Arylamine compound, organic electroluminescent element and electronic equipment
By using a specific structure of aromatic amine compounds in the luminescence auxiliary layer of an organic electroluminescent device, the challenges of luminescence efficiency and lifetime improvement in the prior art are solved, achieving more efficient exciton generation and longer device lifetime.
Patent Information
- Application Number
- CN202311602036.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-11-28
- Publication Date
- 2025-05-30
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
There is room for improvement in the luminous efficiency and lifetime of existing organic electroluminescent devices, especially in improving exciton generation efficiency and preventing exciton transfer to the connected layer.
An aromatic amine compound with a specific structure is used as the luminescent auxiliary layer material. By introducing phenanthrene into the triarylamine containing hydrogen pyrene, hole mobility and hole transport performance are improved, thereby improving the luminescence efficiency and lifetime of the device.
The luminescence efficiency and lifetime of organic electroluminescent devices are significantly improved, and by improving hole transport performance, the exciton generation efficiency is enhanced and the transfer of excitons to the connected layer is reduced.
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Figure CN120058659A_ABST
Abstract
Description
Technical Field
[0001] The present invention belongs to the technical field of organic electroluminescence, and more specifically, relates to an arylamine compound, an organic electroluminescent device, and an electronic device. Background Art
[0002] An organic light emitting diode is a self-luminous display device based on organic electroluminescent materials. Different from existing liquid crystal display devices, it has the characteristics of not requiring a backlight source and being thin, and is a technology suitable for flexible device devices (flexible light emitting display devices).
[0003] Organic electroluminescent materials are high-molecular or small-molecular organic materials that can emit light under the action of an electric field. In order to improve the stability and efficiency of organic electroluminescent materials in organic electroluminescent devices, multiple layers of organic thin films are prepared between the anode and the cathode. The above-mentioned organic thin film layers can be divided into a hole injection layer, a hole transport layer, a light-emitting layer host, a light-emitting layer dopant, an electron transport layer, and an electron injection layer.
[0004] Based on the light-emitting materials (blue, green, and red three-color light materials) used in the above-mentioned light-emitting layer, a display device with high color saturation is prepared. According to the latest technical reports, white light for large-size displays is achieved by mixing blue light-emitting materials and yellow light-emitting materials or orange light-emitting materials, and blue light-emitting materials, green light-emitting materials, and red light-emitting materials are used in small-size displays.
[0005] When an electric field is applied between the anode and the cathode of an organic electroluminescent device, holes are injected from the anode, and the injected holes move to the light-emitting layer through the hole transport layer. At the same time, electrons are injected from the cathode, and the injected electrons move to the light-emitting layer through the electron transport layer. The holes and electrons that move to the light-emitting layer combine to form excitons. When the excitons transition from the excited state to the ground state, energy will be released in the form of light, realizing the light emission of the device.
[0006] The efficiency of an organic electroluminescent device can generally be divided into internal luminous efficiency and external luminous efficiency. The internal luminous efficiency is related to the light conversion efficiency of excitons generated in the organic layer (such as the hole transport layer, the light-emitting layer, and the electron transport layer, etc.) between the first electrode (for example, the anode) and the second electrode (for example, the cathode). In the theoretical values of the above-mentioned light conversion efficiency, fluorescence is 25% and phosphorescence is 100%. The external luminous efficiency is related to the light extraction efficiency of the light emitted from the organic layer to the outside of the organic electroluminescent device. Generally, the external light extraction efficiency is about 20% of the internal luminous efficiency.
[0007] In order to ensure high efficiency and high color saturation, factors such as 1) energy levels and 2) electron movement of the peripheral functional layers related to the light-emitting layer should be considered. It is most important to improve the exciton generation efficiency in the light-emitting layer by adjusting the movement of holes and electrons injected from the electrodes. In addition to improving the exciton generation efficiency, in order to prevent excitons from transferring to the adjacent layers, the energy level of the lowest unoccupied molecular orbital (LUMO) of the hole transport layer is higher than that of the light-emitting layer, or the energy level of the highest occupied molecular orbital (HOMO) of the electron transport layer is lower than that of the light-emitting layer. Recently, it has been clarified that the triplet energy level of the peripheral functional layer also affects the light-emitting efficiency. In order to fabricate high-efficiency and long-lifetime organic electroluminescent devices, materials with high triplet energy levels and high lowest unoccupied molecular orbital (LUMO) energy levels are required. Summary of the Invention
[0008] In view of the above-mentioned defects or improvement requirements of the prior art, the present invention provides an arylamine compound, which can be used as a high-performance light-emitting auxiliary layer material and can significantly improve the device performance when used in an organic electroluminescent device.
[0009] The technical solution adopted by the present invention to solve its technical problems is: an arylamine compound having a structure shown in formula (1),
[0010]
[0011] wherein, L 1 and L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,
[0012] R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heteroalkenyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;
[0013] A is a divalent ethyl group, r is selected from 0 or 1, and when r is 0, A and the bonds connected on both sides do not exist;
[0014] Ar 1 is *-L 3 -R3 ,
[0015] L 3 is selected from a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
[0016] R 3 is selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
[0017] When the substituents in the "substituted or unsubstituted" are substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, a C1-C10 alkyl, a C3-C10 cycloalkyl, a C1-C10 alkoxy, a C6-C30 aryl, a C3-C30 heteroaryl,
[0018] In the sub-heteroarylene, heterocycloalkyl, heterocycloalkenyl, heteroaryl, the heteroatoms are each independently at least one of N, O, S, Si, P.
[0019] Specifically, the divalent ethyl group is preferably -CH 2 -CH 2 -.
[0020] Furthermore, in an embodiment of the present invention, the aromatic amine compound has the structures shown in formulas (2)-(4):
[0021]
[0022] wherein, L 1 , L 2 , R 1 , R 2 , Ar 1 are defined as above.
[0023] In an alternative embodiment of the present invention, the Ar 1 is *-L 3 -R 3 , L 3 is selected from a single bond, phenylene, biphenylene, naphthylene, anthrylene, phenanthrylene, fluoranthenylene, pyrenylene, perylenylene, terphenylenylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, fluorenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirobifluorenylene,
[0024] R 3Selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, and any one of two or more combinations of the above groups.
[0025] R 3 When being dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, it may or may not be substituted by phenyl.
[0026] In an alternative embodiment of the present invention, L 1 and L 2 each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group.
[0027] In an alternative embodiment of the present invention, L 1 and L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted phenylene naphthyl group, a substituted or unsubstituted phenylene anthracenyl group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted terphenyl group.
[0028] In an alternative embodiment of the present invention, R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl.
[0029] Preferably, R 1 and R 2 are the same or different and each independently hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, terphenyl.
[0030] In an alternative embodiment of the present invention, the present invention further provides a preparation, the preparation comprising at least one of the above-mentioned arylamine compounds and at least one solvent.
[0031] In an alternative embodiment of the present invention, the present invention further provides an organic electroluminescent element, comprising:
[0032] a first electrode;
[0033] a second electrode arranged to face the first electrode; and
[0034] one or more organic material layers disposed between the first electrode and the second electrode and including a light-emitting layer,
[0035] wherein one or more of the organic material layers contain the arylamine compound of the present invention.
[0036] Specifically, in an embodiment of the present invention, a hole transport layer is included between the first electrode and the light-emitting layer, and a light-emitting auxiliary layer is included between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer contains the arylamine compound of the present invention. The present invention further provides an electronic device, which includes a display device and a lighting device, and is provided with the above-mentioned organic electroluminescent element.
[0037] Generally speaking, compared with the prior art by the above technical solution conceived by the present invention, the following beneficial effects can be achieved:
[0038] 1. For the arylamine compound of the present invention, by introducing a phenanthryl group into the triarylamine containing hydroanthracene, the hole mobility is improved, the hole transport performance is improved, and further the light-emitting efficiency of the device is improved. The organic light-emitting device prepared from the arylamine compound of the present invention has good improvements in light-emitting efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS
[0039] Figure 1 It is a schematic diagram of the device structure of an organic electroluminescent element according to an embodiment of the present invention, wherein the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the light-emitting auxiliary layer 4, the light-emitting layer 5, the electron transport layer 6, the electron injection layer 7, and the second electrode layer 8 DETAILED DESCRIPTION OF THE EMBODIMENTS
[0040] Exemplary embodiments will now be described in detail, and their examples are illustrated in the drawings, wherein the same reference numerals always refer to the same elements. In this regard, the exemplary embodiments may have different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below only by referring to the drawings for purposes of illustration. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. The expression "at least one (kind) of" modifies the entire list of elements when it is before or after the list of elements and does not modify the individual elements of the list.
[0041] It will be understood that when an element is referred to as being "on" another element, it can be in direct contact with the other element or there can be intervening elements therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.
[0042] It will be understood that although the terms first, second, third, etc. may be used herein to describe various elements, components (parts), regions, layers, and / or portions (sections), these elements, components (parts), regions, layers, and / or portions should not be limited by these terms. These terms are only used to distinguish one element, component (part), region, layer, or portion (section) from another element, component (part), region, layer, or portion (section). Thus, without departing from the teachings of this embodiment, the first element, component (part), region, layer, or portion (section) discussed below may be referred to as the second element, component (part), region, layer, or portion (section).
[0043] It will be further understood that the terms "comprising" or "including" when used in this specification indicate the presence of the stated features, regions, wholes, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, wholes, steps, operations, elements, components, and / or their groups.
[0044] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the relevant art and the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.
[0045] As used herein, "about" or "approximately" includes the stated value and means within an acceptable deviation range for the specific value as determined by one of ordinary skill in the art in view of the measurements discussed and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean a deviation within one or more standard deviation ranges relative to the stated value, or within the ranges of ±30%, 20%, 10%, 5%.
[0046] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the protection scope of the present invention. In addition, it should be understood that after reading the content disclosed in the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the protection scope defined by the present invention.
[0047] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; unless otherwise specified, the reagents, materials, etc. used in the following examples can all be obtained from commercial sources.
[0048] Glossary of Terms
[0049] As used in the present invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.
[0050] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 10 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.
[0051] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, etc.
[0052] As used in the present invention, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic group having 2 to 10 carbon atoms, and at least one heteroatom is contained in the ring, and the heteroatom is selected from O, S, N, P, Si.
[0053] As used in the present invention, the term "alkoxy" refers to a straight-chain, branched-chain or cyclic chain. The number of carbon atoms in the alkoxy is not particularly limited herein, but the alkoxy preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, benzyloxy.
[0054] As used in the present invention, the term "cycloalkenyl" refers to an unsaturated carbocyclic ring and does not have aromaticity.
[0055] As used in the present invention, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring and does not have aromaticity.
[0056] As used in the present invention, the term "aryl having 6 to 60 carbon atoms" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl may have a form in which two or more of the rings are simply linked to each other or fused to each other. Examples of such aryls include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, and the like.
[0057] As used in the present invention, the term "arylene" refers to a divalent aryl derived by removing one hydrogen atom from "aryl". For example, phenyl becomes phenylene after removing one hydrogen atom, and naphthyl becomes naphthylene after removing one hydrogen atom.
[0058] As used in the present invention, the term "heteroaryl having 3 to 60 carbon atoms" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 - 3 carbons in the ring, is replaced by a heteroatom such as N, O, S, P, B or Si. Further, such a heteroaryl may have a form in which two or more of the rings are simply linked to each other or fused to each other or fused to an aryl. Examples of such heteroaryls include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furyl, thienyl, benzofuryl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuryl, dibenzothienyl, etc., and the present invention is not limited thereto.
[0059] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl derived by removing one hydrogen atom from "heteroaryl". For example, pyridyl becomes pyridylene after removing one hydrogen atom.
[0060] As used in the present invention, the term "silyl" refers to a trisubstituted silyl, such as trimethylsilyl, triphenylsilyl, and the like.
[0061] As used in the present invention, in the expression "Z group having X - Y carbon atoms" or "Z group of C(X - Y)", "having X - Y carbon atoms" means the number of carbon atoms of the Z group when it is unsubstituted, excluding the carbon atoms of the substituents when it is substituted. For example, aryl having 6 to 60 carbon atoms means that when unsubstituted, the number of carbon atoms in the aryl is any integer from 6 to 60, that is, when unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20... 60.
[0062] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where substitution occurs can be the position where the hydrogen atom is replaced. That is, this position is not limited to a specific position as long as the hydrogen at this position can be replaced by a substituent. For example, the carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto,
[0063]
[0064] which indicates the substitution position. "Unsubstituted" means retaining a hydrogen atom, and in this case, the hydrogen atom includes protium, deuterium, and tritium.
[0065] When there are two or more substituents, the two or more substituents can be the same or different.
[0066] As used in the present invention, the term "terphenyl" includes
[0067] As used in the present invention, the hydrogen atom includes protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms from natural sources, or deuterium atoms may be introduced by deuterating a part or all of the starting compounds. If deuterium atoms are introduced from the starting materials, the deuteration rate can be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate can also be 1% or more, or 5% or more, or 10% or more. If the deuteration rate is not 100%, it represents a mixture of deuterated compounds and non-deuterated compounds, or a mixture of fully deuterated compounds and incompletely deuterated compounds, or a mixture of fully deuterated compounds, non-deuterated compounds, and incompletely deuterated compounds.
[0068] As used in the present invention, terms such as the first, the second, A, B, etc. are used. The above terms are only used to distinguish the components and do not limit the nature or order of the components corresponding to the terms.
[0069] Organic electroluminescent element
[0070] The structure used in the organic electroluminescent element of the present invention is a publicly known structure, which includes an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound of the present invention.
[0071] The organic layer may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.
[0072] The light-emitting element of the present invention can emit fluorescence or phosphorescence or a combination of them, and the light-emitting element can emit light singly or in series with multiple light-emitting units.
[0073] As simple light-emitting elements, the following can be cited, but are not limited to,
[0074] (1) Hole transport layer / fluorescent light-emitting layer / electron transport layer;
[0075] (2) Hole transport layer / phosphorescent light-emitting layer / electron transport layer;
[0076] (3) Hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;
[0077] (4) Hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;
[0078] (5) Hole transport layer / fluorescent light-emitting layer / spacer layer / phosphorescent light-emitting layer / electron transport layer;
[0079] (6) Hole transport layer / electron blocking layer / fluorescent light-emitting layer / electron transport layer;
[0080] (7) Hole transport layer / electron blocking layer / fluorescent light-emitting layer / hole blocking layer / electron transport layer;
[0081] (8) Hole transport layer / electron blocking layer / phosphorescent light-emitting layer / electron transport layer;
[0082] (9) Hole transport layer / electron blocking layer / phosphorescent light-emitting layer / hole blocking layer / electron transport layer;
[0083] (10) Hole injection layer / hole transport layer / phosphorescent light-emitting layer / electron transport layer / electron injection layer;
[0084] (11) Hole injection layer / hole transport layer / fluorescent light-emitting layer / electron transport layer / electron injection layer;
[0085] (12) Hole injection layer / hole transport layer / electron blocking layer / phosphorescent light-emitting layer / electron transport layer / electron injection layer;
[0086] (13) Hole injection layer / hole transport layer / electron blocking layer / fluorescent light-emitting layer / electron transport layer / electron injection layer;
[0087] Each of the above phosphorescent / fluorescent light-emitting layers can emit light of different colors.
[0088] As a tandem organic electroluminescent device, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can generally also be referred to as a charge generation layer, an electron extraction layer, a linking layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, in order to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer, or to adjust the carrier balance, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer.
[0089] When the organic light-emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.
[0090] The organic electroluminescent device of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers are formed by using the compound of formula (1).
[0091] As the cathode material, a material with a low work function is usually used to facilitate electron injection into the organic material layer.
[0092] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes.
[0093] The hole transport material is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately be a material with a high hole mobility that receives holes from the anode or the hole injection layer and transfers the holes to the light-emitting layer.
[0094] The light-emitting material can be a material that respectively receives holes and electrons from the hole transport layer and the electron transport layer and combines the holes and electrons to emit light in the visible light region. The light-emitting layer material includes a host material and a doping material.
[0095] The electron transport material is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can be a material with a high electron mobility that receives electrons from the cathode and transfers the electrons to the light-emitting layer.
[0096] The electron injection layer is a layer that injects electrons from the electrode.
[0097] The hole blocking layer is a layer that blocks holes from reaching the cathode.
[0098] The electron blocking layer is a layer that blocks electrons from reaching the anode.
[0099] According to the materials used, the organic light-emitting device of the present specification can be a top-emitting device, a bottom-emitting device, or a double-emission device.
[0100] The charge generation layer refers to the intermediate layer between the anode and the cathode in a tandem structure device, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and efficiently transport carriers.
[0101] The core of the present invention is to provide an arylamine compound having the structure shown in formula (1),
[0102]
[0103] wherein, L 1 and L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,
[0104] R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heteroalkenyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;
[0105] A is a divalent ethyl group, r is selected from 0 or 1, and when r is 0, A and the bonds connected on both sides do not exist;
[0106] Ar 1 is *-L 3 -R 3 ;
[0107] L 3 is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroaryl group;
[0108] R 3 is selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroaryl group;
[0109] The substituents in the "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, silyl, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, a C3-C30 heteroaryl group,
[0110] In the arylhetero group, heterocycloalkyl group, heterocycloalkenyl group, and heteroaryl group, the heteroatoms are each independently at least one of N, O, S, Si, and P.
[0111] Specifically, the arylamine compound includes the following structure:
[0112]
[0113]
[0114]
[0115]
[0116]
[0117] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and well-known synthesis methods. The methods of the present invention are only exemplary, and the compounds obtained by substituting the above reactants in the general formula with commercially available raw materials or methods of the prior art are also included within the scope of this application.
[0118] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and well-known synthesis methods. There are various synthesis methods for the compounds of the present invention, and the following general formula is only one of the synthesis methods:
[0119]
[0120] R 5 When it is not hydrogen, the intermediate synthesis method is as follows:
[0121]
[0122] When it is not hydrogen and / or L 4 When it is not a single bond, the intermediate synthesis method is as follows:
[0123]
[0124] The specific synthesis examples of this application are as follows:
[0125] Synthesis Example 1:
[0126] Preparation of Compound 1-1
[0127]
[0128] (1) First, dissolve C-1: 2-bromopyrene (42.0 g, 149.4 mmol) in ethyl acetate (500 mL), then add Raney nickel (20 g) and react at room temperature for 48 hours. After the reaction is completed, remove the catalyst using a diatomaceous earth column, add Pd / C (10.0 g) catalyst, and carry out the hydrogenation reaction again at room temperature under a hydrogen pressure of 100 psi for 72 hours. After the reaction is completed, remove the solvent under reduced pressure, and the product is separated and purified by a silica gel column to obtain pure C: 2-bromo-4,5,9,10-tetrahydrobenzopyrene (35.7 g, yield 83%).
[0129] LC-MS(APCI): 285.82(M+H + )
[0130] (2) Under a nitrogen atmosphere, add compound B: 9-phenanthrylamine; (35.9 g, 186.3 mmol), A: 4-(4-bromophenyl)-dibenzofuran (50.0 g, 155.2 mmol) to a three-necked flask, add toluene (300 ml), heat under reflux for 0.5 h, cool to 70 - 80 °C, and slowly add sodium tert-butoxide (22.3 g, 232.8 mmol), Pd 2 (dba) 3 (2.80 g, 3.1 mmol), xphos (11.8 g, 24.8 mmol). After the system is stable, heat to 100 - 110 °C for 2 hours. Lower the temperature to room temperature, add 300 ml of water, stir and separate with 100 ml of toluene, extract the aqueous phase once with 200 ml of toluene, carry out liquid-liquid extraction, dry the organic phase over anhydrous sodium sulfate, filter and concentrate to dryness, and recrystallize with 1000 ml of toluene, filter to obtain intermediate compound A-B (43.0 g, 98.8 mmol, 64%).
[0131] LC-MS(APCI): 436.46(M+H + )
[0132] (3) Under a nitrogen atmosphere, add compound C: 2-bromo-4,5,9,10-tetrahydrobenzopyrene (20.0 g, 70.4 mmol) and compound A-B (33.6 g, 77.4 mmol) to a three-necked flask, add xylene (300 mL), add NaOtBu (10.1 g, 105.6 mmol), add bis(tri-tert-butylphosphine)palladium(0) (2.1 g, 4.10 mmol), then heat and stir for 4 hours. Lower the temperature to room temperature, filter to remove the base, concentrate the xylene under reduced pressure, and recrystallize with 160 mL of ethyl acetate to obtain the target compound 1-1 (29.3 g, 45.76 mmol, 65%).
[0133] LC-MS(APCI): 640.56 (M+H + )
[0134] Synthesis Example 2: Preparation of Compound 1-2
[0135]
[0136] Compound 1-2 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, where 4-(4-bromophenyl)dibenzothiophene was used instead of Compound A, to obtain Compound 1-2 (16.5 g, yield 73%).
[0137] LC-MS(APCI): 657.83 (M+H + )
[0138] Synthesis Example 3: Preparation of Compound 1-12
[0139]
[0140] In a nitrogen system, D-1 (1 equivalent) was dissolved in toluene solvent, and D-2: phenylboronic acid (0.9 equivalent) was added. K 2 CO 3 (4 equivalents) was added to the solution. Tetrahydrofuran solvent was added, and 0.05 equivalent of palladium was added. The mixture was refluxed and stirred at 80 °C. After the reaction was completed, ethyl acetate and distilled water were mixed for extraction. Magnesium sulfate was used to remove the water in the organic layer. Wet column chromatography was carried out using n-hexane and ethyl acetate to obtain the solid compound D-1-2.
[0141] Compound 1-12 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, to obtain Compound 1-12 (20.9 g, yield 80%), where Compound D was used instead of Compound A, and the synthesis method of Compound D was referred to the above steps.
[0142] LC-MS(APCI): 765.77 (M+H + )
[0143] Synthesis Example 4: Preparation of Compound 1-15
[0144]
[0145] Compound 1-15 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, to obtain Compound 1-15 (17.3 g, yield 75%), where 1-bromopyrene was used instead of Compound C-1, and Compound E was used instead of Compound A, and the synthesis method of Compound E was referred to Example 3.
[0146] LC-MS(APCI): 689.45 (M+H + )
[0147] Synthesis Example 5: Preparation of Compound 1-23
[0148]
[0149] Put F-2 (65 g, 237.8 mmol), n-bromo succinimide (42.32 g, 237.8 mmol), and dichloromethane (1.2 L) into a round-bottom flask respectively, and stir at room temperature for 4 hours. After the reaction is completed, add distilled water, and extract the reaction product with dichloromethane and water. Then dry and concentrate the organic layer with MgSO4. Then recrystallize with dichloromethane and n-hexane to obtain F-3 (74.55 g, 89%).
[0150] Compound 1-23 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1, and Compound 1-23 (18.7 g, yield 72%) was obtained, where Compound F was used instead of Compound A, and the synthesis method of Compound F was referred to the synthesis of Compound D in Example 3.
[0151] LC-MS(APCI): 733.57 (M+H + )
[0152] Synthesis Example 6: Preparation of Compound 1-40
[0153]
[0154] Compound 1-40 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1, and Compound 1-40 (16.8 g, yield 76%) was obtained. Among them, 1-bromopyrene was used instead of Compound C-1, and 2-bromodibenzofuran was used instead of Compound A.
[0155] LC-MS(APCI): 565.21 (M+H + )
[0156] Example 7: Preparation of Compound 1-42
[0157]
[0158] Compound 1-42 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1, and Compound 1-42 (18.6 g, yield 68%) was obtained. Among them, 1-bromopyrene was used instead of Compound C-1, and 1-bromodibenzothiophene was used instead of Compound A.
[0159] LC-MS(APCI): 581.23 (M+H + )
[0160] Synthesis Example 8: Preparation of Compound 1-65
[0161]
[0162] (1) First, dissolve α-1: 2,7-dibromopyrene (42.0 g) in ethyl acetate (500 mL), then add Raney nickel (20.0 g) and react at room temperature for 48 hours. After confirming the completion of the reaction by TLC, remove the catalyst using a diatomaceous earth column, add Pd / C (10.0 g), and perform hydrogenation reaction again at room temperature for 72 hours under a hydrogen pressure of about 100 psi. After the reaction is completed, remove the solvent under reduced pressure, and purify the product by silica gel column chromatography to obtain pure β-1: 4,5,9,10-tetrahydropyrene (32.0 g).
[0163] LC-MS (APCI): 363.38 (M+H + )
[0164] (2) Under a nitrogen atmosphere, add β-1 (30.0 g, 83.10 mmol), benzenebromonic acid (26.0 g, 83.1 mmol), Pd(OAc) 2 (0.18 g, 0.82 mmol), 100 ml (78.7 mmol) of 2 mol / L aqueous potassium carbonate (K 2 CO 3 ) solution, 500 mg (3.31 mmol) of tris(ortho-methylphenyl)phosphine, and 200.0 ml of 1,2-dimethoxyethane (abbreviation: dimethoxyethane) to the reaction flask, and stir at 800 °C for 9 hours. After the reaction is completed, the extracted solid is recovered by suction filtration. Then dissolve it in toluene and filter through diatomaceous earth and alumina. After washing the filtrate with water and saturated salt solution, dry it with magnesium sulfate. After natural filtration, concentrate the filtrate to obtain the target substance γ-1 (15.0 g).
[0165] LC-MS (APCI): 362.54 (M+H + )
[0166] Compound 1-65 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, and Compound 1-65 (18.4 g, yield 65%) was obtained, where Compound F in Example 5 was used instead of Compound A, and Compound γ-1 was used instead of Compound C.
[0167] LC-MS (APCI): 809.23 (M+H + )
[0168] Synthesis Example 9: Preparation of Compound 1-71
[0169] Compound 1-71 was synthesized according to the synthesis method of compound 1-1 in Example 1, except that compound c-1 was used instead of compound C, and 3-bromo-7-phenyldibenzofuran was used instead of compound A, to obtain compound 1-71 (17.3 g, yield 75%).
[0170] LC-MS(APCI): 717.85(M+H + )
[0171] Example 10: Preparation of Compound 1-80
[0172]
[0173] Compound 1-80 was synthesized according to the synthesis method of compound 1-1 in Example 1, with compound 1-80-1 replacing compound C, compound 1-80-2 replacing compound A, and compound 1-80-3 replacing compound B, to obtain compound 1-80 (14.9 g, yield 68%). The synthesis methods of compounds 1-80-1, 1-80-2, and 1-80-3 refer to Example 9 and Example 5 respectively.
[0174] LC-MS(APCI): 793.24(M+H + )
[0175] Example 11: Preparation of Compound 1-85
[0176]
[0177] Compound 1-85 was synthesized according to the synthesis method of compound 1-1 in Example 1, with compound 1-85-1 replacing compound C, to obtain compound 1-85 (15.6 g, yield 71%). The synthesis method of compound 1-85-1 refers to Example 9 and Example 5.
[0178] LC-MS(APCI): 691.78(M+H + )
[0179] Example 12: Preparation of Compound 1-87
[0180]
[0181] Compound 1-87 was synthesized according to the synthesis method of compound 1-1 in Example 1, with compound 1-87-1 replacing compound A and compound 1-85-1 replacing compound C, to obtain compound 1-87 (19.5 g, yield 75%). The synthesis method of compound 1-87-1 refers to Example 5.
[0182] LC-MS(APCI): 739.21(M+H+ )
[0183] Example 13: Preparation of Compound 1-98
[0184]
[0185] Compound 1-98 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1. Using 4-(4-bromophenyl)dibenzothiophene instead of Compound A and Compound 1-98-2 instead of Compound C, Compound 1-98 (17.1 g, yield 66%) was obtained. The synthesis method of Compound 1-98-2 refers to the synthesis methods of Example 9 and Example 5.
[0186] LC-MS(APCI): 707.06(M+H + )
[0187] Example 14: Preparation of Compound 1-104
[0188]
[0189] Compound 1-104 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1. Using 1-104-1 instead of Compound A and Compound 1-140-2 instead of Compound C, Compound 1-104 (16.5 g, yield 62%) was obtained. Among them, the syntheses of Compounds 1-104-1 and 1-140-2 refer to the syntheses of Compound G in Example 11 and Compound F-3 in Example 5 respectively.
[0190] LC-MS(APCI): 631.49(M+H + )
[0191] Example 15: Preparation of Compound 1-105
[0192]
[0193] Compound P: 1-bromodibenzothiophene (10 mmol) was added to 50 ml of acetic acid, heated to 80 °C, and hydrogen peroxide (40 mmol) was slowly added dropwise, and the reaction was continuously heated for 2 hours. After the reaction was completed, it was cooled, allowed to stand, and filtered. The filtered residue was washed with ethanol 3 times and then dried to obtain white needle-like crystals P-1 (yield 90%).
[0194] Compound 1-105 was synthesized by referring to the synthesis method of Compound 1-1 in Example 1. Using 1-104-1 instead of Compound A and Compound 1-105-1 instead of Compound C, Compound 1-105 (14.3 g, yield 74%) was obtained. Among them, the synthesis of Compound 1-105-1 refers to the synthesis of Example 10.
[0195] LC-MS(APCI): 663.75 (M+H + )
[0196] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the above compounds and known synthesis methods. Other structures can also be obtained with reference to the above synthesis methods and conventional synthesis means in the art.
[0197] The following application examples further illustrate the application of the compounds described in the present invention in the preparation of organic electroluminescent devices.
[0198] Application Example 1:
[0199] This example provides an organic electroluminescent device, as Figure 1 shown, including a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting auxiliary layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a second electrode layer 8.
[0200] Comparative Example 1
[0201] HATCN was evaporated on an ITO substrate to form a first hole injection layer (HIL) with a thickness of , HT was evaporated on the above first hole injection layer to form a hole transport layer (HTL) with a thickness of , EB was evaporated on the above hole transport layer to form a light-emitting auxiliary layer (EBL) with a thickness of , GH+GD (3 wt%) was evaporated on the light-emitting auxiliary layer to form a light-emitting layer (EML) with a thickness of , an electron transport layer (ETL) with a thickness of was sequentially evaporated, and Al (with a thickness of ) was evaporated to form a cathode, thereby manufacturing an organic electroluminescent device.
[0202] The structural formula of the device involved is as follows:
[0203]
[0204] Comparative Example 2
[0205] The organic electroluminescent device of Comparative Example 2 was prepared by the same method as in the embodiment of Comparative Example 1, except that the light-emitting auxiliary layer (EBL) was replaced by compound EB-1 instead of compound EB in the embodiment of Comparative Example 1.
[0206] Comparative Example 3
[0207] The organic electroluminescent device of Comparative Example 3 was prepared by the same method as in the embodiment of Comparative Example 1, except that the light-emitting auxiliary layer (EBL) was replaced by compound EB-2 instead of compound EB in the embodiment of Comparative Example 1.
[0208] Device Example 1
[0209] The organic electroluminescent device of Device Example 1 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-1 from Compound EB in the implementation scheme of Comparative Example 1.
[0210] Device Example 2
[0211] The organic electroluminescent device of Device Example 2 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-2 from Compound EB.
[0212] Device Example 3
[0213] The organic electroluminescent device of Device Example 3 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-12 from EB.
[0214] Device Example 4
[0215] The organic electroluminescent device of Device Example 4 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-15 from Compound EB.
[0216] Device Example 5
[0217] The organic electroluminescent device of Device Example 5 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-23 from Compound EB in the implementation scheme of Comparative Example 1.
[0218] Device Example 6
[0219] The organic electroluminescent device of Device Example 6 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-40 from Compound EB.
[0220] Device Example 7
[0221] The organic electroluminescent device of Device Example 7 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-42 from Compound EB in the implementation scheme of Comparative Example 1.
[0222] Device Example 8
[0223] The organic electroluminescent device of Device Example 8 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-65 instead of Compound EB in the Embodiment of Comparative Example 1.
[0224] Device Example 9
[0225] The organic electroluminescent device of Device Example 9 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-71 instead of Compound EB in the Embodiment of Comparative Example 1.
[0226] Device Example 10
[0227] The organic electroluminescent device of Device Example 10 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-80 instead of Compound EB in the Embodiment of Comparative Example 1.
[0228] Device Example 11
[0229] The organic electroluminescent device of Device Example 11 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-85 instead of Compound EB in the Embodiment of Comparative Example 1.
[0230] Device Example 12
[0231] The organic electroluminescent device of Device Example 12 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-87 instead of Compound EB in the Embodiment of Comparative Example 1.
[0232] Device Example 13
[0233] The organic electroluminescent device of Device Example 13 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-98 instead of Compound EB in the Embodiment of Comparative Example 1.
[0234] Device Example 14
[0235] The organic electroluminescent device of Device Example 14 was prepared by the same method as in the Embodiment of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-104 instead of Compound EB in the Embodiment of Comparative Example 1.
[0236] Device Example 15
[0237] The organic electroluminescent device of Device Example 15 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 1-105 instead of Compound EB in the implementation scheme of Comparative Example 1.
[0238] Evaluation of Organic Electroluminescent Element
[0239] Lifetime test method: A voltage was applied to the obtained organic electroluminescent element so that the current density reached 30 mA / cm 2 , and the time until the luminance became 95% of the initial luminance (LT95 (unit: hours)) was measured. Taking the lifetime of Comparative Example 1 as 100%, the relative lifetime values of each comparative example and example were obtained.
[0240] The driving voltage was tested at a current density of 15 mA / cm 2 . Taking the driving voltage of Comparative Example 1 as 100%, the relative driving voltage values of each comparative example and example were obtained.
[0241] The current efficiency was tested at a current density of 15 mA / cm 2 . Taking the current efficiency of Comparative Example 1 as 100%, the relative current efficiency values of each comparative example and example were obtained. The test results are shown in Table 1.
[0242] Table 1
[0243]
[0244]
[0245] From the results shown in Table 1 above, it can be seen that when the organic compound of the present invention is applied in the emission auxiliary layer, compared with the comparative examples, the driving voltage is reduced, and the luminous efficiency and lifetime are significantly improved. Therefore, the compounds of the present invention are suitable for preparing high-performance organic electroluminescent elements.
[0246] It is easy for those skilled in the art to understand that the above are only the preferred embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention should be included within the protection scope of the present invention.
Claims
1. An aromatic amine compound, characterized in that, the aromatic amine compound has the structure shown in formula (1), Among them, L 1 and L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group. R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heteroalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; A is a divalent ethyl group, r is selected from 0 or 1, when r is 0, A and the bonds connected on both sides do not exist; Ar 1 is *-L 3 -R 3 , L 3 Selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; R 3 selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; when the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, the heteroatoms in the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl are each independently at least one of N, O, S, Si, and P.
2. An aromatic amine compound according to claim 1, characterized in that, the aromatic amine compound has the structures shown in formulas (2)-(4): Among them, L 1 、L 2 、R 1 、R 2 、Ar 1 are defined in the same way as in Claim 1.
3. An aromatic amine compound according to claim 1 or 2, characterized in that, The Ar 1 is *-L 3 -R 3 wherein L 3 is selected from a single bond, phenylene, biphenylene, naphthylene, anthrylene, phenanthrylene, fluoranthenylene, pyrenylene, perylenylene, terphenylenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, R 3 selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, and any one of two or more combinations of the above groups.
4. An aromatic amine compound according to claim 1 or 2, characterized in that, L 1 and L 2 each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group.
5. An aromatic amine compound according to claim 1 or 2, characterized in that, L 1 and L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted phenylanthryl, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted terphenylene.
6. An aromatic amine compound according to claim 1 or 2, characterized in that, R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl.
7. An aromatic amine compound according to claim 1 or 2, characterized in that, the aromatic amine compound includes the following structure:
8. An organic electroluminescent element, characterized in that, the organic electroluminescent element includes: a first electrode; a second electrode arranged to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode and including a light-emitting layer, wherein one or more of the organic material layers contain the aromatic amine compound according to any one of claims 1-7.
9. An organic electroluminescent element according to claim 8, characterized in that, the organic material layer contains a light-emitting auxiliary layer, and the light-emitting auxiliary layer contains the aromatic amine compound according to any one of claims 1-7.
10. An electronic device, characterized in that, the electronic device includes the organic electroluminescent element according to claim 9.