Aromatic amine compound, electroluminescent device and display device

Abstract

The invention discloses an aromatic amine compound, an electroluminescent device and a display device, and belongs to the technical field of display, and the aromatic amine compound can improve the performance of the electroluminescent device.

Description

Aromatic Amine Compound, Electroluminescent Device and Display Device

[0001] Cross-reference

[0002] This disclosure claims the priority of a Chinese patent application with the application number 202311220949.8 and the title "An Aromatic Amine Compound for Organic Electroluminescent Devices, Its Preparation Method and Application", filed on September 20, 2023. The entire content of this Chinese patent application is incorporated herein by reference in its entirety.

[0003] This disclosure relates to the field of display technologies, and specifically, to an aromatic amine compound, an electroluminescent device and a display device.

[0004] An electroluminescent device can emit light by itself under the drive of an electric current. An electroluminescent device generally includes at least an anode, a functional layer and a cathode arranged in a stacked manner; the holes provided by the anode and the electrons provided by the cathode are recombined in the functional layer, causing the functional layer 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, full colorization, etc., and have extremely high research and development value and broad application prospects.

[0006] It should be noted that the information disclosed in the above background art section is only used to enhance the understanding of the background of this disclosure, and thus may include information that does not constitute the prior art known to those of ordinary skill in the art.

[0007] Summary of the invention

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

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

[0010] Wherein, L 1 is selected from a single bond, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;

[0011] Q 1 、Q 2 and Q 3Each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and Q 1 、Q 2 and Q 3 at least one of them contains at least one of the groups represented by Chemical Formula P1 to Chemical Formula P6:

[0012] Among them, Ar 4 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, a substituted or unsubstituted naphthacenyl group having 14 to 30 carbon atoms;

[0013] Said R 4 and R 5 are the same or different, and each independently selected from 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, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

[0014] R 6 is C(R 7 R 8 )); R 7 and R 8 are each independently selected from hydrogen, deuterium, fluorine, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;

[0015] Said p represents an integer from 0 to 6; when p is greater than 1, any two R 4 are the same or different;

[0016] Said q represents an integer from 0 to 4; when q is greater than 1, any two R 5 are the same or different;

[0017] Said x represents an integer from 0 to 3; when x is greater than 1, any two R 5 are the same or different;

[0018] k is an integer from 2 to 4; any two R 7 are the same or different; any two R 8 are the same or different;

[0019] When L 1 、Q1 and Q 2 and Q 3 and R 4 and R 5 and R 7 and R 8 and Ar 4 When there are substituents, the 1 and Q 1 and Q 2 and Q 3 and R 4 and R 5 and R 7 and R 8 and Ar 4 substituents of can be the same or different and are each independently selected from deuterium, halogen, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms, arylamino 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;

[0020] represents a linking bond.

[0021] According to another aspect of the present disclosure, there is provided an electroluminescent device, wherein the electroluminescent device has an organic layer, and the organic layer includes the above-mentioned aromatic amine compound.

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

[0023] It should be understood that the above general description and the following detailed description are only exemplary and explanatory, and cannot limit the present disclosure.

[0024] The accompanying drawings herein are incorporated into the specification and constitute a part of the specification, showing embodiments consistent with the present disclosure, and are used together with the specification to explain the principles of the present disclosure. Obviously, the accompanying drawings in the following description are only some embodiments of the present disclosure, and those of ordinary skill in the art can obtain other drawings based on these drawings without creative efforts.

[0025] FIG. 1 is a schematic structural diagram of an electroluminescent device in an embodiment of the present disclosure.

[0026] FIG. 2 is a partial structural schematic diagram of a display panel in an embodiment of the present disclosure.

[0027] Example embodiments will now be described more fully with reference to the accompanying drawings. However, the example embodiments can be implemented in various 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 concept of the example embodiments to those skilled in the art. Like reference numerals in the figures denote like or similar structures and thus their detailed description will be omitted. In addition, the drawings are only 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 relative relationship of one component of an icon to another component, these terms are used in this specification only for convenience, for example, according to the directions of the examples described in the drawings. It can be understood that if the device of the icon is turned upside down, the component described as "upper" will become the component "lower". When a structure is "on" another structure, it may mean that a structure is integrally formed on another structure, or that a structure is "directly" disposed on another structure, or that a structure is "indirectly" disposed on another structure through another 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 "comprising" and "having" are used to mean an open inclusion and mean that there may be additional elements / components / etc. in addition to the listed elements / components / etc.; the terms "first", "second", "third", etc. are used only as labels and are not a limitation on 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 various 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 concept of the example embodiments to those skilled in the art. Like reference numerals in the figures denote like or similar structures and thus their detailed description will be omitted. In addition, the drawings are only schematic illustrations of the present disclosure and are not necessarily drawn to scale.

[0031] In the present disclosure, the description method of "each independently selected from..." should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that within the same group, the specific options expressed between 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, chlorine, which means that: 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 the biphenyl, and the number q' of the 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 the present disclosure, an unpositioned linking bond refers to a single bond extending from a ring system It means that one end of the linking bond can be connected to any feasible position in the ring system penetrated by the bond, 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 unpositioned linking bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connection mode 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 of the molecule through an unpositioned linking bond extending from the middle of one benzene ring, and the meaning it represents includes any possible connection mode shown in formulas (X'-1) to (X'-4).

[0035] The unpositioned 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 connected to 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 through an unpositioned linking bond, and the meaning it represents includes any possible connection mode shown in formulas (Y-1) to (Y-7).

[0036] In the present disclosure, in the G group with a substituted or unsubstituted carbon atom number of M, the carbon atom number of the G group is M, and this carbon atom number M does not consider the carbon atoms on the substituent; for example, in the G group with a methyl-substituted carbon atom number of M, the total number of carbon atoms is M + 1. Correspondingly, in the aryl group with a substituted or unsubstituted carbon atom number of M or the heteroaryl group with a substituted or unsubstituted carbon atom number of M, the carbon atom number M does not count the carbon atoms on the substituent, but only considers the carbon atoms on the aromatic ring or heteroaromatic ring. For example, is an aryl group having 6 carbon atoms substituted with methyl; is an unsubstituted arylene group having 12 carbon atoms.

[0037] In the present disclosure, when no specific definition is provided otherwise, "hetero" means including at least 1 heteroatom such as B, N, O, S, Se, Si or P in a functional group and the remaining atoms are carbon, hydrogen and deuterium. An unsubstituted alkyl group may be a "saturated alkyl group" without any double bond or triple bond.

[0038] In the present disclosure, "alkyl" may include a straight-chain alkyl group or a branched-chain alkyl group. The alkyl group may have 1 to 18 carbon atoms. In the present disclosure, a numerical range such as "1 to 18" means each integer in the given range; for example, "an alkyl group having 1 to 18 carbon atoms" means an alkyl group that may contain 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, 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. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and pentyl.

[0040] In the present disclosure, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. The cycloalkyl group may have 5 to 10 carbon atoms. In the present disclosure, a numerical range such as "a cycloalkyl group having 5 to 10 carbon atoms" means each integer in the given range; for example, "a cycloalkyl group having 5 to 10 carbon atoms" means a cycloalkyl group that may contain 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms.

[0041] Optionally, specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0042] In the present disclosure, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused polycyclic aryl group conjugated through carbon-carbon bonds, or two or more fused polycyclic aryl groups conjugated through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as the aryl groups in the present disclosure. Among them, the fused polycyclic aryl group can include, for example, bicyclic fused aryl groups (e.g., naphthyl), tricyclic fused aryl groups (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl group 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 groups. Examples of aryl groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, and the like. In the present disclosure, biphenyl can be understood as an aryl group substituted by a phenyl group or an unsubstituted aryl group. In the present disclosure, the arylene group involved refers to a divalent group formed by an aryl group further losing one hydrogen atom.

[0043] In the present disclosure, the substituted aryl group can be one or more hydrogen atoms in the aryl group substituted by, such as deuterium atoms, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, alkoxy groups, or other groups.

[0044] In the present disclosure, a heteroaryl is a monovalent aromatic ring or a derivative thereof that contains at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se, and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc., without being limited thereto. Among them, thienyl, furyl, phenanthrolinyl, etc. are heteroaryls of the single aromatic ring system type, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl are heteroaryls of the polycyclic system type conjugated through carbon-carbon bonds.

[0045] In the present disclosure, a substituted heteroaryl can be one or more hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, alkoxy groups, etc.

[0046] The present disclosure provides an aromatic amine compound, which can be applied to an electroluminescent device to improve the performance of the electroluminescent device. Specifically, at least some of the film layers in the electroluminescent device can adopt the aromatic amine compound provided by the present disclosure. For example, the electroluminescent device has an organic layer, and the organic layer contains the aromatic amine compound provided by the present disclosure. The organic layer containing the aromatic amine compound provided by the present disclosure can also contain other components, or can only contain the aromatic amine compound provided by the embodiments of the present disclosure.

[0047] Optionally, the electroluminescent device can at least include 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 can be located in the functional layer between the two electrodes or outside the two electrodes to facilitate light extraction.

[0048] Optionally, referring to FIG. 1, the two electrodes (the first electrode and the second electrode) of the electroluminescent device can be the anode 1 and the cathode 9 of the electroluminescent device respectively. For example, the first electrode can be used as the anode and the second electrode can be used 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. Electrons and holes recombine in the functional layer and emit light.

[0049] In the present disclosure, referring to FIG. 1, the functional layer of the electroluminescent device can include a light-emitting functional layer 5. Electrons and holes can recombine in the light-emitting functional layer to form excitons, thereby causing the light-emitting functional layer to emit light. Optionally, the light-emitting functional layer can be a small-molecule organic light-emitting functional layer, a macromolecule polymer light-emitting functional layer, or a quantum dot light-emitting functional layer. Thus, the electroluminescent device can 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 FIG. 1, the functional layer of the electroluminescent device can further include a first functional layer (hole transport region) located between the light-emitting functional layer and the anode. The first functional layer can inject the holes injected from the anode into the light-emitting functional layer. For example, the first functional layer can 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 all of the hole injection layer, the hole transport layer, and the electron blocking layer at the same time, the anode, the hole injection layer, the hole transport layer, the electron blocking layer, and the light-emitting functional layer are stacked in sequence. Some aromatic amine compounds provided in 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 light-emitting efficiency of the electroluminescent device, improving the device lifetime of the electroluminescent device, and reducing the driving voltage of the electroluminescent device.

[0051] In some embodiments of the present disclosure, referring to FIG. 1, the functional layer of the electroluminescent device can further include a second functional layer (electron transport region) located between the light-emitting functional layer and the cathode. The second functional layer can inject the electrons injected from the cathode into the light-emitting functional layer. For example, the second functional layer can 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 all of the electron injection layer, the electron transport layer, and the 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 the embodiments of the present disclosure, the materials of the respective film layers of the second functional layer can be selected as needed. Any film layer can be an organic material, an inorganic material, or a hybrid material of an organic material and an inorganic material.

[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 can improve the electron-hole separation efficiency, and thus play a role similar to that of the anode or the cathode. The charge generation layer is adjacent to the first functional layer and can inject holes into the first functional layer, and thus play a role similar to that of the anode with respect to the first functional layer; the charge generation layer is adjacent to the second functional layer and can inject electrons into the second functional layer, and thus play a role similar to that of the cathode with respect to the second functional layer. When the electroluminescent device is 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 FIG. 1, the electroluminescent device further includes a cover layer 10 provided on the light-emitting side; some arylamine compounds provided by the present disclosure are particularly suitable for application to this cover layer to improve the light extraction efficiency of the electroluminescent device or to improve the lifespan of the electroluminescent device. In one example, the electroluminescent device includes a first electrode, a light-emitting functional layer, a second electrode, and a cover layer that are sequentially stacked; the cover layer is located on the light-emitting side of the electroluminescent device; the cover layer includes one or more aromatic amine compounds provided by the present disclosure. In this example, the second electrode may be a cathode or an anode. In other words, when the electroluminescent device emits light from the first electrode, the cover layer is provided on the side of the first electrode away from the second electrode; conversely, when the electroluminescent device emits light from the second electrode, the cover layer is provided on the side of the second electrode away from the first electrode.

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

[0055] The present disclosure provides an arylamine compound, wherein the structural formula of the arylamine compound is shown as Chemical Formula A or Chemical Formula B:

[0056] wherein, L 1 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;

[0057] Q 1 、Q 2 and Q 3 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and Q1 , Q 2 and Q 3 at least one of them contains at least one of the groups represented by Chemical Formula P1 to Chemical Formula P6 as follows:

[0058] Among them, Ar 4 is selected from hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted naphthyl fused with cycloalkane with 14 to 30 carbon atoms;

[0059] The said R 4 and R 5 are the same or different, and each independently is selected from any one of deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms;

[0060] R 6 is C(R 7 R 8 ); R 7 and R 8 are each independently selected from hydrogen, deuterium, fluorine, alkyl with 1 to 4 carbon atoms, substituted or unsubstituted aryl with 6 to 12 carbon atoms;

[0061] The said p represents an integer from 0 to 6; when p is greater than 1, any two R 4 are the same or different;

[0062] The said q represents an integer from 0 to 4; when q is greater than 1, any two R 5 are the same or different;

[0063] The said x represents an integer from 0 to 3; when x is greater than 1, any two R 5 are the same or different;

[0064] k is an integer from 2 to 4; any two R 7 are the same or different; any two R 8 are the same or different;

[0065] When L 1 , Q 1 , Q 2 , Q 3 , R 4 , R5 , R 7 , R 8 , Ar 4 When there are substituents, the substituents of the said L 1 , Q 1 , Q 2 , Q 3 , R 4 , R 5 , R 7 , R 8 , Ar 4 can be the same or different and are each independently selected from deuterium, halogen, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, alkyl with 1 to 30 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, alkenyl with 2 to 30 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 3 to 30 carbon atoms;

[0066] represents a connecting bond.

[0067] The aromatic amine compound provided by the embodiment of the present disclosure has a structure shown in Chemical Formula A or Chemical Formula B, and at least includes at least one of the groups shown in Chemical Formula P1 to Chemical Formula P6. Introducing at least one of the groups shown in Chemical Formula P1 to Chemical Formula P6 into the triarylamine structure can effectively improve the film-forming performance of the compound. Specifically, in the groups shown in Chemical Formula P1 to Chemical Formula P4, there is a large steric hindrance between the Ar 4 group on the naphthalene ring and the triarylamine main group. Therefore, the plane where the triarylamine main group is located, the plane where the naphthalene ring is located, and the plane where the Ar 4 group is located will present a certain angle, thereby improving the stereoscopic property of the aromatic amine compound and reducing the stacking between molecules, thereby improving the film-forming property. In the groups shown in Chemical Formula P5 to Chemical Formula P6, there is a cycloalkane structure on the benzene ring, which can also improve the stereoscopic property of the aromatic amine compound, thereby reducing the stacking between molecules and improving the film-forming property. Moreover, in some specific types of compounds, the aromatic amine compound also has improved electrochemical characteristics or optical characteristics, 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, wherein, Ar 4 is selected from substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted naphthacenyl with 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 naphthacene (such as acenaphthenyl, deuterated acenaphthenyl, etc.) introduced by the aromatic amine compound has strong electron-donating ability (increasing the electron cloud density), which can improve the hole mobility. And compared with naphthalene, acenaphthenyl or deuterated acenaphthenyl will increase the molecular weight, which can improve the thermal stability (high glass transition temperature) of the aromatic amine compound and ensure that the device has a good lifespan. At the same time, naphthacene increases the molecular weight (which can also improve the solubility of the material and facilitate the cleaning of the evaporation mask), but has little effect on the sublimation temperature, which is beneficial to the evaporation process. The groups shown in Chemical Formula P5 to Chemical Formula P6 enhance the anisotropy of the material through the twisted structure and steric hindrance, effectively increasing the lateral steric hindrance of the material. When this aromatic amine compound is applied to the first functional layer, especially when applied to common film layers such as the hole injection layer or the hole transport layer, this aromatic amine compound can improve the device crosstalk and lateral leakage conditions. At the same time, by introducing D or some stable fragments for modification, a series of excellent organic materials can be synthesized, which can be used as hole transport materials. At the same time, the groups shown in Chemical Formula P5 to Chemical Formula P6 can make this aromatic amine compound have a large refractive index, so that this aromatic amine compound can be applied to the cover layer.

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

[0071] Wherein, Ar 3 is selected from any one of the following groups:

[0072] Ar 1 and Ar 2 can be the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, or any one of substituted or unsubstituted cycloalkylnaphthalenes; at least one or more heteroatoms of O, S, N, Si are contained in the heteroaryl group;

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

[0074] When Ar 1 、Ar 2 、Ar 4 、R 1 -R 5 has substituents, the substituents of the said Ar 1 、Ar 2 、Ar 4 、R 1 -R 5 can be the same or different and are each independently selected from deuterium, halogen, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, alkyl with 1 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, and aryl with 6 to 30 carbon atoms;

[0075] When Ar 3 is selected from , all the hydrogens on at least one benzene ring directly connected to the naphthyl group are completely replaced by deuterium;

[0076] The said m represents an integer from 0 to 5;

[0077] The said n represents an integer from 0 to 5;

[0078] The said o represents an integer from 0 to 4.

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

[0080] Technicians found that after the Ar 3 group is selected as a naphthyl structure or cycloalkylnaphthalene structure with a large steric hindrance, when the connection position includes at least the 1,8-position or 2,3-position, the formed connection angle can effectively avoid the stacking between molecules and improve the film-forming property; at the same time, when all the hydrogens on the benzene ring directly connected to the naphthyl structure or cycloalkylnaphthalene structure are completely replaced by deuterium, the service life of the device can be improved. Further, when the connection position of the benzene ring and the naphthyl structure or cycloalkylnaphthalene structure is the 1,8-position or 2,3-position and all the hydrogens on the benzene ring are completely replaced by deuterium, the effect of improving the device life is more obvious; in addition, in Ar 3Introducing a naphthyl structure or a cycloalkylnaphthalene structure with a linking position at 2,3- is more effective in improving device performance than introducing a naphthyl structure or a cycloalkylnaphthalene structure with a linking position at 1,8-. This is because the naphthyl structure or the cycloalkylnaphthalene structure with a linking position at 2,3- has a larger physical property adjustment space, can effectively block exciton recombination at the interface, and further improve 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 light emission efficiency of the device, reduce the energy consumption of the device, lower the driving voltage, and also extend the service life of the device. Additionally, when a cycloalkylnaphthalene structure is introduced at the Ar 3 position, not only can the same characteristics as those of the introduced naphthyl structure be ensured, but also the solubility of the aromatic amine compound can be increased, which is convenient for cleaning the evaporation mask plate. At the same time, it can also improve the sublimation temperature to a certain extent, which is beneficial to improving the device stability.

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

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

[0083] In an 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 an embodiment of the present disclosure, in the first type of aromatic amine compound, the Ar 1 , Ar 2 , Ar 4 each independently is selected from one of the structures represented by the following formula A-1 to formula A-34, which may be substituted or unsubstituted:

[0085] In an example, when the formula A1 to formula A34 have substituents, the substituents on the formula A1 to formula A34 can be deuterium. For example, the Ar 1 , Ar 2 , Ar 4 each independently is selected from a substituted or unsubstituted group A'; the unsubstituted group A' is independently selected from the formula A1 to formula A34; the substituted group A' is a substituent formed by substituting at least one hydrogen 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 structures shown below:

[0087] Furthermore, when Ar 3 is selected from any one of, the hydrogen on the benzene ring directly connected to Ar 4 in the group can be arbitrarily substituted with deuterium, and the hydrogen on the benzene ring connected to N on the main structure at the bonding position can be arbitrarily substituted with deuterium to improve the device life; exemplarily, its structure can be: 3 This structure can be understood as one of the deuterated compound forms of compound 130; or it can be

[0088] This structure can be understood as one of the deuterated compound forms of compound 130; or it can be This structure can be understood as one of the deuterated compound forms of Compound 136. There are many other compounds with this property, which will not be listed and numbered one by one here. To obtain such deuterated compounds, it is only necessary to select starting materials with deuterium substitution during preparation, and the preparation process is the same as that of the non-deuterated compounds with the same structure.

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

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

[0091] Add Compound a and Compound b to a solvent, heat under reflux in an inert atmosphere for 0.5 - 1.5 h, then cool to below 80 °C, add potassium carbonate and tetrakis(triphenylphosphine)palladium, and continue refluxing for 8 - 10 h. After the reaction is completed, wash with water, extract the organic phase with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, evaporate the organic phase by rotary evaporation to obtain a crude product, and recrystallize and purify the crude product with dichloromethane and n-heptane to obtain Compound c;

[0092] Add Compound c and Compound d to a solvent, heat under reflux in an inert atmosphere for 1.5 - 2 h, add sodium tert-butoxide, 2 - (dicyclohexylphosphino)-2',6'-dimethoxybiphenyl, and tris(dibenzylideneacetone)dipalladium, and continue refluxing for 8 - 10 h. After the reaction is completed, quench with water, add dichloromethane and water for extraction, dry the organic phase with anhydrous magnesium sulfate, evaporate the organic phase by rotary evaporation, and recrystallize and purify by column chromatography using toluene and n-heptane to obtain the product;

[0093] Among them, the Compound a is selected from one of them;

[0094] The Compound b is selected from

[0095] The Compound d is selected from

[0096] Ar 1 、Ar 2 、Ar 4They 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; at least one or more heteroatoms selected from O, S, N, and Si are contained in the heteroaryl group;

[0097] Said R 1 ~R 5 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 Ar 1 、Ar 2 、Ar 4 、R 1 -R 5 has a substituent, the substituents of said Ar 1 、Ar 2 、Ar 4 、R 1 -R 5 may be the same or different and each independently is 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, an alkenyl group having 2 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms;

[0099] Said m represents an integer from 0 to 5;

[0100] Said n represents an integer from 0 to 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 linking bond.

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

[0106] According to one aspect of the present disclosure, the present disclosure further provides an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, and 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] Among them, 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, there is also provided a display device, which 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. By introducing a naphthyl structure or a cycloalkylnaphthyl structure with a linking position at the 1,8-position or 2,3-position at the Ar 3 position, the formed linking angle can increase its steric hindrance, avoid stacking between molecules, and improve the film-forming property.

[0112] 2. By introducing a naphthyl structure or a cycloalkylnaphthyl structure with a linking position at the 2,3-position at the Ar 3 position, the first type of aromatic amine compound has a larger space for physical property adjustment, can effectively block the recombination of excitons at the interface, and further improve the mobility.

[0113] 3. When a cycloalkylnaphthyl structure is introduced at the Ar 3 position of the aromatic amine compound, it can not only ensure the same characteristics as those introduced with a naphthyl structure, but also increase the solubility of the aromatic amine compound, facilitate the cleaning of the evaporation mask, and can also improve the sublimation temperature to a certain extent, which is beneficial to improving the device stability.

[0114] 4. By adjusting the substituents on the aromatic amine compound, a series of materials with different characteristics can be effectively obtained. For example, introducing groups such as dibenzofuran, carbazole, and fluorene in the structure can ensure that the aromatic amine compound has high T1 characteristics, 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), high hole mobility, can be used as a hole transport material, an electron blocking material or a light-emitting layer material, improve the device lifetime and current efficiency, and can significantly reduce the device voltage.

[0116] In one embodiment of the present disclosure, the first type of aromatic amine compound of the present disclosure is applicable to light-emitting elements, display panels, and electronic devices, and is particularly applicable to organic electroluminescent devices. The electronic device of the present disclosure is a device including at least one layer of an organic compound, and the device may also include 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 of the present disclosure can be prepared by using representative reactions such as 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, L 2 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-fused naphthalene) introduced in the second type of aromatic amine compound has a strong electron-donating ability (increasing the electron cloud density), which can improve the hole mobility; and compared with naphthalene, its molecular weight increases, which can enhance the thermal stability of the molecule (for example, increasing the glass transition temperature), ensuring that the device has a good lifespan. At the same time, the cycloalkylnaphthalene increases the molecular weight (which can also improve the solubility of the material and facilitate 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 through a twisted structure and steric hindrance, effectively increasing the lateral steric hindrance of the material, and thus can improve the device crosstalk and lateral leakage conditions. 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-transporting materials.

[0121] Through a large number of verifications, the inventors found that compared with the first type of aromatic amine compounds containing structural formulas P1 to P4, this second type of aromatic amine compound has a faster migration rate, which has a very effective result in improving the device performance. Moreover, this second type of aromatic amine compound also has a deeper HOMO energy level, which enables it to be applied in the electron blocking layer, facilitating the improvement of the hole injection speed from the hole transport layer to the light-emitting functional layer and making up for the defect of slow migration rate in the related art of the light-emitting auxiliary layer (especially blue).

[0122] In one example, R 5 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 hydrogens on the naphthalene ring of 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 hydrogens on the naphthalene ring of unsubstituted W6 with deuterium.

[0127] In one embodiment of the second type of aromatic amine compound, the L 2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group.

[0128] In one embodiment of the second type of aromatic amine compound, when the L 2 has a substituent, the substituent on the L 2 is selected from deuterium, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms; when the number of substituents on the L 2 is multiple, any two substituents are the same or different. In particular, the substituent on the L 2 is selected from deuterium or an aryl group having 6 to 12 carbon atoms.

[0129] In one example, when the L 2 has a substituent, the substituent on the L 2 is deuterium: L2 at least one hydrogen on is replaced by deuterium, such as L 2 all hydrogens on are replaced by deuterium.

[0130] In one embodiment of the second type of aromatic amine compound, unsubstituted L 2 is selected from the group consisting of the following structures:

[0131] In one embodiment of the second type of aromatic amine compound, the Q 2 is selected from The Q 3 is selected from Wherein, Ar 5 and Ar 6 are the same or different, and each independently is selected from a substituted or unsubstituted group W1, and the unsubstituted group W1 is selected from:

[0132] Wherein, the substituted group W1 is a group formed by substituting 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 for the unsubstituted group W1; and when the number of substituents on the substituted group W1 is multiple, any two substituents are 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, L 3 and L 4 are the same or different, and each independently is selected from a single bond, a substituted or unsubstituted group W2, and the unsubstituted group W2 is selected from:

[0135] Among them, the substituted group W2 is a group formed by substituting 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 for the unsubstituted group W2, and when the number of substituents on the substituted group W2 is plural, any two substituents are the same or different.

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

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

[0138] ------Represents a chemical bond;

[0139] Among them, the substituted group W3 is a group formed by substituting one or more hydrogens of the unsubstituted group W3 with deuterium. For example, the substituted group W3 is a group formed by substituting each hydrogen of the unsubstituted group W3 with deuterium.

[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] Among them, the substituted compound W4 is a compound formed by substituting one or more hydrogens of the unsubstituted compound W4 with deuterium.

[0142] In one example, the substituted compound W4 is a compound formed by substituting each hydrogen of the unsubstituted compound W4 with deuterium.

[0143] In another example, the substituted compound W4 is all SP on the unsubstituted compound W4 2A 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. The structural formula of the third type of aromatic amine compound is shown in Chemical Formula II:

[0145] Wherein, L 2 is selected from a single bond, a substituted or unsubstituted aryl group with 6 - 30 carbon atoms, and a substituted or unsubstituted heteroaryl group with 3 - 30 carbon atoms; wherein, Q 2 and Q 3 are each independently selected from a substituted or unsubstituted aryl group with 6 - 50 carbon atoms and a substituted or unsubstituted heteroaryl group with 3 - 50 carbon atoms, and at least one of Q 2 and Q 3 contains a fused aromatic heterocycle, and each heteroatom in the fused aromatic heterocycle is independently selected from N, O, and S.

[0146] This third type of aromatic amine compound has a high refractive index and high thermal stability, and can be applied to the cover layer of an electroluminescent device, thereby improving the performance of the electroluminescent device. This third type of aromatic amine compound takes aromatic amine as the core and introduces a fused aromatic heterocycle (containing heteroatoms), thereby increasing the polarizability of the third type of aromatic amine compound; introducing the group P6 into this third type of aromatic amine compound can increase its refractive index, thereby improving the light extraction efficiency of the electroluminescent device. Moreover, by introducing the group P6 and the fused aromatic heterocycle, the refractive index value of this third type of aromatic amine compound in the wavelength range of 450 - 630 nm can be 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 Q 2 and Q 3 has a fused aromatic heterocycle, which makes the angle between aromatic groups of this third type of aromatic amine compound small, has good planarity and strong conjugation, thereby facilitating the increase of its refractive index and the enhancement of its light absorption intensity at 400 nm, and increasing the absorption of ultraviolet light. The group P6 is introduced into this third type of aromatic amine compound, which makes this third type of aromatic amine compound maintain a high refractive index while appropriately increasing the three-dimensionality of the structure, thereby improving the film-forming performance of the material (such as increasing its glass transition temperature).

[0147] In one embodiment of the third type of aromatic amine compound, at least one of the Q 2 and Q 3 contains the following fused aromatic heterocyclic groups:

[0148] Among them, X 1 is selected from C(Y 6 Y 7 ), NY 8 , O, S; X 2 is selected from NY 8 , O, S;

[0149] Y 1 , Y 2 , Y 3 , Y 4 are each independently selected from CY 8 or N, and only one is selected from N; Y 5 , Y 6 , Y 7 , Y 8 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.

[0150] In one embodiment of the third type of aromatic amine compound, X 1 is selected from O, S; X 2 is selected from O, S; Y 8 is selected from hydrogen, deuterium; Y 5 is selected from hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl.

[0151] In one embodiment of the third type of aromatic amine compound, Q 2 and Q 3 at least one of which is selected from the group consisting of the following groups:

[0152] In one embodiment of the third type of aromatic amine compound, when Q 2 does not contain a fused heteroaromatic ring, Q 2 is selected from a substituted or unsubstituted group W5; when Q 3 does not contain a fused heteroaromatic ring, Q 3 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] Among them, the substituted group W5 is a group formed by substituting the unsubstituted group W5 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 6 to 10 carbon atoms, and aryl substituents having 6 to 12 carbon atoms. When the number of substituents on the substituted group W5 is multiple, any two substituents are the same or different.

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

[0156] In one embodiment of the third type of aromatic amine compound, the L 2 is selected from phenylene, biphenylene, terphenylene, naphthylene, dibenzofuranylene, and dibenzothiophenylene. In one example, L 2 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 the aromatic amine compound provided by 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 by the embodiment of the present disclosure. For example, the material of the hole injection layer may be a mixture of the first type of aromatic amine compound provided by the embodiment of the present disclosure and a doping material, or a mixture of the second type of aromatic amine compound and a doping material.

[0159] In some other embodiments of the present disclosure, the hole injection layer may adopt other materials other than the aromatic amine compound 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 may also be selected from p-type dopants with 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 by 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 by 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 by the embodiment of the present disclosure, or the material of the hole transport layer may be the second type of aromatic amine compound provided by the embodiment of the present disclosure. In another example, the hole transport layer may include a plurality of sub-hole transport layers stacked in sequence, 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 by the embodiment of the present disclosure. In another example, the hole transport layer may include a plurality of sub-hole transport layers stacked in sequence, 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 by 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 adopt other materials other than the aromatic amine compound provided by the present disclosure. For example, an arylamine-based hole transport material or a carbazole-based hole transport material may be selected, such as one or more of NPB, TPD, BAFLP, 4DFLDPBi, CBP, PCzPA, and TCTA.

[0162] In one example, an open mask may be used to sequentially evaporate and deposit to form a hole injection layer and a hole transport layer. Further, the thickness of the hole injection layer is 5-20 nm; the thickness of the hole transport layer is 80-120 nm.

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

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

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

[0166] In an embodiment of the present disclosure, the peak value of the photoluminescence wavelength of the first functional layer is not greater than 450 nm, for example, between 400 nm and 450 nm. In this way, only a very small part or no light in the light emitted by the light-emitting functional layer has sufficient energy to cause the first functional layer to emit light, thereby avoiding the decrease in the light purity of the light emitted by the electroluminescent device.

[0167] In an embodiment of the present disclosure, the peak value of the photoluminescence wavelength of the first functional layer is λ1, and the peak value of the photoluminescence wavelength of the light-emitting functional layer is λ2, and λ2 - λ1 is not less than 5 nm, especially not less than 20 nm. In this way, it is possible to make the photoluminescence of the light-emitting functional layer not cause the photoluminescence of the first functional layer as much as possible.

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

[0169] In an 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. Further, 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 greater than 0.25 eV.

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

[0171] In an embodiment of the present disclosure, the display panel may include sub-pixels arranged in an array, and each sub-pixel is an electroluminescent device (for example, all are OLEDs). In the example of FIG. 2, the display device includes a red electroluminescent device, a green electroluminescent device, and a blue electroluminescent device. In the example of FIG. 2, 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, for example, 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, for example, 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 that are sequentially stacked.

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

[0173] Wherein, 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). Wherein, THK(HTL) is the thickness of the hole transport layer HTL.

[0176] In one example, the thickness of the hole transport region film layer (i.e., the thickness of the first functional layer) > the thickness of the electron transport region (i.e., the thickness of the second functional layer).

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

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

[0179] In the above examples, the microcavities of the red, green, and blue electroluminescent devices can be regulated, so that the display panel can achieve the optimal white light efficiency. The microcavity regulation is mainly adjusted by the thickness of the hole transport region. Due to the poor blue light efficiency and high driving voltage, this is related to the energy level barriers and hole mobility of the hole transport layer, the light-emitting auxiliary layer, and the light-emitting functional layer. In one example, the blue light performance can be improved by increasing the energy level and mobility of the light-emitting auxiliary layer of the blue electroluminescent device. The microcavity structure for achieving the best white light efficiency through different thicknesses.

[0180] In an embodiment of the present disclosure, the light-emitting functional layer is an organic light-emitting functional layer, and the organic light-emitting functional layer may include a host material and a guest material. In one example, the host material can be a single material, for example, a host material having both electron-transporting function and hole-transporting function. In another example, the host material may include a hole-type host material mainly for transporting holes and an electron-type host material mainly for transporting electrons. The guest material can be a fluorescent material or a phosphorescent material. Of course, according to needs, the organic light-emitting functional layer can also adopt other implementation forms.

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

[0182] In another example, the host material can be a carbazole derivative or an azine derivative; the guest material can be an organometallic complex (such as an organoiridium complex or an organoplatinum complex), etc.

[0183] In an embodiment of the present disclosure, a fine metal mask (FMM) can be used for evaporation deposition to form an electron blocking layer (in some embodiments, it can also be called a light-emitting auxiliary layer) and an organic light-emitting functional layer. 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 the 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 host material and a blue light guest material, and the thickness is 10 to 30 nm; the doping ratio of the blue light guest material is 1% to 10%. For example, the doping ratio of the blue light 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 the thickness is 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-emission assisting layer of the red electroluminescent device is 50 to 100 nm; the light-emission functional layer (organic light-emission 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 FIG. 2, the display device includes a red electroluminescent device, a green electroluminescent device, and a blue electroluminescent device. It can 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 FIG. 2. For example, at least one of the red electroluminescent device, the green electroluminescent device, and the blue electroluminescent device is missing, or an electroluminescent device with a new color is added.

[0188] In one embodiment of the present disclosure, the hole blocking layer may be made of an aromatic heterocyclic compound, including but not limited to one or more of imidazole derivatives, pyrazine derivatives, quinoline derivatives, isoquinoline derivatives, or phenanthroline derivatives. In one example, the material of the hole blocking layer is a compound with a nitrogen-containing six-membered ring structure or a compound having a phosphine oxide group on the heterocycle. Among them, the imidazole derivatives include but are not limited to one or more of benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives; the pyrazine derivatives include pyrimidine derivatives or / and 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, pyrazine derivatives, quinoline derivatives, isoquinoline derivatives, or phenanthroline derivatives. In one example, the material of the hole blocking layer is a compound with a nitrogen-containing six-membered ring structure or a compound having a phosphine oxide group on the heterocycle. Among them, the imidazole derivatives include but are not limited to one or more of benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives; the pyrazine derivatives include pyrimidine derivatives or / and 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 some other embodiments of the present disclosure, the electron transport layer may also be made of an inorganic material, such as doped or undoped zinc oxide and the like.

[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, etc.

[0192] In one embodiment of the present disclosure, at least two of the materials 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 ranges from 390 to 430 nm.

[0194] In one embodiment of the present disclosure, the peak of the photoluminescence wavelength of the second functional layer is λ3, the peak of the photoluminescence wavelength of the light-emitting functional layer is λ2, and λ2 - λ3 is greater than 20 nm, especially not less than 30 nm. In this way, the photoluminescence of the light-emitting functional layer can be made not to cause the photoluminescence of the second functional layer as much as possible.

[0195] In one embodiment of the present disclosure, an open mask can be used to separately evaporate and deposit the hole blocking layer, the electron transport layer, and the electron injection layer; the thickness of the hole blocking layer is 1 to 20 nm; the thickness of the electron transport layer is 10 to 50 nm; 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, IZO, etc. Further, the thickness of the anode is between 80 and 200 nm. Optionally, the anode is a transparent anode, and the electroluminescent device can emit light from the anode side. Further, 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 as a reflective layer, such as the anode being a composite electrode formed by Ag / ITO, Al / ITO, Ag / IZO, Al / IZO, etc. The thickness of the metal in the composite electrode can be between 10 and 100 nm; the thickness of the oxide layer is between 5 and 20 nm. Among them, 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. Further, 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 lower work function (such as Al, Ag, Mg, etc.), or an alloy containing a metal material with a low work function (such as an aluminum-magnesium alloy). Of course, the cathode can also use a conductive metal oxide such as IGZO.

[0200] Optionally, when the electroluminescent device emits light from the anode side, the cathode can have a relatively large thickness so as to have a relatively high reflectivity. For example, the thickness of the cathode is not less than 80 nm. Further, 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 can have a relatively small thickness so as to have a relatively high transmittance. For example, the thickness of the cathode is in the range of 10-20 nm. Further, the transmittance of the cathode at 550 nm is greater than 45%.

[0202] In an embodiment of the present disclosure, an open mask can be used to sequentially evaporate and deposit a metal cathode and a cover layer.

[0203] In an 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] Further, the material of the cover layer has a relatively 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 the related art, the material of the cover layer also has a relatively low light absorption intensity for light with a relatively short wavelength. For example, for light with a wavelength of about 400 nm, the light absorption intensity remains relatively low. On the one hand, the cover layer cannot filter and absorb short-wavelength light; on the other hand, short-wavelength light in the environment can pass through the cover layer and irradiate the functional layer, which may accelerate the aging rate of the functional layer.

[0206] In an embodiment of the present disclosure, the material of the cover layer can adopt the third aromatic amine compound provided by the present disclosure. This aromatic amine compound not only has a relatively large refractive index, but also has a relatively small absorbance for light with a wavelength greater than 450 nm (for example, light in the wavelength range of 450-630 nm) (which is beneficial to the emission of visible light), and has a relatively strong light absorption intensity for light with a wavelength of 400 nm and shorter wavelengths. Therefore, the cover layer can not only improve the light extraction efficiency of the electroluminescent device through a high refractive index without affecting the normal emission of visible light, but also protect the functional layer by absorbing short-wavelength light (especially ultraviolet light), which is beneficial to improving the lifespan of the device.

[0207] As follows, some exemplary compounds are synthesized and their properties are tested.

[0208] Synthesis of intermediate compound c-1

[0209] Compound a-1 [(8-phenyl-1-naphthyl)-boronic acid] (24.81 g; 100 mmol) and compound b [1,4-deuterated p-bromobiphenyl] (23.99 g; 100 mmol) were added to a reaction flask, and 250 mL of a THF / H 2 O mixed solvent (volume ratio 1 - 5:1) was added. After heating under reflux in a nitrogen atmosphere for 1 h, the temperature was then lowered to below 80 °C, potassium carbonate (27.64 g; 200 mmol) was added, then [tetrakis(triphenylphosphine)palladium] (1.16 g; 1 mmol) was added, and the temperature was raised to reflux and the reaction was carried out for 8 - 12 h. After the reaction was completed, the mixture was washed with water, the organic phase was extracted with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered by suction, 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-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)-boronic acid] (24.81 g; 100 mmol) and compound b [1,4-deuterated p-bromobiphenyl] (23.99 g; 100 mmol) were added to a reaction flask, and 250 ml of a THF / H 2 O mixed solvent (volume ratio 1 - 5:1) was added. After heating under reflux in a nitrogen atmosphere for 1 h, the temperature was then lowered to below 80 °C, potassium carbonate (27.64 g; 200 mmol) was added, then [tetrakis(triphenylphosphine)palladium] (1.16 g; 1 mmol) was added, and the temperature was raised to reflux and the reaction was carried out for 8 - 12 h. After the reaction was completed, the mixture was washed with water, the organic phase was extracted with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered by suction, 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] The intermediate compound c-1 (3.63 g; 10 mmol) and compound d [N-(4-(-1-naphthyl)phenyl)-4-biphenylamine] (3.71 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was evaporated to dryness, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain compound 5 (5.35 g, 82%), and by HPLC test, the purity was 99%. 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-fluoren-2-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was evaporated to dryness, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain compound 23 (5.61 g, 78%), and by HPLC test, the purity was 99.10%. LC / MS (m / z) (M+): 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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, dichloromethane and water were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain compound 72 (4.78 g, 69%), and by HPLC test, the purity was 99.35%. LC / MS (m / z) (M+): 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-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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, dichloromethane and water were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain compound 85 (5.84 g, 76%), and by HPLC test, the purity was 99%. LC / MS (m / z) (M+): 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-fluoren-2-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was evaporated to dryness, passed through a silica gel column, and recrystallized with toluene and n-heptane to obtain compound 170 (5.79 g, 81%). After testing by HPLC, the purity was 99.11%. LC / MS (m / z) (M+): 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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was evaporated to dryness, passed through a silica gel column, and recrystallized with toluene and n-heptane to obtain compound 187 (4.75 g, 69%). After testing by HPLC, the purity was 99.24%. LC / MS (m / z) (M+): 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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain compound 196 (6.49 g, 85%), and by HPLC test, the purity was 99.60%. LC / MS (m / z) (M+): 764.31.

[0227] Synthesis of deuterated compound 170D of compound 170

[0228] Intermediate compound c-2 (3.63 g; 10 mmol) and compound e [N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine] (4.77 g; 10 mmol) were added to a reaction flask, 100 ml of toluene was added, and under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain deuterated compound 170D of compound 170 (4.82 g, 67%), and by HPLC test, the purity was 99.11%. LC / MS (m / z) (M+): 719.34.

[0229] Synthesis of deuterated compound 187D of compound 187

[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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain the deuterated compound 187D of compound 187 (4.02 g, 58%). After testing by HPLC, the purity was 99.24%. LC / MS (m / z) (M+): 693.29.

[0231] Synthesis of the deuterated compound 196D of compound 196

[0232] The intermediate compound c-2 (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 under a nitrogen atmosphere, the mixture was heated to reflux for 2 h. After cooling, sodium tert-butoxide (1.44 g; 15 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.082 g; 0.2 mmol) and tris(dibenzylideneacetone)dipalladium (0.092 g; 10 mmol) were added, and then the mixture was heated to reflux and reacted for 8 - 12 h. After the reaction was completed, the reaction was quenched by adding water, extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was rotary evaporated, and after passing through a silica gel column, recrystallization was carried out using toluene and n-heptane to obtain the deuterated compound 196D of compound 196 (5.84 g, 76%). After testing by HPLC, the purity was 99.60%. LC / MS (m / z) (M+): 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. The 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 the above synthesis 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 was B3LYP / 6-31G**; ROE is the reorganization energy. It is generally believed that a small absolute value of ROE indicates a tendency of high mobility.

[0237] Table 1.1

[0238] Device Preparation Example A1.1

[0239] In this preparation example, an aromatic amine compound was used as the electron blocking layer material in the preparation of OLED devices. Five different blue OLEDs were prepared using Compound D-1, Compound D-2, Compound 5, Compound 187, and Compound 187D as the electron blocking layer, namely: Comparative Device A1.1A (the material of the electron blocking layer is Compound D-1), Comparative Device A1.1B (the material of the electron blocking layer is Compound D-2), Test Device A1.1A (the material of the electron blocking layer is Compound 5), Test Device A1.1B (the material of the electron blocking layer is Compound 187), and Test Device A1.1C (the material of the electron blocking layer is Compound 187D). The layers other than the electron blocking layer of Comparative Device A1.1A and Comparative Device A1.1B, and Test Devices A1.1A to A1.1C have the same materials and thicknesses.

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

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

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

[0243] Deposit an electron blocking layer and a blue light emitting layer using a fine metal mask (FMM). The thickness of the electron blocking layer is 5 nm. The blue light emitting layer includes a blue light host and a blue light guest, and the mass ratio of the blue light host to the blue light guest is 97:3;

[0244] Deposit an electron blocking layer, an electron transport layer, and an electron injection layer using Open mask;

[0245] Finally, deposit a metal cathode using Open mask.

[0246] For device information, refer to Table 1.2.

[0247] Table 1.2

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

[0249] The performance of each prepared OLED device was measured. Taking the performance of the comparative device A1.1A as the 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 devices A1.1A and A1.1B, for the devices prepared with the aromatic amine compound of the present invention (test devices A1.1A to A1.1C), various performances have been improved. This is related to the fact that the aromatic amine compound of the present invention forms a special connection angle by using the 1,8-position or 2,3-position connection at the Ar 3 position, enabling it to have a relatively fast mobility and a high T1, which allows more excitons to recombine and emit light in the light-emitting layer. In addition, the test device A1.1C has a significantly improved lifespan compared to the test device A1.1B. This is because the C-D (carbon-deuterium) bond vibrates at a lower frequency, and its zero-point base energy is lower than that of the corresponding C-H (carbon-hydrogen) bond, while their transition state activation energies are similar. This makes the C-D bond breakage require more energy than the C-H bond breakage, so the C-D bond is relatively more stable than the C-H 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, an aromatic amine compound was used as a hole transport layer material in the preparation of OLED devices. Four different blue OLEDs were prepared using Compound D-3, Compound 85, Compound 196, and Compound 196D as electron blocking layers, 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 films 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 methods of each functional layer are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, etc., which will not be elaborated here. Only some process details and test methods in the preparation process are supplemented and described as follows:

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

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

[0256] Deposit an electron blocking layer and a blue light-emitting layer using a fine metal mask (FMM). The thickness of the electron blocking layer is 5 nm. The blue light-emitting layer includes a blue light host and a blue light guest, with a thickness of 20 nm, and the mass ratio of the blue light host to the blue light guest is 97:3;

[0257] Deposit a hole blocking layer, an electron transport layer, and an electron injection layer using an Open mask;

[0258] Finally, deposit a metal cathode using an Open mask.

[0259] See Table 1.4 for device information.

[0260] Table 1.4

[0261] Except for the material of the hole transport layer, the molecular structural formulas of the materials of each layer are as follows:

[0262] The performance of the prepared OLED devices was measured. Taking the performance of the OLED device prepared using Comparative Example 3 as the raw material as the benchmark, the performance of each other OLED device 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 with the aromatic amine compound of the present invention has a relatively fast mobility, which is beneficial to the hole transfer to the light-emitting layer, forming more excitons and improving the device performance.

[0265] The following synthesis method is adopted to obtain intermediate compounds III-1 to III-6, and then some compounds of the exemplary embodiments disclosed herein are mainly synthesized through Buchwald-Harting reaction and Suzuki reaction.

[0266] Intermediate compound III-1

[0267] Under nitrogen protection, intermediate compound I-1 (5-bromoacenaphthene) (10 g, 42.90 mmol), intermediate compound II-1 (4-chlorophenylboronic acid) (7.72 g, 49.34 mmol) and potassium carbonate (11.86 g, 85.80 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, heated and stirred until dissolved, then tetrakis(triphenylphosphine)palladium (0.74 g, 0.64 mmol) was added, and the mixture was heated under reflux. The reaction was monitored by TLC. After the reaction was completed, the mixture was washed with water, extracted with dichloromethane, the solvent was removed by a rotary evaporator, and then passed through a silica gel column with n-heptane and dichloromethane (10:1) to remove the solvent. The resulting pale yellow solid was recrystallized, filtered by suction, and dried under vacuum to obtain intermediate compound III-1, yield: 72%, purity 98%; MS: 264.07.

[0268] Referring to the synthesis method of intermediate compound III-1, the reaction was carried out by replacing intermediate compound III-1 with intermediate compounds II-2 to II-6 respectively, and intermediate compounds III-2 to III-6 could be obtained correspondingly.

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

[0270] Table 2.1

[0271] Reacting the intermediate compounds of series III with diarylamine compounds, the following exemplary compounds disclosed herein can be synthesized:

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

[0273] Synthesis of Compound B1

[0274] Dissolve intermediate compound Ⅲ-1 (5.58 g, 21 mmol) and N-(4-(1-naphthyl)phenyl)-4-biphenylamine (diamine a2-H corresponding to intermediate a2) (7.43 g, 20 mmol) in toluene solvent, stir under nitrogen protection until reflux, then successively add sodium tert-butoxide, Sphos, and Pd2(dba)3 and heat under reflux overnight. After the reaction is completed, cool to room temperature, then add distilled water to the reaction solution and extract the reaction solution with the organic solvent dichloromethane (DCM). Then dry the extracted organic layer with magnesium sulfate and remove the solvent using a rotary evaporator. Purify the remaining substance by column chromatography and remove the solvent using a rotary evaporator. Recrystallize the solid with toluene / n-heptane to obtain Compound B1; purity: 99.63%, yield: 87%, MS: 599.26; molecular weight is C46H33N.

[0275] Referring to the synthesis method of Compound B1, replace diamine a2-H with diamine a41-H, diamine a57-H, diamine a13-H, diamine a154-H, diamine a156-H, and diamine a221-H respectively to synthesize and obtain Compound B9, Compound B10, Compound B18, Compound B37, Compound B58, and Compound B172. The raw materials, synthesis yields, purities, and MS of Compound B9, Compound B10, Compound B18, Compound B37, Compound B58, and Compound B172 are shown in Table 2.2.

[0276] Table 2.2

[0277] Synthesis of Compound B17

[0278] The intermediate compound III-3 (7.16 g, 21 mmol) and N-(4-(1-naphthyl)phenyl)-4-biphenylamine (the diarylamine a2-H corresponding to intermediate a2) (7.43 g, 20 mmol) were dissolved in toluene solvent, stirred under nitrogen protection until refluxing, and then sodium tert-butoxide, Sphos, and Pd2(dba)3 were added successively and heated under reflux overnight. After the reaction was completed, the temperature was lowered to room temperature. Then, distilled water was added to the reaction solution and the reaction solution was extracted with the organic solvent dichloromethane (DCM). Then, the extracted organic layer was dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substance was purified by column chromatography, and the solvent was removed using a rotary evaporator. The solid was recrystallized with toluene / n-heptane to obtain compound B17; purity: 99.7%, yield: 86%, MS: 675.29; the molecular weight is C52H37N.

[0279] Referring to the synthesis method of compound B17, the diarylamine a4-H, diarylamine a111-H, diarylamine a104-H, and diarylamine a217-H were used to replace the diarylamine a2-H respectively to synthesize and obtain compound B19, compound B136, compound B139, and compound B258. The raw materials, synthesis yields, purities, and MS of compound B19, compound B136, compound B139, and compound B258 are shown in Table 2.3.

[0280] Table 2.3

[0281] Synthesis of the partially deuterated compound B17D of compound B17

[0282] Under nitrogen protection, compound B17 (6.75 g, 10 mmol), deuterated benzene (89 ml, 1 mol), trifluoromethanesulfonic acid (9.43, 60 mmol), and 500 ml of 1,4-dioxane were added to a three-necked flask, and the reaction was carried out at 90 °C overnight. The reaction was monitored by TLC. After the reaction was completed, it was cooled to room temperature. It was extracted with dichloromethane and deionized water, and the organic phase was washed with water until neutral. Water was removed with anhydrous magnesium sulfate, and the organic phase was dried by rotary evaporation. Recrystallization was carried out with dichloromethane and n-heptane to obtain a pale yellow product, and compound B17D was obtained; yield: 43%; purity: 99.53%; MS[M+H]+: 708.29. All the hydrogens attached to the sp2 hybridized carbons in compound B17 were deuterated to form compound B17D.

[0283] In the embodiments of the present disclosure, the above-mentioned partial exemplary compounds were also compared with a control compound in terms of properties. The structure of the control compound is as follows:

[0284] The physicochemical properties of the above control compounds and compounds B10, B17, B19, and B224 were simulated using the simulation software Spartan (basis set / functional: B3LYP / 6-31G**). The results are shown in Table 2.4. Among them, ROE is the reorganization energy. It is generally believed that a smaller absolute value of ROE indicates a higher mobility trend.

[0285] Table 2.4

[0286] Device Fabrication and Test Example 2.1

[0287] Multiple organic light-emitting devices were fabricated using the following method, and the driving voltage, luminous efficiency, and lifespan of the organic light-emitting devices were tested. The fabrication process of the organic light-emitting devices is as follows:

[0288] The pre-prepared ITO substrate was cleaned and dried. The ITO substrate had an ITO layer as the anode; 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 cover layer were sequentially formed on the anode by evaporation.

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

[0290] The material of the hole transport layer was compound HT2.1, with a thickness of 110 nm;

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

[0292] The material of the hole blocking layer was compound HB2.1, with a thickness of 10 nm;

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

[0294] The material of the electron injection layer was Yb, with a thickness of 5 nm;

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

[0296] The material of the cover layer was CP2.1, with a thickness of 70 nm.

[0297] In the device preparation and testing example 2.1, according to the different materials used for the electron blocking layer of the organic light-emitting device, the organic light-emitting devices are divided into a reference device B2.1 (the material of the electron blocking layer is compound EBL1-Ref), a test device B2.1A (the material of the electron blocking layer is compound B37), a test device B2.1B (the material of the electron blocking layer is compound B160), and a test device B2.1C (the material of the electron blocking layer is compound B193). The only difference among the reference device B2.1, the test device B2.1A, the test device B2.1B, and the test device B2.1C is the material of the electron blocking layer, and the materials and thicknesses of the other film layers are the same. Among them, 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 lifetime of the reference device B2.1, the test device B2.1A, the test device B2.1B, and the test device B2.1C were tested, and the test results are shown in Table 2.5. In Table 2.5, the test data of each device were normalized based on the reference device B2.1. Among them, the lifetime is the T95 lifetime, the test temperature is room temperature, and the current density used for the test is 15 mA / cm 2 ; the efficiency is the current efficiency, and the current density during the test is 15 mA / cm 2 .

[0300] Table 2.5

[0301] Compared with the reference device B2.1, the test devices B2.1A to B2.1C have higher efficiency and longer lifetime. This is because the materials of the electron blocking layers in the test devices B2.1A to B2.1C introduce cycloalkylnaphthalene, which improves the mobility of the materials and has relatively shallow energy levels, and the relatively twisted structure can reduce quenching and crystallization caused by molecular stacking, thereby improving the efficiency and lifetime.

[0302] Device Preparation and Testing Example 2.2

[0303] Multiple organic light-emitting devices were prepared by the following method and the driving voltage, luminous efficiency, and lifetime of the organic light-emitting devices were tested. The preparation process of the organic light-emitting device is as follows:

[0304] The pre-prepared ITO substrate is cleaned and dried. The ITO substrate has an ITO layer as the anode; on the anode, 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 cover layer are sequentially formed by evaporation coating process.

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

[0306] The material of the hole transport layer is compound HT2.1, and the thickness is 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 20 nm;

[0308] The material of the hole blocking layer is compound HB2.1, and the thickness is 10 nm;

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

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

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

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

[0313] In the preparation and testing example 2.2 of this device, according to the different materials used for the electron blocking layer of the organic electroluminescent device, the organic electroluminescent device is divided into a reference device B2.2 (the material of the electron blocking layer is compound EBL2-Ref), a test device B2.2A (the material of the electron blocking layer is compound B1), a test device B2.2B (the material of the electron blocking layer is compound B10), a test device B2.2C (the material of the electron blocking layer is compound B17), and a test device B2.2D (the material of the electron blocking layer is compound B19). The only difference among the reference device B2.2, the test device B2.2A, the test device B2.2B, the test device B2.2C, and the test device B2.2D is the different materials of the electron blocking layer, and the materials and thicknesses of the other film layers are the same. Among them, the thickness of the electron blocking layer is 10 nm.

[0314] The driving voltage, luminous efficiency, and lifetime of the reference device B2.2, test devices B2.2A, B2.2B, B2.2C, and 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 with reference to the reference device B2.2. Among them, the lifetime is the T95 lifetime, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; the efficiency is the current efficiency, and the current density during the test is 15 mA / cm 2 .

[0315] Table 2.6

[0316] Compared with the reference device B2.2, the test devices B2.2A to B2.2D have higher efficiency and longer lifetime. This is because the materials of the electron blocking layers in the test devices B2.2A to B2.2D introduce cycloalkylnaphthalene, which improves the mobility of the materials and has relatively shallow energy levels, and the relatively twisted structure can reduce quenching and crystallization caused by molecular stacking, thereby improving the efficiency and lifetime.

[0317] Device Fabrication and Test Example 2.3

[0318] Multiple organic light-emitting devices were fabricated using the following method and the driving voltage, luminous efficiency, and lifetime of the organic light-emitting devices were tested. The fabrication process of the organic light-emitting devices is as follows:

[0319] The pre-prepared ITO substrate was cleaned and dried. The ITO substrate has an ITO layer as the anode; on the anode, 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 cover layer were sequentially formed by evaporation.

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

[0321] The material of the hole transport layer is 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 20 nm;

[0323] The material of the hole blocking layer is compound HB2.1, with 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 5 nm;

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

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

[0328] In the preparation and testing example 2.3 of this device, according to the different materials used for the electron blocking layer of the organic light-emitting device, the organic light-emitting devices are divided into a reference device B2.3 (the material of the electron blocking layer is compound EBL3-Ref) and a test device B2.3A (the material of the electron blocking layer is compound B17). The only difference between the reference device B2.3 and the test device B2.3A lies in the different materials of the electron blocking layer, and the materials and thicknesses of the remaining film layers are the same. Among them, the thickness of the electron blocking layer is 10 nm.

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

[0330] Table 2.7

[0331] Compared with the reference device B2.3, the test device B2.3A has a lower driving voltage, a higher efficiency and a longer lifetime. Compared with the compound EBL3-Ref, the compound B17 has a deeper HOMO energy level, which is more conducive to the injection of holes into the organic light-emitting layer; compared with the compound EBL3-Ref, the compound B17 has a faster mobility, which is conducive to the reduction of the driving voltage.

[0332] Device Preparation and Testing Example 2.4

[0333] Multiple organic light-emitting devices are prepared by the following method and the driving voltage, luminous efficiency and lifetime of the organic light-emitting devices are tested. The preparation process of the organic light-emitting device is as follows:

[0334] The pre-prepared ITO substrate is cleaned and dried. The ITO substrate has an ITO layer as the anode; on the anode, 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 cover layer are sequentially formed by evaporation coating.

[0335] The material of the hole injection layer is 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 material of the hole transport layer is 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 20 nm;

[0339] The material of the hole blocking layer is compound HB2.1, with 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 5 nm;

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

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

[0344] In the preparation and test example 2.4 of this device, according to the difference in the hole transport compound 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 devices are divided into reference device B2.4A (the hole transport compound is compound HT1-Ref), reference device B2.4B (the hole transport compound is compound HT2-Ref), test device B2.4A (the hole transport compound is compound B58), and test device B2.4B (the hole transport 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 was normalized with reference device B2.4A as the benchmark. In Table 2.9, the test data of each device was normalized with reference device B2.4B as the benchmark. Among them, 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 ; the efficiency is the current efficiency, and the current density during the test is 15 mA / cm 2 .

[0346] Table 2.8

[0347] Table 2.9

[0348] Compared with reference device B2.4A, test device B2.4A has higher efficiency and longer lifespan. This is because the material of the hole transport layer in test device B2.4A introduces cycloalkylnaphthalene and diphenylfluorene groups, which improves the mobility of the material and has relatively shallow energy levels. And the diphenylfluorene group has a large steric structure, which can inhibit aggregation crystallization and thus improve the film-forming property of the material.

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

[0350] Device Preparation and Test Example 2.5

[0351] Multiple organic electroluminescent devices were prepared by the following method and the driving voltage, luminous efficiency, and lifespan of the organic electroluminescent devices were tested. The preparation process of the organic electroluminescent device is as follows:

[0352] The pre-prepared ITO substrate was cleaned and dried. The ITO substrate has an ITO layer as the anode, and the thickness of the ITO layer is 100 nm; an 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 cover layer were sequentially formed on the anode by evaporation.

[0353] The material of the hole injection layer is compound HT2.5 doped with compound PD2.5. The doping ratio of compound PD2.5 is 2%, and the thickness is 10 nm. The material of the hole transport layer is compound HT2.5, and the thickness is 110 nm. The material of the hole blocking layer is compound HB2.5, and the thickness is 5 nm. The material of the electron transport layer is a mixture of compound ET2.5 and LiQ, and the mixing ratio is 1:1, and the thickness is 30 nm. The material of the electron injection layer is Yb, and the thickness is 5 nm. The material of the cathode is a magnesium-silver alloy, and the thickness is 10 nm. The material of the cover layer is CP2.5, and the thickness is 70 nm.

[0354] In this embodiment, the film layer differences of the prepared organic light-emitting device lie in the electron blocking layer and the organic light-emitting layer, and the materials and thicknesses of the remaining film layers are the same. According to the differences in the electron blocking layer and the organic light-emitting layer, the organic light-emitting device includes:

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

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

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

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

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

[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, and the doping ratio of compounds RH2.5A, RH2.5B and compound RD2.5 is 49:49:2, with a thickness of 45 nm).

[0361] In this Example 2.5, the structural formulas of the materials used are as follows:

[0362] The driving voltages, luminous efficiencies and lifetimes of 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 reference. In Table 2.11, the test data of each device were normalized with reference device B2.5B as the reference. In Table 2.12, the test data of each device were normalized with reference device B2.5C as the reference. Among them, the lifetime is the T95 lifetime, the test temperature is room temperature, and the current density used in the test is 15 mA / cm 2 ; the efficiency is the current efficiency, and the current density during the test is 15 mA / cm 2 .

[0363] Table 2.10

[0364] Table 2.11

[0365] Table 2.12

[0366] Compared with reference device B2.5A, test device B2.5A has higher efficiency; compared with reference device B2.5B, test device B2.5B has higher efficiency; compared with reference device B2.5C, test device B2.5C has higher efficiency. This efficiency difference is mainly due to the fact that the material used in the electron blocking layer / luminescence auxiliary layer of the reference device has a cycloalkylnaphthalene structure, which improves the hole mobility and makes the energy level between the electron blocking layer / luminescence auxiliary layer and the organic light-emitting layer more matched, thereby improving the efficiency and facilitating the reduction of the driving voltage.

[0367] Synthesis example 3.1

[0368] Synthesis of compound C23

[0369] Toluene solvent (150 mL) was added to the reaction flask, followed by 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 nitrogen protection, Pd 2 (dba) 3 (0.183 g, 0.2 mmol), Sphos (0.164 g, 0.4 mmol) was added, nitrogen was inflated and refluxed for 2 hours, and the recrystallized solid was filtered and rinsed with methanol to obtain the intermediate SM3.1c.

[0370] Toluene solvent was added to the bottle, and then intermediate SM3.1c (6.43 g, 15 mmol) and intermediate SM3.1d (4.72 g, 16 mmol) and sodium tert-butoxide (2.16 g, 22.5 mmol) were added in sequence. After nitrogen was charged, palladium acetate (0.034 g, 0.15 mmol) and tri-tert-butylphosphine (0.061 g, 0.3 mmol) were added. The nitrogen charging process was repeated and refluxed for 2 hours. After the reaction was completed, it was cooled to room temperature and filtered through diatomaceous earth to obtain the filtrate. After concentration, it was heated, a small amount of ethanol was added, and it was allowed to stand at room temperature for recrystallization. The recrystallized solid was filtered and washed with ethanol to obtain compound C23, which was a light yellow solid. Purity: 99.57%, yield: 88%, MS: 654.77; C47H30N2O2.

[0371] Referring to the synthesis method of reference compound C23, using raw material 3.1 instead of intermediate SM3.1a, using raw material 3.2 instead of intermediate SM3.1b, and using raw material 3.3 instead of intermediate SM3.1d, compounds C4, C9, C4, C14, C15, C28, C22, C30, C43, C58, and C60 were synthesized. For each compound and the raw materials for synthesizing the compounds, please refer to Table 3.0.

[0372] Table 3.0

[0373] Refractive index test

[0374] The refractive indices of compounds C4, C9, C14, C15, C23, C28, C22, C30, C43, C58, 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, an ellipsometer was used to measure the refractive index of the compounds, and the instrument scanning range was 245 - 1000 nm. The test was carried out by evaporating a thin film on a silicon wafer, and the thickness of the material thin film was 50 nm.

[0376] Table 3.1

[0377] It can be seen from Table 3.1 that the compounds of some embodiments of the present disclosure have a relatively high refractive index. On the one hand, the compounds of the embodiments of the present disclosure can improve the polarizability of the compounds by introducing heteroatoms such as oxygen or nitrogen. On the other hand, when the heterocycle is connected to the benzene ring, it is a planar structure, and the dihedral angle between the plane of the heterocycle and the plane of the adjacent benzene ring (or other aromatic rings) is close to 0, almost in a coplanar state, which increases the conjugation of the compound and is conducive to improving the refractive index of the molecule. At the same time, the enhanced conjugation of the compound also makes the compound have enhanced absorption of ultraviolet light, which is conducive to protecting other functional materials during organic electroluminescence. Moreover, the compounds of the embodiments of the present disclosure have a structure of cycloalkylnaphthalene, which can moderately increase the structural three-dimensionality of the compound while maintaining a high refractive index, and can improve the thermal properties of the material.

[0378] Absorption intensity test and glass transition temperature test

[0379] Absorption intensity test: 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, thin films with a thickness of 50 nm were respectively prepared, and the absorption intensity was measured using a UV spectrophotometer. The test results at two wavelengths of 400 nm and 450 nm are shown in Table 3.2.

[0380] The glass transition temperatures 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 measured. The measurement method was DSC test (select the second heating process, with the temperature ranging from room temperature to 300 °C). The test results are shown in Table 3.2.

[0381] Table 3.2

[0382] It can be seen from Table 3.2 that some of the compounds provided by the embodiments of the present disclosure have strong light absorption intensity at 400 nm. When these compounds are used as the covering layer of an organic electroluminescent device, they can absorb ultraviolet rays in the external environment, thereby protecting the organic electroluminescent device from being damaged by ultraviolet light in the external environment, reducing the aging rate of the organic electroluminescent device, and facilitating the extension of the lifespan of the organic electroluminescent device. At the same time, these compounds basically do not absorb light with a wavelength of 450 nm and longer wavelengths, so they can avoid absorbing the light emitted by the organic electroluminescent device itself, thereby avoiding the influence of light absorption on the light extraction efficiency of the organic electroluminescent device.

[0383] It can be seen from Table 3.2 that some of the compounds provided by the embodiments of the present disclosure have a high glass transition temperature. On the one hand, this is beneficial to the stability of these compounds during the evaporation process. On the other hand, it can prevent the formed film layer from undergoing vitrification, thereby facilitating the maintenance of the stability of the formed film layer. In this way, these compounds have good film-forming properties.

[0384] Device preparation and test Example 3.1

[0385] An organic light-emitting device is fabricated by the following method: A pre-prepared ITO substrate with an ITO thickness of 100 nm is cleaned and dried. Then, a hole injection material and a hole transport material are co-evaporated onto the anode (ITO) successively as the hole injection layer and the hole transport layer, and an electron blocking layer (EBL) material. Subsequently, an organic light-emitting layer is deposited by co-evaporating BH and BD materials. A hole blocking layer (HBL) material, an electron transport layer (ETL) material, and an electron injection layer (EIL) material are deposited onto the organic light-emitting layer. Then, a cathode (magnesium-silver alloy) is deposited. On top of the cathode, a capping layer (CPL) material with a thickness of 65 nm is deposited.

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

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

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

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

[0390] The material of the hole blocking layer is HB2.5, with a thickness of 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, with a thickness of 1 nm.

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

[0394] In this embodiment, a variety of different organic light-emitting devices are fabricated using different capping layer materials. The difference between these organic light-emitting devices lies only in the capping layer materials, while the materials and thicknesses of other film layers are the same. The organic light-emitting devices fabricated in this embodiment include:

[0395] Test device C4 (the capping layer material is compound C4)

[0396] Test device C14 (the capping layer material is compound C14)

[0397] Test device C22 (the capping layer material is compound C22)

[0398] Test device C23 (the capping layer material is compound C23)

[0399] Test device C28 (the covering layer material is compound C28)

[0400] Test device C43 (the covering layer material is compound C43)

[0401] Test device C58 (the covering layer material is compound C58)

[0402] Reference device C3.1 (the covering layer material is compound CP3.1)

[0403] Test device C3.2 (the covering layer material is compound CP3.2)

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

[0405] Table 3.3

[0406] Those skilled in the art will readily conceive of 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 known common general knowledge or conventional technical means in the technical field not disclosed in the present disclosure. The specification and examples are only to be considered as exemplary, and the true scope and spirit of the present disclosure are pointed out by the appended claims.

Claims

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, or 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, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkane naphthyl having 14 to 30 carbon atoms; said R4 and R5 are the same or different and are independently selected from deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cyclo ...30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cyclo any one of a substituted 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, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; the p represents 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 of 2 to 4; any two R7 are the same or different; any two R8 are the same or different; when L1, Q1, Q2, Q3, R4, R5, R7, R8, Ar4 have substituents, the L1, Q1 The substituents of Q2, Q3, R4, R5, R7, R8 and 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. The aromatic amine compound according to claim 1, wherein The R6 is CH2 or CD2, and the k is 2. The aromatic amine compound according to claim 1, wherein The structure of the aromatic amine compound is shown in Formula I below: Wherein, Ar3 is selected from any one of the following groups: Ar1 and Ar2 may be the same or different and each independently represents any one of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkylnaphthyl, and substituted or unsubstituted cycloalkane naphthyl; the heteroaryl contains at least one or more heteroatoms selected from O, S, N, and Si; R1-R3 may be the same or different and each independently represents deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylnaphthyl, any one of a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; when Ar1, Ar2, Ar4, and R1-R5 have substituents, the substituents of Ar1, Ar2, Ar4, and R1-R5 may be the same or different and are independently selected from deuterium, halogen, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; when Ar3 is selected from When there is at least one benzene ring directly connected to the naphthyl group, all hydrogen atoms on the ring are replaced by deuterium; said m represents an integer of 0-5; said n represents an integer of 0-5; and said o represents an integer of 0-4. 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. The aromatic amine compound according to claim 3, wherein The cycloalkylnaphthalene is selected from one of the structures shown below: 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: The aromatic amine compound according to claim 3, wherein The aromatic amine compound is selected from one of the structures shown below: 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. 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. 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. 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. 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: Among them, 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, alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, and heteroaryl groups 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. 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: Describes a chemical bond; wherein the substituted group W3 is a group formed by replacing the unsubstituted group W3 with one or more deuteriums. 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. 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. 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. The aromatic amine compound according to claim 16, wherein At least one of Q2 and Q3 contains the following fused aromatic heterocyclic group: Among them, X1 is selected from C(Y6Y7), NY8, O, S; X2 is selected from NY8, O, S; Y1, Y2, Y3, Y4 are each independently selected from CY8 or N, and only one is selected from N; Y5, Y6, Y7, 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. 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. The aromatic amine compound according to claim 17, wherein At least one of Q2 and Q3 is selected from the group consisting of: 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 a group formed by replacing the unsubstituted group W5 with one or more substituents selected from deuterium, fluorine, chlorine, bromine, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 6 to 10 carbon atoms, and 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. 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. The aromatic amine compound according to claim 16, wherein The L2 is selected from phenylene, biphenylene, terphenylene, naphthylene, dibenzofuranylene, and dibenzothiophenylene. The aromatic amine compound according to claim 16, wherein The aromatic amine compound is selected from the group consisting of the following compounds: 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. 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. 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. 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. 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. 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. 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. A display device comprising the electroluminescent device according to any one of claims 24 to 30.

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