Aromatic amine compounds, electroluminescent device and display apparatus

Abstract

Aromatic amine compounds, an electroluminescent device and a display apparatus, belonging to the technical field of display. The aromatic amine compounds can improve the performance of electroluminescent devices.

Description

Aromatic amine compound, electroluminescent device and display device

[0001] Cross-references

[0002] The present disclosure claims priority to Chinese patent application No. 202311220949.8 filed on September 20, 2023, entitled “Aromatic amine compound for use in organic electroluminescent devices, preparation method and application thereof”, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to the field of display technology, and in particular to an aromatic amine compound, an electroluminescent device, and a display apparatus. Background Art

[0004] Electroluminescent devices (ELDs) are capable of emitting light when driven by an electric current. They typically include at least a stacked anode, a functional layer, and a cathode. Holes provided by the anode and electrons provided by the cathode recombine in the functional layer, causing it to emit light.

[0005] Compared with traditional liquid crystal displays, as a new generation of display technology, electroluminescent devices have the advantages of self-luminescence, wide viewing angle, low power consumption, high response rate, and full color. They have extremely high R&D value and broad application prospects.

[0006] It should be noted that the information disclosed in the above background technology section is only used to enhance the understanding of the background of the present disclosure, and therefore may include information that does not constitute prior art known to ordinary technicians in the field.

[0007] Summary of the Invention

[0008] The purpose of the present disclosure is to overcome the deficiencies of the above-mentioned prior art, provide an aromatic amine compound, an electroluminescent device and a display device, and improve the performance of the electroluminescent device.

[0009] According to a first aspect of the present disclosure, an aromatic amine compound is provided, wherein the structural formula of the aromatic amine compound is as shown in Chemical Formula A or Chemical Formula B:

[0010] wherein L1 is selected from a single bond, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0011] Q1, Q2, and Q3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and at least one of Q1, Q2, and Q3 contains at least one of the groups represented by the following chemical formulas P1 to P6:

[0012] wherein Ar4 is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkane naphthyl group having 14 to 30 carbon atoms;

[0013] R4 and R5 are the same or different and are independently selected from any one of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

[0014] R6 is C(R7R8); R7 and R8 are each independently selected from hydrogen, deuterium, fluorine, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;

[0015] Said p represents an integer of 0-6; when p is greater than 1, any two R4 are the same or different;

[0016] Said q represents an integer of 0-4; when q is greater than 1, any two R5 are the same or different;

[0017] The x represents an integer from 0 to 3; when x is greater than 1, any two R5 are the same or different;

[0018] k is an integer from 2 to 4; any two R7s are the same or different; any two R8s are the same or different;

[0019] When L1, Q1, Q2, Q3, R4, R5, R7, R8, and Ar4 have substituents, the substituents of L1, Q1, Q2, Q3, R4, R5, R7, R8, and Ar4 may be the same or different and are independently selected from any one of deuterium, halogen, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms;

[0020] Represents a connection key.

[0021] According to another aspect of the present disclosure, an electroluminescent device is provided, wherein the electroluminescent device comprises an organic layer, and the organic layer comprises the aromatic amine compound.

[0022] According to yet another aspect of the present disclosure, a display device is provided, comprising the above-mentioned electroluminescent device.

[0023] It is to be understood that the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the disclosure. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] The accompanying drawings are incorporated into and constitute a part of the specification, illustrate embodiments consistent with the present disclosure, and together with the specification, are used to explain the principles of the present disclosure. Obviously, the drawings described below are only some embodiments of the present disclosure, and those skilled in the art can derive other drawings based on these drawings without inventive effort.

[0025] FIG1 is a schematic structural diagram of an electroluminescent device in one embodiment of the present disclosure.

[0026] FIG2 is a schematic diagram of a partial structure of a display panel in one embodiment of the present disclosure. DETAILED DESCRIPTION

[0027] Example embodiments will now be described more fully with reference to the accompanying drawings. However, the example embodiments can be implemented in many forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concepts of the example embodiments to those skilled in the art. Like reference numerals in the figures represent identical or similar structures, and thus their detailed descriptions will be omitted. Furthermore, the figures are merely schematic illustrations of the present disclosure and are not necessarily drawn to scale.

[0028] Although relative terms such as "upper" and "lower" are used in this specification to describe the relationship of one illustrated component to another, these terms are used herein for convenience only, such as in accordance with the orientation of the illustrations in the accompanying drawings. It will be understood that if the illustrated device were flipped upside down, the component described as "upper" would become the component "lower." When a structure is referred to as "on" another structure, this may mean that the structure is integrally formed with the other structure, that the structure is "directly" disposed on the other structure, or that the structure is "indirectly" disposed on the other structure via the other structure.

[0029] The terms "a", "an", "the", "said" and "at least one" are used to indicate the presence of one or more elements / components / etc.; the terms "including" and "having" are used to express open-ended inclusion and mean that additional elements / components / etc. may be present in addition to the listed elements / components / etc.; the terms "first", "second" and "third" etc. are used only as labels and are not intended to limit the quantity of their objects.

[0030] Example embodiments will now be described more fully with reference to the accompanying drawings. However, the example embodiments can be implemented in many forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concepts of the example embodiments to those skilled in the art. Like reference numerals in the figures represent identical or similar structures, and thus their detailed descriptions will be omitted. Furthermore, the figures are merely schematic illustrations of the present disclosure and are not necessarily drawn to scale.

[0031] In this disclosure, the description “… are independently selected from” should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, “ Wherein, each q' is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q' substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q' substituents R" on each benzene ring of biphenyl, and the number q' of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0032] In this disclosure, a non-localized linker refers to a single bond extending from the ring system. It means that one end of the linker can be connected to any feasible position in the ring system through which the linker passes, and the other end is connected to the rest of the compound molecule.

[0033] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0034] For another example, as shown in the following formula (X'), the phenanthryl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0035] A non-positional substituent in the present disclosure refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring by a non-positional bond, and the meaning thereof includes any possible connection method shown in formulas (Y-1) to (Y-7).

[0036] In the present disclosure, in a substituted or unsubstituted G group with M carbon atoms, the carbon number of the G group is M, and the carbon number M does not take into account the carbon number of the substituent; for example, a methyl-substituted G group with M carbon atoms has a total carbon number of M+1. Correspondingly, in a substituted or unsubstituted aryl group with M carbon atoms or a substituted or unsubstituted heteroaryl group with M carbon atoms, the carbon number M does not take into account the carbon number of the substituent, but only takes into account the carbon number of the aromatic ring or heteroaromatic ring. For example, An aromatic group having 6 carbon atoms substituted with a methyl group; It is an unsubstituted arylene group having 12 carbon atoms.

[0037] In the present disclosure, when no specific definition is provided otherwise, "hetero" means that a functional group includes at least one heteroatom such as B, N, O, S, Se, Si or P, and the remaining atoms are carbon, hydrogen and deuterium. The unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.

[0038] In the present disclosure, "alkyl" may include straight-chain alkyl or branched-chain alkyl. An alkyl group may have 1 to 18 carbon atoms. In the present disclosure, a numerical range such as "1 to 18" refers to each integer in the given range; for example, "an alkyl group having 1 to 18 carbon atoms" refers to an alkyl group containing 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, or 18 carbon atoms. In some examples, the alkyl group may also be a small alkyl group having 1 to 5 carbon atoms.

[0039] Optionally, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include but are not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and pentyl.

[0040] In this disclosure, a cycloalkyl group refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 5 to 10 carbon atoms. In this disclosure, references to numerical ranges such as "a cycloalkyl group having 5 to 10 carbon atoms" refer to each integer within the given range; for example, "a cycloalkyl group having 5 to 10 carbon atoms" refers to a cycloalkyl group having 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, and 10 carbon atoms.

[0041] Alternatively, specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the like.

[0042] In the present disclosure, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon conjugation, or two or more condensed ring aryl groups connected by carbon-carbon conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon conjugation can also be considered as aryl of the present disclosure. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present disclosure, biphenyl, terphenyl, etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present disclosure, biphenyl can be understood as an aryl group substituted with a phenyl group, or as an unsubstituted aryl group. In the present disclosure, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0043] In the present disclosure, the substituted aryl group may be an aryl group in which one or more hydrogen atoms are substituted by a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, an alkoxy group or other groups.

[0044] In the present disclosure, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon conjugation, and any aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. For example, a heteroaryl group can include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazole group, a benzofuranyl ... The present invention also includes, but is not limited to, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc. Among them, thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of a polycyclic system type connected by carbon-carbon bonds.

[0045] In the present disclosure, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, an alkoxy group, or the like.

[0046] The present disclosure provides an aromatic amine compound that can be used in an electroluminescent device to improve the performance of the electroluminescent device. Specifically, at least a portion of the film layer in the electroluminescent device can utilize the aromatic amine compound provided by the present disclosure. For example, the electroluminescent device comprises an organic layer containing the aromatic amine compound provided by the present disclosure. The organic layer containing the aromatic amine compound provided by the present disclosure may also contain other components, or may contain only the aromatic amine compound provided by the embodiments of the present disclosure.

[0047] Optionally, the electroluminescent device may include at least two electrodes and a functional layer sandwiched between the two electrodes; the organic layer using the aromatic amine compound provided by the present disclosure in the electroluminescent device may be located in the functional layer between the two electrodes or outside the two electrodes to facilitate improving light extraction efficiency.

[0048] Alternatively, referring to FIG1 , the two electrodes (first electrode and second electrode) of the electroluminescent device can serve as the anode 1 and cathode 9 of the electroluminescent device, respectively. For example, the first electrode can serve as the anode, and the second electrode can serve as the cathode. The anode is used to provide holes to the functional layer, and the cathode is used to provide electrons to the functional layer. The electrons and holes recombine in the functional layer and emit light.

[0049] In the present disclosure, referring to FIG1 , the functional layer of the electroluminescent device may include a light-emitting functional layer 5, in which electrons and holes can recombine to form excitons, thereby causing the light-emitting functional layer to emit light. Optionally, the light-emitting functional layer may be a small molecule organic light-emitting functional layer, a macromolecular polymer light-emitting functional layer, or a quantum dot light-emitting functional layer. In this way, the electroluminescent device may be an organic light-emitting diode (OLED), a polymer light-emitting diode (PLED), or a quantum dot light-emitting diode (QLED).

[0050] In some embodiments of the present disclosure, referring to FIG1 , the functional layer of the electroluminescent device may further include a first functional layer (hole transport region) between the luminescent functional layer and the anode, and the first functional layer may inject the holes injected by the anode into the luminescent functional layer. For example, the first functional layer may include at least one of a hole injection layer 2, a hole transport layer 3, and an electron blocking layer 4. When the first functional layer includes a hole injection layer, a hole transport layer, and an electron blocking layer at the same time, the anode, the hole injection layer, the hole transport layer, the electron blocking layer, and the luminescent functional layer are stacked in sequence. Some aromatic amine compounds provided by the present disclosure are particularly suitable for application in the first functional layer, and can have at least one of the effects of improving the luminous efficiency of the electroluminescent device, improving the device life of the electroluminescent device, and reducing the driving voltage of the electroluminescent device.

[0051] In some embodiments of the present disclosure, referring to FIG1 , the functional layer of the electroluminescent device may further include a second functional layer (electron transport region) located between the light-emitting functional layer and the cathode, and the second functional layer may inject the electrons injected by the cathode into the light-emitting functional layer. For example, the second functional layer may include at least one of an electron injection layer 8, an electron transport layer 7, and a hole blocking layer 6. When the second functional layer includes an electron injection layer, an electron transport layer, and a hole blocking layer at the same time, the cathode, the electron injection layer, the electron transport layer, the hole blocking layer, and the light-emitting functional layer are stacked in sequence. In an embodiment of the present disclosure, the materials of the various film layers of the second functional layer may be selected as needed, and any film layer may be either an organic material, an inorganic material, or a mixture of organic and inorganic materials.

[0052] In some embodiments of the present disclosure, the electroluminescent device may also be a multi-stack structure, that is, a plurality of stacked functional layers may be provided between two electrodes, and a charge generation layer may be provided between two adjacent functional layers. In this embodiment, the charge generation layer may improve the electron-hole separation efficiency, thereby playing a role similar to that of an anode or a cathode. The charge generation layer is adjacent to the first functional layer and is capable of injecting holes into the first functional layer, thereby playing a role similar to that of an anode relative to the first functional layer; the charge generation layer is adjacent to the second functional layer and is capable of injecting electrons into the second functional layer, thereby playing a role similar to that of a cathode relative to the second functional layer. When the electroluminescent device has a multi-stack structure, the structures of any two functional layers may be the same or different.

[0053] In some embodiments of the present disclosure, referring to FIG1 , the electroluminescent device further includes a covering layer 10 disposed on the light-emitting side; some aromatic amine compounds provided in the present disclosure are particularly suitable for application in the covering layer to improve the light-emitting efficiency of the electroluminescent device or to improve the life of the electroluminescent device. In one example, the electroluminescent device includes a first electrode, a light-emitting functional layer, a second electrode, and a covering layer stacked in sequence; the covering layer is located on the light-emitting side of the electroluminescent device; the covering layer includes one or more aromatic amine compounds provided in the present disclosure. In this example, the second electrode can be a cathode or an anode. In other words, when the electroluminescent device emits light from the first electrode, the covering layer is disposed on the side of the first electrode away from the second electrode; conversely, when the electroluminescent device emits light from the second electrode, the covering layer is disposed on the side of the second electrode away from the first electrode.

[0054] In the example of Figure 1 , the electroluminescent device emits light from the cathode side. It is understood that in other examples of the present disclosure, the electroluminescent device may also emit light from the anode side.

[0055] An embodiment of the present disclosure provides an aromatic amine compound, wherein the structural formula of the aromatic amine compound is as shown in Chemical Formula A or Chemical Formula B:

[0056] wherein L1 is selected from a single bond, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0057] Q1, Q2, and Q3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and at least one of Q1, Q2, and Q3 contains at least one of the groups represented by the following chemical formulas P1 to P6:

[0058] wherein Ar4 is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkane naphthyl group having 14 to 30 carbon atoms;

[0059] R4 and R5 are the same or different and are independently selected from any one of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

[0060] R6 is C(R7R8); R7 and R8 are each independently selected from hydrogen, deuterium, fluorine, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;

[0061] Said p represents an integer of 0-6; when p is greater than 1, any two R4 are the same or different;

[0062] Said q represents an integer of 0-4; when q is greater than 1, any two R5 are the same or different;

[0063] The x represents an integer from 0 to 3; when x is greater than 1, any two R5 are the same or different;

[0064] k is an integer from 2 to 4; any two R7s are the same or different; any two R8s are the same or different;

[0065] When L1, Q1, Q2, Q3, R4, R5, R7, R8, and Ar4 have substituents, the substituents of L1, Q1, Q2, Q3, R4, R5, R7, R8, and Ar4 may be the same or different and are independently selected from any one of deuterium, halogen, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms;

[0066] Represents a connection key.

[0067] The aromatic amine compound provided in the embodiment of the present disclosure has a structure shown in Chemical Formula A or Chemical Formula B, which includes at least one of the groups shown in Chemical Formulas P1 to P6. The introduction of at least one of the groups shown in Chemical Formulas P1 to P6 into the triarylamine structure can effectively improve the film-forming properties of the compound. Specifically, in the groups shown in Chemical Formulas P1 to P4, there is a large steric hindrance between the Ar4 group on the naphthalene ring and the triarylamine main group, so the plane where the triarylamine main group is located, the plane where the naphthalene ring is located, and the plane where the Ar4 group is located will present a certain angle, thereby improving the stereoscopic properties of the aromatic amine compound, reducing the stacking between molecules, and thus improving the film-forming properties. In the groups shown in Chemical Formulas P5 to P6, there is a cycloalkane structure on the benzene ring, which can also improve the stereoscopic properties of the aromatic amine compound, thereby reducing the stacking between molecules and thus improving the film-forming properties. Not only that, in some specific types of compounds, the aromatic amine compound also has improvements in electrochemical properties or optical properties, and thus can improve at least one performance of the electroluminescent device when applied to the organic layer of the electroluminescent device.

[0068] In one embodiment of the present disclosure, Ar4 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkane naphthyl group having 14 to 30 carbon atoms.

[0069] In one embodiment of the present disclosure, R6 is CH2 or CD2, and k is 2. In this embodiment, the cycloalkyl naphthalene (such as dihydroacenaphthene, dideuteracenaphthene, etc.) introduced by the aromatic amine compound has a strong electron-donating ability (increases the electron cloud density), which can improve the hole mobility. And relative to naphthalene, dihydroacenaphthene or dideuteracenaphthene will increase the molecular weight, which can improve the thermal stability of the aromatic amine compound (high glass transition temperature) and ensure that the device has a good life. At the same time, cycloalkyl naphthalene increases the molecular weight (and can also improve the solubility of the material, which is convenient for cleaning the evaporation mask), but has little effect on the sublimation temperature, which is beneficial to the evaporation process. The groups shown in Chemical Formulas P5 to P6 improve the anisotropy of the material by distorting the structure and spatial steric hindrance, and effectively improve the lateral steric hindrance of the material. When the aromatic amine compound is applied to the first functional layer, especially when applied to a common film layer such as a hole injection layer or a hole transport layer, the aromatic amine compound can improve the device crosstalk and lateral leakage. By introducing D or some stable fragments for modification, a series of organic materials with excellent performance can be synthesized, which can be used as hole transport materials. At the same time, the groups represented by chemical formulas P5 to P6 can give the aromatic amine compound a large refractive index, thereby making it suitable for use in the cover layer.

[0070] In one embodiment of the present disclosure, a first aromatic amine compound is provided, and the structure of the first aromatic amine compound is shown in the following formula I:

[0071] Wherein, Ar3 is selected from any one of the following groups:

[0072] Ar1 and Ar2 may be the same or different and each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkylnaphthalene; the heteroaryl group contains at least one or more heteroatoms selected from O, S, N, and Si;

[0073] The R1-R3 may be the same or different, and each independently represents any one of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

[0074] When Ar1, Ar2, Ar4, R1-R5 have substituents, the substituents of Ar1, Ar2, Ar4, R1-R5 may be the same or different, and are independently selected from any one of deuterium, halogen, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms, arylamine having 6 to 30 carbon atoms, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, and aryl having 6 to 30 carbon atoms;

[0075] When Ar3 is selected from When all hydrogen atoms on at least one benzene ring directly connected to the naphthyl group are replaced by deuterium;

[0076] Said m represents an integer of 0-5;

[0077] Said n represents an integer of 0-5;

[0078] The o represents an integer of 0-4.

[0079] When the first type of aromatic amine compound introduces a naphthyl structure or a cycloalkylnaphthalene structure (such as an alkylnaphthalene structure) with large steric hindrance, and the connection positions include at least 1,8-positions or 2,3-positions, the connection angle formed at this time can effectively avoid stacking between molecules and improve film forming properties. At the same time, it also has good hole transport ability, appropriate HOMO energy level and T1 value, and high glass transition temperature (Tg), which can effectively improve the luminous efficiency of OLED devices, reduce the driving voltage of the device, and extend its service life and other performance.

[0080] Technicians have discovered that when the Ar3 group is selected as a naphthyl structure or a cycloalkylnaphthalene structure with large steric hindrance, and the connection position includes at least the 1,8-position or the 2,3-position, the connection angle formed can effectively avoid stacking between molecules and improve film forming properties; at the same time, when the hydrogen on the benzene ring directly connected to the naphthyl structure or the cycloalkylnaphthalene structure is completely replaced by deuterium, the service life of the device can be improved. Furthermore, when the connection position between the benzene ring and the naphthyl structure or the cycloalkylnaphthalene structure is the 1,8-position or the 2,3-position, and the hydrogen on the benzene ring is completely replaced by deuterium, the effect of improving the device life is more obvious. In addition, the introduction of a naphthyl structure or cycloalkylnaphthalene structure with a connection position of 2,3- at the Ar3 position is more effective in improving device performance than the introduction of a naphthyl structure or cycloalkylnaphthalene structure with a connection position of 1,8-. This is because the naphthyl structure or cycloalkylnaphthalene structure with a connection position of 2,3- has a larger physical property adjustment space, which can effectively block the exciton from recombining at the interface, further improving the mobility. Therefore, when the aromatic amine compound provided by the present disclosure is used as a hole transport material, it can effectively improve the luminous efficiency of the device, reduce the energy consumption of the device, reduce the driving voltage, and extend the service life of the device. In addition, when the cycloalkylnaphthalene structure is introduced at the Ar3 position, not only can the same characteristics as the introduction of the naphthyl structure be guaranteed, but the solubility of the aromatic amine compound can also be increased, which is convenient for cleaning the evaporation mask. At the same time, the sublimation temperature can be improved to a certain extent, which is beneficial to improving the stability of the device.

[0081] Optionally, the first type of aromatic amine compound is particularly suitable for use in the first functional layer, and in particular is particularly suitable for use in the hole transport layer or the electron blocking layer.

[0082] In one embodiment of the present disclosure, in the first type of aromatic amine compound, the aryl group is selected from any one of a methylfluorenyl group, a cycloalkylfluorenyl group having 5 to 10 carbon atoms, a 9,9-diphenylfluorenyl group, and a spirobifluorenyl group.

[0083] In one embodiment of the present disclosure, in the first type of aromatic amine compound, the cycloalkylnaphthalene is selected from one of the following structures:

[0084] In one embodiment of the present disclosure, in the first type of aromatic amine compound, Ar1, Ar2, and Ar4 are each independently selected from one of the substituted or unsubstituted structures shown in the following formulas A-1 to A-34:

[0085] In one example, when Formulas A1 to A34 have substituents, the substituents on Formulas A1 to A34 may be deuterium. For example, Ar1, Ar2, and Ar4 are each independently selected from a substituted or unsubstituted group A'; the unsubstituted group A' is independently selected from Formulas A1 to A34; and the substituted group A' is a substituent formed by replacing at least one hydrogen atom on the unsubstituted group A' with deuterium.

[0086] In one embodiment of the present disclosure, the first type of aromatic amine compound is selected from one of the following structures:

[0087] Further, when Ar3 is selected from In any of the above cases, the hydrogen on the benzene ring directly connected to Ar3 in the Ar4 group can be arbitrarily replaced by deuterium, and the hydrogen on the benzene ring connected between the connecting bond position and the N on the main structure can be arbitrarily replaced by deuterium to improve the device life; illustratively, its structure can be:

[0088] This structure can be understood as a deuterated form of compound 130; or This structure can be understood as a deuterated form of compound 136. There are many other compounds with this characteristic, which are not listed or numbered here. To obtain these deuterated compounds, simply select deuterium-substituted starting materials during preparation. The preparation process is the same as that for the non-deuterated compounds of the same structure.

[0089] In one embodiment of the present disclosure, the first type of aromatic amine compound is selected from substituted compound A', and the unsubstituted compound A' is selected from the group consisting of compound 1 to compound 609; the substituted compound A' is a compound formed by replacing at least one hydrogen on the unsubstituted compound A' with deuterium.

[0090] The present disclosure also provides a method for preparing a first type of aromatic amine compound, comprising the following steps:

[0091] Compound a and compound b are added to a solvent, heated under reflux for 0.5-1.5 hours under an inert atmosphere, then cooled to below 80°C, potassium carbonate and tetrakis(triphenylphosphine)palladium are added, and the reflux reaction is continued for 8-10 hours. After the reaction is completed, the mixture is washed with water, and the organic phase is extracted with dichloromethane, dried over anhydrous magnesium sulfate, and rotary evaporated to obtain a crude product. The crude product is recrystallized from dichloromethane and n-heptane to obtain compound c.

[0092] Compound c and compound d are added to a solvent, heated under reflux for 1.5-2 hours under an inert atmosphere, and sodium tert-butoxide, 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl and tris(dibenzylideneacetone)dipalladium are added, and the reflux reaction is continued for 8-10 hours. After the reaction is completed, the mixture is quenched with water, extracted with dichloromethane and water, and the organic phase is dried over anhydrous magnesium sulfate, rotary evaporated, and purified by column chromatography using toluene and n-heptane for recrystallization to obtain the product;

[0093] Wherein, the compound a is selected from One of the following;

[0094] The compound b is selected from

[0095] The compound d is selected from

[0096] Ar1, Ar2, and Ar4 may be the same or different and each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkylnaphthalene; the heteroaryl group contains at least one or more heteroatoms selected from O, S, N, and Si;

[0097] The R1 to R5 may be the same or different, and each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

[0098] When Ar1, Ar2, Ar4, R1-R5 have substituents, the substituents of Ar1, Ar2, Ar4, R1-R5 may be the same or different, and are independently selected from any one of deuterium, halogen, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms, arylamine having 6 to 30 carbon atoms, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, and aryl having 6 to 30 carbon atoms;

[0099] Said m represents an integer of 0-5;

[0100] Said n represents an integer of 0-5;

[0101] Said o represents an integer from 0 to 4;

[0102] Said p represents an integer from 0 to 6;

[0103] Said q represents an integer from 0 to 4;

[0104] Represents a connection key.

[0105] According to one aspect of the present disclosure, the present disclosure further provides an application of an aromatic amine compound in preparing an organic electroluminescent device, and in particular provides an application of a first type of aromatic amine compound in preparing an organic electroluminescent device.

[0106] According to one aspect of the present disclosure, the present disclosure also provides an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer includes one or more of the first type of aromatic amine compounds.

[0107] In one embodiment of the present disclosure, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and / or an electron injection layer;

[0108] Wherein, the materials of the hole transport layer, the electron blocking layer and / or the light-emitting layer include one or more of the first type of aromatic amine compounds.

[0109] According to one aspect of the present disclosure, a display device is further provided. The display device includes the electroluminescent device provided by the embodiment of the present disclosure.

[0110] The first type of aromatic amine compound provided by the present disclosure has the following advantages:

[0111] 1. The aromatic amine compound introduces a naphthyl structure or a cycloalkylnaphthalene structure with a connection position of 1,8- or 2,3-position at the Ar3 position. The connection angle formed at this time can increase its steric hindrance, avoid stacking between molecules, and improve film-forming properties.

[0112] 2. The aromatic amine compound introduces a naphthyl structure or a cycloalkylnaphthalene structure with a 2,3-position connection position at the Ar3 position, which has a larger space for adjusting physical properties, can effectively block the exciton recombination at the interface, and further improve the mobility.

[0113] 3. When the aromatic amine compound introduces a cycloalkylnaphthalene structure at the Ar3 position, it can not only ensure the same properties as the introduction of a naphthyl structure, but also increase the solubility of the aromatic amine compound, facilitate the cleaning of the evaporation mask, and at the same time, it can also improve the sublimation temperature to a certain extent, which is beneficial to improving the stability of the device.

[0114] 4. By adjusting the substituents on the aromatic amine compound, a series of materials with different properties can be effectively obtained. For example, the introduction of dibenzofuran, carbazole, fluorene and other groups into the structure ensures that the aromatic amine compound has high T1 characteristics, which can effectively block excitons and improve the performance of the aromatic amine compound.

[0115] 5. The aromatic amine compound has strong hole transport ability, appropriate HOMO energy level and T1 value, high glass transition temperature (Tg), and high hole mobility. It can be used as a hole transport material, electron blocking material or light-emitting layer material to improve the life and current efficiency of the device and significantly reduce the device voltage.

[0116] In one embodiment of the present disclosure, the first type of aromatic amine compound disclosed herein is suitable for use in light-emitting elements, display panels, and electronic devices, and is particularly suitable for use in organic electroluminescent devices. The electronic device disclosed herein is a device comprising a layer of at least one organic compound, which may also comprise an inorganic material or a layer formed entirely of an inorganic material. The electronic device is preferably an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic dye-sensitized solar cell (O-DSSC), an organic optical detector, an organic photoreceptor, an organic field quenching device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser), and an organic plasma emission device. The electronic device is preferably an organic electroluminescent device (OLED).

[0117] The first type of aromatic amine compound disclosed in the present invention can be prepared by using a representative reaction, Buchwald-Hartwig coupling reaction, Suzuki coupling reaction or Heck coupling reaction.

[0118] In one embodiment of the present disclosure, a second type of aromatic amine compound is provided; the structural formula of the second type of aromatic amine compound is shown in Chemical Formula II or Chemical Formula III:

[0119] Wherein, L2 is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0120] The cycloalkylnaphthalene (cycloalkyl naphthalene) introduced by the second type of aromatic amine compound has a strong electron-donating ability (increases the electron cloud density) and can improve the hole mobility; and relative to naphthalene, its molecular weight increases, which can improve the thermal stability of the molecule (for example, increase the glass transition temperature) and ensure that the device has a good lifespan. At the same time, cycloalkylnaphthalene increases the molecular weight (which can also improve the solubility of the material, facilitating the cleaning of the evaporation mask), but has little effect on the sublimation temperature, which is beneficial to the evaporation process. The second type of aromatic amine compound improves the anisotropy of the material by distorting the structure and spatial steric hindrance, effectively improving the lateral steric hindrance of the material, and thus can improve the device crosstalk and lateral leakage. At the same time, by introducing D or some stable fragments for modification, a series of organic materials with excellent performance can be synthesized, which can be used as hole transport materials.

[0121] Through extensive verification, the inventors discovered that compared to the first-class aromatic amine compounds containing structural formulas P1 to P4, this second-class aromatic amine compound has a faster mobility, which is very effective in improving device performance. Furthermore, this second-class aromatic amine compound also has a deeper HOMO energy level, which makes it suitable for use in electron-blocking layers, thereby increasing the speed at which holes are injected from the hole transport layer into the light-emitting functional layer. This also compensates for the slow mobility of the light-emitting auxiliary layer (especially for blue light) in related technologies.

[0122] In one example, R5 is selected from hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms.

[0123] In one embodiment of the present disclosure, is selected from substituted or unsubstituted W6; wherein, unsubstituted W6 is

[0124] The substituted W6 is a substituent formed by replacing one or more hydrogen atoms on the naphthalene ring of the unsubstituted W6 with deuterium.

[0125] In one embodiment of the present disclosure, is selected from substituted or unsubstituted W6; wherein, unsubstituted W6 is

[0126] The substituted W6 is a substituent formed by replacing one or more hydrogen atoms on the naphthalene ring of the unsubstituted W6 with deuterium.

[0127] In one embodiment of the second type of aromatic amine compounds, L2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group.

[0128] In one embodiment of the second type of aromatic amine compound, when L2 has a substituent, the substituent on L2 is selected from deuterium, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, and an alkyl group having 1 to 4 carbon atoms. When there are multiple substituents on L2, any two substituents may be the same or different. In particular, the substituent on L2 is selected from deuterium or an aryl group having 6 to 12 carbon atoms.

[0129] In one example, when L2 has a substituent, the substituent on L2 is deuterium: at least one hydrogen on L2 is replaced by deuterium, for example, all hydrogens on L2 are replaced by deuterium.

[0130] In one embodiment of the second type of aromatic amine compounds, the unsubstituted L2 is selected from the group consisting of the following structures:

[0131] In one embodiment of the second type of aromatic amine compounds, Q2 is selected from The Q3 is selected from Wherein, Ar5 and Ar6 are the same or different and are independently selected from a substituted or unsubstituted group W1, and the unsubstituted group W1 is selected from:

[0132] The substituted group W1 is a group formed by replacing an unsubstituted group W1 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms; and when there are multiple substituents on the substituted group W1, any two substituents may be the same or different.

[0133] In one example, the substituted group W1 is a substituent formed by replacing at least one hydrogen on the unsubstituted group W1 with deuterium, for example, the substituted group W1 is a substituent formed by replacing each hydrogen on the unsubstituted group W1 with deuterium.

[0134] In one embodiment of the second type of aromatic amine compound, L3 and L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted group W2, and the unsubstituted group W2 is selected from:

[0135] The substituted group W2 is a group formed by replacing the unsubstituted group W2 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 20 carbon atoms, and a heteroaryl group with 3 to 20 carbon atoms, and when the number of substituents on the substituted group W2 is multiple, any two substituents are the same or different.

[0136] In one example, the substituted group W2 is a group formed by replacing at least one hydrogen atom on the unsubstituted group W2 with deuterium. For example, the substituted group W2 is a group formed by replacing each hydrogen atom on the unsubstituted group W2 with deuterium.

[0137] In one embodiment of the second type of aromatic amine compound, is selected from substituted or unsubstituted groups W3, and the unsubstituted group W3 is selected from structural formulas a1 to a296:

[0138] ------Describe chemical bonds;

[0139] The substituted group W3 is a group formed by replacing an unsubstituted group W3 with one or more deuterium atoms. For example, the substituted group W3 is a group formed by replacing each hydrogen atom of the unsubstituted group W3 with a deuterium atom.

[0140] In one embodiment of the second type of aromatic amine compound, the aromatic amine compound is selected from substituted or unsubstituted compound W4, and the unsubstituted compound W4 is selected from the group consisting of the following compounds:

[0141] The substituted compound W4 is a compound formed by replacing the unsubstituted compound W4 with one or more deuteriums.

[0142] In one example, the substituted compound W4 is a compound in which each hydrogen atom of the unsubstituted compound W4 is replaced by deuterium.

[0143] In another example, the substituted compound W4 is all SP on the unsubstituted compound W4 2 A compound formed by replacing all hydrogens on hybridized carbon with deuterium.

[0144] In some embodiments of the present disclosure, a third type of aromatic amine compound is provided, and the structural formula of the third type of aromatic amine compound is shown in Chemical Formula II:

[0145] wherein L2 is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; wherein Q2 and Q3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and at least one of Q2 and Q3 contains a fused aromatic heterocycle, and each heteroatom in the fused aromatic heterocycle is each independently selected from N, O and S.

[0146] The third type of aromatic amine compound has a high refractive index and high thermal stability, and can be applied to the covering layer of an electroluminescent device, thereby improving the performance of the electroluminescent device. The third type of aromatic amine compound takes aromatic amine as the core, introduces a fused aromatic heterocycle (containing heteroatoms), and thereby improves the polarizability of the third type of aromatic amine compound; the introduction of the group P6 into the third type of aromatic amine compound can increase its refractive index, thereby improving the light extraction efficiency of the electroluminescent device. Not only that, by introducing the group P6 and the fused aromatic heterocycle, the refractive index value of the third type of aromatic amine compound in the wavelength range of 450 to 630 nm can be made greater than 1.8 and the light absorption intensity is small (less than 0.1), while the absorption at 400 nm is strong. This can absorb ultraviolet light in the light on the basis of improving the light extraction efficiency of visible light, thereby extending the service life of the device. In this example, at least one of Q2 and Q3 contains a fused aromatic heterocycle. This results in a small angle between the aromatic groups of the third aromatic amine compound, good planarity, and strong conjugation, thereby increasing its refractive index and enhancing its absorbance at 400 nm, thereby increasing its absorption of ultraviolet light. The introduction of the group P6 into this third aromatic amine compound allows it to maintain a high refractive index while also appropriately increasing the three-dimensionality of the structure, thereby improving the film-forming properties of the material (e.g., increasing its glass transition temperature).

[0147] In one embodiment of the third type of aromatic amine compound, at least one of Q2 and Q3 contains the following fused aromatic heterocyclic group:

[0148] wherein X1 is selected from C(Y6Y7), NY8, O, S; X2 is selected from NY8, O, S;

[0149] Y1, Y2, Y3, and Y4 are each independently selected from CY8 or N, and only one of them is selected from N; Y5, Y6, Y7, and Y8 are each independently selected from hydrogen, deuterium, an alkyl group with 1 to 30 carbon atoms, an arylene group with 6 to 20 carbon atoms, and a heteroaryl group with 5 to 20 carbon atoms.

[0150] In one embodiment of the third type of aromatic amine compounds, X1 is selected from O and S; X2 is selected from O and S; Y8 is selected from hydrogen and deuterium; Y5 is selected from hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, and phenanthryl.

[0151] In one embodiment of the third type of aromatic amine compounds, at least one of Q2 and Q3 is selected from the group consisting of:

[0152] In one embodiment of the third type of aromatic amine compound, when Q2 does not contain a fused aromatic heterocycle, Q2 is selected from a substituted or unsubstituted group W5; when Q3 does not contain a fused aromatic heterocycle, Q3 is selected from a substituted or unsubstituted group W5;

[0153] The unsubstituted group W5 is selected from an aryl group having 6 to 40 carbon atoms and a heteroaryl group having 5 to 40 carbon atoms;

[0154] The substituted group W5 is a group formed by replacing the unsubstituted group W5 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 6 to 10 carbon atoms, and an aryl group with 6 to 12 carbon atoms, and when there are multiple substituents on the substituted group W5, any two substituents are the same or different.

[0155] In one embodiment of the third type of aromatic amine compounds, the unsubstituted group W5 is selected from biphenyl, terphenyl, naphthyl, naphthyl-substituted phenyl, naphthyl-substituted biphenyl, anthracenyl, anthracenyl-substituted phenyl, anthracenyl-substituted biphenyl, phenanthrenyl, phenanthrenyl-substituted phenyl, and phenanthrenyl-substituted biphenyl.

[0156] In one embodiment of the third type of aromatic amine compound, L2 is selected from phenylene, biphenylene, terphenylene, naphthylene, dibenzofuranylene, and dibenzothiophenylene. In one example, L2 is phenylene.

[0157] In one embodiment of the third type of aromatic amine compound, the aromatic amine compound is selected from the group consisting of the following compounds:

[0158] In one embodiment of the present disclosure, the hole injection layer includes an aromatic amine compound provided in the embodiments of the present disclosure, and in particular, may include the first aromatic amine compound or the second aromatic amine compound provided in the embodiments of the present disclosure. For example, the material of the hole injection layer may be a mixture of the first aromatic amine compound provided in the embodiments of the present disclosure and a dopant material, or a mixture of the second aromatic amine compound and a dopant material.

[0159] In some other embodiments of the present disclosure, the hole injection layer can be made of materials other than the aromatic amine compounds provided by the present disclosure, such as inorganic oxides, including but not limited to molybdenum oxide, silver oxide, tungsten oxide, manganese oxide and other inorganic oxides, and can also be selected from p-type dopants of strong electron-withdrawing systems and dopants of hole transport materials, such as F4TCNQ, HATCN, etc.

[0160] In one embodiment of the present disclosure, the hole transport layer may include the aromatic amine compound provided in the embodiment of the present disclosure, and in particular, may include the first type of aromatic amine compound or the second type of aromatic amine compound provided in the embodiment of the present disclosure. In one example, the material of the hole transport layer may be the first type of aromatic amine compound provided in the embodiment of the present disclosure, or the material of the hole transport layer may be the second type of aromatic amine compound provided in the embodiment of the present disclosure. In another example, the hole transport layer may include a plurality of sequentially stacked sub-hole transport layers, for example, including a first sub-hole transport layer and a second sub-hole transport layer stacked in sequence; the material of one of the first sub-hole transport layer and the second sub-hole transport layer is the first type of aromatic amine compound or the second type of aromatic amine compound provided in the embodiment of the present disclosure. In another example, the hole transport layer may include a plurality of sequentially stacked sub-hole transport layers, for example, including a first sub-hole transport layer and a second sub-hole transport layer stacked in sequence; the materials of the first sub-hole transport layer and the second sub-hole transport layer are both selected from the first type of aromatic amine compound or the second type of aromatic amine compound provided in the embodiment of the present disclosure, and the materials of the first sub-hole transport layer and the second sub-hole transport layer are different.

[0161] In some other embodiments of the present disclosure, the hole transport layer may use materials other than the aromatic amine compounds provided by the present disclosure, for example, aromatic amine hole transport materials or carbazole hole transport materials, such as but not limited to one or more of NPB, TPD, BAFLP, 4DFLDPBi, CBP, PCzPA and TCTA.

[0162] In one example, an open metal mask can be used to sequentially deposit the hole injection layer and the hole transport layer. Further, the hole injection layer has a thickness of 5 to 20 nm, and the hole transport layer has a thickness of 80 to 120 nm.

[0163] In one embodiment of the present disclosure, the electron blocking layer (which may also be referred to as a light-emitting auxiliary layer in some cases) includes the aromatic amine compound provided in the embodiments of the present disclosure, and in particular, may include the first aromatic amine compound or the second aromatic amine compound provided in the embodiments of the present disclosure. For example, the material of the electron blocking layer may be the first aromatic amine compound or the second aromatic amine compound provided in the embodiments of the present disclosure.

[0164] In some other embodiments of the present disclosure, the electron blocking layer may be made of materials other than the aromatic amine compounds provided by the present disclosure, including but not limited to one or more of NPB, TPD, BAFLP, 4DFLDPBi, CBP, PCzPA and TCTA.

[0165] In one example of the present disclosure, the hole injection layer comprises the same material as the hole transport layer. In other words, the hole injection layer comprises two or more materials, one of which is the same as the material of the hole transport layer.

[0166] In one embodiment of the present disclosure, the peak wavelength of the photoluminescence of the first functional layer is no greater than 450 nm, for example, between 400 nm and 450 nm. This ensures that only a small portion of the light emitted by the light-emitting functional layer, or even none of the light, has sufficient energy to cause the first functional layer to emit light, thereby preventing a decrease in the light purity of the electroluminescent device.

[0167] In one embodiment of the present disclosure, the peak photoluminescence wavelength of the first functional layer is λ1, and the peak photoluminescence wavelength of the light-emitting functional layer is λ2. λ2-λ1 is not less than 5 nm, and in particular, may be not less than 20 nm. This minimizes the photoluminescence of the light-emitting functional layer from inducing the photoluminescence of the first functional layer.

[0168] Alternatively, the following method may be used to test the photoluminescence spectrum of each material: evaporate the organic material to form a single-layer thin film with a thickness of 50 nm, and then perform a photoluminescence test on the single-layer thin film under a fluorescence spectrometer.

[0169] In one embodiment of the present disclosure, the HOMO (highest occupied molecular orbital) energy level of the electron blocking layer is equal to or less than the HOMO energy level of the hole transport layer. Furthermore, the absolute value of the difference between the HOMO energy level of the hole transport layer and the HOMO energy level of the electron blocking layer is not less than 0.05 eV and not more than 0.25 eV.

[0170] In one embodiment of the present disclosure, the thickness of the hole transport layer is greater than the thickness of the electron blocking layer.

[0171] In one embodiment of the present disclosure, the display panel may include sub-pixels arranged in an array, each sub-pixel being an electroluminescent device (for example, all being OLEDs). In the example of FIG2 , the display device includes a red electroluminescent device, a green electroluminescent device, and a blue electroluminescent device. In the example of FIG2 , any one of the electroluminescent devices includes an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer (Prime, such as the light-emitting auxiliary layer R-Prime of the red electroluminescent device, the light-emitting auxiliary layer G-Prime of the green electroluminescent device, and the light-emitting auxiliary layer B-Prime of the blue electroluminescent device), an organic light-emitting functional layer (EML, such as the red organic light-emitting functional layer R-EML, the green organic light-emitting functional layer G-EML, and the blue organic light-emitting functional layer B-EML), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), and a cathode, which are stacked in sequence.

[0172] In one example, THK(R-prime)>THK(G-Prime)>THK(B-Prime).

[0173] Among them, THK (R-prime) is the thickness of the light-emitting auxiliary layer R-Prime of the red electroluminescent device; THK (G-prime) is the thickness of the light-emitting auxiliary layer G-Prime of the green electroluminescent device; THK (B-prime) is the thickness of the light-emitting auxiliary layer B-Prime of the blue electroluminescent device.

[0174] In one example, THK(R-prime)>THK(G-Prime)+THK(B-Prime).

[0175] In one example, THK(HTL)>THK(G-Prime)+THK(B-Prime), where THK(HTL) is the thickness of the hole transport layer HTL.

[0176] In one example, the thickness of the film layer in the hole transport region (ie, the thickness of the first functional layer) is greater than the thickness of the electron transport region (ie, the thickness of the second functional layer).

[0177] In one example, THK(HTL)>THK(HBL)+THK(ETL)+THK(EIL), where THK(HBL) is the thickness of the hole blocking layer, THK(ETL) is the thickness of the electron transport layer, and THK(EIL) is the thickness of the electron injection layer.

[0178] In one example, THK(HTL)≥100nm, 50nm≤THK(R-prime)<100nm, 1nm<THK(B-Prime)<30nm; 25nm<THK(G-Prime)≤50nm.

[0179] In the above example, the microcavities of the red, green, and blue electroluminescent devices can be controlled to achieve optimal white light efficiency for the display panel. Microcavity control is primarily achieved by adjusting the thickness of the hole transport region. Blue light efficiency is poor and the driving voltage is high, which is related to the energy level barriers and hole mobility of the hole transport layer, the luminescent auxiliary layer, and the luminescent functional layer. In one example, blue light performance can be improved by increasing the energy level and mobility of the luminescent auxiliary layer of the blue electroluminescent device. A microcavity structure with different thicknesses achieves optimal white light efficiency.

[0180] In one embodiment of the present disclosure, the light-emitting functional layer is an organic light-emitting functional layer, which may include a host material and a guest material. In one example, the host material may be a single material, such as a host material having both electron transport and hole transport functions. In another example, the host material may include a hole-type host material primarily for transporting holes and an electron-type host material primarily for transporting electrons. The guest material may be a fluorescent material or a phosphorescent material. Of course, the organic light-emitting functional layer may also be implemented in other forms as needed.

[0181] In one example, the organic light-emitting functional layer can be a blue organic light-emitting functional layer; after holes and electrons recombine in the blue organic light-emitting functional layer, the blue organic light-emitting functional layer emits blue light. Optionally, the host material of the blue organic light-emitting functional layer includes, but is not limited to, an anthracene derivative of a blue light-emitting material; wherein the anthracene derivative of the blue light-emitting material is selected from AND and / or MAND; and the guest material of the blue organic light-emitting functional layer includes, but is not limited to, a pyrene derivative and / or a styrene derivative DPVBi.

[0182] In another example, the host material may be a carbazole derivative or an azine derivative; the guest material may be an organic metal complex (such as an organic iridium complex or an organic platinum complex).

[0183] In one embodiment of the present disclosure, a fine metal mask (FMM) can be used to form an electron blocking layer (in some embodiments, also referred to as a light-emitting auxiliary layer) and an organic light-emitting functional layer by evaporation. In this embodiment, the electroluminescent device is an organic electroluminescent device (OLED).

[0184] In one example, the thickness of the light-emitting auxiliary layer of a blue electroluminescent device is between 5 and 20 nm. The light-emitting functional layer (organic light-emitting functional layer) of the blue electroluminescent device includes a blue light-emitting host material and a blue light-emitting guest material, and has a thickness of 10 to 30 nm. The doping ratio of the blue light-emitting guest material is between 1% and 10%. For example, the doping ratio of the blue light-emitting guest material is 4%.

[0185] In one example, the thickness of the light-emitting auxiliary layer of the green electroluminescent device is 5 to 20 nm. The light-emitting functional layer (organic light-emitting functional layer) of the green electroluminescent device includes a green host material and a green guest material, and has a thickness of 20 to 50 nm. The doping ratio of the green guest material is 1% to 15%. For example, the doping ratio of the green guest material is 10%.

[0186] In one example, the thickness of the light-emitting auxiliary layer of a red electroluminescent device is 50 to 100 nm. The light-emitting functional layer (organic light-emitting functional layer) of the red electroluminescent device includes a red host material and a red guest material, and has a thickness of 50 to 100 nm. The doping ratio of the red guest material is 1% to 15%. For example, the doping ratio of the red guest material is 2%.

[0187] In the example of FIG2 , the display device includes a red electroluminescent device, a green electroluminescent device, and a blue electroluminescent device. It will be understood that in other embodiments of the present disclosure, the colors of the electroluminescent devices included in the display device may be different from those in the example of FIG2 , for example, at least one of the red electroluminescent device, the green electroluminescent device, and the blue electroluminescent device may be missing or an electroluminescent device of a new color may be added.

[0188] In one embodiment of the present disclosure, the hole blocking layer may be made of aromatic heterocyclic compounds, including but not limited to one or more of imidazole derivatives, oxazine derivatives, quinoline derivatives, isoquinoline derivatives or phenanthroline derivatives. In one example, the material of the hole blocking layer is a compound containing a nitrogen-containing six-membered ring structure or a compound having a phosphine oxide group on the heterocyclic ring. Among them, the imidazole derivatives include but are not limited to one or more of benzimidazole derivatives, imidazopyridine derivatives and benzimidazolephenanthridine derivatives; the oxazine derivatives include pyrimidine derivatives and / or triazine derivatives. Further, the materials of the electron transport layer and the hole blocking layer include but are not limited to one or more of PBD, OXD-7, TAZ, p-EtTAZ, BCP and TPBI.

[0189] In one embodiment of the present disclosure, the electron transport layer may be made of, but not limited to, one or more of, imidazole derivatives, oxazine derivatives, quinoline derivatives, isoquinoline derivatives, or phenanthroline derivatives. In one example, the material of the hole blocking layer is a compound having a nitrogen-containing six-membered ring structure or a compound having a phosphine oxide group on a heterocyclic ring. The imidazole derivatives include, but are not limited to, one or more of benzimidazole derivatives, imidazopyridine derivatives, and benzimidazolephenanthridine derivatives; the oxazine derivatives include pyrimidine derivatives and / or triazine derivatives. Further, the materials of the electron transport layer and the hole blocking layer include, but are not limited to, one or more of PBD, OXD-7, TAZ, p-EtTAZ, BCP, and TPBI.

[0190] In other embodiments of the present disclosure, the electron transport layer may also be made of inorganic materials, such as doped or undoped zinc oxide.

[0191] In one embodiment of the present disclosure, the electron injection layer may be an alkali metal or a metal, such as LiF, Yb, Mg, Ca, and the like.

[0192] In one embodiment of the present disclosure, the materials of at least two layers of the electron injection layer, the electron transport layer, and the hole blocking layer contain triazine groups, which can enable the second functional layer to have better electron transport efficiency.

[0193] In one example, the photoluminescence wavelength (peak) of the second functional layer is in the range of 390-430 nm.

[0194] In one embodiment of the present disclosure, the peak photoluminescence wavelength of the second functional layer is λ3, and the peak photoluminescence wavelength of the light-emitting functional layer is λ2. λ2-λ3 is greater than 20 nm, and in particular, may be no less than 30 nm. This minimizes the photoluminescence of the light-emitting functional layer from inducing photoluminescence in the second functional layer.

[0195] In one embodiment of the present disclosure, an open mask can be used to evaporate and form a hole blocking layer, an electron transport layer and an electron injection layer respectively; the thickness of the hole blocking layer is 1 to 20 nm; the thickness of the electron transport layer is 10 to 50 nm; and the thickness of the electron injection layer is 1 to 10 nm.

[0196] In one embodiment of the present disclosure, the anode is a high work function electrode material, which can inject holes into the first functional layer.

[0197] In one example, the anode can be a transparent conductive metal oxide, such as ITO or IZO. Furthermore, the thickness of the anode is between 80 and 200 nm. Optionally, the anode is transparent, and the electroluminescent device can emit light from the anode side. Furthermore, the anode is close to the driving layer, and the electroluminescent device is a bottom-emitting device.

[0198] In another example, the anode can be provided with a metal layer serving as a reflective layer. For example, the anode can be formed into a composite electrode using Ag / ITO, Al / ITO, Ag / IZO, Al / IZO, etc. The metal thickness in the composite electrode can be between 10 and 100 nm; the oxide layer thickness is between 5 and 20 nm. The oxide layer is in direct contact with the first functional layer. In this example, the electroluminescent device cannot emit light through the anode, so the electroluminescent device emits light from the cathode side. Furthermore, the anode is close to the driving layer, and the electroluminescent device is a top-emitting device.

[0199] In one embodiment of the present disclosure, the cathode can be made of a metal with a low work function (such as Al, Ag, Mg, etc.), or an alloy containing a low work function metal material (such as an aluminum-magnesium alloy). Of course, the cathode can also be made of a conductive metal oxide such as IGZO.

[0200] Optionally, when the electroluminescent device emits light from the anode side, the cathode may have a greater thickness to achieve a higher reflectivity, for example, the thickness of the cathode is not less than 80 nm. Furthermore, the reflectivity of the cathode at 550 nm is greater than 85%.

[0201] Optionally, when the electroluminescent device emits light from the cathode side, the cathode may have a smaller thickness to achieve a higher transmittance, for example, the thickness of the cathode is in the range of 10 to 20 nm. Furthermore, the transmittance of the cathode at 550 nm is greater than 45%.

[0202] In one embodiment of the present disclosure, an open mask may be used to sequentially form a metal cathode and a capping layer by evaporation.

[0203] In one embodiment of the present disclosure, the material of the cover layer has a relatively high refractive index to improve the light extraction efficiency of the electroluminescent device. For example, the refractive index of the material of the cover layer at 460 nm is not less than 1.8.

[0204] Furthermore, the material of the covering layer has a high transmittance for light with a wavelength greater than 450 nm, for example, its light absorption intensity k is less than 0.1.

[0205] In related technologies, the cover layer's material has a low absorption intensity for shorter wavelengths, for example, maintaining a low absorption intensity for light around 400nm. This prevents the cover layer from filtering out short-wavelength light. Furthermore, short-wavelength light in the environment can pass through the cover layer and reach the functional layer, potentially accelerating its aging.

[0206] In one embodiment of the present disclosure, the covering layer can be made of the third aromatic amine compound provided in the present disclosure. This aromatic amine compound not only has a high refractive index, but also has a low absorbance for light with a wavelength greater than 450 nm (e.g., light with a wavelength range of 450 to 630 nm) (favoring the emission of visible light), and has a strong absorption intensity for light with a wavelength of 400 nm and shorter. Therefore, this covering layer not only improves the light extraction efficiency of the electroluminescent device through its high refractive index without affecting the normal emission of visible light, but also protects the functional layer by absorbing short-wavelength light (especially ultraviolet light), thereby improving the life of the device.

[0207] As follows, some exemplary compounds were synthesized and their performance tested.

[0208] Synthesis of intermediate compound c-1

[0209] Compound a-1 [(8-phenyl-1-naphthyl)-boric acid] (24.81 g; 100 mmol) and compound b [1,4-deuterated 4-bromodiphenyl] (23.99 g; 100 mmol) were added to a reaction flask, and 250 mL of a THF / H2O mixed solvent (volume ratio of 1-5:1) was added. After heating to reflux for 1 h under a nitrogen environment, the temperature was lowered to below 80°C, potassium carbonate (27.64 g; 200 mmol) was added, and then [tetrakis(triphenylphosphine)palladium] (1.16 g; 1 mmol) was added. The temperature was raised to reflux and the reaction was carried out for 8-12 h. After the reaction, the reaction mixture was washed with water, and the organic phase was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by recrystallization from dichloromethane and n-heptane to obtain intermediate compound c-1 (27.25 g, 75%), LC / MS (m / z) (M+): 362.05.

[0210] Synthesis of intermediate compound c-2

[0211] Compound a-2 [(3-phenyl-2-naphthyl)-boric acid] (24.81 g; 100 mmol) and compound b [1,4-deuterated 4-bromodiphenyl] (23.99 g; 100 mmol) were added to a reaction flask, and 250 ml of a THF / H2O mixed solvent (volume ratio of 1-5:1) was added. After heating to reflux for 1 h under a nitrogen environment, the temperature was lowered to below 80°C, potassium carbonate (27.64 g; 200 mmol) was added, and then [tetrakis(triphenylphosphine)palladium] (1.16 g; 1 mmol) was added. The temperature was raised to reflux and the reaction was carried out for 8-12 h. After the reaction, the mixture was washed with water, and the organic phase was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by recrystallization with dichloromethane and n-heptane to obtain intermediate compound c-2 (24.62 g, 68%), LC / MS (m / z) (M+): 362.06.

[0212] Other intermediate compounds can be prepared by referring to the above steps and adjusting appropriate reactants.

[0213] Synthesis of compound 5

[0214] Intermediate compound c-1 (3.63 g; 10 mmol) and compound d[N-(4-(1-naphthyl)phenyl)-4-benzidine] (3.71 g; 10 mmol) were added to a reaction flask, and 100 ml of toluene was added. The mixture was heated to reflux under nitrogen for 2 h. The temperature was then lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol), and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added. The mixture was then heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate, dried by rotary evaporation, passed through a silica gel column, and recrystallized using toluene and n-heptane to obtain compound 5 (5.35 g, 82%). The purity was 99% as determined by HPLC. LC / MS (m / z) (M+): 653.31.

[0215] Synthesis of compound 23

[0216] The intermediate compound c-1 (3.63 g; 10 mmol) and compound e [N-(4-(9,9-dimethyl-9H-fluorene-2-)phenyl)-9,9-dimethyl-9H-fluorene-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate, then spin-dried and passed through a silica gel column. The product was then recrystallized using toluene and n-heptane to obtain compound 23 (5.61 g, 78%). HPLC analysis revealed a purity of 99.10%. LC / MS (m / z) (M+) was 719.34.

[0217] Synthesis of compound 72

[0218] The intermediate compound c-1 (3.63 g; 10 mmol) and compound f[N-[4-(3-dibenzofuranyl)phenyl]-[1,1'-biphenyl]-4-amine] (4.12 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate, then spin-dried and passed through a silica gel column. The product was then recrystallized using toluene and n-heptane to obtain compound 72 (4.78 g, 69%). HPLC analysis revealed a purity of 99.35%. LC / MS (m / z) (M+) was 693.29.

[0219] Synthesis of compound 85

[0220] The intermediate compound c-1 (3.63 g; 10 mmol) and compound g [N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-[1,1'-biphenyl]-4-amine] (4.86 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate, then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain compound 85 (5.84 g, 76%). HPLC analysis showed a purity of 99%. LC / MS (m / z) (M+) was 768.34.

[0221] Synthesis of compound 170

[0222] 2-(4-bromophenyl)-3-phenylnaphthalene (3.63 g; 10 mmol) and compound e[N-(4-(9,9-dimethyl-9H-fluorene-2-)phenyl)-9,9-dimethyl-9H-fluorene-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain compound 170 (5.79 g, 81%). HPLC analysis showed a purity of 99.11%. LC / MS (m / z) (M+) was 715.32.

[0223] Synthesis of compound 187

[0224] 2-(4-bromophenyl)-3-phenylnaphthalene (3.63 g; 10 mmol) and compound f[N-[4-(3-dibenzofuranyl)phenyl]-[1,1'-biphenyl]-4-amine] (4.12 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain compound 187 (4.75 g, 69%). HPLC analysis showed a purity of 99.24%. LC / MS (m / z) (M+) was 689.27.

[0225] Synthesis of compound 196

[0226] 2-(4-bromophenyl)-3-phenylnaphthalene (3.63 g; 10 mmol) and compound g[N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-4-amine] (4.86 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain compound 196 (6.49 g, 85%). HPLC analysis showed a purity of 99.60%. LC / MS (m / z) (M+) was 764.31.

[0227] Synthesis of deuterated compound 170D

[0228] The intermediate compound c-2 (3.63 g; 10 mmol) and compound e [N-(4-(9,9-dimethyl-9H-fluorene-2-)phenyl)-9,9-dimethyl-9H-fluorene-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain deuterated compound 170D (4.82 g, 67%). HPLC analysis showed a purity of 99.11%. LC / MS (m / z) (M+) was 719.34.

[0229] Synthesis of deuterated compound 187D

[0230] The intermediate compound c-2 (3.63 g; 10 mmol) and compound f[N-[4-(3-dibenzofuranyl)phenyl]-[1,1'-biphenyl]-4-amine] (4.12 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain deuterated compound 187D (4.02 g, 58%). HPLC analysis showed a purity of 99.24%. LC / MS (m / z) (M+) was 693.29.

[0231] Synthesis of Deuterated Compound 196D

[0232] The intermediate compound c-2 (3.63 g; 10 mmol) and compound g [N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-[1,1'-biphenyl]-4-amine] (4.86 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and the mixture was heated to reflux for 2 h under a nitrogen environment. The temperature was lowered, and sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and the mixture was heated to reflux for 8-12 h. After the reaction was completed, water was added to quench the reaction, and dichloromethane and water were added for extraction. The organic phase was dried over anhydrous magnesium sulfate and then spin-dried to dryness. After passing through a silica gel column, the organic phase was recrystallized using toluene and n-heptane to obtain deuterated compound 196 (5.84 g, 76%). HPLC analysis showed a purity of 99.60%. LC / MS (m / z) (M+) was 768.34.

[0233] Comparative compounds

[0234] The present disclosure provides three different comparative compounds, namely Compound D-1, Compound D-2 and Compound D-3. Compound D-1, Compound D-2 and Compound D-3 are all compounds synthesized and tested in previous studies.

[0235] The structural formulas of compound D-1, compound D-2 and compound D-3 are as follows:

[0236] The physical property data of some of the above synthetic examples and comparative examples are shown in Table 1.1. The data in Table 1.1 were obtained using the simulation software Spartan, and the basis set / functional is B3LYP / 6-31G**; ROE is the reorganization energy. It is generally believed that a small absolute value of ROE indicates a tendency towards high mobility.

[0237] Table 1.1

[0238] Device Preparation Example A1.1

[0239] In this preparation example, aromatic amine compounds were used as electron-blocking layer materials in the fabrication of OLED devices. Five different blue OLEDs were prepared using Compound D-1, Compound D-2, Compound 5, Compound 187, and Compound 187D, respectively, as electron-blocking layers: Comparative device A1.1A (electron-blocking layer made of Compound D-1), Comparative device A1.1B (electron-blocking layer made of Compound D-2), Test device A1.1A (electron-blocking layer made of Compound 5), Test device A1.1B (electron-blocking layer made of Compound 187), and Test device A1.1C (electron-blocking layer made of Compound 187D). All layers other than the electron-blocking layer in Comparative device A1.1A, Comparative device A1.1B, and Test devices A1.1A through A1.1C had the same materials and thicknesses.

[0240] The electrode preparation method and the deposition method of each functional layer in this preparation example are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and will not be described in detail here. Only some process details and testing methods in the preparation process are supplemented as follows:

[0241] forming a pixel driving circuit and an anode on a glass substrate;

[0242] Depositing a hole injection layer and a hole transport layer using a metal mask (Open mask);

[0243] An electron blocking layer and a blue light-emitting layer were deposited using a fine metal mask (FMM). The thickness of the electron blocking layer was 5 nm. The blue light-emitting layer included a blue light host and a blue light guest. The mass ratio of the blue light host to the blue light guest was 97:3.

[0244] Use open mask to deposit electron blocking layer, electron transport layer and electron injection layer;

[0245] Finally, an open mask was used to deposit the metal cathode.

[0246] See Table 1.2 for device information.

[0247] Table 1.2

[0248] In this embodiment, except for the material of the electron blocking layer, the molecular structures of the materials of each layer are as follows:

[0249] The performance of each prepared OLED device was measured, and the performance of the comparative device A1.1A was used as a benchmark (100%). The performance of other OLED devices is shown in Table 1.3.

[0250] Table 1.3 Summary of OLED device performance

[0251] Compared with the comparative device A1.1A and the comparative device A1.1B, the devices prepared using the aromatic amine compound of the present invention (test device A1.1A to test device A1.1C) have improved performance in all aspects. This is related to the fact that the aromatic amine compound of the present invention uses the 1,8-position or 2,3-position connection at the Ar3 position to form a special connection angle, which makes it have faster mobility and high T1, and can enable more excitons to recombine and emit light in the light-emitting layer. In addition, the lifespan of the test device A1.1C is significantly improved compared with the test device A1.1B. This is because the CD (carbon-deuterium) bond vibrates at a lower frequency, and its zero-point basic energy is lower than the corresponding CH (carbon-hydrogen) bond energy, while their transition state activation energies are similar, which makes it take more energy to break the CD bond than to break the CH bond, so the CD bond is more stable than the CH bond. The reason why the performance of the test device A1.1C is relatively higher than that of the comparative device A1.1A is related to the high mobility, which is conducive to exciton recombination, and the twisted structure is conducive to high T1.

[0252] Device Preparation Example 1.2

[0253] In this preparation example, aromatic amine compounds are used as hole transport layer materials in the preparation of OLED devices. Compound D-3, compound 85, compound 196, and compound 196D are used as electron blocking layers to prepare four different blue OLEDs, namely: comparative device A1.2A (the material of the hole transport layer is compound D-3), test device A1.2A (the material of the hole transport layer is compound 85), test device A1.2B (the material of the hole transport layer is compound 196), and test device A1.2C (the material of the hole transport layer is compound 196D). The film layers other than the hole transport layer of comparative device A1.2A and test devices A1.2A to A1.2C have the same materials and thicknesses. The electrode preparation method and the deposition method of each functional layer are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, etc., which will not be repeated here. Only some process details and test methods in the preparation process are supplemented as follows:

[0254] forming a pixel driving circuit and an anode on a glass substrate;

[0255] Depositing a hole injection layer and a hole transport layer using a metal mask (Open mask);

[0256] A fine metal mask (FMM) was used to deposit an electron blocking layer and a blue light-emitting layer. The electron blocking layer had a thickness of 5 nm. The blue light-emitting layer included a blue light host and a blue light guest, and had a thickness of 20 nm. The mass ratio of the blue light host to the blue light guest was 97:3.

[0257] Use open mask to deposit hole blocking layer, electron transport layer and electron injection layer;

[0258] Finally, an open mask was used to deposit the metal cathode.

[0259] For device information, see Table 1.4.

[0260] Table 1.4

[0261] Except for the hole transport layer, the molecular structures of the materials in each layer are as follows:

[0262] The performance of the prepared OLED devices was measured, and the performance of the OLED device prepared using the raw materials of Comparative Example 3 was used as a benchmark. The performance of other OLED devices is shown in Table 5.

[0263] Table 1.5 Summary of OLED device performance

[0264] Compared with the comparative device A1.2A, the device prepared using the aromatic amine compound of the present invention has a relatively fast mobility, which is beneficial for the transport of holes to the light-emitting layer, forming more excitons and improving the device performance.

[0265] The following synthesis method was used to obtain intermediate compounds III-1 to III-6, and then some compounds according to exemplary embodiments of the present disclosure were synthesized mainly through Buchwald-Harting reaction and Suzuki reaction.

[0266] Intermediate compound III-1

[0267] Under nitrogen, intermediate compound I-1 (5-bromoacenaphthene) (10 g, 42.90 mmol) and intermediate compound II-1 (4-chlorophenylboronic acid) (7.72 g, 49.34 mmol) were added to a dry three-necked flask. 100 ml of toluene, 35 ml of ethanol, and 35 ml of deionized water were added and stirred until dissolved. Tetrakis(triphenylphosphine)palladium (0.74 g, 0.64 mmol) was then added and heated to reflux. The reaction was monitored by TLC. After completion of the reaction, the product was washed with water, extracted with dichloromethane, and the solvent was removed by rotary evaporation. The solvent was then removed by passing through a silica gel column using a mixture of n-heptane and dichloromethane (10:1). The resulting pale yellow solid was recrystallized, filtered, and dried in vacuo to obtain intermediate compound III-1 in a 72% yield and 98% purity. MS: 264.07.

[0268] By referring to the synthesis method of intermediate compound III-1, intermediate compound II-2 to intermediate compound II-6 are used to replace intermediate compound III-1 for reaction, and intermediate compounds III-2 to intermediate compound III-6 can be obtained accordingly.

[0269] The raw materials, yields, purities and MS used in the synthesis of intermediate compounds III-2 to III-6 are shown in Table 2.1.

[0270] Table 2.1

[0271] The following exemplary compounds of the present disclosure can be synthesized by reacting the III series intermediate compounds with diarylamine compounds:

[0272] When synthesizing the above exemplary compounds, the following diarylamines can be used as raw materials:

[0273] Synthesis of compound B1

[0274] Intermediate compound III-1 (5.58 g, 21 mmol) and N-(4-(1-naphthyl)phenyl)-4-benzidine (the diarylamine a2-H corresponding to intermediate a2) (7.43 g, 20 mmol) were dissolved in toluene and stirred under nitrogen until refluxed. Then, sodium tert-butoxide, Sphos, and Pd(dba) were added, followed by heating under reflux. The reaction mixture was allowed to react overnight. After the reaction was completed and cooled to room temperature, distilled water was added to the reaction solution and extracted with dichloromethane (DCM). The organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography, and the solvent was removed using a rotary evaporator. The solid was recrystallized from toluene / n-heptane to obtain compound B1; purity: 99.63%, yield: 87%, MS: 599.26, molecular weight: C46H33N.

[0275] Referring to the synthesis method of Compound B1, diarylamine a2-H was replaced with diarylamine a41-H, diarylamine a57-H, diarylamine a13-H, diarylamine a154-H, diarylamine a156-H, and diarylamine a221-H, respectively, to synthesize Compounds B9, B10, B18, B37, B58, and B172. The starting materials, synthesis yields, purities, and MS values ​​for Compounds B9, B10, B18, B37, B58, and B172 are shown in Table 2.2.

[0276] Table 2.2

[0277] Synthesis of compound B17

[0278] Intermediate compound III-3 (7.16 g, 21 mmol) and N-(4-(1-naphthyl)phenyl)-4-benzidine (the diarylamine a2-H corresponding to intermediate a2) (7.43 g, 20 mmol) were dissolved in toluene and stirred under nitrogen until refluxed. Then, sodium tert-butoxide, Sphos, and Pd(dba) were added sequentially and heated under reflux. The reaction mixture was allowed to react overnight. After the reaction was completed and cooled to room temperature, distilled water was added to the reaction solution and extracted with dichloromethane (DCM). The organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography, and the solvent was removed using a rotary evaporator. The solid was recrystallized from toluene / n-heptane to obtain compound B17; purity: 99.7%, yield: 86%, MS: 675.29, molecular weight: C52H37N.

[0279] Referring to the synthesis method of compound B17, compounds B19, B136, B139, and B258 were synthesized by substituting diarylamine a4-H, a111-H, a104-H, and a217-H for diarylamine a2-H, respectively. The starting materials, yields, purities, and MS values ​​for compounds B19, B136, B139, and B258 are shown in Table 2.3.

[0280] Table 2.3

[0281] Synthesis of Partially Deuterated Compound B17D

[0282] Under nitrogen, compound B17 (6.75 g, 10 mmol), deuterated benzene (89 ml, 1 mol), trifluoromethanesulfonic acid (9.43 g, 60 mmol), and 500 ml of 1,4-dioxane were added to a three-necked flask. The reaction was allowed to proceed overnight at 90°C. The reaction was monitored by TLC. Upon completion, the mixture was cooled to room temperature. The mixture was extracted with dichloromethane and deionized water, washed with water until neutral, and then dehydrated with anhydrous magnesium sulfate. The organic phase was dried on a rotary evaporator and recrystallized from dichloromethane and n-heptane to afford a pale yellow product, compound B17D. Yield: 43%; purity: 99.53%; MS [M+H]+: 708.29. All hydrogen atoms attached to the sp2-hybridized carbon atoms in compound B17 were deuterated, forming compound B17D.

[0283] In the embodiments of the present disclosure, the properties of some of the above exemplary compounds are also compared with reference compounds, and the structures of the reference compounds are as follows:

[0284] The physicochemical shapes of the control compound, as well as compounds B10, B17, B19, and B224, were simulated using the Spartan simulation software (basis set / functional: B3LYP / 6-31G**). The results are shown in Table 2.4. ROE stands for reorganization energy, and it is generally believed that a small absolute value of ROE indicates a high mobility.

[0285] Table 2.4

[0286] Device preparation and test example 2.1

[0287] The following method was used to prepare a plurality of organic electroluminescent devices and the driving voltage, luminous efficiency and life of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent devices is as follows:

[0288] The prepared ITO substrate is cleaned and dried, and an ITO layer serving as an anode is formed on the ITO substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially stacked on the anode through an evaporation process.

[0289] The hole injection layer is made of a mixture of compound HT2.1 and compound PD2.1, with a thickness of 20 nm and a doping ratio of compound PD2.1 of 2%.

[0290] The hole transport layer is made of compound HT2.1 with a thickness of 110 nm;

[0291] The material of the organic light-emitting layer is a mixture of compound BH2.1 and compound BD2.1, the doping ratio of compound BD2.1 is 4%, and the thickness is 20nm;

[0292] The hole blocking layer is made of compound HB2.1 and has a thickness of 10 nm;

[0293] The material of the electron transport layer is compound ET2.1, with a thickness of 30 nm;

[0294] The electron injection layer is made of Yb and has a thickness of 5 nm.

[0295] The cathode material is Mg:Ag (2:8) alloy with a thickness of 12 nm;

[0296] The material of the cover layer is CP2.1 and the thickness is 70nm.

[0297] In this device preparation and testing example 2.1, based on the different materials used in the electron blocking layer of the organic electroluminescent device, the organic electroluminescent devices are divided into reference device B2.1 (the electron blocking layer material is compound EBL1-Ref), test device B2.1A (the electron blocking layer material is compound B37), test device B2.1B (the electron blocking layer material is compound B160), and test device B2.1C (the electron blocking layer material is compound B193). The only difference between reference device B2.1, test device B2.1A, test device B2.1B, and test device B2.1C is the material of the electron blocking layer; the materials and thicknesses of the remaining film layers are the same. The thickness of the electron blocking layer is 10 nm.

[0298] The structural formulas of each material are as follows:

[0299] The driving voltage, luminous efficiency, and lifespan of reference device B2.1, test device B2.1A, test device B2.1B, and test device B2.1C were tested. The test results are shown in Table 2.5. In Table 2.5, the test data of each device were normalized based on reference device B2.1. The lifespan is the T95 lifespan, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; Efficiency is current efficiency, and the current density during testing is 15mA / cm 2 .

[0300] Table 2.5

[0301] Compared to reference device B2.1, test devices B2.1A through B2.1C exhibit higher efficiency and longer lifetimes. This is because the electron-blocking layer in test devices B2.1A through B2.1C incorporates cycloalkylnaphthalene, which improves material mobility and provides a relatively shallow energy level. Furthermore, the relatively twisted structure reduces quenching and crystallization caused by molecular stacking, thereby improving efficiency and lifetime.

[0302] Device preparation and test example 2.2

[0303] The following method was used to prepare a plurality of organic electroluminescent devices and the driving voltage, luminous efficiency and life of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent devices is as follows:

[0304] The prepared ITO substrate is cleaned and dried, and an ITO layer serving as an anode is formed on the ITO substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially stacked on the anode through an evaporation process.

[0305] The hole injection layer is made of a mixture of compound HT2.1 and compound PD2.1, with a thickness of 20 nm and a doping ratio of compound PD2.1 of 2%.

[0306] The hole transport layer is made of compound HT2.1 with a thickness of 110 nm;

[0307] The material of the organic light-emitting layer is a mixture of compound BH2.1 and compound BD2.1, the doping ratio of compound BD2.1 is 4%, and the thickness is 20nm;

[0308] The hole blocking layer is made of compound HB2.1 and has a thickness of 10 nm;

[0309] The material of the electron transport layer is compound ET2.1, with a thickness of 30 nm;

[0310] The material of the electron injection layer is compound Yb, with a thickness of 5nm;

[0311] The cathode material is Mg:Ag (2:8) alloy with a thickness of 12 nm;

[0312] The material of the cover layer is CP2.1 and the thickness is 70nm.

[0313] In this device preparation and testing example 2.2, based on the different materials used in the electron blocking layer of the organic electroluminescent device, the organic electroluminescent devices are divided into reference device B2.2 (the electron blocking layer material is compound EBL2-Ref), test device B2.2A (the electron blocking layer material is compound B1), test device B2.2B (the electron blocking layer material is compound B10), test device B2.2C (the electron blocking layer material is compound B17), and test device B2.2D (the electron blocking layer material is compound B19). The only difference between reference device B2.2, test device B2.2A, test device B2.2B, test device B2.2C, and test device B2.2D is the different materials of the electron blocking layer; the materials and thicknesses of the remaining film layers are the same. The thickness of the electron blocking layer is 10 nm.

[0314] The driving voltage, luminous efficiency, and lifespan of the reference device B2.2, test device B2.2A, test device B2.2B, test device B2.2C, and test device B2.2D were tested. The test results are shown in Table 2.6. In Table 2.6, the test data of each device were normalized using the reference device B2.2 as the benchmark. The lifespan refers to the T95 lifespan, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; Efficiency is current efficiency, and the current density during testing is 15mA / cm 2 .

[0315] Table 2.6

[0316] Compared to reference device B2.2, test devices B2.2A through B2.2D exhibit higher efficiency and longer lifetimes. This is because the electron-blocking layer in test devices B2.2A through B2.2D incorporates cycloalkylnaphthalene, which improves material mobility and provides a relatively shallow energy level. Furthermore, the relatively twisted structure reduces quenching and crystallization caused by molecular stacking, thereby improving efficiency and lifetime.

[0317] Device preparation and test example 2.3

[0318] The following method was used to prepare a plurality of organic electroluminescent devices and the driving voltage, luminous efficiency and life of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent devices is as follows:

[0319] The prepared ITO substrate is cleaned and dried, and an ITO layer serving as an anode is formed on the ITO substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially stacked on the anode through an evaporation process.

[0320] The hole injection layer is made of a mixture of compound HT2.1 and compound PD2.1, with a thickness of 20 nm and a doping ratio of compound PD2.1 of 2%.

[0321] The hole transport layer is made of compound HT2.1 with a thickness of 110 nm;

[0322] The material of the organic light-emitting layer is a mixture of compound BH2.1 and compound BD2.1, the doping ratio of compound BD2.1 is 4%, and the thickness is 20nm;

[0323] The hole blocking layer is made of compound HB2.1 and has a thickness of 10 nm;

[0324] The material of the electron transport layer is compound ET2.1, with a thickness of 30 nm;

[0325] The material of the electron injection layer is compound Yb, with a thickness of 5nm;

[0326] The cathode material is Mg:Ag (2:8) alloy with a thickness of 12 nm;

[0327] The material of the cover layer is CP2.1 and the thickness is 70nm.

[0328] In Device Preparation and Testing Example 2.3, the organic electroluminescent devices are divided into reference device B2.3 (electron blocking layer material: compound EBL3-Ref) and test device B2.3A (electron blocking layer material: compound B17), based on the different materials used in their electron blocking layers. The reference device B2.3 and test device B2.3A differ only in the electron blocking layer material; the materials and thicknesses of the remaining layers are the same. The electron blocking layer thickness is 10 nm.

[0329] The driving voltage, luminous efficiency, and lifespan of the reference device B2.3 and the test device B2.3A were tested. The test results are shown in Table 2.7. In Table 2.7, the test data of each device were normalized based on the reference device B2.3. The lifespan is the T95 lifespan, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; Efficiency is current efficiency, and the current density during testing is 15mA / cm 2 .

[0330] Table 2.7

[0331] Compared to the reference device B2.3, the test device B2.3A exhibits lower driving voltage, higher efficiency, and longer lifetime. Compared to compound EBL3-Ref, compound B17 has a deeper HOMO energy level, which facilitates hole injection into the organic light-emitting layer. Compared to compound EBL3-Ref, compound B17 also has a faster mobility, which helps reduce driving voltage.

[0332] Device preparation and testing example 2.4

[0333] The following method was used to prepare a plurality of organic electroluminescent devices and the driving voltage, luminous efficiency and life of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent devices is as follows:

[0334] The prepared ITO substrate is cleaned and dried, and an ITO layer serving as an anode is formed on the ITO substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially stacked on the anode through an evaporation process.

[0335] The hole injection layer is made of a mixture of a hole transport compound and compound PD2.1, with a thickness of 20 nm. The doping ratio of compound PD2.1 is 2%.

[0336] The hole transport layer is made of a hole transport compound with a thickness of 110 nm.

[0337] The material of the electron blocking layer is compound EBL1-Ref, with a thickness of 10 nm;

[0338] The material of the organic light-emitting layer is a mixture of compound BH2.1 and compound BD2.1, the doping ratio of compound BD2.1 is 4%, and the thickness is 20nm;

[0339] The hole blocking layer is made of compound HB2.1 and has a thickness of 10 nm;

[0340] The material of the electron transport layer is compound ET2.1, with a thickness of 30 nm;

[0341] The material of the electron injection layer is compound Yb, with a thickness of 5nm;

[0342] The cathode material is Mg:Ag (2:8) alloy with a thickness of 12 nm;

[0343] The material of the cover layer is CP2.1 and the thickness is 70nm.

[0344] In the device preparation and test example 2.4, according to the different hole-transporting compounds used in the organic electroluminescent device (which results in different materials for the hole injection layer and the hole transport layer of the organic electroluminescent device), the organic electroluminescent device is divided into reference device B2.4A (the hole-transporting compound is compound HT1-Ref), reference device B2.4B (the hole-transporting compound is compound HT2-Ref), test device B2.4A (the hole-transporting compound is compound B58), and test device B2.4B (the hole-transporting compound is compound B224).

[0345] The driving voltage, luminous efficiency, and lifespan of reference device B2.4A, reference device B2.4B, test device B2.4A, and test device B2.4B were tested. The test results are shown in Tables 2.8 and 2.9. In Table 2.8, the test data of each device were normalized using reference device B2.4A as the benchmark. In Table 2.9, the test data of each device were normalized using reference device B2.4B as the benchmark. The lifespan refers to the T95 lifespan, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; Efficiency is current efficiency, and the current density during testing is 15mA / cm 2 .

[0346] Table 2.8

[0347] Table 2.9

[0348] Compared to the reference device B2.4A, the test device B2.4A exhibits higher efficiency and longer lifespan. This is because the hole transport layer in the test device B2.4A incorporates cycloalkylnaphthalene and diphenylfluorene groups, which enhance the material's mobility and provide a relatively shallow energy level. Furthermore, the diphenylfluorene groups have a larger spatial structure, which inhibits aggregation and crystallization, thereby improving the material's film-forming properties.

[0349] Compared to the reference device B2.4B, the test device B2.4B has higher efficiency and longer life. This is because the hole transport layer material in the test device B2.4B reduces the 2- and 3-position substitution of the cycloalkylnaphthalene (when the 2 / 3 positions are substituted simultaneously, a twisted structure is formed), which helps to improve the conjugation of the compound, thereby improving the material mobility and thus the efficiency of the organic electroluminescent device.

[0350] Device preparation and testing example 2.5

[0351] The following method was used to prepare a plurality of organic electroluminescent devices and the driving voltage, luminous efficiency and life of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent devices is as follows:

[0352] The prepared ITO substrate is cleaned and dried. The ITO substrate has an ITO layer as an anode, and the thickness of the ITO layer is 100 nm. A hole injection layer, a hole transport layer, an electron blocking layer (in some cases, it can also be called a light-emitting auxiliary layer), an organic light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer are sequentially stacked on the anode by an evaporation process.

[0353] The hole injection layer is made of HT2.5 doped with PD2.5 at a 2% doping ratio and has a thickness of 10 nm. The hole transport layer is made of HT2.5 and has a thickness of 110 nm. The hole blocking layer is made of HB2.5 and has a thickness of 5 nm. The electron transport layer is a mixture of ET2.5 and LiQ in a 1:1 ratio and has a thickness of 30 nm. The electron injection layer is made of Yb and has a thickness of 5 nm. The cathode is made of a magnesium-silver alloy and has a thickness of 10 nm. The capping layer is made of CP2.5 and has a thickness of 70 nm.

[0354] The difference between the film layers of the organic electroluminescent device prepared in this embodiment lies in the electron blocking layer and the organic light-emitting layer. The materials and thicknesses of the other film layers are the same. Based on the difference between the electron blocking layer and the organic light-emitting layer, the organic electroluminescent device includes:

[0355] Reference device B2.5A (the material of the electron blocking layer is compound EB2.5, with a thickness of 10 nm; the material of the organic light-emitting layer is a mixture of compound BH2.5 and compound BD2.5, with a doping ratio of compound BH2.5 to compound BD2.5 of 96:94, and a thickness of 20 nm)

[0356] Test device B2.5A (the electron blocking layer is made of compound B17, with a thickness of 10 nm; the organic light-emitting layer is made of a mixture of compound BH2.5 and compound BD2.5, with a doping ratio of 96:94 and a thickness of 20 nm)

[0357] Reference device B2.5B (the material of the light-emitting auxiliary layer is compound GP2.5, with a thickness of 40nm; the material of the organic light-emitting layer is a mixture of compounds GH2.5A, GH2.5B and compound GD2.5, with a doping ratio of compounds GH2.5A, GH2.5B and compound GD2.5 of 60:30:10, and a thickness of 32nm)

[0358] Test device B2.5B (the material for the light-emitting auxiliary layer is compound B41, with a thickness of 40nm; the material for the organic light-emitting layer is a mixture of compounds GH2.5A, GH2.5B, and compound GD2.5, with a doping ratio of 60:30:10 for compounds GH2.5A, GH2.5B, and GD2.5, with a thickness of 32nm)

[0359] Reference device B2.5C (the material of the light-emitting auxiliary layer is compound RP2.5, with a thickness of 85nm; the material of the organic light-emitting layer is a mixture of compounds RH2.5A, RH2.5B and compound RD2.5, with a doping ratio of compounds RH2.5A, RH2.5B and compound RD2.5 of 49:49:2, and a thickness of 45nm)

[0360] Test device B2.5C (the material of the light-emitting auxiliary layer is compound B267, with a thickness of 85 nm; the material of the organic light-emitting layer is a mixture of compounds RH2.5A, RH2.5B and compound RD2.5, the doping ratio of compounds RH2.5A, RH2.5B and compound RD2.5 is 49:49:2, and the thickness is 45 nm).

[0361] In this embodiment 2.5, the structural formula of the material used is:

[0362] The driving voltage, luminous efficiency and life of the reference device B2.5A, test device B2.5A, reference device B2.5B, test device B2.5B, reference device B2.5C and test device B2.5C were tested. The test results are shown in Tables 2.10, 2.11 and 2.12. In Table 2.10, the test data of each device were normalized with reference device B2.5A as the benchmark. In Table 2.11, the test data of each device were normalized with reference device B2.5B as the benchmark. In Table 2.12, the test data of each device were normalized with reference device B2.5C as the benchmark. Among them, the life is T95 life, the test temperature is room temperature, and the current density used in the test is 15mA / cm 2 ; Efficiency is current efficiency, and the current density during testing is 15mA / cm 2 .

[0363] Table 2.10

[0364] Table 2.11

[0365] Table 2.12

[0366] Compared to reference device B2.5A, test device B2.5A exhibited higher efficiency; compared to reference device B2.5B, test device B2.5B exhibited higher efficiency; and compared to reference device B2.5C, test device B2.5C exhibited higher efficiency. This efficiency difference is primarily due to the cycloalkylnaphthalene structure used in the electron blocking layer / luminescence-assisting layer of the reference device, which improves hole mobility and better matches the energy levels between the electron blocking layer / luminescence-assisting layer and the organic light-emitting layer, thereby improving efficiency and reducing driving voltage.

[0367] Synthesis example 3.1

[0368] Synthesis of compound C23

[0369] Toluene (150 mL) was added to the reaction flask, followed by the addition of Intermediate SM3.1a (5.58 g, 21 mmol), Intermediate SM3.1b (4.20 g, 20 mmol), and sodium tert-butoxide (2.88 g, 30 mmol). After flushing with nitrogen, Pd2(dba)3 (0.183 g, 0.2 mmol) and Sphos (0.164 g, 0.4 mmol) were added. The mixture was refluxed under nitrogen for 2 hours. The solid was recrystallized by filtration and rinsed with methanol to yield Intermediate SM3.1c.

[0370] Toluene solvent was added to the flask, followed by Intermediate SM3.1c (6.43 g, 15 mmol), Intermediate SM3.1d (4.72 g, 16 mmol), and sodium tert-butoxide (2.16 g, 22.5 mmol). After nitrogen aeration, palladium acetate (0.034 g, 0.15 mmol) and tri-tert-butylphosphine (0.061 g, 0.3 mmol) were added. The nitrogen aeration process was repeated and the mixture was refluxed for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through celite to obtain the filtrate. After concentration, the mixture was heated, a small amount of ethanol was added, and the mixture was allowed to stand at room temperature for recrystallization. The recrystallized solid was filtered and rinsed with ethanol to obtain Compound C23 as a pale yellow solid. Purity: 99.57%, Yield: 88%, MS: 654.77; C47H30N2O2.

[0371] Referring to the synthesis method for compound C23, using starting material 3.1 instead of intermediate SM3.1a, starting material 3.2 instead of intermediate SM3.1b, and starting material 3.3 instead of intermediate SM3.1d, compounds C4, C9, C4, C14, C15, C28, C22, C30, C43, C58, and C60 were synthesized. See Table 3.0 for the individual compounds and the starting materials used to synthesize them.

[0372] Table 3.0

[0373] Refractive index test

[0374] The refractive indices of Compound C4, Compound C9, Compound C14, Compound C15, Compound C23, Compound C28, Compound C22, Compound C30, Compound C43, Compound C58, Compound C60, Compound CP3.1 as a control compound, and Compound CP3.2 as a control compound were tested. The test results are shown in Table 3.1.

[0375] In this refractive index test, the refractive index of the compound was measured using an ellipsometer with a scanning range of 245 to 1000 nm. The test was performed using a silicon wafer vapor-deposited thin film with a thickness of 50 nm.

[0376] Table 3.1

[0377] As can be seen from Table 3.1, the compounds of some embodiments of the present disclosure have a higher refractive index. On the one hand, the compounds of the embodiments of the present disclosure can increase the polarizability of the compounds by introducing heteroatoms such as oxygen or nitrogen. On the other hand, when the heterocyclic ring is connected to the benzene ring, it is a planar structure, and the dihedral angle between the heterocyclic ring plane and the adjacent benzene ring (or other aromatic ring) plane is close to 0, almost in a coplanar state, which increases the conjugation of the compound and helps to increase the refractive index of the molecule. At the same time, the enhanced conjugation of the compound also enhances the absorption of ultraviolet rays by the compound, which helps to improve the protection of other functional materials during organic electroluminescence. In addition, the compounds of the embodiments of the present disclosure have a cycloalkylnaphthalene structure, which can moderately increase the structural stereochemistry of the compound while maintaining a high refractive index, thereby improving the thermal temperature of the material.

[0378] Absorption intensity test and glass transition temperature test

[0379] Absorption intensity test: 50 nm thin films were prepared for compound C4, compound C9, compound C14, compound C15, compound C23, compound C28, compound C22, compound C30, compound C43, compound C58, compound C60, compound CP3.1 as a control compound, and compound CP3.2 as a control compound, and the absorption intensity was tested using an ultraviolet spectrophotometer. The test results at wavelengths of 400 nm and 450 nm are shown in Table 3.2.

[0380] The glass transition temperatures of Compounds C4, C9, C14, C15, C23, C28, C22, C30, C43, C58, C60, and CP3.1 and CP3.2, respectively, were tested using DSC (selecting the second heating step from room temperature to 300°C). The test results are shown in Table 3.2.

[0381] Table 3.2

[0382] As can be seen in Table 3.2, some of the compounds provided in the embodiments of the present disclosure have strong light absorption intensity at 400nm. When used in the cover layer of an organic electroluminescent device, these compounds can absorb ultraviolet light from the external environment, thereby protecting the organic electroluminescent device from damage by ultraviolet light in the external environment, reducing the aging rate of the organic electroluminescent device, and thus extending the life of the organic electroluminescent device. At the same time, these compounds have little absorption of light with wavelengths of 450nm and longer, thus avoiding absorption of the organic electroluminescent device's own light, thereby preventing the impact of light absorption on the light output of the organic electroluminescent device.

[0383] As can be seen from Table 3.2, some of the compounds provided in the embodiments of the present disclosure have relatively high glass transition temperatures. This not only improves the stability of these compounds during the vapor deposition process, but also prevents the formed film from vitrifying, thereby maintaining the stability of the formed film. As such, these compounds have relatively high film-forming properties.

[0384] Device preparation and testing example 3.1

[0385] The organic electroluminescent device was fabricated using the following method: a pre-prepared ITO substrate (100 nm thick) was cleaned and dried; a hole injection material and a hole transport material were co-evaporated onto the anode (ITO) to form the hole injection layer, hole transport layer, and electron blocking layer (EBL) materials; an organic light-emitting layer was then evaporated, including the co-evaporation of BH and BD materials; a hole blocking layer (HBL), electron transport layer (ETL), and electron injection layer (EIL) materials were then evaporated onto the organic light-emitting layer; and a cathode (Mg-Ag alloy) was then evaporated. A capping layer (CPL) material was then evaporated onto the cathode to a thickness of 65 nm.

[0386] The material of the hole injection layer is a mixture of compound PD2.5 and compound HT2.5, the doping ratio of compound PD2.5 is 2%, and the thickness is 10 nm.

[0387] The material of the hole transport layer is compound HT2.5, and the thickness is 110 nm.

[0388] The material of the electron blocking layer is compound EB2.5, and the thickness is 5 nm.

[0389] The material of the organic light-emitting layer is a mixture of compound BH2.5 and compound BD2.5, the doping ratio of compound BD2.5 is 3%, and the thickness is 20 nm.

[0390] The material of the hole blocking layer is HB2.5 and the thickness is 5 nm.

[0391] The material of the electron transport layer is a 1:1 mixture of compound ET2.5 and LiQ, with a thickness of 30 nm.

[0392] The material of the electron injection layer is metal Yb and the thickness is 1 nm.

[0393] The cathode material is magnesium-silver alloy with a thickness of 13nm.

[0394] In this embodiment, a variety of organic electroluminescent devices were prepared using different cover layer materials. The difference between these organic electroluminescent devices lies only in the cover layer material, while the materials and thicknesses of the other film layers are the same. The organic electroluminescent devices prepared in this embodiment include:

[0395] Test device C4 (cover material is compound C4)

[0396] Test device C14 (cover material is compound C14)

[0397] Test device C22 (cover material is compound C22)

[0398] Test device C23 (cover material is compound C23)

[0399] Test device C28 (cover material is compound C28)

[0400] Test device C43 (cover material is compound C43)

[0401] Test device C58 (cover material is compound C58)

[0402] Reference device C3.1 (cover material is compound CP3.1)

[0403] Test device C3.2 (cover material is compound CP3.2)

[0404] The driving voltage, current efficiency and life of test device C4, test device C14, test device C22, test device C23, test device C28, test device C43, test device C58, reference device C3.1 and test device C3.2 were tested. The test results are shown in Table 3.3. The test conditions are a current density of 10 mA / cm 2 In Table 3.3, each test data is normalized based on the test results of reference device C3.1.

[0405] Table 3.3

[0406] Those skilled in the art will readily appreciate other embodiments of the present disclosure after considering the specification and practicing the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the present disclosure that follow the general principles of the present disclosure and include common knowledge or customary techniques in the art not disclosed herein. The description and examples are to be considered as exemplary only, with the true scope and spirit of the present disclosure being indicated by the appended claims.

Claims

1. An aromatic amine compound, wherein The structural formula of the aromatic amine compound is shown in Chemical Formula A or Chemical Formula B: Wherein, L1 is selected from a single bond, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Q1, Q2 and Q3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and at least one of Q1, Q2 and Q3 contains at least one of the groups represented by the following chemical formulas P1 to P6: wherein Ar4 is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkane naphthyl group having 14 to 30 carbon atoms; R4 and R5 are the same or different, and are independently selected from any one of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; R6 is C(R7R8); R7 and R8 are each independently selected from hydrogen, deuterium, fluorine, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Said p represents an integer of 0-6; when p is greater than 1, any two R4 are the same or different; The q represents an integer of 0-4; when q is greater than 1, any two R5 are the same or different; The x represents an integer of 0-3; when x is greater than 1, any two R5 are the same or different; k is an integer from 2 to 4; any two R7s are the same or different; any two R8s are the same or different; When L1, Q1, Q2, Q3, R4, R5, R7, R8, Ar4 have substituents, the substituents of L1, Q1, Q2, Q3, R4, R5, R7, R8, Ar4 may be the same or different, and are independently selected from any one of deuterium, halogen, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms, arylamine having 6 to 30 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkenyl having 2 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, and heteroaryl having 3 to 30 carbon atoms; Represents a connection key.

2. The aromatic amine compound according to claim 1, wherein The R6 is CH2 or CD2, and the k is 2.

3. The aromatic amine compound according to claim 1, wherein The structure of the aromatic amine compound is shown in the following formula I: Wherein, Ar3 is selected from any one of the following groups: Ar1 and Ar2 may be the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkylnaphthalene group, a substituted or unsubstituted cycloalkane naphthyl group or a substituted or unsubstituted cycloalkane naphthyl group. Any one; the heteroaryl group contains at least one or more heteroatoms of O, S, N, and Si; The R1-R3 may be the same or different, and each independently represents any one of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; When Ar1, Ar2, Ar4, R1-R5 have substituents, the substituents of Ar1, Ar2, Ar4, R1-R5 may be the same or different, and are independently selected from any one of deuterium, halogen, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms, arylamine having 6 to 30 carbon atoms, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, and aryl having 6 to 30 carbon atoms; When Ar3 is selected from When at least one of the benzene rings directly connected to the naphthyl group is completely replaced by deuterium; The m represents an integer from 0 to 5; Said n represents an integer of 0-5; The o represents an integer of 0-4.

4. The aromatic amine compound according to claim 3, wherein The aryl group is selected from any one of a methylfluorenyl group, a cycloalkylfluorenyl group having 5 to 10 carbon atoms, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, and a cycloalkanespirofluorene group having 5 to 10 carbon atoms.

5. The aromatic amine compound according to claim 3, wherein The cycloalkylnaphthalene is selected from one of the structures shown below:

6. The aromatic amine compound according to claim 3, wherein The Ar1, Ar2, and Ar4 are each independently selected from a substituted or unsubstituted structure represented by the following formula A-1 to formula A-34:

7. The aromatic amine compound according to claim 3, wherein The aromatic amine compound is selected from one of the structures shown below:

8. The aromatic amine compound according to claim 1, wherein The structural formula of the aromatic amine compound is shown in Chemical Formula II or Chemical Formula III: Wherein, L2 is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

9. The aromatic amine compound according to claim 8, wherein The L2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group.

10. The aromatic amine compound according to claim 9, wherein When L2 has a substituent, the substituent on L2 is selected from deuterium, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, and an alkyl group having 1 to 4 carbon atoms; when there are multiple substituents on L2, any two substituents are the same or different.

11. The aromatic amine compound according to claim 8, wherein The Q2 is selected from The Q3 is selected from Wherein, Ar5 and Ar6 are the same or different and are independently selected from a substituted or unsubstituted group W1, and the unsubstituted group W1 is selected from: Among them, the substituted group W1 is a group formed by replacing the unsubstituted group W1 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 20 carbon atoms, and a heteroaryl group with 3 to 20 carbon atoms; and when the number of substituents on the substituted group W1 is multiple, any two substituents are the same or different.

12. The aromatic amine compound according to claim 11, wherein L3 and L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted group W2, and the unsubstituted group W2 is selected from: The substituted group W2 is an unsubstituted group W2 substituted by one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms. When the number of substituents on the substituted group W2 is multiple, any two substituents are the same or different.

13. The aromatic amine compound according to claim 8, wherein is selected from substituted or unsubstituted groups W3, and the unsubstituted groups W3 are selected from structural formulas a1 to a280: Describe chemical bonds; The substituted group W3 is a group formed by replacing the unsubstituted group W3 with one or more deuteriums.

14. The aromatic amine compound according to claim 8, wherein The aromatic amine compound is selected from substituted or unsubstituted compound W4, and the unsubstituted compound W4 is selected from the group consisting of the following compounds: The substituted compound W4 is a compound in which the unsubstituted compound W4 is substituted by one or more deuteriums.

15. The aromatic amine compound according to claim 14, wherein The substituted compound W4 is all SP on the unsubstituted compound W4 2 A compound formed by replacing all hydrogen on hybridized carbon with deuterium.

16. The aromatic amine compound according to claim 1, wherein The structural formula of the aromatic amine compound is shown in Chemical Formula II: Wherein, L2 is selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 3 to 30 carbon atoms; wherein, Q2 and Q3 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 3 to 50 carbon atoms, and at least one of Q2 and Q3 contains a fused aromatic heterocycle, and each heteroatom in the fused aromatic heterocycle is each independently selected from N, O and S.

17. The aromatic amine compound according to claim 16, wherein At least one of Q2 and Q3 contains the following fused aromatic heterocyclic group: Wherein, X1 is selected from C(Y6Y7), NY8, O, S; X2 is selected from NY8, O, S; Y1, Y2, Y3, and Y4 are each independently selected from CY8 or N, and only one of them is selected from N; Y5, Y6, Y7, and Y8 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an arylene group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms.

18. The aromatic amine compound according to claim 17, wherein X1 is selected from O and S; X2 is selected from O and S; Y8 is selected from hydrogen and deuterium; Y5 is selected from hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl and phenanthryl.

19. The aromatic amine compound according to claim 17, wherein At least one of Q2 and Q3 is selected from the group consisting of:

20. The aromatic amine compound according to claim 16, wherein When Q2 does not contain a fused aromatic heterocycle, Q2 is selected from a substituted or unsubstituted group W5; when Q3 does not contain a fused aromatic heterocycle, Q3 is selected from a substituted or unsubstituted group W5; The unsubstituted group W5 is selected from an aryl group having 6 to 40 carbon atoms and a heteroaryl group having 5 to 40 carbon atoms; Wherein, the substituted group W5 is an unsubstituted group W5 replaced by one or more selected from deuterium, The group W5 is substituted by fluorine, chlorine, bromine, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 6 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; and when the number of substituents on the substituted group W5 is multiple, any two substituents are the same or different.

21. The aromatic amine compound according to claim 20, wherein The unsubstituted group W5 is selected from biphenyl, terphenyl, naphthyl-substituted phenyl, naphthyl-substituted biphenyl, anthracenyl, anthracenyl-substituted phenyl, anthracenyl-substituted biphenyl, phenanthryl, phenanthryl-substituted phenyl, phenanthryl-substituted biphenyl.

22. The aromatic amine compound according to claim 16, wherein The L2 is selected from phenylene, biphenylene, terphenylene, naphthylene, dibenzofuranylene, and dibenzothiophenylene.

23. The aromatic amine compound according to claim 16, wherein The aromatic amine compound is selected from the group consisting of the following compounds:

24. An electroluminescent device, wherein: The electroluminescent device comprises an organic layer, and the organic layer comprises the aromatic amine compound according to any one of claims 1 to 23.

25. The electroluminescent device according to claim 24, wherein The electroluminescent device comprises an anode, a first functional layer, a light-emitting functional layer and a cathode which are stacked in sequence; The aromatic amine compound is located in the first functional layer.

26. The electroluminescent device according to claim 25, wherein The first functional layer includes a hole injection layer, a hole transport layer and an electron blocking layer which are stacked; At least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the aromatic amine compound.

27. The electroluminescent device according to claim 26, wherein: At least one of the hole injection layer, the hole transport layer and the electron blocking layer contains the aromatic amine compound according to any one of claims 3 to 15.

28. The electroluminescent device according to claim 24, wherein: The electroluminescent device comprises a first electrode, a light-emitting functional layer, a second electrode and a covering layer which are stacked in sequence; the covering layer is located at the light-emitting side of the electroluminescent device; and the covering layer comprises the aromatic amine compound.

29. The electroluminescent device according to claim 28, wherein The covering layer comprises the aromatic amine compound according to any one of claims 16 to 23.

30. The electroluminescent device according to any one of claims 24 to 29, wherein: The electroluminescent device is an organic light emitting diode, a polymer light emitting diode or a quantum dot light emitting diode.

31. A display device comprising the electroluminescent device according to any one of claims 24 to 30.

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