Arylamine compound, composition containing arylamine compound and organic electroluminescent device

Abstract

The invention provides an arylamine compound, a composition containing the arylamine compound and an organic electroluminescent device, and the arylamine compound has a series of excellent physical and chemical characteristics and has a good application prospect in the photoelectric field. Specifically, the arylamine compound has excellent photoelectric stability, can effectively resist performance degradation caused by illumination and current change, and ensures stable output of the device in long-time operation. In the aspect of electrical properties, the arylamine compound has a proper HOMO energy level, is beneficial to rapid injection of holes into a light-emitting layer, and shows double advantages of low driving voltage and high light-emitting efficiency. Meanwhile, the arylamine compound also has a relatively long device life due to excellent chemical stability and thermal stability, so that the overall service life of the photoelectric device is prolonged, and the replacement and maintenance cost is reduced.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to an aromatic amine compound, a composition containing the same, and an organic electroluminescent device. Background Technology

[0002] Currently, Organic Light Emitting Diodes (OLEDs), as a leading technology for future displays and lighting, are attracting much attention due to their wide range of applications. OLED technology is not only shining in consumer electronics such as smartphones, tablets, and high-definition TVs, but is also gradually penetrating into wearable devices, automotive displays, indoor lighting, and many other fields, demonstrating extremely broad development prospects. However, despite the significant progress made in OLED technology, its commercialization still faces challenges, especially in key performance indicators such as improving luminous efficiency, reducing driving voltage, and extending lifespan, which require further in-depth research and continuous optimization.

[0003] The core structure of OLED devices is a multi-layered, stacked "sandwich" structure, with metal electrodes serving as the top and bottom boundaries, and various organic thin film layers with different functions precisely arranged in the middle. Under the influence of an electric field, electrons are injected from the cathode and holes are injected from the anode. These electrons travel towards each other within the device, eventually meeting and recombinating in the emissive layer. This recombination process not only involves photon emission but may also dissipate as heat, directly affecting the OLED's luminous efficiency. To maximize light output, researchers are dedicated to optimizing the emissive layer design, particularly focusing on phosphorescent OLEDs, whose efficient triplet emission mechanism opens new avenues for improving brightness and efficiency.

[0004] It is worth noting that the performance of phosphorescent OLEDs is not only constrained by the choice of emitting element but also heavily influenced by the properties of the host material. As a crucial component of the emitting layer, the host material's energy level structure, mobility, and stability have a vital impact on device performance. Optimizing the host material can significantly reduce the device's operating voltage, improve energy conversion efficiency, and effectively extend the device's lifespan. Currently, the main emitting layer materials in organic electroluminescent devices are Alq3, Balq, and DPVBi, but these materials generally have low luminous efficiency. Therefore, developing novel high-performance host materials is of great significance to the development of the OLED field. Summary of the Invention

[0005] In order to overcome the problems existing in the prior art, one of the objectives of the present invention is to provide an aromatic amine compound.

[0006] This application proposes an aromatic amine compound with a suitable HOMO energy level, which is beneficial for hole injection. When this compound is used as a host material for OLEDs, it reduces the accumulation of holes at the emissive layer interface, significantly reduces the driving voltage of the device, and makes hole and electron transport more balanced, which is beneficial to improving the luminous efficiency and lifespan of the device.

[0007] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0008] A first aspect of the present invention provides an aromatic amine compound, the structural formula of which is shown in formula (1):

[0009]

[0010] Among them, X1-X 28 Each is independently selected as CR0 or N;

[0011] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamino; when R0 is C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, or C2-C40 alkynyl, adjacent R0s may be linked to form a fused ring;

[0012] L1 and L2 are selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups;

[0013] Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazoyl, substituted or unsubstituted fluoranthraceneyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthozoyl, substituted or unsubstituted phenanthoxazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, or substituted or unsubstituted benzocarbazole;

[0014] In L1, L2, or Ar1, the substitutions each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, deuterium-substituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, deuterium-substituted C3-C30 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0015] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge.

[0016] The beneficial effects of this invention are:

[0017] The aromatic amine compounds of this invention possess a series of superior physicochemical properties, showing promising application prospects in the optoelectronic field. Specifically, these compounds exhibit excellent photoelectric stability, effectively resisting performance degradation caused by changes in light and current, ensuring stable output of the device during long-term operation. In terms of electrical performance, these aromatic amine compounds possess suitable HOMO energy levels, facilitating rapid hole injection into the emissive layer, demonstrating the dual advantages of low driving voltage and high luminous efficiency. Low driving voltage means that under the same conditions, the device can consume less electrical energy to achieve the same brightness, which is significant for improving energy efficiency and extending the battery life of portable electronic devices. High luminous efficiency is directly related to the light output quality and energy conversion efficiency of the device, providing crucial technical support for energy conservation and emission reduction. Furthermore, these aromatic amine compounds also possess a long device lifespan, thanks to their excellent chemical and thermal stability, resisting environmental erosion of the material structure, thereby extending the overall lifespan of the optoelectronic device and reducing replacement and maintenance costs. Attached Figure Description

[0018] Figure 1 This is a schematic diagram of the organic electroluminescent device structure of the present invention. Detailed Implementation

[0019] The present invention will be further described in detail below through specific embodiments. Unless otherwise specified, the raw materials used in the following embodiments can be obtained from conventional commercial channels or prepared and isolated through simple synthesis; unless otherwise specified, the processes employed are conventional processes in the art.

[0020] Specifically, a first aspect of the present invention relates to an aromatic amine compound having the structural formula shown in formula (1):

[0021]

[0022] Among them, X1-X 28 Each is independently selected as CR0 or N;

[0023] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, and C3-C40 alkylsilyl. The R0 can be a C6-C60 arylsilyl, a C1-C40 alkylboryl, a C6-C60 arylboryl, a C6-C60 monoarylphosphinyl, a C6-C60 diarylphosphinyl, or a C6-C60 arylamino; when R0 is a C1-C40 alkyl, a C1-C40 heteroalkyl, a C2-C40 alkenyl, or a C2-C40 alkynyl, adjacent R0s can be linked to form a fused ring;

[0024] L1 and L2 are selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups;

[0025] Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazoyl, substituted or unsubstituted fluoranthraceneyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthozoyl, substituted or unsubstituted phenanthoxazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, or substituted or unsubstituted benzocarbazole;

[0026] In L1, L2, or Ar1, the substitutions each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, deuterium-substituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, deuterium-substituted C3-C30 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0027] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge.

[0028] In some embodiments of the present invention, the structural formula of the aromatic amine compound is selected from any of the structures shown in formulas (3) to (10):

[0029]

[0030]

[0031] Where e is an integer between 0 and 4; if e ≥ 2 or a larger integer, then each R0 may be the same or different.

[0032] In some preferred embodiments of the present invention, the structural formula of the aromatic amine compound is selected from any of the structures shown in formulas (11) to (18):

[0033]

[0034]

[0035] Where e is an integer from 0 to 4; if e ≥ 2 or a larger integer, then each R0 may be the same or different. In some implementations, X1-X 28 The number of N values ​​is an integer between 0 and 5. It can be 0, 1, 2, 3, 4, 5 or any other range within the range of 0-5, such as 0-1, 0-2, 0-3, 0-4, 1-3 or 2-5.

[0036] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazole, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthazolyl, substituted or unsubstituted phenanthazolyl, substituted or unsubstituted benzophenanthryl, etc. The substituted or unsubstituted benzonaphthofuran, or the substituted or unsubstituted benzocarbazole, wherein each substitution independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C12 cycloalkyl, deuterated C6-C20 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C6-C20 aryl, deuterated C3-C20 heteroaryl, or C1-C6 hydrocarbon-substituted or unsubstituted C3-C20 heteroaryl, and the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0037] In some embodiments of the invention, Ar1, the substitution independently represents substitution by deuterium, fluorine, cyano, tert-butyl, pyridyl, phenyl, tolyl, deuterated phenyl, naphthyl, deuterated naphthyl, dibenzothiophene, dibenzofuranyl, deuterated dibenzofuranyl, adamantyl, carbazole, cyclohexyl, phenylbenzoxazolyl, phenylnaphthoxazolyl, or phenylphenanthrenexazolyl;

[0038] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl, or C6-C30 arylamine. When R0 is a C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, or C2-C20 alkynyl, adjacent R0s can be linked to form a fused ring.

[0039] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl, or C6-C20 arylamine. When R0 is a C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, or C2-C10 alkynyl, adjacent R0s can be linked to form a fused ring.

[0040] In some embodiments of the present invention, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, and C6-C20 aryl. When R0 is a C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, or C2-C10 alkynyl, adjacent R0s can be connected to form a four-membered ring, a five-membered ring, a six-membered ring, or a seven-membered ring. It can be tetramethylcyclohexane, cyclohexane, cyclopentane, or a benzene ring.

[0041] In some embodiments, L1 and L2 are selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C3-C30 heteroarylene groups;

[0042] In some embodiments, L1 and L2 are selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups;

[0043] In some embodiments, L1 and L2 are independently selected from one of the following structural formulas: single bond, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted naphthylene, or deuterated or unsubstituted pyridylene.

[0044] In some embodiments, in L1, L2, or Ar1, the substitution each independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, deuterium-substituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, deuterium-substituted C3-C30 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0045] In some embodiments, in L1, L2, or Ar1, the substitution each independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, deuterium-substituted C6-C20 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C20 aryl, deuterium-substituted C3-C20 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C20 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0046] In some embodiments, in L1, L2, or Ar1, the substitution each independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C4 alkyl, C3-C8 cycloalkyl, C1-C4 alkyl-substituted amino, deuterium-substituted or unsubstituted C6-C10 aryl, C1-C4 alkyl-substituted or unsubstituted C6-C10 aryl, deuterium-substituted or unsubstituted C3-C10 heteroaryl, or C1-C4 alkyl-substituted or unsubstituted C3-C10 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0047] In some embodiments, the aromatic amine compound is one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] A second aspect of the present invention relates to a composition comprising a first host compound and a second host compound; the first host compound is an aromatic amine compound as described in the first aspect; the structural formula of the second host compound is shown in formula (2):

[0059]

[0060] In equation (2), the bridging structure means that L3 can be connected to ring A or to the right aromatic ring.

[0061] In formula (2), ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, or substituted or unsubstituted phenanthrene rings;

[0062] X is selected from NR a CR b R c Or oxygen group elements;

[0063] Z1, Z2, and Z3 are each independently selected from N or CR. d ;

[0064] R a R b and R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, or C6-C30 arylsilyl; or, R b and R c They can be connected to form a ring;

[0065] R1 and R dEach 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 arylphosphine, or C6-C60 arylamine;

[0066] a is an integer from 0 to 4; it can be understood that if a ≥ 2 (such as 2, 3 or 4), then each R1 is either the same or different;

[0067] L3 to L5 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene;

[0068] Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6-C36 aryl groups or substituted or unsubstituted C2-C36 heteroaryl groups;

[0069] The substitutions in rings A, L3-L5, Ar2, and Ar3 each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions.

[0070] In formula (2), the heteroatom in the heteroaryl, heteroaryl, heteroalkyl or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si and Ge.

[0071] In some embodiments, the oxalic elements are selected from O, S, or Se.

[0072] In some embodiments, the oxalic elements are selected from O or S.

[0073] In some implementations, R a R b and R c Each is independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl, or C6-C20 arylsilyl; or, R b and R c They can be connected to form a ring;

[0074] In some implementations, R a R b and R c Each is 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; or, R b and R c They can be connected to form a ring;

[0075] In some implementations, Z1, Z2, and Z3 are all selected from N, or one of them is selected from CR. d The other two are selected from N;

[0076] In some implementations, R1 and R d Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl or C6-C30 arylamino;

[0077] In some implementations, R1 and R d Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl or C6-C20 arylamino;

[0078] In some embodiments, L3 to L5 are each independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene.

[0079] In some embodiments, L3 to L5 are each independently selected from single-bonded, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene.

[0080] In some embodiments, Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C2-C30 heteroaryl groups;

[0081] In some embodiments, Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6-C26 aryl groups or substituted or unsubstituted C2-C26 heteroaryl groups;

[0082] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthazolyl, substituted or unsubstituted phenanthazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, or substituted or unsubstituted benzocarbazole or a combination of at least two of these.

[0083] Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, or combinations thereof.

[0084] In some embodiments, the benzo[a]phenanthrene group comprises Structures such as benzo[c]phenanthrene or benzo[c]phenanthrene.

[0085] In some embodiments, the combination includes at least one of fusion or bonding.

[0086] In some embodiments, the substitution in rings A, L3-L5, Ar2, and Ar3 is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C20 aryl or C1-C6 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0087] In some embodiments, the second host compound satisfies at least one of the following conditions:

[0088] (1) Z1, Z2, and Z3 are all selected from N; or one of them is selected from CH and the other two are selected from N;

[0089] (2) L3-L5 are each independently selected from single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted phenanthoxazolyl or substituted or unsubstituted phenanthiazolyl.

[0090] (3) Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo[a]phenanthryl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzo[a]oxazolyl, substituted or unsubstituted benzo[a]naphthofuranyl, substituted or unsubstituted benzo[a]phenanthrylfuranyl, substituted or unsubstituted naphtho[a]oxazolyl, substituted or unsubstituted phenanthryl[a]oxazolyl, substituted or unsubstituted phenanthrethiazolyl;

[0091] (4) R1 is selected from hydrogen or deuterium;

[0092] (5)X is selected from NR a CR b R c , O or S, where R a R b R c Each is independently selected from methyl or phenyl; or R b and R c The linkage forms a fluorene group;

[0093] (6) In rings A, L3-L5, Ar2 and Ar3, the substitution is independently substituted by at least one of deuterium, phenyl, biphenyl, naphthyl, C1-C6 hydrocarbon substituted or unsubstituted benzoxazolyl, C1-C6 hydrocarbon substituted or unsubstituted naphthoxazolyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

[0094] In some embodiments, the second host compound is selected from one of the following structural formulas, or from one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] In some embodiments, the mass ratio of the first host compound to the second host compound is (0.25-4):1.

[0102] In some embodiments, the mass ratio of the first host compound and the second host compound is selected from 0.25:1, 0.5:1, 1:1, 2:1, 3:1, and 4:1.

[0103] A third aspect of the present invention relates to an organic electroluminescent device comprising an aromatic amine compound as described in the first aspect, or a composition as described in the second aspect.

[0104] In some embodiments, the organic electroluminescent device includes a cathode and an anode, the cathode and the anode being disposed opposite to each other, and a functional layer being provided between the cathode and the anode, the functional layer comprising the aforementioned aromatic amine compound or composition.

[0105] In some embodiments, the functional layer includes a light-emitting layer, and the aforementioned aromatic amine compound or composition may be used alone or after doping to prepare the light-emitting layer.

[0106] In some embodiments, the light-emitting layer is a red light-emitting layer, and the aforementioned aromatic amine compound or composition serves as the red light material of the light-emitting layer. More specifically, the aforementioned aromatic amine compound or composition serves as the main material of the red light-emitting layer.

[0107] A fourth aspect of the present invention relates to a semiconductor device comprising an aromatic amine compound as described in the first aspect, or a composition as described in the second aspect, or an organic electroluminescent device as described in the third aspect.

[0108] In some embodiments, the semiconductor device may be at least one of organic light-emitting cells, organic light-emitting field-effect transistors (OLET), OLED displays, organic electroluminescent lasers (OLEL), organic electroluminescent sensors (OLES), etc.

[0109] Unless otherwise stated, 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, definitions of some terms are provided below. In the event that the definitions of terms provided herein differ from the meanings commonly understood by those skilled in the art, the definitions and interpretations provided herein shall prevail.

[0110] Heteroalkyl refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom, excluding cases where the carbon atom serving as a linking site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl). Exemplary heteroalkyl groups include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, epoxybutane, epoxypentane, epoxyhexane, etc., preferably methoxymethane and epoxypentane.

[0111] Heterocyclic alkyl groups refer to cycloalkyl groups in which at least one carbon atom is replaced by a non-carbon atom, which can be selected from at least one of O, S, N, P, B, Si, Ge, or Se. The number of carbon atoms in a heterocyclic alkyl group can be from 3 to 30, preferably from 3 to 12, more preferably from 3 to 10, and particularly preferably from 3 to 6. Exemplary heterocyclic alkyl groups include: epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0112] An aryl group is an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be monocyclic or polycyclic. In a polycyclic aryl group, at least one ring is an aromatic ring system. The multiple rings in a polycyclic aryl group can be linked together by single bonds or fused together. Exemplary aryl groups include: phenyl, naphthyl, anthraceneyl, phenanthrene, tetraphenyl, pyrene, dinaphthylphenyl, etc. Acenamethanil, benzo[c]pyrene, benzo[g]phenanthryl, benzo[g]triyl, fluorenyl, spirodifluorenyl, benzo[f]fluorenyl, dibenzo[f]fluorenyl, biphenyl, triphenyl, tetraphenyl or fluoranyl.

[0113] A heteroaryl group is defined as an aryl group in which at least one carbon atom is replaced by a non-carbon atom, wherein the non-carbon atom can be selected from at least one of O, S, N, Se, Si, or Ge. Exemplary heteroaryl groups include: pyrrolithyl, pyrrolopyrrolithyl, furanopyrrolithyl, thienopyrrolithyl, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazine, pyridazine, phenazinyl, phenothiazine, phenoxazine, indole, isoindole, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furanofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2-] [D] furanyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, quinazolinoneyl, carbazoyl, azacarbazoyl, diazacarbazoyl, phenanthrynyl, primidyl, acridineyl, dihydroacridyl, phenanthrynyl, oxazolinyl, oxazolyl, oxadiazolyl, benzoisooxazolyl, thiazoyl, benzothiazoyl, benzoisothiazoyl, pyrroloimidazoyl, furazolyl, thienyl, benzothiaphenyl, dibenzothiaphenyl, azadibenzothiaphenyl, diazadibenzothiaphenyl, thienothiaphenyl or o-diazanaphthyl.

[0114] arylene and heteroarylene correspond to divalent groups in aryl and heteroaryl structures, respectively.

[0115] In the terms "alkylsilyl" or "arylsilyl," the number of alkyl or aryl groups can be one to three. "alkylboryl" includes monoalkylboryl and dialkylboryl, "arylboryl" includes monoarylboryl and diarylboryl, and "arylphosphine" includes monoarylphosphine and diarylphosphine. In the terms alkylsilyl, arylsilyl, alkylboryl, arylboryl, and arylphosphine, the defined carbon number refers to the total number of carbons in the group.

[0116] The term "adjacent" refers to two groups or atoms that are directly bonded together, or two groups or atoms that are directly adjacent substituents (i.e., the two substituent sites are directly connected, rather than indirectly connected through other atoms or groups).

[0117] The phrase "a to b carbons of R group with substituted or unsubstituted carbons" refers to the number of carbons when the R group is unsubstituted, excluding the number of carbons of the substituents when the R group is substituted.

[0118] "Substitution" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents). Unless otherwise defined, this invention also includes the substitution of one or more hydrogen atoms by groups formed by the connection of two or more of the substituents described above.

[0119] Maximum number substitution refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0120] The following embodiments are merely for the purpose of understanding the technical invention and should not be regarded as specific limitations of the present invention.

[0121] Unless otherwise specified, the raw materials, reagents or devices used in this invention can be obtained from conventional commercial sources or by existing known methods.

[0122] Example 1: Synthesis of Compound A3

[0123]

[0124] The specific method for synthesizing compound A3 is as follows:

[0125] S1. Compound A3-1 (2-bromo-6-chloronaphthalene, 15.00 g, 62.11 mmol), compound A3-2 (phenylboronic acid, 7.57 g, 62.11 mmol), tetra(triphenylphosphine)palladium (0.72 g, 0.62 mmol), potassium carbonate (21.46 g, 155.27 mmol), tetrahydrofuran (220 mL), and deionized water (75 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent) until compound A3-1 was completely consumed.

[0126] Cool to room temperature, concentrate under reduced pressure to remove some of the solvent, add ethyl acetate (200 mL), wash three times with deionized water (100 mL × 3), separate the contents, dry-pick up the sample onto a silica gel column, and perform silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain a white solid, compound A3-3 (11.05 g, purity: 99.63%, yield: 74.39%), mass spectrometry: 239.05 (M+H).

[0127] S2. Compound A3-3 (9.87 g, 41.36 mmol), compound A3-4 (3-aminobiphenyl 3.50 g, 20.68 mmol), tris(dibenzylideneacetone)dipalladium (0.38 g, 0.41 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.39 g, 0.83 mmol), sodium tert-butoxide (4.97 g, 51.71 mmol), and toluene (350 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 90 °C and reacted for 4 hours. The reaction was monitored by TLC (dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A3-3 was completely consumed.

[0128] The solution was cooled to 60°C, concentrated under reduced pressure to remove the solvent, and ethyl acetate (300 mL) was added. The solution was washed three times with deionized water (100 mL × 3), separated, and loaded onto a silica gel column using a dry chromatography method. The solution was purified by silica gel column chromatography (200–300 mesh silica gel, dichloromethane: n-hexane = 1:5 as eluent). After elution, the solution was concentrated under reduced pressure at 60°C for 1 hour to obtain a white solid, which was compound A3 (7.35 g, purity: 99.97%, yield: 72.26%). The crude compound A3 was purified by sublimation to obtain sublimed pure compound A3 (4.83 g, purity: 99.99%, yield: 65.71%), mass spectrometry: 574.35 (M+H).

[0129] The proton NMR data for compound A3 are as follows: 1H NMR (400MHz, CDCl3) δ7.84 (dd, J=14.9, 3.0Hz, 2H), 7.78-7.72 (m, 6H), 7.60–7.45 (m, 9H), 7.45–7.36 ( m,5H),7.32(t,J=3.0Hz,2H),7.27(t,J=3.0Hz,1H),7.21-7.15(m,4H),7.11(dd,J=15.0,3.1Hz,2H).

[0130] Example 2 Synthesis of compound A21

[0131]

[0132] The synthesis and purification process of compound A21 was the same as that of compound A3, except that compound A3-4 was replaced with 4-(1-naphthyl)aniline (CAS: 125404-00-4) to obtain compound A21 (yield: 76.51%), mass spectrometry: 624.26 (M+H).

[0133] The proton NMR data for compound A21 are as follows: 1 H NMR(400MHz, CDCl3)δ8.95(dd,J=14.3,3.7Hz,1H),8.54–8.46(m,1H),7.92–7.87(m,1H),7.84(dd,J=14.9,3.0Hz, 2H),7.80–7.72(m,6H),7.59–7.45(m,8H),7.45–7.30(m,10H),7.17(t,J=2.9Hz,2H),7.13(dd,J=15.0,3.1Hz,2H).

[0134] Example 3 Synthesis of compound A36

[0135]

[0136] The synthesis and purification process of compound A36 was the same as that of compound A3, except that compound A3-4 was replaced with A36-3 (CAS: 2244205-89-6) to obtain compound A36 (yield: 68.79%), mass spectrometry: 664.26 (M+H).

[0137] The proton NMR data for compound A36 are as follows: 1H NMR(400MHz, CDCl3) δ7.98(dd,J=14.5,3.4Hz,1H),7.84(dd,J=14.9,3.0Hz,2H),7.79(dd,J=14.7,3.2Hz,4H), 7.62–7.51(m,8H),7.51–7.45(m,4H),7.44–7.28(m,10H),7.16(t,J=2.9Hz,2H),7.09(dd,J=15.0,3.1Hz,2H).

[0138] Example 4 Synthesis of compound A62

[0139]

[0140] The synthesis and purification methods of compound A62 were the same as those of compound A3, except that compound 3-2 was replaced with A62-2 (CAS: 1765-93-1) and compound A3-4 was replaced with 4-(1-naphthyl)aniline (CAS: 2244205-89-6) to obtain compound A62 (yield: 74.01%), mass spectrometry: 660.24 (M+H).

[0141] The proton NMR data for compound A62 are as follows: 1 H NMR(400MHz, CDCl3)δ8.95(dd,J=14.3,3.7Hz,1H),8.53–8.47(m,1H),7.92–7.87(m,1H),7.84(dd,J=14.9,3.0H z,2H),7.80–7.75(m,2H),7.59–7.48(m,8H),7.43–7.31(m,8H),7.17(dd,J=5.3,2.4Hz,3H),7.14–7.08(m,5H).

[0142] Example 5: Synthesis of Compound A277

[0143]

[0144] The synthesis and purification process of compound A277 was the same as that of compound A3, except that compound A3-4 was replaced with D9-4-aminobiphenyl (CAS: 344298-96-0) to obtain compound A277 (yield: 68.60%), mass spectrometry: 583.30 (M+H).

[0145] The proton NMR data for compound A277 are as follows: 1H NMR(400MHz, CDCl3) δ7.84(dd,J=14.9,3.0Hz,2H),7.75(dd,J=14.8,3.2Hz,4H),7.56(dd,J=15.0,2.9Hz,2H),7 .53–7.45(m,4H),7.45–7.37(m,4H),7.32(t,J=3.0Hz,2H),7.17(t,J=2.9Hz,2H),7.11(dd,J=15.0,3.1Hz,2H).

[0146] Example 6 Synthesis of compound A52

[0147]

[0148] The specific method for synthesizing compound A52 is as follows:

[0149] S1. Compound A52-1 (5-bromo-2-naphthylamine, 62.11 mmol), compound A3-2 (phenylboronic acid, 7.57 g, 62.11 mmol), tetra(triphenylphosphine)palladium (0.72 g, 0.62 mmol), potassium carbonate (21.46 g, 155.27 mmol), tetrahydrofuran (220 mL), and deionized water (75 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent) until compound A52-1 was completely consumed.

[0150] Cool to room temperature, concentrate under reduced pressure to remove some of the solvent, add ethyl acetate (200 mL), wash three times with deionized water (100 mL × 3), separate the contents, dry-pick up the sample onto a silica gel column, and perform silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain a white solid as compound A52-2 (10.65 g, purity: 99.39%, yield: 71.92%), mass spectrometry: 220.10 (M+H).

[0151] S2. Compound A3-3 (10.00 g, 41.89 mmol), compound 52-2 (9.19 g, 41.89 mmol), tris(dibenzylacetone)palladium (0.38 g, 0.41 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.39 g, 0.83 mmol), sodium tert-butoxide (4.97 g, 51.71 mmol), and toluene (350 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 90 °C and reacted for 4 hours. The reaction was monitored by TLC (dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A3-3 was completely consumed.

[0152] The solution was cooled to 60°C, concentrated under reduced pressure to remove the solvent, and ethyl acetate (300 mL) was added. The solution was washed three times with deionized water (100 mL × 3). The solution was separated, and the sample was loaded onto a silica gel column using a dry chromatography method. The solution was purified by silica gel column chromatography (200–300 mesh silica gel, dichloromethane: n-hexane = 1:5 as eluent). After elution, the solution was concentrated under reduced pressure at 60°C for 1 hour to obtain a white solid, which was compound A52-3 (13.95 g, purity: 99.62%, yield: 72.57%). Mass spectrometry: 422.18 (M+H).

[0153] S3. Compound A52-3 (10.00 g, 23.72 mmol), compound 52-4 (7.64 g, 23.72 mmol, 4-bromo-9-phenyl-9H-fluorene, CAS: 2128245-42-9), tris(dibenzylacetone)palladium (0.21 g, 0.23 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.30 g, 0.67 mmol), cesium carbonate (19.32 g, 59.31 mmol), and toluene (350 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 90 °C and reacted for 4 hours. The reaction was monitored by TLC (dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A52-3 was completely consumed.

[0154] The solution was cooled to 60°C, concentrated under reduced pressure to remove the solvent, and ethyl acetate (300 mL) was added. The solution was washed three times with deionized water (100 mL × 3). The solution was separated, and the mixture was loaded onto a silica gel column using a dry chromatography method. The solution was purified by silica gel column chromatography (200–300 mesh silica gel, dichloromethane: n-hexane = 1:5 as eluent). After elution, the solution was concentrated under reduced pressure at 60°C for 1 hour to obtain a white solid, which was compound A52 (10.74 g, purity: 99.91%, yield: 68.31%). The crude compound A52 was purified by sublimation to obtain sublimed pure compound A52 (7.85 g, purity: 99.95%, yield: 73.09%), mass spectrometry: 663.27 (M+H).

[0155] The proton NMR data for compound A52 are as follows: 1 H NMR(400MHz, CDCl3)δ8.31(dd,J=14.8,3.1Hz,1H),8.22–8.16(m,1H),7.84(dd,J =14.9,3.0Hz,1H),7.81–7.71(m,5H),7.67–7.58(m,4H),7.58–7.45(m,7H),7.45 –7.36(m,5H),7.32(t,J=3.0Hz,1H),7.23–7.15(m,5H),7.11(dd,J=15.0,3.1Hz, 1H), 7.01 (t, J=14.9Hz, 1H), 6.88 (t, J=3.0Hz, 1H), 6.40 (dd, J=15.0, 3.1Hz, 1H).

[0156] Example 7 Synthesis of compound A92

[0157]

[0158] The synthesis and purification process of compound A92 was based on the same method as that of compound A52, with the following differences: reaction S1 involved the reaction of 1-chloro-6-bromonaphthalene with phenylboronic acid; reaction S2 involved the reaction of 6-chloro-1-phenylnaphthalene with 4-pyridin-3-ylaniline (CAS: 82261-42-5); and reaction S3 involved the reaction of the product of S2 with compound A3-3. The resulting compound A92 was obtained (yield: 67.48%), mass spectrometry: 575.24 (M+H).

[0159] The proton NMR data for compound A92 are as follows: 1 H NMR (400MHz, CDCl3) δ9.26–9.21(m,1H),8.74–8.67(m,1H),8.36-8.30(m,1H),8.19(d,J=15.0Hz,1H),8.14(t,J=3.0Hz,1H),7.84(dd,J=14.9,3.0Hz ,1H),7.75(dd,J=14.7,3.2Hz,4H),7.69–7.51(m,6H),7.50–7.34(m,11H), 7.32(t,J=3.0Hz,1H), 7.17(t,J=2.9Hz,1H), 7.11(dd,J=15.0,3.1Hz,1H).

[0160] Example 8 Synthesis of compound A114

[0161]

[0162]

[0163] The synthesis and purification process of compound A114 was based on the same method as that of compound A52. The difference was that compound A114-3 was prepared first. In this process, reaction S1 involved the reaction of 3-bromo-7-chlorodibenzo[B,D]furan (CAS: 2244910-28-7) with compound A114-3, reaction S2 involved the reaction of aniline with the product of S1, and reaction S3 involved the reaction of the product of S2 with 2-chloro-6-phenylnaphthalene to obtain compound A114 (yield: 67.39%), mass spectrometry: 664.26 (M+H).

[0164] The proton NMR data for compound A114 are as follows: 1 H NMR (400MHz, CDCl3) δ8.51(dd,J=13.1,4.8Hz,1H),8.17(t,J=2.7Hz,1H),8.07(d,J=15.0Hz,1H ),8.03(d,J=3.1Hz,1H),7.95(d,J=2.9Hz,1H),7.84(dd,J=14.9,3.0Hz,1H),7.81–7.70(m,7H), 7.56(dd,J=15.0,6.9Hz,3H),7.53–7.45(m,4H),7.41(dd,J=17.7,8.1Hz,4H),7.32(t,J=3.0Hz, 1H),7.24(dd,J=15.6,12.6Hz,3H),7.17(t,J=2.9Hz,1H),7.14-7.05(m,3H),7.04–6.95(m,1H).

[0165] Example 9 Synthesis of compound A169

[0166]

[0167] The synthesis and purification methods of compound A169 were referenced from those of compound A52, with the following differences: reaction S1 involved the reaction of 3-bromo-7-chloroquinoline (CAS: 84973-05-7) with phenylboronic acid; reaction S2 involved the reaction of 4-(1-adamantyl)aniline (CAS: 1459-48-9) with the product of S1; and reaction S3 involved the reaction of the product of S2 with 2-chloro-6-phenylnaphthalene. Compound A169 was obtained (yield: 65.14%), mass spectrometry: 633.32 (M+H).

[0168] The proton NMR data for compound A169 are as follows: 1H NMR (400MHz, CDCl3) δ8.37(dd,J=15.0,3.1Hz,1H),8.31(t,J=2.9Hz,1H),7.99(d,J=2.9Hz,1H),7.84(dd,J=14.9,3.0Hz,1H),7.79–7.72(m,2H), 7.56(dd,J=15.0,2.9Hz,1H),7.54–7.36(m,9H),7.32(t,J=3.0Hz,1H),7 .23–7.16(m,3H),7.10(s,5H),2.06–1.97(m,9H),1.72(t,J=6.2Hz,6H).

[0169] Example 10 Synthesis of Compound A231

[0170]

[0171] The synthesis and purification process of compound A231 was based on the same method as that of compound A52, with the following differences: reaction S1 involved the reaction of 6-bromo-2-aminonaphthalene with pyridine-3-boronic acid (CAS: 1692-25-7); reaction S2 involved the reaction of 3-chlorobenzophenanthrene (CAS: 36288-21-8) with the product of S1; and reaction S3 involved the reaction of the product of S2 with 2-chloro-6-phenylnaphthalene. Compound A231 was obtained (yield: 70.83%), mass spectrometry: 649.26 (M+H).

[0172] The proton NMR data for compound A231 are as follows: 1 H NMR (400MHz, CDCl3) δ9.26–9.22(m,1H),8.92(d,J=15.0Hz,1H),8.84(dd,J=14.1,3.8Hz,1H),8.75– 8.67(m,2H),8.33(dt,J=15.0,3.0Hz,1H),8.08(ddd,J=15.0,9.5,2.9Hz,2H),7.96–7.87(m,2H),7. 84(dd,J=14.9,3.0Hz,1H),7.81–7.72(m,4H),7.72–7.61(m,3H),7.55(ddd,J=14.9,9.7,2.9Hz,2H) ,7.52–7.36(m,8H),7.32(t,J=3.0Hz,1H),7.17(t,J=2.9Hz,1H),7.11(ddd,J=9.1,6.0,3.1Hz,2H).

[0173] Example 11 Synthesis of compound A273

[0174]

[0175] The synthesis and purification process of compound A273 was based on the same method as that of compound A52, with the following differences: reaction S1 involved the reaction of 3-(6-chloro-2-naphthyl)-pyridine with 4-chlorophenylboronic acid; reaction S2 involved the reaction of 3-aminobiphenyl with the product of S1; and reaction S3 involved the reaction of the product of S2 with 1-(3-chlorophenyl)-6-phenylnaphthalene. Compound A273 was obtained (yield: 67.54%), mass spectrometry: 727.30 (M+H).

[0176] The proton NMR data for compound A273 are as follows: 1 H NMR (400MHz, CDCl3) δ9.26–9.23(m,1H),8.73–8.67(m,1H),8.51(dd,J=13.1,4. 8Hz,1H),8.36-8.30(m,1H),8.16(t,J=2.8Hz,1H),8.07(d,J=15.0Hz,1H),7.99( dd,J=15.0,2.9Hz,1H),7.94–7.88(m,1H),7.81–7.71(m,8H),7.59–7.51(m,6H) ,7.51–7.46(m,4H),7.44–7.35(m,6H),7.27(t,J=3.0Hz,2H),7.21-7.14(m,4H).

[0177] Example 12 Synthesis of compound A108

[0178]

[0179]

[0180] The synthesis and purification process of compound A108 is based on the synthesis and purification methods of compound A52. The difference is that A108-2 and A108-4 are prepared first. In reaction S1, A108-2 reacts with 4-aminobiphenyl. In reaction S2, A108-4 reacts with the product of S1. In reaction S3, the product of S2 reacts with A108-4 to obtain compound A108 (yield: 72.13%), mass spectrometry: 794.46 (M+H).

[0181] The proton NMR data for compound A108 are as follows: 1H NMR (400MHz, CDCl3) δ8.19(d,J=15.0Hz,1H),8.14(t,J=2.9Hz,1H),7.84(dd,J=15.0,3.0Hz,1H),7.75(dd,J=14.8,3.2Hz,2H),7 .69–7.61(m,1H),7.61–7.34(m,16H),7.32(t,J=3.0Hz,1H),7.17(t,J=2.9Hz,1H),7.14–7.06(m,3H),1.71(s,8H),0.91(s,24H).

[0182] Example 13 Synthesis of Compound A150

[0183]

[0184] The synthesis and purification methods of compound A150 were the same as those of compound A52, except that reaction S1 involved the reaction of 1-chloro-6-(1-naphthyl)naphthalene with aniline, reaction S2 involved the reaction of A108-4 with the product of S1, and reaction S3 involved the reaction of the product of S2 with 1-chloro-6-(2-naphthyl)naphthalene, to obtain compound A150 (yield: 76.28%), mass spectrometry: 598.25 (M+H).

[0185] The proton NMR data for compound A150 are as follows: 1 H NMR (400MHz, CDCl3) δ8.95 (dd, J=14.2, 3.7Hz, 1H), 8.53–8.47 (m, 1H), 8.24–8 .16(m,3H),8.14(t,J=3.0Hz,1H),8.12–8.04(m,2H),7.99(dd,J=15.0,2.9Hz, 1H),7.93–7.86(m,1H),7.81–7.75(m,2H),7.70–7.53(m,7H),7.51–7.44(m,4H ),7.42–7.30(m,3H),7.29–7.19(m,2H),7.12–7.05(m,2H),7.04–6.96(m,1H).

[0186] Example 14 Synthesis of Compound A285

[0187]

[0188] Compound A21 (15.00 g, 24.05 mmol), platinum dioxide (0.66 g, 2.89 mmol), and heavy water (300 mL) were added to a 500 mL pressure-resistant reactor, purged three times with argon gas, heated to 250 °C, and reacted for 20 hours.

[0189] The sample was cooled to room temperature, and 300 mL of dichloromethane was added. The sample was washed three times with deionized water (100 mL × 3), separated, and loaded onto a silica gel column using a dry chromatography method. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, dichloromethane:n-hexane = 1:5 as eluent). After elution, the sample was concentrated under reduced pressure at 60 °C for 1 hour to obtain the target compound A285 (8.49 g, purity: 99.91%, yield: 53.74%). The crude compound A285 was then purified by sublimation to obtain sublimed pure compound A285 (5.72 g, purity: 99.94%, yield: 67.37%), mass spectrometry: 657.47 (M+H).

[0190] Example 15 Synthesis of compound A311

[0191]

[0192] The synthesis and purification process of compound A311 was the same as that of compound A52. Compound A311 (8.02 g, purity: 99.95%, yield: 74.19%) was obtained and its mass spectrometry result was 715.27 (M+H).

[0193] The proton NMR data for compound A311 are as follows: 1 H NMR (400MHz, CDCl3) δ8.88(d,J=3.1Hz,1H),8.31(dd,J=14.8,3.1Hz,2H),8.21–8.15(m,2H),8.14–8.01(m,3H),7.92(dd,J =15.0,2.9Hz,1H),7.83–7.70(m,8H),7.68–7.60(m,5H),7.54–7.39(m,8H),7.20(d,J=15.0Hz,2H),6.88(t,J=3.0Hz,2H).

[0194] Applications of organic electroluminescent devices

[0195] 1. Structure and fabrication of organic electroluminescent devices

[0196] The aromatic amine compounds of the present invention are combined with a second main compound B to form a composition, and compounds B25, B54, B71, B80, B96, B104 and B128 therein are prepared according to the method in patent CN119490493 A.

[0197] The aromatic amine compounds and compositions of the present invention are applied to the preparation of organic electroluminescent devices, as shown in the appendix. Figure 1As shown, the organic electroluminescent device includes a glass substrate 1, an anode 2, a hole injection layer 3 (HIL), 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, all stacked together.

[0198] The specific fabrication method of organic electroluminescent devices is as follows:

[0199] A glass substrate 1 with an ITO transparent electrode (anode 2) on its surface is provided, and the thickness of the anode is 100 nm;

[0200] The glass substrate 1 was ultrasonically cleaned in ethanol for 10 minutes, then dried at 150°C, and then treated with N2Plasma for 30 minutes. Tris(dicyanomethylene)cyclopropane (NDP-9) and compound HTM 1 were co-deposited on the surface of the anode 2 to form HIL, wherein the weight ratio of compound NDP-9 to compound HTM 1 was 97:3, and the thickness of HIL was 5 nm.

[0201] Compound HTM1 was deposited on the surface of HIL to form HTL1, with a thickness of 60 nm.

[0202] Compound HTM2 was vapor-deposited on the surface of HTL1 to form HTL2, which had a thickness of 10 nm.

[0203] The host material and the red light dopant are co-deposited on the surface of HTL2 to form the light-emitting layer 6, wherein the thickness of the light-emitting layer 6 is 40 nm, and the weight ratio of the host material and the red light dopant is 97%:3%. The host material is the aromatic amine compound, composition or comparative compound 1-3 of this application. The specific combination is listed in Table 1 and Table 2 of the performance test results below.

[0204] ETL material and LiQ are vapor-deposited on the surface of the light-emitting layer 6 to form an ETL, wherein the weight ratio of ETL material to LiQ is 50:50 and the thickness of the ETL is 35nm.

[0205] LiQ is deposited on the surface of ETL to form EIL, and the thickness of EIL is 1 nm.

[0206] Metals Mg and Ag are co-deposited on the surface of EIL to form cathode 9, wherein the weight ratio of Mg to Ag is 1:9 and the thickness of cathode 9 is 100 nm, thus obtaining an organic electroluminescent device.

[0207] The structural formulas of NDP-9, HTM1, HTM2, ETL materials, red light-doped materials, LiQ, RH-N, and comparative compounds 1-3 are as follows:

[0208]

[0209] 2. Device testing conditions and results

[0210] The above-mentioned organic electroluminescent devices were subjected to device performance testing. The compounds prepared in this application and comparative compounds 1-3 were used as host materials for comparison. A constant current power supply (Keithley 2400) was used, and a fixed current density was applied to the light-emitting element. The emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, at 10 mA / cm²... 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm². 2 The lifetime of the LT95 device was tested. The results are shown in Tables 1 and 2 below.

[0211] Application Examples 1-6 and Comparative Examples 1-3 used aromatic amine compounds or comparative compounds as the host material to co-deposit luminescent layers with red light doping materials. The host material of the luminescent layer and the device performance test data are shown in Table 1.

[0212] Table 1

[0213]

[0214]

[0215] Application Examples 7-23 and Comparative Examples 4-6 used a dual-substrate material and a red light-doping material to co-deposit the luminescent layer. The test data of the luminescent layer substrate material and device performance are shown in Table 2.

[0216] Table 2

[0217]

[0218]

[0219] In Table 2, the weight ratios of the first and second main bodies in Application Examples 22 and 23 are 2:8 and 8:2, respectively. Apart from these, in the other embodiments and comparative examples, the weight ratio of the two main body materials is 1:1.

[0220] As can be seen from Tables 1-2, the devices prepared by the compounds and compositions in the embodiments of this application have significantly better device lifetime and luminous efficiency than the devices prepared by the compounds and compositions in the comparative examples. In Table 1, the device lifetime of the aromatic amine compounds of this invention is greater than 350h, and the voltage is significantly lower than that of the devices prepared by the compounds and compositions in the comparative examples. As a single-host red light material, the compounds of this application have lower voltage, higher current efficiency and longer lifetime than the comparative compounds.

[0221] In Table 2, when the compound of this application is paired with the N-type second host compound as a dual host material, it greatly improves the efficiency and lifetime of the device by balancing the hole and electron transport rates and widening the exciton recombination region in the light-emitting layer, compared with comparative compounds 1-3.

[0222] Therefore, the compound material of this application possesses advantages such as high optical and electrical stability, low driving voltage, high luminous efficiency, and long device lifetime, making it suitable as a host material for 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 this application has the potential for application in the AMOLED industry.

[0223] The above description represents the preferred embodiments of the present invention. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of the present invention, and these improvements and modifications are also considered to be within the scope of protection of the present invention.

Claims

1. An aromatic amine compound, characterized in that, The structural formula of the aromatic amine compound is shown in formula (1): Among them, X1-X 28 Each is independently selected as CR0 or N; R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamino; when R0 is C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, or C2-C40 alkynyl, adjacent R0s may be linked to form a fused ring; L1 and L2 are selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups; Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazoyl, substituted or unsubstituted fluoranthraceneyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthozoyl, substituted or unsubstituted phenanthoxazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, or substituted or unsubstituted benzocarbazole; In L1, L2, or Ar1, the substitutions each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, deuterium-substituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, deuterium-substituted C3-C30 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions; The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge.

2. The aromatic amine compound according to claim 1, characterized in that, The structural formula of the aromatic amine compound is selected from any of the structures shown in formula (3) to formula (10): Where e is an integer from 0 to 4; if e is an integer from 2 to 4, then each R0 may be the same or different.

3. The aromatic amine compound according to claim 2, characterized in that, The structural formula of the aromatic amine compound is selected from any of the structures shown in formula (11) to formula (18): Where e is an integer from 0 to 4; if e is an integer from 2 to 4, then each R0 can be the same or different.

4. The aromatic amine compound according to any one of claims 1-3, characterized in that, X1-X 28 The number of choices for N is an integer between 0 and 5; And / or, L1 and L2 are selected from single-bonded, substituted or unsubstituted C6-C20 arylene groups or substituted or unsubstituted C3-C20 heteroarylene groups; And / or, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazole, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthazolyl, substituted or unsubstituted phenanthazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted The substituted benzonaphthofuran, or the substituted or unsubstituted benzocarbazole, wherein each substitution independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C12 cycloalkyl, deuterated C6-C20 aryl, C1-C6 alkyl-substituted or unsubstituted C6-C20 aryl, deuterated C3-C20 heteroaryl, or C1-C6 alkyl-substituted or unsubstituted C3-C20 heteroaryl, the number of substitutions being from monosubstituted to the maximum number of substitutions; And / or, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl, or C6-C30 arylamino; when R0 is a C1-C20 alkyl, adjacent R0s may be linked to form a fused ring; And / or, in L1 or L2, each of the substitutions independently represents being substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C20 aryl substituted or unsubstituted C1-C6 alkyl, or C3-C20 heteroaryl substituted or unsubstituted C1-C6 alkyl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions.

5. The aromatic amine compound according to claim 4, characterized in that, In Ar1, the substitution independently represents substitution by deuterium, fluorine, cyano, tert-butyl, pyridyl, phenyl, tolyl, deuterated phenyl, naphthyl, deuterated naphthyl, dibenzothiophene, dibenzofuranyl, deuterated dibenzofuranyl, adamantyl, carbazole, cyclohexyl, phenylbenzoxazolyl, phenylnaphthoxazolyl, or phenylphenanthrenexazolyl; And / or, L1 and L2 are independently selected from one of the following structural formulas: single bond, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted naphthylene, or deuterated or unsubstituted pyridylene. And / or, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, and C6-C20 aryl; when R0 is C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, or C2-C10 alkynyl, adjacent R0s may be connected to form a four-membered ring, a five-membered ring, a six-membered ring, or a seven-membered ring.

6. The aromatic amine compound according to any one of claims 1-3, characterized in that, Formula (1) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine:

7. A composition, characterized in that: The composition comprises a first host compound and a second host compound, wherein the first host compound is selected from the aromatic amine compounds as described in any one of claims 1-6, and the second host compound has the structure shown in formula (2): In the formula, ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, or substituted or unsubstituted phenanthrene rings; X is selected from NR a CR b R c Or oxalic elements; Z1, Z2, and Z3 are each independently selected from N or CR. d ; R a R b R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, C3-C30 alkylsilyl, or C6-C30 arylsilyl; or, R b and R c Connect them into a ring; R1, R d Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphinyl or C6-C60 arylamine; a is an integer selected from 0 to 4; L3-L5 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene; Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6-C36 aryl or substituted or unsubstituted C2-C36 heteroaryl; The substitutions in rings A, L3-L5, Ar2, and Ar3 are independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphinyl, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions; In formula (2), the heteroatom in the heteroaryl, heteroaryl, heteroalkyl or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si and Ge.

8. The composition according to claim 7, characterized in that: Each of L3-L5 is independently selected from single-bonded, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C6-C20 heteroarylene. And / or, the Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6-C26 aryl or substituted or unsubstituted C2-C26 heteroaryl; And / or, Z1, Z2, and Z3 are all selected from N, or one of them is selected from CR. d The other two are selected from N; And / or, the R1, R d Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl or C6-C20 arylamino; And / or, the R a R b R c Each is independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C6 alkyl-substituted or unsubstituted C6-C20 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C20 heteroaryl, C3-C20 alkylsilyl, or C6-C20 arylsilyl; or, R b and R c Connect them into a ring; And / or, in the rings A, L3-L5, Ar2 and Ar3, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C20 aryl or C1-C6 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

9. The composition according to claim 7, characterized in that: Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted naphthazolyl, substituted or unsubstituted phenanthazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, or substituted or unsubstituted benzocarbazole or a combination thereof; The Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, or combinations thereof.

10. The composition according to claim 7, characterized in that: The second host compound satisfies at least one of the following conditions: (1) Z1, Z2, and Z3 are all selected from N; or one of them is selected from CH and the other two are selected from N; (2) Each of L3-L5 is independently selected from single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted phenanthoxazolyl or substituted or unsubstituted phenanthiazolyl. (3) Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo[a]phenanthryl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzo[a]oxazolyl, substituted or unsubstituted benzo[a]naphthofuranyl, substituted or unsubstituted benzo[a]phenanthrylfuranyl, substituted or unsubstituted naphthozolyl, substituted or unsubstituted phenanthrylazolyl, substituted or unsubstituted phenanthrethiazolyl; (4) The R1 is selected from hydrogen or deuterium; (5)X is selected from NR a CR b R c , O or S, where R a R b R c Each is independently selected from methyl or phenyl; or R b and R c The linkage forms a fluorene group; (6) In the rings A, L3-L5, Ar2 and Ar3, the substitution is independently substituted by at least one of deuterium, phenyl, biphenyl, naphthyl, C1-C6 hydrocarbon group substituted or unsubstituted benzoxazole group, C1-C6 hydrocarbon group substituted or unsubstituted naphthazole group, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

11. The composition according to claim 7, characterized in that, Formula (2) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine:

12. The composition according to claim 7, characterized in that, The mass ratio of the first main compound to the second main compound is 1:(0.25 to 4).

13. An organic electroluminescent device, characterized in that, It includes an anode, a cathode, and a functional layer between the anode layer and the cathode layer, said functional layer comprising an aromatic amine compound as described in any one of claims 1-6, or a composition as described in any one of claims 7-12.

14. A semiconductor device, characterized in that, It comprises an aromatic amine compound as described in any one of claims 1-6, or a composition as described in any one of claims 7-12, or an organic electroluminescent device as described in claim 13.

Images