (M+H).

[0552] Synthesis of Compound B128-4

[0553] 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 B128-4 (8.01 g, purity: 99.62%, yield: 68.31%), mass spectrometry: 340.06 (M+H).

[0554] Synthesis of Compound B128-5

[0555] Referring to the synthesis and purification method of Compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound B128-5 (6.59 g, purity: 99.38%, yield: 72.37%), mass spectrometry: 388.25 (M+H).

[0556] Synthesis of Compound B128

[0557] 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 B128 (6.34 g, purity: 99.96%, yield: 77.24%). After sublimation purification of 6.34 g of the crude product of Compound B128, the sublimation-pure Compound B128 (4.39 g, purity: 99.96%, yield: 69.24%) was obtained, mass spectrometry: 583.26 (M+H).

[0558] 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).

[0559] Examples:

[0560] Examples 1 to 8 provide an aromatic amine compound, which corresponds to compound A2, A50, A68, A79, A81, A99, A116, and A234 prepared by the above operations, respectively.

[0561] Examples 9 to 31 provide a composition for an organic light-emitting device, which is composed of a first host material and a second host material. Among them, the aromatic amine compounds (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 operations are used as the first host material, and the second host compounds (B25, B27, B54, B71, B80, B96, B104, B128) that satisfy the structure of formula (3) are used as the second host material. The mass ratio of the first host material to the second host material is 5:5.

[0562] Example 32 provides a composition for an organic light-emitting device, which is composed of a first host material and a second host material. Among them, the aromatic amine compound A50 prepared by the above operations is used as the first host material, and the second host compound B25 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 2:8.

[0563] Example 33 provides a composition for an organic light-emitting device, which is composed of a first host material and a second host material. Among them, the aromatic amine compound A68 prepared by the above operations is used as the first host material, and the second host compound B54 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 8:2.

[0564] The specific combination methods are listed in the performance test result table below.

[0565] Comparative examples: Comparative examples 1 to 4 provide a compound that can be used in an organic light-emitting device, which corresponds to RH-N, comparative compound 2, comparative compound 3, and comparative compound 4, respectively.

[0566] Comparative examples 5 to 10 provide a composition that can be used in an organic light-emitting device, which is composed of a first host material and a second host material. Among them, the aromatic amine compounds (A50) or comparative compounds 1 to 4 prepared by the above operations are used as the first host material, and the second host compounds (B25, B54) or RH-N that satisfy the structure of formula (3) are 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 methods are listed in the performance test result table below.

[0567] The structural formulas of Comparative Compounds 1 to 4 are as follows:

[0568] 。

[0569] Application Example:

[0570] Fabrication of Organic Light-Emitting Devices

[0571] As shown in the attached Figure 2 The organic light-emitting device includes a 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, which are stacked.

[0572] The specific fabrication process is as follows: A glass substrate with an ITO (indium tin oxide, 100 nm) transparent electrode of 50 mm × 50 mm × 1.0 mm is ultrasonically cleaned in ethanol for 10 minutes, then dried at 150 °C and treated with N2 Plasma for 30 minutes. The washed glass substrate is mounted on the substrate holder of a vacuum evaporation device. Compound NDP-9 and Compound HTM 1 are evaporated in a weight ratio of 97:3 to form a hole injection layer with a film thickness of 10 nm. Immediately thereafter, a layer of HTM1 is evaporated to form a thin film with a film thickness of 60 nm as HTL1 (hole transport layer 1). Then, a layer of HTM2 is evaporated on HTL1 to form a thin film with a film thickness of 10 nm as HTL2 (hole transport layer 2).

[0573] Then, a light-emitting layer with a film thickness of 40 nm is evaporated on HTL2. The raw material of the light-emitting layer consists of a host material and a red light doping material. The mass fraction of the host material is 97%, and the mass fraction of the red light doping material is 3%. The host material is the compound or composition in the above examples and comparative examples.

[0574] An electron transport layer with a film thickness of 35 nm is evaporated on the light-emitting layer. The raw material of the electron transport layer is a mixture composed of ETL and LiQ. In this mixture, the mass ratio of ETL to LiQ is 50:50.

[0575] Then, LiQ is evaporated as an electron injection material (with a thickness of 1 nm) on the electron transport layer. Then, Mg / Ag (with a thickness of 100 nm, and the mass ratio of Mg to Ag is 1:9) is evaporated as the cathode material in a co-evaporation mode to fabricate the organic light-emitting device.

[0576] The structural formulas of NDP-9, HTM1, HTM2, ETL material, red light doping material, LiQ, and RH-N are as follows:

[0577] .

[0578] Evaluation:

[0579] The above organic light-emitting devices were subjected to device performance tests. The compounds prepared in this application and Comparative Compounds 1-4 were used as host materials for comparison respectively. A constant current power supply (Keithley 2400) was used, a fixed current density was passed through the light-emitting element, and a spectro-radiometer (CS 2000) was used to measure the emission spectrum. At the same time, the IVL (current-voltage-luminance) performance of the device was measured at 10 mA / cm 2 , and the LT95 device lifetime was tested at 50 mA / cm 2 . The results are shown in Tables 1 and 2 below.

[0580] The device performance test data of the devices prepared by co-evaporating the arylamine compounds in Examples 1-8 of this application or Comparative Compounds 1-4 as a single host and a red light doping material into the light-emitting layer are shown in Table 1.

[0581] Table 1

[0582]

[0583] The device performance test data of the devices prepared by using the compositions in Examples 9-33 of this application and Comparative Examples 5-10 as double host materials and co-evaporating them with a red light doping material into the light-emitting layer are shown in Table 2.

[0584] Table 2

[0585]

[0586] It can be seen from Tables 1-2 that the device lifetimes and luminous efficiencies of the devices prepared from the compounds and compositions of the examples of this application are significantly better than those of the devices prepared from the compounds and compositions in the comparative examples, and the voltage is significantly lower than that of the devices prepared from the compounds and compositions in the comparative examples.

[0587] Comparison of sublimation temperatures: The definition of sublimation temperature is: at a vacuum degree of 10 -7 Torr, the temperature corresponding to a sublimation rate of 1 Å per second. The test results of some compounds in the examples of the present invention and Comparative Compounds 1-4 are shown in Table 3.

[0588] Table 3

[0589]

[0590] It can be seen from Table 3 that the compounds of the examples of this application have lower sublimation temperatures compared with Comparative Compounds 1-4, which is beneficial to industrial application.

[0591] 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 balanced hole and electron transfer rates and broadened the exciton recombination area in the light-emitting layer, greatly improving the efficiency and life of the device compared with the comparative compound 1-1.

[0592] Therefore, the compound material of the present application has advantages such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a host material in OLED light-emitting devices. It also has a low melting point, which is beneficial for the stability of material evaporation as a molten material. As a host material, the compound of the present application has the potential for application in the AMOLED industry. Furthermore, as a red light host material, the aromatic amine compound shows 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 for 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.

[0593] In addition, since it is impossible to enumerate all the compounds of the present application, the above Tables 1-3 only list the properties of some of the compounds or devices 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 advantages similar to A2, such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

[0594] The above describes the embodiments of the present application in detail, but the present application is not limited to the above embodiments. Various changes can be made within the scope of knowledge possessed by 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 as shown in the following formula (1): Formula (1) In the formula, ring A is selected from the structure shown in the following formula (A-1): ； In the formula, represents the fusion site of the X-containing five-membered ring in formula (1); X is selected from chalcogens, and the chalcogen is O or S; R1 is selected from hydrogen or an aryl group having 6 to 20 carbon atoms; a is an integer from 0 to 4; if a ≥ 2, then each R1 is the same or different; L1 is selected from a single bond; L2 is selected from a single bond, an arylene group having 6 to 20 carbon atoms; B is selected from the substituents shown in the following formula (2); Formula (2) In the formula, ring C is selected from the structures shown below: ； In the formula, represents the fusion site of the N-containing five-membered ring in formula (2); Y is selected from O; Indicates the connection site of L2 in formula (2); Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Ar2 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; the substitution of Ar1 is selected from deuteration, and the substitution in Ar2 means being substituted by deuterium, and the substitution number ranges from single substitution to maximum number of substitutions.

2. The aromatic amine compound according to claim 1, wherein: Each Ar1 is independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution of Ar1 is selected from deuteration, and the substitution number ranges from single substitution to maximum number of substitutions.

3. The arylamine compound according to claim 1, wherein: Ar1 and Ar2 are each independently selected from a phenyl group containing deuterium substitution, a biphenyl group containing deuterium substitution or a naphthyl group containing deuterium substitution.

4. The aromatic amine compound according to claim 1, wherein: L2 is selected from a phenylene group, a biphenylene group or a naphthylene group.

5. The arylamine compound according to claim 1, characterized in that: The aryl group is selected from a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a tetraphenyl group, a pyrenyl group, a chrysenyl group, a benzo[c]phenanthryl group, a fluorenyl group, a benzofluorenyl group, a biphenyl group, a terphenyl group or a fluoranthenyl group.

6. An aromatic amine compound, characterized in that: The aromatic amine compound is one of the following structural formulas: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 7. A composition for an organic light-emitting device, characterized in that: The composition contains a first host compound and a second host compound, and the first host compound is the aromatic amine compound described in any one of claims 1 to 6: The second host compound has a structure represented by 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 a chalcogen element; Z1, Z2 and Z3 are each independently selected from N or CR g ; R d 、R e and R f are each independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl or C6-C30 arylsilyl; the heteroatoms in the heteroalkyl, heterocycloalkyl or heteroaryl are each independently selected from at least one of O, S, N, Se, Si or Ge; R4 and R g each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C6-C60 arylsilyl, C6-C60 arylboron, C6-C60 arylphosphine or C6-C60 arylamine; d is an integer from 0 to 4; if d ≥ 2, then each R1 is the same or different; L3 to L5 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms; Ar3 and Ar4 are each independently selected from a substituted or unsubstituted aryl group having 6 to 36 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 36 carbon atoms; The substitutions in the ring D, L3, L4, L5, Ar3 and Ar4 each independently represent being substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, an amino group substituted by C1-C6 alkyl, a C1-C6 hydrocarbon group-substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a C1-C6 hydrocarbon group-substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the substitution number ranges from single substitution to maximum number of substitutions.

8. The composition for an organic light emitting device according to claim 7, wherein: L3 to L5 are each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group.

9. The composition for an organic light-emitting device according to claim 7, characterized in that: Each of Ar3 to Ar4 is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, fluoranthenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl. The substitutions in Ar3 and Ar4 each independently represent being substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, an amino group substituted by C1-C6 alkyl, a C6-C30 aryl substituted or unsubstituted by C1-C6 hydrocarbon group, a C3-C30 heteroaryl substituted or unsubstituted by C1-C6 hydrocarbon group, and the number of substitutions ranges from single substitution to maximum number of substitutions.

10. The composition for an organic light-emitting device according to claim 7, characterized in that: Ar3 to Ar4 are each independently selected from phenyl containing deuterium substitution, biphenyl containing deuterium substitution or naphthyl containing deuterium substitution.

11. A composition for an organic light emitting device, characterized in that: The composition includes a first host compound and a second host compound. The first host compound is an aromatic amine compound as described in any one of claims 1 to 6: The second host compound is selected from one of the following structural formulas: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 12. The composition for an organic light emitting device according to claim 7, characterized in that: The mass ratio of the first host compound to the second host compound is 8:2 - 2:

8.

13. A composition for an organic light emitting device, characterized in that: The composition further includes at least one third host compound. The third host compound has the structure shown in formula (3) of claim 7 or is an aromatic amine compound as described in any one of claims 1 to 6; the structures of the first, second, and third host compounds are all different.

14. An organic light-emitting device, characterized in that: An aromatic amine compound as described in any one of claims 1 to 6 or a composition for an organic light-emitting device as described in any one of claims 7 to 13.

15. An organic light-emitting device, characterized in that: Comprising a cathode and an anode, the cathode is disposed opposite to the anode, and a light-emitting layer is provided between the cathode and the anode. The light-emitting layer contains an aromatic amine compound as described in any one of claims 1 to 6 or a composition for an organic light-emitting device as described in any one of claims 7 to 13.

Images